DRUG APPROVALS BY DR ANTHONY MELVIN CRASTO
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Alizulatide vixocianine
Alizulatide vixocianine
CAS 2924859-51-6
MF C115H145N17O25S, 2,197.55
L-Serine, N-[6-[2-[7-[1,3-dihydro-1,1-dimethyl-3-(4-sulfobutyl)-2H-benz[e]indol-2-ylidene]-1,3,5-heptatrien-1-yl]-1,1-dimethyl-1H-benz[e]indolio]-1-oxohexyl]-L-α-glutamyl-L-α-glutamyl-L-α-aspartyl-3-cyclohexyl-L-alanyl-L-phenylalanyl-D-seryl-D-arginyl-L-tyrosyl-L-leucyl-L-tryptophyl-, inner salt
4-[2-[7-[3-[6-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2R)-1-[[(2R)-5-carbamimidamido-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(1S)-1-carboxy-2-hydroxyethyl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]amino]-1-oxopentan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-3-cyclohexyl-1-oxopropan-2-yl]amino]-3-carboxy-1-oxopropan-2-yl]amino]-4-carboxy-1-oxobutan-2-yl]amino]-4-carboxy-1-oxobutan-2-yl]amino]-6-oxohexyl]-1,1-dimethylbenzo[e]indol-3-ium-2-yl]hepta-2,4,6-trienylidene]-1,1-dimethylbenzo[e]indol-3-yl]butane-1-sulfonate
diagnostic imaging agent, 8M3Q8XZ6MJ
Alizulatide vixocianine is a polypeptide that can be discovered through polypeptide screening. Polypeptide screening is a research tool mainly based on immunoassay methods to identify active polypeptides. It can be applied to protein interaction, functional analysis, antigenic epitope screening, especially in the fields of active molecule research and development.
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/////////alizulatide vixocianine, diagnostic imaging agent, 8M3Q8XZ6MJ
Aleniglipron
Aleniglipron
CAS 2685823-26-9
MF C49H55FN9O6P MW916.0 g/mol
3-[(1S,2S)-1-[2-[(4S)-3-[3-[4-diethylphosphoryl-3-(methylamino)phenyl]-2-oxoimidazol-1-yl]-2-(4-fluoro-3,5-dimethylphenyl)-4-methyl-6,7-dihydro-4H-pyrazolo[4,3-c]pyridine-5-carbonyl]-5-(oxan-4-yl)indol-1-yl]-2-methylcyclopropyl]-4H-1,2,4-oxadiazol-5-one
glucagon-like peptide 1 (GLP-1) receptor agonist, GSBR-1290, GSBR 1290, Z6XCL6R9SX
Aleniglipron (development code GSBR-1290) is a small-molecule GLP-1 agonist developed by Structure Therapeutics.[1] It is delivered orally and is in a Phase II trial as of 2023.[2][3][4] In June 2024, Structure Therapeutics reported positive topline data from a Phase 2a obesity study in which GSBR-1290 demonstrated clinically meaningful and statistically significant placebo-adjusted mean weight loss and generally favorable safety and tolerability results.[5]
- Aleniglipron Phase 2 Body Composition StudyCTID: NCT07169942Phase: Phase 2Status: Active, not recruitingDate: 2025-10-31
- A Dose-Range Study of Aleniglipron (GSBR-1290) in Participants Living With Obesity or Overweight With at Least One Weight-related ComorbidityCTID: NCT06703021Phase: Phase 2Status: Active, not recruitingDate: 2025-09-15
- A Phase 2b, Dose-range Finding Study of the Efficacy and Safety of Multiple Doses of Aleniglipron (GSBR-1290) in Participants Living With Obesity or Overweight With at Least One Weight-related ComorbidityCTID: NCT06693843Phase: Phase 2Status: Active, not recruitingDate: 2025-08-26
SYN
https://patentscope.wipo.int/search/en/detail.jsf?docId=US367934715&_cid=P10-MJRZ0C-74156-1
Example 2: Synthesis of
3-((1S,2S)-1-(2-((S)-3-(3-(4-(diethylphosphoryl)-3-(methylamino)phenyl)-2-oxo-2,3-dihydro-1H-imidazol-1-yl)-2-(4-fluoro-3,5-dimethylphenyl)-4-methyl-4,5,6,7-tetrahydro-2H-pyrazolo[4,3-c]pyridine-5-carbonyl)-5-(tetrahydro-2H-pyran-4-yl)-1H-indol-1-yl)-2-methylcyclopropyl)-1,2,4-oxadiazol-5(4H)-one (Compound 121a)
Step A: (4-bromo-2-fluorophenyl)diethylphosphine oxide
| 1H NMR (400 MHz, DMSO-d 6) δ 7.63-7.73 (m, 3H), 1.95-2.08 (m, 2H), 1.80-1.92 (m, 2H), 0.80-1.10 (m, 6H). |
Step B: (4-bromo-2-(methylamino)phenyl)diethylphosphine oxide
| 1H NMR (600 MHz, DMSO-d 6) δ 7.75-7.76 (m, 1H), 7.11 (dd, J=13.2, 8.4 Hz, 1H), 6.63-6.80 (m, 2H), 2.71 (d, J=5.4 Hz, 3H), 1.88-1.94 (m, 4H), 0.90-1.05 (m, 6H). |
Step C: tert-butyl (S)-3-(3-(4-(diethylphosphoryl)-3-(methylamino)phenyl)-2-oxo-2,3-dihydro-1H-imidazol-1-yl)-2-(4-fluoro-3,5-dimethylphenyl)-4-methyl-2,4,6,7-tetrahydro-5H-pyrazolo[4,3-c]pyridine-5-carboxylate
Step D: (5)-1-(4-(diethylphosphoryl)-3-(methylamino)phenyl)-3-(2-(4-fluoro-3,5-dimethylphenyl)-4-methyl-4,5,6,7-tetrahydro-2H-pyrazolo[4,3-c]pyridin-3-yl)-1,3-dihydro-2H-imidazol-2-one hydrochloride
Step E: 3-((1S,2S)-1-(2-((S)-3-(3-(4-(diethylphosphoryl)-3-(methylamino) phenyl)-2-oxo-2,3-dihydro-1H-imidazol-1-yl)-2-(4-fluoro-3,5-dimethylphenyl)-4-methyl-4,5,6,7-tetrahydro-2H-pyrazolo[4,3-c]pyridine-5-carbonyl)-5-(tetrahydro-2H-pyran-4-yl)-1H-indol-1-yl)-2-methylcyclopropyl)-1,2,4-oxadiazol-5(4H)-one
PAT
- Heterocyclic glp-1 agonistsPublication Number: EP-4097099-A1Priority Date: 2020-02-07
- Heterocyclic GLP-1 agonistsPublication Number: CN-115698003-APriority Date: 2020-02-07
- Heterocyclic glp-1 agonistsPublication Number: EP-4097099-B9Priority Date: 2020-02-07Grant Date: 2025-04-30
- Heterocyclic glp-1 agonistsPublication Number: EP-4458834-A2Priority Date: 2020-02-07
- Heterocyclic GLP-1 agonistsPublication Number: US-11926643-B2Priority Date: 2020-02-07Grant Date: 2024-03-12
- Heterocyclic GLP-1 agonistsPublication Number: CN-119823184-APriority Date: 2020-02-07
- Heterocyclic GLP-1 agonistsPublication Number: CN-119841865-APriority Date: 2020-02-07
- Heterocyclic GLP-1 agonistsPublication Number: CN-119874775-APriority Date: 2020-02-07
- Heterocyclic GLP-1 agonistsPublication Number: US-11492365-B2Priority Date: 2020-02-07Grant Date: 2022-11-08
- Heterocyclic GLP-1 agonistsPublication Number: CN-115698003-BPriority Date: 2020-02-07Grant Date: 2024-10-11
- Heterocyclic glp-1 agonistsPublication Number: US-2022213130-A1Priority Date: 2020-02-07
- Heterocyclic glp-1 agonistsPublication Number: EP-4097099-B1Priority Date: 2020-02-07Grant Date: 2024-06-26
- Heterocyclic glp-1 agonistsPublication Number: US-2023174565-A1Priority Date: 2020-02-07
- Salts and solid forms of a compound having glp-1 agonist activityPublication Number: WO-2024125602-A1Priority Date: 2022-12-15
- Salts and solid forms of a compound having glp-1 agonist activityPublication Number: EP-4634180-A1Priority Date: 2022-12-15
- Heterocyclic glp-1 agonistsPublication Number: US-2024366639-A1Priority Date: 2021-08-12
- Heterocyclic glp-1 agonistsPublication Number: WO-2023016546-A1Priority Date: 2021-08-12
- Heterocyclic glp-1 agonistsPublication Number: WO-2021155841-A1Priority Date: 2020-02-07
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References
- Mao, Ting; Meng, Qinghua; Zhang, Haizhen; Zhang, Jinqiang J.; Shi, Songting; Guan, Zhibo; Jiang, Xinglong; Zhang, Fang; Lei, Hui; Lin, Xichen (20 June 2023). “760-P: Discovery of GSBR-1290, a Highly Potent, Orally Available, Novel Small Molecule GLP-1 Receptor Agonist”. Diabetes. 72 (Supplement_1) 760-P. doi:10.2337/db23-760-P. S2CID 259430363.
- “Structure Therapeutics Initiates Phase 2a Study of Oral GLP-1 agonist GSBR-1290 for the Treatment of Type 2 Diabetes and Obesity”. BioSpace. 25 May 2023. Retrieved 4 November 2023.
- “Structure announces positive results from oral GLP-1 receptor agonist gsbr-1290”. Bariatric News. 2 October 2023. Retrieved 4 November 2023.
- Satija, Bhanvi (29 September 2023). “Structure Therapeutics surges as early data from obesity pill tops expectations”. Reuters. Retrieved 4 November 2023.
- “Structure Therapeutics Reports Positive Topline Data from its Phase 2a Obesity Study and Capsule to Tablet PK Study for its Oral Non-Peptide Small Molecule GLP-1 Receptor Agonist GSBR-1290”. BioSpace. 2024-06-03. Retrieved 2024-10-24.
| Legal status | |
|---|---|
| Legal status | Investigational |
| Identifiers | |
| IUPAC name | |
| CAS Number | 2685823-26-9 |
| PubChem CID | 164809721 |
| DrugBank | DB18551 |
| UNII | Z6XCL6R9SX |
| Chemical and physical data | |
| Formula | C49H55FN9O6P |
| Molar mass | 916.008 g·mol−1 |
| InChI | |
//////////Aleniglipron, glucagon-like peptide 1 (GLP-1) receptor agonist, GSBR-1290, GSBR 1290, Z6XCL6R9SX
Limnetrelvir
Limnetrelvir
CAS 2923500-04-1
MF C27H23F4N5O4 MW 557.50
N-[(3R)-1-[4-cyano-2-(morpholine-4-carbonyl)-6-(trifluoromethyl)phenyl]pyrrolidin-3-yl]-8-fluoro-2-oxo-1H-quinoline-4-carboxamide
N-{(3R)-1-[4-cyano-2-(morpholine-4-carbonyl)-6-
(trifluoromethyl)phenyl]pyrrolidin-3-yl}-8-fluoro-2-oxo1,2-dihydroquinoline-4-carboxamide
antiviral, ABBV-903, ABBV 903, 4TPS988XGG
Limnetrelvir (ABBV-903) is a MPro inhibitor. Limnetrelvir could be used in antiviral research.
SYN
Example 1 – Synthesis of Compound (2) (R)-N-(1-(4-cyano-2-(morpholine-4-carbonyl)-6-(trifluoromethyl)phenyl)pyrrolidin-3-yl)-8-fluoro-2-oxo-1,2-dihydroquinoline-4-carboxamide
Compound 2F – Synthesis of 8-fluoro-2-oxo-1,2-dihydroquinoline-4-carboxylic acid
[00035] A suspension of 7-fluoroindoline-2,3-dione (55 g, 333 mmol), malonic acid (41.6 g, 400 mmol) and sodium acetate (68.3 g, 833 mmol) in acetic acid (500 mL) was heated at 112 °C overnight. The reaction mixture was cooled to room temperature and poured into cold 0.4 M aqueous HCl (2200 mL). The precipitate was collected by filtration and rinsed thoroughly with ice-cold water (~250 mL) followed by methyl tert-butyl ether (~100 mL) and then concentrated twice from acetonitrile with high vacuum. The materials were largely dissolved into 1 M aqueous NaOH (370 mL) and filtered through diatomaceous earth with a 0.1 M aqueous NaOH (50 mL) rinse. Then the filtrate was washed thrice with dichloromethane (3 x 200 mL) which removed the color. After this aqueous layer was filtered again through diatomaceous earth, it was acidified by the dropwise addition of concentrated aqueous HCl (33 mL, ~0.4 moles). The material was collected by filtration. After prolonged drying under heat and vacuum, the material was treated with water (1 L) and the mixture was made acidic by the addition of a small amount of 1 M aqueous HCl. The suspension was heated to 80 °C and then allowed to slowly cool to room temperature. The resulting material was collected by filtration, washed with 0.01 M aqueous HCl (150 mL) and dried under vacuum at 80 °C to provide the title compound (2F).1H NMR (500 MHz, DMSO-d6) δ ppm 14.00 (bs, 1H), 12.07 (bs, 1H), 8.00 (dd, J = 8.2, 1.2 Hz, 1H), 7.49 (ddd, J = 11.0, 8.1, 1.2 Hz, 1H), 7.23 (ddd, J = 8.2, 8.1, 5.2 Hz, 1H), 6.95 (s, 1H); 13C NMR (101 MHz, DMSO-d6, 90 °C) δ ppm 165.75 – 165.73 (m), 160.30, 148.75 (d, J = 246.0 Hz), 140.85 – 140.80 (m), 128.11 (d, J = 13.7 Hz), 123.85, 121.60 – 121.53 (m), 121.53 – 121.43 (m), 117.70 – 117.65 (m), 115.33 (d, J = 17.2 Hz); 19F NMR (376 MHz, DMSO-d6, 90 °C) δ ppm -130.47 (dd, J = 10.9, 5.3 Hz); MS (APCI, M+H+) m/z 208.
Compound 2G – Synthesis of (R)-N-(1-(4-cyano-2-(morpholine-4-carbonyl)-6-(trifluoromethyl)phenyl)pyrrolidin-3-yl)-8-fluoro-2-oxo-1,2-dihydroquinoline-4-carboxamide (2)
00036] To a mixture of Compound 2F (29.84 g, 144 mmol) in anhydrous N,N-dimethylformamide (360 mL) was added DMTMM (4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-
methylmorpholinium chloride) (43.17 g, 156 mmol) over twelve minutes at room temperature. After the suspension had been stirred forty minutes, it was added over eight minutes to a suspension of Compound 2E (≤120 mmol) and N-methylmorpholine (16 mL, 146 mmol) in N,N-dimethylformamide (120 mL) with a N,N-dimethylformamide (20 mL) rinse. After forty minutes, the reaction mixture was added to rapidly stirred 0.1 M aqueous K2HPO4 (2.5 L) and extracted four times with 4:1 isopropyl acetate / heptanes then once with isopropyl acetate alone. The product, which had begun to precipitate out from the combined extracts, was separated by decantation and filtration, then washed with dichloromethane. The remaining aqueous phase was extracted twice more with isopropyl acetate and all the organic extracts were combined, then washed with additional 0.1 M aqueous K2HPO4 followed by water, dried (Na2SO4), and filtered. The filtrate was concentrated with the dichloromethane wash of the material collected above. The residue was concentrated, dissolved in acetonitrile / CH2Cl2, filtered, and purified by chromatography on silica (20 to 100% acetonitrile / CH2Cl2). The collected fractions were concentrated to a small volume, and stirred in ethyl acetate overnight.
[00037] The suspension was heated at 70 °C for twenty minutes, then allowed to slowly cool to room temperature. Methyl tert-butyl ether was stirred in, the suspension was cooled to 0 °C, and the purified product was collected by filtration with rinses of 1:1 ethyl acetate / methyl tert-butyl ether followed by methyl tert-butyl ether before being dried under vacuum with heat. The material obtained previously from the early extracts were also stirred in ethyl acetate, heated at 70 °C, then allowed to slowly cool to room temperature. Methyl tert-butyl ether was stirred in, the suspension was cooled to 0 °C, and the purified product was collected by filtration with rinses of 1:1 ethyl acetate / methyl tert-butyl ether rinse followed by methyl tert-butyl ether. The material was dried overnight under vacuum to provide the title compound (2).1H NMR (500 MHz, DMSO-d6) δ ppm 11.96 (s, 1H), 9.03 – 8.84 (m, 1H), 8.21 – 8.18 (m, 1H), 7.98 – 7.93 (m, 1H), 7.56 – 7.50 (m, 1H), 7.49 – 7.43 (m, 1H), 7.21 – 7.15 (m, 1H), 6.66 – 6.59 (m, 1H), 4.51 – 4.40 (m, 1H), 3.73 – 3.55 (m, 6H), 3.54 – 3.22 (m, 6H), 2.29 – 2.18 (m, 1H), 2.07 – 1.95 (m, 1H); 1H NMR (400 MHz, DMSO-d6, 90 °C) δ ppm 11.47 (bs, 1H), 8.77 – 8.47 (m, 1H), 8.09 (d, J = 2.1 Hz, 1H), 7.88 (d, J = 2.1 Hz, 1H), 7.54 (dd, J = 8.1, 1.2 Hz, 1H), 7.39 (ddd, J = 11.0, 8.1, 1.2 Hz, 1H), 7.15 (ddd, J = 8.1, 8.1, 5.1 Hz, 1H), 6.60 (s, 1H), 4.54 – 4.43 (m, 1H), 3.74 – 3.20 (m, 12H), 2.31 – 2.21 (m, 1H), 2.06 – 1.96 (m, 1H); 13C NMR (101 MHz, DMSO-d6, 90 °C) δ
ppm 166.61, 165.97, 161.31, 149.59 (d, J = 246.3 Hz), 148.95, 146.10 – 146.03 (m), 136.00, 135.65, 133.13 (q, J = 6.1 Hz), 128.84 – 128.63 (m), 123.76 (q, J = 273.7 Hz), 122.19, 122.16, 122.12, 121.60, 118.99 – 118.91 (m), 117.75, 116.17 (d, J = 17.3 Hz), 105.57, 66.04, 57.95, 51.06, 50.35, 47.74, 42.35, 31.54; 19F NMR (376 MHz, DMSO-d6) δ ppm -57.54 – -58.10 (m), -130.02 – -130.15 (m); 19F NMR (376 MHz, DMSO-d6, 90 °C) δ ppm -58.37 – -58.97 (m), -130.96 (dd, J = 11.0, 5.1 Hz). MS (APCI, M+H+) m/z 558.
PAT
- Pyrrolidine Main Protease Inhibitors as Antiviral AgentsPublication Number: US-2024158368-A1Priority Date: 2022-10-14
- Pyrrolidine main protease inhibitors as antiviral agentsPublication Number: WO-2024081351-A1Priority Date: 2022-10-14
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/////////limnetrelvir, antiviral, ABBV-903, ABBV 903, 4TPS988XGG
Aficamten
Aficamten
C18H19N5O2, 337.4 g/mol
FDA 2025, APPROVALS 2025, Myqorzo, 12/19/2025, To treat symptomatic obstructive hypertrophic cardiomyopathy
CK-3773274, B1I77MH6K1, BAY-3723113; CK 3773274; CK 274; MYQORZO
N-[(1R)-5-(5-ethyl-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1H-inden-1-yl]-1-methylpyrazole-4-carboxamide
- (R)-N-(5-(5-ethyl-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1H-inden-1-yl)-1-methyl-1H-pyrazole-4-carboxamide
- N-((1R)-5-(5-Ethyl-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1H-inden-1-yl)- 1-methyl-1H-pyrazole-4-carboxamide
- OriginatorCytokinetics
- DeveloperBayer; Cytokinetics; Sanofi
- ClassAmides; Cardiovascular therapies; Heart failure therapies; Indenes; Oxadiazoles; Pyrazoles; Small molecules
- Mechanism of ActionCardiac myosin inhibitors
- Orphan Drug StatusYes – Hypertrophic cardiomyopathy
- RegisteredHypertrophic cardiomyopathy
- 20 Dec 2025Cytokinetics plans to launch aficamten in the USA in second half of January 2026
- 19 Dec 2025Registered for Hypertrophic cardiomyopathy in USA (PO)
- 19 Dec 2025Aficamten carries a black box warning for the risk of heart failure
Aficamten, sold under the brand name Myqorzo, is a medication used for the treatment of symptomatic obstructive hypertrophic cardiomyopathy.[1] It is a cardiac myosin inhibitor[2] developed by Cytokinetics.[3][4]
Aficamten binds directly to the motor domain of cardiac myosin and prevents it from entering the force-producing state.[5] This lowers cardiac contractility, leading to reduced left ventricular outflow tract obstruction in people with hypertrophic cardiomyopathy.[5]
Aficamten was approved for medical use in the United States in December 2025.[6]
Medical uses
Aficamten is indicated for the treatment of adults with symptomatic obstructive hypertrophic cardiomyopathy to improve functional capacity and symptoms.[1][6]
Symptomatic obstructive hypertrophic cardiomyopathy is an inherited condition where people have thickened heart muscle and reduced blood flow from the left side of the heart to the rest of the body, causing symptoms such as shortness of breath, fatigue, and potentially life-threatening cardiac events.[6]
SYN
https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2019144041&_cid=P10-MJP428-30255-1
Example 15
Synthesis of Compound 184
1. Synthesis of Intermediate 15-2:
[0262] To a solution of tert-butyl N-[(1R)-5-(N-hydroxycarbamimidoyl)-2,3-dihydro-1H-inden-1-yl] carbamate (16 g, 54.9 mmol, 1.0 equiv) in dioxane (300 mL) was added propanoyl propanoate (8.4 g, 64.5 mmol, 1.2 equiv). The mixture was stirred at 105 oC for 8 h, cooled to r.t., concentrated under reduced pressure, and purified by silica gel
chromatography (EA/PE, 1/9) to give 17.5 g (97%) of tert-butyl N-[(1R)-5-(5-ethyl-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1H-inden-1-yl]carbamate as a white solid.
2. Synthesis of Intermediate 15-3:
[0263] To a solution of tert-butyl N-[(1R)-5-(5-ethyl-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1H-inden-1-yl]carbamate (17.6 g, 53.4 mmol, 1.0 equiv) in DCM (120 mL) was added TFA (24 mL). The mixture was stirred at room temperature overnight and concentrated under reduced pressure. The mixture was then poured into ethanol (50 mL) and water (5 mL) and the pH was adjusted to 12 with sodium hydroxide solution (2 N). The mixture was then extracted with dichloromethane (200 mL) three times. The combined organic layers were dried over anhydrous sodium sulfate and concentrated under reduced pressure to give 11.2 g of (1R)-5-(5-ethyl-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1H-inden-1-amine as a brown oil. 3. Synthesis of Compound 184:
[0264] To a solution of 1-methyl-1H-pyrazole-4-carboxylic acid (6.1 g, 48.4 mmol, 1.0 equiv) in DMF (300 mL) were added DIEA (12.6 g, 97.5 mmol, 2.0 equiv), HOAt (19.8 g, 145.8 mmol, 3.0 equiv), and EDCI (28 g, 146.1 mmol, 3.0 equiv). The mixture was stirred for 15 min, and (1R)-5-(5-ethyl-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1H-inden-1-amine (11.2 g, 48.9 mmol, 1.0 equiv) was then added. The mixture was then stirred for 3 h, diluted with DCM, washed with NH4Cl solution three times, dried over sodium sulfate, concentrated under reduced pressure, and purified by silica gel chromatography (EA/PE, 74/26) to give an intermediate product. The intermediate product was triturated with a mixture of EA and PE (1/10) to afford 14.5 g (88%) of (R)-N-(5-(5-ethyl-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1H-inden-1-yl)-1-methyl-1H-pyrazole-4-carboxamide (Compound 184) as a white solid. LRMS (ES) m/z 338 (M+H). 1H-NMR: (DMSO, 300MHz, ppm): į 8.41 (1H, d, J = 8.4 Hz), 8.16 (1H, s), 7.91-7.79 (3H, m), 7.34 (1H, d, J = 7.9 Hz), 5.53 (1H, q, J = 8.3 Hz), 3.84 (3H, s), 3.13-2.81 (4H, m), 2.44 (1H, dd, J = 7.9, 4.7 Hz), 1.95 (1H, m), 1.33 (3H, t, J = 7.5 Hz).
PAT
https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2021011807&_cid=P10-MJP428-30255-1
(R)-N-(5-(5-ethyl- 1,2,4-oxadiazol-3-yl)-2,3-dihydro-1H-inden-l-yl)-1-methyl-1H-pyrazole-4-carboxamide,
SYN
https://pubs.acs.org/doi/10.1021/acs.jmedchem.1c01290
PAT
- Cardiac sarcomere inhibitorsPublication Number: US-10836755-B2Priority Date: 2018-01-19Grant Date: 2020-11-17
- Cardiac sarcomere inhibitorsPublication Number: US-12065436-B2Priority Date: 2018-01-19Grant Date: 2024-08-20
- Cardiac sarcomere inhibitorsPublication Number: US-2023119665-A1Priority Date: 2018-01-19
- Cardiac sarcomere inhibitorsPublication Number: US-11472796-B2Priority Date: 2018-01-19Grant Date: 2022-10-18
- Cardiac sarcomere inhibitorsPublication Number: US-2025059173-A1Priority Date: 2018-01-19
- Dihydrobenzofuran and indene analogs as myocardial inhibitorsPublication Number: CN-117964573-APriority Date: 2018-01-19
- Cardiac sarcomere inhibitorsPublication Number: TW-202436291-APriority Date: 2018-01-19
- Dihydrobenzofurans and indene analogs as cardiomyome inhibitorsPublication Number: CN-111757875-BPriority Date: 2018-01-19Grant Date: 2024-01-09
- Dihydrobenzofuran and indene analogs as myocardial inhibitorsPublication Number: CN-117924208-APriority Date: 2018-01-19
- Dihydrobenzofuran and indene analogs as inotropic agentsPublication Number: CN-111757875-APriority Date: 2018-01-19
- Cardiac sarcomere inhibitorsPublication Number: TW-I835770-BPriority Date: 2018-01-19Grant Date: 2024-03-21
- Dihydrobenzofuran and inden analogs as cardiac sarcomere inhibitorsPublication Number: EP-3740481-A1Priority Date: 2018-01-19
- Dihydrobenzofuran and inden analogs as cardiac sarcomere inhibitorsPublication Number: EP-3740481-B9Priority Date: 2018-01-19Grant Date: 2024-10-23
- Cardiac sarcomere inhibitorsPublication Number: US-2021147399-A1Priority Date: 2018-01-19
- Cardiac sarcomere inhibitorsPublication Number: EP-4491622-A2Priority Date: 2018-01-19
REF
- Clinical Evaluation of the Effect of Aficamten on <scp>QT</scp>/<scp>QTc</scp> Interval in Healthy ParticipantsPublication Name: Clinical and Translational SciencePublication Date: 2025-04PMCID: PMC11979292PMID: 40200648DOI: 10.1111/cts.70218
- Effect of Hepatic Impairment or Renal Impairment on the Pharmacokinetics of AficamtenPublication Name: Clinical PharmacokineticsPublication Date: 2025-02-05PMCID: PMC11954688PMID: 39907965DOI: 10.1007/s40262-025-01481-9
- The clinical utility of cardiac myosin inhibitors for the management of hypertrophic cardiomyopathy: a scoping reviewPublication Name: Heart Failure ReviewsPublication Date: 2024-12-17PMCID: PMC11802616PMID: 39690360DOI: 10.1007/s10741-024-10476-w
- Obstructive Hypertrophic Cardiomyopathy: A Review of New TherapiesPublication Name: Future CardiologyPublication Date: 2023-10PMID: 37933625DOI: 10.2217/fca-2023-0056
- Aficamten: A Breakthrough Therapy for Symptomatic Obstructive Hypertrophic CardiomyopathyPublication Name: American journal of cardiovascular drugs : drugs, devices, and other interventionsPublication Date: 2023-08-01PMID: 37526885DOI: 10.1007/s40256-023-00599-0
- Synthesis of AficamtenPublication Name: SynfactsPublication Date: 2021-11-17DOI: 10.1055/s-0041-1737088
- Discovery of Aficamten (CK-274), a Next-Generation Cardiac Myosin Inhibitor for the Treatment of Hypertrophic CardiomyopathyPublication Name: Journal of Medicinal ChemistryPublication Date: 2021-10-04PMID: 34606259DOI: 10.1021/acs.jmedchem.1c01290
- Emerging Medical Treatment for Hypertrophic CardiomyopathyPublication Name: Journal of Clinical MedicinePublication Date: 2021-03-01PMCID: PMC7957690PMID: 33804412DOI: 10.3390/jcm10050951
- Small Molecules Acting on Myofilaments as Treatments for Heart and Skeletal Muscle DiseasesPublication Name: International Journal of Molecular SciencesPublication Date: 2020-12-16PMCID: PMC7767104PMID: 33339418DOI: 10.3390/ijms21249599
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Contraindiations
Use with rifampin is contraindicated.[1]
Adverse effects
The US prescription label for aficamten contains a boxed warning that it reduces left ventricular ejection fraction and can cause heart failure due to systolic dysfunction.[1]
History
The effectiveness and safety of aficamten were studied in 282 adults with symptomatic obstructive hypertrophic cardiomyopathy randomly assigned to receive aficamten or placebo for 24 weeks.[6] At the end of the study, participants receiving aficamten had an increase in exercise capacity measured by peak oxygen uptake compared to no change in exercise capacity among those receiving placebo.[6] Also, 59 percent of participants receiving aficamten experienced an improvement in physical activity limitations (measured using the New York Heart Association Classification system) compared to 24 percent of individuals receiving placebo.[6]
Society and culture
Legal status
Aficamten was approved for medical use in the United States in December 2025.[6][7] The US Food and Drug Administration granted the application for aficamten orphan drug and breakthrough therapy designations.[6]
In December 2025, the Committee for Medicinal Products for Human Use of the European Medicines Agency adopted a positive opinion, recommending the granting of a marketing authorization for the medicinal product Myqorzo, intended for the treatment of adults with obstructive hypertrophic cardiomyopathy.[5] The applicant for this medicinal product is Cytokinetics (Ireland) Limited.[5]
Names
Aficamten is the international nonproprietary name.[8]
Aficamten is sold under the brand name Myqorzo.[6]
References
- https://www.accessdata.fda.gov/drugsatfda_docs/label/2025/219083s000lbl.pdf [bare URL PDF]
- Chuang, Chihyuan; Collibee, Scott; Ashcraft, Luke; Wang, Wenyue; Vander Wal, Mark; Wang, Xiaolin; et al. (October 2021). “Discovery of Aficamten (CK-274), a Next-Generation Cardiac Myosin Inhibitor for the Treatment of Hypertrophic Cardiomyopathy”. Journal of Medicinal Chemistry. 64 (19): 14142–14152. doi:10.1021/acs.jmedchem.1c01290. ISSN 0022-2623. PMID 34606259. S2CID 238355647.
- Zhao, Xue; Liu, Hongzhong; Tian, Wei; Fang, Ligang; Yu, Mengyang; Wu, Xiaofei; et al. (2023). “Safety, tolerability, pharmacokinetics, and pharmacodynamics of single and multiple doses of aficamten in healthy Chinese participants: a randomized, double-blind, placebo-controlled, phase 1 study”. Frontiers in Pharmacology. 14 1227470. doi:10.3389/fphar.2023.1227470. PMC 10482267. PMID 37680714.
- Sebastian, Sneha Annie; Padda, Inderbir; Lehr, Eric J.; Johal, Gurpreet (September 2023). “Aficamten: A Breakthrough Therapy for Symptomatic Obstructive Hypertrophic Cardiomyopathy”. American Journal of Cardiovascular Drugs: Drugs, Devices, and Other Interventions. 23 (5): 519–532. doi:10.1007/s40256-023-00599-0. ISSN 1179-187X. PMID 37526885. S2CID 260348901.
- “Myqorzo EPAR”. European Medicines Agency (EMA). 12 December 2025. Retrieved 22 December 2025. Text was copied from this source which is copyright European Medicines Agency. Reproduction is authorized provided the source is acknowledged.
- “FDA approves drug to improve functional capacity and symptoms in adults with rare inherited heart condition”. U.S. Food and Drug Administration (FDA) (Press release). 22 December 2025. Retrieved 22 December 2025.
This article incorporates text from this source, which is in the public domain. - “Cytokinetics Announces FDA Approval of Myqorzo (aficamten) for the Treatment of Adults with Symptomatic Obstructive Hypertrophic Cardiomyopathy to Improve Functional Capacity and Symptoms” (Press release). Cytokinetics. 19 December 2025. Retrieved 22 December 2025 – via GlobeNewswire News Room.
- World Health Organization (2021). “International nonproprietary names for pharmaceutical substances (INN): recommended INN: list 86”. WHO Drug Information. 35 (3). hdl:10665/346562.
Further reading
- Maron, Martin S.; Masri, Ahmad; Choudhury, Lubna; Olivotto, Iacopo; Saberi, Sara; Wang, Andrew; et al. (January 2023). “Phase 2 Study of Aficamten in Patients With Obstructive Hypertrophic Cardiomyopathy”. Journal of the American College of Cardiology. 81 (1): 34–45. doi:10.1016/j.jacc.2022.10.020. hdl:2158/1295661. PMID 36599608. S2CID 255472935.
External links
- Clinical trial number NCT05186818 for “Aficamten vs Placebo in Adults With Symptomatic Obstructive Hypertrophic Cardiomyopathy (SEQUOIA-HCM) (SEQUOIA-HCM)” at ClinicalTrials.gov
| Clinical data | |
|---|---|
| Trade names | Myqorzo |
| Other names | CK-3773274 |
| License data | US DailyMed: Aficamten |
| Routes of administration | By mouth |
| Drug class | Cardiac myosin inhibitor |
| ATC code | None |
| Legal status | |
| Legal status | US: ℞-only[1] |
| Identifiers | |
| IUPAC name | |
| CAS Number | 2364554-48-1 |
| PubChem CID | 139331495 |
| DrugBank | DB18490 |
| ChemSpider | 114935503 |
| UNII | B1I77MH6K1 |
| KEGG | D12253 |
| ChEMBL | ChEMBL4847050 |
| PDB ligand | 6I6 (PDBe, RCSB PDB) |
| Chemical and physical data | |
| Formula | C18H19N5O2 |
| Molar mass | 337.383 g·mol−1 |
| 3D model (JSmol) | Interactive image |
| SMILES | |
| InChI | |
//////////Aficamten, FDA 2025, APPROVALS 2025, Myqorzo, CK-3773274, CK 3773274, B1I77MH6K1, BAY 3723113; CK 3773274; CK 274, MYQORZO
Zoliflodacin
Zoliflodacin
- CAS 1620458-09-4
- AZD-0914
- AZD0914
- FWL2263R77
- ETX0914
MF C22H22FN5O7 MW 487.4 g/mol
FDA 2025, APPROVALS 2025, 12/12/2025, Nuzolvence
(4′R,6′S,7′S)-17′-fluoro-4′,6′-dimethyl-13′-[(4S)-4-methyl-2-oxo-1,3-oxazolidin-3-yl]spiro[1,3-diazinane-5,8′-5,15-dioxa-2,14-diazatetracyclo[8.7.0.02,7.012,16]heptadeca-1(17),10,12(16),13-tetraene]-2,4,6-trione
Spiro[isoxazolo[4,5-g][1,4]oxazino[4,3-a]quinoline-5(6H),5′(2′H)-pyrimidine]-2′,4′,6′(1′H,3′H)-trione, 11-fluoro-1,2,4,4a-tetrahydro-2,4-dimethyl-8-[(4S)-4-methyl-2-oxo-3-oxazolidinyl]-, (2R,4S,4aS)-
(2R,4S,4aS)-11-Fluoro-2,4-dimethyl-8-[(4S)-4-methyl-2-oxo-1,3-oxazolidin-3-yl]-1,2,4,4a-tetrahydro-2′H,6H-spiro[1,4-oxazino[4,3-a][1,2]oxazolo[4,5-g]quinoline-5,5′-pyrimidine]-2′,4′,6′(1′H,3′H)-trione
To treat uncomplicated urogenital gonorrhea due to Neisseria gonorrhoeae
Zoliflodacin, sold under the brand name Nuzolvence, is an antibiotic used for the treatment of antibiotic-resistant Neisseria gonorrhoeae (gonorrhea).[2] Zoliflodacin is being developed as part of a public-private partnership between Innoviva Specialty Therapeutics and the Global Antibiotic Research & Development Partnership (GARDP).[3] Zoliflodacin is taken by mouth.[2]
The most common side effects include low white blood cell counts, headache, dizziness, nausea, and diarrhea.[2]
Zoliflodacin was approved for medical use in the United States in December 2025.[2]
SYN
- Facile Synthesis of Spirocyclic Tetrahydroquinolines via C(sp3)–H Functionalization in a Cascade Redox ProcessDOI: 10.1055/s-0040-1720890Publication Date: 2022Publication Name: Synthesis
- Synthesis of ZoliflodacinDOI: 10.1055/s-0040-1707088Publication Date: 2020Publication Name: Synfacts
SYN
SYN
SYN
SYN
https://patentscope.wipo.int/search/en/detail.jsf?docId=US106042502&_cid=P11-MJMADN-82597-1
(2R,4S,4aS)-11-Fluoro-2,4-dimethyl-8-[(4S)-4-methyl-2-oxo-1,3-oxazolidin-3-yl]-1,2,4,4a-tetrahydro-2′H,6H-spiro[1,4-oxazino[4,3-a][1,2]oxazolo[4,5-g]quinoline-5,5′-pyrimidine]-2′,4′,6′(1′H,3′H)-trione
| 1H NMR (400 MHz, DMSO-d 6) δ: 0.9 (d, 3H), 1.15 (d, 3H), 1.4 (d, 3H), 2.9 (d, 1H), 3.1 (t, 1H), 3.6-3.7 (m, 2H), 3.8-4.0 (m, 1H), 3.9 (d, 1H), 4.1 (d, 1H), 4.2 (q, 1H), 4.6-4.7 (m, 2H), 7.6 (s, 1H), 11.5 (s, 1H), 11.8 (s, 1H). MS (ES) MH +: 488.4 for C 22H 22FN 5O 7, [α] D 20=+224 (c=1; MeOH). |
Alternative Synthesis of Example 5
1H NMR (300 MHz, DMSO-d 6) δ: 1.0 (d, 3H), 1.3 (d, 3H), 1.4 (d, 3H), 3.1 (d, 1H), 3.5-4.3 (m, 7H), 4.5-4.8 (m, 2H), 7.6 (s, 1H), 11.5 (br. s., 1H), 11.7 (br. s., 1H). MS (ES) MH +: 488 for C 22H 22FN 5O 7.
SYN
https://www.sciencedirect.com/topics/biochemistry-genetics-and-molecular-biology/mic90
2.3.2 Chemical synthesis
The synthesis of zoliflodacin described below was reported in 2015 [47]. The first step, starting from 2,3,4-trifluorobenzaldehyde, consists of the protection of the aldehyde function to an acetal group. After deprotonation using n-BuLi, formylation is performed with DMF to introduce an aldehyde group, which is then converted to oxime using hydroxylamine. Chlorination with N-chlorosuccinimide (NCS), followed by reaction with L-alaninol and intramolecular SNAr allows the formation of the benzisoxazole ring. The oxazolidinone moiety is obtained using 1,1′-carbonyldiimidazole (CDI). The deprotection of the aldehyde is then performed in acidic conditions followed by another SNAr at the ortho position of the aldehyde using (2R,6S)-2,6-dimethylmorpholine. Finally, a Knoevenagel condensation between the aldehyde and hexahydropyrimidine-2,4,6-trione is performed, followed by an intramolecular rearrangement consisting in an [1-5] hydride shift and then intramolecular cyclization leading to zoliflodacin (Fig. 5).
PAT
- High throughput screening assay to identify DNA topoisomerase inhibitorsPublication Number: US-12234504-B1Priority Date: 2023-10-16Grant Date: 2025-02-25
- Treatment of pathogenic neisseria sp. infection with triazole antifungal agentsPublication Number: US-2025281464-A1Priority Date: 2022-04-29
- Methods and materials for treatment of neisseria gonorrhoeae infectionPublication Number: WO-2022204231-A2Priority Date: 2021-03-26
- Methods and materials for treatment of neisseria gonorrhoeae infectionPublication Number: EP-4313040-A2Priority Date: 2021-03-26
- Methods and materials for treatment of neisseria gonorrhoeae infectionPublication Number: EP-4313040-A2Priority Date: 2021-03-26
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Medical uses
Zoliflodacin is indicated for the treatment of uncomplicated urogenital gonorrhea in people who weigh at least 77 pounds (35 kg).[2]
Susceptible bacteria
Zoliflodacin has shown in vitro activity against the following species of bacteria:[4] Staphylococcus aureus, Streptococcus pneumoniae, Haemophilus influenzae, Moraxella catarrhalis, Neisseria gonorrhoeae, and Chlamydia trachomatis
Adverse effects
Animal studies showed that zoliflodacin might cause birth defects, pregnancy loss, or male fertility problems.[2]
Mechanism of action
It has a mechanism of action which involves inhibition of bacterial type II topoisomerases.[4][5][6]
History
A high throughput screening campaign aimed at identifying compounds with whole cell antibacterial activity performed at Pharmacia & Upjohn identified compound PNU-286607, a progenitor of Zoliflodacin, as having the desired activity.[7]
Subsequent research at AstraZeneca led to the discovery that the nitroaromatic in PNU-286607 could be replaced with a fused benzisoxazole ring,[8] which allowed for an exploration of different groups at the 3-position of the heterocycle. This work was continued at Entasis Pharmaceuticals where extensive optimization resulted in the discovery of ETX0914.[4]
Researchers tested zoliflodacin in a study with 930 participants who had uncomplicated urogenital gonorrhea.[2] Two-thirds of participants received a single 3-gram dose of zoliflodacin dissolved in water.[2] The other third received the standard treatment of ceftriaxone shot plus azithromycin pill.[2] The study measured how well the medicines cleared the bacteria 4 to 8 days after treatment.[2] The study showed 91% of participants who took zoliflodacin were cured and 96% of participants who received the standard treatment were cured.[2]
Society and culture
Legal status
Zoliflodacin was approved for medical use in the United States in December 2025.[3]
The US Food and Drug Administration (FDA) granted the application for zoliflodacin fast track, qualified infectious disease product, and priority review designations for the uncomplicated urogenital gonorrhea indication.[2] The FDA approval for zoliflodacin was granted to Entasis Therapeutics.[2]
Names
Zoliflodacin is the international nonproprietary name.[9]
Zoliflodacin is sold under the brand name Nuzolvence.[3]
References
- https://innovivaspecialtytherapeutics.com/wp-content/uploads/2025/12/NUZOLVENCE-zoliflodacin-Full-Prescribing-Information-December-2025.pdf [bare URL PDF]
- “FDA Approves Two Oral Therapies to Treat Gonorrhea”. U.S. Food and Drug Administration (FDA) (Press release). 12 December 2025. Retrieved 13 December 2025. This article incorporates text from this source, which is in the public domain.
- Pierre G (12 December 2025). “Nuzolvence (Zoliflodacin) Receives U.S. FDA Approval”. Global Antibiotic Research & Development Partnership (GARDP). Retrieved 13 December 2025.
- Basarab GS, Kern GH, McNulty J, Mueller JP, Lawrence K, Vishwanathan K, et al. (July 2015). “Responding to the challenge of untreatable gonorrhea: ETX0914, a first-in-class agent with a distinct mechanism-of-action against bacterial Type II topoisomerases”. Scientific Reports. 5 (1) 11827. Bibcode:2015NatSR…511827B. doi:10.1038/srep11827. PMC 4501059. PMID 26168713.
- Bradford PA, Miller AA, O’Donnell J, Mueller JP (June 2020). “Zoliflodacin: An Oral Spiropyrimidinetrione Antibiotic for the Treatment of Neisseria gonorrheae, Including Multi-Drug-Resistant Isolates”. ACS Infectious Diseases. 6 (6): 1332–1345. doi:10.1021/acsinfecdis.0c00021. PMID 32329999.
- Pisano L, Giovannuzzi S, Supuran CT (June 2024). “Management of Neisseria gonorrhoeae infection: from drug resistance to drug repurposing”. Expert Opinion on Therapeutic Patents. 34 (6): 511–524. doi:10.1080/13543776.2024.2367005. PMID 38856987.
- Miller AA, Bundy GL, Mott JE, Skepner JE, Boyle TP, Harris DW, et al. (August 2008). “Discovery and characterization of QPT-1, the progenitor of a new class of bacterial topoisomerase inhibitors”. Antimicrobial Agents and Chemotherapy. 52 (8): 2806–2812. doi:10.1128/AAC.00247-08. PMC 2493097. PMID 18519725.
- Basarab GS, Brassil P, Doig P, Galullo V, Haimes HB, Kern G, et al. (November 2014). “Novel DNA gyrase inhibiting spiropyrimidinetriones with a benzisoxazole scaffold: SAR and in vivo characterization”. Journal of Medicinal Chemistry. 57 (21): 9078–9095. doi:10.1021/jm501174m. PMID 25286019.
- World Health Organization (2016). “International nonproprietary names for pharmaceutical substances (INN): recommended INN: list 76”. WHO Drug Information. 30 (3). hdl:10665/331020.
Further reading
- Luckey A, Balasegaram M, Barbee LA, Batteiger TA, Broadhurst H, Cohen SE, et al. (2025). “Zoliflodacin versus ceftriaxone plus azithromycin for treatment of uncomplicated urogenital gonorrhoea: an international, randomised, controlled, open-label, phase 3, non-inferiority clinical trial”. The Lancet. doi:10.1016/S0140-6736(25)01953-1.
- Taylor SN, Marrazzo J, Batteiger BE, Hook EW, Seña AC, Long J, et al. (November 2018). “Single-Dose Zoliflodacin (ETX0914) for Treatment of Urogenital Gonorrhea”. The New England Journal of Medicine. 379 (19): 1835–1845. doi:10.1056/NEJMoa1706988. hdl:1805/19865. PMID 30403954.
External links
- Clinical trial number NCT03959527 for “Zoliflodacin in Uncomplicated Gonorrhoea” at ClinicalTrials.gov
| Clinical data | |
|---|---|
| Trade names | Nuzolvence |
| Other names | AZD0914; ETX0914 |
| AHFS/Drugs.com | Nuzolvence |
| License data | US DailyMed: Zoliflodacin |
| Routes of administration | By mouth |
| Drug class | Antibacterial |
| ATC code | None |
| Legal status | |
| Legal status | US: ℞-only[1][2] |
| Pharmacokinetic data | |
| Bioavailability | 97.8% |
| Metabolism | Liver |
| Onset of action | Fasted: 1.5–2.3 hFed: 4 h |
| Elimination half-life | 5.3–6.3 h |
| Excretion | Feces (79.6%)Urine (18.2%) |
| Identifiers | |
| IUPAC name | |
| PubChem CID | 76685216 |
| DrugBank | 12817 |
| UNII | FWL2263R77 |
| KEGG | D11726 |
| Chemical and physical data | |
| Formula | C22H22FN5O7 |
| Molar mass | 487.444 g·mol−1 |
| 3D model (JSmol) | Interactive image |
| SMILES | |
| InChI | |
//////////Zoliflodacin, FDA 2025, APPROVALS 2025, Nuzolvence, AZD-0914, AZD 0914, FWL2263R77, ETX 0914
Iscartrelvir
Iscartrelvir
CAS 2921711-74-0
MF 2921711-74-0, 526.4 g/mol
N-{(1S,2R)-2-[4-bromo-2-(methylcarbamoyl)-6-nitroanilino]cyclohexyl}isoquinoline-4-carboxamide
antiviral, WU-04, WU 04, W2LTV65R5E
Iscartrelvir is an investigational new drug developed by the Westlake University for the treatment of COVID-19. It targets the SARS-CoV-2 3CL protease, which is crucial for the replication of the virus responsible for COVID-19.[1][2]
Iscartrelvir is a small molecule drug. The usage of the INN stem ‘-trelvir’ in the name indicates that Iscartrelvir is a antiviral 3CL protease inhibitor. Iscartrelvir has a monoisotopic molecular weight of 525.1 Da.
PAT
WO2022150962A1
https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2022150962&_cid=P11-MJKTXT-76321-1
SYN
https://patentscope.wipo.int/search/en/detail.jsf?docId=CN331401594&_cid=P11-MJKTO7-65334-1
PAT
https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2024243841&_cid=P11-MJKTO7-65334-1
N-((1S,2R)-2-((4-bromo-2-(methylcarbamoyl)-6-nitrophenyl)amino)cyclohexyl)isoquinoline-4-carboxamide, and its structure is as follows:
Example 1: Preparation of Compound 1
[0189]A free, amorphous compound 1, a yellow solid, was prepared according to the method disclosed in paragraphs [00121]-[00128] of WO2022150962A1, and was used in the following examples. The specific synthetic steps are shown in steps a to d:
The reagents and conditions for steps a to d are further described below: (a) 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (HATU), N,N-diisopropylethylamine (DIPEA), CH₂Cl₂
or
dichloromethane (DCM), 0°C, 2 h; (b) DIPEA, dimethylformamide (DMF), 80°C, 16 h; (c) 3M ethyl hydrochloride (HCl·EA), CH₂Cl₂ , 1
h ; (d ) HATU, DIPEA, DMF, room temperature, 12 h.
[0191]Step a: Synthesis of N-methyl-5-bromo-2-fluoro-3-nitrobenzamide (I-1)
[0192]A solution of 5-bromo-2-fluoro-3-nitrobenzoic acid (0.8 g, 3.80 mmol) in dichloromethane (20 mL) was stirred at 0 °C. Then, HATU (2.0 g, 5.25 mmol), DIPEA (1.88 mL, 11.4 mmol), and methylamine hydrochloride (0.31 g, 4.5 mmol) were added to the reaction mixture. The mixture was stirred at 0 °C for 2 hours until it became clear. The mixture was extracted three times with dichloromethane, and the combined organic layers were washed with a saturated brine solution. The organic phase was then dried over anhydrous Na₂SO₄ and concentrated
under vacuum. Finally, the mixture was purified by chromatography to give compound I-1 (0.8 g, 76% yield) as a yellow solid.
[0193]Step b: Synthesis of tert-butyl 2-((4-bromo-2-(methylcarbamoyl)-6-nitrophenyl)amino)cyclohexyl)carbamate (I-2)
[0194]A solution of compound I-1 (0.8 g, 2.9 mmol) in 15 mL of DMF was stirred at room temperature. Then, tert-butyl ((1S,2R)-2-aminocyclohexyl)carbamate (0.75 g, 3.5 mmol) (the corresponding stereoisomer of this reagent can be used to synthesize the stereoisomer of compound I-2) and DIPEA (1.44 mL, 8.7 mmol) were added to the reaction mixture. The mixture was heated to 80 °C and stirred for 16 hours. The mixture was extracted three times with ethyl acetate, and the combined organic layers were washed with saturated salt solution. The organic phase was then dried over anhydrous Na₂SO₄ and concentrated under vacuum to give compound
I -2 as a yellow solid, requiring no further purification.
Step c: Synthesis of 2-(2-aminocyclohexyl)amino)-5-bromo-N-methyl-3-nitrobenzamide hydrochloride (I-3)
[0196]A solution of compound I-2 (90 mg, 0.19 mmol) (or the corresponding stereoisomer) in anhydrous dichloromethane (6 mL) was stirred at room temperature. Then, HCl (4 mL, 3 M in ethyl acetate) was added. The mixture was stirred at room temperature for 2 hours. The mixture was concentrated under vacuum to give compound I-3 as a yellow solid, requiring no further purification.
[0197]Step d: Synthesis of N-((1S,2R)-2-((4-bromo-2-(methylcarbamoyl)-6-nitrophenyl)amino)cyclohexyl)isoquinoline-4-carboxamide
[0198]At room temperature, a solution of the corresponding isoquinoline-4-carboxylic acid (1 equivalent) and HATU (1.5 equivalent) in anhydrous DMF (6 mL) was stirred. Then, compound I-3 and DIPEA (5.0 equivalent) were added. The mixture was stirred overnight at room temperature. The mixture was extracted three times with ethyl acetate, and the combined organic layers were washed with saturated brine. The organic phase was then dried over anhydrous Na₂SO₄ and
concentrated under vacuum. Finally, the mixture was purified by chromatography to give compound 1 as a free amorphous solid in yellow form.
PAT
- Aromatic ring-containing pyridone amide compoundsPublication Number: CN-119100980-APriority Date: 2023-06-07
- Crystal of viral protease inhibitor and usePublication Number: WO-2024243841-A1Priority Date: 2023-05-31
- Protease inhibitors, their preparation and usePublication Number: CN-113072497-BPriority Date: 2021-01-12Grant Date: 2023-04-14
- Protease inhibitors, their preparation and usePublication Number: CN-113072497-APriority Date: 2021-01-12
- Protease inhibitors, their preparation and usePublication Number: CN-116751164-APriority Date: 2021-01-12
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| Clinical data | |
|---|---|
| Other names | WPV01; WU-04 |
| Identifiers | |
| IUPAC name | |
| CAS Number | 2921711-74-0 |
| PubChem CID | 156774920 |
| ChemSpider | 129307041 |
| UNII | W2LTV65R5E |
| PDB ligand | J7R (PDBe, RCSB PDB) |
| Chemical and physical data | |
| Formula | C24H24BrN5O4 |
| Molar mass | 526.391 g·mol−1 |
| 3D model (JSmol) | Interactive image |
| SMILES | |
| InChI | |
References
- Yang L, Wang Z (September 2023). “Bench-to-bedside: Innovation of small molecule anti-SARS-CoV-2 drugs in China”. European Journal of Medicinal Chemistry. 257 115503. doi:10.1016/j.ejmech.2023.115503. PMC 10193775. PMID 37229831.
- Hou N, Shuai L, Zhang L, Xie X, Tang K, Zhu Y, et al. (February 2023). “Development of Highly Potent Noncovalent Inhibitors of SARS-CoV-2 3CLpro”. ACS Central Science. 9 (2): 217–227. doi:10.1021/acscentsci.2c01359. PMC 9885526. PMID 36844503.
- Resistance mechanisms of SARS-CoV-2 3CLpro to the non-covalent inhibitor WU-04Publication Name: Cell DiscoveryPublication Date: 2024-04-09PMCID: PMC11003996PMID: 38594245DOI: 10.1038/s41421-024-00673-0
- Identification of Ebselen derivatives as novel SARS-CoV-2 main protease inhibitors: Design, synthesis, biological evaluation, and structure-activity relationships explorationPublication Name: Bioorganic & Medicinal ChemistryPublication Date: 2023-12-15PMID: 37972434DOI: 10.1016/j.bmc.2023.117531
- The molecular mechanism of non-covalent inhibitor WU-04 targeting SARS-CoV-2 3CLpro and computational evaluation of its effectiveness against mainstream coronavirusesPublication Name: Physical chemistry chemical physics : PCCPPublication Date: 2023-09-13PMID: 37655706DOI: 10.1039/d3cp03828a
- Bench-to-bedside: Innovation of small molecule anti-SARS-CoV-2 drugs in ChinaPublication Name: European Journal of Medicinal ChemistryPublication Date: 2023-09-05PMCID: PMC10193775PMID: 37229831DOI: 10.1016/j.ejmech.2023.115503
- Development of Highly Potent Noncovalent Inhibitors of SARS-CoV-2 3CLproPublication Name: ACS Central SciencePublication Date: 2023-01-25PMCID: PMC9885526PMID: 36844503DOI: 10.1021/acscentsci.2c01359
////////iscartrelvir, antiviral, WU-04, WU 04, W2LTV65R5E
Zoracopan
Zoracopan
CAS 2243483-63-6
MF C31H31BrN6O3 MW 615.52
2-Azabicyclo[3.1.0]hexane-3-carboxamide, 2-[2-[3-acetyl-7-methyl-5-(2-methyl-5-pyrimidinyl)-1H-indol-1-yl]acetyl]-N-(6-bromo-3-methyl-2-pyridinyl)-5-methyl-, (1R,3S,5R)-
(1R,3S,5R)-2-{[3-acetyl-7-methyl-5-(2-methylpyrimidin5-yl)-1H-indol-1-yl]acetyl}-N-(6-bromo-3-methylpyridin2-yl)-5-methyl-2-azabicyclo[3.1.0]hexane-3-carboxamide
complement factor D inhibitor, ALXN-2080, ALXN 2080, E7799Y8LXY
Zoracopan is a selective complement factor D (CFD) inhibitor. When administered systemically (orally or intravenously), Zoracopan accumulates and is sustained-released in ocular tissues, primarily in the choroid-retinal pigment epithelium (C-RPE) and/or iridociliary body (I-CB).
Zoracopan is a small molecule drug. The usage of the INN stem ‘-copan’ in the name indicates that Zoracopan is a complement receptor antagonist/complement inhibitor. Zoracopan is under investigation in clinical trial NCT06173596 (A Study to Evaluate Potential Drug Interactions Between ALXN2080 and Itraconazole, Fluconazole & Carbamazepine in Healthy Adults). Zoracopan has a monoisotopic molecular weight of 614.16 Da.
- Safety and Tolerability, PK, and PD Study of Single and Multiple ALXN2080 Doses in Healthy ParticipantsCTID: NCT05428696Phase: Phase 1Status: CompletedDate: 2024-06-07
- A Study to Evaluate Potential Drug Interactions Between ALXN2080 and Itraconazole, Fluconazole & Carbamazepine in Healthy AdultsCTID: NCT06173596Phase: Phase 1Status: CompletedDate: 2024-06-20
- A Study to Investigate the Potential Drug Interactions Between ALXN2080 and Rosuvastatin and Metformin in Healthy Adult ParticipantsCTID: NCT06160414Phase: Phase 1Status: CompletedDate: 2025-04-24
WO2024259085
WO2024137329
SYN
426
https://patentscope.wipo.int/search/en/detail.jsf?docId=US289331902&_cid=P10-MJJEYB-31207-1
SYN
SYN
https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2018160889&_cid=P10-MJJEK1-12570-1
PAT
- Aryl, heteroaryl and heterocyclic pharmaceutical compounds for the treatment of medical disordersPublication Number: JP-7390449-B2Priority Date: 2017-03-01Grant Date: 2023-12-01
- Aryl, heteroaryl, and heterocyclic pharmaceutical compounds for treatment of medical disordersPublication Number: US-11708351-B2Priority Date: 2017-03-01Grant Date: 2023-07-25
- Aryl, heteroaryl and heterocyclic pharmaceutical compounds for the treatment of medical disordersPublication Number: JP-2022174122-APriority Date: 2017-03-01
- Aryl, heteroaryl, and heterocyclic pharmaceutical compounds for the treatment of medical disordersPublication Number: KR-20190126831-APriority Date: 2017-03-01
- Aryl, heteroaryl, and heterocyclic pharmaceutical compounds for treatment of medical disordersPublication Number: US-11084800-B2Priority Date: 2017-03-01Grant Date: 2021-08-10
- Aryl, heteroary, and heterocyclic pharmaceutical compounds for treatment of medical disordersPublication Number: EP-3985002-A1Priority Date: 2017-03-01
- Aryl, heteroaryl, and heterocyclic pharmaceutical compounds for the treatment of medical disordersPublication Number: KR-102632860-B1Priority Date: 2017-03-01Grant Date: 2024-02-02
- Aryi, Heteroaryl, and Heterocyclic Pharmaceutical Compounds for Treatment of Medical DisordersPublication Number: US-2020071301-A1Priority Date: 2017-03-01
- Aryl, Heteroaryl and Heterocyclic Pharmaceutical Compounds for the Treatment of Medical DisordersPublication Number: CN-110603252-APriority Date: 2017-03-01
- Aryl, heteroaryl, and heterocyclic pharmaceutical compounds for treatment of medical disordersPublication Number: US-2022396563-A1Priority Date: 2017-03-01
- Ocular drug depot for complement-mediated disordersPublication Number: US-2023126447-A1Priority Date: 2020-03-10
- Ocular drug depot for complement-mediated disordersPublication Number: WO-2021183555-A1Priority Date: 2020-03-10
- Aryl, heteroaryl, and heterocyclic pharmaceutical compounds for treatment of medical disordersPublication Number: US-12162860-B2Priority Date: 2017-03-01Grant Date: 2024-12-10
- Aryl, heteroaryl, and heterocyclic pharmaceutical compounds for treatment of medical disordersPublication Number: US-2023357199-A1Priority Date: 2017-03-01
- Aryl, heteroary, and heterocyclic pharmaceutical compounds for treatment of medical disordersPublication Number: WO-2018160889-A1Priority Date: 2017-03-01
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////zoracopan, complement factor D inhibitor, ALXN-2080, ALXN 2080, E7799Y8LXY
Zopocianine
Zopocianine
CAS 2206660-94-6, NA SALT 2206660-95-7
MF C74H93N7O27S4, 1,640.83
L-Tyrosine, N-[[[(1S)-1,3-dicarboxypropyl]amino]carbonyl]-L-g-glutamyl-3-[2-(2-aminoethoxy)ethoxy]propanoyl-L-phenylalanyl-O-[6-[2-[1,3-dihydro-3,3-dimethyl-5-sulfo-1-(4-sulfobutyl)-2H-indol-2-ylidene]ethylidene]-2-[2-[3,3-dimethyl-5-sulfo-1-(4-sulfobutyl)-3H-indolium-2-yl]ethenyl]-1-cyclohexen-1-yl]-, inner salt
N-{[(1S)-1,3-dicarboxypropyl]carbamoyl}-L-γ-glutamyl3-[2-(2-aminoethoxy)ethoxy]propanoyl-L-phenylalanylO-[(6Ξ)-2-{(1Ξ)-2-[3,3-dimethyl-1-(4-sulfobutyl)-5-
sulfonato-3H-indol-1-ium-2-yl]ethen-1-yl}-6-{(2Ξ)-2-
[3,3-dimethyl-5-sulfo-1-(4-sulfobutyl)-1,3-dihydro-2Hindol-2-ylidene]ethylidene}cyclohex-1-en-1-yl]-Ltyrosine
diagnostic imaging agent, UD9V5S9M7A, OTL 0078, OTL 78
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/////////zopocianine, diagnostic imaging agent, UD9V5S9M7A, OTL 0078, OTL 78
Zomiradomide
Zomiradomide
CAS 2655656-99-6
MF C45H48F3N7O6S MW871.97
- N-[2-[4-[[6-[2-[[2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-4-yl]amino]ethyl]-2-azaspiro[3.3]heptan-2-yl]methyl]cyclohexyl]-5-(2-hydroxypropan-2-yl)-1,3-benzothiazol-6-yl]-6-(trifluoromethyl)pyridine-2-carboxamide
- N-[2-[trans-4-[[6-[2-[[2-(2,6-Dioxo-3-piperidinyl)-2,3-dihydro-1,3-dioxo-1H-isoindol-4-yl]amino]ethyl]-2-azaspiro[3.3]hept-2-yl]methyl]cyclohexyl]-5-(1-hydroxy-1-methylethyl)-6-benzothiazolyl]-6-(trifluoromethyl)-2-pyridinecarboxamide
antineoplastic, IRAK degrader-1, AQ5UXV5646
Zomiradomide is an orally active PROTAC degrader for IRAK4 (DC50=6 nM), thereby inhibiting the NF-κB signaling pathway. Zomiradomide acts also as a molecular glue, recruiting Ikaros and Aiolos, and mediating their degradation (DC50 for Ikaros is 1 nM), thereby activating the type I IFN signaling pathway.
Zomiradomide is a small molecule protein degrader of interleukin-1 receptor-associated kinase 4 (IRAK4) and the immunomodulatory imide drug (IMiD) substrates Ikaros (IKZF1) and Aiolos (IKZF3), with potential immunomodulating and antineoplastic activities. Upon administration, zomiradomide modulates the E3 (ubiquitin) ligase and targets IRAK4, Ikaros and Aiolos for ubiquitination. This induces proteasome-mediated degradation of IRAK4, Ikaros and Aiolos. The degradation of IRAK4 inhibits IRAK4-mediated signaling and prevents the activation of IRAK4-mediated nuclear factor-kappa B (NF-kB) signaling and decreases the expression of inflammatory cytokines and certain pro-survival factors. This inhibits the proliferation of IRAK4-overactivated tumor cells, which are found in cells harboring MYD88 activating mutations or those with overactivated toll-like receptor (TLR) pathways. The degradation of the transcription factors Ikaros and Aiolos leads to a downregulation of other proteins, including interferon regulatory factor 4 (IRF4), which upregulates type I interferon signaling and further inhibits NF-kB activation. This leads to apoptosis and the inhibition of tumor cell proliferation. IRAK4, a serine/threonine-protein kinase that plays a key role in both the TLR and IL-1R signaling pathways, is activated though the adaptor protein MYD88 and links the TLR and IL-1R signaling pathway to the NF-kB pathway.
SYN
https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2022027058&_cid=P20-MJGJKA-81687-1
Example 1. Synthesis of N-[2-[4-[[6-[2-[[2-(2,6-dioxo-3-piperidyl)-1,3-dioxo-isoindolin-4-yl]amino]ethyl]-2- azaspiro[3.3]heptan-2-yl]methyl]cyclohexyl]-5-(1-hydroxy-1-methyl-ethyl)-1,3-benzothiazol-6-yl]-6-(trifluoromethyl)pyridine-2-carboxamide (Compound A)
[00349] To a solution of 4-[2-(2-azaspiro[3.3]heptan-6-yl)ethylamino]-2-(2,6-dioxo-3-piperidyl)isoindoline -1,3-dione (75.8 mg, 148 umol, TFA salt, Intermediate ATH) in THF (2 mL) was added TEA (15.0 mg, 148 umol), then the mixture stirred at 25 °C for 10 min. Next, HOAc (8.92 mg, 148 umol) and N-[2-(4-formylcyclohexyl)-5-(1-hydroxy-1-methyl-ethyl)-1,3-benzothiazol-6-yl]-6-(trifluoromethyl)pyridine-2-carboxamide (73.0 mg, 148 umol, Intermediate BAX) were added to the mixture and the mixture was stirred at 25 °C for 20 minutes, then NaBH(OAc)3 (62.9 mg, 297 umol) was added to the mixture at 0 °C. The reaction mixture was stirred at 0-25 °C for 2 hours. On completion, the reaction mixture was quenched with H2O (1 mL) and concentrated in vacuo. The residue was purified by prep-HPLC (column: Phenomenex Synergi C18150*25*10 um; mobile phase: [water(0.225%FA)-ACN]; B%: 31%-58%, 9 min) to give the title compound (59.1 mg, 41% yield) as a yellow solid.1H NMR (400 MHz, DMSO-d6) δ 12.54 (s, 1H), 11.09 (s, 1H), 9.06 (s, 1H), 8.49 – 8.44 (m, 1H), 8.38 (t, J = 8.0 Hz, 1H), 8.19 (d, J = 8.0 Hz, 1H), 7.88 (s, 1H), 7.58 (t, J = 8.0 Hz, 1H), 7.10 – 6.99 (m, 2H), 6.47 (t, J = 5.6 Hz, 1H), 6.07 (s, 1H), 5.05 (dd, J = 5.6, 12.8 Hz, 1H), 3.54 – 3.47 (m, 2H), 3.25 – 3.18 (m, 4H), 3.06 – 2.99 (m, 1H), 2.93 – 2.83 (m, 1H), 2.63 – 2.56 (m, 1H), 2.54 (s, 3H), 2.30 – 2.21 (m, 2H), 2.30 – 2.21 (m, 3H), 2.06 – 1.99 (m, 1H), 1.88 – 1.77 (m, 4H), 1.68 – 1.61 (m, 8H), 1.58 – 1.49 (m, 2H), 1.45 – 1.36 (m, 1H), 1.15 – 1.02 (m, 2H); LC-MS (ESI+) m/z 872.2 (M+H)+.
PAT
- Irak degraders and uses thereofPublication Number: US-2024131016-A1Priority Date: 2019-12-17
- Irak degraders and uses thereofPublication Number: EP-4076520-A1Priority Date: 2019-12-17
- IRAK degraders and uses thereofPublication Number: US-11779578-B2Priority Date: 2019-12-17Grant Date: 2023-10-10
- IRAK degraders and uses thereofPublication Number: US-11707457-B2Priority Date: 2019-12-17Grant Date: 2023-07-25
- Methods of treating mutant lymphomasPublication Number: US-2024316004-A1Priority Date: 2020-07-30
- Methods of treating mutant lymphomasPublication Number: US-2022054453-A1Priority Date: 2020-07-30
- Irak degraders and uses thereofPublication Number: US-2023144292-A1Priority Date: 2019-12-17
- Irak degraders and uses thereofPublication Number: WO-2021127190-A1Priority Date: 2019-12-17
- Irak degraders and uses thereofPublication Number: US-2021228562-A1Priority Date: 2019-12-17
- Irak4 degraders and uses thereofPublication Number: EP-4463166-A1Priority Date: 2022-01-14
- Methods of treating mutant lymphomasPublication Number: WO-2022027058-A1Priority Date: 2020-07-30
- Methods of treating mutated lymphomaPublication Number: CN-116133692-APriority Date: 2020-07-30
- Methods of treating mutant lymphomasPublication Number: US-11857535-B2Priority Date: 2020-07-30Grant Date: 2024-01-02
- Methods of treating mutant lymphomasPublication Number: EP-4188374-A1Priority Date: 2020-07-30
- Irak4 degraders and uses thereofPublication Number: WO-2024191788-A1Priority Date: 2023-03-10
- Formulations for treating cancerPublication Number: WO-2024163751-A1Priority Date: 2023-02-01
- Irak4 degraders and uses thereofPublication Number: WO-2024148049-A1Priority Date: 2023-01-04
- Irak4 degraders and uses thereofPublication Number: US-2023277519-A1Priority Date: 2022-01-14
- Irak4 degraders and uses thereofPublication Number: WO-2023137439-A1Priority Date: 2022-01-14
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/////////zomiradomide, antineoplastic, IRAK degrader-1, AQ5UXV5646
Zerencotrep
Zerencotrep
CAS 1628287-16-0
MF C23H20ClF3N4O5, MW 524.88
7-[(4-chlorophenyl)methyl]-1-(3-hydroxypropyl)-3-methyl-8-[3-(trifluoromethoxy)phenoxy]purine-2,6-dione
7-[(4-chlorophenyl)methyl]-1-(3-hydroxypropyl)-3-
methyl-8-[3-(trifluoromethoxy)phenoxy]-3,7-dihydro1H-purine-2,6-dione
transient receptor potential channel 4 and 5 (TRPC4, TRPC5) inhibitor, Pico 145, HC 608, HMIMSYLCWQ
Pico145 (HC-608) is a remarkable inhibitor of TRPC1/4/5 channels, inhibits (-)-englerin A-activated TRPC4/TRPC5 channels, with IC50s of 0.349 and 1.3 nM in cells, and shows no effect on TRPC3, TRPC6, TRPV1, TRPV4, TRPA1, TRPM2, TRPM8.
Zerencotrep is a small molecule drug. The usage of the INN stem ‘-cotrep’ in the name indicates that Zerencotrep is a transient receptor potential canonical channel 5 (TRPC5) antagonist. Zerencotrep has a monoisotopic molecular weight of 524.11 Da.
SYN
https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2014143799&_cid=P22-MJF454-30876-1
The following examples 7a through 7k were prepared using the method of example 6, step 1.
Example 7a 7-(4-chlorobenzyl)-l -(3-hydroxypropyl)-3-methyl-8-(3-(trifluoromethoxy)phenoxy)-l -purine-2,6(3H,7H)-dione
The title compound was prepared using the method of example 6, step 1 and purified
preparative HPLC to give 7-(4-chlorobenzyl)-l -(3-hydroxypropyl)-3-methyl-8-(3-
(trifluoromethoxy)phenoxy)-lH-purine-2,6(3H,7H)-dione (10 mg, 17.3% yield) as white solid. lH-NMR (CD3OD) δ 7.57-7.53(t, IH), 7.46-7.44(d, 2H), 7.37-7.33(m, 4H), 7.26-7.24(d, IH), 5.49(s, 2H), 4.13-4.09(t, IH), 3.64-3.60(t, 2H), 3.42(s, 3H), 1.89-1.86(m, 2H). LCMS retention time 3.059 min; LCMS MH+ 525.
PAT
- Side chain unsaturated 1α-hydroxyvitanim D homologsPublication Number: US-5250523-APriority Date: 1988-04-29Grant Date: 1993-10-05
- Antiviral methods utilizing ribofuranosylthiazolo[4,5-d]pyrimdine derivativesPublication Number: US-4880784-APriority Date: 1987-12-21Grant Date: 1989-11-14
- NEW NUCLEOSIDES AND NUCLEOTIDES AND PROCEDURES FOR THE PREPARATION.Publication Number: NO-893343-LPriority Date: 1987-12-21
- New amidino derivativesPublication Number: JP-H01131145-APriority Date: 1987-09-21
- Oligonucleotides, a process for preparing the same and their application as mediators of the action of interferonPublication Number: US-4476301-APriority Date: 1982-04-29Grant Date: 1984-10-09
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- Pico145 inhibits TRPC4-mediated mICAT and postprandial small intestinal motilityPublication Name: Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapiePublication Date: 2023-12PMID: 37857250DOI: 10.1016/j.biopha.2023.115672
- Human TRPC5 structures reveal interaction of a xanthine-based TRPC1/4/5 inhibitor with a conserved lipid binding sitePublication Name: Communications BiologyPublication Date: 2020-11-23PMCID: PMC7683545PMID: 33230284DOI: 10.1038/s42003-020-01437-8
- Discovery of a Potent and Selective TRPC5 Inhibitor, Efficacious in a Focal Segmental Glomerulosclerosis ModelPublication Name: ACS Medicinal Chemistry LettersPublication Date: 2019-10-22PMCID: PMC6862342PMID: 31749913DOI: 10.1021/acsmedchemlett.9b00430
- Potent, selective, and subunit‐dependent activation of TRPC5 channels by a xanthine derivativePublication Name: British Journal of PharmacologyPublication Date: 2019-09-06PMCID: PMC6811774PMID: 31277085DOI: 10.1111/bph.14791
- Review of Transient Receptor Potential Canonical (TRPC5) Channel Modulators and DiseasesPublication Name: Journal of Medicinal ChemistryPublication Date: 2019-04-03PMID: 30943030DOI: 10.1021/acs.jmedchem.8b01954
///////////zerencotrep, Pico 145, HC 608, HMIMSYLCWQ
New Drug Approvals 
