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Idrebormilast

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Idrebormilast

CAS 2415085-44-6

MF C18H22BNO4, MW 327.18

Pyridine, 3-[(4R)-2-hydroxy-1,2-oxaborolan-4-yl]-5-(4-methoxy-3-propoxyphenyl)-

(4R)-4-[5-(4-methoxy-3-propoxyphenyl)pyridin-3-yl]-1,2-oxaborolan-2-ol
phosphodiesterase 4 (PDE4) inhibitor, non-steroidal anti-inflammatory, M6ZU548FWD, PF07038124, PF 07038124

PF-07038124 is under investigation in clinical trial NCT05298033 (Study of Efficacy, Safety and Tolerability of Crisaborole and PF-07038124 With and Without NBUVB in Vitiligo).

IDREBORMILAST is a small molecule drug with a maximum clinical trial phase of II (across all indications) and has 2 investigational indications.

Study of Efficacy, Safety and Tolerability of Crisaborole and PF-07038124 With and Without NBUVB in VitiligoCTID: NCT05298033Phase: Phase 2Status: CompletedDate: 2024-06-12
PDE4 Inhibition in Seborrheic Dermatitis and Papulopustular RosaceaCTID: NCT06013371Phase: Phase 2Status: TerminatedDate: 2025-04-24
A Study To Determine The Safety, Tolerability, Skin Irritation Potential, And PK Following Topical Application Of PF-07038124 In Healthy ParticipantsCTID: NCT04135560Phase: Phase 1Status: CompletedDate: 2020-05-14
Study to Evaluate the Safety, Local and Systemic Tolerability, and Pharmacokinetics of Multiple-Dose Topical Administration of PF-07038124 in Japanese Healthy ParticipantsCTID: NCT04863417Phase: Phase 1Status: CompletedDate: 2024-01-25
Study To Assess Efficacy, Safety, Tolerability And Pharmacokinetics Of PF-07038124 Ointment In Participants With Atopic Dermatitis Or Plaque PsoriasisCTID: NCT04664153Phase: Phase 2Status: CompletedDate: 2022-08-26

SYN

US11559538, Example 4

https://patentscope.wipo.int/search/en/detail.jsf?docId=US319902318&_cid=P12-MKYUGZ-80893-1

PAT

https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2020070651&_cid=P12-MKYUA5-76010-1

Example 4: (R)-4-(5-(4-methoxy-3-propoxyphenyl)pyridin-3-yl)-1 ,2-oxaborolan-2-ol

Method A:

To a mixture of (R)-(3-((tert-butyldimethylsilyl)oxy)-2-(5-(4-methoxy-3-propoxyphenyl)pyridin-3-yl)propyl)boronic acid (Preparation 6, 55 g, 120 mmol) in IPA (247 mL) was added 5 M hydrogen chloride in IPA (37 mL, 185 mmol) at about 20 °C. The mixture was stirred for about 3 h and concentrated. The residue was diluted with EtOAc (500 mL) and 1 N

HCI (500 mL) was added. The layers were separated and the EtOAc layer was extracted with 0.5 N HCI (2 x 200 mL). The aqueous extracts were combined with the separated acidic aqueous layer and washed with EtOAc (3 x 250 mL). The combined acidic aqueous layers were treated with K3PO4 to pH 5-6. The mixture was extracted with EtOAc (1 x 500 mL, 2 x 200 mL). The combined EtOAc extracts were washed with brine, dried over Na₂S0₄, filtered and concentrated to afford (R)-4-(5-(4-methoxy-3-propoxyphenyl)pyridin-3-yl)-1 ,2-oxaborolan-2-ol (34.5 g, 88%). This was further purified by preparative SFC (Prep SFC Method C) to afford 29 g as a crude product. The crude product was dissolved in methanol (250 mL) and water (50 mL) and stirred at 20 °C for about 30 min before concentrating. The concentrated solution was partitioned between brine and EtOAc. The aqueous layer was separated and extracted with EtOAc. The EtOAc extracts were combined with the separate EtOAc layer and were washed with brine, dried over Na₂S0₄ and concentrated. The residue was dissolved in degassed EtOAc (200 mL) and degassed heptane (100 mL) was added slowly. Heptane was added until a precipitate was observed and and the resulting mixture was stirred overnight under N₂. The solid was filtered to afford 8.08 g of product. The filtrate was concentrated and the residue dissolved in EtOAc (50 mL). Heptane (25 mL) was slowly added and the mixture stirred overnight open to air. The solid was filtered to afford a second batch (6.16 g). This was repeated a second time to afford 3.0 g. The filtrate was stirred overnight to afford additional batches (2.09 g and 3.1 g) respectively. The solid batches were combined to afford (R)-4-(5-(4-methoxy-3-propoxyphenyl)pyridin-3-yl)-1 ,2-oxaborolan-2-ol (22.3 g, 57%) as a crystalline solid. Ή NMR (DMSO-cfe, 400MHz): d 8.70 (d, J = 2.3 Hz, 1 H), 8.68 (s, 1 H), 8.42 (d, J = 2.0 Hz, 1 H), 7.93 (s, 1 H), 7.27 (d, J = 2.0 Hz, 1 H), 7.23-7.26 (m, 1 H), 7.06 (d, J = 8.2 Hz, 1 H), 4.28 (t, J = 8.2 Hz, 1 H), 4.03 (t, J = 6.4 Hz, 2H), 3.86 (t, J = 9.0 Hz, 1 H), 3.81 (s, 3H), 3.46-3.54 (m, 1 H), 1 .71 -1 .80 (m, 2H), 1 .28-1 .35 (m, 1 H), 1 .15 (dd, J = 10.5, 16.4 Hz, 1 H), 1 .00 (t, J = 7.4 Hz, 3H). LCMS m/z = 328 [MH]⁺; RT [Analytical SFC Method B] = 7.30 min. [a]²⁰_D -23.7 (c = 0.9, EtOH).

Elemental analysis calculated (%) for Ci₈H₂₂BN0₄: C 66.08, H 6.78, N 4.28. Found: C 65.86, H 6.59, N 4.18.

Method B:

Step 1 : To THF (18.0 mL) was added 3-(3-((tert-butyldimethylsilyl)oxy)prop-1 -en-2-yl)-5-(4-methoxy-3-propoxyphenyl)pyridine (Preparation 50, 3.0 g, 7.25 mmol), [lr(COD)CI]₂ (CAS 121 12-67-3, 36.9 mg, 0.054 mmol) and (S)[(S_p)-2-(diphenylphosphino)ferrocenyl]-4-isopropyloxazoline (CAS 163169-29-7, 52.4 mg, 0.109 mmol). Additional THF (6.0 mL) was added to the mixture which was warmed to about 50 °C for about 5 min. Catecholborane (10.9 mL, 1 0M in THF) was added to the mixture and stirred at about 50 °C for about 1 h. The mixture was cooled to about 20 °C and treated with HCI (12.2 M, 1 .51 mL) over 1 min. The mixture was held at about 20 °C for about 1 h, afterwhich a precipitate had formed. The mixture was cooled to about 10 °C and filtered. The filtered solid was washed with THF (6.0 mL) and

dried overnight at 35°C under vacuum to afford (R)-4-(5-(4-methoxy-3-propoxyphenyl)pyridine-3-yl)-1 ,2-oxaborolan-2-ol hydrochloride monohydrate (3.98 g, 91 %) as a crystalline solid. ¹H NMR (CD₃OD, 400MHz): d 8.98 (d, J = 1 .5 Hz, 1 H), 8.75 (s, 1 H), 8.67 (d, J = 1 .3 Hz, 1 H), 7.37-7.43 (m, 2H), 7.15 (d, J = 8.3 Hz, 1 H), 4.09 (t, J = 6.5 Hz, 2H), 3.89-3.92 (m, 1 H), 3.86-3.95 (m, 5H), 3.46 (br s, 1 H), 1 .85 (m, 2H), 1 .31 -1 .42 (m, 2H), 1 .08 (t, J = 7.4 Hz, 3H). LCMS m/z = 328 [MH]⁺.

Step 2: To a solution of (R)-4-(5-(4-methoxy-3-propoxyphenyl)pyridine-3-yl)-1 ,2-oxaborolan-2-ol hydrochloride monohydrate (2.0 g, 5.24 mmol) in water (60 ml_) was added EtOAc (20 ml_). To the stirred mixture was added NaOH (1 N) dropwise to adjust the pH of the aqeous layer to 7-8. The mixture was stirred at about 20 °C for about 5 min. The layers were separated and the aqueous layer was extracted with EtOAc (2 x 10 ml_). The combined EtOAc extracts were concentrated. The residue was dissolved in THF/MTBE (1 :3, 22 ml_) and stirred at about 20 °C overnight. The precipitate was filtered and dried under vacuum to afford (R)-4-(5-(4-methoxy-3-propoxyphenyl)pyridine-3-yl)-1 ,2-oxaborolan-2-ol (1 .17 g, 68%) as a crystalline solid. Ή NMR (DMSO-cfe, 400MHz): d 8.70 (d, J = 2.3 Hz, 1 H), 8.68 (s, 1 H), 8.42 (d, J = 2.0 Hz, 1 H), 7.93 (s, 1 H), 7.27 (d, J = 2.0 Hz, 1 H), 7.23-7.26 (m, 1 H), 7.06 (d, J = 8.2 Hz, 1 H), 4.28 (t, J = 8.2 Hz, 1 H), 4.03 (t, J = 6.4 Hz, 2H), 3.86 (t, J = 9.0 Hz, 1 H), 3.81 (s, 3H), 3.46-3.54 (m, 1 H), 1 .71 -1 .80 (m, 2H), 1 .28-1 .35 (m, 1 H), 1 .15 (dd, J = 10.5, 16.4 Hz, 1 H), 1 .00 (t, J = 7.4 Hz, 3H). LCMS m/z = 328 [MH]⁺.

Method C:

To a solution of (R)-(3-((tert-butyldimethylsilyl)oxy)-2-(5-(4-methoxy-3-propoxyphenyl)pyridin-3-yl)propyl)boronic acid (Preparation 6, 29.0 g, 63.1 mmol) in THF (66 mL) was added aqueous HCI (84.2 mL, 252 mmol, 3.0 M) and stirred at 20 °C for about 1 .5 h. The mixture was concentrated. The mixture was diluted with 1 M HCI and extracted with EtOAc (3 x 100 mL). The combined EtOAc extracts were washed with 1 M HCI (3 x 50 mL). The combined aqueous extracts were neutralized with K3PO4 to pH 7-8 and extracted with EtOAc (3 x 100 mL). The combined EtOAc extracts were dried over Na₂S0₄, filtered and concentrated to afford (R)-4-(5-(4-methoxy-3-propoxyphenyl)pyridin-3-yl)-1 ,2-oxaborolan-2-ol (19.0 g, 92%).

This was further purified by preparative SFC (Prep SFC Method C) to afford 18 g of the crude product. The crude product was dissolved in MeOH (100 mL) and water (50 mL). The mixture was partitioned between brine and EtOAc. The layers were separated and the aqueous layer was extracted with EtOAc. The combined EtOAc extracts were washed with brine, dried over Na₂S0₄ and concentrated to afford 15 g of product. The residue was dissolved in EtOAc (60 mL) and heptane (30 mL) was slowly added over about 3 h. The mixture was stirred at about 20 °C overnight. The precipitate was filtered and dried to afford (8.08 g). This process was repeated 2 more times to afford additional batches (2.01 g and 1 .03 g), respectively. The three batches were combined in heptane (100 mL), chilled to about -78 °C for about 10 min, filtered

and dried to afford (R)-4-(5-(4-methoxy-3-propoxyphenyl)pyridin-3-yl)-1 ,2-oxaborolan-2-ol (10.4 g, 51 %) as a crystalline solid. Ή NMR (DMSO -d₆, 400MHz): d 8.70 (d, J = 2.3 Hz, 1 H), 8.68 (s,

1 H), 8.42 (d, J = 2.0 Hz, 1 H), 7.93 (s, 1 H), 7.27 (d, J = 2.0 Hz, 1 H), 7.23-7.26 (m, 1 H), 7.06 (d, J = 8.2 Hz, 1 H), 4.28 (t, J = 8.2 Hz, 1 H), 4.03 (t, J = 6.4 Hz, 2H), 3.86 (t, J = 9.0 Hz, 1 H), 3.81 (s, 3H), 3.46-3.54 (m, 1 H), 1 .71 -1 .80 (m, 2H), 1 .28-1 .35 (m, 1 H), 1 .15 (dd, J = 10.5, 16.4 Hz, 1 H),

1 .00 (t, J = 7.4 Hz, 3H). LCMS m/z = 328 [MH]⁺.

PAT

Substituted 1,2-oxaborolan-2-ols as PDE4 inhibitorsPublication Number: US-11559538-B2Priority Date: 2018-10-05Grant Date: 2023-01-24
Boron-containing PDE4 inhibitorsPublication Number: CN-113166177-BPriority Date: 2018-10-05Grant Date: 2024-09-03
Boron Containing PDE4 InhibitorsPublication Number: US-2021069219-A1Priority Date: 2018-10-05
Boron containing pde4 inhibitorsPublication Number: CA-3114702-CPriority Date: 2018-10-05Grant Date: 2023-08-08
PDE4 INHIBITORS CONTAINING BORONPublication Number: BR-112021005870-B1Priority Date: 2018-10-05
Boron containing pde4 inhibitorsPublication Number: WO-2020070651-A1Priority Date: 2018-10-05
Boron-containing PDE4 inhibitorsPublication Number: CN-113166177-APriority Date: 2018-10-05
Boron Containing PDE4 InhibitorsPublication Number: US-2023148402-A1Priority Date: 2018-10-05
Boron containing pde4 inhibitorsPublication Number: EP-3861001-A1Priority Date: 2018-10-05
Boron-containing PDE4 inhibitorsPublication Number: ES-2974208-T3Priority Date: 2018-10-05Grant Date: 2024-06-26
PDE4 inhibitor (R)-4-(5-(4-methoxy-3-propoxyphenyl)pyridin-3-yl)-1,2-oxaborolan-2-olPublication Number: US-10946031-B2Priority Date: 2018-10-05Grant Date: 2021-03-16
Boron-containing PDE4 inhibitorsPublication Number: KR-102576125-B1Priority Date: 2018-10-05Grant Date: 2023-09-08
Boron-containing PDE4 inhibitorsPublication Number: KR-20210068532-APriority Date: 2018-10-05
Boron containing pde4 inhibitorsPublication Number: EP-3861001-B1Priority Date: 2018-10-05Grant Date: 2023-12-13
Boron Containing PDE4 InhibitorsPublication Number: US-2020108083-A1Priority Date: 2018-10-05
Boron containing pde4 inhibitorsPublication Number: CA-3114702-A1Priority Date: 2018-10-05
boron containing pde4 inhibitorsPublication Number: BR-112021005870-A2Priority Date: 2018-10-05
Boron containing pde4 inhibitorsPublication Number: TW-202027755-APriority Date: 2018-10-05
Stable topical formulations of 1(r)-4-(5-(4-methoxy-3-propoxyphenyl)pyridin-3-yl)-1,2-oxaborolan-2-olPublication Number: CA-3191886-A1Priority Date: 2020-08-20
STABLE TOPICAL FORMULATIONS OF 1(R)-4-(5-(4-METHOXY-3-PROPOXYPHEN IL)PYRIDIN-3-IL)-1,2-OXABOROLAN-2-OL.Publication Number: MX-2023002086-APriority Date: 2020-08-20
Stable topical formulations of 1(r)-4-(5-(4-methoxy-3-propoxyphenyl)pyridin-3-yl)-1,2-oxaborolan-2-olPublication Number: WO-2022038485-A1Priority Date: 2020-08-20
1(R)-4-(5-(4-methoxy-3-propoxyphenyl)pyridin-3-yl)-1,2-oxaborolan-2-ol is a stable partial preparationPublication Number: CN-115916260-APriority Date: 2020-08-20
Stable Topical Formulations of 1(R)-4-(5-(4-Methoxy-3-Propoxphenyl)Pyridin-3-YL)-1,2-OX-Aborolan-2-OLPublication Number: US-2023310472-A1Priority Date: 2020-08-20
Combination therapyPublication Number: WO-2024231312-A2Priority Date: 2023-05-05
Borate derivative and uses thereofPublication Number: EP-4269418-A1Priority Date: 2020-12-25
Stable topical formulations of 1(r)-4-(5-(4-methoxy-3-propoxyphenyl)pyridin-3-yl)-1,2-oxaborolan-2-olPublication Number: EP-4199902-A1Priority Date: 2020-08-20
Stable topical formulation of 1(R)-4-(5-(4-methoxy-3-propoxyphenyl)pyridin-3-yl)-1,2-oxaborolan-2-olPublication Number: JP-2023538362-APriority Date: 2020-08-20
STABLE TOPICAL FORMULATIONS OF 1(R)-4-(5-(4-METHOXY-3-PROPOXYPHENYL)PYRIDIN-3-IL)-1,2-OXABOROLAN-2-OLPublication Number: BR-112023002533-A2Priority Date: 2020-08-20

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Tags: idrebormilast, M6ZU548FWD, non-steroidal anti-inflammatory, PF07038124, phosphodiesterase 4 (PDE4) inhibitor

By DR ANTHONY MELVIN CRASTO Ph.D in ANTI INFLAMATORY, Uncategorized on January 29, 2026.

Latest Posts

Idrebormilast
Idrebormilast CAS 2415085-44-6 MF C18H22BNO4, MW 327.18 Pyridine, 3-[(4R)-2-hydroxy-1,2-oxaborolan-4-yl]-5-(4-methoxy-3-propoxyphenyl)- (4R)-4-[5-(4-methoxy-3-propoxyphenyl)pyridin-3-yl]-1,2-oxaborolan-2-olphosphodiesterase 4 (PDE4) inhibitor, non-steroidal anti-inflammatory, M6ZU548FWD, PF07038124, PF 07038124 PF-07038124 is under investigation in clinical…
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DR ANTHONY MELVIN CRASTO Ph.D

DR ANTHONY MELVIN CRASTO, Born in Mumbai in 1964 and graduated from Mumbai University, Completed his Ph.D from ICT, 1991,Matunga, Mumbai, India, in Organic Chemistry, The thesis topic was Synthesis of Novel Pyrethroid Analogues, Currently he is working with AFRICURE PHARMA, ROW2TECH, NIPER-G, Department of Pharmaceuticals, Ministry of Chemicals and Fertilizers, Govt. of India as ADVISOR, earlier assignment was with GLENMARK LIFE SCIENCES LTD, as CONSUlTANT, Retired from GLENMARK in Jan2022 Research Centre as Principal Scientist, Process Research (bulk actives) at Mahape, Navi Mumbai, India. Total Industry exp 32 plus yrs, Prior to joining Glenmark, he has worked with major multinationals like Hoechst Marion Roussel, now Sanofi, Searle India Ltd, now RPG lifesciences, etc. He has worked with notable scientists like Dr K Nagarajan, Dr Ralph Stapel, Prof S Seshadri, etc, He did custom synthesis for major multinationals in his career like BASF, Novartis, Sanofi, etc., He has worked in Discovery, Natural products, Bulk drugs, Generics, Intermediates, Fine chemicals, Neutraceuticals, GMP, Scaleups, etc, he is now helping millions, has 9 million plus hits on Google on all Organic chemistry websites. His friends call him Open superstar worlddrugtracker. His New Drug Approvals, Green Chemistry International, All about drugs, Eurekamoments, Organic spectroscopy international, etc in organic chemistry are some most read blogs He has hands on experience in initiation and developing novel routes for drug molecules and implementation them on commercial scale over a 32 PLUS year tenure till date Feb 2023, Around 35 plus products in his career. He has good knowledge of IPM, GMP, Regulatory aspects, he has several International patents published worldwide . He has good proficiency in Technology transfer, Spectroscopy, Stereochemistry, Synthesis, Polymorphism etc., He suffered a paralytic stroke/ Acute Transverse mylitis in Dec 2007 and is 90 %Paralysed, He is bound to a wheelchair, this seems to have injected feul in him to help chemists all around the world, he is more active than before and is pushing boundaries, He has 100 million plus hits on Google, 2.5 lakh plus connections on all networking sites, 100 Lakh plus views on dozen plus blogs, 227 countries, 7 continents, He makes himself available to all, contact him on +91 9323115463, email amcrasto@gmail.com, Twitter, @amcrasto , He lives and will die for his family, 90% paralysis cannot kill his soul., Notably he has 38 lakh plus views on New Drug Approvals Blog in 227 countries......https://newdrugapprovals.wordpress.com/ , He appreciates the help he gets from one and all, Friends, Family, Glenmark, Readers, Wellwishers, Doctors, Drug authorities, His Contacts, Physiotherapist, etc He has total of 32 International and Indian awards

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