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Enavogliflozin, DWP-16001

February 26, 2020 9:17 am / Leave a comment

Enavogliflozin, DWP-16001

(2S,3R,4R,5S,6R)-2-(7-chloro-6-(4-cyclopropylbenzyl)-2,3-dihydrobenzofuran-4-yl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

CAS: 1415472-28-4
Chemical Formula: C24H27ClO6
Molecular Weight: 446.92
Elemental Analysis: C, 64.50; H, 6.09; Cl, 7.93; O, 21.48

Green Cross Corp INNOVATOR

Daewoong Pharmaceutical Co Ltd

Enavogliflozin is an antidiabetic (hypoglycemic).

Daewoong is investigating DWJ-304 , a sodium/glucose cotransporter 2 (SGLT-2) inhibitor, for treating type 2 diabetes. By February 2017, preclinical development was underway. Daewoong is developing DWP-16001 , presumed to be enavogliflozin, a SGLT-2 inhibitor, for treating type 2 diabetes. In September 2019, launch was expected in 2023.

PATENT

WO2012165914

DWP-16001 expire in EU states until June 2032 and US in November 2033.

PATENT

US 2014274918

PATENT

US2019169174

Paragraph 0305; 0340; 0347

H NMR (400 MHz, CD₃OD) δ 7.02 (d, J=8.0 Hz, 2H), 6.92 (d, J=8.0 Hz, 2H), 6.81 (s, 1H), 4.59 (t, J=8.8 Hz, 2H), 4.11 (d, J=9.2 Hz, 1H), 3.96 (ABq, Δv_AB=19.0 Hz, J_AB=15.2 Hz, 2H), 3.87-3.84 (m, 1H), 3.67-3.63 (m, 1H), 3.47-3.37 (m, 3H), 3.35-3.33 (m, 3H), 1.85-1.79 (m, 1H), 0.91-0.86 (m, 2H), 0.61-0.57 (m, 2H)

PATENT

WO2017217792 , claiming process for preparing diphenylmethane derivative.

https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2017217792&tab=FULLTEXT&_cid=P21-K72SDW-38338-1

¹H NMR(400 MHz, CD ₃OD) δ 7.02(d, J = 8.0 Hz, 2H), 6.92(d, J = 8.0 Hz, 2H), 6.81(s, 1H), 4.59(t, J = 8.8 Hz, 2H), 4.11(d, J = 9.2 Hz, 1H), 3.96(ABq, Δv _AB = 19.0 Hz, J _AB = 15.2 Hz, 2H), 3.87-3.84(m, 1H), 3.67-3.63(m, 1H), 3.47-3.37(m, 3H), 3.35-3.33(m, 3H), 1.85-1.79(m, 1H), 0.91-0.86(m, 2H), 0.61-0.57(m, 2H); [M+Na] ⁺ 469.

PATENT

WO-2020036382

The present invention relates to a method for producing an intermediate useful for the synthesis of a diphenylmethane derivative that can be used as a SGLT inhibitor. A method for synthesizing a compound of formula 7 according to the present invention has solved the problem of an existing synthesis process which requires an additional process due to the synthesis of Grignard reagent and the management of a related substance. In addition, the process can be simplified by minimizing the formation of the related substance and eliminating the need for reprocessing of reaction products, thereby becoming capable of maximizing a yield of a diphenylmethane derivative.

Process for preparing intermediates of SGLT inhibitor and their use for the synthesis of diphenyl-methane derivative, which can be used as SGLT inhibitors.

Sodium-dependent glucose cotransporters (SGLT) allow the transport of Na + along the concentration gradient simultaneously with the transport of glucose across the concentration gradient. Currently two important SGLT isoforms have been cloned, known as SGLT1 and SGLT2. SGLT1 is located in the intestine, kidney and heart and regulates cardiac glucose transport. SGLT1 is a high affinity low dose transporter and therefore only accounts for a portion of renal glucose reuptake. In contrast, SGLT2 is a low affinity, high dose transporter located primarily in the apica domain of epithelial cells in the early proximal manure tubules. In healthy individuals, over 99% of the plasma glucose filtered out of the renal glomeruli is reabsorbed and less than 1% of the total filtered glucose is excreted in the urine. It is estimated that 90% of renal glucose reuptake is promoted by SGLT2 and the remaining 10% is mediated by SGLT1 in the late proximal canal. Genetic mutations in SGLT2 do not have a particular adverse effect on carbohydrate metabolism but cause increased kidney glucose secretion of about 140 g / day following mutation. Human mutation studies have been the subject of therapeutic studies because SGLT2 is believed to be responsible for most renal glucose resorption.

[3]

Korean Unexamined Patent Publication No. 2017-0142904 discloses a method for producing a diphenylmethane derivative having inhibitory activity against SGLT2. Since the above document prepares diphenylmethane derivatives by a convergent synthesis method in which each group is individually synthesized and then coupled, the synthesis route is more concise and yield is higher than the linear synthesis method disclosed in the prior art. It is disclosed that it can increase and reduce the risks inherent in sequential synthesis pathways.

[4]

However, the preparation method of the diphenylmethane derivative according to Korean Patent Publication No. 2017-0142904 uses a heavy metal such as pyridinium chlorochromate (PCC) to burden safety management, and the Grignard reagent. In addition to the need for a separate manufacturing process, the cost of the additional process is not only incurred, but also the management of the flexible material is necessary because the flexible material from the Grignard reagent manufacturing process is included in the final product. In addition, since the product generated after the reaction between the intermediate and the Grignard reagent includes additional flexible materials, there is a problem that a reprocessing process of such flexible materials is required.

Step 3. 4- bromo- 7- chloro -6- (4- cyclopropylbenzyl ) -2,3- dihydrobenzofuran (Compound 6)

(4-bromo-7-chloro-2,3-dihydrobenzofuran-6-yl) (4-cyclopropylphenyl) methanone (Compound 5) in a mixture of dichloromethane (9.7 mL) and acetonitrile (9.7 mL) at -15 ° C. g, 2.57 mmol) was added Et ₃ SiH (1.2 mL, 7.71 mmol) and BF ₃ -Et ₂ O (0.79 mL, 6.42 mmol) in this order. The reaction mixture was allowed to warm to room temperature and then stirred for 4 hours. After completion of the reaction by TLC, the reaction solution was added with saturated NaHCO ₃aqueous solution (40 mL) to terminate the reaction, and extracted with ethyl acetate. The organic layer obtained by extraction was dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The concentrated residue was purified by silica gel chromatography to give the title compound 6 (0.84 g, 89.9%) as an off-white solid.

[387]

¹ H NMR (500 MHz, CDCl 3): δ 7.07 (d, J = 10.0 Hz, 2H), 6.99 (d, J = 10.0 Hz, 2H), 6.80 (s, 1H), 4.70 (t, J = 11.0 Hz , 2H), 3.97 (s, 2H), 3.26 (t, J = 11.0 Hz, 2H), 1.88-1.84 (m, 1H), 0.95-0.90 (m, 2H), 0.68-0.64 (m, 2H); LC-MS: [M + H] & lt; + & gt; 363.

REFERENCES

1: Markiewicz M, Jungnickel C, Stolte S, Białk-Bielińska A, Kumirska J, Mrozik W. Ultimate biodegradability and ecotoxicity of orally administered antidiabetic drugs. J Hazard Mater. 2017 Jul 5;333:154-161. doi: 10.1016/j.jhazmat.2017.03.030. Epub 2017 Mar 16. PubMed PMID: 28349868.

2: Holt RI. Trials of new anti-diabetes agents. Diabet Med. 2017 Feb;34(2):147. doi: 10.1111/dme.13306. PubMed PMID: 28090726.

/////// DWJ-304, Daewoong Pharmaceutical, DWP-16001, SGLT-2 inhibitor, type 2 diabetes, KOREA, Enavogliflozin

ClC1=C2C(CCO2)=C([C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)C=C1CC4=CC=C(C5CC5)C=C4

Tianagliflozin IND filed by Tianjin Institute of Pharmaceutical research

March 30, 2016 3:20 am / Leave a comment

Tianagliflozin,

taigeliejing, 6-deoxydapagliflozin

Molecular Formula:	C₂₁H₂₅ClO₅
Molecular Weight:	392.8732 g/mol

Tianjin Institute Of Pharmaceutical Research,

(3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-methyloxane-3,4,5-triol

1-[4-Chloro-3-(4-ethoxybenzyl)phenyl]-1,6-dideoxy-b-D-glucopyranose

D-Glucitol, 1,5-anhydro-1-C-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-deoxy-, (1S)-

1–[4–Chloro–3–(4–ethoxybenzyl)phenyl]–1,6–dideoxy–β–d–glucopyranose

6-deoxydapagliflozin

https://pubchem.ncbi.nlm.nih.gov/compound/67891767#section=Top

A SGLT-2 inhibitor potentially for the treatment of type 2 diabetes.

CAS N. 1461750-27-5

The structures of dapagliflozin and 6-deoxydapagliflozin (1)

,deletion of the 6-OH in the sugar moiety of dapagliflozin led to the discovery of a more potent SGLT2 inhibitor, 6-deoxydapagliflozin (1, ). In an in vitro assay, 1 was a more active SGLT2 inhibitor, with IC ₅₀ = 0.67 nM against human SGLT2 (hSGLT2), as compared with 1.1 nM for dapagliflozin, leading to the identification of 1 as the most active SGLT2 inhibitor discovered so far in this field. Also in an in vivo assay, 1 also introduced more urinary glucose in a rat urinary glucose excretion test (UGE) and exhibited more potent blood glucose inhibitory activity in a rat oral glucose tolerance test (OGTT) than dapagliflozin.

Given the fact that 6-dexoydapagliflozin (1) is a very promising SGLT2 inhibitor that could be used to treat type 2 diabetes, led to preclinical trials

 Tianjin Institute Of Pharmaceutical Research,天津药物研究院

SPECTRAL DATA of Tianagliflozin

1 as a white solid (3.65 g, 93 %). R _f = 0.35 (EtOAc);

m.p.: 148–149 °C;

¹H NMR (400 MHz, DMSO-d ₆): δ = 7.35 (d, 1H, J = 8.4 Hz), 7.25 (s, 1H), 7.18 (d, 1H, J = 8.0 Hz), 7.08 (d, 2H, J = 8.4 Hz), 6.81 (d, 2H, J = 8.4 Hz), 4.95 (d, 1H, J = 5.2 Hz, OH), 4.90 (d, 1H, J = 4.4 Hz, OH), 4.79 (d, 1H, J = 5.6 Hz, OH), 3.92–4.01 (m, 5H), 3.24–3.29 (m, 1H), 3.18–3.22 (m, 1H), 3.09–3.15 (m, 1H), 2.89–2.95 (m, 1H), 1.29 (t, 3H, J = 7.0 Hz, CH₂ CH ₃), 1.15 (d, 3H, J = 6.0 Hz, CHCH ₃) ppm;

¹³C NMR (100 MHz, DMSO-d ₆): δ = 156.85, 139.65, 137.82, 131.83, 131.16, 130.58, 129.52, 128.65, 127.14, 114.26, 80.71, 77.98, 75.77, 75.51, 74.81, 62.84, 37.55, 18.19, 14.62 ppm;

IR (KBr): v¯¯¯ = 3,564 (w), 3,385 (s), 2,981 (s), 2,899 (s), 2,861 (s), 1,613 (m), 1,512 (s), 1,477 (m), 1,247 (s), 1,102 (s), 1,045 (s), 1,012 (s) cm⁻¹;

HR–MS: calcd for C₂₁H₂₉ClNO₅ ([M + NH₄]⁺) 410.1729, found 410.1724.

PATENT

CN 103864737

http://www.google.com/patents/CN103864737A?cl=en

PATENT

WO 2014094544

http://www.google.com/patents/WO2014094544A1?cl=en

Figure imgf000032_0001

-27-

1 D1 -6 Optionally, the step (7 ‘) is the step (7’) in place:

LS l- [4 – D (I- Dl- 6)

(DMSO-d _6, 400 MHz), δ 7.35 (d, 1H, J = 8.0 Hz), 7.28 (d, 1H, J ‘. 2.0 Hz), 7.17 (dd, IH, / = 2.0 Hz and 8.4 Hz), 7.05 (d, 2H, _J: 8.8 Hz), 6.79 (d, 2H, 8.8 Hz): 4.924,95 (m, 2H), 4,81 (d, IH, 6,0 Hz), 3.93- 3.99 (m, 5H), 3,85 (d, 1H, J = 10,4 Hz), 3,66 (dd, IH, 5,2 Hz and 11,6 Hz), 3.17-3,28 (m, 3H), 3.02-3.08 _(m: IH), 1.28 (t, 3H, J = 7,0 Hz), 0,80 (s, 9H), -0.05 (s, 3H), -0.09 (s, 3H) .

PATENT

CN 104045614

[0066] The added 100mL dried over anhydrous methanol 0. 5g of sodium metal, nitrogen at room temperature with stirring, until the sodium metal disappeared. Followed by addition of 5. 2g (10mmol) of compound 6, stirring was continued at room temperature for 3 hours. To the reaction system was added 5g strong acid cation exchange resin, stirred at room temperature overnight, the reaction mixture until pH = 7. The resin was removed by suction, and the filtrate evaporated to dryness on a rotary evaporator, the residue was further dried on a vacuum pump to give the product I-D1-6, as a white foamy solid.

PATENT

WO 2014139447

http://link.springer.com/article/10.1007%2Fs40242-014-4043-9#/page-1

Med Chem. 2015;11(4):317-28.

Design of SGLT2 Inhibitors for the Treatment of Type 2 Diabetes: A History Driven by Biology to Chemistry.

Cai W, Jiang L, Xie Y, Liu Y, Liu W, Zhao G¹.

Abstract

A brief history of the design of sodium-dependent glucose cotransporter 2 (SGLT2) inhibitors is reviewed. The design of O-glucoside SGLT2 inhibitors by structural modification of phlorizin, a naturally occurring O-glucoside, in the early stage was a process mainly driven by biology with anticipation of improving SGLT2/SGLT1 selectivity and increasing metabolic stability. Discovery of dapagliflozin, a pioneering C-glucoside SGLT2 inhibitor developed by Bristol-Myers Squibb, represents an important milestone in this history. In the second stage, the design of C-glycoside SGLT2 inhibitors by modifications of the aglycone and glucose moiety of dapagliflozin, an original structural template for almost all C-glycoside SGLT2 inhibitors, was mainly driven by synthetic organic chemistry due to the challenge of designing dapagliflozin derivatives that are patentable, biologically active and synthetically accessible. Structure-activity relationships (SAR) of the SGLT2 inhibitors are also discussed.

http://www.ncbi.nlm.nih.gov/pubmed/25557661

Paper

Discovery of 6-Deoxydapagliflozin as a Highly Potent Sodium-dependent Glucose Cotransporter 2 (SGLT2) Inhibitor for the Treatment of Type 2 Diabetes

Authors: Zhang, Lingyu; Wang, Yuli; Xu, Huaqiang; Shi, Yongheng; Liu, Bingni; Wei, Qunchao; Xu, Weiren; Tang, Lida; Wang, Jianwu; Zhao, Guilong

Source: Medicinal Chemistry, Volume 10, Number 3, May 2014, pp. 304-317(14)

http://www.ingentaconnect.com/content/ben/mc/2014/00000010/00000003/art00009?crawler=true

CLIP

A facile synthesis of 6-deoxydapagliflozin

Keywords. Carbohydrates Drug research Hydrogenolysis Dapagliflozin SGLT2 inhibitor

http://link.springer.com/article/10.1007/s00706-013-1053-0/fulltext.html

The synthetic route to the target compound 1 is shown in Scheme 3. The starting material methyl 2,3,4-tri-O-benzyl-6-deoxy-6-iodo-α–d-glucopyranoside (3) was prepared from commercially available methyl α–d-glucopyranoside (2) according to a known method [5, 6].

Iodide 3 was reductively deiodinated to give 4 in 91 % yield under hydrogenolytic conditions using 10 % Pd/C as catalyst in the presence of Et₃N as base in THF/MeOH at room temperature.

when the iodide 3 was treated with Barton–McCombie reagent (n-Bu₃SnH/AIBN) [7] in toluene at room temperature no reaction occurred; however, when the reaction was carried out at elevated temperatures, such as reflux, a complex mixture formed with only a trace amount (3 %, entry 1) of the desired product 4.

When the iodide 3 was treated with LiAlH₄ in THF at 0 °C to room temperature, another complex mixture was produced with only a trace amount (2 %, entry 2) of 4.

When Pd(OH)₂ was used as the hydrogenolysis catalyst instead of 10 % Pd/C, the desired 4 was indeed formed (14 %, entry 4), but most of the starting material was converted to a few more polar byproducts, which were believed to result from the cleavage of at least one of the benzyl groups.

pdf available

Monatshefte für Chemie – Chemical Monthly

December 2013, Volume 144, Issue 12, pp 1903-1910

http://download.springer.com/static/pdf/721/art%253A10.1007%252Fs00706-013-1053-0.pdf?originUrl=http%3A%2F%2Flink.springer.com%2Farticle%2F10.1007%2Fs00706-013-1053-0&token2=exp=1458808857~acl=%2Fstatic%2Fpdf%2F721%2Fart%25253A10.1007%25252Fs00706-013-1053-0.pdf%3ForiginUrl%3Dhttp%253A%252F%252Flink.springer.com%252Farticle%252F10.1007%252Fs00706-013-1053-0*~hmac=bd1c3c2bdc3712f5540267c99f732b2f7588020a868aa23021792a2a2a58d65e

References

1.Washburn WN (2009) J Med Chem 52:1785
2.Hardman TC, Dubrey SW (2011) Diabetes Ther 2:133
3.Meng M, Ellsworth BA, Nirschl AA, McCann PJ, Patel M, Girotra RN, Wu G, Sher PM, Morrison EP, Biller SA, Zahler R, Deshpande PP, Pullockaran A, Hagan DL, Morgan N, Taylor JR, Obermeier MT, Humphreys WG, Khanna A, Discenza L, Robertson JM, Wang A, Han S, Wetterau JR, Janovitz EB, Flint OP, Whaley JM, Washburn WN (2008) J Med Chem 51:1145
4.Nomura S, Sakamaki S, Hongu M, Kawanishi E, Koga Y, Sakamoto T, Yamamoto Y, Ueta K, Kimata H, Nakayama K, Tsuda-Tsukimoto M (2010) J Med Chem 53:6355
5.Lee JC, Francis S, Georg GI, Dutta D, Gupta V, Tash JS, Yang Y, Zhu J-Y, Schoenbrunn E (2012) J Org Chem 77:3082
6.Bartoszewicz A, Kalek M, Stawinski J (2008) Tetrahedron 64:8843
7.Zhao GL, Lou YY, Zhang LS, Shao H, Xu WR, Tang LD, Zou MX (2012) Synth Commun 42:2885
8.Koto S, Morishima N, Miyata Y, Zen S (1976) Bull Chem Soc Jpn 49:2639
9.Kakinuma H, Oi T, Hashimoto-Tsuchiya Y, Arai M, Kawakita Y, Fukasawa Y, Iida I, Hagima N, Takeuchi H, Chino Y, Asami J, Okumura-Kitajima L, Io F, Yamamoto D, Miyata N, Takahashi T, Uchida S, Yamamoto K (2010) J Med Chem 53:3247
10.Xu J, Egger A, Bernet B, Vasella A (1996) Helv Chim Acta 79:2004
11.Lee SH, Song K-S, Kim JY, Kang M, Lee JS, Cho S-H, Park H-J, Kim J, Lee J (2011) Bioorg Med Chem 19:5813
12.Song K-S, Lee SH, Kim MJ, Seo HJ, Lee J, Lee S-H, Jung ME, Son E-J, Lee MW, Kim J, Lee J (2011) ACS Med Chem Lett 2:182
13.Lee J, Lee S-H, Seo HJ, Son E-J, Lee SH, Jung ME, Lee MW, Han HK, Kim J, Kang J, Lee J (2010) Bioorg Med Chem 18:2178
14.Kim MJ, Lee SH, Park SO, Kang H, Lee JS, Lee KN, Jung ME, Kim J, Lee J (2011) Bioorg Med Chem 19:5468
15.Skaanderup PR, Poulsen CS, Hyldtoft L, Jørgensen MR, Madsen R (2002) Synthesis 1721
Monatshefte fuer Chemie (2013), 144(12), 1903-1910
Medicinal Chemistry (Sharjah, United Arab Emirates) (2014), 10(3), 304-317
Chinese Journal of Structural Chemistry (2014), 33(1), 85-89
Xiandai Yaowu Yu Linchuang (2013), 28(6), 838-841
Chemical Research in Chinese Universities (2014), 30(5), 785-793

////////, SGLT-2 inhibitor, type 2 diabetes, Tianagliflozin, taigeliejing, 6-deoxydapagliflozin, 1461750-27-5

Clc1c(cc(cc1)C2[C@@H]([C@H]([C@@H]([C@H](O2)C)O)O)O)Cc3ccc(cc3)OCC

CCOC1=CC=C(C=C1)CC2=C(C=CC(=C2)C3C(C(C(C(O3)C)O)O)O)Cl

c1(c(cc(cc1)C2OC(C(C(C2O)O)O)C)Cc3ccc(cc3)OCC)Cl

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REFERENCES

Tianagliflozin IND filed by Tianjin Institute of Pharmaceutical research

1–[4–Chloro–3–(4–ethoxybenzyl)phenyl]–1,6–dideoxy–β–d–glucopyranose

Design of SGLT2 Inhibitors for the Treatment of Type 2 Diabetes: A History Driven by Biology to Chemistry.

Abstract

Discovery of 6-Deoxydapagliflozin as a Highly Potent Sodium-dependent Glucose Cotransporter 2 (SGLT2) Inhibitor for the Treatment of Type 2 Diabetes

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Tianagliflozin IND filed by Tianjin Institute of Pharmaceutical research

1–[4–Chloro–3–(4–ethoxybenzyl)phenyl]–1,6–dideoxy–β–d–glucopyranose

Design of SGLT2 Inhibitors for the Treatment of Type 2 Diabetes: A History Driven by Biology to Chemistry.

Abstract

Discovery of 6-Deoxydapagliflozin as a Highly Potent Sodium-dependent Glucose Cotransporter 2 (SGLT2) Inhibitor for the Treatment of Type 2 Diabetes

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