CA2680133A1 - Methods and intermediates for synthesis of selective dpp-iv inhibitors - Google Patents
Methods and intermediates for synthesis of selective dpp-iv inhibitors Download PDFInfo
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- CA2680133A1 CA2680133A1 CA002680133A CA2680133A CA2680133A1 CA 2680133 A1 CA2680133 A1 CA 2680133A1 CA 002680133 A CA002680133 A CA 002680133A CA 2680133 A CA2680133 A CA 2680133A CA 2680133 A1 CA2680133 A1 CA 2680133A1
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- 125000003427 indacenyl group Chemical group 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 150000008040 ionic compounds Chemical class 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- PSACHCMMPFMFAJ-UHFFFAOYSA-N nmm n-methylmorpholine Chemical compound CN1CCOCC1.CN1CCOCC1 PSACHCMMPFMFAJ-UHFFFAOYSA-N 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000003232 p-nitrobenzoyl group Chemical group [N+](=O)([O-])C1=CC=C(C(=O)*)C=C1 0.000 description 1
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- 229910052763 palladium Inorganic materials 0.000 description 1
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- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
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- XOJVVFBFDXDTEG-UHFFFAOYSA-N pristane Chemical compound CC(C)CCCC(C)CCCC(C)CCCC(C)C XOJVVFBFDXDTEG-UHFFFAOYSA-N 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 125000001725 pyrenyl group Chemical group 0.000 description 1
- WGBPCMYISDZTQA-UHFFFAOYSA-N pyrrolidin-1-ylboronic acid Chemical compound OB(O)N1CCCC1 WGBPCMYISDZTQA-UHFFFAOYSA-N 0.000 description 1
- VEBQYHFHXCAREJ-UHFFFAOYSA-N pyrrolidin-2-ylboronic acid Chemical compound OB(O)C1CCCN1 VEBQYHFHXCAREJ-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 230000029964 regulation of glucose metabolic process Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000010956 selective crystallization Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- YJMLRPJMPXRDTD-UHFFFAOYSA-M sodium 3-oxo-3-phenylmethoxy-2-phenylmethoxycarbonyl-2-(pyrrolidin-3-ylamino)propanoate Chemical compound [Na+].C(=O)(OCC1=CC=CC=C1)C(NC1CNCC1)(C(=O)[O-])C(=O)OCC1=CC=CC=C1 YJMLRPJMPXRDTD-UHFFFAOYSA-M 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 229910001427 strontium ion Inorganic materials 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 125000000565 sulfonamide group Chemical group 0.000 description 1
- 125000001174 sulfone group Chemical group 0.000 description 1
- 125000003375 sulfoxide group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000000101 thioether group Chemical group 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 229910001428 transition metal ion Inorganic materials 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- SZYJELPVAFJOGJ-UHFFFAOYSA-N trimethylamine hydrochloride Chemical compound Cl.CN(C)C SZYJELPVAFJOGJ-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/025—Boronic and borinic acid compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/14—Nitrogen atoms not forming part of a nitro radical
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Diabetes (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US89384207P | 2007-03-08 | 2007-03-08 | |
| US60/893,842 | 2007-03-08 | ||
| US95922607P | 2007-07-12 | 2007-07-12 | |
| US60/959,226 | 2007-07-12 | ||
| US2348708P | 2008-01-25 | 2008-01-25 | |
| US61/023,487 | 2008-01-25 | ||
| US2950608P | 2008-02-18 | 2008-02-18 | |
| US61/029,506 | 2008-02-18 | ||
| PCT/US2008/055927 WO2008109681A2 (en) | 2007-03-08 | 2008-03-05 | Methods and intermediates for synthesis of selective dpp-iv inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2680133A1 true CA2680133A1 (en) | 2008-09-12 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002680133A Abandoned CA2680133A1 (en) | 2007-03-08 | 2008-03-05 | Methods and intermediates for synthesis of selective dpp-iv inhibitors |
Country Status (7)
| Country | Link |
|---|---|
| EP (1) | EP2173709A2 (es) |
| CN (1) | CN101679238A (es) |
| AR (1) | AR065666A1 (es) |
| CA (1) | CA2680133A1 (es) |
| MX (1) | MX2009009575A (es) |
| TW (1) | TW200843784A (es) |
| WO (1) | WO2008109681A2 (es) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20080036125A (ko) | 2005-08-01 | 2008-04-24 | 페노믹스 코포레이션 | 헤테로시클릭 보론산 및 그의 유도체의 제조 방법 |
| CL2007002499A1 (es) * | 2006-08-30 | 2008-03-14 | Phenomix Corp | Sales citrato y tartrato de compuestos derivados de acido pirrolidinilaminoacetilpirrolidinboronico, inhibidores de dpp-iv; metodo de preparacion; forma solida; combinacion farmaceutica, util para el tratamiento de diabetes. |
| UY32030A (es) | 2008-08-06 | 2010-03-26 | Boehringer Ingelheim Int | "tratamiento para diabetes en pacientes inapropiados para terapia con metformina" |
| AU2009281122C1 (en) | 2008-08-15 | 2016-04-21 | Boehringer Ingelheim International Gmbh | Purin derivatives for use in the treatment of fab-related diseases |
| AR074990A1 (es) | 2009-01-07 | 2011-03-02 | Boehringer Ingelheim Int | Tratamiento de diabetes en pacientes con un control glucemico inadecuado a pesar de la terapia con metformina |
| TWI466672B (zh) | 2009-01-29 | 2015-01-01 | Boehringer Ingelheim Int | 小兒科病人糖尿病之治療 |
| MX2011008416A (es) | 2009-02-13 | 2011-09-08 | Boehringer Ingelheim Int | Medicaciones antidiabeticas que comprenden un inhibidor de dpp-4 (linagliptina) opcionalmente en combinacion con otros antidiabeticos. |
| KR102668834B1 (ko) | 2009-11-27 | 2024-05-24 | 베링거 인겔하임 인터내셔날 게엠베하 | 리나글립틴과 같은 ｄｐｐ－ｉｖ 억제제를 사용한 유전자형 검사된 당뇨병 환자의 치료 |
| EP2547339A1 (en) | 2010-03-18 | 2013-01-23 | Boehringer Ingelheim International GmbH | Combination of a gpr119 agonist and the dpp-iv inhibitor linagliptin for use in the treatment of diabetes and related conditions |
| ES2935300T3 (es) | 2010-05-05 | 2023-03-03 | Boehringer Ingelheim Int | Combiterapia |
| KR20230051307A (ko) | 2010-06-24 | 2023-04-17 | 베링거 인겔하임 인터내셔날 게엠베하 | 당뇨병 요법 |
| WO2013174767A1 (en) | 2012-05-24 | 2013-11-28 | Boehringer Ingelheim International Gmbh | A xanthine derivative as dpp -4 inhibitor for use in modifying food intake and regulating food preference |
| CN111533675B (zh) * | 2019-11-29 | 2021-09-28 | 杭州华东医药集团新药研究院有限公司 | 杂环硼酸化合物的杂质及其控制方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7317109B2 (en) * | 2003-11-12 | 2008-01-08 | Phenomix Corporation | Pyrrolidine compounds and methods for selective inhibition of dipeptidyl peptidase-IV |
| KR20080036125A (ko) * | 2005-08-01 | 2008-04-24 | 페노믹스 코포레이션 | 헤테로시클릭 보론산 및 그의 유도체의 제조 방법 |
-
2008
- 2008-03-05 MX MX2009009575A patent/MX2009009575A/es not_active Application Discontinuation
- 2008-03-05 CN CN200880015066A patent/CN101679238A/zh active Pending
- 2008-03-05 WO PCT/US2008/055927 patent/WO2008109681A2/en active Application Filing
- 2008-03-05 CA CA002680133A patent/CA2680133A1/en not_active Abandoned
- 2008-03-05 EP EP08743692A patent/EP2173709A2/en not_active Withdrawn
- 2008-03-07 TW TW097108175A patent/TW200843784A/zh unknown
- 2008-03-07 AR ARP080100973A patent/AR065666A1/es not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| EP2173709A2 (en) | 2010-04-14 |
| MX2009009575A (es) | 2009-11-12 |
| WO2008109681A3 (en) | 2008-11-13 |
| CN101679238A (zh) | 2010-03-24 |
| AR065666A1 (es) | 2009-06-24 |
| TW200843784A (en) | 2008-11-16 |
| WO2008109681A2 (en) | 2008-09-12 |
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