RU2018109763A - Способ получения метаболитов (4s)-и (4r)-4-(4-циано-2-метоксифенил)-5-этокси-2,8-диметил-1,4-дигидро-1,6-нафтиридин-3-карбоксамида и их применение - Google Patents
Способ получения метаболитов (4s)-и (4r)-4-(4-циано-2-метоксифенил)-5-этокси-2,8-диметил-1,4-дигидро-1,6-нафтиридин-3-карбоксамида и их применение Download PDFInfo
- Publication number
- RU2018109763A RU2018109763A RU2018109763A RU2018109763A RU2018109763A RU 2018109763 A RU2018109763 A RU 2018109763A RU 2018109763 A RU2018109763 A RU 2018109763A RU 2018109763 A RU2018109763 A RU 2018109763A RU 2018109763 A RU2018109763 A RU 2018109763A
- Authority
- RU
- Russia
- Prior art keywords
- formulas
- naphthyridine
- carboxamide
- methoxyphenyl
- dihydro
- Prior art date
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/4375—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a six-membered ring having nitrogen as a ring heteroatom, e.g. quinolizines, naphthyridines, berberine, vincamine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Cardiology (AREA)
- Urology & Nephrology (AREA)
- Heart & Thoracic Surgery (AREA)
- Vascular Medicine (AREA)
- Hospice & Palliative Care (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Claims (22)
-
- 2. Способ получения соединений формул М1а (S) и M1b (R),
-
,
- отличающийся тем, что соединение формулы rac М1
-
- получают в результате окисления соединения формулы rac (I),
-
- и этот рацемат разделяют с помощью хроматографических методов на хиральной фазе на энантиомеры формул М1а (S) и M1b (R).
- 3. Способ получения соединений формул М2а (S) и M2b (R),
-
,
- отличающийся тем, что соединение формулы rac М2
-
- получают в результате селективного гидроксилирования метильной группы соединения формулы rac М1,
-
- и этот рацемат разделяют с помощью хроматографических методов на хиральной фазе на энантиомеры формул М2а (S) и M2b (R).
- 4. Способ получения соединений формул М3а (S) и M3b (R),
-
,
- отличающийся тем, что соединение формулы rac М3
-
- получают в результате окисления бензилового спирта соединения формулы гас М2,
-
- и этот рацемат разделяют с помощью хроматографических методов на хиральной фазе на энантиомеры формул М3а (S) и M3b (R).
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP15182044.6 | 2015-08-21 | ||
| EP15182044 | 2015-08-21 | ||
| PCT/EP2016/069329 WO2017032627A1 (de) | 2015-08-21 | 2016-08-15 | Verfahren zur herstellung der metaboliten von (4s) und (4r)- 4-(4-cyano-2-methoxyphenyl)-5-ethoxy-2,8-dimethyl-1,4-dihydro-1,6-naphthyridin-3-carboxamid und deren verwendung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU2018109763A true RU2018109763A (ru) | 2019-09-23 |
Family
ID=54007552
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2018109763A RU2018109763A (ru) | 2015-08-21 | 2016-08-15 | Способ получения метаболитов (4s)-и (4r)-4-(4-циано-2-метоксифенил)-5-этокси-2,8-диметил-1,4-дигидро-1,6-нафтиридин-3-карбоксамида и их применение |
Country Status (17)
| Country | Link |
|---|---|
| US (2) | US20180237414A1 (ru) |
| EP (1) | EP3337799A1 (ru) |
| JP (1) | JP2018523698A (ru) |
| KR (1) | KR20180042324A (ru) |
| CN (1) | CN108473488A (ru) |
| AU (1) | AU2016312880A1 (ru) |
| BR (1) | BR112018003379A2 (ru) |
| CA (1) | CA2995887A1 (ru) |
| CL (1) | CL2018000428A1 (ru) |
| CO (1) | CO2018001755A2 (ru) |
| IL (1) | IL257536A (ru) |
| MX (1) | MX2018002105A (ru) |
| PE (1) | PE20180553A1 (ru) |
| RU (1) | RU2018109763A (ru) |
| SG (1) | SG11201801377XA (ru) |
| WO (1) | WO2017032627A1 (ru) |
| ZA (1) | ZA201801865B (ru) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PE20221420A1 (es) * | 2019-10-17 | 2022-09-20 | Bayer Ag | Procedimiento fotoquimico para la preparacion de (4r,4s)-4-(4-ciano-2-metoxifenil)-5-etoxi-2,8-dimetil-1,4-dihidro-1,6-naftiridin-3-carboxamida |
| JOP20220148A1 (ar) * | 2019-10-17 | 2023-01-30 | Bayer Ag | عملية لانتاج استرات أسيلوكسي مثيل من حمض (4s)- (4-سيانو-2-ميثوكسي فنيل)-5-ايثوكسي-2، 8-ثنائي مثيل-1، 4-ثنائي هيدرو-1، 6-نفثيريدين-3-كربوكسيليك |
| WO2021254896A1 (en) | 2020-06-16 | 2021-12-23 | Bayer Aktiengesellschaft | Process for preparing (4s)-4-(4-cyano-2-methoxyphenyl)-5-ethoxy-2,8-dimethyl-1,4-dihydro-1,6-naphthyridine-3-carboxamide enabled by a catalytic asymmetric hantzsch ester reduction |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1028754C (zh) * | 1988-07-12 | 1995-06-07 | 武田药品工业株式会社 | 喹啉衍生物的制备方法 |
| AU692601B2 (en) * | 1994-10-27 | 1998-06-11 | Sumitomo Chemical Company, Limited | Process for producing N-(1-(2,4-dichlorophenyl)ethyl)-2- cyano-3,3-dimethylbutanamide |
| CN1914173A (zh) * | 2003-12-12 | 2007-02-14 | 惠氏公司 | 用于治疗心血管疾病的喹啉化合物 |
| DE102007009494A1 (de) * | 2007-02-27 | 2008-08-28 | Bayer Healthcare Ag | Substituierte 4-Aryl-1, 4-dihydro-1,6-naphthyridinamide und ihre Verwendung |
-
2016
- 2016-08-15 EP EP16750868.8A patent/EP3337799A1/de not_active Withdrawn
- 2016-08-15 CA CA2995887A patent/CA2995887A1/en not_active Abandoned
- 2016-08-15 MX MX2018002105A patent/MX2018002105A/es unknown
- 2016-08-15 AU AU2016312880A patent/AU2016312880A1/en not_active Abandoned
- 2016-08-15 BR BR112018003379-0A patent/BR112018003379A2/pt not_active Application Discontinuation
- 2016-08-15 KR KR1020187007625A patent/KR20180042324A/ko unknown
- 2016-08-15 CN CN201680048529.8A patent/CN108473488A/zh active Pending
- 2016-08-15 WO PCT/EP2016/069329 patent/WO2017032627A1/de active Application Filing
- 2016-08-15 US US15/753,697 patent/US20180237414A1/en not_active Abandoned
- 2016-08-15 RU RU2018109763A patent/RU2018109763A/ru not_active Application Discontinuation
- 2016-08-15 JP JP2018509761A patent/JP2018523698A/ja active Pending
- 2016-08-15 PE PE2018000247A patent/PE20180553A1/es unknown
- 2016-08-15 SG SG11201801377XA patent/SG11201801377XA/en unknown
-
2018
- 2018-02-14 IL IL257536A patent/IL257536A/en unknown
- 2018-02-16 CL CL2018000428A patent/CL2018000428A1/es unknown
- 2018-02-21 CO CONC2018/0001755A patent/CO2018001755A2/es unknown
- 2018-03-20 ZA ZA201801865A patent/ZA201801865B/en unknown
-
2020
- 2020-10-14 US US17/070,371 patent/US20210024490A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| WO2017032627A9 (de) | 2018-04-05 |
| CA2995887A1 (en) | 2017-03-02 |
| SG11201801377XA (en) | 2018-05-30 |
| US20180237414A1 (en) | 2018-08-23 |
| EP3337799A1 (de) | 2018-06-27 |
| AU2016312880A1 (en) | 2018-03-08 |
| IL257536A (en) | 2018-04-30 |
| AU2016312880A9 (en) | 2019-07-25 |
| CO2018001755A2 (es) | 2018-02-28 |
| WO2017032627A1 (de) | 2017-03-02 |
| ZA201801865B (en) | 2019-11-27 |
| PE20180553A1 (es) | 2018-04-02 |
| BR112018003379A2 (pt) | 2018-09-18 |
| US20210024490A1 (en) | 2021-01-28 |
| CL2018000428A1 (es) | 2018-07-20 |
| KR20180042324A (ko) | 2018-04-25 |
| JP2018523698A (ja) | 2018-08-23 |
| MX2018002105A (es) | 2018-06-15 |
| CN108473488A (zh) | 2018-08-31 |
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| Date | Code | Title | Description |
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| FA93 | Acknowledgement of application withdrawn (no request for examination) |
Effective date: 20190816 |