FI107920B - Menetelmä terapeuttisesti käyttökelpoisten fenyylisubstituoitujen 1,4-dihydropyridiinien valmistamiseksi - Google Patents
Menetelmä terapeuttisesti käyttökelpoisten fenyylisubstituoitujen 1,4-dihydropyridiinien valmistamiseksi Download PDFInfo
- Publication number
- FI107920B FI107920B FI945778A FI945778A FI107920B FI 107920 B FI107920 B FI 107920B FI 945778 A FI945778 A FI 945778A FI 945778 A FI945778 A FI 945778A FI 107920 B FI107920 B FI 107920B
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- FI
- Finland
- Prior art keywords
- racemate
- isopropyl
- ch2ch2och3
- och
- cyclopentyl
- Prior art date
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- -1 phenyl-substituted 1,4-dihydropyridines Chemical class 0.000 title claims abstract description 50
- 238000000034 method Methods 0.000 title claims description 23
- 238000002360 preparation method Methods 0.000 title claims description 12
- 230000008569 process Effects 0.000 title claims description 12
- 150000001875 compounds Chemical class 0.000 claims abstract description 57
- 150000002081 enamines Chemical class 0.000 claims abstract 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 83
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 81
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 19
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 16
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 8
- 150000001298 alcohols Chemical class 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- 239000012442 inert solvent Substances 0.000 claims description 6
- 150000001735 carboxylic acids Chemical class 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 229910021529 ammonia Inorganic materials 0.000 claims description 4
- 150000003863 ammonium salts Chemical class 0.000 claims description 4
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 3
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- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 2
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- 238000012360 testing method Methods 0.000 description 15
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- 229910052757 nitrogen Inorganic materials 0.000 description 8
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- FEWLBZQGGXQGSH-UHFFFAOYSA-N 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylic acid Chemical compound CC1=C(C(O)=O)CC(C(O)=O)=C(C)N1 FEWLBZQGGXQGSH-UHFFFAOYSA-N 0.000 description 4
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- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
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- 239000002808 molecular sieve Substances 0.000 description 4
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 4
- UIAGMCDKSXEBJQ-IBGZPJMESA-N 3-o-(2-methoxyethyl) 5-o-propan-2-yl (4s)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COCCOC(=O)C1=C(C)NC(C)=C(C(=O)OC(C)C)[C@H]1C1=CC=CC([N+]([O-])=O)=C1 UIAGMCDKSXEBJQ-IBGZPJMESA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
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- RZJXRRVZIIGCIZ-UHFFFAOYSA-N 4-(3-cyanophenyl)-4-cycloheptyl-1-(2-methoxyethyl)-2,6-dimethylpyridine-3,5-dicarboxylic acid Chemical compound OC(=O)C1=C(C)N(CCOC)C(C)=C(C(O)=O)C1(C=1C=C(C=CC=1)C#N)C1CCCCCC1 RZJXRRVZIIGCIZ-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
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Classifications
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- 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
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D211/84—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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 directly attached to ring carbon atoms
- C07D211/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Neurology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Endocrinology (AREA)
- Physical Education & Sports Medicine (AREA)
- Cardiology (AREA)
- Psychology (AREA)
- Rheumatology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Hospice & Palliative Care (AREA)
- Vascular Medicine (AREA)
- Heart & Thoracic Surgery (AREA)
- Urology & Nephrology (AREA)
- Epidemiology (AREA)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4342196 | 1993-12-10 | ||
| DE4342196A DE4342196A1 (de) | 1993-12-10 | 1993-12-10 | Neue 4-Phenyl-substituierte 1,4-Dihydropyridine |
| DE4342194 | 1993-12-10 | ||
| DE4342194A DE4342194A1 (de) | 1993-12-10 | 1993-12-10 | Halogen-phenyl-substituierte 1,4-Dihydropyridine |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI945778A0 FI945778A0 (fi) | 1994-12-08 |
| FI945778L FI945778L (fi) | 1995-06-11 |
| FI107920B true FI107920B (fi) | 2001-10-31 |
Family
ID=25931955
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI945778A FI107920B (fi) | 1993-12-10 | 1994-12-08 | Menetelmä terapeuttisesti käyttökelpoisten fenyylisubstituoitujen 1,4-dihydropyridiinien valmistamiseksi |
Country Status (25)
| Country | Link |
|---|---|
| US (2) | US6239155B1 (cs) |
| EP (1) | EP0657432B1 (cs) |
| JP (3) | JP3959127B2 (cs) |
| KR (1) | KR100355973B1 (cs) |
| CN (1) | CN1109875A (cs) |
| AT (1) | ATE234286T1 (cs) |
| AU (1) | AU696925B2 (cs) |
| CA (1) | CA2137623C (cs) |
| CZ (1) | CZ288393B6 (cs) |
| DE (1) | DE59410255D1 (cs) |
| DK (1) | DK0657432T3 (cs) |
| ES (1) | ES2193148T3 (cs) |
| FI (1) | FI107920B (cs) |
| HU (1) | HU224442B1 (cs) |
| IL (1) | IL111923A (cs) |
| MX (1) | MX9409573A (cs) |
| MY (1) | MY117887A (cs) |
| NO (1) | NO303630B1 (cs) |
| NZ (1) | NZ270085A (cs) |
| PL (1) | PL306158A1 (cs) |
| PT (1) | PT657432E (cs) |
| RU (1) | RU2155751C2 (cs) |
| SK (1) | SK283409B6 (cs) |
| TW (1) | TW300218B (cs) |
| UA (1) | UA37211C2 (cs) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE59410255D1 (de) * | 1993-12-10 | 2003-04-17 | Bayer Ag | Phenyl-substituierte 1,4-Dihydropyridine mit cerebraler Aktivität |
| LV12200B (lv) * | 1997-07-03 | 1999-04-20 | Gun�rs DUBURS | Antidiabētisks līdzeklis |
| WO2005023768A1 (en) * | 2003-09-11 | 2005-03-17 | Sanmar Speciality Chemicals Limited | An improved process for the preparation of pure nisoldipine |
| WO2009078934A1 (en) * | 2007-12-14 | 2009-06-25 | Merck & Co., Inc. | Mineralocorticoid receptor modulators |
Family Cites Families (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1963188A1 (de) * | 1969-12-17 | 1971-06-24 | Bayer Ag | Neue Cyanphenyl-1,4-dihydropyridinderivate |
| DE1963186C3 (de) * | 1969-12-17 | 1979-02-15 | Bayer Ag, 5090 Leverkusen | Schwefelhaltige 1,4-Dihydropyridin-33-dicarbonsäureester |
| DE2117573C3 (de) * | 1971-04-10 | 1978-07-27 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von unsymmetrischen l,4-Dihydropyridin-3,5dicarbonsäureestern, sowie ihre Verwendung als Arzneimittel |
| DE2117571C3 (de) * | 1971-04-10 | 1979-10-11 | Bayer Ag, 5090 Leverkusen | Unsymmetrische 1,4-Dihydropyridin-33-dicarbonsäureester, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Arzneimittel |
| DE2117572C3 (de) * | 1971-04-10 | 1980-03-20 | Bayer Ag, 5090 Leverkusen | Unsymmetrische 1,4-Dihydropyridin ^-dicarbonsäureester, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Arzneimittel |
| US3932646A (en) * | 1971-04-10 | 1976-01-13 | Farbenfabriken Bayer Ag | Pharmaceutical compositions containing unsymmetrical esters of 1,4-dihydropyridine 3,5-dicarboxylate |
| GB1425729A (en) * | 1973-06-12 | 1976-02-18 | Smith Kline French Lab | 1,4-dihydropyridine compounds |
| US3966946A (en) * | 1973-06-12 | 1976-06-29 | Smith Kline & French Laboratories Limited | 1,4-Dihydropyridine compounds in treating hypertension |
| DE2815578C2 (de) * | 1978-04-11 | 1986-01-16 | Bayer Ag, 5090 Leverkusen | Neue pharmazeutische Verwendung von Nimodipin |
| SE429652B (sv) * | 1978-06-30 | 1983-09-19 | Haessle Ab | 2.6-dimetyl-4-(2.3-diklorfenyl)-1.4-dihydropyridin-3.5-dikarboxylsyra-3-metylester-5-etylester |
| DE2935451A1 (de) | 1979-09-01 | 1981-03-19 | Bayer Ag, 5090 Leverkusen | Optisch aktive 1,4-dihydropyridine, verfahren zu ihrer herstellung und ihre verwendung als arneimittel |
| DE3018259A1 (de) * | 1980-05-13 | 1981-11-19 | Bayer Ag, 5090 Leverkusen | 1,4-dihydropyridine mit unterschiedlichen substituenten in 2- und 6-position, verfahren zu ihrer herstellung und ihre verwendung in arzneimitteln |
| DE3208628A1 (de) | 1982-03-10 | 1983-09-22 | Bayer Ag, 5090 Leverkusen | Neue verbindungen, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| DE3209274A1 (de) * | 1982-03-13 | 1983-09-15 | Bayer Ag, 5090 Leverkusen | Pyridincarbonsaeureester, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| DE3209276A1 (de) * | 1982-03-13 | 1983-09-15 | Bayer Ag, 5090 Leverkusen | Arzneimittel mit antihypoxischer und ischaemie-protektiver wirkung |
| DE3239273A1 (de) | 1982-10-23 | 1984-04-26 | Bayer Ag, 5090 Leverkusen | Tetrahydropyridine, verfahren zu ihrer herstellung sowie ihre verwendung in arzneimitteln |
| JPS6094963A (ja) * | 1983-10-31 | 1985-05-28 | Teijin Ltd | １，４−ジヒドロピリジン−３，５−ジカルボン酸ジエステル誘導体及びその製造法 |
| US5137889A (en) | 1983-12-02 | 1992-08-11 | Otsuka Pharmaceutical Co., Ltd. | Dihydropyridine derivatives and process for preparing the same |
| DE3423105A1 (de) * | 1984-06-22 | 1986-01-02 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung optisch aktiver 1,4-dihydropyridine |
| DE3514865A1 (de) * | 1985-04-25 | 1986-11-06 | Bayer Ag, 5090 Leverkusen | 1,4-dihydropyridin-derivate, verfahren zu ihrer herstellung und ihre verwendung in arzneimitteln |
| DE3544211A1 (de) * | 1985-12-13 | 1987-06-19 | Bayer Ag | Neue, fluorhaltige 1,4-dihydropyridine, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| IT1204459B (it) * | 1986-02-20 | 1989-03-01 | Glaxo Spa | Derivati eterociclici |
| DE3629545A1 (de) * | 1986-08-30 | 1988-03-10 | Bayer Ag | Dihydropyridinverbindungen, verfahren zu ihrer herstellung und ihre verwendung |
| DE3718398A1 (de) | 1987-06-02 | 1988-12-22 | Troponwerke Gmbh & Co Kg | Neue kombinationspraeparate mit antidepressiver wirkung |
| US5114946A (en) | 1987-06-12 | 1992-05-19 | American Cyanamid Company | Transdermal delivery of pharmaceuticals |
| NO890046L (no) * | 1988-01-20 | 1989-07-21 | Bayer Ag | Disubstituerte pyridiner. |
| DE3806277A1 (de) | 1988-02-27 | 1989-09-07 | Troponwerke Gmbh & Co Kg | Verwendung von 1,4-dihydropyridin-derivaten |
| KR940003492B1 (ko) * | 1988-10-27 | 1994-04-23 | 주식회사 유한양행 | 1,4-디하이드로피리딘유도체 및 그의 제조방법 |
| JPH02149563A (ja) * | 1988-11-30 | 1990-06-08 | Nisshin Flour Milling Co Ltd | ２−ハロエトキシカルボニル基を含有する１，４−ジヒドロピリジン誘導体の製造法 |
| JPH03157369A (ja) * | 1989-08-02 | 1991-07-05 | Kaken Pharmaceut Co Ltd | １，４―ジヒドロピリジン誘導体、その製造法およびそれを有効成分とする脳機能改善剤 |
| DE4011695A1 (de) * | 1990-04-11 | 1991-10-17 | Bayer Ag | Verwendung von n-alkylierten 1,4-dihydropyridindicarbonsaeureestern als arzneimittel, neue verbindungen und verfahren zu ihrer herstellung |
| DE4125271A1 (de) * | 1991-07-31 | 1993-02-11 | Bayer Ag | Neue n-alkylierte 1,4-dihydropyridindicarbonsaeureester |
| WO1993006082A1 (en) * | 1991-09-13 | 1993-04-01 | Merck & Co., Inc. | Process for the preparation of 4-substituted-1,4-dihydropyridines |
| US5310917A (en) * | 1991-09-13 | 1994-05-10 | Merck & Co., Inc. | Process for the preparation of 4-substituted-1,4-dihydropydrines |
| ATE146788T1 (de) * | 1992-10-30 | 1997-01-15 | Bayer Ag | 4-heterocyclophenyl substituierte dihydropyridine |
| DE59410255D1 (de) * | 1993-12-10 | 2003-04-17 | Bayer Ag | Phenyl-substituierte 1,4-Dihydropyridine mit cerebraler Aktivität |
-
1994
- 1994-11-28 DE DE59410255T patent/DE59410255D1/de not_active Expired - Lifetime
- 1994-11-28 AT AT94118677T patent/ATE234286T1/de active
- 1994-11-28 PT PT94118677T patent/PT657432E/pt unknown
- 1994-11-28 ES ES94118677T patent/ES2193148T3/es not_active Expired - Lifetime
- 1994-11-28 DK DK94118677T patent/DK0657432T3/da active
- 1994-11-28 EP EP94118677A patent/EP0657432B1/de not_active Expired - Lifetime
- 1994-12-02 US US08/348,399 patent/US6239155B1/en not_active Expired - Fee Related
- 1994-12-07 PL PL94306158A patent/PL306158A1/xx unknown
- 1994-12-07 JP JP33029694A patent/JP3959127B2/ja not_active Expired - Fee Related
- 1994-12-07 IL IL11192394A patent/IL111923A/xx not_active IP Right Cessation
- 1994-12-07 NZ NZ270085A patent/NZ270085A/en unknown
- 1994-12-08 UA UA94129153A patent/UA37211C2/uk unknown
- 1994-12-08 AU AU80305/94A patent/AU696925B2/en not_active Ceased
- 1994-12-08 FI FI945778A patent/FI107920B/fi not_active IP Right Cessation
- 1994-12-08 CA CA002137623A patent/CA2137623C/en not_active Expired - Fee Related
- 1994-12-09 SK SK1531-94A patent/SK283409B6/sk not_active IP Right Cessation
- 1994-12-09 MY MYPI94003294A patent/MY117887A/en unknown
- 1994-12-09 NO NO944788A patent/NO303630B1/no not_active IP Right Cessation
- 1994-12-09 CN CN94112897A patent/CN1109875A/zh active Pending
- 1994-12-09 MX MX9409573A patent/MX9409573A/es unknown
- 1994-12-09 KR KR1019940033435A patent/KR100355973B1/ko not_active Expired - Fee Related
- 1994-12-09 RU RU94043812/04A patent/RU2155751C2/ru not_active IP Right Cessation
- 1994-12-09 HU HU9403552A patent/HU224442B1/hu not_active IP Right Cessation
- 1994-12-09 CZ CZ19943109A patent/CZ288393B6/cs not_active IP Right Cessation
- 1994-12-23 TW TW083112077A patent/TW300218B/zh not_active IP Right Cessation
-
2001
- 2001-02-12 US US09/781,516 patent/US6630494B2/en not_active Expired - Fee Related
-
2006
- 2006-11-22 JP JP2006315990A patent/JP2007084567A/ja active Pending
- 2006-11-22 JP JP2006315995A patent/JP2007091750A/ja active Pending
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PC | Transfer of assignment of patent |
Owner name: BAYER SCHERING PHARMA AKTIENGESELLSCHAFT Free format text: BAYER SCHERING PHARMA AKTIENGESELLSCHAFT |
|
| PC | Transfer of assignment of patent |
Owner name: BAYER SCHERING PHARMA AKTIENGESELLSCHAFT Free format text: BAYER SCHERING PHARMA AKTIENGESELLSCHAFT |
|
| MM | Patent lapsed |