CH661272A5 - Derives de 4,7-dihydropyrazolo (3,4-b)pyridine et composition pharmaceutique a action anti-hypertensive et de vasodilatation coronaire les renfermant. - Google Patents
Derives de 4,7-dihydropyrazolo (3,4-b)pyridine et composition pharmaceutique a action anti-hypertensive et de vasodilatation coronaire les renfermant. Download PDFInfo
- Publication number
- CH661272A5 CH661272A5 CH4198/84A CH419884A CH661272A5 CH 661272 A5 CH661272 A5 CH 661272A5 CH 4198/84 A CH4198/84 A CH 4198/84A CH 419884 A CH419884 A CH 419884A CH 661272 A5 CH661272 A5 CH 661272A5
- Authority
- CH
- Switzerland
- Prior art keywords
- pyridine
- dimethyl
- methyl
- carboxylate
- nitrophenyl
- Prior art date
Links
- 230000024883 vasodilation Effects 0.000 title description 8
- 230000003276 anti-hypertensive effect Effects 0.000 title description 7
- 239000008194 pharmaceutical composition Substances 0.000 title description 2
- -1 1-methylpyrrolidinyl Chemical group 0.000 description 45
- 150000001875 compounds Chemical class 0.000 description 36
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- 238000006243 chemical reaction Methods 0.000 description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
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- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
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- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
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- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
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- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000010253 intravenous injection Methods 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
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)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
- 239000008101 lactose Substances 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- 235000012245 magnesium oxide Nutrition 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- QFXVTBZISYKFSV-UHFFFAOYSA-N methyl 1,6-dimethyl-3-(1-methylpyrrolidin-2-yl)-4-(3-nitrophenyl)-4,7-dihydropyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound COC(=O)C1=C(C)Nc2c(C1c1cccc(c1)[N+]([O-])=O)c(nn2C)C1CCCN1C QFXVTBZISYKFSV-UHFFFAOYSA-N 0.000 description 1
- MKXAVKKSCKRRFM-UHFFFAOYSA-N methyl 1,6-dimethyl-4-(3-nitrophenyl)-3-(3-oxocyclohexyl)-4,7-dihydropyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound COC(=O)C1=C(C)NC(N(N=C2C3CC(=O)CCC3)C)=C2C1C1=CC=CC([N+]([O-])=O)=C1 MKXAVKKSCKRRFM-UHFFFAOYSA-N 0.000 description 1
- ZCKDIPGUBKVYEB-UHFFFAOYSA-N methyl 3-(4-chlorobutyl)-1,6-dimethyl-4-(3-nitrophenyl)-4,7-dihydropyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound COC(=O)C1=C(C)NC(N(N=C2CCCCCl)C)=C2C1C1=CC=CC([N+]([O-])=O)=C1 ZCKDIPGUBKVYEB-UHFFFAOYSA-N 0.000 description 1
- SWBCKEBUIJJINO-UHFFFAOYSA-N methyl 3-cyclopent-3-en-1-yl-1,6-dimethyl-4-(3-nitrophenyl)-4,7-dihydropyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound COC(=O)C1=C(C)NC(N(N=C2C3CC=CC3)C)=C2C1C1=CC=CC([N+]([O-])=O)=C1 SWBCKEBUIJJINO-UHFFFAOYSA-N 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical compound CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 description 1
- 125000006501 nitrophenyl group Chemical group 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 125000005429 oxyalkyl group Chemical group 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 230000010412 perfusion Effects 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 238000011699 spontaneously hypertensive rat Methods 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000025033 vasoconstriction Effects 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three 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
- C07D231/38—Nitrogen atoms
-
- 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
-
- 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
- A61P9/06—Antiarrhythmics
-
- 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
- A61P9/08—Vasodilators for multiple indications
-
- 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58166258A JPS6056979A (ja) | 1983-09-08 | 1983-09-08 | ４，７−ジヒドロピラゾロ〔３，４−ｂ〕ピリジン誘導体およびその製造法 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH661272A5 true CH661272A5 (fr) | 1987-07-15 |
Family
ID=15828039
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH4198/84A CH661272A5 (fr) | 1983-09-08 | 1984-09-03 | Derives de 4,7-dihydropyrazolo (3,4-b)pyridine et composition pharmaceutique a action anti-hypertensive et de vasodilatation coronaire les renfermant. |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4562256A (en, 2012) |
| JP (1) | JPS6056979A (en, 2012) |
| KR (1) | KR910002838B1 (en, 2012) |
| CH (1) | CH661272A5 (en, 2012) |
| DE (1) | DE3432985A1 (en, 2012) |
| FR (1) | FR2551756B1 (en, 2012) |
| GB (1) | GB2146326B (en, 2012) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4873334A (en) * | 1982-10-05 | 1989-10-10 | Shionogi & Co., Ltd. | 4,7-dihydropyrazolo(3,4-b) pyridine derivatives |
| JPS6210087A (ja) * | 1985-07-03 | 1987-01-19 | Shionogi & Co Ltd | ４，７−ジヒドロチエノ〔２，３−ｂ〕ピリジン誘導体，その製造法および循環器系疾患治療剤 |
| US6977262B2 (en) | 2001-02-02 | 2005-12-20 | Mitsubishi Pharma Corporation | Dihydropyrazolopyridine compounds and pharmaceutical use thereof |
| CA2437215A1 (en) * | 2001-02-02 | 2002-08-15 | Mitsubishi Pharma Corporation | Dihydropyrazolopyridine compounds and pharmaceutical use thereof |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3857849A (en) * | 1973-02-28 | 1974-12-31 | Bayer Ag | 2-amino-1,4-dihydropyridine derivatives |
| JPS5965089A (ja) * | 1982-10-05 | 1984-04-13 | Shionogi & Co Ltd | ジヒドロピラゾロ〔３，４−ｂ〕ピリジン誘導体およびその製造法 |
| JPS60197685A (ja) * | 1984-03-19 | 1985-10-07 | Shionogi & Co Ltd | ４，７―ジヒドロピラゾロ［３，４―ｂ］ピリジン誘導体とその製造法 |
| GR79111B (en, 2012) * | 1982-12-20 | 1984-10-02 | Lepetit Spa |
-
1983
- 1983-09-08 JP JP58166258A patent/JPS6056979A/ja active Granted
-
1984
- 1984-08-17 US US06/641,822 patent/US4562256A/en not_active Expired - Fee Related
- 1984-08-28 GB GB08421763A patent/GB2146326B/en not_active Expired
- 1984-09-03 CH CH4198/84A patent/CH661272A5/fr not_active IP Right Cessation
- 1984-09-05 FR FR8413674A patent/FR2551756B1/fr not_active Expired
- 1984-09-05 KR KR1019840005440A patent/KR910002838B1/ko not_active Expired
- 1984-09-07 DE DE19843432985 patent/DE3432985A1/de active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| FR2551756B1 (fr) | 1987-10-02 |
| GB8421763D0 (en) | 1984-10-03 |
| JPH0437833B2 (en, 2012) | 1992-06-22 |
| US4562256A (en) | 1985-12-31 |
| JPS6056979A (ja) | 1985-04-02 |
| DE3432985C2 (en, 2012) | 1993-09-16 |
| FR2551756A1 (fr) | 1985-03-15 |
| GB2146326B (en) | 1987-01-14 |
| KR850002095A (ko) | 1985-05-06 |
| GB2146326A (en) | 1985-04-17 |
| KR910002838B1 (ko) | 1991-05-06 |
| DE3432985A1 (de) | 1985-03-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |