DE3432985A1 - 4,7-dihydropyrazolo(3,4-b)pyridin-derivate und ihre verwendung zur behandlung von erkrankungen des kreislaufsystems - Google Patents
4,7-dihydropyrazolo(3,4-b)pyridin-derivate und ihre verwendung zur behandlung von erkrankungen des kreislaufsystemsInfo
- Publication number
- DE3432985A1 DE3432985A1 DE19843432985 DE3432985A DE3432985A1 DE 3432985 A1 DE3432985 A1 DE 3432985A1 DE 19843432985 DE19843432985 DE 19843432985 DE 3432985 A DE3432985 A DE 3432985A DE 3432985 A1 DE3432985 A1 DE 3432985A1
- Authority
- DE
- Germany
- Prior art keywords
- deep
- dihydropyrazolo
- pyridine
- dimethyl
- nitrophenyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
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- 210000004556 brain Anatomy 0.000 claims abstract description 4
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- -1 1-methylpyrrolidinyl Chemical group 0.000 claims description 32
- 238000000034 method Methods 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 4
- MJZXNRLRDDZKQO-UHFFFAOYSA-N methyl 3-(cyclopentylmethyl)-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=C2CC3CCCC3)C)=C2C1C1=CC=CC([N+]([O-])=O)=C1 MJZXNRLRDDZKQO-UHFFFAOYSA-N 0.000 claims description 3
- WITBTLNUQKCVHQ-UHFFFAOYSA-N methyl 3-cyclohex-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=CCC3)C)=C2C1C1=CC=CC([N+]([O-])=O)=C1 WITBTLNUQKCVHQ-UHFFFAOYSA-N 0.000 claims description 3
- YNBADRVTZLEFNH-UHFFFAOYSA-N methyl nicotinate Chemical compound COC(=O)C1=CC=CN=C1 YNBADRVTZLEFNH-UHFFFAOYSA-N 0.000 claims description 3
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 2
- 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 claims description 2
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- PYAYHRBYGXEUCT-UHFFFAOYSA-N 4-nitro-3-oxo-5-phenylpent-4-enoic acid Chemical class OC(=O)CC(=O)C([N+]([O-])=O)=CC1=CC=CC=C1 PYAYHRBYGXEUCT-UHFFFAOYSA-N 0.000 abstract 1
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- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 150000004729 acetoacetic acid derivatives Chemical class 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
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- 229910052783 alkali metal Inorganic materials 0.000 description 2
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- NDBWNKLVQBRPKV-UHFFFAOYSA-N methyl 1,6-dimethyl-4-(3-nitrophenyl)-3-(4-oxocyclohexyl)-4,7-dihydropyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound COC(=O)C1=C(C)NC(N(N=C2C3CCC(=O)CC3)C)=C2C1C1=CC=CC([N+]([O-])=O)=C1 NDBWNKLVQBRPKV-UHFFFAOYSA-N 0.000 description 2
- KYDQYINOTRDNQN-UHFFFAOYSA-N methyl 3-(1,3-dithiolan-2-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=C2C3SCCS3)C)=C2C1C1=CC=CC([N+]([O-])=O)=C1 KYDQYINOTRDNQN-UHFFFAOYSA-N 0.000 description 2
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- 239000007924 injection Substances 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
- 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
- 238000004519 manufacturing process Methods 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
- JJPSGUGLBKQZLX-UHFFFAOYSA-N methyl 1,6-dimethyl-4-(3-nitrophenyl)-3-(pyrrolidin-1-ylmethyl)-4,7-dihydropyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound COC(=O)C1=C(C)Nc2c(C1c1cccc(c1)[N+]([O-])=O)c(CN1CCCC1)nn2C JJPSGUGLBKQZLX-UHFFFAOYSA-N 0.000 description 1
- VKQFCGNPDRICFG-UHFFFAOYSA-N methyl 2-methylpropyl 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCC(C)C)C1C1=CC=CC=C1[N+]([O-])=O VKQFCGNPDRICFG-UHFFFAOYSA-N 0.000 description 1
- IWZVVPBUORTIKI-UHFFFAOYSA-N methyl 3-(1,4-dioxaspiro[4.5]decan-7-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=C2C3CC4(CCC3)OCCO4)C)=C2C1C1=CC=CC([N+]([O-])=O)=C1 IWZVVPBUORTIKI-UHFFFAOYSA-N 0.000 description 1
- QIOIUEBNSCHVNV-UHFFFAOYSA-N methyl 3-(1-adamantyl)-1,6-dimethyl-4-(3-nitrophenyl)-4,7-dihydropyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound COC(=O)C=1C(C2=C(NC=1C)N(N=C2C12CC3CC(CC(C1)C3)C2)C)C1=CC(=CC=C1)[N+](=O)[O-] QIOIUEBNSCHVNV-UHFFFAOYSA-N 0.000 description 1
- PHOAUAZWOGESEV-UHFFFAOYSA-N methyl 3-(2-methoxyethyl)-1,6-dimethyl-4-(3-nitrophenyl)-4,7-dihydropyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound C1=2C(CCOC)=NN(C)C=2NC(C)=C(C(=O)OC)C1C1=CC=CC([N+]([O-])=O)=C1 PHOAUAZWOGESEV-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
- WQVFVXSGUNHVQT-UHFFFAOYSA-N methyl 3-(cyclopentylmethyl)-1,6-dimethyl-4-(2-nitrophenyl)-4,7-dihydropyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound COC(=O)C1=C(C)NC(N(N=C2CC3CCCC3)C)=C2C1C1=CC=CC=C1[N+]([O-])=O WQVFVXSGUNHVQT-UHFFFAOYSA-N 0.000 description 1
- JYSMBWKUAAZAHE-UHFFFAOYSA-N methyl 3-(cyclopentyloxymethyl)-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=C2COC3CCCC3)C)=C2C1C1=CC=CC([N+]([O-])=O)=C1 JYSMBWKUAAZAHE-UHFFFAOYSA-N 0.000 description 1
- YWGPAZRVYQWDGU-UHFFFAOYSA-N methyl 3-but-3-enyl-1,6-dimethyl-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(CCC=C)nn2C YWGPAZRVYQWDGU-UHFFFAOYSA-N 0.000 description 1
- WINQASRCIOATLX-UHFFFAOYSA-N methyl 3-cyclohex-3-en-1-yl-1,6-dimethyl-4-(2-nitrophenyl)-4,7-dihydropyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound COC(=O)C1=C(C)NC(N(N=C2C3CC=CCC3)C)=C2C1C1=CC=CC=C1[N+]([O-])=O WINQASRCIOATLX-UHFFFAOYSA-N 0.000 description 1
- ALHKQDDIIXDSMQ-UHFFFAOYSA-N methyl 3-cyclopentyl-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=C2C3CCCC3)C)=C2C1C1=CC=CC([N+]([O-])=O)=C1 ALHKQDDIIXDSMQ-UHFFFAOYSA-N 0.000 description 1
- GKSMNBZFSFFBDM-UHFFFAOYSA-N methyl 5-(3-nitrophenyl)-3-oxopent-4-enoate Chemical compound COC(=O)CC(=O)C=CC1=CC=CC([N+]([O-])=O)=C1 GKSMNBZFSFFBDM-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 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
- 150000007522 mineralic acids Chemical class 0.000 description 1
- HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical compound CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 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
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 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
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000007017 scission Effects 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
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 230000002269 spontaneous effect Effects 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
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000003826 tablet Substances 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
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 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
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 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
- 238000005303 weighing Methods 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)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (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 (2)
| Publication Number | Publication Date |
|---|---|
| DE3432985A1 true DE3432985A1 (de) | 1985-03-28 |
| DE3432985C2 DE3432985C2 (enExample) | 1993-09-16 |
Family
ID=15828039
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19843432985 Granted DE3432985A1 (de) | 1983-09-08 | 1984-09-07 | 4,7-dihydropyrazolo(3,4-b)pyridin-derivate und ihre verwendung zur behandlung von erkrankungen des kreislaufsystems |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4562256A (enExample) |
| JP (1) | JPS6056979A (enExample) |
| KR (1) | KR910002838B1 (enExample) |
| CH (1) | CH661272A5 (enExample) |
| DE (1) | DE3432985A1 (enExample) |
| FR (1) | FR2551756B1 (enExample) |
| GB (1) | GB2146326B (enExample) |
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 |
| JP2005501800A (ja) * | 2001-02-02 | 2005-01-20 | 三菱ウェルファーマ株式会社 | ジヒドロピラゾロピリジン化合物およびその医薬用途 |
| US6977262B2 (en) | 2001-02-02 | 2005-12-20 | Mitsubishi Pharma Corporation | Dihydropyrazolopyridine compounds and pharmaceutical use thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0107619A1 (en) * | 1982-10-05 | 1984-05-02 | Shionogi & Co., Ltd. | Dihydropyrazolo(3,4-b)pyridine derivatives and production thereof |
| EP0114273A1 (en) * | 1982-12-20 | 1984-08-01 | GRUPPO LEPETIT S.p.A. | New pharmacologically active pyrazolopyridines |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3857849A (en) * | 1973-02-28 | 1974-12-31 | Bayer Ag | 2-amino-1,4-dihydropyridine derivatives |
| 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 |
-
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
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0107619A1 (en) * | 1982-10-05 | 1984-05-02 | Shionogi & Co., Ltd. | Dihydropyrazolo(3,4-b)pyridine derivatives and production thereof |
| EP0114273A1 (en) * | 1982-12-20 | 1984-08-01 | GRUPPO LEPETIT S.p.A. | New pharmacologically active pyrazolopyridines |
Also Published As
| Publication number | Publication date |
|---|---|
| US4562256A (en) | 1985-12-31 |
| CH661272A5 (fr) | 1987-07-15 |
| GB8421763D0 (en) | 1984-10-03 |
| FR2551756A1 (fr) | 1985-03-15 |
| GB2146326A (en) | 1985-04-17 |
| DE3432985C2 (enExample) | 1993-09-16 |
| KR850002095A (ko) | 1985-05-06 |
| FR2551756B1 (fr) | 1987-10-02 |
| JPS6056979A (ja) | 1985-04-02 |
| JPH0437833B2 (enExample) | 1992-06-22 |
| KR910002838B1 (ko) | 1991-05-06 |
| GB2146326B (en) | 1987-01-14 |
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