FI92066C - Menetelmä valmistaa farmakologisesti arvokkaita pyrido/3',4';4,5/syklohept/1,2-b/indolijohdannaisia - Google Patents
Menetelmä valmistaa farmakologisesti arvokkaita pyrido/3',4';4,5/syklohept/1,2-b/indolijohdannaisia Download PDFInfo
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- FI92066C FI92066C FI891086A FI891086A FI92066C FI 92066 C FI92066 C FI 92066C FI 891086 A FI891086 A FI 891086A FI 891086 A FI891086 A FI 891086A FI 92066 C FI92066 C FI 92066C
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- 238000002360 preparation method Methods 0.000 title claims description 12
- 238000000034 method Methods 0.000 title claims description 6
- 230000008569 process Effects 0.000 title claims description 4
- 150000002475 indoles Chemical class 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 69
- -1 methoxy, hydroxy, acetamido, acetyl Chemical group 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 9
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- 239000002253 acid Substances 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 5
- BOLFFYUDEVMACE-UHFFFAOYSA-N cyclohepta[b]indole Chemical class C1=CC=CC=C2C3=CC=CC=C3N=C21 BOLFFYUDEVMACE-UHFFFAOYSA-N 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
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- 238000002386 leaching Methods 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
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- 238000006243 chemical reaction Methods 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
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- 201000010099 disease Diseases 0.000 description 4
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- QXJMCSBBTMVSJS-UHFFFAOYSA-N 1-(1h-indol-2-yl)ethanone Chemical class C1=CC=C2NC(C(=O)C)=CC2=C1 QXJMCSBBTMVSJS-UHFFFAOYSA-N 0.000 description 3
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- 229910052786 argon Inorganic materials 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
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- HUUPVABNAQUEJW-UHFFFAOYSA-N 1-methylpiperidin-4-one Chemical compound CN1CCC(=O)CC1 HUUPVABNAQUEJW-UHFFFAOYSA-N 0.000 description 2
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- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
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- 241000699670 Mus sp. Species 0.000 description 2
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
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- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
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- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 230000008859 change Effects 0.000 description 2
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- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
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- 239000011737 fluorine Substances 0.000 description 2
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- 208000019622 heart disease Diseases 0.000 description 2
- JBXRLVPILRXPNH-UHFFFAOYSA-N indol-6-one Chemical compound O=C1C=CC2=CC=NC2=C1 JBXRLVPILRXPNH-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- 210000002751 lymph Anatomy 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
- 229960001289 prazosin Drugs 0.000 description 2
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
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- ABJSOROVZZKJGI-OCYUSGCXSA-N (1r,2r,4r)-2-(4-bromophenyl)-n-[(4-chlorophenyl)-(2-fluoropyridin-4-yl)methyl]-4-morpholin-4-ylcyclohexane-1-carboxamide Chemical compound C1=NC(F)=CC(C(NC(=O)[C@H]2[C@@H](C[C@@H](CC2)N2CCOCC2)C=2C=CC(Br)=CC=2)C=2C=CC(Cl)=CC=2)=C1 ABJSOROVZZKJGI-OCYUSGCXSA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- FRAFMLCDGYVHNZ-UHFFFAOYSA-N 2-hydroxy-5-methoxy-3-tridecylcyclohexa-2,5-diene-1,4-dione Chemical compound CCCCCCCCCCCCCC1=C(O)C(=O)C=C(OC)C1=O FRAFMLCDGYVHNZ-UHFFFAOYSA-N 0.000 description 1
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- 101100261000 Caenorhabditis elegans top-3 gene Proteins 0.000 description 1
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- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- METLQVFFFUYXNT-QTPGKHNVSA-N Ervatamine Chemical compound O=C1C[C@H]2[C@H](CC)CN(C)C[C@@]2(C(=O)OC)CC2=C1NC1=CC=CC=C21 METLQVFFFUYXNT-QTPGKHNVSA-N 0.000 description 1
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- 241000042032 Petrocephalus catostoma Species 0.000 description 1
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- 229920002472 Starch Polymers 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
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- 231100000403 acute toxicity Toxicity 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
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- 125000000217 alkyl group Chemical group 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
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- 102000012740 beta Adrenergic Receptors Human genes 0.000 description 1
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- 210000004204 blood vessel Anatomy 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
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- QBKVEAIEIVKHGR-UHFFFAOYSA-M di(ethylidene)azanium;chloride Chemical compound [Cl-].CC=[N+]=CC QBKVEAIEIVKHGR-UHFFFAOYSA-M 0.000 description 1
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- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000036543 hypotension Effects 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- 229930005303 indole alkaloid Natural products 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
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- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000003137 locomotive effect Effects 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
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- 230000007246 mechanism Effects 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
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- MRBDMNSDAVCSSF-UHFFFAOYSA-N phentolamine Chemical compound C1=CC(C)=CC=C1N(C=1C=C(O)C=CC=1)CC1=NCCN1 MRBDMNSDAVCSSF-UHFFFAOYSA-N 0.000 description 1
- 229960001999 phentolamine Drugs 0.000 description 1
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- 102000005962 receptors Human genes 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 239000013558 reference substance Substances 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 1
- CGRKYEALWSRNJS-UHFFFAOYSA-N sodium;2-methylbutan-2-olate Chemical compound [Na+].CCC(C)(C)[O-] CGRKYEALWSRNJS-UHFFFAOYSA-N 0.000 description 1
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- 235000002906 tartaric acid Nutrition 0.000 description 1
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- 150000003892 tartrate salts Chemical class 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
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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
- C07D401/06—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 only aliphatic carbon atoms
-
- 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
- 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
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3807533 | 1988-03-08 | ||
| DE3807533A DE3807533A1 (de) | 1988-03-08 | 1988-03-08 | Pyridocycloheptindol-verbindungen, verfahren zu ihrer herstellung und pharmazeutische mittel, die diese verbindungen enthalten |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| FI891086A0 FI891086A0 (fi) | 1989-03-08 |
| FI891086A7 FI891086A7 (fi) | 1989-09-09 |
| FI92066B FI92066B (fi) | 1994-06-15 |
| FI92066C true FI92066C (fi) | 1994-09-26 |
Family
ID=6349134
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI891086A FI92066C (fi) | 1988-03-08 | 1989-03-08 | Menetelmä valmistaa farmakologisesti arvokkaita pyrido/3',4';4,5/syklohept/1,2-b/indolijohdannaisia |
Country Status (30)
| Country | Link |
|---|---|
| US (1) | US5159080A (en, 2012) |
| JP (1) | JPH0613514B2 (en, 2012) |
| KR (1) | KR910004449B1 (en, 2012) |
| CN (1) | CN1024551C (en, 2012) |
| AT (1) | AT395243B (en, 2012) |
| AU (1) | AU610701B2 (en, 2012) |
| BE (1) | BE1002923A4 (en, 2012) |
| CH (1) | CH677792A5 (en, 2012) |
| CZ (1) | CZ143789A3 (en, 2012) |
| DD (1) | DD283622A5 (en, 2012) |
| DE (1) | DE3807533A1 (en, 2012) |
| DK (1) | DK110089A (en, 2012) |
| FI (1) | FI92066C (en, 2012) |
| FR (1) | FR2628426A1 (en, 2012) |
| GB (1) | GB2216889B (en, 2012) |
| GR (1) | GR1000311B (en, 2012) |
| HU (1) | HU205355B (en, 2012) |
| IE (1) | IE61683B1 (en, 2012) |
| IL (1) | IL89476A (en, 2012) |
| IT (1) | IT1228569B (en, 2012) |
| LU (1) | LU87463A1 (en, 2012) |
| NL (1) | NL8900552A (en, 2012) |
| NO (1) | NO890978L (en, 2012) |
| NZ (1) | NZ228246A (en, 2012) |
| PL (1) | PL159893B1 (en, 2012) |
| PT (1) | PT89941B (en, 2012) |
| SE (1) | SE500580C2 (en, 2012) |
| SU (1) | SU1650012A3 (en, 2012) |
| YU (1) | YU48489A (en, 2012) |
| ZA (1) | ZA891721B (en, 2012) |
-
1988
- 1988-03-08 DE DE3807533A patent/DE3807533A1/de active Granted
-
1989
- 1989-03-01 LU LU87463A patent/LU87463A1/fr unknown
- 1989-03-02 AT AT0047389A patent/AT395243B/de not_active IP Right Cessation
- 1989-03-02 CH CH807/89A patent/CH677792A5/de not_active IP Right Cessation
- 1989-03-02 SE SE8900725A patent/SE500580C2/sv unknown
- 1989-03-02 GB GB8904792A patent/GB2216889B/en not_active Expired - Fee Related
- 1989-03-03 IT IT8919648A patent/IT1228569B/it active
- 1989-03-03 IE IE70089A patent/IE61683B1/en not_active IP Right Cessation
- 1989-03-03 IL IL8947689A patent/IL89476A/en unknown
- 1989-03-07 GR GR890100145A patent/GR1000311B/el unknown
- 1989-03-07 DD DD89326336A patent/DD283622A5/de not_active IP Right Cessation
- 1989-03-07 ZA ZA891721A patent/ZA891721B/xx unknown
- 1989-03-07 DK DK110089A patent/DK110089A/da not_active Application Discontinuation
- 1989-03-07 YU YU00484/89A patent/YU48489A/xx unknown
- 1989-03-07 AU AU31095/89A patent/AU610701B2/en not_active Ceased
- 1989-03-07 NO NO89890978A patent/NO890978L/no unknown
- 1989-03-07 SU SU894613697A patent/SU1650012A3/ru active
- 1989-03-07 CZ CS891437A patent/CZ143789A3/cs unknown
- 1989-03-07 HU HU891112A patent/HU205355B/hu not_active IP Right Cessation
- 1989-03-07 CN CN89102030A patent/CN1024551C/zh not_active Expired - Fee Related
- 1989-03-07 FR FR8902978A patent/FR2628426A1/fr active Granted
- 1989-03-07 NL NL8900552A patent/NL8900552A/nl not_active Application Discontinuation
- 1989-03-07 NZ NZ228246A patent/NZ228246A/en unknown
- 1989-03-07 KR KR1019890002754A patent/KR910004449B1/ko not_active Expired
- 1989-03-08 PT PT89941A patent/PT89941B/pt not_active IP Right Cessation
- 1989-03-08 PL PL1989278135A patent/PL159893B1/pl unknown
- 1989-03-08 JP JP1053974A patent/JPH0613514B2/ja not_active Expired - Lifetime
- 1989-03-08 BE BE8900249A patent/BE1002923A4/fr not_active IP Right Cessation
- 1989-03-08 FI FI891086A patent/FI92066C/fi not_active IP Right Cessation
-
1990
- 1990-12-18 US US07/629,188 patent/US5159080A/en not_active Expired - Fee Related
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| BB | Publication of examined application | ||
| MM | Patent lapsed | ||
| MM | Patent lapsed |
Owner name: MADAUS AKTIENGESELLSCHAFT |