HU205355B - Process for producing indole derivatives and pharmaceutical compositions comprising same - Google Patents
Process for producing indole derivatives and pharmaceutical compositions comprising same Download PDFInfo
- Publication number
- HU205355B HU205355B HU891112A HU111289A HU205355B HU 205355 B HU205355 B HU 205355B HU 891112 A HU891112 A HU 891112A HU 111289 A HU111289 A HU 111289A HU 205355 B HU205355 B HU 205355B
- Authority
- HU
- Hungary
- Prior art keywords
- compound
- formula
- hydrogen
- alkyl
- compounds
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 9
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 7
- 150000002475 indoles Chemical class 0.000 title description 4
- 229940054051 antipsychotic indole derivative Drugs 0.000 title description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 102
- 150000001875 compounds Chemical class 0.000 claims description 98
- 239000001257 hydrogen Substances 0.000 claims description 23
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 14
- 238000002360 preparation method Methods 0.000 claims description 13
- -1 indole compound Chemical class 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- SIKJAQJRHWYJAI-UHFFFAOYSA-N benzopyrrole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical group 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 150000002431 hydrogen Chemical group 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 4
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 230000002829 reductive effect Effects 0.000 claims description 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 2
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims 2
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- BOLFFYUDEVMACE-UHFFFAOYSA-N cyclohepta[b]indole Chemical compound C1=CC=CC=C2C3=CC=CC=C3N=C21 BOLFFYUDEVMACE-UHFFFAOYSA-N 0.000 claims 1
- 230000001335 demethylating effect Effects 0.000 claims 1
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- 239000003814 drug Substances 0.000 claims 1
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 24
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 17
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 17
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
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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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- 229910052760 oxygen Inorganic materials 0.000 description 3
- 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 3
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- 229910000033 sodium borohydride Inorganic materials 0.000 description 3
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- 125000001424 substituent group Chemical group 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
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- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
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- 210000002837 heart atrium Anatomy 0.000 description 1
- 230000000742 histaminergic effect Effects 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- 230000001631 hypertensive effect Effects 0.000 description 1
- 230000036543 hypotension Effects 0.000 description 1
- 229930005303 indole alkaloid Natural products 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 230000000297 inotrophic effect Effects 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 238000009940 knitting Methods 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 210000005246 left atrium Anatomy 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 239000000314 lubricant Substances 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
- 235000011090 malic acid Nutrition 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 230000004899 motility Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 235000010603 pastilles Nutrition 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 230000003334 potential effect Effects 0.000 description 1
- 239000010970 precious metal Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000011158 quantitative evaluation Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000013558 reference substance Substances 0.000 description 1
- 230000008439 repair process Effects 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 210000005070 sphincter Anatomy 0.000 description 1
- 210000000278 spinal cord Anatomy 0.000 description 1
- 230000009154 spontaneous behavior Effects 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000002511 suppository base Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000000948 sympatholitic effect Effects 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
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 150000003892 tartrate salts Chemical class 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
- 238000010998 test method Methods 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- SOBHUZYZLFQYFK-UHFFFAOYSA-K trisodium;hydroxy-[[phosphonatomethyl(phosphonomethyl)amino]methyl]phosphinate Chemical compound [Na+].[Na+].[Na+].OP(O)(=O)CN(CP(O)([O-])=O)CP([O-])([O-])=O SOBHUZYZLFQYFK-UHFFFAOYSA-K 0.000 description 1
- 229940124549 vasodilator Drugs 0.000 description 1
- 239000003071 vasodilator agent Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3807533A DE3807533A1 (de) | 1988-03-08 | 1988-03-08 | Pyridocycloheptindol-verbindungen, verfahren zu ihrer herstellung und pharmazeutische mittel, die diese verbindungen enthalten |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| HUT50175A HUT50175A (en) | 1989-12-28 |
| HU205355B true HU205355B (en) | 1992-04-28 |
Family
ID=6349134
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU891112A HU205355B (en) | 1988-03-08 | 1989-03-07 | Process for producing indole derivatives and pharmaceutical compositions comprising same |
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
Also Published As
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HMM4 | Cancellation of final prot. due to non-payment of fee |