CH624952A5 - - Google Patents
Download PDFInfo
- Publication number
- CH624952A5 CH624952A5 CH1046877A CH1046877A CH624952A5 CH 624952 A5 CH624952 A5 CH 624952A5 CH 1046877 A CH1046877 A CH 1046877A CH 1046877 A CH1046877 A CH 1046877A CH 624952 A5 CH624952 A5 CH 624952A5
- Authority
- CH
- Switzerland
- Prior art keywords
- indole
- derivatives
- formula
- piperidyl
- addition salts
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 claims description 22
- -1 alkoxy radical Chemical class 0.000 claims description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 15
- HNQZRUDJRPSFAU-UHFFFAOYSA-N 2-piperidin-1-yl-1h-indole Chemical class C1CCCCN1C1=CC2=CC=CC=C2N1 HNQZRUDJRPSFAU-UHFFFAOYSA-N 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 9
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- 239000011707 mineral Substances 0.000 claims description 7
- 150000007522 mineralic acids Chemical class 0.000 claims description 7
- 150000007524 organic acids Chemical class 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 6
- 235000005985 organic acids Nutrition 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 239000000460 chlorine Substances 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
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 3
- GJQNVZVOTKFLIU-UHFFFAOYSA-N piperidin-1-ium-4-one;chloride Chemical compound Cl.O=C1CCNCC1 GJQNVZVOTKFLIU-UHFFFAOYSA-N 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- ISJZHGGWQPZRHJ-UHFFFAOYSA-N 2-(3,6-dihydro-2h-pyridin-1-yl)-1h-indole Chemical group C1C=CCCN1C1=CC2=CC=CC=C2N1 ISJZHGGWQPZRHJ-UHFFFAOYSA-N 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 239000013067 intermediate product Substances 0.000 claims 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 12
- 230000007935 neutral effect Effects 0.000 description 11
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 239000000203 mixture Substances 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 239000003814 drug Substances 0.000 description 6
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 6
- CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- 235000010755 mineral Nutrition 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 239000008194 pharmaceutical composition Substances 0.000 description 4
- 235000011044 succinic acid Nutrition 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- WDJQAYUPVJEQJW-UHFFFAOYSA-N chloroform;n,n-diethylethanamine;methanol Chemical compound OC.ClC(Cl)Cl.CCN(CC)CC WDJQAYUPVJEQJW-UHFFFAOYSA-N 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- SXWRTZOXMUOJER-UHFFFAOYSA-N hydron;piperidin-4-one;chloride;hydrate Chemical compound O.Cl.O=C1CCNCC1 SXWRTZOXMUOJER-UHFFFAOYSA-N 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 239000001384 succinic acid Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000005457 ice water Substances 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
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 208000020016 psychiatric disease Diseases 0.000 description 2
- JAVBBFXUGDCHLZ-UHFFFAOYSA-N 1-$l^{1}-oxidanylpropane Chemical compound CCC[O] JAVBBFXUGDCHLZ-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 206010028813 Nausea Diseases 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 206010047700 Vomiting Diseases 0.000 description 1
- RSWGJHLUYNHPMX-ONCXSQPRSA-N abietic acid Chemical class C([C@@H]12)CC(C(C)C)=CC1=CC[C@@H]1[C@]2(C)CCC[C@@]1(C)C(O)=O RSWGJHLUYNHPMX-ONCXSQPRSA-N 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000001430 anti-depressive effect Effects 0.000 description 1
- 230000003474 anti-emetic effect Effects 0.000 description 1
- 230000000648 anti-parkinson Effects 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 229940005513 antidepressants Drugs 0.000 description 1
- 239000000939 antiparkinson agent Substances 0.000 description 1
- 239000008135 aqueous vehicle Substances 0.000 description 1
- 230000003542 behavioural effect Effects 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000001079 digestive effect Effects 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 230000000142 dyskinetic effect Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 230000008693 nausea Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003444 succinic acids Chemical class 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 230000008673 vomiting Effects 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C55/00—Saturated compounds having more than one carboxyl group bound to acyclic carbon atoms
- C07C55/02—Dicarboxylic acids
- C07C55/10—Succinic acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Otolaryngology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH22881A CH628629A5 (en) | 1977-08-26 | 1981-01-14 | Derivatives of piperidylindole and their salts |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7625798A FR2362628A1 (fr) | 1976-08-26 | 1976-08-26 | Nouveaux derives du piperidyl-indole et leurs sels, procede de preparation et application a titre de medicaments |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH624952A5 true CH624952A5 (en, 2012) | 1981-08-31 |
Family
ID=9177152
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1046877A CH624952A5 (en, 2012) | 1976-08-26 | 1977-08-26 | |
| CH22781A CH628344A5 (fr) | 1976-08-26 | 1981-01-14 | Procede de preparation de nouveaux derives du piperidyl-indole et de leurs sels. |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH22781A CH628344A5 (fr) | 1976-08-26 | 1981-01-14 | Procede de preparation de nouveaux derives du piperidyl-indole et de leurs sels. |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US4196209A (en, 2012) |
| JP (1) | JPS5328178A (en, 2012) |
| AT (1) | AT358582B (en, 2012) |
| AU (1) | AU510037B2 (en, 2012) |
| BE (1) | BE858101A (en, 2012) |
| CA (1) | CA1103676A (en, 2012) |
| CH (2) | CH624952A5 (en, 2012) |
| DE (1) | DE2738646C2 (en, 2012) |
| DK (1) | DK142812B (en, 2012) |
| ES (1) | ES461875A1 (en, 2012) |
| FR (1) | FR2362628A1 (en, 2012) |
| GB (1) | GB1556919A (en, 2012) |
| HU (1) | HU172711B (en, 2012) |
| IE (1) | IE45574B1 (en, 2012) |
| LU (1) | LU78028A1 (en, 2012) |
| NL (1) | NL7709383A (en, 2012) |
| PT (1) | PT66953B (en, 2012) |
| SE (1) | SE432595B (en, 2012) |
| ZA (1) | ZA775134B (en, 2012) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2421899A1 (fr) | 1978-01-16 | 1979-11-02 | Roussel Uclaf | Nouveaux derives du tetrahydropyridinyl-indole et leurs sels, le procede de preparation et l'application a titre de medicaments de ces nouveaux produits |
| FR2444678A2 (fr) * | 1978-12-22 | 1980-07-18 | Roussel Uclaf | Nouveau procede de preparation de derives du piperidyl-indole et de leurs sels |
| SE8004129L (sv) * | 1979-07-13 | 1981-01-14 | Roussel Uclaf | Nya tetrahydropyridin-4-yl-indolderivat samt salter derav, framstellning och anvendning derav sasom lekemedel samt kompositioner innehallande dessa foreningar |
| FR2460947A1 (fr) * | 1979-07-13 | 1981-01-30 | Roussel Uclaf | Nouveau derives n-substitues du tetrahydropyridinyl-indole, leurs sels, procede de preparation, application a titre de medicaments et compositions les renfermant |
| DE3035403C2 (de) | 1980-09-19 | 1982-08-26 | Rütgerswerke AG, 6000 Frankfurt | Verfahren zur Herstellung von 5-Chlorindol |
| FR2510111A1 (fr) * | 1981-07-24 | 1983-01-28 | Roussel Uclaf | Nouveaux derives du piperidin-3-yl indole, leurs sels, leur procede de preparation, leur application a titre de medicaments et les compositions pharmaceutiques les renfermant |
| IE55972B1 (en) * | 1982-10-07 | 1991-03-13 | Kefalas As | Phenylindene derivatives,acid addition salts thereof,and methods of preparation |
| US4548939A (en) * | 1984-10-01 | 1985-10-22 | Janssen Pharmaceutica N. V. | 1H-Indol-3-yl containing 1,3-dimethyl-1H-purine-2,6-diones |
| IE58370B1 (en) * | 1985-04-10 | 1993-09-08 | Lundbeck & Co As H | Indole derivatives |
| US4742057A (en) * | 1985-12-05 | 1988-05-03 | Fujisawa Pharmaceutical Co., Ltd. | Antiallergic thiazole compounds |
| FR2608157B1 (fr) * | 1986-12-11 | 1989-09-08 | Roussel Uclaf | Nouveaux derives de l'azaspirodecane, leurs sels, procede de preparation, application a titre de medicaments et compositions les renfermant et intermediaires |
| GB8719167D0 (en) * | 1987-08-13 | 1987-09-23 | Glaxo Group Ltd | Chemical compounds |
| IE61488B1 (en) * | 1987-08-13 | 1994-11-02 | Glaxo Group Ltd | Indole derivatives |
| FR2621586B1 (fr) * | 1987-10-08 | 1990-02-02 | Roussel Uclaf | Nouveaux derives de l'azapirodecane, leur procede de preparation et leur application comme medicaments |
| GB8819024D0 (en) * | 1988-08-10 | 1988-09-14 | Glaxo Group Ltd | Chemical compounds |
| WO1990007926A1 (en) * | 1989-01-20 | 1990-07-26 | Pfizer Inc. | 3-(1,2,5,6-tetrahydropyridyl)-pyrrolopyridines |
| US5643784A (en) * | 1990-12-04 | 1997-07-01 | H, Lundbeck A/S | Indan derivatives |
| DK36291D0 (da) * | 1991-03-01 | 1991-03-01 | Lundbeck & Co As H | Anvendelse af piperidylsubstituerede indolderivater til behandling af kognitive lidelser |
| NZ243065A (en) * | 1991-06-13 | 1995-07-26 | Lundbeck & Co As H | Piperidine derivatives and pharmaceutical compositions |
| US5846982A (en) * | 1996-06-14 | 1998-12-08 | Eli Lilly And Company | Inhibition of serotonin reuptake |
| ES2292636T3 (es) * | 2000-11-29 | 2008-03-16 | Eli Lilly And Company | 1-(2-m-metanosulfanomidofeniletil)-4-(m-trifluorometilfenil)piper. |
| WO2004069828A1 (ja) * | 2003-02-04 | 2004-08-19 | Mitsubishi Pharma Corporation | ピペリジン化合物およびその医薬用途 |
| WO2007050381A2 (en) * | 2005-10-24 | 2007-05-03 | Janssen Pharmaceutica, N.V. | 3-piperidin-4-yl-indole orl-1 receptor modulators |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2872453A (en) * | 1959-02-03 | Indole derivatives | ||
| US3361759A (en) * | 1963-10-07 | 1968-01-02 | Upjohn Co | 3-(2-pyrrolidinyl)-indoles and method of preparation |
| JPS4856687A (en, 2012) * | 1971-11-18 | 1973-08-09 | ||
| FR2193584B1 (en, 2012) * | 1972-07-28 | 1975-08-08 | Roussel Uclaf | |
| DE2322470A1 (de) * | 1973-05-04 | 1974-11-21 | Boehringer Sohn Ingelheim | Neue indolyl-piperidino-(bzw. 1,2,5,6tetrahydro-pyridyl-)butyrophenone und verfahren zu ihrer herstellung |
| FR2258843B1 (en, 2012) * | 1974-01-30 | 1977-09-09 | Roussel Uclaf | |
| IL48508A (en) * | 1974-12-09 | 1979-10-31 | Roussel Uclaf | Pharmaceutical compositions comprising piperidylindole derivatives |
| FR2349331A1 (fr) * | 1976-04-30 | 1977-11-25 | Roussel Uclaf | Nouveaux derives de 2,3 dihydro a/4-(3-indolyl) 1-piperidinyl/methyl 1,4-benzodioxin-2-methanol, un procede pour leur preparation et leur application comme medicaments |
-
1976
- 1976-08-26 FR FR7625798A patent/FR2362628A1/fr active Granted
-
1977
- 1977-07-04 SE SE7707731A patent/SE432595B/xx not_active IP Right Cessation
- 1977-08-01 US US05/820,835 patent/US4196209A/en not_active Expired - Lifetime
- 1977-08-24 ZA ZA00775134A patent/ZA775134B/xx unknown
- 1977-08-24 PT PT66953A patent/PT66953B/pt unknown
- 1977-08-25 NL NL7709383A patent/NL7709383A/xx not_active Application Discontinuation
- 1977-08-25 CA CA285,446A patent/CA1103676A/fr not_active Expired
- 1977-08-25 BE BE180423A patent/BE858101A/xx not_active IP Right Cessation
- 1977-08-25 JP JP10116577A patent/JPS5328178A/ja active Granted
- 1977-08-25 LU LU78028A patent/LU78028A1/xx unknown
- 1977-08-25 ES ES461875A patent/ES461875A1/es not_active Expired
- 1977-08-25 AU AU28213/77A patent/AU510037B2/en not_active Expired
- 1977-08-25 DK DK376577AA patent/DK142812B/da not_active IP Right Cessation
- 1977-08-26 AT AT619677A patent/AT358582B/de not_active IP Right Cessation
- 1977-08-26 HU HU77RO00000938A patent/HU172711B/hu not_active IP Right Cessation
- 1977-08-26 DE DE2738646A patent/DE2738646C2/de not_active Expired
- 1977-08-26 CH CH1046877A patent/CH624952A5/fr not_active IP Right Cessation
- 1977-08-26 GB GB35882/77A patent/GB1556919A/en not_active Expired
- 1977-08-26 IE IE1792/77A patent/IE45574B1/en unknown
-
1981
- 1981-01-14 CH CH22781A patent/CH628344A5/fr not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DE2738646A1 (de) | 1978-03-02 |
| PT66953A (fr) | 1977-09-01 |
| JPS631312B2 (en, 2012) | 1988-01-12 |
| DE2738646C2 (de) | 1985-08-08 |
| CH628344A5 (fr) | 1982-02-26 |
| ZA775134B (en) | 1978-09-27 |
| DK376577A (en, 2012) | 1978-02-27 |
| LU78028A1 (en, 2012) | 1978-04-27 |
| IE45574L (en) | 1978-02-26 |
| GB1556919A (en) | 1979-11-28 |
| AU510037B2 (en) | 1980-06-05 |
| SE7707731L (sv) | 1978-02-27 |
| DK142812B (da) | 1981-02-02 |
| AU2821377A (en) | 1979-03-01 |
| BE858101A (fr) | 1978-02-27 |
| AT358582B (de) | 1980-09-25 |
| US4196209A (en) | 1980-04-01 |
| DK142812C (en, 2012) | 1981-09-21 |
| PT66953B (fr) | 1979-11-12 |
| CA1103676A (fr) | 1981-06-23 |
| JPS5328178A (en) | 1978-03-16 |
| NL7709383A (nl) | 1978-02-28 |
| ATA619677A (de) | 1980-02-15 |
| ES461875A1 (es) | 1978-05-16 |
| FR2362628A1 (fr) | 1978-03-24 |
| SE432595B (sv) | 1984-04-09 |
| HU172711B (hu) | 1978-11-28 |
| FR2362628B1 (en, 2012) | 1979-03-02 |
| IE45574B1 (en) | 1982-10-06 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH624952A5 (en, 2012) | ||
| EP0070767B1 (fr) | Nouveaux dérivés de la quinoléine, leurs sels, leur préparation, leur application comme médicaments et les compositions les renfermant | |
| EP0003199B1 (fr) | Nouveaux dérivés du tétrahydro pyridinyl indole et leurs sels, le procédé de préparation, l'application à titre de médicaments de ces nouveaux produits et les compositions pharmaceutiques les renfermant | |
| EP0107569A1 (fr) | Nouveaux dérivés de la 6-amino 7-hydroxy 4,5,6,7-tétrahydroimidazo/4,5,1-j-k/ /1/ benzazépin-2(1H)-one, leurs sels, leur préparation, leur application à titre de médicaments, les compositions les renfermant | |
| EP0012639B1 (fr) | Nouveaux dérivés de l'acide 3-quinoléine carboxylique, leur procédé de préparation, leur application comme médicament et les compositions pharmaceutiques les renfermant | |
| CH639369A5 (fr) | Benzamides heterocycliques substitues et leurs procedes de preparation. | |
| EP0040573A2 (fr) | Dérivés de l'acide 4-hydroxy 3-quinoléine carboxylique substitués en 2, leur préparation, leur application comme médicament, les compositions les renfermant et les intermédiaires nouveaux obtenus | |
| CH649994A5 (fr) | Derives du 4h-1,2,4-triazole, procedes de preparation et compositions les renfermant. | |
| EP0022408A1 (fr) | Nouveaux dérivés de l'alpha-phényl 2-pyrrolidineméthanol et leurs sels, procédé de préparation, application à titre de médicaments et compositions les renfermant | |
| EP0091328B1 (fr) | Nouveaux dérivés du trans 4-amino benz (c,d) indol-5-ol ainsi que leurs sels, leur préparation, leur application comme médicaments et compositions les renfermant | |
| EP0022705B1 (fr) | Nouveaux dérivés du tétrahydropyridinyl-indole et leurs sels, leur préparation, leur application comme médicaments et les compositions les renfermant | |
| CH627648A5 (fr) | Nouveaux derives de 20,21-dinoreburnamenine, procede de preparation et compositions pharmaceutiques. | |
| EP0021924B1 (fr) | Dérivés de l'indole, procédé pour leur préparation, leur application comme médicaments et compositions pharmaceutiques les contenant | |
| CH619935A5 (en, 2012) | ||
| CH659469A5 (fr) | Derives de l'acide 4-hydroxy 3-quinoleine carboxylique substitues en 2, leur preparation et les medicaments et compositions les renfermant. | |
| CA1128946A (fr) | Procede de preparation de derives du piperidyl-indole | |
| EP0214004B1 (fr) | Dérivés de l'acide 4-OH quinoléine carboxylique substitué en 2 par un groupement dihydroxylé éventuellement éthérifié ou estérifié, procédé et inter-médiaires de préparation, leur application comme médicaments et les compositions les renfermant | |
| EP0176444B1 (fr) | Nouveau procédé de préparation de dérivés du 4 H-1,2-4-triazole, nouveaux triazoles ainsi obtenus, leur applicication comme médicaments et les compositions pharmaceutiques les renfermant | |
| CA1091233A (fr) | Procede de preparation de nouveaux indoles substitues | |
| EP0034529B1 (fr) | Nouveaux dérivés de la triazoloquinazolinone et leurs sels avec les acides, leur préparation, leur application comme médicaments, et les compositions les renfermant | |
| EP0210909B1 (fr) | Nouveaux alcoylamino amides et leurs sels, leur préparation, leur application comme médicaments et les compositions les renfermant | |
| EP0305298A2 (fr) | Nouvelles imidazo benzodiazépines et leurs sels d'addition avec les acides, leur procédé et les intermédiaires de préparation, leur application comme médicaments et les compositions les renfermant | |
| CH529153A (fr) | Procédé de préparation de pyrazolo (1,2-b) phtalazine-1,5 (10H)-diones | |
| CH636350A5 (fr) | Derives de l'acide 2-/(4-quinoleinyl) amino/ 5-fluorobenzoique, leurs procedes de preparation et les compositions pharmaceutiques les renfermant. | |
| CH628629A5 (en) | Derivatives of piperidylindole and their salts |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |