HU184792B - Process for producing tetrahydropyridyl-indol derivatives - Google Patents
Process for producing tetrahydropyridyl-indol derivatives Download PDFInfo
- Publication number
- HU184792B HU184792B HU801536A HU153680A HU184792B HU 184792 B HU184792 B HU 184792B HU 801536 A HU801536 A HU 801536A HU 153680 A HU153680 A HU 153680A HU 184792 B HU184792 B HU 184792B
- Authority
- HU
- Hungary
- Prior art keywords
- formula
- compound
- carbon atoms
- alkyl
- defined above
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 15
- AEYHIZZYMFAUNU-UHFFFAOYSA-N 2-(3,4-dihydro-2h-pyridin-1-yl)-1h-indole Chemical class C1CCC=CN1C1=CC2=CC=CC=C2N1 AEYHIZZYMFAUNU-UHFFFAOYSA-N 0.000 title description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 26
- 150000003839 salts Chemical class 0.000 claims abstract description 26
- 239000002253 acid Substances 0.000 claims abstract description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 20
- -1 nitro, amino Chemical group 0.000 claims abstract description 16
- 238000002360 preparation method Methods 0.000 claims abstract description 15
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 11
- 239000001257 hydrogen Substances 0.000 claims abstract description 11
- 125000005359 phenoxyalkyl group Chemical group 0.000 claims abstract description 10
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims abstract description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 7
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 6
- 150000002367 halogens Chemical group 0.000 claims abstract description 6
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 63
- 239000000460 chlorine Substances 0.000 claims description 15
- 229910052801 chlorine Inorganic materials 0.000 claims description 14
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 9
- 239000011707 mineral Substances 0.000 claims description 9
- 150000007522 mineralic acids Chemical class 0.000 claims description 9
- 150000007524 organic acids Chemical class 0.000 claims description 9
- 150000004820 halides Chemical class 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 239000004480 active ingredient Substances 0.000 claims description 7
- 235000005985 organic acids Nutrition 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 claims description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- 239000011630 iodine Substances 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 125000002346 iodo group Chemical group I* 0.000 claims 2
- 125000006531 (C2-C5) alkyl group Chemical group 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 230000003474 anti-emetic effect Effects 0.000 abstract description 3
- 230000000561 anti-psychotic effect Effects 0.000 abstract description 2
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- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 150000002431 hydrogen Chemical group 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000000304 alkynyl group Chemical group 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 231100000252 nontoxic Toxicity 0.000 abstract 1
- 230000003000 nontoxic effect Effects 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
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- 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 4
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- SKYZYDSNJIOXRL-BTQNPOSSSA-N (6ar)-6-methyl-5,6,6a,7-tetrahydro-4h-dibenzo[de,g]quinoline-10,11-diol;hydrochloride Chemical compound Cl.C([C@H]1N(C)CC2)C3=CC=C(O)C(O)=C3C3=C1C2=CC=C3 SKYZYDSNJIOXRL-BTQNPOSSSA-N 0.000 description 3
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- ULGGPDHVFPOYQP-UHFFFAOYSA-N chloroform;n,n-diethylethanamine;propan-2-one Chemical compound CC(C)=O.ClC(Cl)Cl.CCN(CC)CC ULGGPDHVFPOYQP-UHFFFAOYSA-N 0.000 description 3
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- WIKYUJGCLQQFNW-UHFFFAOYSA-N prochlorperazine Chemical compound C1CN(C)CCN1CCCN1C2=CC(Cl)=CC=C2SC2=CC=CC=C21 WIKYUJGCLQQFNW-UHFFFAOYSA-N 0.000 description 3
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- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 2
- DSCNSPUAQOOMAV-UHFFFAOYSA-N 5-nitro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1h-indole;hydrochloride Chemical compound [Cl-].C12=CC([N+](=O)[O-])=CC=C2NC=C1C1=CC[NH2+]CC1 DSCNSPUAQOOMAV-UHFFFAOYSA-N 0.000 description 2
- FXEDKEZNOJDXPY-UHFFFAOYSA-N 5-nitro-3-(1-propyl-3,6-dihydro-2h-pyridin-4-yl)-1h-indole;hydrochloride Chemical compound Cl.C1N(CCC)CCC(C=2C3=CC(=CC=C3NC=2)[N+]([O-])=O)=C1 FXEDKEZNOJDXPY-UHFFFAOYSA-N 0.000 description 2
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- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
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- SXWRTZOXMUOJER-UHFFFAOYSA-N hydron;piperidin-4-one;chloride;hydrate Chemical compound O.Cl.O=C1CCNCC1 SXWRTZOXMUOJER-UHFFFAOYSA-N 0.000 description 2
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- GJQNVZVOTKFLIU-UHFFFAOYSA-N piperidin-1-ium-4-one;chloride Chemical compound Cl.O=C1CCNCC1 GJQNVZVOTKFLIU-UHFFFAOYSA-N 0.000 description 2
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- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
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- VXWVFZFZYXOBTA-UHFFFAOYSA-N 5-bromo-1h-indole Chemical compound BrC1=CC=C2NC=CC2=C1 VXWVFZFZYXOBTA-UHFFFAOYSA-N 0.000 description 1
- RANMHKQOJANPJJ-UHFFFAOYSA-N 5-chloro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1h-indole Chemical compound C12=CC(Cl)=CC=C2NC=C1C1=CCNCC1 RANMHKQOJANPJJ-UHFFFAOYSA-N 0.000 description 1
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- 238000001816 cooling Methods 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- DZGCGKFAPXFTNM-UHFFFAOYSA-N ethanol;hydron;chloride Chemical compound Cl.CCO DZGCGKFAPXFTNM-UHFFFAOYSA-N 0.000 description 1
- MVEAAGBEUOMFRX-UHFFFAOYSA-N ethyl acetate;hydrochloride Chemical compound Cl.CCOC(C)=O MVEAAGBEUOMFRX-UHFFFAOYSA-N 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000007972 injectable composition Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000011835 investigation 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
- 238000002955 isolation Methods 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([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
- 229940039717 lanolin Drugs 0.000 description 1
- 235000019388 lanolin Nutrition 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000007788 liquid 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
- 238000004519 manufacturing process Methods 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000008693 nausea Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000002687 nonaqueous vehicle Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- GJVFBWCTGUSGDD-UHFFFAOYSA-L pentamethonium bromide Chemical compound [Br-].[Br-].C[N+](C)(C)CCCCC[N+](C)(C)C GJVFBWCTGUSGDD-UHFFFAOYSA-L 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 208000020016 psychiatric disease Diseases 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910001923 silver oxide Inorganic materials 0.000 description 1
- KEAYESYHFKHZAL-BJUDXGSMSA-N sodium-22 Chemical compound [22Na] KEAYESYHFKHZAL-BJUDXGSMSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
-
- 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
-
- 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
- A61P25/24—Antidepressants
-
- 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
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Hospice & Palliative Care (AREA)
- Otolaryngology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7918217A FR2460947A1 (fr) | 1979-07-13 | 1979-07-13 | Nouveau derives n-substitues du tetrahydropyridinyl-indole, leurs sels, procede de preparation, application a titre de medicaments et compositions les renfermant |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU184792B true HU184792B (en) | 1984-10-29 |
Family
ID=9227845
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU801536A HU184792B (en) | 1979-07-13 | 1980-06-20 | Process for producing tetrahydropyridyl-indol derivatives |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US4324790A (en, 2012) |
| EP (1) | EP0022705B1 (en, 2012) |
| JP (2) | JPS5615283A (en, 2012) |
| AT (1) | ATE2954T1 (en, 2012) |
| AU (1) | AU535197B2 (en, 2012) |
| BE (1) | BE884279A (en, 2012) |
| CA (1) | CA1145752A (en, 2012) |
| DE (1) | DE3062614D1 (en, 2012) |
| DK (1) | DK152048C (en, 2012) |
| ES (2) | ES493311A0 (en, 2012) |
| FR (1) | FR2460947A1 (en, 2012) |
| HU (1) | HU184792B (en, 2012) |
| IE (1) | IE50067B1 (en, 2012) |
| PT (1) | PT71549B (en, 2012) |
| SU (1) | SU936813A3 (en, 2012) |
| ZA (2) | ZA803793B (en, 2012) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2533924A1 (fr) * | 1982-10-05 | 1984-04-06 | Roussel Uclaf | Nouveaux derives du 4-(1h-indol-3-yl)a-methyl piperidine-1-ethanol, leurs sels, le procede de preparation, l'application a titre de medicaments et les compositions les renfermant |
| 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 |
| US5214059A (en) * | 1989-07-03 | 1993-05-25 | Hoechst-Roussel Pharmaceuticals Incorporated | 2-(aminoaryl) indoles and indolines as topical antiinflammatory agents for the treatment of skin disorders |
| US5846982A (en) * | 1996-06-14 | 1998-12-08 | Eli Lilly And Company | Inhibition of serotonin reuptake |
| EA013123B1 (ru) * | 2005-04-13 | 2010-02-26 | Ньюрэксон, Инк. | Замещенные индолы, обладающие активностью ингибирования nos |
| CA2643822A1 (en) * | 2006-04-13 | 2007-10-25 | Neuraxon, Inc | 1,5 and 3,6- substituted indole compounds having nos inhibitory activity |
| MX2010005343A (es) * | 2007-11-16 | 2010-08-09 | Neuraxon Inc | Compuestos indola 3, 5-sustituidos que tienen actividad inhibidora de la re-absorcion y el reciclo de nos y norepinefrina. |
| SG185991A1 (en) * | 2007-11-16 | 2012-12-28 | Neuraxon Inc | Indole compounds and methods for treating visceral pain |
| CA2705422A1 (en) * | 2007-11-16 | 2009-05-22 | The Arizona Board Of Regents On Behalf Of The University Of Arizona | Methods for treating visceral pain |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| IL48508A (en) * | 1974-12-09 | 1979-10-31 | Roussel Uclaf | Pharmaceutical compositions comprising piperidylindole derivatives |
| FR2362628A1 (fr) * | 1976-08-26 | 1978-03-24 | Roussel Uclaf | Nouveaux derives du piperidyl-indole et leurs sels, procede de preparation et application a titre de medicaments |
| SU639243A1 (ru) * | 1976-12-27 | 1979-11-25 | Ордена Трудового Красного Знамени Институт Органического Синтеза Ан Латвийской Сср | 1-/4-(4-Фторфенил)-4-оксибутил/ -4- (индолил-31)-1,2,3,6-тетрагидропиридин или его соли, обладающие психотропными свойствами |
| FR2444678A2 (fr) * | 1978-12-22 | 1980-07-18 | Roussel Uclaf | Nouveau procede de preparation de derives du piperidyl-indole et de leurs sels |
-
1979
- 1979-07-13 FR FR7918217A patent/FR2460947A1/fr active Granted
-
1980
- 1980-06-20 HU HU801536A patent/HU184792B/hu not_active IP Right Cessation
- 1980-06-25 ZA ZA00803793A patent/ZA803793B/xx unknown
- 1980-06-25 ZA ZA00803789A patent/ZA803789B/xx unknown
- 1980-06-30 US US06/163,966 patent/US4324790A/en not_active Expired - Lifetime
- 1980-07-02 DE DE8080401005T patent/DE3062614D1/de not_active Expired
- 1980-07-02 EP EP80401005A patent/EP0022705B1/fr not_active Expired
- 1980-07-02 AT AT80401005T patent/ATE2954T1/de not_active IP Right Cessation
- 1980-07-11 SU SU802947298A patent/SU936813A3/ru active
- 1980-07-11 JP JP9408380A patent/JPS5615283A/ja active Granted
- 1980-07-11 BE BE0/201379A patent/BE884279A/fr not_active IP Right Cessation
- 1980-07-11 ES ES493311A patent/ES493311A0/es active Granted
- 1980-07-11 DK DK300180A patent/DK152048C/da not_active IP Right Cessation
- 1980-07-11 CA CA000356009A patent/CA1145752A/fr not_active Expired
- 1980-07-11 PT PT71549A patent/PT71549B/pt unknown
- 1980-07-11 IE IE1456/80A patent/IE50067B1/en unknown
- 1980-07-11 JP JP9408280A patent/JPS5615282A/ja active Granted
- 1980-07-11 ES ES493308A patent/ES8107213A1/es not_active Expired
- 1980-07-11 AU AU60359/80A patent/AU535197B2/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| PT71549B (fr) | 1981-12-14 |
| IE801456L (en) | 1981-01-13 |
| FR2460947A1 (fr) | 1981-01-30 |
| ES8107214A1 (es) | 1981-08-16 |
| DE3062614D1 (en) | 1983-05-11 |
| CA1145752A (fr) | 1983-05-03 |
| FR2460947B1 (en, 2012) | 1981-07-10 |
| BE884279A (fr) | 1981-01-12 |
| ES493308A0 (es) | 1981-08-16 |
| AU535197B2 (en) | 1984-03-08 |
| ZA803793B (en) | 1981-06-24 |
| EP0022705A1 (fr) | 1981-01-21 |
| US4324790A (en) | 1982-04-13 |
| ES493311A0 (es) | 1981-08-16 |
| IE50067B1 (en) | 1986-02-05 |
| ATE2954T1 (de) | 1983-04-15 |
| ES8107213A1 (es) | 1981-08-16 |
| ZA803789B (en) | 1981-06-24 |
| DK152048C (da) | 1988-10-10 |
| DK300180A (da) | 1981-01-14 |
| EP0022705B1 (fr) | 1983-04-06 |
| JPS5615282A (en) | 1981-02-14 |
| AU6035980A (en) | 1981-01-15 |
| SU936813A3 (ru) | 1982-06-15 |
| JPS6348872B2 (en, 2012) | 1988-09-30 |
| PT71549A (fr) | 1980-08-01 |
| JPS5615283A (en) | 1981-02-14 |
| DK152048B (da) | 1988-01-25 |
| JPS6351154B2 (en, 2012) | 1988-10-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 | ||
| HMM4 | Cancellation of final prot. due to non-payment of fee |