NO310461B1 - Serotoninreseptormidler - Google Patents
Serotoninreseptormidler Download PDFInfo
- Publication number
- NO310461B1 NO310461B1 NO19951015A NO951015A NO310461B1 NO 310461 B1 NO310461 B1 NO 310461B1 NO 19951015 A NO19951015 A NO 19951015A NO 951015 A NO951015 A NO 951015A NO 310461 B1 NO310461 B1 NO 310461B1
- Authority
- NO
- Norway
- Prior art keywords
- mmol
- nmr
- dms0
- ethyl
- binding affinity
- Prior art date
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- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 288
- 150000003839 salts Chemical class 0.000 claims abstract description 24
- 101710138068 5-hydroxytryptamine receptor 1D Proteins 0.000 claims abstract description 23
- 101710138638 5-hydroxytryptamine receptor 1A Proteins 0.000 claims abstract description 15
- 239000001257 hydrogen Substances 0.000 claims abstract description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 5
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 5
- 150000002367 halogens Chemical group 0.000 claims abstract description 5
- 101001003232 Mus musculus Immediate early response gene 2 protein Proteins 0.000 claims abstract description 4
- 150000002431 hydrogen Chemical group 0.000 claims abstract 5
- 150000001875 compounds Chemical class 0.000 claims description 185
- 238000002360 preparation method Methods 0.000 claims description 40
- 239000000556 agonist Substances 0.000 claims description 19
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- 239000000825 pharmaceutical preparation Substances 0.000 claims description 11
- 208000019695 Migraine disease Diseases 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 10
- 208000019901 Anxiety disease Diseases 0.000 claims description 9
- 230000036506 anxiety Effects 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 206010020772 Hypertension Diseases 0.000 claims description 7
- 206010002383 Angina Pectoris Diseases 0.000 claims description 5
- 208000020401 Depressive disease Diseases 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 230000000202 analgesic effect Effects 0.000 claims description 3
- 230000001939 inductive effect Effects 0.000 claims 2
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical group O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims 1
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 abstract description 41
- 229940076279 serotonin Drugs 0.000 abstract description 12
- 125000001424 substituent group Chemical group 0.000 abstract description 10
- 239000003795 chemical substances by application Substances 0.000 abstract description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract description 5
- 125000000753 cycloalkyl group Chemical group 0.000 abstract description 3
- 125000003884 phenylalkyl group Chemical group 0.000 abstract description 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract description 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
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- 238000005481 NMR spectroscopy Methods 0.000 description 144
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 113
- 239000007787 solid Substances 0.000 description 90
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 72
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- 235000011152 sodium sulphate Nutrition 0.000 description 22
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- 230000001404 mediated effect Effects 0.000 description 19
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- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 18
- 239000002253 acid Substances 0.000 description 18
- 150000002148 esters Chemical class 0.000 description 18
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- 102100027493 5-hydroxytryptamine receptor 1D Human genes 0.000 description 17
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 17
- 125000005605 benzo group Chemical group 0.000 description 16
- 239000012267 brine Substances 0.000 description 16
- 239000012043 crude product Substances 0.000 description 16
- 238000000354 decomposition reaction Methods 0.000 description 16
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 16
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 15
- 235000019341 magnesium sulphate Nutrition 0.000 description 15
- 239000002904 solvent Substances 0.000 description 15
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 14
- 239000013078 crystal Substances 0.000 description 14
- 150000001408 amides Chemical class 0.000 description 13
- 102100022738 5-hydroxytryptamine receptor 1A Human genes 0.000 description 12
- 150000001412 amines Chemical class 0.000 description 12
- 238000001816 cooling Methods 0.000 description 12
- 239000003960 organic solvent Substances 0.000 description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 11
- 241000700159 Rattus Species 0.000 description 11
- GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 11
- 238000002844 melting Methods 0.000 description 11
- 230000008018 melting Effects 0.000 description 11
- 235000017557 sodium bicarbonate Nutrition 0.000 description 11
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 11
- 238000012360 testing method Methods 0.000 description 11
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- 235000019270 ammonium chloride Nutrition 0.000 description 9
- 239000002585 base Substances 0.000 description 9
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- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 8
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- XXHLZOSDMBLXQU-UHFFFAOYSA-N ethyl 4-piperazin-1-yl-1-benzothiophene-2-carboxylate;hydrochloride Chemical compound Cl.C1=CC=C2SC(C(=O)OCC)=CC2=C1N1CCNCC1 XXHLZOSDMBLXQU-UHFFFAOYSA-N 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
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- 239000013543 active substance Substances 0.000 description 7
- 239000003480 eluent Substances 0.000 description 7
- SMEFDZRBDLRRHP-UHFFFAOYSA-N ethyl 3-[4-[4-(2-phenylethyl)piperazin-1-yl]-1-benzothiophen-2-yl]prop-2-enoate Chemical compound C1=CC=C2SC(C=CC(=O)OCC)=CC2=C1N(CC1)CCN1CCC1=CC=CC=C1 SMEFDZRBDLRRHP-UHFFFAOYSA-N 0.000 description 7
- DEQPJLZHHKPHFU-UHFFFAOYSA-N ethyl 4-[4-(2-phenylethyl)piperazin-1-yl]-1-benzothiophene-2-carboxylate Chemical compound C1=CC=C2SC(C(=O)OCC)=CC2=C1N(CC1)CCN1CCC1=CC=CC=C1 DEQPJLZHHKPHFU-UHFFFAOYSA-N 0.000 description 7
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- 239000011780 sodium chloride Substances 0.000 description 6
- 238000000967 suction filtration Methods 0.000 description 6
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 5
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- LPPWIPBCEKPMPK-UHFFFAOYSA-N ethyl 4-piperazin-1-yl-1-benzothiophene-2-carboxylate Chemical compound C1=CC=C2SC(C(=O)OCC)=CC2=C1N1CCNCC1 LPPWIPBCEKPMPK-UHFFFAOYSA-N 0.000 description 5
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- 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
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D333/56—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D333/58—Radicals substituted by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D333/60—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes 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 carbon atoms of the hetero ring
- C07D333/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D333/70—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 2
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Epidemiology (AREA)
- Anesthesiology (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Confectionery (AREA)
- Jellies, Jams, And Syrups (AREA)
- Dental Preparations (AREA)
- Materials For Medical Uses (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US94700792A | 1992-09-17 | 1992-09-17 | |
| US7969293A | 1993-06-17 | 1993-06-17 | |
| US08/119,791 US5436246A (en) | 1992-09-17 | 1993-09-15 | Serotonin receptor agents |
| PCT/US1993/008865 WO1994006789A1 (en) | 1992-09-17 | 1993-09-17 | Serotonin receptor agents |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO951015D0 NO951015D0 (no) | 1995-03-16 |
| NO951015L NO951015L (no) | 1995-05-15 |
| NO310461B1 true NO310461B1 (no) | 2001-07-09 |
Family
ID=27373532
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19951015A NO310461B1 (no) | 1992-09-17 | 1995-03-16 | Serotoninreseptormidler |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US5436246A (ja) |
| EP (1) | EP0660832B1 (ja) |
| JP (1) | JP3298107B2 (ja) |
| KR (1) | KR100195809B1 (ja) |
| AT (1) | ATE162190T1 (ja) |
| AU (1) | AU671494B2 (ja) |
| CA (1) | CA2144947C (ja) |
| DE (1) | DE69316377T2 (ja) |
| ES (1) | ES2112434T3 (ja) |
| FI (1) | FI951249A0 (ja) |
| GR (1) | GR3026297T3 (ja) |
| HU (1) | HU222725B1 (ja) |
| NO (1) | NO310461B1 (ja) |
| NZ (1) | NZ256561A (ja) |
| WO (1) | WO1994006789A1 (ja) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SK278998B6 (sk) * | 1991-02-01 | 1998-05-06 | Merck Sharp & Dohme Limited | Deriváty imidazolu, triazolu a tetrazolu, spôsob i |
| MX9700693A (es) * | 1994-07-26 | 1997-04-30 | Pfizer | Derivados del 4-indol. |
| FR2735127B1 (fr) * | 1995-06-09 | 1997-08-22 | Pf Medicament | Nouvelles piperazines heteroaromatiques utiles comme medicaments. |
| GB9517381D0 (en) * | 1995-08-24 | 1995-10-25 | Pharmacia Spa | Aryl and heteroaryl piperazine derivatives |
| US6462048B2 (en) * | 1996-03-29 | 2002-10-08 | Pfizer Inc. | Benzyl(idene)-lactam derivatives, their preparation and their use as selective (ant)agonists of 5-HT1A- and/or 5-HT1D receptors |
| CA2250347C (en) | 1996-03-29 | 2006-02-21 | Duphar International Research B.V. | Piperazine and piperidine compounds with high affinity for dopamine-d2 and serotonin-5ht1a receptors |
| FR2761068B1 (fr) * | 1997-03-20 | 1999-04-23 | Synthelabo | Derives de piperazin-4-ylthieno[3,2-c]pyridin-4-yl-2- carboxamide, leur preparation et leur application en therapeutique |
| FR2763243A1 (fr) * | 1997-05-14 | 1998-11-20 | Pf Medicament | Utilisation d'amines indoliques comme medicaments antithrombotiques |
| EP0900792B1 (en) * | 1997-09-02 | 2003-10-29 | Duphar International Research B.V | Piperazine and piperidine derivatives as 5-HT1A and dopamine D2-receptor (ant)agonists |
| TW530054B (en) * | 1997-09-24 | 2003-05-01 | Duphar Int Res | New piperazine and piperidine compounds |
| WO2001009126A1 (en) * | 1999-07-29 | 2001-02-08 | Eli Lilly And Company | Serotonergic benzothiophenes |
| GB0005789D0 (en) * | 2000-03-11 | 2000-05-03 | Knoll Ag | Therapeutic agents |
| CA2440238C (en) * | 2001-03-16 | 2011-09-13 | Abbott Laboratories | Novel amines as histamine-3 receptor ligands and their therapeutic applications |
| US6969730B2 (en) * | 2001-03-16 | 2005-11-29 | Abbott Laboratories | Amines as histamine-3 receptor ligands and their therapeutic applications |
| US20050080084A1 (en) * | 2003-07-11 | 2005-04-14 | Pharmacia Corporation | Compositions of a cyclooxygenase-2 selective inhibitor and a serotonin-modulating agent for the treatment of central nervous system damage |
| CA2536340A1 (en) * | 2003-08-22 | 2005-03-03 | Pharmacia Corporation | Compositions of a cyclooxygenase-2 selective inhibitor and a serotonin modulating agent for the treatment of neoplasia |
| US20050261347A1 (en) * | 2003-10-24 | 2005-11-24 | Wyeth | Dihydrobenzofuranyl alkanamine derivatives and methods for using same |
| US7435837B2 (en) * | 2003-10-24 | 2008-10-14 | Wyeth | Dihydrobenzofuranyl alkanamine derivatives and methods for using same |
| WO2006101454A1 (en) * | 2005-03-21 | 2006-09-28 | S*Bio Pte Ltd | Benzothiophene derivatives: preparation and pharmaceutical applications |
| TWI320783B (en) | 2005-04-14 | 2010-02-21 | Otsuka Pharma Co Ltd | Heterocyclic compound |
| JP4315393B2 (ja) * | 2005-04-14 | 2009-08-19 | 大塚製薬株式会社 | 複素環化合物 |
| TW200716583A (en) * | 2005-04-22 | 2007-05-01 | Wyeth Corp | Crystal forms of {[(2R)-7-(2,6-dichlorophenyl)-5-fluoro-2,3-dihydro-1-benzofuran-2-yl]methyl}amine hydrochloride |
| CA2821480A1 (en) * | 2010-12-20 | 2012-06-28 | Astrazeneca Ab | 2-carboxamide-4-piperazinyl-benzofuran derivative |
| RU2601420C2 (ru) * | 2011-07-28 | 2016-11-10 | Оцука Фармасьютикал Ко., Лтд. | СПОСОБ ПОЛУЧЕНИЯ СОЕДИНЕНИЯ БЕНЗО[b]ТИОФЕНА |
| CN104557896A (zh) * | 2013-10-18 | 2015-04-29 | 沈敬山 | 布瑞哌唑、其关键中间体及其盐的制备方法 |
| CN105732572A (zh) * | 2014-12-10 | 2016-07-06 | 苏州鹏旭医药科技有限公司 | 一种Brexpiprazole中间体的制备方法及Brexpiprazole中间体 |
| EP3150591A1 (en) | 2015-10-02 | 2017-04-05 | Crystal Pharma S.A.U | Process and intermediates for the preparation of benzo[b]thiophene compounds |
| WO2020183011A1 (en) | 2019-03-14 | 2020-09-17 | Institut Curie | Htr1d inhibitors and uses thereof in the treatment of cancer |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK169601B1 (da) * | 1983-10-17 | 1994-12-19 | Duphar Int Res | Piperazinderivater og farmaceutisk præparat indeholdende et sådant derivat, samt piperazinderivater med mellemproduktanvendelse |
| GB8406906D0 (en) * | 1984-03-16 | 1984-04-18 | Akzo Nv | Benzo-thiazole and benzothiophene derivatives |
| DE3571436D1 (en) * | 1984-12-21 | 1989-08-17 | Duphar Int Res | New pharmaceutical compositions having anti-psychotic properties |
| ATE81975T1 (de) * | 1984-12-21 | 1992-11-15 | Duphar Int Res | Arzneimittel mit psychotroper wirkung. |
| ES2052059T3 (es) * | 1988-03-16 | 1994-07-01 | Ciba Geigy Ag | Procedimiento para la obtencion de tiocompuestos. |
| NL8802997A (nl) * | 1988-12-07 | 1990-07-02 | Philips Nv | Weergeefinrichting. |
| US5032598A (en) * | 1989-12-08 | 1991-07-16 | Merck & Co., Inc. | Nitrogens containing heterocyclic compounds as class III antiarrhythmic agents |
| FR2655988B1 (fr) * | 1989-12-20 | 1994-05-20 | Adir Cie | Nouveaux derives de la napht-1-yl piperazine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent. |
| DK203990D0 (da) * | 1990-08-24 | 1990-08-24 | Novo Nordisk As | Piperazinylderivater |
-
1993
- 1993-09-15 US US08/119,791 patent/US5436246A/en not_active Expired - Lifetime
- 1993-09-17 WO PCT/US1993/008865 patent/WO1994006789A1/en active IP Right Grant
- 1993-09-17 AT AT93922253T patent/ATE162190T1/de not_active IP Right Cessation
- 1993-09-17 CA CA002144947A patent/CA2144947C/en not_active Expired - Fee Related
- 1993-09-17 AU AU51321/93A patent/AU671494B2/en not_active Ceased
- 1993-09-17 NZ NZ256561A patent/NZ256561A/en unknown
- 1993-09-17 DE DE69316377T patent/DE69316377T2/de not_active Expired - Fee Related
- 1993-09-17 HU HU9500796A patent/HU222725B1/hu not_active IP Right Cessation
- 1993-09-17 JP JP50837194A patent/JP3298107B2/ja not_active Expired - Fee Related
- 1993-09-17 KR KR1019950701026A patent/KR100195809B1/ko not_active IP Right Cessation
- 1993-09-17 ES ES93922253T patent/ES2112434T3/es not_active Expired - Lifetime
- 1993-09-17 EP EP93922253A patent/EP0660832B1/en not_active Expired - Lifetime
-
1995
- 1995-03-16 NO NO19951015A patent/NO310461B1/no not_active IP Right Cessation
- 1995-03-16 FI FI951249A patent/FI951249A0/fi unknown
-
1998
- 1998-03-06 GR GR980400468T patent/GR3026297T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE69316377T2 (de) | 1998-08-27 |
| WO1994006789A1 (en) | 1994-03-31 |
| NO951015L (no) | 1995-05-15 |
| FI951249A (fi) | 1995-03-16 |
| EP0660832A1 (en) | 1995-07-05 |
| KR100195809B1 (ko) | 1999-06-15 |
| JPH08501559A (ja) | 1996-02-20 |
| FI951249A0 (fi) | 1995-03-16 |
| CA2144947A1 (en) | 1994-03-31 |
| DE69316377D1 (de) | 1998-02-19 |
| HU222725B1 (hu) | 2003-09-29 |
| ES2112434T3 (es) | 1998-04-01 |
| KR950703558A (ko) | 1995-09-20 |
| HU9500796D0 (en) | 1995-05-29 |
| US5436246A (en) | 1995-07-25 |
| AU671494B2 (en) | 1996-08-29 |
| NZ256561A (en) | 1996-06-25 |
| JP3298107B2 (ja) | 2002-07-02 |
| HUT72662A (en) | 1996-05-28 |
| EP0660832B1 (en) | 1998-01-14 |
| CA2144947C (en) | 2000-02-01 |
| NO951015D0 (no) | 1995-03-16 |
| GR3026297T3 (en) | 1998-06-30 |
| AU5132193A (en) | 1994-04-12 |
| ATE162190T1 (de) | 1998-01-15 |
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| Date | Code | Title | Description |
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| MM1K | Lapsed by not paying the annual fees |