AU715785B2 - 1-(pyrazol-3-ylethyl)-4-(indol-3-yl) piperdines as compositions affecting the central nervous system - Google Patents
1-(pyrazol-3-ylethyl)-4-(indol-3-yl) piperdines as compositions affecting the central nervous system Download PDFInfo
- Publication number
- AU715785B2 AU715785B2 AU14432/97A AU1443297A AU715785B2 AU 715785 B2 AU715785 B2 AU 715785B2 AU 14432/97 A AU14432/97 A AU 14432/97A AU 1443297 A AU1443297 A AU 1443297A AU 715785 B2 AU715785 B2 AU 715785B2
- Authority
- AU
- Australia
- Prior art keywords
- ethyl
- methyl
- pyrazolyl
- formula
- piperidyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
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- 238000000034 method Methods 0.000 claims description 30
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- 150000003839 salts Chemical class 0.000 claims description 19
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
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- 239000012071 phase Substances 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical class OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003217 pyrazoles Chemical class 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
- 230000011514 reflex Effects 0.000 description 1
- 201000000980 schizophrenia Diseases 0.000 description 1
- 229940076279 serotonin Drugs 0.000 description 1
- 208000019116 sleep disease Diseases 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000011699 spontaneously hypertensive rat Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 208000011117 substance-related disease Diseases 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- QYTJFOBUAJLXAR-UHFFFAOYSA-N tert-butyl 4-(5-fluoro-1h-indol-3-yl)piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1C1=CNC2=CC=C(F)C=C12 QYTJFOBUAJLXAR-UHFFFAOYSA-N 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- WTVXIBRMWGUIMI-UHFFFAOYSA-N trifluoro($l^{1}-oxidanylsulfonyl)methane Chemical group [O]S(=O)(=O)C(F)(F)F WTVXIBRMWGUIMI-UHFFFAOYSA-N 0.000 description 1
- 125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 239000000080 wetting agent 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
- C07D401/14—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 three or more hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/454—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. pimozide, domperidone
-
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Neurosurgery (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pain & Pain Management (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19602505 | 1996-01-25 | ||
| DE19602505A DE19602505A1 (de) | 1996-01-25 | 1996-01-25 | 1-(Pyrazol-4-Indol-3-yl)-Piperidine |
| PCT/EP1997/000187 WO1997027186A1 (de) | 1996-01-25 | 1997-01-17 | 1-(pyrazol-3-yl-ethyl)-4-(indol-3-yl)-piperidine als das zentralnervensystem beeinflussende mittel |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU1443297A AU1443297A (en) | 1997-08-20 |
| AU715785B2 true AU715785B2 (en) | 2000-02-10 |
Family
ID=7783568
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU14432/97A Ceased AU715785B2 (en) | 1996-01-25 | 1997-01-17 | 1-(pyrazol-3-ylethyl)-4-(indol-3-yl) piperdines as compositions affecting the central nervous system |
Country Status (16)
| Country | Link |
|---|---|
| EP (1) | EP0879234A1 (cs) |
| JP (1) | JP2000503972A (cs) |
| KR (1) | KR19990081970A (cs) |
| CN (1) | CN1209807A (cs) |
| AR (1) | AR005549A1 (cs) |
| AU (1) | AU715785B2 (cs) |
| BR (1) | BR9707467A (cs) |
| CA (1) | CA2244136A1 (cs) |
| CZ (1) | CZ231898A3 (cs) |
| DE (1) | DE19602505A1 (cs) |
| HU (1) | HUP9900980A2 (cs) |
| NO (1) | NO983439L (cs) |
| PL (1) | PL328228A1 (cs) |
| SK (1) | SK99298A3 (cs) |
| WO (1) | WO1997027186A1 (cs) |
| ZA (1) | ZA97572B (cs) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7179823B1 (en) | 1999-11-10 | 2007-02-20 | Takeda Pharmaceutical Company Limited | 5-membered n-heterocyclic compounds with hypoglycemic and hypolipidemic activity |
| US7507729B2 (en) | 2005-10-11 | 2009-03-24 | Hoffmann-La Roche Inc. | Substituted imidazo-[1,5-a][1,2,4]triazolo[1,5-d][1,4] benzodiazepine derivatives |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001021614A1 (en) * | 1999-09-09 | 2001-03-29 | H. Lundbeck A/S | 5-aminoalkyl and 5-aminocarbonyl substituted indoles |
| US7309703B2 (en) | 2000-08-14 | 2007-12-18 | Ortho Mcneil Pharmaceutical, Inc. | Substituted pyrazoles |
| US7332494B2 (en) | 2000-08-14 | 2008-02-19 | Janssen Pharmaceutica, N.V. | Method for treating allergies using substituted pyrazoles |
| US20050026927A1 (en) * | 2001-11-14 | 2005-02-03 | Henning Boettcher | Pyrazole derivatives as psychopharmaceuticals |
| EP1945213A4 (en) * | 2005-10-24 | 2009-12-02 | Janssen Pharmaceutica Nv | MODULATORS OF THE R3-PIPERIDINE-4-YL-INDOLE ORL-1 RECEPTOR |
| TWI548630B (zh) | 2011-04-06 | 2016-09-11 | Ｌｇ生命科學有限公司 | １－（３－氰基－１－異丙基－吲哚－５－基）吡唑－４－羧酸結晶型及其製造方法 |
| US20240000750A1 (en) * | 2020-11-04 | 2024-01-04 | Lg Chem, Ltd. | Method for preparing crystalline particles of 1-(3-cyano-1-isopropyl-indole-5-yl)pyrazole-4-carboxylic acid, and pharmaceutical composition comprising same |
| WO2025021120A1 (zh) * | 2023-07-24 | 2025-01-30 | 上海翊石医药科技有限公司 | 一类5-ht2a受体激动剂及其制备方法和应用 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0708102A1 (en) * | 1994-10-05 | 1996-04-24 | Eli Lilly And Company | 5-HT1F agonists for the treatment of migraine |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2060816C3 (de) * | 1970-12-10 | 1980-09-04 | Merck Patent Gmbh, 6100 Darmstadt | 4-Phenylpiperidinderivate Verfahren zu ihrer Herstellung und pharmazeutische Zubereitungen enthaltend diese Verbindungen |
| DE2258033A1 (de) * | 1972-11-27 | 1974-05-30 | Merck Patent Gmbh | Verfahren zur herstellung von pyrazolderivaten |
| GB8719167D0 (en) * | 1987-08-13 | 1987-09-23 | Glaxo Group Ltd | Chemical compounds |
| US5045550A (en) * | 1990-09-20 | 1991-09-03 | Warner-Lambert Co. | Substituted tetrahydropyridines as central nervous system agents |
-
1996
- 1996-01-25 DE DE19602505A patent/DE19602505A1/de not_active Withdrawn
-
1997
- 1997-01-17 CN CN97191852A patent/CN1209807A/zh active Pending
- 1997-01-17 JP JP9526493A patent/JP2000503972A/ja active Pending
- 1997-01-17 SK SK992-98A patent/SK99298A3/sk unknown
- 1997-01-17 CZ CZ982318A patent/CZ231898A3/cs unknown
- 1997-01-17 HU HU9900980A patent/HUP9900980A2/hu unknown
- 1997-01-17 WO PCT/EP1997/000187 patent/WO1997027186A1/de not_active Application Discontinuation
- 1997-01-17 CA CA002244136A patent/CA2244136A1/en not_active Abandoned
- 1997-01-17 PL PL97328228A patent/PL328228A1/xx unknown
- 1997-01-17 KR KR1019980705688A patent/KR19990081970A/ko not_active Withdrawn
- 1997-01-17 AU AU14432/97A patent/AU715785B2/en not_active Ceased
- 1997-01-17 BR BR9707467A patent/BR9707467A/pt unknown
- 1997-01-17 EP EP97901049A patent/EP0879234A1/de not_active Withdrawn
- 1997-01-23 ZA ZA9700572A patent/ZA97572B/xx unknown
- 1997-01-24 AR ARP970100297A patent/AR005549A1/es unknown
-
1998
- 1998-07-24 NO NO983439A patent/NO983439L/no unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0708102A1 (en) * | 1994-10-05 | 1996-04-24 | Eli Lilly And Company | 5-HT1F agonists for the treatment of migraine |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7179823B1 (en) | 1999-11-10 | 2007-02-20 | Takeda Pharmaceutical Company Limited | 5-membered n-heterocyclic compounds with hypoglycemic and hypolipidemic activity |
| US7507729B2 (en) | 2005-10-11 | 2009-03-24 | Hoffmann-La Roche Inc. | Substituted imidazo-[1,5-a][1,2,4]triazolo[1,5-d][1,4] benzodiazepine derivatives |
Also Published As
| Publication number | Publication date |
|---|---|
| KR19990081970A (ko) | 1999-11-15 |
| CZ231898A3 (cs) | 1998-10-14 |
| NO983439D0 (no) | 1998-07-24 |
| ZA97572B (en) | 1997-08-04 |
| AU1443297A (en) | 1997-08-20 |
| CA2244136A1 (en) | 1997-07-31 |
| SK99298A3 (en) | 1999-01-11 |
| DE19602505A1 (de) | 1997-07-31 |
| NO983439L (no) | 1998-09-25 |
| PL328228A1 (en) | 1999-01-18 |
| BR9707467A (pt) | 1999-07-20 |
| AR005549A1 (es) | 1999-06-23 |
| WO1997027186A1 (de) | 1997-07-31 |
| HUP9900980A2 (hu) | 1999-07-28 |
| CN1209807A (zh) | 1999-03-03 |
| EP0879234A1 (de) | 1998-11-25 |
| JP2000503972A (ja) | 2000-04-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FGA | Letters patent sealed or granted (standard patent) | ||
| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |