HRP980441A2 - 2-(4-aryl or heteroaryl-piperazin-1-ylmethyl)-1h-indole derivatives - Google Patents
2-(4-aryl or heteroaryl-piperazin-1-ylmethyl)-1h-indole derivativesInfo
- Publication number
- HRP980441A2 HRP980441A2 HR60/055,764A HRP980441A HRP980441A2 HR P980441 A2 HRP980441 A2 HR P980441A2 HR P980441 A HRP980441 A HR P980441A HR P980441 A2 HRP980441 A2 HR P980441A2
- Authority
- HR
- Croatia
- Prior art keywords
- fluoro
- diseases
- piperazin
- hydrogen
- ylmethyl
- Prior art date
Links
- 229940054051 antipsychotic indole derivative Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 62
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 claims description 34
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 32
- 229910052739 hydrogen Inorganic materials 0.000 claims description 27
- 239000001257 hydrogen Substances 0.000 claims description 27
- 201000010099 disease Diseases 0.000 claims description 26
- 125000001153 fluoro group Chemical group F* 0.000 claims description 20
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 19
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 18
- 241000124008 Mammalia Species 0.000 claims description 18
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 17
- 229960003638 dopamine Drugs 0.000 claims description 17
- 239000000126 substance Substances 0.000 claims description 16
- 201000009032 substance abuse Diseases 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- 208000020016 psychiatric disease Diseases 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 150000002431 hydrogen Chemical class 0.000 claims description 11
- 101150043870 Drd4 gene Proteins 0.000 claims description 10
- 125000001246 bromo group Chemical group Br* 0.000 claims description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 10
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- 208000019553 vascular disease Diseases 0.000 claims description 9
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 8
- 206010012335 Dependence Diseases 0.000 claims description 8
- 230000000694 effects Effects 0.000 claims description 8
- 208000030533 eye disease Diseases 0.000 claims description 8
- 231100000736 substance abuse Toxicity 0.000 claims description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- 208000018737 Parkinson disease Diseases 0.000 claims description 7
- 239000003136 dopamine receptor stimulating agent Substances 0.000 claims description 7
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 7
- 206010047700 Vomiting Diseases 0.000 claims description 6
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 6
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- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 201000000980 schizophrenia Diseases 0.000 claims description 5
- YXEZZMBABNHVFB-UHFFFAOYSA-N 5-fluoro-2-[[4-[3-(trifluoromethyl)phenyl]piperazin-1-yl]methyl]-1h-indole Chemical compound C=1C2=CC(F)=CC=C2NC=1CN(CC1)CCN1C1=CC=CC(C(F)(F)F)=C1 YXEZZMBABNHVFB-UHFFFAOYSA-N 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- HAEDOALGQUCLFO-UHFFFAOYSA-N 2-[[4-(6-chloropyridazin-3-yl)piperazin-1-yl]methyl]-5-fluoro-1h-indole Chemical compound C=1C2=CC(F)=CC=C2NC=1CN(CC1)CCN1C1=CC=C(Cl)N=N1 HAEDOALGQUCLFO-UHFFFAOYSA-N 0.000 claims description 3
- HHOWJZHPIBYIAE-UHFFFAOYSA-N 2-[[4-[3-(trifluoromethyl)phenyl]piperazin-1-yl]methyl]-1h-indole Chemical compound FC(F)(F)C1=CC=CC(N2CCN(CC=3NC4=CC=CC=C4C=3)CC2)=C1 HHOWJZHPIBYIAE-UHFFFAOYSA-N 0.000 claims description 3
- PQOIDBZLMJMYCD-UHFFFAOYSA-N 5-fluoro-2-[(4-pyridin-2-ylpiperazin-1-yl)methyl]-1h-indole Chemical compound C=1C2=CC(F)=CC=C2NC=1CN(CC1)CCN1C1=CC=CC=N1 PQOIDBZLMJMYCD-UHFFFAOYSA-N 0.000 claims description 3
- MWPFXEHMGAJJCD-UHFFFAOYSA-N 5-fluoro-2-[[4-(4-fluorophenyl)piperazin-1-yl]methyl]-1h-indole Chemical compound C1=CC(F)=CC=C1N1CCN(CC=2NC3=CC=C(F)C=C3C=2)CC1 MWPFXEHMGAJJCD-UHFFFAOYSA-N 0.000 claims description 3
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- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 2
- FRPJGTNLZNXQEX-UHFFFAOYSA-N 2-[[4-(2-pyridinyl)-1-piperazinyl]methyl]-1H-benzimidazole Chemical compound N=1C2=CC=CC=C2NC=1CN(CC1)CCN1C1=CC=CC=N1 FRPJGTNLZNXQEX-UHFFFAOYSA-N 0.000 claims description 2
- RRXFCJOMSDWWCA-UHFFFAOYSA-N 2-[[4-(4-fluorophenyl)piperazin-1-yl]methyl]-1h-benzimidazole Chemical compound C1=CC(F)=CC=C1N1CCN(CC=2NC3=CC=CC=C3N=2)CC1 RRXFCJOMSDWWCA-UHFFFAOYSA-N 0.000 claims description 2
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims description 2
- ZSKFERSPBICNGI-UHFFFAOYSA-N 6-fluoro-2-[(4-pyridin-2-ylpiperazin-1-yl)methyl]-1h-benzimidazole Chemical compound N=1C2=CC(F)=CC=C2NC=1CN(CC1)CCN1C1=CC=CC=N1 ZSKFERSPBICNGI-UHFFFAOYSA-N 0.000 claims description 2
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 2
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- -1 hydrocarbon radicals Chemical class 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000000243 solution Substances 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
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- 238000002474 experimental method Methods 0.000 description 7
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- OHCQJHSOBUTRHG-KGGHGJDLSA-N FORSKOLIN Chemical compound O=C([C@@]12O)C[C@](C)(C=C)O[C@]1(C)[C@@H](OC(=O)C)[C@@H](O)[C@@H]1[C@]2(C)[C@@H](O)CCC1(C)C OHCQJHSOBUTRHG-KGGHGJDLSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
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- DKGZKTPJOSAWFA-UHFFFAOYSA-N spiperone Chemical compound C1=CC(F)=CC=C1C(=O)CCCN1CCC2(C(NCN2C=2C=CC=CC=2)=O)CC1 DKGZKTPJOSAWFA-UHFFFAOYSA-N 0.000 description 5
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- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
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- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
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- TZQTUVKKDQHARM-UHFFFAOYSA-N (5-fluoro-1h-indol-2-yl)-[4-[3-(trifluoromethyl)phenyl]piperazin-1-yl]methanone Chemical compound C=1C2=CC(F)=CC=C2NC=1C(=O)N(CC1)CCN1C1=CC=CC(C(F)(F)F)=C1 TZQTUVKKDQHARM-UHFFFAOYSA-N 0.000 description 3
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
-
- 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
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- 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
- A61P25/20—Hypnotics; Sedatives
-
- 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
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
-
- 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
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Psychiatry (AREA)
- Heart & Thoracic Surgery (AREA)
- Anesthesiology (AREA)
- Ophthalmology & Optometry (AREA)
- Addiction (AREA)
- Cardiology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US5576497P | 1997-08-15 | 1997-08-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP980441A2 true HRP980441A2 (en) | 1999-04-30 |
Family
ID=22000003
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR60/055,764A HRP980441A2 (en) | 1997-08-15 | 1998-08-14 | 2-(4-aryl or heteroaryl-piperazin-1-ylmethyl)-1h-indole derivatives |
Country Status (30)
| Country | Link |
|---|---|
| EP (1) | EP1003739A2 (fr) |
| JP (1) | JP2002536291A (fr) |
| KR (1) | KR20010022507A (fr) |
| CN (1) | CN1265660A (fr) |
| AP (1) | AP9801321A0 (fr) |
| AR (1) | AR017019A1 (fr) |
| AU (1) | AU8457298A (fr) |
| BG (1) | BG104069A (fr) |
| BR (1) | BR9811557A (fr) |
| CA (1) | CA2297486C (fr) |
| CO (1) | CO4960656A1 (fr) |
| DZ (1) | DZ2583A1 (fr) |
| EA (1) | EA200000023A1 (fr) |
| HR (1) | HRP980441A2 (fr) |
| HU (1) | HUP0003425A3 (fr) |
| ID (1) | ID23803A (fr) |
| IL (1) | IL133960A0 (fr) |
| IS (1) | IS5336A (fr) |
| MA (1) | MA24632A1 (fr) |
| NO (1) | NO20000722L (fr) |
| OA (1) | OA11286A (fr) |
| PA (1) | PA8457001A1 (fr) |
| PE (1) | PE106299A1 (fr) |
| PL (1) | PL338947A1 (fr) |
| SK (1) | SK1352000A3 (fr) |
| TN (1) | TNSN98151A1 (fr) |
| TR (1) | TR200000414T2 (fr) |
| UY (1) | UY25144A1 (fr) |
| WO (1) | WO1999009025A2 (fr) |
| ZA (1) | ZA987304B (fr) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU744539B2 (en) * | 1997-10-27 | 2002-02-28 | Neurosearch A/S | Heteroaryl diazacycloalkanes as cholinergic ligands at nicotinic acetylcholine receptors |
| EP0953567A3 (fr) * | 1998-04-29 | 2003-04-02 | Pfizer Products Inc. | Dérivés de piperazin-, piperidine- et tetrahydropyridine bicyclique substitués, leur préparation et leur utilisation comme agents a activité dopaminergique (recepteur D4 de la dopamine) centrale |
| EP1246817B1 (fr) | 1999-12-30 | 2004-06-23 | H. Lundbeck A/S | Derives de 4-phenyle-1-piperazinyle, -piperidinyle et -tetrahydropyridyle |
| GB0017952D0 (en) * | 2000-07-22 | 2000-09-13 | Univ Manchester | Treatment of dyskinesia |
| EP1177792A3 (fr) | 2000-07-27 | 2002-10-23 | Pfizer Products Inc. | Ligands dopamine d4 destines au traitement des troubles associees a la cherche de la nouveaute |
| AU2002336273A1 (en) * | 2001-03-09 | 2002-09-24 | Ortho-Mcneil Pharmaceutical, Inc. | Heterocyclic compounds and their use as histamine h4 ligands. |
| CA2497827A1 (fr) | 2002-09-06 | 2004-03-18 | Janssen Pharmaceutica, N.V. | Composes heterocycliques |
| WO2004108671A1 (fr) * | 2003-06-06 | 2004-12-16 | Suven Life Sciences Limited | Indoles substitues dotes d'une affinite pour le recepteur de la serotonine, leur procede de fabrication et compositions pharmaceutiques les contenant |
| EP2253315A1 (fr) | 2004-03-30 | 2010-11-24 | Takeda Pharmaceutical Company Limited | Dérivés d'acide alkoxypropanoique |
| US7572805B2 (en) | 2004-07-14 | 2009-08-11 | Bristol-Myers Squibb Company | Pyrrolo(oxo)isoquinolines as 5HT ligands |
| US7618980B2 (en) | 2004-07-14 | 2009-11-17 | Bristol-Myers Squibb Company | Pyrrolo(oxo)quinolines as 5HT ligands |
| JO2769B1 (en) | 2005-10-26 | 2014-03-15 | جانسين فارماسوتيكا ان. في | Rapid decomposition of physiologically antagonistic agents of the 2-dopamine receptor |
| JO2642B1 (en) | 2006-12-08 | 2012-06-17 | جانسين فارماسوتيكا ان. في | Dopamine 2 receptor antagonists are rapidly hydrolyzed |
| JO2849B1 (en) * | 2007-02-13 | 2015-03-15 | جانسين فارماسوتيكا ان. في | Dopamine 2 receptor antagonists are rapidly hydrolyzed |
| JP5431305B2 (ja) | 2007-04-23 | 2014-03-05 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | 高速解離性ドパミン２受容体アンタゴニストとしての４−アルコキシピリダジン誘導体 |
| WO2008128996A1 (fr) | 2007-04-23 | 2008-10-30 | Janssen Pharmaceutica N.V. | Thia(dia)zoles en tant qu'antagonistes du récepteur de la dopamine à dissociation rapide |
| EP2310374B1 (fr) | 2008-07-03 | 2012-10-31 | Janssen Pharmaceutica N.V. | 6-(1-pipérazinyl)-pyridazines substituées comme antagonistes du récepteur 5-ht6 |
| EP2307374B1 (fr) | 2008-07-31 | 2017-01-25 | Janssen Pharmaceutica NV | Pyridines à substitution pipérazin-1-yl-trifluorométhyle en tant qu'antagonistes du récepteur de la dopamine 2 à dissociation rapide |
| US11266640B2 (en) * | 2017-09-20 | 2022-03-08 | Hangzhou Innogate Pharma Co., Ltd. | Polycyclic compound acting as IDO inhibitor and/or IDO-HDAC dual inhibitor |
| US20230150980A1 (en) * | 2020-04-22 | 2023-05-18 | Anima Biotech Inc. | Collagen 1 translation inhibitors and methods of use thereof |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB944443A (fr) * | 1959-09-25 | 1900-01-01 | ||
| ES2097341T3 (es) * | 1991-07-03 | 1997-04-01 | Upjohn Co | Indoles sustituidos como farmacos para el tratamiento del sida. |
| JPH05255089A (ja) * | 1991-12-18 | 1993-10-05 | Sanwa Kagaku Kenkyusho Co Ltd | 抗ウイルス剤 |
| JPH08502958A (ja) * | 1992-10-23 | 1996-04-02 | メルク シヤープ エンド ドーム リミテツド | ドーパミンレセプターサブタイプリガンド |
| AU6215594A (en) * | 1993-03-18 | 1994-10-11 | Merck Sharp & Dohme Limited | Indole derivatives as dopamine d4 antagonists |
| GB9305644D0 (en) * | 1993-03-18 | 1993-05-05 | Merck Sharp & Dohme | Therapeutic agents |
| WO1994024105A1 (fr) * | 1993-04-15 | 1994-10-27 | Merck Sharp & Dohme Limited | Derives d'indole utiles comme antagonistes de la dopamine d4 |
| DE4414113A1 (de) * | 1994-04-22 | 1995-10-26 | Merck Patent Gmbh | 3-Indolylpiperidine |
| TW406075B (en) * | 1994-12-13 | 2000-09-21 | Upjohn Co | Alkyl substituted piperidinyl and piperazinyl anti-AIDS compounds |
| ZA968661B (en) * | 1995-11-17 | 1998-04-14 | Upjohn Co | Oxazolidinone antibacterial agent with tricyclic substituents. |
| TW504510B (en) * | 1996-05-10 | 2002-10-01 | Janssen Pharmaceutica Nv | 2,4-diaminopyrimidine derivatives |
-
1998
- 1998-08-05 AU AU84572/98A patent/AU8457298A/en not_active Abandoned
- 1998-08-05 TR TR2000/00414T patent/TR200000414T2/xx unknown
- 1998-08-05 EP EP98935229A patent/EP1003739A2/fr not_active Withdrawn
- 1998-08-05 CN CN98807831A patent/CN1265660A/zh active Pending
- 1998-08-05 IL IL13396098A patent/IL133960A0/xx unknown
- 1998-08-05 JP JP2000509706A patent/JP2002536291A/ja active Pending
- 1998-08-05 HU HU0003425A patent/HUP0003425A3/hu unknown
- 1998-08-05 AP APAP/P/1998/001321A patent/AP9801321A0/en unknown
- 1998-08-05 PL PL98338947A patent/PL338947A1/xx unknown
- 1998-08-05 CA CA002297486A patent/CA2297486C/fr not_active Expired - Fee Related
- 1998-08-05 ID IDW20000197A patent/ID23803A/id unknown
- 1998-08-05 WO PCT/IB1998/001198 patent/WO1999009025A2/fr not_active Ceased
- 1998-08-05 BR BR9811557-0A patent/BR9811557A/pt not_active IP Right Cessation
- 1998-08-05 KR KR1020007001093A patent/KR20010022507A/ko not_active Ceased
- 1998-08-05 SK SK135-2000A patent/SK1352000A3/sk unknown
- 1998-08-05 EA EA200000023A patent/EA200000023A1/ru unknown
- 1998-08-10 PE PE1998000717A patent/PE106299A1/es not_active Application Discontinuation
- 1998-08-10 PA PA19988457001A patent/PA8457001A1/es unknown
- 1998-08-12 MA MA25210A patent/MA24632A1/fr unknown
- 1998-08-12 DZ DZ980193A patent/DZ2583A1/fr active
- 1998-08-12 TN TNTNSN98151A patent/TNSN98151A1/fr unknown
- 1998-08-13 AR ARP980104021A patent/AR017019A1/es unknown
- 1998-08-14 HR HR60/055,764A patent/HRP980441A2/hr not_active Application Discontinuation
- 1998-08-14 ZA ZA9807304A patent/ZA987304B/xx unknown
- 1998-08-14 CO CO98046788A patent/CO4960656A1/es unknown
- 1998-08-17 UY UY25144A patent/UY25144A1/es not_active Application Discontinuation
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2000
- 2000-01-10 BG BG104069A patent/BG104069A/xx unknown
- 2000-01-11 IS IS5336A patent/IS5336A/is unknown
- 2000-02-08 OA OA1200000030A patent/OA11286A/en unknown
- 2000-02-14 NO NO20000722A patent/NO20000722L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| DZ2583A1 (fr) | 2003-02-22 |
| AR017019A1 (es) | 2001-08-22 |
| TR200000414T2 (tr) | 2000-08-21 |
| WO1999009025A3 (fr) | 1999-04-15 |
| CO4960656A1 (es) | 2000-09-25 |
| OA11286A (en) | 2003-10-22 |
| KR20010022507A (ko) | 2001-03-15 |
| SK1352000A3 (en) | 2000-08-14 |
| BG104069A (en) | 2001-05-31 |
| IL133960A0 (en) | 2001-04-30 |
| ID23803A (id) | 2000-05-11 |
| PL338947A1 (en) | 2000-12-04 |
| JP2002536291A (ja) | 2002-10-29 |
| HUP0003425A3 (en) | 2002-02-28 |
| EP1003739A2 (fr) | 2000-05-31 |
| CA2297486C (fr) | 2005-05-03 |
| UY25144A1 (es) | 2000-12-29 |
| ZA987304B (en) | 2000-02-14 |
| PE106299A1 (es) | 1999-11-02 |
| NO20000722D0 (no) | 2000-02-14 |
| AP9801321A0 (en) | 2000-02-14 |
| CA2297486A1 (fr) | 1999-02-25 |
| TNSN98151A1 (fr) | 2005-03-15 |
| MA24632A1 (fr) | 1999-04-01 |
| HUP0003425A2 (hu) | 2001-10-28 |
| PA8457001A1 (es) | 2000-09-29 |
| WO1999009025A2 (fr) | 1999-02-25 |
| CN1265660A (zh) | 2000-09-06 |
| IS5336A (is) | 2000-01-11 |
| NO20000722L (no) | 2000-02-14 |
| EA200000023A1 (ru) | 2000-08-28 |
| AU8457298A (en) | 1999-03-08 |
| BR9811557A (pt) | 2000-08-22 |
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