ES2193923T3 - Ciano-indoles como inhibidores de recaptura de serotonina y ligandos del receptor 5-ht2c. - Google Patents
Ciano-indoles como inhibidores de recaptura de serotonina y ligandos del receptor 5-ht2c.Info
- Publication number
- ES2193923T3 ES2193923T3 ES00400193T ES00400193T ES2193923T3 ES 2193923 T3 ES2193923 T3 ES 2193923T3 ES 00400193 T ES00400193 T ES 00400193T ES 00400193 T ES00400193 T ES 00400193T ES 2193923 T3 ES2193923 T3 ES 2193923T3
- Authority
- ES
- Spain
- Prior art keywords
- branched
- linear
- group
- optionally substituted
- groups
- 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.)
- Expired - Lifetime
Links
- 102100024959 5-hydroxytryptamine receptor 2C Human genes 0.000 title 1
- 101710138093 5-hydroxytryptamine receptor 2C Proteins 0.000 title 1
- 239000003112 inhibitor Substances 0.000 title 1
- 239000003446 ligand Substances 0.000 title 1
- 238000011084 recovery Methods 0.000 title 1
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 title 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 4
- 125000001072 heteroaryl group Chemical group 0.000 abstract 4
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 3
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 abstract 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 125000000592 heterocycloalkyl group Chemical group 0.000 abstract 2
- 125000003107 substituted aryl group Chemical group 0.000 abstract 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 1
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 abstract 1
- 125000006590 (C2-C6) alkenylene group Chemical group 0.000 abstract 1
- 125000006591 (C2-C6) alkynylene group Chemical group 0.000 abstract 1
- POXWDTQUDZUOGP-UHFFFAOYSA-N 1h-1,4-diazepine Chemical compound N1C=CC=NC=C1 POXWDTQUDZUOGP-UHFFFAOYSA-N 0.000 abstract 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- UEZROEGYRDHMRV-UHFFFAOYSA-N [1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound O=C1C=CN=C2SC=CN12 UEZROEGYRDHMRV-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000004122 cyclic group Chemical group 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical compound C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 abstract 1
- 125000001624 naphthyl group Chemical group 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 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
- C07D401/02—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 two hetero rings
- C07D401/12—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 two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
-
- 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
- A61P25/22—Anxiolytics
-
- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
-
- 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
- C07D403/06—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 carbon chain containing only aliphatic carbon atoms
-
- 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
-
- 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
- C07D403/14—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 three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biomedical Technology (AREA)
- General Health & Medical Sciences (AREA)
- Neurology (AREA)
- Veterinary Medicine (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Hospice & Palliative Care (AREA)
- Addiction (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Compuestos de fórmula (I): **FORMULA** en la cual: ¿ R1 y R2 representan independientemente un átomo de hidrógeno o un grupo alquilo, (C1-C6) lineal o ramificado, ¿ A representa un grupo alquileno (C1-C6) lineal o ramificado, un grupo alquenileno (C2-C6) lineal o ramificado, o un grupo alquinileno (C2-C6) lineal o ramificado, ¿ G1 representa un grupo -N.~R3 , en el cual R3 y R4 representan independientemente un átomo R4 de hidrógeno, un grupo alquilo (C1-C6) lineal o ramificado, arilo eventualmente sustituido y arilalquilo (C1-C6) lineal o ramificado, o bien G1 representa un grupo heterocicloalquilo, unido con A por uno cualquiera de los eslabones del ciclo y eventualmente sustituido en una cualquiera de las posiciones del ciclo por un grupo seleccionado entre arilo eventualmente sustituido, arilalquilo (C1-C6) lineal o ramificado eventualmente sustituido, heteroarilo eventualmente sustituido, sus enantiómeros, diastereoisómeros, así como sus sales de adición de un ácido o de una base farmacéuticamente aceptable, entendiéndose que: por grupo heterocicloalquilo, se entienden los grupos piperidina, piperazina, 1, 4-diazepina o pirrolidina, por grupo arilo, se entiende un grupo seleccionado entre fenilo o naftilo, por grupo heteroarilo, se entienden los grupos piridina, 2 - oxo - 2, 3 - dihidro - 1H - indol, 5 - oxo - 5H - [1, 3]tiazolo[3, 2 - a]pirimidina o 2, 4 - dioxo - 1, 4 - dihidro - 3 - (2H) - quinazolina, el término eventualmente sustituido que se asigna a las expresiones arilo, arilalquilo, heteroarilo, significa que los grupos en cuestión son sustituidos en su parte cíclica por uno o varios átomos de halógeno, y/o grupos alquilo (C1-C6) lineal o ramificado, alcoxi (C1-C6) lineal o ramificado, hidroxi, perhalogenuro de alquilo (C1-C6) lineal o ramificado, amino (eventualmente sustituido por uno o dos grupos alquilo (C1-C6) lineal o ramificado), y/o nitro, entendiéndose que los grupos heteroarilo pueden además ser sustituidos por un grupo oxo.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9900801A FR2788772B1 (fr) | 1999-01-26 | 1999-01-26 | Nouveaux composes cyano-indoles inhibiteurs de recapture de serotonine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2193923T3 true ES2193923T3 (es) | 2003-11-16 |
Family
ID=9541208
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES00400193T Expired - Lifetime ES2193923T3 (es) | 1999-01-26 | 2000-01-26 | Ciano-indoles como inhibidores de recaptura de serotonina y ligandos del receptor 5-ht2c. |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US6239129B1 (es) |
| EP (1) | EP1023898B1 (es) |
| JP (1) | JP2000212162A (es) |
| KR (1) | KR100445389B1 (es) |
| CN (1) | CN1155570C (es) |
| AT (1) | ATE234093T1 (es) |
| AU (1) | AU761084B2 (es) |
| BR (1) | BR0000158A (es) |
| CA (1) | CA2297279C (es) |
| DE (1) | DE60001591T2 (es) |
| DK (1) | DK1023898T3 (es) |
| EA (1) | EA003146B1 (es) |
| ES (1) | ES2193923T3 (es) |
| FR (1) | FR2788772B1 (es) |
| HK (1) | HK1029584A1 (es) |
| HU (1) | HUP0000308A2 (es) |
| MX (1) | MXPA00000856A (es) |
| NO (1) | NO314801B1 (es) |
| NZ (1) | NZ502494A (es) |
| PL (1) | PL338027A1 (es) |
| SI (1) | SI1023898T1 (es) |
| ZA (1) | ZA200000336B (es) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2001247562A (ja) * | 2000-03-07 | 2001-09-11 | Daicel Chem Ind Ltd | アミド化合物及びその製造方法 |
| AU2426602A (en) * | 2000-11-20 | 2002-05-27 | Biovitrum Ab | Piperazinylpyrazine compounds as agonist or antagonist of serotonin 5ht-2 receptor |
| SE0004245D0 (sv) | 2000-11-20 | 2000-11-20 | Pharmacia Ab | Novel compounds and their use |
| WO2002079152A1 (en) | 2001-03-29 | 2002-10-10 | Bristol-Myers Squibb Company | Cyclopropylindole derivatives as selective serotonin reuptake inhibitors |
| NZ537982A (en) * | 2002-09-17 | 2007-05-31 | Hoffmann La Roche | 2,7-substituted indoles and their use as 5-HT6 modulators |
| US7129264B2 (en) * | 2003-04-16 | 2006-10-31 | Bristol-Myers Squibb Company | Biarylmethyl indolines and indoles as antithromboembolic agents |
| EP1689389A4 (en) * | 2003-12-04 | 2009-06-17 | Nat Health Research Institutes | Indole compounds |
| FR2884251B1 (fr) * | 2005-04-08 | 2007-07-13 | Servier Lab | Derives de piperazine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| WO2015066344A1 (en) | 2013-11-01 | 2015-05-07 | Arena Pharmaceuticals, Inc. | 5-ht2c receptor agonists and compositions and methods of use |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK181190D0 (da) * | 1990-07-30 | 1990-07-30 | Lundbeck & Co As H | 3-aryl-indol- eller 3-aryl-indazolderivater |
| TW270114B (es) * | 1993-10-22 | 1996-02-11 | Hoffmann La Roche | |
| DE19500689A1 (de) * | 1995-01-12 | 1996-07-18 | Merck Patent Gmbh | Indolpiperidin-Derivate |
| US5912256A (en) * | 1996-06-20 | 1999-06-15 | Eli Lilly And Company | Compounds having effects on serotonin-related systems |
| JP3560986B2 (ja) * | 1997-01-13 | 2004-09-02 | 山之内製薬株式会社 | ５―ｈｔ２ｃ受容体作用薬及びアミノアルキルインダゾール誘導体 |
-
1999
- 1999-01-26 FR FR9900801A patent/FR2788772B1/fr not_active Expired - Fee Related
-
2000
- 2000-01-24 CA CA002297279A patent/CA2297279C/fr not_active Expired - Fee Related
- 2000-01-24 JP JP14544A patent/JP2000212162A/ja active Pending
- 2000-01-25 EA EA200000068A patent/EA003146B1/ru not_active IP Right Cessation
- 2000-01-25 NZ NZ502494A patent/NZ502494A/en unknown
- 2000-01-25 NO NO20000373A patent/NO314801B1/no unknown
- 2000-01-25 AU AU13553/00A patent/AU761084B2/en not_active Ceased
- 2000-01-25 PL PL00338027A patent/PL338027A1/xx not_active Application Discontinuation
- 2000-01-25 KR KR10-2000-0003388A patent/KR100445389B1/ko not_active IP Right Cessation
- 2000-01-25 MX MXPA00000856A patent/MXPA00000856A/es not_active IP Right Cessation
- 2000-01-25 BR BR0000158-9A patent/BR0000158A/pt not_active Withdrawn
- 2000-01-25 US US09/490,909 patent/US6239129B1/en not_active Expired - Fee Related
- 2000-01-26 DK DK00400193T patent/DK1023898T3/da active
- 2000-01-26 ZA ZA200000336A patent/ZA200000336B/xx unknown
- 2000-01-26 DE DE60001591T patent/DE60001591T2/de not_active Expired - Fee Related
- 2000-01-26 AT AT00400193T patent/ATE234093T1/de not_active IP Right Cessation
- 2000-01-26 ES ES00400193T patent/ES2193923T3/es not_active Expired - Lifetime
- 2000-01-26 CN CNB001011561A patent/CN1155570C/zh not_active Expired - Fee Related
- 2000-01-26 SI SI200030063T patent/SI1023898T1/xx unknown
- 2000-01-26 EP EP00400193A patent/EP1023898B1/fr not_active Expired - Lifetime
- 2000-01-26 HU HU0000308A patent/HUP0000308A2/hu unknown
-
2001
- 2001-01-12 HK HK01100310A patent/HK1029584A1/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| NO314801B1 (no) | 2003-05-26 |
| CN1155570C (zh) | 2004-06-30 |
| FR2788772A1 (fr) | 2000-07-28 |
| US6239129B1 (en) | 2001-05-29 |
| DE60001591D1 (de) | 2003-04-17 |
| EA003146B1 (ru) | 2003-02-27 |
| SI1023898T1 (en) | 2003-06-30 |
| CA2297279C (fr) | 2004-05-18 |
| DE60001591T2 (de) | 2003-12-24 |
| EA200000068A3 (ru) | 2000-10-30 |
| HUP0000308A2 (en) | 2002-06-29 |
| DK1023898T3 (da) | 2003-06-10 |
| FR2788772B1 (fr) | 2001-03-02 |
| NO20000373D0 (no) | 2000-01-25 |
| MXPA00000856A (es) | 2002-03-08 |
| JP2000212162A (ja) | 2000-08-02 |
| EP1023898A1 (fr) | 2000-08-02 |
| BR0000158A (pt) | 2000-09-19 |
| EA200000068A2 (ru) | 2000-08-28 |
| ZA200000336B (en) | 2000-08-15 |
| AU1355300A (en) | 2000-07-27 |
| AU761084B2 (en) | 2003-05-29 |
| HU0000308D0 (en) | 2000-03-28 |
| ATE234093T1 (de) | 2003-03-15 |
| HK1029584A1 (en) | 2001-04-06 |
| EP1023898B1 (fr) | 2003-03-12 |
| KR100445389B1 (ko) | 2004-08-25 |
| NO20000373L (no) | 2000-07-27 |
| PL338027A1 (en) | 2000-07-31 |
| NZ502494A (en) | 2001-06-29 |
| CN1266057A (zh) | 2000-09-13 |
| CA2297279A1 (fr) | 2000-07-26 |
| KR20010006587A (ko) | 2001-01-26 |
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