ES2272809T3 - Nuevos derivados de 4,5-dihidro-1h-pirazol con actividad antagonista de cb1. - Google Patents
Nuevos derivados de 4,5-dihidro-1h-pirazol con actividad antagonista de cb1. Download PDFInfo
- Publication number
- ES2272809T3 ES2272809T3 ES02799408T ES02799408T ES2272809T3 ES 2272809 T3 ES2272809 T3 ES 2272809T3 ES 02799408 T ES02799408 T ES 02799408T ES 02799408 T ES02799408 T ES 02799408T ES 2272809 T3 ES2272809 T3 ES 2272809T3
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- Prior art keywords
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- alkyl
- hydroxy
- substituted
- amino
- 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
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- 239000005557 antagonist Substances 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 5
- 125000003118 aryl group Chemical group 0.000 abstract 5
- -1 trifluoromethoxy, nitro, amino Chemical group 0.000 abstract 5
- 125000003545 alkoxy group Chemical group 0.000 abstract 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 4
- 229910052731 fluorine Inorganic materials 0.000 abstract 3
- 125000001153 fluoro group Chemical group F* 0.000 abstract 3
- 125000001544 thienyl group Chemical group 0.000 abstract 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 abstract 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- 125000003342 alkenyl group Chemical group 0.000 abstract 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 2
- 125000000392 cycloalkenyl group Chemical group 0.000 abstract 2
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 2
- 125000004404 heteroalkyl group Chemical group 0.000 abstract 2
- 125000000592 heterocycloalkyl group Chemical group 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 125000000468 ketone group Chemical group 0.000 abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- 125000004076 pyridyl group Chemical group 0.000 abstract 2
- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 abstract 2
- 125000001424 substituent group Chemical group 0.000 abstract 2
- 229910052717 sulfur Inorganic materials 0.000 abstract 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 abstract 1
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 abstract 1
- 125000000081 (C5-C8) cycloalkenyl group Chemical group 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 abstract 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 abstract 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 abstract 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000005842 heteroatom Chemical group 0.000 abstract 1
- 125000005885 heterocycloalkylalkyl group Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000001624 naphthyl group Chemical group 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
- 239000011593 sulfur Substances 0.000 abstract 1
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 abstract 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 abstract 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/06—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
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- A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
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- A61P1/12—Antidiarrhoeals
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- A61P11/06—Antiasthmatics
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- 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
- C07D401/06—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 carbon chain containing only aliphatic carbon atoms
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- 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
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- 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
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- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
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- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Neurology (AREA)
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- Diabetes (AREA)
- Pain & Pain Management (AREA)
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- Psychiatry (AREA)
- Obesity (AREA)
- Psychology (AREA)
- Oncology (AREA)
- Ophthalmology & Optometry (AREA)
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- Communicable Diseases (AREA)
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Compuestos de la **fórmula**, en donde - R y R1 independientemente representan fenilo, tienilo o piridilo, los cuales son grupos que pueden estar sustituidos con 1, 2, 3 ó 4 sustituyentes Y, que pueden ser los mismos o diferentes, del grupo alquilo de C1-3 o alcoxi, hidroxi, halógeno, trifluorometilo, trifluorometiltio, trifluorometoxi, nitro, amino, mono- o dialquil de (C1-2)-amino, mono- o dialquil de (C1-2)-amido, alquil (C1-3)-sulfonilo de, dimetilsulfamido, alcoxi de C1-3-carbonilo, carboxilo, trifluorometilsulfonilo, ciano, carbamoilo, sulfamoilo y acetilo, o R y/o R1 representan naftilo, - R2 representa hidrógeno, hidroxi, alcoxi de C1-3, acetiloxi o propioniloxi, - R3 representa un átomo de hidrógeno o un grupo alquilo de C1-8 ramificado o no ramificado o un grupo cicloalquilo de C3-7 donde el grupo alquilo o grupo cicloalquilo puede estar sustituido con un grupo hidroxi, - R4 representa un grupo heteroalquilo de C2-10 ramificado o no ramificado, un grupo heterocicloalquilo no aromático de C3-8 o un grupo heterocicloalquil- alquilo no aromático de C4-10 cuyos grupos contienen uno o más heteroátomos del grupo (O, N, S) o un grupo -SO2-, cuyo grupo heteroalquilo ramificado o no ramificado de C2-10, grupo heterocicloalquilo no aromático de C3-8 o grupo heterocicloalquil-alquilo de C4-10no aromático puede estar sustituido con un grupo ceto, un grupo trifluorometilo, un grupo alquilo de C1-3, hidroxi, amino, monoalquilamino o un grupo dialquilamino o un átomo de flúor o R4 representa un grupo amino, hidroxi, fenoxi, o un grupo benciloxi, o R4 representa un grupo alcoxi de C1-8, alquenilo de C3-8, cicloalquenilo de C5-8, o un grupo cicloalquenilalquilo de C6-9 cuyos grupos pueden contener un átomo de azufre, nitrógeno u oxígeno, un grupo ceto o un grupo -SO2-, cuyos grupos alcoxi, alquenilo y cicloalquenilo pueden estar sustituidos con un grupo hidroxi, un grupo trifluorometilo, un grupo amino, un grupo monoalquilamino o un grupo dialquilamino o un átomo de flúor, o R4 representa un grupo alquilo de C2-5 cuyo grupo alquilo contiene un átomo de flúor o R4 representa un grupo imidazolilalquilo, bencilo, piridilmetilo, fenetilo o tienilo, o R4 representa un fenilo sustituido, bencilo, piridilo, tienilo, piridilmetilo o un grupo fenetilo, en donde los anillos aromáticos están sustituidos con 1, 2 ó 3 de los sustituyentes Y, en donde Y tiene el significado como se indicó anteriormente.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP01203850 | 2001-09-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2272809T3 true ES2272809T3 (es) | 2007-05-01 |
Family
ID=8181043
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES02799408T Expired - Lifetime ES2272809T3 (es) | 2001-09-21 | 2002-09-17 | Nuevos derivados de 4,5-dihidro-1h-pirazol con actividad antagonista de cb1. |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US7528162B2 (es) |
| EP (1) | EP1429761B1 (es) |
| JP (1) | JP4313671B2 (es) |
| KR (1) | KR100903760B1 (es) |
| CN (2) | CN1555262A (es) |
| AR (1) | AR036596A1 (es) |
| AT (1) | ATE344663T1 (es) |
| AU (1) | AU2002333852B2 (es) |
| BR (1) | BR0212044A (es) |
| CA (1) | CA2456606C (es) |
| DE (1) | DE60215960T2 (es) |
| DK (1) | DK1429761T3 (es) |
| ES (1) | ES2272809T3 (es) |
| HR (1) | HRP20040085A2 (es) |
| HU (1) | HUP0401567A3 (es) |
| IL (2) | IL160081A0 (es) |
| MX (1) | MXPA04002583A (es) |
| NO (1) | NO20041176L (es) |
| PL (1) | PL368441A1 (es) |
| PT (1) | PT1429761E (es) |
| RU (1) | RU2299199C2 (es) |
| SI (1) | SI1429761T1 (es) |
| UA (1) | UA78523C2 (es) |
| WO (1) | WO2003026647A1 (es) |
| ZA (1) | ZA200402099B (es) |
Families Citing this family (102)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2272809T3 (es) | 2001-09-21 | 2007-05-01 | Solvay Pharm Bv | Nuevos derivados de 4,5-dihidro-1h-pirazol con actividad antagonista de cb1. |
| ATE486842T1 (de) | 2002-03-12 | 2010-11-15 | Merck Sharp & Dohme | Substituierte amide |
| US7129239B2 (en) | 2002-10-28 | 2006-10-31 | Pfizer Inc. | Purine compounds and uses thereof |
| US7247628B2 (en) | 2002-12-12 | 2007-07-24 | Pfizer, Inc. | Cannabinoid receptor ligands and uses thereof |
| US7772188B2 (en) | 2003-01-28 | 2010-08-10 | Ironwood Pharmaceuticals, Inc. | Methods and compositions for the treatment of gastrointestinal disorders |
| US7329658B2 (en) | 2003-02-06 | 2008-02-12 | Pfizer Inc | Cannabinoid receptor ligands and uses thereof |
| US7176210B2 (en) | 2003-02-10 | 2007-02-13 | Pfizer Inc. | Cannabinoid receptor ligands and uses thereof |
| US7145012B2 (en) | 2003-04-23 | 2006-12-05 | Pfizer Inc. | Cannabinoid receptor ligands and uses thereof |
| US7141669B2 (en) | 2003-04-23 | 2006-11-28 | Pfizer Inc. | Cannabiniod receptor ligands and uses thereof |
| US7268133B2 (en) | 2003-04-23 | 2007-09-11 | Pfizer, Inc. Patent Department | Cannabinoid receptor ligands and uses thereof |
| US7232823B2 (en) | 2003-06-09 | 2007-06-19 | Pfizer, Inc. | Cannabinoid receptor ligands and uses thereof |
| TW200511990A (en) * | 2003-09-02 | 2005-04-01 | Solvay Pharm Gmbh | Novel medical uses of 4, 5-dihydro-1h-pyrazole derivatives having cb1-antagonistic activity |
| US20050239859A2 (en) * | 2003-09-03 | 2005-10-27 | Solvay Pharmaceuticals Gmbh | Novel medical uses of 4,5-dihydro-1h-pyrazole derivatives having cb1- antagonistic activity |
| FR2861302A1 (fr) * | 2003-10-24 | 2005-04-29 | Sanofi Synthelabo | Utilisation d'un derive du pyrazole, pour la preparation de medicaments utiles dans la prevention et le traitement du syndrome metabolique. |
| CA2543338A1 (en) * | 2003-10-24 | 2005-05-06 | Solvay Pharmaceuticals Gmbh | Novel medical uses of compounds showing cb1-antagonistic activity and combination treatment involving said compounds |
| FR2861303A1 (fr) * | 2003-10-24 | 2005-04-29 | Sanofi Synthelabo | Utilisation d'un derive de pyrazole pour la preparation de medicaments utiles dans la prevention et le traitement du syndrome metabolique |
| TW200528102A (en) * | 2003-10-24 | 2005-09-01 | Solvay Pharm Gmbh | Novel medical combination treatment of obesity involving 4,5-dihydro-1h-pyrazole derivatives having cb1-antagonistic activity |
| FR2861301B1 (fr) * | 2003-10-24 | 2008-07-11 | Sanofi Synthelabo | Utilisation du derive du pyrazole pour la preparation de medicaments utiles dans la prevention et le traitement du syndrome metabolique. |
| FR2861300B1 (fr) * | 2003-10-24 | 2008-07-11 | Sanofi Synthelabo | Utilisation d'un derive du pyrazole, pour la preparation de medicaments utiles dans la prevention et le traitement du syndrome metabolique |
| US20050124660A1 (en) * | 2003-10-27 | 2005-06-09 | Jochen Antel | Novel medical uses of compounds showing CB1-antagonistic activity and combination treatment involving said compounds |
| US20050143441A1 (en) * | 2003-10-27 | 2005-06-30 | Jochen Antel | Novel medical combination treatment of obesity involving 4,5-dihydro-1H-pyrazole derivatives having CB1-antagonistic activity |
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