CA2457922A1 - Nouveaux analogues de pyrazole agissant sur les recepteurs cannabinoides - Google Patents
Nouveaux analogues de pyrazole agissant sur les recepteurs cannabinoides Download PDFInfo
- Publication number
- CA2457922A1 CA2457922A1 CA002457922A CA2457922A CA2457922A1 CA 2457922 A1 CA2457922 A1 CA 2457922A1 CA 002457922 A CA002457922 A CA 002457922A CA 2457922 A CA2457922 A CA 2457922A CA 2457922 A1 CA2457922 A1 CA 2457922A1
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- Prior art keywords
- ring
- group
- members
- alkyl
- substituted
- 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.)
- Abandoned
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- 102000018208 Cannabinoid Receptor Human genes 0.000 title claims abstract description 14
- 108050007331 Cannabinoid receptor Proteins 0.000 title claims abstract description 14
- 150000003217 pyrazoles Chemical class 0.000 title abstract description 19
- 238000000034 method Methods 0.000 claims abstract description 23
- -1 COOX3 Chemical group 0.000 claims description 174
- 125000006413 ring segment Chemical group 0.000 claims description 172
- 125000000217 alkyl group Chemical group 0.000 claims description 147
- 229910052757 nitrogen Inorganic materials 0.000 claims description 120
- 125000005842 heteroatom Chemical group 0.000 claims description 107
- 125000000623 heterocyclic group Chemical group 0.000 claims description 105
- 229910052760 oxygen Inorganic materials 0.000 claims description 71
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 70
- 229910052717 sulfur Inorganic materials 0.000 claims description 69
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 66
- 125000006307 alkoxy benzyl group Chemical group 0.000 claims description 64
- 125000001072 heteroaryl group Chemical group 0.000 claims description 64
- 150000001875 compounds Chemical class 0.000 claims description 61
- 125000004432 carbon atom Chemical group C* 0.000 claims description 54
- 229910052736 halogen Inorganic materials 0.000 claims description 45
- 150000002367 halogens Chemical class 0.000 claims description 45
- 125000003545 alkoxy group Chemical group 0.000 claims description 44
- 125000004414 alkyl thio group Chemical group 0.000 claims description 44
- 229910052799 carbon Inorganic materials 0.000 claims description 44
- 125000003282 alkyl amino group Chemical group 0.000 claims description 43
- 125000002837 carbocyclic group Chemical group 0.000 claims description 43
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 41
- 125000003118 aryl group Chemical group 0.000 claims description 40
- 150000003949 imides Chemical group 0.000 claims description 38
- 150000003839 salts Chemical class 0.000 claims description 38
- 125000002619 bicyclic group Chemical group 0.000 claims description 34
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 33
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 32
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 32
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 30
- 125000003367 polycyclic group Chemical group 0.000 claims description 29
- 125000004585 polycyclic heterocycle group Chemical group 0.000 claims description 28
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 27
- 125000000169 tricyclic heterocycle group Chemical group 0.000 claims description 26
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 16
- 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 claims description 16
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 16
- 125000004312 morpholin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC([H])(*)C1([H])[H] 0.000 claims description 16
- 125000004572 morpholin-3-yl group Chemical group N1C(COCC1)* 0.000 claims description 16
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 16
- 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims description 16
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 16
- 102000009132 CB1 Cannabinoid Receptor Human genes 0.000 claims description 14
- 108010073366 CB1 Cannabinoid Receptor Proteins 0.000 claims description 14
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- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims 27
- XSXHWVKGUXMUQE-UHFFFAOYSA-N osmium dioxide Inorganic materials O=[Os]=O XSXHWVKGUXMUQE-UHFFFAOYSA-N 0.000 claims 9
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- 239000008194 pharmaceutical composition Substances 0.000 claims 1
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- 125000001424 substituent group Chemical group 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 230000027455 binding Effects 0.000 description 14
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- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 239000012267 brine Substances 0.000 description 10
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
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- 241000700159 Rattus Species 0.000 description 6
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
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- LWMPFIOTEAXAGV-UHFFFAOYSA-N piperidin-1-amine Chemical compound NN1CCCCC1 LWMPFIOTEAXAGV-UHFFFAOYSA-N 0.000 description 5
- 239000011593 sulfur Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
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Abstract
L'invention concerne des analogues de pyrazole cannabimim~tiques. L'invention concerne ~galement de nouveaux analogues de pyrazole am~lior~s pr~sentant de hautes affinit~s et/ou s~lectivit~s pour le r~cepteur cannabino~de GB1. L'invention concerne en outre des pr~parations pharmaceutiques dans lesquelles sont utilis~es les analogues de l'invention, ainsi que des m~thodes d'administration de quantit~s efficaces d'un point de vue th~rapeutique des analogues de l'invention afin d'obtenir un effet physiologique.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US31651501P | 2001-08-31 | 2001-08-31 | |
| US60/316,515 | 2001-08-31 | ||
| PCT/US2002/027644 WO2003020217A2 (fr) | 2001-08-31 | 2002-08-29 | Nouveaux analogues de pyrazole agissant sur les recepteurs cannabinoides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2457922A1 true CA2457922A1 (fr) | 2003-03-13 |
Family
ID=23229374
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002457922A Abandoned CA2457922A1 (fr) | 2001-08-31 | 2002-08-29 | Nouveaux analogues de pyrazole agissant sur les recepteurs cannabinoides |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP1421077A4 (fr) |
| JP (1) | JP2005507875A (fr) |
| AU (1) | AU2002331766A1 (fr) |
| CA (1) | CA2457922A1 (fr) |
| WO (1) | WO2003020217A2 (fr) |
Families Citing this family (88)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2340445A1 (fr) | 1998-05-04 | 1999-11-11 | The University Of Connecticut | Nouveaux cannabinoides analgesiques et immunomodulateurs |
| US7589220B2 (en) | 1998-06-09 | 2009-09-15 | University Of Connecticut | Inhibitors of the anandamide transporter |
| US7161016B1 (en) | 1998-11-24 | 2007-01-09 | University Of Connecticut | Cannabimimetic lipid amides as useful medications |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3041343A (en) * | 1959-10-14 | 1962-06-26 | Sandoz Ltd | 4-(thienyl-2'')-and 4-(pyridyl-3'')-5-aminopyrazoles |
| FR2692575B1 (fr) * | 1992-06-23 | 1995-06-30 | Sanofi Elf | Nouveaux derives du pyrazole, procede pour leur preparation et compositions pharmaceutiques les contenant. |
| FR2742148B1 (fr) * | 1995-12-08 | 1999-10-22 | Sanofi Sa | Nouveaux derives du pyrazole-3-carboxamide, procede pour leur preparation et compositions pharmaceutiques les contenant |
| US5939429A (en) * | 1997-09-30 | 1999-08-17 | Virginia Commonwealth University | Cardiovascular uses of cannabinoid compounds |
| WO2001058869A2 (fr) * | 2000-02-11 | 2001-08-16 | Bristol-Myers Squibb Company | Modulateurs de recepteurs aux cannabinoides, leurs procedes de preparation et utilisations de modulateurs de recepteurs aux cannabinoides pour le traitement de maladies respiratoires et non respiratoires |
-
2002
- 2002-08-29 CA CA002457922A patent/CA2457922A1/fr not_active Abandoned
- 2002-08-29 WO PCT/US2002/027644 patent/WO2003020217A2/fr not_active Ceased
- 2002-08-29 AU AU2002331766A patent/AU2002331766A1/en not_active Abandoned
- 2002-08-29 JP JP2003524531A patent/JP2005507875A/ja active Pending
- 2002-08-29 EP EP02768751A patent/EP1421077A4/fr not_active Withdrawn
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| Publication number | Publication date |
|---|---|
| JP2005507875A (ja) | 2005-03-24 |
| EP1421077A4 (fr) | 2004-11-17 |
| AU2002331766A1 (en) | 2003-03-18 |
| WO2003020217A2 (fr) | 2003-03-13 |
| WO2003020217A3 (fr) | 2003-08-21 |
| EP1421077A2 (fr) | 2004-05-26 |
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