AR073631A1 - Antagonistas del receptor transitorio potencial de vanilloides 1 ( trpv1) utiles para tratar inflamacion y dolor - Google Patents
Antagonistas del receptor transitorio potencial de vanilloides 1 ( trpv1) utiles para tratar inflamacion y dolorInfo
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- AR073631A1 AR073631A1 ARP090103975A ARP090103975A AR073631A1 AR 073631 A1 AR073631 A1 AR 073631A1 AR P090103975 A ARP090103975 A AR P090103975A AR P090103975 A ARP090103975 A AR P090103975A AR 073631 A1 AR073631 A1 AR 073631A1
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- Prior art keywords
- dihydro
- urea
- indazol
- chromen
- benzopyran
- Prior art date
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- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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Abstract
Reivindicacion 1: Un compuesto caracterizado porque responde a la formula (1) o una sal solvato, prodroga, sal de una prodroga aceptables para uso farmacéutico, o una combinacion de los mismos, donde R1 representa un grupo de formula (a), (b), (c) o (d); Rx, en cada caso, representa sustituyente(s) opcional(es) sobre cualquier posicion sustituible del anillo bicíclico seleccionados entre el grupo que consiste de alquilo, halogeno, haloalquilo, OH, O(alquilo), O(haloalquilo), NH2, N(H)(alquilo), y N(alquilo)2; Ra es hidrogeno o metilo; R2 y R3 son iguales o diferentes, y son cada uno en forma independiente hidrogeno, alquilo C1-5, o haloalquilo; o R2 y R3, junto con el átomo de carbono al cual se encuentran unidos, forman un anillo cicloalquilo monocíclico de 3 a 6 átomos de carbono, opcionalmente sustituido con 1, 2 o 3 sustituyentes seleccionados entre el grupo que consiste de alquilo y halogeno; R4 en cada caso, representa sustituyente(s) opcional(es) sobre cualquier posicion sustituible del anillo bicíclico seleccionados entre el grupo que consiste de alquilo, halogeno, haloalquilo, O(alquilo), O(haloalquilo), y SCF3; y m y n son cada uno en forma independiente 0, 1, 2 o 3; con la condicion de que el compuesto no es N-(7-tert-butil-3,4-dihidro-2H-cromen-4-il)-N'-1H-indazol-4-ilurea; N-1H-indazol-4-il-N'-[7-(trifluorometil)-3,4-dihidro-2H-cromen-4-il]urea; N-isoquinolin-5-il-N'-[7-(trifluorometil)-3,4-dihidro-2H-cromen-4-il]urea; N-1H-indazol-4-il-N'-(6-metil-3,4-dihidro-2H-cromen-4-il)urea; N-isoquinolin-5-il-N'-(6-metil-3,4-dihidro-2H-cromen-4-il)urea; N-(6-fluoro-3,4-dihidro-2H-cromen-4-il)-N'-1H-indazol-4-ilurea; N-(6-fluoro-3,4-dihidro-2H-cromen-4-il)-N'-isoquinolin-5-ilurea; N-(6-cloro-7-metil-3,4-dihidro-2H-cromen-4-il)-N'-1H-indazol-4-ilurea; N-(6-cloro-7-metil-3,4-dihidro-2H-cromen-4-il)-N'-isoquinolin-5-ilurea; N-3,4-dihidro-2H-cromen-4-il-N'-1H-indazol-4-ilurea; N-(7-tert-butil-3,4-dihidro-2H-cromen-4-il)-N'-(3metilisoquinolin-5-il)urea; N-(6-fluoro-3,4-dihidro-2H-cromen-4-il)-N'-(3-metilisoquinolin-5-il)urea; N-(6-metil-3,4-dihidro-2H-cromen-4-il)-N'-(3-metilisoquinolin-5-il)urea; N-isoquinolin-5-il-N'-(8-piperidin-1-il-3,4-dihidro-2H-cromen-4-il)urea; N-3,4-dihidro-2H-cromen-4-il-N'-isoquinolin-5-ilurea; (+)-N-isoquinolin-5-il-N'-[7-(trifluorometil)-3,4-dihidro-2H-cromen-4-il]urea; (-)-N-isoquinolin-5-il-N'-[7-(trifluorometil)-3,4-dihidro-2H-cromen-4-il]urea; N-1H-indazol-4-il-N'-[8-(trifluorometil)-3,4-dihidro-2H-cromen-4-il]urea; (-)-N-1H-indazol-4-il-N'-[7-(trifluorometil)-3,4-dihidro-2H-cromen-4-il]urea; (+)-N-1H-indazol-4-il-N'-[7-(trifluorometil)-3,4-dihidro-2H-cromen-4-il]urea; N-1H-indazol-4-il-N'-(8-piperidin-1-il-3,4-dihidro-2H-cromen-4-il)urea; N-(8-tert-butil-3,4-dihidro-2H-cromen-4-il)-N'-1H-indazol-4-ilurea; N-[8-cloro-7-(trifluorometil)-3,4-dihidro-2H-cromen-4-il]-N'-1H-indazol-4-ilurea; (+)-N-(8-tert-butil-3,4-dihidro-2H-cromen-4-il)-N'-1H-indazol-4-ilurea; (-)-N-(8-tert-butil-3,4-dihidro-2H-cromen-4-il)-N'-1H-indazol-4-ilurea; N-1H-indazol-4-il-N'-[8-(trifluorometoxi)-3,4-dihidro-2H-cromen-4-il]urea; N-[8-fluoro-7-(trifluorometil)-3,4-dihidro-2H-cromen-4-il]-N'-1H-indazol-4-ilurea; N-1H-indazol-4-il-N'-[7-(trifluorometoxi)-3,4-dihidro-2H-cromen-4-il]urea; N-(6-fluoro-2-metil-3,4-dihidro-2H-cromen-4-il)-N'-1H-indazol-4-ilurea; N-1H-indazol-4-il-N'-(7-metoxi-2,2-dimetil-3,4-dihidro-2H-cromen-4-il)urea; N-1H-indazol-4-il-N'-(7-metoxi-2,2,8-trimetil-3,4-dihidro-2H-cromen-4-il)urea; N-1H-indazol-4-il-N'-(2,2,8-trimetil-3,4-dihidro-2H-cromen-4-il)urea; N-1H-indazol-4-il-N'-(7-metoxi-2,2-dimetil-8-propil-3,4-dihidro-2H-cromen-4-il)urea; N-(2,2-dimetil-3,4-dihidro-2H-cromen-4-il)-N'-1H-indazol-4-ilurea; N-(7-fluoro-2,2-dimetil-3,4-dihidro-2H-cromen-4-il)-N'-1H-indazol-4-ilurea; N-(7-fluoro-2,2-dietil-3,4-dihidro-2H-cromen-4-il)-N'-1H-indazol-4-ilurea; N-(7,8-difluoro-2,2-dimetil-3,4-dihidro-2H-cromen-4-il)-N'-1H-indazol-4-ilurea; N-(7-(3,3-dimetilbutil)-3,4-dihidro-2H-cromen-4-il)-N'-1H-indazol-4-ilurea; N-(7-tert-butil-2,2-dimetil-3,4-dihidro-2H-cromen-4-il)-N'-1H-indazol-4-ilurea; N-(2,2-dietil-7-fluoro-3,4-dihidro-2H-cromen-4-il)-N'-(1-metil-1H-indazol-4-il)urea; N-(7,8-difluoro-3,4-dihidro-2H-cromen-4-il)-N'-1H-indazol-4-ilurea; N-(7-fluoro-2,2-dipropil-3,4-dihidro-2H-cromen-4-il)-N'-1H-indazol-4-ilurea; N-(2,2-dibutil-7-fluoro-3,4-dihidro-2H-cromen-4-il)-N'-1H-indazol-4-ilurea; N-(2-tert-butil-7-fluoro-3,4-dihidro-2H-cromen-4-il)-N'-1H-indazol-4-ilurea; N-(2-tert-butil-7-fluoro-3,4-dihidro-2H-cromen-4-il)-N'-(1-metil-1H-indazol-4-il)urea; N-(8-tert-butil-3,4-dihidro-2H-cromen-4-il)-N'-(7-hidroxi-5,6,7,8-tetrahidronaftalen-1-il)urea; N-(7-hidroxi-5,6,7,8-tetrahidronaftalen-1-il)-N'-(6-metil-3,4-dihidro-2H-cromen-4-il)urea; N-[(4R)-3,4-dihidro-2H-cromen-4-il]-N'-(7-hidroxi-5,6,7,8-tetrahidronaftalen-1-il)urea; N-[(4S)-3,4-dihidro-2H-cromen-4-il]-N'-(7-hidroxi-5,6,7,8-tetrahidronaftalen-1-il)urea; 1-(1H-indazol-4-il)-3-(espiro[croman-2,1'-ciclohexan]-4-il)urea; 1-(7-fluoroespiro[croman-2,1'-ciclohexan]-4-il)-3-(1H-indazol-4-il)urea; 1-(7-fluoroespiro[croman-2,1'-cicIobutan]-4-il)-3-(1H-indazol-4-il)urea; 1-(7-fluoroespiro[croman-2,1'-ciclobutan]-4-il)-3-(1-metil-1H-indazol-4-il)urea; 1-(6,7-dimetilespiro[croman-2,1'-ciclohexan]-4-il)-3-(1H-indazol-4-il)urea; 1-(6,8-dicloroespiro[croman-2,1'-ciclohexan]-4-il)-3-(1H-indazol-4-il)urea; 1-(6-cloroespiro[croman-2,1l-ciclohexan]-4-il)-3-(1H-indazol-4-il)urea; 1-(7-tertbutilespiro[croman-2,1'-ciclobutan]-4-il)-3-(1H-indazol-4-il)urea, 1-(6,8-difluoroespiro[croman-2,1'-ciclohexan]-4-il)-3-(1H-indazol-4-il)urea; 1-(6-etoxiespiro[croman-2,1'-ciclohexan]-4-il)-3-(1H-indazol-4-il)urea; 1-(1H-indazol-4-il)-3-(6-metilespiro[croman-2,1'-ciclopentan]-4-il)urea; 1-(7-etoxiespiro[croman-2,1'-ciclopentan]-4-il)-3-(1H-indazol-4-il)urea; 1-(6,7-dimetilespiro[croman-2,1'-ciclopentan]-4-il)-3-(1H-indazol-4-il)urea; 1-(7-fluoroespiro[croman-2,1l-ciclopentan]-4-il)-3-(1H-indazol-4-il)urea; 1-(1-metil-1H-indazol-4-il)-3-(espiro[croman-2,1'-ciclohexan]-4-il)urea; 1-(1H-indazol-4-il)-3-(7-metoxiespiro[croman-2,1'-ciclohexan]-4-il)urea; (+- )1-(3,4-dihidro-2,2-dimetil-2H-1-benzopiran-4-il)-3-(isoquinolin-5-il)urea; (+- )1-(7-cloro-3,4-dihidro-2,2-dimetil-2H-1-benzopiran-4-il)-3-(isoquinolin-5-il)urea; (+- )1-(6-bromo-3,4-dihidro-2,2-dimetil-2H-1-benzopiran-4-il)-3-(isoquinolin-5-il)urea; (+- )1-(6-metoxi-3,4-dihidro-2,2-dimetil-2H-1-benzopiran-4-il)-3-(isoquinolin-5-il)urea; (+- )1-(7-metoxi-3,4-dihidro-2,2-dimetil-2H-1-benzopiran-4-il)-3-(isoquinolin-5-il)urea; (+- )1-(6-metil-3,4-dihidro-2,2-dimetil-2H-1-benzopiran-4-il)-3-(isoquinolin-5-il)urea; (+- )1-(7-metoxi-3,4-dihidro-2,2-dimetil-2H-1-benzopiran-4-il)-3-(1-metilisoquinoIin-5-il)urea; (+- )1-(6-bromo-3,4-dihidro-2,2-dimetil-2H-1-benzopiran-4-il)-3-(1-metilisoquinolin-5-il)urea; (+- )1-(6-metil-3,4-dihidro-2,2-dimetil-2H-1-benzopiran-4-il)-3-(1-metilisoquinolin-5-il)urea; (+- )1-(3,4-dihidro-2,2-dimetil-2H-1-benzopiran-4-il)-3-(1-metilisoquinolin-5-il)urea; (+- )1-(3,4-dihidro-espiro-[2H-1-benzopiran-2,1'-ciclobutan]-4-il)-3-(isoquinolin-5-il)urea; (+)1-(3,4-dihidro-espiro-[2H-1-benzopiran-2,1'-ciclobutan]-4-il)-3-(isoquinolin-5-il)urea; (-)1-(3,4-dihidro-espiro-[2H-1-benzopiran-2,1'-ciclobutan]-4-il)-3-(isoquinolin-5-il)urea; (+- )1-(3,4-dihidro-espiro-[2H-1-benzopiran-2,1'-ciclobutan]-4-il)-3-(8-cloroisoquinolin-5-il)urea; (+- )1-(3,4-dihidro-espiro-[2H-1-benzopiran-2,1'-ciclobutan]-4-il)-3-(3-metilisoquinolin-5-il)urea; (+- )1-(3,4-dihidro-espiro-[2H-1-benzopiran-2,1'-ciclobutan]-4-il)-3-(1-metilisoquinolin-5-il)urea; (+- )1-(3,4-dihidro-6-metil-espiro-[2H-1-benzopiran-2,1'-ciclobutan]-4-il)-3-(isoquinolin-5-il)urea; (+- )1-(3,4-dihidro-7-metil-espiro-[2H-1-benzopiran-2,1'-ciclobutan]-4-il)-3-(isoquinolin-5-il)urea; (+- )1-(3,4-dihidro-6-fluoro-espiro-[2H-1-benzopiran-2,1'-ciclobutan]-4-il)-3-(isoquinolin-5-il)urea; (+)1-(3,4-dihidro-6-fluoro-espiro-[2H-1-benzopiran-2,1'-ciclobutan]-4-il)-3-(isoquinolin-5-il)urea; (-)1-(3,4-dihidro-6-fluoro-espiro-[2H-1-benzopiran-2,1'-ciclobutan]-4-il)-3-(isoquinolin-5-il)urea; (+- )1-(3,4-dihidro-7-metoxi-espiro-[2H-1-benzopiran-2,1'-ciclobutan]-4-il)-3-(isoquinolin-5-il)urea; 1-(6,8-difluoro-3,4-dihidro-espiro-[2H-1-benzopiran-2,1'-ciclobutan]-4-il)-3-(isoquinolin-5-il)urea; (+- )1-(8-cloro-3,4-dihidro-espiro-[2H-1-benzopiran-2,1'-ciclobutan]-4-il)-3-(isoquinolin-5-il)urea; (+- )1-(3,4-dihidro-6-metoxi-espiro-[2H-1-benzopiran-2,1'-ciclobutan]-4-il)-3-(isoquinolin-5-il)urea; clorhidrato de (+- )1-(7-difluorometoxi-3,4-dihidro-espiro-[2H-1-benzopiran-2,1'-ciclobutan]-4-il)-3-(isoquinolin-5-il)urea; (+- )1-(7-difluorometoxi-3,4-dihidro-espiro-[2H-1-benzopiran-2,1'-ciclobutan]-4-il)-3-(3-metilisoquinolin-5-il)urea; (+- )1-(7-cloro-3,4-dihidro-espiro-[2H-1-benzopiran-2,1'-ciclobutan]-4-il)-3-(3-metilisoquinolin-5-il)urea; (+)1-(6,8-difluoro-3,4-dihidro-espiro-[2H-1-benzopiran-2,1'-ciclobutan]-4-il)-3-(isoquinolin-5-il)urea; (-)1-(6,8-difluoro-3,4-dihidro-espiro-[2H-1-benzopiran-2,1'-ciclobutan]-4-il)-3-(isoquinolin-5-il)urea; (+- )1-(3,4-dihidro-8-difluorometoxi-espiro-[2H-1-benzopiran-2,1'-ciclobutan]-4-il)-3-(isoquinolin-5-il)urea; (+- )1-(6-cloro-3,4-dihidro-espiro-[2H-1-benzopiran-2,1'-ciclobutan]-4-il)-3-(isoquinolin-5-il)urea; (-)1-(6-cloro-3,4-dihidro-espiro-[2H-1-benzopiran-2,1'-ciclobutan]-4-il)-3-(isoquinolin-5-il)urea; (+- )1-(6-bromo-3,4-dihidro-espiro-[2H-1-benzopiran-2,1'-ciclobutan]-4-il)-3-(isoquinolin-5-il)urea; (+- )1-(6,8-dicloro-3,4-dihidro-espiro-[2H-1-benzopiran-2,1'-ciclobutan]-4-il)-3-(isoquinolin-5-il)urea; (+- )1-(6-bromo-3,4-dihidro-7-metilespiro-[2H-1-benzopiran-2,1'-ciclobutan]-4-il)-3-(isoquinolin-5-il)urea; (+- )1-(6,7-dicloro-3,4-dihidro-espiro-[2H-1-benzopiran-2,1'-ciclobutan]-4-il)-3-(isoquinolin-5-il)urea; (+- )1-(6-cloro-3,4-dihidro-7-metilespiro-[2H-1-benzopiran-2,1'-ciclobutan]-4-il)-3-(isoquinolin-5-il)urea; (+- )1-(6-cloro-3,4-dihidro-espiro-[2H-1-benzopiran-2,1'-ciclobutan]-4-il)-3-(8-cloroisoquinolin-5-il)urea; (+- )1-(6-fluoro-3
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-
2009
- 2009-10-15 CN CN2009801412472A patent/CN102186836A/zh active Pending
- 2009-10-15 US US12/579,821 patent/US8604053B2/en active Active
- 2009-10-15 JP JP2011532227A patent/JP2012505907A/ja active Pending
- 2009-10-15 UY UY0001032180A patent/UY32180A/es not_active Application Discontinuation
- 2009-10-15 PA PA20098845601A patent/PA8845601A1/es unknown
- 2009-10-15 TW TW098134972A patent/TW201020236A/zh unknown
- 2009-10-15 AR ARP090103975A patent/AR073631A1/es not_active Application Discontinuation
- 2009-10-15 WO PCT/US2009/060732 patent/WO2010045401A1/en active Application Filing
- 2009-10-15 MX MX2011004081A patent/MX2011004081A/es not_active Application Discontinuation
- 2009-10-15 EP EP09740591A patent/EP2352726A1/en not_active Withdrawn
- 2009-10-15 CA CA2737768A patent/CA2737768A1/en not_active Abandoned
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MX2011004081A (es) | 2011-05-31 |
CA2737768A1 (en) | 2010-04-22 |
US8604053B2 (en) | 2013-12-10 |
CN102186836A (zh) | 2011-09-14 |
PA8845601A1 (es) | 2010-05-26 |
UY32180A (es) | 2010-05-31 |
EP2352726A1 (en) | 2011-08-10 |
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