AR053011A1 - Compuestos de heteroarilo como inhibidores del receptor p2y1, composiciones farmaceuticas que los contienen y su uso en la manufactura de un medicamento para el tratamiento de un trastorno tromboembolico - Google Patents
Compuestos de heteroarilo como inhibidores del receptor p2y1, composiciones farmaceuticas que los contienen y su uso en la manufactura de un medicamento para el tratamiento de un trastorno tromboembolicoInfo
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- AR053011A1 AR053011A1 ARP060100185A ARP060100185A AR053011A1 AR 053011 A1 AR053011 A1 AR 053011A1 AR P060100185 A ARP060100185 A AR P060100185A AR P060100185 A ARP060100185 A AR P060100185A AR 053011 A1 AR053011 A1 AR 053011A1
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
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- C07D213/72—Nitrogen atoms
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- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
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- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- 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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- C07D401/14—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 three or more hetero rings
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- C07D405/14—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 three or more hetero rings
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- 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
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- 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
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Abstract
Compuestos de heteroarilo y análogos de los mismos, los cuales son inhibidores selectivos del receptor humano P2Y1. También diversas composiciones farmacéuticas de los mismos y uso en la fabricacion de medicamentos para el tratamiento de enfermedades en respuesta a la modulacion de la actividad del receptor P2Y1, tales como trastornos tromboembolicos. Reivindicacion 1: Un compuesto de la formula (1), o un estereoisomero, tautomero, sal farmacéuticamente aceptable, solvato, o fármaco del mismo, caracterizado porque: el anillo A es un heteroarilo de 5 a 6 miembros que comprende: átomos de carbono y 1-4 heteroátomos en el anillo seleccionados de N, NR11, S(O)p, y O, en donde el heteroarilo es sustituido con 0-4 R1; el anillo B es fenilo sustituido con 0-4 R7, piridilo sustituido con 0-3 R7, o tienilo sustituido con 0-2 R7; X es NH o NMe; Y es O u S; R1 es, independientemente cada vez que se presenta, F, Cl, Br, I, CF3, -CF2CF3, OCF3, -OCF2CF2H, -OCF2CF3, SiMe3, - (CRfRf)r-ORc, SRc, CN, NO2, -(CRfRf)r-NR12R13, -(CRfRf)r-C(O)Rc, -(CRfRf)r-CO2Rc, -(CRfRf)r-C(O)NR12R13, -C(O)NR14(CRfRf)tN12R13, -(CRfRf)r-OC(O)NR12R13, -(CRfRf)r-NR14C(O)NR12R13, -(CRfRf)r-NR14C(O)Rd, -(CRfRf)r-NR14C(O)ORh, -NR14(CRfRf)nC(O)Rd, - NR14CO(CRfRf)nORc, -(CH2)r-CR13(=NORc), -(CH2)r-C(NH2)(=NORc), -S(O)pNR12R13, -(CRfRf)r-NR14S(O)pNR12R13, -NR14SO2CF3, -NR14S(O)pRd, -S(O)2CF3, -S(O)Rd, -S(O)2Rd -OP(O)(OEt)2, -O(CH2)2OP(O)(OEt)2, 4,4,5,5-tetrametil-1,3,2-dioxaborolanilo, alquilo C1- 8 sustituido con 0-2 Ra, alquenilo C2-8 sustituido con 0-2 Ra, alquinilo C2-8 sustituido con 0-2 Ra, carbocicloC3-13-(CRfRf)r- substituido con 0-5 Rb, o (CRfRf)r-heterociclo de 5 a 10 miembros que comprende: átomos de carbono y 1-4 heteroátomos seleccionados de N, NR11, O, y S(O)p, en donde el heterociclo es sustituido con 0-5 Rb; alternativamente, dos R1 se combinan con los átomos de carbono a los cuales se enlazan, forman un carbociclo o heterociclo de 5 a 7 miembros que comprende: átomos de carbono y 0-3 heteroátomos adicionales seleccionados de N, NR11, O, y S(O)p, 0-2 carbonilos, y 0-2 enlaces dobles, en donde el carbociclo o heterociclo es sustituido con 0-4 Rb; R5 es un -(CRfRf)n-carbocicloC3-10 substituido con 1-4 R5a, o un -(CRfRf)n-heterociclo de 5 a 10 miembros que comprende: átomos de carbono y 1-4 heteroátomos seleccionados de N, NR11, O, y S(O)p, en donde el heterociclo es sustituido con 0-4 R5a; R5a es, independientemente cada vez que se presenta F, Cl, Br, I, -(CRiRi)r-ORc, SRc, CN, NO2, CF3, -CF2CF3, OCF3, -OCF2CF2H, -OCF2CF3, -NR12R13, -C(O)Rc, -C(O)ORc, -C(O)NR12R13, -NR14C(O)Rd, -S(O)pNR12R13, -S(O)Rd, -S(O)2Rd, -Si(Me)3, Si(alquilo C1-4)3, haloalquilo C1-4, haloalquiloxi C1-4, alquiloxi C1-4, alquiltio C1-4, alquiloC1-4-C(O), alquiloC1-4-O-C(O), alquiloC1-4-C(O)NH, alquilo C1-4 sustituido con 0-2 Ra, alquenilo C2-8 sustituido con 0-2 Ra, alquinilo C2-8 sustituido con 0-2 Ra, -(CRfRf)r-carbocicloC3-10 substituido con 0-3 Re, o -(CRfRf)r- heterociclo de 5 a 10 miembros que comprenden: átomos de carbono y 1-4 heteroátomos seleccionados de N, NR11, O, y S(O)p, en donde el heterociclo es sustituido con 0-3 Re; alternativamente, dos grupos R5a, junto con los átomos a los cuales se enlazan, forman un anillo carbocíclico o heterocíclico de 5 a 7 miembros que comprende: átomos de carbono y 0-2 heteroátomos seleccionados de N, NR11, O, y S(O)p, 0-1 carbonilo, y 0-3 enlaces dobles, en donde el anillo carbocíclico o heterocíclico es sustituido con 0-3 Re; R7 es, independientemente cada vez que se presenta, H, F, Cl, Br, I, OCF3, CF3, ORc, SRc, CN, NO2, -NR12R13, -C(O)Rc, -C(O)ORc, -C(O)NR12R13, -NR14C(O)Rd, -S(O)pNR12R13, -S(O)Rd, -S(O)2Rd, alquilo C1-8 substituido con 0-2 Ra, alquenilo C2.8 substituido con 0-2 Ra, alquinilo C2_8 substituido con 0-2 Ra, (CRfRf)r-carbocicloC3-10 sustituido con 0-3 Rb, o (CRfRf)r-heterociclo de 5 a 10 miembros que comprenden: átomos de carbono y 1-4 heteroátomos seleccionados de N, NR7b, O, y S(O)p, en donde el heterociclo es sustituido con 0-3 Rb; alternativamente, dos R7 pueden formar un anillo carbocíclico o heterocíclico de 5 a 7 miembros que comprende: átomos de carbono y 0-3 heteroátomos en el anillo seleccionados de O, N, NR7b, y S(O)p, en donde el anillo carbocíclico o heterocíclico es sustituido con 0-3 R7c; R7b es, independientemente cada vez que se presenta, H, alquilo C1-4, alquiloC1-4C(O)-, fenilo-C(O)-, bencilo-C(O)-, bencilo-S(O)2-, alquiloC1-4NHC(O)-, (alquiloC1-4)2NC(O)-, fenilo-NHC(O)-, bencilo-NHC(O)-, alquiloC1-4-S(O)2-, fenilo-S(O)2-, fenilo sustituido con 0-3 Rb, o bencilo sustituido con 0-3 Rb; R7c es, independientemente cada vez que se presenta, H, F, Cl, Br, I, OCF3, CF3, ORc, SRc, CN, NO2, -NR12R13, -C(O)Rc, -C(O)ORc, -C(O)NR12R13, -NR14C(O)Rd, -S(O)pNR12R13, -S(O)Rd, -S(O)2Rd, alquilo C1-4, fenilo sustituido con 0-3 Rb, o bencilo sustituido con 0-3 Rb; R11 es, independientemente cada vez que se presenta, H, alquilo C1-6 substituido con 1-5 fluor, -(CRfRf)rC(O)NR12R13, alquilo C1-8 substituido con 0-2 Ra, alquenilo C2-8 substituido con 0-2 Ra, alquinilo C2-8 substituido con 0-2 Ra, alquiloC1-6C(O)-, cicloalquiloC3-6-alquiloC1-3-C(O)-, cicloalquiloC3-6C(O)-, fenilo- C(O)-, bencilo-C(O)-, alquiloC1-6NHC(O)-, (alquiloC1-6)2NC(O)-, fenilo-NHC(O)-, bencilo-NHC(O)-, fenilo-alquiloC1-6NC(O)-, bencilo-alquiloC1-6NC(O)-, alquiloC1-4-S(O)2-, fenilo-S(O)2-, bencilo-S(O)2-, -(CRfRf)r-carbocicloC3-10, o -(CRfRf)r- heterociclo de 5 a 10 miembros que comprenden: átomos de carbono y 1-4 heteroátomos seleccionados de N, NRf, O, y S(O)p; en donde el fenilo, bencilo, carbociclo, y heterociclo son sustituidos con 0-3 Rb; R12 es, independientemente cada vez que se presenta, H, alquilo C1-6 substituido con 1-5 fluor, -(CRfRf)r-C(O)NRfRf, alquilo C1-6, alquiloC1-6C(O)-, alquiloC1-4OC(O)-, ariloC6-10-CH2-OC(O)-, ariloC6-10-CH2-C(O)-, alquiloC1-4-C(O)O-alquiloC1-4-OC(O)-, ariloC6-10-C(O)O-alquiloC1-4-OC(O)-, alquiloC1-6-NHC(O)-, ariloC6-10-NHC(O)-, (heteroarilo de 5 a 10 miembros)-NHC(O)-, (heteroarilo de 5 a 10 miembros)-CH2-OC(O)-, (heteroarilo de 5 a 10 miembros)-C(O)-, ariloC6-10-alquiloC0-4-C(O)-, alquiloC 1-6-S(O)2-, ariloC6-10-S(O)2-, (heterorilo de 5 a 10 miembros)-S(O)2-, o ariloC6-10-alquiloC1-4-S(O)2-, -(CRfRf)n-ariloC6-10, -(CRfRf)n-heterociclo de 5 a 10 miembros; en donde el alquilo, fenilo y arilo son sustituidos con 0-2 Rg; el heteroarilo de 5 a 10 miembros es sustituido con 0-2 Rg y comprende: átomos de carbono y 1-4 heteroátomos seleccionados de N, NRf, O, y S(O)p; el heterociclo de 5 a 10 miembros es sustituido con 0-2 Rg y comprende: átomos de carbono y 1-4 heteroátomos seleccionados de N, NRf, O, y S(O)p; R13 es, independientemente cada vez que se presenta, H, alquilo C1-6, o -(CH2)n-fenilo; alternativamente, R12 y R13, cuando se enlazan al mismo nitrogeno, se combinan para formar un anillo heterocíclico de 5 a 10 miembros que comprenden: átomos de carbono y 1-2 heteroátomos adicionales seleccionados de N, NRf, O, y S(O)p; R14 es, independientemente cada vez que se presenta, H, alquilo C1-6, sustituido con 0-2 R14a, alquenilo C2-6 substituido con 0-2 R14a, alquinilo C2-6 substituido con 0-2 R14a, (CH2)r- carbocicloC3-10 substituido con 0-3 Rg, o (CH2)r-heterociclo de 5 a 10 miembros que comprenden: átomos de carbono y 1-4 heteroátomos seleccionados de N, NRf, O, y S(O)p, en donde el heterociclo es sustituido con 0-3 Rg; R14a es, independientemente cada vez que se presenta, H, alquilo C1-4, ORf, Cl, F, Br, I, =O, CF3, CN, NO2, NR12R13, -C(O)Rf, -C(O)ORf-, -C(O)NR12R13, o -S(O)pRf; Ra es, independiente cada vez que se presenta, H, F, OCF3, CF3, -(CRfRf)rORc, -(CRfRf)rSRc, CN, -(CRfRf)rNR12R13, - (CRfRf)rC(O)Rc, -(CRfRf)rC(O)ORc, -(CRfRf)r-C(O)NR12R13, -(CRfRf)r-NR14C(O)Rd -(CRfRf)rS(O)pNR12R13, -(CRfRf)rS(O)Rd, -(CRfRf)rS(O)2Rd, alquilo C1-4 substituido con 1-5 fluor, (CH2)r-carbocicloC3-10 substituido con 0-3 Re, o (CH2)r-heterociclo de 5 a 10 miembros que comprenden: átomos de carbono y 1-4 heteroátomos seleccionados de N, NRf, O, y S(O)p, en donde el heterociclo es sustituido con 0-3 Re; Rb es, independientemente cada vez que se presenta, H, =O, F, Cl, Br, I, -(CH2)r-ORc, SRc, CN, NO2, CF3, OCF3, -(CRfRf)rNR12R13, -C(O)Rc, -(CH2)r-C(O)ORc, -(CH2)r C(O)NR12R13, -NR14C(O)Rd, -S(O)PNR12R13, -S(O)Rd, -S(O)2Rd, haloalquilo C1-4, haloalquiloxi C1-4, alquilo C1-4 substituido con 0-2 Ra, alquenilo C2-6 substituido con 0-2 Ra, alquinilo C2-6 substituido con 0-2 Ra, (CH2)r-carbocicloC3-10 substituido con 0-3 Re, o (CH2)r-heterociclo de 5 a 10 miembros que comprenden: átomos de carbono y 1-4 heteroátomos seleccionados de N, NRf, O, y S(O)p, en donde el heterociclo es sustituido con 0-3 Re; Rc es, independientemente cada vez que se presenta, H, -OP(O)(OEt)2, alquilo C1-8 substituido con 0-2 Re, alquenilo C2-8 substituido con 0-2 Re, alquinilo C2-8 substituido con 0-2 Re, (CRfRf)r-cicloalquiloC3-8 substituido con 0-2 Re, (CRfRf)r-ariloC6-10 substituido con 0-2 Re, o (CRfRf)r-heterociclo de 5 a 10 miembros que comprenden: átomos de carbono y 1-4 heteroátomos seleccionados de N, NRf, O, y S(O)p, en donde el heterociclo es sustituido con 0-2 Re; Rd es, independientemente cada vez que se presenta, CF3, OH, alcoxi C1-4, alquilo C1-6, (CH2)r-carbocicloC3-10 substituido con 0-2 Re, o (CH2)r-heterociclo de 5 a 10 miembros que comprenden: átomos de carbono y 1-4 heteroátomos seleccionados de N, NRf, O, y S(O)p, en donde el heterociclo es sustituido con 0-2 Re; Re es, independientemente cada vez que se presenta, H, =O, -(CH2)r-ORf, F, Cl, Br, I, CN, NO2, -(CH2)r-NR12R13, -C(O)Rf, -(CH2)r-C(O)ORf, -NR14C(O)Rf, -(CH2)r-C(O)NR12R13, -SO2NR12R13, - NR14SO2NR12R13, -NR14SO2-alquiloC1-4, -NR14SO2CF3, -NR14SO2-fenilo, -S(O)2CF3, -S(O)p-alquiloC1-4, -S(O)p-fenilo, -(CF2)rCF3, Si(alquiloC1-4)3, alquilo C1-8 substituido con 0-2 Rg, alquenilo C2-8 substituido con 0-2 Rg, alquinilo C2-8 substituido con 0-2 Rg, (CH2)r-cicloalquiloC3-8 substituido con 0-2 Rg, (CH2)r-ariloC6-10 substituido con 0-2 Rg, o (CH2)r-heterociclo de 5 a 10 miembr
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-
2006
- 2006-01-17 AT AT06733718T patent/ATE499370T1/de not_active IP Right Cessation
- 2006-01-17 AU AU2006206611A patent/AU2006206611A1/en not_active Abandoned
- 2006-01-17 JP JP2007552205A patent/JP2008527043A/ja active Pending
- 2006-01-17 WO PCT/US2006/001535 patent/WO2006078621A2/en active Application Filing
- 2006-01-17 US US11/333,050 patent/US7645778B2/en active Active
- 2006-01-17 EP EP06733718A patent/EP1954696B1/en active Active
- 2006-01-17 DE DE602006020327T patent/DE602006020327D1/de active Active
- 2006-01-17 KR KR1020077018794A patent/KR20070100894A/ko not_active Application Discontinuation
- 2006-01-17 MX MX2007008434A patent/MX2007008434A/es not_active Application Discontinuation
- 2006-01-18 AR ARP060100185A patent/AR053011A1/es unknown
- 2006-01-18 TW TW095101894A patent/TW200638934A/zh unknown
- 2006-01-18 PE PE2006000076A patent/PE20061120A1/es not_active Application Discontinuation
-
2007
- 2007-07-17 NO NO20073665A patent/NO20073665L/no not_active Application Discontinuation
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2009
- 2009-11-17 US US12/619,702 patent/US8273772B2/en active Active
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WO2006078621A9 (en) | 2008-06-19 |
WO2006078621A2 (en) | 2006-07-27 |
US7645778B2 (en) | 2010-01-12 |
NO20073665L (no) | 2007-10-18 |
MX2007008434A (es) | 2007-07-25 |
EP1954696A2 (en) | 2008-08-13 |
EP1954696B1 (en) | 2011-02-23 |
KR20070100894A (ko) | 2007-10-12 |
WO2006078621A3 (en) | 2006-10-05 |
AU2006206611A1 (en) | 2006-07-27 |
PE20061120A1 (es) | 2006-10-13 |
WO2006078621B1 (en) | 2006-10-26 |
US8273772B2 (en) | 2012-09-25 |
ATE499370T1 (de) | 2011-03-15 |
US20060173002A1 (en) | 2006-08-03 |
DE602006020327D1 (de) | 2011-04-07 |
JP2008527043A (ja) | 2008-07-24 |
TW200638934A (en) | 2006-11-16 |
US20100093689A1 (en) | 2010-04-15 |
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