HRP20100017T1 - Derivati heteroaril-alkilkarbamata, postupak njihovog dobivanja i njihova upotreba kao inhibitora enzima faah - Google Patents

Derivati heteroaril-alkilkarbamata, postupak njihovog dobivanja i njihova upotreba kao inhibitora enzima faah Download PDF

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HRP20100017T1
HRP20100017T1 HR20100017T HRP20100017T HRP20100017T1 HR P20100017 T1 HRP20100017 T1 HR P20100017T1 HR 20100017 T HR20100017 T HR 20100017T HR P20100017 T HRP20100017 T HR P20100017T HR P20100017 T1 HRP20100017 T1 HR P20100017T1
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Croatia
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ethyl
group
oxazolidinedione
pyridyl
groups
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HR20100017T
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English (en)
Inventor
Abouabdellah Ahmed
Bartsch-Li R�gine
Hoornaert Christian
Ravet Antoine
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Sanofi-Aventis
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Publication of HRP20100017T1 publication Critical patent/HRP20100017T1/hr

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Abstract

Spoj opće formule (I) ,naznačen time štoA se bira iz jedne ili više skupina X, Y i/ili Z; X predstavlja metilensku skupinu, izborno supstituiranu s jednom ili dvije C1-6-alkilne, C3-7-cikloalkilne ili C3-7 cikloalkil-C1-3-alkilenske skupine; Y predstavlja bilo C2-alkenilensku skupinu, izborno supstituiranu s jednom ili dvije C1-6-alkilne, C3-7-cikloalkilne ili C3-7-cikloalkil-C1-3-alkilenske skupine; ili C2-alkinilensku skupinu; Z predstavlja skupinu formule: ;m predstavlja cijeli broj od 1 do 5; p i q predstavljaju cijele brojeve i definirani su tako da p + q je broj od 1 do 5; n predstavlja cijeli broj od 1 do 7; R1 predstavlja skupinu R2, izborno supstituiranu s jednom ili više skupina R3 i/ili R4;R2 predstavlja skupinu koju se bira između piridila, pirimidinila, piridazinila, pirazinila, triazinila, pirolila, furila, tienila, imidazolila, oksazolila, tiazolila, pirazolila, izoksazolila, izotiazolila, oksadiazolila, tiadiazolila, triazolila, tetrazolila, naftila, kinolinila, tetrahidrokinolinila, izokinolinila, tetrahidroizokinolinila, 2-okso-3,4-dihidrokinolinila, 1-okso-3,4-dihidroizokinolinila, kinazolinila, kinoksalinila, ftalazinila, cinolinila, naftiridinila, benzofuranila, dihidrobenzofuranila, benzotienila, dihidrobenzotienila, indolila, indolinila, indazolila, izoindolila, benzimidazolila, benzoksazolila, benzizoksazolila, benzotiazolila, benzizotiazolila, benzotriazolila, benzoksadiazolila, benzotiadiazolila, pirolopiridila, furopiridila, tienopiridila, imidazopiridila, oksazolopiridila, tiazolopiridila, pirazolopiridila, izoksazolopiridila ili izotiazolopiridila; R3 predstavlja skupinu koju se bira između atoma halogena ili cijano, nitro, C1-6-alkila, C1-6-alkoksi, hidroksilne, C1-6-tioalkilne, C1-6-fluoralkilne, C1-6-fluoralkoksi, C1-6-fluortioalkilne, NR5R6, NR5COR6, NR5CO2R6, NR5SO2R6, COR5, CO2R5, CONR5R6, SO2R5, SO2NR5R6 ili -O-(C1-3-alkilen)-O skupine; R4 predstavlja skupinu koju se bira između fenilne, feniloksi, benziloksi, naftilne, piridilne, pirimidinilne, piridazinilne ili pirazinilne skupine; jedna ili više skupina R4 može biti supstituirana s jednom ili više istovjetnih ili različitih skupina R3; R5 i R6, međusobno neovisno, predstavljaju atom vodika ili C1-6-alkilnu skupinu, ili s jednim ili više atoma koji ih nose tvore prsten, kojeg se bira između azetidinskog, pirolidinskog, piperidinskog, morfolinskog, tiomorfolinskog, azepinskog ili piperazinskog prstena, gdje je taj prsten izborno supstituiran s C1-6-alkilnom ili benzilnom skupinom; R7 predstavlja atom vodika ili C1-6-alkilnu skupinu; R8 predstavlja atom vodika ili C1-6-alkilnu, C3-7-cikloalkilnu ili C3-7-cikloalkil-C1-3-alkilensku skupinu; u obliku baze ili u obliku adicijske soli s kiselinom, hidrata ili solvata. Patent sadrži još 10 patentnih zahtjeva.

Claims (11)

1. Spoj opće formule (I) [image] , naznačen time što A se bira iz jedne ili više skupina X, Y i/ili Z; X predstavlja metilensku skupinu, izborno supstituiranu s jednom ili dvije C1-6-alkilne, C3-7-cikloalkilne ili C3-7 cikloalkil-C1-3-alkilenske skupine; Y predstavlja bilo C2-alkenilensku skupinu, izborno supstituiranu s jednom ili dvije C1-6-alkilne, C3-7-cikloalkilne ili C3-7-cikloalkil-C1-3-alkilenske skupine; ili C2-alkinilensku skupinu; Z predstavlja skupinu formule: [image] ; m predstavlja cijeli broj od 1 do 5; p i q predstavljaju cijele brojeve i definirani su tako da p + q je broj od 1 do 5; n predstavlja cijeli broj od 1 do 7; R1 predstavlja skupinu R2, izborno supstituiranu s jednom ili više skupina R3 i/ili R4; R2 predstavlja skupinu koju se bira između piridila, pirimidinila, piridazinila, pirazinila, triazinila, pirolila, furila, tienila, imidazolila, oksazolila, tiazolila, pirazolila, izoksazolila, izotiazolila, oksadiazolila, tiadiazolila, triazolila, tetrazolila, naftila, kinolinila, tetrahidrokinolinila, izokinolinila, tetrahidroizokinolinila, 2-okso-3,4-dihidrokinolinila, 1-okso-3,4-dihidroizokinolinila, kinazolinila, kinoksalinila, ftalazinila, cinolinila, naftiridinila, benzofuranila, dihidrobenzofuranila, benzotienila, dihidrobenzotienila, indolila, indolinila, indazolila, izoindolila, benzimidazolila, benzoksazolila, benzizoksazolila, benzotiazolila, benzizotiazolila, benzotriazolila, benzoksadiazolila, benzotiadiazolila, pirolopiridila, furopiridila, tienopiridila, imidazopiridila, oksazolopiridila, tiazolopiridila, pirazolopiridila, izoksazolopiridila ili izotiazolopiridila; R3 predstavlja skupinu koju se bira između atoma halogena ili cijano, nitro, C1-6-alkila, C1-6-alkoksi, hidroksilne, C1-6-tioalkilne, C1-6-fluoralkilne, C1-6-fluoralkoksi, C1-6-fluortioalkilne, NR5R6, NR5COR6, NR5CO2R6, NR5SO2R6, COR5, CO2R5, CONR5R6, SO2R5, SO2NR5R6 ili -O-(C1-3-alkilen)-O skupine; R4 predstavlja skupinu koju se bira između fenilne, feniloksi, benziloksi, naftilne, piridilne, pirimidinilne, piridazinilne ili pirazinilne skupine; jedna ili više skupina R4 može biti supstituirana s jednom ili više istovjetnih ili različitih skupina R3; R5 i R6, međusobno neovisno, predstavljaju atom vodika ili C1-6-alkilnu skupinu, ili s jednim ili više atoma koji ih nose tvore prsten, kojeg se bira između azetidinskog, pirolidinskog, piperidinskog, morfolinskog, tiomorfolinskog, azepinskog ili piperazinskog prstena, gdje je taj prsten izborno supstituiran s C1-6-alkilnom ili benzilnom skupinom; R7 predstavlja atom vodika ili C1-6-alkilnu skupinu; R8 predstavlja atom vodika ili C1-6-alkilnu, C3-7-cikloalkilnu ili C3-7-cikloalkil-C1-3-alkilensku skupinu; u obliku baze ili u obliku adicijske soli s kiselinom, hidrata ili solvata.
2. Spoj formule (I) u skladu s patentnim zahtjevom 1, naznačen time što A se bira iz jedne ili više skupina X i/ili Y; X predstavlja metilensku skupinu; Y predstavlja C2-alkinilensku skupinu; n predstavlja cijeli broj od 1 do 5; R1 predstavlja skupinu R2, izborno supstituiranu s jednom ili više skupina R3 i/ili R4; R2 predstavlja skupinu koju se bira između piridila, pirimidinila, piridazinila, imidazolila, oksazolila, pirazolila, izoksazolila, oksadiazolila, naftila, kinolinila, izokinolinila, dihidroizokinolinila, 2-okso-3,4-dihidrokinolinila, indolila, benzimidazolila ili pirolopiridila; R3 predstavlja skupinu koju se bira između atoma halogena ili C1-6-alkilne, C1-6-alkoksi ili NR5R6 skupine; R4 predstavlja skupinu koju se bira između fenilne, naftilne ili piridilne skupine; jedna ili više skupina R4 može biti supstituirana s jednom ili više istovjetnih ili različitih skupina R3; R5 i R6, međusobno neovisno, predstavljaju C1-6-alkilnu skupinu; R7 predstavlja atom vodika ili C1-6-alkilnu skupinu; R8 predstavlja atom vodika ili C1-6-alkilnu, C3-7-cikloalkilnu ili C3-7-cikloalkil-C1-3-alkilensku skupinu; u obliku baze ili u obliku adicijske soli s kiselinom, hidrata ili solvata.
3. Spoj formule (I) u skladu s patentnim zahtjevom 1 ili 2, naznačen time što R2 predstavlja skupinu koju se bira između piridila, pirimidinila, oksazolila, izoksazolila, naftila, kinolinila ili izokinolinila.
4. Spoj formule (I) u skladu s bilo kojim od patentnih zahtjeva 1 do 3, naznačen time što R7 predstavlja atom vodika; R8 predstavlja atom vodika ili C1-6-alkilnu skupinu; u obliku baze ili u obliku adicijske soli s kiselinom, hidrata ili solvata.
5. Postupak dobivanja spoja formule (I) u skladu s bilo kojim od patentnih zahtjeva 1 do 4, naznačen time što uključuje korak koji se sastoji u prevođenju karbamatnog estera opće formule (IV) [image] , u kojoj A, n, R1 i R7 su definirani kao u formuli (I) u skladu s patentnim zahtjevom 1, gdje R predstavlja metilnu ili etilnu skupinu, aminolizom, uz upotrebu amina opće formule R8NH2, u kojoj R8 je definiran kao u formuli (I) u skladu s patentnim zahtjevom 1.
6. Postupak dobivanja spoja formule (I) u skladu s bilo kojim od patentnih zahtjeva 1 do 4, naznačen time što uključuje korak koji se sastoji u prevođenju oksazolidindionskog derivata opće formule (VII) [image] , u kojoj A, n, R1 i R7 su definirani kao u formuli (I) u skladu s patentnim zahtjevom 1, aminolizom, uz upotrebu amina opće formule R8NH2, u kojoj R8 je definiran kao u formuli (I) u skladu s patentnim zahtjevom 1.
7. Spoj opće formule (IV) [image] , naznačen time što A, n, R1 i R7 su definirani kao u formuli (I) u skladu s patentnim zahtjevom 1; a R predstavlja metilnu ili etilnu skupinu; pri čemu su isključeni sljedeći spojevi: – etil-2-[({[2-(5-hidroksi-1H-indol-3-il)etil]amino}karbonil)oksi]propanoat; i – etil-2-[({[2-[[5-(fenilmethoksi)-1H-indol-3-il]etil]amino}karbonil)oksi]propanoat.
8. Spoj opće formule (VII) [image] , naznačen time što A, n, R1 i R7 su definirani kao u formuli (I) u skladu s patentnim zahtjevom 1; pri čemu su isključeni sljedeći spojevi: – 2-[2-(2,4-diokso-3-oksazolidinil)etil]-1-metilpiridinijev jodid; – 2-[2-(2,4-diokso-3-oksazolidinil)etil]-5-etil-1-metilpiridinijev jodid; – 4-[2-(2,4-diokso-3-oksazolidinil)etil]-1-metilpiridinijev jodid; – 5-metil-3-[2-(4-piridil)etil]-2,4-oksazolidindion-hidroklorid; – 5-metil-3-[2-(2-piridil)etil]-2,4-oksazolidindion-hidroklorid; – 3-[5-(imidazo[1,2-a]pirid-5-il)pentil]-2,4-oksazolidindion; – 3-[2-(5-metil-4-tiazolil)etil]-2,4-oksazolidindion; – 3-[2-(1H-pirol-2-il)etil]-2,4-oksazolidindion; – 3-[2-(2-tienil)etil]-2,4-oksazolidindion; – 3-[3-(2-tienil)propil]-2,4-oksazolidindion; – 3-[4-(2-tienil)butil]-2,4-oksazolidindion; – 5-metil-3-[2-(2-tienil)etil]-2,4-oksazolidindion; – 5-etil-3-[2-(2-tienil)etil]-2,4-oksazolidindion; – 3-[2-(3-tienil)etil]-2,4-oksazolidindion; – 3-[2-(5-metil-2-tienil)etil]-2,4-oksazolidindion; – 3-[2-(5-acetil-2-tienil)etil]-2,4-oksazolidindion; – 3-[2-(5-brom-2-tienil)etil]-2,4-oksazolidindion; – 5-[2-(2,4-diokso-3-oksazolidinil)etil]-2-tiofenkarbaldehid; – 3-[3-(1-indolinil)propil]-2,4-oksazolidindion; – 3-[3-(1-indolinil)propil]-5-metil-2,4-oksazolidindion; – 3-[2-(2-piridil)etil]-2,4-oksazolidindion; – 3-[2-(5-etil-2-piridil)etil]-5-metil-2,4-oksazolidindion; – 5-etil-3-[2-(5-etil-2-piridil)etil]-2,4-oksazolidindion; – 3-[2-(5-etil-2-piridil)etil]-5-izopropil-2,4-oksazolidindion; – 3-[2-(4-piridil)etil]-2,4-oksazolidindion; – 5-etil-3-[2-(4-piridil)etil]-2,4-oksazolidindion; – 5-etil-3-[2-(2-piridil)etil]-2,4-oksazolidindion; – 5-izopropil-3-[2-(4-piridil)etil]-2,4-oksazolidindion; – 5-izopropil-3-[2-(2-piridil)etil]-2,4-oksazolidindion; i – 3-[2-(5-etil-2-piridil)etil]-2,4-oksazolidindion.
9. Farmaceutski pripravak, naznačen time što sadrži najmanje jedan spoj formule (I) u skladu s bilo kojim od patentnih zahtjeva 1 do 4, u obliku baze ili farmaceutski prihvatljive soli, hidrata ili soli, hidrata ili solvata, i izborno sadrži jednu ili više farmaceutski prihvatljivih pomoćnih tvari.
10. Spoj formule (I) u skladu s bilo kojim od patentnih zahtjeva 1 do 4, u obliku baze ili farmaceutski prihvatljive soli, hidrata ili soli, hidrata ili solvata, naznačen time što je namijenjen upotrebi kao medikament.
11. Upotreba spoja formule (I) u skladu s bilo kojim od patentnih zahtjeva 1 do 4, u obliku baze ili farmaceutski prihvatljive soli, hidrata ili soli, hidrata ili solvata, naznačen time što se navedeni spoj koristi u pripravi medikamenta za sprječavanje ili liječenje akutne ili kronične boli, vrtoglavice, povraćanja, mučnine, poremećaja hranjenja, neuroloških i psihijatrijskih patologija, akutnih ili kroničnih neurodegenerativnih bolesti, epilepsije, poremećaja spavanja, kardiovaskularnih bolesti, bubrežene ishemije, raka, poremećaja imunosnog sustava, alergijskih bolesti, parazitskih, virusnih ili bakterijskih zaraznih bolesti, upalnih bolesti, osteoporoze, stanja očiju, stanja pluća, gastrointestinalnih bolesti ili inkontinencije mokraće.
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FR2866886A1 (fr) 2005-09-02
RS51246B (sr) 2010-12-31
ZA200606724B (en) 2007-12-27
RU2364586C2 (ru) 2009-08-20
DK1720829T3 (da) 2010-03-01
BRPI0508193A (pt) 2007-08-14
JP2007524705A (ja) 2007-08-30
JP4824668B2 (ja) 2011-11-30
MA28367A1 (fr) 2006-12-01
DE602005017122D1 (de) 2009-11-26
AR047973A1 (es) 2006-03-15
SI1720829T1 (sl) 2010-02-26
US7645757B2 (en) 2010-01-12
CN1926097A (zh) 2007-03-07
WO2005090292A1 (fr) 2005-09-29

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