DK2502921T3 - Arylsulfonamid-CCR3-antagonister - Google Patents

Arylsulfonamid-CCR3-antagonister Download PDF

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DK2502921T3
DK2502921T3 DK12170040.5T DK12170040T DK2502921T3 DK 2502921 T3 DK2502921 T3 DK 2502921T3 DK 12170040 T DK12170040 T DK 12170040T DK 2502921 T3 DK2502921 T3 DK 2502921T3
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alkyl
optionally substituted
heteroaryl
certain embodiments
heterocyclyl
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Tai Wei Ly
Jared Andrew Forrester
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Axikin Pharmaceuticals Inc
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Claims (15)

1. Forbindelse med formel I:
(I) eller en enantiomer, en blanding af enantiomerer, en blanding af to eller flere diastereomerer, en tautomer eller en blanding af to eller flere tautomerer deraf; eller et farmaceutisk acceptabelt salt, solvat eller hydrat deraf; hvor: R1, R2, R3, R4 og R5 hver for sig er hydrogen, halo eller Ci_ 6alkyl; hvor to af R1, R2, R3, R4 og R5 er halo eller Ci_6alkyl, og de resterende tre er hydrogen; R6 er cyano eller nitro; R7 er (a) halo, cyano, nitro, oxo eller guanidin; (b) Ci_6alkyl, C2_6alkenyl, C2-6alkynyl, C3_7Cycloalkyl, C6_i4aryl, C7_i5aralkyl, heteroaryl eller heterocyclyl; eller (c) -C(0)Rla, - C(0)0Rla, -C (0) NRlbRlc, -C (NRla)NRlbRlc, -0Rla, -0C(0)Rla, -0C(0)0Rla, OC (0)NRlbRlc, -0C (=NRla) NRlbRlc, -0S(0)Rla, -0S(0)2Rla, OS (0) NRlbRlc, -OS (0) 2NRlbRlc, -NRlbRlc, -NRlaC (0) Rla, -NRlaC (0) 0Rld, -NRlaC (0) NRlbRlc, -NRlaC (=NRld) NRlbRlc, -NRlaS (0) Rld, -NRlaS (0) 2Rld, -NRlaS (0)NRlbRlc, -NRlaS (0) 2NRlbRlc, -SRla, -S(0)Rla, -S(0)2Rla, - S (0) NRlbRlc eller -S (0) 2NRlbRlc; X er 0 eller S; RYa er -C(0)Rla, med det forbehold at RYa ikke er -C(0)H; m er 1; n er 1; p er 0; og Rla, Rlb, RlG og Rld hver for sig er hydrogen, Ci_6alkyl, C2_ 6alkenyl, C2_6alkynyl, C3-7cycloalkyl, C6-i4aryl, heteroaryl eller heterocyclyl; eller hvert par af Rlb og Rlc sammen med N-atomet, hvortil de er bundet, uafhængigt danner heteroaryl eller heterocyclyl; hvor hver alkyl, alkenyl, alkynyl, cycloalkyl, aryl, aralkyl, heterocyclyl og heteroaryl eventuelt er substitueret med en eller flere grupper, der hver for sig er udvalgt blandt (a) cyano, halo og nitro; (b) Ci-6alkyl, C2-6alkenyl, C2-6alkynyl, C3-7cycloalkyl, C6-i4aryl, C7-i5aralkyl, heteroaryl og heterocyclyl, der hver eventuelt er substitueret med en eller flere, i én udførelsesform, en, to, tre eller fire, substituenter Q; og (c) -C(0)Ra, -C (0) 0Ra, -C (0)NRbRc, -C (NRa) NRbRc, -0Ra, -0C(0)Ra, - OC (0) 0Ra, -0C(0)NRbRc, - 0C (=NRa) NRbRc, -0S(0)Ra, -OS (0) 2Ra, -OS (0) NRbRc, -OS (0) 2NRbR°, -NRbRc, -NRaC (0) Rd, -NRaC(0)0Rd, NRaC (0)NRbR°, -NRaC (=NRd)NRbRc, -NRaS (0) Rd, -NRaS (0) 2Rd, NRaS (0)NRbRc, -NRaS (0) 2NRbR°, -SRa, -S(0)Ra, -S(0)2Ra, -S(0)NRbRc og -S(0)2NRbRc, hvor Ra, Rb, Rc og Rd hver for sig er (i) hydrogen; (ii) Ci_6alkyl, C2_6alkenyl, C2_6alkynyl, C3_ 7cycloalkyl, C6-i4aryl, C7-i5aralkyl, heteroaryl eller heterocyclyl, der hver eventuelt er substitueret med en eller flere substituenter Q; eller (iii) Rb og Rc sammen med N-atomet, hvortil de er bundet, danner heterocyclyl, der eventuelt er substitueret med en eller flere substituenter Q; hvor hvert Q er udvalgt uafhængigt fra gruppen, der består af (a) cyano, halo og nitro; (b) Ci_6alkyl, C2_6alkenyl, C2_ 6alkynyl, C3-7cycloalkyl, C6-i4aryl, C7-i5aralkyl, heteroaryl og heterocyclyl; og (c) -C(0)Re, -C(0)0Re, -C (0) NRfRg, -C (NRe) NRfRg, -0Re, -0C(0)Re, -OC (0) 0Re, -OC (0) NRfRg, -OC (=NRe) NRfRg, -0S(0)Re, -OS (0) 2Re, -OS (0) NRfRg, -OS (0) 2NRfRg, -NRfRg, -NReC (0) Rh, NReC(0)0Rh, -NReC (0) NRfRg, -NReC (=NRh) NRfRg, -NReS (0) Rh, NReS (0) 2Rh, -NReS (0) NRfRg, -NReS (0) 2NRfRg, -SRe, -S(0)Re, -S(0)2Re, -S (0) NRfRg og -S (0) 2NRfRg; hvor Re, Rf, Rg og Rh hver for sig er (i) hydrogen; (ii) Ci-6alkyl, C2-6alkenyl, C2_6alkynyl, C3- 7cycloalkyl, C6-i4aryl, C7-isaralkyl, heteroaryl eller heterocyclyl; eller (iii) Rf og Rg sammen med N-atomet, hvortil de er bundet, danner heterocyclyl.
2. Forbindelse ifølge krav 1, hvor Rla er (b) Ci_6alkyl, der eventuelt er substitueret med en, to eller tre substituenter, der hver er udvalgt uafhængigt blandt cyano, halo, C3_7cycloalkyl, C6-i4aryl, heteroaryl, heterocyclyl, -C(0)Ra, -C(0)0Ra og -SRa, hvor cycloalkyl, aryl, heteroaryl og heterocyclyl hver eventuelt yderligere er substitueret med en, to eller tre substituenter, der hver for sig er halo eller Ci_6alkyl; (c) Ci_6alkenyl, der eventuelt er substitueret med C6-i4aryl; (d) C3_7cycloalkyl, der eventuelt er substitueret med en eller to Ci_6alkyl; (e) C6-i4aryl, der eventuelt er substitueret med en, to eller tre substituenter, der hver er udvalgt uafhængigt blandt halo, nitro, cyano, -0Ra, -C(0)Ra og Ci_6alkyl, hvor alkyl eventuelt yderligere er substitueret med en, to eller tre halo; (f) heteroaryl, der eventuelt er substitueret med en, to eller tre substituenter, der hver for sig er halo eller Ci-6alkyl; eller (g) heterocyclyl; eller hvor Rla er Ci_6alkyl, C2-6alkenyl, C3_7Cycloalkyl, C6-i4aryl, heteroaryl eller heterocyclyl, der hver eventuelt er substitueret med en eller to substituenter, der hver er udvalgt uafhængigt blandt halo, cyano, nitro, Ci_6alkyl, C3-7cycloalkyl, C6-i4aryl, heteroaryl, heterocyclyl, -0Ra, -SRa og -C(0)Ra, hvor alkyl, cycloalkyl, aryl, heteroaryl og heterocyclyl hver eventuelt yderligere er substitueret med en eller to substituenter, der hver for sig er halo eller Ci_ 6alkyl; eller hvor Rla er Ci-6alkyl, C2-6alkenyl, C3-7Cycloalkyl, C6-i4aryl, heteroaryl eller heterocyclyl, der hver eventuelt er substitueret med en eller to substituenter, der hver for sig er udvalgt blandt fluor, chlor, cyano, nitro, methyl, trifluormethyl, ethyl, methoxy, ethoxy, methylthio, (lS,2S,4R)-7,7-dimethylbicyclo[2.2.1]-heptyl, phenyl, chlorphenyl, furanyl, morpholinyl, acetyl, propionyl og ethoxycarbonyl; eller hvor Rla er (b) Ci_6alkyl, der eventuelt er substitueret med en substituent, der er udvalgt blandt chlor, cyano, ethoxy, methylthio, (1 S, 25, 4R)-7,7-dimethylbicyclo[2.2.1]-heptyl, phenyl, chlorphenyl, furanyl, morpholinyl, propionyl og ethoxycarbonyl; (c) C2-6alkenyl, der eventuelt er substitueret med phenyl; (d) C3-7cycloalkyl; (e) C6-i4aryl, der eventuelt er substitueret med en eller to substituenter, der hver for sig er udvalgt blandt fluor, chlor, cyano, nitro, methyl, trifluormethyl, ethyl, methoxy og acetyl; (f) heteroaryl, der eventuelt er substitueret med en eller to methyl; eller (g) heterocyclyl; eller hvor Rla er (b) methyl, ethyl, propyl, butyl eller pentyl, der hver eventuelt er substitueret med en substituent, der er udvalgt blandt chlor, cyano, ethoxy, methylthio, (1S,2S, 4R) -7,7-dimethylbicyclo[2.2.1]-heptyl, phenyl, chlorphenyl, furanyl, morpholinyl, propionyl og ethoxycarbonyl; (c) ethenyl eller allyl, der hver eventuelt er substitueret med phenyl; (d) cyclobutyl, cyclopentyl eller cyclohexyl; (e) phenyl, der eventuelt er substitueret med en eller to substituenter, der hver for sig er udvalgt blandt fluor, chlor, cyano, nitro, methyl, trifluormethyl, ethyl, methoxy og acetyl; (f) furanyl, thienyl, isoxazolyl, pyrazolyl, 1,2,3-thiadiazolyl, pyridinyl, pyrazyl, benzofuranyl, benzo[c] [1,2,5]oxadiazolyl, benzothienyl eller benzothiazolyl, der hver eventuelt er substitueret med en eller to methyl; eller (g) morpholinyl.
3. Forbindelse ifølge krav 1 eller 2, hvor to af R1, R2, R3, R4 og R5 er chlor eller methyl, og de resterende tre er hydrogen.
4. Forbindelse ifølge krav 3, hvor R1, R3 og R5 er hydrogen, og R2 og R4 er chlor eller methyl; fortrinsvis hvor R2 og R4 er chlor; eller fortrinsvis hvor R2 og R4 er methyl.
5. Forbindelse ifølge krav 3, hvor R2, R3 og R5 er hydrogen, og R1 og R4 er chlor eller methyl; fortrinsvis hvor R1 og R4 er chlor; eller fortrinsvis hvor R1 og R4 er methyl.
6. Forbindelse ifølge et hvilket som helst af kravene 1 til 5, hvor R7 er Ci-6alkyl.
7. Forbindelse ifølge krav 1, der er udvalgt fra gruppen, der består af:
190 og enantiomerer, blandinger af enantiomerer, blandinger af to eller flere diastereomerer, tautomerer og blandinger af to eller flere tautomerer deraf; og farmaceutisk acceptable salte, solvater og hydrater deraf.
8. Forbindelse ifølge et hvilket som helst af kravene 1 til 7, hvor forbindelsen er et hydrochloridsalt.
9. Farmaceutisk præparat, der omfatter en forbindelse ifølge et hvilket som helst af kravene 1 til 8 eller et farmaceutisk acceptabelt salt, solvat, hydrat eller en farmaceutisk acceptabel stereoisomer eller tautomer deraf; og et eller flere farmaceutisk acceptable bærematerialer eller excipienser; og eventuelt yderligere omatter et andet terapeutisk middel.
10. Farmaceutisk præparat ifølge krav 9, hvor præparatet er formuleret til administration som enkeltdosis; eventuelt hvor præparatet er formuleret som en oral, parenteral eller intravenøs dosisform; hvor den orale dosisform fortrinsvis er en tablet eller en kapsel.
11. Forbindelse ifølge et hvilket som helst af kravene 1 til 8 eller farmaceutisk præparat ifølge krav 9 eller 10 til anvendelse i en fremgangsmåde til behandling, forebyggelse eller bedring af et eller flere symptomer på en CCR3-medieret forstyrrelse, sygdom eller tilstand.
12. Forbindelse ifølge et hvilket som helst af kravene 1 til 8 eller farmaceutisk præparat ifølge krav 9 eller 10 til anvendelse i: en fremgangsmåde til behandling, forebyggelse eller bedring af et eller flere symptomer på en eosinofilrelateret forstyrrelse, sygdom eller tilstand; eller en fremgangsmåde til behandling, forebyggelse eller bedring af et eller flere symptomer på en basofilrelateret forstyrrelse, sygdom eller tilstand; eller en fremgangsmåde til behandling, forebyggelse eller bedring af et eller flere symptomer på en mastcellerelateret forstyrrelse, sygdom eller tilstand.
13. Forbindelse ifølge et hvilket som helst af kravene 1 til 8 eller farmaceutisk præparat ifølge krav 9 eller 10 til anvendelse i en fremgangsmåde til behandling, forebyggelse eller bedring af et eller flere symptomer på en inflammationssygdom.
14. Forbindelse til anvendelse ifølge et hvilket som helst af kravene 11 til 13, hvor forstyrrelsen, sygdommen eller tilstanden er udvalgt fra gruppen, der består af astma, allergisk astma, anstrengelsesastma, allergisk rhinitis, helårs allergisk rhinitis, sæsonbetinget allergisk rhinitis, atopisk dermatitis, kontaktoverfølsomhed, kontaktdermatitis, conjunctivitis, allergisk conjunctivitis, eosinofil bronkitis, fødevareallergier, eosinofil gastroenteritis, inflammatorisk tarmsygdom, ulcerativ colitis, Crohns sygdom, mastocytose, hyper-IgE-syndrom, systemisk lupus erythematous, psoriasis, akne, multipel sklerose, allograftafstødning, reperfusionsskade, Churg-Strauss-syndrom, sinusitis, basofil leukæmi, kronisk urticaria, basofil leukocytose, eksem, KOL (kronisk obstruktiv lungesygdom), arthritis, rheumatoid arthritis, psoriatisk arthritis, osteoarthritis og kardiovaskulære forstyrrelser; eller hvor forstyrrelsen, sygdommen eller tilstanden er astma, anstrengelsesastma, allergisk rhinitis, atopisk dermatitis, kronisk obstruktiv lungesygdom eller allergisk conjunctivitis.
15. Forbindelse til anvendelse ifølge et hvilket som helst af kravene 11 til 14, hvor forbindelsen er til oral, parenteral eller topisk administration; og/eller hvor forbindelsen er til administration i kombination med et andet terapeutisk middel.
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