DE60209736T2 - Piperidinverbindungen, die sich als modulatoren der chemokinrezeptoraktivität eignen - Google Patents
Piperidinverbindungen, die sich als modulatoren der chemokinrezeptoraktivität eignen Download PDFInfo
- Publication number
- DE60209736T2 DE60209736T2 DE60209736T DE60209736T DE60209736T2 DE 60209736 T2 DE60209736 T2 DE 60209736T2 DE 60209736 T DE60209736 T DE 60209736T DE 60209736 T DE60209736 T DE 60209736T DE 60209736 T2 DE60209736 T2 DE 60209736T2
- Authority
- DE
- Germany
- Prior art keywords
- carbonyl
- bipiperidin
- dichlorophenoxy
- benzenesulfonamide
- alkyl
- 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.)
- Expired - Lifetime
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- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical class C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 title claims description 9
- 230000000694 effects Effects 0.000 title description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 244
- 150000001875 compounds Chemical class 0.000 claims description 226
- -1 nitro, hydroxy Chemical group 0.000 claims description 216
- 229910052739 hydrogen Inorganic materials 0.000 claims description 64
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 52
- 238000000034 method Methods 0.000 claims description 51
- 239000001257 hydrogen Substances 0.000 claims description 49
- 239000002904 solvent Substances 0.000 claims description 48
- 229940124530 sulfonamide Drugs 0.000 claims description 43
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 38
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 33
- 150000003839 salts Chemical class 0.000 claims description 32
- 125000003545 alkoxy group Chemical group 0.000 claims description 28
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 27
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 27
- 229910052736 halogen Inorganic materials 0.000 claims description 25
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 22
- 125000000623 heterocyclic group Chemical group 0.000 claims description 22
- 125000005843 halogen group Chemical group 0.000 claims description 19
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 19
- 150000002431 hydrogen Chemical class 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
- 239000012453 solvate Substances 0.000 claims description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 11
- 239000003814 drug Substances 0.000 claims description 10
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 9
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 9
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 9
- 125000004043 oxo group Chemical group O=* 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 8
- NVKOAYGOEXSEII-WGSAOQKQSA-N C1=CC(C)=CC=C1S(=O)(=O)NC(=O)[C@@H]1CC[C@@H](N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)[C@@H]1CC[C@@H](N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 NVKOAYGOEXSEII-WGSAOQKQSA-N 0.000 claims description 6
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- 239000002168 alkylating agent Substances 0.000 claims description 6
- 229940100198 alkylating agent Drugs 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 6
- 125000003107 substituted aryl group Chemical group 0.000 claims description 6
- ZDWNUSDUXVXKFB-UHFFFAOYSA-N 4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-n-propan-2-ylsulfonylpiperidine-1-carboxamide Chemical compound C1CN(C(=O)NS(=O)(=O)C(C)C)CCC1N1CCC(OC=2C=C(Cl)C(Cl)=CC=2)CC1 ZDWNUSDUXVXKFB-UHFFFAOYSA-N 0.000 claims description 5
- SQTLUXJWUCHKMT-UHFFFAOYSA-N 4-bromo-n,n-diphenylaniline Chemical compound C1=CC(Br)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 SQTLUXJWUCHKMT-UHFFFAOYSA-N 0.000 claims description 5
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 5
- 150000001204 N-oxides Chemical class 0.000 claims description 5
- 239000007822 coupling agent Substances 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- REIZYHKXRGEBEI-UHFFFAOYSA-N 4-[4-(2,4-dichloro-3-methylphenoxy)piperidin-1-yl]-n-(2-methylphenyl)sulfonylpiperidine-1-carboxamide Chemical compound CC1=CC=CC=C1S(=O)(=O)NC(=O)N1CCC(N2CCC(CC2)OC=2C(=C(C)C(Cl)=CC=2)Cl)CC1 REIZYHKXRGEBEI-UHFFFAOYSA-N 0.000 claims description 4
- HZUZFBPRVMJMHT-UHFFFAOYSA-N 4-[4-(2,4-dichloro-3-methylphenoxy)piperidin-1-yl]-n-(4-fluorophenyl)sulfonylpiperidine-1-carboxamide Chemical compound CC1=C(Cl)C=CC(OC2CCN(CC2)C2CCN(CC2)C(=O)NS(=O)(=O)C=2C=CC(F)=CC=2)=C1Cl HZUZFBPRVMJMHT-UHFFFAOYSA-N 0.000 claims description 4
- FHLJNJSZPGMALO-UHFFFAOYSA-N 4-[4-(3,4-dichloro-2-methylphenoxy)piperidin-1-yl]-n-(4-methylphenyl)sulfonylpiperidine-1-carboxamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)N1CCC(N2CCC(CC2)OC=2C(=C(Cl)C(Cl)=CC=2)C)CC1 FHLJNJSZPGMALO-UHFFFAOYSA-N 0.000 claims description 4
- IUWXMHJXYHLXSR-UHFFFAOYSA-N 4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-n-(2,4,5-trifluorophenyl)sulfonylpiperidine-1-carboxamide Chemical compound C1=C(F)C(F)=CC(F)=C1S(=O)(=O)NC(=O)N1CCC(N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 IUWXMHJXYHLXSR-UHFFFAOYSA-N 0.000 claims description 4
- YISQPKPMJJVCCU-UHFFFAOYSA-N 4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-n-(2,5-dichlorothiophen-3-yl)sulfonylpiperidine-1-carboxamide Chemical compound S1C(Cl)=CC(S(=O)(=O)NC(=O)N2CCC(CC2)N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)=C1Cl YISQPKPMJJVCCU-UHFFFAOYSA-N 0.000 claims description 4
- SWEHCFKMAYPEHK-UHFFFAOYSA-N 4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-n-(2,5-difluorophenyl)sulfonylpiperidine-1-carboxamide Chemical compound FC1=CC=C(F)C(S(=O)(=O)NC(=O)N2CCC(CC2)N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)=C1 SWEHCFKMAYPEHK-UHFFFAOYSA-N 0.000 claims description 4
- FJXUEXJXAXDKTR-UHFFFAOYSA-N 4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-n-(4,5-dichlorothiophen-2-yl)sulfonylpiperidine-1-carboxamide Chemical compound S1C(Cl)=C(Cl)C=C1S(=O)(=O)NC(=O)N1CCC(N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 FJXUEXJXAXDKTR-UHFFFAOYSA-N 0.000 claims description 4
- QVLZVRFIGXNZMN-UHFFFAOYSA-N 4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-n-(4-methylphenyl)sulfonylpiperidine-1-carboxamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)N1CCC(N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 QVLZVRFIGXNZMN-UHFFFAOYSA-N 0.000 claims description 4
- IGCXNQLEJAPTMB-UHFFFAOYSA-N 4-[4-(4-chloro-2-methylphenoxy)piperidin-1-yl]-n-(2-methylphenyl)sulfonylpiperidine-1-carboxamide Chemical compound CC1=CC(Cl)=CC=C1OC1CCN(C2CCN(CC2)C(=O)NS(=O)(=O)C=2C(=CC=CC=2)C)CC1 IGCXNQLEJAPTMB-UHFFFAOYSA-N 0.000 claims description 4
- PQHXPPICWGPBON-IYARVYRRSA-N C1=C(Cl)C(Cl)=CC=C1OC1CCN([C@@H]2CC[C@H](CC2)C(=O)NS(=O)(=O)C=2C=CC=CC=2)CC1 Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCN([C@@H]2CC[C@H](CC2)C(=O)NS(=O)(=O)C=2C=CC=CC=2)CC1 PQHXPPICWGPBON-IYARVYRRSA-N 0.000 claims description 4
- PAEZTKREROBBNB-WGSAOQKQSA-N CC1=CC=CC=C1S(=O)(=O)NC(=O)[C@@H]1CC[C@@H](N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 Chemical compound CC1=CC=CC=C1S(=O)(=O)NC(=O)[C@@H]1CC[C@@H](N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 PAEZTKREROBBNB-WGSAOQKQSA-N 0.000 claims description 4
- 150000001266 acyl halides Chemical class 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- JJPRHDAPWGULRR-UHFFFAOYSA-N n-(3-chloro-5-fluoro-2-methylphenyl)sulfonyl-4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]piperidine-1-carboxamide Chemical compound CC1=C(Cl)C=C(F)C=C1S(=O)(=O)NC(=O)N1CCC(N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 JJPRHDAPWGULRR-UHFFFAOYSA-N 0.000 claims description 4
- BGBZPKPXJHATBP-UHFFFAOYSA-N n-(4-chloro-2,5-difluorophenyl)sulfonyl-4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]piperidine-1-carboxamide Chemical compound C1=C(Cl)C(F)=CC(S(=O)(=O)NC(=O)N2CCC(CC2)N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)=C1F BGBZPKPXJHATBP-UHFFFAOYSA-N 0.000 claims description 4
- ZFLFDJDKLXKKDY-UHFFFAOYSA-N n-(5-chloro-2,4-difluorophenyl)sulfonyl-4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]piperidine-1-carboxamide Chemical compound C1=C(Cl)C(F)=CC(F)=C1S(=O)(=O)NC(=O)N1CCC(N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 ZFLFDJDKLXKKDY-UHFFFAOYSA-N 0.000 claims description 4
- RYOAZTXPWXIRGP-UHFFFAOYSA-N n-(5-chlorothiophen-2-yl)sulfonyl-4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]piperidine-1-carboxamide Chemical compound S1C(Cl)=CC=C1S(=O)(=O)NC(=O)N1CCC(N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 RYOAZTXPWXIRGP-UHFFFAOYSA-N 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 4
- 238000002560 therapeutic procedure Methods 0.000 claims description 4
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 3
- STXMJDYUJFBELE-UHFFFAOYSA-N 4-[4-(2,4-dichlorophenoxy)piperidin-1-yl]-n-(4-methylphenyl)sulfonylpiperidine-1-carboxamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)N1CCC(N2CCC(CC2)OC=2C(=CC(Cl)=CC=2)Cl)CC1 STXMJDYUJFBELE-UHFFFAOYSA-N 0.000 claims description 3
- RDZRONBJZUCQAD-UHFFFAOYSA-N 4-[4-(2-chloro-4-fluorophenoxy)piperidin-1-yl]-n-(2-methylphenyl)sulfonylpiperidine-1-carboxamide Chemical compound CC1=CC=CC=C1S(=O)(=O)NC(=O)N1CCC(N2CCC(CC2)OC=2C(=CC(F)=CC=2)Cl)CC1 RDZRONBJZUCQAD-UHFFFAOYSA-N 0.000 claims description 3
- LPHIWCBAJGQIIF-UHFFFAOYSA-N 4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-n-methyl-n-(4-methylphenyl)sulfonylpiperidine-1-carboxamide Chemical compound C=1C=C(C)C=CC=1S(=O)(=O)N(C)C(=O)N(CC1)CCC1N(CC1)CCC1OC1=CC=C(Cl)C(Cl)=C1 LPHIWCBAJGQIIF-UHFFFAOYSA-N 0.000 claims description 3
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 3
- XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 claims description 3
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 3
- 239000012948 isocyanate Substances 0.000 claims description 3
- 150000002513 isocyanates Chemical class 0.000 claims description 3
- CXBGWBYHXGZMTD-UHFFFAOYSA-N n-(4-bromothiophen-2-yl)sulfonyl-4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]piperidine-1-carboxamide Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCN(C2CCN(CC2)C(=O)NS(=O)(=O)C=2SC=C(Br)C=2)CC1 CXBGWBYHXGZMTD-UHFFFAOYSA-N 0.000 claims description 3
- HBRSFVOYUOMDPA-UHFFFAOYSA-N n-(4-chloro-2,5-dimethylphenyl)sulfonyl-4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]piperidine-1-carboxamide Chemical compound C1=C(Cl)C(C)=CC(S(=O)(=O)NC(=O)N2CCC(CC2)N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)=C1C HBRSFVOYUOMDPA-UHFFFAOYSA-N 0.000 claims description 3
- SHRVEEBUQYOBLS-UHFFFAOYSA-N n-benzylsulfonyl-4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]piperidine-1-carboxamide Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCN(C2CCN(CC2)C(=O)NS(=O)(=O)CC=2C=CC=CC=2)CC1 SHRVEEBUQYOBLS-UHFFFAOYSA-N 0.000 claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 229960005141 piperazine Drugs 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 150000003456 sulfonamides Chemical class 0.000 claims description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- YMACOJXOWHVFPA-UHFFFAOYSA-N 4-[4-(2,4-dichloro-3-fluorophenoxy)piperidin-1-yl]-n-(2-methylphenyl)sulfonylpiperidine-1-carboxamide Chemical compound CC1=CC=CC=C1S(=O)(=O)NC(=O)N1CCC(N2CCC(CC2)OC=2C(=C(F)C(Cl)=CC=2)Cl)CC1 YMACOJXOWHVFPA-UHFFFAOYSA-N 0.000 claims description 2
- HZSIJCWSKQVTBQ-UHFFFAOYSA-N 4-[4-(2,4-dichloro-3-fluorophenoxy)piperidin-1-yl]-n-(4-methylphenyl)sulfonylpiperidine-1-carboxamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)N1CCC(N2CCC(CC2)OC=2C(=C(F)C(Cl)=CC=2)Cl)CC1 HZSIJCWSKQVTBQ-UHFFFAOYSA-N 0.000 claims description 2
- HFWLILWGBZWYRI-UHFFFAOYSA-N 4-[4-(2,4-dichloro-3-methylphenoxy)piperidin-1-yl]-n-(4-methylphenyl)sulfonylpiperidine-1-carboxamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)N1CCC(N2CCC(CC2)OC=2C(=C(C)C(Cl)=CC=2)Cl)CC1 HFWLILWGBZWYRI-UHFFFAOYSA-N 0.000 claims description 2
- JOQJAHXOGPPLHV-UHFFFAOYSA-N 4-[4-(2-chloro-4-fluorophenoxy)piperidin-1-yl]-n-(4-fluorophenyl)sulfonylpiperidine-1-carboxamide Chemical compound C1=CC(F)=CC=C1S(=O)(=O)NC(=O)N1CCC(N2CCC(CC2)OC=2C(=CC(F)=CC=2)Cl)CC1 JOQJAHXOGPPLHV-UHFFFAOYSA-N 0.000 claims description 2
- RSUJBLZGGJXMPA-UHFFFAOYSA-N 4-[4-(2-chloro-4-fluorophenoxy)piperidin-1-yl]-n-(4-methylphenyl)sulfonylpiperidine-1-carboxamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)N1CCC(N2CCC(CC2)OC=2C(=CC(F)=CC=2)Cl)CC1 RSUJBLZGGJXMPA-UHFFFAOYSA-N 0.000 claims description 2
- HJNPTYXKCYNFHI-UHFFFAOYSA-N 4-[4-(3,4-dichloro-2-methylphenoxy)piperidin-1-yl]-n-(2-methylphenyl)sulfonylpiperidine-1-carboxamide Chemical compound CC1=CC=CC=C1S(=O)(=O)NC(=O)N1CCC(N2CCC(CC2)OC=2C(=C(Cl)C(Cl)=CC=2)C)CC1 HJNPTYXKCYNFHI-UHFFFAOYSA-N 0.000 claims description 2
- JZWQTITXFPEKEB-UHFFFAOYSA-N 4-[4-(3,4-dichloro-2-methylphenoxy)piperidin-1-yl]-n-(4-fluorophenyl)sulfonylpiperidine-1-carboxamide Chemical compound CC1=C(Cl)C(Cl)=CC=C1OC1CCN(C2CCN(CC2)C(=O)NS(=O)(=O)C=2C=CC(F)=CC=2)CC1 JZWQTITXFPEKEB-UHFFFAOYSA-N 0.000 claims description 2
- CLHMIPRHBVGJLN-UHFFFAOYSA-N 4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-4-methyl-n-(2-methylphenyl)sulfonylpiperidine-1-carboxamide Chemical compound CC1=CC=CC=C1S(=O)(=O)NC(=O)N1CCC(C)(N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 CLHMIPRHBVGJLN-UHFFFAOYSA-N 0.000 claims description 2
- YCMJYSJIIXJFAN-UHFFFAOYSA-N 4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-4-methyl-n-[3-(trifluoromethyl)phenyl]sulfonylpiperidine-1-carboxamide Chemical compound C1CC(C)(N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CCN1C(=O)NS(=O)(=O)C1=CC=CC(C(F)(F)F)=C1 YCMJYSJIIXJFAN-UHFFFAOYSA-N 0.000 claims description 2
- DCFPBKYFTBZCLT-UHFFFAOYSA-N 4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-n-(1,1-dioxothiolan-3-yl)sulfonylpiperidine-1-carboxamide Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCN(C2CCN(CC2)C(=O)NS(=O)(=O)C2CS(=O)(=O)CC2)CC1 DCFPBKYFTBZCLT-UHFFFAOYSA-N 0.000 claims description 2
- STBLJTMWOFWZNU-UHFFFAOYSA-N 4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-n-(2,5-dimethoxyphenyl)sulfonylpiperidine-1-carboxamide Chemical compound COC1=CC=C(OC)C(S(=O)(=O)NC(=O)N2CCC(CC2)N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)=C1 STBLJTMWOFWZNU-UHFFFAOYSA-N 0.000 claims description 2
- UOWPMQNCLJZBEA-UHFFFAOYSA-N 4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-n-(2-methoxyphenyl)sulfonylpiperidine-1-carboxamide Chemical compound COC1=CC=CC=C1S(=O)(=O)NC(=O)N1CCC(N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 UOWPMQNCLJZBEA-UHFFFAOYSA-N 0.000 claims description 2
- IGLADUDHPDHSRD-UHFFFAOYSA-N 4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-n-(2-methylphenyl)sulfonylpiperidine-1-carboxamide Chemical compound CC1=CC=CC=C1S(=O)(=O)NC(=O)N1CCC(N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 IGLADUDHPDHSRD-UHFFFAOYSA-N 0.000 claims description 2
- ZNIHOYUYQMMJSD-UHFFFAOYSA-N 4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-n-(2-morpholin-4-ylpyridin-3-yl)sulfonylpiperidine-1-carboxamide Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCN(C2CCN(CC2)C(=O)NS(=O)(=O)C=2C(=NC=CC=2)N2CCOCC2)CC1 ZNIHOYUYQMMJSD-UHFFFAOYSA-N 0.000 claims description 2
- RYFIOOFJCDQMTQ-UHFFFAOYSA-N 4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-n-(2-piperidin-1-ylpyridin-3-yl)sulfonylpiperidine-1-carboxamide Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCN(C2CCN(CC2)C(=O)NS(=O)(=O)C=2C(=NC=CC=2)N2CCCCC2)CC1 RYFIOOFJCDQMTQ-UHFFFAOYSA-N 0.000 claims description 2
- QASDPIRCOYWLRS-UHFFFAOYSA-N 4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-n-(3,4-dimethoxyphenyl)sulfonylpiperidine-1-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1S(=O)(=O)NC(=O)N1CCC(N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 QASDPIRCOYWLRS-UHFFFAOYSA-N 0.000 claims description 2
- MPZGRQNIZNSJFU-UHFFFAOYSA-N 4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-n-(4-fluorophenyl)sulfonyl-4-methylpiperidine-1-carboxamide Chemical compound C1CC(C)(N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CCN1C(=O)NS(=O)(=O)C1=CC=C(F)C=C1 MPZGRQNIZNSJFU-UHFFFAOYSA-N 0.000 claims description 2
- KGIUUTHNCGIMIN-UHFFFAOYSA-N 4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-n-(4-hydroxyphenyl)sulfonylpiperidine-1-carboxamide Chemical compound C1=CC(O)=CC=C1S(=O)(=O)NC(=O)N1CCC(N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 KGIUUTHNCGIMIN-UHFFFAOYSA-N 0.000 claims description 2
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Landscapes
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| JP2009526014A (ja) * | 2006-02-10 | 2009-07-16 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | Ｃｘｃｒ３受容体拮抗薬としてのピペリジン誘導体 |
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| ES2489040T3 (es) | 2008-12-03 | 2014-09-01 | The Scripps Research Institute | Cultivos de células madre |
| PT3297438T (pt) | 2015-05-21 | 2022-01-25 | Chemocentryx Inc | Moduladores de ccr2 |
| MA50665A (fr) | 2017-09-25 | 2020-08-05 | Chemocentryx Inc | Polythérapie utilisant un antagoniste du récepteur 2 de la chimiokine (ccr2) et un inhibiteur pd-1/pd-l1 |
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| US20190269664A1 (en) | 2018-01-08 | 2019-09-05 | Chemocentryx, Inc. | Methods of treating solid tumors with ccr2 antagonists |
| TWI730297B (zh) * | 2018-02-27 | 2021-06-11 | 日商組合化學工業股份有限公司 | 巰基酚化合物的製造方法及巰基酚化合物的中間體 |
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| US5889006A (en) | 1995-02-23 | 1999-03-30 | Schering Corporation | Muscarinic antagonists |
| US5696267A (en) | 1995-05-02 | 1997-12-09 | Schering Corporation | Substituted oximes, hydrazones and olefins as neurokinin antagonists |
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| SE0200844D0 (sv) | 2002-03-19 | 2002-03-19 | Astrazeneca Ab | Chemical compounds |
| SE0200843D0 (sv) | 2002-03-19 | 2002-03-19 | Astrazeneca Ab | Chemical compounds |
| SE0202838D0 (sv) | 2002-09-24 | 2002-09-24 | Astrazeneca Ab | Chemical compounds |
| SE0300850D0 (sv) | 2003-03-25 | 2003-03-25 | Astrazeneca Ab | Chemical compounds |
| SE0300957D0 (sv) | 2003-04-01 | 2003-04-01 | Astrazeneca Ab | Chemical compounds |
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-
2002
- 2002-07-01 EP EP05018449A patent/EP1604982A1/en not_active Withdrawn
- 2002-07-01 PT PT02747793T patent/PT1404667E/pt unknown
- 2002-07-01 CA CA002452597A patent/CA2452597A1/en not_active Abandoned
- 2002-07-01 AT AT02747793T patent/ATE319703T1/de not_active IP Right Cessation
- 2002-07-01 US US10/480,625 patent/US7307090B2/en not_active Expired - Fee Related
- 2002-07-01 CN CNA028162714A patent/CN1545509A/zh active Pending
- 2002-07-01 JP JP2003510654A patent/JP3857270B2/ja not_active Expired - Fee Related
- 2002-07-01 NZ NZ530202A patent/NZ530202A/en unknown
- 2002-07-01 DK DK02747793T patent/DK1404667T3/da active
- 2002-07-01 WO PCT/SE2002/001311 patent/WO2003004487A1/en not_active Ceased
- 2002-07-01 HU HU0401886A patent/HUP0401886A2/hu unknown
- 2002-07-01 EP EP02747793A patent/EP1404667B1/en not_active Expired - Lifetime
- 2002-07-01 IL IL15925602A patent/IL159256A0/xx unknown
- 2002-07-01 RU RU2004100839/04A patent/RU2004100839A/ru not_active Application Discontinuation
- 2002-07-01 PL PL02368041A patent/PL368041A1/xx not_active Application Discontinuation
- 2002-07-01 KR KR10-2004-7000023A patent/KR20040013090A/ko not_active Ceased
- 2002-07-01 DE DE60209736T patent/DE60209736T2/de not_active Expired - Lifetime
- 2002-07-01 BR BR0210733-3A patent/BR0210733A/pt not_active IP Right Cessation
- 2002-07-01 MX MXPA03011722A patent/MXPA03011722A/es active IP Right Grant
- 2002-07-01 ES ES02747793T patent/ES2258642T3/es not_active Expired - Lifetime
- 2002-07-02 AR ARP020102488A patent/AR042401A1/es not_active Application Discontinuation
- 2002-07-02 SA SA02230184A patent/SA02230184B1/ar unknown
-
2003
- 2003-12-19 NO NO20035729A patent/NO20035729L/no not_active Application Discontinuation
- 2003-12-29 CO CO03112957A patent/CO5540307A2/es not_active Application Discontinuation
- 2003-12-30 IS IS7094A patent/IS7094A/is unknown
-
2006
- 2006-06-07 CY CY20061100755T patent/CY1106095T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AR042401A1 (es) | 2005-06-22 |
| EP1404667A1 (en) | 2004-04-07 |
| US20040235894A1 (en) | 2004-11-25 |
| HK1062559A1 (en) | 2004-11-12 |
| CN1545509A (zh) | 2004-11-10 |
| CA2452597A1 (en) | 2003-01-16 |
| CO5540307A2 (es) | 2005-07-29 |
| JP3857270B2 (ja) | 2006-12-13 |
| ES2258642T3 (es) | 2006-09-01 |
| EP1404667B1 (en) | 2006-03-08 |
| US7307090B2 (en) | 2007-12-11 |
| WO2003004487A1 (en) | 2003-01-16 |
| EP1604982A1 (en) | 2005-12-14 |
| KR20040013090A (ko) | 2004-02-11 |
| DK1404667T3 (da) | 2006-07-10 |
| RU2004100839A (ru) | 2005-06-20 |
| MXPA03011722A (es) | 2004-03-19 |
| SA02230184B1 (ar) | 2007-03-25 |
| ATE319703T1 (de) | 2006-03-15 |
| DE60209736D1 (de) | 2006-05-04 |
| JP2004536112A (ja) | 2004-12-02 |
| IL159256A0 (en) | 2004-06-01 |
| IS7094A (is) | 2003-12-30 |
| PT1404667E (pt) | 2006-07-31 |
| PL368041A1 (en) | 2005-03-21 |
| BR0210733A (pt) | 2004-07-20 |
| NZ530202A (en) | 2005-06-24 |
| NO20035729L (no) | 2004-02-23 |
| CY1106095T1 (el) | 2011-06-08 |
| HUP0401886A2 (hu) | 2004-12-28 |
| NO20035729D0 (no) | 2003-12-19 |
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