JP2004525892A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2004525892A5 JP2004525892A5 JP2002563137A JP2002563137A JP2004525892A5 JP 2004525892 A5 JP2004525892 A5 JP 2004525892A5 JP 2002563137 A JP2002563137 A JP 2002563137A JP 2002563137 A JP2002563137 A JP 2002563137A JP 2004525892 A5 JP2004525892 A5 JP 2004525892A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- trifluoromethyl
- bis
- formula
- methanone
- 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.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 claims 43
- 125000000217 alkyl group Chemical group 0.000 claims 22
- -1 NH-phenyl Chemical group 0.000 claims 13
- 229910052739 hydrogen Inorganic materials 0.000 claims 12
- 239000001257 hydrogen Substances 0.000 claims 12
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 12
- 229910052736 halogen Inorganic materials 0.000 claims 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 9
- 150000002367 halogens Chemical class 0.000 claims 8
- 125000002757 morpholinyl group Chemical group 0.000 claims 8
- 125000004193 piperazinyl group Chemical group 0.000 claims 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 6
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 6
- 125000001153 fluoro group Chemical group F* 0.000 claims 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims 4
- 239000002253 acid Substances 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 125000003373 pyrazinyl group Chemical group 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- 125000005988 1,1-dioxo-thiomorpholinyl group Chemical group 0.000 claims 2
- 125000005987 1-oxo-thiomorpholinyl group Chemical group 0.000 claims 2
- 102000002002 Neurokinin-1 Receptors Human genes 0.000 claims 2
- 108010040718 Neurokinin-1 Receptors Proteins 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 239000002464 receptor antagonist Substances 0.000 claims 2
- 229940044551 receptor antagonist Drugs 0.000 claims 2
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims 2
- GJMIULBZYICSMI-SFTDATJTSA-N 1-[4-[(3R,4S)-1-[3,5-bis(trifluoromethyl)benzoyl]-3-(4-chlorophenyl)piperidin-4-yl]piperazin-1-yl]-2,2,2-trifluoroethanone Chemical compound FC(C=1C=C(C(=O)N2C[C@H]([C@H](CC2)N2CCN(CC2)C(C(F)(F)F)=O)C2=CC=C(C=C2)Cl)C=C(C1)C(F)(F)F)(F)F GJMIULBZYICSMI-SFTDATJTSA-N 0.000 claims 1
- CGARRQSZKTWYFN-NSOVKSMOSA-N 1-[4-[(3R,4S)-1-[3,5-bis(trifluoromethyl)benzoyl]-3-phenylpiperidin-4-yl]piperazin-1-yl]-2-phenylethanone Chemical compound FC(C=1C=C(C(=O)N2C[C@H]([C@H](CC2)N2CCN(CC2)C(CC2=CC=CC=C2)=O)C2=CC=CC=C2)C=C(C1)C(F)(F)F)(F)F CGARRQSZKTWYFN-NSOVKSMOSA-N 0.000 claims 1
- GJMIULBZYICSMI-UHFFFAOYSA-N 1-[4-[1-[3,5-bis(trifluoromethyl)benzoyl]-3-(4-chlorophenyl)piperidin-4-yl]piperazin-1-yl]-2,2,2-trifluoroethanone Chemical compound C1CN(C(=O)C(F)(F)F)CCN1C1C(C=2C=CC(Cl)=CC=2)CN(C(=O)C=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)CC1 GJMIULBZYICSMI-UHFFFAOYSA-N 0.000 claims 1
- VURZIUHIBJZQJU-ZEQRLZLVSA-N 2-[4-[(3R,4S)-1-[3,5-bis(trifluoromethyl)benzoyl]-3-phenylpiperidin-4-yl]piperazin-1-yl]-N,N-dimethylacetamide Chemical compound FC(C=1C=C(C(=O)N2C[C@H]([C@H](CC2)N2CCN(CC2)CC(=O)N(C)C)C2=CC=CC=C2)C=C(C1)C(F)(F)F)(F)F VURZIUHIBJZQJU-ZEQRLZLVSA-N 0.000 claims 1
- XILVWQMCIFIHBH-VMPREFPWSA-N 2-[4-[(3R,4S)-1-[3,5-bis(trifluoromethyl)benzoyl]-3-phenylpiperidin-4-yl]piperazin-1-yl]-N-(2,6-dimethylphenyl)acetamide Chemical compound FC(C=1C=C(C(=O)N2C[C@H]([C@H](CC2)N2CCN(CC2)CC(=O)NC2=C(C=CC=C2C)C)C2=CC=CC=C2)C=C(C1)C(F)(F)F)(F)F XILVWQMCIFIHBH-VMPREFPWSA-N 0.000 claims 1
- XFCPGAHDBKKEEC-UHFFFAOYSA-N 4-[3,5-bis(trifluoromethyl)phenyl]-4-[4-(cyclopropylmethyl)piperazin-1-yl]-3-(4-methylphenyl)piperidine-1-carbaldehyde Chemical compound C1=CC(C)=CC=C1C1C(C=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)(N2CCN(CC3CC3)CC2)CCN(C=O)C1 XFCPGAHDBKKEEC-UHFFFAOYSA-N 0.000 claims 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
- PFQVGWLVKBANFL-SFTDATJTSA-N FC(C=1C=C(C(=O)N2C[C@H]([C@H](CC2)N2CC(CC2)=O)C2=CC=CC=C2)C=C(C1)C(F)(F)F)(F)F Chemical compound FC(C=1C=C(C(=O)N2C[C@H]([C@H](CC2)N2CC(CC2)=O)C2=CC=CC=C2)C=C(C1)C(F)(F)F)(F)F PFQVGWLVKBANFL-SFTDATJTSA-N 0.000 claims 1
- FMVSQTXHPKIBOG-NSOVKSMOSA-N FC(C=1C=C(C(=O)N2C[C@H]([C@H](CC2)N2CCN(CC2)CC(=O)NC2=CC=C(C=C2)F)C2=CC=CC=C2)C=C(C1)C(F)(F)F)(F)F Chemical compound FC(C=1C=C(C(=O)N2C[C@H]([C@H](CC2)N2CCN(CC2)CC(=O)NC2=CC=C(C=C2)F)C2=CC=CC=C2)C=C(C1)C(F)(F)F)(F)F FMVSQTXHPKIBOG-NSOVKSMOSA-N 0.000 claims 1
- RGVRXDVQDCRDNG-SFTDATJTSA-N FC(C=1C=C(C=C(C1)C(F)(F)F)C(=O)N1C[C@H]([C@H](CC1)N1CCS(CC1)=O)C1=CC=CC=C1)(F)F Chemical compound FC(C=1C=C(C=C(C1)C(F)(F)F)C(=O)N1C[C@H]([C@H](CC1)N1CCS(CC1)=O)C1=CC=CC=C1)(F)F RGVRXDVQDCRDNG-SFTDATJTSA-N 0.000 claims 1
- RSCZASMERGDWQG-NSOVKSMOSA-N [(3R,4S)-4-(4-benzylpiperazin-1-yl)-3-phenylpiperidin-1-yl]-[3,5-bis(trifluoromethyl)phenyl]methanone Chemical compound C(C1=CC=CC=C1)N1CCN(CC1)[C@@H]1[C@@H](CN(CC1)C(=O)C1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F)C1=CC=CC=C1 RSCZASMERGDWQG-NSOVKSMOSA-N 0.000 claims 1
- CCXDRJAINCWDAQ-SFTDATJTSA-N [3,5-bis(trifluoromethyl)phenyl]-[(3R,4S)-3-(4-chlorophenyl)-4-morpholin-4-ylpiperidin-1-yl]methanone Chemical compound FC(C=1C=C(C=C(C1)C(F)(F)F)C(=O)N1C[C@H]([C@H](CC1)N1CCOCC1)C1=CC=C(C=C1)Cl)(F)F CCXDRJAINCWDAQ-SFTDATJTSA-N 0.000 claims 1
- QDZJLISLPHCAPG-PKTZIBPZSA-N [3,5-bis(trifluoromethyl)phenyl]-[(3R,4S)-3-(4-chlorophenyl)-4-phenylpiperidin-1-yl]methanone Chemical compound FC(C=1C=C(C=C(C1)C(F)(F)F)C(=O)N1C[C@H]([C@H](CC1)C1=CC=CC=C1)C1=CC=C(C=C1)Cl)(F)F QDZJLISLPHCAPG-PKTZIBPZSA-N 0.000 claims 1
- NTDHCKSZBFQTJJ-VXKWHMMOSA-N [3,5-bis(trifluoromethyl)phenyl]-[(3R,4S)-3-(4-fluorophenyl)-4-(4-methylpiperazin-1-yl)piperidin-1-yl]methanone Chemical compound FC(C=1C=C(C=C(C1)C(F)(F)F)C(=O)N1C[C@H]([C@H](CC1)N1CCN(CC1)C)C1=CC=C(C=C1)F)(F)F NTDHCKSZBFQTJJ-VXKWHMMOSA-N 0.000 claims 1
- OJCHNZGIVNTAKX-SFTDATJTSA-N [3,5-bis(trifluoromethyl)phenyl]-[(3R,4S)-3-(4-fluorophenyl)-4-morpholin-4-ylpiperidin-1-yl]methanone Chemical compound FC(C=1C=C(C=C(C1)C(F)(F)F)C(=O)N1C[C@H]([C@H](CC1)N1CCOCC1)C1=CC=C(C=C1)F)(F)F OJCHNZGIVNTAKX-SFTDATJTSA-N 0.000 claims 1
- MPHLYYLVNQTJED-SFTDATJTSA-N [3,5-bis(trifluoromethyl)phenyl]-[(3R,4S)-3-(4-fluorophenyl)-4-piperazin-1-ylpiperidin-1-yl]methanone Chemical compound FC(C=1C=C(C=C(C1)C(F)(F)F)C(=O)N1C[C@H]([C@H](CC1)N1CCNCC1)C1=CC=C(C=C1)F)(F)F MPHLYYLVNQTJED-SFTDATJTSA-N 0.000 claims 1
- PSRRKURJBFCJJI-ZEQRLZLVSA-N [3,5-bis(trifluoromethyl)phenyl]-[(3R,4S)-3-phenyl-4-(4-pyrazin-2-ylpiperazin-1-yl)piperidin-1-yl]methanone Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(C(=O)N2C[C@H]([C@H](CC2)N2CCN(CC2)C=2N=CC=NC=2)C=2C=CC=CC=2)=C1 PSRRKURJBFCJJI-ZEQRLZLVSA-N 0.000 claims 1
- PFNJHPGSNGDBSO-SFTDATJTSA-N [3,5-bis(trifluoromethyl)phenyl]-[(3R,4S)-3-phenyl-4-piperazin-1-ylpiperidin-1-yl]methanone Chemical compound FC(C=1C=C(C=C(C1)C(F)(F)F)C(=O)N1C[C@H]([C@H](CC1)N1CCNCC1)C1=CC=CC=C1)(F)F PFNJHPGSNGDBSO-SFTDATJTSA-N 0.000 claims 1
- BRJRXLQWTMSQBS-SFTDATJTSA-N [3,5-bis(trifluoromethyl)phenyl]-[(3R,4S)-3-phenyl-4-thiomorpholin-4-ylpiperidin-1-yl]methanone Chemical compound FC(C=1C=C(C=C(C1)C(F)(F)F)C(=O)N1C[C@H]([C@H](CC1)N1CCSCC1)C1=CC=CC=C1)(F)F BRJRXLQWTMSQBS-SFTDATJTSA-N 0.000 claims 1
- UDRBQEGZZSNZJV-PKTZIBPZSA-N [3,5-bis(trifluoromethyl)phenyl]-[(3R,4S)-4-(3-bromophenyl)-3-phenylpiperidin-1-yl]methanone Chemical compound FC(C=1C=C(C=C(C1)C(F)(F)F)C(=O)N1C[C@H]([C@H](CC1)C1=CC(=CC=C1)Br)C1=CC=CC=C1)(F)F UDRBQEGZZSNZJV-PKTZIBPZSA-N 0.000 claims 1
- QOPIJTBAENVABP-ZEQRLZLVSA-N [3,5-bis(trifluoromethyl)phenyl]-[(3R,4S)-4-(4-cyclopropylpiperazin-1-yl)-3-phenylpiperidin-1-yl]methanone Chemical compound FC(C=1C=C(C=C(C1)C(F)(F)F)C(=O)N1C[C@H]([C@H](CC1)N1CCN(CC1)C1CC1)C1=CC=CC=C1)(F)F QOPIJTBAENVABP-ZEQRLZLVSA-N 0.000 claims 1
- SVAYRKLDOZPACO-VXKWHMMOSA-N [3,5-bis(trifluoromethyl)phenyl]-[(3R,4S)-4-(4-methylpiperazin-1-yl)-3-phenylpiperidin-1-yl]methanone Chemical compound FC(C=1C=C(C=C(C1)C(F)(F)F)C(=O)N1C[C@H]([C@H](CC1)N1CCN(CC1)C)C1=CC=CC=C1)(F)F SVAYRKLDOZPACO-VXKWHMMOSA-N 0.000 claims 1
- VWNSKHONTPQIBQ-SXOMAYOGSA-N [3,5-bis(trifluoromethyl)phenyl]-[(3R,4S)-4-(4-morpholin-4-ylphenyl)-3-phenylpiperidin-1-yl]methanone Chemical compound FC(C=1C=C(C=C(C1)C(F)(F)F)C(=O)N1C[C@H]([C@H](CC1)C1=CC=C(C=C1)N1CCOCC1)C1=CC=CC=C1)(F)F VWNSKHONTPQIBQ-SXOMAYOGSA-N 0.000 claims 1
- VXKCYYXJWDLBCZ-FTJBHMTQSA-N [3,5-bis(trifluoromethyl)phenyl]-[(3R,4S)-4-[4-(2-methoxyethylamino)phenyl]-3-phenylpiperidin-1-yl]methanone Chemical compound FC(C=1C=C(C=C(C1)C(F)(F)F)C(=O)N1C[C@H]([C@H](CC1)C1=CC=C(C=C1)NCCOC)C1=CC=CC=C1)(F)F VXKCYYXJWDLBCZ-FTJBHMTQSA-N 0.000 claims 1
- JYFFYYUGBWGEKI-IZLXSDGUSA-N [3,5-bis(trifluoromethyl)phenyl]-[(3R,4S)-4-[4-(4-methylpiperazin-1-yl)phenyl]-3-phenylpiperidin-1-yl]methanone Chemical compound FC(C=1C=C(C=C(C1)C(F)(F)F)C(=O)N1C[C@H]([C@H](CC1)C1=CC=C(C=C1)N1CCN(CC1)C)C1=CC=CC=C1)(F)F JYFFYYUGBWGEKI-IZLXSDGUSA-N 0.000 claims 1
- RFBURTLUSXOIHK-DQEYMECFSA-N [3,5-bis(trifluoromethyl)phenyl]-[(3R,4S)-4-[4-(cyclopropylmethyl)piperazin-1-yl]-3-(4-fluorophenyl)piperidin-1-yl]methanone Chemical compound FC(C=1C=C(C=C(C1)C(F)(F)F)C(=O)N1C[C@H]([C@H](CC1)N1CCN(CC1)CC1CC1)C1=CC=C(C=C1)F)(F)F RFBURTLUSXOIHK-DQEYMECFSA-N 0.000 claims 1
- HDGHBMSKSIBEPD-DQEYMECFSA-N [3,5-bis(trifluoromethyl)phenyl]-[(3R,4S)-4-[4-(cyclopropylmethyl)piperazin-1-yl]-3-phenylpiperidin-1-yl]methanone Chemical compound FC(C=1C=C(C=C(C1)C(F)(F)F)C(=O)N1C[C@H]([C@H](CC1)N1CCN(CC1)CC1CC1)C1=CC=CC=C1)(F)F HDGHBMSKSIBEPD-DQEYMECFSA-N 0.000 claims 1
- JEIFPGIGTTZXDQ-DQEYMECFSA-N [3,5-bis(trifluoromethyl)phenyl]-[(3R,4S)-4-[4-(morpholine-4-carbonyl)piperazin-1-yl]-3-phenylpiperidin-1-yl]methanone Chemical compound FC(C=1C=C(C(=O)N2C[C@H]([C@H](CC2)N2CCN(CC2)C(=O)N2CCOCC2)C2=CC=CC=C2)C=C(C1)C(F)(F)F)(F)F JEIFPGIGTTZXDQ-DQEYMECFSA-N 0.000 claims 1
- IXPJTNGFNRDHMI-SFTDATJTSA-N [3,5-bis(trifluoromethyl)phenyl]-[(3R,4S)-4-morpholin-4-yl-3-phenylpiperidin-1-yl]methanone Chemical compound FC(C=1C=C(C=C(C1)C(F)(F)F)C(=O)N1C[C@H]([C@H](CC1)N1CCOCC1)C1=CC=CC=C1)(F)F IXPJTNGFNRDHMI-SFTDATJTSA-N 0.000 claims 1
- XRUKHJOJTLIFMF-UHFFFAOYSA-N [3,5-bis(trifluoromethyl)phenyl]-[3-(4-chlorophenyl)-4-[4-(cyclopropylmethyl)piperazin-1-yl]piperidin-1-yl]methanone Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(C(=O)N2CC(C(CC2)N2CCN(CC3CC3)CC2)C=2C=CC(Cl)=CC=2)=C1 XRUKHJOJTLIFMF-UHFFFAOYSA-N 0.000 claims 1
- MMWYCGIIXQMACZ-UHFFFAOYSA-N [3,5-bis(trifluoromethyl)phenyl]-[3-(4-chlorophenyl)-4-pyrrolidin-1-ylpiperidin-1-yl]methanone Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(C(=O)N2CC(C(CC2)N2CCCC2)C=2C=CC(Cl)=CC=2)=C1 MMWYCGIIXQMACZ-UHFFFAOYSA-N 0.000 claims 1
- NTDHCKSZBFQTJJ-UHFFFAOYSA-N [3,5-bis(trifluoromethyl)phenyl]-[3-(4-fluorophenyl)-4-(4-methylpiperazin-1-yl)piperidin-1-yl]methanone Chemical compound C1CN(C)CCN1C1C(C=2C=CC(F)=CC=2)CN(C(=O)C=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)CC1 NTDHCKSZBFQTJJ-UHFFFAOYSA-N 0.000 claims 1
- IMBFYCYNNWNYJR-UHFFFAOYSA-N [3,5-bis(trifluoromethyl)phenyl]-[3-(4-methylphenyl)-4-(4-methylpiperazin-1-yl)piperidin-1-yl]methanone Chemical compound C1CN(C)CCN1C1C(C=2C=CC(C)=CC=2)CN(C(=O)C=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)CC1 IMBFYCYNNWNYJR-UHFFFAOYSA-N 0.000 claims 1
- VWNHFOMGPDXVQE-UHFFFAOYSA-N [3,5-bis(trifluoromethyl)phenyl]-[3-(4-methylphenyl)-4-[4-(morpholine-4-carbonyl)piperazin-1-yl]piperidin-1-yl]methanone Chemical compound C1=CC(C)=CC=C1C1C(N2CCN(CC2)C(=O)N2CCOCC2)CCN(C(=O)C=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)C1 VWNHFOMGPDXVQE-UHFFFAOYSA-N 0.000 claims 1
- QOPIJTBAENVABP-UHFFFAOYSA-N [3,5-bis(trifluoromethyl)phenyl]-[4-(4-cyclopropylpiperazin-1-yl)-3-phenylpiperidin-1-yl]methanone Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(C(=O)N2CC(C(CC2)N2CCN(CC2)C2CC2)C=2C=CC=CC=2)=C1 QOPIJTBAENVABP-UHFFFAOYSA-N 0.000 claims 1
- SVAYRKLDOZPACO-UHFFFAOYSA-N [3,5-bis(trifluoromethyl)phenyl]-[4-(4-methylpiperazin-1-yl)-3-phenylpiperidin-1-yl]methanone Chemical compound C1CN(C)CCN1C1C(C=2C=CC=CC=2)CN(C(=O)C=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)CC1 SVAYRKLDOZPACO-UHFFFAOYSA-N 0.000 claims 1
- ZWZOUGJACPPJBQ-UHFFFAOYSA-N [3,5-bis(trifluoromethyl)phenyl]-[4-[4-(2-hydroxyethyl)piperazin-1-yl]-3-phenylpiperidin-1-yl]methanone Chemical compound C1CN(CCO)CCN1C1C(C=2C=CC=CC=2)CN(C(=O)C=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)CC1 ZWZOUGJACPPJBQ-UHFFFAOYSA-N 0.000 claims 1
- HDGHBMSKSIBEPD-UHFFFAOYSA-N [3,5-bis(trifluoromethyl)phenyl]-[4-[4-(cyclopropylmethyl)piperazin-1-yl]-3-phenylpiperidin-1-yl]methanone Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(C(=O)N2CC(C(CC2)N2CCN(CC3CC3)CC2)C=2C=CC=CC=2)=C1 HDGHBMSKSIBEPD-UHFFFAOYSA-N 0.000 claims 1
- UQABNGOOEFUUOI-ZEQRLZLVSA-N [4-[(3R,4S)-1-[3,5-bis(trifluoromethyl)benzoyl]-3-phenylpiperidin-4-yl]piperazin-1-yl]-cyclopropylmethanone Chemical compound FC(C=1C=C(C=C(C1)C(F)(F)F)C(=O)N1C[C@H]([C@H](CC1)N1CCN(CC1)C(=O)C1CC1)C1=CC=CC=C1)(F)F UQABNGOOEFUUOI-ZEQRLZLVSA-N 0.000 claims 1
- IKDCKWKTTNIJRM-UHFFFAOYSA-N [4-[1-[3,5-bis(trifluoromethyl)benzoyl]-3-(4-methylphenyl)piperidin-4-yl]piperazin-1-yl]-cyclopropylmethanone Chemical compound C1=CC(C)=CC=C1C1C(N2CCN(CC2)C(=O)C2CC2)CCN(C(=O)C=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)C1 IKDCKWKTTNIJRM-UHFFFAOYSA-N 0.000 claims 1
- UQABNGOOEFUUOI-UHFFFAOYSA-N [4-[1-[3,5-bis(trifluoromethyl)benzoyl]-3-phenylpiperidin-4-yl]piperazin-1-yl]-cyclopropylmethanone Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(C(=O)N2CC(C(CC2)N2CCN(CC2)C(=O)C2CC2)C=2C=CC=CC=2)=C1 UQABNGOOEFUUOI-UHFFFAOYSA-N 0.000 claims 1
- 230000010933 acylation Effects 0.000 claims 1
- 238000005917 acylation reaction Methods 0.000 claims 1
- 230000029936 alkylation Effects 0.000 claims 1
- 238000005804 alkylation reaction Methods 0.000 claims 1
- 238000005576 amination reaction Methods 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 238000006264 debenzylation reaction Methods 0.000 claims 1
- 230000001590 oxidative effect Effects 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP01102557 | 2001-02-06 | ||
| PCT/EP2002/000851 WO2002062784A1 (en) | 2001-02-06 | 2002-01-28 | Piperidinee derivatives as neurokinin 1 antagonists |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2004525892A JP2004525892A (ja) | 2004-08-26 |
| JP2004525892A5 true JP2004525892A5 (cg-RX-API-DMAC7.html) | 2005-06-09 |
| JP4181409B2 JP4181409B2 (ja) | 2008-11-12 |
Family
ID=8176398
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002563137A Expired - Fee Related JP4181409B2 (ja) | 2001-02-06 | 2002-01-28 | ニューロキニン１アンタゴニストとしてのピペリジン誘導体 |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US6642226B2 (cg-RX-API-DMAC7.html) |
| EP (1) | EP1360184B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JP4181409B2 (cg-RX-API-DMAC7.html) |
| KR (1) | KR100566470B1 (cg-RX-API-DMAC7.html) |
| CN (1) | CN1229373C (cg-RX-API-DMAC7.html) |
| AR (1) | AR035427A1 (cg-RX-API-DMAC7.html) |
| AT (1) | ATE292128T1 (cg-RX-API-DMAC7.html) |
| AU (1) | AU2002228072B2 (cg-RX-API-DMAC7.html) |
| BR (1) | BR0206915A (cg-RX-API-DMAC7.html) |
| CA (1) | CA2435946C (cg-RX-API-DMAC7.html) |
| DE (1) | DE60203481T2 (cg-RX-API-DMAC7.html) |
| DK (1) | DK1360184T3 (cg-RX-API-DMAC7.html) |
| ES (1) | ES2238560T3 (cg-RX-API-DMAC7.html) |
| MX (1) | MXPA03006991A (cg-RX-API-DMAC7.html) |
| PT (1) | PT1360184E (cg-RX-API-DMAC7.html) |
| WO (1) | WO2002062784A1 (cg-RX-API-DMAC7.html) |
| ZA (1) | ZA200305887B (cg-RX-API-DMAC7.html) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| UA81918C2 (uk) * | 2002-10-08 | 2008-02-25 | Янссен Фармацевтика Н.В. | Заміщені похідні 1,4-дипіперидин-4-ілпіперазину та їх застосування як нейрокінінових антагоністів |
| JO2485B1 (en) * | 2002-12-23 | 2009-01-20 | شركة جانسين فارماسوتيكا ان. في | 1-Piperidine-3-Yl-4-Piperidine-4-Yl-Piperazine derivatives substituted and used as quinine antagonists |
| JO2696B1 (en) * | 2002-12-23 | 2013-03-03 | شركة جانسين فارماسوتيكا ان. في | Derivatives of 1-piperdine-4-yl-4-biprolidine-3-yl-piperazine substituted and used as quinine antagonists |
| ES2282731T3 (es) * | 2002-12-23 | 2007-10-16 | Janssen Pharmaceutica N.V. | Derivados de 1-piperidin-4-il-4-azetidin-3-il-piperazina sustituida y su uso como antagonistas de neuroquininas. |
| ATE400568T1 (de) * | 2002-12-23 | 2008-07-15 | Janssen Pharmaceutica Nv | Substituierte 4-(4-piperidin-yl-piperazin-1-yl)- azepan-derivate und ihre verwendung als tachykinin-antagonisten |
| AU2004246817A1 (en) | 2003-06-10 | 2004-12-23 | Janssen Pharmaceutica N.V. | Substituted 1, 4-di-piperidin-4-yl-piperazine derivative combined with an opioid analgesic and their use for the treatment of pain and side-effects associated with opioid-based treatments |
| JO2525B1 (en) * | 2004-04-08 | 2010-03-17 | شركة جانسين فارماسوتيكا ان. في | Derived 4-alkyl-and-4-canoelperidine derivatives and their use as anti-neroquin |
| US7635698B2 (en) * | 2004-12-29 | 2009-12-22 | Millennium Pharmaceuticals, Inc. | Compounds useful as chemokine receptor antagonists |
| US7880002B2 (en) * | 2004-12-29 | 2011-02-01 | Millennium Pharmaceuticals, Inc. | Substituted piperazinyl-pyrrolidine compounds useful as chemokine receptor antagonists |
| US7879838B2 (en) * | 2005-02-16 | 2011-02-01 | Schering Corporation | Heteroaryl substituted pyrazinyl-piperazine-piperidines with CXCR3 antagonist activity |
| BRPI0606187A2 (pt) | 2005-02-25 | 2009-06-09 | Hoffmann La Roche | comprimidos com capacidade de dispersão da substáncia do fármaco melhorada |
| EA014239B1 (ru) * | 2005-03-08 | 2010-10-29 | Янссен Фармацевтика Н.В. | Производные диаза-спиро-[4,4]нонана в качестве антагонистов нейрокинина (nk1) |
| EP1948607B1 (en) | 2005-09-16 | 2010-04-07 | Janssen Pharmaceutica, N.V. | Cyclopropyl amines as modulators of the histamine h3 receptor |
| WO2007053499A2 (en) | 2005-11-01 | 2007-05-10 | Millennium Pharmaceuticals, Inc. | Compounds useful as antagonists of ccr2 |
| US8067457B2 (en) | 2005-11-01 | 2011-11-29 | Millennium Pharmaceuticals, Inc. | Compounds useful as antagonists of CCR2 |
| CN101605767A (zh) | 2006-12-14 | 2009-12-16 | 詹森药业有限公司 | 制备哌嗪基苯甲酰胺衍生物和二氮杂环庚烷基苯甲酰胺衍生物的方法 |
| CA2676357A1 (en) | 2007-01-24 | 2008-07-31 | Glaxo Group Limited | Pharmaceutical compositions comprising 3, 5-diamin0-6- (2, 3-dichl0phenyl) -l, 2, 4-triazine or r (-) -2, 4-diamino-5- (2, 3-dichlorophenyl) -6-fluoromethyl pyrimidine and an nk1 |
| US8063075B2 (en) * | 2008-06-10 | 2011-11-22 | Hoffmann-La Roche Inc. | Pyrrolidine ether derivatives as NK3 receptor antagonists |
| WO2010081851A1 (en) | 2009-01-14 | 2010-07-22 | Genoscience Pharma | Piperidin-4-ylpiperazine compounds for the treatment of hcv infection |
| DK2729147T3 (en) | 2011-07-04 | 2017-12-18 | Irbm - Science Park S P A | NK-1 RECEPTOR ANTAGONISTS FOR TREATMENT OF CORNOVA |
| EP3758688B1 (en) | 2018-02-26 | 2024-03-27 | Ospedale San Raffaele S.r.l. | Nk-1 antagonists for use in the treatment of ocular pain |
| US12115154B2 (en) | 2020-12-16 | 2024-10-15 | Srx Cardio, Llc | Compounds for the modulation of proprotein convertase subtilisin/kexin type 9 (PCSK9) |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH545288A (de) | 1966-08-18 | 1974-01-31 | Sandoz Ag | Verfahren zur Herstellung neuer Piperidon-Derivate |
| IL111960A (en) | 1993-12-17 | 1999-12-22 | Merck & Co Inc | Morpholines and thiomorpholines their preparation and pharmaceutical compositions containing them |
| ATE364606T1 (de) | 1993-12-29 | 2007-07-15 | Merck Sharp & Dohme | Substituierte morpholinderivate und ihre verwendung als arzneimittel |
| TW385308B (en) | 1994-03-04 | 2000-03-21 | Merck & Co Inc | Prodrugs of morpholine tachykinin receptor antagonists |
| TW531537B (en) * | 1995-12-27 | 2003-05-11 | Janssen Pharmaceutica Nv | 1-(1,2-disubstituted piperidinyl)-4-substituted piperidine derivatives |
| GB9600235D0 (en) | 1996-01-05 | 1996-03-06 | Pfizer Ltd | Therapeutic agents |
| US5972938A (en) | 1997-12-01 | 1999-10-26 | Merck & Co., Inc. | Method for treating or preventing psychoimmunological disorders |
| US6291465B1 (en) | 1999-03-09 | 2001-09-18 | Hoffmann-La Roche Inc. | Biphenyl derivatives |
| US6291496B1 (en) | 1999-12-27 | 2001-09-18 | Andrew J. Dannenberg | Treating cancers associated with overexpression of class I family of receptor tyrosine kinases |
-
2002
- 2002-01-25 US US10/057,450 patent/US6642226B2/en not_active Expired - Fee Related
- 2002-01-28 BR BR0206915-6A patent/BR0206915A/pt not_active IP Right Cessation
- 2002-01-28 CN CNB028046064A patent/CN1229373C/zh not_active Expired - Fee Related
- 2002-01-28 KR KR1020037010336A patent/KR100566470B1/ko not_active Expired - Fee Related
- 2002-01-28 DE DE60203481T patent/DE60203481T2/de not_active Expired - Lifetime
- 2002-01-28 PT PT02710043T patent/PT1360184E/pt unknown
- 2002-01-28 DK DK02710043T patent/DK1360184T3/da active
- 2002-01-28 CA CA002435946A patent/CA2435946C/en not_active Expired - Fee Related
- 2002-01-28 AT AT02710043T patent/ATE292128T1/de not_active IP Right Cessation
- 2002-01-28 EP EP02710043A patent/EP1360184B1/en not_active Expired - Lifetime
- 2002-01-28 JP JP2002563137A patent/JP4181409B2/ja not_active Expired - Fee Related
- 2002-01-28 MX MXPA03006991A patent/MXPA03006991A/es active IP Right Grant
- 2002-01-28 AU AU2002228072A patent/AU2002228072B2/en not_active Ceased
- 2002-01-28 ES ES02710043T patent/ES2238560T3/es not_active Expired - Lifetime
- 2002-01-28 WO PCT/EP2002/000851 patent/WO2002062784A1/en not_active Ceased
- 2002-02-01 AR ARP020100349A patent/AR035427A1/es unknown
-
2003
- 2003-07-30 ZA ZA2003/05887A patent/ZA200305887B/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2004525892A5 (cg-RX-API-DMAC7.html) | ||
| RU2436776C2 (ru) | ДИАРИЛАМИН-СОДЕРЖАЩИЕ СОЕДИНЕНИЯ, КОМПОЗИЦИИ И ИХ ПРИМЕНЕНИЕ В КАЧЕСТВЕ МОДУЛЯТОРОВ РЕЦЕПТОРОВ с-КIT | |
| RU2497822C2 (ru) | Селективные к bcl-2 агенты, вызывающие апоптоз, для лечения рака и иммунных заболеваний | |
| RU2011127232A (ru) | Апоптоз-индуцирующие средства для лечения рака и иммунных и аутоиммунных заболеваний | |
| RU2003136097A (ru) | Производные фенилпиридинкарбонилпиперазина | |
| JP2004534010A5 (cg-RX-API-DMAC7.html) | ||
| RU2007118538A (ru) | Производные хинолина | |
| RU2003131693A (ru) | Новые ингибиторы тирозин киназ | |
| JP2013517283A5 (cg-RX-API-DMAC7.html) | ||
| JP4181409B2 (ja) | ニューロキニン１アンタゴニストとしてのピペリジン誘導体 | |
| JP2011515462A5 (cg-RX-API-DMAC7.html) | ||
| JP2006522771A5 (cg-RX-API-DMAC7.html) | ||
| RU2000129161A (ru) | Производное 1-[(1-замещенного-4-пиперидинил)метил]-4-пиперидина, способ его получения, фармацевтическая композиция, содержащая указанное соединение, и промежуточный продукт | |
| RU2005114489A (ru) | N-акрил-4-метиленамино-3-гидрокси-2-пиридоны в качестве противомикробных препаратов | |
| JP2002533326A5 (cg-RX-API-DMAC7.html) | ||
| JP2005533803A5 (cg-RX-API-DMAC7.html) | ||
| JP2006504761A5 (cg-RX-API-DMAC7.html) | ||
| JP2010538076A5 (cg-RX-API-DMAC7.html) | ||
| JP2002535323A5 (cg-RX-API-DMAC7.html) | ||
| JP2006505590A5 (cg-RX-API-DMAC7.html) | ||
| JP2006501306A5 (cg-RX-API-DMAC7.html) | ||
| RU2010138577A (ru) | ИНГИБИТОРЫ РЕЦЕПТОРА ХЕМОКИНА CxCR3 | |
| MXPA05010816A (es) | Derivados de 4-(4- (heterociclilalcox}fenil)- 1-(heterociclil- carbonil) piperidina y compuestos relacionados como antagonistas de h3 de la histamina para el tratamiento de enfermedades neurologicas tales como alzheimer. | |
| RU2010108687A (ru) | Ариловые эфиры пирролидина в качестве антагонистов рецепторов nk3 | |
| JP2006510609A5 (cg-RX-API-DMAC7.html) |