ZA200305887B - Piperidine derivatives as neurokinin 1 antagonists - Google Patents
Piperidine derivatives as neurokinin 1 antagonists Download PDFInfo
- Publication number
- ZA200305887B ZA200305887B ZA2003/05887A ZA200305887A ZA200305887B ZA 200305887 B ZA200305887 B ZA 200305887B ZA 2003/05887 A ZA2003/05887 A ZA 2003/05887A ZA 200305887 A ZA200305887 A ZA 200305887A ZA 200305887 B ZA200305887 B ZA 200305887B
- Authority
- ZA
- South Africa
- Prior art keywords
- phenyl
- trifluoromethyl
- bis
- methanone
- piperidin
- Prior art date
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- 229940127387 Neurokinin 1 Antagonists Drugs 0.000 title description 2
- 150000003053 piperidines Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 101
- 125000000217 alkyl group Chemical group 0.000 claims description 48
- 229910052736 halogen Inorganic materials 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 24
- 239000001257 hydrogen Substances 0.000 claims description 24
- 150000002431 hydrogen Chemical class 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- 150000002367 halogens Chemical class 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 125000001153 fluoro group Chemical group F* 0.000 claims description 10
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 10
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
- 239000003814 drug Substances 0.000 claims description 9
- -1 bromo, morpholinyl Chemical group 0.000 claims description 8
- 125000002757 morpholinyl group Chemical group 0.000 claims description 8
- 229940044551 receptor antagonist Drugs 0.000 claims description 8
- 239000002464 receptor antagonist Substances 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 102000002002 Neurokinin-1 Receptors Human genes 0.000 claims description 6
- 108010040718 Neurokinin-1 Receptors Proteins 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 125000004193 piperazinyl group Chemical group 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- 125000005988 1,1-dioxo-thiomorpholinyl group Chemical group 0.000 claims description 4
- 125000005987 1-oxo-thiomorpholinyl group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 230000001590 oxidative effect Effects 0.000 claims description 4
- 125000003386 piperidinyl group Chemical group 0.000 claims description 4
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 claims description 3
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 3
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- SKVLOVMYMAQCLU-UHFFFAOYSA-N [3,5-bis(trifluoromethyl)phenyl]-[4-(4-cyclopropylpiperazin-1-yl)-3-(4-methylphenyl)piperidin-1-yl]methanone Chemical compound C1=CC(C)=CC=C1C1C(N2CCN(CC2)C2CC2)CCN(C(=O)C=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)C1 SKVLOVMYMAQCLU-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 230000002152 alkylating effect Effects 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
- 230000002140 halogenating effect Effects 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 6
- 201000010099 disease Diseases 0.000 claims 4
- 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
- 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
- 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
- 102100021260 Galactosylgalactosylxylosylprotein 3-beta-glucuronosyltransferase 1 Human genes 0.000 claims 1
- 101000894906 Homo sapiens Galactosylgalactosylxylosylprotein 3-beta-glucuronosyltransferase 1 Proteins 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
- 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
- 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
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- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/10—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
- C07D211/16—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with acylated ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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
- C07D211/56—Nitrogen atoms
- C07D211/58—Nitrogen atoms attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D401/04—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 directly linked by a ring-member-to-ring-member bond
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- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Pulmonology (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Immunology (AREA)
- Hospice & Palliative Care (AREA)
- Rheumatology (AREA)
- Addiction (AREA)
- Psychology (AREA)
- Ophthalmology & Optometry (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Otolaryngology (AREA)
- Dermatology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
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 (1)
| Publication Number | Publication Date |
|---|---|
| ZA200305887B true ZA200305887B (en) | 2005-01-26 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA2003/05887A ZA200305887B (en) | 2001-02-06 | 2003-07-30 | Piperidine derivatives as neurokinin 1 antagonists |
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|---|---|
| US (1) | US6642226B2 (enExample) |
| EP (1) | EP1360184B1 (enExample) |
| JP (1) | JP4181409B2 (enExample) |
| KR (1) | KR100566470B1 (enExample) |
| CN (1) | CN1229373C (enExample) |
| AR (1) | AR035427A1 (enExample) |
| AT (1) | ATE292128T1 (enExample) |
| AU (1) | AU2002228072B2 (enExample) |
| BR (1) | BR0206915A (enExample) |
| CA (1) | CA2435946C (enExample) |
| DE (1) | DE60203481T2 (enExample) |
| DK (1) | DK1360184T3 (enExample) |
| ES (1) | ES2238560T3 (enExample) |
| MX (1) | MXPA03006991A (enExample) |
| PT (1) | PT1360184E (enExample) |
| WO (1) | WO2002062784A1 (enExample) |
| ZA (1) | ZA200305887B (enExample) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CA2509090C (en) * | 2002-12-23 | 2012-01-24 | Janssen Pharmaceutica N.V. | Substituted 4-(4-piperidin-4-yl-piperazin-1-yl)-azepane derivatives and their use as neurokinin antagonists |
| ATE354572T1 (de) * | 2002-12-23 | 2007-03-15 | Janssen Pharmaceutica Nv | Substituierte 1-piperidin-4-yl-4-azetidin-3-yl- piperazinderivate und deren verwendung als neurokininantagonisten |
| 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 |
| JP2006527236A (ja) | 2003-06-10 | 2006-11-30 | 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 | オピオイド鎮痛薬と組合せた置換1,4−ジ−ピペリジン−4−イル−ピペラジン誘導体ならびに疼痛およびオピオイドに基づく処置に伴う副作用の処置のためのそれらの使用 |
| 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 |
| WO2006071875A1 (en) | 2004-12-29 | 2006-07-06 | Millennium Pharmaceuticals, Inc. | Compounds useful as chemokine receptor antagonists |
| US7635698B2 (en) * | 2004-12-29 | 2009-12-22 | Millennium Pharmaceuticals, Inc. | Compounds useful as chemokine receptor antagonists |
| MX2007009949A (es) * | 2005-02-16 | 2007-09-26 | Schering Corp | Pirazinil-piperazin-piperidinas sustituidas con heteroarilo con actividad antagonista de cxcr3. |
| JP2008531509A (ja) | 2005-02-25 | 2008-08-14 | エフ.ホフマン−ラ ロシュ アーゲー | 医薬品成分の改良された分散性を有する錠剤 |
| CN101137657B (zh) * | 2005-03-08 | 2011-02-02 | 詹森药业有限公司 | 作为神经激肽(nk1)拮抗剂的二氮杂-螺-[4.4]-壬烷衍生物 |
| SI1948607T1 (sl) | 2005-09-16 | 2010-07-30 | Janssen Pharmaceutica Nv | Ciklopropil amini kot modulatorji histaminskega H3 receptorja |
| US8067415B2 (en) | 2005-11-01 | 2011-11-29 | Millennium Pharmaceuticals, Inc. | Compounds useful as antagonists of CCR2 |
| WO2007053498A1 (en) | 2005-11-01 | 2007-05-10 | Millennium Pharmaceuticals, Inc. | Compounds useful as antagonists of ccr2 |
| SI2121636T1 (sl) | 2006-12-14 | 2017-06-30 | Janssen Pharmaceutica N.V. | Postopek za pripravo derivatov piperazinila in diazepanil benzamida |
| EP2117538A1 (en) | 2007-01-24 | 2009-11-18 | Glaxo Group Limited | Pharmaceutical compositions comprising 2-methoxy-5- (5-trifluoromethyl-tetrazol-i-yl-benzyl) - (2s-phenyl-piperidin-3s-yl-) |
| 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 |
| ES2672099T3 (es) | 2011-07-04 | 2018-06-12 | Irbm - Science Park S.P.A. | Antagonistas del receptor NK-1 para el tratamiento de la neovascularización corneal |
| ES2980110T3 (es) | 2018-02-26 | 2024-09-30 | Ospedale San Raffaele Srl | Antagonistas de NK-1 para uso en el tratamiento del dolor ocular |
| 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 |
| SK283070B6 (sk) | 1993-12-29 | 2003-02-04 | Merck Sharp & Dohme Limited | Substituované morfolínové deriváty, spôsob ich výroby, farmaceutický prostriedok s ich obsahom a ich použitie |
| IL112778A0 (en) | 1994-03-04 | 1995-05-26 | Merck & Co Inc | Substituted heterocycles, their preparation and pharmaceutical compositions containing them |
| 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 |
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2002
- 2002-01-25 US US10/057,450 patent/US6642226B2/en not_active Expired - Fee Related
- 2002-01-28 EP EP02710043A patent/EP1360184B1/en not_active Expired - Lifetime
- 2002-01-28 AU AU2002228072A patent/AU2002228072B2/en not_active Ceased
- 2002-01-28 MX MXPA03006991A patent/MXPA03006991A/es active IP Right Grant
- 2002-01-28 WO PCT/EP2002/000851 patent/WO2002062784A1/en not_active Ceased
- 2002-01-28 CA CA002435946A patent/CA2435946C/en not_active Expired - Fee Related
- 2002-01-28 JP JP2002563137A patent/JP4181409B2/ja not_active Expired - Fee Related
- 2002-01-28 CN CNB028046064A patent/CN1229373C/zh not_active Expired - Fee Related
- 2002-01-28 DE DE60203481T patent/DE60203481T2/de not_active Expired - Lifetime
- 2002-01-28 ES ES02710043T patent/ES2238560T3/es not_active Expired - Lifetime
- 2002-01-28 BR BR0206915-6A patent/BR0206915A/pt not_active IP Right Cessation
- 2002-01-28 PT PT02710043T patent/PT1360184E/pt unknown
- 2002-01-28 KR KR1020037010336A patent/KR100566470B1/ko not_active Expired - Fee Related
- 2002-01-28 AT AT02710043T patent/ATE292128T1/de not_active IP Right Cessation
- 2002-01-28 DK DK02710043T patent/DK1360184T3/da active
- 2002-02-01 AR ARP020100349A patent/AR035427A1/es unknown
-
2003
- 2003-07-30 ZA ZA2003/05887A patent/ZA200305887B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU2002228072B2 (en) | 2006-08-03 |
| CN1229373C (zh) | 2005-11-30 |
| US20020151547A1 (en) | 2002-10-17 |
| ES2238560T3 (es) | 2005-09-01 |
| JP4181409B2 (ja) | 2008-11-12 |
| WO2002062784A1 (en) | 2002-08-15 |
| JP2004525892A (ja) | 2004-08-26 |
| WO2002062784A8 (en) | 2002-10-03 |
| DE60203481D1 (de) | 2005-05-04 |
| CA2435946C (en) | 2008-10-07 |
| AR035427A1 (es) | 2004-05-26 |
| KR100566470B1 (ko) | 2006-03-31 |
| US6642226B2 (en) | 2003-11-04 |
| EP1360184A1 (en) | 2003-11-12 |
| BR0206915A (pt) | 2004-02-03 |
| DE60203481T2 (de) | 2006-02-16 |
| KR20030070619A (ko) | 2003-08-30 |
| EP1360184B1 (en) | 2005-03-30 |
| PT1360184E (pt) | 2005-06-30 |
| CN1491222A (zh) | 2004-04-21 |
| MXPA03006991A (es) | 2003-11-18 |
| ATE292128T1 (de) | 2005-04-15 |
| DK1360184T3 (da) | 2005-08-01 |
| CA2435946A1 (en) | 2002-08-15 |
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