JP2006528939A5 - - Google Patents
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- JP2006528939A5 JP2006528939A5 JP2006529693A JP2006529693A JP2006528939A5 JP 2006528939 A5 JP2006528939 A5 JP 2006528939A5 JP 2006529693 A JP2006529693 A JP 2006529693A JP 2006529693 A JP2006529693 A JP 2006529693A JP 2006528939 A5 JP2006528939 A5 JP 2006528939A5
- Authority
- JP
- Japan
- Prior art keywords
- carbonyl
- piperidine
- isopropyl
- alkyl
- diazepane
- 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.)
- Pending
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- 125000000217 alkyl group Chemical group 0.000 claims description 37
- 150000001875 compounds Chemical class 0.000 claims description 28
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- 229910052736 halogen Inorganic materials 0.000 claims description 14
- 150000002367 halogens Chemical class 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 6
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 5
- 125000001072 heteroaryl group Chemical group 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 125000004043 oxo group Chemical group O=* 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 2
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 2
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 2
- 125000005947 C1-C6 alkylsulfonyloxy group Chemical group 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000003368 amide group Chemical group 0.000 claims description 2
- 125000003435 aroyl group Chemical group 0.000 claims description 2
- 125000005533 aryl carboxamido group Chemical group 0.000 claims description 2
- 125000005421 aryl sulfonamido group Chemical group 0.000 claims description 2
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 2
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims 8
- 239000012453 solvate Substances 0.000 claims 8
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 3
- -1 alkyl amide Chemical class 0.000 claims 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 3
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims 2
- 125000002098 pyridazinyl group Chemical group 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 2
- KWDBHXUIVWIYBV-UHFFFAOYSA-N (4-cyclobutyl-1,4-diazepan-1-yl)-[1-[6-(trifluoromethyl)pyridin-3-yl]piperidin-4-yl]methanone Chemical compound C1=NC(C(F)(F)F)=CC=C1N1CCC(C(=O)N2CCN(CCC2)C2CCC2)CC1 KWDBHXUIVWIYBV-UHFFFAOYSA-N 0.000 claims 1
- FOCIOGAYZXDVNE-UHFFFAOYSA-N (4-cyclobutylpiperazin-1-yl)-[1-[5-(trifluoromethyl)pyridin-2-yl]piperidin-4-yl]methanone Chemical compound N1=CC(C(F)(F)F)=CC=C1N1CCC(C(=O)N2CCN(CC2)C2CCC2)CC1 FOCIOGAYZXDVNE-UHFFFAOYSA-N 0.000 claims 1
- RRJSINFOJNXLNR-UHFFFAOYSA-N (4-cyclobutylpiperazin-1-yl)-[1-[6-(trifluoromethyl)pyridin-2-yl]piperidin-4-yl]methanone Chemical compound FC(F)(F)C1=CC=CC(N2CCC(CC2)C(=O)N2CCN(CC2)C2CCC2)=N1 RRJSINFOJNXLNR-UHFFFAOYSA-N 0.000 claims 1
- CGZUTBPQKHYXHB-UHFFFAOYSA-N (4-cyclobutylpiperazin-1-yl)-[1-[6-(trifluoromethyl)pyridin-3-yl]piperidin-4-yl]methanone Chemical compound C1=NC(C(F)(F)F)=CC=C1N1CCC(C(=O)N2CCN(CC2)C2CCC2)CC1 CGZUTBPQKHYXHB-UHFFFAOYSA-N 0.000 claims 1
- UWBDQNMCVFXIEG-UHFFFAOYSA-N (4-propan-2-yl-1,4-diazepan-1-yl)-[1-[2-(trifluoromethyl)pyrimidin-5-yl]piperidin-4-yl]methanone Chemical compound C1CN(C(C)C)CCCN1C(=O)C1CCN(C=2C=NC(=NC=2)C(F)(F)F)CC1 UWBDQNMCVFXIEG-UHFFFAOYSA-N 0.000 claims 1
- YNYDAHYVQHWLCL-UHFFFAOYSA-N (4-propan-2-yl-1,4-diazepan-1-yl)-[1-[4-(trifluoromethoxy)phenyl]piperidin-4-yl]methanone Chemical compound C1CN(C(C)C)CCCN1C(=O)C1CCN(C=2C=CC(OC(F)(F)F)=CC=2)CC1 YNYDAHYVQHWLCL-UHFFFAOYSA-N 0.000 claims 1
- RHQPBLRDTLVCNW-UHFFFAOYSA-N (4-propan-2-yl-1,4-diazepan-1-yl)-[1-[4-(trifluoromethyl)phenyl]piperidin-4-yl]methanone Chemical compound C1CN(C(C)C)CCCN1C(=O)C1CCN(C=2C=CC(=CC=2)C(F)(F)F)CC1 RHQPBLRDTLVCNW-UHFFFAOYSA-N 0.000 claims 1
- CUKZNHDZOYVRAQ-UHFFFAOYSA-N (4-propan-2-yl-1,4-diazepan-1-yl)-[1-[5-(trifluoromethyl)pyrazin-2-yl]piperidin-4-yl]methanone Chemical compound C1CN(C(C)C)CCCN1C(=O)C1CCN(C=2N=CC(=NC=2)C(F)(F)F)CC1 CUKZNHDZOYVRAQ-UHFFFAOYSA-N 0.000 claims 1
- XSHLQKFEJZWYBC-UHFFFAOYSA-N (4-propan-2-yl-1,4-diazepan-1-yl)-[1-[6-(trifluoromethyl)pyridazin-3-yl]piperidin-4-yl]methanone Chemical compound C1CN(C(C)C)CCCN1C(=O)C1CCN(C=2N=NC(=CC=2)C(F)(F)F)CC1 XSHLQKFEJZWYBC-UHFFFAOYSA-N 0.000 claims 1
- AHHPKVQYHXNBQN-UHFFFAOYSA-N (4-propan-2-yl-1,4-diazepan-1-yl)-[1-[6-(trifluoromethyl)pyridin-3-yl]piperidin-4-yl]methanone Chemical compound C1CN(C(C)C)CCCN1C(=O)C1CCN(C=2C=NC(=CC=2)C(F)(F)F)CC1 AHHPKVQYHXNBQN-UHFFFAOYSA-N 0.000 claims 1
- ZIOOSRUNDOXLPW-UHFFFAOYSA-N (4-propan-2-ylpiperazin-1-yl)-(1-quinolin-6-ylpiperidin-4-yl)methanone Chemical compound C1CN(C(C)C)CCN1C(=O)C1CCN(C=2C=C3C=CC=NC3=CC=2)CC1 ZIOOSRUNDOXLPW-UHFFFAOYSA-N 0.000 claims 1
- MHKSPEWRVFTDJC-UHFFFAOYSA-N (4-propan-2-ylpiperazin-1-yl)-[1-[5-(trifluoromethyl)pyrazin-2-yl]piperidin-4-yl]methanone Chemical compound C1CN(C(C)C)CCN1C(=O)C1CCN(C=2N=CC(=NC=2)C(F)(F)F)CC1 MHKSPEWRVFTDJC-UHFFFAOYSA-N 0.000 claims 1
- RKLASZGSKPZKHZ-UHFFFAOYSA-N (4-propan-2-ylpiperazin-1-yl)-[1-[6-(trifluoromethyl)pyridin-3-yl]piperidin-4-yl]methanone Chemical compound C1CN(C(C)C)CCN1C(=O)C1CCN(C=2C=NC(=CC=2)C(F)(F)F)CC1 RKLASZGSKPZKHZ-UHFFFAOYSA-N 0.000 claims 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- IYCDHQCNQZDYNU-UHFFFAOYSA-N 1-[4-[4-(4-cyclobutyl-1,4-diazepane-1-carbonyl)piperidin-1-yl]phenyl]ethanone Chemical compound C1=CC(C(=O)C)=CC=C1N1CCC(C(=O)N2CCN(CCC2)C2CCC2)CC1 IYCDHQCNQZDYNU-UHFFFAOYSA-N 0.000 claims 1
- MFPZTWLLRLSDCU-UHFFFAOYSA-N 1-[4-[4-(4-propan-2-yl-1,4-diazepane-1-carbonyl)piperidin-1-yl]phenyl]ethanone Chemical compound C1CN(C(C)C)CCCN1C(=O)C1CCN(C=2C=CC(=CC=2)C(C)=O)CC1 MFPZTWLLRLSDCU-UHFFFAOYSA-N 0.000 claims 1
- HLBMQESPSJOCCX-UHFFFAOYSA-N 1-[4-[4-(4-propan-2-yl-1,4-diazepane-1-carbonyl)piperidin-1-yl]phenyl]propan-1-one Chemical compound C1=CC(C(=O)CC)=CC=C1N1CCC(C(=O)N2CCN(CCC2)C(C)C)CC1 HLBMQESPSJOCCX-UHFFFAOYSA-N 0.000 claims 1
- IRBVOJGLAFAATL-UHFFFAOYSA-N 2,3-difluoro-4-[4-(4-propan-2-yl-1,4-diazepane-1-carbonyl)piperidin-1-yl]benzonitrile Chemical compound C1CN(C(C)C)CCCN1C(=O)C1CCN(C=2C(=C(F)C(C#N)=CC=2)F)CC1 IRBVOJGLAFAATL-UHFFFAOYSA-N 0.000 claims 1
- OIOOYJNTCPEDFV-UHFFFAOYSA-N 2,5-difluoro-4-[4-(4-propan-2-yl-1,4-diazepane-1-carbonyl)piperidin-1-yl]benzonitrile Chemical compound C1CN(C(C)C)CCCN1C(=O)C1CCN(C=2C(=CC(=C(F)C=2)C#N)F)CC1 OIOOYJNTCPEDFV-UHFFFAOYSA-N 0.000 claims 1
- MEZQPJQVIZGCIB-UHFFFAOYSA-N 2-chloro-4-[4-(4-cyclobutyl-1,4-diazepane-1-carbonyl)piperidin-1-yl]benzonitrile Chemical compound C1=C(C#N)C(Cl)=CC(N2CCC(CC2)C(=O)N2CCN(CCC2)C2CCC2)=C1 MEZQPJQVIZGCIB-UHFFFAOYSA-N 0.000 claims 1
- CRZONISEZDXWMR-UHFFFAOYSA-N 2-chloro-4-[4-(4-propan-2-yl-1,4-diazepane-1-carbonyl)piperidin-1-yl]benzonitrile Chemical compound C1CN(C(C)C)CCCN1C(=O)C1CCN(C=2C=C(Cl)C(C#N)=CC=2)CC1 CRZONISEZDXWMR-UHFFFAOYSA-N 0.000 claims 1
- HUUSEIICYFJWRU-UHFFFAOYSA-N 2-fluoro-4-[4-(4-propan-2-yl-1,4-diazepane-1-carbonyl)piperidin-1-yl]benzonitrile Chemical compound C1CN(C(C)C)CCCN1C(=O)C1CCN(C=2C=C(F)C(C#N)=CC=2)CC1 HUUSEIICYFJWRU-UHFFFAOYSA-N 0.000 claims 1
- PJXCYUMXRYLLPB-UHFFFAOYSA-N 3,5-difluoro-4-[4-(4-propan-2-yl-1,4-diazepane-1-carbonyl)piperidin-1-yl]benzonitrile Chemical compound C1CN(C(C)C)CCCN1C(=O)C1CCN(C=2C(=CC(=CC=2F)C#N)F)CC1 PJXCYUMXRYLLPB-UHFFFAOYSA-N 0.000 claims 1
- BTRCWAYXXBYDCQ-UHFFFAOYSA-N 3-chloro-4-[4-(4-cyclobutyl-1,4-diazepane-1-carbonyl)piperidin-1-yl]benzonitrile Chemical compound ClC1=CC(C#N)=CC=C1N1CCC(C(=O)N2CCN(CCC2)C2CCC2)CC1 BTRCWAYXXBYDCQ-UHFFFAOYSA-N 0.000 claims 1
- WYZARVUPDPRZCA-UHFFFAOYSA-N 3-chloro-4-[4-(4-propan-2-yl-1,4-diazepane-1-carbonyl)piperidin-1-yl]benzonitrile Chemical compound C1CN(C(C)C)CCCN1C(=O)C1CCN(C=2C(=CC(=CC=2)C#N)Cl)CC1 WYZARVUPDPRZCA-UHFFFAOYSA-N 0.000 claims 1
- WGTWDMGPOFCRMS-UHFFFAOYSA-N 3-fluoro-4-[4-(4-propan-2-yl-1,4-diazepane-1-carbonyl)piperidin-1-yl]benzonitrile Chemical compound C1CN(C(C)C)CCCN1C(=O)C1CCN(C=2C(=CC(=CC=2)C#N)F)CC1 WGTWDMGPOFCRMS-UHFFFAOYSA-N 0.000 claims 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- SBLKISJOQPOXNM-UHFFFAOYSA-N 4-[4-(4-cyclobutyl-1,4-diazepane-1-carbonyl)piperidin-1-yl]-2,5-difluorobenzonitrile Chemical compound C1=C(C#N)C(F)=CC(N2CCC(CC2)C(=O)N2CCN(CCC2)C2CCC2)=C1F SBLKISJOQPOXNM-UHFFFAOYSA-N 0.000 claims 1
- JKDIFUZVTSXGST-UHFFFAOYSA-N 4-[4-(4-cyclobutyl-1,4-diazepane-1-carbonyl)piperidin-1-yl]-2-(trifluoromethyl)benzonitrile Chemical compound C1=C(C#N)C(C(F)(F)F)=CC(N2CCC(CC2)C(=O)N2CCN(CCC2)C2CCC2)=C1 JKDIFUZVTSXGST-UHFFFAOYSA-N 0.000 claims 1
- ZDXLCSGJHVTVHM-UHFFFAOYSA-N 4-[4-(4-cyclobutyl-1,4-diazepane-1-carbonyl)piperidin-1-yl]-2-fluorobenzonitrile Chemical compound C1=C(C#N)C(F)=CC(N2CCC(CC2)C(=O)N2CCN(CCC2)C2CCC2)=C1 ZDXLCSGJHVTVHM-UHFFFAOYSA-N 0.000 claims 1
- LWMXYGRIPRADKA-UHFFFAOYSA-N 4-[4-(4-cyclobutyl-1,4-diazepane-1-carbonyl)piperidin-1-yl]benzonitrile Chemical compound C1CCN(C2CCC2)CCN1C(=O)C(CC1)CCN1C1=CC=C(C#N)C=C1 LWMXYGRIPRADKA-UHFFFAOYSA-N 0.000 claims 1
- FKLPIYRPQZWNHW-UHFFFAOYSA-N 4-[4-(4-cyclobutyl-1,4-diazepane-1-carbonyl)piperidin-1-yl]pyridine-2-carbonitrile Chemical compound C1CCN(C2CCC2)CCN1C(=O)C(CC1)CCN1C1=CC=NC(C#N)=C1 FKLPIYRPQZWNHW-UHFFFAOYSA-N 0.000 claims 1
- AGLOUAIOTHNXJX-UHFFFAOYSA-N 4-[4-(4-cyclobutylpiperazine-1-carbonyl)piperidin-1-yl]-2-(trifluoromethyl)benzonitrile Chemical compound C1=C(C#N)C(C(F)(F)F)=CC(N2CCC(CC2)C(=O)N2CCN(CC2)C2CCC2)=C1 AGLOUAIOTHNXJX-UHFFFAOYSA-N 0.000 claims 1
- XOZZNXMLZSVHRO-UHFFFAOYSA-N 4-[4-(4-cyclobutylpiperazine-1-carbonyl)piperidin-1-yl]-2-fluorobenzonitrile Chemical compound C1=C(C#N)C(F)=CC(N2CCC(CC2)C(=O)N2CCN(CC2)C2CCC2)=C1 XOZZNXMLZSVHRO-UHFFFAOYSA-N 0.000 claims 1
- CFUNZNFORJABNT-UHFFFAOYSA-N 4-[4-(4-cyclobutylpiperazine-1-carbonyl)piperidin-1-yl]-3,5-difluorobenzonitrile Chemical compound FC1=CC(C#N)=CC(F)=C1N1CCC(C(=O)N2CCN(CC2)C2CCC2)CC1 CFUNZNFORJABNT-UHFFFAOYSA-N 0.000 claims 1
- MHRVMXWAOUZACF-UHFFFAOYSA-N 4-[4-(4-cyclobutylpiperazine-1-carbonyl)piperidin-1-yl]benzonitrile Chemical compound C1CN(C2CCC2)CCN1C(=O)C(CC1)CCN1C1=CC=C(C#N)C=C1 MHRVMXWAOUZACF-UHFFFAOYSA-N 0.000 claims 1
- DUKXZNSTFXIDHV-UHFFFAOYSA-N 4-[4-(4-cyclobutylpiperazine-1-carbonyl)piperidin-1-yl]naphthalene-1-carbonitrile Chemical compound C1CN(C=2C3=CC=CC=C3C(C#N)=CC=2)CCC1C(=O)N(CC1)CCN1C1CCC1 DUKXZNSTFXIDHV-UHFFFAOYSA-N 0.000 claims 1
- NIEDPANBEFZRHH-UHFFFAOYSA-N 4-[4-(4-cyclopentylpiperazine-1-carbonyl)piperidin-1-yl]benzonitrile Chemical compound C1CN(C2CCCC2)CCN1C(=O)C(CC1)CCN1C1=CC=C(C#N)C=C1 NIEDPANBEFZRHH-UHFFFAOYSA-N 0.000 claims 1
- MTHVTAPHINRJDM-UHFFFAOYSA-N 4-[4-(4-propan-2-yl-1,4-diazepane-1-carbonyl)piperidin-1-yl]-2-(trifluoromethyl)benzonitrile Chemical compound C1CN(C(C)C)CCCN1C(=O)C1CCN(C=2C=C(C(C#N)=CC=2)C(F)(F)F)CC1 MTHVTAPHINRJDM-UHFFFAOYSA-N 0.000 claims 1
- ZKWGORSBDXZHIH-UHFFFAOYSA-N 4-[4-(4-propan-2-yl-1,4-diazepane-1-carbonyl)piperidin-1-yl]benzonitrile Chemical compound C1CN(C(C)C)CCCN1C(=O)C1CCN(C=2C=CC(=CC=2)C#N)CC1 ZKWGORSBDXZHIH-UHFFFAOYSA-N 0.000 claims 1
- ONXFDJQBIODPRP-UHFFFAOYSA-N 4-[4-(4-propan-2-yl-1,4-diazepane-1-carbonyl)piperidin-1-yl]naphthalene-1-carbonitrile Chemical compound C1CN(C(C)C)CCCN1C(=O)C1CCN(C=2C3=CC=CC=C3C(C#N)=CC=2)CC1 ONXFDJQBIODPRP-UHFFFAOYSA-N 0.000 claims 1
- PBMGIRHMQNGTDP-UHFFFAOYSA-N 4-[4-(4-propan-2-ylpiperazine-1-carbonyl)piperidin-1-yl]benzonitrile Chemical compound C1CN(C(C)C)CCN1C(=O)C1CCN(C=2C=CC(=CC=2)C#N)CC1 PBMGIRHMQNGTDP-UHFFFAOYSA-N 0.000 claims 1
- FZPZUNGFQLGPKM-KRWDZBQOSA-N 4-[4-[(3s)-3-methyl-4-propan-2-ylpiperazine-1-carbonyl]piperidin-1-yl]benzonitrile Chemical compound C1[C@H](C)N(C(C)C)CCN1C(=O)C1CCN(C=2C=CC(=CC=2)C#N)CC1 FZPZUNGFQLGPKM-KRWDZBQOSA-N 0.000 claims 1
- VUUOLWFOTDPJKR-HDICACEKSA-N 4-[4-[(3s,5r)-4-cyclobutyl-3,5-dimethylpiperazine-1-carbonyl]piperidin-1-yl]benzonitrile Chemical compound N1([C@H](C)CN(C[C@@H]1C)C(=O)C1CCN(CC1)C=1C=CC(=CC=1)C#N)C1CCC1 VUUOLWFOTDPJKR-HDICACEKSA-N 0.000 claims 1
- INYZZCRJVZBNDL-UHFFFAOYSA-N 5-[4-(4-cyclobutyl-1,4-diazepane-1-carbonyl)piperidin-1-yl]pyridine-2-carbonitrile Chemical compound C1CCN(C2CCC2)CCN1C(=O)C(CC1)CCN1C1=CC=C(C#N)N=C1 INYZZCRJVZBNDL-UHFFFAOYSA-N 0.000 claims 1
- IXJGJVGOBIPHMQ-UHFFFAOYSA-N 5-[4-(4-propan-2-yl-1,4-diazepane-1-carbonyl)piperidin-1-yl]pyridine-2-carbonitrile Chemical compound C1CN(C(C)C)CCCN1C(=O)C1CCN(C=2C=NC(=CC=2)C#N)CC1 IXJGJVGOBIPHMQ-UHFFFAOYSA-N 0.000 claims 1
- FHDDKNRLIJOKNI-UHFFFAOYSA-N 5-[4-(4-propan-2-ylpiperazine-1-carbonyl)piperidin-1-yl]pyridine-2-carbonitrile Chemical compound C1CN(C(C)C)CCN1C(=O)C1CCN(C=2C=NC(=CC=2)C#N)CC1 FHDDKNRLIJOKNI-UHFFFAOYSA-N 0.000 claims 1
- SNJNSMATZNKRMC-INIZCTEOSA-N 5-[4-[(3s)-3-methyl-4-propan-2-ylpiperazine-1-carbonyl]piperidin-1-yl]pyridine-2-carbonitrile Chemical compound C1[C@H](C)N(C(C)C)CCN1C(=O)C1CCN(C=2C=NC(=CC=2)C#N)CC1 SNJNSMATZNKRMC-INIZCTEOSA-N 0.000 claims 1
- RCFSFZKEYOPOKZ-UHFFFAOYSA-N 6-[4-(4-cyclobutyl-1,4-diazepane-1-carbonyl)piperidin-1-yl]pyridine-3-carbonitrile Chemical compound C1CCN(C2CCC2)CCN1C(=O)C(CC1)CCN1C1=CC=C(C#N)C=N1 RCFSFZKEYOPOKZ-UHFFFAOYSA-N 0.000 claims 1
- FVSIPSKRKYIVTL-UHFFFAOYSA-N 6-[4-(4-cyclobutylpiperazine-1-carbonyl)piperidin-1-yl]pyridine-3-carbonitrile Chemical compound C1CN(C2CCC2)CCN1C(=O)C(CC1)CCN1C1=CC=C(C#N)C=N1 FVSIPSKRKYIVTL-UHFFFAOYSA-N 0.000 claims 1
- JMYKEGRRYRKCTO-UHFFFAOYSA-N 6-[4-(4-propan-2-ylpiperazine-1-carbonyl)piperidin-1-yl]pyridine-3-carbonitrile Chemical compound C1CN(C(C)C)CCN1C(=O)C1CCN(C=2N=CC(=CC=2)C#N)CC1 JMYKEGRRYRKCTO-UHFFFAOYSA-N 0.000 claims 1
- GICALJMBTQYCBH-INIZCTEOSA-N 6-[4-[(3s)-3-methyl-4-propan-2-ylpiperazine-1-carbonyl]piperidin-1-yl]pyridine-3-carbonitrile Chemical compound C1[C@H](C)N(C(C)C)CCN1C(=O)C1CCN(C=2N=CC(=CC=2)C#N)CC1 GICALJMBTQYCBH-INIZCTEOSA-N 0.000 claims 1
- FWBBCLHRILPGFZ-UHFFFAOYSA-N 6-[4-[4-(3-methylbutyl)piperazine-1-carbonyl]piperidin-1-yl]pyridine-3-carbonitrile Chemical compound C1CN(CCC(C)C)CCN1C(=O)C1CCN(C=2N=CC(=CC=2)C#N)CC1 FWBBCLHRILPGFZ-UHFFFAOYSA-N 0.000 claims 1
- 208000012902 Nervous system disease Diseases 0.000 claims 1
- 208000025966 Neurological disease Diseases 0.000 claims 1
- KJWQIEHRABBFJY-AWEZNQCLSA-N [(3s)-3-methyl-4-propan-2-ylpiperazin-1-yl]-[1-[5-(trifluoromethyl)pyrazin-2-yl]piperidin-4-yl]methanone Chemical compound C1[C@H](C)N(C(C)C)CCN1C(=O)C1CCN(C=2N=CC(=NC=2)C(F)(F)F)CC1 KJWQIEHRABBFJY-AWEZNQCLSA-N 0.000 claims 1
- FMXNDUUAVIXCII-AWEZNQCLSA-N [(3s)-3-methyl-4-propan-2-ylpiperazin-1-yl]-[1-[6-(trifluoromethyl)pyridazin-3-yl]piperidin-4-yl]methanone Chemical compound C1[C@H](C)N(C(C)C)CCN1C(=O)C1CCN(C=2N=NC(=CC=2)C(F)(F)F)CC1 FMXNDUUAVIXCII-AWEZNQCLSA-N 0.000 claims 1
- BABJJMGJRHTHRU-HNNXBMFYSA-N [(3s)-3-methyl-4-propan-2-ylpiperazin-1-yl]-[1-[6-(trifluoromethyl)pyridin-3-yl]piperidin-4-yl]methanone Chemical compound C1[C@H](C)N(C(C)C)CCN1C(=O)C1CCN(C=2C=NC(=CC=2)C(F)(F)F)CC1 BABJJMGJRHTHRU-HNNXBMFYSA-N 0.000 claims 1
- KIRMECPPPIDOMB-UHFFFAOYSA-N [1-(2-methylquinolin-4-yl)piperidin-4-yl]-(4-propan-2-yl-1,4-diazepan-1-yl)methanone Chemical compound C1CN(C(C)C)CCCN1C(=O)C1CCN(C=2C3=CC=CC=C3N=C(C)C=2)CC1 KIRMECPPPIDOMB-UHFFFAOYSA-N 0.000 claims 1
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| JP2008516922A (ja) * | 2004-10-15 | 2008-05-22 | グラクソ グループ リミテッド | ヒスタミン受容体リガンドとしてのピロリジン誘導体 |
| ATE450525T1 (de) * | 2005-06-20 | 2009-12-15 | Schering Corp | Kohlenstoffgebundene substituierte piperidine und derivate daraus als histamin-h3-antagonisten |
| TW200738676A (en) * | 2005-06-20 | 2007-10-16 | Schering Corp | Heteroatom-linked substituted piperidines and derivatives thereof useful as histamine H3 antagonists |
| DE602006018301D1 (de) | 2005-06-22 | 2010-12-30 | Pfizer Prod Inc | Histamin-3-rezeptorantagonisten |
| US7851474B2 (en) | 2005-08-02 | 2010-12-14 | Neurogen Corporation | Dipiperazinyl ketones and related analogues |
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| US9108948B2 (en) | 2006-06-23 | 2015-08-18 | Abbvie Inc. | Cyclopropyl amine derivatives |
| BRPI0712823A2 (pt) | 2006-06-23 | 2012-07-24 | Abbott Lab | derivados de ciclopropil amina como moduladores de receptor de histamina h3 |
| JP2010520199A (ja) * | 2007-03-02 | 2010-06-10 | シェーリング コーポレイション | ピペリジン誘導体およびその使用方法 |
| TW200902007A (en) * | 2007-05-25 | 2009-01-16 | Astrazeneca Ab | Spirocyclopropyl piperidine derivatives |
| JP5603770B2 (ja) * | 2007-05-31 | 2014-10-08 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | Ｃｃｒ２受容体拮抗薬およびその使用 |
| CA2688585A1 (en) | 2007-06-11 | 2008-12-18 | F. Hoffmann-La Roche Ag | Cyclohexyl derivatives |
| DK2195293T3 (da) | 2007-08-22 | 2014-02-03 | Astrazeneca Ab | Cyclopropylamidderivater |
| US8288389B2 (en) | 2007-09-06 | 2012-10-16 | Glaxo Group Limited | Piperazine derivative having affinity for the histamine H3 receptor |
| US20100130477A1 (en) * | 2008-11-25 | 2010-05-27 | Astrazeneca Ab | Spirocyclobutyl Piperidine Derivatives |
| CN102256963B (zh) | 2008-12-19 | 2014-06-11 | 贝林格尔.英格海姆国际有限公司 | 作为ccr2受体拮抗剂用于治疗炎症、哮喘和copd的环状嘧啶-4-甲酰胺 |
| TW201039825A (en) | 2009-02-20 | 2010-11-16 | Astrazeneca Ab | Cyclopropyl amide derivatives 983 |
| US9186353B2 (en) | 2009-04-27 | 2015-11-17 | Abbvie Inc. | Treatment of osteoarthritis pain |
| ES2674275T3 (es) | 2009-12-17 | 2018-06-28 | Centrexion Therapeutics Corporation | Antagonistas del receptor CCR2 y usos de los mismos |
| US20110201622A1 (en) * | 2010-02-18 | 2011-08-18 | Collins Craig D | Solid Forms Comprising A Cyclopropyl Amide Derivative |
| BR112012020629A2 (pt) | 2010-02-18 | 2018-06-19 | Astrazeneca Ab | forma cristalina, e, método para a terapia de um distúrbio |
| JP5646736B2 (ja) | 2010-05-12 | 2014-12-24 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | 新規ｃｃｒ２受容体アンタゴニスト、これらの製造方法、及び薬物としてのこれらの使用 |
| WO2011141474A1 (en) | 2010-05-12 | 2011-11-17 | Boehringer Ingelheim International Gmbh | Novel ccr2 receptor antagonists, method for producing the same, and use thereof as medicaments |
| WO2011144501A1 (en) | 2010-05-17 | 2011-11-24 | Boehringer Ingelheim International Gmbh | Ccr2 antagonists and uses thereof |
| WO2011147772A1 (en) | 2010-05-25 | 2011-12-01 | Boehringer Ingelheim International Gmbh | Ccr2 receptor antagonists |
| US8962656B2 (en) | 2010-06-01 | 2015-02-24 | Boehringer Ingelheim International Gmbh | CCR2 antagonists |
| WO2012037258A1 (en) | 2010-09-16 | 2012-03-22 | Abbott Laboratories | Processes for preparing 1,2-substituted cyclopropyl derivatives |
| EP2731941B1 (en) | 2011-07-15 | 2019-05-08 | Boehringer Ingelheim International GmbH | Novel and selective ccr2 antagonists |
| AR088256A1 (es) | 2011-10-08 | 2014-05-21 | Novartis Ag | Derivados de carbamato / urea como antagonistas del receptor h3 |
| WO2013151982A1 (en) | 2012-04-03 | 2013-10-10 | Arena Pharmaceuticals, Inc. | Methods and compounds useful in treating pruritus, and methods for identifying such compounds |
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| US9034874B2 (en) | 2012-07-20 | 2015-05-19 | Novartis Ag | Carbamate/urea derivatives |
| PT3317270T (pt) | 2015-07-02 | 2020-08-24 | Centrexion Therapeutics Corp | (4-((3r,4r)-3-metoxitetrahidro-pirano-4-ilamino)piperidina-1-il)(5-metil-6-(((2r,6s)-6-(p-tolil)tetrahidro-2h-pirano-2-il)metilamino)pirimidina-4-il)citrato de metanona |
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2004
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- 2004-04-21 AU AU2004238447A patent/AU2004238447C1/en not_active Expired - Fee Related
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- 2004-04-21 WO PCT/EP2004/004245 patent/WO2004101546A1/en not_active Ceased
- 2004-04-21 RU RU2005136368/04A patent/RU2005136368A/ru not_active Application Discontinuation
- 2004-04-21 KR KR1020057019965A patent/KR20050121268A/ko not_active Withdrawn
- 2004-04-21 DE DE602004015269T patent/DE602004015269D1/de not_active Expired - Lifetime
- 2004-04-21 TW TW093111027A patent/TW200503713A/zh unknown
- 2004-04-21 JP JP2006529693A patent/JP2006528939A/ja active Pending
- 2004-04-21 PT PT04728561T patent/PT1615909E/pt unknown
- 2004-04-21 AR ARP040101348A patent/AR044045A1/es not_active Application Discontinuation
- 2004-04-21 EP EP04728561A patent/EP1615909B1/en not_active Expired - Lifetime
- 2004-04-21 MX MXPA05011352A patent/MXPA05011352A/es active IP Right Grant
- 2004-04-21 ES ES04728561T patent/ES2311152T3/es not_active Expired - Lifetime
- 2004-04-21 PL PL04728561T patent/PL1615909T3/pl unknown
- 2004-04-21 US US10/553,803 patent/US7592347B2/en not_active Expired - Fee Related
- 2004-04-21 HR HR20080541T patent/HRP20080541T3/xx unknown
- 2004-04-21 BR BRPI0409611-8A patent/BRPI0409611A/pt not_active IP Right Cessation
-
2005
- 2005-10-19 MA MA28564A patent/MA27675A1/fr unknown
- 2005-10-21 CO CO05106973A patent/CO5700754A2/es not_active Application Discontinuation
- 2005-11-21 IS IS8134A patent/IS8134A/is unknown
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