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
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- 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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| PL1802307T3 (pl) * | 2004-10-15 | 2008-07-31 | Glaxo Group Ltd | Pochodne pirolidyny jako ligandy receptorów histaminowych |
| EP1902046B1 (en) | 2005-06-20 | 2009-12-02 | Schering Corporation | Piperidine derivatives useful as histamine h3 antagonists |
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| JP2009506987A (ja) * | 2005-08-02 | 2009-02-19 | ニューロゲン コーポレイション | ジピペラジニルケトンおよび関連する類似体 |
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| JP2009521448A (ja) | 2005-12-21 | 2009-06-04 | シェーリング コーポレイション | ヒスタミンｈ３アンタゴニストとして有用なフェノキシピペリジンおよびそのアナログ |
| US9108948B2 (en) | 2006-06-23 | 2015-08-18 | Abbvie Inc. | Cyclopropyl amine derivatives |
| CN101472887A (zh) | 2006-06-23 | 2009-07-01 | 艾博特公司 | 作为组胺h3受体调节物的环丙胺衍生物 |
| EP2136805A2 (en) * | 2007-03-02 | 2009-12-30 | Schering Corporation | Piperidinyl-piperidine and piperazinyl-piperidine for use in the treatment of diabetes or pain |
| TW200902007A (en) * | 2007-05-25 | 2009-01-16 | Astrazeneca Ab | Spirocyclopropyl piperidine derivatives |
| CA2687931C (en) | 2007-05-31 | 2016-05-24 | Boehringer Ingelheim International Gmbh | Ccr2 receptor antagonists and uses thereof |
| CA2688585A1 (en) | 2007-06-11 | 2008-12-18 | F. Hoffmann-La Roche Ag | Cyclohexyl derivatives |
| BRPI0815591B8 (pt) | 2007-08-22 | 2021-05-25 | Astrazeneca Ab | composto, composição farmacêutica, e, uso de um composto. |
| WO2009030716A1 (en) | 2007-09-06 | 2009-03-12 | 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 |
| CN103724328B (zh) | 2008-12-19 | 2015-10-14 | 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 |
| PL2513093T3 (pl) | 2009-12-17 | 2015-03-31 | Centrexion Therapeutics Corp | Nowi antagoniści receptora CCR2 i ich zastosowanie |
| WO2011102793A1 (en) * | 2010-02-18 | 2011-08-25 | Astrazeneca Ab | Solid forms comprising a cyclopropyl amide derivative |
| AU2011218492B2 (en) * | 2010-02-18 | 2014-11-13 | Astrazeneca Ab | New crystalline form of a cyclopropyl benzamide derivative |
| EP2569295B1 (en) | 2010-05-12 | 2014-11-19 | Boehringer Ingelheim International GmbH | New ccr2 receptor antagonists, method for producing the same, and use thereof as medicaments |
| JP2013526507A (ja) | 2010-05-12 | 2013-06-24 | 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、その製造方法及び薬物としてのその使用 |
| US8841313B2 (en) | 2010-05-17 | 2014-09-23 | Boehringer Ingelheim International Gmbh | CCR2 antagonists and uses thereof |
| JP5636094B2 (ja) | 2010-05-25 | 2014-12-03 | 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受容体アンタゴニスト |
| EP2576538B1 (en) | 2010-06-01 | 2015-10-28 | Boehringer Ingelheim International GmbH | New CCR2 antagonists |
| WO2012037258A1 (en) | 2010-09-16 | 2012-03-22 | Abbott Laboratories | Processes for preparing 1,2-substituted cyclopropyl derivatives |
| WO2013010839A1 (en) | 2011-07-15 | 2013-01-24 | 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 |
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| ATE365209T1 (de) | 1992-05-14 | 2007-07-15 | Baylor College Medicine | Mutierte steroidhormonrezeptoren, methoden für ihre benutzung und molekularer schalter für gentherapie |
| US5364791A (en) | 1992-05-14 | 1994-11-15 | Elisabetta Vegeto | Progesterone receptor having C. terminal hormone binding domain truncations |
| IL115420A0 (en) | 1994-09-26 | 1995-12-31 | Zeneca Ltd | Aminoheterocyclic derivatives |
| GB9516709D0 (en) | 1995-08-15 | 1995-10-18 | Zeneca Ltd | Medicament |
| GB9526546D0 (en) | 1995-12-23 | 1996-02-28 | Pfizer Ltd | Compounds useful in therapy |
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| PE20020507A1 (es) | 2000-10-17 | 2002-06-25 | Schering Corp | Compuestos no-imidazoles como antagonistas del receptor histamina h3 |
| CA2432825A1 (en) * | 2000-12-15 | 2002-06-20 | Emory University | Nonpeptide agonists and antagonists of vasopressin receptors |
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| AU2002254114A1 (en) | 2001-03-23 | 2002-10-08 | Eli Lilly And Company | Non-imidazole aryl alkylamines compounds as histamine h3 receptor antagonists, preparation and therapeutic uses |
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| WO2003088967A1 (en) | 2002-04-18 | 2003-10-30 | Schering Corporation | (1-4-piperidinyl) benzimidazole derivatives useful as histamine h3 antagonists |
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2004
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- 2004-04-21 HR HR20080541T patent/HRP20080541T3/xx unknown
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- 2004-04-21 DE DE602004015269T patent/DE602004015269D1/de not_active Expired - Lifetime
- 2004-04-21 KR KR1020057019965A patent/KR20050121268A/ko not_active Withdrawn
- 2004-04-21 WO PCT/EP2004/004245 patent/WO2004101546A1/en not_active Ceased
- 2004-04-21 CA CA002523431A patent/CA2523431A1/en not_active Abandoned
- 2004-04-21 BR BRPI0409611-8A patent/BRPI0409611A/pt not_active IP Right Cessation
- 2004-04-21 EP EP04728561A patent/EP1615909B1/en not_active Expired - Lifetime
- 2004-04-21 AT AT04728561T patent/ATE402165T1/de not_active IP Right Cessation
- 2004-04-21 TW TW093111027A patent/TW200503713A/zh unknown
- 2004-04-21 AR ARP040101348A patent/AR044045A1/es not_active Application Discontinuation
- 2004-04-21 JP JP2006529693A patent/JP2006528939A/ja active Pending
- 2004-04-21 US US10/553,803 patent/US7592347B2/en not_active Expired - Fee Related
- 2004-04-21 PT PT04728561T patent/PT1615909E/pt unknown
- 2004-04-21 PL PL04728561T patent/PL1615909T3/pl unknown
- 2004-04-21 RU RU2005136368/04A patent/RU2005136368A/ru not_active Application Discontinuation
- 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 SI SI200430886T patent/SI1615909T1/sl unknown
-
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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