CA2521330A1 - Inhibiteurs des canaux calciques comprenant du benzhydryle espace de la piperazine - Google Patents
Inhibiteurs des canaux calciques comprenant du benzhydryle espace de la piperazine Download PDFInfo
- Publication number
- CA2521330A1 CA2521330A1 CA002521330A CA2521330A CA2521330A1 CA 2521330 A1 CA2521330 A1 CA 2521330A1 CA 002521330 A CA002521330 A CA 002521330A CA 2521330 A CA2521330 A CA 2521330A CA 2521330 A1 CA2521330 A1 CA 2521330A1
- Authority
- CA
- Canada
- Prior art keywords
- phenyl
- fluoro
- bis
- piperazin
- hexyl
- 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.)
- Abandoned
Links
- 102000003922 Calcium Channels Human genes 0.000 title claims abstract description 33
- 108090000312 Calcium Channels Proteins 0.000 title claims abstract description 33
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 title abstract description 14
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical compound C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 title description 12
- 239000003112 inhibitor Substances 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 125
- 230000000694 effects Effects 0.000 claims abstract description 27
- 125000004193 piperazinyl group Chemical group 0.000 claims abstract description 9
- 239000000203 mixture Substances 0.000 claims description 37
- 125000001424 substituent group Chemical group 0.000 claims description 31
- 125000000217 alkyl group Chemical group 0.000 claims description 27
- 229910052757 nitrogen Inorganic materials 0.000 claims description 25
- 125000003118 aryl group Chemical group 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 21
- 125000005842 heteroatom Chemical group 0.000 claims description 17
- 229910052760 oxygen Inorganic materials 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
- 125000003342 alkenyl group Chemical group 0.000 claims description 15
- 125000005843 halogen group Chemical group 0.000 claims description 15
- 229910052717 sulfur Inorganic materials 0.000 claims description 15
- 125000000304 alkynyl group Chemical group 0.000 claims description 12
- -1 6,6-Bis-(4-fluoro-phenyl)-1-[4-{2-phenylsulfanyl-ethyl)-piperazin-1-yl]-hexan-one Chemical compound 0.000 claims description 9
- 125000005647 linker group Chemical group 0.000 claims description 9
- 238000011282 treatment Methods 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 7
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- 230000002452 interceptive effect Effects 0.000 claims description 5
- 150000001408 amides Chemical class 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000005018 aryl alkenyl group Chemical group 0.000 claims description 3
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- AIJBJWQSZXTWLZ-UHFFFAOYSA-N ethyl 1-[6,6-bis(4-fluorophenyl)hexyl]-4-[(3,4,5-trimethoxyphenyl)methyl]piperazine-2-carboxylate Chemical compound C1CN(CCCCCC(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)C(C(=O)OCC)CN1CC1=CC(OC)=C(OC)C(OC)=C1 AIJBJWQSZXTWLZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims 2
- KWVFXCVHYOLFNX-UHFFFAOYSA-N 1-(1,3-benzodioxol-5-ylmethyl)-4-[6,6-bis(4-fluorophenyl)hexyl]piperazine Chemical compound C1=CC(F)=CC=C1C(C=1C=CC(F)=CC=1)CCCCCN1CCN(CC=2C=C3OCOC3=CC=2)CC1 KWVFXCVHYOLFNX-UHFFFAOYSA-N 0.000 claims 1
- OUGOONSOCAIFKF-UHFFFAOYSA-N 1-(4-amino-2,3,5-trimethylphenoxy)-3-[4-[6,6-bis(4-fluorophenyl)hexyl]piperazin-1-yl]propan-2-ol Chemical compound CC1=C(N)C(C)=CC(OCC(O)CN2CCN(CCCCCC(C=3C=CC(F)=CC=3)C=3C=CC(F)=CC=3)CC2)=C1C OUGOONSOCAIFKF-UHFFFAOYSA-N 0.000 claims 1
- MPZPVPAIGBGCJW-UHFFFAOYSA-N 1-[2-(1,3-benzodioxol-5-yloxy)ethyl]-4-[6,6-bis(4-fluorophenyl)hexyl]piperazine Chemical compound C1=CC(F)=CC=C1C(C=1C=CC(F)=CC=1)CCCCCN1CCN(CCOC=2C=C3OCOC3=CC=2)CC1 MPZPVPAIGBGCJW-UHFFFAOYSA-N 0.000 claims 1
- LIYFZWGHCBXXMR-UHFFFAOYSA-N 1-[4-(1,3-benzothiazol-2-yl)piperazin-1-yl]-6,6-bis(4-fluorophenyl)hexan-1-one Chemical compound C1=CC(F)=CC=C1C(C=1C=CC(F)=CC=1)CCCCC(=O)N1CCN(C=2SC3=CC=CC=C3N=2)CC1 LIYFZWGHCBXXMR-UHFFFAOYSA-N 0.000 claims 1
- BXQXDBCUCOHWAV-UHFFFAOYSA-N 1-[4-(2-anilinoethyl)piperazin-1-yl]-6,6-bis(4-fluorophenyl)hexan-1-one Chemical compound C1=CC(F)=CC=C1C(C=1C=CC(F)=CC=1)CCCCC(=O)N1CCN(CCNC=2C=CC=CC=2)CC1 BXQXDBCUCOHWAV-UHFFFAOYSA-N 0.000 claims 1
- DRBJWKBCCWABCG-UHFFFAOYSA-N 1-[4-(3,4-dimethoxybenzoyl)piperazin-1-yl]-6,6-bis(4-fluorophenyl)hexan-1-one Chemical compound C1=C(OC)C(OC)=CC=C1C(=O)N1CCN(C(=O)CCCCC(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)CC1 DRBJWKBCCWABCG-UHFFFAOYSA-N 0.000 claims 1
- LDTQHKVLRQRFEB-UHFFFAOYSA-N 1-[4-(3,5-dibromo-4-hydroxybenzoyl)piperazin-1-yl]-6,6-bis(4-fluorophenyl)hexan-1-one Chemical compound C1=C(Br)C(O)=C(Br)C=C1C(=O)N1CCN(C(=O)CCCCC(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)CC1 LDTQHKVLRQRFEB-UHFFFAOYSA-N 0.000 claims 1
- JLPSMXPDEKOWNN-UHFFFAOYSA-N 1-[4-(3,5-ditert-butyl-4-hydroxybenzoyl)piperazin-1-yl]-6,6-bis(4-fluorophenyl)hexan-1-one Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(C(=O)N2CCN(CC2)C(=O)CCCCC(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)=C1 JLPSMXPDEKOWNN-UHFFFAOYSA-N 0.000 claims 1
- HTTLIQFTUASLKJ-UHFFFAOYSA-N 1-[4-(3,5-ditert-butyl-4-methoxybenzoyl)-2-methylpiperazin-1-yl]-6,6-bis(4-fluorophenyl)hexan-1-one Chemical compound C1=C(C(C)(C)C)C(OC)=C(C(C)(C)C)C=C1C(=O)N1CC(C)N(C(=O)CCCCC(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)CC1 HTTLIQFTUASLKJ-UHFFFAOYSA-N 0.000 claims 1
- MBFAOOZDUTUYCE-UHFFFAOYSA-N 1-[4-(3,5-ditert-butyl-4-methoxybenzoyl)-3-methylpiperazin-1-yl]-6,6-bis(4-fluorophenyl)hexan-1-one Chemical compound C1=C(C(C)(C)C)C(OC)=C(C(C)(C)C)C=C1C(=O)N1C(C)CN(C(=O)CCCCC(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)CC1 MBFAOOZDUTUYCE-UHFFFAOYSA-N 0.000 claims 1
- IKXBGIDOAZUISA-UHFFFAOYSA-N 1-[4-(3,5-ditert-butyl-4-methoxybenzoyl)piperazin-1-yl]-6,6-bis(4-fluorophenyl)hexan-1-one Chemical compound C1=C(C(C)(C)C)C(OC)=C(C(C)(C)C)C=C1C(=O)N1CCN(C(=O)CCCCC(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)CC1 IKXBGIDOAZUISA-UHFFFAOYSA-N 0.000 claims 1
- OVQOLXYGJJAFNK-UHFFFAOYSA-N 1-[4-(3,5-ditert-butylbenzoyl)-2-methylpiperazin-1-yl]-6,6-bis(4-fluorophenyl)hexan-1-one Chemical compound CC1CN(C(=O)C=2C=C(C=C(C=2)C(C)(C)C)C(C)(C)C)CCN1C(=O)CCCCC(C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 OVQOLXYGJJAFNK-UHFFFAOYSA-N 0.000 claims 1
- PJBAXJSEDXDPOU-UHFFFAOYSA-N 1-[4-(3,5-ditert-butylbenzoyl)piperazin-1-yl]-6,6-bis(4-fluorophenyl)hexan-1-one Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC(C(=O)N2CCN(CC2)C(=O)CCCCC(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)=C1 PJBAXJSEDXDPOU-UHFFFAOYSA-N 0.000 claims 1
- HCCUPFWMVFHHQT-UHFFFAOYSA-N 1-[4-(4-bromobenzoyl)piperazin-1-yl]-6,6-bis(4-fluorophenyl)hexan-1-one Chemical compound C1=CC(F)=CC=C1C(C=1C=CC(F)=CC=1)CCCCC(=O)N1CCN(C(=O)C=2C=CC(Br)=CC=2)CC1 HCCUPFWMVFHHQT-UHFFFAOYSA-N 0.000 claims 1
- SOIRKNRHZGNDJB-UHFFFAOYSA-N 1-[4-(4-tert-butylbenzoyl)-2-methylpiperazin-1-yl]-6,6-bis(4-fluorophenyl)hexan-1-one Chemical compound CC1CN(C(=O)C=2C=CC(=CC=2)C(C)(C)C)CCN1C(=O)CCCCC(C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 SOIRKNRHZGNDJB-UHFFFAOYSA-N 0.000 claims 1
- WHRDRCYBGWDOEN-UHFFFAOYSA-N 1-[4-(4-tert-butylbenzoyl)piperazin-1-yl]-6,6-bis(4-fluorophenyl)hexan-1-one Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)N1CCN(C(=O)CCCCC(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)CC1 WHRDRCYBGWDOEN-UHFFFAOYSA-N 0.000 claims 1
- KAXARLDIZPGNAE-UHFFFAOYSA-N 1-[4-[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]piperazin-1-yl]-6,6-bis(4-fluorophenyl)hexan-1-one Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CN2CCN(CC2)C(=O)CCCCC(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)=C1 KAXARLDIZPGNAE-UHFFFAOYSA-N 0.000 claims 1
- WFWWRMLXRXPPQR-UHFFFAOYSA-N 1-[4-[(3,5-ditert-butyl-4-methoxyphenyl)methyl]piperazin-1-yl]-6,6-bis(4-fluorophenyl)hexan-1-one Chemical compound C1=C(C(C)(C)C)C(OC)=C(C(C)(C)C)C=C1CN1CCN(C(=O)CCCCC(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)CC1 WFWWRMLXRXPPQR-UHFFFAOYSA-N 0.000 claims 1
- OPPQVYZVXUVKLS-UHFFFAOYSA-N 1-[4-[2-(1,3-benzodioxol-5-yloxy)ethyl]piperazin-1-yl]-6,6-bis(4-fluorophenyl)hexan-1-one Chemical compound C1=CC(F)=CC=C1C(C=1C=CC(F)=CC=1)CCCCC(=O)N1CCN(CCOC=2C=C3OCOC3=CC=2)CC1 OPPQVYZVXUVKLS-UHFFFAOYSA-N 0.000 claims 1
- UYXJZQPUDGJORK-UHFFFAOYSA-N 1-[4-[2-(1,3-benzothiazol-2-ylsulfanyl)ethyl]piperazin-1-yl]-6,6-bis(4-fluorophenyl)hexan-1-one Chemical compound C1=CC(F)=CC=C1C(C=1C=CC(F)=CC=1)CCCCC(=O)N1CCN(CCSC=2SC3=CC=CC=C3N=2)CC1 UYXJZQPUDGJORK-UHFFFAOYSA-N 0.000 claims 1
- SNXMRAJPZLZZFT-UHFFFAOYSA-N 1-[4-[2-(2,4-dichlorophenoxy)ethyl]piperazin-1-yl]-6,6-bis(4-fluorophenyl)hexan-1-one Chemical compound C1=CC(F)=CC=C1C(C=1C=CC(F)=CC=1)CCCCC(=O)N1CCN(CCOC=2C(=CC(Cl)=CC=2)Cl)CC1 SNXMRAJPZLZZFT-UHFFFAOYSA-N 0.000 claims 1
- PSRGIXGZLGGOSO-UHFFFAOYSA-N 1-[4-[2-(2,4-difluorophenoxy)ethyl]piperazin-1-yl]-6,6-bis(4-fluorophenyl)hexan-1-one Chemical compound C1=CC(F)=CC=C1C(C=1C=CC(F)=CC=1)CCCCC(=O)N1CCN(CCOC=2C(=CC(F)=CC=2)F)CC1 PSRGIXGZLGGOSO-UHFFFAOYSA-N 0.000 claims 1
- VIAUSJSHIODTCE-UHFFFAOYSA-N 1-[4-[2-(3,4-dimethoxyphenoxy)ethyl]piperazin-1-yl]-6,6-bis(4-fluorophenyl)hexan-1-one Chemical compound C1=C(OC)C(OC)=CC=C1OCCN1CCN(C(=O)CCCCC(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)CC1 VIAUSJSHIODTCE-UHFFFAOYSA-N 0.000 claims 1
- KCGXZHIKOJAOJM-UHFFFAOYSA-N 1-[4-[2-(4-fluorophenoxy)ethyl]piperazin-1-yl]-6,6-bis(4-fluorophenyl)hexan-1-one Chemical compound C1=CC(F)=CC=C1OCCN1CCN(C(=O)CCCCC(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)CC1 KCGXZHIKOJAOJM-UHFFFAOYSA-N 0.000 claims 1
- CPTKYPFGVHVBBO-UHFFFAOYSA-N 1-[4-[2-(benzylamino)ethyl]piperazin-1-yl]-6,6-bis(4-fluorophenyl)hexan-1-one Chemical compound C1=CC(F)=CC=C1C(C=1C=CC(F)=CC=1)CCCCC(=O)N1CCN(CCNCC=2C=CC=CC=2)CC1 CPTKYPFGVHVBBO-UHFFFAOYSA-N 0.000 claims 1
- VIASYJOUNFCJCN-UHFFFAOYSA-N 1-[4-[2-[(4-chlorophenyl)methylamino]ethyl]piperazin-1-yl]-6,6-bis(4-fluorophenyl)hexan-1-one Chemical compound C1=CC(F)=CC=C1C(C=1C=CC(F)=CC=1)CCCCC(=O)N1CCN(CCNCC=2C=CC(Cl)=CC=2)CC1 VIASYJOUNFCJCN-UHFFFAOYSA-N 0.000 claims 1
- CDYDWCPPDZIFJI-UHFFFAOYSA-N 1-[4-[2-[(4-tert-butylphenyl)methylamino]ethyl]piperazin-1-yl]-6,6-bis(4-fluorophenyl)hexan-1-one Chemical compound C1=CC(C(C)(C)C)=CC=C1CNCCN1CCN(C(=O)CCCCC(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)CC1 CDYDWCPPDZIFJI-UHFFFAOYSA-N 0.000 claims 1
- QHSLTWMAYPJDHE-UHFFFAOYSA-N 1-[4-[3,5-bis(trifluoromethyl)benzoyl]piperazin-1-yl]-6,6-bis(4-fluorophenyl)hexan-1-one Chemical compound C1=CC(F)=CC=C1C(C=1C=CC(F)=CC=1)CCCCC(=O)N1CCN(C(=O)C=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)CC1 QHSLTWMAYPJDHE-UHFFFAOYSA-N 0.000 claims 1
- AOHLSLQKXPWNJV-UHFFFAOYSA-N 1-[4-[3,5-ditert-butyl-4-[2-(dimethylamino)ethoxy]benzoyl]piperazin-1-yl]-6,6-bis(4-fluorophenyl)hexan-1-one Chemical compound C1=C(C(C)(C)C)C(OCCN(C)C)=C(C(C)(C)C)C=C1C(=O)N1CCN(C(=O)CCCCC(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)CC1 AOHLSLQKXPWNJV-UHFFFAOYSA-N 0.000 claims 1
- CUJHIPJUXJPNCR-UHFFFAOYSA-N 1-[4-[3-(4-amino-2,3,5-trimethylphenoxy)-2-hydroxypropyl]piperazin-1-yl]-6,6-bis(4-fluorophenyl)hexan-1-one Chemical compound CC1=C(N)C(C)=CC(OCC(O)CN2CCN(CC2)C(=O)CCCCC(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)=C1C CUJHIPJUXJPNCR-UHFFFAOYSA-N 0.000 claims 1
- YAKJSSNUJBUIOJ-UHFFFAOYSA-N 1-[4-[bis(4-fluorophenyl)methoxy]butyl]-4-[(3,4,5-trimethoxyphenyl)methyl]piperazine Chemical compound COC1=C(OC)C(OC)=CC(CN2CCN(CCCCOC(C=3C=CC(F)=CC=3)C=3C=CC(F)=CC=3)CC2)=C1 YAKJSSNUJBUIOJ-UHFFFAOYSA-N 0.000 claims 1
- CWOYRMQVUCWPTB-UHFFFAOYSA-N 1-[6,6-bis(4-fluorophenyl)hexanoyl]-4-(3,5-ditert-butyl-4-hydroxybenzoyl)piperazin-2-one Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(C(=O)N2CC(=O)N(C(=O)CCCCC(C=3C=CC(F)=CC=3)C=3C=CC(F)=CC=3)CC2)=C1 CWOYRMQVUCWPTB-UHFFFAOYSA-N 0.000 claims 1
- QVUSIJOIPBNJJJ-UHFFFAOYSA-N 1-[6,6-bis(4-fluorophenyl)hexanoyl]-4-(3,5-ditert-butyl-4-methoxybenzoyl)piperazin-2-one Chemical compound C1=C(C(C)(C)C)C(OC)=C(C(C)(C)C)C=C1C(=O)N1CC(=O)N(C(=O)CCCCC(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)CC1 QVUSIJOIPBNJJJ-UHFFFAOYSA-N 0.000 claims 1
- OSGOHAVUPVXVKI-UHFFFAOYSA-N 1-[6,6-bis(4-fluorophenyl)hexyl]-4-(2-phenoxyethyl)piperazine Chemical compound C1=CC(F)=CC=C1C(C=1C=CC(F)=CC=1)CCCCCN1CCN(CCOC=2C=CC=CC=2)CC1 OSGOHAVUPVXVKI-UHFFFAOYSA-N 0.000 claims 1
- CWFLQNPJVNOFTA-UHFFFAOYSA-N 1-[6,6-bis(4-fluorophenyl)hexyl]-4-(2-phenylsulfanylethyl)piperazine Chemical compound C1=CC(F)=CC=C1C(C=1C=CC(F)=CC=1)CCCCCN1CCN(CCSC=2C=CC=CC=2)CC1 CWFLQNPJVNOFTA-UHFFFAOYSA-N 0.000 claims 1
- OANLFJVXKYVMDB-UHFFFAOYSA-N 1-[6,6-bis(4-fluorophenyl)hexyl]-4-(3,4,5-trimethoxybenzoyl)piperazin-2-one Chemical compound COC1=C(OC)C(OC)=CC(C(=O)N2CC(=O)N(CCCCCC(C=3C=CC(F)=CC=3)C=3C=CC(F)=CC=3)CC2)=C1 OANLFJVXKYVMDB-UHFFFAOYSA-N 0.000 claims 1
- AKEOQIGPKJVFBH-UHFFFAOYSA-N 1-[6,6-bis(4-fluorophenyl)hexyl]-4-(3,5-ditert-butyl-4-methoxybenzoyl)piperazin-2-one Chemical compound C1=C(C(C)(C)C)C(OC)=C(C(C)(C)C)C=C1C(=O)N1CC(=O)N(CCCCCC(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)CC1 AKEOQIGPKJVFBH-UHFFFAOYSA-N 0.000 claims 1
- ALKNWKFWYPAJOU-UHFFFAOYSA-N 1-[6,6-bis(4-fluorophenyl)hexyl]-4-(9h-thioxanthen-9-yl)piperazine Chemical compound C1=CC(F)=CC=C1C(C=1C=CC(F)=CC=1)CCCCCN1CCN(C2C3=CC=CC=C3SC3=CC=CC=C32)CC1 ALKNWKFWYPAJOU-UHFFFAOYSA-N 0.000 claims 1
- NSQDOOVDRZZCIH-UHFFFAOYSA-N 1-[6,6-bis(4-fluorophenyl)hexyl]-4-[(3,4,5-trimethoxyphenyl)methyl]piperazine-2-carboxylic acid Chemical compound COC1=C(OC)C(OC)=CC(CN2CC(N(CCCCCC(C=3C=CC(F)=CC=3)C=3C=CC(F)=CC=3)CC2)C(O)=O)=C1 NSQDOOVDRZZCIH-UHFFFAOYSA-N 0.000 claims 1
- UPTFULKJNIHEGP-UHFFFAOYSA-N 1-[6,6-bis(4-fluorophenyl)hexyl]-4-[(3,4-dimethoxyphenyl)methyl]piperazine Chemical compound C1=C(OC)C(OC)=CC=C1CN1CCN(CCCCCC(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)CC1 UPTFULKJNIHEGP-UHFFFAOYSA-N 0.000 claims 1
- XVQGPTPHXYSOOC-UHFFFAOYSA-N 1-[6,6-bis(4-fluorophenyl)hexyl]-4-[(3,5-ditert-butyl-4-methoxyphenyl)methyl]piperazin-2-one Chemical compound C1=C(C(C)(C)C)C(OC)=C(C(C)(C)C)C=C1CN1CC(=O)N(CCCCCC(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)CC1 XVQGPTPHXYSOOC-UHFFFAOYSA-N 0.000 claims 1
- XRYLRSPQAGGXGI-UHFFFAOYSA-N 1-[6,6-bis(4-fluorophenyl)hexyl]-4-[(3,5-ditert-butyl-4-methoxyphenyl)methyl]piperazine Chemical compound C1=C(C(C)(C)C)C(OC)=C(C(C)(C)C)C=C1CN1CCN(CCCCCC(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)CC1 XRYLRSPQAGGXGI-UHFFFAOYSA-N 0.000 claims 1
- GQDFRLDUWXFTSJ-UHFFFAOYSA-N 1-[6,6-bis(4-fluorophenyl)hexyl]-4-[(3,5-ditert-butylphenyl)methyl]piperazine Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC(CN2CCN(CCCCCC(C=3C=CC(F)=CC=3)C=3C=CC(F)=CC=3)CC2)=C1 GQDFRLDUWXFTSJ-UHFFFAOYSA-N 0.000 claims 1
- LARUGYACKUHGCL-UHFFFAOYSA-N 1-[6,6-bis(4-fluorophenyl)hexyl]-4-[(4-bromophenyl)methyl]piperazine Chemical compound C1=CC(F)=CC=C1C(C=1C=CC(F)=CC=1)CCCCCN1CCN(CC=2C=CC(Br)=CC=2)CC1 LARUGYACKUHGCL-UHFFFAOYSA-N 0.000 claims 1
- VMZTXEFNNUROEK-UHFFFAOYSA-N 1-[6,6-bis(4-fluorophenyl)hexyl]-4-[(4-tert-butylphenyl)methyl]piperazine Chemical compound C1=CC(C(C)(C)C)=CC=C1CN1CCN(CCCCCC(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)CC1 VMZTXEFNNUROEK-UHFFFAOYSA-N 0.000 claims 1
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- AJKNMIVMHRLNMM-UHFFFAOYSA-N 1-[6,6-bis(4-fluorophenyl)hexyl]-4-[2-(4-fluorophenoxy)ethyl]piperazine Chemical compound C1=CC(F)=CC=C1OCCN1CCN(CCCCCC(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)CC1 AJKNMIVMHRLNMM-UHFFFAOYSA-N 0.000 claims 1
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- HJRPKCUMFDYICI-UHFFFAOYSA-N 1-[9,9-bis(4-fluorophenyl)nonyl]-4-[(3,4,5-trimethoxyphenyl)methyl]piperazine Chemical compound COC1=C(OC)C(OC)=CC(CN2CCN(CCCCCCCCC(C=3C=CC(F)=CC=3)C=3C=CC(F)=CC=3)CC2)=C1 HJRPKCUMFDYICI-UHFFFAOYSA-N 0.000 claims 1
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- PRFCNFBEYSWBGY-UHFFFAOYSA-N 2-[4-[[4-[6,6-bis(4-fluorophenyl)hexyl]piperazin-1-yl]methyl]-2,6-ditert-butylphenoxy]-n,n-dimethylethanamine Chemical compound C1=C(C(C)(C)C)C(OCCN(C)C)=C(C(C)(C)C)C=C1CN1CCN(CCCCCC(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)CC1 PRFCNFBEYSWBGY-UHFFFAOYSA-N 0.000 claims 1
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Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/409,868 | 2003-04-08 | ||
| US10/409,868 US6943168B2 (en) | 1998-06-30 | 2003-04-08 | Calcium channel inhibitors comprising benzhydril spaced from piperazine |
| PCT/CA2004/000539 WO2004089922A2 (fr) | 1998-06-30 | 2004-04-08 | Inhibiteurs des canaux calciques comprenant du benzhydryle espace de la piperazine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2521330A1 true CA2521330A1 (fr) | 2004-10-21 |
Family
ID=35452387
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002521330A Abandoned CA2521330A1 (fr) | 2003-04-08 | 2004-04-08 | Inhibiteurs des canaux calciques comprenant du benzhydryle espace de la piperazine |
Country Status (3)
| Country | Link |
|---|---|
| EP (1) | EP1611116A2 (fr) |
| JP (1) | JP2006522742A (fr) |
| CA (1) | CA2521330A1 (fr) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009132454A1 (fr) * | 2008-04-28 | 2009-11-05 | Neuromed Pharmaceuticals Ltd. | Di-t-butylphényle piperazines utilisées comme inhibiteurs des canaux calciques |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3125577A (en) * | 1964-03-17 | N-substttuted piperazinoalkyl | ||
| US3030366A (en) * | 1961-01-25 | 1962-04-17 | Lakeside Lab Inc | Piperazinoalkyl glycolamides |
| US3205134A (en) * | 1961-11-14 | 1965-09-07 | Colgate Palmolive Co | Antidepressant benzilates of piperazinoalkanols |
| HU174215B (hu) * | 1976-12-15 | 1979-11-28 | Richter Gedeon Vegyeszet | Sposob poluchenija novykh proizvodnykh piperazina i kislotnykh additivnykh i chetvjortichnykh solej |
| JPS6147466A (ja) * | 1984-08-10 | 1986-03-07 | Dainippon Pharmaceut Co Ltd | アミン誘導体 |
| JPS61155358A (ja) * | 1984-12-21 | 1986-07-15 | Suntory Ltd | ジアリール酪酸誘導体 |
| FR2595695B1 (fr) * | 1986-03-12 | 1988-12-02 | Synthelabo | Derives de n-(((hydroxy-2 phenyl) (phenyl) methylene) amino-2) ethyl) acetamide, leur preparation et leur application en therapeutique |
| EP0441226A1 (fr) * | 1990-01-29 | 1991-08-14 | J. URIACH & CIA. S.A. | (cyanométhyl)pyridines utiles comme antagonistes du PAF |
| FR2673182A1 (fr) * | 1991-02-22 | 1992-08-28 | Univ Caen | Piperazines n,n'-disubstituees, leur procede de preparation et leur application en therapeutique. |
| US6458781B1 (en) * | 1998-04-27 | 2002-10-01 | David Thomas Connor | Substituted diarylalkyl amides as calcium channel antagonists |
| US6387897B1 (en) * | 1998-06-30 | 2002-05-14 | Neuromed Technologies, Inc. | Preferentially substituted calcium channel blockers |
| US6011035A (en) * | 1998-06-30 | 2000-01-04 | Neuromed Technologies Inc. | Calcium channel blockers |
| US6492375B2 (en) * | 1998-06-30 | 2002-12-10 | Neuromed Technologies, Inc. | Partially saturated calcium channel blockers |
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2004
- 2004-04-08 EP EP04726395A patent/EP1611116A2/fr not_active Withdrawn
- 2004-04-08 JP JP2006504105A patent/JP2006522742A/ja active Pending
- 2004-04-08 CA CA002521330A patent/CA2521330A1/fr not_active Abandoned
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009132454A1 (fr) * | 2008-04-28 | 2009-11-05 | Neuromed Pharmaceuticals Ltd. | Di-t-butylphényle piperazines utilisées comme inhibiteurs des canaux calciques |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2006522742A (ja) | 2006-10-05 |
| EP1611116A2 (fr) | 2006-01-04 |
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| Date | Code | Title | Description |
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| EEER | Examination request | ||
| FZDE | Discontinued |