JP2006514110A5 - - Google Patents
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- JP2006514110A5 JP2006514110A5 JP2005506646A JP2005506646A JP2006514110A5 JP 2006514110 A5 JP2006514110 A5 JP 2006514110A5 JP 2005506646 A JP2005506646 A JP 2005506646A JP 2005506646 A JP2005506646 A JP 2005506646A JP 2006514110 A5 JP2006514110 A5 JP 2006514110A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- substituted
- alkyl
- alkoxy
- amino
- 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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- 229910052736 halogen Inorganic materials 0.000 claims 86
- 150000002367 halogens Chemical class 0.000 claims 86
- -1 cyano, nitro, amino Chemical group 0.000 claims 82
- 125000000217 alkyl group Chemical group 0.000 claims 68
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 64
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 46
- 229910052757 nitrogen Inorganic materials 0.000 claims 37
- 229910052739 hydrogen Inorganic materials 0.000 claims 36
- 239000001257 hydrogen Substances 0.000 claims 36
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims 25
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 24
- 125000001624 naphthyl group Chemical group 0.000 claims 24
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 20
- 125000004414 alkyl thio group Chemical group 0.000 claims 20
- 125000002619 bicyclic group Chemical group 0.000 claims 20
- 125000000623 heterocyclic group Chemical group 0.000 claims 20
- 125000002950 monocyclic group Chemical group 0.000 claims 20
- 229910052760 oxygen Inorganic materials 0.000 claims 20
- 125000004076 pyridyl group Chemical group 0.000 claims 20
- 229920006395 saturated elastomer Polymers 0.000 claims 20
- 125000005842 heteroatom Chemical group 0.000 claims 19
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 19
- 125000005493 quinolyl group Chemical group 0.000 claims 19
- 125000001424 substituent group Chemical group 0.000 claims 19
- 125000002837 carbocyclic group Chemical group 0.000 claims 18
- 125000000304 alkynyl group Chemical group 0.000 claims 17
- 125000001041 indolyl group Chemical group 0.000 claims 17
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 17
- 125000003118 aryl group Chemical group 0.000 claims 16
- 150000002431 hydrogen Chemical class 0.000 claims 16
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 15
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 claims 15
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims 15
- 125000001072 heteroaryl group Chemical group 0.000 claims 13
- 125000005956 isoquinolyl group Chemical group 0.000 claims 13
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 13
- 125000000168 pyrrolyl group Chemical group 0.000 claims 12
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 11
- 239000003814 drug Substances 0.000 claims 11
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims 11
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 10
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 10
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 10
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 10
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 10
- 230000002265 prevention Effects 0.000 claims 10
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 10
- 150000003839 salts Chemical class 0.000 claims 10
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 9
- 125000003373 pyrazinyl group Chemical group 0.000 claims 9
- 125000002098 pyridazinyl group Chemical group 0.000 claims 9
- 150000001875 compounds Chemical class 0.000 claims 8
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims 8
- 125000002883 imidazolyl group Chemical group 0.000 claims 8
- 125000003226 pyrazolyl group Chemical group 0.000 claims 8
- 125000003545 alkoxy group Chemical group 0.000 claims 6
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims 6
- 125000004193 piperazinyl group Chemical group 0.000 claims 6
- 125000003282 alkyl amino group Chemical group 0.000 claims 5
- 238000004519 manufacturing process Methods 0.000 claims 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims 4
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 4
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims 4
- 229910052717 sulfur Inorganic materials 0.000 claims 4
- 208000014001 urinary system disease Diseases 0.000 claims 4
- LRQKBLKVPFOOQJ-YFKPBYRVSA-N L-norleucine Chemical compound CCCC[C@H]([NH3+])C([O-])=O LRQKBLKVPFOOQJ-YFKPBYRVSA-N 0.000 claims 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- 208000031220 Hemophilia Diseases 0.000 claims 2
- 208000009292 Hemophilia A Diseases 0.000 claims 2
- 208000032843 Hemorrhage Diseases 0.000 claims 2
- 208000001953 Hypotension Diseases 0.000 claims 2
- 206010061218 Inflammation Diseases 0.000 claims 2
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 claims 2
- 108091006335 Prostaglandin I receptors Proteins 0.000 claims 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims 2
- 125000004104 aryloxy group Chemical group 0.000 claims 2
- 208000034158 bleeding Diseases 0.000 claims 2
- 230000000740 bleeding effect Effects 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000004122 cyclic group Chemical group 0.000 claims 2
- 230000036543 hypotension Effects 0.000 claims 2
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 claims 2
- 230000004054 inflammatory process Effects 0.000 claims 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 2
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 claims 2
- 239000002464 receptor antagonist Substances 0.000 claims 2
- 229940044551 receptor antagonist Drugs 0.000 claims 2
- NKYAUAPTBSOUDC-HSZRJFAPSA-N (2r)-2-[[6-(4-phenylmethoxyphenyl)pyrimidin-4-yl]amino]-3-pyridin-2-ylpropanoic acid Chemical compound C([C@H](C(=O)O)NC=1N=CN=C(C=1)C=1C=CC(OCC=2C=CC=CC=2)=CC=1)C1=CC=CC=N1 NKYAUAPTBSOUDC-HSZRJFAPSA-N 0.000 claims 1
- IVXYMIGMIKJMTF-HXUWFJFHSA-N (2r)-2-[[6-(4-phenylmethoxyphenyl)pyrimidin-4-yl]amino]hexanoic acid Chemical compound C1=NC(N[C@H](CCCC)C(O)=O)=CC(C=2C=CC(OCC=3C=CC=CC=3)=CC=2)=N1 IVXYMIGMIKJMTF-HXUWFJFHSA-N 0.000 claims 1
- RRYFPNITZGCUPZ-XMMPIXPASA-N (2r)-3-phenyl-2-[[6-(4-phenylmethoxyphenyl)pyrimidin-4-yl]amino]propanoic acid Chemical compound C([C@H](C(=O)O)NC=1N=CN=C(C=1)C=1C=CC(OCC=2C=CC=CC=2)=CC=1)C1=CC=CC=C1 RRYFPNITZGCUPZ-XMMPIXPASA-N 0.000 claims 1
- HWTOGNKGQOFCBO-QFIPXVFZSA-N (2s)-2-[[5-fluoro-6-(4-phenylmethoxyphenyl)pyrimidin-4-yl]amino]-3-phenylpropanoic acid Chemical compound C([C@@H](C(=O)O)NC=1C(=C(N=CN=1)C=1C=CC(OCC=2C=CC=CC=2)=CC=1)F)C1=CC=CC=C1 HWTOGNKGQOFCBO-QFIPXVFZSA-N 0.000 claims 1
- PDSGMAQAFXECJJ-QHCPKHFHSA-N (2s)-2-[[6-(3-fluoro-4-phenylmethoxyphenyl)pyrimidin-4-yl]amino]-3-phenylpropanoic acid Chemical compound C([C@@H](C(=O)O)NC=1N=CN=C(C=1)C=1C=C(F)C(OCC=2C=CC=CC=2)=CC=1)C1=CC=CC=C1 PDSGMAQAFXECJJ-QHCPKHFHSA-N 0.000 claims 1
- NKGMJNPPTFVLSC-QFIPXVFZSA-N (2s)-2-[[6-(3-fluoro-4-phenylmethoxyphenyl)pyrimidin-4-yl]amino]-3-pyridin-2-ylpropanoic acid Chemical compound C([C@@H](C(=O)O)NC=1N=CN=C(C=1)C=1C=C(F)C(OCC=2C=CC=CC=2)=CC=1)C1=CC=CC=N1 NKGMJNPPTFVLSC-QFIPXVFZSA-N 0.000 claims 1
- NKYAUAPTBSOUDC-QHCPKHFHSA-N (2s)-2-[[6-(4-phenylmethoxyphenyl)pyrimidin-4-yl]amino]-3-pyridin-2-ylpropanoic acid Chemical compound C([C@@H](C(=O)O)NC=1N=CN=C(C=1)C=1C=CC(OCC=2C=CC=CC=2)=CC=1)C1=CC=CC=N1 NKYAUAPTBSOUDC-QHCPKHFHSA-N 0.000 claims 1
- IVXYMIGMIKJMTF-FQEVSTJZSA-N (2s)-2-[[6-(4-phenylmethoxyphenyl)pyrimidin-4-yl]amino]hexanoic acid Chemical compound C1=NC(N[C@@H](CCCC)C(O)=O)=CC(C=2C=CC(OCC=3C=CC=CC=3)=CC=2)=N1 IVXYMIGMIKJMTF-FQEVSTJZSA-N 0.000 claims 1
- KKYBUEZMYJYNRH-QFIPXVFZSA-N (2s)-2-[[6-[4-(1,3-benzodioxol-5-yl)phenyl]pyrimidin-4-yl]amino]-3-phenylpropanoic acid Chemical compound C([C@@H](C(=O)O)NC=1N=CN=C(C=1)C=1C=CC(=CC=1)C=1C=C2OCOC2=CC=1)C1=CC=CC=C1 KKYBUEZMYJYNRH-QFIPXVFZSA-N 0.000 claims 1
- JEHSGHRHLCWGMV-DEOSSOPVSA-N (2s)-2-[[6-[4-(2-phenylethoxy)phenyl]pyrimidin-4-yl]amino]-3-pyridin-2-ylpropanoic acid Chemical compound C([C@@H](C(=O)O)NC=1N=CN=C(C=1)C=1C=CC(OCCC=2C=CC=CC=2)=CC=1)C1=CC=CC=N1 JEHSGHRHLCWGMV-DEOSSOPVSA-N 0.000 claims 1
- NXLNNDZBYAPAOS-DEOSSOPVSA-N (2s)-2-[[6-[4-(3-methoxyphenyl)phenyl]pyrimidin-4-yl]amino]-3-phenylpropanoic acid Chemical compound COC1=CC=CC(C=2C=CC(=CC=2)C=2N=CN=C(N[C@@H](CC=3C=CC=CC=3)C(O)=O)C=2)=C1 NXLNNDZBYAPAOS-DEOSSOPVSA-N 0.000 claims 1
- ZICORNPLGVZWKU-DEOSSOPVSA-N (2s)-2-[[6-[4-(4-methoxyphenyl)phenyl]pyrimidin-4-yl]amino]-3-phenylpropanoic acid Chemical compound C1=CC(OC)=CC=C1C1=CC=C(C=2N=CN=C(N[C@@H](CC=3C=CC=CC=3)C(O)=O)C=2)C=C1 ZICORNPLGVZWKU-DEOSSOPVSA-N 0.000 claims 1
- KOZJIVOBVPPTRB-NRFANRHFSA-N (2s)-2-[[6-[4-(cyclopropylmethoxy)phenyl]pyrimidin-4-yl]amino]-3-(4-fluorophenyl)propanoic acid Chemical compound C([C@@H](C(=O)O)NC=1N=CN=C(C=1)C=1C=CC(OCC2CC2)=CC=1)C1=CC=C(F)C=C1 KOZJIVOBVPPTRB-NRFANRHFSA-N 0.000 claims 1
- DOSOWINAIXZXBP-NRFANRHFSA-N (2s)-2-[[6-[4-(cyclopropylmethoxy)phenyl]pyrimidin-4-yl]amino]-3-phenylpropanoic acid Chemical compound C([C@@H](C(=O)O)NC=1N=CN=C(C=1)C=1C=CC(OCC2CC2)=CC=1)C1=CC=CC=C1 DOSOWINAIXZXBP-NRFANRHFSA-N 0.000 claims 1
- WCIVSDPGCGNDDJ-DEOSSOPVSA-N (2s)-2-[[6-[4-(phenoxymethyl)phenyl]pyrimidin-4-yl]amino]-3-phenylpropanoic acid Chemical compound C([C@@H](C(=O)O)NC=1N=CN=C(C=1)C=1C=CC(COC=2C=CC=CC=2)=CC=1)C1=CC=CC=C1 WCIVSDPGCGNDDJ-DEOSSOPVSA-N 0.000 claims 1
- WCLXNNJSMFBVDT-DEOSSOPVSA-N (2s)-2-[[6-[4-[(2-fluorophenyl)methoxy]phenyl]pyrimidin-4-yl]amino]-3-phenylpropanoic acid Chemical compound C([C@@H](C(=O)O)NC=1N=CN=C(C=1)C=1C=CC(OCC=2C(=CC=CC=2)F)=CC=1)C1=CC=CC=C1 WCLXNNJSMFBVDT-DEOSSOPVSA-N 0.000 claims 1
- ITEUWUMKZSPMJB-DEOSSOPVSA-N (2s)-2-[[6-[4-[(3,5-difluorophenyl)methoxy]phenyl]pyrimidin-4-yl]amino]-3-phenylpropanoic acid Chemical compound C([C@@H](C(=O)O)NC=1N=CN=C(C=1)C=1C=CC(OCC=2C=C(F)C=C(F)C=2)=CC=1)C1=CC=CC=C1 ITEUWUMKZSPMJB-DEOSSOPVSA-N 0.000 claims 1
- YCDNYEBBPDRCPP-QHCPKHFHSA-N (2s)-2-[[6-[4-[(3,5-difluorophenyl)methoxy]phenyl]pyrimidin-4-yl]amino]-3-pyridin-2-ylpropanoic acid Chemical compound C([C@@H](C(=O)O)NC=1N=CN=C(C=1)C=1C=CC(OCC=2C=C(F)C=C(F)C=2)=CC=1)C1=CC=CC=N1 YCDNYEBBPDRCPP-QHCPKHFHSA-N 0.000 claims 1
- HBRFANHFQXCKEY-SANMLTNESA-N (2s)-2-[[6-[4-[(3,5-dimethoxyphenyl)methoxy]phenyl]pyrimidin-4-yl]amino]-3-phenylpropanoic acid Chemical compound COC1=CC(OC)=CC(COC=2C=CC(=CC=2)C=2N=CN=C(N[C@@H](CC=3C=CC=CC=3)C(O)=O)C=2)=C1 HBRFANHFQXCKEY-SANMLTNESA-N 0.000 claims 1
- YPSCYRRLZIEVQQ-VWLOTQADSA-N (2s)-2-[[6-[4-[(3,5-dimethoxyphenyl)methoxy]phenyl]pyrimidin-4-yl]amino]-3-pyridin-2-ylpropanoic acid Chemical compound COC1=CC(OC)=CC(COC=2C=CC(=CC=2)C=2N=CN=C(N[C@@H](CC=3N=CC=CC=3)C(O)=O)C=2)=C1 YPSCYRRLZIEVQQ-VWLOTQADSA-N 0.000 claims 1
- CDYAZGSXKBVOFC-DEOSSOPVSA-N (2s)-2-[[6-[4-[(3-fluorophenyl)methoxy]phenyl]pyrimidin-4-yl]amino]-3-phenylpropanoic acid Chemical compound C([C@@H](C(=O)O)NC=1N=CN=C(C=1)C=1C=CC(OCC=2C=C(F)C=CC=2)=CC=1)C1=CC=CC=C1 CDYAZGSXKBVOFC-DEOSSOPVSA-N 0.000 claims 1
- PSXGSFPFCUSNHR-QHCPKHFHSA-N (2s)-2-[[6-[4-[(3-fluorophenyl)methoxy]phenyl]pyrimidin-4-yl]amino]-3-pyridin-2-ylpropanoic acid Chemical compound C([C@@H](C(=O)O)NC=1N=CN=C(C=1)C=1C=CC(OCC=2C=C(F)C=CC=2)=CC=1)C1=CC=CC=N1 PSXGSFPFCUSNHR-QHCPKHFHSA-N 0.000 claims 1
- YRYPTCVIRZWGBQ-VWLOTQADSA-N (2s)-2-[[6-[4-[(3-methoxyphenyl)methoxy]phenyl]pyrimidin-4-yl]amino]-3-phenylpropanoic acid Chemical compound COC1=CC=CC(COC=2C=CC(=CC=2)C=2N=CN=C(N[C@@H](CC=3C=CC=CC=3)C(O)=O)C=2)=C1 YRYPTCVIRZWGBQ-VWLOTQADSA-N 0.000 claims 1
- ZTQIPTCVCJTZSF-DEOSSOPVSA-N (2s)-2-[[6-[4-[(3-methoxyphenyl)methoxy]phenyl]pyrimidin-4-yl]amino]-3-pyridin-2-ylpropanoic acid Chemical compound COC1=CC=CC(COC=2C=CC(=CC=2)C=2N=CN=C(N[C@@H](CC=3N=CC=CC=3)C(O)=O)C=2)=C1 ZTQIPTCVCJTZSF-DEOSSOPVSA-N 0.000 claims 1
- YKOVOXGNQHYDLO-DEOSSOPVSA-N (2s)-2-[[6-[4-[(4-fluorophenyl)methoxy]phenyl]pyrimidin-4-yl]amino]-3-phenylpropanoic acid Chemical compound C([C@@H](C(=O)O)NC=1N=CN=C(C=1)C=1C=CC(OCC=2C=CC(F)=CC=2)=CC=1)C1=CC=CC=C1 YKOVOXGNQHYDLO-DEOSSOPVSA-N 0.000 claims 1
- WPIWAEAPTLYFQX-DEOSSOPVSA-N (2s)-3-(3-hydroxyphenyl)-2-[[6-(4-phenylmethoxyphenyl)pyrimidin-4-yl]amino]propanoic acid Chemical compound C([C@@H](C(=O)O)NC=1N=CN=C(C=1)C=1C=CC(OCC=2C=CC=CC=2)=CC=1)C1=CC=CC(O)=C1 WPIWAEAPTLYFQX-DEOSSOPVSA-N 0.000 claims 1
- ROIMBOHNEUBGRV-DEOSSOPVSA-N (2s)-3-(4-chlorophenyl)-2-[[6-(4-phenylmethoxyphenyl)pyrimidin-4-yl]amino]propanoic acid Chemical compound C([C@@H](C(=O)O)NC=1N=CN=C(C=1)C=1C=CC(OCC=2C=CC=CC=2)=CC=1)C1=CC=C(Cl)C=C1 ROIMBOHNEUBGRV-DEOSSOPVSA-N 0.000 claims 1
- AFRDMVIWRZTGGG-NRFANRHFSA-N (2s)-3-(4-chlorophenyl)-2-[[6-[4-(cyclopropylmethoxy)phenyl]pyrimidin-4-yl]amino]propanoic acid Chemical compound C([C@@H](C(=O)O)NC=1N=CN=C(C=1)C=1C=CC(OCC2CC2)=CC=1)C1=CC=C(Cl)C=C1 AFRDMVIWRZTGGG-NRFANRHFSA-N 0.000 claims 1
- MEDKYBICTTVCDA-DEOSSOPVSA-N (2s)-3-(4-fluorophenyl)-2-[[6-(4-phenylmethoxyphenyl)pyrimidin-4-yl]amino]propanoic acid Chemical compound C([C@@H](C(=O)O)NC=1N=CN=C(C=1)C=1C=CC(OCC=2C=CC=CC=2)=CC=1)C1=CC=C(F)C=C1 MEDKYBICTTVCDA-DEOSSOPVSA-N 0.000 claims 1
- DIJXGISWAISVKY-SANMLTNESA-N (2s)-3-[3-(2-aminoethoxy)phenyl]-2-[[6-(4-phenylmethoxyphenyl)pyrimidin-4-yl]amino]propanoic acid Chemical compound NCCOC1=CC=CC(C[C@H](NC=2N=CN=C(C=2)C=2C=CC(OCC=3C=CC=CC=3)=CC=2)C(O)=O)=C1 DIJXGISWAISVKY-SANMLTNESA-N 0.000 claims 1
- RGQRBJNDTRNIPO-PMERELPUSA-N (2s)-3-[3-(2-morpholin-4-ylethoxy)phenyl]-2-[[6-(4-phenylmethoxyphenyl)pyrimidin-4-yl]amino]propanoic acid Chemical compound C([C@@H](C(=O)O)NC=1N=CN=C(C=1)C=1C=CC(OCC=2C=CC=CC=2)=CC=1)C(C=1)=CC=CC=1OCCN1CCOCC1 RGQRBJNDTRNIPO-PMERELPUSA-N 0.000 claims 1
- DIQYJMGQWDEHSP-NDEPHWFRSA-N (2s)-3-[3-[2-(dimethylamino)ethoxy]phenyl]-2-[[6-(4-phenylmethoxyphenyl)pyrimidin-4-yl]amino]propanoic acid Chemical compound CN(C)CCOC1=CC=CC(C[C@H](NC=2N=CN=C(C=2)C=2C=CC(OCC=3C=CC=CC=3)=CC=2)C(O)=O)=C1 DIQYJMGQWDEHSP-NDEPHWFRSA-N 0.000 claims 1
- RRYFPNITZGCUPZ-DEOSSOPVSA-N (2s)-3-phenyl-2-[[6-(4-phenylmethoxyphenyl)pyrimidin-4-yl]amino]propanoic acid Chemical compound C([C@@H](C(=O)O)NC=1N=CN=C(C=1)C=1C=CC(OCC=2C=CC=CC=2)=CC=1)C1=CC=CC=C1 RRYFPNITZGCUPZ-DEOSSOPVSA-N 0.000 claims 1
- WONHOFUMZAMNNZ-VWLOTQADSA-N (2s)-3-phenyl-2-[[6-[4-(2-phenylethoxy)phenyl]pyrimidin-4-yl]amino]propanoic acid Chemical compound C([C@@H](C(=O)O)NC=1N=CN=C(C=1)C=1C=CC(OCCC=2C=CC=CC=2)=CC=1)C1=CC=CC=C1 WONHOFUMZAMNNZ-VWLOTQADSA-N 0.000 claims 1
- CBGSRTIDTAZXIT-VWLOTQADSA-N (2s)-3-phenyl-2-[[6-[4-(2-phenylethynyl)phenyl]pyrimidin-4-yl]amino]propanoic acid Chemical compound C([C@@H](C(=O)O)NC=1N=CN=C(C=1)C=1C=CC(=CC=1)C#CC=1C=CC=CC=1)C1=CC=CC=C1 CBGSRTIDTAZXIT-VWLOTQADSA-N 0.000 claims 1
- NHDPWOURSIOXND-QHCPKHFHSA-N (2s)-3-phenyl-2-[[6-[4-(2-pyrrol-1-ylethoxy)phenyl]pyrimidin-4-yl]amino]propanoic acid Chemical compound C([C@@H](C(=O)O)NC=1N=CN=C(C=1)C=1C=CC(OCCN2C=CC=C2)=CC=1)C1=CC=CC=C1 NHDPWOURSIOXND-QHCPKHFHSA-N 0.000 claims 1
- NPBDURIQAHDPGY-QHCPKHFHSA-N (2s)-3-phenyl-2-[[6-[4-(pyridin-3-ylmethoxy)phenyl]pyrimidin-4-yl]amino]propanoic acid Chemical compound C([C@@H](C(=O)O)NC=1N=CN=C(C=1)C=1C=CC(OCC=2C=NC=CC=2)=CC=1)C1=CC=CC=C1 NPBDURIQAHDPGY-QHCPKHFHSA-N 0.000 claims 1
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- 241001465754 Metazoa Species 0.000 claims 1
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 claims 1
- 208000012931 Urologic disease Diseases 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000003705 anilinocarbonyl group Chemical group O=C([*])N([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 125000006639 cyclohexyl carbonyl group Chemical group 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000006332 fluoro benzoyl group Chemical group 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 1
- 125000003831 tetrazolyl group Chemical group 0.000 claims 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 claims 1
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Families Citing this family (28)
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| ATE327744T1 (de) | 2001-03-20 | 2006-06-15 | Sanol Arznei Schwarz Gmbh | Neue verwendung von peptidverbindungen bei der behandlung von nicht-neuropathischem entzündungsschmerz |
| DE60100055T2 (de) | 2001-03-21 | 2003-07-24 | Schwarz Pharma Ag | Neue Verwendung einer Klasse von Peptidverbindungen zur Behandlung von Allodynie oder andere Arten von chronischen oder Phantomschmerzen |
| BRPI0417101A (pt) | 2003-12-02 | 2007-02-06 | Sanol Arznei Schwarz Gmbh | uso de compostos de peptìdeo para tratamento de dor neuropática central |
| JP4772690B2 (ja) * | 2003-12-03 | 2011-09-14 | ワイエム・バイオサイエンシズ・オーストラリア・ピーティーワイ・リミテッド | チューブリン阻害剤 |
| EP1604655A1 (en) | 2004-06-09 | 2005-12-14 | Schwarz Pharma Ag | Novel use of peptide compounds for treating pain in trigeminal neuralgia |
| MX2007002269A (es) | 2004-08-27 | 2007-06-15 | Sanol Arznei Schwarz Gmbh | Uso novedoso de compuestos peptidos para tratar dolor por c??ncer de huesos, dolor inducido por quimioterapia y nucleosidos. |
| WO2006029735A1 (en) * | 2004-09-15 | 2006-03-23 | Bayer Healthcare Ag | Diagnostics and therapeutics for diseases associated with prostaglandin 12 receptor (ptgir) |
| HN2005000795A (es) * | 2004-10-15 | 2010-08-19 | Aventis Pharma Inc | Pirimidinas como antagonistas del receptor de prostaglandina d2 |
| PE20070404A1 (es) | 2005-07-29 | 2007-05-10 | Wyeth Corp | Compuestos derivados de cianopirrol-sulfonamida como moduladores del receptor de progesterona |
| PE20070341A1 (es) * | 2005-07-29 | 2007-04-13 | Wyeth Corp | Derivados de pirrol como moduladores del receptor de progesterona |
| PE20070182A1 (es) | 2005-07-29 | 2007-03-06 | Wyeth Corp | Derivados cianopirrol-fenil amida como moduladores del receptor de progesterona |
| KR20080040692A (ko) | 2005-08-02 | 2008-05-08 | 렉시컨 파마슈티컬스 인코퍼레이티드 | 단백질 키나제 억제제로서의 2-아미노아릴 피리딘 |
| KR20150003925A (ko) | 2006-06-15 | 2015-01-09 | 유씨비 파르마 게엠베하 | 상승적 항경련 효과를 갖는 약제학적 조성물 |
| US20080242694A1 (en) * | 2006-09-18 | 2008-10-02 | D Sidocky Neil R | Amino-substituted heterocycles, compositions thereof, and methods of treatment therewith |
| JO3598B1 (ar) * | 2006-10-10 | 2020-07-05 | Infinity Discovery Inc | الاحماض والاسترات البورونية كمثبطات اميد هيدروليز الحامض الدهني |
| WO2009132310A1 (en) | 2008-04-25 | 2009-10-29 | Wisconsin Alumni Research Foundation | Inhibitors of udp-galactopyranose mutase thwart mycobacterial growth |
| US20100060985A1 (en) | 2008-09-09 | 2010-03-11 | Fujifilm Corporation | Method for producing polarizing plate, and automobile's windshield |
| MY154000A (en) | 2008-09-22 | 2015-04-30 | Cayman Chem Co | Multiheteroaryl compounds as inhibitors of h-pgds and their use for treating prostaglandin d2 mediated diseases |
| AR081331A1 (es) | 2010-04-23 | 2012-08-08 | Cytokinetics Inc | Amino- pirimidinas composiciones de las mismas y metodos para el uso de los mismos |
| AR081626A1 (es) | 2010-04-23 | 2012-10-10 | Cytokinetics Inc | Compuestos amino-piridazinicos, composiciones farmaceuticas que los contienen y uso de los mismos para tratar trastornos musculares cardiacos y esqueleticos |
| US9133123B2 (en) | 2010-04-23 | 2015-09-15 | Cytokinetics, Inc. | Certain amino-pyridines and amino-triazines, compositions thereof, and methods for their use |
| US8759380B2 (en) | 2011-04-22 | 2014-06-24 | Cytokinetics, Inc. | Certain heterocycles, compositions thereof, and methods for their use |
| AR094929A1 (es) | 2013-02-28 | 2015-09-09 | Bristol Myers Squibb Co | Derivados de fenilpirazol como inhibidores potentes de rock1 y rock2 |
| JP6423372B2 (ja) | 2013-02-28 | 2018-11-14 | ブリストル−マイヤーズ スクイブ カンパニーＢｒｉｓｔｏｌ−Ｍｙｅｒｓ Ｓｑｕｉｂｂ Ｃｏｍｐａｎｙ | 強力なｒｏｃｋ１およびｒｏｃｋ２阻害剤としてのフェニルピラゾール誘導体 |
| DK3013813T3 (da) | 2013-06-27 | 2019-06-03 | Pfizer | Heteroaromatiske forbindelser og anvendelse deraf som dopamin-d1-ligander |
| WO2015013322A1 (en) * | 2013-07-22 | 2015-01-29 | The Regents Of The University Of Colorado, A Body Corporate | Silylalkyloxyaryl compounds and methods for treating cancer |
| US9994547B2 (en) | 2014-10-06 | 2018-06-12 | Takeda Pharmaceutical Company Limited | Heteroarylamide inhibitors of TBK1 |
| US10080757B2 (en) | 2016-03-11 | 2018-09-25 | Wisconsin Alumni Research Foundation | Inhibitors of UDP-galactopyranose mutase |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US4259489A (en) * | 1977-12-22 | 1981-03-31 | Kyowa Gas Chemical Industry Co. Ltd. | 2,3-Dicyanopyrazines |
| WO1996033972A1 (en) * | 1995-04-28 | 1996-10-31 | Glaxo Group Limited | Methods for synthesizing diverse collections of pyridines, pyrimidines, 1,4-dihydro derivatives thereof, and piperidine derivatives |
| HUP0001232A3 (en) * | 1996-12-23 | 2001-02-28 | Elan Pharmaceuticals Inc San F | Cycloalkyl, lactam, lactone derivatives and their thio analogues inhibiting betha-amyloid peptide release and/or its synthesis and pharmaceutical compositions containing the compounds |
| GB2323842A (en) * | 1997-04-04 | 1998-10-07 | Ferring Bv | Pyridine derivatives |
| AU2623900A (en) * | 1999-01-22 | 2000-08-07 | American Home Products Corporation | Compounds which inhibit leukocyte adhesion mediated by vla-4 |
| US20020058606A1 (en) * | 1999-05-10 | 2002-05-16 | Gonzalez Maria Isabel | Treatment of sexual dysfunction |
| CN1241909C (zh) * | 2000-03-16 | 2006-02-15 | 弗·哈夫曼-拉罗切有限公司 | 用作ip拮抗剂的羧酸衍生物 |
| WO2002040008A2 (en) * | 2000-11-17 | 2002-05-23 | Warner-Lambert Company Llc | Treatment of sexual dysfunction with non peptide bombesin receptor antagonists |
| CN100415770C (zh) * | 2001-05-30 | 2008-09-03 | 诺瓦提斯公司 | 2－{[n－(2－氨基－3－(杂芳基或芳基)丙酰基)－氨基酰基]－氨基}－烷基硼酸衍生物 |
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- 2003-10-29 HR HR20050529A patent/HRP20050529A2/xx not_active Application Discontinuation
- 2003-10-29 PL PL376993A patent/PL376993A1/pl unknown
- 2003-10-29 EP EP03810952A patent/EP1575919A1/en not_active Withdrawn
- 2003-10-29 AU AU2003276201A patent/AU2003276201A1/en not_active Abandoned
- 2003-10-29 BR BR0316191-9A patent/BR0316191A/pt not_active IP Right Cessation
- 2003-10-29 WO PCT/EP2003/011976 patent/WO2004043926A1/en not_active Ceased
- 2003-10-29 JP JP2005506646A patent/JP2006514110A/ja active Pending
- 2003-10-29 KR KR1020057008288A patent/KR20050074571A/ko not_active Withdrawn
- 2003-10-29 US US10/534,174 patent/US20060089371A1/en not_active Abandoned
- 2003-11-07 UY UY28072A patent/UY28072A1/es not_active Application Discontinuation
- 2003-11-10 PE PE2003001135A patent/PE20040672A1/es not_active Application Discontinuation
- 2003-11-10 AR ARP030104130A patent/AR042023A1/es not_active Application Discontinuation
- 2003-11-10 HN HN2003000353A patent/HN2003000353A/es unknown
- 2003-11-10 TW TW092131351A patent/TW200418799A/zh unknown
-
2005
- 2005-05-11 MA MA28277A patent/MA27491A1/fr unknown
- 2005-05-11 EC EC2005005789A patent/ECSP055789A/es unknown
- 2005-06-08 CO CO05055462A patent/CO5580824A2/es not_active Application Discontinuation
- 2005-06-09 NO NO20052797A patent/NO20052797D0/no not_active Application Discontinuation
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