KR20050074571A - Ip 수용체 길항제로서의 페닐 또는 헤테로아릴 아미노알칸 유도체 - Google Patents
Ip 수용체 길항제로서의 페닐 또는 헤테로아릴 아미노알칸 유도체 Download PDFInfo
- Publication number
- KR20050074571A KR20050074571A KR1020057008288A KR20057008288A KR20050074571A KR 20050074571 A KR20050074571 A KR 20050074571A KR 1020057008288 A KR1020057008288 A KR 1020057008288A KR 20057008288 A KR20057008288 A KR 20057008288A KR 20050074571 A KR20050074571 A KR 20050074571A
- Authority
- KR
- South Korea
- Prior art keywords
- phenyl
- optionally substituted
- halogen
- pyrimidin
- mono
- 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.)
- Withdrawn
Links
- -1 heteroaryl amino alkane Chemical class 0.000 title claims abstract description 326
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 title claims abstract description 148
- 239000002464 receptor antagonist Substances 0.000 title claims abstract description 11
- 229940044551 receptor antagonist Drugs 0.000 title claims abstract description 11
- 150000001875 compounds Chemical class 0.000 claims abstract description 160
- 238000011282 treatment Methods 0.000 claims abstract description 31
- 108091006335 Prostaglandin I receptors Proteins 0.000 claims abstract description 27
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 20
- 230000002265 prevention Effects 0.000 claims abstract description 12
- 208000002193 Pain Diseases 0.000 claims abstract description 11
- 201000010099 disease Diseases 0.000 claims abstract description 11
- 239000004480 active ingredient Substances 0.000 claims abstract description 10
- 206010061218 Inflammation Diseases 0.000 claims abstract description 9
- 208000035475 disorder Diseases 0.000 claims abstract description 9
- 230000004054 inflammatory process Effects 0.000 claims abstract description 9
- 208000001953 Hypotension Diseases 0.000 claims abstract description 8
- 230000036543 hypotension Effects 0.000 claims abstract description 8
- 208000032843 Hemorrhage Diseases 0.000 claims abstract description 7
- 230000000740 bleeding effect Effects 0.000 claims abstract description 7
- 230000036407 pain Effects 0.000 claims abstract description 7
- 208000031220 Hemophilia Diseases 0.000 claims abstract description 6
- 208000009292 Hemophilia A Diseases 0.000 claims abstract description 6
- 208000034158 bleeding Diseases 0.000 claims abstract description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 172
- 125000000217 alkyl group Chemical group 0.000 claims description 132
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 94
- 150000002367 halogens Chemical class 0.000 claims description 92
- 229910052757 nitrogen Inorganic materials 0.000 claims description 82
- 239000001257 hydrogen Substances 0.000 claims description 77
- 229910052739 hydrogen Inorganic materials 0.000 claims description 77
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 53
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 51
- 125000000623 heterocyclic group Chemical group 0.000 claims description 51
- 125000001624 naphthyl group Chemical group 0.000 claims description 51
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 50
- 125000002837 carbocyclic group Chemical group 0.000 claims description 46
- 229910052760 oxygen Inorganic materials 0.000 claims description 44
- 229920006395 saturated elastomer Polymers 0.000 claims description 43
- 125000001424 substituent group Chemical group 0.000 claims description 42
- 238000000034 method Methods 0.000 claims description 41
- 125000004414 alkyl thio group Chemical group 0.000 claims description 40
- 125000005842 heteroatom Chemical group 0.000 claims description 40
- 125000004076 pyridyl group Chemical group 0.000 claims description 40
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 36
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 36
- 125000002015 acyclic group Chemical group 0.000 claims description 36
- 125000001041 indolyl group Chemical group 0.000 claims description 36
- 125000000304 alkynyl group Chemical group 0.000 claims description 35
- 125000003118 aryl group Chemical group 0.000 claims description 34
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 34
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 claims description 32
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 31
- 125000005493 quinolyl group Chemical group 0.000 claims description 31
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 28
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 27
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 27
- 125000001072 heteroaryl group Chemical group 0.000 claims description 26
- 150000002431 hydrogen Chemical class 0.000 claims description 26
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 26
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 24
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 23
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 23
- 150000003839 salts Chemical class 0.000 claims description 22
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 21
- 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 description 21
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 21
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 21
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 20
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 19
- 125000002883 imidazolyl group Chemical group 0.000 claims description 18
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 17
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 17
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 16
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical group FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 16
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 16
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 16
- 239000003814 drug Substances 0.000 claims description 15
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 15
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 14
- 125000004193 piperazinyl group Chemical group 0.000 claims description 13
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
- 229910052717 sulfur Inorganic materials 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 229940079593 drug Drugs 0.000 claims description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 8
- 125000003282 alkyl amino group Chemical group 0.000 claims description 7
- 125000004122 cyclic group Chemical group 0.000 claims description 7
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 7
- LRQKBLKVPFOOQJ-YFKPBYRVSA-N L-norleucine Chemical compound CCCC[C@H]([NH3+])C([O-])=O LRQKBLKVPFOOQJ-YFKPBYRVSA-N 0.000 claims description 6
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 6
- 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 description 5
- 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 description 4
- DOSOWINAIXZXBP-OAQYLSRUSA-N (2r)-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-OAQYLSRUSA-N 0.000 claims description 4
- 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 description 4
- 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 description 4
- 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 description 4
- LJWRRKQTPFBURL-QFIPXVFZSA-N (2s)-3-phenyl-2-[[6-(6-phenylmethoxypyridin-3-yl)pyrimidin-4-yl]amino]propanoic acid Chemical compound C([C@@H](C(=O)O)NC=1N=CN=C(C=1)C=1C=NC(OCC=2C=CC=CC=2)=CC=1)C1=CC=CC=C1 LJWRRKQTPFBURL-QFIPXVFZSA-N 0.000 claims description 4
- 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 description 4
- 239000004727 Noryl Substances 0.000 claims description 4
- 229920001207 Noryl Polymers 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 claims description 4
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 4
- 230000002485 urinary effect Effects 0.000 claims description 4
- 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 description 3
- 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 description 3
- 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 description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 3
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
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- 230000028327 secretion Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 230000001953 sensory effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- 229940054269 sodium pyruvate Drugs 0.000 description 1
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
- PPASLZSBLFJQEF-RXSVEWSESA-M sodium-L-ascorbate Chemical class [Na+].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RXSVEWSESA-M 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
- 239000008275 solid aerosol Substances 0.000 description 1
- 238000010532 solid phase synthesis reaction Methods 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 208000020431 spinal cord injury Diseases 0.000 description 1
- 210000003594 spinal ganglia Anatomy 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 125000003638 stannyl group Chemical group [H][Sn]([H])([H])* 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000012058 sterile packaged powder Substances 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- UUZRNCDGBZOORO-MHZLTWQESA-N tert-butyl (2s)-3-phenyl-2-[[4-(4-phenylmethoxyphenyl)pyrimidin-2-yl]amino]propanoate Chemical compound C([C@@H](C(=O)OC(C)(C)C)NC=1N=C(C=CN=1)C=1C=CC(OCC=2C=CC=CC=2)=CC=1)C1=CC=CC=C1 UUZRNCDGBZOORO-MHZLTWQESA-N 0.000 description 1
- QOISWWBTZMFUEL-UHFFFAOYSA-N tert-butyl 2-amino-3-phenylpropanoate Chemical compound CC(C)(C)OC(=O)C(N)CC1=CC=CC=C1 QOISWWBTZMFUEL-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- OSBSFAARYOCBHB-UHFFFAOYSA-N tetrapropylammonium Chemical compound CCC[N+](CCC)(CCC)CCC OSBSFAARYOCBHB-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000006090 thiamorpholinyl sulfone group Chemical group 0.000 description 1
- 125000001984 thiazolidinyl group Chemical group 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 210000003437 trachea Anatomy 0.000 description 1
- 230000037317 transdermal delivery Effects 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 210000000626 ureter Anatomy 0.000 description 1
- 210000001635 urinary tract Anatomy 0.000 description 1
- 230000008728 vascular permeability Effects 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 229930195724 β-lactose Natural products 0.000 description 1
Classifications
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/34—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
- C07C229/36—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton containing six-membered aromatic rings with at least one amino group and one carboxyl group bound to the same carbon atom of the carbon skeleton
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/38—Nitrogen atoms
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
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- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
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- C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
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- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
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- C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
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- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/38—Nitrogen atoms
- C07D277/42—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
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- Plural Heterocyclic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP02025024.7 | 2002-11-11 | ||
| EP02025024 | 2002-11-11 | ||
| EP03011397.1 | 2003-05-20 | ||
| EP03011397 | 2003-05-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20050074571A true KR20050074571A (ko) | 2005-07-18 |
Family
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| EP (1) | EP1575919A1 (enExample) |
| JP (1) | JP2006514110A (enExample) |
| KR (1) | KR20050074571A (enExample) |
| AR (1) | AR042023A1 (enExample) |
| AU (1) | AU2003276201A1 (enExample) |
| BR (1) | BR0316191A (enExample) |
| CA (1) | CA2505361A1 (enExample) |
| CO (1) | CO5580824A2 (enExample) |
| EC (1) | ECSP055789A (enExample) |
| HN (1) | HN2003000353A (enExample) |
| HR (1) | HRP20050529A2 (enExample) |
| MA (1) | MA27491A1 (enExample) |
| NO (1) | NO20052797L (enExample) |
| PE (1) | PE20040672A1 (enExample) |
| PL (1) | PL376993A1 (enExample) |
| TW (1) | TW200418799A (enExample) |
| UY (1) | UY28072A1 (enExample) |
| WO (1) | WO2004043926A1 (enExample) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
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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 |
| PT1243263E (pt) | 2001-03-21 | 2003-03-31 | Sanol Arznei Schwarz Gmbh | Nova utilizacao de uma classe peptidica de composto para o tratamento de alodinia ou de outros tipos diferentes de dor cronica ou fantasma |
| WO2005053667A1 (en) | 2003-12-02 | 2005-06-16 | Schwarz Pharma Ag | Novel use of peptide compounds for treating central neuropathic pain |
| ATE497949T1 (de) * | 2003-12-03 | 2011-02-15 | Ym Biosciences Australia Pty | Tubulininhibitoren |
| 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 |
| 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 |
| PE20070404A1 (es) * | 2005-07-29 | 2007-05-10 | Wyeth Corp | Compuestos derivados de cianopirrol-sulfonamida como moduladores del receptor de progesterona |
| AU2006275403A1 (en) | 2005-08-02 | 2007-02-08 | Lexicon Pharmaceuticals, Inc. | 2-aminoaryl pyridines as protein kinases inhibitors |
| EP2462990B2 (en) | 2006-06-15 | 2018-04-18 | UCB Pharma GmbH | Pharmaceutical composition comprising lacosamide and levetiracetam with synergistic anticonvulsant effect |
| 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 |
| WO2010033977A2 (en) | 2008-09-22 | 2010-03-25 | Cayman Chemical Company | 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 |
| US9133123B2 (en) | 2010-04-23 | 2015-09-15 | Cytokinetics, Inc. | Certain amino-pyridines and amino-triazines, compositions thereof, and methods for their use |
| 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 |
| US8759380B2 (en) | 2011-04-22 | 2014-06-24 | Cytokinetics, Inc. | Certain heterocycles, compositions thereof, and methods for their use |
| US9828345B2 (en) | 2013-02-28 | 2017-11-28 | Bristol-Myers Squibb Company | Phenylpyrazole derivatives as potent ROCK1 and ROCK2 inhibitors |
| TW201444798A (zh) | 2013-02-28 | 2014-12-01 | 必治妥美雅史谷比公司 | 作爲強效rock1及rock2抑制劑之苯基吡唑衍生物 |
| FI3421462T3 (fi) | 2013-06-27 | 2023-06-26 | Pfizer | Heteroaromaattisia yhdisteitä ja niiden käyttö dopamiini-d1-ligandeina |
| 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 |
|---|---|---|---|---|
| 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 |
| JP3812952B2 (ja) * | 1996-12-23 | 2006-08-23 | エラン ファーマシューティカルズ,インコーポレイテッド | シクロアルキル、ラクタム、ラクトンおよびその関連化合物およびその医薬組成物、並びに該化合物を用いたβ−アミロイドペプチドの放出および/またはその合成を阻害する方法 |
| 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 |
| KR100523119B1 (ko) * | 2000-03-16 | 2005-10-20 | 에프. 호프만-라 로슈 아게 | Ip 길항제로서의 카복실산 유도체 |
| HUP0301892A3 (en) * | 2000-11-17 | 2005-06-28 | Warner Lambert Company Llc Mor | Pharmaceutical compositions for treatment of sexual dysfunction and their preparation |
| ATE317850T1 (de) * | 2001-05-30 | 2006-03-15 | Novartis Pharma Gmbh | 2-((n-(2-amino-3-(heteroaryl- oder - aryl)propionyl)aminoacyl)amino)- alkylboronsäurederivate |
-
2003
- 2003-10-29 EP EP03810952A patent/EP1575919A1/en not_active Withdrawn
- 2003-10-29 HR HR20050529A patent/HRP20050529A2/xx not_active Application Discontinuation
- 2003-10-29 AU AU2003276201A patent/AU2003276201A1/en not_active Abandoned
- 2003-10-29 US US10/534,174 patent/US20060089371A1/en not_active Abandoned
- 2003-10-29 KR KR1020057008288A patent/KR20050074571A/ko not_active Withdrawn
- 2003-10-29 BR BR0316191-9A patent/BR0316191A/pt not_active IP Right Cessation
- 2003-10-29 CA CA002505361A patent/CA2505361A1/en not_active Abandoned
- 2003-10-29 WO PCT/EP2003/011976 patent/WO2004043926A1/en not_active Ceased
- 2003-10-29 PL PL376993A patent/PL376993A1/pl unknown
- 2003-10-29 JP JP2005506646A patent/JP2006514110A/ja active Pending
- 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 HN HN2003000353A patent/HN2003000353A/es unknown
- 2003-11-10 TW TW092131351A patent/TW200418799A/zh unknown
- 2003-11-10 AR ARP030104130A patent/AR042023A1/es not_active Application Discontinuation
-
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/NO20052797L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| WO2004043926A1 (en) | 2004-05-27 |
| UY28072A1 (es) | 2004-06-30 |
| CA2505361A1 (en) | 2004-05-27 |
| TW200418799A (en) | 2004-10-01 |
| AR042023A1 (es) | 2005-06-08 |
| CO5580824A2 (es) | 2005-11-30 |
| MA27491A1 (fr) | 2005-08-01 |
| NO20052797D0 (no) | 2005-06-09 |
| HRP20050529A2 (en) | 2006-08-31 |
| HN2003000353A (es) | 2003-11-23 |
| AU2003276201A1 (en) | 2004-06-03 |
| US20060089371A1 (en) | 2006-04-27 |
| ECSP055789A (es) | 2005-08-11 |
| PE20040672A1 (es) | 2004-10-29 |
| JP2006514110A (ja) | 2006-04-27 |
| EP1575919A1 (en) | 2005-09-21 |
| PL376993A1 (pl) | 2006-01-23 |
| BR0316191A (pt) | 2005-09-27 |
| NO20052797L (no) | 2005-06-09 |
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Patent event date: 20050510 Patent event code: PA01051R01D Comment text: International Patent Application |
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