AU2003276201A1 - Phenyl or heteroaryl amino alkane derivatives as ip receptor antagonist - Google Patents
Phenyl or heteroaryl amino alkane derivatives as ip receptor antagonist Download PDFInfo
- Publication number
- AU2003276201A1 AU2003276201A1 AU2003276201A AU2003276201A AU2003276201A1 AU 2003276201 A1 AU2003276201 A1 AU 2003276201A1 AU 2003276201 A AU2003276201 A AU 2003276201A AU 2003276201 A AU2003276201 A AU 2003276201A AU 2003276201 A1 AU2003276201 A1 AU 2003276201A1
- Authority
- AU
- Australia
- Prior art keywords
- phenyl
- optionally substituted
- halogen
- amino
- pyrimidin
- 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
- -1 heteroaryl amino alkane Chemical class 0.000 title claims description 264
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 title claims description 171
- 239000002464 receptor antagonist Substances 0.000 title claims description 10
- 229940044551 receptor antagonist Drugs 0.000 title claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 172
- 150000001875 compounds Chemical class 0.000 claims description 166
- 125000000217 alkyl group Chemical group 0.000 claims description 141
- 150000002367 halogens Chemical group 0.000 claims description 96
- 125000003545 alkoxy group Chemical group 0.000 claims description 83
- 229910052739 hydrogen Inorganic materials 0.000 claims description 81
- 239000001257 hydrogen Substances 0.000 claims description 77
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 52
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 51
- 125000000623 heterocyclic group Chemical group 0.000 claims description 49
- 125000001624 naphthyl group Chemical group 0.000 claims description 49
- 229910052757 nitrogen Inorganic materials 0.000 claims description 49
- 125000003282 alkyl amino group Chemical group 0.000 claims description 48
- 125000002837 carbocyclic group Chemical group 0.000 claims description 46
- 229910052760 oxygen Inorganic materials 0.000 claims description 42
- 125000004076 pyridyl group Chemical group 0.000 claims description 42
- 229920006395 saturated elastomer Polymers 0.000 claims description 42
- 125000001424 substituent group Chemical group 0.000 claims description 42
- 125000005842 heteroatom Chemical group 0.000 claims description 40
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 40
- 125000001041 indolyl group Chemical group 0.000 claims description 39
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 38
- 125000004414 alkyl thio group Chemical group 0.000 claims description 38
- 125000003118 aryl group Chemical group 0.000 claims description 37
- 150000002431 hydrogen Chemical class 0.000 claims description 35
- 125000000304 alkynyl group Chemical group 0.000 claims description 34
- 238000000034 method Methods 0.000 claims description 34
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 33
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 32
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 claims description 31
- 125000005493 quinolyl group Chemical group 0.000 claims description 31
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 29
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 29
- 238000011282 treatment Methods 0.000 claims description 29
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 28
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 27
- 125000001072 heteroaryl group Chemical group 0.000 claims description 24
- 108091006335 Prostaglandin I receptors Proteins 0.000 claims description 22
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 22
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 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
- 150000003839 salts Chemical class 0.000 claims description 21
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 20
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 19
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 18
- 125000002883 imidazolyl group Chemical group 0.000 claims description 18
- 125000003342 alkenyl group Chemical group 0.000 claims description 17
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 17
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 16
- 239000003814 drug Substances 0.000 claims description 15
- 238000011321 prophylaxis Methods 0.000 claims description 14
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 13
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 13
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 claims description 13
- 229960005190 phenylalanine Drugs 0.000 claims description 13
- 235000008729 phenylalanine Nutrition 0.000 claims description 13
- 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
- 239000004480 active ingredient Substances 0.000 claims description 10
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 10
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
- 208000014001 urinary system disease Diseases 0.000 claims description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 8
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 8
- 208000002193 Pain Diseases 0.000 claims description 8
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 8
- 125000004122 cyclic group Chemical group 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 8
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 8
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 8
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 7
- 208000001953 Hypotension Diseases 0.000 claims description 7
- 206010061218 Inflammation Diseases 0.000 claims description 7
- 230000036543 hypotension Effects 0.000 claims description 7
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 7
- 230000004054 inflammatory process Effects 0.000 claims description 7
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 7
- 208000032843 Hemorrhage Diseases 0.000 claims description 6
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 claims description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 6
- 208000031220 Hemophilia Diseases 0.000 claims description 5
- 208000009292 Hemophilia A Diseases 0.000 claims description 5
- 125000002947 alkylene group Chemical group 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
- 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
- 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 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
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical group C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 4
- 208000012931 Urologic disease Diseases 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 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 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
- 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 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
- 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 3
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 3
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 3
- 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 2
- 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
- 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
- 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
- BAXFDSRVKTZJDJ-FQEVSTJZSA-N (2s)-2-[[6-[4-[(3,5-difluorophenyl)methoxy]phenyl]pyrimidin-4-yl]amino]hexanoic acid Chemical compound C1=NC(N[C@@H](CCCC)C(O)=O)=CC(C=2C=CC(OCC=3C=C(F)C=C(F)C=3)=CC=2)=N1 BAXFDSRVKTZJDJ-FQEVSTJZSA-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
- XDGNQXAMWWFMBC-QFIPXVFZSA-N (2s)-2-[[6-[4-[(3,5-dimethoxyphenyl)methoxy]phenyl]pyrimidin-4-yl]amino]hexanoic acid Chemical compound C1=NC(N[C@@H](CCCC)C(O)=O)=CC(C=2C=CC(OCC=3C=C(OC)C=C(OC)C=3)=CC=2)=N1 XDGNQXAMWWFMBC-QFIPXVFZSA-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
- FNNPJWTZQROXCR-NRFANRHFSA-N (2s)-2-[[6-[4-[(3-methoxyphenyl)methoxy]phenyl]pyrimidin-4-yl]amino]hexanoic acid Chemical compound C1=NC(N[C@@H](CCCC)C(O)=O)=CC(C=2C=CC(OCC=3C=C(OC)C=CC=3)=CC=2)=N1 FNNPJWTZQROXCR-NRFANRHFSA-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
- 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 description 2
- 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 description 2
- 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 description 2
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- 241001465754 Metazoa Species 0.000 claims description 2
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- 125000003705 anilinocarbonyl group Chemical group O=C([*])N([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000006639 cyclohexyl carbonyl group Chemical group 0.000 claims description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 1
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims 1
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims 1
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- CRVRWEQIJGJUJV-DEOSSOPVSA-N methyl (2s)-2-[[6-[4-(benzenesulfonamido)phenyl]pyrimidin-4-yl]amino]-3-phenylpropanoate Chemical compound C([C@@H](C(=O)OC)NC=1N=CN=C(C=1)C=1C=CC(NS(=O)(=O)C=2C=CC=CC=2)=CC=1)C1=CC=CC=C1 CRVRWEQIJGJUJV-DEOSSOPVSA-N 0.000 description 1
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Classifications
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- 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
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- 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
-
- 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
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- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
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- C—CHEMISTRY; METALLURGY
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- 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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- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- 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
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—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
- 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
- C07D241/20—Nitrogen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—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
- 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
- C07D261/14—Nitrogen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—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
- 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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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D401/10—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 linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D401/12—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 linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/10—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
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- Life Sciences & Earth Sciences (AREA)
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- Bioinformatics & Cheminformatics (AREA)
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- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
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- Urology & Nephrology (AREA)
- Pulmonology (AREA)
- Diabetes (AREA)
- Pain & Pain Management (AREA)
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- Rheumatology (AREA)
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- Pregnancy & Childbirth (AREA)
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- 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)
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Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
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| EP02025024.7 | 2002-11-11 | ||
| EP02025024 | 2002-11-11 | ||
| EP03011397.1 | 2003-05-20 | ||
| EP03011397 | 2003-05-20 | ||
| PCT/EP2003/011976 WO2004043926A1 (en) | 2002-11-11 | 2003-10-29 | Phenyl or heteroaryl amino alkane derivatives as ip receptor antagonist |
Publications (1)
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| AU2003276201A1 true AU2003276201A1 (en) | 2004-06-03 |
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Family Applications (1)
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| AU2003276201A Abandoned AU2003276201A1 (en) | 2002-11-11 | 2003-10-29 | Phenyl or heteroaryl amino alkane derivatives as ip receptor antagonist |
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| US (1) | US20060089371A1 (OSRAM) |
| EP (1) | EP1575919A1 (OSRAM) |
| JP (1) | JP2006514110A (OSRAM) |
| KR (1) | KR20050074571A (OSRAM) |
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| AU (1) | AU2003276201A1 (OSRAM) |
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| CA (1) | CA2505361A1 (OSRAM) |
| CO (1) | CO5580824A2 (OSRAM) |
| EC (1) | ECSP055789A (OSRAM) |
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| HR (1) | HRP20050529A2 (OSRAM) |
| MA (1) | MA27491A1 (OSRAM) |
| NO (1) | NO20052797L (OSRAM) |
| PE (1) | PE20040672A1 (OSRAM) |
| PL (1) | PL376993A1 (OSRAM) |
| TW (1) | TW200418799A (OSRAM) |
| UY (1) | UY28072A1 (OSRAM) |
| WO (1) | WO2004043926A1 (OSRAM) |
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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)
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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 |
| 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 |
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- 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
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- 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
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2005
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- 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 |
| KR20050074571A (ko) | 2005-07-18 |
| 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 |
| 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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