JP2008516986A5 - - Google Patents
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- Publication number
- JP2008516986A5 JP2008516986A5 JP2007537015A JP2007537015A JP2008516986A5 JP 2008516986 A5 JP2008516986 A5 JP 2008516986A5 JP 2007537015 A JP2007537015 A JP 2007537015A JP 2007537015 A JP2007537015 A JP 2007537015A JP 2008516986 A5 JP2008516986 A5 JP 2008516986A5
- Authority
- JP
- Japan
- Prior art keywords
- thiadiazol
- indazol
- amino
- propyl
- amine
- 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.)
- Granted
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- -1 C 1 -C 6 alkyl Chemical group 0.000 claims description 14
- 150000001412 amines Chemical class 0.000 claims description 4
- CIYWRUPCUDLZQJ-SFHVURJKSA-N (2s)-1-n-(5-isoquinolin-6-yl-1,3,4-thiadiazol-2-yl)-3-(3-methoxyphenyl)propane-1,2-diamine Chemical compound COC1=CC=CC(C[C@H](N)CNC=2SC(=NN=2)C=2C=C3C=CN=CC3=CC=2)=C1 CIYWRUPCUDLZQJ-SFHVURJKSA-N 0.000 claims description 2
- MPVYGYCIQMIWIP-IBGZPJMESA-N (2s)-1-n-(5-isoquinolin-6-yl-1,3,4-thiadiazol-2-yl)-3-(3-methylphenyl)propane-1,2-diamine Chemical compound CC1=CC=CC(C[C@H](N)CNC=2SC(=NN=2)C=2C=C3C=CN=CC3=CC=2)=C1 MPVYGYCIQMIWIP-IBGZPJMESA-N 0.000 claims description 2
- SKWJYWSNFQTPIW-SFHVURJKSA-N (2s)-1-n-(5-isoquinolin-6-yl-1,3,4-thiadiazol-2-yl)-3-(4-methoxyphenyl)propane-1,2-diamine Chemical compound C1=CC(OC)=CC=C1C[C@H](N)CNC1=NN=C(C=2C=C3C=CN=CC3=CC=2)S1 SKWJYWSNFQTPIW-SFHVURJKSA-N 0.000 claims description 2
- UFFYOAWCSOACPD-SFHVURJKSA-N (2s)-1-n-(5-isoquinolin-6-yl-1,3,4-thiadiazol-2-yl)-3-[3-(trifluoromethyl)phenyl]propane-1,2-diamine Chemical compound C([C@@H](CNC=1SC(=NN=1)C=1C=C2C=CN=CC2=CC=1)N)C1=CC=CC(C(F)(F)F)=C1 UFFYOAWCSOACPD-SFHVURJKSA-N 0.000 claims description 2
- WZOVTPHXONVIIJ-SFHVURJKSA-N (2s)-1-n-(5-isoquinolin-6-yl-1,3,4-thiadiazol-2-yl)-3-[4-(trifluoromethyl)phenyl]propane-1,2-diamine Chemical compound C([C@@H](CNC=1SC(=NN=1)C=1C=C2C=CN=CC2=CC=1)N)C1=CC=C(C(F)(F)F)C=C1 WZOVTPHXONVIIJ-SFHVURJKSA-N 0.000 claims description 2
- AKPXLNAJRWSZJY-HNNXBMFYSA-N (2s)-1-n-[5-(1h-indazol-5-yl)-1,3,4-thiadiazol-2-yl]-3-(4-methoxyphenyl)propane-1,2-diamine Chemical compound C1=CC(OC)=CC=C1C[C@H](N)CNC1=NN=C(C=2C=C3C=NNC3=CC=2)S1 AKPXLNAJRWSZJY-HNNXBMFYSA-N 0.000 claims description 2
- JCNFACQBFPFBPG-SFHVURJKSA-N (2s)-1-n-[5-(1h-indazol-5-yl)-1,3,4-thiadiazol-2-yl]-3-(4-propan-2-ylphenyl)propane-1,2-diamine Chemical compound C1=CC(C(C)C)=CC=C1C[C@H](N)CNC1=NN=C(C=2C=C3C=NNC3=CC=2)S1 JCNFACQBFPFBPG-SFHVURJKSA-N 0.000 claims description 2
- OSHTXJHXSUZMOX-HNNXBMFYSA-N (2s)-1-n-[5-(1h-indazol-5-yl)-1,3,4-thiadiazol-2-yl]-3-[3-(trifluoromethyl)phenyl]propane-1,2-diamine Chemical compound C([C@@H](CNC=1SC(=NN=1)C=1C=C2C=NNC2=CC=1)N)C1=CC=CC(C(F)(F)F)=C1 OSHTXJHXSUZMOX-HNNXBMFYSA-N 0.000 claims description 2
- BRTIFMBVAUCZIX-HNNXBMFYSA-N (2s)-1-n-[5-(1h-indazol-5-yl)-1,3,4-thiadiazol-2-yl]-3-[4-(trifluoromethyl)phenyl]propane-1,2-diamine Chemical compound C([C@@H](CNC=1SC(=NN=1)C=1C=C2C=NNC2=CC=1)N)C1=CC=C(C(F)(F)F)C=C1 BRTIFMBVAUCZIX-HNNXBMFYSA-N 0.000 claims description 2
- VTWBUGFMCLNISB-IBGZPJMESA-N (2s)-1-n-[5-(1h-indazol-5-yl)-1,3,4-thiadiazol-2-yl]-3-naphthalen-2-ylpropane-1,2-diamine Chemical compound C1=CC=CC2=CC(C[C@@H](CNC=3SC(=NN=3)C=3C=C4C=NNC4=CC=3)N)=CC=C21 VTWBUGFMCLNISB-IBGZPJMESA-N 0.000 claims description 2
- MHOYBFWKTMXWPK-INIZCTEOSA-N (2s)-1-n-[5-(3-methyl-2h-indazol-5-yl)-1,3,4-thiadiazol-2-yl]-3-(2-methylphenyl)propane-1,2-diamine Chemical compound C([C@H](N)CNC1=NN=C(S1)C1=CC=C2NN=C(C2=C1)C)C1=CC=CC=C1C MHOYBFWKTMXWPK-INIZCTEOSA-N 0.000 claims description 2
- QOVXYSJPVFXJRF-INIZCTEOSA-N (2s)-1-n-[5-(3-methyl-2h-indazol-5-yl)-1,3,4-thiadiazol-2-yl]-3-(3-methylphenyl)propane-1,2-diamine Chemical compound C([C@H](N)CNC1=NN=C(S1)C1=CC=C2NN=C(C2=C1)C)C1=CC=CC(C)=C1 QOVXYSJPVFXJRF-INIZCTEOSA-N 0.000 claims description 2
- RJESZRNJZYVXEA-INIZCTEOSA-N (2s)-1-n-[5-(3-methyl-2h-indazol-5-yl)-1,3,4-thiadiazol-2-yl]-3-(4-methylphenyl)propane-1,2-diamine Chemical compound C([C@H](N)CNC1=NN=C(S1)C1=CC=C2NN=C(C2=C1)C)C1=CC=C(C)C=C1 RJESZRNJZYVXEA-INIZCTEOSA-N 0.000 claims description 2
- GATDANXASIBFTP-SFHVURJKSA-N (2s)-1-n-[5-(3-methyl-2h-indazol-5-yl)-1,3,4-thiadiazol-2-yl]-3-(4-propan-2-ylphenyl)propane-1,2-diamine Chemical compound C1=CC(C(C)C)=CC=C1C[C@H](N)CNC1=NN=C(C=2C=C3C(C)=NNC3=CC=2)S1 GATDANXASIBFTP-SFHVURJKSA-N 0.000 claims description 2
- GGQSOEXSCZITMC-HNNXBMFYSA-N (2s)-1-n-[5-(3-methyl-2h-indazol-5-yl)-1,3,4-thiadiazol-2-yl]-3-[3-(trifluoromethyl)phenyl]propane-1,2-diamine Chemical compound C([C@H](N)CNC1=NN=C(S1)C1=CC=C2NN=C(C2=C1)C)C1=CC=CC(C(F)(F)F)=C1 GGQSOEXSCZITMC-HNNXBMFYSA-N 0.000 claims description 2
- JBXAHSUTPSPXBN-IBGZPJMESA-N (2s)-1-n-[5-(3-methyl-2h-indazol-5-yl)-1,3,4-thiadiazol-2-yl]-3-naphthalen-2-ylpropane-1,2-diamine Chemical compound C1=CC=CC2=CC(C[C@H](N)CNC3=NN=C(S3)C3=CC=C4NN=C(C4=C3)C)=CC=C21 JBXAHSUTPSPXBN-IBGZPJMESA-N 0.000 claims description 2
- SUQRKPOSKOIDNI-AWEZNQCLSA-N (2s)-1-n-[5-(3-methyl-2h-pyrazolo[3,4-b]pyridin-5-yl)-1,3,4-thiadiazol-2-yl]-3-[3-(trifluoromethyl)phenyl]propane-1,2-diamine Chemical compound C([C@H](N)CNC1=NN=C(S1)C1=CN=C2NN=C(C2=C1)C)C1=CC=CC(C(F)(F)F)=C1 SUQRKPOSKOIDNI-AWEZNQCLSA-N 0.000 claims description 2
- IXYCOMDIYWCTHT-KRWDZBQOSA-N (2s)-3-(2,4-dichlorophenyl)-1-n-(5-isoquinolin-6-yl-1,3,4-thiadiazol-2-yl)propane-1,2-diamine Chemical compound C([C@@H](CNC=1SC(=NN=1)C=1C=C2C=CN=CC2=CC=1)N)C1=CC=C(Cl)C=C1Cl IXYCOMDIYWCTHT-KRWDZBQOSA-N 0.000 claims description 2
- QGBOALFDSLDKNK-AWEZNQCLSA-N (2s)-3-(2,4-dichlorophenyl)-1-n-[5-(1h-indazol-5-yl)-1,3,4-thiadiazol-2-yl]propane-1,2-diamine Chemical compound C([C@@H](CNC=1SC(=NN=1)C=1C=C2C=NNC2=CC=1)N)C1=CC=C(Cl)C=C1Cl QGBOALFDSLDKNK-AWEZNQCLSA-N 0.000 claims description 2
- ZJVCNOOQHUYJRJ-AWEZNQCLSA-N (2s)-3-(2,4-dichlorophenyl)-1-n-[5-(3-methyl-2h-indazol-5-yl)-1,3,4-thiadiazol-2-yl]propane-1,2-diamine Chemical compound C([C@H](N)CNC1=NN=C(S1)C1=CC=C2NN=C(C2=C1)C)C1=CC=C(Cl)C=C1Cl ZJVCNOOQHUYJRJ-AWEZNQCLSA-N 0.000 claims description 2
- LNUQTGZAAJAREX-AWEZNQCLSA-N (2s)-3-(2-bromophenyl)-1-n-[5-(3-methyl-2h-indazol-5-yl)-1,3,4-thiadiazol-2-yl]propane-1,2-diamine Chemical compound C([C@H](N)CNC1=NN=C(S1)C1=CC=C2NN=C(C2=C1)C)C1=CC=CC=C1Br LNUQTGZAAJAREX-AWEZNQCLSA-N 0.000 claims description 2
- MEXRTWCANVVSBH-AWEZNQCLSA-N (2s)-3-(2-chlorophenyl)-1-n-[5-(3-methyl-2h-indazol-5-yl)-1,3,4-thiadiazol-2-yl]propane-1,2-diamine Chemical compound C([C@H](N)CNC1=NN=C(S1)C1=CC=C2NN=C(C2=C1)C)C1=CC=CC=C1Cl MEXRTWCANVVSBH-AWEZNQCLSA-N 0.000 claims description 2
- HWNFHXRWNZRYDL-HNNXBMFYSA-N (2s)-3-(2-methoxyphenyl)-1-n-[5-(3-methyl-2h-indazol-5-yl)-1,3,4-thiadiazol-2-yl]propane-1,2-diamine Chemical compound COC1=CC=CC=C1C[C@H](N)CNC1=NN=C(C=2C=C3C(C)=NNC3=CC=2)S1 HWNFHXRWNZRYDL-HNNXBMFYSA-N 0.000 claims description 2
- UDIXICAWQICGPN-ZDUSSCGKSA-N (2s)-3-(3,4-dichlorophenyl)-1-n-[5-(1h-indazol-5-yl)-1,3,4-thiadiazol-2-yl]propane-1,2-diamine Chemical compound C([C@@H](CNC=1SC(=NN=1)C=1C=C2C=NNC2=CC=1)N)C1=CC=C(Cl)C(Cl)=C1 UDIXICAWQICGPN-ZDUSSCGKSA-N 0.000 claims description 2
- BKIUGHHFPOHSFU-ZDUSSCGKSA-N (2s)-3-(3,4-dichlorophenyl)-1-n-[5-(3-methyl-2h-indazol-5-yl)-1,3,4-thiadiazol-2-yl]propane-1,2-diamine Chemical compound C([C@H](N)CNC1=NN=C(S1)C1=CC=C2NN=C(C2=C1)C)C1=CC=C(Cl)C(Cl)=C1 BKIUGHHFPOHSFU-ZDUSSCGKSA-N 0.000 claims description 2
- NQKAFIFFMXPFFK-ZDUSSCGKSA-N (2s)-3-(3,4-difluorophenyl)-1-n-[5-(3-methyl-2h-indazol-5-yl)-1,3,4-thiadiazol-2-yl]propane-1,2-diamine Chemical compound C([C@H](N)CNC1=NN=C(S1)C1=CC=C2NN=C(C2=C1)C)C1=CC=C(F)C(F)=C1 NQKAFIFFMXPFFK-ZDUSSCGKSA-N 0.000 claims description 2
- WLUVOFFSQYABAV-SFHVURJKSA-N (2s)-3-(3,5-difluorophenyl)-1-n-(5-isoquinolin-6-yl-1,3,4-thiadiazol-2-yl)propane-1,2-diamine Chemical compound C([C@@H](CNC=1SC(=NN=1)C=1C=C2C=CN=CC2=CC=1)N)C1=CC(F)=CC(F)=C1 WLUVOFFSQYABAV-SFHVURJKSA-N 0.000 claims description 2
- WGKWUIDLGLLSSD-HNNXBMFYSA-N (2s)-3-(3,5-difluorophenyl)-1-n-[5-(3-methyl-2h-indazol-5-yl)-1,3,4-thiadiazol-2-yl]propane-1,2-diamine Chemical class C([C@H](N)CNC1=NN=C(S1)C1=CC=C2NN=C(C2=C1)C)C1=CC(F)=CC(F)=C1 WGKWUIDLGLLSSD-HNNXBMFYSA-N 0.000 claims description 2
- BDYKWAPSVQOKEM-HNNXBMFYSA-N (2s)-3-(3-bromophenyl)-1-n-[5-(3-methyl-2h-indazol-5-yl)-1,3,4-thiadiazol-2-yl]propane-1,2-diamine Chemical compound C([C@H](N)CNC1=NN=C(S1)C1=CC=C2NN=C(C2=C1)C)C1=CC=CC(Br)=C1 BDYKWAPSVQOKEM-HNNXBMFYSA-N 0.000 claims description 2
- HHNFRVFYHNQUPY-HNNXBMFYSA-N (2s)-3-(3-chlorophenyl)-1-n-[5-(3-methyl-2h-indazol-5-yl)-1,3,4-thiadiazol-2-yl]propane-1,2-diamine Chemical compound C([C@H](N)CNC1=NN=C(S1)C1=CC=C2NN=C(C2=C1)C)C1=CC=CC(Cl)=C1 HHNFRVFYHNQUPY-HNNXBMFYSA-N 0.000 claims description 2
- GJYYNOOZSHSFLL-HNNXBMFYSA-N (2s)-3-(3-fluorophenyl)-1-n-[5-(3-methyl-2h-indazol-5-yl)-1,3,4-thiadiazol-2-yl]propane-1,2-diamine Chemical compound C([C@H](N)CNC1=NN=C(S1)C1=CC=C2NN=C(C2=C1)C)C1=CC=CC(F)=C1 GJYYNOOZSHSFLL-HNNXBMFYSA-N 0.000 claims description 2
- WUJAVWRRJCESGL-HNNXBMFYSA-N (2s)-3-(4-bromophenyl)-1-n-[5-(1h-indazol-5-yl)-1,3,4-thiadiazol-2-yl]propane-1,2-diamine Chemical compound C([C@@H](CNC=1SC(=NN=1)C=1C=C2C=NNC2=CC=1)N)C1=CC=C(Br)C=C1 WUJAVWRRJCESGL-HNNXBMFYSA-N 0.000 claims description 2
- ONUGNDNQFFQLIQ-HNNXBMFYSA-N (2s)-3-(4-bromophenyl)-1-n-[5-(3-methyl-2h-indazol-5-yl)-1,3,4-thiadiazol-2-yl]propane-1,2-diamine Chemical compound C([C@H](N)CNC1=NN=C(S1)C1=CC=C2NN=C(C2=C1)C)C1=CC=C(Br)C=C1 ONUGNDNQFFQLIQ-HNNXBMFYSA-N 0.000 claims description 2
- NHCKWRFRGQYSQI-HNNXBMFYSA-N (2s)-3-(4-chlorophenyl)-1-n-[5-(1h-indazol-5-yl)-1,3,4-thiadiazol-2-yl]propane-1,2-diamine Chemical compound C([C@@H](CNC=1SC(=NN=1)C=1C=C2C=NNC2=CC=1)N)C1=CC=C(Cl)C=C1 NHCKWRFRGQYSQI-HNNXBMFYSA-N 0.000 claims description 2
- VFMSDTSKEUYQCV-HNNXBMFYSA-N (2s)-3-(4-chlorophenyl)-1-n-[5-(3-methyl-2h-indazol-5-yl)-1,3,4-thiadiazol-2-yl]propane-1,2-diamine Chemical compound C([C@H](N)CNC1=NN=C(S1)C1=CC=C2NN=C(C2=C1)C)C1=CC=C(Cl)C=C1 VFMSDTSKEUYQCV-HNNXBMFYSA-N 0.000 claims description 2
- KGPGGEAIINZPGB-KRWDZBQOSA-N (2s)-3-(4-ethylphenyl)-1-n-[5-(3-methyl-2h-indazol-5-yl)-1,3,4-thiadiazol-2-yl]propane-1,2-diamine Chemical compound C1=CC(CC)=CC=C1C[C@H](N)CNC1=NN=C(C=2C=C3C(C)=NNC3=CC=2)S1 KGPGGEAIINZPGB-KRWDZBQOSA-N 0.000 claims description 2
- DAVGDRIAVUPUIO-HNNXBMFYSA-N (2s)-3-(4-fluorophenyl)-1-n-[5-(3-methyl-2h-indazol-5-yl)-1,3,4-thiadiazol-2-yl]propane-1,2-diamine Chemical compound C([C@H](N)CNC1=NN=C(S1)C1=CC=C2NN=C(C2=C1)C)C1=CC=C(F)C=C1 DAVGDRIAVUPUIO-HNNXBMFYSA-N 0.000 claims description 2
- LTZPKHBMMKQKEQ-HNNXBMFYSA-N (2s)-3-(4-methoxyphenyl)-1-n-[5-(3-methyl-2h-indazol-5-yl)-1,3,4-thiadiazol-2-yl]propane-1,2-diamine Chemical compound C1=CC(OC)=CC=C1C[C@H](N)CNC1=NN=C(C=2C=C3C(C)=NNC3=CC=2)S1 LTZPKHBMMKQKEQ-HNNXBMFYSA-N 0.000 claims description 2
- OKMSQBGAVTWSMQ-ORAYPTAESA-N (2s,3s)-1-n-(5-isoquinolin-6-yl-1,3,4-thiadiazol-2-yl)-3-[4-(trifluoromethyl)phenyl]butane-1,2-diamine Chemical compound C1([C@@H]([C@H](N)CNC=2SC(=NN=2)C=2C=C3C=CN=CC3=CC=2)C)=CC=C(C(F)(F)F)C=C1 OKMSQBGAVTWSMQ-ORAYPTAESA-N 0.000 claims description 2
- CNPURSDMOWDNOQ-UHFFFAOYSA-N 4-methoxy-7h-pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound COC1=NC(N)=NC2=C1C=CN2 CNPURSDMOWDNOQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 11
- 125000003118 aryl group Chemical group 0.000 claims 9
- 125000000623 heterocyclic group Chemical group 0.000 claims 9
- 150000001875 compounds Chemical class 0.000 claims 6
- 229910052799 carbon Inorganic materials 0.000 claims 5
- 239000008194 pharmaceutical composition Substances 0.000 claims 5
- 150000003839 salts Chemical class 0.000 claims 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 125000005843 halogen group Chemical group 0.000 claims 3
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 230000001404 mediated effect Effects 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- RFPGTVPPSYVZOU-SFHVURJKSA-N (2s)-3-(4-chlorophenyl)-1-n-(5-isoquinolin-6-yl-1,3,4-thiadiazol-2-yl)propane-1,2-diamine Chemical compound C([C@@H](CNC=1SC(=NN=1)C=1C=C2C=CN=CC2=CC=1)N)C1=CC=C(Cl)C=C1 RFPGTVPPSYVZOU-SFHVURJKSA-N 0.000 claims 1
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 1
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 1
- 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims 1
- ZNEYXIQCZSZWHZ-UHFFFAOYSA-N 5-(3-methyl-2h-indazol-5-yl)-1,3,4-thiadiazol-2-amine Chemical class C1=C2C(C)=NNC2=CC=C1C1=NN=C(N)S1 ZNEYXIQCZSZWHZ-UHFFFAOYSA-N 0.000 claims 1
- HOSGXJWQVBHGLT-UHFFFAOYSA-N 6-hydroxy-3,4-dihydro-1h-quinolin-2-one Chemical group N1C(=O)CCC2=CC(O)=CC=C21 HOSGXJWQVBHGLT-UHFFFAOYSA-N 0.000 claims 1
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 1
- 241000124008 Mammalia Species 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 108091000080 Phosphotransferase Proteins 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 125000002837 carbocyclic group Chemical group 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000036571 hydration Effects 0.000 claims 1
- 238000006703 hydration reaction Methods 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 102000020233 phosphotransferase Human genes 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 229940124597 therapeutic agent Drugs 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- OZRBMKPJQPZFEV-INIZCTEOSA-N (2s)-3-(4-chlorophenyl)-2-n-methyl-1-n-[5-(3-methyl-2h-indazol-5-yl)-1,3,4-thiadiazol-2-yl]propane-1,2-diamine Chemical class C([C@@H](CNC=1SC(=NN=1)C=1C=C2C(C)=NNC2=CC=1)NC)C1=CC=C(Cl)C=C1 OZRBMKPJQPZFEV-INIZCTEOSA-N 0.000 description 1
- 238000004252 FT/ICR mass spectrometry Methods 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US61901004P | 2004-10-18 | 2004-10-18 | |
| US60/619,010 | 2004-10-18 | ||
| PCT/US2005/037374 WO2006044860A2 (en) | 2004-10-18 | 2005-10-18 | Thiadiazole compounds and methods of use |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2008516986A JP2008516986A (ja) | 2008-05-22 |
| JP2008516986A5 true JP2008516986A5 (enExample) | 2008-11-20 |
| JP4931823B2 JP4931823B2 (ja) | 2012-05-16 |
Family
ID=36203652
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007537015A Expired - Fee Related JP4931823B2 (ja) | 2004-10-18 | 2005-10-18 | チアジアゾール化合物及び使用方法 |
Country Status (15)
| Country | Link |
|---|---|
| US (3) | US7354944B2 (enExample) |
| EP (1) | EP1809282B1 (enExample) |
| JP (1) | JP4931823B2 (enExample) |
| KR (1) | KR20070073791A (enExample) |
| CN (1) | CN101389335A (enExample) |
| AU (1) | AU2005295441B2 (enExample) |
| BR (1) | BRPI0516609A (enExample) |
| CA (1) | CA2583217C (enExample) |
| EA (1) | EA012181B1 (enExample) |
| ES (1) | ES2400689T3 (enExample) |
| IL (1) | IL182203A0 (enExample) |
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-
2005
- 2005-10-18 EP EP05812533A patent/EP1809282B1/en not_active Expired - Lifetime
- 2005-10-18 ES ES05812533T patent/ES2400689T3/es not_active Expired - Lifetime
- 2005-10-18 JP JP2007537015A patent/JP4931823B2/ja not_active Expired - Fee Related
- 2005-10-18 CA CA2583217A patent/CA2583217C/en not_active Expired - Fee Related
- 2005-10-18 US US11/251,846 patent/US7354944B2/en not_active Expired - Lifetime
- 2005-10-18 AU AU2005295441A patent/AU2005295441B2/en not_active Ceased
- 2005-10-18 KR KR1020077008816A patent/KR20070073791A/ko not_active Ceased
- 2005-10-18 MX MX2007004551A patent/MX2007004551A/es active IP Right Grant
- 2005-10-18 CN CNA2005800356937A patent/CN101389335A/zh active Pending
- 2005-10-18 EA EA200700886A patent/EA012181B1/ru not_active IP Right Cessation
- 2005-10-18 WO PCT/US2005/037374 patent/WO2006044860A2/en not_active Ceased
- 2005-10-18 BR BRPI0516609-8A patent/BRPI0516609A/pt not_active IP Right Cessation
-
2007
- 2007-03-26 IL IL182203A patent/IL182203A0/en unknown
- 2007-05-16 ZA ZA200703975A patent/ZA200703975B/xx unknown
- 2007-05-17 MA MA29916A patent/MA29029B1/fr unknown
-
2008
- 2008-03-19 US US12/077,633 patent/US7919514B2/en active Active
- 2008-03-19 US US12/077,634 patent/US7700636B2/en active Active
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