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 (https=) | 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 (https=) |
| EP (1) | EP1809282B1 (https=) |
| JP (1) | JP4931823B2 (https=) |
| KR (1) | KR20070073791A (https=) |
| CN (1) | CN101389335A (https=) |
| AU (1) | AU2005295441B2 (https=) |
| BR (1) | BRPI0516609A (https=) |
| CA (1) | CA2583217C (https=) |
| EA (1) | EA012181B1 (https=) |
| ES (1) | ES2400689T3 (https=) |
| IL (1) | IL182203A0 (https=) |
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| MX (1) | MX2007004551A (https=) |
| WO (1) | WO2006044860A2 (https=) |
| ZA (1) | ZA200703975B (https=) |
Families Citing this family (47)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1809282B1 (en) | 2004-10-18 | 2013-01-09 | Amgen, Inc | Thiadiazole compounds and methods of use |
| WO2007007054A1 (en) * | 2005-07-08 | 2007-01-18 | Cancer Research Technology Limited | Phthalamides, succinimides and related compounds and their use as pharmaceuticals |
| WO2007084391A2 (en) * | 2006-01-18 | 2007-07-26 | Amgen Inc. | Thiazole compounds as protein kinase b ( pkb) inhibitors |
| DE102006030479A1 (de) | 2006-07-01 | 2008-03-20 | Merck Patent Gmbh | Indazolderivate |
| US8492378B2 (en) | 2006-08-03 | 2013-07-23 | Takeda Pharmaceutical Company Limited | GSK-3β inhibitor |
| DE102007002717A1 (de) | 2007-01-18 | 2008-07-24 | Merck Patent Gmbh | Heterocyclische Indazolderivate |
| DE102007022565A1 (de) | 2007-05-14 | 2008-11-20 | Merck Patent Gmbh | Heterocyclische Indazolderivate |
| US8648069B2 (en) | 2007-06-08 | 2014-02-11 | Abbvie Inc. | 5-substituted indazoles as kinase inhibitors |
| US7919504B2 (en) * | 2007-07-17 | 2011-04-05 | Amgen Inc. | Thiadiazole modulators of PKB |
| EP2173728A2 (en) * | 2007-07-17 | 2010-04-14 | Amgen Inc. | Heterocyclic modulators of pkb |
| DE102008038222A1 (de) | 2008-08-18 | 2010-02-25 | Merck Patent Gmbh | Indazol-5-carbonsäurehydrazid-derivate |
| DE102008038221A1 (de) | 2008-08-18 | 2010-02-25 | Merck Patent Gmbh | 7-Azaindolderivate |
| DE102008038220A1 (de) | 2008-08-18 | 2010-02-25 | Merck Patent Gmbh | Oxadiazolderivate |
| EP2387570A1 (en) * | 2009-01-15 | 2011-11-23 | Amgen, Inc | Fluoroisoquinoline substituted thiazole compounds and methods of use |
| JO2998B1 (ar) | 2010-06-04 | 2016-09-05 | Amgen Inc | مشتقات بيبيريدينون كمثبطات mdm2 لعلاج السرطان |
| US9376425B2 (en) | 2011-09-27 | 2016-06-28 | Amgen, Inc. | Heterocyclic compounds as MDM2 inhibitors for the treatment of cancer |
| US8729263B2 (en) | 2012-08-13 | 2014-05-20 | Novartis Ag | 1,4-disubstituted pyridazine analogs there of and methods for treating SMN-deficiency-related conditions |
| US9040712B2 (en) | 2013-01-23 | 2015-05-26 | Novartis Ag | Thiadiazole analogs thereof and methods for treating SMN-deficiency-related-conditions |
| WO2014130470A1 (en) | 2013-02-19 | 2014-08-28 | Amgen Inc. | Cis-morpholinone and other compounds as mdm2 inhibitors for the treatment of cancer |
| MX374513B (es) | 2013-03-14 | 2025-03-06 | Amgen Inc | Compuestos de morfolinona de ácido heteroarilo como inhibidores mdm2 para el tratamiento de cáncer. |
| CN105358530A (zh) | 2013-06-10 | 2016-02-24 | 美国安进公司 | 制备mdm2抑制剂的方法及其结晶形式 |
| KR20210130843A (ko) | 2013-07-31 | 2021-11-01 | 노파르티스 아게 | 1,4-이치환된 피리다진 유사체 및 smn-결핍-관련 상태를 치료하기 위한 그의 용도 |
| BR112016010564A2 (pt) | 2013-11-11 | 2017-10-10 | Amgen Inc | terapia de combinação incluindo um inibidor de mdm2 e um ou mais agentes farmaceuticamente ativos para tratamento de cânceres |
| EA030730B1 (ru) | 2013-12-19 | 2018-09-28 | Идорсиа Фармасьютиклз Лтд | Антибактериальные производные 1h-индазола и 1h-индола |
| RU2624857C1 (ru) * | 2016-01-26 | 2017-07-07 | федеральное государственное бюджетное образовательное учреждение высшего образования "Санкт-Петербургская государственная химико-фармацевтическая академия" Министерства здравоохранения Российской Федерации (ФГБОУ ВО СПХФА Минздрава России) | Фармацевтическая композиция с противогрибковой активностью и способ ее получения |
| US20190060286A1 (en) | 2016-02-29 | 2019-02-28 | University Of Florida Research Foundation, Incorpo | Chemotherapeutic Methods |
| US11352328B2 (en) | 2016-07-12 | 2022-06-07 | Arisan Therapeutics Inc. | Heterocyclic compounds for the treatment of arenavirus |
| AU2018273356B2 (en) | 2017-05-22 | 2021-09-16 | Amgen Inc. | KRAS G12C inhibitors and methods of using the same |
| WO2019028440A1 (en) | 2017-08-04 | 2019-02-07 | Skyhawk Therapeutics, Inc. | METHODS AND COMPOSITIONS FOR MODULATING SPLICING |
| AU2018329920B2 (en) | 2017-09-08 | 2022-12-01 | Amgen Inc. | Inhibitors of KRAS G12C and methods of using the same |
| US10342786B2 (en) | 2017-10-05 | 2019-07-09 | Fulcrum Therapeutics, Inc. | P38 kinase inhibitors reduce DUX4 and downstream gene expression for the treatment of FSHD |
| BR112020006677A2 (pt) | 2017-10-05 | 2020-10-06 | Fulcrum Therapeutics, Inc. | uso de inibidores p38 para reduzir a expressão de dux4 |
| CA3098574A1 (en) | 2018-05-04 | 2019-11-07 | Amgen Inc. | Kras g12c inhibitors and methods of using the same |
| MX2020012204A (es) | 2018-06-11 | 2021-03-31 | Amgen Inc | Inhibidores de kras g12c para tratar el cáncer. |
| US11285156B2 (en) | 2018-06-12 | 2022-03-29 | Amgen Inc. | Substituted piperazines as KRAS G12C inhibitors |
| AU2019327555B2 (en) | 2018-08-31 | 2025-01-16 | Amgen, Inc. | Processes for preparing a MDM2 inhibitor |
| JP7377679B2 (ja) | 2018-11-19 | 2023-11-10 | アムジエン・インコーポレーテツド | がん治療のためのｋｒａｓｇ１２ｃ阻害剤及び１種以上の薬学的に活性な追加の薬剤を含む併用療法 |
| US12419865B2 (en) | 2018-12-06 | 2025-09-23 | Arisan Therapeutics Inc. | Compounds for the treatment of arenavirus infection |
| WO2020163248A1 (en) | 2019-02-04 | 2020-08-13 | Skyhawk Therapeutics, Inc. | Methods and compositions for modulating splicing |
| EP3920915A4 (en) | 2019-02-05 | 2022-10-05 | Skyhawk Therapeutics, Inc. | METHODS AND COMPOSITIONS FOR MODULATING SPLICE |
| CN114126613A (zh) | 2019-02-05 | 2022-03-01 | 斯基霍克疗法公司 | 用于调节剪接的方法和组合物 |
| CN113661162A (zh) | 2019-02-06 | 2021-11-16 | 斯基霍克疗法公司 | 用于调节剪接的方法和组合物 |
| WO2020163544A1 (en) | 2019-02-06 | 2020-08-13 | Skyhawk Therapeutics, Inc. | Methods and compositions for modulating splicing |
| EP3738593A1 (en) | 2019-05-14 | 2020-11-18 | Amgen, Inc | Dosing of kras inhibitor for treatment of cancers |
| WO2020236947A1 (en) | 2019-05-21 | 2020-11-26 | Amgen Inc. | Solid state forms |
| US20240139193A1 (en) | 2019-10-15 | 2024-05-02 | Amgen Inc. | Combination therapy of kras inhibitor and shp2 inhibitor for treatment of cancers |
| US20230028414A1 (en) | 2019-12-16 | 2023-01-26 | Amgen Inc. | Dosing regimen of kras g12c inhibitor |
Family Cites Families (53)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3452035A (en) * | 1966-12-23 | 1969-06-24 | American Cyanamid Co | 2 - amino - 5 - (5 - nitro - 1 - substituted-2 - imidazolyl) - 1,3,4 - thiadiazoles and oxadiazoles |
| US3904756A (en) * | 1966-12-23 | 1975-09-09 | American Cyanamid Co | Substituted nitroimidazolyl thiadiazoles and oxadiazoles as antibacterial agents and growth promoting compounds |
| US3991200A (en) * | 1974-04-25 | 1976-11-09 | American Cyanamid Company | Substituted nitroimidazolyl thiadiazoles and oxadiazoles as antibacterial agents and growth promoting compounds |
| US3666860A (en) | 1966-12-23 | 1972-05-30 | Gerald Berkelhammer | Substituted nitroimidazolylthiadiazoles and oxadiazoles as antiprotozoal agents |
| US3842174A (en) * | 1966-12-23 | 1974-10-15 | American Cyanamid Co | Substituted nitroimidazolylthiadiazoles and oxadiazoles as antiprotozoal agents |
| US3740434A (en) * | 1966-12-23 | 1973-06-19 | American Cyanamid Co | Substituted nitroimidazolylthiadiazoles and oxadiazoles as antiprotozoal agents |
| US3830924A (en) * | 1966-12-23 | 1974-08-20 | American Cyanamid Co | Substituted nitroimidazolyl-thiadiazoles as growth promoting agents |
| US3666830A (en) * | 1971-01-21 | 1972-05-30 | Gen Electric | Lead compound catalyzed siloxane resin system |
| US4086238A (en) * | 1976-06-21 | 1978-04-25 | Velsicol Chemical Corporation | 1-Thiadiazolyl-4-methoxymethyl-5-hydroxyimidazolidinones |
| DE2640601C2 (de) * | 1976-09-09 | 1985-11-28 | Agfa-Gevaert Ag, 5090 Leverkusen | Farbphotographisches Material mit 2-Äquivalent-Gelbkupplern |
| DE3407505A1 (de) | 1984-03-01 | 1985-09-05 | A. Nattermann & Cie GmbH, 5000 Köln | Neue benzothiazin-carbonsaeureamide mit antiarthritischer wirksamkeit |
| FR2572074B1 (fr) * | 1984-10-18 | 1987-07-17 | Sanofi Sa | Derives du thiadiazole actifs sur le systeme nerveux central, procede d'obtention et compositions pharmaceutiques les contenant |
| FR2636628B1 (fr) * | 1988-08-25 | 1990-12-28 | Sanofi Sa | Derives du thiadiazole-1,3,4, leur procede d'obtention et compositions pharmaceutiques en contenant |
| HUT69739A (en) | 1992-03-26 | 1995-09-28 | Dowelanco | Process for producing n-heterocyclic nitroanilines and fungicides containing the compounds |
| JPH08151364A (ja) * | 1994-02-18 | 1996-06-11 | Nissan Chem Ind Ltd | 含窒素環状化合物および除草剤 |
| AU5845096A (en) | 1995-05-31 | 1996-12-18 | Nissan Chemical Industries Ltd. | 5-pyrazolecarboxamide derivatives and plant disease control agent |
| US20050053594A1 (en) * | 1995-11-16 | 2005-03-10 | Dario Alessi | RAC-PK as a therapeutic agent or in diagnostics, screening method for agents and process for activating RAC-PK |
| JP2000502097A (ja) | 1995-12-20 | 2000-02-22 | メディカル、リサーチ、カウンシル | タンパク質合成の制御、および作用薬のスクリーニング法 |
| AU1924099A (en) | 1997-12-18 | 1999-07-05 | Lyonnaise Industrielle Pharmaceutique (Lipha) | Piperazine derivatives useful as hypoglycemic agents |
| WO1999035164A1 (en) * | 1998-01-09 | 1999-07-15 | Arizona Board Of Regents, A Body Corporate, Acting On Behalf Of Arizona State University | Anti-cryptococcal peptides |
| US6323315B1 (en) * | 1999-09-10 | 2001-11-27 | Basf Aktiengesellschaft | Dolastatin peptides |
| US6797820B2 (en) * | 1999-12-17 | 2004-09-28 | Vicuron Pharmaceuticals Inc. | Succinate compounds, compositions and methods of use and preparation |
| US6852752B2 (en) * | 1999-12-17 | 2005-02-08 | Vicuron Pharmaceuticals Inc. | Urea compounds, compositions and methods of use and preparation |
| EP1237862A1 (en) | 1999-12-17 | 2002-09-11 | Versicor, Inc. | Succinate compounds, compositions and methods of use and preparation |
| US6420400B1 (en) * | 2000-04-07 | 2002-07-16 | Kinetek Pharmaceuticals, Inc. | Antiproliferative 1,2,3-thiadiazole compounds |
| AR032653A1 (es) * | 2001-02-09 | 2003-11-19 | Telik Inc | Inhibidores heterociclicos del trasportador de glicina 2 composiciones farmaceuticas, uso y metodos. |
| US20040106540A1 (en) * | 2001-04-10 | 2004-06-03 | Barnett Stanley F | Method of treating cancer |
| FR2832713B1 (fr) * | 2001-11-23 | 2004-02-13 | Sanofi Synthelabo | Derives de 4-(1,3,4-thiadiazol-2-yl)-1,4-diazabicyclo[3.2.2] nonane, leur preparation et leur application en therapeutique |
| EP1496981A2 (en) | 2002-04-08 | 2005-01-19 | Merck & Co., Inc. | Method of treating cancer |
| RU2004135386A (ru) * | 2002-05-06 | 2005-07-20 | Вертекс Фармасьютикалз Инкорпорейтед (Us) | Тиадиазолы или оксадиазолы и их применение в качестве ингибиторов протеинкиназы jak |
| MXPA04010966A (es) | 2002-05-07 | 2005-01-25 | Neurosearch As | Derivados novedosos de biarilo diazabiciclico. |
| GB0218625D0 (en) | 2002-08-10 | 2002-09-18 | Astex Technology Ltd | Pharmaceutical compounds |
| EP1785425B1 (en) * | 2002-09-30 | 2009-03-25 | NeuroSearch A/S | 1,4-Diazabicycloalkane derivatives, their preparation and use |
| EP1410844A1 (en) * | 2002-10-15 | 2004-04-21 | Centre National De La Recherche Scientifique (Cnrs) | Silicon-based porous catalytic system for oligomerising light olefins |
| US20040102360A1 (en) * | 2002-10-30 | 2004-05-27 | Barnett Stanley F. | Combination therapy |
| AR043057A1 (es) * | 2002-10-30 | 2005-07-13 | Vertex Pharma | Compuestos derivados de piridintiazoles como inhibidores de la quinasa rock y otras proteinas quinasa |
| TWI335913B (en) | 2002-11-15 | 2011-01-11 | Vertex Pharma | Diaminotriazoles useful as inhibitors of protein kinases |
| US20050004186A1 (en) * | 2002-12-20 | 2005-01-06 | Pfizer Inc | MEK inhibiting compounds |
| CN1809354A (zh) | 2003-04-24 | 2006-07-26 | 麦克公司 | Akt活性抑制剂 |
| WO2005014554A1 (en) | 2003-08-08 | 2005-02-17 | Astex Therapeutics Limited | 1h-indazole-3-carboxamide compounds as mapkap kinase modulators |
| CA2536253A1 (en) | 2003-08-20 | 2005-03-03 | Vertex Pharmaceuticals Incorporated | Aminofurazan compounds useful as protein kinase inhibitors |
| EP1658072A4 (en) * | 2003-08-21 | 2009-03-25 | Pfizer Prod Inc | Compounds for the Treatment of Neurodegenerative Diseases |
| US20050143384A1 (en) * | 2003-10-30 | 2005-06-30 | Eric Sartori | Amide thiadiazole inhibitors of plasminogen activator inhibitor-1 |
| JP2007510667A (ja) | 2003-11-07 | 2007-04-26 | スミスクライン ビーチャム （コーク） リミテッド | 癌の治療法 |
| BRPI0508970A (pt) | 2004-03-19 | 2007-08-21 | Penn State Res Found | método combinatórios e composições para o tratamento de melanoma |
| US7232820B2 (en) * | 2004-04-01 | 2007-06-19 | Pfizer Inc | Thiadiazole-amine compounds for the treatment of neurodegenerative disorders |
| WO2005113762A1 (en) | 2004-05-18 | 2005-12-01 | Pfizer Products Inc. | CRYSTAL STRUCTURE OF PROTEIN KINASE B-α (AKT-1) AND USES THEREOF |
| EP1758920A1 (en) * | 2004-05-21 | 2007-03-07 | Mpex Pharmaceuticals, Inc. | Bacterial efflux pump inhibitors and methods of treating bacterial infections |
| JP2008506669A (ja) * | 2004-07-16 | 2008-03-06 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | 神経変性疾患の処置に適するピペリジン、ピペラジンもしくはモルホリンの二量体化合物またはそれらの７−員同族体 |
| EP1809282B1 (en) * | 2004-10-18 | 2013-01-09 | Amgen, Inc | Thiadiazole compounds and methods of use |
| ATE493415T1 (de) | 2004-10-20 | 2011-01-15 | Neurosearch As | Neue diazabizyklische arylderivate und medizinische verwendung dafür |
| WO2007084391A2 (en) | 2006-01-18 | 2007-07-26 | Amgen Inc. | Thiazole compounds as protein kinase b ( pkb) inhibitors |
| US20080242694A1 (en) | 2006-09-18 | 2008-10-02 | D Sidocky Neil R | Amino-substituted heterocycles, compositions thereof, and methods of treatment therewith |
-
2005
- 2005-10-18 EP EP05812533A patent/EP1809282B1/en not_active Expired - Lifetime
- 2005-10-18 US US11/251,846 patent/US7354944B2/en not_active Expired - Lifetime
- 2005-10-18 MX MX2007004551A patent/MX2007004551A/es active IP Right Grant
- 2005-10-18 WO PCT/US2005/037374 patent/WO2006044860A2/en not_active Ceased
- 2005-10-18 KR KR1020077008816A patent/KR20070073791A/ko not_active Ceased
- 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 EA EA200700886A patent/EA012181B1/ru not_active IP Right Cessation
- 2005-10-18 BR BRPI0516609-8A patent/BRPI0516609A/pt not_active IP Right Cessation
- 2005-10-18 ES ES05812533T patent/ES2400689T3/es not_active Expired - Lifetime
- 2005-10-18 AU AU2005295441A patent/AU2005295441B2/en not_active Ceased
- 2005-10-18 CN CNA2005800356937A patent/CN101389335A/zh active Pending
-
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 not_active Expired - Lifetime
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