JP2009503107A5 - - Google Patents
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- JP2009503107A5 JP2009503107A5 JP2008525195A JP2008525195A JP2009503107A5 JP 2009503107 A5 JP2009503107 A5 JP 2009503107A5 JP 2008525195 A JP2008525195 A JP 2008525195A JP 2008525195 A JP2008525195 A JP 2008525195A JP 2009503107 A5 JP2009503107 A5 JP 2009503107A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- chloro
- alkyl
- thiazol
- carboxylic acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- 125000000217 alkyl group Chemical group 0.000 claims 32
- 150000003839 salts Chemical class 0.000 claims 18
- 229910052736 halogen Inorganic materials 0.000 claims 13
- 150000002367 halogens Chemical class 0.000 claims 13
- 150000001875 compounds Chemical class 0.000 claims 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims 12
- 125000001188 haloalkyl group Chemical group 0.000 claims 12
- -1 thiocarbamoyl Chemical group 0.000 claims 10
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 9
- 125000003545 alkoxy group Chemical group 0.000 claims 8
- 125000001589 carboacyl group Chemical group 0.000 claims 8
- 125000004438 haloalkoxy group Chemical group 0.000 claims 8
- 125000005024 alkenyl aryl group Chemical group 0.000 claims 7
- 125000002877 alkyl aryl group Chemical group 0.000 claims 7
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims 7
- 125000003118 aryl group Chemical group 0.000 claims 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 7
- 125000001072 heteroaryl group Chemical group 0.000 claims 7
- 239000008194 pharmaceutical composition Substances 0.000 claims 7
- 239000012453 solvate Substances 0.000 claims 7
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 6
- 201000010099 disease Diseases 0.000 claims 6
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 6
- 125000002252 acyl group Chemical group 0.000 claims 5
- 125000003342 alkenyl group Chemical group 0.000 claims 5
- 125000000304 alkynyl group Chemical group 0.000 claims 5
- 125000004103 aminoalkyl group Chemical group 0.000 claims 5
- 125000003435 aroyl group Chemical group 0.000 claims 5
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 5
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims 5
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims 5
- 125000004663 dialkyl amino group Chemical group 0.000 claims 5
- 125000005117 dialkylcarbamoyl group Chemical group 0.000 claims 5
- 125000004404 heteroalkyl group Chemical group 0.000 claims 5
- 125000000623 heterocyclic group Chemical group 0.000 claims 5
- 125000004043 oxo group Chemical group O=* 0.000 claims 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 4
- 239000003937 drug carrier Substances 0.000 claims 4
- 239000003981 vehicle Substances 0.000 claims 4
- 201000004681 Psoriasis Diseases 0.000 claims 3
- 239000004480 active ingredient Substances 0.000 claims 3
- 239000012752 auxiliary agent Substances 0.000 claims 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- JOMOAMJPPUFTSI-UHFFFAOYSA-N 4-(4-chlorophenyl)-1,3-thiazole-2-carboxylic acid Chemical compound S1C(C(=O)O)=NC(C=2C=CC(Cl)=CC=2)=C1 JOMOAMJPPUFTSI-UHFFFAOYSA-N 0.000 claims 2
- ZDRVLAOYDGQLFI-UHFFFAOYSA-N 4-[[4-(4-chlorophenyl)-1,3-thiazol-2-yl]amino]phenol;hydrochloride Chemical compound Cl.C1=CC(O)=CC=C1NC1=NC(C=2C=CC(Cl)=CC=2)=CS1 ZDRVLAOYDGQLFI-UHFFFAOYSA-N 0.000 claims 2
- 201000001320 Atherosclerosis Diseases 0.000 claims 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 206010038933 Retinopathy of prematurity Diseases 0.000 claims 2
- 230000033115 angiogenesis Effects 0.000 claims 2
- 206010003246 arthritis Diseases 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 230000003463 hyperproliferative effect Effects 0.000 claims 2
- 208000027866 inflammatory disease Diseases 0.000 claims 2
- 108010035597 sphingosine kinase Proteins 0.000 claims 2
- XXZQDEHSQNRYCH-UHFFFAOYSA-N 1-(1,3-benzothiazol-2-yl)-3-[4-chloro-3-(trifluoromethyl)phenyl]urea Chemical compound C1=C(Cl)C(C(F)(F)F)=CC(NC(=O)NC=2SC3=CC=CC=C3N=2)=C1 XXZQDEHSQNRYCH-UHFFFAOYSA-N 0.000 claims 1
- DGLLHELENVMDCN-UHFFFAOYSA-N 1-(5-chloro-1,3-benzoxazol-2-yl)-3-[4-chloro-3-(trifluoromethyl)phenyl]urea Chemical compound C1=C(Cl)C(C(F)(F)F)=CC(NC(=O)NC=2OC3=CC=C(Cl)C=C3N=2)=C1 DGLLHELENVMDCN-UHFFFAOYSA-N 0.000 claims 1
- AXFYUQKIYMVFPR-UHFFFAOYSA-N 1-[4-(4-chlorophenyl)-1,3-thiazol-2-yl]-3-[4-chloro-3-(trifluoromethyl)phenyl]urea Chemical compound C1=C(Cl)C(C(F)(F)F)=CC(NC(=O)NC=2SC=C(N=2)C=2C=CC(Cl)=CC=2)=C1 AXFYUQKIYMVFPR-UHFFFAOYSA-N 0.000 claims 1
- OECHURISVRKTLG-UHFFFAOYSA-N 2,4-dichloro-n-[4-(4-chlorophenyl)-1,3-thiazol-2-yl]benzamide Chemical compound C1=CC(Cl)=CC=C1C1=CSC(NC(=O)C=2C(=CC(Cl)=CC=2)Cl)=N1 OECHURISVRKTLG-UHFFFAOYSA-N 0.000 claims 1
- NLTOQIMGHXWPMK-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-yl)-n-[4-(4-chlorophenyl)-1,3-thiazol-2-yl]acetamide Chemical compound C1=CC(Cl)=CC=C1C1=CSC(NC(=O)CC=2C=C3OCOC3=CC=2)=N1 NLTOQIMGHXWPMK-UHFFFAOYSA-N 0.000 claims 1
- JHVALSRTUOVNLL-UHFFFAOYSA-N 2-(3-bromo-4-methoxyphenyl)ethanamine Chemical compound COC1=CC=C(CCN)C=C1Br JHVALSRTUOVNLL-UHFFFAOYSA-N 0.000 claims 1
- CFXGLQURELTJPS-UHFFFAOYSA-N 2-chloro-n-[4-(4-chlorophenyl)-1,3-thiazol-2-yl]-2-phenylacetamide Chemical compound C=1C=CC=CC=1C(Cl)C(=O)NC(SC=1)=NC=1C1=CC=C(Cl)C=C1 CFXGLQURELTJPS-UHFFFAOYSA-N 0.000 claims 1
- MKEWYPDSJFOTDY-UHFFFAOYSA-N 3-(1,3-benzodioxol-5-yl)-n-[4-(4-chlorophenyl)-1,3-thiazol-2-yl]prop-2-enamide Chemical compound C1=CC(Cl)=CC=C1C1=CSC(NC(=O)C=CC=2C=C3OCOC3=CC=2)=N1 MKEWYPDSJFOTDY-UHFFFAOYSA-N 0.000 claims 1
- NMNPWVCDFOCDQH-UHFFFAOYSA-N 3-(4-chlorophenyl)-n-(1-methylpiperidin-4-yl)benzamide Chemical compound C1CN(C)CCC1NC(=O)C1=CC=CC(C=2C=CC(Cl)=CC=2)=C1 NMNPWVCDFOCDQH-UHFFFAOYSA-N 0.000 claims 1
- WLJSOFDFVHVTOM-UHFFFAOYSA-N 3-(4-chlorophenyl)-n-(2-pyridin-4-ylethyl)benzamide Chemical compound C1=CC(Cl)=CC=C1C1=CC=CC(C(=O)NCCC=2C=CN=CC=2)=C1 WLJSOFDFVHVTOM-UHFFFAOYSA-N 0.000 claims 1
- GHBZMRXTLNSNRV-UHFFFAOYSA-N 3-(4-chlorophenyl)-n-(4-hydroxyphenyl)benzamide Chemical compound C1=CC(O)=CC=C1NC(=O)C1=CC=CC(C=2C=CC(Cl)=CC=2)=C1 GHBZMRXTLNSNRV-UHFFFAOYSA-N 0.000 claims 1
- ZOVNKLPTYAKFKG-UHFFFAOYSA-N 3-(4-chlorophenyl)-n-(pyridin-4-ylmethyl)benzamide Chemical compound C1=CC(Cl)=CC=C1C1=CC=CC(C(=O)NCC=2C=CN=CC=2)=C1 ZOVNKLPTYAKFKG-UHFFFAOYSA-N 0.000 claims 1
- SUBHPZIAKSTONB-UHFFFAOYSA-N 3-(4-chlorophenyl)-n-[2-(1-methylpyrrolidin-2-yl)ethyl]benzamide Chemical compound CN1CCCC1CCNC(=O)C1=CC=CC(C=2C=CC(Cl)=CC=2)=C1 SUBHPZIAKSTONB-UHFFFAOYSA-N 0.000 claims 1
- KVLXOQWRFPIDSA-UHFFFAOYSA-N 4-(4-chlorophenyl)-n,n-bis(3-phenylpropyl)-1,3-thiazol-2-amine Chemical compound C1=CC(Cl)=CC=C1C1=CSC(N(CCCC=2C=CC=CC=2)CCCC=2C=CC=CC=2)=N1 KVLXOQWRFPIDSA-UHFFFAOYSA-N 0.000 claims 1
- OQKOGDJJSOSKPB-UHFFFAOYSA-N 4-(4-chlorophenyl)-n-(2-ethylsulfanylethyl)-1,3-thiazole-2-carboxamide Chemical compound S1C(C(=O)NCCSCC)=NC(C=2C=CC(Cl)=CC=2)=C1 OQKOGDJJSOSKPB-UHFFFAOYSA-N 0.000 claims 1
- CNABCJTVHNTWHU-UHFFFAOYSA-N 4-(4-chlorophenyl)-n-(2-morpholin-4-ylethyl)-1,3-thiazole-2-carboxamide Chemical compound C1=CC(Cl)=CC=C1C1=CSC(C(=O)NCCN2CCOCC2)=N1 CNABCJTVHNTWHU-UHFFFAOYSA-N 0.000 claims 1
- AKWXPICOKLLXBU-UHFFFAOYSA-N 4-(4-chlorophenyl)-n-(2-pyridin-4-ylethyl)-1,3-thiazole-2-carboxamide Chemical compound C1=CC(Cl)=CC=C1C1=CSC(C(=O)NCCC=2C=CN=CC=2)=N1 AKWXPICOKLLXBU-UHFFFAOYSA-N 0.000 claims 1
- OHPOJONOXDZHAG-UHFFFAOYSA-N 4-(4-chlorophenyl)-n-(2h-tetrazol-5-yl)-1,3-thiazole-2-carboxamide Chemical compound C1=CC(Cl)=CC=C1C1=CSC(C(=O)NC=2NN=NN=2)=N1 OHPOJONOXDZHAG-UHFFFAOYSA-N 0.000 claims 1
- GWOXSEIVOLIYKK-UHFFFAOYSA-N 4-(4-chlorophenyl)-n-(3,5-difluorophenyl)-1,3-thiazole-2-carboxamide Chemical compound FC1=CC(F)=CC(NC(=O)C=2SC=C(N=2)C=2C=CC(Cl)=CC=2)=C1 GWOXSEIVOLIYKK-UHFFFAOYSA-N 0.000 claims 1
- ZTFOJPVGBWIMLA-UHFFFAOYSA-N 4-(4-chlorophenyl)-n-(3-pyrrolidin-1-ylpropyl)-1,3-thiazole-2-carboxamide Chemical compound C1=CC(Cl)=CC=C1C1=CSC(C(=O)NCCCN2CCCC2)=N1 ZTFOJPVGBWIMLA-UHFFFAOYSA-N 0.000 claims 1
- KOIHYAURWODXTR-UHFFFAOYSA-N 4-(4-chlorophenyl)-n-(4-methylpiperazin-1-yl)-1,3-thiazole-2-carboxamide Chemical compound C1CN(C)CCN1NC(=O)C1=NC(C=2C=CC(Cl)=CC=2)=CS1 KOIHYAURWODXTR-UHFFFAOYSA-N 0.000 claims 1
- DMSUBVRSIXBFJX-UHFFFAOYSA-N 4-(4-chlorophenyl)-n-(pyridin-4-ylmethyl)-1,3-thiazole-2-carboxamide Chemical compound C1=CC(Cl)=CC=C1C1=CSC(C(=O)NCC=2C=CN=CC=2)=N1 DMSUBVRSIXBFJX-UHFFFAOYSA-N 0.000 claims 1
- MRWIBGMGTLOEQY-UHFFFAOYSA-N 4-(4-chlorophenyl)-n-[(2,5-difluorophenoxy)methyl]-1,3-thiazol-2-amine Chemical compound FC1=CC=C(F)C(OCNC=2SC=C(N=2)C=2C=CC(Cl)=CC=2)=C1 MRWIBGMGTLOEQY-UHFFFAOYSA-N 0.000 claims 1
- OJDWUDAKHJRDNN-UHFFFAOYSA-N 4-(4-chlorophenyl)-n-[(3,4,5-trifluorophenyl)methyl]-1,3-thiazole-2-carboxamide Chemical compound FC1=C(F)C(F)=CC(CNC(=O)C=2SC=C(N=2)C=2C=CC(Cl)=CC=2)=C1 OJDWUDAKHJRDNN-UHFFFAOYSA-N 0.000 claims 1
- VHDKRCKKTULFEB-UHFFFAOYSA-N 4-(4-chlorophenyl)-n-[(3,4-difluorophenyl)methyl]-1,3-thiazole-2-carboxamide Chemical compound C1=C(F)C(F)=CC=C1CNC(=O)C1=NC(C=2C=CC(Cl)=CC=2)=CS1 VHDKRCKKTULFEB-UHFFFAOYSA-N 0.000 claims 1
- YHYONVFXLNNQGM-UHFFFAOYSA-N 4-(4-chlorophenyl)-n-[(3,5-difluorophenoxy)methyl]-1,3-thiazol-2-amine Chemical compound FC1=CC(F)=CC(OCNC=2SC=C(N=2)C=2C=CC(Cl)=CC=2)=C1 YHYONVFXLNNQGM-UHFFFAOYSA-N 0.000 claims 1
- QOBTYVQRMWHRPF-UHFFFAOYSA-N 4-(4-chlorophenyl)-n-[(3,5-difluorophenyl)methoxymethyl]-1,3-thiazol-2-amine Chemical compound FC1=CC(F)=CC(COCNC=2SC=C(N=2)C=2C=CC(Cl)=CC=2)=C1 QOBTYVQRMWHRPF-UHFFFAOYSA-N 0.000 claims 1
- ZENLJWIPVJEMJW-UHFFFAOYSA-N 4-(4-chlorophenyl)-n-[(3,5-difluorophenyl)methyl]-1,3-thiazole-2-carboxamide Chemical compound FC1=CC(F)=CC(CNC(=O)C=2SC=C(N=2)C=2C=CC(Cl)=CC=2)=C1 ZENLJWIPVJEMJW-UHFFFAOYSA-N 0.000 claims 1
- DQASMKMLMHDJJU-UHFFFAOYSA-N 4-(4-chlorophenyl)-n-[(4-methylsulfanylphenyl)methyl]-1,3-thiazole-2-carboxamide Chemical compound C1=CC(SC)=CC=C1CNC(=O)C1=NC(C=2C=CC(Cl)=CC=2)=CS1 DQASMKMLMHDJJU-UHFFFAOYSA-N 0.000 claims 1
- KPKPPIXNQBLHTR-UHFFFAOYSA-N 4-(4-chlorophenyl)-n-[(4-methylsulfonylphenyl)methyl]-1,3-thiazole-2-carboxamide Chemical compound C1=CC(S(=O)(=O)C)=CC=C1CNC(=O)C1=NC(C=2C=CC(Cl)=CC=2)=CS1 KPKPPIXNQBLHTR-UHFFFAOYSA-N 0.000 claims 1
- ZCBVFZDCDHNHCF-UHFFFAOYSA-N 4-(4-chlorophenyl)-n-[(4-phenoxyphenyl)methyl]-1,3-thiazole-2-carboxamide Chemical compound C1=CC(Cl)=CC=C1C1=CSC(C(=O)NCC=2C=CC(OC=3C=CC=CC=3)=CC=2)=N1 ZCBVFZDCDHNHCF-UHFFFAOYSA-N 0.000 claims 1
- RTGHXPPMBKVCTM-UHFFFAOYSA-N 4-(4-chlorophenyl)-n-[(4-phenylphenyl)methyl]-1,3-thiazole-2-carboxamide Chemical compound C1=CC(Cl)=CC=C1C1=CSC(C(=O)NCC=2C=CC(=CC=2)C=2C=CC=CC=2)=N1 RTGHXPPMBKVCTM-UHFFFAOYSA-N 0.000 claims 1
- IFWOHNVBUYLOEI-UHFFFAOYSA-N 4-(4-chlorophenyl)-n-[1-(4-chlorophenyl)ethyl]-1,3-thiazole-2-carboxamide Chemical compound C=1C=C(Cl)C=CC=1C(C)NC(=O)C(SC=1)=NC=1C1=CC=C(Cl)C=C1 IFWOHNVBUYLOEI-UHFFFAOYSA-N 0.000 claims 1
- UXLPKDLHMWRDIJ-UHFFFAOYSA-N 4-(4-chlorophenyl)-n-[2-(1-methylpyrrolidin-2-yl)ethyl]-1,3-thiazole-2-carboxamide Chemical compound CN1CCCC1CCNC(=O)C1=NC(C=2C=CC(Cl)=CC=2)=CS1 UXLPKDLHMWRDIJ-UHFFFAOYSA-N 0.000 claims 1
- PZJLDKJCCCDDIW-UHFFFAOYSA-N 4-(4-chlorophenyl)-n-[2-(3-phenoxyphenyl)ethyl]-1,3-thiazole-2-carboxamide Chemical compound C1=CC(Cl)=CC=C1C1=CSC(C(=O)NCCC=2C=C(OC=3C=CC=CC=3)C=CC=2)=N1 PZJLDKJCCCDDIW-UHFFFAOYSA-N 0.000 claims 1
- ADBSXJWMIUZKJS-UHFFFAOYSA-N 4-(4-chlorophenyl)-n-[[2-fluoro-4-(trifluoromethyl)phenyl]methyl]-1,3-thiazole-2-carboxamide Chemical compound FC1=CC(C(F)(F)F)=CC=C1CNC(=O)C1=NC(C=2C=CC(Cl)=CC=2)=CS1 ADBSXJWMIUZKJS-UHFFFAOYSA-N 0.000 claims 1
- CAZFHBYGNLQFER-UHFFFAOYSA-N 4-(4-chlorophenyl)-n-[[3-(trifluoromethoxy)phenyl]methyl]-1,3-thiazole-2-carboxamide Chemical compound FC(F)(F)OC1=CC=CC(CNC(=O)C=2SC=C(N=2)C=2C=CC(Cl)=CC=2)=C1 CAZFHBYGNLQFER-UHFFFAOYSA-N 0.000 claims 1
- WZVIYVPBQQMXMD-UHFFFAOYSA-N 4-(4-chlorophenyl)-n-[[3-fluoro-5-(trifluoromethyl)phenyl]methyl]-1,3-thiazole-2-carboxamide Chemical compound FC(F)(F)C1=CC(F)=CC(CNC(=O)C=2SC=C(N=2)C=2C=CC(Cl)=CC=2)=C1 WZVIYVPBQQMXMD-UHFFFAOYSA-N 0.000 claims 1
- SXOHLKXSDBTUFP-UHFFFAOYSA-N 4-(4-chlorophenyl)-n-[[4-(dimethylamino)phenyl]methyl]-1,3-thiazole-2-carboxamide Chemical compound C1=CC(N(C)C)=CC=C1CNC(=O)C1=NC(C=2C=CC(Cl)=CC=2)=CS1 SXOHLKXSDBTUFP-UHFFFAOYSA-N 0.000 claims 1
- UICBMRBPNWZWRK-UHFFFAOYSA-N 4-(4-chlorophenyl)-n-[[4-(trifluoromethoxy)phenyl]methyl]-1,3-thiazole-2-carboxamide Chemical compound C1=CC(OC(F)(F)F)=CC=C1CNC(=O)C1=NC(C=2C=CC(Cl)=CC=2)=CS1 UICBMRBPNWZWRK-UHFFFAOYSA-N 0.000 claims 1
- SSWAMBVBVKXNLQ-UHFFFAOYSA-N 4-(4-chlorophenyl)-n-[[4-(trifluoromethyl)phenyl]methyl]-1,3-thiazole-2-carboxamide Chemical compound C1=CC(C(F)(F)F)=CC=C1CNC(=O)C1=NC(C=2C=CC(Cl)=CC=2)=CS1 SSWAMBVBVKXNLQ-UHFFFAOYSA-N 0.000 claims 1
- RKVHRUFKAKZOLX-UHFFFAOYSA-N 4-(4-chlorophenyl)-n-[[4-chloro-3-(trifluoromethyl)phenyl]methyl]-1,3-thiazole-2-carboxamide Chemical compound C1=C(Cl)C(C(F)(F)F)=CC(CNC(=O)C=2SC=C(N=2)C=2C=CC(Cl)=CC=2)=C1 RKVHRUFKAKZOLX-UHFFFAOYSA-N 0.000 claims 1
- ZSORJFUSMDSAKG-UHFFFAOYSA-N 4-(4-chlorophenyl)-n-[[4-fluoro-3-(trifluoromethyl)phenyl]methyl]-1,3-thiazole-2-carboxamide Chemical compound C1=C(C(F)(F)F)C(F)=CC=C1CNC(=O)C1=NC(C=2C=CC(Cl)=CC=2)=CS1 ZSORJFUSMDSAKG-UHFFFAOYSA-N 0.000 claims 1
- 208000037260 Atherosclerotic Plaque Diseases 0.000 claims 1
- 208000005590 Choroidal Neovascularization Diseases 0.000 claims 1
- 206010060823 Choroidal neovascularisation Diseases 0.000 claims 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 1
- 201000004624 Dermatitis Diseases 0.000 claims 1
- 206010012689 Diabetic retinopathy Diseases 0.000 claims 1
- 208000010412 Glaucoma Diseases 0.000 claims 1
- 206010020751 Hypersensitivity Diseases 0.000 claims 1
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 1
- 208000007766 Kaposi sarcoma Diseases 0.000 claims 1
- 206010029113 Neovascularisation Diseases 0.000 claims 1
- 102000001253 Protein Kinase Human genes 0.000 claims 1
- 208000019802 Sexually transmitted disease Diseases 0.000 claims 1
- 210000001744 T-lymphocyte Anatomy 0.000 claims 1
- 206010052779 Transplant rejections Diseases 0.000 claims 1
- PZCQOEHBQGSXSO-UHFFFAOYSA-N [2,3-di(butanoyloxy)-5-[[4-(4-chlorophenyl)-1,3-thiazol-2-yl]carbamoyl]phenyl] butanoate Chemical compound CCCC(=O)OC1=C(OC(=O)CCC)C(OC(=O)CCC)=CC(C(=O)NC=2SC=C(N=2)C=2C=CC(Cl)=CC=2)=C1 PZCQOEHBQGSXSO-UHFFFAOYSA-N 0.000 claims 1
- HDGAEBHQSHBUSQ-UHFFFAOYSA-N [2-[3-[[4-(4-chlorophenyl)-1,3-thiazol-2-yl]amino]-3-oxoprop-1-enyl]phenyl] butanoate Chemical compound CCCC(=O)OC1=CC=CC=C1C=CC(=O)NC1=NC(C=2C=CC(Cl)=CC=2)=CS1 HDGAEBHQSHBUSQ-UHFFFAOYSA-N 0.000 claims 1
- AXHSMWBCELHSRU-UHFFFAOYSA-N [2-amino-4-[2-[[4-(4-chlorophenyl)-1,3-thiazol-2-yl]amino]-2-oxoethyl]phenyl] butanoate Chemical compound C1=C(N)C(OC(=O)CCC)=CC=C1CC(=O)NC1=NC(C=2C=CC(Cl)=CC=2)=CS1 AXHSMWBCELHSRU-UHFFFAOYSA-N 0.000 claims 1
- XAWIVBYCTSRRRP-UHFFFAOYSA-N [3-[3-[[4-(4-chlorophenyl)-1,3-thiazol-2-yl]amino]-3-oxoprop-1-enyl]phenyl] butanoate Chemical compound CCCC(=O)OC1=CC=CC(C=CC(=O)NC=2SC=C(N=2)C=2C=CC(Cl)=CC=2)=C1 XAWIVBYCTSRRRP-UHFFFAOYSA-N 0.000 claims 1
- SGSIZWOUVBWSNA-UHFFFAOYSA-N [4-[2-[(6-chloro-1,3-benzothiazol-2-yl)amino]-2-oxoethyl]-2-methoxyphenyl] butanoate Chemical compound C1=C(OC)C(OC(=O)CCC)=CC=C1CC(=O)NC1=NC2=CC=C(Cl)C=C2S1 SGSIZWOUVBWSNA-UHFFFAOYSA-N 0.000 claims 1
- BFWSBGOFOQEUCD-UHFFFAOYSA-N [4-[2-[[4-(4-chlorophenyl)-1,3-thiazol-2-yl]amino]-2-oxoethyl]-2-methoxyphenyl] butanoate Chemical compound C1=C(OC)C(OC(=O)CCC)=CC=C1CC(=O)NC1=NC(C=2C=CC(Cl)=CC=2)=CS1 BFWSBGOFOQEUCD-UHFFFAOYSA-N 0.000 claims 1
- VEJJENMKYJGMPH-UHFFFAOYSA-N [4-[2-[[4-(4-chlorophenyl)-1,3-thiazol-2-yl]amino]-2-oxoethyl]-2-nitrophenyl] butanoate Chemical compound C1=C([N+]([O-])=O)C(OC(=O)CCC)=CC=C1CC(=O)NC1=NC(C=2C=CC(Cl)=CC=2)=CS1 VEJJENMKYJGMPH-UHFFFAOYSA-N 0.000 claims 1
- SSBHMRZURYSKSW-UHFFFAOYSA-N [4-[3-[[4-(4-bromophenyl)-1,3-thiazol-2-yl]amino]-3-oxoprop-1-enyl]-2-methoxyphenyl] butanoate Chemical compound C1=C(OC)C(OC(=O)CCC)=CC=C1C=CC(=O)NC1=NC(C=2C=CC(Br)=CC=2)=CS1 SSBHMRZURYSKSW-UHFFFAOYSA-N 0.000 claims 1
- BXVHSOIZPUQVPC-UHFFFAOYSA-N [4-[3-[[4-(4-chlorophenyl)-1,3-thiazol-2-yl]amino]-3-oxoprop-1-enyl]-2-methoxyphenyl] acetate Chemical compound C1=C(OC(C)=O)C(OC)=CC(C=CC(=O)NC=2SC=C(N=2)C=2C=CC(Cl)=CC=2)=C1 BXVHSOIZPUQVPC-UHFFFAOYSA-N 0.000 claims 1
- GYHDLXIGKBXZCB-UHFFFAOYSA-N [4-[3-[[4-(4-chlorophenyl)-1,3-thiazol-2-yl]amino]-3-oxoprop-1-enyl]-2-methoxyphenyl] butanoate Chemical compound C1=C(OC)C(OC(=O)CCC)=CC=C1C=CC(=O)NC1=NC(C=2C=CC(Cl)=CC=2)=CS1 GYHDLXIGKBXZCB-UHFFFAOYSA-N 0.000 claims 1
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| CN103159686A (zh) * | 2011-12-09 | 2013-06-19 | 天津市国际生物医药联合研究院 | 一种hiv-1蛋白酶的脲类抑制剂 |
| AU2013229177B2 (en) | 2012-03-06 | 2017-03-23 | Lupin Limited | Thiazole derivatives as alpha 7 nAChR modulators |
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| CN103772376B (zh) * | 2012-10-24 | 2017-01-11 | 中国医学科学院医药生物技术研究所 | 取代的苯并-1,3-杂唑类化合物、其制备方法及用途 |
| US20150299178A1 (en) | 2012-11-12 | 2015-10-22 | Lupin Limited | Thiazole Derivatives as Alpha 7 NACHR Modulators |
| DE102013226711A1 (de) * | 2013-12-19 | 2015-06-25 | Beiersdorf Ag | Verwendung von Alkylamidothiazolen in kosmetischen oder dermatologischen Zubereitungen zur Prophylaxe vor und Behandlung von sensibler Haut |
| NZ716494A (en) | 2014-04-28 | 2017-07-28 | Omeros Corp | Processes and intermediates for the preparation of a pde10 inhibitor |
| NZ630803A (en) | 2014-04-28 | 2016-03-31 | Omeros Corp | Optically active pde10 inhibitor |
| AU2015281799B2 (en) | 2014-06-26 | 2019-11-28 | Central Adelaide Local Health Network Incorporated | Enzyme interacting agents |
| HK1243636A1 (zh) * | 2014-11-18 | 2018-07-20 | Rutgers, The State University Of New Jersey | 用於治疗代谢疾病和癌症的新的线粒体解偶联剂 |
| WO2016085933A1 (en) | 2014-11-24 | 2016-06-02 | The Board Of Trustees Of The University Of Illinois | Method of preventing or treating a pulmonary disease or condition |
| BR112017022936A2 (pt) | 2015-04-24 | 2018-07-17 | Omeros Corp | inibidores da pde10 e composições e métodos relacionados |
| US11028061B2 (en) * | 2015-07-27 | 2021-06-08 | Sanford Burnham Prebys Medical Discovery Institute | Modulators of myocyte lipid accumulation and insulin resistance and methods of use thereof |
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| CN107056755B (zh) * | 2015-12-07 | 2019-02-22 | 苏州信诺维医药科技有限公司 | 五元杂环酰胺类wnt通路抑制剂 |
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| KR102732033B1 (ko) * | 2019-07-26 | 2024-11-20 | 아주대학교산학협력단 | Tlr7 및 tlr9의 신호전달 경로를 억제하는 신규한 소분자 화합물 및 그 용도 |
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2006
- 2006-08-03 US US11/462,153 patent/US20070032531A1/en not_active Abandoned
- 2006-08-03 WO PCT/US2006/030327 patent/WO2007019251A2/en not_active Ceased
- 2006-08-03 CA CA002617788A patent/CA2617788A1/en not_active Abandoned
- 2006-08-03 AU AU2006278592A patent/AU2006278592A1/en not_active Abandoned
- 2006-08-03 JP JP2008525195A patent/JP2009503107A/ja active Pending
- 2006-08-03 EP EP06800721A patent/EP1928848A2/en not_active Withdrawn
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2008
- 2008-01-22 IL IL188932A patent/IL188932A0/en unknown
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2009
- 2009-11-30 US US12/627,812 patent/US20100137315A1/en not_active Abandoned