JP2014501266A5 - - Google Patents
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- JP2014501266A5 JP2014501266A5 JP2013546672A JP2013546672A JP2014501266A5 JP 2014501266 A5 JP2014501266 A5 JP 2014501266A5 JP 2013546672 A JP2013546672 A JP 2013546672A JP 2013546672 A JP2013546672 A JP 2013546672A JP 2014501266 A5 JP2014501266 A5 JP 2014501266A5
- Authority
- JP
- Japan
- Prior art keywords
- fluoro
- methyl
- carboxylic acid
- amide
- ethylcarbamoyl
- 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 description 43
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 37
- 150000001875 compounds Chemical class 0.000 claims description 24
- 125000003545 alkoxy group Chemical group 0.000 claims description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims description 23
- 239000001257 hydrogen Substances 0.000 claims description 23
- 229910052736 halogen Inorganic materials 0.000 claims description 21
- 150000002367 halogens Chemical group 0.000 claims description 21
- 125000001072 heteroaryl group Chemical group 0.000 claims description 21
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 17
- -1 halocycloalkoxyalkyl Chemical group 0.000 claims description 16
- 125000001188 haloalkyl group Chemical group 0.000 claims description 15
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 15
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 10
- 125000003107 substituted aryl group Chemical group 0.000 claims description 10
- 125000004858 cycloalkoxyalkyl group Chemical group 0.000 claims description 9
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 9
- 125000005347 halocycloalkyl group Chemical group 0.000 claims description 9
- 125000004461 halocycloalkylalkyl group Chemical group 0.000 claims description 9
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 8
- 125000005120 alkyl cycloalkyl alkyl group Chemical group 0.000 claims description 6
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 6
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 125000004994 halo alkoxy alkyl group Chemical group 0.000 claims description 5
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 4
- 125000005081 alkoxyalkoxyalkyl group Chemical group 0.000 claims description 4
- 125000005112 cycloalkylalkoxy group Chemical group 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000004993 haloalkoxycarbonyl group Chemical group 0.000 claims description 3
- 125000006769 halocycloalkoxy group Chemical group 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000005113 hydroxyalkoxy group Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 11
- 206010018364 Glomerulonephritis Diseases 0.000 claims 8
- HXIYCKAAQPHZBM-UHFFFAOYSA-N 3-methyl-1,2-oxazole-5-carboxylic acid Chemical compound CC=1C=C(C(O)=O)ON=1 HXIYCKAAQPHZBM-UHFFFAOYSA-N 0.000 claims 4
- RGTBLCLLSZPOKR-UHFFFAOYSA-N 5-methyl-1,2,4-oxadiazole Chemical compound CC1=NC=NO1 RGTBLCLLSZPOKR-UHFFFAOYSA-N 0.000 claims 4
- XGWFJBFNAQHLEF-UHFFFAOYSA-N 9-anthroic acid Chemical compound C1=CC=C2C(C(=O)O)=C(C=CC=C3)C3=CC2=C1 XGWFJBFNAQHLEF-UHFFFAOYSA-N 0.000 claims 4
- 208000005777 Lupus Nephritis Diseases 0.000 claims 4
- 208000015446 immunoglobulin a vasculitis Diseases 0.000 claims 4
- 208000017169 kidney disease Diseases 0.000 claims 4
- 201000008383 nephritis Diseases 0.000 claims 4
- WMMGHBYADJNEOC-UHFFFAOYSA-N 3-methoxy-1,2-oxazole-5-carboxylic acid Chemical compound COC=1C=C(C(O)=O)ON=1 WMMGHBYADJNEOC-UHFFFAOYSA-N 0.000 claims 3
- 241001272720 Medialuna californiensis Species 0.000 claims 3
- 125000000842 isoxazolyl group Chemical group 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 125000002098 pyridazinyl group Chemical group 0.000 claims 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 3
- 125000002883 imidazolyl group Chemical group 0.000 claims 2
- OXSHWXONCQEHCW-GFCCVEGCSA-N n-[3-[[(1r)-1-[5-[5-chloro-3-fluoro-2-(2-methyltetrazol-5-yl)phenyl]-3-fluoropyridin-2-yl]ethyl]carbamoyl]oxetan-3-yl]-2-methoxypyrimidine-5-carboxamide Chemical compound C1=NC(OC)=NC=C1C(=O)NC1(C(=O)N[C@H](C)C=2C(=CC(=CN=2)C=2C(=C(F)C=C(Cl)C=2)C2=NN(C)N=N2)F)COC1 OXSHWXONCQEHCW-GFCCVEGCSA-N 0.000 claims 2
- CAOFUTXBTGKTNT-GFCCVEGCSA-N n-[3-[[(1r)-1-[5-[5-chloro-3-fluoro-2-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]-3-fluoropyridin-2-yl]ethyl]carbamoyl]oxetan-3-yl]-2-methoxypyrimidine-5-carboxamide Chemical compound C1=NC(OC)=NC=C1C(=O)NC1(C(=O)N[C@H](C)C=2C(=CC(=CN=2)C=2C(=C(F)C=C(Cl)C=2)C=2N=C(C)ON=2)F)COC1 CAOFUTXBTGKTNT-GFCCVEGCSA-N 0.000 claims 2
- GRSLJWFHSQYERQ-SNVBAGLBSA-N n-[3-[[(1r)-1-[5-[5-chloro-3-fluoro-2-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]-3-fluoropyridin-2-yl]ethyl]carbamoyl]oxetan-3-yl]-5-methyl-1,3,4-oxadiazole-2-carboxamide Chemical compound N([C@H](C)C=1C(=CC(=CN=1)C=1C(=C(F)C=C(Cl)C=1)C=1N=C(C)ON=1)F)C(=O)C1(NC(=O)C=2OC(C)=NN=2)COC1 GRSLJWFHSQYERQ-SNVBAGLBSA-N 0.000 claims 2
- LSWDLQVHQFWVKW-GFCCVEGCSA-N n-[3-[[(1r)-1-[5-[5-chloro-3-fluoro-2-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]-3-fluoropyridin-2-yl]ethyl]carbamoyl]oxetan-3-yl]pyridazine-3-carboxamide Chemical compound N([C@H](C)C=1C(=CC(=CN=1)C=1C(=C(F)C=C(Cl)C=1)C=1N=C(C)ON=1)F)C(=O)C1(NC(=O)C=2N=NC=CC=2)COC1 LSWDLQVHQFWVKW-GFCCVEGCSA-N 0.000 claims 2
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 2
- MIIQJAUWHSUTIT-UHFFFAOYSA-N 1,2-oxazole-5-carboxylic acid Chemical compound OC(=O)C1=CC=NO1 MIIQJAUWHSUTIT-UHFFFAOYSA-N 0.000 claims 1
- BUAGQNHTYLAQCU-UHFFFAOYSA-N 3-[(2-methoxyacetyl)amino]oxetane-3-carboxylic acid Chemical compound COCC(=O)NC1(C(O)=O)COC1 BUAGQNHTYLAQCU-UHFFFAOYSA-N 0.000 claims 1
- MEPBSYZELXUPLN-GFCCVEGCSA-N 5-amino-n-[3-[[(1r)-1-[5-[5-chloro-3-fluoro-2-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]-3-fluoropyridin-2-yl]ethyl]carbamoyl]oxetan-3-yl]pyridine-3-carboxamide Chemical compound N([C@H](C)C=1C(=CC(=CN=1)C=1C(=C(F)C=C(Cl)C=1)C=1N=C(C)ON=1)F)C(=O)C1(NC(=O)C=2C=C(N)C=NC=2)COC1 MEPBSYZELXUPLN-GFCCVEGCSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- DTMIQGWAUKXLMT-CYBMUJFWSA-N methyl 2-chloro-6-[3-fluoro-4-[(1r)-1-[[3-(1,2-oxazole-5-carbonylamino)oxetane-3-carbonyl]amino]ethyl]phenyl]benzoate Chemical compound COC(=O)C1=C(Cl)C=CC=C1C(C=C1F)=CC=C1[C@@H](C)NC(=O)C1(NC(=O)C=2ON=CC=2)COC1 DTMIQGWAUKXLMT-CYBMUJFWSA-N 0.000 claims 1
- CWJWJHIDQXXJLE-GFCCVEGCSA-N methyl 2-chloro-6-[3-fluoro-4-[(1r)-1-[[3-(3,3,3-trifluoropropanoylamino)oxetane-3-carbonyl]amino]ethyl]phenyl]benzoate Chemical compound COC(=O)C1=C(Cl)C=CC=C1C(C=C1F)=CC=C1[C@@H](C)NC(=O)C1(NC(=O)CC(F)(F)F)COC1 CWJWJHIDQXXJLE-GFCCVEGCSA-N 0.000 claims 1
- SRAVZAAZSZSOJS-CQSZACIVSA-N methyl 2-chloro-6-[3-fluoro-4-[(1r)-1-[[3-(pyrimidine-5-carbonylamino)oxetane-3-carbonyl]amino]ethyl]phenyl]benzoate Chemical compound COC(=O)C1=C(Cl)C=CC=C1C(C=C1F)=CC=C1[C@@H](C)NC(=O)C1(NC(=O)C=2C=NC=NC=2)COC1 SRAVZAAZSZSOJS-CQSZACIVSA-N 0.000 claims 1
- GLIUFPYQUKVKGM-LLVKDONJSA-N methyl 2-chloro-6-[3-fluoro-4-[(1r)-1-[[3-[(2,2,2-trifluoroacetyl)amino]oxetane-3-carbonyl]amino]ethyl]phenyl]benzoate Chemical compound COC(=O)C1=C(Cl)C=CC=C1C(C=C1F)=CC=C1[C@@H](C)NC(=O)C1(NC(=O)C(F)(F)F)COC1 GLIUFPYQUKVKGM-LLVKDONJSA-N 0.000 claims 1
- FNUJSJPEYKYQDN-CQSZACIVSA-N methyl 2-chloro-6-[3-fluoro-4-[(1r)-1-[[3-[(3-methyl-1,2-oxazole-5-carbonyl)amino]oxetane-3-carbonyl]amino]ethyl]phenyl]benzoate Chemical compound COC(=O)C1=C(Cl)C=CC=C1C(C=C1F)=CC=C1[C@@H](C)NC(=O)C1(NC(=O)C=2ON=C(C)C=2)COC1 FNUJSJPEYKYQDN-CQSZACIVSA-N 0.000 claims 1
- MWQLTYPGCVGPCZ-SNVBAGLBSA-N n-[(1r)-1-[4-[3,5-dichloro-2-(2,2-difluoroethoxy)phenyl]-2-fluorophenyl]ethyl]-3-[(2,2,2-trifluoroacetyl)amino]oxetane-3-carboxamide Chemical compound N([C@H](C)C=1C(=CC(=CC=1)C=1C(=C(Cl)C=C(Cl)C=1)OCC(F)F)F)C(=O)C1(NC(=O)C(F)(F)F)COC1 MWQLTYPGCVGPCZ-SNVBAGLBSA-N 0.000 claims 1
- PNXLQFRHHHRCHN-SNVBAGLBSA-N n-[(1r)-1-[4-[5-chloro-3-fluoro-2-(2-methyltetrazol-5-yl)phenyl]-2-fluorophenyl]ethyl]-3-[(2,2,2-trifluoroacetyl)amino]oxetane-3-carboxamide Chemical compound N([C@H](C)C=1C(=CC(=CC=1)C=1C(=C(F)C=C(Cl)C=1)C1=NN(C)N=N1)F)C(=O)C1(NC(=O)C(F)(F)F)COC1 PNXLQFRHHHRCHN-SNVBAGLBSA-N 0.000 claims 1
- ZYTIZDWKWBIHRN-LLVKDONJSA-N n-[(1r)-1-[5-[3,5-dichloro-2-(2,2-difluoroethoxy)phenyl]-3-fluoropyridin-2-yl]ethyl]-3-[(2-methoxyacetyl)amino]oxetane-3-carboxamide Chemical compound N([C@H](C)C=1C(=CC(=CN=1)C=1C(=C(Cl)C=C(Cl)C=1)OCC(F)F)F)C(=O)C1(NC(=O)COC)COC1 ZYTIZDWKWBIHRN-LLVKDONJSA-N 0.000 claims 1
- HOCRRXWEMNJJHV-SECBINFHSA-N n-[(1r)-1-[5-[5-chloro-3-fluoro-2-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]-3-fluoropyridin-2-yl]ethyl]-3-[(2,2,2-trifluoroacetyl)amino]oxetane-3-carboxamide Chemical compound N([C@H](C)C=1C(=CC(=CN=1)C=1C(=C(F)C=C(Cl)C=1)C=1N=C(C)ON=1)F)C(=O)C1(NC(=O)C(F)(F)F)COC1 HOCRRXWEMNJJHV-SECBINFHSA-N 0.000 claims 1
- QVHUHDRWZBREHP-GFCCVEGCSA-N n-[(1r)-1-[5-[5-chloro-3-fluoro-2-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]-3-fluoropyridin-2-yl]ethyl]-3-[[3-fluoro-5-(trifluoromethyl)benzoyl]amino]oxetane-3-carboxamide Chemical compound N([C@H](C)C=1C(=CC(=CN=1)C=1C(=C(F)C=C(Cl)C=1)C=1N=C(C)ON=1)F)C(=O)C1(NC(=O)C=2C=C(C=C(F)C=2)C(F)(F)F)COC1 QVHUHDRWZBREHP-GFCCVEGCSA-N 0.000 claims 1
- TVIHSGNVGMFCOO-GFCCVEGCSA-N n-[3-[[(1r)-1-[4-[3,5-dichloro-2-(2,2-difluoroethoxy)phenyl]-2-fluorophenyl]ethyl]carbamoyl]oxetan-3-yl]-1,2-oxazole-5-carboxamide Chemical compound N([C@H](C)C=1C(=CC(=CC=1)C=1C(=C(Cl)C=C(Cl)C=1)OCC(F)F)F)C(=O)C1(NC(=O)C=2ON=CC=2)COC1 TVIHSGNVGMFCOO-GFCCVEGCSA-N 0.000 claims 1
- RZQSOEQLZFJFFD-CYBMUJFWSA-N n-[3-[[(1r)-1-[4-[3,5-dichloro-2-(2,2-difluoroethoxy)phenyl]-2-fluorophenyl]ethyl]carbamoyl]oxetan-3-yl]-2-methoxypyrimidine-5-carboxamide Chemical compound C1=NC(OC)=NC=C1C(=O)NC1(C(=O)N[C@H](C)C=2C(=CC(=CC=2)C=2C(=C(Cl)C=C(Cl)C=2)OCC(F)F)F)COC1 RZQSOEQLZFJFFD-CYBMUJFWSA-N 0.000 claims 1
- LMQBUNABDATEJZ-GFCCVEGCSA-N n-[3-[[(1r)-1-[4-[3,5-dichloro-2-(2,2-difluoroethoxy)phenyl]-2-fluorophenyl]ethyl]carbamoyl]oxetan-3-yl]-3-methoxy-1,2-oxazole-5-carboxamide Chemical compound O1N=C(OC)C=C1C(=O)NC1(C(=O)N[C@H](C)C=2C(=CC(=CC=2)C=2C(=C(Cl)C=C(Cl)C=2)OCC(F)F)F)COC1 LMQBUNABDATEJZ-GFCCVEGCSA-N 0.000 claims 1
- QUODQZASWJEYAM-LLVKDONJSA-N n-[3-[[(1r)-1-[4-[3,5-dichloro-2-(2,2-difluoroethoxy)phenyl]-2-fluorophenyl]ethyl]carbamoyl]oxetan-3-yl]-5-methyl-1,3,4-oxadiazole-2-carboxamide Chemical compound N([C@H](C)C=1C(=CC(=CC=1)C=1C(=C(Cl)C=C(Cl)C=1)OCC(F)F)F)C(=O)C1(NC(=O)C=2OC(C)=NN=2)COC1 QUODQZASWJEYAM-LLVKDONJSA-N 0.000 claims 1
- BQYDRNLLJKBIEI-CYBMUJFWSA-N n-[3-[[(1r)-1-[4-[5-chloro-3-fluoro-2-(2-methyltetrazol-5-yl)phenyl]-2-fluorophenyl]ethyl]carbamoyl]oxetan-3-yl]-2-methoxypyrimidine-5-carboxamide Chemical compound C1=NC(OC)=NC=C1C(=O)NC1(C(=O)N[C@H](C)C=2C(=CC(=CC=2)C=2C(=C(F)C=C(Cl)C=2)C2=NN(C)N=N2)F)COC1 BQYDRNLLJKBIEI-CYBMUJFWSA-N 0.000 claims 1
- DDBPJLLSDPDUAU-GFCCVEGCSA-N n-[3-[[(1r)-1-[4-[5-chloro-3-fluoro-2-(2-methyltetrazol-5-yl)phenyl]-2-fluorophenyl]ethyl]carbamoyl]oxetan-3-yl]-3-methoxy-1,2-oxazole-5-carboxamide Chemical compound O1N=C(OC)C=C1C(=O)NC1(C(=O)N[C@H](C)C=2C(=CC(=CC=2)C=2C(=C(F)C=C(Cl)C=2)C2=NN(C)N=N2)F)COC1 DDBPJLLSDPDUAU-GFCCVEGCSA-N 0.000 claims 1
- XEPXEQLAYKAMTP-CYBMUJFWSA-N n-[3-[[(1r)-1-[4-[5-chloro-3-fluoro-2-(2-methyltetrazol-5-yl)phenyl]-2-fluorophenyl]ethyl]carbamoyl]oxetan-3-yl]-3-methyl-1,2-oxazole-5-carboxamide Chemical compound N([C@H](C)C=1C(=CC(=CC=1)C=1C(=C(F)C=C(Cl)C=1)C1=NN(C)N=N1)F)C(=O)C1(NC(=O)C=2ON=C(C)C=2)COC1 XEPXEQLAYKAMTP-CYBMUJFWSA-N 0.000 claims 1
- VISBFCYEAMWAIG-CYBMUJFWSA-N n-[3-[[(1r)-1-[4-[5-chloro-3-fluoro-2-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]-2-fluorophenyl]ethyl]carbamoyl]oxetan-3-yl]-2-methoxypyrimidine-5-carboxamide Chemical compound C1=NC(OC)=NC=C1C(=O)NC1(C(=O)N[C@H](C)C=2C(=CC(=CC=2)C=2C(=C(F)C=C(Cl)C=2)C=2N=C(C)ON=2)F)COC1 VISBFCYEAMWAIG-CYBMUJFWSA-N 0.000 claims 1
- JEISKSYXIZFGBQ-CYBMUJFWSA-N n-[3-[[(1r)-1-[4-[5-chloro-3-fluoro-2-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]-2-fluorophenyl]ethyl]carbamoyl]oxetan-3-yl]-3-methyl-1,2-oxazole-5-carboxamide Chemical compound N([C@H](C)C=1C(=CC(=CC=1)C=1C(=C(F)C=C(Cl)C=1)C=1N=C(C)ON=1)F)C(=O)C1(NC(=O)C=2ON=C(C)C=2)COC1 JEISKSYXIZFGBQ-CYBMUJFWSA-N 0.000 claims 1
- QRJFVILHVIPGKL-LLVKDONJSA-N n-[3-[[(1r)-1-[5-[3,5-dichloro-2-(2,2-difluoroethoxy)phenyl]-3-fluoropyridin-2-yl]ethyl]carbamoyl]oxetan-3-yl]-1,2-oxazole-5-carboxamide Chemical compound N([C@H](C)C=1C(=CC(=CN=1)C=1C(=C(Cl)C=C(Cl)C=1)OCC(F)F)F)C(=O)C1(NC(=O)C=2ON=CC=2)COC1 QRJFVILHVIPGKL-LLVKDONJSA-N 0.000 claims 1
- ZTAZAUFEMTZULS-GFCCVEGCSA-N n-[3-[[(1r)-1-[5-[3,5-dichloro-2-(2,2-difluoroethoxy)phenyl]-3-fluoropyridin-2-yl]ethyl]carbamoyl]oxetan-3-yl]-2-methoxypyrimidine-5-carboxamide Chemical compound C1=NC(OC)=NC=C1C(=O)NC1(C(=O)N[C@H](C)C=2C(=CC(=CN=2)C=2C(=C(Cl)C=C(Cl)C=2)OCC(F)F)F)COC1 ZTAZAUFEMTZULS-GFCCVEGCSA-N 0.000 claims 1
- JZNLJBXURXFTNR-LLVKDONJSA-N n-[3-[[(1r)-1-[5-[3,5-dichloro-2-(2,2-difluoroethoxy)phenyl]-3-fluoropyridin-2-yl]ethyl]carbamoyl]oxetan-3-yl]-3-methoxy-1,2-oxazole-5-carboxamide Chemical compound O1N=C(OC)C=C1C(=O)NC1(C(=O)N[C@H](C)C=2C(=CC(=CN=2)C=2C(=C(Cl)C=C(Cl)C=2)OCC(F)F)F)COC1 JZNLJBXURXFTNR-LLVKDONJSA-N 0.000 claims 1
- FGAZQSUHSMGEAD-GFCCVEGCSA-N n-[3-[[(1r)-1-[5-[3,5-dichloro-2-(2,2-difluoroethoxy)phenyl]-3-fluoropyridin-2-yl]ethyl]carbamoyl]oxetan-3-yl]-3-methyl-1,2-oxazole-5-carboxamide Chemical compound N([C@H](C)C=1C(=CC(=CN=1)C=1C(=C(Cl)C=C(Cl)C=1)OCC(F)F)F)C(=O)C1(NC(=O)C=2ON=C(C)C=2)COC1 FGAZQSUHSMGEAD-GFCCVEGCSA-N 0.000 claims 1
- MXBKUQQIAJRWAI-SNVBAGLBSA-N n-[3-[[(1r)-1-[5-[3,5-dichloro-2-(2,2-difluoroethoxy)phenyl]-3-fluoropyridin-2-yl]ethyl]carbamoyl]oxetan-3-yl]-5-methyl-1,3,4-oxadiazole-2-carboxamide Chemical compound N([C@H](C)C=1C(=CC(=CN=1)C=1C(=C(Cl)C=C(Cl)C=1)OCC(F)F)F)C(=O)C1(NC(=O)C=2OC(C)=NN=2)COC1 MXBKUQQIAJRWAI-SNVBAGLBSA-N 0.000 claims 1
- LLDFSJPKIXSOIR-GFCCVEGCSA-N n-[3-[[(1r)-1-[5-[3,5-dichloro-2-(2,2-difluoroethoxy)phenyl]-3-fluoropyridin-2-yl]ethyl]carbamoyl]oxetan-3-yl]pyrimidine-5-carboxamide Chemical compound N([C@H](C)C=1C(=CC(=CN=1)C=1C(=C(Cl)C=C(Cl)C=1)OCC(F)F)F)C(=O)C1(NC(=O)C=2C=NC=NC=2)COC1 LLDFSJPKIXSOIR-GFCCVEGCSA-N 0.000 claims 1
- KUCUOSJPMAZFBW-GFCCVEGCSA-N n-[3-[[(1r)-1-[5-[5-chloro-3-fluoro-2-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]-3-fluoropyridin-2-yl]ethyl]carbamoyl]oxetan-3-yl]-1-methylimidazole-2-carboxamide Chemical compound N([C@H](C)C=1C(=CC(=CN=1)C=1C(=C(F)C=C(Cl)C=1)C=1N=C(C)ON=1)F)C(=O)C1(NC(=O)C=2N(C=CN=2)C)COC1 KUCUOSJPMAZFBW-GFCCVEGCSA-N 0.000 claims 1
- DURQIALVBWTDJS-GFCCVEGCSA-N n-[3-[[(1r)-1-[5-[5-chloro-3-fluoro-2-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]-3-fluoropyridin-2-yl]ethyl]carbamoyl]oxetan-3-yl]-1-methylimidazole-4-carboxamide Chemical compound N([C@H](C)C=1C(=CC(=CN=1)C=1C(=C(F)C=C(Cl)C=1)C=1N=C(C)ON=1)F)C(=O)C1(NC(=O)C=2N=CN(C)C=2)COC1 DURQIALVBWTDJS-GFCCVEGCSA-N 0.000 claims 1
- TYOISXNHARBOSC-SNVBAGLBSA-N n-[3-[[(1r)-1-[5-[5-chloro-3-fluoro-2-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]-3-fluoropyridin-2-yl]ethyl]carbamoyl]oxetan-3-yl]-4-methylthiadiazole-5-carboxamide Chemical compound N([C@H](C)C=1C(=CC(=CN=1)C=1C(=C(F)C=C(Cl)C=1)C=1N=C(C)ON=1)F)C(=O)C1(NC(=O)C2=C(N=NS2)C)COC1 TYOISXNHARBOSC-SNVBAGLBSA-N 0.000 claims 1
- TWUIXZVQIZSZNL-GFCCVEGCSA-N n-[3-[[(1r)-1-[5-[5-chloro-3-fluoro-2-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]-3-fluoropyridin-2-yl]ethyl]carbamoyl]oxetan-3-yl]pyridazine-4-carboxamide Chemical compound N([C@H](C)C=1C(=CC(=CN=1)C=1C(=C(F)C=C(Cl)C=1)C=1N=C(C)ON=1)F)C(=O)C1(NC(=O)C=2C=NN=CC=2)COC1 TWUIXZVQIZSZNL-GFCCVEGCSA-N 0.000 claims 1
- RQARWLFYEUNZFN-CYBMUJFWSA-N n-[3-[[(1r)-1-[5-[5-chloro-3-fluoro-2-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]-3-fluoropyridin-2-yl]ethyl]carbamoyl]oxetan-3-yl]pyridine-3-carboxamide Chemical compound N([C@H](C)C=1C(=CC(=CN=1)C=1C(=C(F)C=C(Cl)C=1)C=1N=C(C)ON=1)F)C(=O)C1(NC(=O)C=2C=NC=CC=2)COC1 RQARWLFYEUNZFN-CYBMUJFWSA-N 0.000 claims 1
- OGHMZCQTJNUTPP-GFCCVEGCSA-N n-[3-[[(1r)-1-[5-[5-chloro-3-fluoro-2-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]-3-fluoropyridin-2-yl]ethyl]carbamoyl]oxetan-3-yl]pyrimidine-5-carboxamide Chemical compound N([C@H](C)C=1C(=CC(=CN=1)C=1C(=C(F)C=C(Cl)C=1)C=1N=C(C)ON=1)F)C(=O)C1(NC(=O)C=2C=NC=NC=2)COC1 OGHMZCQTJNUTPP-GFCCVEGCSA-N 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- BXCZJWHJYRELHY-UHFFFAOYSA-N thiadiazole-5-carboxylic acid Chemical compound OC(=O)C1=CN=NS1 BXCZJWHJYRELHY-UHFFFAOYSA-N 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 11
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| EP10197030.9 | 2010-12-27 | ||
| PCT/EP2011/073717 WO2012089601A1 (en) | 2010-12-27 | 2011-12-22 | New biaryl amide derivatives |
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| JP2014501266A JP2014501266A (ja) | 2014-01-20 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US8912221B2 (en) * | 2010-12-27 | 2014-12-16 | Hoffmann-La Roche Inc. | Biaryl amide derivatives |
| CN105294520A (zh) * | 2015-11-23 | 2016-02-03 | 大连九信生物化工科技有限公司 | 一种2-（2’,2’-二氟乙氧基）-6-三氟甲基苯基丙基硫醚的合成工艺 |
| JP7673982B2 (ja) * | 2019-10-02 | 2025-05-09 | ドメイン・セラピューティクス | プロスタグランジンｅ２（ｐｇｅ２）ｅｐ４受容体アンタゴニスト |
| TW202120479A (zh) | 2019-11-27 | 2021-06-01 | 瑞士商先正達農作物保護公司 | 用於製備具有3-含硫取代基的5-氯-吡啶-2-羧酸及羧酸酯之方法 |
| TW202134214A (zh) | 2020-03-04 | 2021-09-16 | 瑞士商先正達農作物保護公司 | 用於製備具有3-含硫取代基的5-氯-吡啶-2-甲酸醯胺以及甲酸鹽之方法 |
| US20230348366A1 (en) * | 2020-10-01 | 2023-11-02 | Bayer Aktiengesellschaft | Benzaldehyde oximes and method for producing same |
| TW202229238A (zh) | 2020-10-09 | 2022-08-01 | 瑞士商先正達農作物保護公司 | 用於製備５－（１－氰基環丙基）－吡啶－２－甲酸、酯、醯胺和腈之方法 |
| CN114671747B (zh) * | 2022-04-08 | 2024-10-29 | 浙江永太科技股份有限公司 | 一种4-氯-2-氟苯甲醛的合成方法 |
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| AR038377A1 (es) * | 2002-02-08 | 2005-01-12 | Merck & Co Inc | Derivados de n-bifenil-aminocicloalcancarboxamida (con sustitucion con metilo) |
| US7163951B2 (en) * | 2002-08-29 | 2007-01-16 | Merck & Co., Inc. | N-biarylmethyl aminocycloalkanecarboxamide derivatives |
| CN1832922A (zh) * | 2003-08-07 | 2006-09-13 | 默克公司 | 磺酰基取代的n－(联芳基甲基)氨基环丙烷甲酰胺类 |
| JP2007526311A (ja) * | 2004-03-02 | 2007-09-13 | メルク エンド カムパニー インコーポレーテッド | ブラジキニンアンタゴニストとしてのアミノシクロプロパンカルボキサミド誘導体 |
| BRPI0510019A (pt) * | 2004-05-13 | 2007-09-25 | Boehringer Ingelheim Int | amidas de ácido tiofenocarboxìlico substituìdas, sua preparação e seu uso como medicamento |
| DE102004047840A1 (de) * | 2004-09-29 | 2006-03-30 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue substituierte Thiophencarbonsäureamide, deren Herstellung und deren Verwendung als Arzneimittel |
| HUP0600808A3 (en) * | 2006-10-27 | 2008-09-29 | Richter Gedeon Nyrt | New benzamide derivatives as bradykinin antagonists, process for their preparation and pharmaceutical compositions containing them |
| BRPI0819831A2 (pt) * | 2007-11-29 | 2019-09-24 | Boehringer Ingelheim Int | derivados de amidas de áciodo 6,7-diidro-5h-imidazo[1,2-a]imidazol-3-carboxílico |
| AP2011005808A0 (en) | 2009-02-26 | 2011-08-31 | Boehringer Ingelheim Int | Compounds as bradykinin B1 antagonists. |
| WO2010097374A1 (de) | 2009-02-26 | 2010-09-02 | Boehringer Ingelheim International Gmbh | Verbindungen als bradykinin-b1-antagonisten |
| US8470820B2 (en) * | 2010-01-22 | 2013-06-25 | Hoffman-La Roche Inc. | Nitrogen-containing heteroaryl derivatives |
| WO2012066549A1 (en) * | 2010-11-15 | 2012-05-24 | Ramot At Tel-Aviv University Ltd. | Dipeptide analogs for treating conditions associated with amyloid fibril formation |
| AR084070A1 (es) * | 2010-12-02 | 2013-04-17 | Constellation Pharmaceuticals Inc | Inhibidores del bromodominio y usos de los mismos |
| US8912221B2 (en) * | 2010-12-27 | 2014-12-16 | Hoffmann-La Roche Inc. | Biaryl amide derivatives |
| US8592426B2 (en) * | 2011-01-24 | 2013-11-26 | Hoffmann—La Roche Inc. | Aryl-benzocycloalkyl amide derivatives |
| WO2013072813A2 (en) * | 2011-11-17 | 2013-05-23 | Pfizer Inc. | Cytotoxic peptides and antibody drug conjugates thereof |
| US9326973B2 (en) * | 2012-01-13 | 2016-05-03 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
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- 2011-12-22 BR BR112013016431A patent/BR112013016431A2/pt not_active IP Right Cessation
- 2011-12-22 KR KR1020137018955A patent/KR20140014114A/ko not_active Withdrawn
- 2011-12-22 EP EP11799718.9A patent/EP2658848A1/en not_active Withdrawn
- 2011-12-22 WO PCT/EP2011/073717 patent/WO2012089601A1/en not_active Ceased
- 2011-12-22 RU RU2013133280/04A patent/RU2013133280A/ru not_active Application Discontinuation
- 2011-12-22 CN CN201180059302.0A patent/CN103249727B/zh not_active Expired - Fee Related
- 2011-12-22 MX MX2013005753A patent/MX2013005753A/es unknown
- 2011-12-22 JP JP2013546672A patent/JP2014501266A/ja active Pending
- 2011-12-22 CA CA2822188A patent/CA2822188A1/en not_active Abandoned
- 2011-12-27 AR ARP110104949A patent/AR084606A1/es not_active Application Discontinuation
-
2014
- 2014-10-29 US US14/527,299 patent/US20150065516A1/en not_active Abandoned
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