JP2013525293A5 - - Google Patents
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- JP2013525293A5 JP2013525293A5 JP2013504278A JP2013504278A JP2013525293A5 JP 2013525293 A5 JP2013525293 A5 JP 2013525293A5 JP 2013504278 A JP2013504278 A JP 2013504278A JP 2013504278 A JP2013504278 A JP 2013504278A JP 2013525293 A5 JP2013525293 A5 JP 2013525293A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- amino
- phenyl
- fluoro
- difluoro
- 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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- 125000000217 alkyl group Chemical group 0.000 claims 106
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 76
- -1 nitro, hydroxy, cyano, carboxy, amino Chemical group 0.000 claims 58
- 229910052757 nitrogen Inorganic materials 0.000 claims 56
- 125000003545 alkoxy group Chemical group 0.000 claims 31
- 229910052736 halogen Inorganic materials 0.000 claims 30
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 24
- 125000003118 aryl group Chemical group 0.000 claims 20
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 18
- 229920006395 saturated elastomer Polymers 0.000 claims 17
- 125000001424 substituent group Chemical group 0.000 claims 17
- 229910052760 oxygen Inorganic materials 0.000 claims 15
- 150000002367 halogens Chemical class 0.000 claims 14
- 229910052739 hydrogen Inorganic materials 0.000 claims 14
- 125000005842 heteroatom Chemical group 0.000 claims 13
- 125000002252 acyl group Chemical group 0.000 claims 12
- 125000000623 heterocyclic group Chemical group 0.000 claims 12
- 229910052717 sulfur Inorganic materials 0.000 claims 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 11
- 239000000460 chlorine Substances 0.000 claims 9
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 8
- 229910052801 chlorine Inorganic materials 0.000 claims 8
- 229910052731 fluorine Inorganic materials 0.000 claims 8
- 125000005843 halogen group Chemical group 0.000 claims 8
- 239000001257 hydrogen Substances 0.000 claims 8
- 125000004043 oxo group Chemical group O=* 0.000 claims 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 7
- 150000003839 salts Chemical class 0.000 claims 7
- 229940124530 sulfonamide Drugs 0.000 claims 7
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 6
- 239000000825 pharmaceutical preparation Substances 0.000 claims 6
- 239000012453 solvate Substances 0.000 claims 6
- NTTQCLSBWRKUIJ-UHFFFAOYSA-N 2,3-dihydroimidazo[1,2-c]quinazoline Chemical class C1=CC=C2C3=NCCN3C=NC2=C1 NTTQCLSBWRKUIJ-UHFFFAOYSA-N 0.000 claims 5
- 229910052799 carbon Inorganic materials 0.000 claims 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims 4
- 125000004423 acyloxy group Chemical group 0.000 claims 4
- 125000004171 alkoxy aryl group Chemical group 0.000 claims 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 4
- 125000005466 alkylenyl group Chemical group 0.000 claims 4
- 125000004104 aryloxy group Chemical group 0.000 claims 4
- 229910052794 bromium Inorganic materials 0.000 claims 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 4
- 125000005059 halophenyl group Chemical group 0.000 claims 4
- 125000001072 heteroaryl group Chemical group 0.000 claims 4
- 125000005553 heteroaryloxy group Chemical group 0.000 claims 4
- 125000004076 pyridyl group Chemical group 0.000 claims 4
- 150000003456 sulfonamides Chemical class 0.000 claims 4
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 3
- 239000013066 combination product Substances 0.000 claims 3
- 229940127555 combination product Drugs 0.000 claims 3
- 150000004677 hydrates Chemical class 0.000 claims 3
- RDSACQWTXKSHJT-NSHDSACASA-N n-[3,4-difluoro-2-(2-fluoro-4-iodoanilino)-6-methoxyphenyl]-1-[(2s)-2,3-dihydroxypropyl]cyclopropane-1-sulfonamide Chemical compound C1CC1(C[C@H](O)CO)S(=O)(=O)NC=1C(OC)=CC(F)=C(F)C=1NC1=CC=C(I)C=C1F RDSACQWTXKSHJT-NSHDSACASA-N 0.000 claims 3
- DROIHSMGGKKIJT-UHFFFAOYSA-N propane-1-sulfonamide Chemical compound CCCS(N)(=O)=O DROIHSMGGKKIJT-UHFFFAOYSA-N 0.000 claims 3
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 2
- 125000004509 1,3,4-oxadiazol-2-yl group Chemical group O1C(=NN=C1)* 0.000 claims 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 2
- 125000006620 amino-(C1-C6) alkyl group Chemical group 0.000 claims 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 2
- 125000004421 aryl sulphonamide group Chemical group 0.000 claims 2
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 229910052740 iodine Inorganic materials 0.000 claims 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 2
- 125000002950 monocyclic group Chemical group 0.000 claims 2
- IIOJJZKXHLUULQ-UHFFFAOYSA-N n-[3,4-difluoro-2-(2-fluoro-4-iodoanilino)phenyl]-1-(2,3-dihydroxypropyl)cyclopropane-1-sulfonamide Chemical compound C=1C=C(F)C(F)=C(NC=2C(=CC(I)=CC=2)F)C=1NS(=O)(=O)C1(CC(O)CO)CC1 IIOJJZKXHLUULQ-UHFFFAOYSA-N 0.000 claims 2
- VQLUFKCIQCLFPG-UHFFFAOYSA-N n-[3,4-difluoro-2-(2-fluoro-4-iodoanilino)phenyl]thiophene-3-sulfonamide Chemical compound C=1C=C(I)C=C(F)C=1NC1=C(F)C(F)=CC=C1NS(=O)(=O)C=1C=CSC=1 VQLUFKCIQCLFPG-UHFFFAOYSA-N 0.000 claims 2
- PFAXMTRQGWBENF-UHFFFAOYSA-N n-[8-[3-[2-(hydroxymethyl)morpholin-4-yl]propoxy]-7-methoxy-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl]pyridine-3-carboxamide Chemical compound C1=CC=2C3=NCCN3C(NC(=O)C=3C=NC=CC=3)=NC=2C(OC)=C1OCCCN1CCOC(CO)C1 PFAXMTRQGWBENF-UHFFFAOYSA-N 0.000 claims 2
- 229960003966 nicotinamide Drugs 0.000 claims 2
- 235000005152 nicotinamide Nutrition 0.000 claims 2
- 239000011570 nicotinamide Substances 0.000 claims 2
- 125000005545 phthalimidyl group Chemical group 0.000 claims 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims 2
- QDXGKRWDQCEABB-UHFFFAOYSA-N pyrimidine-5-carboxamide Chemical compound NC(=O)C1=CN=CN=C1 QDXGKRWDQCEABB-UHFFFAOYSA-N 0.000 claims 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 239000000126 substance Substances 0.000 claims 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- MBIZXFATKUQOOA-UHFFFAOYSA-N 1,3,4-thiadiazole Chemical compound C1=NN=CS1 MBIZXFATKUQOOA-UHFFFAOYSA-N 0.000 claims 1
- 125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 claims 1
- OBQIGBKEHBRNCV-UHFFFAOYSA-N 1-(2,3-dihydroxypropyl)-n-[3,4,6-trifluoro-2-(4-fluoro-2-iodoanilino)phenyl]cyclopropane-1-sulfonamide Chemical compound FC=1C=C(F)C(F)=C(NC=2C(=CC(F)=CC=2)I)C=1NS(=O)(=O)C1(CC(O)CO)CC1 OBQIGBKEHBRNCV-UHFFFAOYSA-N 0.000 claims 1
- JBTLRKNMGRLWFC-UHFFFAOYSA-N 1-(2,3-dihydroxypropyl)-n-[6-ethyl-3,4-difluoro-2-(2-fluoro-4-iodoanilino)phenyl]cyclopropane-1-sulfonamide Chemical compound C1CC1(CC(O)CO)S(=O)(=O)NC=1C(CC)=CC(F)=C(F)C=1NC1=CC=C(I)C=C1F JBTLRKNMGRLWFC-UHFFFAOYSA-N 0.000 claims 1
- ORULZBOLSODREC-UHFFFAOYSA-N 1-chloro-n-[3,4-difluoro-2-(2-fluoro-4-iodoanilino)phenyl]methanesulfonamide Chemical compound FC1=CC=C(NS(=O)(=O)CCl)C(NC=2C(=CC(I)=CC=2)F)=C1F ORULZBOLSODREC-UHFFFAOYSA-N 0.000 claims 1
- ZBOJTTGEUFVTAT-UHFFFAOYSA-N 2,5-dichloro-n-[3,4-difluoro-2-(2-fluoro-4-iodoanilino)phenyl]thiophene-3-sulfonamide Chemical compound C=1C=C(I)C=C(F)C=1NC1=C(F)C(F)=CC=C1NS(=O)(=O)C=1C=C(Cl)SC=1Cl ZBOJTTGEUFVTAT-UHFFFAOYSA-N 0.000 claims 1
- MWYDSXOGIBMAET-UHFFFAOYSA-N 2-amino-N-[7-methoxy-8-(3-morpholin-4-ylpropoxy)-2,3-dihydro-1H-imidazo[1,2-c]quinazolin-5-ylidene]pyrimidine-5-carboxamide Chemical compound NC1=NC=C(C=N1)C(=O)N=C1N=C2C(=C(C=CC2=C2N1CCN2)OCCCN1CCOCC1)OC MWYDSXOGIBMAET-UHFFFAOYSA-N 0.000 claims 1
- BEMUPKPURPXIOV-UHFFFAOYSA-N 2-amino-n-[7-methoxy-8-(3-morpholin-4-ylpropoxy)-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl]-4-propylpyrimidine-5-carboxamide Chemical compound CCCC1=NC(N)=NC=C1C(=O)NC1=NC2=C(OC)C(OCCCN3CCOCC3)=CC=C2C2=NCCN12 BEMUPKPURPXIOV-UHFFFAOYSA-N 0.000 claims 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
- ZMSIFDIKIXVLDF-UHFFFAOYSA-N 2-methyl-1,3,4-oxadiazole Chemical compound CC1=NN=CO1 ZMSIFDIKIXVLDF-UHFFFAOYSA-N 0.000 claims 1
- QXDAKFBVTWGQHQ-UHFFFAOYSA-N 2-nitroacetamide Chemical compound NC(=O)C[N+]([O-])=O QXDAKFBVTWGQHQ-UHFFFAOYSA-N 0.000 claims 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 1
- UEOOZGNXIKEFSN-UHFFFAOYSA-N 3-bromo-5-chloro-n-[3,4-difluoro-2-(2-fluoro-4-iodoanilino)phenyl]thiophene-2-sulfonamide Chemical compound C=1C=C(I)C=C(F)C=1NC1=C(F)C(F)=CC=C1NS(=O)(=O)C=1SC(Cl)=CC=1Br UEOOZGNXIKEFSN-UHFFFAOYSA-N 0.000 claims 1
- DVUCRMPDQKMMKG-UHFFFAOYSA-N 3-chloro-n-[3,4-difluoro-2-(2-fluoro-4-iodoanilino)phenyl]propane-1-sulfonamide Chemical compound FC1=CC=C(NS(=O)(=O)CCCCl)C(NC=2C(=CC(I)=CC=2)F)=C1F DVUCRMPDQKMMKG-UHFFFAOYSA-N 0.000 claims 1
- AIBYAZOXYIOMCN-UHFFFAOYSA-N 4-[[3,4-difluoro-2-(2-fluoro-4-iodoanilino)phenyl]sulfamoyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1S(=O)(=O)NC1=CC=C(F)C(F)=C1NC1=CC=C(I)C=C1F AIBYAZOXYIOMCN-UHFFFAOYSA-N 0.000 claims 1
- BWNMSXPTALLYAA-UHFFFAOYSA-N 4-bromo-5-chloro-n-[3,4-difluoro-2-(2-fluoro-4-iodoanilino)phenyl]thiophene-2-sulfonamide Chemical compound C=1C=C(I)C=C(F)C=1NC1=C(F)C(F)=CC=C1NS(=O)(=O)C1=CC(Br)=C(Cl)S1 BWNMSXPTALLYAA-UHFFFAOYSA-N 0.000 claims 1
- XYSDQSBVOZVFKL-UHFFFAOYSA-N 5-(5-chloro-1,2,4-thiadiazol-3-yl)-n-[3,4-difluoro-2-(2-fluoro-4-iodoanilino)phenyl]thiophene-2-sulfonamide Chemical compound C=1C=C(I)C=C(F)C=1NC1=C(F)C(F)=CC=C1NS(=O)(=O)C(S1)=CC=C1C1=NSC(Cl)=N1 XYSDQSBVOZVFKL-UHFFFAOYSA-N 0.000 claims 1
- LYBVWNSFKARNDN-UHFFFAOYSA-N 5-bromo-n-[3,4-difluoro-2-(2-fluoro-4-iodoanilino)phenyl]thiophene-2-sulfonamide Chemical compound C=1C=C(I)C=C(F)C=1NC1=C(F)C(F)=CC=C1NS(=O)(=O)C1=CC=C(Br)S1 LYBVWNSFKARNDN-UHFFFAOYSA-N 0.000 claims 1
- OQSVNYNBDCDYTP-UHFFFAOYSA-N 5-chloro-n-[3,4-difluoro-2-(2-fluoro-4-iodoanilino)phenyl]-1,3-dimethylpyrazole-4-sulfonamide Chemical compound CC1=NN(C)C(Cl)=C1S(=O)(=O)NC1=CC=C(F)C(F)=C1NC1=CC=C(I)C=C1F OQSVNYNBDCDYTP-UHFFFAOYSA-N 0.000 claims 1
- RMTIXSPGGZTJJP-UHFFFAOYSA-N 5-chloro-n-[3,4-difluoro-2-(2-fluoro-4-iodoanilino)phenyl]thiophene-2-sulfonamide Chemical compound C=1C=C(I)C=C(F)C=1NC1=C(F)C(F)=CC=C1NS(=O)(=O)C1=CC=C(Cl)S1 RMTIXSPGGZTJJP-UHFFFAOYSA-N 0.000 claims 1
- 241000156724 Antirhea Species 0.000 claims 1
- 206010006187 Breast cancer Diseases 0.000 claims 1
- 208000026310 Breast neoplasm Diseases 0.000 claims 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 1
- 206010009944 Colon cancer Diseases 0.000 claims 1
- 208000001333 Colorectal Neoplasms Diseases 0.000 claims 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 1
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 150000001721 carbon Chemical group 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000006312 cyclopentyl amino group Chemical group [H]N(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 125000000131 cyclopropyloxy group Chemical group C1(CC1)O* 0.000 claims 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims 1
- 206010073071 hepatocellular carcinoma Diseases 0.000 claims 1
- 231100000844 hepatocellular carcinoma Toxicity 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- VFQXVTODMYMSMJ-UHFFFAOYSA-N isonicotinamide Chemical compound NC(=O)C1=CC=NC=C1 VFQXVTODMYMSMJ-UHFFFAOYSA-N 0.000 claims 1
- 201000005202 lung cancer Diseases 0.000 claims 1
- 208000020816 lung neoplasm Diseases 0.000 claims 1
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 229940126601 medicinal product Drugs 0.000 claims 1
- 201000001441 melanoma Diseases 0.000 claims 1
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 1
- AJDKPDGQECETSC-UHFFFAOYSA-N methyl 3-[[3,4-difluoro-2-(2-fluoro-4-iodoanilino)phenyl]sulfamoyl]thiophene-2-carboxylate Chemical compound S1C=CC(S(=O)(=O)NC=2C(=C(F)C(F)=CC=2)NC=2C(=CC(I)=CC=2)F)=C1C(=O)OC AJDKPDGQECETSC-UHFFFAOYSA-N 0.000 claims 1
- NXCFMWRKXKDJFD-UHFFFAOYSA-N methyl 5-[[3,4-difluoro-2-(2-fluoro-4-iodoanilino)phenyl]sulfamoyl]-1-methylpyrrole-2-carboxylate Chemical compound CN1C(C(=O)OC)=CC=C1S(=O)(=O)NC1=CC=C(F)C(F)=C1NC1=CC=C(I)C=C1F NXCFMWRKXKDJFD-UHFFFAOYSA-N 0.000 claims 1
- YSVNJRJKOSRWLI-UHFFFAOYSA-N n-[2-(2,4-dichloroanilino)-3,4-difluorophenyl]cyclopropanesulfonamide Chemical compound C=1C=C(Cl)C=C(Cl)C=1NC1=C(F)C(F)=CC=C1NS(=O)(=O)C1CC1 YSVNJRJKOSRWLI-UHFFFAOYSA-N 0.000 claims 1
- IKSNKNDSWYHLPH-UHFFFAOYSA-N n-[2-(4-chloro-2-fluoroanilino)-3,4-difluorophenyl]cyclopropanesulfonamide Chemical compound C=1C=C(Cl)C=C(F)C=1NC1=C(F)C(F)=CC=C1NS(=O)(=O)C1CC1 IKSNKNDSWYHLPH-UHFFFAOYSA-N 0.000 claims 1
- CMLJEMBUAYQSHE-UHFFFAOYSA-N n-[2-(4-tert-butyl-2-chloroanilino)-3,4-difluorophenyl]cyclopropanesulfonamide Chemical compound ClC1=CC(C(C)(C)C)=CC=C1NC1=C(F)C(F)=CC=C1NS(=O)(=O)C1CC1 CMLJEMBUAYQSHE-UHFFFAOYSA-N 0.000 claims 1
- JDKJCGUGODIUCP-UHFFFAOYSA-N n-[3,4,6-trifluoro-2-(2-fluoro-4-iodoanilino)phenyl]cyclopropanesulfonamide Chemical compound C=1C=C(I)C=C(F)C=1NC1=C(F)C(F)=CC(F)=C1NS(=O)(=O)C1CC1 JDKJCGUGODIUCP-UHFFFAOYSA-N 0.000 claims 1
- RDSACQWTXKSHJT-LLVKDONJSA-N n-[3,4-difluoro-2-(2-fluoro-4-iodoanilino)-6-methoxyphenyl]-1-[(2r)-2,3-dihydroxypropyl]cyclopropane-1-sulfonamide Chemical compound C1CC1(C[C@@H](O)CO)S(=O)(=O)NC=1C(OC)=CC(F)=C(F)C=1NC1=CC=C(I)C=C1F RDSACQWTXKSHJT-LLVKDONJSA-N 0.000 claims 1
- IGZSTXFYPGEPCA-UHFFFAOYSA-N n-[3,4-difluoro-2-(2-fluoro-4-iodoanilino)-6-methoxyphenyl]cyclobutanesulfonamide Chemical compound C1CCC1S(=O)(=O)NC=1C(OC)=CC(F)=C(F)C=1NC1=CC=C(I)C=C1F IGZSTXFYPGEPCA-UHFFFAOYSA-N 0.000 claims 1
- NATWBOPSBSGOTR-UHFFFAOYSA-N n-[3,4-difluoro-2-(2-fluoro-4-iodoanilino)-6-methoxyphenyl]methanesulfonamide Chemical compound COC1=CC(F)=C(F)C(NC=2C(=CC(I)=CC=2)F)=C1NS(C)(=O)=O NATWBOPSBSGOTR-UHFFFAOYSA-N 0.000 claims 1
- JQXQUUADCBDUKT-UHFFFAOYSA-N n-[3,4-difluoro-2-(2-fluoro-4-iodoanilino)phenyl]-1,2-dimethylimidazole-4-sulfonamide Chemical compound CN1C(C)=NC(S(=O)(=O)NC=2C(=C(F)C(F)=CC=2)NC=2C(=CC(I)=CC=2)F)=C1 JQXQUUADCBDUKT-UHFFFAOYSA-N 0.000 claims 1
- LRQDUHDUFGEDCZ-UHFFFAOYSA-N n-[3,4-difluoro-2-(2-fluoro-4-iodoanilino)phenyl]-1-methyl-3-(trifluoromethyl)pyrazole-4-sulfonamide Chemical compound FC(F)(F)C1=NN(C)C=C1S(=O)(=O)NC1=CC=C(F)C(F)=C1NC1=CC=C(I)C=C1F LRQDUHDUFGEDCZ-UHFFFAOYSA-N 0.000 claims 1
- JBCRBCONSWQXRR-UHFFFAOYSA-N n-[3,4-difluoro-2-(2-fluoro-4-iodoanilino)phenyl]-1-methylcyclopropane-1-sulfonamide Chemical compound C=1C=C(F)C(F)=C(NC=2C(=CC(I)=CC=2)F)C=1NS(=O)(=O)C1(C)CC1 JBCRBCONSWQXRR-UHFFFAOYSA-N 0.000 claims 1
- AHCKUVNFSOZGCR-UHFFFAOYSA-N n-[3,4-difluoro-2-(2-fluoro-4-iodoanilino)phenyl]-2,2,2-trifluoroethanesulfonamide Chemical compound FC1=CC=C(NS(=O)(=O)CC(F)(F)F)C(NC=2C(=CC(I)=CC=2)F)=C1F AHCKUVNFSOZGCR-UHFFFAOYSA-N 0.000 claims 1
- XZUMXDZUUIJWGR-UHFFFAOYSA-N n-[3,4-difluoro-2-(2-fluoro-4-iodoanilino)phenyl]-2,4-dimethyl-1,3-thiazole-5-sulfonamide Chemical compound S1C(C)=NC(C)=C1S(=O)(=O)NC1=CC=C(F)C(F)=C1NC1=CC=C(I)C=C1F XZUMXDZUUIJWGR-UHFFFAOYSA-N 0.000 claims 1
- AOCWYPLAWSBNRY-UHFFFAOYSA-N n-[3,4-difluoro-2-(2-fluoro-4-iodoanilino)phenyl]-2,5-dimethylfuran-3-sulfonamide Chemical compound O1C(C)=CC(S(=O)(=O)NC=2C(=C(F)C(F)=CC=2)NC=2C(=CC(I)=CC=2)F)=C1C AOCWYPLAWSBNRY-UHFFFAOYSA-N 0.000 claims 1
- VEXVCCJKINTCTA-UHFFFAOYSA-N n-[3,4-difluoro-2-(2-fluoro-4-iodoanilino)phenyl]-2,5-dimethylthiophene-3-sulfonamide Chemical compound S1C(C)=CC(S(=O)(=O)NC=2C(=C(F)C(F)=CC=2)NC=2C(=CC(I)=CC=2)F)=C1C VEXVCCJKINTCTA-UHFFFAOYSA-N 0.000 claims 1
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- KXINABDPZGHHMU-UHFFFAOYSA-N n-[3,4-difluoro-2-(2-fluoro-4-iodoanilino)phenyl]-2-methyl-5-(trifluoromethyl)furan-3-sulfonamide Chemical compound O1C(C(F)(F)F)=CC(S(=O)(=O)NC=2C(=C(F)C(F)=CC=2)NC=2C(=CC(I)=CC=2)F)=C1C KXINABDPZGHHMU-UHFFFAOYSA-N 0.000 claims 1
- HKZCEJSUKXYCNP-UHFFFAOYSA-N n-[3,4-difluoro-2-(2-fluoro-4-iodoanilino)phenyl]-2-methylpropane-2-sulfonamide Chemical compound CC(C)(C)S(=O)(=O)NC1=CC=C(F)C(F)=C1NC1=CC=C(I)C=C1F HKZCEJSUKXYCNP-UHFFFAOYSA-N 0.000 claims 1
- SKCRWQSUCTYHGF-UHFFFAOYSA-N n-[3,4-difluoro-2-(2-fluoro-4-iodoanilino)phenyl]-3,5-dimethyl-1,2-oxazole-4-sulfonamide Chemical compound CC1=NOC(C)=C1S(=O)(=O)NC1=CC=C(F)C(F)=C1NC1=CC=C(I)C=C1F SKCRWQSUCTYHGF-UHFFFAOYSA-N 0.000 claims 1
- BTFOPFBZQNDQJQ-UHFFFAOYSA-N n-[3,4-difluoro-2-(2-fluoro-4-iodoanilino)phenyl]-3-hydroxypropane-1-sulfonamide Chemical compound OCCCS(=O)(=O)NC1=CC=C(F)C(F)=C1NC1=CC=C(I)C=C1F BTFOPFBZQNDQJQ-UHFFFAOYSA-N 0.000 claims 1
- ZAPKGWUTWAQODO-UHFFFAOYSA-N n-[3,4-difluoro-2-(2-fluoro-4-iodoanilino)phenyl]-5-methyl-1,2-oxazole-4-sulfonamide Chemical compound O1N=CC(S(=O)(=O)NC=2C(=C(F)C(F)=CC=2)NC=2C(=CC(I)=CC=2)F)=C1C ZAPKGWUTWAQODO-UHFFFAOYSA-N 0.000 claims 1
- PCMHLGPVEQYHPG-UHFFFAOYSA-N n-[3,4-difluoro-2-(2-fluoro-4-iodoanilino)phenyl]-5-methylthiophene-2-sulfonamide Chemical compound S1C(C)=CC=C1S(=O)(=O)NC1=CC=C(F)C(F)=C1NC1=CC=C(I)C=C1F PCMHLGPVEQYHPG-UHFFFAOYSA-N 0.000 claims 1
- XSPQMZQPXNTOOE-UHFFFAOYSA-N n-[3,4-difluoro-2-(2-fluoro-4-iodoanilino)phenyl]-n-methylcyclopropanesulfonamide Chemical compound C1CC1S(=O)(=O)N(C)C1=CC=C(F)C(F)=C1NC1=CC=C(I)C=C1F XSPQMZQPXNTOOE-UHFFFAOYSA-N 0.000 claims 1
- KSWCSEXYKHVUHP-UHFFFAOYSA-N n-[3,4-difluoro-2-(2-fluoro-4-iodoanilino)phenyl]benzenesulfonamide Chemical compound C=1C=C(I)C=C(F)C=1NC1=C(F)C(F)=CC=C1NS(=O)(=O)C1=CC=CC=C1 KSWCSEXYKHVUHP-UHFFFAOYSA-N 0.000 claims 1
- FPPMHVSDXJYUKL-UHFFFAOYSA-N n-[3,4-difluoro-2-(2-fluoro-4-iodoanilino)phenyl]butane-1-sulfonamide Chemical compound CCCCS(=O)(=O)NC1=CC=C(F)C(F)=C1NC1=CC=C(I)C=C1F FPPMHVSDXJYUKL-UHFFFAOYSA-N 0.000 claims 1
- CORRTDDVKPNIRC-UHFFFAOYSA-N n-[3,4-difluoro-2-(2-fluoro-4-iodoanilino)phenyl]butane-2-sulfonamide Chemical compound CCC(C)S(=O)(=O)NC1=CC=C(F)C(F)=C1NC1=CC=C(I)C=C1F CORRTDDVKPNIRC-UHFFFAOYSA-N 0.000 claims 1
- QVFCQVIAXHDDAM-UHFFFAOYSA-N n-[3,4-difluoro-2-(2-fluoro-4-iodoanilino)phenyl]cyclohexanesulfonamide Chemical compound C=1C=C(I)C=C(F)C=1NC1=C(F)C(F)=CC=C1NS(=O)(=O)C1CCCCC1 QVFCQVIAXHDDAM-UHFFFAOYSA-N 0.000 claims 1
- XPONOSPNILDOOQ-UHFFFAOYSA-N n-[3,4-difluoro-2-(2-fluoro-4-iodoanilino)phenyl]cyclopentanesulfonamide Chemical compound C=1C=C(I)C=C(F)C=1NC1=C(F)C(F)=CC=C1NS(=O)(=O)C1CCCC1 XPONOSPNILDOOQ-UHFFFAOYSA-N 0.000 claims 1
- RLWZDTUAZCEHGP-UHFFFAOYSA-N n-[3,4-difluoro-2-(2-fluoro-4-iodoanilino)phenyl]cyclopropanesulfonamide Chemical compound C=1C=C(I)C=C(F)C=1NC1=C(F)C(F)=CC=C1NS(=O)(=O)C1CC1 RLWZDTUAZCEHGP-UHFFFAOYSA-N 0.000 claims 1
- XDGYXPPEVYEFTJ-UHFFFAOYSA-N n-[3,4-difluoro-2-(2-fluoro-4-iodoanilino)phenyl]furan-2-sulfonamide Chemical compound C=1C=C(I)C=C(F)C=1NC1=C(F)C(F)=CC=C1NS(=O)(=O)C1=CC=CO1 XDGYXPPEVYEFTJ-UHFFFAOYSA-N 0.000 claims 1
- GDUQFUXTPDOHRM-UHFFFAOYSA-N n-[3,4-difluoro-2-(2-fluoro-4-iodoanilino)phenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=C(F)C(F)=C1NC1=CC=C(I)C=C1F GDUQFUXTPDOHRM-UHFFFAOYSA-N 0.000 claims 1
- OJEFRCWRZRAHAS-UHFFFAOYSA-N n-[3,4-difluoro-2-(2-fluoro-4-iodoanilino)phenyl]propane-2-sulfonamide Chemical compound CC(C)S(=O)(=O)NC1=CC=C(F)C(F)=C1NC1=CC=C(I)C=C1F OJEFRCWRZRAHAS-UHFFFAOYSA-N 0.000 claims 1
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- XJOADFGFTJCTOD-UHFFFAOYSA-N n-[3,4-difluoro-2-(4-iodo-2-methylanilino)phenyl]cyclopropanesulfonamide Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=CC=C1NS(=O)(=O)C1CC1 XJOADFGFTJCTOD-UHFFFAOYSA-N 0.000 claims 1
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- KPUFBHNWKRJCPC-UHFFFAOYSA-N n-[6-ethoxy-3,4-difluoro-2-(4-fluoro-2-iodoanilino)phenyl]cyclopropanesulfonamide Chemical compound C1CC1S(=O)(=O)NC=1C(OCC)=CC(F)=C(F)C=1NC1=CC=C(F)C=C1I KPUFBHNWKRJCPC-UHFFFAOYSA-N 0.000 claims 1
- MYZQRTALORWOFJ-UHFFFAOYSA-N n-[7-methoxy-8-(3-morpholin-4-ylpropoxy)-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl]pyrimidine-5-carboxamide Chemical compound C1=CC=2C3=NCCN3C(NC(=O)C=3C=NC=NC=3)=NC=2C(OC)=C1OCCCN1CCOCC1 MYZQRTALORWOFJ-UHFFFAOYSA-N 0.000 claims 1
- WJTQKNQTKYYWRW-UHFFFAOYSA-N n-[8-[2-(4-ethylmorpholin-2-yl)ethoxy]-7-methoxy-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl]pyridine-3-carboxamide Chemical compound C1N(CC)CCOC1CCOC1=CC=C(C=2N(CCN=2)C(NC(=O)C=2C=NC=CC=2)=N2)C2=C1OC WJTQKNQTKYYWRW-UHFFFAOYSA-N 0.000 claims 1
- XYVNDTVSILQGKM-UHFFFAOYSA-N n-[8-[2-(dimethylamino)ethoxy]-7-methoxy-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl]pyrimidine-5-carboxamide Chemical compound N=1C=2C(OC)=C(OCCN(C)C)C=CC=2C2=NCCN2C=1NC(=O)C1=CN=CN=C1 XYVNDTVSILQGKM-UHFFFAOYSA-N 0.000 claims 1
- FYGKNFXODIEWJB-UHFFFAOYSA-N n-[8-[3-(dimethylamino)propoxy]-7-methoxy-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl]-1-oxidopyridin-1-ium-3-carboxamide Chemical compound N=1C=2C(OC)=C(OCCCN(C)C)C=CC=2C2=NCCN2C=1NC(=O)C1=CC=C[N+]([O-])=C1 FYGKNFXODIEWJB-UHFFFAOYSA-N 0.000 claims 1
- BQDLTRWPXDTWFK-HDICACEKSA-N n-[8-[3-[(2r,6s)-2,6-dimethylmorpholin-4-yl]propoxy]-7-methoxy-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl]pyridine-3-carboxamide Chemical compound C1=CC=2C3=NCCN3C(NC(=O)C=3C=NC=CC=3)=NC=2C(OC)=C1OCCCN1C[C@H](C)O[C@H](C)C1 BQDLTRWPXDTWFK-HDICACEKSA-N 0.000 claims 1
- LTQFHGCERMMMMZ-IYBDPMFKSA-N n-[8-[3-[(2s,6r)-2,6-dimethylmorpholin-4-yl]propoxy]-7-methoxy-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl]-2,4-dimethyl-1,3-thiazole-5-carboxamide Chemical compound C1=CC=2C3=NCCN3C(NC(=O)C3=C(N=C(C)S3)C)=NC=2C(OC)=C1OCCCN1C[C@H](C)O[C@H](C)C1 LTQFHGCERMMMMZ-IYBDPMFKSA-N 0.000 claims 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 208000002154 non-small cell lung carcinoma Diseases 0.000 claims 1
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- OJNHERVKFUWZGH-UHFFFAOYSA-N pyrrolidin-1-yl hydrogen carbonate Chemical compound OC(=O)ON1CCCC1 OJNHERVKFUWZGH-UHFFFAOYSA-N 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
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- 0 CC(C(**)=*C1)=C1O Chemical compound CC(C(**)=*C1)=C1O 0.000 description 3
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| EP2168583A1 (en) | 2008-09-24 | 2010-03-31 | Bayer Schering Pharma Aktiengesellschaft | Use of substituted 2,3-dihydroimidazo[1,2-c]quinazolines for the treatment of myeloma |
| UA113280C2 (xx) | 2010-11-11 | 2017-01-10 | АМІНОСПИРТЗАМІЩЕНІ ПОХІДНІ 2,3-ДИГІДРОІМІДАЗО$1,2-c]ХІНАЗОЛІНУ, ПРИДАТНІ ДЛЯ ЛІКУВАННЯ ГІПЕРПРОЛІФЕРАТИВНИХ ПОРУШЕНЬ І ЗАХВОРЮВАНЬ, ПОВ'ЯЗАНИХ З АНГІОГЕНЕЗОМ | |
| JO3733B1 (ar) * | 2011-04-05 | 2021-01-31 | Bayer Ip Gmbh | استخدام 3,2-دايهيدروايميدازو[1, 2 -c]كوينازولينات مستبدلة |
| EP2508525A1 (en) | 2011-04-05 | 2012-10-10 | Bayer Pharma Aktiengesellschaft | Substituted 2,3-dihydroimidazo[1,2-c]quinazoline salts |
| WO2014160034A1 (en) * | 2013-03-14 | 2014-10-02 | The Board Of Trustees Of The Leland Stanford Junior University | Aldehyde dehydrogenase-1 modulators and methods of use thereof |
| AP2015008750A0 (en) | 2013-04-08 | 2015-09-30 | Bayer Pharma AG | Use of substituted 2,3-dihydroimidazo[1,2-c] quinazolines for treating lymphomas |
| WO2015082376A2 (en) * | 2013-12-03 | 2015-06-11 | Bayer Pharma Aktiengesellschaft | Use of pi3k-inhibitors |
| EA201791974A1 (ru) * | 2015-03-09 | 2018-05-31 | Байер Фарма Акциенгезельшафт | Комбинации, содержащие замещенный 2,3-дигидроимидазо[1,2-с]хиназолин |
| WO2016142313A1 (en) * | 2015-03-09 | 2016-09-15 | Bayer Pharma Aktiengesellschaft | Use of substituted 2,3-dihydroimidazo[1,2-c]quinazolines |
| WO2017153220A1 (en) * | 2016-03-08 | 2017-09-14 | Bayer Pharma Aktiengesellschaft | 2—amino—n— [7—methoxy—2, 3-dihydroimidazo-[1, 2-c] quinazolin-5-yl] pyrimidine—5—carboxamides |
| CA3068324A1 (en) | 2017-06-28 | 2019-01-03 | Bayer Consumer Care Ag | Combination of a pi3k-inhibitor with an androgen receptor antagonist |
| US11498923B2 (en) | 2017-12-13 | 2022-11-15 | Merck Sharp & Dohme Llc | Substituted imidazo[1,2-c]quinazolines as A2A antagonists |
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| US5023252A (en) | 1985-12-04 | 1991-06-11 | Conrex Pharmaceutical Corporation | Transdermal and trans-membrane delivery of drugs |
| US5011472A (en) | 1988-09-06 | 1991-04-30 | Brown University Research Foundation | Implantable delivery system for biological factors |
| WO2004029055A1 (en) * | 2002-09-30 | 2004-04-08 | Bayer Pharmaceuticals Corporation | Fused azole-pyrimidine derivatives |
| JP4323793B2 (ja) | 2002-12-16 | 2009-09-02 | キヤノン株式会社 | ズームレンズ及びそれを有する光学機器 |
| DE102004064002B4 (de) | 2004-08-04 | 2019-05-09 | Continental Automotive Gmbh | System zum Überwachen einer Sensorvorrichtung |
| US8101799B2 (en) * | 2005-07-21 | 2012-01-24 | Ardea Biosciences | Derivatives of N-(arylamino) sulfonamides as inhibitors of MEK |
| MX2008002114A (es) * | 2005-07-21 | 2008-04-17 | Ardea Biosciences Inc | Inhibidores de n-(arilamino)-sulfonamida de mek. |
| AR064106A1 (es) * | 2006-12-05 | 2009-03-11 | Bayer Schering Pharma Ag | Derivados de 2,3-dihidroimidazo [1,2-c] quinazolina sustituida utiles para el tratamiento de enfermedades y trastornos hiper-proliferativos asociados con la angiogenesis |
| CN102131771A (zh) * | 2008-04-14 | 2011-07-20 | 阿迪生物科学公司 | 组合物及其制备和使用方法 |
| EP2168583A1 (en) * | 2008-09-24 | 2010-03-31 | Bayer Schering Pharma Aktiengesellschaft | Use of substituted 2,3-dihydroimidazo[1,2-c]quinazolines for the treatment of myeloma |
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2011
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- 2011-04-14 KR KR1020127029890A patent/KR20130098155A/ko not_active Withdrawn
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- 2011-04-14 AU AU2011240003A patent/AU2011240003A1/en not_active Abandoned
- 2011-04-14 CN CN201180029827.XA patent/CN102958540B/zh not_active Expired - Fee Related
- 2011-04-14 JP JP2013504278A patent/JP5886271B2/ja not_active Expired - Fee Related
- 2011-04-14 PH PH1/2012/502069A patent/PH12012502069A1/en unknown
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- 2011-04-14 MA MA35308A patent/MA34158B1/fr unknown
- 2011-04-14 PE PE2012002028A patent/PE20130191A1/es not_active Application Discontinuation
- 2011-04-14 EP EP11714553A patent/EP2558126A2/en not_active Withdrawn
- 2011-04-14 CA CA2796253A patent/CA2796253A1/en not_active Abandoned
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2012
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- 2012-10-12 TN TNP2012000493A patent/TN2012000493A1/en unknown
- 2012-10-15 EC ECSP12012261 patent/ECSP12012261A/es unknown
- 2012-10-16 CO CO12182241A patent/CO6620036A2/es not_active Application Discontinuation
- 2012-10-16 CR CR20120524A patent/CR20120524A/es unknown
- 2012-10-16 CL CL2012002887A patent/CL2012002887A1/es unknown
- 2012-10-16 CU CU2012000150A patent/CU20120150A7/es unknown
- 2012-10-16 DO DO2012000269A patent/DOP2012000269A/es unknown
- 2012-11-15 ZA ZA2012/08616A patent/ZA201208616B/en unknown
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