KR20130098155A - 치환된 ２,３-디히드로이미다조［１,２-ｃ］퀴나졸린-함유 조합물 - Google Patents
치환된 ２,３-디히드로이미다조［１,２-ｃ］퀴나졸린-함유 조합물 Download PDFInfo
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- KR20130098155A KR20130098155A KR1020127029890A KR20127029890A KR20130098155A KR 20130098155 A KR20130098155 A KR 20130098155A KR 1020127029890 A KR1020127029890 A KR 1020127029890A KR 20127029890 A KR20127029890 A KR 20127029890A KR 20130098155 A KR20130098155 A KR 20130098155A
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- Prior art keywords
- alkyl
- amino
- phenyl
- fluoro
- difluoro
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- NTTQCLSBWRKUIJ-UHFFFAOYSA-N 2,3-dihydroimidazo[1,2-c]quinazoline Chemical class C1=CC=C2C3=NCCN3C=NC2=C1 NTTQCLSBWRKUIJ-UHFFFAOYSA-N 0.000 title claims abstract description 14
- -1 aryl sulfonamide compound Chemical class 0.000 claims abstract description 228
- 150000003839 salts Chemical class 0.000 claims abstract description 53
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 46
- 239000012453 solvate Substances 0.000 claims abstract description 43
- 239000008177 pharmaceutical agent Substances 0.000 claims abstract description 27
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 27
- 238000011282 treatment Methods 0.000 claims abstract description 26
- 239000003814 drug Substances 0.000 claims abstract description 22
- 150000004677 hydrates Chemical class 0.000 claims abstract description 18
- 201000011510 cancer Diseases 0.000 claims abstract description 17
- 230000002265 prevention Effects 0.000 claims abstract description 7
- 238000004519 manufacturing process Methods 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 206
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 150
- 229910052757 nitrogen Inorganic materials 0.000 claims description 97
- 229910052736 halogen Inorganic materials 0.000 claims description 60
- 150000001875 compounds Chemical class 0.000 claims description 58
- 125000003545 alkoxy group Chemical group 0.000 claims description 54
- 125000003118 aryl group Chemical group 0.000 claims description 40
- 150000002367 halogens Chemical class 0.000 claims description 40
- 125000001424 substituent group Chemical group 0.000 claims description 35
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 32
- 229910052739 hydrogen Inorganic materials 0.000 claims description 32
- 229920006395 saturated elastomer Polymers 0.000 claims description 29
- 229910052717 sulfur Inorganic materials 0.000 claims description 26
- 125000005842 heteroatom Chemical group 0.000 claims description 25
- 206010009944 Colon cancer Diseases 0.000 claims description 24
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 21
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 20
- 229910052731 fluorine Inorganic materials 0.000 claims description 20
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 20
- 239000000460 chlorine Substances 0.000 claims description 18
- 229910052801 chlorine Inorganic materials 0.000 claims description 18
- 125000000623 heterocyclic group Chemical group 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- 125000004043 oxo group Chemical group O=* 0.000 claims description 16
- 206010006187 Breast cancer Diseases 0.000 claims description 15
- 208000026310 Breast neoplasm Diseases 0.000 claims description 15
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 15
- 206010073071 hepatocellular carcinoma Diseases 0.000 claims description 15
- 231100000844 hepatocellular carcinoma Toxicity 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 14
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims description 14
- 201000002528 pancreatic cancer Diseases 0.000 claims description 14
- 208000008443 pancreatic carcinoma Diseases 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 12
- 125000002252 acyl group Chemical group 0.000 claims description 12
- 125000006620 amino-(C1-C6) alkyl group Chemical group 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
- 201000001441 melanoma Diseases 0.000 claims description 12
- 229940124530 sulfonamide Drugs 0.000 claims description 12
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 125000004423 acyloxy group Chemical group 0.000 claims description 8
- 125000004171 alkoxy aryl group Chemical group 0.000 claims description 8
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 8
- 125000005466 alkylenyl group Chemical group 0.000 claims description 8
- 125000004104 aryloxy group Chemical group 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 8
- 125000005059 halophenyl group Chemical group 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 8
- 125000004076 pyridyl group Chemical group 0.000 claims description 8
- 150000003456 sulfonamides Chemical class 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 6
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- DROIHSMGGKKIJT-UHFFFAOYSA-N propane-1-sulfonamide Chemical compound CCCS(N)(=O)=O DROIHSMGGKKIJT-UHFFFAOYSA-N 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 4
- 125000004509 1,3,4-oxadiazol-2-yl group Chemical group O1C(=NN=C1)* 0.000 claims description 4
- 208000001333 Colorectal Neoplasms Diseases 0.000 claims description 4
- 229910052770 Uranium Inorganic materials 0.000 claims description 4
- 125000004442 acylamino group Chemical group 0.000 claims description 4
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
- 208000020816 lung neoplasm Diseases 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 4
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 4
- 125000002950 monocyclic group Chemical group 0.000 claims description 4
- 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 description 4
- 208000002154 non-small cell lung carcinoma Diseases 0.000 claims description 4
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 4
- QDXGKRWDQCEABB-UHFFFAOYSA-N pyrimidine-5-carboxamide Chemical compound NC(=O)C1=CN=CN=C1 QDXGKRWDQCEABB-UHFFFAOYSA-N 0.000 claims description 4
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 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 description 3
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 3
- 125000004421 aryl sulphonamide group Chemical group 0.000 claims description 3
- 125000002619 bicyclic group Chemical group 0.000 claims description 3
- 201000005202 lung cancer Diseases 0.000 claims description 3
- 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 description 3
- 125000005545 phthalimidyl group Chemical group 0.000 claims description 3
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 2
- MBIZXFATKUQOOA-UHFFFAOYSA-N 1,3,4-thiadiazole Chemical compound C1=NN=CS1 MBIZXFATKUQOOA-UHFFFAOYSA-N 0.000 claims description 2
- 125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 claims description 2
- OBQIGBKEHBRNCV-UHFFFAOYSA-N 1-(2,3-dihydroxypropyl)-n-[3,4,6-trifluoro-2-(4-fluoro-2-iodoanilino)phenyl]cyclopropane-1-sulfonamide Chemical class 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- KTFDYVNEGTXQCV-UHFFFAOYSA-N 2-Thiophenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CS1 KTFDYVNEGTXQCV-UHFFFAOYSA-N 0.000 claims description 2
- RWCMUSCEPMWINC-UHFFFAOYSA-N 2-amino-n-[7-methoxy-8-(3-morpholin-4-ylpropoxy)-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl]-1,3-thiazole-5-carboxamide Chemical compound C1=CC=2C3=NCCN3C(NC(=O)C=3SC(N)=NC=3)=NC=2C(OC)=C1OCCCN1CCOCC1 RWCMUSCEPMWINC-UHFFFAOYSA-N 0.000 claims description 2
- NFNLEBOQOSHXAE-UHFFFAOYSA-N 2-amino-n-[7-methoxy-8-(3-morpholin-4-ylpropoxy)-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl]-4-methyl-1,3-thiazole-5-carboxamide Chemical compound C1=CC=2C3=NCCN3C(NC(=O)C3=C(N=C(N)S3)C)=NC=2C(OC)=C1OCCCN1CCOCC1 NFNLEBOQOSHXAE-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 2
- ZMSIFDIKIXVLDF-UHFFFAOYSA-N 2-methyl-1,3,4-oxadiazole Chemical compound CC1=NN=CO1 ZMSIFDIKIXVLDF-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- OQSVNYNBDCDYTP-UHFFFAOYSA-N 5-chloro-n-[3,4-difluoro-2-(2-fluoro-4-iodoanilino)phenyl]-1,3-dimethylpyrazole-4-sulfonamide Chemical class 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 description 2
- 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 description 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 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 description 2
- 125000000131 cyclopropyloxy group Chemical group C1(CC1)O* 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 2
- VFQXVTODMYMSMJ-UHFFFAOYSA-N isonicotinamide Chemical compound NC(=O)C1=CC=NC=C1 VFQXVTODMYMSMJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims description 2
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
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- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
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- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
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- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP10160109 | 2010-04-16 | ||
| EP10160109.4 | 2010-04-16 | ||
| PCT/EP2011/055917 WO2011128407A2 (en) | 2010-04-16 | 2011-04-14 | Substituted 2,3-dihydroimidazo[1,2-c]quinazoline-containing combinations |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20130098155A true KR20130098155A (ko) | 2013-09-04 |
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| KR1020127029890A Withdrawn KR20130098155A (ko) | 2010-04-16 | 2011-04-14 | 치환된 ２,３-디히드로이미다조［１,２-ｃ］퀴나졸린-함유 조합물 |
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|---|---|
| US (1) | US20130184270A1 (enExample) |
| EP (1) | EP2558126A2 (enExample) |
| JP (1) | JP5886271B2 (enExample) |
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| CN (1) | CN102958540B (enExample) |
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Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| CA2908776C (en) | 2013-04-08 | 2021-08-10 | Bayer Pharma Aktiengesellschaft | 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 |
| KR20180013851A (ko) * | 2015-03-09 | 2018-02-07 | 바이엘 파마 악티엔게젤샤프트 | 치환된 2,3-디히드로이미다조[1,2-c]퀴나졸린-함유 조합물 |
| MX2017011607A (es) * | 2015-03-09 | 2018-04-10 | Bayer Pharma AG | Uso de 2,3-dihidroimidazol[1,2-c]quinazolinas sustituidas. |
| CN108884098B (zh) * | 2016-03-08 | 2021-09-14 | 拜耳制药股份公司 | 2-氨基-N-[7-甲氧基-2,3-二氢咪唑并[1,2-c]喹唑啉-5-基]嘧啶-5-甲酰胺类 |
| US11185549B2 (en) | 2017-06-28 | 2021-11-30 | Bayer Consumer Care Ag | Combination of a PI3K-inhibitor with an androgen receptor antagonist |
| EP3723754A4 (en) * | 2017-12-13 | 2021-05-19 | Merck Sharp & Dohme Corp. | IMIDAZO [1,2-C] QUINAZOLINE-5-AMINE COMPOUNDS WITH PROPERTIES OF A2A ANTAGONIST |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| SI1549652T1 (sl) * | 2002-09-30 | 2009-04-30 | Bayer Healthcare Ag | Kondenzirani azolpirimidinski derivati |
| 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 |
| CA2618218C (en) * | 2005-07-21 | 2015-06-30 | Ardea Biosciences, Inc. | N-(arylamino)-sulfonamide inhibitors of mek |
| US8101799B2 (en) * | 2005-07-21 | 2012-01-24 | Ardea Biosciences | Derivatives of N-(arylamino) sulfonamides as inhibitors of 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 |
| BRPI0911297A2 (pt) * | 2008-04-14 | 2019-09-24 | Ardea Biosciences Inc | composição e métodos para preparo e uso das mesmas |
| 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 |
-
2011
- 2011-04-14 KR KR1020127029890A patent/KR20130098155A/ko not_active Withdrawn
- 2011-04-14 MX MX2012012064A patent/MX2012012064A/es unknown
- 2011-04-14 US US13/640,994 patent/US20130184270A1/en not_active Abandoned
- 2011-04-14 EA EA201201414A patent/EA201201414A8/ru unknown
- 2011-04-14 SG SG2012075511A patent/SG184550A1/en unknown
- 2011-04-14 EP EP11714553A patent/EP2558126A2/en not_active Withdrawn
- 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 WO PCT/EP2011/055917 patent/WO2011128407A2/en not_active Ceased
- 2011-04-14 BR BR112012026480A patent/BR112012026480A2/pt not_active IP Right Cessation
- 2011-04-14 CA CA2796253A patent/CA2796253A1/en not_active Abandoned
- 2011-04-14 MA MA35308A patent/MA34158B1/fr unknown
- 2011-04-14 PH PH1/2012/502069A patent/PH12012502069A1/en unknown
- 2011-04-14 AU AU2011240003A patent/AU2011240003A1/en not_active Abandoned
- 2011-04-14 PE PE2012002028A patent/PE20130191A1/es not_active Application Discontinuation
-
2012
- 2012-10-11 IL IL222356A patent/IL222356A0/en unknown
- 2012-10-12 TN TNP2012000493A patent/TN2012000493A1/en unknown
- 2012-10-15 EC ECSP12012261 patent/ECSP12012261A/es unknown
- 2012-10-16 CR CR20120524A patent/CR20120524A/es unknown
- 2012-10-16 DO DO2012000269A patent/DOP2012000269A/es unknown
- 2012-10-16 CU CU2012000150A patent/CU20120150A7/es unknown
- 2012-10-16 CL CL2012002887A patent/CL2012002887A1/es unknown
- 2012-10-16 CO CO12182241A patent/CO6620036A2/es not_active Application Discontinuation
- 2012-11-15 ZA ZA2012/08616A patent/ZA201208616B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EA201201414A1 (ru) | 2013-04-30 |
| EP2558126A2 (en) | 2013-02-20 |
| ZA201208616B (en) | 2015-08-26 |
| CU20120150A7 (es) | 2013-02-26 |
| DOP2012000269A (es) | 2012-12-15 |
| MX2012012064A (es) | 2012-12-17 |
| IL222356A0 (en) | 2012-12-31 |
| EA201201414A8 (ru) | 2013-12-30 |
| WO2011128407A2 (en) | 2011-10-20 |
| CN102958540B (zh) | 2015-09-02 |
| CO6620036A2 (es) | 2013-02-15 |
| SG184550A1 (en) | 2012-11-29 |
| PE20130191A1 (es) | 2013-02-21 |
| JP5886271B2 (ja) | 2016-03-16 |
| WO2011128407A3 (en) | 2012-02-23 |
| CL2012002887A1 (es) | 2013-01-18 |
| BR112012026480A2 (pt) | 2016-08-16 |
| AU2011240003A1 (en) | 2012-11-08 |
| PH12012502069A1 (en) | 2013-02-04 |
| CN102958540A (zh) | 2013-03-06 |
| WO2011128407A9 (en) | 2011-12-22 |
| CR20120524A (es) | 2013-01-09 |
| ECSP12012261A (es) | 2012-11-30 |
| JP2013525293A (ja) | 2013-06-20 |
| MA34158B1 (fr) | 2013-04-03 |
| TN2012000493A1 (en) | 2014-04-01 |
| US20130184270A1 (en) | 2013-07-18 |
| CA2796253A1 (en) | 2011-10-20 |
| HK1182937A1 (en) | 2013-12-13 |
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