CA2796253A1 - Substituted 2,3-dihydroimidazo[1,2-c]quinazoline-containing combinations - Google Patents
Substituted 2,3-dihydroimidazo[1,2-c]quinazoline-containing combinations Download PDFInfo
- Publication number
- CA2796253A1 CA2796253A1 CA2796253A CA2796253A CA2796253A1 CA 2796253 A1 CA2796253 A1 CA 2796253A1 CA 2796253 A CA2796253 A CA 2796253A CA 2796253 A CA2796253 A CA 2796253A CA 2796253 A1 CA2796253 A1 CA 2796253A1
- Authority
- CA
- Canada
- Prior art keywords
- amino
- 6alkyl
- 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.)
- Abandoned
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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 29
- 150000003839 salts Chemical class 0.000 claims abstract description 54
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 47
- 239000012453 solvate Substances 0.000 claims abstract description 43
- 238000011282 treatment Methods 0.000 claims abstract description 31
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 27
- 239000008177 pharmaceutical agent Substances 0.000 claims abstract description 26
- 239000003814 drug Substances 0.000 claims abstract description 24
- 201000011510 cancer Diseases 0.000 claims abstract description 17
- 125000004421 aryl sulphonamide group Chemical group 0.000 claims abstract description 9
- 238000002360 preparation method Methods 0.000 claims abstract description 9
- 238000011321 prophylaxis Methods 0.000 claims abstract description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 167
- -1 nitro, hydroxy, cyano, carboxy, amino Chemical group 0.000 claims description 165
- 229910052736 halogen Inorganic materials 0.000 claims description 60
- 150000001875 compounds Chemical class 0.000 claims description 57
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 54
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 48
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 48
- 125000000217 alkyl group Chemical group 0.000 claims description 41
- 125000003118 aryl group Chemical group 0.000 claims description 38
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 35
- 125000001424 substituent group Chemical group 0.000 claims description 34
- 229910052739 hydrogen Inorganic materials 0.000 claims description 32
- 125000003545 alkoxy group Chemical group 0.000 claims description 29
- 229920006395 saturated elastomer Polymers 0.000 claims description 29
- 150000002367 halogens Chemical class 0.000 claims description 27
- 229910052757 nitrogen Inorganic materials 0.000 claims description 27
- 208000002154 non-small cell lung carcinoma Diseases 0.000 claims description 27
- 125000005842 heteroatom Chemical group 0.000 claims description 26
- 206010009944 Colon cancer Diseases 0.000 claims description 24
- 229910052717 sulfur Inorganic materials 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
- 125000002252 acyl group Chemical group 0.000 claims description 20
- 229910052731 fluorine Inorganic materials 0.000 claims description 20
- 125000000623 heterocyclic group Chemical group 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
- 239000001257 hydrogen Substances 0.000 claims description 16
- 125000004043 oxo group Chemical group O=* 0.000 claims description 16
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 15
- 206010006187 Breast cancer 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
- 208000026310 Breast neoplasm Diseases 0.000 claims description 14
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 14
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 14
- 125000005843 halogen group Chemical group 0.000 claims description 13
- 210000003494 hepatocyte Anatomy 0.000 claims description 13
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims description 13
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 13
- 201000002528 pancreatic cancer Diseases 0.000 claims description 13
- 208000008443 pancreatic carcinoma Diseases 0.000 claims description 13
- 201000009030 Carcinoma Diseases 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 201000001441 melanoma Diseases 0.000 claims description 12
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 229940124530 sulfonamide Drugs 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
- 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
- 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
- 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 7
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 7
- 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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 229910052740 iodine Inorganic materials 0.000 claims description 6
- 125000000325 methylidene group Chemical group [H]C([H])=* 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
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 5
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 5
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 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 description 5
- 125000006700 (C1-C6) alkylthio 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
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 4
- WMSPXQIQBQAWLL-UHFFFAOYSA-N cyclopropanesulfonamide Chemical compound NS(=O)(=O)C1CC1 WMSPXQIQBQAWLL-UHFFFAOYSA-N 0.000 claims description 4
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- VUWZPRWSIVNGKG-UHFFFAOYSA-N fluoromethane Chemical compound F[CH2] VUWZPRWSIVNGKG-UHFFFAOYSA-N 0.000 claims description 4
- 125000004785 fluoromethoxy group Chemical group [H]C([H])(F)O* 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 208000020816 lung neoplasm Diseases 0.000 claims description 4
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 4
- 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 description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000005545 phthalimidyl group Chemical group 0.000 claims description 4
- 125000003226 pyrazolyl group Chemical group 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
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 claims description 3
- 108010081348 HRT1 protein Hairy Proteins 0.000 claims description 3
- 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 claims description 3
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 3
- 201000005202 lung cancer Diseases 0.000 claims description 3
- 125000004178 (C1-C4) alkyl 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 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 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
- DDZSGPZIFZFUSF-SNVBAGLBSA-N 1-[(2r)-2,3-dihydroxypropyl]-n-[3,4,6-trifluoro-2-(2-fluoro-4-iodoanilino)phenyl]cyclopropane-1-sulfonamide Chemical compound FC=1C=C(F)C(F)=C(NC=2C(=CC(I)=CC=2)F)C=1NS(=O)(=O)C1(C[C@@H](O)CO)CC1 DDZSGPZIFZFUSF-SNVBAGLBSA-N 0.000 claims description 2
- DDZSGPZIFZFUSF-JTQLQIEISA-N 1-[(2s)-2,3-dihydroxypropyl]-n-[3,4,6-trifluoro-2-(2-fluoro-4-iodoanilino)phenyl]cyclopropane-1-sulfonamide Chemical compound FC=1C=C(F)C(F)=C(NC=2C(=CC(I)=CC=2)F)C=1NS(=O)(=O)C1(C[C@H](O)CO)CC1 DDZSGPZIFZFUSF-JTQLQIEISA-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
- 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
- AIMJAFTWPZNFBS-UHFFFAOYSA-N 2-amino-n-[7-methoxy-8-(3-morpholin-4-ylpropoxy)-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl]pyridine-4-carboxamide Chemical compound C1=CC=2C3=NCCN3C(NC(=O)C=3C=C(N)N=CC=3)=NC=2C(OC)=C1OCCCN1CCOCC1 AIMJAFTWPZNFBS-UHFFFAOYSA-N 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
- 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 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 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 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
- NNYLEQRGZWSNKY-UHFFFAOYSA-N 6-(cyclopentylamino)-n-[7-methoxy-8-(3-morpholin-4-ylpropoxy)-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl]pyridine-3-carboxamide Chemical compound C1=CC=2C3=NCCN3C(NC(=O)C=3C=NC(NC4CCCC4)=CC=3)=NC=2C(OC)=C1OCCCN1CCOCC1 NNYLEQRGZWSNKY-UHFFFAOYSA-N 0.000 claims description 2
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-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
- 125000006295 amino methylene group Chemical group [H]N(*)C([H])([H])* 0.000 claims description 2
- 150000001721 carbon Chemical group 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 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
- HNQIVZYLYMDVSB-NJFSPNSNSA-N methanesulfonamide Chemical compound [14CH3]S(N)(=O)=O HNQIVZYLYMDVSB-NJFSPNSNSA-N 0.000 claims description 2
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 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
- 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
- MLMKRJYFUDHWDR-UHFFFAOYSA-N n-[3,4-difluoro-2-(2-fluoro-4-iodoanilino)-6-(2-methoxyethoxy)phenyl]-1-(2,3-dihydroxypropyl)cyclopropane-1-sulfonamide Chemical compound C1CC1(CC(O)CO)S(=O)(=O)NC=1C(OCCOC)=CC(F)=C(F)C=1NC1=CC=C(I)C=C1F MLMKRJYFUDHWDR-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- XVZHLDZBHKUIHN-UHFFFAOYSA-N n-[3,4-difluoro-2-(2-fluoro-4-iodoanilino)-6-methoxyphenyl]-1-[3-hydroxy-2-(hydroxymethyl)propyl]cyclopropane-1-sulfonamide Chemical compound C1CC1(CC(CO)CO)S(=O)(=O)NC=1C(OC)=CC(F)=C(F)C=1NC1=CC=C(I)C=C1F XVZHLDZBHKUIHN-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
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- 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
- A61K31/4406—Non condensed pyridines; Hydrogenated derivatives thereof only substituted in position 3, e.g. zimeldine
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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
- A61K31/5375—1,4-Oxazines, e.g. morpholine
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
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- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
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| 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 |
| US9999623B2 (en) | 2013-04-08 | 2018-06-19 | 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 |
| EA201791974A1 (ru) * | 2015-03-09 | 2018-05-31 | Байер Фарма Акциенгезельшафт | Комбинации, содержащие замещенный 2,3-дигидроимидазо[1,2-с]хиназолин |
| CA2978807A1 (en) * | 2015-03-09 | 2016-09-15 | Bayer Pharma Aktiengesellschaft | Use of substituted 2,3-dihydroimidazo[1,2-c]quinazolines |
| EP3426657B1 (en) * | 2016-03-08 | 2022-07-13 | Bayer Pharma Aktiengesellschaft | 2 amino n [7 methoxy 2, 3-dihydroimidazo-[1, 2-c]quinazolin-5-yl]pyrimidine 5 carboxamides |
| WO2019002068A1 (en) | 2017-06-28 | 2019-01-03 | Bayer Consumer Care Ag | COMBINATION OF A PI3K INHIBITOR AND AN ANDROGEN RECEPTOR ANTAGONIST |
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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 |
| PT2042504E (pt) * | 2002-09-30 | 2011-09-07 | Bayer Schering Pharma Ag | Derivados da azolepirimidina fundida |
| 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 |
| AU2006272837B2 (en) * | 2005-07-21 | 2012-08-23 | Ardea Biosciences, Inc. | N-(arylamino)-sulfonamide 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 BR BR112012026480A patent/BR112012026480A2/pt not_active IP Right Cessation
- 2011-04-14 AU AU2011240003A patent/AU2011240003A1/en not_active Abandoned
- 2011-04-14 MA MA35308A patent/MA34158B1/fr unknown
- 2011-04-14 SG SG2012075511A patent/SG184550A1/en unknown
- 2011-04-14 WO PCT/EP2011/055917 patent/WO2011128407A2/en not_active Ceased
- 2011-04-14 MX MX2012012064A patent/MX2012012064A/es 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 US US13/640,994 patent/US20130184270A1/en not_active Abandoned
- 2011-04-14 JP JP2013504278A patent/JP5886271B2/ja not_active Expired - Fee Related
- 2011-04-14 PH PH1/2012/502069A patent/PH12012502069A1/en unknown
- 2011-04-14 KR KR1020127029890A patent/KR20130098155A/ko not_active Withdrawn
- 2011-04-14 EA EA201201414A patent/EA201201414A8/ru unknown
- 2011-04-14 CA CA2796253A patent/CA2796253A1/en not_active Abandoned
- 2011-04-14 CN CN201180029827.XA patent/CN102958540B/zh not_active Expired - Fee Related
-
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 CL CL2012002887A patent/CL2012002887A1/es unknown
- 2012-10-16 CR CR20120524A patent/CR20120524A/es unknown
- 2012-10-16 CU CU2012000150A patent/CU20120150A7/es unknown
- 2012-10-16 CO CO12182241A patent/CO6620036A2/es not_active Application Discontinuation
- 2012-10-16 DO DO2012000269A patent/DOP2012000269A/es unknown
- 2012-11-15 ZA ZA2012/08616A patent/ZA201208616B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ZA201208616B (en) | 2015-08-26 |
| CU20120150A7 (es) | 2013-02-26 |
| EA201201414A8 (ru) | 2013-12-30 |
| TN2012000493A1 (en) | 2014-04-01 |
| CN102958540A (zh) | 2013-03-06 |
| WO2011128407A2 (en) | 2011-10-20 |
| WO2011128407A9 (en) | 2011-12-22 |
| BR112012026480A2 (pt) | 2016-08-16 |
| IL222356A0 (en) | 2012-12-31 |
| PH12012502069A1 (en) | 2013-02-04 |
| EP2558126A2 (en) | 2013-02-20 |
| CL2012002887A1 (es) | 2013-01-18 |
| MA34158B1 (fr) | 2013-04-03 |
| MX2012012064A (es) | 2012-12-17 |
| AU2011240003A1 (en) | 2012-11-08 |
| JP2013525293A (ja) | 2013-06-20 |
| WO2011128407A3 (en) | 2012-02-23 |
| SG184550A1 (en) | 2012-11-29 |
| CN102958540B (zh) | 2015-09-02 |
| PE20130191A1 (es) | 2013-02-21 |
| CR20120524A (es) | 2013-01-09 |
| JP5886271B2 (ja) | 2016-03-16 |
| HK1182937A1 (en) | 2013-12-13 |
| DOP2012000269A (es) | 2012-12-15 |
| EA201201414A1 (ru) | 2013-04-30 |
| CO6620036A2 (es) | 2013-02-15 |
| US20130184270A1 (en) | 2013-07-18 |
| KR20130098155A (ko) | 2013-09-04 |
| ECSP12012261A (es) | 2012-11-30 |
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| EEER | Examination request |
Effective date: 20160407 |
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| FZDE | Discontinued |
Effective date: 20181127 |