JP2013536253A5 - - Google Patents
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- JP2013536253A5 JP2013536253A5 JP2013526299A JP2013526299A JP2013536253A5 JP 2013536253 A5 JP2013536253 A5 JP 2013536253A5 JP 2013526299 A JP2013526299 A JP 2013526299A JP 2013526299 A JP2013526299 A JP 2013526299A JP 2013536253 A5 JP2013536253 A5 JP 2013536253A5
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- JP
- Japan
- Prior art keywords
- group
- alkyl
- chloro
- methyl
- substituted
- 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.)
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- 125000003545 alkoxy group Chemical group 0.000 claims 27
- 125000000217 alkyl group Chemical group 0.000 claims 20
- 229910052736 halogen Inorganic materials 0.000 claims 20
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 17
- -1 amino, carboxyl Chemical group 0.000 claims 17
- 150000002367 halogens Chemical class 0.000 claims 17
- 125000001424 substituent group Chemical group 0.000 claims 15
- 150000001875 compounds Chemical class 0.000 claims 14
- 229910052739 hydrogen Inorganic materials 0.000 claims 13
- 239000001257 hydrogen Substances 0.000 claims 13
- 125000003277 amino group Chemical group 0.000 claims 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 12
- 125000003282 alkyl amino group Chemical group 0.000 claims 11
- 150000003839 salts Chemical class 0.000 claims 11
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims 10
- 150000002431 hydrogen Chemical class 0.000 claims 10
- 229910052760 oxygen Inorganic materials 0.000 claims 9
- 125000005257 alkyl acyl group Chemical group 0.000 claims 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims 8
- 229920006395 saturated elastomer Polymers 0.000 claims 8
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 7
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims 6
- 125000004760 (C1-C4) alkylsulfonylamino group Chemical group 0.000 claims 6
- 125000000623 heterocyclic group Chemical group 0.000 claims 6
- 229910052717 sulfur Inorganic materials 0.000 claims 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims 5
- 125000001153 fluoro group Chemical group F* 0.000 claims 5
- 125000003003 spiro group Chemical group 0.000 claims 5
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims 4
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims 4
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 4
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 4
- 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims 4
- 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims 4
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 4
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 4
- 206010020718 hyperplasia Diseases 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 206010028980 Neoplasm Diseases 0.000 claims 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 125000005843 halogen group Chemical group 0.000 claims 3
- 125000005842 heteroatom Chemical group 0.000 claims 3
- 230000002390 hyperplastic effect Effects 0.000 claims 3
- 125000002757 morpholinyl group Chemical group 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 125000004193 piperazinyl group Chemical group 0.000 claims 3
- 125000004547 quinazolin-6-yl group Chemical group N1=CN=CC2=CC(=CC=C12)* 0.000 claims 3
- 239000002994 raw material Substances 0.000 claims 3
- 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical group C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims 2
- NKANXQFJJICGDU-QPLCGJKRSA-N Tamoxifen Chemical compound C=1C=CC=CC=1C(/CC)=C(C=1C=CC(OCCN(C)C)=CC=1)/C1=CC=CC=C1 NKANXQFJJICGDU-QPLCGJKRSA-N 0.000 claims 2
- 125000003368 amide group Chemical group 0.000 claims 2
- 229960003328 benzoyl peroxide Drugs 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 2
- 239000002552 dosage form Substances 0.000 claims 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000002541 furyl group Chemical group 0.000 claims 2
- 239000003018 immunosuppressive agent Substances 0.000 claims 2
- 239000003112 inhibitor Substances 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims 2
- 238000006467 substitution reaction Methods 0.000 claims 2
- 229940124597 therapeutic agent Drugs 0.000 claims 2
- 125000000335 thiazolyl group Chemical group 0.000 claims 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- UAADZBLHQJCZQF-FNORWQNLSA-N (e)-n-[4-(3-chloro-4-fluoroanilino)-7-(2-methyl-2,7-diazaspiro[4.5]decan-7-yl)quinazolin-6-yl]-4-piperidin-1-ylbut-2-enamide Chemical compound C1N(C)CCC21CN(C=1C(=CC3=C(NC=4C=C(Cl)C(F)=CC=4)N=CN=C3C=1)NC(=O)\C=C\CN1CCCCC1)CCC2 UAADZBLHQJCZQF-FNORWQNLSA-N 0.000 claims 1
- QRLCOKUUHXYTRD-SNAWJCMRSA-N (e)-n-[4-(3-chloro-4-fluoroanilino)-7-(7-oxabicyclo[2.2.1]heptan-3-yloxy)quinazolin-6-yl]-4-piperidin-1-ylbut-2-enamide Chemical compound C1=C(Cl)C(F)=CC=C1NC(C1=C2)=NC=NC1=CC(OC1C3CCC(O3)C1)=C2NC(=O)\C=C\CN1CCCCC1 QRLCOKUUHXYTRD-SNAWJCMRSA-N 0.000 claims 1
- UQPXIVIEBNLQFI-SNAWJCMRSA-N (e)-n-[4-(3-chloro-4-fluoroanilino)-7-(8-oxabicyclo[3.2.1]octan-3-yloxy)quinazolin-6-yl]-4-piperidin-1-ylbut-2-enamide Chemical compound C1=C(Cl)C(F)=CC=C1NC(C1=C2)=NC=NC1=CC(OC1CC3CCC(O3)C1)=C2NC(=O)\C=C\CN1CCCCC1 UQPXIVIEBNLQFI-SNAWJCMRSA-N 0.000 claims 1
- LJWNMAODVOTUAM-SNAWJCMRSA-N (e)-n-[4-(3-chloro-4-fluoroanilino)-7-[(7-methyl-7-azaspiro[3.5]nonan-2-yl)methoxy]quinazolin-6-yl]-4-(dimethylamino)but-2-enamide Chemical compound N1=CN=C2C=C(OCC3CC4(C3)CCN(C)CC4)C(NC(=O)/C=C/CN(C)C)=CC2=C1NC1=CC=C(F)C(Cl)=C1 LJWNMAODVOTUAM-SNAWJCMRSA-N 0.000 claims 1
- CWGYREFEPBBLMM-ONEGZZNKSA-N (e)-n-[4-(3-chloro-4-fluoroanilino)-7-[(7-methyl-7-azaspiro[3.5]nonan-2-yl)methoxy]quinazolin-6-yl]but-2-enamide Chemical compound N1=CN=C2C=C(OCC3CC4(C3)CCN(C)CC4)C(NC(=O)/C=C/C)=CC2=C1NC1=CC=C(F)C(Cl)=C1 CWGYREFEPBBLMM-ONEGZZNKSA-N 0.000 claims 1
- OYDVXDQSNXBQHS-SNAWJCMRSA-N (e)-n-[4-(3-chloro-4-fluoroanilino)-7-[(7-methyl-7-azaspiro[3.5]nonan-2-yl)methoxy]quinazolin-6-yl]pent-2-enamide Chemical compound N1=CN=C2C=C(OCC3CC4(C3)CCN(C)CC4)C(NC(=O)/C=C/CC)=CC2=C1NC1=CC=C(F)C(Cl)=C1 OYDVXDQSNXBQHS-SNAWJCMRSA-N 0.000 claims 1
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-dimethylaminopyridine Substances CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims 1
- 208000036764 Adenocarcinoma of the esophagus Diseases 0.000 claims 1
- 206010005003 Bladder cancer Diseases 0.000 claims 1
- 208000003174 Brain Neoplasms Diseases 0.000 claims 1
- 206010006187 Breast cancer Diseases 0.000 claims 1
- 208000026310 Breast neoplasm Diseases 0.000 claims 1
- GAGWJHPBXLXJQN-UORFTKCHSA-N Capecitabine Chemical compound C1=C(F)C(NC(=O)OCCCCC)=NC(=O)N1[C@H]1[C@H](O)[C@H](O)[C@@H](C)O1 GAGWJHPBXLXJQN-UORFTKCHSA-N 0.000 claims 1
- GAGWJHPBXLXJQN-UHFFFAOYSA-N Capecitabine Natural products C1=C(F)C(NC(=O)OCCCCC)=NC(=O)N1C1C(O)C(O)C(C)O1 GAGWJHPBXLXJQN-UHFFFAOYSA-N 0.000 claims 1
- DLGOEMSEDOSKAD-UHFFFAOYSA-N Carmustine Chemical compound ClCCNC(=O)N(N=O)CCCl DLGOEMSEDOSKAD-UHFFFAOYSA-N 0.000 claims 1
- 206010008342 Cervix carcinoma Diseases 0.000 claims 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 1
- 206010009944 Colon cancer Diseases 0.000 claims 1
- 208000001333 Colorectal Neoplasms Diseases 0.000 claims 1
- CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 claims 1
- 206010014733 Endometrial cancer Diseases 0.000 claims 1
- 206010014759 Endometrial neoplasm Diseases 0.000 claims 1
- HKVAMNSJSFKALM-GKUWKFKPSA-N Everolimus Chemical compound C1C[C@@H](OCCO)[C@H](OC)C[C@@H]1C[C@@H](C)[C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@](O)(O2)[C@H](C)CC[C@H]2C[C@H](OC)/C(C)=C/C=C/C=C/[C@@H](C)C[C@@H](C)C(=O)[C@H](OC)[C@H](O)/C(C)=C/[C@@H](C)C(=O)C1 HKVAMNSJSFKALM-GKUWKFKPSA-N 0.000 claims 1
- VWUXBMIQPBEWFH-WCCTWKNTSA-N Fulvestrant Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3[C@H](CCCCCCCCCS(=O)CCCC(F)(F)C(F)(F)F)CC2=C1 VWUXBMIQPBEWFH-WCCTWKNTSA-N 0.000 claims 1
- 208000032612 Glial tumor Diseases 0.000 claims 1
- 201000010915 Glioblastoma multiforme Diseases 0.000 claims 1
- 206010018338 Glioma Diseases 0.000 claims 1
- 208000008839 Kidney Neoplasms Diseases 0.000 claims 1
- 239000005517 L01XE01 - Imatinib Substances 0.000 claims 1
- 239000003798 L01XE11 - Pazopanib Substances 0.000 claims 1
- 208000019693 Lung disease Diseases 0.000 claims 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 1
- 241000124008 Mammalia Species 0.000 claims 1
- 229940121849 Mitotic inhibitor Drugs 0.000 claims 1
- ZDZOTLJHXYCWBA-VCVYQWHSSA-N N-debenzoyl-N-(tert-butoxycarbonyl)-10-deacetyltaxol Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C=4C=CC=CC=4)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 ZDZOTLJHXYCWBA-VCVYQWHSSA-N 0.000 claims 1
- 208000015914 Non-Hodgkin lymphomas Diseases 0.000 claims 1
- 206010030137 Oesophageal adenocarcinoma Diseases 0.000 claims 1
- 206010061534 Oesophageal squamous cell carcinoma Diseases 0.000 claims 1
- 206010033128 Ovarian cancer Diseases 0.000 claims 1
- 206010061535 Ovarian neoplasm Diseases 0.000 claims 1
- 229930012538 Paclitaxel Natural products 0.000 claims 1
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims 1
- 206010060862 Prostate cancer Diseases 0.000 claims 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 1
- 206010038389 Renal cancer Diseases 0.000 claims 1
- 208000036765 Squamous cell carcinoma of the esophagus Diseases 0.000 claims 1
- 208000005718 Stomach Neoplasms Diseases 0.000 claims 1
- 101710183280 Topoisomerase Proteins 0.000 claims 1
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims 1
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 125000004442 acylamino group Chemical group 0.000 claims 1
- 229940100198 alkylating agent Drugs 0.000 claims 1
- 239000002168 alkylating agent Substances 0.000 claims 1
- 230000000340 anti-metabolite Effects 0.000 claims 1
- 230000000259 anti-tumor effect Effects 0.000 claims 1
- 229940100197 antimetabolite Drugs 0.000 claims 1
- 239000002256 antimetabolite Substances 0.000 claims 1
- 239000002246 antineoplastic agent Substances 0.000 claims 1
- VSRXQHXAPYXROS-UHFFFAOYSA-N azanide;cyclobutane-1,1-dicarboxylic acid;platinum(2+) Chemical compound [NH2-].[NH2-].[Pt+2].OC(=O)C1(C(O)=O)CCC1 VSRXQHXAPYXROS-UHFFFAOYSA-N 0.000 claims 1
- 229960000397 bevacizumab Drugs 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 229960004117 capecitabine Drugs 0.000 claims 1
- AOGYCOYQMAVAFD-UHFFFAOYSA-M carbonochloridate Chemical compound [O-]C(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-M 0.000 claims 1
- 229960004562 carboplatin Drugs 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 229960005243 carmustine Drugs 0.000 claims 1
- 201000007455 central nervous system cancer Diseases 0.000 claims 1
- 208000025997 central nervous system neoplasm Diseases 0.000 claims 1
- 201000010881 cervical cancer Diseases 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 239000003638 chemical reducing agent Substances 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 230000001684 chronic effect Effects 0.000 claims 1
- DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 claims 1
- 229960004316 cisplatin Drugs 0.000 claims 1
- 229960004397 cyclophosphamide Drugs 0.000 claims 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
- 229960003668 docetaxel Drugs 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 208000028653 esophageal adenocarcinoma Diseases 0.000 claims 1
- 208000007276 esophageal squamous cell carcinoma Diseases 0.000 claims 1
- 229960005167 everolimus Drugs 0.000 claims 1
- 229960002258 fulvestrant Drugs 0.000 claims 1
- 206010017758 gastric cancer Diseases 0.000 claims 1
- 229960005277 gemcitabine Drugs 0.000 claims 1
- SDUQYLNIPVEERB-QPPQHZFASA-N gemcitabine Chemical compound O=C1N=C(N)C=CN1[C@H]1C(F)(F)[C@H](O)[C@@H](CO)O1 SDUQYLNIPVEERB-QPPQHZFASA-N 0.000 claims 1
- 208000005017 glioblastoma Diseases 0.000 claims 1
- 208000002409 gliosarcoma Diseases 0.000 claims 1
- 239000003102 growth factor Substances 0.000 claims 1
- 201000010536 head and neck cancer Diseases 0.000 claims 1
- 208000014829 head and neck neoplasm Diseases 0.000 claims 1
- 229940022353 herceptin Drugs 0.000 claims 1
- 239000005556 hormone Substances 0.000 claims 1
- 229940088597 hormone Drugs 0.000 claims 1
- KTUFNOKKBVMGRW-UHFFFAOYSA-N imatinib Chemical compound C1CN(C)CCN1CC1=CC=C(C(=O)NC=2C=C(NC=3N=C(C=CN=3)C=3C=NC=CC=3)C(C)=CC=2)C=C1 KTUFNOKKBVMGRW-UHFFFAOYSA-N 0.000 claims 1
- 229960002411 imatinib Drugs 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 229960003444 immunosuppressant agent Drugs 0.000 claims 1
- 229940125721 immunosuppressive agent Drugs 0.000 claims 1
- 125000001786 isothiazolyl group Chemical group 0.000 claims 1
- 201000010982 kidney cancer Diseases 0.000 claims 1
- 229960003881 letrozole Drugs 0.000 claims 1
- HPJKCIUCZWXJDR-UHFFFAOYSA-N letrozole Chemical compound C1=CC(C#N)=CC=C1C(N1N=CN=C1)C1=CC=C(C#N)C=C1 HPJKCIUCZWXJDR-UHFFFAOYSA-N 0.000 claims 1
- 201000007270 liver cancer Diseases 0.000 claims 1
- 208000014018 liver neoplasm Diseases 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
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- NCZQDYVBQGDYSN-UHFFFAOYSA-N n-[4-(3-chloro-4-fluoroanilino)-7-[(2-methyl-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-4-yl)methoxy]quinazolin-6-yl]prop-2-enamide Chemical compound C12CN(C)CC2CCC1COC(C(=CC1=2)NC(=O)C=C)=CC1=NC=NC=2NC1=CC=C(F)C(Cl)=C1 NCZQDYVBQGDYSN-UHFFFAOYSA-N 0.000 claims 1
- YQHUCWCDHISMJX-UHFFFAOYSA-N n-[4-(3-chloro-4-fluoroanilino)-7-[(5-methyl-5-azaspiro[2.4]heptan-2-yl)methoxy]quinazolin-6-yl]prop-2-enamide Chemical compound C1N(C)CCC11C(COC=2C(=CC3=C(NC=4C=C(Cl)C(F)=CC=4)N=CN=C3C=2)NC(=O)C=C)C1 YQHUCWCDHISMJX-UHFFFAOYSA-N 0.000 claims 1
- BQMYDVOWFBYDAV-UHFFFAOYSA-N n-[4-(3-chloro-4-fluoroanilino)-7-[(6-methyl-6-azaspiro[2.5]octan-2-yl)methoxy]quinazolin-6-yl]prop-2-enamide Chemical compound C1CN(C)CCC11C(COC=2C(=CC3=C(NC=4C=C(Cl)C(F)=CC=4)N=CN=C3C=2)NC(=O)C=C)C1 BQMYDVOWFBYDAV-UHFFFAOYSA-N 0.000 claims 1
- VOJWEAFYQFRFOG-UHFFFAOYSA-N n-[4-(3-chloro-4-fluoroanilino)-7-[(7-methyl-7-azabicyclo[2.2.1]heptan-3-yl)methoxy]quinazolin-6-yl]prop-2-enamide Chemical compound CN1C(C2)CCC1C2COC(C(=CC1=2)NC(=O)C=C)=CC1=NC=NC=2NC1=CC=C(F)C(Cl)=C1 VOJWEAFYQFRFOG-UHFFFAOYSA-N 0.000 claims 1
- KJBZQIKLKWQVLL-UHFFFAOYSA-N n-[4-(3-chloro-4-fluoroanilino)-7-[(7-methyl-7-azaspiro[3.5]nonan-2-yl)methoxy]quinazolin-6-yl]prop-2-enamide Chemical compound C1CN(C)CCC11CC(COC=2C(=CC3=C(NC=4C=C(Cl)C(F)=CC=4)N=CN=C3C=2)NC(=O)C=C)C1 KJBZQIKLKWQVLL-UHFFFAOYSA-N 0.000 claims 1
- JFUDQORFBVGLMB-UHFFFAOYSA-N n-[4-(3-chloro-4-fluoroanilino)-7-[(8-methyl-1-oxa-8-azaspiro[4.5]decan-2-yl)methoxy]quinazolin-6-yl]prop-2-enamide Chemical compound C1CN(C)CCC11OC(COC=2C(=CC3=C(NC=4C=C(Cl)C(F)=CC=4)N=CN=C3C=2)NC(=O)C=C)CC1 JFUDQORFBVGLMB-UHFFFAOYSA-N 0.000 claims 1
- JGSKJUYVTDKFKT-UHFFFAOYSA-N n-[4-(3-chloro-4-fluoroanilino)-7-[(8-methyl-1-oxa-8-azaspiro[4.5]decan-3-yl)methoxy]quinazolin-6-yl]prop-2-enamide Chemical compound C1CN(C)CCC11OCC(COC=2C(=CC3=C(NC=4C=C(Cl)C(F)=CC=4)N=CN=C3C=2)NC(=O)C=C)C1 JGSKJUYVTDKFKT-UHFFFAOYSA-N 0.000 claims 1
- VXROPYQMLFHZBA-UHFFFAOYSA-N n-[4-(3-chloro-4-fluoroanilino)-7-[(8-methyl-1-oxa-8-azaspiro[4.5]decan-3-yl)oxy]quinazolin-6-yl]prop-2-enamide Chemical compound C1CN(C)CCC11OCC(OC=2C(=CC3=C(NC=4C=C(Cl)C(F)=CC=4)N=CN=C3C=2)NC(=O)C=C)C1 VXROPYQMLFHZBA-UHFFFAOYSA-N 0.000 claims 1
- BXZUUQKJSRTWMD-UHFFFAOYSA-N n-[4-(3-chloro-4-fluoroanilino)-7-[(8-methyl-8-azabicyclo[3.2.1]octan-3-yl)oxy]quinazolin-6-yl]prop-2-enamide Chemical compound CN1C(C2)CCC1CC2OC(C(=CC1=2)NC(=O)C=C)=CC1=NC=NC=2NC1=CC=C(F)C(Cl)=C1 BXZUUQKJSRTWMD-UHFFFAOYSA-N 0.000 claims 1
- FGYHOZIXSUEJDM-UHFFFAOYSA-N n-[4-(3-chloro-4-fluoroanilino)-7-[2-(3-methyl-3-azabicyclo[3.2.1]octan-8-yl)ethoxy]quinazolin-6-yl]prop-2-enamide Chemical compound C1N(C)CC2CCC1C2CCOC(C(=CC1=2)NC(=O)C=C)=CC1=NC=NC=2NC1=CC=C(F)C(Cl)=C1 FGYHOZIXSUEJDM-UHFFFAOYSA-N 0.000 claims 1
- YAPFODKXVWEFPW-UHFFFAOYSA-N n-[4-(3-chloro-4-fluoroanilino)-7-[2-(6-methyl-6-azaspiro[2.5]octan-2-yl)ethoxy]quinazolin-6-yl]prop-2-enamide Chemical compound C1CN(C)CCC11C(CCOC=2C(=CC3=C(NC=4C=C(Cl)C(F)=CC=4)N=CN=C3C=2)NC(=O)C=C)C1 YAPFODKXVWEFPW-UHFFFAOYSA-N 0.000 claims 1
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| PCT/CN2011/001466 WO2012027960A1 (zh) | 2010-08-30 | 2011-08-30 | 苯胺取代的喹唑啉衍生物及其制备方法与应用 |
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| JP5688877B2 (ja) | 2005-11-11 | 2015-03-25 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | 癌疾患の治療用キナゾリン誘導体 |
| PT2451445T (pt) | 2009-07-06 | 2019-07-10 | Boehringer Ingelheim Int | Processo para secagem de bibw2992, dos seus sais e de formulações farmacêuticas sólidas compreendendo este ingrediente ativo |
| CN102382106A (zh) * | 2010-08-30 | 2012-03-21 | 黄振华 | 苯胺取代的喹唑啉衍生物 |
| WO2012122058A2 (en) | 2011-03-04 | 2012-09-13 | Newgen Therapeutics, Inc. | Alkyne substituted quinazoline compound and methods of use |
| WO2012155339A1 (zh) | 2011-05-17 | 2012-11-22 | 江苏康缘药业股份有限公司 | 4-苯胺-6-丁烯酰胺-7-烷醚喹唑啉衍生物及其制备方法和用途 |
| CN103717590B (zh) * | 2011-05-17 | 2016-05-11 | 江苏康缘药业股份有限公司 | 喹唑啉-7-醚化合物及使用方法 |
| EP2716633B1 (en) * | 2011-05-26 | 2017-05-17 | Xuanzhu Pharma Co., Ltd. | Quinazoline derivative as tyrosine-kinase inhibitor, preparation method therefor and application thereof |
| CN103965174B (zh) * | 2013-02-01 | 2016-05-11 | 通化济达医药有限公司 | 含有锌结合基的喹唑啉基egfr酪氨酸激酶抑制剂 |
| TWI609012B (zh) | 2013-04-28 | 2017-12-21 | 廣東東陽光藥業有限公司 | 氨基喹唑啉類衍生物及其鹽和使用方法 |
| WO2015007219A1 (en) * | 2013-07-18 | 2015-01-22 | Shanghai Fochon Pharmaceutical Co Ltd | Quinazoline derivatives, compositions thereof, and use as pharmaceuticals |
| US9242965B2 (en) | 2013-12-31 | 2016-01-26 | Boehringer Ingelheim International Gmbh | Process for the manufacture of (E)-4-N,N-dialkylamino crotonic acid in HX salt form and use thereof for synthesis of EGFR tyrosine kinase inhibitors |
| JP6674027B2 (ja) * | 2015-12-25 | 2020-04-01 | シュアンチュー ファーマ カンパニー，リミティド | キナゾリン誘導体の結晶及びその調製方法 |
| US10633364B2 (en) | 2015-12-25 | 2020-04-28 | Xuanzhu Pharma Co., Ltd. | Crystals of quinazoline derivative and preparation method therefor |
| ES2903416T3 (es) * | 2016-04-28 | 2022-04-01 | Jiangsu Hengrui Medicine Co | Método de preparación de un inhibidor de tirosina quinasa y de un derivado del mismo |
| CN107721986A (zh) * | 2016-08-12 | 2018-02-23 | 山东轩竹医药科技有限公司 | 喹唑啉类酪氨酸激酶抑制剂的晶型 |
| CN107721985A (zh) * | 2016-08-12 | 2018-02-23 | 山东轩竹医药科技有限公司 | 喹唑啉类酪氨酸激酶抑制剂的晶型 |
| CN107721987A (zh) * | 2016-08-12 | 2018-02-23 | 山东轩竹医药科技有限公司 | 喹唑啉类酪氨酸激酶抑制剂的晶型 |
| WO2018028673A1 (zh) * | 2016-08-12 | 2018-02-15 | 山东轩竹医药科技有限公司 | 喹唑啉衍生物类酪氨酸激酶抑制剂的盐及其晶型 |
| WO2019170088A1 (zh) * | 2018-03-06 | 2019-09-12 | 北京赛特明强医药科技有限公司 | 一种噁嗪并喹唑啉与噁嗪并喹啉类化合物及其制备方法和应用 |
| CN110498804A (zh) * | 2018-05-18 | 2019-11-26 | 山东轩竹医药科技有限公司 | 喹唑啉衍生物类酪氨酸激酶抑制剂的新用途 |
| JP2022502495A (ja) | 2018-09-25 | 2022-01-11 | ブラック ダイアモンド セラピューティクス，インコーポレイティド | チロシンキナーゼ阻害剤としてのキナゾリン誘導体、組成物、それらの作製方法、およびそれらの使用 |
| CN111773225A (zh) * | 2019-04-04 | 2020-10-16 | 山东轩竹医药科技有限公司 | Kras及其突变体表达抑制剂 |
| CN111777620A (zh) * | 2019-04-04 | 2020-10-16 | 山东轩竹医药科技有限公司 | 酪氨酸激酶抑制剂的新用途 |
| CN111777621B (zh) * | 2019-04-04 | 2023-03-10 | 山东轩竹医药科技有限公司 | 喹唑啉衍生物类酪氨酸激酶抑制剂的新用途 |
| AU2020328598A1 (en) | 2019-08-15 | 2022-03-03 | Black Diamond Therapeutics, Inc. | Alkynyl quinazoline compounds |
| CN110963972A (zh) * | 2019-11-21 | 2020-04-07 | 苏州明锐医药科技有限公司 | 一种喹唑啉衍生物及其制备方法与药物用途 |
| US20240166626A1 (en) * | 2021-02-09 | 2024-05-23 | Thomas Jefferson University | Compounds and Methods for Preventing, Treating, or Ameliorating Airway Disease |
| CN113264888A (zh) * | 2021-03-04 | 2021-08-17 | 江苏康可得生物技术股份有限公司 | 酪氨酸激酶抑制剂及其药物应用 |
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| DE10042061A1 (de) | 2000-08-26 | 2002-03-07 | Boehringer Ingelheim Pharma | Bicyclische Heterocyclen,diese Verbindungen enthaltende Arzneimittel, deren Verwendung und Verfahren zu ihrer Herstellung |
| DE10042060A1 (de) * | 2000-08-26 | 2002-03-07 | Boehringer Ingelheim Pharma | Bicyclische Heterocyclen, diese Verbindungen enthaltende Arzneimittel, deren Verwendung und Verfahren zu ihrer Herstellung |
| US7576074B2 (en) * | 2002-07-15 | 2009-08-18 | Rice Kenneth D | Receptor-type kinase modulators and methods of use |
| PE20040945A1 (es) * | 2003-02-05 | 2004-12-14 | Warner Lambert Co | Preparacion de quinazolinas substituidas |
| KR20080095915A (ko) | 2004-05-06 | 2008-10-29 | 워너-램버트 캄파니 엘엘씨 | 4-페닐아미노-퀴나졸린-6-일-아미드 |
| EP1957468A2 (en) * | 2005-09-06 | 2008-08-20 | T.K. Signal Ltd. | Polyalkylene glycol derivatives of 4 - (phenylamino)quinazolines useful as irreversible inhibitors of epidermal growth factor receptor tyrosine kinase |
| JP5688877B2 (ja) * | 2005-11-11 | 2015-03-25 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | 癌疾患の治療用キナゾリン誘導体 |
| ATE446294T1 (de) * | 2005-11-15 | 2009-11-15 | Array Biopharma Inc | N4-phenyl-chinazolin-4-aminderivate und verwandte verbindungen als inhibitoren der erbb-typ-i- rezeptortyrosinkinase zur behandlung hyperproliferativer krankheiten |
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| ES2553114T3 (es) * | 2009-07-29 | 2015-12-04 | Nerviano Medical Sciences S.R.L. | Sales de inhibidor de plk |
| CN102382106A (zh) | 2010-08-30 | 2012-03-21 | 黄振华 | 苯胺取代的喹唑啉衍生物 |
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| US8764172B2 (en) * | 2010-09-03 | 2014-07-01 | Seiko Epson Corporation | Printing apparatus, printing material cartridge, adaptor for printing material container, and circuit board |
| CN102452989B (zh) * | 2010-10-19 | 2014-10-22 | 山东轩竹医药科技有限公司 | 苯胺取代的喹唑啉衍生物 |
| US8541576B2 (en) * | 2010-12-17 | 2013-09-24 | Nerviano Medical Sciences Srl | Substituted pyrazolo-quinazoline derivatives as kinase inhibitors |
| WO2012155339A1 (zh) * | 2011-05-17 | 2012-11-22 | 江苏康缘药业股份有限公司 | 4-苯胺-6-丁烯酰胺-7-烷醚喹唑啉衍生物及其制备方法和用途 |
| EP2716633B1 (en) | 2011-05-26 | 2017-05-17 | Xuanzhu Pharma Co., Ltd. | Quinazoline derivative as tyrosine-kinase inhibitor, preparation method therefor and application thereof |
| CA2908098A1 (en) * | 2013-03-15 | 2014-09-25 | Celgene Avilomics Research, Inc. | Mk2 inhibitors and uses thereof |
| CN105431437B (zh) * | 2013-07-02 | 2020-03-10 | 理森制药股份公司 | PI3K蛋白激酶抑制剂，特别是δ抑制剂和/或γ抑制剂 |
| CN108078990B (zh) * | 2016-11-23 | 2023-06-02 | 山东轩竹医药科技有限公司 | 喹唑啉衍生物类酪氨酸激酶抑制剂的新用途 |
-
2010
- 2010-08-30 CN CN2010102661778A patent/CN102382106A/zh active Pending
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2011
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- 2011-08-30 WO PCT/CN2011/001466 patent/WO2012027960A1/zh not_active Ceased
- 2011-08-30 DK DK11820990.7T patent/DK2612860T3/en active
- 2011-08-30 EP EP11820990.7A patent/EP2612860B1/en not_active Not-in-force
- 2011-08-30 JP JP2013526299A patent/JP5964305B2/ja not_active Expired - Fee Related
- 2011-08-30 HU HUE11820990A patent/HUE032572T2/en unknown
- 2011-08-30 CN CN201180041772.4A patent/CN103347876B/zh not_active Expired - Fee Related
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2017
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- 2017-08-07 US US15/670,160 patent/US10507209B2/en active Active
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2018
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