RU2202551C2 - Замещенные 3-цианохинолины - Google Patents
Замещенные 3-цианохинолины Download PDFInfo
- Publication number
- RU2202551C2 RU2202551C2 RU99123060/04A RU99123060A RU2202551C2 RU 2202551 C2 RU2202551 C2 RU 2202551C2 RU 99123060/04 A RU99123060/04 A RU 99123060/04A RU 99123060 A RU99123060 A RU 99123060A RU 2202551 C2 RU2202551 C2 RU 2202551C2
- Authority
- RU
- Russia
- Prior art keywords
- amino
- carbon atoms
- cyano
- carbonitrile
- quinolinecarbonitrile
- Prior art date
Links
- QZZYYBQGTSGDPP-UHFFFAOYSA-N quinoline-3-carbonitrile Chemical class C1=CC=CC2=CC(C#N)=CN=C21 QZZYYBQGTSGDPP-UHFFFAOYSA-N 0.000 title claims abstract 5
- 150000001875 compounds Chemical class 0.000 claims abstract 58
- 238000000034 method Methods 0.000 claims abstract 20
- 230000033228 biological regulation Effects 0.000 claims abstract 2
- 239000003814 drug Substances 0.000 claims abstract 2
- 230000005764 inhibitory process Effects 0.000 claims abstract 2
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 155
- 125000000217 alkyl group Chemical group 0.000 claims 47
- -1 halogenmethyl Chemical group 0.000 claims 38
- 229910052739 hydrogen Inorganic materials 0.000 claims 29
- 239000001257 hydrogen Substances 0.000 claims 29
- 150000003839 salts Chemical class 0.000 claims 28
- 125000003545 alkoxy group Chemical group 0.000 claims 21
- 125000004663 dialkyl amino group Chemical group 0.000 claims 20
- 150000002431 hydrogen Chemical class 0.000 claims 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 16
- 229910052736 halogen Inorganic materials 0.000 claims 15
- 150000002367 halogens Chemical group 0.000 claims 15
- 125000001424 substituent group Chemical group 0.000 claims 15
- 206010028980 Neoplasm Diseases 0.000 claims 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 11
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 10
- 125000004076 pyridyl group Chemical group 0.000 claims 10
- 241000124008 Mammalia Species 0.000 claims 9
- 125000000304 alkynyl group Chemical group 0.000 claims 8
- 238000006243 chemical reaction Methods 0.000 claims 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 8
- 125000004849 alkoxymethyl group Chemical group 0.000 claims 7
- 125000004414 alkyl thio group Chemical group 0.000 claims 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims 7
- 239000012634 fragment Substances 0.000 claims 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 6
- 229910052794 bromium Inorganic materials 0.000 claims 6
- 229910052801 chlorine Inorganic materials 0.000 claims 6
- 239000000460 chlorine Substances 0.000 claims 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 5
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 5
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims 5
- 229910052731 fluorine Inorganic materials 0.000 claims 5
- 239000011737 fluorine Substances 0.000 claims 5
- 125000005843 halogen group Chemical group 0.000 claims 5
- 238000010438 heat treatment Methods 0.000 claims 5
- 230000002401 inhibitory effect Effects 0.000 claims 5
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 5
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims 5
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 5
- MJOPKUFLFODTKP-UHFFFAOYSA-N 6-amino-4-(3-chloro-4-fluoroanilino)-7-methoxyquinoline-3-carbonitrile Chemical compound C=12C=C(N)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=C(F)C(Cl)=C1 MJOPKUFLFODTKP-UHFFFAOYSA-N 0.000 claims 4
- 150000001408 amides Chemical class 0.000 claims 4
- 230000008029 eradication Effects 0.000 claims 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
- 102000001253 Protein Kinase Human genes 0.000 claims 3
- 230000004071 biological effect Effects 0.000 claims 3
- 108060006633 protein kinase Proteins 0.000 claims 3
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims 2
- XFOAIBYWZWBMSL-UHFFFAOYSA-N 4-(3-hydroxy-2-methylanilino)-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=CC(O)=C1C XFOAIBYWZWBMSL-UHFFFAOYSA-N 0.000 claims 2
- AJSYUAVIQGKJFW-UHFFFAOYSA-N 6-amino-4-(3,4-dibromoanilino)quinoline-3-carbonitrile Chemical compound C12=CC(N)=CC=C2N=CC(C#N)=C1NC1=CC=C(Br)C(Br)=C1 AJSYUAVIQGKJFW-UHFFFAOYSA-N 0.000 claims 2
- ZRTXZWXHWPAXFT-UHFFFAOYSA-N 6-amino-4-(3-bromoanilino)quinoline-3-carbonitrile Chemical compound C12=CC(N)=CC=C2N=CC(C#N)=C1NC1=CC=CC(Br)=C1 ZRTXZWXHWPAXFT-UHFFFAOYSA-N 0.000 claims 2
- JSRLAMXXELZKLJ-UHFFFAOYSA-N 6-amino-4-[3-(trifluoromethyl)anilino]quinoline-3-carbonitrile Chemical compound C12=CC(N)=CC=C2N=CC(C#N)=C1NC1=CC=CC(C(F)(F)F)=C1 JSRLAMXXELZKLJ-UHFFFAOYSA-N 0.000 claims 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 2
- RAJARJQLBQRING-UHFFFAOYSA-N BrC=1C=C(C=CC1)NC1=C(C=NC2=CC(=C(C=C12)C(C(=O)N)=CCN(C)C)OC)C#N Chemical compound BrC=1C=C(C=CC1)NC1=C(C=NC2=CC(=C(C=C12)C(C(=O)N)=CCN(C)C)OC)C#N RAJARJQLBQRING-UHFFFAOYSA-N 0.000 claims 2
- 102000043136 MAP kinase family Human genes 0.000 claims 2
- 108091054455 MAP kinase family Proteins 0.000 claims 2
- 125000005118 N-alkylcarbamoyl group Chemical group 0.000 claims 2
- UMAUXDSUHUAKMF-UHFFFAOYSA-N chembl111586 Chemical compound C=12C=C(O)C(O)=CC2=NC=C(C#N)C=1NC1=CC=CC(Br)=C1 UMAUXDSUHUAKMF-UHFFFAOYSA-N 0.000 claims 2
- 239000003153 chemical reaction reagent Substances 0.000 claims 2
- 210000001072 colon Anatomy 0.000 claims 2
- 102000052116 epidermal growth factor receptor activity proteins Human genes 0.000 claims 2
- 108700015053 epidermal growth factor receptor activity proteins Proteins 0.000 claims 2
- 210000003238 esophagus Anatomy 0.000 claims 2
- 210000003734 kidney Anatomy 0.000 claims 2
- 210000004072 lung Anatomy 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 210000000214 mouth Anatomy 0.000 claims 2
- YOHYSYJDKVYCJI-UHFFFAOYSA-N n-[3-[[6-[3-(trifluoromethyl)anilino]pyrimidin-4-yl]amino]phenyl]cyclopropanecarboxamide Chemical compound FC(F)(F)C1=CC=CC(NC=2N=CN=C(NC=3C=C(NC(=O)C4CC4)C=CC=3)C=2)=C1 YOHYSYJDKVYCJI-UHFFFAOYSA-N 0.000 claims 2
- LUNOJOWDCVLIRF-UHFFFAOYSA-N n-[3-cyano-4-(3,4-dibromoanilino)quinolin-6-yl]prop-2-enamide Chemical compound C1=C(Br)C(Br)=CC=C1NC1=C(C#N)C=NC2=CC=C(NC(=O)C=C)C=C12 LUNOJOWDCVLIRF-UHFFFAOYSA-N 0.000 claims 2
- GRPHFCRERCRTMQ-UHFFFAOYSA-N n-[4-(3-bromoanilino)-3-cyanoquinolin-6-yl]-4-(dimethylamino)but-2-ynamide Chemical compound C12=CC(NC(=O)C#CCN(C)C)=CC=C2N=CC(C#N)=C1NC1=CC=CC(Br)=C1 GRPHFCRERCRTMQ-UHFFFAOYSA-N 0.000 claims 2
- YWUDVJHTWSRLEL-UHFFFAOYSA-N n-[4-(3-bromoanilino)-3-cyanoquinolin-6-yl]-4-hydroxybut-2-ynamide Chemical compound C12=CC(NC(=O)C#CCO)=CC=C2N=CC(C#N)=C1NC1=CC=CC(Br)=C1 YWUDVJHTWSRLEL-UHFFFAOYSA-N 0.000 claims 2
- MXBVVVDUUIDCNR-UHFFFAOYSA-N n-[4-(3-bromoanilino)-3-cyanoquinolin-6-yl]-4-methoxybut-2-ynamide Chemical compound C12=CC(NC(=O)C#CCOC)=CC=C2N=CC(C#N)=C1NC1=CC=CC(Br)=C1 MXBVVVDUUIDCNR-UHFFFAOYSA-N 0.000 claims 2
- SAYBFCUQRKDDCV-UHFFFAOYSA-N n-[4-(3-bromoanilino)-3-cyanoquinolin-6-yl]-4-morpholin-4-ylbut-2-ynamide Chemical compound BrC1=CC=CC(NC=2C3=CC(NC(=O)C#CCN4CCOCC4)=CC=C3N=CC=2C#N)=C1 SAYBFCUQRKDDCV-UHFFFAOYSA-N 0.000 claims 2
- 210000001672 ovary Anatomy 0.000 claims 2
- 210000003800 pharynx Anatomy 0.000 claims 2
- 208000030761 polycystic kidney disease Diseases 0.000 claims 2
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 claims 2
- 125000004550 quinolin-6-yl group Chemical group N1=CC=CC2=CC(=CC=C12)* 0.000 claims 2
- 210000002784 stomach Anatomy 0.000 claims 2
- 210000003932 urinary bladder Anatomy 0.000 claims 2
- ITGIYLMMAABTHC-ONEGZZNKSA-N (e)-4-(dimethylazaniumyl)but-2-enoate Chemical compound CN(C)C\C=C\C(O)=O ITGIYLMMAABTHC-ONEGZZNKSA-N 0.000 claims 1
- RLYNGYDVXRKEOO-XQHVRGAUSA-N (e)-but-2-enoic acid Chemical compound C\C=C\C(O)=O.C\C=C\C(O)=O RLYNGYDVXRKEOO-XQHVRGAUSA-N 0.000 claims 1
- IYVDPTGYWDFGTF-VOTSOKGWSA-N (e)-n-[4-(3-bromoanilino)-3-cyanoquinolin-6-yl]-3-chloroprop-2-enamide Chemical compound C12=CC(NC(=O)/C=C/Cl)=CC=C2N=CC(C#N)=C1NC1=CC=CC(Br)=C1 IYVDPTGYWDFGTF-VOTSOKGWSA-N 0.000 claims 1
- IYVDPTGYWDFGTF-SREVYHEPSA-N (z)-n-[4-(3-bromoanilino)-3-cyanoquinolin-6-yl]-3-chloroprop-2-enamide Chemical compound C12=CC(NC(=O)\C=C/Cl)=CC=C2N=CC(C#N)=C1NC1=CC=CC(Br)=C1 IYVDPTGYWDFGTF-SREVYHEPSA-N 0.000 claims 1
- KXQYGHZAGFHMDJ-ARJAWSKDSA-N (z)-n-[4-(3-chloro-4-fluoroanilino)-3-cyanoquinolin-6-yl]-4-(dimethylamino)but-2-enamide Chemical compound C12=CC(NC(=O)\C=C/CN(C)C)=CC=C2N=CC(C#N)=C1NC1=CC=C(F)C(Cl)=C1 KXQYGHZAGFHMDJ-ARJAWSKDSA-N 0.000 claims 1
- RIQABCQFNMRXGD-IHWYPQMZSA-N (z)-n-[4-(3-chloro-4-fluoroanilino)-3-cyanoquinolin-6-yl]-4-methoxybut-2-enamide Chemical compound C12=CC(NC(=O)\C=C/COC)=CC=C2N=CC(C#N)=C1NC1=CC=C(F)C(Cl)=C1 RIQABCQFNMRXGD-IHWYPQMZSA-N 0.000 claims 1
- RTJPSNFGGWVYTF-UHFFFAOYSA-N 2-(4-bromoanilino)-6-nitroquinoline-3-carbonitrile Chemical compound N#CC1=CC2=CC([N+](=O)[O-])=CC=C2N=C1NC1=CC=C(Br)C=C1 RTJPSNFGGWVYTF-UHFFFAOYSA-N 0.000 claims 1
- FMVZTGRYLGQXNY-UHFFFAOYSA-N 2-(methoxymethoxy)quinoline-3-carbonitrile Chemical compound COCOc1nc2ccccc2cc1C#N FMVZTGRYLGQXNY-UHFFFAOYSA-N 0.000 claims 1
- PLLQEHQPJCWDSJ-UHFFFAOYSA-N 2-[(3,4-dimethoxyphenyl)methylamino]-6,7-diethoxyquinoline-3-carbonitrile Chemical compound COC=1C=C(C=CC=1OC)CNC1=NC2=CC(=C(C=C2C=C1C#N)OCC)OCC PLLQEHQPJCWDSJ-UHFFFAOYSA-N 0.000 claims 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims 1
- XGQFVVQUVDLUAW-UHFFFAOYSA-N 3-[(3-cyano-6,7-dimethoxyquinolin-4-yl)amino]-2-methylbenzoic acid Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=CC(C(O)=O)=C1C XGQFVVQUVDLUAW-UHFFFAOYSA-N 0.000 claims 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 1
- 125000006305 3-iodophenyl group Chemical group [H]C1=C([H])C(I)=C([H])C(*)=C1[H] 0.000 claims 1
- TZNVNORLQOCTMY-UHFFFAOYSA-N 4-(2,4-dihydroxyanilino)-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=C(O)C=C1O TZNVNORLQOCTMY-UHFFFAOYSA-N 0.000 claims 1
- FNAOGFPOADZWDT-UHFFFAOYSA-N 4-(2-amino-4,5-dimethylanilino)-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC(C)=C(C)C=C1N FNAOGFPOADZWDT-UHFFFAOYSA-N 0.000 claims 1
- GGSWVTQHMOCNJI-UHFFFAOYSA-N 4-(2-chloro-4-hydroxyanilino)-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=C(O)C=C1Cl GGSWVTQHMOCNJI-UHFFFAOYSA-N 0.000 claims 1
- QUSXJYUXWFSQPQ-UHFFFAOYSA-N 4-(2-hydroxy-5-methylanilino)-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC(C)=CC=C1O QUSXJYUXWFSQPQ-UHFFFAOYSA-N 0.000 claims 1
- GCNKUJAIEDINLA-UHFFFAOYSA-N 4-(2-hydroxy-6-methylanilino)-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=C(C)C=CC=C1O GCNKUJAIEDINLA-UHFFFAOYSA-N 0.000 claims 1
- RUGCZQOSGFAGFE-UHFFFAOYSA-N 4-(3,4-dibromoanilino)-6-nitroquinoline-3-carbonitrile Chemical compound C12=CC([N+](=O)[O-])=CC=C2N=CC(C#N)=C1NC1=CC=C(Br)C(Br)=C1 RUGCZQOSGFAGFE-UHFFFAOYSA-N 0.000 claims 1
- LNBBTBLPDKHCPQ-UHFFFAOYSA-N 4-(3,4-dichloroanilino)-6-nitroquinoline-3-carbonitrile Chemical compound C12=CC([N+](=O)[O-])=CC=C2N=CC(C#N)=C1NC1=CC=C(Cl)C(Cl)=C1 LNBBTBLPDKHCPQ-UHFFFAOYSA-N 0.000 claims 1
- WYUJPMJLGOVLKG-UHFFFAOYSA-N 4-(3,4-difluoroanilino)-6-nitroquinoline-3-carbonitrile Chemical compound C12=CC([N+](=O)[O-])=CC=C2N=CC(C#N)=C1NC1=CC=C(F)C(F)=C1 WYUJPMJLGOVLKG-UHFFFAOYSA-N 0.000 claims 1
- PPNMPEHEXLGGID-UHFFFAOYSA-N 4-(3,4-dimethoxyanilino)-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C1=C(OC)C(OC)=CC=C1NC1=C(C#N)C=NC2=CC(OC)=C(OC)C=C12 PPNMPEHEXLGGID-UHFFFAOYSA-N 0.000 claims 1
- MBEJRIMUDFCZSL-UHFFFAOYSA-N 4-(3,5-dibromo-4-hydroxyanilino)-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC(Br)=C(O)C(Br)=C1 MBEJRIMUDFCZSL-UHFFFAOYSA-N 0.000 claims 1
- YJBYKRFNOYCMSK-UHFFFAOYSA-N 4-(3,5-dichloro-4-hydroxyanilino)-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC(Cl)=C(O)C(Cl)=C1 YJBYKRFNOYCMSK-UHFFFAOYSA-N 0.000 claims 1
- XBFPRUXDYAQIOC-UHFFFAOYSA-N 4-(3-acetylanilino)-6,7-diethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OCC)C(OCC)=CC2=NC=C(C#N)C=1NC1=CC=CC(C(C)=O)=C1 XBFPRUXDYAQIOC-UHFFFAOYSA-N 0.000 claims 1
- MZQKSJFIOAVZJR-UHFFFAOYSA-N 4-(3-aminoanilino)-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=CC(N)=C1 MZQKSJFIOAVZJR-UHFFFAOYSA-N 0.000 claims 1
- PVGQFSJIEXPGDS-UHFFFAOYSA-N 4-(3-azidoanilino)-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=CC(N=[N+]=[N-])=C1 PVGQFSJIEXPGDS-UHFFFAOYSA-N 0.000 claims 1
- WLEQBEYGUJEPBI-UHFFFAOYSA-N 4-(3-bromo-4-fluoroanilino)-6-nitroquinoline-3-carbonitrile Chemical compound C12=CC([N+](=O)[O-])=CC=C2N=CC(C#N)=C1NC1=CC=C(F)C(Br)=C1 WLEQBEYGUJEPBI-UHFFFAOYSA-N 0.000 claims 1
- JCGYXRCAGZQKRK-UHFFFAOYSA-N 4-(3-bromo-4-fluoroanilino)-7-methoxy-6-nitroquinoline-3-carbonitrile Chemical compound C=12C=C([N+]([O-])=O)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=C(F)C(Br)=C1 JCGYXRCAGZQKRK-UHFFFAOYSA-N 0.000 claims 1
- BOXDQGATHFGEIB-UHFFFAOYSA-N 4-(3-bromo-4-methylanilino)-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=C(C)C(Br)=C1 BOXDQGATHFGEIB-UHFFFAOYSA-N 0.000 claims 1
- UHTFOMCCUZQBMM-UHFFFAOYSA-N 4-(3-bromoanilino)-5,8-dimethoxyquinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C(OC)=CC=C(OC)C2=C1NC1=CC=CC(Br)=C1 UHTFOMCCUZQBMM-UHFFFAOYSA-N 0.000 claims 1
- VXMFIYMOOZZNJO-UHFFFAOYSA-N 4-(3-bromoanilino)-6,7,8-trimethoxyquinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C(OC)=C(OC)C(OC)=CC2=C1NC1=CC=CC(Br)=C1 VXMFIYMOOZZNJO-UHFFFAOYSA-N 0.000 claims 1
- NVHCPPNJEXAXNA-UHFFFAOYSA-N 4-(3-bromoanilino)-6,7-bis(2-methoxyethoxy)quinoline-3-carbonitrile Chemical compound C=12C=C(OCCOC)C(OCCOC)=CC2=NC=C(C#N)C=1NC1=CC=CC(Br)=C1 NVHCPPNJEXAXNA-UHFFFAOYSA-N 0.000 claims 1
- PADYONKQSSWAFW-UHFFFAOYSA-N 4-(3-bromoanilino)-6,7-dibutoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OCCCC)C(OCCCC)=CC2=NC=C(C#N)C=1NC1=CC=CC(Br)=C1 PADYONKQSSWAFW-UHFFFAOYSA-N 0.000 claims 1
- ZXILYRWRAKLTOG-UHFFFAOYSA-N 4-(3-bromoanilino)-6,7-diethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OCC)C(OCC)=CC2=NC=C(C#N)C=1NC1=CC=CC(Br)=C1 ZXILYRWRAKLTOG-UHFFFAOYSA-N 0.000 claims 1
- CQKFTSMPIIYOBX-UHFFFAOYSA-N 4-(3-bromoanilino)-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=CC(Br)=C1 CQKFTSMPIIYOBX-UHFFFAOYSA-N 0.000 claims 1
- LRIHFKGXXJKDDD-UHFFFAOYSA-N 4-(3-bromoanilino)-6,7-dipropoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OCCC)C(OCCC)=CC2=NC=C(C#N)C=1NC1=CC=CC(Br)=C1 LRIHFKGXXJKDDD-UHFFFAOYSA-N 0.000 claims 1
- BWXDTMBEXXDSQD-UHFFFAOYSA-N 4-(3-bromoanilino)-6-(3-pyrrolidin-1-ylpropylamino)quinoline-3-carbonitrile Chemical compound BrC1=CC=CC(NC=2C3=CC(NCCCN4CCCC4)=CC=C3N=CC=2C#N)=C1 BWXDTMBEXXDSQD-UHFFFAOYSA-N 0.000 claims 1
- MCIICVWNGVSLPW-UHFFFAOYSA-N 4-(3-bromoanilino)-6-(dimethylamino)quinoline-3-carbonitrile;hydrochloride Chemical compound Cl.C12=CC(N(C)C)=CC=C2N=CC(C#N)=C1NC1=CC=CC(Br)=C1 MCIICVWNGVSLPW-UHFFFAOYSA-N 0.000 claims 1
- IKOYWGLBVGPRAG-UHFFFAOYSA-N 4-(3-bromoanilino)-6-ethoxy-7-methoxyquinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C=C(OC)C(OCC)=CC2=C1NC1=CC=CC(Br)=C1 IKOYWGLBVGPRAG-UHFFFAOYSA-N 0.000 claims 1
- IYPAMCYSGUYVAN-UHFFFAOYSA-N 4-(3-bromoanilino)-6-methoxy-7-(3-morpholin-4-ylpropoxy)quinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C=C(OCCCN3CCOCC3)C(OC)=CC2=C1NC1=CC=CC(Br)=C1 IYPAMCYSGUYVAN-UHFFFAOYSA-N 0.000 claims 1
- SNLXBZYKYWEIOV-UHFFFAOYSA-N 4-(3-bromoanilino)-6-nitroquinoline-3-carbonitrile Chemical compound C12=CC([N+](=O)[O-])=CC=C2N=CC(C#N)=C1NC1=CC=CC(Br)=C1 SNLXBZYKYWEIOV-UHFFFAOYSA-N 0.000 claims 1
- WCNVEOXERDZIOX-UHFFFAOYSA-N 4-(3-bromoanilino)-7-ethoxy-6-methoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OCC)=CC2=NC=C(C#N)C=1NC1=CC=CC(Br)=C1 WCNVEOXERDZIOX-UHFFFAOYSA-N 0.000 claims 1
- JGTPCHRGCCPWCC-UHFFFAOYSA-N 4-(3-bromoanilino)-7-ethoxy-6-nitroquinoline-3-carbonitrile Chemical compound C=12C=C([N+]([O-])=O)C(OCC)=CC2=NC=C(C#N)C=1NC1=CC=CC(Br)=C1 JGTPCHRGCCPWCC-UHFFFAOYSA-N 0.000 claims 1
- QHDFGPMRPDDNDN-UHFFFAOYSA-N 4-(3-bromoanilino)-7-methoxy-6-(3-morpholin-4-ylpropoxy)quinoline-3-carbonitrile Chemical compound C=12C=C(OCCCN3CCOCC3)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=CC(Br)=C1 QHDFGPMRPDDNDN-UHFFFAOYSA-N 0.000 claims 1
- BISJVYCVPJVRKJ-UHFFFAOYSA-N 4-(3-bromoanilino)-7-methoxy-6-nitroquinoline-3-carbonitrile Chemical compound C=12C=C([N+]([O-])=O)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=CC(Br)=C1 BISJVYCVPJVRKJ-UHFFFAOYSA-N 0.000 claims 1
- NUBVTRDETNNCGY-UHFFFAOYSA-N 4-(3-bromoanilino)-7-methoxyquinoline-3-carbonitrile Chemical compound N#CC=1C=NC2=CC(OC)=CC=C2C=1NC1=CC=CC(Br)=C1 NUBVTRDETNNCGY-UHFFFAOYSA-N 0.000 claims 1
- OESIRSGDGHCWFH-UHFFFAOYSA-N 4-(3-bromoanilino)-8-[(dimethylamino)methyl]-6-nitroquinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C(CN(C)C)=CC([N+]([O-])=O)=CC2=C1NC1=CC=CC(Br)=C1 OESIRSGDGHCWFH-UHFFFAOYSA-N 0.000 claims 1
- PYGUWPNNELOZLP-UHFFFAOYSA-N 4-(3-bromoanilino)-8-methoxyquinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C(OC)=CC=CC2=C1NC1=CC=CC(Br)=C1 PYGUWPNNELOZLP-UHFFFAOYSA-N 0.000 claims 1
- AFOMMVJBDXYOAA-UHFFFAOYSA-N 4-(3-bromoanilino)-8-methyl-6-nitroquinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C(C)=CC([N+]([O-])=O)=CC2=C1NC1=CC=CC(Br)=C1 AFOMMVJBDXYOAA-UHFFFAOYSA-N 0.000 claims 1
- JPDTVCOEUUQNSS-UHFFFAOYSA-N 4-(3-bromophenoxy)-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1OC1=CC=CC(Br)=C1 JPDTVCOEUUQNSS-UHFFFAOYSA-N 0.000 claims 1
- GLDODVVYHDNXHG-UHFFFAOYSA-N 4-(3-chloro-2-thiophen-3-yloxyanilino)-6-nitroquinoline-3-carbonitrile Chemical compound ClC=1C(=C(C=CC=1)NC1=C(C=NC2=CC=C(C=C12)[N+](=O)[O-])C#N)OC=1C=CSC=1 GLDODVVYHDNXHG-UHFFFAOYSA-N 0.000 claims 1
- VJTVBWNBERHDKM-UHFFFAOYSA-N 4-(3-chloro-4-fluoroanilino)-6,7-diethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OCC)C(OCC)=CC2=NC=C(C#N)C=1NC1=CC=C(F)C(Cl)=C1 VJTVBWNBERHDKM-UHFFFAOYSA-N 0.000 claims 1
- VCNRVJKPJCKMIG-UHFFFAOYSA-N 4-(3-chloro-4-fluoroanilino)-6-nitroquinoline-3-carbonitrile Chemical compound C12=CC([N+](=O)[O-])=CC=C2N=CC(C#N)=C1NC1=CC=C(F)C(Cl)=C1 VCNRVJKPJCKMIG-UHFFFAOYSA-N 0.000 claims 1
- IJAFEDNMGMKIIZ-UHFFFAOYSA-N 4-(3-chloro-4-fluoroanilino)-7-methoxy-6-nitroquinoline-3-carbonitrile Chemical compound C=12C=C([N+]([O-])=O)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=C(F)C(Cl)=C1 IJAFEDNMGMKIIZ-UHFFFAOYSA-N 0.000 claims 1
- DUDXBCAIXIMAKI-UHFFFAOYSA-N 4-(3-chloro-4-hydroxyanilino)-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=C(O)C(Cl)=C1 DUDXBCAIXIMAKI-UHFFFAOYSA-N 0.000 claims 1
- OTTMSKLASSZGJD-UHFFFAOYSA-N 4-(3-chloro-4-methoxyanilino)-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C1=C(Cl)C(OC)=CC=C1NC1=C(C#N)C=NC2=CC(OC)=C(OC)C=C12 OTTMSKLASSZGJD-UHFFFAOYSA-N 0.000 claims 1
- OSNTXNDDUYHOPC-UHFFFAOYSA-N 4-(3-chloro-4-methylanilino)-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=C(C)C(Cl)=C1 OSNTXNDDUYHOPC-UHFFFAOYSA-N 0.000 claims 1
- PSZDFZSOCJHJRP-UHFFFAOYSA-N 4-(3-chloro-4-phenylsulfanylanilino)-6,7-diethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OCC)C(OCC)=CC2=NC=C(C#N)C=1NC(C=C1Cl)=CC=C1SC1=CC=CC=C1 PSZDFZSOCJHJRP-UHFFFAOYSA-N 0.000 claims 1
- FDTYUDRPBMYHKE-UHFFFAOYSA-N 4-(3-chloro-4-phenylsulfanylanilino)-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC(C=C1Cl)=CC=C1SC1=CC=CC=C1 FDTYUDRPBMYHKE-UHFFFAOYSA-N 0.000 claims 1
- XEYIOOPOGZOAEP-UHFFFAOYSA-N 4-(3-chloroanilino)-6,7-diethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OCC)C(OCC)=CC2=NC=C(C#N)C=1NC1=CC=CC(Cl)=C1 XEYIOOPOGZOAEP-UHFFFAOYSA-N 0.000 claims 1
- HLBGGOYPNRIHFH-UHFFFAOYSA-N 4-(3-chloroanilino)-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=CC(Cl)=C1 HLBGGOYPNRIHFH-UHFFFAOYSA-N 0.000 claims 1
- FNRKKHMPSZQHEJ-UHFFFAOYSA-N 4-(3-chloroanilino)-6-nitroquinoline-3-carbonitrile Chemical compound C12=CC([N+](=O)[O-])=CC=C2N=CC(C#N)=C1NC1=CC=CC(Cl)=C1 FNRKKHMPSZQHEJ-UHFFFAOYSA-N 0.000 claims 1
- CCECSDRSBLPTHW-UHFFFAOYSA-N 4-(3-cyanoanilino)-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=CC(C#N)=C1 CCECSDRSBLPTHW-UHFFFAOYSA-N 0.000 claims 1
- QEPNPWOGJRAAOQ-UHFFFAOYSA-N 4-(3-cyanoanilino)-6-nitroquinoline-3-carbonitrile Chemical compound C12=CC([N+](=O)[O-])=CC=C2N=CC(C#N)=C1NC1=CC=CC(C#N)=C1 QEPNPWOGJRAAOQ-UHFFFAOYSA-N 0.000 claims 1
- PLWCWVLZUBYBEW-UHFFFAOYSA-N 4-(3-ethynylanilino)-6-nitroquinoline-3-carbonitrile Chemical compound C12=CC([N+](=O)[O-])=CC=C2N=CC(C#N)=C1NC1=CC=CC(C#C)=C1 PLWCWVLZUBYBEW-UHFFFAOYSA-N 0.000 claims 1
- OLNMDVMEJYNZBA-UHFFFAOYSA-N 4-(3-fluoroanilino)-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=CC(F)=C1 OLNMDVMEJYNZBA-UHFFFAOYSA-N 0.000 claims 1
- ZFLQLVUBCSNBJL-UHFFFAOYSA-N 4-(3-fluoroanilino)-6-nitroquinoline-3-carbonitrile Chemical compound C12=CC([N+](=O)[O-])=CC=C2N=CC(C#N)=C1NC1=CC=CC(F)=C1 ZFLQLVUBCSNBJL-UHFFFAOYSA-N 0.000 claims 1
- WAJLIMOCEJPQKH-UHFFFAOYSA-N 4-(3-hydroxy-4-methoxyanilino)-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C1=C(O)C(OC)=CC=C1NC1=C(C#N)C=NC2=CC(OC)=C(OC)C=C12 WAJLIMOCEJPQKH-UHFFFAOYSA-N 0.000 claims 1
- ORXRAXFKEQIAIH-UHFFFAOYSA-N 4-(3-hydroxy-4-methoxyanilino)-8-methoxy-6-nitroquinoline-3-carbonitrile Chemical compound C1=C(O)C(OC)=CC=C1NC1=C(C#N)C=NC2=C(OC)C=C([N+]([O-])=O)C=C12 ORXRAXFKEQIAIH-UHFFFAOYSA-N 0.000 claims 1
- GOYDWBWGOZQPPQ-UHFFFAOYSA-N 4-(3-hydroxy-4-methoxyanilino)-8-methoxyquinoline-3-carbonitrile Chemical compound C1=C(O)C(OC)=CC=C1NC1=C(C#N)C=NC2=C(OC)C=CC=C12 GOYDWBWGOZQPPQ-UHFFFAOYSA-N 0.000 claims 1
- ADYHMPMHENUUSX-UHFFFAOYSA-N 4-(3-hydroxy-4-methylanilino)-5,8-dimethoxyquinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C(OC)=CC=C(OC)C2=C1NC1=CC=C(C)C(O)=C1 ADYHMPMHENUUSX-UHFFFAOYSA-N 0.000 claims 1
- HDYIFTHEJLLDHZ-UHFFFAOYSA-N 4-(3-hydroxy-4-methylanilino)-6,7,8-trimethoxyquinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C(OC)=C(OC)C(OC)=CC2=C1NC1=CC=C(C)C(O)=C1 HDYIFTHEJLLDHZ-UHFFFAOYSA-N 0.000 claims 1
- RMENKSJNOQJIGF-UHFFFAOYSA-N 4-(3-hydroxy-4-methylanilino)-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=C(C)C(O)=C1 RMENKSJNOQJIGF-UHFFFAOYSA-N 0.000 claims 1
- DPAMNPPLTWUUOW-UHFFFAOYSA-N 4-(3-hydroxy-4-methylanilino)-6-methoxy-7-(2-morpholin-4-ylethoxy)quinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C=C(OCCN3CCOCC3)C(OC)=CC2=C1NC1=CC=C(C)C(O)=C1 DPAMNPPLTWUUOW-UHFFFAOYSA-N 0.000 claims 1
- CCGQJNCMOBQUDD-UHFFFAOYSA-N 4-(3-hydroxy-4-methylanilino)-6-methoxyquinoline-3-carbonitrile Chemical compound C12=CC(OC)=CC=C2N=CC(C#N)=C1NC1=CC=C(C)C(O)=C1 CCGQJNCMOBQUDD-UHFFFAOYSA-N 0.000 claims 1
- OYLCGAMUHLRDOV-UHFFFAOYSA-N 4-(3-hydroxy-4-methylanilino)-7-methoxy-6-(3-morpholin-4-ylpropoxy)quinoline-3-carbonitrile Chemical compound C=12C=C(OCCCN3CCOCC3)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=C(C)C(O)=C1 OYLCGAMUHLRDOV-UHFFFAOYSA-N 0.000 claims 1
- ILIFRLHRZPLVLV-UHFFFAOYSA-N 4-(3-hydroxy-4-methylanilino)-7-methoxyquinoline-3-carbonitrile Chemical compound N#CC=1C=NC2=CC(OC)=CC=C2C=1NC1=CC=C(C)C(O)=C1 ILIFRLHRZPLVLV-UHFFFAOYSA-N 0.000 claims 1
- RFRODPJRPJJUKI-UHFFFAOYSA-N 4-(3-hydroxy-4-methylanilino)-8-methoxy-6-nitroquinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C(OC)=CC([N+]([O-])=O)=CC2=C1NC1=CC=C(C)C(O)=C1 RFRODPJRPJJUKI-UHFFFAOYSA-N 0.000 claims 1
- QPFBREGJTDLPBW-UHFFFAOYSA-N 4-(3-hydroxy-4-methylanilino)-8-methoxyquinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C(OC)=CC=CC2=C1NC1=CC=C(C)C(O)=C1 QPFBREGJTDLPBW-UHFFFAOYSA-N 0.000 claims 1
- IKUBPVIBISSEJV-UHFFFAOYSA-N 4-(3-hydroxyanilino)-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=CC(O)=C1 IKUBPVIBISSEJV-UHFFFAOYSA-N 0.000 claims 1
- DLQVSGGYBADFFQ-UHFFFAOYSA-N 4-(3-iodoanilino)-6-nitroquinoline-3-carbonitrile Chemical compound C12=CC([N+](=O)[O-])=CC=C2N=CC(C#N)=C1NC1=CC=CC(I)=C1 DLQVSGGYBADFFQ-UHFFFAOYSA-N 0.000 claims 1
- CFEACTBBVRNDBB-UHFFFAOYSA-N 4-(3-methoxyanilino)-6-nitroquinoline-3-carbonitrile Chemical compound COC1=CC=CC(NC=2C3=CC(=CC=C3N=CC=2C#N)[N+]([O-])=O)=C1 CFEACTBBVRNDBB-UHFFFAOYSA-N 0.000 claims 1
- FMAZODAHMSMUNK-UHFFFAOYSA-N 4-(3-methylanilino)-6-nitroquinoline-3-carbonitrile Chemical compound CC1=CC=CC(NC=2C3=CC(=CC=C3N=CC=2C#N)[N+]([O-])=O)=C1 FMAZODAHMSMUNK-UHFFFAOYSA-N 0.000 claims 1
- FHZKUQUEIDJHNY-UHFFFAOYSA-N 4-(3-methylsulfanylanilino)-6-nitroquinoline-3-carbonitrile Chemical compound CSC1=CC=CC(NC=2C3=CC(=CC=C3N=CC=2C#N)[N+]([O-])=O)=C1 FHZKUQUEIDJHNY-UHFFFAOYSA-N 0.000 claims 1
- UFBPAPKMTIFMAC-UHFFFAOYSA-N 4-(4-bromo-3-hydroxyanilino)-8-methoxyquinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C(OC)=CC=CC2=C1NC1=CC=C(Br)C(O)=C1 UFBPAPKMTIFMAC-UHFFFAOYSA-N 0.000 claims 1
- DNGLYZBHHHXJDG-UHFFFAOYSA-N 4-(4-bromophenyl)sulfanyl-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1SC1=CC=C(Br)C=C1 DNGLYZBHHHXJDG-UHFFFAOYSA-N 0.000 claims 1
- KBQXQEITHBAZNL-UHFFFAOYSA-N 4-(4-chloro-2-fluoro-5-hydroxyanilino)-5,8-dimethoxyquinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C(OC)=CC=C(OC)C2=C1NC1=CC(O)=C(Cl)C=C1F KBQXQEITHBAZNL-UHFFFAOYSA-N 0.000 claims 1
- NXQUVEFCIXDBGX-UHFFFAOYSA-N 4-(4-chloro-2-fluoro-5-hydroxyanilino)-6,7,8-trimethoxyquinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C(OC)=C(OC)C(OC)=CC2=C1NC1=CC(O)=C(Cl)C=C1F NXQUVEFCIXDBGX-UHFFFAOYSA-N 0.000 claims 1
- AHEZGLOWOWBLAP-UHFFFAOYSA-N 4-(4-chloro-2-fluoro-5-hydroxyanilino)-6-methoxy-7-(2-morpholin-4-ylethoxy)quinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C=C(OCCN3CCOCC3)C(OC)=CC2=C1NC1=CC(O)=C(Cl)C=C1F AHEZGLOWOWBLAP-UHFFFAOYSA-N 0.000 claims 1
- RDVLPEPWSGCECJ-UHFFFAOYSA-N 4-(4-chloro-2-fluoro-5-hydroxyanilino)-6-methoxy-7-(3-morpholin-4-ylpropoxy)quinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C=C(OCCCN3CCOCC3)C(OC)=CC2=C1NC1=CC(O)=C(Cl)C=C1F RDVLPEPWSGCECJ-UHFFFAOYSA-N 0.000 claims 1
- CPMQZDLBPYFFLC-UHFFFAOYSA-N 4-(4-chloro-2-fluoro-5-hydroxyanilino)-6-methoxyquinoline-3-carbonitrile Chemical compound C12=CC(OC)=CC=C2N=CC(C#N)=C1NC1=CC(O)=C(Cl)C=C1F CPMQZDLBPYFFLC-UHFFFAOYSA-N 0.000 claims 1
- ISCIEBIOIJWXOX-UHFFFAOYSA-N 4-(4-chloro-2-fluoro-5-hydroxyanilino)-7-[2-(dimethylamino)ethoxy]-6-methoxyquinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C=C(OCCN(C)C)C(OC)=CC2=C1NC1=CC(O)=C(Cl)C=C1F ISCIEBIOIJWXOX-UHFFFAOYSA-N 0.000 claims 1
- WUTUYQSMZJUIDT-UHFFFAOYSA-N 4-(4-chloro-2-fluoro-5-hydroxyanilino)-7-[3-(dimethylamino)propoxy]-6-methoxyquinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C=C(OCCCN(C)C)C(OC)=CC2=C1NC1=CC(O)=C(Cl)C=C1F WUTUYQSMZJUIDT-UHFFFAOYSA-N 0.000 claims 1
- AWVIKPDIAVKVTD-UHFFFAOYSA-N 4-(4-chloro-2-fluoro-5-hydroxyanilino)-7-methoxyquinoline-3-carbonitrile Chemical compound N#CC=1C=NC2=CC(OC)=CC=C2C=1NC1=CC(O)=C(Cl)C=C1F AWVIKPDIAVKVTD-UHFFFAOYSA-N 0.000 claims 1
- HXFOGGVVVXAAAY-UHFFFAOYSA-N 4-(4-chloro-2-fluoroanilino)-5,8-dimethoxyquinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C(OC)=CC=C(OC)C2=C1NC1=CC=C(Cl)C=C1F HXFOGGVVVXAAAY-UHFFFAOYSA-N 0.000 claims 1
- DCCQITVOSPOELC-UHFFFAOYSA-N 4-(4-chloro-2-fluoroanilino)-6,7,8-trimethoxyquinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C(OC)=C(OC)C(OC)=CC2=C1NC1=CC=C(Cl)C=C1F DCCQITVOSPOELC-UHFFFAOYSA-N 0.000 claims 1
- AGDGNPMRBLYEBN-UHFFFAOYSA-N 4-(4-chloro-2-fluoroanilino)-6,7-dihydroxyquinoline-3-carbonitrile Chemical compound C=12C=C(O)C(O)=CC2=NC=C(C#N)C=1NC1=CC=C(Cl)C=C1F AGDGNPMRBLYEBN-UHFFFAOYSA-N 0.000 claims 1
- AZGVCABJHURYHG-UHFFFAOYSA-N 4-(4-chloro-2-fluoroanilino)-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=C(Cl)C=C1F AZGVCABJHURYHG-UHFFFAOYSA-N 0.000 claims 1
- UCTHWZMWNQJTQN-UHFFFAOYSA-N 4-(4-chloro-2-fluoroanilino)-6-methoxy-7-(3-morpholin-4-ylpropoxy)quinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C=C(OCCCN3CCOCC3)C(OC)=CC2=C1NC1=CC=C(Cl)C=C1F UCTHWZMWNQJTQN-UHFFFAOYSA-N 0.000 claims 1
- QDMNXRDMMAATAQ-UHFFFAOYSA-N 4-(4-chloro-2-fluoroanilino)-6-methoxy-7-phenylmethoxyquinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C=C(OCC=3C=CC=CC=3)C(OC)=CC2=C1NC1=CC=C(Cl)C=C1F QDMNXRDMMAATAQ-UHFFFAOYSA-N 0.000 claims 1
- WGZXUJZAMNFXSU-UHFFFAOYSA-N 4-(4-chloro-2-fluoroanilino)-6-methoxyquinoline-3-carbonitrile Chemical compound C12=CC(OC)=CC=C2N=CC(C#N)=C1NC1=CC=C(Cl)C=C1F WGZXUJZAMNFXSU-UHFFFAOYSA-N 0.000 claims 1
- ZRBPCTDCKOQMBZ-UHFFFAOYSA-N 4-(4-chloro-2-fluoroanilino)-7-(3-chloropropoxy)-6-methoxyquinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C=C(OCCCCl)C(OC)=CC2=C1NC1=CC=C(Cl)C=C1F ZRBPCTDCKOQMBZ-UHFFFAOYSA-N 0.000 claims 1
- JSZSIBBREFGLGJ-UHFFFAOYSA-N 4-(4-chloro-2-fluoroanilino)-7-ethoxyquinoline-3-carbonitrile Chemical compound N#CC=1C=NC2=CC(OCC)=CC=C2C=1NC1=CC=C(Cl)C=C1F JSZSIBBREFGLGJ-UHFFFAOYSA-N 0.000 claims 1
- NBFFJZSLOQTJKX-UHFFFAOYSA-N 4-(4-chloro-2-fluoroanilino)-7-hydroxyquinoline-3-carbonitrile Chemical compound N#CC=1C=NC2=CC(O)=CC=C2C=1NC1=CC=C(Cl)C=C1F NBFFJZSLOQTJKX-UHFFFAOYSA-N 0.000 claims 1
- UFUCDVGCMNVASM-UHFFFAOYSA-N 4-(4-chloro-2-fluoroanilino)-7-methoxy-6-(3-morpholin-4-ylpropoxy)quinoline-3-carbonitrile Chemical compound C=12C=C(OCCCN3CCOCC3)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=C(Cl)C=C1F UFUCDVGCMNVASM-UHFFFAOYSA-N 0.000 claims 1
- RWPARJNAESKYRJ-UHFFFAOYSA-N 4-(4-chloro-2-fluoroanilino)-7-methoxy-6-nitroquinoline-3-carbonitrile Chemical compound C=12C=C([N+]([O-])=O)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=C(Cl)C=C1F RWPARJNAESKYRJ-UHFFFAOYSA-N 0.000 claims 1
- NIFSUEUBPCVATA-UHFFFAOYSA-N 4-(4-chloro-2-fluoroanilino)-7-methoxyquinoline-3-carbonitrile Chemical compound N#CC=1C=NC2=CC(OC)=CC=C2C=1NC1=CC=C(Cl)C=C1F NIFSUEUBPCVATA-UHFFFAOYSA-N 0.000 claims 1
- VUELXWCNULTVCB-UHFFFAOYSA-N 4-(4-chloro-2-fluoroanilino)-8-methoxy-6-nitroquinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C(OC)=CC([N+]([O-])=O)=CC2=C1NC1=CC=C(Cl)C=C1F VUELXWCNULTVCB-UHFFFAOYSA-N 0.000 claims 1
- VHNUHNWRNYABHC-UHFFFAOYSA-N 4-(4-chloro-2-fluoroanilino)-8-methoxyquinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C(OC)=CC=CC2=C1NC1=CC=C(Cl)C=C1F VHNUHNWRNYABHC-UHFFFAOYSA-N 0.000 claims 1
- INWVUMKNCRPNHB-UHFFFAOYSA-N 4-(4-chloro-2-methylanilino)-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=C(Cl)C=C1C INWVUMKNCRPNHB-UHFFFAOYSA-N 0.000 claims 1
- HLURNMSMPHQXLV-UHFFFAOYSA-N 4-(4-ethylanilino)-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C1=CC(CC)=CC=C1NC1=C(C#N)C=NC2=CC(OC)=C(OC)C=C12 HLURNMSMPHQXLV-UHFFFAOYSA-N 0.000 claims 1
- PICBGXSASXFIAL-UHFFFAOYSA-N 4-(4-fluoroanilino)-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=C(F)C=C1 PICBGXSASXFIAL-UHFFFAOYSA-N 0.000 claims 1
- NAPDTERTUWQXNR-UHFFFAOYSA-N 4-(4-hydroxy-2-methylanilino)-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=C(O)C=C1C NAPDTERTUWQXNR-UHFFFAOYSA-N 0.000 claims 1
- ACACRWSZUZUTEJ-UHFFFAOYSA-N 4-(4-hydroxy-2-methylanilino)-6-methoxy-7-(3-morpholin-4-ylpropoxy)quinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C=C(OCCCN3CCOCC3)C(OC)=CC2=C1NC1=CC=C(O)C=C1C ACACRWSZUZUTEJ-UHFFFAOYSA-N 0.000 claims 1
- OQUDHJHVQGCUOJ-UHFFFAOYSA-N 4-(4-hydroxy-3,5-dimethylanilino)-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC(C)=C(O)C(C)=C1 OQUDHJHVQGCUOJ-UHFFFAOYSA-N 0.000 claims 1
- IVWBIVZBYRCUFO-UHFFFAOYSA-N 4-(5-chloro-2-hydroxyanilino)-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC(Cl)=CC=C1O IVWBIVZBYRCUFO-UHFFFAOYSA-N 0.000 claims 1
- PAOLEDZAKLCSFE-UHFFFAOYSA-N 4-(5-chloro-2-methoxyanilino)-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound COC1=CC=C(Cl)C=C1NC1=C(C#N)C=NC2=CC(OC)=C(OC)C=C12 PAOLEDZAKLCSFE-UHFFFAOYSA-N 0.000 claims 1
- REBRBTLJKXGAAU-UHFFFAOYSA-N 4-(cyclohexylamino)-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1CCCCC1 REBRBTLJKXGAAU-UHFFFAOYSA-N 0.000 claims 1
- SFPGNABUJLHMNQ-UHFFFAOYSA-N 4-(diethylamino)but-2-enamide Chemical compound CCN(CC)CC=CC(N)=O SFPGNABUJLHMNQ-UHFFFAOYSA-N 0.000 claims 1
- TYPPJPWWUXMGRI-UHFFFAOYSA-N 4-(diethylamino)but-2-enoic acid Chemical compound CCN(CC)CC=CC(O)=O TYPPJPWWUXMGRI-UHFFFAOYSA-N 0.000 claims 1
- UATCEBVVGUUBAF-UHFFFAOYSA-N 4-[(2-aminophenyl)methylamino]-6,7-diethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OCC)C(OCC)=CC2=NC=C(C#N)C=1NCC1=CC=CC=C1N UATCEBVVGUUBAF-UHFFFAOYSA-N 0.000 claims 1
- KSTABQDMPVWBQA-UHFFFAOYSA-N 4-[(3,4-dichlorophenyl)methylamino]-6,7-diethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OCC)C(OCC)=CC2=NC=C(C#N)C=1NCC1=CC=C(Cl)C(Cl)=C1 KSTABQDMPVWBQA-UHFFFAOYSA-N 0.000 claims 1
- UNVQEGYJIRTKEA-UHFFFAOYSA-N 4-[(3,4-difluorophenyl)methylamino]-6,7-diethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OCC)C(OCC)=CC2=NC=C(C#N)C=1NCC1=CC=C(F)C(F)=C1 UNVQEGYJIRTKEA-UHFFFAOYSA-N 0.000 claims 1
- MOMWLTJRHZNPRC-UHFFFAOYSA-N 4-[(3-bromophenyl)methylamino]-6,7-diethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OCC)C(OCC)=CC2=NC=C(C#N)C=1NCC1=CC=CC(Br)=C1 MOMWLTJRHZNPRC-UHFFFAOYSA-N 0.000 claims 1
- JVPPPJVZGREELP-UHFFFAOYSA-N 4-[2-(2-hydroxyethyl)anilino]-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=CC=C1CCO JVPPPJVZGREELP-UHFFFAOYSA-N 0.000 claims 1
- XHHYAWSDIXRRAO-UHFFFAOYSA-N 4-[3-(chloromethyl)anilino]-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=CC(CCl)=C1 XHHYAWSDIXRRAO-UHFFFAOYSA-N 0.000 claims 1
- OVFOWMBZHBTKLD-UHFFFAOYSA-N 4-[3-(dimethylamino)anilino]-5,8-dimethoxyquinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C(OC)=CC=C(OC)C2=C1NC1=CC=CC(N(C)C)=C1 OVFOWMBZHBTKLD-UHFFFAOYSA-N 0.000 claims 1
- LMPUEJSCCKBFOV-UHFFFAOYSA-N 4-[3-(dimethylamino)anilino]-6,7,8-trimethoxyquinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C(OC)=C(OC)C(OC)=CC2=C1NC1=CC=CC(N(C)C)=C1 LMPUEJSCCKBFOV-UHFFFAOYSA-N 0.000 claims 1
- OLPCFXOXZCAXNQ-UHFFFAOYSA-N 4-[3-(dimethylamino)anilino]-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=CC(N(C)C)=C1 OLPCFXOXZCAXNQ-UHFFFAOYSA-N 0.000 claims 1
- LFDLSQQIFSWTPB-UHFFFAOYSA-N 4-[3-(dimethylamino)anilino]-6-nitroquinoline-3-carbonitrile Chemical compound CN(C)C1=CC=CC(NC=2C3=CC(=CC=C3N=CC=2C#N)[N+]([O-])=O)=C1 LFDLSQQIFSWTPB-UHFFFAOYSA-N 0.000 claims 1
- OGLPBSWSMKAWCR-UHFFFAOYSA-N 4-[3-(dimethylamino)anilino]-8-methoxyquinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C(OC)=CC=CC2=C1NC1=CC=CC(N(C)C)=C1 OGLPBSWSMKAWCR-UHFFFAOYSA-N 0.000 claims 1
- VEWKMHYYBJASDM-UHFFFAOYSA-N 4-[3-(hydroxymethyl)-2-methylanilino]-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=CC(CO)=C1C VEWKMHYYBJASDM-UHFFFAOYSA-N 0.000 claims 1
- GEUFKSXFZJFSDI-UHFFFAOYSA-N 4-[3-(hydroxymethyl)anilino]-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=CC(CO)=C1 GEUFKSXFZJFSDI-UHFFFAOYSA-N 0.000 claims 1
- ZTHKSSJRIANSFO-UHFFFAOYSA-N 4-[4-(2-hydroxyethyl)anilino]-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=C(CCO)C=C1 ZTHKSSJRIANSFO-UHFFFAOYSA-N 0.000 claims 1
- JPFSELHYKCHNJV-UHFFFAOYSA-N 4-[4-(dimethylamino)anilino]-6-nitroquinoline-3-carbonitrile Chemical compound C1=CC(N(C)C)=CC=C1NC1=C(C#N)C=NC2=CC=C([N+]([O-])=O)C=C12 JPFSELHYKCHNJV-UHFFFAOYSA-N 0.000 claims 1
- VSEAWQWXSBESSQ-UHFFFAOYSA-N 4-[4-chloro-3-(trifluoromethyl)anilino]-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=C(Cl)C(C(F)(F)F)=C1 VSEAWQWXSBESSQ-UHFFFAOYSA-N 0.000 claims 1
- OFWSZEIPLOQZGP-UHFFFAOYSA-N 4-[[4-(3-bromoanilino)-3-cyanoquinolin-6-yl]amino]-2-methylidene-4-oxobutanoic acid Chemical compound C12=CC(NC(=O)CC(=C)C(=O)O)=CC=C2N=CC(C#N)=C1NC1=CC=CC(Br)=C1 OFWSZEIPLOQZGP-UHFFFAOYSA-N 0.000 claims 1
- SHNLPCUCDONAQF-UHFFFAOYSA-N 4-anilino-6,7-diethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OCC)C(OCC)=CC2=NC=C(C#N)C=1NC1=CC=CC=C1 SHNLPCUCDONAQF-UHFFFAOYSA-N 0.000 claims 1
- YYARKMZWFMYHGW-UHFFFAOYSA-N 4-bromo-n-[4-(3-bromo-4-fluoroanilino)-3-cyano-7-methoxyquinolin-6-yl]but-2-enamide Chemical compound C=12C=C(NC(=O)C=CCBr)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=C(F)C(Br)=C1 YYARKMZWFMYHGW-UHFFFAOYSA-N 0.000 claims 1
- LQFDQJDIWFMWHN-UHFFFAOYSA-N 4-morpholin-4-ylbut-2-enoic acid Chemical compound OC(=O)C=CCN1CCOCC1 LQFDQJDIWFMWHN-UHFFFAOYSA-N 0.000 claims 1
- YIUAOQMDEABCMH-UHFFFAOYSA-N 6,7-diethoxy-4-(3-fluoroanilino)quinoline-3-carbonitrile Chemical compound C=12C=C(OCC)C(OCC)=CC2=NC=C(C#N)C=1NC1=CC=CC(F)=C1 YIUAOQMDEABCMH-UHFFFAOYSA-N 0.000 claims 1
- BTUDPTQPRPWGQY-UHFFFAOYSA-N 6,7-diethoxy-4-(4-fluoro-2-methylanilino)quinoline-3-carbonitrile Chemical compound C=12C=C(OCC)C(OCC)=CC2=NC=C(C#N)C=1NC1=CC=C(F)C=C1C BTUDPTQPRPWGQY-UHFFFAOYSA-N 0.000 claims 1
- OGVXUORKCBXMAD-UHFFFAOYSA-N 6,7-diethoxy-4-(4-fluoroanilino)quinoline-3-carbonitrile Chemical compound C=12C=C(OCC)C(OCC)=CC2=NC=C(C#N)C=1NC1=CC=C(F)C=C1 OGVXUORKCBXMAD-UHFFFAOYSA-N 0.000 claims 1
- KLJORPXEIAZGDJ-UHFFFAOYSA-N 6,7-diethoxy-4-(n-methylanilino)quinoline-3-carbonitrile Chemical compound C=12C=C(OCC)C(OCC)=CC2=NC=C(C#N)C=1N(C)C1=CC=CC=C1 KLJORPXEIAZGDJ-UHFFFAOYSA-N 0.000 claims 1
- YXCSSHCCXLUHDG-UHFFFAOYSA-N 6,7-dimethoxy-4-(2-methylanilino)quinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=CC=C1C YXCSSHCCXLUHDG-UHFFFAOYSA-N 0.000 claims 1
- QBPFCLKAEGQCJR-UHFFFAOYSA-N 6,7-dimethoxy-4-(2-methylsulfanylanilino)quinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=CC=C1SC QBPFCLKAEGQCJR-UHFFFAOYSA-N 0.000 claims 1
- ZSJDOQUXSFYFRM-UHFFFAOYSA-N 6,7-dimethoxy-4-(3-methylsulfanylanilino)quinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=CC(SC)=C1 ZSJDOQUXSFYFRM-UHFFFAOYSA-N 0.000 claims 1
- WEOXCMIQDJTOOP-UHFFFAOYSA-N 6,7-dimethoxy-4-(3-nitroanilino)quinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=CC([N+]([O-])=O)=C1 WEOXCMIQDJTOOP-UHFFFAOYSA-N 0.000 claims 1
- VVHLRJCWFVPVSW-UHFFFAOYSA-N 6,7-dimethoxy-4-(3-phenoxyanilino)quinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC(C=1)=CC=CC=1OC1=CC=CC=C1 VVHLRJCWFVPVSW-UHFFFAOYSA-N 0.000 claims 1
- PLZHSFDPFHDSRA-UHFFFAOYSA-N 6,7-dimethoxy-4-(4-methoxy-2-methylanilino)quinoline-3-carbonitrile Chemical compound CC1=CC(OC)=CC=C1NC1=C(C#N)C=NC2=CC(OC)=C(OC)C=C12 PLZHSFDPFHDSRA-UHFFFAOYSA-N 0.000 claims 1
- JXLUYPNXIHHINO-UHFFFAOYSA-N 6,7-dimethoxy-4-(4-methylanilino)quinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=C(C)C=C1 JXLUYPNXIHHINO-UHFFFAOYSA-N 0.000 claims 1
- DRHDIJVDQNOQEI-UHFFFAOYSA-N 6,7-dimethoxy-4-(4-methylsulfanylanilino)quinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=C(SC)C=C1 DRHDIJVDQNOQEI-UHFFFAOYSA-N 0.000 claims 1
- GSVIQADQNZROAL-UHFFFAOYSA-N 6,7-dimethoxy-4-(4-phenoxyanilino)quinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC(C=C1)=CC=C1OC1=CC=CC=C1 GSVIQADQNZROAL-UHFFFAOYSA-N 0.000 claims 1
- LYWXXIOBMCQLNJ-UHFFFAOYSA-N 6,7-dimethoxy-4-(pyridin-3-ylamino)quinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=CN=C1 LYWXXIOBMCQLNJ-UHFFFAOYSA-N 0.000 claims 1
- NPVUUFCFLLPVCM-UHFFFAOYSA-N 6,7-dimethoxy-4-[3-(trifluoromethyl)anilino]quinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=CC(C(F)(F)F)=C1 NPVUUFCFLLPVCM-UHFFFAOYSA-N 0.000 claims 1
- WHMRDYJJAXPWGX-UHFFFAOYSA-N 6,7-dimethoxy-4-[4-(trifluoromethyl)anilino]quinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=C(C(F)(F)F)C=C1 WHMRDYJJAXPWGX-UHFFFAOYSA-N 0.000 claims 1
- MTPYYINKVPVYNQ-UHFFFAOYSA-N 6-(dimethylamino)-4-(3-methoxyanilino)quinoline-3-carbonitrile;hydrochloride Chemical compound Cl.COC1=CC=CC(NC=2C3=CC(=CC=C3N=CC=2C#N)N(C)C)=C1 MTPYYINKVPVYNQ-UHFFFAOYSA-N 0.000 claims 1
- LEACUGBTKYYIDG-UHFFFAOYSA-N 6-amino-4-(3,4-difluoroanilino)quinoline-3-carbonitrile Chemical compound C12=CC(N)=CC=C2N=CC(C#N)=C1NC1=CC=C(F)C(F)=C1 LEACUGBTKYYIDG-UHFFFAOYSA-N 0.000 claims 1
- WMIBAZLHGIVWSU-UHFFFAOYSA-N 6-amino-4-(3-bromo-4-fluoroanilino)-7-methoxyquinoline-3-carbonitrile Chemical compound C=12C=C(N)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=C(F)C(Br)=C1 WMIBAZLHGIVWSU-UHFFFAOYSA-N 0.000 claims 1
- CLGJOTLYNXUVES-UHFFFAOYSA-N 6-amino-4-(3-bromo-4-fluoroanilino)quinoline-3-carbonitrile Chemical compound C12=CC(N)=CC=C2N=CC(C#N)=C1NC1=CC=C(F)C(Br)=C1 CLGJOTLYNXUVES-UHFFFAOYSA-N 0.000 claims 1
- DXWBLHXTKOUIHA-UHFFFAOYSA-N 6-amino-4-(3-bromoanilino)-7-ethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(N)C(OCC)=CC2=NC=C(C#N)C=1NC1=CC=CC(Br)=C1 DXWBLHXTKOUIHA-UHFFFAOYSA-N 0.000 claims 1
- IMBMTYREOJZAAW-UHFFFAOYSA-N 6-amino-4-(3-bromoanilino)-7-methoxyquinoline-3-carbonitrile Chemical compound C=12C=C(N)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=CC(Br)=C1 IMBMTYREOJZAAW-UHFFFAOYSA-N 0.000 claims 1
- PFVDWAYDYKHDEH-UHFFFAOYSA-N 6-amino-4-(3-bromoanilino)-8-[(dimethylamino)methyl]quinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C(CN(C)C)=CC(N)=CC2=C1NC1=CC=CC(Br)=C1 PFVDWAYDYKHDEH-UHFFFAOYSA-N 0.000 claims 1
- GFPFGXYUPCOMGW-UHFFFAOYSA-N 6-amino-4-(3-bromoanilino)-8-methoxyquinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C(OC)=CC(N)=CC2=C1NC1=CC=CC(Br)=C1 GFPFGXYUPCOMGW-UHFFFAOYSA-N 0.000 claims 1
- DRHNHDZBMACOEW-UHFFFAOYSA-N 6-amino-4-(3-chloro-2-thiophen-3-yloxyanilino)quinoline-3-carbonitrile Chemical compound NC=1C=C2C(=C(C=NC2=CC=1)C#N)NC1=C(C(=CC=C1)Cl)OC=1C=CSC=1 DRHNHDZBMACOEW-UHFFFAOYSA-N 0.000 claims 1
- WMSREFWREGHLAP-UHFFFAOYSA-N 6-amino-4-(3-chloro-4-fluoroanilino)quinoline-3-carbonitrile Chemical compound C12=CC(N)=CC=C2N=CC(C#N)=C1NC1=CC=C(F)C(Cl)=C1 WMSREFWREGHLAP-UHFFFAOYSA-N 0.000 claims 1
- IUHXMKMPNZOIIR-UHFFFAOYSA-N 6-amino-4-(3-chloroanilino)quinoline-3-carbonitrile Chemical compound C12=CC(N)=CC=C2N=CC(C#N)=C1NC1=CC=CC(Cl)=C1 IUHXMKMPNZOIIR-UHFFFAOYSA-N 0.000 claims 1
- PDQUVNBKITWFNZ-UHFFFAOYSA-N 6-amino-4-(3-cyanoanilino)quinoline-3-carbonitrile Chemical compound C12=CC(N)=CC=C2N=CC(C#N)=C1NC1=CC=CC(C#N)=C1 PDQUVNBKITWFNZ-UHFFFAOYSA-N 0.000 claims 1
- MJPIXAAXFZASFT-UHFFFAOYSA-N 6-amino-4-(3-ethynylanilino)quinoline-3-carbonitrile Chemical compound C12=CC(N)=CC=C2N=CC(C#N)=C1NC1=CC=CC(C#C)=C1 MJPIXAAXFZASFT-UHFFFAOYSA-N 0.000 claims 1
- UPINFBFRHUFCMT-UHFFFAOYSA-N 6-amino-4-(3-fluoroanilino)quinoline-3-carbonitrile Chemical compound C12=CC(N)=CC=C2N=CC(C#N)=C1NC1=CC=CC(F)=C1 UPINFBFRHUFCMT-UHFFFAOYSA-N 0.000 claims 1
- BCAYGAKYRNJRSZ-UHFFFAOYSA-N 6-amino-4-(3-hydroxy-4-methoxyanilino)-8-methoxyquinoline-3-carbonitrile Chemical compound C1=C(O)C(OC)=CC=C1NC1=C(C#N)C=NC2=C(OC)C=C(N)C=C12 BCAYGAKYRNJRSZ-UHFFFAOYSA-N 0.000 claims 1
- DWJCHBHBLILFOB-UHFFFAOYSA-N 6-amino-4-(3-hydroxy-4-methylanilino)-8-methoxyquinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C(OC)=CC(N)=CC2=C1NC1=CC=C(C)C(O)=C1 DWJCHBHBLILFOB-UHFFFAOYSA-N 0.000 claims 1
- JSCNIEOKVSQSKM-UHFFFAOYSA-N 6-amino-4-(3-iodoanilino)quinoline-3-carbonitrile Chemical compound C12=CC(N)=CC=C2N=CC(C#N)=C1NC1=CC=CC(I)=C1 JSCNIEOKVSQSKM-UHFFFAOYSA-N 0.000 claims 1
- OXXUZYBVAKGKQB-UHFFFAOYSA-N 6-amino-4-(3-methoxyanilino)quinoline-3-carbonitrile Chemical compound COC1=CC=CC(NC=2C3=CC(N)=CC=C3N=CC=2C#N)=C1 OXXUZYBVAKGKQB-UHFFFAOYSA-N 0.000 claims 1
- PNHLUCIDSVSCDW-UHFFFAOYSA-N 6-amino-4-(3-methylanilino)quinoline-3-carbonitrile Chemical compound CC1=CC=CC(NC=2C3=CC(N)=CC=C3N=CC=2C#N)=C1 PNHLUCIDSVSCDW-UHFFFAOYSA-N 0.000 claims 1
- IHOAIURDVZHDEQ-UHFFFAOYSA-N 6-amino-4-(3-methylsulfanylanilino)quinoline-3-carbonitrile Chemical compound CSC1=CC=CC(NC=2C3=CC(N)=CC=C3N=CC=2C#N)=C1 IHOAIURDVZHDEQ-UHFFFAOYSA-N 0.000 claims 1
- BPRJKKPJMZUBDG-UHFFFAOYSA-N 6-amino-4-(3-propan-2-ylanilino)quinoline-3-carbonitrile Chemical compound CC(C)C1=CC=CC(NC=2C3=CC(N)=CC=C3N=CC=2C#N)=C1 BPRJKKPJMZUBDG-UHFFFAOYSA-N 0.000 claims 1
- SIBQYOKZVKAXSA-UHFFFAOYSA-N 6-amino-4-(4-bromoanilino)quinoline-3-carbonitrile Chemical compound C12=CC(N)=CC=C2N=CC(C#N)=C1NC1=CC=C(Br)C=C1 SIBQYOKZVKAXSA-UHFFFAOYSA-N 0.000 claims 1
- VPGQEKLTHYYHRA-UHFFFAOYSA-N 6-amino-4-(4-chloro-2-fluoroanilino)-7-methoxyquinoline-3-carbonitrile Chemical compound C=12C=C(N)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=C(Cl)C=C1F VPGQEKLTHYYHRA-UHFFFAOYSA-N 0.000 claims 1
- NNUBNOJEKVJYEQ-UHFFFAOYSA-N 6-amino-4-[3-(dimethylamino)anilino]quinoline-3-carbonitrile Chemical compound CN(C)C1=CC=CC(NC=2C3=CC(N)=CC=C3N=CC=2C#N)=C1 NNUBNOJEKVJYEQ-UHFFFAOYSA-N 0.000 claims 1
- ATKJDNWWCUYWGP-UHFFFAOYSA-N 6-amino-4-[4-(dimethylamino)anilino]quinoline-3-carbonitrile Chemical compound C1=CC(N(C)C)=CC=C1NC1=C(C#N)C=NC2=CC=C(N)C=C12 ATKJDNWWCUYWGP-UHFFFAOYSA-N 0.000 claims 1
- YOOVBYGMAALDAY-UHFFFAOYSA-N 6-ethoxy-4-(3-hydroxy-4-methylanilino)-7-methoxyquinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C=C(OC)C(OCC)=CC2=C1NC1=CC=C(C)C(O)=C1 YOOVBYGMAALDAY-UHFFFAOYSA-N 0.000 claims 1
- WPUZJCWFDMOJQH-UHFFFAOYSA-N 6-iodo-4-(3-methoxyanilino)quinoline-3-carbonitrile Chemical compound COC1=CC=CC(NC=2C3=CC(I)=CC=C3N=CC=2C#N)=C1 WPUZJCWFDMOJQH-UHFFFAOYSA-N 0.000 claims 1
- WCOAJGXFODNEJR-UHFFFAOYSA-N 6-methoxy-4-(2-methylsulfanylanilino)-7-(3-morpholin-4-ylpropoxy)quinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C=C(OCCCN3CCOCC3)C(OC)=CC2=C1NC1=CC=CC=C1SC WCOAJGXFODNEJR-UHFFFAOYSA-N 0.000 claims 1
- HZFKBQSCERCMGV-UHFFFAOYSA-N 6-nitro-4-(3-propan-2-ylanilino)quinoline-3-carbonitrile Chemical compound CC(C)C1=CC=CC(NC=2C3=CC(=CC=C3N=CC=2C#N)[N+]([O-])=O)=C1 HZFKBQSCERCMGV-UHFFFAOYSA-N 0.000 claims 1
- CRYQEVRYEJPICG-UHFFFAOYSA-N 6-nitro-4-[3-(trifluoromethoxy)anilino]quinoline-3-carbonitrile Chemical compound C12=CC([N+](=O)[O-])=CC=C2N=CC(C#N)=C1NC1=CC=CC(OC(F)(F)F)=C1 CRYQEVRYEJPICG-UHFFFAOYSA-N 0.000 claims 1
- WUVXAOGFNCAWFT-UHFFFAOYSA-N 6-nitro-4-[3-(trifluoromethyl)anilino]quinoline-3-carbonitrile Chemical compound C12=CC([N+](=O)[O-])=CC=C2N=CC(C#N)=C1NC1=CC=CC(C(F)(F)F)=C1 WUVXAOGFNCAWFT-UHFFFAOYSA-N 0.000 claims 1
- PVZCNRGQTKOEAH-UHFFFAOYSA-N 7-[2-(dimethylamino)ethoxy]-4-(3-hydroxy-4-methylanilino)-6-methoxyquinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C=C(OCCN(C)C)C(OC)=CC2=C1NC1=CC=C(C)C(O)=C1 PVZCNRGQTKOEAH-UHFFFAOYSA-N 0.000 claims 1
- ZUZYWMSAFACAAG-UHFFFAOYSA-N 7-ethoxy-4-(3-hydroxy-4-methylanilino)-6-methoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OCC)=CC2=NC=C(C#N)C=1NC1=CC=C(C)C(O)=C1 ZUZYWMSAFACAAG-UHFFFAOYSA-N 0.000 claims 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
- AVKRWJGYHFZIQI-UHFFFAOYSA-N 8-(3-bromoanilino)-[1,3]dioxolo[4,5-g]quinoline-7-carbonitrile Chemical compound BrC1=CC=CC(NC=2C3=CC=4OCOC=4C=C3N=CC=2C#N)=C1 AVKRWJGYHFZIQI-UHFFFAOYSA-N 0.000 claims 1
- OMJZUXOYCMTLLW-UHFFFAOYSA-N 8-methoxy-4-(2,4,6-trifluoroanilino)quinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C(OC)=CC=CC2=C1NC1=C(F)C=C(F)C=C1F OMJZUXOYCMTLLW-UHFFFAOYSA-N 0.000 claims 1
- KQQLOZGNRKQDIE-UHFFFAOYSA-N BrC=1C=C(C=CC1)NC1=C(C=NC2=CC(=C(C=C12)C(C(=O)N)=CCN(C)C)OCC)C#N Chemical compound BrC=1C=C(C=CC1)NC1=C(C=NC2=CC(=C(C=C12)C(C(=O)N)=CCN(C)C)OCC)C#N KQQLOZGNRKQDIE-UHFFFAOYSA-N 0.000 claims 1
- HUFZDVAQAIUTDV-UHFFFAOYSA-N BrC=1C=C(C=CC1)NC1=C(C=NC2=CC=C(C=C12)C(C(=O)N)=CCN(C)C)C#N Chemical compound BrC=1C=C(C=CC1)NC1=C(C=NC2=CC=C(C=C12)C(C(=O)N)=CCN(C)C)C#N HUFZDVAQAIUTDV-UHFFFAOYSA-N 0.000 claims 1
- DUDIDVYPJSIFRP-UHFFFAOYSA-N BrC=1C=C(C=CC1)NC1=C(C=NC2=CC=C(C=C12)C(C(=O)N)=CCNC)C#N Chemical compound BrC=1C=C(C=CC1)NC1=C(C=NC2=CC=C(C=C12)C(C(=O)N)=CCNC)C#N DUDIDVYPJSIFRP-UHFFFAOYSA-N 0.000 claims 1
- 208000026310 Breast neoplasm Diseases 0.000 claims 1
- WISASWSOACPVPH-UHFFFAOYSA-N CCN(CC)CC=C(C(N)=O)C(C=C(C(N=C1)=C2)C(NC3=CC(Br)=CC=C3)=C1C#N)=C2OC Chemical compound CCN(CC)CC=C(C(N)=O)C(C=C(C(N=C1)=C2)C(NC3=CC(Br)=CC=C3)=C1C#N)=C2OC WISASWSOACPVPH-UHFFFAOYSA-N 0.000 claims 1
- PVKCFTOFUIKUJZ-UHFFFAOYSA-N CCN(CC)CC=C(C(N)=O)C(C=C12)=CC(OC)=C1N=CC(C#N)=C2NC1=CC(Br)=CC=C1 Chemical compound CCN(CC)CC=C(C(N)=O)C(C=C12)=CC(OC)=C1N=CC(C#N)=C2NC1=CC(Br)=CC=C1 PVKCFTOFUIKUJZ-UHFFFAOYSA-N 0.000 claims 1
- QUJOEBKOWUZPNK-UHFFFAOYSA-N CCN(CC)CC=C(C(N)=O)C(C=C12)=CC=C1N=CC(C#N)=C2NC1=CC(Br)=CC=C1 Chemical compound CCN(CC)CC=C(C(N)=O)C(C=C12)=CC=C1N=CC(C#N)=C2NC1=CC(Br)=CC=C1 QUJOEBKOWUZPNK-UHFFFAOYSA-N 0.000 claims 1
- WCZDOSFVSPGHJB-UHFFFAOYSA-N CCOC(C=C(C1=C2)N=CC(C#N)=C1NC1=CC(Br)=CC=C1)=C2C(C(N)=O)=CCBr Chemical compound CCOC(C=C(C1=C2)N=CC(C#N)=C1NC1=CC(Br)=CC=C1)=C2C(C(N)=O)=CCBr WCZDOSFVSPGHJB-UHFFFAOYSA-N 0.000 claims 1
- ZMWPGHJIIXPGJR-UHFFFAOYSA-N CCOC(C=C(C1=C2)N=CC(C#N)=C1NC1=CC(Br)=CC=C1)=C2C(C(N)=O)=CCN1CCOCC1 Chemical compound CCOC(C=C(C1=C2)N=CC(C#N)=C1NC1=CC(Br)=CC=C1)=C2C(C(N)=O)=CCN1CCOCC1 ZMWPGHJIIXPGJR-UHFFFAOYSA-N 0.000 claims 1
- DHRJECPTWNVIRL-UHFFFAOYSA-N CN(C)CC=C(C(N)=O)C(C=C(C(N=C1)=C2)C(NC(C=C3)=CC(Br)=C3F)=C1C#N)=C2OC Chemical compound CN(C)CC=C(C(N)=O)C(C=C(C(N=C1)=C2)C(NC(C=C3)=CC(Br)=C3F)=C1C#N)=C2OC DHRJECPTWNVIRL-UHFFFAOYSA-N 0.000 claims 1
- FYBRQONELTZVIV-UHFFFAOYSA-N CN(C)CC=C(C(N)=O)C(C=C12)=CC(OC)=C1N=CC(C#N)=C2NC1=CC(Br)=CC=C1 Chemical compound CN(C)CC=C(C(N)=O)C(C=C12)=CC(OC)=C1N=CC(C#N)=C2NC1=CC(Br)=CC=C1 FYBRQONELTZVIV-UHFFFAOYSA-N 0.000 claims 1
- QKHICLWDVMBYPB-UHFFFAOYSA-N COC(C=C(C1=C2)N=CC(C#N)=C1NC1=CC(Br)=CC=C1)=C2C(C(N)=O)=CCN1CCOCC1 Chemical compound COC(C=C(C1=C2)N=CC(C#N)=C1NC1=CC(Br)=CC=C1)=C2C(C(N)=O)=CCN1CCOCC1 QKHICLWDVMBYPB-UHFFFAOYSA-N 0.000 claims 1
- QXQUAHVHTYZGHA-UHFFFAOYSA-N COC(C=C(C=C12)C(C(N)=O)=CCBr)=C1N=CC(C#N)=C2NC1=CC(Br)=CC=C1 Chemical compound COC(C=C(C=C12)C(C(N)=O)=CCBr)=C1N=CC(C#N)=C2NC1=CC(Br)=CC=C1 QXQUAHVHTYZGHA-UHFFFAOYSA-N 0.000 claims 1
- ZDAADSXPYYFWNE-UHFFFAOYSA-N COC(C=C(C=C12)C(C(N)=O)=CCN3CCOCC3)=C1N=CC(C#N)=C2NC1=CC(Br)=CC=C1 Chemical compound COC(C=C(C=C12)C(C(N)=O)=CCN3CCOCC3)=C1N=CC(C#N)=C2NC1=CC(Br)=CC=C1 ZDAADSXPYYFWNE-UHFFFAOYSA-N 0.000 claims 1
- INOMEHXQVGAUMT-UHFFFAOYSA-N COCC=C(C(N)=O)C(C=C12)=CC=C1N=CC(C#N)=C2NC1=CC(Br)=CC=C1 Chemical compound COCC=C(C(N)=O)C(C=C12)=CC=C1N=CC(C#N)=C2NC1=CC(Br)=CC=C1 INOMEHXQVGAUMT-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- WXZKIKQSGYISMT-UHFFFAOYSA-N ClC=1C(=C(C=CC=1)NC1=C(C=NC2=CC=C(C=C12)NC(C=C)=O)C#N)OC=1C=CSC=1 Chemical compound ClC=1C(=C(C=CC=1)NC1=C(C=NC2=CC=C(C=C12)NC(C=C)=O)C#N)OC=1C=CSC=1 WXZKIKQSGYISMT-UHFFFAOYSA-N 0.000 claims 1
- ZSXGLVDWWRXATF-UHFFFAOYSA-N N,N-dimethylformamide dimethyl acetal Chemical compound COC(OC)N(C)C ZSXGLVDWWRXATF-UHFFFAOYSA-N 0.000 claims 1
- WXYBQHVGNHSYBJ-UHFFFAOYSA-N N-(3-bromophenyl)-N-(3-cyano-6,7-dihydroxyquinolin-4-yl)acetamide Chemical compound N#CC=1C=NC2=CC(O)=C(O)C=C2C=1N(C(=O)C)C1=CC=CC(Br)=C1 WXYBQHVGNHSYBJ-UHFFFAOYSA-N 0.000 claims 1
- CTDCXHMAQLCDPT-UHFFFAOYSA-N N-[4-(3-chloro-2-thiophen-3-yloxyanilino)-3-cyanoquinolin-6-yl]but-2-ynamide Chemical compound ClC=1C(=C(C=CC=1)NC1=C(C=NC2=CC=C(C=C12)NC(C#CC)=O)C#N)OC=1C=CSC=1 CTDCXHMAQLCDPT-UHFFFAOYSA-N 0.000 claims 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims 1
- KYEGVJNWCFQOKX-UHFFFAOYSA-N OC1=C(C=CC(=C1)C)NC1=NC2=CC(=C(C=C2C=C1C#N)OC)OC Chemical compound OC1=C(C=CC(=C1)C)NC1=NC2=CC(=C(C=C2C=C1C#N)OC)OC KYEGVJNWCFQOKX-UHFFFAOYSA-N 0.000 claims 1
- 125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 230000010933 acylation Effects 0.000 claims 1
- 238000005917 acylation reaction Methods 0.000 claims 1
- 125000006319 alkynyl amino group Chemical group 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 229910021529 ammonia Inorganic materials 0.000 claims 1
- 150000008064 anhydrides Chemical class 0.000 claims 1
- 150000001448 anilines Chemical class 0.000 claims 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 238000009835 boiling Methods 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000002843 carboxylic acid group Chemical group 0.000 claims 1
- 239000003638 chemical reducing agent Substances 0.000 claims 1
- 239000012320 chlorinating reagent Substances 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 239000012024 dehydrating agents Substances 0.000 claims 1
- 239000003937 drug carrier Chemical group 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- LFKYBJLFJOOKAE-UHFFFAOYSA-N imidazol-2-ylidenemethanone Chemical compound O=C=C1N=CC=N1 LFKYBJLFJOOKAE-UHFFFAOYSA-N 0.000 claims 1
- 230000001771 impaired effect Effects 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- 229910052740 iodine Chemical group 0.000 claims 1
- 239000011630 iodine Chemical group 0.000 claims 1
- 210000005075 mammary gland Anatomy 0.000 claims 1
- ADTHOQASRLCLRF-UHFFFAOYSA-N n-[3-[(3-cyano-6,7-dimethoxyquinolin-4-yl)amino]phenyl]acetamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=CC(NC(C)=O)=C1 ADTHOQASRLCLRF-UHFFFAOYSA-N 0.000 claims 1
- YPKIJBWMDLKPTG-UHFFFAOYSA-N n-[3-cyano-4-(3,4-difluoroanilino)quinolin-6-yl]but-2-ynamide Chemical compound C12=CC(NC(=O)C#CC)=CC=C2N=CC(C#N)=C1NC1=CC=C(F)C(F)=C1 YPKIJBWMDLKPTG-UHFFFAOYSA-N 0.000 claims 1
- SQGPYBQAQIKBQS-UHFFFAOYSA-N n-[3-cyano-4-(3,4-difluoroanilino)quinolin-6-yl]prop-2-enamide Chemical compound C1=C(F)C(F)=CC=C1NC1=C(C#N)C=NC2=CC=C(NC(=O)C=C)C=C12 SQGPYBQAQIKBQS-UHFFFAOYSA-N 0.000 claims 1
- RLAZEQDNCUQRSX-UHFFFAOYSA-N n-[3-cyano-4-(3-cyanoanilino)quinolin-6-yl]-4-piperidin-1-ylbut-2-ynamide Chemical compound C1CCCCN1CC#CC(=O)NC(C=C12)=CC=C1N=CC(C#N)=C2NC1=CC=CC(C#N)=C1 RLAZEQDNCUQRSX-UHFFFAOYSA-N 0.000 claims 1
- VMWRFOQWNJQIMZ-UHFFFAOYSA-N n-[3-cyano-4-(3-cyanoanilino)quinolin-6-yl]prop-2-enamide Chemical compound C12=CC(NC(=O)C=C)=CC=C2N=CC(C#N)=C1NC1=CC=CC(C#N)=C1 VMWRFOQWNJQIMZ-UHFFFAOYSA-N 0.000 claims 1
- BBBFROLYSXGUOP-UHFFFAOYSA-N n-[3-cyano-4-(3-ethynylanilino)quinolin-6-yl]-4-piperidin-1-ylbut-2-ynamide Chemical compound C1CCCCN1CC#CC(=O)NC(C=C12)=CC=C1N=CC(C#N)=C2NC1=CC=CC(C#C)=C1 BBBFROLYSXGUOP-UHFFFAOYSA-N 0.000 claims 1
- WFMBJUVKYJBICW-UHFFFAOYSA-N n-[3-cyano-4-(3-ethynylanilino)quinolin-6-yl]but-2-ynamide Chemical compound C12=CC(NC(=O)C#CC)=CC=C2N=CC(C#N)=C1NC1=CC=CC(C#C)=C1 WFMBJUVKYJBICW-UHFFFAOYSA-N 0.000 claims 1
- WQTFCVASSZGLCT-UHFFFAOYSA-N n-[3-cyano-4-(3-ethynylanilino)quinolin-6-yl]prop-2-enamide Chemical compound C12=CC(NC(=O)C=C)=CC=C2N=CC(C#N)=C1NC1=CC=CC(C#C)=C1 WQTFCVASSZGLCT-UHFFFAOYSA-N 0.000 claims 1
- XNWKTBYXWIDLCZ-UHFFFAOYSA-N n-[3-cyano-4-(3-fluoroanilino)quinolin-6-yl]prop-2-enamide Chemical compound FC1=CC=CC(NC=2C3=CC(NC(=O)C=C)=CC=C3N=CC=2C#N)=C1 XNWKTBYXWIDLCZ-UHFFFAOYSA-N 0.000 claims 1
- RKKMOSSRGMBZAO-UHFFFAOYSA-N n-[3-cyano-4-(3-iodoanilino)quinolin-6-yl]prop-2-enamide Chemical compound IC1=CC=CC(NC=2C3=CC(NC(=O)C=C)=CC=C3N=CC=2C#N)=C1 RKKMOSSRGMBZAO-UHFFFAOYSA-N 0.000 claims 1
- VYLDYNHWUMJQMD-UHFFFAOYSA-N n-[3-cyano-4-(3-methoxyanilino)quinolin-6-yl]-4-piperidin-1-ylbut-2-ynamide Chemical compound COC1=CC=CC(NC=2C3=CC(NC(=O)C#CCN4CCCCC4)=CC=C3N=CC=2C#N)=C1 VYLDYNHWUMJQMD-UHFFFAOYSA-N 0.000 claims 1
- HMNIDDVKONQLPW-UHFFFAOYSA-N n-[3-cyano-4-(3-methoxyanilino)quinolin-6-yl]but-2-ynamide Chemical compound COC1=CC=CC(NC=2C3=CC(NC(=O)C#CC)=CC=C3N=CC=2C#N)=C1 HMNIDDVKONQLPW-UHFFFAOYSA-N 0.000 claims 1
- JEVROOVJYXQOEZ-UHFFFAOYSA-N n-[3-cyano-4-(3-methoxyanilino)quinolin-6-yl]prop-2-enamide Chemical compound COC1=CC=CC(NC=2C3=CC(NC(=O)C=C)=CC=C3N=CC=2C#N)=C1 JEVROOVJYXQOEZ-UHFFFAOYSA-N 0.000 claims 1
- QMRGXXWQJSOWEE-UHFFFAOYSA-N n-[3-cyano-4-(3-methylanilino)quinolin-6-yl]but-2-ynamide Chemical compound C12=CC(NC(=O)C#CC)=CC=C2N=CC(C#N)=C1NC1=CC=CC(C)=C1 QMRGXXWQJSOWEE-UHFFFAOYSA-N 0.000 claims 1
- NOPOIBJRWQZCGR-UHFFFAOYSA-N n-[3-cyano-4-(3-methylanilino)quinolin-6-yl]prop-2-enamide Chemical compound CC1=CC=CC(NC=2C3=CC(NC(=O)C=C)=CC=C3N=CC=2C#N)=C1 NOPOIBJRWQZCGR-UHFFFAOYSA-N 0.000 claims 1
- WUWIZNDWEZIYSB-UHFFFAOYSA-N n-[3-cyano-4-(3-propan-2-ylanilino)quinolin-6-yl]but-2-ynamide Chemical compound C12=CC(NC(=O)C#CC)=CC=C2N=CC(C#N)=C1NC1=CC=CC(C(C)C)=C1 WUWIZNDWEZIYSB-UHFFFAOYSA-N 0.000 claims 1
- MQWPQDJSSWDVTQ-UHFFFAOYSA-N n-[3-cyano-4-(3-propan-2-ylanilino)quinolin-6-yl]prop-2-enamide Chemical compound CC(C)C1=CC=CC(NC=2C3=CC(NC(=O)C=C)=CC=C3N=CC=2C#N)=C1 MQWPQDJSSWDVTQ-UHFFFAOYSA-N 0.000 claims 1
- QSMHWFXKNHCJSQ-UHFFFAOYSA-N n-[3-cyano-4-[3-(dimethylamino)anilino]quinolin-6-yl]prop-2-enamide Chemical compound CN(C)C1=CC=CC(NC=2C3=CC(NC(=O)C=C)=CC=C3N=CC=2C#N)=C1 QSMHWFXKNHCJSQ-UHFFFAOYSA-N 0.000 claims 1
- VVNVIMKVRAEOEX-UHFFFAOYSA-N n-[3-cyano-4-[3-(trifluoromethyl)anilino]quinolin-6-yl]but-2-ynamide Chemical compound C12=CC(NC(=O)C#CC)=CC=C2N=CC(C#N)=C1NC1=CC=CC(C(F)(F)F)=C1 VVNVIMKVRAEOEX-UHFFFAOYSA-N 0.000 claims 1
- JSPHYZXDFYTYMG-UHFFFAOYSA-N n-[3-cyano-4-[4-(dimethylamino)anilino]quinolin-6-yl]prop-2-enamide Chemical compound C1=CC(N(C)C)=CC=C1NC1=C(C#N)C=NC2=CC=C(NC(=O)C=C)C=C12 JSPHYZXDFYTYMG-UHFFFAOYSA-N 0.000 claims 1
- KEQGHXFVKOQNQC-UHFFFAOYSA-N n-[4-(3-bromo-4-fluoroanilino)-3-cyano-7-methoxyquinolin-6-yl]-4-morpholin-4-ylbut-2-enamide Chemical compound C=12C=C(NC(=O)C=CCN3CCOCC3)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=C(F)C(Br)=C1 KEQGHXFVKOQNQC-UHFFFAOYSA-N 0.000 claims 1
- AKTAELVLHHYTPP-UHFFFAOYSA-N n-[4-(3-bromo-4-fluoroanilino)-3-cyanoquinolin-6-yl]-4-(diethylamino)but-2-enamide Chemical compound C12=CC(NC(=O)C=CCN(CC)CC)=CC=C2N=CC(C#N)=C1NC1=CC=C(F)C(Br)=C1 AKTAELVLHHYTPP-UHFFFAOYSA-N 0.000 claims 1
- OFGJOXKWOLGBRC-UHFFFAOYSA-N n-[4-(3-bromo-4-fluoroanilino)-3-cyanoquinolin-6-yl]-4-(dimethylamino)but-2-enamide Chemical compound C12=CC(NC(=O)C=CCN(C)C)=CC=C2N=CC(C#N)=C1NC1=CC=C(F)C(Br)=C1 OFGJOXKWOLGBRC-UHFFFAOYSA-N 0.000 claims 1
- HYAJGYAMFMLZDR-UHFFFAOYSA-N n-[4-(3-bromo-4-fluoroanilino)-3-cyanoquinolin-6-yl]-4-(dimethylamino)but-2-ynamide Chemical compound C12=CC(NC(=O)C#CCN(C)C)=CC=C2N=CC(C#N)=C1NC1=CC=C(F)C(Br)=C1 HYAJGYAMFMLZDR-UHFFFAOYSA-N 0.000 claims 1
- SPXOEZKLWIVPKM-UHFFFAOYSA-N n-[4-(3-bromo-4-fluoroanilino)-3-cyanoquinolin-6-yl]-4-morpholin-4-ylbut-2-enamide Chemical compound C1=C(Br)C(F)=CC=C1NC(C1=C2)=C(C#N)C=NC1=CC=C2NC(=O)C=CCN1CCOCC1 SPXOEZKLWIVPKM-UHFFFAOYSA-N 0.000 claims 1
- QWSSCGSSNDSGPP-UHFFFAOYSA-N n-[4-(3-bromoanilino)-3-cyano-7-methoxyquinolin-6-yl]-4-chlorobut-2-enamide Chemical compound C=12C=C(NC(=O)C=CCCl)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=CC(Br)=C1 QWSSCGSSNDSGPP-UHFFFAOYSA-N 0.000 claims 1
- PLQLHGCLAWKBJG-UHFFFAOYSA-N n-[4-(3-bromoanilino)-3-cyano-7-methoxyquinolin-6-yl]but-2-ynamide Chemical compound C=12C=C(NC(=O)C#CC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=CC(Br)=C1 PLQLHGCLAWKBJG-UHFFFAOYSA-N 0.000 claims 1
- HKLOKSUROGEMSK-UHFFFAOYSA-N n-[4-(3-bromoanilino)-3-cyano-7-methoxyquinolin-6-yl]prop-2-enamide Chemical compound C=12C=C(NC(=O)C=C)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=CC(Br)=C1 HKLOKSUROGEMSK-UHFFFAOYSA-N 0.000 claims 1
- KBJXOMLMGJAGKB-UHFFFAOYSA-N n-[4-(3-bromoanilino)-3-cyano-8-[(dimethylamino)methyl]quinolin-6-yl]acetamide Chemical compound N#CC1=CN=C2C(CN(C)C)=CC(NC(C)=O)=CC2=C1NC1=CC=CC(Br)=C1 KBJXOMLMGJAGKB-UHFFFAOYSA-N 0.000 claims 1
- LERVYVZYFPUODM-UHFFFAOYSA-N n-[4-(3-bromoanilino)-3-cyano-8-[(dimethylamino)methyl]quinolin-6-yl]but-2-ynamide Chemical compound C12=CC(NC(=O)C#CC)=CC(CN(C)C)=C2N=CC(C#N)=C1NC1=CC=CC(Br)=C1 LERVYVZYFPUODM-UHFFFAOYSA-N 0.000 claims 1
- GJYOWCCGMOXTJG-UHFFFAOYSA-N n-[4-(3-bromoanilino)-3-cyano-8-[(dimethylamino)methyl]quinolin-6-yl]prop-2-enamide Chemical compound N#CC1=CN=C2C(CN(C)C)=CC(NC(=O)C=C)=CC2=C1NC1=CC=CC(Br)=C1 GJYOWCCGMOXTJG-UHFFFAOYSA-N 0.000 claims 1
- CQFOPPHLPZNBKO-UHFFFAOYSA-N n-[4-(3-bromoanilino)-3-cyanoquinolin-6-yl]-2-(morpholin-4-ylmethyl)prop-2-enamide Chemical compound BrC1=CC=CC(NC=2C3=CC(NC(=O)C(=C)CN4CCOCC4)=CC=C3N=CC=2C#N)=C1 CQFOPPHLPZNBKO-UHFFFAOYSA-N 0.000 claims 1
- PTSZXFBVOGOHCV-UHFFFAOYSA-N n-[4-(3-bromoanilino)-3-cyanoquinolin-6-yl]-2-chloroacetamide Chemical compound C12=CC(NC(=O)CCl)=CC=C2N=CC(C#N)=C1NC1=CC=CC(Br)=C1 PTSZXFBVOGOHCV-UHFFFAOYSA-N 0.000 claims 1
- RRPOWKSQIHLYPG-UHFFFAOYSA-N n-[4-(3-bromoanilino)-3-cyanoquinolin-6-yl]-2-methylprop-2-enamide Chemical compound C12=CC(NC(=O)C(=C)C)=CC=C2N=CC(C#N)=C1NC1=CC=CC(Br)=C1 RRPOWKSQIHLYPG-UHFFFAOYSA-N 0.000 claims 1
- HXFGGFIRXYTMPO-UHFFFAOYSA-N n-[4-(3-bromoanilino)-3-cyanoquinolin-6-yl]-4-(4-ethylpiperazin-1-yl)but-2-ynamide Chemical compound C1CN(CC)CCN1CC#CC(=O)NC1=CC=C(N=CC(C#N)=C2NC=3C=C(Br)C=CC=3)C2=C1 HXFGGFIRXYTMPO-UHFFFAOYSA-N 0.000 claims 1
- PMOGPFDGDJBBQR-UHFFFAOYSA-N n-[4-(3-bromoanilino)-3-cyanoquinolin-6-yl]-4-(4-methylpiperazin-1-yl)but-2-ynamide Chemical compound C1CN(C)CCN1CC#CC(=O)NC1=CC=C(N=CC(C#N)=C2NC=3C=C(Br)C=CC=3)C2=C1 PMOGPFDGDJBBQR-UHFFFAOYSA-N 0.000 claims 1
- UYTOXOMHJMCOKH-UHFFFAOYSA-N n-[4-(3-bromoanilino)-3-cyanoquinolin-6-yl]-4-(diethylamino)but-2-ynamide Chemical compound C12=CC(NC(=O)C#CCN(CC)CC)=CC=C2N=CC(C#N)=C1NC1=CC=CC(Br)=C1 UYTOXOMHJMCOKH-UHFFFAOYSA-N 0.000 claims 1
- NYRBHASTRFCNHY-UHFFFAOYSA-N n-[4-(3-bromoanilino)-3-cyanoquinolin-6-yl]-4-(dipropylamino)but-2-ynamide Chemical compound C12=CC(NC(=O)C#CCN(CCC)CCC)=CC=C2N=CC(C#N)=C1NC1=CC=CC(Br)=C1 NYRBHASTRFCNHY-UHFFFAOYSA-N 0.000 claims 1
- OXGRVGJNLBMVAH-UHFFFAOYSA-N n-[4-(3-bromoanilino)-3-cyanoquinolin-6-yl]-4-[di(propan-2-yl)amino]but-2-ynamide Chemical compound C12=CC(NC(=O)C#CCN(C(C)C)C(C)C)=CC=C2N=CC(C#N)=C1NC1=CC=CC(Br)=C1 OXGRVGJNLBMVAH-UHFFFAOYSA-N 0.000 claims 1
- JNBUZUCZWYMEFZ-UHFFFAOYSA-N n-[4-(3-bromoanilino)-3-cyanoquinolin-6-yl]-4-[tert-butyl(dimethyl)silyl]oxybut-2-ynamide Chemical compound C12=CC(NC(=O)C#CCO[Si](C)(C)C(C)(C)C)=CC=C2N=CC(C#N)=C1NC1=CC=CC(Br)=C1 JNBUZUCZWYMEFZ-UHFFFAOYSA-N 0.000 claims 1
- KPTBCNWYGZERPK-UHFFFAOYSA-N n-[4-(3-bromoanilino)-3-cyanoquinolin-6-yl]-4-piperidin-1-ylbut-2-ynamide Chemical compound BrC1=CC=CC(NC=2C3=CC(NC(=O)C#CCN4CCCCC4)=CC=C3N=CC=2C#N)=C1 KPTBCNWYGZERPK-UHFFFAOYSA-N 0.000 claims 1
- KGUJQEYRHHBQRF-UHFFFAOYSA-N n-[4-(3-bromoanilino)-3-cyanoquinolin-6-yl]acetamide Chemical compound C12=CC(NC(=O)C)=CC=C2N=CC(C#N)=C1NC1=CC=CC(Br)=C1 KGUJQEYRHHBQRF-UHFFFAOYSA-N 0.000 claims 1
- PBDJWRUCRSLDEM-UHFFFAOYSA-N n-[4-(3-bromoanilino)-3-cyanoquinolin-6-yl]but-2-ynamide Chemical compound C12=CC(NC(=O)C#CC)=CC=C2N=CC(C#N)=C1NC1=CC=CC(Br)=C1 PBDJWRUCRSLDEM-UHFFFAOYSA-N 0.000 claims 1
- JKBHSBZUZPGJAH-UHFFFAOYSA-N n-[4-(3-bromoanilino)-3-cyanoquinolin-6-yl]butanamide Chemical compound C12=CC(NC(=O)CCC)=CC=C2N=CC(C#N)=C1NC1=CC=CC(Br)=C1 JKBHSBZUZPGJAH-UHFFFAOYSA-N 0.000 claims 1
- MSLIBSZZLAWHQM-UHFFFAOYSA-N n-[4-(3-bromoanilino)-3-cyanoquinolin-6-yl]prop-2-enamide Chemical compound BrC1=CC=CC(NC=2C3=CC(NC(=O)C=C)=CC=C3N=CC=2C#N)=C1 MSLIBSZZLAWHQM-UHFFFAOYSA-N 0.000 claims 1
- QAIWBHUZZZOVEO-UHFFFAOYSA-N n-[4-(3-bromoanilino)-3-cyanoquinolin-6-yl]propanamide Chemical compound C12=CC(NC(=O)CC)=CC=C2N=CC(C#N)=C1NC1=CC=CC(Br)=C1 QAIWBHUZZZOVEO-UHFFFAOYSA-N 0.000 claims 1
- VHGGLPYMJXZJFI-UHFFFAOYSA-N n-[4-(3-bromoanilino)quinazolin-6-yl]-4-methoxybut-2-enamide Chemical compound C12=CC(NC(=O)C=CCOC)=CC=C2N=CN=C1NC1=CC=CC(Br)=C1 VHGGLPYMJXZJFI-UHFFFAOYSA-N 0.000 claims 1
- FZGMFMLMNGWHRX-UHFFFAOYSA-N n-[4-(3-chloro-4-fluoroanilino)-3-cyanoquinolin-6-yl]-2-(morpholin-4-ylmethyl)prop-2-enamide Chemical compound C1=C(Cl)C(F)=CC=C1NC(C1=C2)=C(C#N)C=NC1=CC=C2NC(=O)C(=C)CN1CCOCC1 FZGMFMLMNGWHRX-UHFFFAOYSA-N 0.000 claims 1
- WZKCFGBQMSKKQQ-UHFFFAOYSA-N n-[4-(3-chloro-4-fluoroanilino)-3-cyanoquinolin-6-yl]-4-(diethylamino)but-2-enamide Chemical compound C12=CC(NC(=O)C=CCN(CC)CC)=CC=C2N=CC(C#N)=C1NC1=CC=C(F)C(Cl)=C1 WZKCFGBQMSKKQQ-UHFFFAOYSA-N 0.000 claims 1
- VMBCEWCTCURUPS-UHFFFAOYSA-N n-[4-(3-chloro-4-fluoroanilino)-3-cyanoquinolin-6-yl]-4-(diethylamino)but-2-ynamide Chemical compound C12=CC(NC(=O)C#CCN(CC)CC)=CC=C2N=CC(C#N)=C1NC1=CC=C(F)C(Cl)=C1 VMBCEWCTCURUPS-UHFFFAOYSA-N 0.000 claims 1
- KXQYGHZAGFHMDJ-UHFFFAOYSA-N n-[4-(3-chloro-4-fluoroanilino)-3-cyanoquinolin-6-yl]-4-(dimethylamino)but-2-enamide Chemical compound C12=CC(NC(=O)C=CCN(C)C)=CC=C2N=CC(C#N)=C1NC1=CC=C(F)C(Cl)=C1 KXQYGHZAGFHMDJ-UHFFFAOYSA-N 0.000 claims 1
- IRNUPYILYRKBDU-UHFFFAOYSA-N n-[4-(3-chloro-4-fluoroanilino)-3-cyanoquinolin-6-yl]-4-(dimethylamino)but-2-ynamide Chemical compound C12=CC(NC(=O)C#CCN(C)C)=CC=C2N=CC(C#N)=C1NC1=CC=C(F)C(Cl)=C1 IRNUPYILYRKBDU-UHFFFAOYSA-N 0.000 claims 1
- QFBZIQWYXFSVHH-UHFFFAOYSA-N n-[4-(3-chloro-4-fluoroanilino)-3-cyanoquinolin-6-yl]-4-methoxybut-2-ynamide Chemical compound C12=CC(NC(=O)C#CCOC)=CC=C2N=CC(C#N)=C1NC1=CC=C(F)C(Cl)=C1 QFBZIQWYXFSVHH-UHFFFAOYSA-N 0.000 claims 1
- USKFPOBBUSZDCR-UHFFFAOYSA-N n-[4-(3-chloro-4-fluoroanilino)-3-cyanoquinolin-6-yl]-4-morpholin-4-ylbut-2-enamide Chemical compound C1=C(Cl)C(F)=CC=C1NC(C1=C2)=C(C#N)C=NC1=CC=C2NC(=O)C=CCN1CCOCC1 USKFPOBBUSZDCR-UHFFFAOYSA-N 0.000 claims 1
- GPLSEURFJLQXHR-UHFFFAOYSA-N n-[4-(3-chloro-4-fluoroanilino)-3-cyanoquinolin-6-yl]but-2-ynamide Chemical compound C12=CC(NC(=O)C#CC)=CC=C2N=CC(C#N)=C1NC1=CC=C(F)C(Cl)=C1 GPLSEURFJLQXHR-UHFFFAOYSA-N 0.000 claims 1
- CYCQVROTABWGKI-UHFFFAOYSA-N n-[4-(3-chloro-4-fluoroanilino)-3-cyanoquinolin-6-yl]prop-2-enamide Chemical compound C1=C(Cl)C(F)=CC=C1NC1=C(C#N)C=NC2=CC=C(NC(=O)C=C)C=C12 CYCQVROTABWGKI-UHFFFAOYSA-N 0.000 claims 1
- SFXWFZYYIXZARH-UHFFFAOYSA-N n-[4-(3-chloroanilino)-3-cyanoquinolin-6-yl]but-2-ynamide Chemical compound C12=CC(NC(=O)C#CC)=CC=C2N=CC(C#N)=C1NC1=CC=CC(Cl)=C1 SFXWFZYYIXZARH-UHFFFAOYSA-N 0.000 claims 1
- GASFMMJWWWYIBV-UHFFFAOYSA-N n-[4-(3-chloroanilino)-3-cyanoquinolin-6-yl]prop-2-enamide Chemical compound ClC1=CC=CC(NC=2C3=CC(NC(=O)C=C)=CC=C3N=CC=2C#N)=C1 GASFMMJWWWYIBV-UHFFFAOYSA-N 0.000 claims 1
- HZFFAOYHSJFYAC-UHFFFAOYSA-N n-[4-(4-bromoanilino)-3-cyanoquinolin-6-yl]but-2-ynamide Chemical compound C12=CC(NC(=O)C#CC)=CC=C2N=CC(C#N)=C1NC1=CC=C(Br)C=C1 HZFFAOYHSJFYAC-UHFFFAOYSA-N 0.000 claims 1
- JQOCJKUVECLNAC-UHFFFAOYSA-N n-[4-(4-bromoanilino)-3-cyanoquinolin-6-yl]prop-2-enamide Chemical compound C1=CC(Br)=CC=C1NC1=C(C#N)C=NC2=CC=C(NC(=O)C=C)C=C12 JQOCJKUVECLNAC-UHFFFAOYSA-N 0.000 claims 1
- 230000017066 negative regulation of growth Effects 0.000 claims 1
- 150000007530 organic bases Chemical class 0.000 claims 1
- WMOZUHUKRDBJEF-UHFFFAOYSA-N s-[[3-[(3-cyano-6,7-dimethoxyquinolin-4-yl)amino]phenyl]methyl] ethanethioate Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=CC(CSC(C)=O)=C1 WMOZUHUKRDBJEF-UHFFFAOYSA-N 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 229940124597 therapeutic agent Drugs 0.000 claims 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 claims 1
- 230000003827 upregulation Effects 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 abstract 2
- 238000003786 synthesis reaction Methods 0.000 abstract 2
- 102000004278 Receptor Protein-Tyrosine Kinases Human genes 0.000 abstract 1
- 108090000873 Receptor Protein-Tyrosine Kinases Proteins 0.000 abstract 1
- 201000010099 disease Diseases 0.000 abstract 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 230000007721 medicinal effect Effects 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 0 Cc1c(*)c(c(**)c(*)cc2)c2c(*)c1* Chemical compound Cc1c(*)c(c(**)c(*)cc2)c2c(*)c1* 0.000 description 2
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- 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
- A61K31/47—Quinolines; Isoquinolines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D215/14—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/18—Halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
- C07D215/233—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/36—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/38—Nitrogen atoms
- C07D215/42—Nitrogen atoms attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Urology & Nephrology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Quinoline Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US82660497A | 1997-04-03 | 1997-04-03 | |
| US08/826,604 | 1997-04-03 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU99123060A RU99123060A (ru) | 2001-10-20 |
| RU2202551C2 true RU2202551C2 (ru) | 2003-04-20 |
Family
ID=25247041
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU99123060/04A RU2202551C2 (ru) | 1997-04-03 | 1998-04-02 | Замещенные 3-цианохинолины |
Country Status (26)
| Country | Link |
|---|---|
| EP (1) | EP0973746B1 (https=) |
| JP (2) | JP4537500B2 (https=) |
| KR (1) | KR100531969B1 (https=) |
| CN (1) | CN1121391C (https=) |
| AR (1) | AR012313A1 (https=) |
| AT (1) | ATE250583T1 (https=) |
| AU (1) | AU750906B2 (https=) |
| BR (1) | BR9808478A (https=) |
| CA (1) | CA2285241C (https=) |
| CZ (1) | CZ299136B6 (https=) |
| DE (1) | DE69818442T2 (https=) |
| DK (1) | DK0973746T3 (https=) |
| ES (1) | ES2209124T3 (https=) |
| HU (1) | HU229549B1 (https=) |
| IL (1) | IL132192A0 (https=) |
| NO (1) | NO313827B1 (https=) |
| NZ (1) | NZ337782A (https=) |
| PL (1) | PL196471B1 (https=) |
| PT (1) | PT973746E (https=) |
| RU (1) | RU2202551C2 (https=) |
| SK (1) | SK284922B6 (https=) |
| TR (1) | TR199902946T2 (https=) |
| TW (1) | TWI228492B (https=) |
| UA (1) | UA73073C2 (https=) |
| WO (1) | WO1998043960A1 (https=) |
| ZA (1) | ZA982771B (https=) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2317290C2 (ru) * | 2003-07-31 | 2008-02-20 | Санофи-Авентис | Производные аминохинолина и их применение в качестве лигандов аденозина а3 |
| RU2345069C2 (ru) * | 2003-08-19 | 2009-01-27 | Уайт Холдингз Корпорейшн | Способ получения 4-амино-3-хинолинкарбонитрилов |
| RU2536102C2 (ru) * | 2009-09-14 | 2014-12-20 | Цзянсу Хэнжуй Медицин Ко., Лтд. | Производные 6-аминохиназолина или 3-цианохинолина, способы их получения и их применение в качестве ингибитора рецепторных тирозинкиназ egfr или her-2 |
| RU2600928C2 (ru) * | 2010-06-09 | 2016-10-27 | Тяньцзинь Химэй Байо-Тек Ко., Лтд | Цианохинолиновые производные |
| RU2631321C2 (ru) * | 2012-07-12 | 2017-09-21 | Цзянсу Хэнжуй Медсин Ко., Лтд. | Кристаллическая форма i дималеата ингибитора тирозинкиназы и способ ее получения |
Families Citing this family (376)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998013350A1 (en) | 1996-09-25 | 1998-04-02 | Zeneca Limited | Qinoline derivatives inhibiting the effect of growth factors such as vegf |
| GB9718972D0 (en) | 1996-09-25 | 1997-11-12 | Zeneca Ltd | Chemical compounds |
| ES2289791T3 (es) | 1997-08-22 | 2008-02-01 | Astrazeneca Ab | Derivados de oxindolilquinazolina como inhibidores de la angiogenesis. |
| US6270747B1 (en) | 1998-08-18 | 2001-08-07 | The University Of California | In vitro and in vivo assay for agents which treat mucus hypersecretion |
| AU2004200300A1 (en) * | 1998-09-29 | 2004-02-19 | Wyeth Holdings Corporation | Substituted 3-cyanoquinolines as Protein Tyrosine Kinases Inhibitors |
| IL142092A0 (en) | 1998-09-29 | 2002-03-10 | American Cyanamid Co | Substituted 3-cyanoquinolines as protein tyrosine kinases inhibitors |
| ATE255575T1 (de) * | 1998-09-29 | 2003-12-15 | Wyeth Corp | Substituierte 3-cyanochinoline als protein tyrosine kinase inhibitoren |
| US6288082B1 (en) | 1998-09-29 | 2001-09-11 | American Cyanamid Company | Substituted 3-cyanoquinolines |
| US6297258B1 (en) | 1998-09-29 | 2001-10-02 | American Cyanamid Company | Substituted 3-cyanoquinolines |
| GB9904103D0 (en) | 1999-02-24 | 1999-04-14 | Zeneca Ltd | Quinoline derivatives |
| CA2361174C (en) * | 1999-02-27 | 2009-10-27 | Boehringer Ingelheim Pharma Kg | 4-amino-quinazoline and quinoline derivatives having an inhibitory effect on signal transduction mediated by tyrosine kinases |
| US6355636B1 (en) | 1999-04-21 | 2002-03-12 | American Cyanamid Company | Substituted 3-cyano-[1.7],[1.5], and [1.8] naphthyridine inhibitors of tyrosine kinases |
| ES2216884T3 (es) * | 1999-04-21 | 2004-11-01 | Wyeth Holdings Corporation | 3-ciano-(1.7),(1.5) y (1.8)-naftiridina sustituidas que son inhibidores de tirosina-quinasas. |
| US6548496B2 (en) | 1999-04-21 | 2003-04-15 | American Cyanamid Company | Substituted 3-cyano-[1.7], [1.5], and [1.8] naphthyridine inhibitors of tyrosine kinases |
| GB9910577D0 (en) * | 1999-05-08 | 1999-07-07 | Zeneca Ltd | Chemical compounds |
| GB9910580D0 (en) * | 1999-05-08 | 1999-07-07 | Zeneca Ltd | Chemical compounds |
| GB9910579D0 (en) * | 1999-05-08 | 1999-07-07 | Zeneca Ltd | Chemical compounds |
| HK1044769B (zh) * | 1999-06-21 | 2005-02-25 | 贝林格尔英格海姆法玛两合公司 | 雙環雜環化合物,含有該化合物的藥物組合物,該化合物的用途及其製備方法 |
| US7192698B1 (en) | 1999-08-17 | 2007-03-20 | Purdue Research Foundation | EphA2 as a diagnostic target for metastatic cancer |
| US6927203B1 (en) | 1999-08-17 | 2005-08-09 | Purdue Research Foundation | Treatment of metastatic disease |
| KR100881105B1 (ko) | 1999-11-05 | 2009-02-02 | 아스트라제네카 아베 | Vegf 억제제로서의 퀴나졸린 유도체 |
| DK1242382T3 (da) * | 1999-12-29 | 2007-05-07 | Wyeth Corp | Tricycliske proteinkinaseinhibitorer |
| US6638929B2 (en) | 1999-12-29 | 2003-10-28 | Wyeth | Tricyclic protein kinase inhibitors |
| US6384051B1 (en) | 2000-03-13 | 2002-05-07 | American Cyanamid Company | Method of treating or inhibiting colonic polyps |
| CN1190197C (zh) * | 2000-03-13 | 2005-02-23 | 惠氏控股公司 | 氰基喹啉用于制备治疗或抑制结肠息肉药物中的用途 |
| AR035851A1 (es) * | 2000-03-28 | 2004-07-21 | Wyeth Corp | 3-cianoquinolinas, 3-ciano-1,6-naftiridinas y 3-ciano-1,7-naftiridinas como inhibidoras de proteina quinasas |
| US6608048B2 (en) | 2000-03-28 | 2003-08-19 | Wyeth Holdings | Tricyclic protein kinase inhibitors |
| US6521618B2 (en) | 2000-03-28 | 2003-02-18 | Wyeth | 3-cyanoquinolines, 3-cyano-1,6-naphthyridines, and 3-cyano-1,7-naphthyridines as protein kinase inhibitors |
| ES2267748T3 (es) | 2000-04-07 | 2007-03-16 | Astrazeneca Ab | Compuestos de quinazolina. |
| US6627634B2 (en) | 2000-04-08 | 2003-09-30 | Boehringer Ingelheim Pharma Kg | Bicyclic heterocycles, pharmaceutical compositions containing them, their use, and processes for preparing them |
| WO2001077104A1 (de) * | 2000-04-08 | 2001-10-18 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Bicyclische heterocyclen, diese verbindungen enthaltende arzneimittel, deren verwendung und verfahren zu ihrer herstellung |
| AU2002216758A1 (en) * | 2000-07-03 | 2002-01-14 | Astrazeneca Ab | Quinazolines with therapeutic use |
| US6576644B2 (en) * | 2000-09-06 | 2003-06-10 | Bristol-Myers Squibb Co. | Quinoline inhibitors of cGMP phosphodiesterase |
| US7101976B1 (en) | 2000-09-12 | 2006-09-05 | Purdue Research Foundation | EphA2 monoclonal antibodies and methods of making and using same |
| US7067532B2 (en) | 2000-11-02 | 2006-06-27 | Astrazeneca | Substituted quinolines as antitumor agents |
| EP1337513A1 (en) * | 2000-11-02 | 2003-08-27 | AstraZeneca AB | 4-substituted quinolines as antitumor agents |
| US7019012B2 (en) | 2000-12-20 | 2006-03-28 | Boehringer Ingelheim International Pharma Gmbh & Co. Kg | Quinazoline derivatives and pharmaceutical compositions containing them |
| BR0116600A (pt) | 2000-12-29 | 2004-02-10 | Wyeth Corp | Método para a preparação regiosseletiva de benzo(g)quinolina-3-carbonitrilas e benzo(g)quinazolinas substituìdas |
| SE0101675D0 (sv) * | 2001-05-11 | 2001-05-11 | Astrazeneca Ab | Novel composition |
| EP1412367A4 (en) | 2001-06-21 | 2006-05-03 | Ariad Pharma Inc | NEW CHINOLINE AND ITS USE |
| WO2003000266A1 (en) * | 2001-06-21 | 2003-01-03 | Ariad Pharmaceuticals, Inc. | Novel quinolines and uses thereof |
| WO2003008409A1 (en) * | 2001-07-16 | 2003-01-30 | Astrazeneca Ab | Quinoline derivatives and their use as tyrosine kinase inhibitors |
| UA77200C2 (en) | 2001-08-07 | 2006-11-15 | Wyeth Corp | Antineoplastic combination of cci-779 and bkb-569 |
| AR037438A1 (es) * | 2001-11-27 | 2004-11-10 | Wyeth Corp | 3-cianoquinolinas como inhibidores de egf-r y her2 quinasas, un proceso para su preparacion, composiciones farmaceuticas y el uso de dichos compuestos para la fabricacion de medicamentos |
| WO2003048159A1 (en) * | 2001-12-05 | 2003-06-12 | Astrazeneca Ab | Quinoline derivatives |
| AU2002365664A1 (en) * | 2001-12-05 | 2003-06-17 | Astrazeneca Ab | Quinoline derivatives as antitumour agents |
| GB0129099D0 (en) * | 2001-12-05 | 2002-01-23 | Astrazeneca Ab | Chemical compounds |
| AU2002347359A1 (en) * | 2001-12-05 | 2003-06-17 | Astrazeneca Ab | Quinoline derivatives |
| WO2003064399A1 (fr) * | 2002-01-28 | 2003-08-07 | Ube Industries, Ltd. | Procede de production de derive de quinazolin-4-one |
| US20040132101A1 (en) | 2002-09-27 | 2004-07-08 | Xencor | Optimized Fc variants and methods for their generation |
| KR100984595B1 (ko) | 2002-03-13 | 2010-09-30 | 어레이 바이오파마 인크. | Mek 억제제로서의 n3 알킬화 벤즈이미다졸 유도체 |
| US7235537B2 (en) | 2002-03-13 | 2007-06-26 | Array Biopharma, Inc. | N3 alkylated benzimidazole derivatives as MEK inhibitors |
| JP2005536462A (ja) * | 2002-04-30 | 2005-12-02 | ユン ジン ファーマスーチカル インダストリーズ カンパニー リミテッド | カスパーゼ−3阻害剤としてのキノリン誘導体、この製造方法及びこれを含む薬剤学的組成物 |
| TWI275390B (en) * | 2002-04-30 | 2007-03-11 | Wyeth Corp | Process for the preparation of 7-substituted-3- quinolinecarbonitriles |
| DE10221018A1 (de) | 2002-05-11 | 2003-11-27 | Boehringer Ingelheim Pharma | Verwendung von Hemmern der EGFR-vermittelten Signaltransduktion zur Behandlung von gutartiger Prostatahyperplasie (BPH)/Prostatahypertrophie |
| WO2004008099A2 (en) | 2002-07-15 | 2004-01-22 | Genentech, Inc. | METHODS FOR IDENTIFYING TUMORS THAT ARE RESPONSIVE TO TREATMENT WITH ANTI-ErbB2 ANTIBODIES |
| US7576074B2 (en) | 2002-07-15 | 2009-08-18 | Rice Kenneth D | Receptor-type kinase modulators and methods of use |
| EP1553975B8 (en) | 2002-09-27 | 2023-04-12 | Xencor, Inc. | Optimized fc variants and methods for their generation |
| GB0225579D0 (en) * | 2002-11-02 | 2002-12-11 | Astrazeneca Ab | Chemical compounds |
| US20060167026A1 (en) * | 2003-01-06 | 2006-07-27 | Hiroyuki Nawa | Antipsychotic molecular-targeting epithelial growth factor receptor |
| CL2004000016A1 (es) | 2003-01-21 | 2005-04-15 | Wyeth Corp | Compuesto derivado de cloruro de 4-amino-2-butenoilo o una sal farmaceuticamente aceptable del mismo; procedimiento para preparar dicho compuesto, util como intermediario en la sintesis de compuestos inhibidores de proteina quinasa tirosina. |
| WO2004069827A1 (en) * | 2003-02-03 | 2004-08-19 | Astrazeneca Ab | Quinoline derivatives and use thereof as antitumor agents |
| WO2004069249A1 (en) * | 2003-02-03 | 2004-08-19 | Astrazeneca Ab | 3-cyano-quinoline derivatives as non-receptor tyrosine kinase inhibitors |
| WO2004069250A1 (en) * | 2003-02-03 | 2004-08-19 | Astrazeneca Ab | 3-cyano-quinoline derivatives as non-receptor tyrosine kinase inhibitors |
| US7223749B2 (en) | 2003-02-20 | 2007-05-29 | Boehringer Ingelheim International Gmbh | Bicyclic heterocycles, pharmaceutical compositions containing these compounds, their use and processes for preparing them |
| US20090010920A1 (en) | 2003-03-03 | 2009-01-08 | Xencor, Inc. | Fc Variants Having Decreased Affinity for FcyRIIb |
| US7135575B2 (en) | 2003-03-03 | 2006-11-14 | Array Biopharma, Inc. | P38 inhibitors and methods of use thereof |
| EP1606305A4 (en) | 2003-03-12 | 2009-06-24 | Vasgene Therapeutics Inc | NUCLEIC ACID COMPOUNDS FOR THE INHIBITION OF ANGIOGENESIS AND TUMOR GROWTH |
| US7381410B2 (en) | 2003-03-12 | 2008-06-03 | Vasgene Therapeutics, Inc. | Polypeptide compounds for inhibiting angiogenesis and tumor growth |
| UA80607C2 (en) * | 2003-04-09 | 2007-10-10 | White Holdings Corp | Process for the preparation of 3-cyano-6-alkoxy-7-nitro-4-quinolines |
| WO2004108703A1 (en) * | 2003-06-05 | 2004-12-16 | Astrazeneca Ab | Pyrazinyl 3-cyanoquinoline derivatives for use in the treatment of tumours |
| WO2004108704A1 (en) * | 2003-06-05 | 2004-12-16 | Astrazeneca Ab | Pyrimidin-4-yl 3-cyanoquinoline derivatives for use in the treatment of tumours |
| AU2004253967B2 (en) | 2003-07-03 | 2010-02-18 | Cytovia, Inc. | 4-arylamino-quinazolines as activators of caspases and inducers of apoptosis |
| US8309562B2 (en) | 2003-07-03 | 2012-11-13 | Myrexis, Inc. | Compounds and therapeutical use thereof |
| WO2006074147A2 (en) | 2005-01-03 | 2006-07-13 | Myriad Genetics, Inc. | Nitrogen containing bicyclic compounds and therapeutical use thereof |
| BRPI0412577A (pt) | 2003-07-31 | 2006-09-19 | Sanofi Aventis | derivados de aminoquinolina e seu uso como ligantes de adenosina a3 |
| US7144907B2 (en) | 2003-09-03 | 2006-12-05 | Array Biopharma Inc. | Heterocyclic inhibitors of MEK and methods of use thereof |
| US7538120B2 (en) | 2003-09-03 | 2009-05-26 | Array Biopharma Inc. | Method of treating inflammatory diseases |
| US7399865B2 (en) | 2003-09-15 | 2008-07-15 | Wyeth | Protein tyrosine kinase enzyme inhibitors |
| EP2210607B1 (en) | 2003-09-26 | 2011-08-17 | Exelixis Inc. | N-[3-fluoro-4-({6-(methyloxy)-7-[(3-morpholin-4-ylpropyl)oxy]quinolin-4-yl}oxy)phenyl]-N'-(4-fluorophenyl)cyclopropane-1,1-dicarboxamide for the treatment of cancer |
| US9714282B2 (en) | 2003-09-26 | 2017-07-25 | Xencor, Inc. | Optimized Fc variants and methods for their generation |
| US7456189B2 (en) | 2003-09-30 | 2008-11-25 | Boehringer Ingelheim International Gmbh | Bicyclic heterocycles, medicaments containing these compounds, their use and processes for their preparation |
| DE10349113A1 (de) | 2003-10-17 | 2005-05-12 | Boehringer Ingelheim Pharma | Verfahren zur Herstellung von Aminocrotonylverbindungen |
| EP2478912B1 (en) | 2003-11-06 | 2016-08-31 | Seattle Genetics, Inc. | Auristatin conjugates with anti-HER2 or anti-CD22 antibodies and their use in therapy |
| AU2003291245A1 (en) * | 2003-11-06 | 2004-06-06 | Wyeth | 4-anilino-3-quinolinecarbonitriles for the treatment of chronic myelogenous leukemia (cml) |
| US7732616B2 (en) | 2003-11-19 | 2010-06-08 | Array Biopharma Inc. | Dihydropyridine and dihydropyridazine derivatives as inhibitors of MEK and methods of use thereof |
| CN1905873A (zh) | 2003-11-19 | 2007-01-31 | 阵列生物制药公司 | Mek的杂环抑制剂及其使用方法 |
| US7517994B2 (en) | 2003-11-19 | 2009-04-14 | Array Biopharma Inc. | Heterocyclic inhibitors of MEK and methods of use thereof |
| NZ590160A (en) | 2003-11-21 | 2012-07-27 | Array Biopharma Inc | AKT protein kinase inhibitors |
| MXPA06007018A (es) * | 2003-12-18 | 2006-08-31 | Janssen Pharmaceutica Nv | Derivados de 3-ciano-quinolino con actividad anti-proliferativa. |
| MXPA06007017A (es) | 2003-12-18 | 2006-08-31 | Janssen Pharmaceutica Nv | Derivados de pirido y pirimidopirimidina como agentes antiproliferativos. |
| GT200500008A (es) * | 2004-01-16 | 2005-08-16 | Intermediarios de quinolina como inhibidores de receptores de tirosina quinasas y la sintesis de los mismos | |
| SE0400284D0 (sv) * | 2004-02-10 | 2004-02-10 | Astrazeneca Ab | Novel compounds |
| TW200529846A (en) | 2004-02-20 | 2005-09-16 | Wyeth Corp | 3-quinolinecarbonitrile protein kinase inhibitors |
| CN101072797B (zh) | 2004-03-12 | 2012-05-09 | 瓦斯基因治疗公司 | 结合ephb4、抑制血管发生和肿瘤生长的抗体 |
| DK1730196T3 (da) | 2004-03-12 | 2011-03-28 | Vasgene Therapeutics Inc | EphB4-bindende antistoffer til inhibering af antiogenese og tumorvækst |
| ES2425749T3 (es) | 2004-03-31 | 2013-10-17 | The General Hospital Corporation | Método para determinar la respuesta del cáncer a tratamientos dirigidos al receptor del factor de crecimiento epidérmico |
| KR20080095915A (ko) | 2004-05-06 | 2008-10-29 | 워너-램버트 캄파니 엘엘씨 | 4-페닐아미노-퀴나졸린-6-일-아미드 |
| NZ579482A (en) | 2004-06-01 | 2011-02-25 | Genentech Inc | Antibody drug conjugates and methods |
| EP2471813B1 (en) | 2004-07-15 | 2014-12-31 | Xencor, Inc. | Optimized Fc variants |
| DK1791565T3 (en) | 2004-09-23 | 2016-08-01 | Genentech Inc | Cysteingensplejsede antibodies and conjugates |
| CA2581423A1 (en) | 2004-09-23 | 2006-03-30 | Vasgene Therapeutics, Inc. | Polipeptide compounds for inhibiting angiogenesis and tumor growth |
| ZA200703912B (en) | 2004-10-20 | 2008-09-25 | Serono Lab | 3-arylamino pyridine derivatives |
| JO3000B1 (ar) | 2004-10-20 | 2016-09-05 | Genentech Inc | مركبات أجسام مضادة . |
| US8367805B2 (en) | 2004-11-12 | 2013-02-05 | Xencor, Inc. | Fc variants with altered binding to FcRn |
| AU2005304624B2 (en) | 2004-11-12 | 2010-10-07 | Xencor, Inc. | Fc variants with altered binding to FcRn |
| HUP0402371A2 (en) * | 2004-11-15 | 2006-09-28 | Sanofi Aventis | Novel 125-i-labeled amino-quinoline derivatives |
| NI200700147A (es) | 2004-12-08 | 2019-05-10 | Janssen Pharmaceutica Nv | Derivados de quinazolina inhibidores de cinasas dirigidos a multip |
| US8258145B2 (en) | 2005-01-03 | 2012-09-04 | Myrexis, Inc. | Method of treating brain cancer |
| CN102580084B (zh) | 2005-01-21 | 2016-11-23 | 健泰科生物技术公司 | Her抗体的固定剂量给药 |
| KR101313702B1 (ko) | 2005-02-03 | 2013-10-04 | 와이어쓰 | 제피티니브 및/또는 에를로티니브 내성암 치료용 약제학적 조성물 |
| EP1850874B1 (en) | 2005-02-23 | 2013-10-16 | Genentech, Inc. | Extending time to disease progression or survival in ovarian cancer patients using pertuzumab |
| ES2405785T3 (es) | 2005-05-18 | 2013-06-03 | Array Biopharma Inc. | Inhibidores heterocíclicos de MEK y métodos de uso de los mismos |
| EP1888529A2 (en) * | 2005-05-18 | 2008-02-20 | Wyeth | 3-cyanoquinoline inhibitors of tpl2 kinase and methods of making and using the same |
| CN101203494A (zh) * | 2005-05-25 | 2008-06-18 | 惠氏公司 | 合成经取代3-氰基喹啉和其中间物的方法 |
| WO2007008943A2 (en) | 2005-07-08 | 2007-01-18 | Xencor, Inc. | Optimized anti-ep-cam antibodies |
| WO2007041635A2 (en) | 2005-10-03 | 2007-04-12 | Xencor, Inc. | Fc variants with optimized fc receptor binding properties |
| CA2627497C (en) | 2005-10-28 | 2014-10-14 | Takeda Pharmaceutical Company Limited | Heterocyclic amide compound and use thereof |
| EP1942937A1 (en) | 2005-11-04 | 2008-07-16 | Wyeth | Antineoplastic combinations with mtor inhibitor, herceptin, and/or hki-272 |
| 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 |
| RS52298B (sr) | 2006-01-31 | 2012-12-31 | Array Biopharma Inc. | Inhibitori kinaze i postupak njihove upotrebe |
| US8063050B2 (en) | 2006-07-06 | 2011-11-22 | Array Biopharma Inc. | Hydroxylated and methoxylated pyrimidyl cyclopentanes as AKT protein kinase inhibitors |
| ATE532789T1 (de) | 2006-07-06 | 2011-11-15 | Array Biopharma Inc | Dihydrothienopyrimidine als akt-proteinkinase- inhibitoren |
| CA2656566C (en) | 2006-07-06 | 2014-06-17 | Array Biopharma Inc. | Dihydrofuro pyrimidines as akt protein kinase inhibitors |
| ATE523499T1 (de) | 2006-07-06 | 2011-09-15 | Array Biopharma Inc | Cyclopenta [d]-pyrimidine als akt-proteinkinasehemmer |
| JP2009542778A (ja) | 2006-07-13 | 2009-12-03 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | Mtkiキナゾリン誘導体 |
| PL2383297T3 (pl) | 2006-08-14 | 2013-06-28 | Xencor Inc | Zoptymalizowane przeciwciała ukierunkowane na CD19 |
| ES2372217T3 (es) | 2006-09-12 | 2012-01-17 | Genentech, Inc. | Procedimientos y composiciones para el diagnóstico y tratamiento del cáncer de pulmón utilizando el gen de pdgfra, kit o kdr como marcador genético. |
| AU2007299080B2 (en) | 2006-09-18 | 2013-04-18 | Boehringer Ingelheim International Gmbh | Method for treating cancer harboring EGFR mutations |
| EP1921070A1 (de) | 2006-11-10 | 2008-05-14 | Boehringer Ingelheim Pharma GmbH & Co. KG | Bicyclische Heterocyclen, diese Verbindungen enthaltende Arzneimittel, deren Verwendung und Verfahren zu ihrer Herstelllung |
| AU2008212999A1 (en) | 2007-02-06 | 2008-08-14 | Boehringer Ingelheim International Gmbh | Bicyclic heterocycles, drugs containing said compounds, use thereof, and method for production thereof |
| SI2132573T1 (sl) | 2007-03-02 | 2014-07-31 | Genentech, Inc. | Napovedovanje odziva na inhibitor dimerizacije HER na osnovi nizke ekspresije HER3 |
| EP2176298B1 (en) | 2007-05-30 | 2017-11-15 | Xencor, Inc. | Methods and compositions for inhibiting cd32b expressing cells |
| PL2171090T3 (pl) | 2007-06-08 | 2013-09-30 | Genentech Inc | Markery ekspresji genów odporności guza na leczenie hamujące HER2 |
| CN101918373B (zh) | 2007-07-05 | 2013-06-05 | 阵列生物制药公司 | 作为akt蛋白激酶抑制剂的嘧啶基环戊烷 |
| WO2009006567A2 (en) | 2007-07-05 | 2009-01-08 | Array Biopharma Inc. | Pyrimidyl cyclopentanes as akt protein kinase inhibitors |
| US8846683B2 (en) | 2007-07-05 | 2014-09-30 | Array Biopharma, Inc. | Pyrimidyl cyclopentanes as Akt protein kinase inhibitors |
| US9409886B2 (en) | 2007-07-05 | 2016-08-09 | Array Biopharma Inc. | Pyrimidyl cyclopentanes as AKT protein kinase inhibitors |
| AU2008281849B2 (en) | 2007-07-27 | 2013-11-28 | Janssen Pharmaceutica Nv | Pyrrolopyrimidines |
| CA2696164C (en) | 2007-08-13 | 2018-06-12 | Vasgene Therapeutics, Inc. | Cancer treatment using humanized antibodies that bind to ephb4 |
| CN101148439B (zh) * | 2007-09-14 | 2011-06-22 | 东南大学 | 一种吉非替尼的制备方法 |
| US8022216B2 (en) | 2007-10-17 | 2011-09-20 | Wyeth Llc | Maleate salts of (E)-N-{4-[3-chloro-4-(2-pyridinylmethoxy)anilino]-3-cyano-7-ethoxy-6-quinolinyl}-4-(dimethylamino)-2-butenamide and crystalline forms thereof |
| HRP20150279T1 (hr) | 2007-12-26 | 2015-05-08 | Xencor, Inc. | Fc inaäśice s promijenjenim vezanjem na fcrn |
| ES2422733T3 (es) | 2008-01-09 | 2013-09-13 | Array Biopharma Inc | Pirimidilciclopentanos hidroxilados como inhibidores de proteínas cinasas AKT |
| EP2240455B1 (en) | 2008-01-09 | 2012-12-26 | Array Biopharma, Inc. | Hydroxylated pyrimidyl cyclopentane as akt protein kinase inhibitor |
| TWI472339B (zh) | 2008-01-30 | 2015-02-11 | Genentech Inc | 包含結合至her2結構域ii之抗體及其酸性變異體的組合物 |
| US8497369B2 (en) | 2008-02-07 | 2013-07-30 | Boehringer Ingelheim International Gmbh | Spirocyclic heterocycles medicaments containing said compounds, use thereof and method for their production |
| DE102008009609A1 (de) | 2008-02-18 | 2009-08-20 | Freie Universität Berlin | Substituierte 4-(Indol-3-yl)chinazoline und deren Verwendung und Herstellung |
| US12492253B1 (en) | 2008-02-25 | 2025-12-09 | Xencor, Inc. | Anti-human C5 antibodies |
| NZ589143A (en) | 2008-05-14 | 2012-02-24 | Genomic Health Inc | Colorectal cancer response prediction based on AREG EREG DUSP6 and SLC26A3 expression levels |
| BRPI0914790A2 (pt) | 2008-06-17 | 2015-10-20 | Wyeth Llc | uso de um composto de vinorelbina e um composto de hki-272, composição farmacêutica e produto e kit para o tratamento de neoplasma |
| HRP20160044T1 (hr) | 2008-08-04 | 2016-02-26 | Merck Patent Gmbh | Novi spojevi fenilamino izonikotinamida |
| US8669273B2 (en) | 2008-08-04 | 2014-03-11 | Wyeth Llc | Antineoplastic combinations of 4-anilino-3-cyanoquinolines and capecitabine |
| EP2313397B1 (de) | 2008-08-08 | 2016-04-20 | Boehringer Ingelheim International GmbH | Cyclohexyloxy-substituierte heterocyclen, diese verbindungen enthaltende arzneimittel, deren verwendung und verfahren zu ihrer herstellung |
| US8993630B2 (en) | 2008-11-10 | 2015-03-31 | Bayer Intellectual Property Gmbh | Substituted sulphonamido phenoxybenzamides |
| CA2743449C (en) | 2008-11-12 | 2016-10-18 | Ariad Pharmaceuticals, Inc. | Pyrazinopyrazines and derivatives as kinase inhibitors |
| NZ779754A (en) | 2009-01-16 | 2023-04-28 | Exelixis Inc | Malate salt of n-(4-{ [6,7-bis(methyloxy)quinolin-4-yl] oxy} phenyl)-n’-(4-fluorophenyl)cyclopropane-1,1-dicarboxamide, and crystalline forms thereof for the treatment of cancer |
| DK3000467T3 (da) | 2009-04-06 | 2023-03-27 | Wyeth Llc | Behandling med neratinib mod brystkræft |
| 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 |
| US9345661B2 (en) | 2009-07-31 | 2016-05-24 | Genentech, Inc. | Subcutaneous anti-HER2 antibody formulations and uses thereof |
| UA108618C2 (uk) | 2009-08-07 | 2015-05-25 | Застосування c-met-модуляторів в комбінації з темозоломідом та/або променевою терапією для лікування раку | |
| WO2011028952A1 (en) | 2009-09-02 | 2011-03-10 | Xencor, Inc. | Compositions and methods for simultaneous bivalent and monovalent co-engagement of antigens |
| EP2491015A1 (en) | 2009-10-21 | 2012-08-29 | Bayer Pharma Aktiengesellschaft | Substituted benzosulphonamides |
| US20120269803A1 (en) | 2009-10-21 | 2012-10-25 | Bayer Intellectual Property Gmbh | Substituted benzosulphonamides |
| EP2491014A1 (en) | 2009-10-21 | 2012-08-29 | Bayer Pharma Aktiengesellschaft | Substituted halophenoxybenzamide derivatives |
| CN102770456B (zh) | 2009-12-04 | 2018-04-06 | 弗·哈夫曼-拉罗切有限公司 | 多特异性抗体、抗体类似物、组合物和方法 |
| RU2012132278A (ru) | 2010-01-12 | 2014-02-20 | Ф. Хоффманн-Ля Рош Аг | Трициклические гетероциклические соединения, содержащие их композиции и способы их применения |
| AU2011222867B2 (en) | 2010-03-04 | 2014-03-06 | Annika Algars | Method for selecting patients for treatment with an EGFR inhibitor |
| US20130096104A1 (en) | 2010-03-17 | 2013-04-18 | Genentech, Inc. | Imidazopyridine compounds, compositions and methods of use |
| JP2013528357A (ja) | 2010-03-29 | 2013-07-11 | ザイムワークス,インコーポレイテッド | 強化又は抑制されたエフェクター機能を有する抗体 |
| WO2011130654A1 (en) | 2010-04-16 | 2011-10-20 | Genentech, Inc. | Fox03a as predictive biomarker for pi3k/akt kinase pathway inhibitor efficacy |
| EP2566477B1 (en) * | 2010-05-07 | 2015-09-02 | GlaxoSmithKline Intellectual Property Development Limited | Amino-quinolines as kinase inhibitors |
| WO2011146568A1 (en) | 2010-05-19 | 2011-11-24 | Genentech, Inc. | Predicting response to a her inhibitor |
| ES2598530T3 (es) * | 2010-07-14 | 2017-01-27 | Betta Pharmaceuticals Co., Ltd. | Nuevos derivados heterocíclicos condensados útiles como inhibidores de la tirosina quinasa c-Met |
| UY33549A (es) * | 2010-08-10 | 2012-01-31 | Glaxo Group Ltd | Quinolil aminas como agentes inhibidores de las quinasas |
| TW201217387A (en) | 2010-09-15 | 2012-05-01 | Hoffmann La Roche | Azabenzothiazole compounds, compositions and methods of use |
| WO2012055953A1 (en) | 2010-10-29 | 2012-05-03 | Bayer Pharma Aktiengesellschaft | Substituted phenoxypyridines |
| EP2637692A4 (en) | 2010-11-12 | 2014-09-10 | Scott & White Healthcare | ANTIBODIES TO THE ENDOTHELIAL TUMOR MARKER 8 |
| BR112013011520A2 (pt) | 2010-11-19 | 2019-09-24 | Hoffmann La Roche | pirazolo piridinas e pirazolo piridinas e seu uso como inibidores de tyk2 |
| WO2012085176A1 (en) | 2010-12-23 | 2012-06-28 | F. Hoffmann-La Roche Ag | Tricyclic pyrazinone compounds, compositions and methods of use thereof as janus kinase inhibitors |
| US9604963B2 (en) | 2011-03-04 | 2017-03-28 | Glaxosmithkline Intellectual Property Development Limited | Amino-quinolines as kinase inhibitors |
| AU2012225246B2 (en) | 2011-03-10 | 2016-01-21 | Omeros Corporation | Generation of anti-FN14 monoclonal antibodies by ex-vivo accelerated antibody evolution |
| CN102675287A (zh) * | 2011-03-11 | 2012-09-19 | 江苏恒瑞医药股份有限公司 | (e)-n-[4-[[3-氯-4-(2-吡啶基甲氧基)苯基]氨基]-3-氰基-7-乙氧基-6-喹啉基]-3-[(2r)-1-甲基吡咯烷-2-基]丙-2-烯酰胺的可药用的盐、其制备方法及其在医药上的应用 |
| WO2012135781A1 (en) | 2011-04-01 | 2012-10-04 | Genentech, Inc. | Combinations of akt inhibitor compounds and chemotherapeutic agents, and methods of use |
| RU2013148817A (ru) | 2011-04-01 | 2015-05-10 | Дженентек, Инк. | Комбинации соединений-ингибиторов акт и мек и способы их применения |
| EP2714037B1 (en) | 2011-05-25 | 2016-07-13 | Université Paris Descartes | Erk inhibitors for use in treating spinal muscular atrophy |
| WO2013007768A1 (en) | 2011-07-13 | 2013-01-17 | F. Hoffmann-La Roche Ag | Tricyclic heterocyclic compounds, compositions and methods of use thereof as jak inhibitors |
| WO2013007765A1 (en) | 2011-07-13 | 2013-01-17 | F. Hoffmann-La Roche Ag | Fused tricyclic compounds for use as inhibitors of janus kinases |
| WO2013025446A2 (en) | 2011-08-12 | 2013-02-21 | Omeros Corporation | Anti-fzd10 monoclonal antibodies and methods for their use |
| KR20140047160A (ko) | 2011-08-12 | 2014-04-21 | 에프. 호프만-라 로슈 아게 | 인다졸 화합물, 조성물 및 사용 방법 |
| TWI547494B (zh) | 2011-08-18 | 2016-09-01 | 葛蘭素史克智慧財產發展有限公司 | 作為激酶抑制劑之胺基喹唑啉類 |
| CN103827115A (zh) | 2011-09-20 | 2014-05-28 | 弗·哈夫曼-拉罗切有限公司 | 咪唑并吡啶化合物、组合物和使用方法 |
| CN103906735B (zh) | 2011-11-04 | 2016-12-07 | 霍夫曼-拉罗奇有限公司 | 新芳基-喹啉衍生物 |
| CN103204825B (zh) | 2012-01-17 | 2015-03-04 | 上海科州药物研发有限公司 | 作为蛋白激酶抑制剂的苯并噻唑化合物及其制备方法和用途 |
| AU2013229786B2 (en) | 2012-03-08 | 2017-06-22 | Halozyme, Inc. | Conditionally active anti-epidermal growth factor receptor antibodies and methods of use thereof |
| US20130259867A1 (en) | 2012-03-27 | 2013-10-03 | Genentech, Inc. | Diagnosis and treatments relating to her3 inhibitors |
| AR092529A1 (es) | 2012-09-13 | 2015-04-22 | Glaxosmithkline Llc | Compuesto de aminoquinazolina, composicion farmaceutica que lo comprende y uso de dicho compuesto para la preparacion de un medicamento |
| TW201425307A (zh) | 2012-09-13 | 2014-07-01 | Glaxosmithkline Llc | 作為激酶抑制劑之胺基-喹啉類 |
| CA2902132C (en) | 2013-02-21 | 2020-09-22 | Glaxosmithkline Intellectual Property Development Limited | Quinazolines as kinase inhibitors |
| KR20150130491A (ko) | 2013-03-13 | 2015-11-23 | 제넨테크, 인크. | 피라졸로 화합물 및 그것의 용도 |
| US9227978B2 (en) | 2013-03-15 | 2016-01-05 | Araxes Pharma Llc | Covalent inhibitors of Kras G12C |
| CN103275001B (zh) * | 2013-06-14 | 2015-02-18 | 苏州明锐医药科技有限公司 | 4-氨基-3-喹啉甲腈衍生物的制备方法 |
| EP3041474B1 (en) | 2013-09-05 | 2020-03-18 | Genentech, Inc. | Antiproliferative compounds |
| EP3043822A1 (en) | 2013-09-11 | 2016-07-20 | The J. David Gladstone Institutes, A Testamentary Trust Established under The Will of J. David Gladstone | Compositions for preparing cardiomyocytes |
| JP6282745B2 (ja) | 2013-09-12 | 2018-02-21 | ハロザイム インコーポレイテッド | 修飾抗上皮成長因子受容体抗体およびその使用法 |
| BR112015032713B1 (pt) | 2013-09-17 | 2023-03-21 | Obi Pharma, Inc | Composto, composição farmacêutica, uso de uma quantidade terapeuticamente efetiva da composição farmacêutica, e uso do composto |
| TW201605857A (zh) | 2013-10-03 | 2016-02-16 | 赫孚孟拉羅股份公司 | Cdk8之醫療性抑制劑及其用途 |
| JO3805B1 (ar) | 2013-10-10 | 2021-01-31 | Araxes Pharma Llc | مثبطات كراس جي12سي |
| JP2017507900A (ja) | 2013-12-17 | 2017-03-23 | ジェネンテック, インコーポレイテッド | Pd−1軸結合アンタゴニスト及び抗her2抗体を使用してher2陽性がんを治療する方法 |
| WO2015095423A2 (en) | 2013-12-17 | 2015-06-25 | Genentech, Inc. | Combination therapy comprising ox40 binding agonists and pd-1 axis binding antagonists |
| 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 |
| AU2015206603B9 (en) | 2014-01-14 | 2019-07-18 | Dana-Farber Cancer Institute, Inc. | Compositions and methods for identification, assessment, prevention, and treatment of melanoma using PD-L1 isoforms |
| KR20160146747A (ko) | 2014-03-31 | 2016-12-21 | 제넨테크, 인크. | 항혈관신생제 및 ox40 결합 효능제를 포함하는 조합 요법 |
| SG11201607969XA (en) | 2014-03-31 | 2016-10-28 | Genentech Inc | Anti-ox40 antibodies and methods of use |
| CN107074823B (zh) | 2014-09-05 | 2021-05-04 | 基因泰克公司 | 治疗性化合物及其用途 |
| EP3193866A1 (en) | 2014-09-19 | 2017-07-26 | Genentech, Inc. | Use of cbp/ep300 and bet inhibitors for treatment of cancer |
| CA2963091A1 (en) | 2014-10-06 | 2016-04-14 | Dana-Farber Cancer Institute, Inc. | Angiopoietin-2 biomarkers predictive of anti-immune checkpoint response |
| CN107912040B (zh) | 2014-10-10 | 2021-04-06 | 基因泰克公司 | 作为组蛋白脱甲基酶抑制剂的吡咯烷酰胺化合物 |
| CA2966523A1 (en) | 2014-11-03 | 2016-05-12 | Genentech, Inc. | Assays for detecting t cell immune subsets and methods of use thereof |
| WO2016073380A1 (en) | 2014-11-03 | 2016-05-12 | Genentech, Inc. | Method and biomarkers for predicting efficacy and evaluation of an ox40 agonist treatment |
| US20160152720A1 (en) | 2014-11-06 | 2016-06-02 | Genentech, Inc. | Combination therapy comprising ox40 binding agonists and tigit inhibitors |
| CN107108613B (zh) | 2014-11-10 | 2020-02-25 | 基因泰克公司 | 布罗莫结构域抑制剂及其用途 |
| MA40940A (fr) | 2014-11-10 | 2017-09-19 | Constellation Pharmaceuticals Inc | Pyrrolopyridines substituées utilisées en tant qu'inhibiteurs de bromodomaines |
| MA40943A (fr) | 2014-11-10 | 2017-09-19 | Constellation Pharmaceuticals Inc | Pyrrolopyridines substituées utilisées en tant qu'inhibiteurs de bromodomaines |
| SG10201807625PA (en) | 2014-11-17 | 2018-10-30 | Genentech Inc | Combination therapy comprising ox40 binding agonists and pd-1 axis binding antagonists |
| EP3632915A1 (en) | 2014-11-27 | 2020-04-08 | Genentech, Inc. | 4,5,6,7-tetrahydro-1 h-pyrazolo[4,3-c]pyridin-3-amine compounds as cbp and/or ep300 inhibitors |
| KR20170094165A (ko) | 2014-12-23 | 2017-08-17 | 제넨테크, 인크. | 화학요법-내성 암을 치료 및 진단하는 조성물 및 방법 |
| JP2018503373A (ja) | 2014-12-30 | 2018-02-08 | ジェネンテック, インコーポレイテッド | がんの予後診断及び治療のための方法及び組成物 |
| WO2016112251A1 (en) | 2015-01-09 | 2016-07-14 | Genentech, Inc. | 4,5-dihydroimidazole derivatives and their use as histone demethylase (kdm2b) inhibitors |
| EP3242872B1 (en) | 2015-01-09 | 2019-07-03 | Genentech, Inc. | (piperidin-3-yl)(naphthalen-2-yl)methanone derivatives and related compounds as inhibitors of the histone demethylase kdm2b for the treatment of cancer |
| EP3242874B1 (en) | 2015-01-09 | 2018-10-31 | Genentech, Inc. | Pyridazinone derivatives and their use in the treatment of cancer |
| EP3250571B1 (en) | 2015-01-29 | 2022-11-30 | Genentech, Inc. | Therapeutic compounds and uses thereof |
| WO2016123387A1 (en) | 2015-01-30 | 2016-08-04 | Genentech, Inc. | Therapeutic compounds and uses thereof |
| MA41598A (fr) | 2015-02-25 | 2018-01-02 | Constellation Pharmaceuticals Inc | Composés thérapeutiques de pyridazine et leurs utilisations |
| MA41866A (fr) | 2015-03-31 | 2018-02-06 | Massachusetts Gen Hospital | Molécules à auto-assemblage pour l'administration ciblée de médicaments |
| KR20180002653A (ko) | 2015-04-07 | 2018-01-08 | 제넨테크, 인크. | 효능작용 활성을 갖는 항원 결합 복합체 및 사용 방법 |
| ES2898765T3 (es) | 2015-04-10 | 2022-03-08 | Araxes Pharma Llc | Compuestos de quinazolina sustituidos y métodos de uso de los mismos |
| ES2835866T5 (es) | 2015-05-12 | 2024-12-02 | Hoffmann La Roche | Procedimientos terapéuticos y de diagnóstico para el cáncer |
| ES2789500T5 (es) | 2015-05-29 | 2023-09-20 | Hoffmann La Roche | Procedimientos terapéuticos y de diagnóstico para el cáncer |
| JP2018521019A (ja) | 2015-06-08 | 2018-08-02 | ジェネンテック, インコーポレイテッド | 抗ox40抗体を使用して癌を治療する方法 |
| MX2017015937A (es) | 2015-06-08 | 2018-12-11 | Genentech Inc | Métodos de tratamiento del cáncer con anticuerpos anti-ox40 y antagonistas de unión al eje de pd-1. |
| KR102689256B1 (ko) | 2015-06-17 | 2024-07-30 | 제넨테크, 인크. | Pd-1 축 결합 길항제 및 탁산을 사용하여 국소적 진행성 또는 전이성 유방암을 치료하는 방법 |
| PL3456717T3 (pl) * | 2015-07-06 | 2021-10-25 | Gilead Sciences, Inc. | Pochodna 4,6-diaminochinolino-3-karbonitrylu jako modulator cot (cancer osaka thyroid) do leczenia choroby zapalnej |
| NZ738538A (en) | 2015-07-06 | 2019-06-28 | Gilead Sciences Inc | 6-amino-quinoline-3-carbonitrils as cot modulators |
| ES2862727T3 (es) | 2015-08-26 | 2021-10-07 | Fundacion Del Sector Publico Estatal Centro Nac De Investigaciones Oncologicas Carlos Iii F S P Cnio | Compuestos tricíclicos condensados como inhibidores de proteínas quinasas |
| US10935544B2 (en) | 2015-09-04 | 2021-03-02 | Obi Pharma, Inc. | Glycan arrays and method of use |
| PE20181046A1 (es) | 2015-09-25 | 2018-07-03 | Genentech Inc | Anticuerpos anti-tigit y metodos de uso |
| EP3356349A1 (en) | 2015-09-28 | 2018-08-08 | Araxes Pharma LLC | Inhibitors of kras g12c mutant proteins |
| EP3356347A1 (en) | 2015-09-28 | 2018-08-08 | Araxes Pharma LLC | Inhibitors of kras g12c mutant proteins |
| WO2017058805A1 (en) | 2015-09-28 | 2017-04-06 | Araxes Pharma Llc | Inhibitors of kras g12c mutant proteins |
| WO2017058902A1 (en) | 2015-09-28 | 2017-04-06 | Araxes Pharma Llc | Inhibitors of kras g12c mutant proteins |
| EP3356359B1 (en) | 2015-09-28 | 2021-10-20 | Araxes Pharma LLC | Inhibitors of kras g12c mutant proteins |
| WO2017058728A1 (en) | 2015-09-28 | 2017-04-06 | Araxes Pharma Llc | Inhibitors of kras g12c mutant proteins |
| JP6740354B2 (ja) | 2015-10-05 | 2020-08-12 | ザ トラスティーズ オブ コロンビア ユニバーシティー イン ザ シティー オブ ニューヨーク | オートファジーの流れ及びホスホリパーゼd及びタウを含むタンパク質凝集体のクリアランスの活性化剤ならびにタンパク質症の治療方法 |
| KR20180081596A (ko) | 2015-11-16 | 2018-07-16 | 아락세스 파마 엘엘씨 | 치환된 헤테로사이클릭 그룹을 포함하는 2-치환된 퀴나졸린 화합물 및 이의 사용 방법 |
| MY196817A (en) | 2015-12-16 | 2023-05-03 | Genentech Inc | Process for the preparation of tricyclic pi3k inhibitor compounds and methods for using the same for the treatment of cancer |
| KR20180097615A (ko) | 2016-01-08 | 2018-08-31 | 에프. 호프만-라 로슈 아게 | Pd-1 축 결합 길항물질 및 항-cea/항-cd3 이중특이성 항체를 사용하는 cea-양성 암의 치료 방법 |
| JP6821693B2 (ja) | 2016-02-29 | 2021-01-27 | ジェネンテック, インコーポレイテッド | がんのための治療方法及び診断方法 |
| BR112018070097A2 (pt) | 2016-03-29 | 2019-02-12 | Obi Pharma, Inc. | anticorpo, hibridoma, composição farmacêutica, método para tratar câncer em um indivíduo, método para inibir a proliferação de células cancerígenas, método para diagnosticar o câncer em um indivíduo, método para tratar um paciente humano, método para fazer imagens de um indivíduo, conjugado de fármaco-anticorpo (adc), método para tratar câncer, anticorpo biespecífico e método para preparar uma população de anticorpos homogêneos |
| US10980894B2 (en) | 2016-03-29 | 2021-04-20 | Obi Pharma, Inc. | Antibodies, pharmaceutical compositions and methods |
| KR20180134347A (ko) | 2016-04-15 | 2018-12-18 | 제넨테크, 인크. | 암의 진단 및 치료 방법 |
| KR20190003958A (ko) | 2016-04-15 | 2019-01-10 | 제넨테크, 인크. | 암의 치료 및 모니터링 방법 |
| MX2018012493A (es) | 2016-04-15 | 2019-06-06 | Genentech Inc | Métodos para controlar y tratar el cáncer. |
| KR20230110820A (ko) | 2016-04-22 | 2023-07-25 | 오비아이 파머 인코퍼레이티드 | 글로보 계열 항원을 통한 면역 활성화 또는 면역 조정에의한 암 면역요법 |
| US20190151346A1 (en) | 2016-05-10 | 2019-05-23 | INSERM (Institute National de la Santé et de la Recherche Médicale) | Combinations therapies for the treatment of cancer |
| EP3464270B1 (en) | 2016-05-24 | 2022-02-23 | Genentech, Inc. | Heterocyclic inhibitors of cbp/ep300 and their use in the treatment of cancer |
| JP7014736B2 (ja) | 2016-05-24 | 2022-02-01 | ジェネンテック, インコーポレイテッド | がんの処置のためのピラゾロピリジン誘導体 |
| US20200129519A1 (en) | 2016-06-08 | 2020-04-30 | Genentech, Inc. | Diagnostic and therapeutic methods for cancer |
| WO2017214452A1 (en) | 2016-06-08 | 2017-12-14 | Xencor, Inc. | Treatment of igg4-related diseases with anti-cd19 antibodies crossbinding to cd32b |
| CA3029457A1 (en) | 2016-06-30 | 2018-01-04 | Gilead Sciences, Inc. | 4,6-diaminoquinazolines as cot modulators and methods of use thereof |
| CN110072545A (zh) | 2016-07-27 | 2019-07-30 | 台湾浩鼎生技股份有限公司 | 免疫原性/治疗性聚糖组合物及其用途 |
| US11643456B2 (en) | 2016-07-29 | 2023-05-09 | Obi Pharma, Inc. | Human antibodies, pharmaceutical compositions and methods |
| WO2018027204A1 (en) | 2016-08-05 | 2018-02-08 | Genentech, Inc. | Multivalent and multiepitopic anitibodies having agonistic activity and methods of use |
| WO2018029124A1 (en) | 2016-08-08 | 2018-02-15 | F. Hoffmann-La Roche Ag | Therapeutic and diagnostic methods for cancer |
| WO2018064510A1 (en) | 2016-09-29 | 2018-04-05 | Araxes Pharma Llc | Inhibitors of kras g12c mutant proteins |
| CA3038712A1 (en) | 2016-10-06 | 2018-04-12 | Genentech, Inc. | Therapeutic and diagnostic methods for cancer |
| WO2018081648A2 (en) | 2016-10-29 | 2018-05-03 | Genentech, Inc. | Anti-mic antibidies and methods of use |
| TWI822055B (zh) | 2016-11-21 | 2023-11-11 | 台灣浩鼎生技股份有限公司 | 共軛生物分子、醫藥組成物及方法 |
| US11136308B2 (en) | 2017-01-26 | 2021-10-05 | Araxes Pharma Llc | Substituted quinazoline and quinazolinone compounds and methods of use thereof |
| EP3573954A1 (en) | 2017-01-26 | 2019-12-04 | Araxes Pharma LLC | Fused bicyclic benzoheteroaromatic compounds and methods of use thereof |
| JP7327802B2 (ja) | 2017-01-26 | 2023-08-16 | アラクセス ファーマ エルエルシー | 縮合ヘテロ-ヘテロ二環式化合物およびその使用方法 |
| WO2018140599A1 (en) | 2017-01-26 | 2018-08-02 | Araxes Pharma Llc | Benzothiophene and benzothiazole compounds and methods of use thereof |
| WO2018140513A1 (en) | 2017-01-26 | 2018-08-02 | Araxes Pharma Llc | 1-(3-(6-(3-hydroxynaphthalen-1-yl)benzofuran-2-yl)azetidin-1yl)prop-2-en-1-one derivatives and similar compounds as kras g12c modulators for treating cancer |
| TW201837467A (zh) | 2017-03-01 | 2018-10-16 | 美商建南德克公司 | 用於癌症之診斷及治療方法 |
| CN110505883A (zh) | 2017-04-13 | 2019-11-26 | 豪夫迈·罗氏有限公司 | 供治疗癌症的方法中使用的白介素-2免疫缀合物,cd40激动剂,和任选地pd-1轴结合拮抗剂 |
| US10745385B2 (en) | 2017-05-25 | 2020-08-18 | Araxes Pharma Llc | Covalent inhibitors of KRAS |
| WO2018218069A1 (en) | 2017-05-25 | 2018-11-29 | Araxes Pharma Llc | Quinazoline derivatives as modulators of mutant kras, hras or nras |
| CN110869357A (zh) | 2017-05-25 | 2020-03-06 | 亚瑞克西斯制药公司 | 化合物及其用于治疗癌症的使用方法 |
| JP7760242B2 (ja) | 2017-07-21 | 2025-10-27 | ジェネンテック, インコーポレイテッド | がんの治療法及び診断法 |
| MX2020000903A (es) | 2017-08-11 | 2020-07-22 | Genentech Inc | Anticuerpos anti-cd8 y usos de los mismos. |
| KR102811888B1 (ko) | 2017-09-08 | 2025-05-27 | 에프. 호프만-라 로슈 아게 | 암의 진단 및 치료 방법 |
| US11369608B2 (en) | 2017-10-27 | 2022-06-28 | University Of Virginia Patent Foundation | Compounds and methods for regulating, limiting, or inhibiting AVIL expression |
| TW201923089A (zh) | 2017-11-06 | 2019-06-16 | 美商建南德克公司 | 癌症之診斷及治療方法 |
| AU2019207535B2 (en) | 2018-01-15 | 2021-12-23 | Epiaxis Therapeutics Pty Ltd | Agents and methods for predicting response to therapy |
| CA3088198A1 (en) | 2018-01-26 | 2019-08-01 | Exelixis, Inc. | Compounds for the treatment of kinase-dependent disorders |
| CR20250117A (es) | 2018-01-26 | 2025-05-09 | Exelixis Inc | COMPUESTOS PARA EL TRATAMIENTO DE TRASTORNOS DEPENDIENTES DE CINASAS (Divisional 2020-0355) |
| CN117402114A (zh) | 2018-01-26 | 2024-01-16 | 埃克塞里艾克西斯公司 | 用于治疗激酶依赖性病症的化合物 |
| CN111836831A (zh) | 2018-02-26 | 2020-10-27 | 豪夫迈·罗氏有限公司 | 用于抗tigit拮抗剂抗体和抗pd-l1拮抗剂抗体治疗的给药 |
| JP2021524744A (ja) | 2018-05-21 | 2021-09-16 | ナノストリング テクノロジーズ,インコーポレイティド | 分子遺伝子シグネチャーとその使用方法 |
| MY205645A (en) | 2018-06-23 | 2024-11-02 | Genentech Inc | Methods of treating lung cancer with a pd-1 axis binding antagonist, a platinum agent, and a topoisomerase ii inhibitor |
| TW202504930A (zh) | 2018-06-27 | 2025-02-01 | 台灣浩鼎生技股份有限公司 | 用於糖蛋白工程的糖苷合成酶變體及其使用方法 |
| CN108752248A (zh) * | 2018-07-17 | 2018-11-06 | 常州大学 | 一种合成1-(3-乙氧基-4-甲氧基)苯基-2-甲磺酰基乙胺的方法 |
| WO2020018789A1 (en) | 2018-07-18 | 2020-01-23 | Genentech, Inc. | Methods of treating lung cancer with a pd-1 axis binding antagonist, an antimetabolite, and a platinum agent |
| MX2021000887A (es) | 2018-08-01 | 2021-03-31 | Araxes Pharma Llc | Compuestos espiroheterociclicos y metodos de uso de los mismos para el tratamiento de cancer. |
| EP3847154A1 (en) | 2018-09-03 | 2021-07-14 | F. Hoffmann-La Roche AG | Carboxamide and sulfonamide derivatives useful as tead modulators |
| AU2019342099A1 (en) | 2018-09-19 | 2021-04-08 | Genentech, Inc. | Therapeutic and diagnostic methods for bladder cancer |
| KR102739487B1 (ko) | 2018-09-21 | 2024-12-10 | 제넨테크, 인크. | 3중-음성 유방암에 대한 진단 방법 |
| US12404540B2 (en) | 2018-10-17 | 2025-09-02 | The University Of Queensland | Epigenetic biomarker and uses therefor |
| EP3867646A1 (en) | 2018-10-18 | 2021-08-25 | F. Hoffmann-La Roche AG | Diagnostic and therapeutic methods for sarcomatoid kidney cancer |
| CN113396230A (zh) | 2019-02-08 | 2021-09-14 | 豪夫迈·罗氏有限公司 | 癌症的诊断和治疗方法 |
| CN113677994B (zh) | 2019-02-27 | 2025-09-09 | 外延轴治疗股份有限公司 | 用于评估t细胞功能和预测对疗法的应答的方法和药剂 |
| WO2020176748A1 (en) | 2019-02-27 | 2020-09-03 | Genentech, Inc. | Dosing for treatment with anti-tigit and anti-cd20 or anti-cd38 antibodies |
| WO2020223233A1 (en) | 2019-04-30 | 2020-11-05 | Genentech, Inc. | Prognostic and therapeutic methods for colorectal cancer |
| CN114269376A (zh) | 2019-05-03 | 2022-04-01 | 豪夫迈·罗氏有限公司 | 用抗pd-l1抗体治疗癌症的方法 |
| TWI770527B (zh) | 2019-06-14 | 2022-07-11 | 美商基利科學股份有限公司 | Cot 調節劑及其使用方法 |
| CN112300279A (zh) | 2019-07-26 | 2021-02-02 | 上海复宏汉霖生物技术股份有限公司 | 针对抗cd73抗体和变体的方法和组合物 |
| TWI873176B (zh) | 2019-09-04 | 2025-02-21 | 美商建南德克公司 | Cd8結合劑及其用途 |
| JP2022551422A (ja) | 2019-09-26 | 2022-12-09 | エグゼリクシス, インコーポレイテッド | ピリドン化合物およびタンパク質キナーゼの調節における使用の方法 |
| JP2022548978A (ja) | 2019-09-27 | 2022-11-22 | ジェネンテック, インコーポレイテッド | 薬抗tigit及び抗pd-l1アンタゴニスト抗体を用いた処置のための投薬 |
| JP2023511472A (ja) | 2019-10-29 | 2023-03-20 | エフ・ホフマン-ラ・ロシュ・アクチェンゲゼルシャフト | がんの治療のための二官能性化合物 |
| KR20220092580A (ko) | 2019-11-06 | 2022-07-01 | 제넨테크, 인크. | 혈액암의 치료를 위한 진단과 치료 방법 |
| TW202130618A (zh) | 2019-11-13 | 2021-08-16 | 美商建南德克公司 | 治療性化合物及使用方法 |
| WO2021119505A1 (en) | 2019-12-13 | 2021-06-17 | Genentech, Inc. | Anti-ly6g6d antibodies and methods of use |
| CA3164995A1 (en) | 2019-12-20 | 2021-06-24 | Erasca, Inc. | Tricyclic pyridones and pyrimidones |
| TW202142230A (zh) | 2020-01-27 | 2021-11-16 | 美商建南德克公司 | 用於以抗tigit拮抗體抗體治療癌症之方法 |
| WO2022050954A1 (en) | 2020-09-04 | 2022-03-10 | Genentech, Inc. | Dosing for treatment with anti-tigit and anti-pd-l1 antagonist antibodies |
| WO2021194481A1 (en) | 2020-03-24 | 2021-09-30 | Genentech, Inc. | Dosing for treatment with anti-tigit and anti-pd-l1 antagonist antibodies |
| WO2021177980A1 (en) | 2020-03-06 | 2021-09-10 | Genentech, Inc. | Combination therapy for cancer comprising pd-1 axis binding antagonist and il6 antagonist |
| CA3175541A1 (en) | 2020-03-30 | 2021-10-07 | Gilead Sciences, Inc. | Solid forms of (s)-6-(((1-(bicyclo[1.1.1]pentan-1-yl)-1h-1,2,3-triazol-4-yl)2-methyl-1-oxo-1,2- dihydroisoquinolin-5-yl)methyl)))amino)8-chloro-(neopentylamino)quinoline-3-carb onitrile a cot inhibitor compound |
| JP7446475B2 (ja) | 2020-04-02 | 2024-03-08 | ギリアード サイエンシーズ, インコーポレイテッド | Cot阻害剤化合物を調製するためのプロセス |
| WO2021202959A1 (en) | 2020-04-03 | 2021-10-07 | Genentech, Inc. | Therapeutic and diagnostic methods for cancer |
| EP4143345A1 (en) | 2020-04-28 | 2023-03-08 | Genentech, Inc. | Methods and compositions for non-small cell lung cancer immunotherapy |
| AU2021293038A1 (en) | 2020-06-16 | 2023-02-02 | F. Hoffmann-La Roche Ag | Methods and compositions for treating triple-negative breast cancer |
| KR20230024368A (ko) | 2020-06-18 | 2023-02-20 | 제넨테크, 인크. | 항-tigit 항체 및 pd-1 축 결합 길항제를 사용한 치료 |
| EP4172628A1 (en) | 2020-06-30 | 2023-05-03 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods for predicting the risk of recurrence and/or death of patients suffering from a solid cancer after preoperative adjuvant therapy and radical surgery |
| US20230235408A1 (en) | 2020-06-30 | 2023-07-27 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods for predicting the risk of recurrence and/or death of patients suffering from a solid cancer after preoperative adjuvant therapies |
| WO2022006386A1 (en) * | 2020-07-02 | 2022-01-06 | Enliven Therapeutics, Inc. | Alkyne quinazoline derivatives as inhibitors of erbb2 |
| US11787775B2 (en) | 2020-07-24 | 2023-10-17 | Genentech, Inc. | Therapeutic compounds and methods of use |
| JP2023536602A (ja) | 2020-08-03 | 2023-08-28 | ジェネンテック, インコーポレイテッド | リンパ腫のための診断及び治療方法 |
| EP4194443A4 (en) * | 2020-08-10 | 2024-10-09 | Abbisko Therapeutics Co., Ltd. | Efgr inhibitor, preparation method therefor, and application thereof |
| WO2022036146A1 (en) | 2020-08-12 | 2022-02-17 | Genentech, Inc. | Diagnostic and therapeutic methods for cancer |
| CA3193273A1 (en) | 2020-08-27 | 2022-03-03 | Enosi Therapeutics Corporation | Methods and compositions to treat autoimmune diseases and cancer |
| JP2023544450A (ja) | 2020-09-23 | 2023-10-23 | エラスカ・インコーポレイテッド | 三環式ピリドン及びピリミドン |
| CN116406291A (zh) | 2020-10-05 | 2023-07-07 | 基因泰克公司 | 用抗fcrh5/抗cd3双特异性抗体进行治疗的给药 |
| WO2022133345A1 (en) | 2020-12-18 | 2022-06-23 | Erasca, Inc. | Tricyclic pyridones and pyrimidones |
| AU2022221124A1 (en) | 2021-02-12 | 2023-08-03 | F. Hoffmann-La Roche Ag | Bicyclic tetrahydroazepine derivatives for the treatment of cancer |
| CA3211063A1 (en) | 2021-02-19 | 2022-08-25 | Exelixis, Inc. | Pyridone compounds and methods of use |
| KR20240026948A (ko) | 2021-05-25 | 2024-02-29 | 에라스카, 아이엔씨. | 황 함유 헤테로방향족 트리사이클릭 kras 억제제 |
| WO2022266206A1 (en) | 2021-06-16 | 2022-12-22 | Erasca, Inc. | Kras inhibitor conjugates |
| AU2022315530A1 (en) | 2021-07-20 | 2024-01-18 | Ags Therapeutics Sas | Extracellular vesicles from microalgae, their preparation, and uses |
| TW202321261A (zh) | 2021-08-10 | 2023-06-01 | 美商伊瑞斯卡公司 | 選擇性kras抑制劑 |
| US12110276B2 (en) | 2021-11-24 | 2024-10-08 | Genentech, Inc. | Pyrazolo compounds and methods of use thereof |
| US12275745B2 (en) | 2021-11-24 | 2025-04-15 | Genentech, Inc. | Therapeutic compounds and methods of use |
| WO2023144127A1 (en) | 2022-01-31 | 2023-08-03 | Ags Therapeutics Sas | Extracellular vesicles from microalgae, their biodistribution upon administration, and uses |
| TW202342018A (zh) | 2022-03-04 | 2023-11-01 | 美商奇奈特生物製藥公司 | Mek激酶抑制劑 |
| IL315770A (en) | 2022-04-01 | 2024-11-01 | Genentech Inc | Dosage for treatment with bispecific anti-FCRH5/anti-CD3 antibodies |
| JP2025517650A (ja) | 2022-05-11 | 2025-06-10 | ジェネンテック, インコーポレイテッド | 抗FcRH5/抗CD3二重特異性抗体による処置のための投与 |
| KR20250022049A (ko) | 2022-06-07 | 2025-02-14 | 제넨테크, 인크. | 항-pd-l1 길항제 및 항-tigit 길항제 항체를 포함하는, 폐암 치료의 효율을 결정하는 방법 |
| CN115057776B (zh) * | 2022-06-15 | 2023-08-22 | 必维申瓯质量技术服务温州有限公司 | 2-萘甲酸乙酯衍生物的合成方法 |
| AU2023305619A1 (en) | 2022-07-13 | 2025-01-23 | F. Hoffmann-La Roche Ag | Dosing for treatment with anti-fcrh5/anti-cd3 bispecific antibodies |
| KR20250040020A (ko) | 2022-07-19 | 2025-03-21 | 제넨테크, 인크. | 항-fcrh5/항-cd3 이중특이성 항체로 치료하기 위한 투약법 |
| WO2024033457A1 (en) | 2022-08-11 | 2024-02-15 | F. Hoffmann-La Roche Ag | Bicyclic tetrahydrothiazepine derivatives |
| JP2025526726A (ja) | 2022-08-11 | 2025-08-15 | エフ・ホフマン-ラ・ロシュ・アクチェンゲゼルシャフト | 二環式テトラヒドロアゼピン誘導体 |
| AU2023322638A1 (en) | 2022-08-11 | 2024-11-28 | F. Hoffmann-La Roche Ag | Bicyclic tetrahydrothiazepine derivatives |
| AU2023322637A1 (en) | 2022-08-11 | 2024-11-14 | F. Hoffmann-La Roche Ag | Bicyclic tetrahydrothiazepine derivatives |
| JP2025538859A (ja) | 2022-10-21 | 2025-12-02 | 公益財団法人川崎市産業振興財団 | 非吸着性またはスーパーステルス小胞 |
| WO2024088808A1 (en) | 2022-10-24 | 2024-05-02 | Ags Therapeutics Sas | Extracellular vesicles from microalgae, their biodistribution upon intranasal administration, and uses thereof |
| KR20250093336A (ko) | 2022-10-25 | 2025-06-24 | 제넨테크, 인크. | 다발성 골수종에 대한 치료 및 진단 방법 |
| EP4665735A1 (en) | 2023-02-17 | 2025-12-24 | Erasca, Inc. | Kras inhibitors |
| AU2024270495A1 (en) | 2023-05-05 | 2025-10-09 | Genentech, Inc. | Dosing for treatment with anti-fcrh5/anti-cd3 bispecific antibodies |
| KR20260021689A (ko) | 2023-06-08 | 2026-02-13 | 제넨테크, 인크. | 림프종 진단 및 치료 방법을 위한 대식세포 시그니처 |
| WO2025024257A1 (en) | 2023-07-21 | 2025-01-30 | Genentech, Inc. | Diagnostic and therapeutic methods for cancer |
| TW202515614A (zh) | 2023-08-25 | 2025-04-16 | 美商建南德克公司 | 治療非小細胞肺癌之方法及組成物 |
| WO2025176843A1 (en) | 2024-02-21 | 2025-08-28 | Ags Therapeutics Sas | Microalgae extracellular vesicle based gene therapy vectors (mev-gtvs), their preparation, and uses thereof |
| WO2026030464A1 (en) | 2024-07-30 | 2026-02-05 | Genentech, Inc. | Dosage regimen for reducing cytokine release syndrome (crs) with anti-fcrh5/anti-cd3 bispecific antibodies in multiple myeloma therapy |
| WO2026030476A1 (en) | 2024-07-30 | 2026-02-05 | Genentech, Inc. | Precision medicine for optimal dosage of combined therapies systems and methods of use thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1996009294A1 (en) * | 1994-09-19 | 1996-03-28 | The Wellcome Foundation Limited | Substituted heteroaromatic compounds and their use in medicine |
| WO1997014681A1 (en) * | 1995-10-16 | 1997-04-24 | Fujisawa Pharmaceutical Co., Ltd. | Heterocyclic compounds as h+-atpases |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9004483D0 (en) * | 1990-02-28 | 1990-04-25 | Erba Carlo Spa | New aryl-and heteroarylethenylene derivatives and process for their preparation |
| AU7228896A (en) * | 1995-10-16 | 1997-05-07 | Fujisawa Pharmaceutical Co., Ltd. | Heterocyclic compounds as h+-atpases |
-
1998
- 1998-02-04 UA UA99116029A patent/UA73073C2/uk unknown
- 1998-04-01 ZA ZA9802771A patent/ZA982771B/xx unknown
- 1998-04-02 TR TR1999/02946T patent/TR199902946T2/xx unknown
- 1998-04-02 KR KR10-1999-7009125A patent/KR100531969B1/ko not_active Expired - Lifetime
- 1998-04-02 CN CN98805734A patent/CN1121391C/zh not_active Expired - Lifetime
- 1998-04-02 PL PL335999A patent/PL196471B1/pl unknown
- 1998-04-02 CZ CZ0351799A patent/CZ299136B6/cs not_active IP Right Cessation
- 1998-04-02 SK SK1357-99A patent/SK284922B6/sk not_active IP Right Cessation
- 1998-04-02 BR BR9808478-0A patent/BR9808478A/pt not_active Application Discontinuation
- 1998-04-02 EP EP98914417A patent/EP0973746B1/en not_active Expired - Lifetime
- 1998-04-02 CA CA2285241A patent/CA2285241C/en not_active Expired - Lifetime
- 1998-04-02 HU HU0002112A patent/HU229549B1/hu unknown
- 1998-04-02 JP JP54198198A patent/JP4537500B2/ja not_active Expired - Lifetime
- 1998-04-02 IL IL13219298A patent/IL132192A0/xx not_active IP Right Cessation
- 1998-04-02 TW TW087104964A patent/TWI228492B/zh not_active IP Right Cessation
- 1998-04-02 NZ NZ337782A patent/NZ337782A/en not_active IP Right Cessation
- 1998-04-02 WO PCT/US1998/006480 patent/WO1998043960A1/en not_active Ceased
- 1998-04-02 DE DE69818442T patent/DE69818442T2/de not_active Expired - Lifetime
- 1998-04-02 PT PT98914417T patent/PT973746E/pt unknown
- 1998-04-02 AU AU68777/98A patent/AU750906B2/en not_active Expired
- 1998-04-02 ES ES98914417T patent/ES2209124T3/es not_active Expired - Lifetime
- 1998-04-02 DK DK98914417T patent/DK0973746T3/da active
- 1998-04-02 AR ARP980101506A patent/AR012313A1/es active IP Right Grant
- 1998-04-02 RU RU99123060/04A patent/RU2202551C2/ru active
- 1998-04-02 AT AT98914417T patent/ATE250583T1/de active
-
1999
- 1999-10-01 NO NO19994798A patent/NO313827B1/no not_active IP Right Cessation
-
2009
- 2009-04-28 JP JP2009109693A patent/JP5086301B2/ja not_active Expired - Lifetime
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1996009294A1 (en) * | 1994-09-19 | 1996-03-28 | The Wellcome Foundation Limited | Substituted heteroaromatic compounds and their use in medicine |
| WO1997014681A1 (en) * | 1995-10-16 | 1997-04-24 | Fujisawa Pharmaceutical Co., Ltd. | Heterocyclic compounds as h+-atpases |
Non-Patent Citations (2)
| Title |
|---|
| PRICE С.С., BOEKELHEIDE V., "A SYNTESIS OF SUBSTITUTED 4-AMINOQUINOLINES", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1946, vol.68, no.6, pp.1246-1250. * |
| REWCASTLE G.W., "TYROSINE KINASE INHIBITORS...", JOURNAL OF MEDICINAL CHEMISTRY, 1995, vol.38, no.18, pp.3482-3487. GASIT A., "TYRPHOSTINS...", JOURNAL OF MEDICINAL CHEMISTRY, 1996, vol.39, no.11, pp.2170-2177. * |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2317290C2 (ru) * | 2003-07-31 | 2008-02-20 | Санофи-Авентис | Производные аминохинолина и их применение в качестве лигандов аденозина а3 |
| RU2345069C2 (ru) * | 2003-08-19 | 2009-01-27 | Уайт Холдингз Корпорейшн | Способ получения 4-амино-3-хинолинкарбонитрилов |
| RU2536102C2 (ru) * | 2009-09-14 | 2014-12-20 | Цзянсу Хэнжуй Медицин Ко., Лтд. | Производные 6-аминохиназолина или 3-цианохинолина, способы их получения и их применение в качестве ингибитора рецепторных тирозинкиназ egfr или her-2 |
| RU2600928C2 (ru) * | 2010-06-09 | 2016-10-27 | Тяньцзинь Химэй Байо-Тек Ко., Лтд | Цианохинолиновые производные |
| RU2631321C2 (ru) * | 2012-07-12 | 2017-09-21 | Цзянсу Хэнжуй Медсин Ко., Лтд. | Кристаллическая форма i дималеата ингибитора тирозинкиназы и способ ее получения |
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| RU2202551C2 (ru) | Замещенные 3-цианохинолины | |
| RU99123060A (ru) | Замещенные 3-цианохинолины | |
| KR100817423B1 (ko) | 시아노퀴놀린을 포함하는 결장 폴립의 치료 또는 억제를 위한 약제학적 조성물 | |
| EP0860433B1 (en) | Quinoline derivatives and quinazoline derivatives inhibiting autophosphorylation of growth factor receptor originating in platelet and pharmaceutical compositions containing the same | |
| RU2362773C2 (ru) | Производные хиназолина для торможения роста раковых клеток и способ их получения | |
| CA2223016C (en) | Protein tyrosine kinase aryl and heteroaryl quinazoline compounds having selective inhibition of her-2 autophosphorylation properties | |
| JP2003526686A5 (https=) | ||
| CN1160338C (zh) | N-[4-(3-氯-4-氟-苯基氨基)-7-(3-吗啉-4-基-丙氧基)-喹唑啉-6-基]-丙烯酰胺,不可逆的酪氨酸激酶抑制剂 | |
| JP2008542267A (ja) | 3−シアノ−キノリンと、それにより製造される中間体とを調製する方法 | |
| JP2001515071A (ja) | 置換キナゾリン誘導体およびチロシンキナーゼインヒビターとしてのそれらの使用 | |
| JP2002525359A (ja) | プロテインチロシンキナーゼインヒビターとしての置換3−シアノキノリン | |
| JPWO1997017329A1 (ja) | 血小板由来成長因子受容体自己リン酸化を阻害するキノリン誘導体ならびにキナゾリン誘導体およびそれらを含有する薬学的組成物 | |
| BRPI0407249A (pt) | Preparação de quinazolinas substituìdas | |
| AP2004003059A0 (en) | Salt forms of E-2-methoxy-N-(3-(4-(3-methyl-pyridin-3-yloxyl)-phenylamino)-quinazolin-6-yl)-allyl)-acetamide, its preparation and its use against cancer | |
| JP2003509500A (ja) | 治療用キナゾリン誘導体 | |
| RU2004131641A (ru) | Новые соединения | |
| RU98110007A (ru) | Конденсированные тропановые производные в качестве ингибиторов обратного захвата нейромедиаторов | |
| EP1100788B1 (en) | Substituted quinazoline derivatives | |
| HU194836B (en) | Process for producing 2-/phenyl-alkyl/-3-/amino-alkyl/-4/3h/-quinazolinnone derivatives and pharmaceutical compositions containing them | |
| JP2009538306A (ja) | 4−ハロゲン化キノリン中間体を調製する方法 | |
| RU96124804A (ru) | Производные хинолина как антагонисты nk, рецептора тахикинина | |
| RU2345079C2 (ru) | Производные диаминопирролохиназолинов в качестве ингибиторов протеинтирозинкиназы | |
| EA200200733A1 (ru) | Новые гетероарильные производные, их получение и применение | |
| RU2007135508A (ru) | Производные хиназолина в качестве ингибиторов тирозинкиназы | |
| MXPA01000987A (en) | Substituted quinazoline derivatives |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PC43 | Official registration of the transfer of the exclusive right without contract for inventions |
Effective date: 20150213 |