JP2016519685A5 - - Google Patents
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- Publication number
- JP2016519685A5 JP2016519685A5 JP2016507671A JP2016507671A JP2016519685A5 JP 2016519685 A5 JP2016519685 A5 JP 2016519685A5 JP 2016507671 A JP2016507671 A JP 2016507671A JP 2016507671 A JP2016507671 A JP 2016507671A JP 2016519685 A5 JP2016519685 A5 JP 2016519685A5
- Authority
- JP
- Japan
- Prior art keywords
- sulfonamide
- fluorophenyl
- fluoropropane
- morpholinoquinazolin
- methoxy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- -1 n- propyl Chemical group 0.000 claims 45
- 150000001875 compounds Chemical class 0.000 claims 41
- 230000000694 effects Effects 0.000 claims 13
- 229910052799 carbon Inorganic materials 0.000 claims 9
- 229910052736 halogen Inorganic materials 0.000 claims 9
- 150000002367 halogens Chemical class 0.000 claims 9
- 238000000034 method Methods 0.000 claims 7
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Natural products C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 5
- 150000001408 amides Chemical class 0.000 claims 5
- 125000001072 heteroaryl group Chemical group 0.000 claims 5
- 239000000203 mixture Substances 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims 3
- 206010028980 Neoplasm Diseases 0.000 claims 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 3
- 201000011510 cancer Diseases 0.000 claims 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims 3
- 230000003389 potentiating effect Effects 0.000 claims 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 3
- 125000003107 substituted aryl group Chemical group 0.000 claims 3
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims 2
- 239000013610 patient sample Substances 0.000 claims 2
- 210000003800 pharynx Anatomy 0.000 claims 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 2
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 claims 1
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical class C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 claims 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 claims 1
- RXYPXQSKLGGKOL-UHFFFAOYSA-O 1,4-dimethylpiperazin-1-ium Chemical compound CN1CC[NH+](C)CC1 RXYPXQSKLGGKOL-UHFFFAOYSA-O 0.000 claims 1
- HQOFCYFPTWLSNU-UHFFFAOYSA-N 1-[4-[6-[2-fluoro-3-(propylsulfonylamino)phenyl]-8-methoxy-4-morpholin-4-ylquinazolin-2-yl]phenyl]-3-methylurea Chemical compound CCCS(=O)(=O)NC1=CC=CC(C=2C=C3C(N4CCOCC4)=NC(=NC3=C(OC)C=2)C=2C=CC(NC(=O)NC)=CC=2)=C1F HQOFCYFPTWLSNU-UHFFFAOYSA-N 0.000 claims 1
- PONJYXCDURJRQT-UHFFFAOYSA-N 1-[4-[6-[3-[(2,6-difluorophenyl)sulfonylamino]-2-fluorophenyl]-8-methoxy-4-morpholin-4-ylquinazolin-2-yl]phenyl]-3-methylurea Chemical compound CNC(=O)Nc1ccc(cc1)-c1nc(N2CCOCC2)c2cc(cc(OC)c2n1)-c1cccc(NS(=O)(=O)c2c(F)cccc2F)c1F PONJYXCDURJRQT-UHFFFAOYSA-N 0.000 claims 1
- AXWLKJWVMMAXBD-UHFFFAOYSA-N 1-butylpiperidine Chemical compound CCCCN1CCCCC1 AXWLKJWVMMAXBD-UHFFFAOYSA-N 0.000 claims 1
- LPCWDBCEHWHJGX-UHFFFAOYSA-N 1-ethyl-2-methylpiperidine Chemical compound CCN1CCCCC1C LPCWDBCEHWHJGX-UHFFFAOYSA-N 0.000 claims 1
- PAMIQIKDUOTOBW-UHFFFAOYSA-O 1-methylpiperidin-1-ium Chemical compound C[NH+]1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-O 0.000 claims 1
- YQOPNAOQGQSUHF-UHFFFAOYSA-N 1-propan-2-ylpyrrolidine Chemical compound CC(C)N1CCCC1 YQOPNAOQGQSUHF-UHFFFAOYSA-N 0.000 claims 1
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 claims 1
- NNWUEBIEOFQMSS-UHFFFAOYSA-N 2-Methylpiperidine Chemical compound CC1CCCCN1 NNWUEBIEOFQMSS-UHFFFAOYSA-N 0.000 claims 1
- CKAGEKRKCUKMLU-UHFFFAOYSA-N 2-[2-(6-aminopyridin-3-yl)-6-[2-fluoro-3-(3-fluoropropylsulfonylamino)phenyl]-4-morpholin-4-ylquinazolin-8-yl]oxyacetic acid 2,2,2-trifluoroacetic acid Chemical compound FC(C(=O)O)(F)F.NC1=CC=C(C=N1)C1=NC2=C(C=C(C=C2C(=N1)N1CCOCC1)C1=C(C(=CC=C1)NS(=O)(=O)CCCF)F)OCC(=O)O CKAGEKRKCUKMLU-UHFFFAOYSA-N 0.000 claims 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims 1
- ZFHHGBADWRUTKG-UHFFFAOYSA-N 3-fluoro-n-[2-fluoro-3-[2-(1h-indazol-4-yl)-4-morpholin-4-ylpyrido[3,2-d]pyrimidin-6-yl]phenyl]propane-1-sulfonamide Chemical compound FCCCS(=O)(=O)NC1=CC=CC(C=2N=C3C(N4CCOCC4)=NC(=NC3=CC=2)C=2C=3C=NNC=3C=CC=2)=C1F ZFHHGBADWRUTKG-UHFFFAOYSA-N 0.000 claims 1
- HVCNXQOWACZAFN-UHFFFAOYSA-O 4-ethylmorpholin-4-ium Chemical compound CC[NH+]1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-O 0.000 claims 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims 1
- BWLUMTFWVZZZND-UHFFFAOYSA-N Dibenzylamine Chemical compound C=1C=CC=CC=1CNCC1=CC=CC=C1 BWLUMTFWVZZZND-UHFFFAOYSA-N 0.000 claims 1
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Divinylene sulfide Natural products C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 1
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims 1
- 101001051706 Homo sapiens Ribosomal protein S6 kinase beta-1 Proteins 0.000 claims 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims 1
- 206010025323 Lymphomas Diseases 0.000 claims 1
- BAVYZALUXZFZLV-UHFFFAOYSA-O Methylammonium ion Chemical compound [NH3+]C BAVYZALUXZFZLV-UHFFFAOYSA-O 0.000 claims 1
- AZEFSIAYOQKQFU-HNNXBMFYSA-N N-[3-[2-(2-amino-4-methylpyrimidin-5-yl)-4-[(3S)-3-methylmorpholin-4-yl]pyrido[3,2-d]pyrimidin-6-yl]-2-fluorophenyl]-2,5-difluorobenzenesulfonamide Chemical compound NC1=NC=C(C(=N1)C)C=1N=C(C2=C(N=1)C=CC(=N2)C=1C(=C(C=CC=1)NS(=O)(=O)C1=C(C=CC(=C1)F)F)F)N1[C@H](COCC1)C AZEFSIAYOQKQFU-HNNXBMFYSA-N 0.000 claims 1
- HNNSHBLYLKUEKC-HNNXBMFYSA-N N-[3-[2-(2-amino-4-methylpyrimidin-5-yl)-4-[(3S)-3-methylmorpholin-4-yl]pyrido[3,2-d]pyrimidin-6-yl]-2-fluorophenyl]-3-fluoropropane-1-sulfonamide Chemical compound C[C@H]1COCCN1c1nc(nc2ccc(nc12)-c1cccc(NS(=O)(=O)CCCF)c1F)-c1cnc(N)nc1C HNNSHBLYLKUEKC-HNNXBMFYSA-N 0.000 claims 1
- GOYNWVKPYAPRGK-UHFFFAOYSA-N N-[3-[2-(2-amino-4-methylpyrimidin-5-yl)-4-morpholin-4-ylpyrido[3,2-d]pyrimidin-6-yl]-2-fluorophenyl]-3-fluoropropane-1-sulfonamide Chemical compound NC1=NC=C(C(=N1)C)C=1N=C(C2=C(N=1)C=CC(=N2)C=1C(=C(C=CC=1)NS(=O)(=O)CCCF)F)N1CCOCC1 GOYNWVKPYAPRGK-UHFFFAOYSA-N 0.000 claims 1
- HWGPFCJQFPPBOD-QGZVFWFLSA-N N-[3-[2-(2-aminopyrimidin-5-yl)-8-(2-fluoroethoxy)-4-[(3R)-3-methylmorpholin-4-yl]quinazolin-6-yl]-2-fluorophenyl]-3-fluoropropane-1-sulfonamide Chemical compound NC1=NC=C(C=N1)C1=NC2=C(C=C(C=C2C(=N1)N1[C@@H](COCC1)C)C=1C(=C(C=CC1)NS(=O)(=O)CCCF)F)OCCF HWGPFCJQFPPBOD-QGZVFWFLSA-N 0.000 claims 1
- MTGTVPVITJOLCP-QGZVFWFLSA-N N-[3-[2-(2-aminopyrimidin-5-yl)-8-ethoxy-4-[(3R)-3-methylmorpholin-4-yl]quinazolin-6-yl]-2-fluorophenyl]-3-fluoropropane-1-sulfonamide Chemical compound NC1=NC=C(C=N1)C1=NC2=C(C=C(C=C2C(=N1)N1[C@@H](COCC1)C)C=1C(=C(C=CC1)NS(=O)(=O)CCCF)F)OCC MTGTVPVITJOLCP-QGZVFWFLSA-N 0.000 claims 1
- MTGTVPVITJOLCP-KRWDZBQOSA-N N-[3-[2-(2-aminopyrimidin-5-yl)-8-ethoxy-4-[(3S)-3-methylmorpholin-4-yl]quinazolin-6-yl]-2-fluorophenyl]-3-fluoropropane-1-sulfonamide Chemical compound CCOc1cc(cc2c(nc(nc12)-c1cnc(N)nc1)N1CCOC[C@@H]1C)-c1cccc(NS(=O)(=O)CCCF)c1F MTGTVPVITJOLCP-KRWDZBQOSA-N 0.000 claims 1
- SSZKHFIPLIWYMR-QGZVFWFLSA-N N-[3-[2-(2-aminopyrimidin-5-yl)-8-ethyl-4-[(3R)-3-methylmorpholin-4-yl]quinazolin-6-yl]-2-fluorophenyl]-3-fluoropropane-1-sulfonamide Chemical compound CCc1cc(cc2c(nc(nc12)-c1cnc(N)nc1)N1CCOC[C@H]1C)-c1cccc(NS(=O)(=O)CCCF)c1F SSZKHFIPLIWYMR-QGZVFWFLSA-N 0.000 claims 1
- BLMATCSJUYYMEA-MRXNPFEDSA-N N-[3-[2-(5-aminopyrazin-2-yl)-8-methoxy-4-[(3R)-3-methylmorpholin-4-yl]quinazolin-6-yl]-2-fluorophenyl]-3-fluoropropane-1-sulfonamide Chemical compound NC=1N=CC(=NC1)C1=NC2=C(C=C(C=C2C(=N1)N1[C@@H](COCC1)C)C=1C(=C(C=CC1)NS(=O)(=O)CCCF)F)OC BLMATCSJUYYMEA-MRXNPFEDSA-N 0.000 claims 1
- SOMFDSKXOLISGB-QGZVFWFLSA-N N-[3-[2-(6-amino-4-cyanopyridin-3-yl)-8-methoxy-4-[(3R)-3-methylmorpholin-4-yl]quinazolin-6-yl]-2-fluorophenyl]-3-fluoropropane-1-sulfonamide Chemical compound NC1=CC(=C(C=N1)C1=NC2=C(C=C(C=C2C(=N1)N1[C@@H](COCC1)C)C=1C(=C(C=CC1)NS(=O)(=O)CCCF)F)OC)C#N SOMFDSKXOLISGB-QGZVFWFLSA-N 0.000 claims 1
- LFAONIZWKJTNQP-OAHLLOKOSA-N N-[3-[2-(6-amino-4-fluoropyridin-3-yl)-4-[(3R)-3-methylmorpholin-4-yl]pyrido[3,2-d]pyrimidin-6-yl]-2-fluorophenyl]-3-fluoropropane-1-sulfonamide Chemical compound NC1=CC(=C(C=N1)C=1N=C(C2=C(N=1)C=CC(=N2)C=1C(=C(C=CC=1)NS(=O)(=O)CCCF)F)N1[C@@H](COCC1)C)F LFAONIZWKJTNQP-OAHLLOKOSA-N 0.000 claims 1
- LFAONIZWKJTNQP-HNNXBMFYSA-N N-[3-[2-(6-amino-4-fluoropyridin-3-yl)-4-[(3S)-3-methylmorpholin-4-yl]pyrido[3,2-d]pyrimidin-6-yl]-2-fluorophenyl]-3-fluoropropane-1-sulfonamide Chemical compound C[C@H]1COCCN1c1nc(nc2ccc(nc12)-c1cccc(NS(=O)(=O)CCCF)c1F)-c1cnc(N)cc1F LFAONIZWKJTNQP-HNNXBMFYSA-N 0.000 claims 1
- VSYCXHPMCJAWEN-MRXNPFEDSA-N N-[3-[2-(6-amino-4-fluoropyridin-3-yl)-8-methoxy-4-[(3R)-3-methylmorpholin-4-yl]quinazolin-6-yl]-2-fluorophenyl]-3-fluoropropane-1-sulfonamide Chemical compound NC1=CC(=C(C=N1)C1=NC2=C(C=C(C=C2C(=N1)N1[C@@H](COCC1)C)C=1C(=C(C=CC=1)NS(=O)(=O)CCCF)F)OC)F VSYCXHPMCJAWEN-MRXNPFEDSA-N 0.000 claims 1
- SAEYUAYUMCLKCT-KRWDZBQOSA-N N-[3-[2-(6-amino-4-methylpyridin-3-yl)-4-[(3S)-3-methylmorpholin-4-yl]pyrido[3,2-d]pyrimidin-6-yl]-2-fluorophenyl]-3-fluoropropane-1-sulfonamide Chemical compound NC1=CC(=C(C=N1)C=1N=C(C2=C(N=1)C=CC(=N2)C=1C(=C(C=CC=1)NS(=O)(=O)CCCF)F)N1[C@H](COCC1)C)C SAEYUAYUMCLKCT-KRWDZBQOSA-N 0.000 claims 1
- IGHWXSSWNCXBBT-QGZVFWFLSA-N N-[3-[2-(6-amino-5-fluoropyridin-3-yl)-8-(2-fluoroethoxy)-4-[(3R)-3-methylmorpholin-4-yl]quinazolin-6-yl]-2-fluorophenyl]-3-fluoropropane-1-sulfonamide Chemical compound NC1=C(C=C(C=N1)C1=NC2=C(C=C(C=C2C(=N1)N1[C@@H](COCC1)C)C=1C(=C(C=CC1)NS(=O)(=O)CCCF)F)OCCF)F IGHWXSSWNCXBBT-QGZVFWFLSA-N 0.000 claims 1
- XPNSJZCJXAMCPP-MRXNPFEDSA-N N-[3-[2-(6-amino-5-fluoropyridin-3-yl)-8-methoxy-4-[(3R)-3-methylmorpholin-4-yl]quinazolin-6-yl]-2-fluorophenyl]-3-fluoropropane-1-sulfonamide Chemical compound NC1=C(C=C(C=N1)C1=NC2=C(C=C(C=C2C(=N1)N1[C@@H](COCC1)C)C=1C(=C(C=CC=1)NS(=O)(=O)CCCF)F)OC)F XPNSJZCJXAMCPP-MRXNPFEDSA-N 0.000 claims 1
- HKHWEKMHOSDGTA-HXUWFJFHSA-N N-[3-[2-(6-aminopyridin-3-yl)-4-[(3R)-3-methylmorpholin-4-yl]-8-pyrrolidin-1-ylquinazolin-6-yl]-2-fluorophenyl]-3-fluoropropane-1-sulfonamide Chemical compound C[C@@H]1COCCN1c1nc(nc2c(cc(cc12)-c1cccc(NS(=O)(=O)CCCF)c1F)N1CCCC1)-c1ccc(N)nc1 HKHWEKMHOSDGTA-HXUWFJFHSA-N 0.000 claims 1
- IOPPHACWXKLSDE-INIZCTEOSA-N N-[3-[2-(6-aminopyridin-3-yl)-4-[(3S)-3-methylmorpholin-4-yl]pyrido[3,2-d]pyrimidin-6-yl]-2-fluorophenyl]-3-fluoropropane-1-sulfonamide Chemical compound C[C@H]1COCCN1c1nc(nc2ccc(nc12)-c1cccc(NS(=O)(=O)CCCF)c1F)-c1ccc(N)nc1 IOPPHACWXKLSDE-INIZCTEOSA-N 0.000 claims 1
- KWKYMTIODSCPKX-UHFFFAOYSA-N N-[3-[2-(6-aminopyridin-3-yl)-8-methyl-4-morpholin-4-ylquinazolin-6-yl]-2-fluorophenyl]-3-fluoropropane-1-sulfonamide Chemical compound Cc1cc(cc2c(nc(nc12)-c1ccc(N)nc1)N1CCOCC1)-c1cccc(NS(=O)(=O)CCCF)c1F KWKYMTIODSCPKX-UHFFFAOYSA-N 0.000 claims 1
- HNTNRJOWCSMYHF-GOSISDBHSA-N N-[3-[8-ethoxy-2-[2-(methylamino)pyrimidin-5-yl]-4-[(3R)-3-methylmorpholin-4-yl]quinazolin-6-yl]-2-fluorophenyl]-3-fluoropropane-1-sulfonamide Chemical compound C(C)OC=1C=C(C=C2C(=NC(=NC12)C=1C=NC(=NC1)NC)N1[C@@H](COCC1)C)C=1C(=C(C=CC1)NS(=O)(=O)CCCF)F HNTNRJOWCSMYHF-GOSISDBHSA-N 0.000 claims 1
- DVGGRJLRAMFKKA-UHFFFAOYSA-N N-[4-[6-[2-fluoro-3-(3-fluoropropylsulfonylamino)phenyl]-8-methoxy-4-morpholin-4-ylquinazolin-2-yl]phenyl]acetamide Chemical compound FC1=C(C=CC=C1NS(=O)(=O)CCCF)C=1C=C2C(=NC(=NC2=C(C=1)OC)C1=CC=C(C=C1)NC(C)=O)N1CCOCC1 DVGGRJLRAMFKKA-UHFFFAOYSA-N 0.000 claims 1
- XWRHMVYXGFTVIT-UHFFFAOYSA-N N-[5-[6-[2-fluoro-3-(3-fluoropropylsulfonylamino)phenyl]-8-methoxy-4-morpholin-4-ylquinazolin-2-yl]pyridin-2-yl]acetamide Chemical compound COc1cc(cc2c(nc(nc12)-c1ccc(NC(C)=O)nc1)N1CCOCC1)-c1cccc(NS(=O)(=O)CCCF)c1F XWRHMVYXGFTVIT-UHFFFAOYSA-N 0.000 claims 1
- RXCVUDCDCGBNDA-UHFFFAOYSA-N Nc1ccc(cn1)-c1nc(N2CCOCC2)c2cc(cc(OCCO)c2n1)-c1cccc(NS(=O)(=O)CCCF)c1F Chemical compound Nc1ccc(cn1)-c1nc(N2CCOCC2)c2cc(cc(OCCO)c2n1)-c1cccc(NS(=O)(=O)CCCF)c1F RXCVUDCDCGBNDA-UHFFFAOYSA-N 0.000 claims 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-O Piperidinium(1+) Chemical compound C1CC[NH2+]CC1 NQRYJNQNLNOLGT-UHFFFAOYSA-O 0.000 claims 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-O Pyrrolidinium ion Chemical compound C1CC[NH2+]C1 RWRDLPDLKQPQOW-UHFFFAOYSA-O 0.000 claims 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 claims 1
- 102100024908 Ribosomal protein S6 kinase beta-1 Human genes 0.000 claims 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims 1
- 235000011054 acetic acid Nutrition 0.000 claims 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 1
- 201000005188 adrenal gland cancer Diseases 0.000 claims 1
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- GBZBHGCSKIUCSA-UHFFFAOYSA-N n-[3-[2-(6-aminopyridin-3-yl)-8-methyl-4-morpholin-4-ylquinazolin-6-yl]-2-fluorophenyl]propane-1-sulfonamide Chemical compound CCCS(=O)(=O)NC1=CC=CC(C=2C=C3C(N4CCOCC4)=NC(=NC3=C(C)C=2)C=2C=NC(N)=CC=2)=C1F GBZBHGCSKIUCSA-UHFFFAOYSA-N 0.000 claims 1
- VGSGDGSPVDLAGZ-UHFFFAOYSA-N n-[3-[2-[6-(2-aminoethylamino)pyridin-3-yl]-8-methoxy-4-morpholin-4-ylquinazolin-6-yl]-2-fluorophenyl]propane-1-sulfonamide Chemical compound CCCS(=O)(=O)NC1=CC=CC(C=2C=C3C(N4CCOCC4)=NC(=NC3=C(OC)C=2)C=2C=NC(NCCN)=CC=2)=C1F VGSGDGSPVDLAGZ-UHFFFAOYSA-N 0.000 claims 1
- SAWOLQUFBIQXMM-OAHLLOKOSA-N n-[3-[2-[6-amino-4-(trifluoromethyl)pyridin-3-yl]-4-[(3r)-3-methylmorpholin-4-yl]pyrido[3,2-d]pyrimidin-6-yl]-2-fluorophenyl]-3-fluoropropane-1-sulfonamide Chemical compound C[C@@H]1COCCN1C1=NC(C=2C(=CC(N)=NC=2)C(F)(F)F)=NC2=CC=C(C=3C(=C(NS(=O)(=O)CCCF)C=CC=3)F)N=C12 SAWOLQUFBIQXMM-OAHLLOKOSA-N 0.000 claims 1
- SAWOLQUFBIQXMM-HNNXBMFYSA-N n-[3-[2-[6-amino-4-(trifluoromethyl)pyridin-3-yl]-4-[(3s)-3-methylmorpholin-4-yl]pyrido[3,2-d]pyrimidin-6-yl]-2-fluorophenyl]-3-fluoropropane-1-sulfonamide Chemical compound C[C@H]1COCCN1C1=NC(C=2C(=CC(N)=NC=2)C(F)(F)F)=NC2=CC=C(C=3C(=C(NS(=O)(=O)CCCF)C=CC=3)F)N=C12 SAWOLQUFBIQXMM-HNNXBMFYSA-N 0.000 claims 1
- JMSLSWNGLUWSGI-UHFFFAOYSA-N n-[3-[8-(2-aminoethoxy)-2-(6-aminopyridin-3-yl)-4-morpholin-4-ylquinazolin-6-yl]-2-fluorophenyl]-3-fluoropropane-1-sulfonamide Chemical compound N1=C2C(OCCN)=CC(C=3C(=C(NS(=O)(=O)CCCF)C=CC=3)F)=CC2=C(N2CCOCC2)N=C1C1=CC=C(N)N=C1 JMSLSWNGLUWSGI-UHFFFAOYSA-N 0.000 claims 1
- RRCKEUACSSHIDV-LJQANCHMSA-N n-[3-[8-ethoxy-4-[(3r)-3-methylmorpholin-4-yl]-2-(1h-pyrrolo[2,3-b]pyridin-5-yl)quinazolin-6-yl]-2-fluorophenyl]-3-fluoropropane-1-sulfonamide Chemical compound N1=C(C=2C=C3C=CNC3=NC=2)N=C2C(OCC)=CC(C=3C(=C(NS(=O)(=O)CCCF)C=CC=3)F)=CC2=C1N1CCOC[C@H]1C RRCKEUACSSHIDV-LJQANCHMSA-N 0.000 claims 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 claims 1
- 210000003739 neck Anatomy 0.000 claims 1
- 229910017604 nitric acid Inorganic materials 0.000 claims 1
- 210000001672 ovary Anatomy 0.000 claims 1
- 210000000496 pancreas Anatomy 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 229910052700 potassium Inorganic materials 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- DROIHSMGGKKIJT-UHFFFAOYSA-N propane-1-sulfonamide Chemical compound CCCS(N)(=O)=O DROIHSMGGKKIJT-UHFFFAOYSA-N 0.000 claims 1
- 235000019260 propionic acid Nutrition 0.000 claims 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims 1
- 210000002307 prostate Anatomy 0.000 claims 1
- 150000003222 pyridines Chemical class 0.000 claims 1
- 125000004943 pyrimidin-6-yl group Chemical group N1=CN=CC=C1* 0.000 claims 1
- 150000003230 pyrimidines Chemical class 0.000 claims 1
- 150000003233 pyrroles Chemical class 0.000 claims 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims 1
- 210000000664 rectum Anatomy 0.000 claims 1
- 239000000523 sample Substances 0.000 claims 1
- 210000003491 skin Anatomy 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 210000002784 stomach Anatomy 0.000 claims 1
- 229940124530 sulfonamide Drugs 0.000 claims 1
- 239000011975 tartaric acid Substances 0.000 claims 1
- 235000002906 tartaric acid Nutrition 0.000 claims 1
- 230000002381 testicular Effects 0.000 claims 1
- 229930192474 thiophene Natural products 0.000 claims 1
- 210000001685 thyroid gland Anatomy 0.000 claims 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-O triethanolammonium Chemical compound OCC[NH+](CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-O 0.000 claims 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 claims 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 claims 1
- DRDCQJADRSJFFD-UHFFFAOYSA-N tris-hydroxymethyl-methyl-ammonium Chemical compound OC[N+](C)(CO)CO DRDCQJADRSJFFD-UHFFFAOYSA-N 0.000 claims 1
- 210000003932 urinary bladder Anatomy 0.000 claims 1
- 210000004291 uterus Anatomy 0.000 claims 1
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| SG11201804901WA (en) | 2015-12-22 | 2018-07-30 | SHY Therapeutics LLC | Compounds for the treatment of cancer and inflammatory disease |
| JP2019519593A (ja) * | 2016-07-06 | 2019-07-11 | ザ・リージェンツ・オブ・ザ・ユニバーシティ・オブ・ミシガンＴｈｅ Ｒｅｇｅｎｔｓ Ｏｆ Ｔｈｅ Ｕｎｉｖｅｒｓｉｔｙ Ｏｆ Ｍｉｃｈｉｇａｎ | ＭＥＫ／ＰＩ３Ｋ及びｍＴＯＲ／ＭＥＫ／ＰＩ３Ｋ生物学的経路の多官能性阻害剤、並びに同多官能性阻害剤を用いた治療方法 |
| CN108239075B (zh) * | 2016-12-26 | 2021-07-02 | 中国医学科学院药物研究所 | 喹唑啉类化合物及其制备方法、用途和药物组合物 |
| CN108239074B (zh) * | 2016-12-26 | 2021-07-06 | 中国医学科学院药物研究所 | 喹唑啉类化合物及其制备方法、用途和药物组合物 |
| CA3048546A1 (en) * | 2016-12-26 | 2018-07-05 | Institute Of Materia Medica, Chinese Academy Of Medical Sciences | Quinazoline compound and preparation method, application, and pharmaceutical compostion thereof |
| CN108239076B (zh) * | 2016-12-26 | 2021-07-06 | 中国医学科学院药物研究所 | 喹唑啉类化合物及其制备方法、用途和药物组合物 |
| WO2018212774A1 (en) * | 2017-05-17 | 2018-11-22 | Vanderbilt University | Quinazoline compounds as modulators of ras signaling |
| CA3066939A1 (en) | 2017-06-21 | 2018-12-27 | SHY Therapeutics LLC | Compounds that interact with the ras superfamily for the treatment of cancers, inflammatory diseases, rasopathies, and fibrotic disease |
| US10695296B2 (en) * | 2017-07-14 | 2020-06-30 | Asana Biosciences, Llc | Formulations, methods, kit, and dosage forms for improved stability of an active pharmaceutical ingredient |
| CN108623582A (zh) * | 2017-10-10 | 2018-10-09 | 河南省锐达医药科技有限公司 | 一类新型含取代基吡啶并嘧啶化合物的制备方法 |
| WO2020132071A1 (en) | 2018-12-19 | 2020-06-25 | Shy Therapeutics. Llc | Compounds that interact with the ras superfamily for the treatment of cancers, inflammatory diseases, rasopathies, and f1brotic disease |
| CN111499634B (zh) * | 2019-01-31 | 2023-05-12 | 贝达药业股份有限公司 | 一种喹唑啉化合物及其在医药上的应用 |
| CN112341434B (zh) * | 2019-08-08 | 2021-11-26 | 恩瑞生物医药科技（上海）有限公司 | PI3K/mTOR蛋白降解靶向嵌合体类化合物及其制备方法和医药用途 |
| HUE067805T2 (hu) | 2019-11-01 | 2024-11-28 | Fmc Corp | Hatékony új eljárás 2-amino-5-klór-N,3-dimetilbenzamid elõállítására |
| CN115894606A (zh) | 2019-11-04 | 2023-04-04 | 锐新医药公司 | Ras抑制剂 |
| KR20230067635A (ko) | 2020-09-15 | 2023-05-16 | 레볼루션 메디슨즈, 인크. | 암의 치료에서 ras 억제제로서 인돌 유도체 |
| JP2023549540A (ja) * | 2020-11-18 | 2023-11-27 | デシフェラ・ファーマシューティカルズ，エルエルシー | Ｇｃｎ２およびｐｅｒｋキナーゼ阻害剤およびその使用方法 |
| CN118852330A (zh) | 2021-05-05 | 2024-10-29 | 锐新医药公司 | 用于治疗癌症的ras抑制剂 |
| CN113416181B (zh) * | 2021-08-02 | 2022-05-03 | 四川大学 | 喹唑啉类衍生物及其用途 |
| AR127308A1 (es) | 2021-10-08 | 2024-01-10 | Revolution Medicines Inc | Inhibidores ras |
| WO2023131122A1 (zh) * | 2022-01-04 | 2023-07-13 | 劲方医药科技(上海)有限公司 | 稠环取代的六元杂环化合物及其制法和用途 |
| CN115894211A (zh) * | 2022-11-10 | 2023-04-04 | 山东龙立恒医药有限公司 | 一种3-羟基-4-甲基苯甲酸的制备方法 |
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| GB0428475D0 (en) | 2004-12-30 | 2005-02-02 | 4 Aza Bioscience Nv | Pyrido(3,2-D)pyrimidine derivatives and pharmaceutical compositions useful as medicines for the treatment of autoimmune disorders |
| GB0503506D0 (en) | 2005-02-21 | 2005-03-30 | 4 Aza Bioscience Nv | Substituted pyrido(2,3-d) pyrimidine derivatives and pharmaceutical compositions useful as medicines for the treatment of autoimmune disorders |
| TW200801012A (en) * | 2006-04-26 | 2008-01-01 | Piramed Ltd | Phosphoinositide 3-kinase inhibitor compounds and methods of use |
| UY31137A1 (es) * | 2007-06-14 | 2009-01-05 | Smithkline Beecham Corp | Derivados de quinazolina como inhibidores de la pi3 quinasa |
| WO2009039140A1 (en) * | 2007-09-17 | 2009-03-26 | Smithkline Beecham Corporation | Pyridopyrimidine derivatives as pi3 kinase inhibitors |
| WO2009108637A1 (en) * | 2008-02-25 | 2009-09-03 | Prometheus Laboratories, Inc. | Drug selection for breast cancer therapy using antibody-based arrays |
| WO2010037765A2 (en) * | 2008-10-03 | 2010-04-08 | Merck Serono S.A. | 4-morpholino-pyrido[3,2-d]pyrimidines |
| EP2531498B1 (en) * | 2010-02-05 | 2016-07-13 | Novartis AG | Compounds and compositions as protein kinase inhibitors |
| EP2539337A1 (en) * | 2010-02-22 | 2013-01-02 | F. Hoffmann-La Roche AG | Pyrido[3,2-d]pyrimidine pi3k delta inhibitor compounds and methods of use |
| WO2012118492A1 (en) * | 2011-03-01 | 2012-09-07 | Array Biopharma Inc. | Heterocyclic sulfonamides as raf inhibitors |
-
2014
- 2014-04-11 KR KR1020157032374A patent/KR20150143672A/ko not_active Abandoned
- 2014-04-11 BR BR112015025901A patent/BR112015025901A8/pt not_active Application Discontinuation
- 2014-04-11 CN CN201480033247.1A patent/CN105283454B/zh not_active Expired - Fee Related
- 2014-04-11 RU RU2015148359A patent/RU2015148359A/ru not_active Application Discontinuation
- 2014-04-11 EP EP14725852.9A patent/EP2984088B1/en not_active Not-in-force
- 2014-04-11 WO PCT/US2014/033727 patent/WO2014169167A1/en not_active Ceased
- 2014-04-11 AU AU2014250836A patent/AU2014250836C1/en not_active Ceased
- 2014-04-11 MX MX2015014387A patent/MX2015014387A/es unknown
- 2014-04-11 CA CA2909310A patent/CA2909310A1/en not_active Abandoned
- 2014-04-11 US US14/783,903 patent/US9499495B2/en not_active Expired - Fee Related
- 2014-04-11 JP JP2016507671A patent/JP6496301B2/ja not_active Expired - Fee Related
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2015
- 2015-10-11 IL IL242020A patent/IL242020B/en not_active IP Right Cessation
- 2015-10-16 ZA ZA2015/07750A patent/ZA201507750B/en unknown
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2016
- 2016-10-11 US US15/290,788 patent/US9757382B2/en not_active Expired - Fee Related
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2017
- 2017-04-28 US US15/581,330 patent/US10226468B2/en not_active Expired - Fee Related
-
2018
- 2018-10-11 IL IL262314A patent/IL262314A/en unknown
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2019
- 2019-01-24 US US16/256,365 patent/US10912779B2/en not_active Expired - Fee Related
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2020
- 2020-11-05 US US17/090,513 patent/US20210113578A1/en not_active Abandoned
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