JP2020504139A5 - - Google Patents
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- Publication number
- JP2020504139A5 JP2020504139A5 JP2019537063A JP2019537063A JP2020504139A5 JP 2020504139 A5 JP2020504139 A5 JP 2020504139A5 JP 2019537063 A JP2019537063 A JP 2019537063A JP 2019537063 A JP2019537063 A JP 2019537063A JP 2020504139 A5 JP2020504139 A5 JP 2020504139A5
- Authority
- JP
- Japan
- Prior art keywords
- group
- quinoxaline
- triazolo
- dimethyl
- piperidine
- 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 ethylenedioxy group Chemical group 0.000 claims description 203
- 229910052757 nitrogen Inorganic materials 0.000 claims description 159
- BCIIMDOZSUCSEN-UHFFFAOYSA-N piperidin-4-amine Chemical compound NC1CCNCC1 BCIIMDOZSUCSEN-UHFFFAOYSA-N 0.000 claims description 150
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 96
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 49
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 42
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 28
- 150000001875 compounds Chemical class 0.000 claims description 15
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 8
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 8
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 claims description 8
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 6
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 5
- 229940002612 prodrug Drugs 0.000 claims description 5
- 239000000651 prodrug Substances 0.000 claims description 5
- WJJMNDUMQPNECX-UHFFFAOYSA-N dipicolinic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=N1 WJJMNDUMQPNECX-UHFFFAOYSA-N 0.000 claims description 4
- JSQCGWYNOZMHJE-UHFFFAOYSA-N 1-[2-chloro-4-(1-piperidin-1-yl-[1,2,4]triazolo[4,3-a]quinoxalin-8-yl)phenyl]-N,N-dimethylpiperidin-4-amine Chemical compound CN(C1CCN(CC1)C1=C(C=C(C=C1)C1=CC=C2N=CC=3N(C2=C1)C(=NN=3)N1CCCCC1)Cl)C JSQCGWYNOZMHJE-UHFFFAOYSA-N 0.000 claims description 3
- AWBDUOMWRGDOKR-KDURUIRLSA-N 1-[2-chloro-6-(trifluoromethyl)-4-[1-[(3R,5S)-3,4,5-trimethylpiperazin-1-yl]-[1,2,4]triazolo[4,3-a]quinoxalin-8-yl]phenyl]-N,N-dimethylpiperidin-4-amine Chemical compound CN(C1CCN(CC1)C1=C(C=C(C=C1C(F)(F)F)C1=CC=C2N=CC=3N(C2=C1)C(=NN=3)N1C[C@@H](N([C@@H](C1)C)C)C)Cl)C AWBDUOMWRGDOKR-KDURUIRLSA-N 0.000 claims description 3
- HBRKAOFGYWODRB-KDURUIRLSA-N 1-[2-fluoro-6-(trifluoromethyl)-4-[1-[(3R,5S)-3,4,5-trimethylpiperazin-1-yl]-[1,2,4]triazolo[4,3-a]quinoxalin-8-yl]phenyl]-N,N-dimethylpiperidin-4-amine Chemical compound CN(C1CCN(CC1)C1=C(C=C(C=C1C(F)(F)F)C1=CC=C2N=CC=3N(C2=C1)C(=NN=3)N1C[C@@H](N([C@@H](C1)C)C)C)F)C HBRKAOFGYWODRB-KDURUIRLSA-N 0.000 claims description 3
- NQNYGHMIJGDQDL-HDICACEKSA-N 3-[2-chloro-6-(trifluoromethyl)-4-[1-[(3R,5S)-3,4,5-trimethylpiperazin-1-yl]-[1,2,4]triazolo[4,3-a]quinoxalin-8-yl]phenoxy]-N,N-dimethylpropan-1-amine Chemical compound ClC1=C(OCCCN(C)C)C(=CC(=C1)C1=CC=C2N=CC=3N(C2=C1)C(=NN=3)N1C[C@@H](N([C@@H](C1)C)C)C)C(F)(F)F NQNYGHMIJGDQDL-HDICACEKSA-N 0.000 claims description 3
- DIXUBLFTHVMWLR-HDICACEKSA-N 3-[2-fluoro-6-(trifluoromethyl)-4-[1-[(3R,5S)-3,4,5-trimethylpiperazin-1-yl]-[1,2,4]triazolo[4,3-a]quinoxalin-8-yl]phenoxy]-N,N-dimethylpropan-1-amine Chemical compound FC1=C(OCCCN(C)C)C(=CC(=C1)C1=CC=C2N=CC=3N(C2=C1)C(=NN=3)N1C[C@@H](N([C@@H](C1)C)C)C)C(F)(F)F DIXUBLFTHVMWLR-HDICACEKSA-N 0.000 claims description 3
- RABLNLIHIGOBNY-KDURUIRLSA-N 3-[4-[1-[(3R,5S)-3,5-dimethylpiperidin-1-yl]-[1,2,4]triazolo[4,3-a]quinoxalin-8-yl]-2-(trifluoromethyl)phenoxy]-N,N-dimethylpropan-1-amine Chemical compound CN(CCCOC1=C(C=C(C=C1)C1=CC=C2N=CC=3N(C2=C1)C(=NN=3)N1C[C@@H](C[C@@H](C1)C)C)C(F)(F)F)C RABLNLIHIGOBNY-KDURUIRLSA-N 0.000 claims description 3
- JHUPAEUBHORZLR-BGYRXZFFSA-N N,N-dimethyl-1-[2-(trifluoromethyl)-4-[1-[(3S,5R)-3,4,5-trimethylpiperazin-1-yl]-[1,2,4]triazolo[4,3-a]quinoxalin-8-yl]phenyl]piperidin-4-amine Chemical compound CN(C1CCN(CC1)C1=C(C=C(C=C1)C1=CC=C2N=CC=3N(C2=C1)C(=NN=3)N1C[C@@H](N([C@@H](C1)C)C)C)C(F)(F)F)C JHUPAEUBHORZLR-BGYRXZFFSA-N 0.000 claims description 3
- IZOHQVJQWJYVRY-KDURUIRLSA-N N,N-dimethyl-3-[2-(trifluoromethyl)-4-[1-[(3R,5S)-3,4,5-trimethylpiperazin-1-yl]-[1,2,4]triazolo[4,3-a]quinoxalin-8-yl]phenoxy]propan-1-amine Chemical compound CN(CCCOC1=C(C=C(C=C1)C1=CC=C2N=CC=3N(C2=C1)C(=NN=3)N1C[C@@H](N([C@@H](C1)C)C)C)C(F)(F)F)C IZOHQVJQWJYVRY-KDURUIRLSA-N 0.000 claims description 3
- REBUNDZNCXGPSB-UHFFFAOYSA-N N,N-dimethyl-3-[4-(1-piperidin-1-yl-[1,2,4]triazolo[4,3-a]quinoxalin-8-yl)phenoxy]propan-1-amine Chemical compound CN(CCCOC1=CC=C(C=C1)C1=CC=C2N=CC=3N(C2=C1)C(=NN=3)N1CCCCC1)C REBUNDZNCXGPSB-UHFFFAOYSA-N 0.000 claims description 3
- FQXBWQABGBJRSC-UHFFFAOYSA-N N,N-dimethyl-3-[4-[1-(4-methylpiperazin-1-yl)-[1,2,4]triazolo[4,3-a]quinoxalin-8-yl]phenoxy]propan-1-amine Chemical compound CN(C)CCCOC1=CC=C(C=C1)C1=CC=C2N=CC=3N(C2=C1)C(=NN=3)N1CCN(CC1)C FQXBWQABGBJRSC-UHFFFAOYSA-N 0.000 claims description 3
- QHHINYLYLKQVHH-BGYRXZFFSA-N N-ethyl-1-[2-(trifluoromethyl)-4-[1-[(3R,5S)-3,4,5-trimethylpiperazin-1-yl]-[1,2,4]triazolo[4,3-a]quinoxalin-8-yl]phenyl]piperidin-4-amine Chemical compound C(C)NC1CCN(CC1)C1=C(C=C(C=C1)C1=CC=C2N=CC=3N(C2=C1)C(=NN=3)N1C[C@@H](N([C@@H](C1)C)C)C)C(F)(F)F QHHINYLYLKQVHH-BGYRXZFFSA-N 0.000 claims description 3
- DGWGSNCNMUVWDC-KDURUIRLSA-N N-methyl-1-[2-(trifluoromethyl)-4-[1-[(3S,5R)-3,4,5-trimethylpiperazin-1-yl]-[1,2,4]triazolo[4,3-a]quinoxalin-8-yl]phenyl]piperidin-4-amine Chemical compound CNC1CCN(CC1)C1=C(C=C(C=C1)C1=CC=C2N=CC=3N(C2=C1)C(=NN=3)N1C[C@@H](N([C@@H](C1)C)C)C)C(F)(F)F DGWGSNCNMUVWDC-KDURUIRLSA-N 0.000 claims description 3
- PYSRDFNFIZKLFZ-UHFFFAOYSA-N 1-[2-fluoro-4-(1-piperidin-1-yl-[1,2,4]triazolo[4,3-a]quinoxalin-8-yl)phenyl]-N,N-dimethylpiperidin-4-amine Chemical compound CN(C1CCN(CC1)C1=C(C=C(C=C1)C1=CC=C2N=CC=3N(C2=C1)C(=NN=3)N1CCCCC1)F)C PYSRDFNFIZKLFZ-UHFFFAOYSA-N 0.000 claims description 2
- PTYSLACARNYDSH-BGYRXZFFSA-N 1-[4-[1-[(3S,5R)-3,5-dimethylpiperidin-1-yl]-[1,2,4]triazolo[4,3-a]quinoxalin-8-yl]-2-(trifluoromethyl)phenyl]-N,N-dimethylpiperidin-4-amine Chemical compound CN(C1CCN(CC1)C1=C(C=C(C=C1)C1=CC=C2N=CC=3N(C2=C1)C(=NN=3)N1C[C@@H](C[C@@H](C1)C)C)C(F)(F)F)C PTYSLACARNYDSH-BGYRXZFFSA-N 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 32
- 229910052739 hydrogen Inorganic materials 0.000 claims 20
- 239000001257 hydrogen Substances 0.000 claims 20
- 150000002431 hydrogen Chemical class 0.000 claims 11
- 125000003277 amino group Chemical group 0.000 claims 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 9
- 229910052736 halogen Inorganic materials 0.000 claims 9
- 150000002367 halogens Chemical class 0.000 claims 9
- 125000000623 heterocyclic group Chemical group 0.000 claims 9
- DEQANNDTNATYII-OULOTJBUSA-N (4r,7s,10s,13r,16s,19r)-10-(4-aminobutyl)-19-[[(2r)-2-amino-3-phenylpropanoyl]amino]-16-benzyl-n-[(2r,3r)-1,3-dihydroxybutan-2-yl]-7-[(1r)-1-hydroxyethyl]-13-(1h-indol-3-ylmethyl)-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentazacycloicosane-4-carboxa Chemical compound C([C@@H](N)C(=O)N[C@H]1CSSC[C@H](NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCCCN)NC(=O)[C@@H](CC=2C3=CC=CC=C3NC=2)NC(=O)[C@H](CC=2C=CC=CC=2)NC1=O)C(=O)N[C@H](CO)[C@H](O)C)C1=CC=CC=C1 DEQANNDTNATYII-OULOTJBUSA-N 0.000 claims 8
- 108010016076 Octreotide Proteins 0.000 claims 8
- 229960002700 octreotide Drugs 0.000 claims 8
- ZBNZXTGUTAYRHI-UHFFFAOYSA-N Dasatinib Chemical compound C=1C(N2CCN(CCO)CC2)=NC(C)=NC=1NC(S1)=NC=C1C(=O)NC1=C(C)C=CC=C1Cl ZBNZXTGUTAYRHI-UHFFFAOYSA-N 0.000 claims 7
- 239000002067 L01XE06 - Dasatinib Substances 0.000 claims 7
- GXJABQQUPOEUTA-RDJZCZTQSA-N bortezomib Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)B(O)O)NC(=O)C=1N=CC=NC=1)C1=CC=CC=C1 GXJABQQUPOEUTA-RDJZCZTQSA-N 0.000 claims 7
- 229960001467 bortezomib Drugs 0.000 claims 7
- 229960002448 dasatinib Drugs 0.000 claims 7
- 239000005536 L01XE08 - Nilotinib Substances 0.000 claims 6
- NWIBSHFKIJFRCO-WUDYKRTCSA-N Mytomycin Chemical compound C1N2C(C(C(C)=C(N)C3=O)=O)=C3[C@@H](COC(N)=O)[C@@]2(OC)[C@@H]2[C@H]1N2 NWIBSHFKIJFRCO-WUDYKRTCSA-N 0.000 claims 6
- 206010028980 Neoplasm Diseases 0.000 claims 6
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 6
- 239000002246 antineoplastic agent Substances 0.000 claims 6
- MXWHMTNPTTVWDM-NXOFHUPFSA-N mitoguazone Chemical compound NC(N)=N\N=C(/C)\C=N\N=C(N)N MXWHMTNPTTVWDM-NXOFHUPFSA-N 0.000 claims 6
- 229960003539 mitoguazone Drugs 0.000 claims 6
- HHZIURLSWUIHRB-UHFFFAOYSA-N nilotinib Chemical compound C1=NC(C)=CN1C1=CC(NC(=O)C=2C=C(NC=3N=C(C=CN=3)C=3C=NC=CC=3)C(C)=CC=2)=CC(C(F)(F)F)=C1 HHZIURLSWUIHRB-UHFFFAOYSA-N 0.000 claims 6
- 229960001346 nilotinib Drugs 0.000 claims 6
- 125000004193 piperazinyl group Chemical group 0.000 claims 6
- 125000003386 piperidinyl group Chemical group 0.000 claims 6
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims 6
- 229960004528 vincristine Drugs 0.000 claims 6
- OGWKCGZFUXNPDA-XQKSVPLYSA-N vincristine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](OC(C)=O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-XQKSVPLYSA-N 0.000 claims 6
- OGWKCGZFUXNPDA-UHFFFAOYSA-N vincristine Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(OC(C)=O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-UHFFFAOYSA-N 0.000 claims 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 5
- CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 claims 5
- 125000004423 acyloxy group Chemical group 0.000 claims 5
- 125000003342 alkenyl group Chemical group 0.000 claims 5
- 125000004414 alkyl thio group Chemical group 0.000 claims 5
- 125000000304 alkynyl group Chemical group 0.000 claims 5
- 125000003118 aryl group Chemical group 0.000 claims 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims 5
- 229960004397 cyclophosphamide Drugs 0.000 claims 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 5
- 125000003396 thiol group Chemical group [H]S* 0.000 claims 5
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 4
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 4
- UHDGCWIWMRVCDJ-CCXZUQQUSA-N Cytarabine Chemical compound O=C1N=C(N)C=CN1[C@H]1[C@@H](O)[C@H](O)[C@@H](CO)O1 UHDGCWIWMRVCDJ-CCXZUQQUSA-N 0.000 claims 4
- AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 claims 4
- 239000005411 L01XE02 - Gefitinib Substances 0.000 claims 4
- IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical group [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 claims 4
- 229960000684 cytarabine Drugs 0.000 claims 4
- 229960002584 gefitinib Drugs 0.000 claims 4
- XGALLCVXEZPNRQ-UHFFFAOYSA-N gefitinib Chemical compound C=12C=C(OCCCN3CCOCC3)C(OC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 XGALLCVXEZPNRQ-UHFFFAOYSA-N 0.000 claims 4
- 125000001072 heteroaryl group Chemical group 0.000 claims 4
- 125000005415 substituted alkoxy group Chemical group 0.000 claims 4
- 108010006654 Bleomycin Proteins 0.000 claims 3
- 239000002136 L01XE07 - Lapatinib Substances 0.000 claims 3
- 229930012538 Paclitaxel Natural products 0.000 claims 3
- 206010060862 Prostate cancer Diseases 0.000 claims 3
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 3
- BPEGJWRSRHCHSN-UHFFFAOYSA-N Temozolomide Chemical compound O=C1N(C)N=NC2=C(C(N)=O)N=CN21 BPEGJWRSRHCHSN-UHFFFAOYSA-N 0.000 claims 3
- QNSRYVDGWDXBHV-UHFFFAOYSA-N [1,2,4]triazolo[4,3-a]quinoxaline Chemical group C1=CC=C2N3C=NN=C3C=NC2=C1 QNSRYVDGWDXBHV-UHFFFAOYSA-N 0.000 claims 3
- 125000003368 amide group Chemical group 0.000 claims 3
- YTKUWDBFDASYHO-UHFFFAOYSA-N bendamustine Chemical compound ClCCN(CCCl)C1=CC=C2N(C)C(CCCC(O)=O)=NC2=C1 YTKUWDBFDASYHO-UHFFFAOYSA-N 0.000 claims 3
- 229960002707 bendamustine Drugs 0.000 claims 3
- 150000001555 benzenes Chemical group 0.000 claims 3
- 229960001561 bleomycin Drugs 0.000 claims 3
- OYVAGSVQBOHSSS-UAPAGMARSA-O bleomycin A2 Chemical compound N([C@H](C(=O)N[C@H](C)[C@@H](O)[C@H](C)C(=O)N[C@@H]([C@H](O)C)C(=O)NCCC=1SC=C(N=1)C=1SC=C(N=1)C(=O)NCCC[S+](C)C)[C@@H](O[C@H]1[C@H]([C@@H](O)[C@H](O)[C@H](CO)O1)O[C@@H]1[C@H]([C@@H](OC(N)=O)[C@H](O)[C@@H](CO)O1)O)C=1N=CNC=1)C(=O)C1=NC([C@H](CC(N)=O)NC[C@H](N)C(N)=O)=NC(N)=C1C OYVAGSVQBOHSSS-UAPAGMARSA-O 0.000 claims 3
- 201000011510 cancer Diseases 0.000 claims 3
- DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 claims 3
- 229960004316 cisplatin Drugs 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- HOMGKSMUEGBAAB-UHFFFAOYSA-N ifosfamide Chemical compound ClCCNP1(=O)OCCCN1CCCl HOMGKSMUEGBAAB-UHFFFAOYSA-N 0.000 claims 3
- 229960001101 ifosfamide Drugs 0.000 claims 3
- 229960004891 lapatinib Drugs 0.000 claims 3
- BCFGMOOMADDAQU-UHFFFAOYSA-N lapatinib Chemical compound O1C(CNCCS(=O)(=O)C)=CC=C1C1=CC=C(N=CN=C2NC=3C=C(Cl)C(OCC=4C=C(F)C=CC=4)=CC=3)C2=C1 BCFGMOOMADDAQU-UHFFFAOYSA-N 0.000 claims 3
- 230000003211 malignant effect Effects 0.000 claims 3
- 229960004857 mitomycin Drugs 0.000 claims 3
- 229960001592 paclitaxel Drugs 0.000 claims 3
- 150000003216 pyrazines Chemical group 0.000 claims 3
- 150000003230 pyrimidines Chemical group 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 claims 3
- 229960004964 temozolomide Drugs 0.000 claims 3
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- UEJJHQNACJXSKW-UHFFFAOYSA-N 2-(2,6-dioxopiperidin-3-yl)-1H-isoindole-1,3(2H)-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1C1CCC(=O)NC1=O UEJJHQNACJXSKW-UHFFFAOYSA-N 0.000 claims 2
- AOJJSUZBOXZQNB-VTZDEGQISA-N 4'-epidoxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-VTZDEGQISA-N 0.000 claims 2
- WYWHKKSPHMUBEB-UHFFFAOYSA-N 6-Mercaptoguanine Natural products N1C(N)=NC(=S)C2=C1N=CN2 WYWHKKSPHMUBEB-UHFFFAOYSA-N 0.000 claims 2
- MLDQJTXFUGDVEO-UHFFFAOYSA-N BAY-43-9006 Chemical compound C1=NC(C(=O)NC)=CC(OC=2C=CC(NC(=O)NC=3C=C(C(Cl)=CC=3)C(F)(F)F)=CC=2)=C1 MLDQJTXFUGDVEO-UHFFFAOYSA-N 0.000 claims 2
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 claims 2
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| US10981918B2 (en) | 2018-07-20 | 2021-04-20 | Grünenthal GmbH | Further substituted triazolo quinoxaline derivatives |
| WO2021004482A1 (zh) * | 2019-07-10 | 2021-01-14 | 上海瑛派药业有限公司 | 取代的吡唑并喹唑啉酮化合物及其应用 |
| CN112457306A (zh) * | 2019-09-06 | 2021-03-09 | 上海瑛派药业有限公司 | 3,5-二取代吡唑化合物作为激酶抑制剂及其应用 |
| EP4028400A4 (en) * | 2019-09-12 | 2023-09-06 | Impact Therapeutics (Shanghai), Inc | SUBSTITUTED IMIDAZOQUINOXALINE COMPOUNDS AND THEIR USES |
| KR102629489B1 (ko) | 2020-04-29 | 2024-01-29 | 썬전 샥 컴퍼니 리미티드 | 음향장치 및 그 자기회로조립체 |
| KR102458689B1 (ko) * | 2020-07-08 | 2022-10-25 | 원광대학교산학협력단 | 피페리딘 화합물 및 이의 제조 방법 |
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| EP4423089A4 (en) * | 2023-01-18 | 2025-01-08 | Antengene Discovery Limited | PRMT5 INHIBITOR COMPOUNDS AND THEIR USES |
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| US3989816A (en) | 1975-06-19 | 1976-11-02 | Nelson Research & Development Company | Vehicle composition containing 1-substituted azacycloheptan-2-ones |
| US4444762A (en) | 1980-04-04 | 1984-04-24 | Nelson Research & Development Company | Vehicle composition containing 1-substituted azacyclopentan-2-ones |
| EP2303890A4 (en) * | 2008-06-19 | 2012-04-11 | Progenics Pharm Inc | INHIBITORS OF PHOSPHATIDYLINOSITE-3-KINASE |
| DE102010025786A1 (de) * | 2010-07-01 | 2012-01-05 | Merck Patent Gmbh | Pyrazolochinoline |
| CN102399218A (zh) * | 2010-09-16 | 2012-04-04 | 和记黄埔医药（上海）有限公司 | 一类并合三杂环及其作为pi3k抑制剂的用途 |
| WO2012034526A1 (en) | 2010-09-16 | 2012-03-22 | Hutchison Medipharma Limited | Fused heteroaryls and their uses |
| CN103124731B (zh) * | 2010-09-16 | 2016-01-20 | 和记黄埔医药（上海）有限公司 | 稠合的杂芳基化合物及其应用 |
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