ME02601B - Novi derivati indolizina, postupak njihove pripreme i farmaceutski preparati koji ih sadrže za liječenje karcinoma - Google Patents
Novi derivati indolizina, postupak njihove pripreme i farmaceutski preparati koji ih sadrže za liječenje karcinomaInfo
- Publication number
- ME02601B ME02601B MEP-2017-28A MEP201728A ME02601B ME 02601 B ME02601 B ME 02601B ME P201728 A MEP201728 A ME P201728A ME 02601 B ME02601 B ME 02601B
- Authority
- ME
- Montenegro
- Prior art keywords
- dihydro
- formula
- compound
- hydroxyphenyl
- group
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title 1
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 41
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 18
- -1 atom halogens Chemical group 0.000 claims 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 13
- 229910052757 nitrogen Inorganic materials 0.000 claims 10
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 9
- 239000002253 acid Substances 0.000 claims 8
- 125000003118 aryl group Chemical group 0.000 claims 8
- 150000003839 salts Chemical class 0.000 claims 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 7
- 239000003513 alkali Substances 0.000 claims 6
- 125000004432 carbon atom Chemical group C* 0.000 claims 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 6
- 229910052736 halogen Inorganic materials 0.000 claims 5
- 239000000825 pharmaceutical preparation Substances 0.000 claims 5
- 125000006685 (C1-C6) polyhaloalkyl group Chemical group 0.000 claims 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims 4
- 125000001072 heteroaryl group Chemical group 0.000 claims 4
- 125000005842 heteroatom Chemical group 0.000 claims 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 4
- 229910052760 oxygen Inorganic materials 0.000 claims 4
- 239000001301 oxygen Substances 0.000 claims 4
- 229910052717 sulfur Inorganic materials 0.000 claims 4
- 239000011593 sulfur Chemical group 0.000 claims 4
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 3
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 3
- 206010028980 Neoplasm Diseases 0.000 claims 3
- 201000011510 cancer Diseases 0.000 claims 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 2
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 2
- LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 claims 2
- MVXVYAKCVDQRLW-UHFFFAOYSA-N 1h-pyrrolo[2,3-b]pyridine Chemical compound C1=CN=C2NC=CC2=C1 MVXVYAKCVDQRLW-UHFFFAOYSA-N 0.000 claims 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 2
- 206010033128 Ovarian cancer Diseases 0.000 claims 2
- 206010061535 Ovarian neoplasm Diseases 0.000 claims 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 2
- 206010035226 Plasma cell myeloma Diseases 0.000 claims 2
- 208000006664 Precursor Cell Lymphoblastic Leukemia-Lymphoma Diseases 0.000 claims 2
- 206010060862 Prostate cancer Diseases 0.000 claims 2
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- 206010041067 Small cell lung cancer Diseases 0.000 claims 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims 2
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 150000001412 amines Chemical class 0.000 claims 2
- 239000002585 base Substances 0.000 claims 2
- 230000015572 biosynthetic process Effects 0.000 claims 2
- 210000004556 brain Anatomy 0.000 claims 2
- 210000000481 breast Anatomy 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 208000032852 chronic lymphocytic leukemia Diseases 0.000 claims 2
- 208000029742 colonic neoplasm Diseases 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 2
- 210000003238 esophagus Anatomy 0.000 claims 2
- 201000003444 follicular lymphoma Diseases 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 claims 2
- 210000004185 liver Anatomy 0.000 claims 2
- 208000003747 lymphoid leukemia Diseases 0.000 claims 2
- 230000003211 malignant effect Effects 0.000 claims 2
- 201000001441 melanoma Diseases 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 201000000050 myeloid neoplasm Diseases 0.000 claims 2
- 208000002154 non-small cell lung carcinoma Diseases 0.000 claims 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims 2
- 238000002360 preparation method Methods 0.000 claims 2
- 238000000926 separation method Methods 0.000 claims 2
- 208000000587 small cell lung carcinoma Diseases 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 238000003786 synthesis reaction Methods 0.000 claims 2
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims 2
- 210000004291 uterus Anatomy 0.000 claims 2
- 125000006091 1,3-dioxolane group Chemical group 0.000 claims 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical group C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 1
- LMTDPKYREUZYAO-UHFFFAOYSA-N 1,4-dioxepane Chemical group C1COCCOC1 LMTDPKYREUZYAO-UHFFFAOYSA-N 0.000 claims 1
- ZNGWEEUXTBNKFR-UHFFFAOYSA-N 1,4-oxazepane Chemical compound C1CNCCOC1 ZNGWEEUXTBNKFR-UHFFFAOYSA-N 0.000 claims 1
- NDOVLWQBFFJETK-UHFFFAOYSA-N 1,4-thiazinane 1,1-dioxide Chemical compound O=S1(=O)CCNCC1 NDOVLWQBFFJETK-UHFFFAOYSA-N 0.000 claims 1
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 claims 1
- CYXQJHOJIQTXLE-UHFFFAOYSA-N 2,3-dihydro-1h-pyrrolizine Chemical group C1=CN2CCCC2=C1 CYXQJHOJIQTXLE-UHFFFAOYSA-N 0.000 claims 1
- KVTUSMPNLUCCQO-UHFFFAOYSA-N 3,3-difluoropyrrolidine Chemical compound FC1(F)CCNC1 KVTUSMPNLUCCQO-UHFFFAOYSA-N 0.000 claims 1
- YRLORWPBJZEGBX-UHFFFAOYSA-N 3,4-dihydro-2h-1,4-benzoxazine Chemical compound C1=CC=C2NCCOC2=C1 YRLORWPBJZEGBX-UHFFFAOYSA-N 0.000 claims 1
- PJUAZOILWQCDCF-BHVANESWSA-N 3-[5-chloro-2-[(3S)-3-(morpholin-4-ylmethyl)-3,4-dihydro-1H-isoquinoline-2-carbonyl]phenyl]-N-(4-hydroxyphenyl)-N-(1-methylindol-5-yl)-5,6,7,8-tetrahydroindolizine-1-carboxamide Chemical compound Cn1ccc2cc(ccc12)N(C(=O)c1cc(-c2cc(Cl)ccc2C(=O)N2Cc3ccccc3C[C@H]2CN2CCOCC2)n2CCCCc12)c1ccc(O)cc1 PJUAZOILWQCDCF-BHVANESWSA-N 0.000 claims 1
- WQYAZBFZFIUIPL-UHFFFAOYSA-N 3-fluoroazetidine Chemical compound FC1CNC1 WQYAZBFZFIUIPL-UHFFFAOYSA-N 0.000 claims 1
- AVPAYFOQPGPSCC-UHFFFAOYSA-N 3-methoxyazetidine Chemical compound COC1CNC1 AVPAYFOQPGPSCC-UHFFFAOYSA-N 0.000 claims 1
- BWRWNUQAQPAYCK-UHFFFAOYSA-N 3-methoxypyrrolidine Chemical compound COC1CCNC1 BWRWNUQAQPAYCK-UHFFFAOYSA-N 0.000 claims 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims 1
- MJYFVDNMTKLGTH-UHFFFAOYSA-N 4-bromo-6-(3,4-dichlorophenyl)sulfanyl-1-[[4-(dimethylcarbamoyl)phenyl]methyl]indole-2-carboxylic acid Chemical compound BrC1=C2C=C(N(C2=CC(=C1)SC1=CC(=C(C=C1)Cl)Cl)CC1=CC=C(C=C1)C(N(C)C)=O)C(=O)O MJYFVDNMTKLGTH-UHFFFAOYSA-N 0.000 claims 1
- OURXRFYZEOUCRM-UHFFFAOYSA-N 4-hydroxymorpholine Chemical compound ON1CCOCC1 OURXRFYZEOUCRM-UHFFFAOYSA-N 0.000 claims 1
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- QYASHELNMUPRKF-UHFFFAOYSA-N 5,6,7,8-tetrahydroindolizine Chemical group C1CCCN2C=CC=C21 QYASHELNMUPRKF-UHFFFAOYSA-N 0.000 claims 1
- 208000023275 Autoimmune disease Diseases 0.000 claims 1
- PZFRTTBLYIXHRY-UHFFFAOYSA-N C1OCCN2C=CC=C21 Chemical group C1OCCN2C=CC=C21 PZFRTTBLYIXHRY-UHFFFAOYSA-N 0.000 claims 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 1
- VLYLIWNHYCPHAP-XIFFEERXSA-N Cc1ccc(cc1F)N(C(=O)c1cc(-c2cc(Cl)ccc2C(=O)N2Cc3ccccc3C[C@H]2CN2CCOCC2)n2CCOCc12)c1ccc(O)cc1 Chemical compound Cc1ccc(cc1F)N(C(=O)c1cc(-c2cc(Cl)ccc2C(=O)N2Cc3ccccc3C[C@H]2CN2CCOCC2)n2CCOCc12)c1ccc(O)cc1 VLYLIWNHYCPHAP-XIFFEERXSA-N 0.000 claims 1
- DQMIWSSTWOZOAE-HKBQPEDESA-N Cn1cc(cn1)N(C(=O)c1cc(-c2cc(Cl)ccc2C(=O)N2Cc3ccccc3C[C@H]2CN2CCOCC2)n2CCCCc12)c1ccc(O)cc1 Chemical compound Cn1cc(cn1)N(C(=O)c1cc(-c2cc(Cl)ccc2C(=O)N2Cc3ccccc3C[C@H]2CN2CCOCC2)n2CCCCc12)c1ccc(O)cc1 DQMIWSSTWOZOAE-HKBQPEDESA-N 0.000 claims 1
- IVXQXWNWNDYCPO-BHVANESWSA-N Cn1ccc2cc(ccc12)N(C(=O)c1cc(-c2cc(Cl)ccc2C(=O)N2Cc3ccccc3C[C@H]2CN2CCOCC2)n2ccccc12)c1ccc(O)cc1 Chemical compound Cn1ccc2cc(ccc12)N(C(=O)c1cc(-c2cc(Cl)ccc2C(=O)N2Cc3ccccc3C[C@H]2CN2CCOCC2)n2ccccc12)c1ccc(O)cc1 IVXQXWNWNDYCPO-BHVANESWSA-N 0.000 claims 1
- FZQUJWJPFIZNTR-UMSFTDKQSA-N Cn1ncc2cc(ccc12)N(C(=O)c1cc(-c2cc3OCOc3cc2C(=O)N2Cc3ccccc3C[C@H]2CN2CCOCC2)n2CCCCc12)c1ccc(O)cc1 Chemical compound Cn1ncc2cc(ccc12)N(C(=O)c1cc(-c2cc3OCOc3cc2C(=O)N2Cc3ccccc3C[C@H]2CN2CCOCC2)n2CCCCc12)c1ccc(O)cc1 FZQUJWJPFIZNTR-UMSFTDKQSA-N 0.000 claims 1
- 206010009944 Colon cancer Diseases 0.000 claims 1
- 238000007341 Heck reaction Methods 0.000 claims 1
- NHRIZCZTVRYRON-UMSFTDKQSA-N Oc1ccc(cc1)N(C(=O)c1cc(-c2cc3OCCOc3cc2C(=O)N2Cc3ccccc3C[C@H]2CN2CCOCC2)n2CCCCc12)c1ccccc1 Chemical compound Oc1ccc(cc1)N(C(=O)c1cc(-c2cc3OCCOc3cc2C(=O)N2Cc3ccccc3C[C@H]2CN2CCOCC2)n2CCCCc12)c1ccccc1 NHRIZCZTVRYRON-UMSFTDKQSA-N 0.000 claims 1
- 229940079156 Proteasome inhibitor Drugs 0.000 claims 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 1
- 150000001263 acyl chlorides Chemical class 0.000 claims 1
- 125000003172 aldehyde group Chemical group 0.000 claims 1
- 150000008064 anhydrides Chemical class 0.000 claims 1
- 230000000340 anti-metabolite Effects 0.000 claims 1
- 229940100197 antimetabolite Drugs 0.000 claims 1
- 239000002256 antimetabolite Substances 0.000 claims 1
- 239000002246 antineoplastic agent Substances 0.000 claims 1
- XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 claims 1
- 235000010290 biphenyl Nutrition 0.000 claims 1
- 239000004305 biphenyl Substances 0.000 claims 1
- 125000002837 carbocyclic group Chemical group 0.000 claims 1
- 150000007942 carboxylates Chemical class 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- 230000008878 coupling Effects 0.000 claims 1
- 238000010168 coupling process Methods 0.000 claims 1
- 238000005859 coupling reaction Methods 0.000 claims 1
- 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 238000010511 deprotection reaction Methods 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 231100000024 genotoxic Toxicity 0.000 claims 1
- 230000001738 genotoxic effect Effects 0.000 claims 1
- 208000026278 immune system disease Diseases 0.000 claims 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims 1
- IJKXJZJLJSCTHE-UHFFFAOYSA-N indolizin-1-ol Chemical group C1=CC=CC2=C(O)C=CN21 IJKXJZJLJSCTHE-UHFFFAOYSA-N 0.000 claims 1
- 239000000543 intermediate Substances 0.000 claims 1
- 229940043355 kinase inhibitor Drugs 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 1
- 230000000394 mitotic effect Effects 0.000 claims 1
- VYXJULKGMXJVGI-XIFFEERXSA-N n-(4-hydroxyphenyl)-3-[6-[(3s)-3-(morpholin-4-ylmethyl)-3,4-dihydro-1h-isoquinoline-2-carbonyl]-1,3-benzodioxol-5-yl]-n-phenyl-5,6,7,8-tetrahydroindolizine-1-carboxamide Chemical compound C1=CC(O)=CC=C1N(C=1C=CC=CC=1)C(=O)C1=C2CCCCN2C(C=2C(=CC=3OCOC=3C=2)C(=O)N2[C@@H](CC3=CC=CC=C3C2)CN2CCOCC2)=C1 VYXJULKGMXJVGI-XIFFEERXSA-N 0.000 claims 1
- CTPOEKJMQNXTSZ-XIFFEERXSA-N n-(4-hydroxyphenyl)-3-[6-[(3s)-3-(morpholin-4-ylmethyl)-3,4-dihydro-1h-isoquinoline-2-carbonyl]-1,3-benzodioxol-5-yl]-n-phenylindolizine-1-carboxamide Chemical compound C1=CC(O)=CC=C1N(C=1C=CC=CC=1)C(=O)C1=C2C=CC=CN2C(C=2C(=CC=3OCOC=3C=2)C(=O)N2[C@@H](CC3=CC=CC=C3C2)CN2CCOCC2)=C1 CTPOEKJMQNXTSZ-XIFFEERXSA-N 0.000 claims 1
- ZQDDAXHWZXNRGJ-DHUJRADRSA-N n-(4-hydroxyphenyl)-n-(1-methylindol-5-yl)-3-[6-[(3s)-3-(morpholin-4-ylmethyl)-3,4-dihydro-1h-isoquinoline-2-carbonyl]-1,3-benzodioxol-5-yl]-5,6,7,8-tetrahydroindolizine-1-carboxamide Chemical compound C([C@@H]1CC2=CC=CC=C2CN1C(=O)C1=CC=2OCOC=2C=C1C1=CC(=C2CCCCN21)C(=O)N(C=1C=C2C=CN(C2=CC=1)C)C=1C=CC(O)=CC=1)N1CCOCC1 ZQDDAXHWZXNRGJ-DHUJRADRSA-N 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 229910052763 palladium Inorganic materials 0.000 claims 1
- 238000005897 peptide coupling reaction Methods 0.000 claims 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims 1
- 239000003757 phosphotransferase inhibitor Substances 0.000 claims 1
- IWELDVXSEVIIGI-UHFFFAOYSA-N piperazin-2-one Chemical compound O=C1CNCCN1 IWELDVXSEVIIGI-UHFFFAOYSA-N 0.000 claims 1
- 239000002574 poison Substances 0.000 claims 1
- 231100000614 poison Toxicity 0.000 claims 1
- 230000000861 pro-apoptotic effect Effects 0.000 claims 1
- 239000003207 proteasome inhibitor Substances 0.000 claims 1
- 230000001681 protective effect Effects 0.000 claims 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- LTXJLQINBYSQFU-UHFFFAOYSA-N pyrimidin-5-ol Chemical group OC1=CN=CN=C1 LTXJLQINBYSQFU-UHFFFAOYSA-N 0.000 claims 1
- 238000001959 radiotherapy Methods 0.000 claims 1
- 125000003003 spiro group Chemical group 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
Classifications
-
- 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
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- 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
- A61K31/472—Non-condensed isoquinolines, e.g. papaverine
- A61K31/4725—Non-condensed isoquinolines, e.g. papaverine containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Indole Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
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| FR1200193A FR2986002B1 (fr) | 2012-01-24 | 2012-01-24 | Nouveaux derives d'indolizine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| PCT/FR2013/050136 WO2013110890A1 (fr) | 2012-01-24 | 2013-01-23 | Nouveaux derives d'indolizine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| EP13704189.3A EP2807159B1 (fr) | 2012-01-24 | 2013-01-23 | Nouveaux derives d'indolizine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent pour le traitement du cancer |
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| FR2986002B1 (fr) | 2012-01-24 | 2014-02-21 | Servier Lab | Nouveaux derives d'indolizine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| FR3008979B1 (fr) | 2013-07-23 | 2015-07-24 | Servier Lab | Nouveaux derives phosphates, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| FR3008978A1 (fr) * | 2013-07-23 | 2015-01-30 | Servier Lab | "nouveaux derives d'indole et de pyrrole, leur procede de preparation et les compositions pharmaceutiques qui les contiennent" |
| FR3008976A1 (fr) | 2013-07-23 | 2015-01-30 | Servier Lab | "nouveaux derives d'indolizine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent" |
| FR3008977A1 (fr) | 2013-07-23 | 2015-01-30 | Servier Lab | Nouveaux derives d'isoindoline ou d'isoquinoline, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| FR3008975A1 (fr) * | 2013-07-23 | 2015-01-30 | Servier Lab | Nouveaux derives de pyrrole, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| FR3015483B1 (fr) * | 2013-12-23 | 2016-01-01 | Servier Lab | Nouveaux derives de thienopyrimidine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| US20150320755A1 (en) | 2014-04-16 | 2015-11-12 | Infinity Pharmaceuticals, Inc. | Combination therapies |
| WO2016190847A1 (en) * | 2015-05-26 | 2016-12-01 | Calitor Sciences, Llc | Substituted heteroaryl compounds and methods of use |
| FR3037958B1 (fr) * | 2015-06-23 | 2019-01-25 | Les Laboratoires Servier | Nouveaux derives d'hydroxy-acide, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| FR3037959B1 (fr) * | 2015-06-23 | 2017-08-04 | Servier Lab | Nouveaux derives bicycliques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| FR3037956B1 (fr) * | 2015-06-23 | 2017-08-04 | Servier Lab | Nouveaux derives d'acide amine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| WO2017013271A1 (en) * | 2015-07-23 | 2017-01-26 | Les Laboratoires Servier | Combination of an inhibitor of phosphatidylinositol 3-kinase delta and a bcl-2 inhibitor, uses and pharmaceutical compositions thereof |
| UY37316A (es) | 2016-07-07 | 2018-01-31 | Servier Lab | Dispersión sólida farmacéutica de un inhibidor de bcl-2, composiciones farmacéuticas de ésta, y usos para el tratamiento de cáncer |
| WO2018015526A1 (en) | 2016-07-22 | 2018-01-25 | Les Laboratoires Servier | Combination of a bcl-2 inhibitor and a mcl-1 inhibitor, uses and pharmaceutical compositions thereof |
| WO2018158225A1 (en) | 2017-02-28 | 2018-09-07 | Les Laboratoires Servier | Combination of a bcl-2 inhibitor and a mdm2 inhibitor, uses and pharmaceutical compositions thereof |
| TWI672302B (zh) * | 2017-07-06 | 2019-09-21 | 法商施維雅藥廠 | Bcl-2抑制劑之新結晶型、其製備方法及含其之醫藥組合物 |
| JP2020528062A (ja) | 2017-07-27 | 2020-09-17 | 江蘇恒瑞医薬股▲ふん▼有限公司 | ピペラジンヘテロアリール誘導体、その製造方法、およびその医薬での使用 |
| FR3072679B1 (fr) * | 2017-10-25 | 2020-10-30 | Servier Lab | Nouveaux derives macrocycliques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| WO2019134970A1 (en) | 2018-01-05 | 2019-07-11 | Les Laboratoires Servier | Novel salts of a bcl-2 inhibitor,related crystalline forms,method for preparing the same and pharmaceutical compositions containing the same |
| CN111801320A (zh) | 2018-01-10 | 2020-10-20 | 里科瑞尔姆Ip控股有限责任公司 | 苯甲酰胺化合物 |
| CA3090177A1 (en) | 2018-02-16 | 2019-08-22 | Abbvie Inc. | Selective bcl-2 inhibitors in combination with an anti-pd-1 or an anti-pd-l1 antibody for the treatment of cancers |
| CN113840609A (zh) * | 2019-05-14 | 2021-12-24 | 法国施维雅药厂 | 用于治疗Bcl-2介导的携带Gly101Val突变的癌症的Bcl-2抑制剂 |
| US20230092679A1 (en) | 2019-05-20 | 2023-03-23 | Novartis Ag | Mcl-1 inhibitor antibody-drug conjugates and methods of use |
| CA3202759A1 (en) | 2020-11-24 | 2022-06-02 | Novartis Ag | Mcl-1 inhibitor antibody-drug conjugates and methods of use |
| JP2024505562A (ja) | 2021-02-02 | 2024-02-06 | レス ラボラトイレス セルビエル | 選択的ｂｃｌ－ｘｌ ｐｒｏｔａｃ化合物及び使用の方法 |
| MX2023010692A (es) * | 2021-03-12 | 2023-09-19 | Eil Therapeutics Inc | Compuestos que tienen tetrahidroindolizina-1-carboxamida como inhibidores de bcl-2. |
| WO2023129553A1 (en) * | 2021-12-29 | 2023-07-06 | Eil Therapeutics, Inc. | Bcl-2 inhibitors |
| JP2025517435A (ja) | 2022-05-20 | 2025-06-05 | ノバルティス アーゲー | 抗新生物薬化合物の抗体－薬物コンジュゲートおよびその使用の方法 |
| EP4525925A1 (en) | 2022-05-20 | 2025-03-26 | Novartis AG | Epha2 bcl-xl inhibitor antibody-drug conjugates and methods of use thereof |
| IL317103A (en) | 2022-05-20 | 2025-01-01 | Novartis Ag | Antibody-drug conjugates of MET inhibitor BCL-XL and methods of using them |
| WO2024189481A1 (en) | 2023-03-10 | 2024-09-19 | Novartis Ag | Panras inhibitor antibody-drug conjugates and methods of use thereof |
| WO2025111431A1 (en) | 2023-11-22 | 2025-05-30 | Les Laboratoires Servier | Anti-cd7 antibody-drug conjugates and methods of use thereof |
| WO2025111450A1 (en) | 2023-11-22 | 2025-05-30 | Les Laboratoires Servier | Anti-cd74 antibody-drug conjugates and methods of use thereof |
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| US5932590A (en) * | 1996-12-05 | 1999-08-03 | Merck & Co., Inc. | Inhibitors of farnesyl-protein transferase |
| NZ531378A (en) * | 2001-09-19 | 2006-11-30 | Aventis Pharma S | Indolizines as kinase protein inhibitors suitable for treating solid tumours |
| EP1501514B1 (en) | 2002-05-03 | 2012-12-19 | Exelixis, Inc. | Protein kinase modulators and methods of use |
| US20050070570A1 (en) | 2003-06-18 | 2005-03-31 | 4Sc Ag | Novel potassium channels modulators |
| AU2005277223C1 (en) * | 2004-08-20 | 2009-05-21 | The Regents Of The University Of Michigan | Small molecule inhibitors of anti-apoptotic Bcl-2 family members and the uses thereof |
| MY162157A (en) * | 2007-04-16 | 2017-05-31 | Abbott Lab | Substituted indole mcl-1 inhibitors |
| CA2707445A1 (en) | 2007-11-30 | 2009-06-11 | Biota Scientific Management Pty Ltd | Tetrahydro-isoquinoline ppat inhibitors as antibacterial agents |
| WO2009073845A1 (en) | 2007-12-07 | 2009-06-11 | Linde North America, Inc. | Methods for monitoring hydrogen fueling systems |
| JP5496915B2 (ja) * | 2008-02-13 | 2014-05-21 | シージーアイ ファーマシューティカルズ，インコーポレーテッド | ６−アリール−イミダゾ［１，２−ａ］ピラジン誘導体、その製造方法、及びその使用方法 |
| US20120095211A1 (en) | 2010-09-22 | 2012-04-19 | Intermune, Inc. | Substituted proline inhibitors of hepatitis c virus replication |
| US9346795B2 (en) | 2011-05-25 | 2016-05-24 | Bristol-Myers Squibb Company | Substituted sulfonamides useful as antiapoptotic Bcl inhibitors |
| FR2986002B1 (fr) * | 2012-01-24 | 2014-02-21 | Servier Lab | Nouveaux derives d'indolizine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| FR3008976A1 (fr) | 2013-07-23 | 2015-01-30 | Servier Lab | "nouveaux derives d'indolizine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent" |
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2014
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- 2014-06-27 PH PH12014501488A patent/PH12014501488B1/en unknown
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- 2014-07-04 GT GT201400142A patent/GT201400142A/es unknown
- 2014-07-09 EC ECIEPI20148606A patent/ECSP14008606A/es unknown
- 2014-07-10 CL CL2014001829A patent/CL2014001829A1/es unknown
- 2014-07-11 ZA ZA2014/05101A patent/ZA201405101B/en unknown
- 2014-07-16 IL IL233663A patent/IL233663B/en active IP Right Grant
- 2014-07-21 CU CU2014000089A patent/CU20140089A7/es unknown
- 2014-07-22 NI NI201400081A patent/NI201400081A/es unknown
- 2014-08-07 MA MA37278A patent/MA35903B1/fr unknown
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2015
- 2015-07-15 US US14/799,840 patent/US9603854B2/en active Active
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2017
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- 2017-02-09 US US15/428,493 patent/US10258626B2/en active Active
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