JP2016525529A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2016525529A5 JP2016525529A5 JP2016528512A JP2016528512A JP2016525529A5 JP 2016525529 A5 JP2016525529 A5 JP 2016525529A5 JP 2016528512 A JP2016528512 A JP 2016528512A JP 2016528512 A JP2016528512 A JP 2016528512A JP 2016525529 A5 JP2016525529 A5 JP 2016525529A5
- Authority
- JP
- Japan
- Prior art keywords
- group
- branched
- tetrahydroisoquinoline
- linear
- methyl
- 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
Links
- 150000001875 compounds Chemical class 0.000 claims 51
- 239000002253 acid Substances 0.000 claims 39
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 38
- 125000003118 aryl group Chemical group 0.000 claims 33
- 150000003839 salts Chemical class 0.000 claims 28
- 125000000753 cycloalkyl group Chemical group 0.000 claims 23
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 23
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 21
- 125000001072 heteroaryl group Chemical group 0.000 claims 20
- 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 18
- 125000000217 alkyl group Chemical group 0.000 claims 17
- -1 (morpholin-4-yl) methyl group Chemical group 0.000 claims 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 15
- 229910052757 nitrogen Inorganic materials 0.000 claims 14
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 13
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 13
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 13
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 11
- 150000007513 acids Chemical class 0.000 claims 10
- 125000004432 carbon atom Chemical group C* 0.000 claims 10
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 8
- 125000002619 bicyclic group Chemical group 0.000 claims 8
- 125000005843 halogen group Chemical group 0.000 claims 8
- AEZGJQRFXBCLEN-HKBQPEDESA-N CN(C(=O)c1cc(-c2cc3CCN(Cc3cc2C(=O)N2Cc3ccccc3C[C@H]2CN2CCOCC2)C(O)=O)n(C)c1C)c1ccc(O)cc1 Chemical compound CN(C(=O)c1cc(-c2cc3CCN(Cc3cc2C(=O)N2Cc3ccccc3C[C@H]2CN2CCOCC2)C(O)=O)n(C)c1C)c1ccc(O)cc1 AEZGJQRFXBCLEN-HKBQPEDESA-N 0.000 claims 7
- 229910052736 halogen Inorganic materials 0.000 claims 7
- 150000002367 halogens Chemical class 0.000 claims 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 7
- 239000008194 pharmaceutical composition Substances 0.000 claims 7
- 125000006685 (C1-C6) polyhaloalkyl group Chemical group 0.000 claims 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 6
- 125000003545 alkoxy group Chemical group 0.000 claims 6
- 125000004104 aryloxy group Chemical group 0.000 claims 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 6
- 239000003814 drug Substances 0.000 claims 6
- 125000005842 heteroatom Chemical group 0.000 claims 6
- 238000004519 manufacturing process Methods 0.000 claims 6
- 238000000034 method Methods 0.000 claims 6
- 125000002950 monocyclic group Chemical group 0.000 claims 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 6
- 229910052760 oxygen Inorganic materials 0.000 claims 6
- 239000001301 oxygen Substances 0.000 claims 6
- 125000003003 spiro group Chemical group 0.000 claims 6
- 229910052717 sulfur Inorganic materials 0.000 claims 6
- 239000011593 sulfur Substances 0.000 claims 6
- 125000000304 alkynyl group Chemical group 0.000 claims 5
- 150000001768 cations Chemical class 0.000 claims 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims 5
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 4
- 206010028980 Neoplasm Diseases 0.000 claims 4
- 125000003342 alkenyl group Chemical group 0.000 claims 4
- 125000005110 aryl thio group Chemical group 0.000 claims 4
- 201000011510 cancer Diseases 0.000 claims 4
- 125000002837 carbocyclic group Chemical group 0.000 claims 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 4
- 125000004043 oxo group Chemical group O=* 0.000 claims 4
- 238000000926 separation method Methods 0.000 claims 4
- 125000001424 substituent group Chemical group 0.000 claims 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 4
- 125000004185 ester group Chemical group 0.000 claims 3
- 230000007062 hydrolysis Effects 0.000 claims 3
- 238000006460 hydrolysis reaction Methods 0.000 claims 3
- 208000023275 Autoimmune disease Diseases 0.000 claims 2
- 208000010839 B-cell chronic lymphocytic leukemia Diseases 0.000 claims 2
- 206010005003 Bladder cancer Diseases 0.000 claims 2
- 208000019838 Blood disease Diseases 0.000 claims 2
- 208000003174 Brain Neoplasms Diseases 0.000 claims 2
- 206010006187 Breast cancer Diseases 0.000 claims 2
- 208000026310 Breast neoplasm Diseases 0.000 claims 2
- UGBQHKNALULYFT-OAQYLSRUSA-N C[C@@H]1Cc2ccccc2CN1C(=O)c1cc2CN(CCc2cc1-c1cc(C(=O)N(C)c2ccc(O)cc2)c(C)n1C)C(O)=O Chemical compound C[C@@H]1Cc2ccccc2CN1C(=O)c1cc2CN(CCc2cc1-c1cc(C(=O)N(C)c2ccc(O)cc2)c(C)n1C)C(O)=O UGBQHKNALULYFT-OAQYLSRUSA-N 0.000 claims 2
- 206010009944 Colon cancer Diseases 0.000 claims 2
- 208000000461 Esophageal Neoplasms Diseases 0.000 claims 2
- 208000031422 Lymphocytic Chronic B-Cell Leukemia Diseases 0.000 claims 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims 2
- 208000015914 Non-Hodgkin lymphomas Diseases 0.000 claims 2
- 206010030155 Oesophageal carcinoma Diseases 0.000 claims 2
- 206010033128 Ovarian cancer Diseases 0.000 claims 2
- 206010061535 Ovarian neoplasm Diseases 0.000 claims 2
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-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
- 206010041067 Small cell lung cancer Diseases 0.000 claims 2
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims 2
- 208000002495 Uterine Neoplasms Diseases 0.000 claims 2
- 230000010933 acylation Effects 0.000 claims 2
- 238000005917 acylation reaction Methods 0.000 claims 2
- 150000001412 amines Chemical class 0.000 claims 2
- 230000006907 apoptotic process Effects 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- 230000001363 autoimmune Effects 0.000 claims 2
- 230000015572 biosynthetic process Effects 0.000 claims 2
- 235000010290 biphenyl Nutrition 0.000 claims 2
- 239000004305 biphenyl Substances 0.000 claims 2
- 210000004556 brain Anatomy 0.000 claims 2
- 210000000481 breast Anatomy 0.000 claims 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- 239000003153 chemical reaction reagent Substances 0.000 claims 2
- 208000032852 chronic lymphocytic leukemia Diseases 0.000 claims 2
- 210000001072 colon Anatomy 0.000 claims 2
- 208000029742 colonic neoplasm Diseases 0.000 claims 2
- 230000008878 coupling Effects 0.000 claims 2
- 238000010168 coupling process Methods 0.000 claims 2
- 238000005859 coupling reaction Methods 0.000 claims 2
- 208000035250 cutaneous malignant susceptibility to 1 melanoma Diseases 0.000 claims 2
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 claims 2
- 235000011180 diphosphates Nutrition 0.000 claims 2
- 201000004101 esophageal cancer Diseases 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 210000002816 gill Anatomy 0.000 claims 2
- 208000014951 hematologic disease Diseases 0.000 claims 2
- 208000018706 hematopoietic system disease Diseases 0.000 claims 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 2
- 208000026278 immune system disease Diseases 0.000 claims 2
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims 2
- 239000000543 intermediate Substances 0.000 claims 2
- 201000007270 liver cancer Diseases 0.000 claims 2
- 208000014018 liver neoplasm Diseases 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
- 201000000050 myeloid neoplasm Diseases 0.000 claims 2
- 125000001624 naphthyl group Chemical group 0.000 claims 2
- 125000006574 non-aromatic ring group Chemical group 0.000 claims 2
- 208000002154 non-small cell lung carcinoma Diseases 0.000 claims 2
- 238000005897 peptide coupling reaction Methods 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 150000003254 radicals Chemical class 0.000 claims 2
- 208000000587 small cell lung carcinoma Diseases 0.000 claims 2
- 239000007858 starting material Substances 0.000 claims 2
- 238000005694 sulfonylation reaction Methods 0.000 claims 2
- 238000003786 synthesis reaction Methods 0.000 claims 2
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims 2
- 210000003932 urinary bladder Anatomy 0.000 claims 2
- 201000005112 urinary bladder cancer Diseases 0.000 claims 2
- 206010046766 uterine cancer Diseases 0.000 claims 2
- GNFLFHZJXXFDRA-UHFFFAOYSA-N 1,2-dimethylpyrrole Chemical compound CC1=CC=CN1C GNFLFHZJXXFDRA-UHFFFAOYSA-N 0.000 claims 1
- DRXOPQFEWDRGKT-UHFFFAOYSA-N 1,5-dimethylpyrrole-2-carbonitrile Chemical compound CC1=CC=C(C#N)N1C DRXOPQFEWDRGKT-UHFFFAOYSA-N 0.000 claims 1
- ZVOCBNCKNQJAFL-UHFFFAOYSA-N 1-methylpyrrolo[2,3-b]pyridine Chemical compound C1=CN=C2N(C)C=CC2=C1 ZVOCBNCKNQJAFL-UHFFFAOYSA-N 0.000 claims 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims 1
- ZAIVVAGEIPDXTO-WJOKGBTCSA-N 3-[2-[2-[4-[(dimethylamino)methyl]phenyl]acetyl]-7-[(3R)-3-methyl-3,4-dihydro-1H-isoquinoline-2-carbonyl]-3,4-dihydro-1H-isoquinolin-6-yl]-N-(4-hydroxyphenyl)-N-methyl-5,6,7,8-tetrahydroindolizine-1-carboxamide Chemical compound C[C@@H]1Cc2ccccc2CN1C(=O)c1cc2CN(CCc2cc1-c1cc(C(=O)N(C)c2ccc(O)cc2)c2CCCCn12)C(=O)Cc1ccc(CN(C)C)cc1 ZAIVVAGEIPDXTO-WJOKGBTCSA-N 0.000 claims 1
- JZAUOSYMVYCYDR-JGCGQSQUSA-N 3-[2-[2-[4-[2-(dimethylamino)ethoxy]phenyl]acetyl]-7-[(3R)-3-methyl-3,4-dihydro-1H-isoquinoline-2-carbonyl]-3,4-dihydro-1H-isoquinolin-6-yl]-N-(4-hydroxyphenyl)-N-methyl-5,6,7,8-tetrahydroindolizine-1-carboxamide Chemical compound C[C@@H]1Cc2ccccc2CN1C(=O)c1cc2CN(CCc2cc1-c1cc(C(=O)N(C)c2ccc(O)cc2)c2CCCCn12)C(=O)Cc1ccc(OCCN(C)C)cc1 JZAUOSYMVYCYDR-JGCGQSQUSA-N 0.000 claims 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims 1
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims 1
- UZFMOKQJFYMBGY-UHFFFAOYSA-N 4-hydroxy-TEMPO Chemical compound CC1(C)CC(O)CC(C)(C)N1[O] UZFMOKQJFYMBGY-UHFFFAOYSA-N 0.000 claims 1
- QYASHELNMUPRKF-UHFFFAOYSA-N 5,6,7,8-tetrahydroindolizine Chemical compound C1CCCN2C=CC=C21 QYASHELNMUPRKF-UHFFFAOYSA-N 0.000 claims 1
- RFKIFIKTFDVAPX-XIFFEERXSA-N 6-[4-[(4-hydroxyphenyl)-propylcarbamoyl]-1,5-dimethylpyrrol-2-yl]-7-[(3S)-3-(morpholin-4-ylmethyl)-3,4-dihydro-1H-isoquinoline-2-carbonyl]-3,4-dihydro-1H-isoquinoline-2-carboxylic acid Chemical compound CCCN(C(=O)c1cc(-c2cc3CCN(Cc3cc2C(=O)N2Cc3ccccc3C[C@H]2CN2CCOCC2)C(O)=O)n(C)c1C)c1ccc(O)cc1 RFKIFIKTFDVAPX-XIFFEERXSA-N 0.000 claims 1
- ANESXWDARVOCOY-UMSFTDKQSA-N 6-[4-[butyl-(4-hydroxyphenyl)carbamoyl]-1,5-dimethylpyrrol-2-yl]-7-[(3S)-3-(morpholin-4-ylmethyl)-3,4-dihydro-1H-isoquinoline-2-carbonyl]-3,4-dihydro-1H-isoquinoline-2-carboxylic acid Chemical compound CCCCN(C(=O)c1cc(-c2cc3CCN(Cc3cc2C(=O)N2Cc3ccccc3C[C@H]2CN2CCOCC2)C(O)=O)n(C)c1C)c1ccc(O)cc1 ANESXWDARVOCOY-UMSFTDKQSA-N 0.000 claims 1
- BCEQFIZLMALFBJ-MGBGTMOVSA-N N-(4-hydroxyphenyl)-N-methyl-3-[7-[(3R)-3-methyl-3,4-dihydro-1H-isoquinoline-2-carbonyl]-2-[2-[3-(4-methylpiperazin-1-yl)phenyl]acetyl]-3,4-dihydro-1H-isoquinolin-6-yl]-5,6,7,8-tetrahydroindolizine-1-carboxamide Chemical compound C[C@@H]1Cc2ccccc2CN1C(=O)c1cc2CN(CCc2cc1-c1cc(C(=O)N(C)c2ccc(O)cc2)c2CCCCn12)C(=O)Cc1cccc(c1)N1CCN(C)CC1 BCEQFIZLMALFBJ-MGBGTMOVSA-N 0.000 claims 1
- WESHRFBTAOBSPA-MGBGTMOVSA-N N-(4-hydroxyphenyl)-N-methyl-3-[7-[(3R)-3-methyl-3,4-dihydro-1H-isoquinoline-2-carbonyl]-2-[2-[4-(4-methylpiperazin-1-yl)phenyl]acetyl]-3,4-dihydro-1H-isoquinolin-6-yl]-5,6,7,8-tetrahydroindolizine-1-carboxamide Chemical compound C[C@@H]1Cc2ccccc2CN1C(=O)c1cc2CN(CCc2cc1-c1cc(C(=O)N(C)c2ccc(O)cc2)c2CCCCn12)C(=O)Cc1ccc(cc1)N1CCN(C)CC1 WESHRFBTAOBSPA-MGBGTMOVSA-N 0.000 claims 1
- LSDBELUKOABOBK-MGBGTMOVSA-N N-(4-hydroxyphenyl)-N-methyl-3-[7-[(3R)-3-methyl-3,4-dihydro-1H-isoquinoline-2-carbonyl]-2-[2-[4-(morpholin-4-ylmethyl)phenyl]acetyl]-3,4-dihydro-1H-isoquinolin-6-yl]-5,6,7,8-tetrahydroindolizine-1-carboxamide Chemical compound C[C@@H]1Cc2ccccc2CN1C(=O)c1cc2CN(CCc2cc1-c1cc(C(=O)N(C)c2ccc(O)cc2)c2CCCCn12)C(=O)Cc1ccc(CN2CCOCC2)cc1 LSDBELUKOABOBK-MGBGTMOVSA-N 0.000 claims 1
- MLDJYPAJCQNMQN-UUWRZZSWSA-N N-(4-hydroxyphenyl)-N-methyl-3-[7-[(3R)-3-methyl-3,4-dihydro-1H-isoquinoline-2-carbonyl]-2-[2-[4-[(4-methylpiperazin-1-yl)methyl]phenyl]acetyl]-3,4-dihydro-1H-isoquinolin-6-yl]-5,6,7,8-tetrahydroindolizine-1-carboxamide Chemical compound C[C@@H]1Cc2ccccc2CN1C(=O)c1cc2CN(CCc2cc1-c1cc(C(=O)N(C)c2ccc(O)cc2)c2CCCCn12)C(=O)Cc1ccc(CN2CCN(C)CC2)cc1 MLDJYPAJCQNMQN-UUWRZZSWSA-N 0.000 claims 1
- UCZOGTLOGCSHIN-RWYGWLOXSA-N N-butyl-N-(4-hydroxyphenyl)-1,2-dimethyl-5-[7-[(3S)-3-(morpholin-4-ylmethyl)-3,4-dihydro-1H-isoquinoline-2-carbonyl]-2-(2-phenylacetyl)-3,4-dihydro-1H-isoquinolin-6-yl]pyrrole-3-carboxamide Chemical compound C(CCC)N(C(=O)C1=C(N(C(=C1)C=1C=C2CCN(CC2=CC=1C(=O)N1CC2=CC=CC=C2C[C@H]1CN1CCOCC1)C(CC1=CC=CC=C1)=O)C)C)C1=CC=C(C=C1)O UCZOGTLOGCSHIN-RWYGWLOXSA-N 0.000 claims 1
- 229940079156 Proteasome inhibitor Drugs 0.000 claims 1
- 150000001263 acyl chlorides 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
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 150000007942 carboxylates Chemical class 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims 1
- 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 125000000524 functional group Chemical group 0.000 claims 1
- 231100000024 genotoxic Toxicity 0.000 claims 1
- 230000001738 genotoxic effect Effects 0.000 claims 1
- 230000002140 halogenating effect Effects 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000004531 indol-5-yl group Chemical group [H]N1C([H])=C([H])C2=C([H])C(*)=C([H])C([H])=C12 0.000 claims 1
- HOBCFUWDNJPFHB-UHFFFAOYSA-N indolizine Chemical compound C1=CC=CN2C=CC=C21 HOBCFUWDNJPFHB-UHFFFAOYSA-N 0.000 claims 1
- 125000001041 indolyl group Chemical group 0.000 claims 1
- 150000002500 ions Chemical class 0.000 claims 1
- 229940043355 kinase inhibitor Drugs 0.000 claims 1
- 230000011987 methylation Effects 0.000 claims 1
- 238000007069 methylation reaction Methods 0.000 claims 1
- 230000000394 mitotic effect Effects 0.000 claims 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 239000003757 phosphotransferase inhibitor Substances 0.000 claims 1
- 239000002574 poison Substances 0.000 claims 1
- 231100000614 poison Toxicity 0.000 claims 1
- 108090000765 processed proteins & peptides Proteins 0.000 claims 1
- 239000003207 proteasome inhibitor Substances 0.000 claims 1
- 238000001959 radiotherapy Methods 0.000 claims 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR13/57276 | 2013-07-23 | ||
| FR1357276A FR3008977A1 (fr) | 2013-07-23 | 2013-07-23 | Nouveaux derives d'isoindoline ou d'isoquinoline, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| PCT/EP2014/065764 WO2015011164A1 (en) | 2013-07-23 | 2014-07-22 | New isoindoline or isoquinoline compounds, a process for their preparation and pharmaceutical compositions containing them |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016525529A JP2016525529A (ja) | 2016-08-25 |
| JP2016525529A5 true JP2016525529A5 (enExample) | 2017-08-31 |
| JP6395829B2 JP6395829B2 (ja) | 2018-09-26 |
Family
ID=49911606
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016528512A Active JP6395829B2 (ja) | 2013-07-23 | 2014-07-22 | 新規イソインドリン又はイソキノリン化合物、それらの調製のためのプロセス及びそれらを含有する医薬組成物 |
Country Status (49)
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| EA037300B1 (ru) | 2016-04-20 | 2021-03-05 | Бристол-Маерс Сквибб Компани | Замещенные бициклические гетероциклические соединения |
| AU2019295765B2 (en) | 2018-06-27 | 2024-08-29 | Yumanity, Inc. | Proteasome activity enhancing compounds |
| CA3158241A1 (en) * | 2019-11-15 | 2021-05-20 | Wuhan Ll Science And Technology Development Co., Ltd. | Rock inhibitor and preparation method therefor and use thereof |
| CN112010796B (zh) * | 2020-09-17 | 2022-04-22 | 浙江大学 | 光学活性3-(1,1-二氟-2-氧-2-芳基乙基)异吲哚啉-1-酮衍生物制备方法 |
| US12245355B2 (en) | 2021-02-19 | 2025-03-04 | Mevion Medical Systems, Inc. | Gantry for a particle therapy system |
| EP4313964A1 (en) * | 2021-03-24 | 2024-02-07 | Les Laboratoires Servier | New process for the synthesis of 5-{5-chloro-2-[(3s)-3- [(morpholin-4-yl)methyl]-3,4-dihydroisoquinoline-2(1h )-carbonyl]phenyl}-1,2-dimethyl-1h-pyrrole-3-carboxylic acid derivatives and its application for the production of pharmaceutical compounds |
| JP2025508803A (ja) | 2022-02-24 | 2025-04-10 | レ ラボラトワール セルヴィエ | ５－［７－（３，４－ジヒドロ－１ｈ－イソキノリン－２－カルボニル）－１，２，３，４－テトラヒドロイソキノリン－６－イル］－１ｈ－ピロール－３－カルボキサミド誘導体、それを含有する医薬組成物及びアポトーシス促進剤としてのその使用 |
| PE20251072A1 (es) | 2022-05-20 | 2025-04-10 | Novartis Ag | Conjugados de anticuerpo-farmaco de compuestos antineoplasicos y metodos de uso de los mismos |
| KR20250149173A (ko) * | 2023-03-31 | 2025-10-15 | 미쓰이 가가쿠 가부시키가이샤 | 카바메이트 화합물 |
| TW202540186A (zh) | 2023-11-22 | 2025-10-16 | 瑞士商諾華公司 | 抗ｃｄ７抗體藥物結合物及其使用方法 |
| PY24103486A (es) | 2023-11-22 | 2025-06-06 | Servier Lab | Conjugados de anticuerpo anti-cd74-fármaco y métodos de uso de los mismos |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2484209C (en) | 2002-05-03 | 2013-06-11 | Exelixis, Inc. | Protein kinase modulators and methods of use |
| WO2004096774A1 (en) | 2003-05-01 | 2004-11-11 | Glaxo Group Limited | Acyl isoindoline derivatives and acyl isoquinoline derivatives as anti-viral agents |
| US20050070570A1 (en) | 2003-06-18 | 2005-03-31 | 4Sc Ag | Novel potassium channels modulators |
| US8557812B2 (en) * | 2004-08-20 | 2013-10-15 | The Regents Of The University Of Michigan | Small molecule inhibitors of anti-apoptotic BCL-2 family members and the uses thereof |
| CN101039662A (zh) * | 2004-08-20 | 2007-09-19 | 密执安州立大学董事会 | 抗－细胞凋亡bcl－2家族成员的小分子抑制剂及其应用 |
| RU2007128987A (ru) * | 2005-02-15 | 2009-03-27 | Ново Нордиск А/С (DK) | 3,4-дигидро-1н-изохинолин-2-карбоновой кислоты 5-аминопиридин-2-2-иловые эфиры |
| ES2705599T3 (es) | 2007-04-16 | 2019-03-26 | Abbvie Inc | Indoles sustituidos en la posición 7 como inhibidores de mcl-1 |
| WO2009073545A2 (en) | 2007-11-30 | 2009-06-11 | Maxthera, Inc. | Tetrahydro-isoquinoline ppat inhibitors as antibacterial agents |
| NZ587039A (en) | 2008-02-13 | 2013-01-25 | Gilead Connecticut Inc | 6-aryl-imidazo[1, 2-a]pyrazine derivatives, method of making, and method of use thereof |
| US7984530B2 (en) | 2008-02-14 | 2011-07-26 | Tory Reynolds | Pet waste vacuum system and apparatus, disposable liners therefor, and a method of collecting pet waste using same |
| JP2014521595A (ja) * | 2011-05-25 | 2014-08-28 | ブリストル−マイヤーズ スクイブ カンパニー | 抗アポトーシスＢｃｌ阻害剤として有用な置換スルホンアミド |
| US9126979B2 (en) * | 2011-12-23 | 2015-09-08 | Novartis Ag | Compounds for inhibiting the interaction of BCL2 with binding partners |
| EP2798432A4 (en) | 2011-12-27 | 2015-07-22 | Intel Corp | METHODS AND SYSTEMS FOR CONTROLLING POWER SUPPLY NETWORKS DURING AN ACTIVE STATE OF A PERIODICALLY TRIGGERED DOMAIN IN ACCORDANCE WITH PERIODICALLY RELEASED DOMAIN LOADING CONDITIONS |
| 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 |
| 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 |
| FR3008979B1 (fr) * | 2013-07-23 | 2015-07-24 | Servier Lab | Nouveaux derives phosphates, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
-
2013
- 2013-07-23 FR FR1357276A patent/FR3008977A1/fr not_active Withdrawn
-
2014
- 2014-07-13 JO JOP/2014/0223A patent/JO3457B1/ar active
- 2014-07-15 UY UY0001035664A patent/UY35664A/es active IP Right Grant
- 2014-07-22 HR HRP20190277TT patent/HRP20190277T1/hr unknown
- 2014-07-22 GE GEAP201414063A patent/GEP20207070B/en unknown
- 2014-07-22 WO PCT/EP2014/065764 patent/WO2015011164A1/en not_active Ceased
- 2014-07-22 ME MEP-2019-35A patent/ME03346B/me unknown
- 2014-07-22 TR TR2018/19155T patent/TR201819155T4/tr unknown
- 2014-07-22 GE GEAP201914063A patent/GEAP201914063A/en unknown
- 2014-07-22 NZ NZ716155A patent/NZ716155A/en unknown
- 2014-07-22 MX MX2016000904A patent/MX365373B/es active IP Right Grant
- 2014-07-22 MY MYPI2016700106A patent/MY193619A/en unknown
- 2014-07-22 TN TN2016000003A patent/TN2016000003A1/en unknown
- 2014-07-22 KR KR1020167004570A patent/KR102008431B1/ko active Active
- 2014-07-22 LT LTEP14741648.1T patent/LT3024826T/lt unknown
- 2014-07-22 UA UAA201601395A patent/UA117490C2/uk unknown
- 2014-07-22 PE PE2016000023A patent/PE20160241A1/es unknown
- 2014-07-22 HU HUE14741648A patent/HUE041443T2/hu unknown
- 2014-07-22 EP EP14741648.1A patent/EP3024826B1/en active Active
- 2014-07-22 TW TW103125161A patent/TWI560184B/zh not_active IP Right Cessation
- 2014-07-22 AR ARP140102713A patent/AR097009A1/es active IP Right Grant
- 2014-07-22 RS RS20190150A patent/RS58344B1/sr unknown
- 2014-07-22 CN CN201811358313.9A patent/CN109456324B/zh active Active
- 2014-07-22 PL PL14741648T patent/PL3024826T3/pl unknown
- 2014-07-22 SI SI201431038T patent/SI3024826T1/sl unknown
- 2014-07-22 US US14/905,985 patent/US9809574B2/en active Active
- 2014-07-22 BR BR112016001080-9A patent/BR112016001080B1/pt active IP Right Grant
- 2014-07-22 PT PT14741648T patent/PT3024826T/pt unknown
- 2014-07-22 JP JP2016528512A patent/JP6395829B2/ja active Active
- 2014-07-22 HK HK16106761.6A patent/HK1218754A1/zh unknown
- 2014-07-22 DK DK14741648.1T patent/DK3024826T3/en active
- 2014-07-22 CA CA2919572A patent/CA2919572C/en active Active
- 2014-07-22 RU RU2016106003A patent/RU2689305C2/ru active
- 2014-07-22 MA MA38801A patent/MA38801B1/fr unknown
- 2014-07-22 AP AP2016008989A patent/AP2016008989A0/xx unknown
- 2014-07-22 ES ES14741648T patent/ES2711371T3/es active Active
- 2014-07-22 MD MDA20160018A patent/MD4793C1/ro not_active IP Right Cessation
- 2014-07-22 AU AU2014295101A patent/AU2014295101B2/en active Active
- 2014-07-22 EA EA201600122A patent/EA032301B1/ru unknown
- 2014-07-22 CN CN201480042422.3A patent/CN105431422B/zh active Active
- 2014-07-22 CU CUP2016000010A patent/CU24352B1/xx unknown
- 2014-07-22 SG SG11201600205XA patent/SG11201600205XA/en unknown
-
2016
- 2016-01-03 IL IL243449A patent/IL243449A0/en active IP Right Grant
- 2016-01-06 PH PH12016500034A patent/PH12016500034A1/en unknown
- 2016-01-11 ZA ZA2016/00198A patent/ZA201600198B/en unknown
- 2016-01-11 DO DO2016000009A patent/DOP2016000009A/es unknown
- 2016-01-15 CR CR20160030A patent/CR20160030A/es unknown
- 2016-01-20 CL CL2016000148A patent/CL2016000148A1/es unknown
- 2016-01-21 SA SA516370439A patent/SA516370439B1/ar unknown
- 2016-01-21 NI NI201600016A patent/NI201600016A/es unknown
-
2017
- 2017-09-14 US US15/704,330 patent/US10689364B2/en active Active
-
2019
- 2019-02-11 CY CY20191100175T patent/CY1121247T1/el unknown
-
2020
- 2020-05-04 US US16/865,799 patent/US11028070B2/en active Active
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| AU2023203860B2 (en) | Modulators of the integrated stress pathway | |
| AU2018360854B2 (en) | Modulators of the integrated stress pathway | |
| RU2016106003A (ru) | Новые изоиндолиновые или изохинолиновые соединения, способ их получения и фармацевтические композиции, содержащие их | |
| KR20250029954A (ko) | 피리도[4,3-d]피리미딘 화합물 | |
| JP6529085B2 (ja) | 複素環化合物 | |
| CA2433021C (en) | Isoindole-imide compounds, compositions, and uses thereof | |
| JP6505023B2 (ja) | Ｃｎｓおよび他の障害を治療するための、ｐｄｅ４アイソザイムの阻害薬としてのアザベンゾイミダゾール化合物 | |
| JP2024517772A (ja) | 置換された２－（２，６－ジオキソピペリジン－３－イル）－５－（１－ピペリジン－４－イル）イソインドリン－１，３－ジオン誘導体及びその使用 | |
| JP2019525962A (ja) | ケモカイン受容体調節剤及びそれの使用 | |
| JP2021501779A (ja) | 統合的ストレス経路の調節剤 | |
| KR20110031475A (ko) | 트리아졸로피리딘 ｊａｋ 억제제 화합물 및 방법 | |
| JP2016531108A5 (enExample) | ||
| RU2014130125A (ru) | Новые пиррольные соединения, способ их получения и фармацевтические композиции, содержащие их | |
| BR102014017997A2 (pt) | compostos do tipo fosfato, um processo para sua preparação e composições farmacêuticas contendo os mesmos | |
| RU2016106002A (ru) | Новые индольные и пиррольные соединения, способ их получения и фармацевтические композиции, содержащие их | |
| JP5608098B2 (ja) | キナーゼ阻害薬としてのピラゾロピリジン | |
| KR20250100539A (ko) | 피리도[4,3-d]피리미딘 화합물 | |
| JP2021521266A5 (enExample) | ||
| WO2016115869A1 (zh) | Flt3激酶的新型抑制剂及其用途 | |
| TW202438498A (zh) | 雜環化合物之用途 | |
| ES2742078T3 (es) | Piridonas bicíclicas novedosas como moduladores de gamma-secretasa | |
| ES2782113T3 (es) | Compuestos de quinolina fusionados como inhibidores de PI3K/mTor | |
| JP6837072B2 (ja) | ６，７−ジヒドロ−５Ｈ−ピラゾロ［５，１−ｂ］［１，３］オキサジン−２−カルボキサミド化合物 | |
| WO2020102150A1 (en) | Heterocyclic derivatives as pi3k inhibitors | |
| CN107848971B (zh) | 杂环化合物 |