JP2022189853A5 - - Google Patents
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- JP2022189853A5 JP2022189853A5 JP2022161777A JP2022161777A JP2022189853A5 JP 2022189853 A5 JP2022189853 A5 JP 2022189853A5 JP 2022161777 A JP2022161777 A JP 2022161777A JP 2022161777 A JP2022161777 A JP 2022161777A JP 2022189853 A5 JP2022189853 A5 JP 2022189853A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrrolo
- methyl
- fluoro
- pyridin
- isopropyl
- 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.)
- Pending
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- 150000001875 compounds Chemical class 0.000 claims 58
- 125000000217 alkyl group Chemical group 0.000 claims 55
- 150000003839 salts Chemical class 0.000 claims 53
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 24
- 125000001424 substituent group Chemical group 0.000 claims 24
- 208000032839 leukemia Diseases 0.000 claims 23
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 22
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 22
- 125000001475 halogen functional group Chemical group 0.000 claims 22
- 125000002947 alkylene group Chemical group 0.000 claims 15
- 125000003118 aryl group Chemical group 0.000 claims 15
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims 14
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 12
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 10
- 125000003545 alkoxy group Chemical group 0.000 claims 10
- 239000003814 drug Substances 0.000 claims 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 10
- 125000004966 cyanoalkyl group Chemical group 0.000 claims 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims 8
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 8
- 206010028980 Neoplasm Diseases 0.000 claims 7
- 201000011510 cancer Diseases 0.000 claims 7
- 201000008968 osteosarcoma Diseases 0.000 claims 7
- 125000003282 alkyl amino group Chemical group 0.000 claims 6
- 125000001072 heteroaryl group Chemical group 0.000 claims 6
- 208000006664 Precursor Cell Lymphoblastic Leukemia-Lymphoma Diseases 0.000 claims 5
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- 125000006698 (C1-C3) dialkylamino group Chemical group 0.000 claims 4
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 4
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 4
- 125000006719 (C6-C10) aryl (C1-C6) alkyl group Chemical group 0.000 claims 4
- 208000024893 Acute lymphoblastic leukemia Diseases 0.000 claims 4
- 208000014697 Acute lymphocytic leukaemia Diseases 0.000 claims 4
- 208000031261 Acute myeloid leukaemia Diseases 0.000 claims 4
- 101100310927 Caenorhabditis elegans sra-4 gene Proteins 0.000 claims 4
- 125000004663 dialkyl amino group Chemical group 0.000 claims 4
- 125000004438 haloalkoxy group Chemical group 0.000 claims 4
- 208000003747 lymphoid leukemia Diseases 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims 3
- 208000028018 Lymphocytic leukaemia Diseases 0.000 claims 3
- 201000003793 Myelodysplastic syndrome Diseases 0.000 claims 3
- 230000001684 chronic effect Effects 0.000 claims 3
- 201000005962 mycosis fungoides Diseases 0.000 claims 3
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims 2
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 2
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims 2
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 2
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 2
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 2
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 2
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 2
- 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims 2
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 2
- 125000006568 (C4-C7) heterocycloalkyl group Chemical group 0.000 claims 2
- AOWUERVCHHESOK-UHFFFAOYSA-N 4-methyl-5-[[4-(5-phenylpyrrolo[3,2-d]pyrimidin-7-yl)piperidin-1-yl]methyl]-1H-indole-2-carbonitrile Chemical compound CC1=C2C=C(NC2=CC=C1CN1CCC(CC1)C1=CN(C2=C1N=CN=C2)C1=CC=CC=C1)C#N AOWUERVCHHESOK-UHFFFAOYSA-N 0.000 claims 2
- AXLYOFDTQBTULH-UHFFFAOYSA-N 5-(4-fluorophenyl)-7-[1-(1H-indol-5-ylmethyl)piperidin-4-yl]pyrrolo[3,2-d]pyrimidine Chemical compound N1C=CC2=CC(=CC=C12)CN1CCC(CC1)C1=CN(C2=C1N=CN=C2)C1=CC=C(C=C1)F AXLYOFDTQBTULH-UHFFFAOYSA-N 0.000 claims 2
- NZFUXGOJCWWYMP-UHFFFAOYSA-N 5-(4-fluorophenyl)-7-[1-(1H-indol-6-ylmethyl)piperidin-4-yl]pyrrolo[3,2-d]pyrimidine Chemical compound N1C=CC2=CC=C(C=C12)CN1CCC(CC1)C1=CN(C2=C1N=CN=C2)C1=CC=C(C=C1)F NZFUXGOJCWWYMP-UHFFFAOYSA-N 0.000 claims 2
- NBZBGHGDHAQDIR-UHFFFAOYSA-N 5-[[4-[5-(3-fluorophenyl)pyrrolo[3,2-d]pyrimidin-7-yl]piperidin-1-yl]methyl]-4-methyl-1H-indole-2-carbonitrile Chemical compound FC=1C=C(C=CC=1)N1C=C(C=2N=CN=CC=21)C1CCN(CC1)CC=1C(=C2C=C(NC2=CC=1)C#N)C NBZBGHGDHAQDIR-UHFFFAOYSA-N 0.000 claims 2
- AEWLCMCBYHNFOW-UHFFFAOYSA-N 5-[[4-[5-(4-fluorophenyl)pyrrolo[3,2-d]pyrimidin-7-yl]piperidin-1-yl]methyl]-1,3-dihydrobenzimidazol-2-one Chemical compound FC1=CC=C(C=C1)N1C=C(C=2N=CN=CC=21)C1CCN(CC1)CC1=CC2=C(NC(N2)=O)C=C1 AEWLCMCBYHNFOW-UHFFFAOYSA-N 0.000 claims 2
- 239000005973 Carvone Substances 0.000 claims 2
- 206010018429 Glucose tolerance impaired Diseases 0.000 claims 2
- 206010022489 Insulin Resistance Diseases 0.000 claims 2
- 206010025323 Lymphomas Diseases 0.000 claims 2
- 101710169972 Menin Proteins 0.000 claims 2
- 102100030550 Menin Human genes 0.000 claims 2
- 201000009906 Meningitis Diseases 0.000 claims 2
- 208000034578 Multiple myelomas Diseases 0.000 claims 2
- 208000033776 Myeloid Acute Leukemia Diseases 0.000 claims 2
- 208000014767 Myeloproliferative disease Diseases 0.000 claims 2
- 201000007224 Myeloproliferative neoplasm Diseases 0.000 claims 2
- 102100022678 Nucleophosmin Human genes 0.000 claims 2
- 108010025568 Nucleophosmin Proteins 0.000 claims 2
- 206010035226 Plasma cell myeloma Diseases 0.000 claims 2
- 208000001280 Prediabetic State Diseases 0.000 claims 2
- 208000033759 Prolymphocytic T-Cell Leukemia Diseases 0.000 claims 2
- 208000026651 T-cell prolymphocytic leukemia Diseases 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 206010012601 diabetes mellitus Diseases 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 201000001421 hyperglycemia Diseases 0.000 claims 2
- 230000002401 inhibitory effect Effects 0.000 claims 2
- 230000003993 interaction Effects 0.000 claims 2
- 125000004043 oxo group Chemical group O=* 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 201000009104 prediabetes syndrome Diseases 0.000 claims 2
- 230000008707 rearrangement Effects 0.000 claims 2
- 238000006467 substitution reaction Methods 0.000 claims 2
- 150000003573 thiols Chemical class 0.000 claims 2
- 208000008732 thymoma Diseases 0.000 claims 2
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- XIXQEFDSHZNZJN-UHFFFAOYSA-N 1-(4-fluorophenyl)-3-[1-(3-methylbutyl)piperidin-4-yl]pyrrolo[2,3-c]pyridine Chemical compound FC1=CC=C(C=C1)N1C=C(C=2C1=CN=CC=2)C1CCN(CC1)CCC(C)C XIXQEFDSHZNZJN-UHFFFAOYSA-N 0.000 claims 1
- SRGUIEOVCQHJSZ-UHFFFAOYSA-N 1-[2-(cyclopropylmethoxy)-4-fluorophenyl]-3-[1-[(4-fluorophenyl)methyl]piperidin-4-yl]pyrrolo[2,3-c]pyridine Chemical compound C1(CC1)COC1=C(C=CC(=C1)F)N1C=C(C=2C1=CN=CC=2)C1CCN(CC1)CC1=CC=C(C=C1)F SRGUIEOVCQHJSZ-UHFFFAOYSA-N 0.000 claims 1
- ZDUIYLWRQYRZMM-UHFFFAOYSA-N 1-methyl-5-[[4-(5-phenylpyrrolo[3,2-d]pyrimidin-7-yl)piperidin-1-yl]methyl]indole-2-carbonitrile Chemical compound CN1C(=CC2=CC(=CC=C12)CN1CCC(CC1)C1=CN(C2=C1N=CN=C2)C1=CC=CC=C1)C#N ZDUIYLWRQYRZMM-UHFFFAOYSA-N 0.000 claims 1
- IZPBYWFFWWVESM-UHFFFAOYSA-N 2-[1-[1-(cyclohexylmethyl)piperidin-4-yl]-2-oxoimidazo[4,5-c]pyridin-3-yl]-5-fluoro-N-methyl-N-propan-2-ylbenzamide Chemical compound C1(CCCCC1)CN1CCC(CC1)N1C(N(C=2C=NC=CC=21)C1=C(C(=O)N(C)C(C)C)C=C(C=C1)F)=O IZPBYWFFWWVESM-UHFFFAOYSA-N 0.000 claims 1
- RPYKXJCTCQRJBH-UHFFFAOYSA-N 2-[1-[1-[(2-cyano-4-methyl-1H-indol-5-yl)methyl]piperidin-4-yl]-2-oxoimidazo[4,5-c]pyridin-3-yl]-5-fluoro-N-methyl-N-propan-2-ylbenzamide Chemical compound C(#N)C=1NC2=CC=C(C(=C2C=1)C)CN1CCC(CC1)N1C(N(C=2C=NC=CC=21)C1=C(C(=O)N(C)C(C)C)C=C(C=C1)F)=O RPYKXJCTCQRJBH-UHFFFAOYSA-N 0.000 claims 1
- JAPYTDKJOUMBJB-UHFFFAOYSA-N 2-[3-(1,2,3,3a,4,5,6,6a-octahydrocyclopenta[c]pyrrol-5-yl)pyrrolo[2,3-c]pyridin-1-yl]-5-fluoro-N-methyl-N-propan-2-ylbenzamide Chemical compound FC=1C=CC(=C(C(=O)N(C)C(C)C)C=1)N1C=C(C=2C1=CN=CC=2)C1CC2C(CNC2)C1 JAPYTDKJOUMBJB-UHFFFAOYSA-N 0.000 claims 1
- ZCVFYPAATGWSQL-UHFFFAOYSA-N 2-[3-(1-benzylpiperidin-3-yl)pyrrolo[2,3-c]pyridin-1-yl]-5-fluoro-N-methyl-N-propan-2-ylbenzamide Chemical compound C(C1=CC=CC=C1)N1CC(CCC1)C1=CN(C2=CN=CC=C21)C1=C(C(=O)N(C)C(C)C)C=C(C=C1)F ZCVFYPAATGWSQL-UHFFFAOYSA-N 0.000 claims 1
- XBFQBMKWTFTZHA-UHFFFAOYSA-N 2-[3-(1-benzylpiperidin-4-yl)pyrrolo[2,3-c]pyridin-1-yl]-5-fluoro-N,N-di(propan-2-yl)benzamide Chemical compound C(C1=CC=CC=C1)N1CCC(CC1)C1=CN(C2=CN=CC=C21)C1=C(C(=O)N(C(C)C)C(C)C)C=C(C=C1)F XBFQBMKWTFTZHA-UHFFFAOYSA-N 0.000 claims 1
- PBHDVHHSEKDSDQ-UHFFFAOYSA-N 2-[3-(1-benzylpiperidin-4-yl)pyrrolo[2,3-c]pyridin-1-yl]-5-fluoro-N-(2-hydroxyethyl)-N-propan-2-ylbenzamide Chemical compound C(C1=CC=CC=C1)N1CCC(CC1)C1=CN(C2=CN=CC=C21)C1=C(C(=O)N(C(C)C)CCO)C=C(C=C1)F PBHDVHHSEKDSDQ-UHFFFAOYSA-N 0.000 claims 1
- QFWUZXFDJJGYKV-UHFFFAOYSA-N 2-[3-(1-benzylpiperidin-4-yl)pyrrolo[2,3-c]pyridin-1-yl]-N-ethyl-5-fluoro-N-propan-2-ylbenzamide Chemical compound C(C1=CC=CC=C1)N1CCC(CC1)C1=CN(C2=CN=CC=C21)C1=C(C(=O)N(C(C)C)CC)C=C(C=C1)F QFWUZXFDJJGYKV-UHFFFAOYSA-N 0.000 claims 1
- GNRUAVDVINTFNZ-UHFFFAOYSA-N 2-[3-(2-azaspiro[3.5]nonan-7-yl)pyrrolo[2,3-c]pyridin-1-yl]-5-fluoro-N-methyl-N-propan-2-ylbenzamide Chemical compound C1NCC11CCC(CC1)C1=CN(C2=CN=CC=C21)C1=C(C(=O)N(C)C(C)C)C=C(C=C1)F GNRUAVDVINTFNZ-UHFFFAOYSA-N 0.000 claims 1
- FJGZIHPNPBZSOX-UHFFFAOYSA-N 2-[3-(2-benzylpiperidin-4-yl)pyrrolo[2,3-c]pyridin-1-yl]-5-fluoro-N-methyl-N-propan-2-ylbenzamide Chemical compound C(C1=CC=CC=C1)C1NCCC(C1)C1=CN(C2=CN=CC=C21)C1=C(C(=O)N(C)C(C)C)C=C(C=C1)F FJGZIHPNPBZSOX-UHFFFAOYSA-N 0.000 claims 1
- ABWVTIOXFQAURQ-UHFFFAOYSA-N 2-[3-(azepan-4-yl)pyrrolo[2,3-c]pyridin-1-yl]-5-fluoro-N-methyl-N-propan-2-ylbenzamide Chemical compound N1CCC(CCC1)C1=CN(C2=CN=CC=C21)C1=C(C(=O)N(C)C(C)C)C=C(C=C1)F ABWVTIOXFQAURQ-UHFFFAOYSA-N 0.000 claims 1
- OWMGURMREYGDAM-JWTNVVGKSA-N 2-[3-[(2S,6R)-2,6-dimethylpiperidin-4-yl]pyrrolo[2,3-c]pyridin-1-yl]-5-fluoro-N-methyl-N-propan-2-ylbenzamide Chemical compound C[C@@H]1N[C@@H](CC(C1)C1=CN(C2=CN=CC=C21)C1=C(C(=O)N(C)C(C)C)C=C(C=C1)F)C OWMGURMREYGDAM-JWTNVVGKSA-N 0.000 claims 1
- XAXUJCHREYFUBA-UHFFFAOYSA-N 2-[3-[1-(2,3-dihydro-1H-indene-2-carbonyl)piperidin-4-yl]pyrrolo[2,3-c]pyridin-1-yl]-5-fluoro-N-methyl-N-propan-2-ylbenzamide Chemical compound C1C(CC2=CC=CC=C12)C(=O)N1CCC(CC1)C1=CN(C2=CN=CC=C21)C1=C(C(=O)N(C)C(C)C)C=C(C=C1)F XAXUJCHREYFUBA-UHFFFAOYSA-N 0.000 claims 1
- RCQFNPWOYDTKLE-UHFFFAOYSA-N 2-[3-[1-(cyclohexylmethyl)piperidin-3-yl]pyrrolo[2,3-c]pyridin-1-yl]-5-fluoro-N-methyl-N-propan-2-ylbenzamide Chemical compound C1(CCCCC1)CN1CC(CCC1)C1=CN(C2=CN=CC=C21)C1=C(C(=O)N(C)C(C)C)C=C(C=C1)F RCQFNPWOYDTKLE-UHFFFAOYSA-N 0.000 claims 1
- HWEKRJPBDJVSIZ-UHFFFAOYSA-N 2-[3-[1-[(2-chlorophenyl)methyl]piperidin-4-yl]pyrrolo[2,3-c]pyridin-1-yl]-5-fluoro-N-methyl-N-propan-2-ylbenzamide Chemical compound ClC1=C(CN2CCC(CC2)C2=CN(C3=CN=CC=C32)C2=C(C(=O)N(C)C(C)C)C=C(C=C2)F)C=CC=C1 HWEKRJPBDJVSIZ-UHFFFAOYSA-N 0.000 claims 1
- CIJIBZLZEMVRNN-UHFFFAOYSA-N 2-[3-[1-[(2-cyano-1H-indol-5-yl)methyl]piperidin-4-yl]pyrrolo[2,3-c]pyridin-1-yl]-5-fluoro-N-methyl-N-propan-2-ylbenzamide Chemical compound C(#N)C=1NC2=CC=C(C=C2C=1)CN1CCC(CC1)C1=CN(C2=CN=CC=C21)C1=C(C(=O)N(C)C(C)C)C=C(C=C1)F CIJIBZLZEMVRNN-UHFFFAOYSA-N 0.000 claims 1
- UUZMZNDGNAJKKG-UHFFFAOYSA-N 2-[3-[1-[(2-cyano-1H-indol-6-yl)methyl]piperidin-4-yl]pyrrolo[2,3-c]pyridin-1-yl]-5-fluoro-N-methyl-N-propan-2-ylbenzamide Chemical compound C(#N)C=1NC2=CC(=CC=C2C=1)CN1CCC(CC1)C1=CN(C2=CN=CC=C21)C1=C(C(=O)N(C)C(C)C)C=C(C=C1)F UUZMZNDGNAJKKG-UHFFFAOYSA-N 0.000 claims 1
- ZBQLAKASBVKIAV-UHFFFAOYSA-N 2-[3-[1-[(2-cyano-4-methyl-1H-indol-5-yl)methyl]piperidin-4-yl]pyrrolo[2,3-c]pyridin-1-yl]-5-fluoro-N-methyl-N-propan-2-ylbenzamide Chemical compound C(#N)C=1NC2=CC=C(C(=C2C=1)C)CN1CCC(CC1)C1=CN(C2=CN=CC=C21)C1=C(C(=O)N(C)C(C)C)C=C(C=C1)F ZBQLAKASBVKIAV-UHFFFAOYSA-N 0.000 claims 1
- VSASREGZPZLOKS-UHFFFAOYSA-N 2-[3-[1-[(3,3-difluorocyclobutyl)methyl]piperidin-4-yl]pyrrolo[2,3-c]pyridin-1-yl]-5-fluoro-N-methyl-N-propan-2-ylbenzamide Chemical compound FC1(CC(C1)CN1CCC(CC1)C1=CN(C2=CN=CC=C21)C1=C(C(=O)N(C)C(C)C)C=C(C=C1)F)F VSASREGZPZLOKS-UHFFFAOYSA-N 0.000 claims 1
- ZBGAIYIJDJITII-UHFFFAOYSA-N 2-[3-[1-[(3-cyano-3-methyl-2-oxo-1H-indol-6-yl)methyl]piperidin-3-yl]pyrrolo[2,3-c]pyridin-1-yl]-5-fluoro-N-methyl-N-propan-2-ylbenzamide Chemical compound C(#N)C1(C(NC2=CC(=CC=C12)CN1CC(CCC1)C1=CN(C2=CN=CC=C21)C1=C(C(=O)N(C)C(C)C)C=C(C=C1)F)=O)C ZBGAIYIJDJITII-UHFFFAOYSA-N 0.000 claims 1
- YXUSKCJKQISSTB-UHFFFAOYSA-N 2-[3-[1-[(4-acetamidophenyl)methyl]piperidin-4-yl]pyrrolo[2,3-c]pyridin-1-yl]-5-fluoro-N-methyl-N-propan-2-ylbenzamide Chemical compound C(C)(=O)NC1=CC=C(CN2CCC(CC2)C2=CN(C3=CN=CC=C32)C2=C(C(=O)N(C)C(C)C)C=C(C=C2)F)C=C1 YXUSKCJKQISSTB-UHFFFAOYSA-N 0.000 claims 1
- RIDIINLIWVJVHO-UHFFFAOYSA-N 2-[3-[1-[(4-chlorophenyl)methyl]piperidin-4-yl]pyrrolo[2,3-c]pyridin-1-yl]-5-fluoro-N-methyl-N-propan-2-ylbenzamide Chemical compound ClC1=CC=C(CN2CCC(CC2)C2=CN(C3=CN=CC=C32)C2=C(C(=O)N(C)C(C)C)C=C(C=C2)F)C=C1 RIDIINLIWVJVHO-UHFFFAOYSA-N 0.000 claims 1
- QPRVWBHQESZCNS-UHFFFAOYSA-N 2-[3-[1-[(4-cyanophenyl)methyl]piperidin-4-yl]pyrrolo[2,3-c]pyridin-1-yl]-5-fluoro-N-methyl-N-propan-2-ylbenzamide Chemical compound C(#N)C1=CC=C(CN2CCC(CC2)C2=CN(C3=CN=CC=C32)C2=C(C(=O)N(C)C(C)C)C=C(C=C2)F)C=C1 QPRVWBHQESZCNS-UHFFFAOYSA-N 0.000 claims 1
- PFKJUGUDCFJNPM-UHFFFAOYSA-N 2-[3-[1-[2-(3-cyanophenyl)ethyl]piperidin-4-yl]pyrrolo[2,3-c]pyridin-1-yl]-5-fluoro-N-methyl-N-propan-2-ylbenzamide Chemical compound C(#N)C=1C=C(CCN2CCC(CC2)C2=CN(C3=CN=CC=C32)C2=C(C(=O)N(C)C(C)C)C=C(C=C2)F)C=CC=1 PFKJUGUDCFJNPM-UHFFFAOYSA-N 0.000 claims 1
- CHFLZGSUOZVSDZ-UHFFFAOYSA-N 2-[3-[1-[2-[4-(2-cyanopropan-2-yl)phenyl]ethyl]piperidin-4-yl]pyrrolo[2,3-c]pyridin-1-yl]-5-fluoro-N-methyl-N-propan-2-ylbenzamide Chemical compound C(#N)C(C)(C)C1=CC=C(CCN2CCC(CC2)C2=CN(C3=CN=CC=C32)C2=C(C(=O)N(C)C(C)C)C=C(C=C2)F)C=C1 CHFLZGSUOZVSDZ-UHFFFAOYSA-N 0.000 claims 1
- NRPLUEYJMLPTMM-UHFFFAOYSA-N 2-[3-[4-(dimethylamino)cyclohexyl]pyrrolo[2,3-c]pyridin-1-yl]-5-fluoro-N-methyl-N-propan-2-ylbenzamide Chemical compound CN(C1CCC(CC1)C1=CN(C2=CN=CC=C21)C1=C(C(=O)N(C)C(C)C)C=C(C=C1)F)C NRPLUEYJMLPTMM-UHFFFAOYSA-N 0.000 claims 1
- XPQITFYEPCCQEK-VWLOTQADSA-N 2-[5-[[(3R)-3-[1-[4-fluoro-2-[methyl(propan-2-yl)carbamoyl]phenyl]pyrrolo[2,3-c]pyridin-3-yl]piperidin-1-yl]methyl]-2-oxo-3H-benzimidazol-1-yl]ethyl acetate Chemical compound C(C)(=O)OCCN1C(NC2=C1C=CC(=C2)CN1C[C@H](CCC1)C1=CN(C2=CN=CC=C21)C1=C(C=C(C=C1)F)C(N(C)C(C)C)=O)=O XPQITFYEPCCQEK-VWLOTQADSA-N 0.000 claims 1
- IYXMPYVGTQCCHR-FAIXQHPJSA-N 2-[5-[[(3R)-3-[1-[4-fluoro-2-[methyl(propan-2-yl)carbamoyl]phenyl]pyrrolo[2,3-c]pyridin-3-yl]piperidin-1-yl]methyl]-2-oxo-3H-benzimidazol-1-yl]ethyl octadecanoate Chemical compound C(CCCCCCCCCCCCCCCCC)(=O)OCCN1C(NC2=C1C=CC(=C2)CN1C[C@H](CCC1)C1=CN(C2=CN=CC=C21)C1=C(C=C(C=C1)F)C(N(C)C(C)C)=O)=O IYXMPYVGTQCCHR-FAIXQHPJSA-N 0.000 claims 1
- NOLZECYFLCHANA-UHFFFAOYSA-N 2-[7-[1-[(2-cyano-4-methyl-1H-indol-5-yl)methyl]piperidin-4-yl]pyrrolo[3,2-d]pyrimidin-5-yl]-5-fluoro-N,N-dimethylbenzamide Chemical compound C(#N)C=1NC2=CC=C(C(=C2C=1)C)CN1CCC(CC1)C1=CN(C2=C1N=CN=C2)C1=C(C(=O)N(C)C)C=C(C=C1)F NOLZECYFLCHANA-UHFFFAOYSA-N 0.000 claims 1
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- WULPVXMYNOYQCP-UHFFFAOYSA-N 5-fluoro-2-[3-[4-[2-(methanesulfonamido)-6-azaspiro[3.4]octan-6-yl]cyclohexyl]pyrrolo[2,3-c]pyridin-1-yl]-N,N-di(propan-2-yl)benzamide Chemical compound FC=1C=CC(=C(C(=O)N(C(C)C)C(C)C)C=1)N1C=C(C=2C1=CN=CC=2)C1CCC(CC1)N1CC2(CC(C2)NS(=O)(=O)C)CC1 WULPVXMYNOYQCP-UHFFFAOYSA-N 0.000 claims 1
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- RJPUEKPXGXOJEJ-UHFFFAOYSA-N 5-fluoro-N-methyl-2-[3-(2-methyl-3,4-dihydro-1H-isoquinolin-6-yl)pyrrolo[2,3-c]pyridin-1-yl]-N-propan-2-ylbenzamide Chemical compound FC=1C=CC(=C(C(=O)N(C)C(C)C)C=1)N1C=C(C=2C1=CN=CC=2)C=1C=C2CCN(CC2=CC=1)C RJPUEKPXGXOJEJ-UHFFFAOYSA-N 0.000 claims 1
- IIBSSCWXLRIVGA-UHFFFAOYSA-N 5-fluoro-N-methyl-2-[3-(4-phenoxycyclohexyl)pyrrolo[2,3-c]pyridin-1-yl]-N-propan-2-ylbenzamide Chemical compound FC=1C=CC(=C(C(=O)N(C)C(C)C)C=1)N1C=C(C=2C1=CN=CC=2)C1CCC(CC1)OC1=CC=CC=C1 IIBSSCWXLRIVGA-UHFFFAOYSA-N 0.000 claims 1
- NZSQKVQMNPCGEA-UHFFFAOYSA-N 5-fluoro-N-methyl-2-[3-[1-(1-phenylethyl)piperidin-4-yl]pyrrolo[2,3-c]pyridin-1-yl]-N-propan-2-ylbenzamide Chemical compound FC=1C=CC(=C(C(=O)N(C)C(C)C)C=1)N1C=C(C=2C1=CN=CC=2)C1CCN(CC1)C(C)C1=CC=CC=C1 NZSQKVQMNPCGEA-UHFFFAOYSA-N 0.000 claims 1
- TYLADDKSZMGEMN-UHFFFAOYSA-N 5-fluoro-N-methyl-2-[3-[1-(2-phenylacetyl)piperidin-4-yl]pyrrolo[2,3-c]pyridin-1-yl]-N-propan-2-ylbenzamide Chemical compound FC=1C=CC(=C(C(=O)N(C)C(C)C)C=1)N1C=C(C=2C1=CN=CC=2)C1CCN(CC1)C(CC1=CC=CC=C1)=O TYLADDKSZMGEMN-UHFFFAOYSA-N 0.000 claims 1
- VWDROPJYXWASPC-UHFFFAOYSA-N 5-fluoro-N-methyl-2-[3-[1-(oxan-4-ylmethyl)piperidin-4-yl]pyrrolo[2,3-c]pyridin-1-yl]-N-propan-2-ylbenzamide Chemical compound FC=1C=CC(=C(C(=O)N(C)C(C)C)C=1)N1C=C(C=2C1=CN=CC=2)C1CCN(CC1)CC1CCOCC1 VWDROPJYXWASPC-UHFFFAOYSA-N 0.000 claims 1
- NUTOOXDDEKBEIW-UHFFFAOYSA-N 5-fluoro-N-methyl-2-[3-[1-[(2-methylphenyl)methyl]piperidin-4-yl]pyrrolo[2,3-c]pyridin-1-yl]-N-propan-2-ylbenzamide Chemical compound FC=1C=CC(=C(C(=O)N(C)C(C)C)C=1)N1C=C(C=2C1=CN=CC=2)C1CCN(CC1)CC1=C(C=CC=C1)C NUTOOXDDEKBEIW-UHFFFAOYSA-N 0.000 claims 1
- FZZUAOXLWQTRIV-UHFFFAOYSA-N 5-fluoro-N-methyl-2-[3-[1-[(2-oxo-1,3-dihydrobenzimidazol-5-yl)methyl]piperidin-3-yl]pyrrolo[2,3-c]pyridin-1-yl]-N-propan-2-ylbenzamide Chemical compound FC=1C=CC(=C(C(=O)N(C)C(C)C)C=1)N1C=C(C=2C1=CN=CC=2)C1CN(CCC1)CC1=CC2=C(NC(N2)=O)C=C1 FZZUAOXLWQTRIV-UHFFFAOYSA-N 0.000 claims 1
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| NZ510587A (en) * | 1998-09-18 | 2003-11-28 | Abbott Gmbh & Co | 4-aminopyrrolopyrimidines as kinase inhibitors |
| AU2006239632B2 (en) | 2005-04-25 | 2012-03-15 | Merck Patent Gmbh | Novel AZA- heterocycles serving as kinase inhibitors |
| WO2010066629A2 (en) * | 2008-12-09 | 2010-06-17 | F. Hoffmann-La Roche Ag | Novel azaindoles |
| GB201004311D0 (en) * | 2010-03-15 | 2010-04-28 | Proximagen Ltd | New enzyme inhibitor compounds |
| TWI500617B (zh) * | 2010-05-31 | 2015-09-21 | Ono Pharmaceutical Co | Purine ketone derivatives |
| CN103958510B (zh) | 2011-10-03 | 2016-10-19 | 北卡罗来纳大学教堂山分校 | 用于治疗癌症的吡咯并嘧啶化合物 |
| US8377946B1 (en) * | 2011-12-30 | 2013-02-19 | Pharmacyclics, Inc. | Pyrazolo[3,4-d]pyrimidine and pyrrolo[2,3-d]pyrimidine compounds as kinase inhibitors |
| EP2878601B1 (en) * | 2012-07-27 | 2018-03-28 | Riken | Agent for treating or controlling recurrence of acute myelogenous leukemia |
| BR112015011171A2 (pt) | 2012-11-15 | 2017-07-11 | Pharmacyclics Inc | compostos de pirrolopirimidina como inibidores da quinase |
| WO2014199171A1 (en) * | 2013-06-12 | 2014-12-18 | Proximagen Limited | New therapeutic uses of enzyme inhibitors |
| EP3057970A1 (en) * | 2013-10-18 | 2016-08-24 | Medivation Technologies, Inc. | Heterocyclic compounds and methods of use |
| EP3269367B1 (en) | 2015-03-11 | 2020-10-07 | Riken | Therapeutic agent for intractable leukemia |
| MX2019003091A (es) * | 2016-09-16 | 2019-07-08 | Vitae Pharmaceuticals Inc | Inhibidores de la interaccion de menina-mll. |
-
2017
- 2017-09-15 MX MX2019003091A patent/MX2019003091A/es unknown
- 2017-09-15 JP JP2019514787A patent/JP2019529421A/ja not_active Withdrawn
- 2017-09-15 ES ES17772585T patent/ES2948949T3/es active Active
- 2017-09-15 AR ARP170102556A patent/AR109658A1/es active IP Right Grant
- 2017-09-15 EP EP17772585.0A patent/EP3512850B1/en active Active
- 2017-09-15 WO PCT/US2017/051780 patent/WO2018053267A1/en not_active Ceased
- 2017-09-15 CN CN201780063763.2A patent/CN110325533B/zh active Active
- 2017-09-15 CN CN202410398451.9A patent/CN118359610A/zh active Pending
- 2017-09-15 EP EP23167055.5A patent/EP4230627A3/en active Pending
- 2017-09-15 FI FIEP17772585.0T patent/FI3512850T3/fi active
- 2017-09-15 PL PL17772585.0T patent/PL3512850T3/pl unknown
- 2017-09-15 US US16/333,852 patent/US10899758B2/en active Active
- 2017-09-15 IL IL265028A patent/IL265028B/en unknown
- 2017-09-15 CA CA3036987A patent/CA3036987A1/en active Pending
- 2017-09-15 IL IL295972A patent/IL295972A/en unknown
- 2017-09-15 AU AU2017326006A patent/AU2017326006B2/en active Active
- 2017-09-15 DK DK17772585.0T patent/DK3512850T3/da active
- 2017-09-15 KR KR1020197010730A patent/KR102536029B1/ko active Active
- 2017-09-15 TW TW106131767A patent/TWI757340B/zh active
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2019
- 2019-03-15 MX MX2022013841A patent/MX2022013841A/es unknown
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2020
- 2020-08-11 US US16/990,657 patent/US11739085B2/en active Active
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2022
- 2022-10-06 JP JP2022161777A patent/JP2022189853A/ja active Pending
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2023
- 2023-05-18 US US18/320,111 patent/US20240124447A1/en not_active Abandoned
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2024
- 2024-11-08 JP JP2024195965A patent/JP2025022910A/ja active Pending
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