JP2013519707A5 - - Google Patents
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- JP2013519707A5 JP2013519707A5 JP2012553318A JP2012553318A JP2013519707A5 JP 2013519707 A5 JP2013519707 A5 JP 2013519707A5 JP 2012553318 A JP2012553318 A JP 2012553318A JP 2012553318 A JP2012553318 A JP 2012553318A JP 2013519707 A5 JP2013519707 A5 JP 2013519707A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrrolo
- pyrimidine
- ylamino
- pyridin
- cyclopentyl
- 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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- FJWYXWJQDPCIEZ-UHFFFAOYSA-N 7-cyclopentyl-2-[[5-(3,8-diazabicyclo[3.2.1]octane-3-carbonyl)pyridin-2-yl]amino]-n,n-dimethylpyrrolo[2,3-d]pyrimidine-6-carboxamide Chemical compound CN(C)C(=O)C1=CC2=CN=C(NC=3N=CC(=CC=3)C(=O)N3CC4CCC(N4)C3)N=C2N1C1CCCC1 FJWYXWJQDPCIEZ-UHFFFAOYSA-N 0.000 claims description 3
- PBGMYLLXSOFMTR-ZWKOTPCHSA-N 7-cyclopentyl-n,n-dimethyl-2-[[5-[(1s,6r)-3-oxo-4,9-diazabicyclo[4.2.1]nonan-4-yl]pyridin-2-yl]amino]pyrrolo[2,3-d]pyrimidine-6-carboxamide Chemical compound C([C@@]1(CC[C@](C2)(N1)[H])[H])C(=O)N2C(C=N1)=CC=C1NC(N=C12)=NC=C1C=C(C(=O)N(C)C)N2C1CCCC1 PBGMYLLXSOFMTR-ZWKOTPCHSA-N 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims 33
- 150000001875 compounds Chemical class 0.000 claims 30
- 229910052757 nitrogen Inorganic materials 0.000 claims 24
- 125000000217 alkyl group Chemical group 0.000 claims 18
- -1 5- (9-hydroxy-1,5,7-trimethyl-3,7-diazabicyclo [3.3.1] nonane-3-carbonyl) pyridin-2-ylamino Chemical group 0.000 claims 15
- 206010028980 Neoplasm Diseases 0.000 claims 12
- 201000011510 cancer Diseases 0.000 claims 10
- 125000001424 substituent group Chemical group 0.000 claims 9
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 4
- 229910052805 deuterium Inorganic materials 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- ZDRGTMWWJMXNIG-JGAZGGJJSA-N O=C1C[C@@H]2[C@H](CN1C=1C=CC(=NC1)NC=1N=CC3=C(N1)NC(=C3)C(=O)N)CNC2.CN(C2=CC=CC=C2)C Chemical compound O=C1C[C@@H]2[C@H](CN1C=1C=CC(=NC1)NC=1N=CC3=C(N1)NC(=C3)C(=O)N)CNC2.CN(C2=CC=CC=C2)C ZDRGTMWWJMXNIG-JGAZGGJJSA-N 0.000 claims 3
- 239000004480 active ingredient Substances 0.000 claims 3
- 239000000654 additive Substances 0.000 claims 3
- 230000000996 additive effect Effects 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 239000003937 drug carrier Substances 0.000 claims 3
- 201000001441 melanoma Diseases 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 229940124597 therapeutic agent Drugs 0.000 claims 3
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 206010025323 Lymphomas Diseases 0.000 claims 2
- 208000025205 Mantle-Cell Lymphoma Diseases 0.000 claims 2
- 208000034578 Multiple myelomas Diseases 0.000 claims 2
- 206010035226 Plasma cell myeloma Diseases 0.000 claims 2
- 206010042971 T-cell lymphoma Diseases 0.000 claims 2
- 208000027585 T-cell non-Hodgkin lymphoma Diseases 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 210000004027 cell Anatomy 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 2
- 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 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 210000003739 neck Anatomy 0.000 claims 2
- 125000004043 oxo group Chemical group O=* 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 2
- 210000001685 thyroid gland Anatomy 0.000 claims 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- JCRUSEOGJUANIE-UHFFFAOYSA-N 2-[[5-(3,4,6,7,8,8a-hexahydro-1h-pyrrolo[1,2-a]pyrazine-2-carbonyl)pyridin-2-yl]amino]-7-cyclopentyl-n,n-dimethylpyrrolo[2,3-d]pyrimidine-6-carboxamide Chemical compound CN(C)C(=O)C1=CC2=CN=C(NC=3N=CC(=CC=3)C(=O)N3CC4CCCN4CC3)N=C2N1C1CCCC1 JCRUSEOGJUANIE-UHFFFAOYSA-N 0.000 claims 1
- WBCAOAIDJLJRCZ-UHFFFAOYSA-N 7-(3-tert-butylphenyl)-2-[[5-(3,8-diazabicyclo[3.2.1]octane-3-carbonyl)pyridin-2-yl]amino]-n,n-dimethylpyrrolo[2,3-d]pyrimidine-6-carboxamide Chemical compound CN(C)C(=O)C1=CC2=CN=C(NC=3N=CC(=CC=3)C(=O)N3CC4CCC(N4)C3)N=C2N1C1=CC=CC(C(C)(C)C)=C1 WBCAOAIDJLJRCZ-UHFFFAOYSA-N 0.000 claims 1
- VTSDFHMWTKRCAL-UHFFFAOYSA-N 7-(4-tert-butylphenyl)-2-[[5-(3,8-diazabicyclo[3.2.1]octane-3-carbonyl)pyridin-2-yl]amino]-n,n-dimethylpyrrolo[2,3-d]pyrimidine-6-carboxamide Chemical compound CN(C)C(=O)C1=CC2=CN=C(NC=3N=CC(=CC=3)C(=O)N3CC4CCC(N4)C3)N=C2N1C1=CC=C(C(C)(C)C)C=C1 VTSDFHMWTKRCAL-UHFFFAOYSA-N 0.000 claims 1
- YYUJVQQJCJMRSG-UHFFFAOYSA-N 7-[4-(2-cyanopropan-2-yl)phenyl]-2-[[5-(3,8-diazabicyclo[3.2.1]octane-8-carbonyl)pyridin-2-yl]amino]-n,n-dimethylpyrrolo[2,3-d]pyrimidine-6-carboxamide Chemical compound CN(C)C(=O)C1=CC2=CN=C(NC=3N=CC(=CC=3)C(=O)N3C4CCC3CNC4)N=C2N1C1=CC=C(C(C)(C)C#N)C=C1 YYUJVQQJCJMRSG-UHFFFAOYSA-N 0.000 claims 1
- HBBBOMMFSYNTJJ-SJORKVTESA-N 7-cyclobutyl-n,n-dimethyl-2-[[5-[(1r,6s)-3-oxo-4,9-diazabicyclo[4.2.1]nonan-4-yl]pyridin-2-yl]amino]pyrrolo[2,3-d]pyrimidine-6-carboxamide Chemical compound C([C@]1(CC[C@@](C2)(N1)[H])[H])C(=O)N2C(C=N1)=CC=C1NC(N=C12)=NC=C1C=C(C(=O)N(C)C)N2C1CCC1 HBBBOMMFSYNTJJ-SJORKVTESA-N 0.000 claims 1
- QVFRZHXKIZTYEZ-UHFFFAOYSA-N 7-cycloheptyl-2-[[5-(2,5-diazabicyclo[2.2.1]heptane-2-carbonyl)pyridin-2-yl]amino]-n,n-dimethylpyrrolo[2,3-d]pyrimidine-6-carboxamide Chemical compound CN(C)C(=O)C1=CC2=CN=C(NC=3N=CC(=CC=3)C(=O)N3C4CC(NC4)C3)N=C2N1C1CCCCCC1 QVFRZHXKIZTYEZ-UHFFFAOYSA-N 0.000 claims 1
- KSBSIXFKBIRVML-RBUKOAKNSA-N 7-cyclohexyl-n,n-dimethyl-2-[[5-[(1s,6r)-3-oxo-4,9-diazabicyclo[4.2.1]nonan-4-yl]pyridin-2-yl]amino]pyrrolo[2,3-d]pyrimidine-6-carboxamide Chemical compound C([C@@]1(CC[C@](C2)(N1)[H])[H])C(=O)N2C(C=N1)=CC=C1NC(N=C12)=NC=C1C=C(C(=O)N(C)C)N2C1CCCCC1 KSBSIXFKBIRVML-RBUKOAKNSA-N 0.000 claims 1
- VMHOCSPSLUBLHE-UHFFFAOYSA-N 7-cyclopentyl-2-[[5-(3,6-diazabicyclo[3.2.1]octane-3-carbonyl)pyridin-2-yl]amino]-n,n-dimethylpyrrolo[2,3-d]pyrimidine-6-carboxamide Chemical compound CN(C)C(=O)C1=CC2=CN=C(NC=3N=CC(=CC=3)C(=O)N3CC4NCC(C4)C3)N=C2N1C1CCCC1 VMHOCSPSLUBLHE-UHFFFAOYSA-N 0.000 claims 1
- MGVGOHXTHDTWHQ-UHFFFAOYSA-N 7-cyclopentyl-2-[[5-(3,8-diazabicyclo[3.2.1]octane-3-carbonyl)-4-methylpyridin-2-yl]amino]-n,n-dimethylpyrrolo[2,3-d]pyrimidine-6-carboxamide Chemical compound CN(C)C(=O)C1=CC2=CN=C(NC=3N=CC(=C(C)C=3)C(=O)N3CC4CCC(N4)C3)N=C2N1C1CCCC1 MGVGOHXTHDTWHQ-UHFFFAOYSA-N 0.000 claims 1
- SOBQJDMKGXGEQA-UHFFFAOYSA-N 7-cyclopentyl-2-[[5-(3,8-diazabicyclo[3.2.1]octane-3-carbonyl)-6-methylpyridin-2-yl]amino]-n,n-dimethylpyrrolo[2,3-d]pyrimidine-6-carboxamide Chemical compound CN(C)C(=O)C1=CC2=CN=C(NC=3N=C(C)C(C(=O)N4CC5CCC(N5)C4)=CC=3)N=C2N1C1CCCC1 SOBQJDMKGXGEQA-UHFFFAOYSA-N 0.000 claims 1
- QUGUCRTXIGFAAB-UHFFFAOYSA-N 7-cyclopentyl-2-[[5-(3,8-diazabicyclo[3.2.1]octane-8-carbonyl)pyridin-2-yl]amino]-n,n-dimethylpyrrolo[2,3-d]pyrimidine-6-carboxamide Chemical compound CN(C)C(=O)C1=CC2=CN=C(NC=3N=CC(=CC=3)C(=O)N3C4CCC3CNC4)N=C2N1C1CCCC1 QUGUCRTXIGFAAB-UHFFFAOYSA-N 0.000 claims 1
- IUMNOHMCVRQIFR-UHFFFAOYSA-N 7-cyclopentyl-2-[[5-(3,9-diazabicyclo[3.3.1]nonane-3-carbonyl)pyridin-2-yl]amino]-n,n-dimethylpyrrolo[2,3-d]pyrimidine-6-carboxamide Chemical compound CN(C)C(=O)C1=CC2=CN=C(NC=3N=CC(=CC=3)C(=O)N3CC4CCCC(N4)C3)N=C2N1C1CCCC1 IUMNOHMCVRQIFR-UHFFFAOYSA-N 0.000 claims 1
- JMYHPWJJCGPKPL-UXHICEINSA-N 7-cyclopentyl-2-[[5-[(1r,6s)-4,9-diazabicyclo[4.2.1]nonane-4-carbonyl]pyridin-2-yl]amino]-n,n-dimethylpyrrolo[2,3-d]pyrimidine-6-carboxamide Chemical compound C([C@@]1(CC[C@](CC2)(N1)[H])[H])N2C(=O)C(C=N1)=CC=C1NC(N=C12)=NC=C1C=C(C(=O)N(C)C)N2C1CCCC1 JMYHPWJJCGPKPL-UXHICEINSA-N 0.000 claims 1
- LCQFIXPBRDGHGG-HKUYNNGSSA-N 7-cyclopentyl-2-[[5-[(1s,4s)-2,5-diazabicyclo[2.2.1]heptane-2-carbonyl]pyridin-2-yl]amino]-n,n-dimethylpyrrolo[2,3-d]pyrimidine-6-carboxamide Chemical compound C([C@]1(NC[C@]2([H])C1)[H])N2C(=O)C(C=N1)=CC=C1NC(N=C12)=NC=C1C=C(C(=O)N(C)C)N2C1CCCC1 LCQFIXPBRDGHGG-HKUYNNGSSA-N 0.000 claims 1
- JMYHPWJJCGPKPL-VQTJNVASSA-N 7-cyclopentyl-2-[[5-[(1s,6r)-4,9-diazabicyclo[4.2.1]nonane-4-carbonyl]pyridin-2-yl]amino]-n,n-dimethylpyrrolo[2,3-d]pyrimidine-6-carboxamide Chemical compound C([C@]1(CC[C@@](CC2)(N1)[H])[H])N2C(=O)C(C=N1)=CC=C1NC(N=C12)=NC=C1C=C(C(=O)N(C)C)N2C1CCCC1 JMYHPWJJCGPKPL-VQTJNVASSA-N 0.000 claims 1
- UHLMUTYUXRIVIZ-UHFFFAOYSA-N 7-cyclopentyl-n,n-dimethyl-2-[[5-(1-oxo-3,4,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazin-2-yl)pyridin-2-yl]amino]pyrrolo[2,3-d]pyrimidine-6-carboxamide Chemical compound CN(C)C(=O)C1=CC2=CN=C(NC=3N=CC(=CC=3)N3C(C4CCCN4CC3)=O)N=C2N1C1CCCC1 UHLMUTYUXRIVIZ-UHFFFAOYSA-N 0.000 claims 1
- PBGMYLLXSOFMTR-UHFFFAOYSA-N 7-cyclopentyl-n,n-dimethyl-2-[[5-(3-oxo-4,9-diazabicyclo[4.2.1]nonan-4-yl)pyridin-2-yl]amino]pyrrolo[2,3-d]pyrimidine-6-carboxamide Chemical compound CN(C)C(=O)C1=CC2=CN=C(NC=3N=CC(=CC=3)N3C(CC4CCC(N4)C3)=O)N=C2N1C1CCCC1 PBGMYLLXSOFMTR-UHFFFAOYSA-N 0.000 claims 1
- RGGRAERHROXLKH-UHFFFAOYSA-N 7-cyclopentyl-n,n-dimethyl-2-[[5-(8-methyl-3,8-diazabicyclo[3.2.1]octane-3-carbonyl)pyridin-2-yl]amino]pyrrolo[2,3-d]pyrimidine-6-carboxamide Chemical compound CN(C)C(=O)C1=CC2=CN=C(NC=3N=CC(=CC=3)C(=O)N3CC4CCC(N4C)C3)N=C2N1C1CCCC1 RGGRAERHROXLKH-UHFFFAOYSA-N 0.000 claims 1
- GAAOQIXOPLWYKD-AREMUKBSSA-N 7-cyclopentyl-n,n-dimethyl-2-[[5-[(5r)-2-oxo-1-oxa-3,9-diazaspiro[4.5]decan-3-yl]pyridin-2-yl]amino]pyrrolo[2,3-d]pyrimidine-6-carboxamide Chemical compound N1=C2N(C3CCCC3)C(C(=O)N(C)C)=CC2=CN=C1NC(N=C1)=CC=C1N(C(O1)=O)C[C@@]21CCCNC2 GAAOQIXOPLWYKD-AREMUKBSSA-N 0.000 claims 1
- GAAOQIXOPLWYKD-SANMLTNESA-N 7-cyclopentyl-n,n-dimethyl-2-[[5-[(5s)-2-oxo-1-oxa-3,9-diazaspiro[4.5]decan-3-yl]pyridin-2-yl]amino]pyrrolo[2,3-d]pyrimidine-6-carboxamide Chemical compound N1=C2N(C3CCCC3)C(C(=O)N(C)C)=CC2=CN=C1NC(N=C1)=CC=C1N(C(O1)=O)C[C@]21CCCNC2 GAAOQIXOPLWYKD-SANMLTNESA-N 0.000 claims 1
- 208000024893 Acute lymphoblastic leukemia Diseases 0.000 claims 1
- 208000014697 Acute lymphocytic leukaemia Diseases 0.000 claims 1
- 206010003571 Astrocytoma Diseases 0.000 claims 1
- 208000010839 B-cell chronic lymphocytic leukemia Diseases 0.000 claims 1
- 208000003950 B-cell lymphoma Diseases 0.000 claims 1
- 206010006187 Breast cancer Diseases 0.000 claims 1
- 208000026310 Breast neoplasm Diseases 0.000 claims 1
- KXGOPETVBIUYIZ-RDJZCZTQSA-N C1(CCCC1)N1C(=CC2=C1N=C(N=C2)NC1=NC=C(C=C1)C(=O)N1[C@@H]2CN[C@H](C1)C2)C(=O)O Chemical compound C1(CCCC1)N1C(=CC2=C1N=C(N=C2)NC1=NC=C(C=C1)C(=O)N1[C@@H]2CN[C@H](C1)C2)C(=O)O KXGOPETVBIUYIZ-RDJZCZTQSA-N 0.000 claims 1
- YFEWOOFDUZLOIC-KGLIPLIRSA-N CN(C)C(C(N1)=CC2=C1N=C(NC(C=C1)=NC=C1N(C[C@H](CC1)N[C@H]1C1)C1=O)N=C2)=O Chemical compound CN(C)C(C(N1)=CC2=C1N=C(NC(C=C1)=NC=C1N(C[C@H](CC1)N[C@H]1C1)C1=O)N=C2)=O YFEWOOFDUZLOIC-KGLIPLIRSA-N 0.000 claims 1
- HYBFEEHWCKOPDK-LOCPCMAASA-N CN1C[C@@H]2[C@H](C1)CN(C2=O)C=2C=CC(=NC2)NC=2N=CC1=C(N2)NC(=C1)C(=O)N.CN(C1=CC=CC=C1)C Chemical compound CN1C[C@@H]2[C@H](C1)CN(C2=O)C=2C=CC(=NC2)NC=2N=CC1=C(N2)NC(=C1)C(=O)N.CN(C1=CC=CC=C1)C HYBFEEHWCKOPDK-LOCPCMAASA-N 0.000 claims 1
- 208000000461 Esophageal Neoplasms Diseases 0.000 claims 1
- 201000008808 Fibrosarcoma Diseases 0.000 claims 1
- 208000004463 Follicular Adenocarcinoma Diseases 0.000 claims 1
- 208000032612 Glial tumor Diseases 0.000 claims 1
- 201000010915 Glioblastoma multiforme Diseases 0.000 claims 1
- 206010018338 Glioma Diseases 0.000 claims 1
- 208000017604 Hodgkin disease Diseases 0.000 claims 1
- 208000021519 Hodgkin lymphoma Diseases 0.000 claims 1
- 208000010747 Hodgkins lymphoma Diseases 0.000 claims 1
- 208000007766 Kaposi sarcoma Diseases 0.000 claims 1
- 206010023347 Keratoacanthoma Diseases 0.000 claims 1
- 208000031671 Large B-Cell Diffuse Lymphoma Diseases 0.000 claims 1
- 208000031422 Lymphocytic Chronic B-Cell Leukemia Diseases 0.000 claims 1
- DQLSKESTXRBFDP-UHFFFAOYSA-N N-methyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide Chemical compound CNC(=O)C1=CC2=C(N=CN=C2)N1 DQLSKESTXRBFDP-UHFFFAOYSA-N 0.000 claims 1
- 206010029260 Neuroblastoma Diseases 0.000 claims 1
- 208000015914 Non-Hodgkin lymphomas Diseases 0.000 claims 1
- JBXOTMIKJBDPAN-UHFFFAOYSA-N O=C1CC2(CN1C=1C=CC(=NC1)NC=1N=CC3=C(N1)NC(=C3)C(=O)N)CC3CCC(C2)N3.CN(C3=CC=CC=C3)C Chemical compound O=C1CC2(CN1C=1C=CC(=NC1)NC=1N=CC3=C(N1)NC(=C3)C(=O)N)CC3CCC(C2)N3.CN(C3=CC=CC=C3)C JBXOTMIKJBDPAN-UHFFFAOYSA-N 0.000 claims 1
- HTYLRIVMHDTPTG-MHDYBILJSA-N O=C1N(C[C@@H]2[C@H]1CNC2)C=2C=CC(=NC2)NC=2N=CC1=C(N2)NC(=C1)C(=O)N.CN(C1=CC=CC=C1)C Chemical compound O=C1N(C[C@@H]2[C@H]1CNC2)C=2C=CC(=NC2)NC=2N=CC1=C(N2)NC(=C1)C(=O)N.CN(C1=CC=CC=C1)C HTYLRIVMHDTPTG-MHDYBILJSA-N 0.000 claims 1
- HTYLRIVMHDTPTG-JGAZGGJJSA-N O=C1N(C[C@H]2[C@@H]1CNC2)C=2C=CC(=NC2)NC=2N=CC1=C(N2)NC(=C1)C(=O)N.CN(C1=CC=CC=C1)C Chemical compound O=C1N(C[C@H]2[C@@H]1CNC2)C=2C=CC(=NC2)NC=2N=CC1=C(N2)NC(=C1)C(=O)N.CN(C1=CC=CC=C1)C HTYLRIVMHDTPTG-JGAZGGJJSA-N 0.000 claims 1
- IPDGOMUDPWXKHK-UHFFFAOYSA-N O=C1OC2(CN1C=1C=CC(=NC1)NC=1N=CC3=C(N1)NC(=C3)C(=O)N)CCNCC2.CN(C2=CC=CC=C2)C Chemical compound O=C1OC2(CN1C=1C=CC(=NC1)NC=1N=CC3=C(N1)NC(=C3)C(=O)N)CCNCC2.CN(C2=CC=CC=C2)C IPDGOMUDPWXKHK-UHFFFAOYSA-N 0.000 claims 1
- ZXNFGCLFKLHORU-UHFFFAOYSA-N O=C1OC2(CN1C=1C=CC(=NC1)NC=1N=CC3=C(N1)NC(=C3)C(=O)N)CNCCC2.CN(C2=CC=CC=C2)C Chemical compound O=C1OC2(CN1C=1C=CC(=NC1)NC=1N=CC3=C(N1)NC(=C3)C(=O)N)CNCCC2.CN(C2=CC=CC=C2)C ZXNFGCLFKLHORU-UHFFFAOYSA-N 0.000 claims 1
- 206010030155 Oesophageal carcinoma Diseases 0.000 claims 1
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims 1
- 208000006664 Precursor Cell Lymphoblastic Leukemia-Lymphoma Diseases 0.000 claims 1
- 206010060862 Prostate cancer Diseases 0.000 claims 1
- 201000000582 Retinoblastoma Diseases 0.000 claims 1
- 206010039491 Sarcoma Diseases 0.000 claims 1
- 201000010208 Seminoma Diseases 0.000 claims 1
- 210000001744 T-lymphocyte Anatomy 0.000 claims 1
- 201000006083 Xeroderma Pigmentosum Diseases 0.000 claims 1
- BVCRERJDOOBZOH-UHFFFAOYSA-N bicyclo[2.2.1]heptanyl Chemical group C1C[C+]2CC[C-]1C2 BVCRERJDOOBZOH-UHFFFAOYSA-N 0.000 claims 1
- 210000000481 breast Anatomy 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 210000003169 central nervous system Anatomy 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 208000032852 chronic lymphocytic leukemia Diseases 0.000 claims 1
- 230000001886 ciliary effect Effects 0.000 claims 1
- 210000001072 colon Anatomy 0.000 claims 1
- 208000035250 cutaneous malignant susceptibility to 1 melanoma Diseases 0.000 claims 1
- 206010012818 diffuse large B-cell lymphoma Diseases 0.000 claims 1
- 210000002615 epidermis Anatomy 0.000 claims 1
- 201000004101 esophageal cancer Diseases 0.000 claims 1
- 210000003238 esophagus Anatomy 0.000 claims 1
- 201000000497 familial melanoma Diseases 0.000 claims 1
- 230000003325 follicular Effects 0.000 claims 1
- 210000000232 gallbladder Anatomy 0.000 claims 1
- 208000005017 glioblastoma Diseases 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 210000003128 head Anatomy 0.000 claims 1
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2014
- 2014-12-12 US US14/568,410 patent/US9309252B2/en active Active
-
2015
- 2015-10-28 SM SM201500265T patent/SMT201500265B/it unknown
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