JP2011516536A5 - - Google Patents
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- Publication number
- JP2011516536A5 JP2011516536A5 JP2011503505A JP2011503505A JP2011516536A5 JP 2011516536 A5 JP2011516536 A5 JP 2011516536A5 JP 2011503505 A JP2011503505 A JP 2011503505A JP 2011503505 A JP2011503505 A JP 2011503505A JP 2011516536 A5 JP2011516536 A5 JP 2011516536A5
- Authority
- JP
- Japan
- Prior art keywords
- cancer
- methyl
- isopropyl
- piperazin
- ylmethyl
- 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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- 150000001875 compounds Chemical class 0.000 claims 16
- 229910052739 hydrogen Inorganic materials 0.000 claims 14
- 239000001257 hydrogen Substances 0.000 claims 14
- 125000000217 alkyl group Chemical group 0.000 claims 13
- 206010028980 Neoplasm Diseases 0.000 claims 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 9
- 125000000623 heterocyclic group Chemical group 0.000 claims 9
- 201000011510 cancer Diseases 0.000 claims 8
- 229910052757 nitrogen Inorganic materials 0.000 claims 8
- 229910052717 sulfur Inorganic materials 0.000 claims 8
- 150000001204 N-oxides Chemical class 0.000 claims 7
- 150000003839 salts Chemical class 0.000 claims 7
- 239000012453 solvate Substances 0.000 claims 7
- 201000001441 melanoma Diseases 0.000 claims 6
- -1 4-methyl-piperazin-1-ylmethyl Chemical group 0.000 claims 5
- 206010009944 Colon cancer Diseases 0.000 claims 5
- 150000002431 hydrogen Chemical class 0.000 claims 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 4
- 208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 claims 4
- 208000010833 Chronic myeloid leukaemia Diseases 0.000 claims 4
- 208000033761 Myelogenous Chronic BCR-ABL Positive Leukemia Diseases 0.000 claims 4
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims 4
- 206010060862 Prostate cancer Diseases 0.000 claims 4
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 4
- 206010041067 Small cell lung cancer Diseases 0.000 claims 4
- 208000024770 Thyroid neoplasm Diseases 0.000 claims 4
- 125000005842 heteroatom Chemical group 0.000 claims 4
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims 4
- 208000002154 non-small cell lung carcinoma Diseases 0.000 claims 4
- 125000004043 oxo group Chemical group O=* 0.000 claims 4
- 201000002528 pancreatic cancer Diseases 0.000 claims 4
- 208000008443 pancreatic carcinoma Diseases 0.000 claims 4
- 208000000587 small cell lung carcinoma Diseases 0.000 claims 4
- 201000002510 thyroid cancer Diseases 0.000 claims 4
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims 4
- 208000001333 Colorectal Neoplasms Diseases 0.000 claims 3
- 208000032612 Glial tumor Diseases 0.000 claims 3
- 206010018338 Glioma Diseases 0.000 claims 3
- 206010027480 Metastatic malignant melanoma Diseases 0.000 claims 3
- 210000004027 cell Anatomy 0.000 claims 3
- 201000011243 gastrointestinal stromal tumor Diseases 0.000 claims 3
- GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical group C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 claims 3
- 208000032839 leukemia Diseases 0.000 claims 3
- 208000021039 metastatic melanoma Diseases 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 3
- 208000024893 Acute lymphoblastic leukemia Diseases 0.000 claims 2
- 208000014697 Acute lymphocytic leukaemia Diseases 0.000 claims 2
- 208000036762 Acute promyelocytic leukaemia Diseases 0.000 claims 2
- 206010003571 Astrocytoma Diseases 0.000 claims 2
- 208000003950 B-cell lymphoma Diseases 0.000 claims 2
- 206010005003 Bladder cancer Diseases 0.000 claims 2
- 206010006187 Breast cancer Diseases 0.000 claims 2
- 208000026310 Breast neoplasm Diseases 0.000 claims 2
- 208000011691 Burkitt lymphomas Diseases 0.000 claims 2
- 201000009030 Carcinoma Diseases 0.000 claims 2
- 208000000461 Esophageal Neoplasms Diseases 0.000 claims 2
- 208000006168 Ewing Sarcoma Diseases 0.000 claims 2
- 201000008808 Fibrosarcoma Diseases 0.000 claims 2
- 206010051066 Gastrointestinal stromal tumour Diseases 0.000 claims 2
- 102100034051 Heat shock protein HSP 90-alpha Human genes 0.000 claims 2
- 208000017604 Hodgkin disease Diseases 0.000 claims 2
- 208000021519 Hodgkin lymphoma Diseases 0.000 claims 2
- 208000010747 Hodgkins lymphoma Diseases 0.000 claims 2
- 101001016865 Homo sapiens Heat shock protein HSP 90-alpha Proteins 0.000 claims 2
- 208000008839 Kidney Neoplasms Diseases 0.000 claims 2
- 239000005517 L01XE01 - Imatinib Substances 0.000 claims 2
- 208000031671 Large B-Cell Diffuse Lymphoma Diseases 0.000 claims 2
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 2
- 206010025323 Lymphomas Diseases 0.000 claims 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 2
- 208000034578 Multiple myelomas Diseases 0.000 claims 2
- 201000003793 Myelodysplastic syndrome Diseases 0.000 claims 2
- 208000014767 Myeloproliferative disease Diseases 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
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-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
- 206010038019 Rectal adenocarcinoma Diseases 0.000 claims 2
- 206010048829 Rectal adenoma Diseases 0.000 claims 2
- 206010038389 Renal cancer Diseases 0.000 claims 2
- 208000000453 Skin Neoplasms Diseases 0.000 claims 2
- 208000005718 Stomach Neoplasms 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
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims 2
- SZQAMLOTJYQITA-UHFFFAOYSA-N [5-hydroxy-4-[5-[(4-methylpiperazin-1-yl)methyl]-1,3-dihydroisoindole-2-carbonyl]-2-propan-2-ylphenyl] n,n-dimethylcarbamate Chemical compound C1=C(OC(=O)N(C)C)C(C(C)C)=CC(C(=O)N2CC3=CC(CN4CCN(C)CC4)=CC=C3C2)=C1O SZQAMLOTJYQITA-UHFFFAOYSA-N 0.000 claims 2
- 208000009956 adenocarcinoma Diseases 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- GXJABQQUPOEUTA-RDJZCZTQSA-N bortezomib Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)B(O)O)NC(=O)C=1N=CC=NC=1)C1=CC=CC=C1 GXJABQQUPOEUTA-RDJZCZTQSA-N 0.000 claims 2
- 229960001467 bortezomib Drugs 0.000 claims 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 201000007455 central nervous system cancer Diseases 0.000 claims 2
- 208000025997 central nervous system neoplasm Diseases 0.000 claims 2
- 230000001886 ciliary effect Effects 0.000 claims 2
- 208000029742 colonic neoplasm Diseases 0.000 claims 2
- 208000035250 cutaneous malignant susceptibility to 1 melanoma Diseases 0.000 claims 2
- 206010012818 diffuse large B-cell lymphoma Diseases 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 210000002615 epidermis Anatomy 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
- 206010017758 gastric cancer Diseases 0.000 claims 2
- 208000005017 glioblastoma Diseases 0.000 claims 2
- 201000005787 hematologic cancer Diseases 0.000 claims 2
- 208000019691 hematopoietic and lymphoid cell neoplasm Diseases 0.000 claims 2
- 208000024200 hematopoietic and lymphoid system neoplasm Diseases 0.000 claims 2
- 208000029824 high grade glioma Diseases 0.000 claims 2
- KTUFNOKKBVMGRW-UHFFFAOYSA-N imatinib Chemical compound C1CN(C)CCN1CC1=CC=C(C(=O)NC=2C=C(NC=3N=C(C=CN=3)C=3C=NC=CC=3)C(C)=CC=2)C=C1 KTUFNOKKBVMGRW-UHFFFAOYSA-N 0.000 claims 2
- 229960002411 imatinib Drugs 0.000 claims 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 201000010982 kidney cancer Diseases 0.000 claims 2
- 201000007270 liver cancer Diseases 0.000 claims 2
- 208000014018 liver neoplasm Diseases 0.000 claims 2
- 201000005202 lung cancer Diseases 0.000 claims 2
- 208000020816 lung neoplasm Diseases 0.000 claims 2
- 210000004698 lymphocyte Anatomy 0.000 claims 2
- 230000003211 malignant effect Effects 0.000 claims 2
- 201000011614 malignant glioma Diseases 0.000 claims 2
- 201000008806 mesenchymal cell neoplasm Diseases 0.000 claims 2
- 230000001394 metastastic effect Effects 0.000 claims 2
- 206010061289 metastatic neoplasm Diseases 0.000 claims 2
- 208000025113 myeloid leukemia Diseases 0.000 claims 2
- 201000008968 osteosarcoma Diseases 0.000 claims 2
- 201000005528 peripheral nervous system neoplasm Diseases 0.000 claims 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 201000001281 rectum adenocarcinoma Diseases 0.000 claims 2
- 201000003780 rectum adenoma Diseases 0.000 claims 2
- 201000009410 rhabdomyosarcoma Diseases 0.000 claims 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 201000000849 skin cancer Diseases 0.000 claims 2
- 206010041823 squamous cell carcinoma Diseases 0.000 claims 2
- 201000011549 stomach cancer Diseases 0.000 claims 2
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 2
- 210000001685 thyroid gland Anatomy 0.000 claims 2
- 201000005112 urinary bladder cancer Diseases 0.000 claims 2
- AWHWOJQRBMXEMX-UHFFFAOYSA-N (2,4-dimethoxy-5-propan-2-ylphenyl)-[5-[(4-methylpiperazin-1-yl)methyl]-1,3-dihydroisoindol-2-yl]methanone Chemical compound C1=C(C(C)C)C(OC)=CC(OC)=C1C(=O)N1CC2=CC(CN3CCN(C)CC3)=CC=C2C1 AWHWOJQRBMXEMX-UHFFFAOYSA-N 0.000 claims 1
- RWJDRTNSGKKICC-UHFFFAOYSA-N (2-hydroxy-4-methoxy-5-propan-2-ylphenyl)-[5-[(4-methylpiperazin-1-yl)methyl]-1,3-dihydroisoindol-2-yl]methanone Chemical compound C1=C(C(C)C)C(OC)=CC(O)=C1C(=O)N1CC2=CC(CN3CCN(C)CC3)=CC=C2C1 RWJDRTNSGKKICC-UHFFFAOYSA-N 0.000 claims 1
- BALPSFBLOVZCFJ-UHFFFAOYSA-N (4-hydroxy-2-methoxy-5-propan-2-ylphenyl)-[5-[(4-methylpiperazin-1-yl)methyl]-1,3-dihydroisoindol-2-yl]methanone Chemical compound COC1=CC(O)=C(C(C)C)C=C1C(=O)N1CC2=CC(CN3CCN(C)CC3)=CC=C2C1 BALPSFBLOVZCFJ-UHFFFAOYSA-N 0.000 claims 1
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
- 208000031261 Acute myeloid leukaemia Diseases 0.000 claims 1
- 208000010839 B-cell chronic lymphocytic leukemia Diseases 0.000 claims 1
- 206010055113 Breast cancer metastatic Diseases 0.000 claims 1
- 206010008342 Cervix carcinoma Diseases 0.000 claims 1
- 208000022072 Gallbladder Neoplasms Diseases 0.000 claims 1
- 206010017993 Gastrointestinal neoplasms Diseases 0.000 claims 1
- 101001012157 Homo sapiens Receptor tyrosine-protein kinase erbB-2 Proteins 0.000 claims 1
- 208000007766 Kaposi sarcoma Diseases 0.000 claims 1
- 208000031422 Lymphocytic Chronic B-Cell Leukemia Diseases 0.000 claims 1
- 241000124008 Mammalia Species 0.000 claims 1
- 208000033776 Myeloid Acute Leukemia Diseases 0.000 claims 1
- 206010029260 Neuroblastoma Diseases 0.000 claims 1
- 102100030086 Receptor tyrosine-protein kinase erbB-2 Human genes 0.000 claims 1
- 208000015634 Rectal Neoplasms Diseases 0.000 claims 1
- 201000010208 Seminoma Diseases 0.000 claims 1
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 claims 1
- FMMCBTKUCXDRLO-UHFFFAOYSA-N [2,4-bis(methoxymethoxy)-5-propan-2-ylphenyl]-[5-[(4-methylpiperazin-1-yl)methyl]-1,3-dihydroisoindol-2-yl]methanone Chemical compound C1=C(C(C)C)C(OCOC)=CC(OCOC)=C1C(=O)N1CC2=CC(CN3CCN(C)CC3)=CC=C2C1 FMMCBTKUCXDRLO-UHFFFAOYSA-N 0.000 claims 1
- WJAFKWCVPKKBGZ-UHFFFAOYSA-N [2-hydroxy-4-(methoxymethoxy)-5-propan-2-ylphenyl]-[5-[(4-methylpiperazin-1-yl)methyl]-1,3-dihydroisoindol-2-yl]methanone Chemical compound C1=C(C(C)C)C(OCOC)=CC(O)=C1C(=O)N1CC2=CC(CN3CCN(C)CC3)=CC=C2C1 WJAFKWCVPKKBGZ-UHFFFAOYSA-N 0.000 claims 1
- DIKNBPCALKQCPW-UHFFFAOYSA-N [4-[5-[(4-methylpiperazin-1-yl)methyl]-1,3-dihydroisoindole-2-carbonyl]-2-propan-2-yl-5-(pyrrolidine-1-carbonyloxy)phenyl] pyrrolidine-1-carboxylate Chemical compound C1CCCN1C(=O)OC=1C=C(OC(=O)N2CCCC2)C(C(C)C)=CC=1C(=O)N(CC1=C2)CC1=CC=C2CN1CCN(C)CC1 DIKNBPCALKQCPW-UHFFFAOYSA-N 0.000 claims 1
- ZPZYLJFCZPEYKY-UHFFFAOYSA-N [4-[5-[(4-methylpiperazin-1-yl)methyl]-1,3-dihydroisoindole-2-carbonyl]-5-(2-methylpropanoyloxy)-2-propan-2-ylphenyl] 2-methylpropanoate Chemical compound C1=C(C(C)C)C(OC(=O)C(C)C)=CC(OC(=O)C(C)C)=C1C(=O)N1CC2=CC(CN3CCN(C)CC3)=CC=C2C1 ZPZYLJFCZPEYKY-UHFFFAOYSA-N 0.000 claims 1
- DPGWTHWBSQXWLN-UHFFFAOYSA-N [4-[5-[(4-methylpiperazin-1-yl)methyl]-1,3-dihydroisoindole-2-carbonyl]-5-(morpholine-4-carbonyloxy)-2-propan-2-ylphenyl] morpholine-4-carboxylate Chemical compound C1COCCN1C(=O)OC=1C=C(OC(=O)N2CCOCC2)C(C(C)C)=CC=1C(=O)N(CC1=C2)CC1=CC=C2CN1CCN(C)CC1 DPGWTHWBSQXWLN-UHFFFAOYSA-N 0.000 claims 1
- AZTYLHKKDGSPJJ-UHFFFAOYSA-N [4-hydroxy-2-(methoxymethoxy)-5-propan-2-ylphenyl]-[5-[(4-methylpiperazin-1-yl)methyl]-1,3-dihydroisoindol-2-yl]methanone Chemical compound COCOC1=CC(O)=C(C(C)C)C=C1C(=O)N1CC2=CC(CN3CCN(C)CC3)=CC=C2C1 AZTYLHKKDGSPJJ-UHFFFAOYSA-N 0.000 claims 1
- LHQYQZUUURBMLU-UHFFFAOYSA-N [5-(2,2-dimethylpropanoyloxy)-4-[5-[(4-methylpiperazin-1-yl)methyl]-1,3-dihydroisoindole-2-carbonyl]-2-propan-2-ylphenyl] 2,2-dimethylpropanoate Chemical compound C1=C(OC(=O)C(C)(C)C)C(C(C)C)=CC(C(=O)N2CC3=CC(CN4CCN(C)CC4)=CC=C3C2)=C1OC(=O)C(C)(C)C LHQYQZUUURBMLU-UHFFFAOYSA-N 0.000 claims 1
- LFNVHOYUFYCRFV-UHFFFAOYSA-N [5-(diethylcarbamoyloxy)-4-[5-[(4-methylpiperazin-1-yl)methyl]-1,3-dihydroisoindole-2-carbonyl]-2-propan-2-ylphenyl] n,n-diethylcarbamate Chemical compound C1=C(C(C)C)C(OC(=O)N(CC)CC)=CC(OC(=O)N(CC)CC)=C1C(=O)N1CC2=CC(CN3CCN(C)CC3)=CC=C2C1 LFNVHOYUFYCRFV-UHFFFAOYSA-N 0.000 claims 1
- FRCZIBDEGYRAOE-UHFFFAOYSA-N [5-(dimethylcarbamoyloxy)-4-[5-[(4-methylpiperazin-1-yl)methyl]-1,3-dihydroisoindole-2-carbonyl]-2-propan-2-ylphenyl] n,n-dimethylcarbamate Chemical compound C1=C(OC(=O)N(C)C)C(C(C)C)=CC(C(=O)N2CC3=CC(CN4CCN(C)CC4)=CC=C3C2)=C1OC(=O)N(C)C FRCZIBDEGYRAOE-UHFFFAOYSA-N 0.000 claims 1
- QTRMNIWSMPZZFQ-UHFFFAOYSA-N [5-hydroxy-2-[5-[(4-methylpiperazin-1-yl)methyl]-1,3-dihydroisoindole-2-carbonyl]-4-propan-2-ylphenyl] morpholine-4-carboxylate Chemical compound C1COCCN1C(=O)OC=1C=C(O)C(C(C)C)=CC=1C(=O)N(CC1=C2)CC1=CC=C2CN1CCN(C)CC1 QTRMNIWSMPZZFQ-UHFFFAOYSA-N 0.000 claims 1
- RGIUMTFGGDIKBF-UHFFFAOYSA-N [5-hydroxy-2-[5-[(4-methylpiperazin-1-yl)methyl]-1,3-dihydroisoindole-2-carbonyl]-4-propan-2-ylphenyl] n,n-diethylcarbamate Chemical compound CCN(CC)C(=O)OC1=CC(O)=C(C(C)C)C=C1C(=O)N1CC2=CC(CN3CCN(C)CC3)=CC=C2C1 RGIUMTFGGDIKBF-UHFFFAOYSA-N 0.000 claims 1
- JORQZLDRJSPOIC-UHFFFAOYSA-N [5-hydroxy-2-[5-[(4-methylpiperazin-1-yl)methyl]-1,3-dihydroisoindole-2-carbonyl]-4-propan-2-ylphenyl] n,n-dimethylcarbamate Chemical compound C1=C(O)C(C(C)C)=CC(C(=O)N2CC3=CC(CN4CCN(C)CC4)=CC=C3C2)=C1OC(=O)N(C)C JORQZLDRJSPOIC-UHFFFAOYSA-N 0.000 claims 1
- WBWBTTYOQVXARG-UHFFFAOYSA-N [5-hydroxy-2-[5-[(4-methylpiperazin-1-yl)methyl]-1,3-dihydroisoindole-2-carbonyl]-4-propan-2-ylphenyl] pyrrolidine-1-carboxylate Chemical compound C1CCCN1C(=O)OC=1C=C(O)C(C(C)C)=CC=1C(=O)N(CC1=C2)CC1=CC=C2CN1CCN(C)CC1 WBWBTTYOQVXARG-UHFFFAOYSA-N 0.000 claims 1
- MRVIBWKULAOJDC-UHFFFAOYSA-N [5-hydroxy-4-[5-[(4-methylpiperazin-1-yl)methyl]-1,3-dihydroisoindole-2-carbonyl]-2-propan-2-ylphenyl] morpholine-4-carboxylate Chemical compound OC=1C=C(OC(=O)N2CCOCC2)C(C(C)C)=CC=1C(=O)N(CC1=C2)CC1=CC=C2CN1CCN(C)CC1 MRVIBWKULAOJDC-UHFFFAOYSA-N 0.000 claims 1
- XUEUKRNPYQWRER-UHFFFAOYSA-N [5-hydroxy-4-[5-[(4-methylpiperazin-1-yl)methyl]-1,3-dihydroisoindole-2-carbonyl]-2-propan-2-ylphenyl] n,n-diethylcarbamate Chemical compound C1=C(C(C)C)C(OC(=O)N(CC)CC)=CC(O)=C1C(=O)N1CC2=CC(CN3CCN(C)CC3)=CC=C2C1 XUEUKRNPYQWRER-UHFFFAOYSA-N 0.000 claims 1
- FTJHBVVSBFSORP-UHFFFAOYSA-N [5-hydroxy-4-[5-[(4-methylpiperazin-1-yl)methyl]-1,3-dihydroisoindole-2-carbonyl]-2-propan-2-ylphenyl] pyrrolidine-1-carboxylate Chemical compound OC=1C=C(OC(=O)N2CCCC2)C(C(C)C)=CC=1C(=O)N(CC1=C2)CC1=CC=C2CN1CCN(C)CC1 FTJHBVVSBFSORP-UHFFFAOYSA-N 0.000 claims 1
- 230000002159 abnormal effect Effects 0.000 claims 1
- 230000001154 acute effect Effects 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 230000004663 cell proliferation Effects 0.000 claims 1
- 201000010881 cervical cancer Diseases 0.000 claims 1
- 230000001684 chronic effect Effects 0.000 claims 1
- 208000032852 chronic lymphocytic leukemia Diseases 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000003325 follicular Effects 0.000 claims 1
- 201000010175 gallbladder cancer Diseases 0.000 claims 1
- 210000001035 gastrointestinal tract Anatomy 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 claims 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims 1
- 230000000527 lymphocytic effect Effects 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 1
- 208000007538 neurilemmoma Diseases 0.000 claims 1
- 239000006187 pill Substances 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 201000005825 prostate adenocarcinoma Diseases 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
- 206010038038 rectal cancer Diseases 0.000 claims 1
- 201000001275 rectum cancer Diseases 0.000 claims 1
- 206010039667 schwannoma Diseases 0.000 claims 1
- 208000024891 symptom Diseases 0.000 claims 1
- 208000001608 teratocarcinoma Diseases 0.000 claims 1
- HDDPBYRSCZNVJF-UHFFFAOYSA-N tert-butyl [2-[5-[(4-methylpiperazin-1-yl)methyl]-1,3-dihydroisoindole-2-carbonyl]-5-[(2-methylpropan-2-yl)oxycarbonyloxy]-4-propan-2-ylphenyl] carbonate Chemical compound C1=C(OC(=O)OC(C)(C)C)C(C(C)C)=CC(C(=O)N2CC3=CC(CN4CCN(C)CC4)=CC=C3C2)=C1OC(=O)OC(C)(C)C HDDPBYRSCZNVJF-UHFFFAOYSA-N 0.000 claims 1
- WDAFDFNREQPREF-UHFFFAOYSA-N tert-butyl [5-(dimethylcarbamoyloxy)-2-[5-[(4-methylpiperazin-1-yl)methyl]-1,3-dihydroisoindole-2-carbonyl]-4-propan-2-ylphenyl] carbonate Chemical compound C1=C(OC(=O)N(C)C)C(C(C)C)=CC(C(=O)N2CC3=CC(CN4CCN(C)CC4)=CC=C3C2)=C1OC(=O)OC(C)(C)C WDAFDFNREQPREF-UHFFFAOYSA-N 0.000 claims 1
- 208000030901 thyroid gland follicular carcinoma Diseases 0.000 claims 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US4425608P | 2008-04-11 | 2008-04-11 | |
| GBGB0806527.8A GB0806527D0 (en) | 2008-04-11 | 2008-04-11 | Pharmaceutical compounds |
| GB0806527.8 | 2008-04-11 | ||
| US61/044,256 | 2008-04-11 | ||
| PCT/GB2009/050358 WO2009125230A1 (en) | 2008-04-11 | 2009-04-09 | Pharmaceutical compounds |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2011516536A JP2011516536A (ja) | 2011-05-26 |
| JP2011516536A5 true JP2011516536A5 (enExample) | 2012-05-24 |
| JP5653903B2 JP5653903B2 (ja) | 2015-01-14 |
Family
ID=39433425
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011503505A Expired - Fee Related JP5653903B2 (ja) | 2008-04-11 | 2009-04-09 | 医薬化合物 |
Country Status (14)
| Country | Link |
|---|---|
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| JP (1) | JP5653903B2 (enExample) |
| CY (1) | CY1115256T1 (enExample) |
| DK (1) | DK2271618T3 (enExample) |
| ES (1) | ES2469797T3 (enExample) |
| GB (1) | GB0806527D0 (enExample) |
| HR (1) | HRP20140516T1 (enExample) |
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| RS (1) | RS53389B (enExample) |
| SI (1) | SI2271618T1 (enExample) |
| TW (1) | TWI453201B (enExample) |
| WO (1) | WO2009125230A1 (enExample) |
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| EP1883402A2 (en) * | 2005-04-13 | 2008-02-06 | Astex Therapeutics Limited | Hydroxybenzamide derivatives and their use as inhibitors of hsp90 |
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| GB201009853D0 (en) | 2010-06-11 | 2010-07-21 | Chroma Therapeutics Ltd | HSP90 inhibitors |
| WO2012064671A1 (en) * | 2010-11-08 | 2012-05-18 | The Ohio State University Research Foundation | Compositions and methods for increasing drug efficacy in cancer |
| US10729692B2 (en) * | 2017-02-26 | 2020-08-04 | Institute For Cancer Research | Dual inhibition of CDK and HSP90 destabilize HIF1alpha and synergistically induces cancer cell death |
| EP4093731A1 (en) * | 2020-01-20 | 2022-11-30 | Neophore Limited | Isoindoline derivatives which bind to an atp binding site |
| GB202008201D0 (en) * | 2020-06-01 | 2020-07-15 | Neophore Ltd | Inhibitor compounds |
| GB202110373D0 (en) * | 2021-07-19 | 2021-09-01 | Neophore Ltd | Inhibitor compounds |
| GB202117224D0 (en) * | 2021-11-29 | 2022-01-12 | Neophore Ltd | Inhibitor compounds |
| GB202117225D0 (en) * | 2021-11-29 | 2022-01-12 | Neophore Ltd | Protac compounds |
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-
2008
- 2008-04-11 GB GBGB0806527.8A patent/GB0806527D0/en not_active Ceased
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2009
- 2009-04-09 EP EP09731468.6A patent/EP2271618B1/en active Active
- 2009-04-09 WO PCT/GB2009/050358 patent/WO2009125230A1/en not_active Ceased
- 2009-04-09 JP JP2011503505A patent/JP5653903B2/ja not_active Expired - Fee Related
- 2009-04-09 ES ES09731468.6T patent/ES2469797T3/es active Active
- 2009-04-09 PT PT97314686T patent/PT2271618E/pt unknown
- 2009-04-09 HR HRP20140516AT patent/HRP20140516T1/hr unknown
- 2009-04-09 RS RS20140346A patent/RS53389B/sr unknown
- 2009-04-09 PL PL09731468T patent/PL2271618T3/pl unknown
- 2009-04-09 SI SI200930943T patent/SI2271618T1/sl unknown
- 2009-04-09 DK DK09731468.6T patent/DK2271618T3/da active
- 2009-04-10 TW TW098112063A patent/TWI453201B/zh not_active IP Right Cessation
-
2010
- 2010-10-12 US US12/902,658 patent/US8383619B2/en not_active Expired - Fee Related
-
2013
- 2013-01-30 US US13/753,904 patent/US8664218B2/en not_active Expired - Fee Related
-
2014
- 2014-07-07 CY CY20141100506T patent/CY1115256T1/el unknown
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