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 | |
| US61/044,256 | 2008-04-11 | ||
| GBGB0806527.8A GB0806527D0 (en) | 2008-04-11 | 2008-04-11 | Pharmaceutical compounds |
| GB0806527.8 | 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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Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1877379B1 (en) * | 2005-04-13 | 2013-01-16 | Astex Therapeutics Limited | Hydroxybenzamide derivatives and their use as inhibitors of hsp90 |
| US9730912B2 (en) | 2006-10-12 | 2017-08-15 | Astex Therapeutics Limited | Pharmaceutical compounds |
| GB201009853D0 (en) * | 2010-06-11 | 2010-07-21 | Chroma Therapeutics Ltd | HSP90 inhibitors |
| US9044474B2 (en) * | 2010-11-08 | 2015-06-02 | The Ohio State University | 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 |
| US20230061002A1 (en) * | 2020-01-20 | 2023-03-02 | Neophore Limited | Isoindoline derivatives which bind to an atp binding site |
| US20230183197A1 (en) * | 2020-06-01 | 2023-06-15 | Neophore Limited | Inhibitors of mlh1 and/or pms2 for cancer treatment |
| 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 |
Family Cites Families (91)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4910506A (enExample) | 1972-05-31 | 1974-01-30 | ||
| US4582909A (en) | 1984-02-02 | 1986-04-15 | Warner-Lambert Company | Benzobicyclic lactam acids and derivatives as cognition activators |
| US4666828A (en) | 1984-08-15 | 1987-05-19 | The General Hospital Corporation | Test for Huntington's disease |
| US4760064A (en) | 1984-12-18 | 1988-07-26 | Otsuka Pharmaceutical Co., Ltd. | Carbostyril compounds, compositions containing same and processes for preparing same |
| US4683202A (en) | 1985-03-28 | 1987-07-28 | Cetus Corporation | Process for amplifying nucleic acid sequences |
| US4801531A (en) | 1985-04-17 | 1989-01-31 | Biotechnology Research Partners, Ltd. | Apo AI/CIII genomic polymorphisms predictive of atherosclerosis |
| CA1340191C (en) | 1988-06-13 | 1998-12-15 | Katsuhiro Imaki | Derivatives of p-substituted phenyl ester of pivalic acid |
| US4990511A (en) | 1988-08-03 | 1991-02-05 | Takeda Chemical Industries, Ltd. | Amide compounds, their production and use |
| US5272057A (en) | 1988-10-14 | 1993-12-21 | Georgetown University | Method of detecting a predisposition to cancer by the use of restriction fragment length polymorphism of the gene for human poly (ADP-ribose) polymerase |
| US5192659A (en) | 1989-08-25 | 1993-03-09 | Genetype Ag | Intron sequence analysis method for detection of adjacent and remote locus alleles as haplotypes |
| GB8926560D0 (en) | 1989-11-24 | 1990-01-17 | Zambeletti Spa L | Pharmaceuticals |
| US5124350A (en) | 1990-06-28 | 1992-06-23 | G. D. Searle & Co. | Leukotriene b4 antagonists |
| CA2049481A1 (en) | 1990-08-27 | 1992-02-28 | Jill Ann Panetta | Method of treating inflammatory bowel disease |
| FR2669029B1 (fr) | 1990-11-14 | 1994-09-02 | Adir | Nouveaux derives de la n-benzoyl proline, leur procede de preparation et les compositions pharmaceutiques qui les contiennent. |
| US5280046A (en) | 1991-02-22 | 1994-01-18 | The University Of Colorado Foundation, Inc. | Method of treating type I diabetes |
| WO1992017467A1 (en) | 1991-04-06 | 1992-10-15 | Dr Lo. Zambeletti S.P.A. | Substituted azacyclic compounds, process for their preparation and their use as analgesics |
| US5633283A (en) | 1995-01-23 | 1997-05-27 | Eli Lilly And Company | Method for treating multiple sclerosis |
| WO1998004689A1 (en) | 1995-07-31 | 1998-02-05 | Urocor, Inc. | Biomarkers and targets for diagnosis, prognosis and management of prostate disease |
| US6218529B1 (en) | 1995-07-31 | 2001-04-17 | Urocor, Inc. | Biomarkers and targets for diagnosis, prognosis and management of prostate, breast and bladder cancer |
| JP3855026B2 (ja) | 1996-01-16 | 2006-12-06 | 富士レビオ株式会社 | アミド誘導体の製造方法 |
| CA2242879C (en) | 1996-01-29 | 2009-05-26 | The Regents Of The University Of California | Method for treating sexual dysfunctions |
| GB9606187D0 (en) | 1996-03-23 | 1996-05-29 | Inst Of Food Research | Production of vanillin |
| JP2000507955A (ja) | 1996-04-03 | 2000-06-27 | メルク エンド カンパニー インコーポレーテッド | ファルネシル―タンパク質転移酵素の阻害剤 |
| WO1997039750A1 (en) | 1996-04-19 | 1997-10-30 | The Regents Of The University Of California | Treatment of mood/affective disorders by glutamatergic upmodulators |
| IL118657A0 (en) | 1996-06-14 | 1996-10-16 | Arad Dorit | Inhibitors for picornavirus proteases |
| EP0973778A1 (en) | 1997-03-07 | 2000-01-26 | Novo Nordisk A/S | 4,5,6,7-TETRAHYDRO-THIENO 3,2-c]PYRIDINE DERIVATIVES, THEIR PREPARATION AND USE |
| UY24949A1 (es) | 1997-04-08 | 2001-04-30 | Smithkline Beecham Corp | Compuestos calcilíticos |
| WO1998047885A1 (en) | 1997-04-18 | 1998-10-29 | Smithkline Beecham Plc | A bicyclic aryl or a bicyclic heterocyclic ring containing compounds having a combined 5ht1a, 5ht1b and 5ht1d receptor antagonistic activity |
| US6329368B1 (en) | 1997-05-09 | 2001-12-11 | The Regents Of The University Of California | Endocrine modulation with positive modulators of AMPA type glutamate receptors |
| WO1999021422A1 (en) | 1997-10-27 | 1999-05-06 | Cortex Pharmaceuticals, Inc. | Treatment of schizophrenia with ampakines and neuroleptics |
| WO1999029705A2 (en) | 1997-12-08 | 1999-06-17 | Glycomed Incorporated | Sialyl lewis x and sialyl lewis a glycomimetics |
| EP1165492A1 (en) | 1999-03-30 | 2002-01-02 | Pharmacor Inc. | Hydroxyphenyl derivatives with hiv integrase inhibitory properties |
| DE19955283A1 (de) | 1999-11-17 | 2001-05-23 | Aventis Res & Tech Gmbh & Co | Verfahren zur enantioselektiven Gewinnung von Aminosäuren und Aminosäurederivaten unter Verwendung von Racemisierungskatalysatoren |
| AU1624801A (en) | 1999-11-19 | 2001-05-30 | Corvas International, Inc. | Plasminogen activator inhibitor antagonists related applications |
| AU2001243158A1 (en) | 2000-02-18 | 2001-08-27 | Merck And Co., Inc. | Inhibitors of prenyl-protein transferase |
| CN1244561C (zh) | 2000-05-11 | 2006-03-08 | 布里斯托尔-迈尔斯斯奎布公司 | 可用作生长激素促分泌素的四氢异喹啉类似物 |
| CA2408913A1 (en) | 2000-05-16 | 2001-11-22 | Takeda Chemical Industries, Ltd. | Melanin-concentrating hormone antagonist |
| CA2308994A1 (en) | 2000-05-19 | 2001-11-19 | Aegera Therapeutics Inc. | Neuroprotective compounds |
| DE10024939A1 (de) | 2000-05-19 | 2001-11-29 | Bayer Ag | Neue Diphenylmethanderivate für Arzneimittel |
| FR2812876B1 (fr) | 2000-08-08 | 2002-09-27 | Galderma Res & Dev | Nouveaux composes bi-aromatiques activateurs des recepteurs de type ppar-gamma et leur utilisation dans des compositions cosmetiques ou pharmaceutiques |
| MXPA03001654A (es) | 2000-08-25 | 2004-09-10 | Warner Lambert Co | Proceso para la elaboracion del acido n-aril-antranilico y sus derivados. |
| CN100370975C (zh) | 2000-12-18 | 2008-02-27 | 株式会社医药分子设计研究所 | 炎症性细胞因子产生游离抑制剂 |
| US6649606B1 (en) | 2001-11-09 | 2003-11-18 | Bristol-Myers Squibb Co. | Tetrahydroisoquinoline analogs as modulators of chemokine receptor activity |
| AU2002366362A1 (en) | 2001-12-18 | 2003-06-30 | Bayer Aktiengesellschaft | 2-substituted pyrrolo(2.1-a)isoquinolines against cancer |
| AU2002366811B2 (en) | 2001-12-20 | 2009-01-15 | Osi Pharmaceuticals, Inc. | Pyrimidine A2B selective antagonist compounds, their synthesis and use |
| ATE374753T1 (de) | 2001-12-21 | 2007-10-15 | Vernalis Cambridge Ltd | 3-(2,4)dihydroxyphenyl-4-phenylpyrazole und deren medizinische verwendung |
| US20030203915A1 (en) | 2002-04-05 | 2003-10-30 | Xinqin Fang | Nitric oxide donors, compositions and methods of use related applications |
| CN1658849A (zh) | 2002-06-05 | 2005-08-24 | 株式会社医药分子设计研究所 | Ap－1和nfat活化抑制剂 |
| CA2488342A1 (en) | 2002-06-05 | 2003-12-18 | Institute Of Medicinal Molecular Design, Inc. | Therapeutic drug for diabetes |
| AU2003242131A1 (en) | 2002-06-05 | 2003-12-22 | Institute Of Medicinal Molecular Design, Inc. | Immunity-related protein kinase inhibitors |
| WO2003103665A1 (ja) | 2002-06-06 | 2003-12-18 | 株式会社医薬分子設計研究所 | 抗アレルギー薬 |
| SE0202133D0 (sv) | 2002-07-08 | 2002-07-08 | Astrazeneca Ab | Novel compounds |
| CA2499465A1 (en) | 2002-07-16 | 2004-01-22 | Amura Therapeutics Limited | Biologically active compounds |
| JP2006505571A (ja) | 2002-10-15 | 2006-02-16 | リゲル ファーマシューテイカルズ、インコーポレイテッド | 置換されたインドール及びｈｃｖ阻害剤としてのその使用 |
| TWI228885B (en) | 2003-01-23 | 2005-03-01 | Mediatek Inc | Method for controlling a mobile communication device to enter a power-saving mode and to recover timing after the mobile communication device leaves the power-saving mode |
| DK1611112T3 (da) | 2003-02-11 | 2012-11-19 | Cancer Res Inst | Isoxazolforbindelser som hæmmere af varmechokproteiner |
| RU2324493C2 (ru) | 2003-02-20 | 2008-05-20 | Юниверсити Оф Коннектикут Хелт Сентер | Способ применения композиций, содержащих белки теплового шока или альфа-2-макроглобулин, для лечения рака и инфекционных болезней |
| EP1597256A1 (en) | 2003-02-21 | 2005-11-23 | Pfizer Inc. | N-heterocyclyl-substituted amino-thiazole derivatives as protein kinase inhibitors |
| MXPA05011597A (es) | 2003-04-30 | 2005-12-15 | Novartis Ag | Derivados de aminopropanol como moduladores del receptor 1-fosfato de esfingosina. |
| CN100567242C (zh) | 2003-06-27 | 2009-12-09 | 协和发酵麒麟株式会社 | Hsp90家族蛋白质阻断剂 |
| GB0315111D0 (en) | 2003-06-27 | 2003-07-30 | Cancer Rec Tech Ltd | Substituted 5-membered ring compounds and their use |
| TWI322806B (en) | 2003-06-30 | 2010-04-01 | Mitsubishi Tanabe Pharma Corp | Process of preparating 3-acylaminobenzofuran-2-carboxylic acid derivatives |
| KR20060054308A (ko) | 2003-07-16 | 2006-05-22 | 가부시키가이샤 이야쿠 분지 셋케이 겐쿠쇼 | 피부 색소침착의 치료제 |
| NZ544756A (en) | 2003-07-22 | 2009-09-25 | Astex Therapeutics Ltd | 3,4-Disubstituted 1H-pyrazole compounds and their use as cyclin dependent kinases (CDK) and glycogen synthase kinase-3 (GSK-3) modulators |
| DE602004027504D1 (de) | 2003-07-24 | 2010-07-15 | Leo Pharma As | Aminobenzophenonverbindungen |
| KR20060054408A (ko) | 2003-07-28 | 2006-05-22 | 얀센 파마슈티카 엔.브이. | 벤즈이미다졸, 벤즈티아졸 및 벤즈옥사졸 유도체 및ｌｔａ4 ｈ 조정자로서의 그의 용도 |
| DE10335584B4 (de) | 2003-07-31 | 2006-06-29 | Philipps-Universität Marburg | Verfahren zur Herstellung zyklischer Moleküle |
| DE10335726A1 (de) | 2003-08-05 | 2005-03-03 | Bayer Cropscience Gmbh | Verwendung von Hydroxyaromaten als Safener |
| WO2005016889A1 (en) | 2003-08-08 | 2005-02-24 | Virginia Commonwealth University | Compounds having antiestrogenic and tissue selective estrogenic properties |
| WO2005023818A2 (en) | 2003-09-10 | 2005-03-17 | Gpc Biotech Ag | Heterobicyclic compounds as pharmaceutically active agents |
| EP1687268A1 (en) | 2003-11-10 | 2006-08-09 | Schering Aktiengesellschaft | Benzylether amine compounds useful as ccr-5 antagonists |
| WO2005063222A1 (ja) | 2003-12-26 | 2005-07-14 | Kyowa Hakko Kogyo Co., Ltd. | Hsp90ファミリー蛋白質阻害剤 |
| US7351709B2 (en) | 2004-06-09 | 2008-04-01 | Wyeth | Estrogen receptor ligands |
| MX2007001127A (es) | 2004-07-27 | 2007-07-11 | Sgx Pharmaceuticals Inc | Moduladores de pirrolo-piridina cinasa. |
| 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 |
| DE102004049078A1 (de) | 2004-10-08 | 2006-04-13 | Merck Patent Gmbh | Phenylpyrazole |
| US7208630B2 (en) | 2004-10-27 | 2007-04-24 | University Of Kansas | Heat shock protein 90 inhibitors |
| WO2006051808A1 (ja) | 2004-11-09 | 2006-05-18 | Kyowa Hakko Kogyo Co., Ltd. | Hsp90ファミリー蛋白質阻害剤 |
| DK1848694T3 (da) | 2005-02-07 | 2010-01-25 | Hoffmann La Roche | Heterocykliske substituerede phenylmethanoner som inhibitorer af glycintransporter |
| US20060183902A1 (en) | 2005-02-15 | 2006-08-17 | Baxter Ellen W | Dihydroindolyl methanones as alpha 1a/1d adrenoreceptor modulators for the treatment of benign prostatic hypertrophy and lower urinary tract symptoms |
| CN101123954B (zh) | 2005-02-21 | 2011-07-13 | 协和发酵麒麟株式会社 | 抗肿瘤剂 |
| EP1877379B1 (en) | 2005-04-13 | 2013-01-16 | Astex Therapeutics Limited | Hydroxybenzamide derivatives and their use as inhibitors of hsp90 |
| EP1879863A1 (en) * | 2005-05-03 | 2008-01-23 | Pfizer, Inc. | Amide resorcinol compounds |
| US7425633B2 (en) | 2005-08-26 | 2008-09-16 | National Health Research Institutes | Pyrrolidine compounds |
| US7754725B2 (en) | 2006-03-01 | 2010-07-13 | Astex Therapeutics Ltd. | Dihydroxyphenyl isoindolymethanones |
| EP2073803B1 (en) | 2006-10-12 | 2018-09-19 | Astex Therapeutics Limited | Pharmaceutical combinations |
| US8883790B2 (en) | 2006-10-12 | 2014-11-11 | Astex Therapeutics Limited | Pharmaceutical combinations |
| WO2008044027A2 (en) | 2006-10-12 | 2008-04-17 | Astex Therapeutics Limited | Pharmaceutical compounds having hsp90 inhibitory or modulating activity |
| GB0620259D0 (en) | 2006-10-12 | 2006-11-22 | Astex Therapeutics Ltd | Pharmaceutical compounds |
| US8277807B2 (en) | 2006-10-12 | 2012-10-02 | Astex Therapeutics Limited | Pharmaceutical combinations |
| US9730912B2 (en) | 2006-10-12 | 2017-08-15 | Astex Therapeutics Limited | Pharmaceutical compounds |
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2008
- 2008-04-11 GB GBGB0806527.8A patent/GB0806527D0/en not_active Ceased
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2009
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- 2009-04-09 WO PCT/GB2009/050358 patent/WO2009125230A1/en not_active Ceased
- 2009-04-09 EP EP09731468.6A patent/EP2271618B1/en active Active
- 2009-04-09 PT PT97314686T patent/PT2271618E/pt unknown
- 2009-04-09 SI SI200930943T patent/SI2271618T1/sl unknown
- 2009-04-09 PL PL09731468T patent/PL2271618T3/pl unknown
- 2009-04-09 ES ES09731468.6T patent/ES2469797T3/es active Active
- 2009-04-09 DK DK09731468.6T patent/DK2271618T3/da active
- 2009-04-09 HR HRP20140516AT patent/HRP20140516T1/hr unknown
- 2009-04-09 JP JP2011503505A patent/JP5653903B2/ja not_active Expired - Fee Related
- 2009-04-10 TW TW098112063A patent/TWI453201B/zh not_active IP Right Cessation
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2010
- 2010-10-12 US US12/902,658 patent/US8383619B2/en not_active Expired - Fee Related
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2013
- 2013-01-30 US US13/753,904 patent/US8664218B2/en not_active Expired - Fee Related
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2014
- 2014-07-07 CY CY20141100506T patent/CY1115256T1/el unknown