JP2008528470A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2008528470A5 JP2008528470A5 JP2007551745A JP2007551745A JP2008528470A5 JP 2008528470 A5 JP2008528470 A5 JP 2008528470A5 JP 2007551745 A JP2007551745 A JP 2007551745A JP 2007551745 A JP2007551745 A JP 2007551745A JP 2008528470 A5 JP2008528470 A5 JP 2008528470A5
- Authority
- JP
- Japan
- Prior art keywords
- acid
- cancer
- benzoylamino
- salt
- ylamide
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 150000003839 salts Chemical class 0.000 claims 27
- 239000002253 acid Substances 0.000 claims 20
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 12
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 9
- 150000001875 compounds Chemical class 0.000 claims 9
- OVPNQJVDAFNBDN-UHFFFAOYSA-N 4-(2,6-dichlorobenzamido)-N-(piperidin-4-yl)-pyrazole-3-carboxamide Chemical class ClC1=CC=CC(Cl)=C1C(=O)NC1=CNN=C1C(=O)NC1CCNCC1 OVPNQJVDAFNBDN-UHFFFAOYSA-N 0.000 claims 7
- 201000010099 disease Diseases 0.000 claims 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 7
- 238000004519 manufacturing process Methods 0.000 claims 7
- 206010028980 Neoplasm Diseases 0.000 claims 6
- 239000003814 drug Substances 0.000 claims 6
- 201000011510 cancer Diseases 0.000 claims 5
- 229940098779 methanesulfonic acid Drugs 0.000 claims 5
- 238000011282 treatment Methods 0.000 claims 5
- 235000011054 acetic acid Nutrition 0.000 claims 4
- 239000007864 aqueous solution Substances 0.000 claims 4
- 239000013078 crystal Substances 0.000 claims 4
- 238000000034 method Methods 0.000 claims 4
- 238000000634 powder X-ray diffraction Methods 0.000 claims 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 3
- -1 carboxylic acid piperidin-4-yl amide mesylate Chemical class 0.000 claims 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims 3
- 239000003960 organic solvent Substances 0.000 claims 3
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 claims 2
- WXTMDXOMEHJXQO-UHFFFAOYSA-N 2,5-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC(O)=CC=C1O WXTMDXOMEHJXQO-UHFFFAOYSA-N 0.000 claims 2
- KPGXRSRHYNQIFN-UHFFFAOYSA-N 2-oxoglutaric acid Chemical compound OC(=O)CCC(=O)C(O)=O KPGXRSRHYNQIFN-UHFFFAOYSA-N 0.000 claims 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims 2
- 208000010839 B-cell chronic lymphocytic leukemia Diseases 0.000 claims 2
- 208000003950 B-cell lymphoma Diseases 0.000 claims 2
- 206010006187 Breast cancer Diseases 0.000 claims 2
- 208000026310 Breast neoplasm Diseases 0.000 claims 2
- 206010009944 Colon cancer Diseases 0.000 claims 2
- 102000003903 Cyclin-dependent kinases Human genes 0.000 claims 2
- 108090000266 Cyclin-dependent kinases Proteins 0.000 claims 2
- 208000000461 Esophageal Neoplasms Diseases 0.000 claims 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- 208000031671 Large B-Cell Diffuse Lymphoma Diseases 0.000 claims 2
- 208000031422 Lymphocytic Chronic B-Cell Leukemia Diseases 0.000 claims 2
- 206010025323 Lymphomas Diseases 0.000 claims 2
- 241000124008 Mammalia Species 0.000 claims 2
- QIAFMBKCNZACKA-UHFFFAOYSA-N N-benzoylglycine Chemical compound OC(=O)CNC(=O)C1=CC=CC=C1 QIAFMBKCNZACKA-UHFFFAOYSA-N 0.000 claims 2
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 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
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 2
- 206010060862 Prostate cancer Diseases 0.000 claims 2
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 2
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims 2
- 210000004027 cell Anatomy 0.000 claims 2
- 208000032852 chronic lymphocytic leukemia Diseases 0.000 claims 2
- 208000029742 colonic neoplasm Diseases 0.000 claims 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 claims 2
- 206010012818 diffuse large B-cell lymphoma Diseases 0.000 claims 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 claims 2
- 201000004101 esophageal cancer Diseases 0.000 claims 2
- 238000010438 heat treatment Methods 0.000 claims 2
- 201000005787 hematologic cancer Diseases 0.000 claims 2
- 208000024200 hematopoietic and lymphoid system neoplasm Diseases 0.000 claims 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims 2
- 230000002452 interceptive effect Effects 0.000 claims 2
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 claims 2
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 claims 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims 2
- 150000007522 mineralic acids Chemical class 0.000 claims 2
- XTEGVFVZDVNBPF-UHFFFAOYSA-N naphthalene-1,5-disulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1S(O)(=O)=O XTEGVFVZDVNBPF-UHFFFAOYSA-N 0.000 claims 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims 2
- 150000007524 organic acids Chemical class 0.000 claims 2
- PXQPEWDEAKTCGB-UHFFFAOYSA-N orotic acid Chemical compound OC(=O)C1=CC(=O)NC(=O)N1 PXQPEWDEAKTCGB-UHFFFAOYSA-N 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- BCIIMDOZSUCSEN-UHFFFAOYSA-N piperidin-4-amine Chemical compound NC1CCNCC1 BCIIMDOZSUCSEN-UHFFFAOYSA-N 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- 125000006239 protecting group Chemical class 0.000 claims 2
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N thiocyanic acid Chemical compound SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims 2
- 208000030901 thyroid gland follicular carcinoma Diseases 0.000 claims 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims 1
- AIMFJYDQGGFYOE-UHFFFAOYSA-N 1-[(2,6-dichlorobenzoyl)amino]-n-piperidin-4-ylpyrazole-3-carboxamide Chemical compound ClC1=CC=CC(Cl)=C1C(=O)NN1N=C(C(=O)NC2CCNCC2)C=C1 AIMFJYDQGGFYOE-UHFFFAOYSA-N 0.000 claims 1
- LDMOEFOXLIZJOW-UHFFFAOYSA-N 1-dodecanesulfonic acid Chemical compound CCCCCCCCCCCCS(O)(=O)=O LDMOEFOXLIZJOW-UHFFFAOYSA-N 0.000 claims 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 claims 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims 1
- UOQHWNPVNXSDDO-UHFFFAOYSA-N 3-bromoimidazo[1,2-a]pyridine-6-carbonitrile Chemical compound C1=CC(C#N)=CN2C(Br)=CN=C21 UOQHWNPVNXSDDO-UHFFFAOYSA-N 0.000 claims 1
- JLAKCHGEEBPDQI-UHFFFAOYSA-N 4-(4-fluorobenzyl)piperidine Chemical compound C1=CC(F)=CC=C1CC1CCNCC1 JLAKCHGEEBPDQI-UHFFFAOYSA-N 0.000 claims 1
- UDWFVMLBVNIEIL-UHFFFAOYSA-N 4-[(2,6-dichlorobenzoyl)amino]-1H-pyrazole-5-carboxylic acid piperidine Chemical compound N1CCCCC1.ClC1=C(C(=O)NC=2C(=NNC2)C(=O)O)C(=CC=C1)Cl UDWFVMLBVNIEIL-UHFFFAOYSA-N 0.000 claims 1
- BRZQYVXJAZMSBB-UHFFFAOYSA-N 4-[(2,6-dichlorobenzoyl)amino]-1h-pyrazole-5-carboxylic acid Chemical compound OC(=O)C1=NNC=C1NC(=O)C1=C(Cl)C=CC=C1Cl BRZQYVXJAZMSBB-UHFFFAOYSA-N 0.000 claims 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims 1
- 208000024893 Acute lymphoblastic leukemia Diseases 0.000 claims 1
- 208000014697 Acute lymphocytic leukaemia Diseases 0.000 claims 1
- 208000023275 Autoimmune disease Diseases 0.000 claims 1
- 239000005711 Benzoic acid Substances 0.000 claims 1
- 206010005003 Bladder cancer Diseases 0.000 claims 1
- 108091007914 CDKs Proteins 0.000 claims 1
- LSPHULWDVZXLIL-UHFFFAOYSA-N Camphoric acid Natural products CC1(C)C(C(O)=O)CCC1(C)C(O)=O LSPHULWDVZXLIL-UHFFFAOYSA-N 0.000 claims 1
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 claims 1
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 claims 1
- 206010008342 Cervix carcinoma Diseases 0.000 claims 1
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 claims 1
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 claims 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims 1
- 208000004463 Follicular Adenocarcinoma Diseases 0.000 claims 1
- DSLZVSRJTYRBFB-UHFFFAOYSA-N Galactaric acid Natural products OC(=O)C(O)C(O)C(O)C(O)C(O)=O DSLZVSRJTYRBFB-UHFFFAOYSA-N 0.000 claims 1
- IAJILQKETJEXLJ-UHFFFAOYSA-N Galacturonsaeure Natural products O=CC(O)C(O)C(O)C(O)C(O)=O IAJILQKETJEXLJ-UHFFFAOYSA-N 0.000 claims 1
- 208000022072 Gallbladder Neoplasms Diseases 0.000 claims 1
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 claims 1
- 102000002254 Glycogen Synthase Kinase 3 Human genes 0.000 claims 1
- 108010014905 Glycogen Synthase Kinase 3 Proteins 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
- 208000008839 Kidney Neoplasms Diseases 0.000 claims 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 1
- 208000015914 Non-Hodgkin lymphomas Diseases 0.000 claims 1
- 206010061534 Oesophageal squamous cell carcinoma Diseases 0.000 claims 1
- 239000005642 Oleic acid Substances 0.000 claims 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims 1
- 235000021314 Palmitic acid Nutrition 0.000 claims 1
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims 1
- 208000006664 Precursor Cell Lymphoblastic Leukemia-Lymphoma Diseases 0.000 claims 1
- 206010038389 Renal cancer Diseases 0.000 claims 1
- 201000010208 Seminoma Diseases 0.000 claims 1
- 208000000453 Skin Neoplasms Diseases 0.000 claims 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims 1
- 208000036765 Squamous cell carcinoma of the esophagus Diseases 0.000 claims 1
- 235000021355 Stearic acid Nutrition 0.000 claims 1
- 208000005718 Stomach Neoplasms Diseases 0.000 claims 1
- 206010042971 T-cell lymphoma Diseases 0.000 claims 1
- 208000027585 T-cell non-Hodgkin lymphoma Diseases 0.000 claims 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims 1
- 208000024770 Thyroid neoplasm Diseases 0.000 claims 1
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims 1
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 claims 1
- 208000036142 Viral infection Diseases 0.000 claims 1
- 230000002159 abnormal effect Effects 0.000 claims 1
- 229960000583 acetic acid Drugs 0.000 claims 1
- 239000001361 adipic acid Substances 0.000 claims 1
- 235000011037 adipic acid Nutrition 0.000 claims 1
- 229960000250 adipic acid Drugs 0.000 claims 1
- IAJILQKETJEXLJ-QTBDOELSSA-N aldehydo-D-glucuronic acid Chemical compound O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)C(O)=O IAJILQKETJEXLJ-QTBDOELSSA-N 0.000 claims 1
- 239000000783 alginic acid Substances 0.000 claims 1
- 235000010443 alginic acid Nutrition 0.000 claims 1
- 229960001126 alginic acid Drugs 0.000 claims 1
- 229920000615 alginic acid Polymers 0.000 claims 1
- 150000004781 alginic acids Chemical class 0.000 claims 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 claims 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims 1
- 125000006242 amine protecting group Chemical group 0.000 claims 1
- 235000010323 ascorbic acid Nutrition 0.000 claims 1
- 239000011668 ascorbic acid Substances 0.000 claims 1
- 229960005070 ascorbic acid Drugs 0.000 claims 1
- 235000003704 aspartic acid Nutrition 0.000 claims 1
- 229960005261 aspartic acid Drugs 0.000 claims 1
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims 1
- 229940092714 benzenesulfonic acid Drugs 0.000 claims 1
- 235000010233 benzoic acid Nutrition 0.000 claims 1
- 229960004365 benzoic acid Drugs 0.000 claims 1
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 claims 1
- LSPHULWDVZXLIL-QUBYGPBYSA-N camphoric acid Chemical compound CC1(C)[C@H](C(O)=O)CC[C@]1(C)C(O)=O LSPHULWDVZXLIL-QUBYGPBYSA-N 0.000 claims 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 230000004663 cell proliferation Effects 0.000 claims 1
- 210000003169 central nervous system Anatomy 0.000 claims 1
- 201000010881 cervical cancer Diseases 0.000 claims 1
- 239000000625 cyclamic acid and its Na and Ca salt Substances 0.000 claims 1
- HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 claims 1
- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 210000002615 epidermis Anatomy 0.000 claims 1
- 208000007276 esophageal squamous cell carcinoma Diseases 0.000 claims 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 claims 1
- 239000001530 fumaric acid Substances 0.000 claims 1
- DSLZVSRJTYRBFB-DUHBMQHGSA-N galactaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)C(O)=O DSLZVSRJTYRBFB-DUHBMQHGSA-N 0.000 claims 1
- 201000010175 gallbladder cancer Diseases 0.000 claims 1
- 206010017758 gastric cancer Diseases 0.000 claims 1
- 229960005219 gentisic acid Drugs 0.000 claims 1
- 235000012208 gluconic acid Nutrition 0.000 claims 1
- 229950006191 gluconic acid Drugs 0.000 claims 1
- 229940097043 glucuronic acid Drugs 0.000 claims 1
- 235000013922 glutamic acid Nutrition 0.000 claims 1
- 239000004220 glutamic acid Substances 0.000 claims 1
- 229960002989 glutamic acid Drugs 0.000 claims 1
- 238000002329 infrared spectrum Methods 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 229940045996 isethionic acid Drugs 0.000 claims 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims 1
- 201000010982 kidney cancer Diseases 0.000 claims 1
- 239000004310 lactic acid Substances 0.000 claims 1
- 235000014655 lactic acid Nutrition 0.000 claims 1
- 229940099563 lactobionic acid Drugs 0.000 claims 1
- 208000032839 leukemia Diseases 0.000 claims 1
- 201000007270 liver cancer Diseases 0.000 claims 1
- 208000014018 liver neoplasm Diseases 0.000 claims 1
- 201000005202 lung cancer Diseases 0.000 claims 1
- 208000020816 lung neoplasm Diseases 0.000 claims 1
- 210000002751 lymph Anatomy 0.000 claims 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims 1
- 239000011976 maleic acid Substances 0.000 claims 1
- 239000001630 malic acid Substances 0.000 claims 1
- 229940099690 malic acid Drugs 0.000 claims 1
- 235000011090 malic acid Nutrition 0.000 claims 1
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- 201000001441 melanoma Diseases 0.000 claims 1
- 201000008806 mesenchymal cell neoplasm Diseases 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 claims 1
- WUYZRUOVGJFWLD-UHFFFAOYSA-N n-piperidin-4-yl-1h-pyrazole-5-carboxamide Chemical compound C=1C=NNC=1C(=O)NC1CCNCC1 WUYZRUOVGJFWLD-UHFFFAOYSA-N 0.000 claims 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 claims 1
- 230000004770 neurodegeneration Effects 0.000 claims 1
- 208000015122 neurodegenerative disease Diseases 0.000 claims 1
- 239000011664 nicotinic acid Substances 0.000 claims 1
- 235000001968 nicotinic acid Nutrition 0.000 claims 1
- 229960003512 nicotinic acid Drugs 0.000 claims 1
- 208000002154 non-small cell lung carcinoma Diseases 0.000 claims 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims 1
- 229960002446 octanoic acid Drugs 0.000 claims 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims 1
- 229960002969 oleic acid Drugs 0.000 claims 1
- 229960005010 orotic acid Drugs 0.000 claims 1
- 235000006408 oxalic acid Nutrition 0.000 claims 1
- WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 claims 1
- 201000002528 pancreatic cancer Diseases 0.000 claims 1
- 208000008443 pancreatic carcinoma Diseases 0.000 claims 1
- 210000001428 peripheral nervous system Anatomy 0.000 claims 1
- WSHYKIAQCMIPTB-UHFFFAOYSA-M potassium;2-oxo-3-(3-oxo-1-phenylbutyl)chromen-4-olate Chemical compound [K+].[O-]C=1C2=CC=CC=C2OC(=O)C=1C(CC(=O)C)C1=CC=CC=C1 WSHYKIAQCMIPTB-UHFFFAOYSA-M 0.000 claims 1
- 230000002062 proliferating effect Effects 0.000 claims 1
- 238000011321 prophylaxis Methods 0.000 claims 1
- 235000019260 propionic acid Nutrition 0.000 claims 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims 1
- 201000000849 skin cancer Diseases 0.000 claims 1
- 239000001632 sodium acetate Substances 0.000 claims 1
- 235000017281 sodium acetate Nutrition 0.000 claims 1
- 239000000243 solution Substances 0.000 claims 1
- 239000008117 stearic acid Substances 0.000 claims 1
- 201000011549 stomach cancer Diseases 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 239000011975 tartaric acid Substances 0.000 claims 1
- 235000002906 tartaric acid Nutrition 0.000 claims 1
- 208000001608 teratocarcinoma Diseases 0.000 claims 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 201000002510 thyroid cancer Diseases 0.000 claims 1
- 230000004614 tumor growth Effects 0.000 claims 1
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims 1
- 201000005112 urinary bladder cancer Diseases 0.000 claims 1
- 229940005605 valeric acid Drugs 0.000 claims 1
- 230000009385 viral infection Effects 0.000 claims 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US64597305P | 2005-01-21 | 2005-01-21 | |
| US60/645,973 | 2005-01-21 | ||
| GB0501475.8 | 2005-01-22 | ||
| GB0501475A GB0501475D0 (en) | 2005-01-22 | 2005-01-22 | Pharmaceutical compounds |
| PCT/GB2006/000207 WO2006077426A2 (en) | 2005-01-21 | 2006-01-20 | 4- (2, 6-DICHLOROBENZOYLAMINO) -lH-PYRAZOLE-3 -CARBOXYLIC ACID PIPERIDIN- 4 -YLAMID ACID ADDITION SALTS AS KINASE INHIBITORS |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2008528470A JP2008528470A (ja) | 2008-07-31 |
| JP2008528470A5 true JP2008528470A5 (enExample) | 2009-03-12 |
| JP5184892B2 JP5184892B2 (ja) | 2013-04-17 |
Family
ID=36129898
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007551745A Expired - Fee Related JP5184892B2 (ja) | 2005-01-21 | 2006-01-20 | キナーゼ阻害剤としての４−（２，６−ジクロロ−ベンゾイルアミノ）−１ｈ−ピラゾール−３−カルボン酸ピペリジン−４−イルアミドの酸付加塩 |
Country Status (18)
| Country | Link |
|---|---|
| US (2) | US8013163B2 (enExample) |
| EP (1) | EP1846393B1 (enExample) |
| JP (1) | JP5184892B2 (enExample) |
| KR (1) | KR101344691B1 (enExample) |
| AR (1) | AR054425A1 (enExample) |
| AU (1) | AU2006207323B2 (enExample) |
| BR (1) | BRPI0606594A2 (enExample) |
| CA (1) | CA2593560C (enExample) |
| IL (1) | IL184504A (enExample) |
| MA (1) | MA29256B1 (enExample) |
| MX (1) | MX2007008783A (enExample) |
| NO (1) | NO340738B1 (enExample) |
| NZ (1) | NZ556471A (enExample) |
| PE (2) | PE20091785A1 (enExample) |
| RU (1) | RU2410385C2 (enExample) |
| SA (1) | SA06260465B1 (enExample) |
| TN (1) | TNSN07277A1 (enExample) |
| WO (1) | WO2006077426A2 (enExample) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101204247B1 (ko) * | 2003-07-22 | 2012-11-22 | 아스텍스 테라퓨틱스 리미티드 | 3,4-이치환된 1ｈ-피라졸 화합물 및 그의 시클린 의존성키나제 (ｃｄｋ) 및 글리코겐 합성효소 키나제-3(ｇｓｋ-3) 조정제로서 용도 |
| US20080139620A1 (en) * | 2005-01-21 | 2008-06-12 | Astex Therapeutics Limited | Pyrazole Derivatives For The Inhibition Of Cdk's And Gsk's |
| KR101346886B1 (ko) * | 2005-01-21 | 2014-01-02 | 아스텍스 테라퓨틱스 리미티드 | 제약 화합물 |
| US8404718B2 (en) * | 2005-01-21 | 2013-03-26 | Astex Therapeutics Limited | Combinations of pyrazole kinase inhibitors |
| AR054425A1 (es) * | 2005-01-21 | 2007-06-27 | Astex Therapeutics Ltd | Sales de adicion de piperidin 4-il- amida de acido 4-(2,6-dicloro-benzoilamino) 1h-pirazol-3-carboxilico. |
| MX2007008809A (es) * | 2005-01-21 | 2007-09-07 | Astex Therapeutics Ltd | Combinaciones de inhibidores de pirazol cinasa y otros agentes antitumor. |
| CA2594474C (en) * | 2005-01-21 | 2016-03-29 | Astex Therapeutics Limited | Pharmaceutical compounds |
| AR052559A1 (es) * | 2005-01-21 | 2007-03-21 | Astex Therapeutics Ltd | Derivados de pirazol para inhibir cdk's y gsk's |
| US20090036607A1 (en) * | 2005-03-03 | 2009-02-05 | Mitsubishi Rayon Co., Ltd. | Polymer particle, resin composition containing same, and molded body |
| RS52715B (sr) | 2005-04-13 | 2013-08-30 | Astex Therapeutics Limited | Derivati hidroksibenzamida i njihova primena kao inhibitora hsp90 |
| US20090318500A1 (en) * | 2006-05-05 | 2009-12-24 | Astex Therapeutics Limited | 4-(2, 6-Dichloro-benzoylamino)-1H-pyrazole-3-carboxylic acid (1-methanesulphonyl-piperidin-4-yl)-amide for the Treatment of Cancer |
| EP2026805A1 (en) * | 2006-05-08 | 2009-02-25 | Astex Therapeutics Limited | Pharmaceutical combinations of diazole derivatives for cancer treatment |
| JP2009543771A (ja) * | 2006-07-14 | 2009-12-10 | アステックス・セラピューティクス・リミテッド | 医薬化合物 |
| US8883790B2 (en) | 2006-10-12 | 2014-11-11 | Astex Therapeutics Limited | Pharmaceutical combinations |
| US9730912B2 (en) | 2006-10-12 | 2017-08-15 | Astex Therapeutics Limited | Pharmaceutical compounds |
| GB0620259D0 (en) | 2006-10-12 | 2006-11-22 | Astex Therapeutics Ltd | Pharmaceutical compounds |
| WO2008044041A1 (en) | 2006-10-12 | 2008-04-17 | Astex Therapeutics Limited | Pharmaceutical combinations |
| US7858663B1 (en) * | 2007-10-31 | 2010-12-28 | Pisgah Laboratories, Inc. | Physical and chemical properties of thyroid hormone organic acid addition salts |
| MX2010007154A (es) * | 2007-12-27 | 2010-10-05 | Kissei Pharmaceutical | Monosebacato de derivado de pirazol. |
| UY32297A (es) * | 2008-12-22 | 2010-05-31 | Almirall Sa | Sal mesilato de 5-(2-{[6-(2,2-difluoro-2-fenilitoxi) hexil]amino}-1-hidroxietil)-8-hidroxiquinolin-2( 1h)-ona como agonista del receptor b(beta)2 acrenérgico |
| PE20181446A1 (es) | 2016-03-17 | 2018-09-12 | Hoffmann La Roche | Derivados de 5-etil-4-metil-pirazol-3-carboxamida con actividad como de taar |
| US11077110B2 (en) | 2016-03-18 | 2021-08-03 | Tufts Medical Center | Compositions and methods for treating and preventing metabolic disorders |
| WO2018039324A1 (en) | 2016-08-23 | 2018-03-01 | Eisai R&D Management Co., Ltd. | Combination therapies for the treatment of hepatocellular carcinoma |
| WO2018170447A1 (en) | 2017-03-16 | 2018-09-20 | Eisai R&D Management Co., Ltd. | Combination therapies for the treatment of breast cancer |
Family Cites Families (133)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2917432A (en) | 1954-10-05 | 1959-12-15 | Burroughs Wellcome Co | Leukemia treatment |
| US3046301A (en) | 1959-10-29 | 1962-07-24 | Burroughs Wellcome Co | Method of making chlorambucil |
| GB1354939A (en) | 1971-10-28 | 1974-06-05 | Ici Ltd | Process for the manufacture of 1,1,2-triphenylalk-1-enes |
| US4005063A (en) | 1973-10-11 | 1977-01-25 | Abbott Laboratories | [Des-gly]10 -GnRH nonapeptide anide analogs in position 6 having ovulation-inducing activity |
| GB1524747A (en) | 1976-05-11 | 1978-09-13 | Ici Ltd | Polypeptide |
| US4282361A (en) | 1978-03-16 | 1981-08-04 | Massachusetts Institute Of Technology | Synthesis for 7-alkylamino-3-methylpyrazolo [4,3-d]pyrimidines |
| DE2845574A1 (de) | 1978-10-19 | 1980-04-24 | Deutsches Krebsforsch | Durch heterocyclische ringe oder alkylreste substituierte analoga von ccnu und verfahren zu deren herstellung |
| LU88769I2 (fr) | 1982-07-23 | 1996-11-05 | Zeneca Ltd | Bicalutamide et ses sels et esters pharmaceutiquement acceptables (Casodex (R)) |
| US4978672A (en) | 1986-03-07 | 1990-12-18 | Ciba-Geigy Corporation | Alpha-heterocyclc substituted tolunitriles |
| JPS6425763A (en) | 1987-04-24 | 1989-01-27 | Mitsubishi Chem Ind | Pyrazoles and insecticide and acaricide containing said pyrazoles as active ingredient |
| US5164196A (en) | 1987-05-19 | 1992-11-17 | Ventech Research, Inc. | Crotoxin complex as cytotoxic agent |
| US5002755A (en) | 1988-02-18 | 1991-03-26 | Vanderbilt University | Method of controlling nephrotoxicity of anti-tumor plaintum compounds |
| AU7885991A (en) | 1990-05-26 | 1991-12-31 | Byk Gulden Lomberg Chemische Fabrik Gmbh | 1,4-dihydropyridines for application in combatting resistance to drugs |
| IL100110A0 (en) | 1990-12-26 | 1992-08-18 | American Cyanamid Co | Insecticidal and synergistic miticidal compositions |
| HU219131B (hu) | 1991-10-18 | 2001-02-28 | Monsanto Co. | Módszer és fungicid készítmény növények torsgombabetegségének gátlására és a hatóanyagok |
| NZ258392A (en) | 1992-11-13 | 1997-09-22 | Idec Pharma Corp | Chimeric and radiolabelled antibodies to the b lymphocyte cellsurface antigen bp35 (cd-20) and their use in the treatment of b cell lymphona |
| NZ257770A (en) | 1992-12-17 | 1997-02-24 | Pfizer | 3- acylpyrazole and pyrazolo[3,4-d]pyrimidine derivatives |
| US5773001A (en) | 1994-06-03 | 1998-06-30 | American Cyanamid Company | Conjugates of methyltrithio antitumor agents and intermediates for their synthesis |
| EP0788358B1 (en) | 1994-11-10 | 2004-03-31 | Millennium Pharmaceuticals, Inc. | Use of pyrazole compounds for the treatment of glomerulonephritis, cancer, atherosclerosis or restenosis |
| US5502068A (en) | 1995-01-31 | 1996-03-26 | Synphar Laboratories, Inc. | Cyclopropylpyrroloindole-oligopeptide anticancer agents |
| US5675024A (en) | 1995-11-22 | 1997-10-07 | Allergan | Aryl or heteroaryl amides of tetrahydronaphthalene, chroman, thiochroman and 1,2,3,4,-tetrahydroquinoline carboxylic acids, having an electron withdrawing substituent in the aromatic or heteroaromatic moiety, having retinoid-like biological activity |
| US5663357A (en) | 1995-11-22 | 1997-09-02 | Allergan | Substituted heteroarylamides having retinoid-like biological activity |
| US6066738A (en) | 1996-01-30 | 2000-05-23 | Merck & Co., Inc. | Inhibitors of farnesyl-protein transferase |
| JP2000507956A (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−タンパク質トランスフェラーゼ阻害剤 |
| JP2000509371A (ja) | 1996-04-03 | 2000-07-25 | 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―タンパク質トランスフェラーゼ阻害剤 |
| WO1997036897A1 (en) | 1996-04-03 | 1997-10-09 | Merck & Co., Inc. | Inhibitors of farnesyl-protein transferase |
| ES2246513T3 (es) | 1996-05-03 | 2006-02-16 | Abbott Laboratories | Nuevos peptidos anti-angiogenicos, polinucleotidos que los codifican y procedimientos de inhibicion de la angiogenesis. |
| ATE265997T1 (de) | 1996-06-21 | 2004-05-15 | Allergan Inc | Substituierte tetrahydronaphthalin- und dihydronaphthalin-derivate mit einer retinoiden und/oder retinoid antagonist-ähnlichen biologischen aktivität |
| TW523506B (en) | 1996-12-18 | 2003-03-11 | Ono Pharmaceutical Co | Sulfonamide or carbamide derivatives and drugs containing the same as active ingredients |
| US6020357A (en) | 1996-12-23 | 2000-02-01 | Dupont Pharmaceuticals Company | Nitrogen containing heteroaromatics as factor Xa inhibitors |
| HUP0000735A3 (en) | 1996-12-23 | 2002-03-28 | Bristol Myers Squibb Pharma Co | Nitrogen containing heteroaromatics as factor xa inhibitors |
| US6306393B1 (en) | 1997-03-24 | 2001-10-23 | Immunomedics, Inc. | Immunotherapy of B-cell malignancies using anti-CD22 antibodies |
| CN1281588C (zh) | 1997-04-25 | 2006-10-25 | 美国辉瑞有限公司 | 制备吡唑并嘧啶酮类化合物的新型中间体 |
| WO1998052941A1 (en) | 1997-05-22 | 1998-11-26 | G.D. Searle And Co. | PYRAZOLE DERIVATIVES AS p38 KINASE INHIBITORS |
| JP2002507968A (ja) | 1997-06-19 | 2002-03-12 | デュポン ファーマシューティカルズ カンパニー | 中性のＰ１特異性基を有するＸａ因子阻害剤 |
| JP3811006B2 (ja) | 1997-12-19 | 2006-08-16 | シエーリング アクチエンゲゼルシャフト | 抗凝血物質類としてのオルト−アントラニルアミド誘導体類 |
| BR9813835A (pt) | 1997-12-22 | 2000-10-10 | Du Pont Pharm Co | Composto, composição farmacêutica e método de tratamento ou prevenção de uma desordem tromboembólica |
| WO1999067235A1 (en) | 1998-06-25 | 1999-12-29 | Sumitomo Pharmaceuticals Co., Ltd. | Five-membered ring compounds |
| JP2000186092A (ja) | 1998-12-22 | 2000-07-04 | Kyowa Hakko Kogyo Co Ltd | Ｕｃｎ−０１の製造法 |
| EP1058549A4 (en) | 1998-12-23 | 2003-11-12 | Bristol Myers Squibb Pharma Co | FACTOR Xa OR THROMBIN INHIBITORS |
| DE60003025T2 (de) | 1999-04-02 | 2004-03-18 | Bristol-Myers Squibb Pharma Co. | Arylsulfonyle als faktor xa inhibitoren |
| PT1169038E (pt) | 1999-04-15 | 2012-10-26 | Bristol Myers Squibb Co | Inibidores cíclicos da proteína tirosina cinase |
| US6166244A (en) | 1999-05-07 | 2000-12-26 | Allergan Sales, Inc. | Oxygen, sulfur and nitrogen substituted cyclohexene and cyclohexane derivatives having retinoid-like biological activity |
| CA2371904A1 (en) | 1999-05-24 | 2000-11-30 | Bing-Yan Zhu | Inhibitors of factor xa |
| FR2795726A1 (fr) | 1999-06-30 | 2001-01-05 | Aventis Cropscience Sa | Nouveaux pyrazoles fongicides |
| PE20010306A1 (es) | 1999-07-02 | 2001-03-29 | Agouron Pharma | Compuestos de indazol y composiciones farmaceuticas que los contienen utiles para la inhibicion de proteina kinasa |
| WO2001014331A2 (en) | 1999-08-24 | 2001-03-01 | Regents Of The University Of California | Non-quinoline inhibitors of malaria parasites |
| CZ2002961A3 (cs) | 1999-09-17 | 2002-08-14 | Millennium Pharmaceuticals, Inc. | Benzamidy a příbuzné sloučeniny pro inhibici faktoru Xa |
| CZ2002959A3 (cs) | 1999-09-17 | 2002-07-17 | Millennium Pharmaceuticals, Inc. | Inhibitory faktoru Xa |
| US6632815B2 (en) | 1999-09-17 | 2003-10-14 | Millennium Pharmaceuticals, Inc. | Inhibitors of factor Xa |
| US6485907B1 (en) | 2000-01-11 | 2002-11-26 | Syngenta Participations Ag | PCR-based detection of Rhizoctonia cerealis |
| HN2001000008A (es) | 2000-01-21 | 2003-12-11 | Inc Agouron Pharmaceuticals | Compuesto de amida y composiciones farmaceuticas para inhibir proteinquinasas, y su modo de empleo |
| WO2001058869A2 (en) | 2000-02-11 | 2001-08-16 | Bristol-Myers Squibb Company | Cannabinoid receptor modulators, their processes of preparation, and use of cannabinoid receptor modulators in treating respiratory and non-respiratory diseases |
| WO2001064643A2 (en) | 2000-02-29 | 2001-09-07 | Cor Therapeutics, Inc. | BENZAMIDES AND RELATED INHIBITORS OF FACTOR Xa |
| WO2001068585A1 (en) | 2000-03-14 | 2001-09-20 | Fujisawa Pharmaceutical Co., Ltd. | Novel amide compounds |
| AU4878601A (en) | 2000-04-20 | 2001-11-07 | Mitsubishi Corporation | Aromatic amide compounds |
| JP2004509064A (ja) | 2000-04-27 | 2004-03-25 | アボット・ラボラトリーズ | 置換フェニルファルネシルトランスフェラーゼ阻害剤 |
| US6414013B1 (en) | 2000-06-19 | 2002-07-02 | Pharmacia & Upjohn S.P.A. | Thiophene compounds, process for preparing the same, and pharmaceutical compositions containing the same background of the invention |
| WO2002000651A2 (en) | 2000-06-27 | 2002-01-03 | Bristol-Myers Squibb Pharma Company | Factor xa inhibitors |
| BR0112856A (pt) | 2000-07-31 | 2003-07-01 | Smithkline Beecham Plc | Método para o tratamento dos distúrbios, composto ou um sal ou solvato deste, processo para a preparação dos mesmos, composição farmacêutico, método de tratamento e/ou profilaxia de um ou mais dos distúrbios, uso de um composto, e, método para o tratamento de diabetes, grande depressão, depressão manìaca, ansiedade, esquizofrenia e distúrbios do sono, em mamìferos humanos e não humanos |
| IL154016A0 (en) | 2000-08-31 | 2003-07-31 | Pfizer Prod Inc | Pyrazole derivatives and their use as protein kinase inhibitors |
| MXPA03002297A (es) | 2000-09-15 | 2003-06-06 | Vertex Pharma | Compuestos de triazol utiles como inhibidores de proteina cinasa. |
| EP1414804A1 (en) | 2000-10-20 | 2004-05-06 | Bristol-Myers Squibb Pharma Company | Acylsemicarbazides and their use as cyclin dependent kinase (cdk) inhibitors |
| US6455559B1 (en) | 2001-07-19 | 2002-09-24 | Pharmacia Italia S.P.A. | Phenylacetamido-pyrazole derivatives, process for their preparation and their use as antitumor agents |
| ES2375491T3 (es) | 2000-12-21 | 2012-03-01 | Vertex Pharmaceuticals Incorporated | Compuestos de pirazol útiles como agentes inhibidores de las prote�?na-quinasas. |
| DE10064823A1 (de) | 2000-12-22 | 2002-06-27 | Knoll Ag | Integrinrezeptorliganden |
| US6995162B2 (en) | 2001-01-12 | 2006-02-07 | Amgen Inc. | Substituted alkylamine derivatives and methods of use |
| US7105682B2 (en) * | 2001-01-12 | 2006-09-12 | Amgen Inc. | Substituted amine derivatives and methods of use |
| US6878714B2 (en) | 2001-01-12 | 2005-04-12 | Amgen Inc. | Substituted alkylamine derivatives and methods of use |
| GB0102687D0 (en) * | 2001-02-02 | 2001-03-21 | Pharmacia & Upjohn Spa | Oxazolyl-pyrazole derivatives active as kinase inhibitors,process for their preparation and pharmaceutical compositions comprising them |
| MY130778A (en) | 2001-02-09 | 2007-07-31 | Vertex Pharma | Heterocyclic inhibitiors of erk2 and uses thereof |
| US20050260277A1 (en) | 2001-02-28 | 2005-11-24 | Giles Brian C | Method and formula for anti-tumor and anti-matastatic effect |
| ATE509913T1 (de) | 2001-03-05 | 2011-06-15 | Du Pont | Heterozyklische diamide zur bekämpfung wirbelloser schädlinge |
| GB0106661D0 (en) | 2001-03-16 | 2001-05-09 | Pfizer Ltd | Pharmaceutically active compounds |
| WO2002074312A1 (en) | 2001-03-16 | 2002-09-26 | Pfizer Limited | Pyrazolo`4,3-d.pyrimidinone compounds as cgmp pde inhibitors |
| WO2002074298A1 (en) | 2001-03-21 | 2002-09-26 | Ono Pharmaceutical Co., Ltd. | Il-6 production inhibitors |
| RU2344123C9 (ru) | 2001-04-16 | 2009-05-20 | Шеринг Корпорейшн | 3,4-дизамещенные циклобутен-1,2-дионы как лиганды схс-хемокинового рецептора |
| US6905669B2 (en) | 2001-04-24 | 2005-06-14 | Supergen, Inc. | Compositions and methods for reestablishing gene transcription through inhibition of DNA methylation and histone deacetylase |
| RU2332415C2 (ru) * | 2001-04-27 | 2008-08-27 | Вертекс Фармасьютикалз Инкорпорейтед | Производные пиразола, полезные в качестве ингибиторов протеинкиназы |
| WO2002092002A2 (en) | 2001-05-11 | 2002-11-21 | The Burnham Institute | Screening, diagnostic and therapeutic methods relating to riz |
| WO2002094183A2 (en) | 2001-05-18 | 2002-11-28 | Tap Pharmaceutical Products Inc. | A method for tumor treatment with fumagillol derivatives |
| KR100849815B1 (ko) | 2001-05-21 | 2008-07-31 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 비방향족 헤테로시클릭 고리를 포함하는 디아미드 무척추해충 방제제 |
| WO2002101007A2 (en) | 2001-06-13 | 2002-12-19 | Genesoft Pharmaceuticals, Inc | Antipathogenic benzamide compounds |
| US6916798B2 (en) | 2001-08-03 | 2005-07-12 | Vertex Pharmaceuticals Incorporated | Inhibitors of GSK-3 and uses thereof |
| AUPR738301A0 (en) | 2001-08-30 | 2001-09-20 | Starpharma Limited | Chemotherapeutic agents |
| EP1421077A4 (en) | 2001-08-31 | 2004-11-17 | Univ Connecticut | NEW PYRAZOLANALOGS ON CANNABINOID RECEPTORS |
| CA2465978C (en) | 2001-09-14 | 2015-04-07 | Soon Hyung Woo | Inhibitors of histone deacetylase |
| HN2002000317A (es) * | 2001-11-02 | 2003-05-21 | Pfizer | Inhibidores de pde9 para tratamiento de trastornos cardiovasculares |
| US6919359B2 (en) | 2001-11-08 | 2005-07-19 | Pfizer Inc | Azabicyclic-substituted-heteroaryl compounds for the treatment of disease |
| AU2002350217A1 (en) | 2001-12-04 | 2003-06-17 | Bristol-Myers Squibb Company | Glycinamides as factor xa inhibitors |
| GEP20063909B (en) | 2002-01-22 | 2006-08-25 | Warner Lambert Co | 2-(PYRIDIN-2-YLAMINO)-PYRIDO[2,3d] PYRIMIDIN-7-ONES |
| US7205307B2 (en) | 2002-02-14 | 2007-04-17 | Icagen, Inc. | Pyrimidines as novel openers of potassium ion channels |
| RU2394022C2 (ru) | 2002-03-04 | 2010-07-10 | МЕРК ЭйчДиЭйСи Рисерч, ЛЛС | Способы индукции конечной дифференцировки |
| ATE486600T1 (de) | 2002-03-12 | 2010-11-15 | Merck Sharp & Dohme | Di-aryl-substituierte tetrazol-modulatoren des metabotropen glutamat-rezeptors-5 |
| EP1348707B1 (en) | 2002-03-28 | 2010-08-25 | Ustav Experimentalni Botaniky AV CR, v.v.i. (Institute of Experimental Botany Academy of Sciences of the Czech Republic, PRO) | Pyrazolo[4,3-d]pyrimidines, processes for their preparation and methods for therapy |
| US6995168B2 (en) | 2002-05-31 | 2006-02-07 | Euro-Celtique S.A. | Triazaspiro compounds useful for treating or preventing pain |
| AU2003249369A1 (en) | 2002-06-21 | 2004-01-06 | Cellular Genomics, Inc. | Certain amino-substituted monocycles as kinase modulators |
| GB0218625D0 (en) | 2002-08-10 | 2002-09-18 | Astex Technology Ltd | Pharmaceutical compounds |
| AR041291A1 (es) | 2002-09-19 | 2005-05-11 | Schering Corp | Imidazopiridinas como inhibidores de quinasa dependientes de ciclina |
| WO2004039795A2 (en) | 2002-10-29 | 2004-05-13 | Fujisawa Pharmaceutical Co., Ltd. | Amide compounds for the treatment of hyperlipidemia |
| US20050026877A1 (en) | 2002-12-03 | 2005-02-03 | Novacea, Inc. | Pharmaceutical compositions comprising active vitamin D compounds |
| US7202257B2 (en) | 2003-12-24 | 2007-04-10 | Deciphera Pharmaceuticals, Llc | Anti-inflammatory medicaments |
| US7144911B2 (en) | 2002-12-31 | 2006-12-05 | Deciphera Pharmaceuticals Llc | Anti-inflammatory medicaments |
| US7169797B2 (en) | 2003-02-14 | 2007-01-30 | Abbott Laboratories | Protein-tyrosine phosphatase inhibitors and uses thereof |
| US7320989B2 (en) | 2003-02-28 | 2008-01-22 | Encysive Pharmaceuticals, Inc. | Pyridine, pyrimidine, quinoline, quinazoline, and naphthalene urotensin-II receptor antagonists |
| AR043633A1 (es) | 2003-03-20 | 2005-08-03 | Schering Corp | Ligandos de receptores de canabinoides |
| WO2004099127A1 (en) | 2003-05-07 | 2004-11-18 | Novo Nordisk A/S | Novel compounds as kinase inhibitors |
| JP2006525987A (ja) | 2003-05-09 | 2006-11-16 | ファルマシア・アンド・アップジョン・カンパニー・エルエルシー | 置換ピリミジン誘導体 |
| US20070167500A1 (en) | 2003-06-27 | 2007-07-19 | Takayuki Maruyama | Remedy for urinary tract diseases |
| WO2005000309A2 (en) | 2003-06-27 | 2005-01-06 | Ionix Pharmaceuticals Limited | Chemical compounds |
| TWI372050B (en) | 2003-07-03 | 2012-09-11 | Astex Therapeutics Ltd | (morpholin-4-ylmethyl-1h-benzimidazol-2-yl)-1h-pyrazoles |
| KR101204247B1 (ko) | 2003-07-22 | 2012-11-22 | 아스텍스 테라퓨틱스 리미티드 | 3,4-이치환된 1ｈ-피라졸 화합물 및 그의 시클린 의존성키나제 (ｃｄｋ) 및 글리코겐 합성효소 키나제-3(ｇｓｋ-3) 조정제로서 용도 |
| SE0303396D0 (sv) | 2003-12-16 | 2003-12-16 | Astrazeneca Ab | Chemical compounds |
| CA2556872C (en) | 2004-02-20 | 2015-05-12 | Chiron Corporation | Modulation of inflammatory and metastatic processes |
| DK1725528T3 (da) | 2004-03-11 | 2013-09-02 | 4Sc Ag | Sulfonylpyrroler som hdac-inhibitorer |
| US20060084691A1 (en) | 2004-10-18 | 2006-04-20 | Bilal Piperdi | Combined treatment with bortezomib and an epidermal growth factor receptor kinase inhibitor |
| CA2594474C (en) | 2005-01-21 | 2016-03-29 | Astex Therapeutics Limited | Pharmaceutical compounds |
| AR052559A1 (es) | 2005-01-21 | 2007-03-21 | Astex Therapeutics Ltd | Derivados de pirazol para inhibir cdk's y gsk's |
| US20080139620A1 (en) | 2005-01-21 | 2008-06-12 | Astex Therapeutics Limited | Pyrazole Derivatives For The Inhibition Of Cdk's And Gsk's |
| US8404718B2 (en) | 2005-01-21 | 2013-03-26 | Astex Therapeutics Limited | Combinations of pyrazole kinase inhibitors |
| MX2007008809A (es) | 2005-01-21 | 2007-09-07 | Astex Therapeutics Ltd | Combinaciones de inhibidores de pirazol cinasa y otros agentes antitumor. |
| AR054425A1 (es) | 2005-01-21 | 2007-06-27 | Astex Therapeutics Ltd | Sales de adicion de piperidin 4-il- amida de acido 4-(2,6-dicloro-benzoilamino) 1h-pirazol-3-carboxilico. |
| KR101346886B1 (ko) | 2005-01-21 | 2014-01-02 | 아스텍스 테라퓨틱스 리미티드 | 제약 화합물 |
| JPWO2006085685A1 (ja) | 2005-02-09 | 2008-06-26 | 武田薬品工業株式会社 | ピラゾール化合物 |
| KR20080027908A (ko) | 2005-06-30 | 2008-03-28 | 프로시디온 리미티드 | Ｇｐｃｒ 효능제 |
| US20090318500A1 (en) | 2006-05-05 | 2009-12-24 | Astex Therapeutics Limited | 4-(2, 6-Dichloro-benzoylamino)-1H-pyrazole-3-carboxylic acid (1-methanesulphonyl-piperidin-4-yl)-amide for the Treatment of Cancer |
| EP2026805A1 (en) | 2006-05-08 | 2009-02-25 | Astex Therapeutics Limited | Pharmaceutical combinations of diazole derivatives for cancer treatment |
| EP2043635A2 (en) | 2006-06-29 | 2009-04-08 | Astex Therapeutics Limited | Pharmaceutical combinations |
| US20090263398A1 (en) | 2006-07-14 | 2009-10-22 | Astex Therapeutics Limited | Pharmaceutical combinations |
| JP2009543771A (ja) | 2006-07-14 | 2009-12-10 | アステックス・セラピューティクス・リミテッド | 医薬化合物 |
| WO2008007122A2 (en) | 2006-07-14 | 2008-01-17 | Astex Therapeutics Limited | Combinations of pyrazole derivatives for the inhibition of cdks and gsk's |
| EP2046327A1 (en) | 2006-07-21 | 2009-04-15 | Astex Therapeutics Limited | Medical use of cyclin dependent kinases inhibitors |
| WO2008044041A1 (en) | 2006-10-12 | 2008-04-17 | Astex Therapeutics Limited | Pharmaceutical combinations |
-
2006
- 2006-01-19 AR ARP060100203A patent/AR054425A1/es active IP Right Grant
- 2006-01-20 PE PE2009001082A patent/PE20091785A1/es active IP Right Grant
- 2006-01-20 NZ NZ556471A patent/NZ556471A/en not_active IP Right Cessation
- 2006-01-20 BR BRPI0606594-5A patent/BRPI0606594A2/pt not_active Application Discontinuation
- 2006-01-20 PE PE2006000078A patent/PE20061018A1/es not_active Application Discontinuation
- 2006-01-20 CA CA2593560A patent/CA2593560C/en not_active Expired - Fee Related
- 2006-01-20 WO PCT/GB2006/000207 patent/WO2006077426A2/en not_active Ceased
- 2006-01-20 EP EP06700762.5A patent/EP1846393B1/en not_active Expired - Lifetime
- 2006-01-20 US US11/814,458 patent/US8013163B2/en not_active Expired - Fee Related
- 2006-01-20 AU AU2006207323A patent/AU2006207323B2/en not_active Ceased
- 2006-01-20 RU RU2007131100/04A patent/RU2410385C2/ru not_active IP Right Cessation
- 2006-01-20 MX MX2007008783A patent/MX2007008783A/es active IP Right Grant
- 2006-01-20 JP JP2007551745A patent/JP5184892B2/ja not_active Expired - Fee Related
- 2006-01-21 SA SA6260465A patent/SA06260465B1/ar unknown
-
2007
- 2007-07-09 IL IL184504A patent/IL184504A/en active IP Right Grant
- 2007-07-20 TN TNP2007000277A patent/TNSN07277A1/en unknown
- 2007-07-27 NO NO20073957A patent/NO340738B1/no not_active IP Right Cessation
- 2007-08-16 MA MA30146A patent/MA29256B1/fr unknown
- 2007-08-17 KR KR1020077018925A patent/KR101344691B1/ko not_active Expired - Fee Related
-
2011
- 2011-07-22 US US13/188,887 patent/US8293767B2/en not_active Expired - Fee Related
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2008528470A5 (enExample) | ||
| RU2410385C2 (ru) | Соединения для использования в фармацевтике | |
| EP3345906B1 (en) | 2-arylamino pyridine, pyridine or triazine derivative, preparation method and use thereof | |
| JP5064024B2 (ja) | イマチニブの製造方法、及び該方法により製造されたイマチニブ | |
| TWI549953B (zh) | ７－環戊基－２－（５－哌－１－基－吡啶－２－基胺基）－７ｈ－吡咯并［２，３－ｄ］嘧啶－６－羧酸二甲醯胺之鹽類及其製備方法 | |
| CN105722840B (zh) | 作为PI3K、mTOR抑制剂的稠合喹啉化合物 | |
| AU2019218187B2 (en) | Dioxinoquinoline compounds, preparation method and uses thereof | |
| JP2023536948A (ja) | Ｅｇｆｒ阻害剤およびその製造方法と応用 | |
| JP2009542608A5 (enExample) | ||
| JP2008528467A5 (enExample) | ||
| EP2997030A1 (en) | Pyrrolo[2,3-d]pyrimidine derivatives, process for their preparation and their use as kinase inhibitors | |
| CN107922348A (zh) | 双环杂环酰胺衍生物 | |
| EP2885304B1 (en) | Pyrrolopyrazoles as n-type calcium channel blockers | |
| CN102675323A (zh) | 吡咯并[2,1-f][1,2,4]三嗪衍生物及其抗肿瘤用途 | |
| WO2021163629A1 (en) | Inhibitors of ulk1/2 and methods of using same | |
| JP2025081599A (ja) | Ｅｇｆｒキナーゼを阻害する化合物、調製方法、及びその使用 | |
| CN110078730B (zh) | 作为pi3k/mtor抑制剂的喹啉取代的稠合喹啉化合物 | |
| KR102433023B1 (ko) | 디옥시노퀴놀린 화합물, 이의 제조방법 및 용도 | |
| CN1913897A (zh) | 新颖化合物及其组合物、制备方法和/或治疗方法 | |
| EP3750894B1 (en) | Urea-substituted aromatic ring-linked dioxazoline compound, preparation method therefor, and uses thereof | |
| AU2007254258A1 (en) | Crystalline forms of 5-chloro-6- (2, 6-difluoro-4- [3- (methylamino) propoxy] phenyl)-N-((1S)-2, 2, 2,-trifluoro-1-methylethyl] [1,2,4] triazolo [1,5-a] pyrimidin-7-amine salts | |
| JP7765105B2 (ja) | ピリミジン－４，６－ジアミン誘導体およびその製造方法と薬学上の応用 | |
| TWI455932B (zh) | 4－(2,6－二氯苯甲醯胺基)－1h－吡唑－3－羧酸哌啶－4－基醯胺之酸加成鹽、製備方法及用途 | |
| CN104119343A (zh) | 2-三氟甲基噻二唑类化合物及其用途 |