JP2008506761A5 - - Google Patents
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- Publication number
- JP2008506761A5 JP2008506761A5 JP2007522032A JP2007522032A JP2008506761A5 JP 2008506761 A5 JP2008506761 A5 JP 2008506761A5 JP 2007522032 A JP2007522032 A JP 2007522032A JP 2007522032 A JP2007522032 A JP 2007522032A JP 2008506761 A5 JP2008506761 A5 JP 2008506761A5
- Authority
- JP
- Japan
- Prior art keywords
- carboxylic acid
- thiazole
- hydrogen
- cancer
- benzoylamino
- 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.)
- Withdrawn
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- 125000001183 hydrocarbyl group Chemical group 0.000 claims 29
- 229910052739 hydrogen Inorganic materials 0.000 claims 26
- 239000001257 hydrogen Substances 0.000 claims 26
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 22
- -1 tautomers Chemical class 0.000 claims 22
- 125000003545 alkoxy group Chemical group 0.000 claims 20
- 229910052736 halogen Inorganic materials 0.000 claims 20
- 150000002367 halogens Chemical class 0.000 claims 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 18
- 125000002837 carbocyclic group Chemical group 0.000 claims 18
- 125000004432 carbon atom Chemical group C* 0.000 claims 18
- 125000000623 heterocyclic group Chemical group 0.000 claims 18
- 150000001875 compounds Chemical class 0.000 claims 14
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 11
- 229910052731 fluorine Inorganic materials 0.000 claims 11
- 239000011737 fluorine Substances 0.000 claims 11
- 229910052717 sulfur Inorganic materials 0.000 claims 8
- 150000001204 N-oxides Chemical class 0.000 claims 7
- 206010028980 Neoplasm Diseases 0.000 claims 7
- 150000002431 hydrogen Chemical class 0.000 claims 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 7
- 150000003839 salts Chemical class 0.000 claims 7
- 239000012453 solvate Substances 0.000 claims 7
- 125000002947 alkylene group Chemical group 0.000 claims 6
- 125000004429 atom Chemical group 0.000 claims 6
- 201000011510 cancer Diseases 0.000 claims 6
- 229910052760 oxygen Inorganic materials 0.000 claims 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 6
- 125000001424 substituent group Chemical group 0.000 claims 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 4
- 201000005787 hematologic cancer Diseases 0.000 claims 3
- 208000024200 hematopoietic and lymphoid system neoplasm Diseases 0.000 claims 3
- 230000002265 prevention Effects 0.000 claims 3
- 208000024891 symptom Diseases 0.000 claims 3
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 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
- 206010025323 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
- 206010060862 Prostate cancer Diseases 0.000 claims 2
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 2
- DGYIJVNZSDYBOE-UHFFFAOYSA-N [CH2]C1=CC=NC=C1 Chemical group [CH2]C1=CC=NC=C1 DGYIJVNZSDYBOE-UHFFFAOYSA-N 0.000 claims 2
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 2
- 210000004027 cell Anatomy 0.000 claims 2
- 208000029742 colonic neoplasm Diseases 0.000 claims 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 2
- 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
- 201000004101 esophageal cancer Diseases 0.000 claims 2
- 230000001404 mediated effect Effects 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- GNFBDRVLKIAIAI-UHFFFAOYSA-N 4-(cyclopentanecarbonylamino)-n-(5-piperazin-1-ylpyridin-2-yl)-1,2-thiazole-3-carboxamide Chemical compound C1CCCC1C(=O)NC1=CSN=C1C(=O)NC(N=C1)=CC=C1N1CCNCC1 GNFBDRVLKIAIAI-UHFFFAOYSA-N 0.000 claims 1
- DYIHGFOHKQDOFZ-UHFFFAOYSA-N 4-[(2,6-dichlorobenzoyl)amino]-n-(1-methylpiperidin-4-yl)-1,2-thiazole-3-carboxamide Chemical compound C1CN(C)CCC1NC(=O)C1=NSC=C1NC(=O)C1=C(Cl)C=CC=C1Cl DYIHGFOHKQDOFZ-UHFFFAOYSA-N 0.000 claims 1
- AXTNWXOQUGZQEN-UHFFFAOYSA-N 4-[(2,6-dichlorobenzoyl)amino]-n-(1-methylsulfonylpiperidin-4-yl)-1,2-thiazole-3-carboxamide Chemical compound C1CN(S(=O)(=O)C)CCC1NC(=O)C1=NSC=C1NC(=O)C1=C(Cl)C=CC=C1Cl AXTNWXOQUGZQEN-UHFFFAOYSA-N 0.000 claims 1
- OJDSVYGVQABZKY-UHFFFAOYSA-N 4-[(2,6-dichlorobenzoyl)amino]-n-(4-piperazin-1-ylphenyl)-1,2-thiazole-3-carboxamide Chemical compound ClC1=CC=CC(Cl)=C1C(=O)NC1=CSN=C1C(=O)NC1=CC=C(N2CCNCC2)C=C1 OJDSVYGVQABZKY-UHFFFAOYSA-N 0.000 claims 1
- ZGAOBUVBYJMOIO-UHFFFAOYSA-N 4-[(2,6-dichlorobenzoyl)amino]-n-(5-piperazin-1-ylpyridin-2-yl)-1,2-thiazole-3-carboxamide Chemical compound ClC1=CC=CC(Cl)=C1C(=O)NC1=CSN=C1C(=O)NC1=CC=C(N2CCNCC2)C=N1 ZGAOBUVBYJMOIO-UHFFFAOYSA-N 0.000 claims 1
- IGQKVMFJQYYNHP-UHFFFAOYSA-N 4-benzamido-n-(4-piperazin-1-ylphenyl)-1,2-thiazole-3-carboxamide Chemical compound N=1SC=C(NC(=O)C=2C=CC=CC=2)C=1C(=O)NC(C=C1)=CC=C1N1CCNCC1 IGQKVMFJQYYNHP-UHFFFAOYSA-N 0.000 claims 1
- RUDIFZNAIWMHCD-UHFFFAOYSA-N 5-(1-phenylethylamino)-n-piperidin-4-yl-1,3-thiazole-4-carboxamide Chemical compound C=1C=CC=CC=1C(C)NC=1SC=NC=1C(=O)NC1CCNCC1 RUDIFZNAIWMHCD-UHFFFAOYSA-N 0.000 claims 1
- JNYPMZYCAWPDQM-UHFFFAOYSA-N 5-(benzylamino)-n-piperidin-4-yl-1,3-thiazole-4-carboxamide Chemical compound N1=CSC(NCC=2C=CC=CC=2)=C1C(=O)NC1CCNCC1 JNYPMZYCAWPDQM-UHFFFAOYSA-N 0.000 claims 1
- ZVEIEBFLWBOITR-UHFFFAOYSA-N 5-[(2,6-dichlorobenzoyl)amino]-n-(4-piperazin-1-ylphenyl)-1,3-thiazole-4-carboxamide Chemical compound ClC1=CC=CC(Cl)=C1C(=O)NC1=C(C(=O)NC=2C=CC(=CC=2)N2CCNCC2)N=CS1 ZVEIEBFLWBOITR-UHFFFAOYSA-N 0.000 claims 1
- UVPSVMSAVYAYOK-UHFFFAOYSA-N 5-[(2,6-dichlorophenyl)methylamino]-n-piperidin-4-yl-1,3-thiazole-4-carboxamide Chemical compound ClC1=CC=CC(Cl)=C1CNC1=C(C(=O)NC2CCNCC2)N=CS1 UVPSVMSAVYAYOK-UHFFFAOYSA-N 0.000 claims 1
- HEYUDERTMFOHRY-UHFFFAOYSA-N 5-[(2,6-difluorobenzoyl)amino]-n-piperidin-4-yl-1,3-thiazole-4-carboxamide Chemical compound FC1=CC=CC(F)=C1C(=O)NC1=C(C(=O)NC2CCNCC2)N=CS1 HEYUDERTMFOHRY-UHFFFAOYSA-N 0.000 claims 1
- QSXRFTZWQXQGNZ-UHFFFAOYSA-N 5-[(2-ethoxybenzoyl)amino]-n-piperidin-4-yl-1,3-thiazole-4-carboxamide Chemical compound CCOC1=CC=CC=C1C(=O)NC1=C(C(=O)NC2CCNCC2)N=CS1 QSXRFTZWQXQGNZ-UHFFFAOYSA-N 0.000 claims 1
- NOIVZCHOIWNQBZ-UHFFFAOYSA-N 5-[(2-methoxyphenyl)methylamino]-n-(5-piperazin-1-ylpyridin-2-yl)-1,3-thiazole-4-carboxamide Chemical compound COC1=CC=CC=C1CNC1=C(C(=O)NC=2N=CC(=CC=2)N2CCNCC2)N=CS1 NOIVZCHOIWNQBZ-UHFFFAOYSA-N 0.000 claims 1
- QSSSHSCAYCKMPX-UHFFFAOYSA-N 5-[(2-methoxyphenyl)methylamino]-n-piperidin-4-yl-1,3-thiazole-4-carboxamide Chemical compound COC1=CC=CC=C1CNC1=C(C(=O)NC2CCNCC2)N=CS1 QSSSHSCAYCKMPX-UHFFFAOYSA-N 0.000 claims 1
- DHHFLNWAAJEZHD-UHFFFAOYSA-N 5-anilino-n-(4-piperazin-1-ylphenyl)-1,3-thiazole-4-carboxamide Chemical compound N1=CSC(NC=2C=CC=CC=2)=C1C(=O)NC(C=C1)=CC=C1N1CCNCC1 DHHFLNWAAJEZHD-UHFFFAOYSA-N 0.000 claims 1
- NRYMLBIVHGSKFQ-UHFFFAOYSA-N 5-anilino-n-(5-piperazin-1-ylpyridin-2-yl)-1,3-thiazole-4-carboxamide Chemical compound N1=CSC(NC=2C=CC=CC=2)=C1C(=O)NC(N=C1)=CC=C1N1CCNCC1 NRYMLBIVHGSKFQ-UHFFFAOYSA-N 0.000 claims 1
- CFDOJVDGZDCKBF-UHFFFAOYSA-N 5-anilino-n-phenyl-1,3-thiazole-4-carboxamide Chemical compound N1=CSC(NC=2C=CC=CC=2)=C1C(=O)NC1=CC=CC=C1 CFDOJVDGZDCKBF-UHFFFAOYSA-N 0.000 claims 1
- JEPQOIAPDXCGNY-UHFFFAOYSA-N 5-anilino-n-pyridin-2-yl-1,3-thiazole-4-carboxamide Chemical compound N1=CSC(NC=2C=CC=CC=2)=C1C(=O)NC1=CC=CC=N1 JEPQOIAPDXCGNY-UHFFFAOYSA-N 0.000 claims 1
- GYHGJFOIBSHDGP-UHFFFAOYSA-N 5-benzamido-n-(4-piperazin-1-ylphenyl)-1,3-thiazole-4-carboxamide Chemical compound N1=CSC(NC(=O)C=2C=CC=CC=2)=C1C(=O)NC(C=C1)=CC=C1N1CCNCC1 GYHGJFOIBSHDGP-UHFFFAOYSA-N 0.000 claims 1
- 208000024893 Acute lymphoblastic leukemia Diseases 0.000 claims 1
- 208000014697 Acute lymphocytic leukaemia Diseases 0.000 claims 1
- 208000031261 Acute myeloid leukaemia Diseases 0.000 claims 1
- 208000036762 Acute promyelocytic leukaemia Diseases 0.000 claims 1
- 208000023275 Autoimmune disease Diseases 0.000 claims 1
- 208000010839 B-cell chronic lymphocytic leukemia Diseases 0.000 claims 1
- 208000003950 B-cell lymphoma Diseases 0.000 claims 1
- 208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 claims 1
- 206010005003 Bladder cancer Diseases 0.000 claims 1
- 108091007914 CDKs Proteins 0.000 claims 1
- 206010008342 Cervix carcinoma Diseases 0.000 claims 1
- 208000010833 Chronic myeloid leukaemia Diseases 0.000 claims 1
- 208000004463 Follicular Adenocarcinoma Diseases 0.000 claims 1
- 208000022072 Gallbladder Neoplasms Diseases 0.000 claims 1
- 208000017604 Hodgkin disease Diseases 0.000 claims 1
- 208000021519 Hodgkin lymphoma Diseases 0.000 claims 1
- 208000010747 Hodgkins lymphoma Diseases 0.000 claims 1
- 208000007766 Kaposi sarcoma Diseases 0.000 claims 1
- 208000008839 Kidney Neoplasms Diseases 0.000 claims 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 1
- 208000031422 Lymphocytic Chronic B-Cell Leukemia Diseases 0.000 claims 1
- 201000003793 Myelodysplastic syndrome Diseases 0.000 claims 1
- 208000033761 Myelogenous Chronic BCR-ABL Positive Leukemia Diseases 0.000 claims 1
- 208000033776 Myeloid Acute Leukemia Diseases 0.000 claims 1
- 208000015914 Non-Hodgkin lymphomas Diseases 0.000 claims 1
- 206010061534 Oesophageal squamous cell carcinoma Diseases 0.000 claims 1
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims 1
- 208000006664 Precursor Cell Lymphoblastic Leukemia-Lymphoma Diseases 0.000 claims 1
- 206010038389 Renal cancer Diseases 0.000 claims 1
- 201000010208 Seminoma Diseases 0.000 claims 1
- 208000000453 Skin Neoplasms Diseases 0.000 claims 1
- 208000036765 Squamous cell carcinoma of the esophagus Diseases 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
- 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
- 230000001154 acute effect Effects 0.000 claims 1
- 210000003169 central nervous system Anatomy 0.000 claims 1
- 201000010881 cervical cancer Diseases 0.000 claims 1
- 208000032852 chronic lymphocytic leukemia Diseases 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 210000002615 epidermis Anatomy 0.000 claims 1
- 208000007276 esophageal squamous cell carcinoma Diseases 0.000 claims 1
- 230000003325 follicular Effects 0.000 claims 1
- 201000010175 gallbladder cancer Diseases 0.000 claims 1
- 206010017758 gastric cancer Diseases 0.000 claims 1
- 208000019691 hematopoietic and lymphoid cell neoplasm Diseases 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 201000010982 kidney cancer Diseases 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
- 210000004324 lymphatic system Anatomy 0.000 claims 1
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 201000001441 melanoma Diseases 0.000 claims 1
- 201000008806 mesenchymal cell neoplasm Diseases 0.000 claims 1
- CZFWPBQREYHQTP-UHFFFAOYSA-N n-(2-hydroxyphenyl)-5-[(2,4,6-trichlorobenzoyl)amino]-1,3-thiazole-4-carboxamide Chemical compound OC1=CC=CC=C1NC(=O)C1=C(NC(=O)C=2C(=CC(Cl)=CC=2Cl)Cl)SC=N1 CZFWPBQREYHQTP-UHFFFAOYSA-N 0.000 claims 1
- GYMPJRRJQGCMMT-UHFFFAOYSA-N n-(3-hydroxyphenyl)-5-[(2,4,6-trichlorobenzoyl)amino]-1,3-thiazole-4-carboxamide Chemical compound OC1=CC=CC(NC(=O)C2=C(SC=N2)NC(=O)C=2C(=CC(Cl)=CC=2Cl)Cl)=C1 GYMPJRRJQGCMMT-UHFFFAOYSA-N 0.000 claims 1
- XQTOTFALQIOYTR-UHFFFAOYSA-N n-(4-morpholin-4-ylphenyl)-5-[(2,4,6-trichlorobenzoyl)amino]-1,3-thiazole-4-carboxamide Chemical compound ClC1=CC(Cl)=CC(Cl)=C1C(=O)NC1=C(C(=O)NC=2C=CC(=CC=2)N2CCOCC2)N=CS1 XQTOTFALQIOYTR-UHFFFAOYSA-N 0.000 claims 1
- YYUPIQKOMRVZRP-UHFFFAOYSA-N n-(4-piperazin-1-ylphenyl)-5-[(2,4,6-trichlorobenzoyl)amino]-1,3-thiazole-4-carboxamide Chemical compound ClC1=CC(Cl)=CC(Cl)=C1C(=O)NC1=C(C(=O)NC=2C=CC(=CC=2)N2CCNCC2)N=CS1 YYUPIQKOMRVZRP-UHFFFAOYSA-N 0.000 claims 1
- SMBSJQSGNJXZGT-UHFFFAOYSA-N n-(5-piperazin-1-ylpyridin-2-yl)-4-[(2,4,6-trichlorobenzoyl)amino]-1,2-thiazole-3-carboxamide Chemical compound ClC1=CC(Cl)=CC(Cl)=C1C(=O)NC1=CSN=C1C(=O)NC1=CC=C(N2CCNCC2)C=N1 SMBSJQSGNJXZGT-UHFFFAOYSA-N 0.000 claims 1
- HYSBSYXHANLYEH-UHFFFAOYSA-N n-(5-piperazin-1-ylpyridin-2-yl)-5-[(2,4,6-trichlorobenzoyl)amino]-1,3-thiazole-4-carboxamide Chemical compound ClC1=CC(Cl)=CC(Cl)=C1C(=O)NC1=C(C(=O)NC=2N=CC(=CC=2)N2CCNCC2)N=CS1 HYSBSYXHANLYEH-UHFFFAOYSA-N 0.000 claims 1
- ZPNBQORASPWJLW-UHFFFAOYSA-N n-[1-(oxan-4-yl)piperidin-4-yl]-5-[(2,4,6-trichlorobenzoyl)amino]-1,3-thiazole-4-carboxamide Chemical compound ClC1=CC(Cl)=CC(Cl)=C1C(=O)NC1=C(C(=O)NC2CCN(CC2)C2CCOCC2)N=CS1 ZPNBQORASPWJLW-UHFFFAOYSA-N 0.000 claims 1
- ARKJZJOONVBQJC-UHFFFAOYSA-N n-[4-(methoxymethoxy)cyclohexyl]-5-[(2,4,6-trichlorobenzoyl)amino]-1,3-thiazole-4-carboxamide Chemical compound C1CC(OCOC)CCC1NC(=O)C1=C(NC(=O)C=2C(=CC(Cl)=CC=2Cl)Cl)SC=N1 ARKJZJOONVBQJC-UHFFFAOYSA-N 0.000 claims 1
- OUYKHNHVHUGDCD-UHFFFAOYSA-N n-phenyl-5-[(2,4,6-trichlorobenzoyl)amino]-1,3-thiazole-4-carboxamide Chemical compound ClC1=CC(Cl)=CC(Cl)=C1C(=O)NC1=C(C(=O)NC=2C=CC=CC=2)N=CS1 OUYKHNHVHUGDCD-UHFFFAOYSA-N 0.000 claims 1
- FRHSRHLFGOLDSR-UHFFFAOYSA-N n-piperidin-4-yl-5-(pyridin-3-ylamino)-1,3-thiazole-4-carboxamide Chemical compound N1=CSC(NC=2C=NC=CC=2)=C1C(=O)NC1CCNCC1 FRHSRHLFGOLDSR-UHFFFAOYSA-N 0.000 claims 1
- DJJZIVUJHYIGEJ-UHFFFAOYSA-N n-piperidin-4-yl-5-[(2,4,6-trichlorobenzoyl)amino]-1,3-thiazole-4-carboxamide Chemical compound ClC1=CC(Cl)=CC(Cl)=C1C(=O)NC1=C(C(=O)NC2CCNCC2)N=CS1 DJJZIVUJHYIGEJ-UHFFFAOYSA-N 0.000 claims 1
- IBYYUUTWTXZSRR-UHFFFAOYSA-N n-pyridin-2-yl-5-[(2,4,6-trichlorobenzoyl)amino]-1,3-thiazole-4-carboxamide Chemical compound ClC1=CC(Cl)=CC(Cl)=C1C(=O)NC1=C(C(=O)NC=2N=CC=CC=2)N=CS1 IBYYUUTWTXZSRR-UHFFFAOYSA-N 0.000 claims 1
- 230000004770 neurodegeneration Effects 0.000 claims 1
- 208000015122 neurodegenerative disease Diseases 0.000 claims 1
- 208000002154 non-small cell lung carcinoma Diseases 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
- 230000002062 proliferating effect Effects 0.000 claims 1
- 201000000849 skin cancer Diseases 0.000 claims 1
- 201000011549 stomach cancer Diseases 0.000 claims 1
- 208000001608 teratocarcinoma Diseases 0.000 claims 1
- 201000002510 thyroid cancer Diseases 0.000 claims 1
- 210000001685 thyroid gland Anatomy 0.000 claims 1
- 208000030901 thyroid gland follicular carcinoma Diseases 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
- 230000009385 viral infection Effects 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0416373A GB0416373D0 (en) | 2004-07-22 | 2004-07-22 | Pharmaceutical compounds |
| GB0501310A GB0501310D0 (en) | 2005-01-22 | 2005-01-22 | Pharmaceutical compounds |
| PCT/GB2005/002888 WO2006008545A2 (en) | 2004-07-22 | 2005-07-22 | Thiazole and isothiazole derivatives as protein kinase inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2008506761A JP2008506761A (ja) | 2008-03-06 |
| JP2008506761A5 true JP2008506761A5 (enExample) | 2008-08-14 |
Family
ID=35478265
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007522032A Withdrawn JP2008506761A (ja) | 2004-07-22 | 2005-07-22 | プロテインキナーゼ阻害剤としてのチアゾールおよびイソチアゾール誘導体 |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US20080167309A1 (enExample) |
| EP (1) | EP1781647A2 (enExample) |
| JP (1) | JP2008506761A (enExample) |
| WO (1) | WO2006008545A2 (enExample) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BRPI0606644A2 (pt) * | 2005-01-14 | 2009-07-14 | Hoffmann La Roche | derivados de 4-carboxamida tiazola |
| US8119655B2 (en) | 2005-10-07 | 2012-02-21 | Takeda Pharmaceutical Company Limited | Kinase inhibitors |
| ES2382162T3 (es) | 2005-11-08 | 2012-06-05 | F. Hoffmann-La Roche Ag | Derivados de tiazolo[4,5-c]piridina como antagonistas de receptor MGLU5 |
| US7951824B2 (en) | 2006-02-17 | 2011-05-31 | Hoffman-La Roche Inc. | 4-aryl-pyridine-2-carboxyamide derivatives |
| JP4884072B2 (ja) * | 2006-05-12 | 2012-02-22 | 三井化学アグロ株式会社 | 複素環誘導体ならびにその殺虫剤としての使用方法 |
| JP2010505962A (ja) | 2006-10-09 | 2010-02-25 | 武田薬品工業株式会社 | キナーゼ阻害剤 |
| JP5103604B2 (ja) * | 2006-10-31 | 2012-12-19 | メルク・シャープ・アンド・ドーム・コーポレーション | プロテインキナーゼ阻害剤としての２−アミノチアゾール−４−カルボン酸アミド |
| CA2703979A1 (en) * | 2007-10-29 | 2009-05-07 | Schering Corporation | Heterocyclic ether and thioether derivatives and methods of use thereof |
| CN102186856B (zh) | 2008-08-22 | 2014-09-24 | 诺华股份有限公司 | 作为cdk抑制剂的吡咯并嘧啶化合物 |
| UY33227A (es) | 2010-02-19 | 2011-09-30 | Novartis Ag | Compuestos de pirrolopirimidina como inhibidores de la cdk4/6 |
| AR083797A1 (es) * | 2010-11-10 | 2013-03-20 | Novartis Ag | Succinato de dimetil-amida del acido 7-ciclopentil-2-(5-piperazin-1-il-piridin-2-il-amino)-7h-pirrolo-[2,3-d]pirimidin-6-carboxilico, proceso para prepararla, intermediarios de dicha sintesis y proceso de preparacion de los mismos |
| JP6759073B2 (ja) * | 2015-12-28 | 2020-09-23 | キヤノン株式会社 | インク、インクカートリッジ、及びインクジェット記録方法 |
| KR20210119444A (ko) | 2019-01-23 | 2021-10-05 | 노파르티스 아게 | 7-사이클로펜틸-2-(5-피페라진-1-일-피리딘-2-일아미노)-7h-피롤로[2,3-d]피리미딘-6-카복실산 디메틸아미드의 석신산염의 신규한 결정질 형태 |
| CA3198024A1 (en) | 2020-11-13 | 2022-05-19 | Sampath Kumar Anandan | Dichlorophenol hsd17b13 inhibitors and uses thereof |
| US20240208959A1 (en) * | 2021-04-05 | 2024-06-27 | Inipharm, Inc. | Thiazole/isothiazole hsd17b13 inhibitors and uses thereof |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6927216B2 (en) * | 2000-10-03 | 2005-08-09 | Bristol-Myers Squibb Pharma Company | Cyclic sulfonyl compounds as inhibitors of metalloproteases |
| US7105682B2 (en) * | 2001-01-12 | 2006-09-12 | Amgen Inc. | Substituted amine derivatives and methods of use |
| US6995162B2 (en) * | 2001-01-12 | 2006-02-07 | Amgen Inc. | Substituted alkylamine derivatives and methods of use |
-
2005
- 2005-07-22 US US11/572,305 patent/US20080167309A1/en not_active Abandoned
- 2005-07-22 WO PCT/GB2005/002888 patent/WO2006008545A2/en not_active Ceased
- 2005-07-22 JP JP2007522032A patent/JP2008506761A/ja not_active Withdrawn
- 2005-07-22 EP EP05762253A patent/EP1781647A2/en not_active Withdrawn
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