HRP20140790T1 - Inhibitori aktivnosti akt - Google Patents
Inhibitori aktivnosti akt Download PDFInfo
- Publication number
- HRP20140790T1 HRP20140790T1 HRP20140790AT HRP20140790T HRP20140790T1 HR P20140790 T1 HRP20140790 T1 HR P20140790T1 HR P20140790A T HRP20140790A T HR P20140790AT HR P20140790 T HRP20140790 T HR P20140790T HR P20140790 T1 HRP20140790 T1 HR P20140790T1
- Authority
- HR
- Croatia
- Prior art keywords
- methyl
- ethyl
- pyrazol
- amino
- chloro
- Prior art date
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- 239000003112 inhibitor Substances 0.000 title claims 4
- 150000001875 compounds Chemical class 0.000 claims 9
- 150000003839 salts Chemical class 0.000 claims 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 7
- 208000008770 Multiple Hamartoma Syndrome Diseases 0.000 claims 6
- 201000002847 Cowden syndrome Diseases 0.000 claims 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- AFJRDFWMXUECEW-LBPRGKRZSA-N N-[(2S)-1-amino-3-(3-fluorophenyl)propan-2-yl]-5-chloro-4-(4-chloro-2-methyl-3-pyrazolyl)-2-thiophenecarboxamide Chemical compound CN1N=CC(Cl)=C1C1=C(Cl)SC(C(=O)N[C@H](CN)CC=2C=C(F)C=CC=2)=C1 AFJRDFWMXUECEW-LBPRGKRZSA-N 0.000 claims 3
- 206010028980 Neoplasm Diseases 0.000 claims 3
- 201000011510 cancer Diseases 0.000 claims 3
- 208000032839 leukemia Diseases 0.000 claims 3
- AXTAPYRUEKNRBA-JTQLQIEISA-N n-[(2s)-1-amino-3-(3,4-difluorophenyl)propan-2-yl]-5-chloro-4-(4-chloro-2-methylpyrazol-3-yl)furan-2-carboxamide Chemical compound CN1N=CC(Cl)=C1C1=C(Cl)OC(C(=O)N[C@H](CN)CC=2C=C(F)C(F)=CC=2)=C1 AXTAPYRUEKNRBA-JTQLQIEISA-N 0.000 claims 3
- 239000000825 pharmaceutical preparation Substances 0.000 claims 3
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 2
- 201000007815 Bannayan-Riley-Ruvalcaba syndrome Diseases 0.000 claims 2
- 208000003174 Brain Neoplasms Diseases 0.000 claims 2
- 206010006187 Breast cancer Diseases 0.000 claims 2
- 208000026310 Breast neoplasm Diseases 0.000 claims 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
- 208000012609 Cowden disease Diseases 0.000 claims 2
- 206010051066 Gastrointestinal stromal tumour Diseases 0.000 claims 2
- 208000032612 Glial tumor Diseases 0.000 claims 2
- 206010018338 Glioma Diseases 0.000 claims 2
- 208000022010 Lhermitte-Duclos disease Diseases 0.000 claims 2
- 208000034578 Multiple myelomas Diseases 0.000 claims 2
- 206010035226 Plasma cell myeloma Diseases 0.000 claims 2
- 239000002246 antineoplastic agent Substances 0.000 claims 2
- 229940034982 antineoplastic agent Drugs 0.000 claims 2
- 210000004027 cell Anatomy 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 239000000460 chlorine Substances 0.000 claims 2
- 201000011243 gastrointestinal stromal tumor Diseases 0.000 claims 2
- 208000005017 glioblastoma Diseases 0.000 claims 2
- AHDFWNJLFALBJP-JTQLQIEISA-N n-[(2s)-1-amino-3-(3,4-difluorophenyl)propan-2-yl]-5-chloro-4-(4-chloro-2-methylpyrazol-3-yl)thiophene-2-carboxamide Chemical compound CN1N=CC(Cl)=C1C1=C(Cl)SC(C(=O)N[C@H](CN)CC=2C=C(F)C(F)=CC=2)=C1 AHDFWNJLFALBJP-JTQLQIEISA-N 0.000 claims 2
- ZEESWPRDQGWOMU-AWEZNQCLSA-N n-[(2s)-1-amino-3-(3-fluorophenyl)propan-2-yl]-4-(4-chloro-2-methylpyrazol-3-yl)-5-methylthiophene-2-carboxamide Chemical compound CC=1SC(C(=O)N[C@H](CN)CC=2C=C(F)C=CC=2)=CC=1C1=C(Cl)C=NN1C ZEESWPRDQGWOMU-AWEZNQCLSA-N 0.000 claims 2
- YXVKCDFTJDTHCC-LBPRGKRZSA-N n-[(2s)-1-amino-3-(3-fluorophenyl)propan-2-yl]-5-chloro-4-(4-chloro-2-methylpyrazol-3-yl)furan-2-carboxamide Chemical compound CN1N=CC(Cl)=C1C1=C(Cl)OC(C(=O)N[C@H](CN)CC=2C=C(F)C=CC=2)=C1 YXVKCDFTJDTHCC-LBPRGKRZSA-N 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims 2
- YNSCKPCDFIDINW-UHFFFAOYSA-N 3-[[2-[[1-[2-(dimethylamino)acetyl]-6-methoxy-4,4-dimethyl-2,3-dihydroquinolin-7-yl]amino]-7h-pyrrolo[2,3-d]pyrimidin-4-yl]amino]thiophene-2-carboxamide Chemical compound COC1=CC(C(CCN2C(=O)CN(C)C)(C)C)=C2C=C1NC(N=C1NC=CC1=1)=NC=1NC=1C=CSC=1C(N)=O YNSCKPCDFIDINW-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
- 208000010839 B-cell chronic lymphocytic leukemia 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
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- 208000011691 Burkitt lymphomas Diseases 0.000 claims 1
- 206010008342 Cervix carcinoma Diseases 0.000 claims 1
- 208000010833 Chronic myeloid leukaemia Diseases 0.000 claims 1
- 206010009944 Colon cancer Diseases 0.000 claims 1
- 229940123780 DNA topoisomerase I inhibitor Drugs 0.000 claims 1
- 229940124087 DNA topoisomerase II inhibitor Drugs 0.000 claims 1
- 206010014733 Endometrial cancer Diseases 0.000 claims 1
- 206010014759 Endometrial neoplasm Diseases 0.000 claims 1
- 208000031637 Erythroblastic Acute Leukemia Diseases 0.000 claims 1
- 208000036566 Erythroleukaemia Diseases 0.000 claims 1
- 208000000461 Esophageal Neoplasms Diseases 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 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
- 208000005726 Inflammatory Breast Neoplasms Diseases 0.000 claims 1
- 206010021980 Inflammatory carcinoma of the breast Diseases 0.000 claims 1
- 208000008839 Kidney Neoplasms Diseases 0.000 claims 1
- 206010061523 Lip and/or oral cavity cancer 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
- 206010025323 Lymphomas Diseases 0.000 claims 1
- 208000035490 Megakaryoblastic Acute Leukemia Diseases 0.000 claims 1
- 206010027406 Mesothelioma Diseases 0.000 claims 1
- 208000003445 Mouth Neoplasms 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
- 208000001894 Nasopharyngeal Neoplasms Diseases 0.000 claims 1
- 206010061306 Nasopharyngeal cancer Diseases 0.000 claims 1
- 206010029260 Neuroblastoma Diseases 0.000 claims 1
- 208000033755 Neutrophilic Chronic Leukemia Diseases 0.000 claims 1
- 208000015914 Non-Hodgkin lymphomas Diseases 0.000 claims 1
- 206010030155 Oesophageal carcinoma Diseases 0.000 claims 1
- 208000007452 Plasmacytoma Diseases 0.000 claims 1
- 208000006664 Precursor Cell Lymphoblastic Leukemia-Lymphoma Diseases 0.000 claims 1
- 206010038389 Renal cancer Diseases 0.000 claims 1
- 208000004337 Salivary Gland Neoplasms Diseases 0.000 claims 1
- 206010061934 Salivary gland cancer Diseases 0.000 claims 1
- 206010039491 Sarcoma 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
- 208000024313 Testicular Neoplasms Diseases 0.000 claims 1
- 206010057644 Testis cancer Diseases 0.000 claims 1
- 208000024770 Thyroid neoplasm Diseases 0.000 claims 1
- 239000000365 Topoisomerase I Inhibitor Substances 0.000 claims 1
- 239000000317 Topoisomerase II Inhibitor Substances 0.000 claims 1
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims 1
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 claims 1
- 206010047741 Vulval cancer Diseases 0.000 claims 1
- 208000004354 Vulvar Neoplasms Diseases 0.000 claims 1
- 208000008383 Wilms tumor Diseases 0.000 claims 1
- ZUSWDTWYONAOPH-UHFFFAOYSA-N [2-(trifluoromethyl)phenyl]hydrazine;hydrochloride Chemical group [Cl-].[NH3+]NC1=CC=CC=C1C(F)(F)F ZUSWDTWYONAOPH-UHFFFAOYSA-N 0.000 claims 1
- 208000021841 acute erythroid leukemia Diseases 0.000 claims 1
- 208000037833 acute lymphoblastic T-cell leukemia Diseases 0.000 claims 1
- 208000013593 acute megakaryoblastic leukemia Diseases 0.000 claims 1
- 208000020700 acute megakaryocytic leukemia Diseases 0.000 claims 1
- 229940100198 alkylating agent Drugs 0.000 claims 1
- 239000002168 alkylating agent Substances 0.000 claims 1
- 230000033115 angiogenesis Effects 0.000 claims 1
- 230000000340 anti-metabolite Effects 0.000 claims 1
- 229940044684 anti-microtubule agent Drugs 0.000 claims 1
- 229940100197 antimetabolite Drugs 0.000 claims 1
- 239000002256 antimetabolite Substances 0.000 claims 1
- 206010003246 arthritis Diseases 0.000 claims 1
- 230000003115 biocidal effect Effects 0.000 claims 1
- 210000000481 breast Anatomy 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 230000022131 cell cycle Effects 0.000 claims 1
- 201000010881 cervical cancer Diseases 0.000 claims 1
- 208000032852 chronic lymphocytic leukemia Diseases 0.000 claims 1
- 201000010903 chronic neutrophilic leukemia Diseases 0.000 claims 1
- 210000001072 colon Anatomy 0.000 claims 1
- 208000029742 colonic neoplasm Diseases 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 201000004101 esophageal cancer Diseases 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 201000003444 follicular lymphoma Diseases 0.000 claims 1
- 206010017758 gastric cancer Diseases 0.000 claims 1
- 201000009277 hairy cell leukemia Diseases 0.000 claims 1
- 201000010536 head and neck cancer Diseases 0.000 claims 1
- 208000014829 head and neck neoplasm Diseases 0.000 claims 1
- 206010073071 hepatocellular carcinoma Diseases 0.000 claims 1
- 239000002944 hormone and hormone analog Substances 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 239000002955 immunomodulating agent Substances 0.000 claims 1
- 201000004653 inflammatory breast carcinoma Diseases 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 210000003734 kidney Anatomy 0.000 claims 1
- 201000010982 kidney cancer Diseases 0.000 claims 1
- 210000004185 liver Anatomy 0.000 claims 1
- 208000014018 liver neoplasm Diseases 0.000 claims 1
- 210000004072 lung Anatomy 0.000 claims 1
- 201000005202 lung cancer Diseases 0.000 claims 1
- 208000020816 lung neoplasm Diseases 0.000 claims 1
- 230000003211 malignant effect Effects 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 201000001441 melanoma Diseases 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- UDAOQMCGORPPQS-HNNXBMFYSA-N n-[(2s)-1-amino-3-(2,5-difluorophenyl)propan-2-yl]-4-(2,4-dimethylpyrazol-3-yl)-5-methylthiophene-2-carboxamide Chemical compound C1=NN(C)C(C2=C(SC(=C2)C(=O)N[C@H](CN)CC=2C(=CC=C(F)C=2)F)C)=C1C UDAOQMCGORPPQS-HNNXBMFYSA-N 0.000 claims 1
- RCFCVKZDKPOLRD-ZDUSSCGKSA-N n-[(2s)-1-amino-3-(2,5-difluorophenyl)propan-2-yl]-4-(4-chloro-2-methylpyrazol-3-yl)-5-methylthiophene-2-carboxamide Chemical compound CC=1SC(C(=O)N[C@H](CN)CC=2C(=CC=C(F)C=2)F)=CC=1C1=C(Cl)C=NN1C RCFCVKZDKPOLRD-ZDUSSCGKSA-N 0.000 claims 1
- NWDQAHYVYXLEML-ZDUSSCGKSA-N n-[(2s)-1-amino-3-(2,5-difluorophenyl)propan-2-yl]-5-chloro-4-(2,4-dimethylpyrazol-3-yl)thiophene-2-carboxamide Chemical compound C1=NN(C)C(C2=C(SC(=C2)C(=O)N[C@H](CN)CC=2C(=CC=C(F)C=2)F)Cl)=C1C NWDQAHYVYXLEML-ZDUSSCGKSA-N 0.000 claims 1
- JSJGBMLLKLKKQU-LBPRGKRZSA-N n-[(2s)-1-amino-3-(2,5-difluorophenyl)propan-2-yl]-5-chloro-4-(2-methylpyrazol-3-yl)thiophene-2-carboxamide Chemical compound CN1N=CC=C1C1=C(Cl)SC(C(=O)N[C@H](CN)CC=2C(=CC=C(F)C=2)F)=C1 JSJGBMLLKLKKQU-LBPRGKRZSA-N 0.000 claims 1
- UFJFTHRSOPAVHU-NSHDSACASA-N n-[(2s)-1-amino-3-(2,5-difluorophenyl)propan-2-yl]-5-chloro-4-(4-chloro-2-methylpyrazol-3-yl)thiophene-2-carboxamide Chemical compound CN1N=CC(Cl)=C1C1=C(Cl)SC(C(=O)N[C@H](CN)CC=2C(=CC=C(F)C=2)F)=C1 UFJFTHRSOPAVHU-NSHDSACASA-N 0.000 claims 1
- OEKZHEJEIOCDHK-AWEZNQCLSA-N n-[(2s)-1-amino-3-(2,5-difluorophenyl)propan-2-yl]-5-methyl-4-(2-methylpyrazol-3-yl)thiophene-2-carboxamide Chemical compound CC=1SC(C(=O)N[C@H](CN)CC=2C(=CC=C(F)C=2)F)=CC=1C1=CC=NN1C OEKZHEJEIOCDHK-AWEZNQCLSA-N 0.000 claims 1
- CLBIMBSYSMQLIE-AWEZNQCLSA-N n-[(2s)-1-amino-3-(3,4-difluorophenyl)propan-2-yl]-4-(2,4-dimethylpyrazol-3-yl)-5-methylfuran-2-carboxamide Chemical compound C1=NN(C)C(C2=C(OC(=C2)C(=O)N[C@H](CN)CC=2C=C(F)C(F)=CC=2)C)=C1C CLBIMBSYSMQLIE-AWEZNQCLSA-N 0.000 claims 1
- WJEXAFJBQQFUHK-AWEZNQCLSA-N n-[(2s)-1-amino-3-(3,4-difluorophenyl)propan-2-yl]-4-(2,4-dimethylpyrazol-3-yl)-5-methylthiophene-2-carboxamide Chemical compound C1=NN(C)C(C2=C(SC(=C2)C(=O)N[C@H](CN)CC=2C=C(F)C(F)=CC=2)C)=C1C WJEXAFJBQQFUHK-AWEZNQCLSA-N 0.000 claims 1
- HKUUGKCGHFCAMJ-ZDUSSCGKSA-N n-[(2s)-1-amino-3-(3,4-difluorophenyl)propan-2-yl]-4-(4-chloro-2-ethylpyrazol-3-yl)-5-methylfuran-2-carboxamide Chemical compound CCN1N=CC(Cl)=C1C1=C(C)OC(C(=O)N[C@H](CN)CC=2C=C(F)C(F)=CC=2)=C1 HKUUGKCGHFCAMJ-ZDUSSCGKSA-N 0.000 claims 1
- KKRPHDUBELVRDO-LBPRGKRZSA-N n-[(2s)-1-amino-3-(3,4-difluorophenyl)propan-2-yl]-4-(4-chloro-2-methylpyrazol-3-yl)-5-methylfuran-2-carboxamide Chemical compound CC=1OC(C(=O)N[C@H](CN)CC=2C=C(F)C(F)=CC=2)=CC=1C1=C(Cl)C=NN1C KKRPHDUBELVRDO-LBPRGKRZSA-N 0.000 claims 1
- GDLCAQCCQOYNNX-LBPRGKRZSA-N n-[(2s)-1-amino-3-(3,4-difluorophenyl)propan-2-yl]-4-(4-chloro-2-methylpyrazol-3-yl)-5-methylthiophene-2-carboxamide Chemical compound CC=1SC(C(=O)N[C@H](CN)CC=2C=C(F)C(F)=CC=2)=CC=1C1=C(Cl)C=NN1C GDLCAQCCQOYNNX-LBPRGKRZSA-N 0.000 claims 1
- GOVBVZGPHFRQMC-LBPRGKRZSA-N n-[(2s)-1-amino-3-(3,4-difluorophenyl)propan-2-yl]-5-chloro-4-(2,4-dimethylpyrazol-3-yl)furan-2-carboxamide Chemical compound C1=NN(C)C(C2=C(OC(=C2)C(=O)N[C@H](CN)CC=2C=C(F)C(F)=CC=2)Cl)=C1C GOVBVZGPHFRQMC-LBPRGKRZSA-N 0.000 claims 1
- FNQAIJFYSVGPAX-ZDUSSCGKSA-N n-[(2s)-1-amino-3-(3,4-difluorophenyl)propan-2-yl]-5-chloro-4-(2-ethyl-4-methylpyrazol-3-yl)thiophene-2-carboxamide Chemical compound CCN1N=CC(C)=C1C1=C(Cl)SC(C(=O)N[C@H](CN)CC=2C=C(F)C(F)=CC=2)=C1 FNQAIJFYSVGPAX-ZDUSSCGKSA-N 0.000 claims 1
- LMSNGALZABVVRE-NSHDSACASA-N n-[(2s)-1-amino-3-(3,4-difluorophenyl)propan-2-yl]-5-chloro-4-(2-methylpyrazol-3-yl)furan-2-carboxamide Chemical compound CN1N=CC=C1C1=C(Cl)OC(C(=O)N[C@H](CN)CC=2C=C(F)C(F)=CC=2)=C1 LMSNGALZABVVRE-NSHDSACASA-N 0.000 claims 1
- VJBLJMGAIQOKGY-NSHDSACASA-N n-[(2s)-1-amino-3-(3,4-difluorophenyl)propan-2-yl]-5-chloro-4-(2-methylpyrazol-3-yl)thiophene-2-carboxamide Chemical compound CN1N=CC=C1C1=C(Cl)SC(C(=O)N[C@H](CN)CC=2C=C(F)C(F)=CC=2)=C1 VJBLJMGAIQOKGY-NSHDSACASA-N 0.000 claims 1
- WBNREKJRGKMSSO-NSHDSACASA-N n-[(2s)-1-amino-3-(3,4-difluorophenyl)propan-2-yl]-5-chloro-4-(4-chloro-2-ethylpyrazol-3-yl)furan-2-carboxamide Chemical compound CCN1N=CC(Cl)=C1C1=C(Cl)OC(C(=O)N[C@H](CN)CC=2C=C(F)C(F)=CC=2)=C1 WBNREKJRGKMSSO-NSHDSACASA-N 0.000 claims 1
- IYWMCXIXRQMCTO-NSHDSACASA-N n-[(2s)-1-amino-3-(3,4-difluorophenyl)propan-2-yl]-5-chloro-4-(4-chloro-2-ethylpyrazol-3-yl)thiophene-2-carboxamide Chemical compound CCN1N=CC(Cl)=C1C1=C(Cl)SC(C(=O)N[C@H](CN)CC=2C=C(F)C(F)=CC=2)=C1 IYWMCXIXRQMCTO-NSHDSACASA-N 0.000 claims 1
- GEERYZLEENSFSF-ZDUSSCGKSA-N n-[(2s)-1-amino-3-(3,4-difluorophenyl)propan-2-yl]-5-methyl-4-(2-methylpyrazol-3-yl)furan-2-carboxamide Chemical compound CC=1OC(C(=O)N[C@H](CN)CC=2C=C(F)C(F)=CC=2)=CC=1C1=CC=NN1C GEERYZLEENSFSF-ZDUSSCGKSA-N 0.000 claims 1
- AQPCBAMOJTVEJF-ZDUSSCGKSA-N n-[(2s)-1-amino-3-(3,4-difluorophenyl)propan-2-yl]-5-methyl-4-(2-methylpyrazol-3-yl)thiophene-2-carboxamide Chemical compound CC=1SC(C(=O)N[C@H](CN)CC=2C=C(F)C(F)=CC=2)=CC=1C1=CC=NN1C AQPCBAMOJTVEJF-ZDUSSCGKSA-N 0.000 claims 1
- ZHRRTRMAUXYQGN-INIZCTEOSA-N n-[(2s)-1-amino-3-(3-fluorophenyl)propan-2-yl]-4-(2,4-dimethylpyrazol-3-yl)-5-ethylthiophene-2-carboxamide Chemical compound CCC=1SC(C(=O)N[C@H](CN)CC=2C=C(F)C=CC=2)=CC=1C1=C(C)C=NN1C ZHRRTRMAUXYQGN-INIZCTEOSA-N 0.000 claims 1
- ZZFNSPOSIYTYMY-INIZCTEOSA-N n-[(2s)-1-amino-3-(3-fluorophenyl)propan-2-yl]-4-(2,4-dimethylpyrazol-3-yl)-5-methylthiophene-2-carboxamide Chemical compound C1=NN(C)C(C2=C(SC(=C2)C(=O)N[C@H](CN)CC=2C=C(F)C=CC=2)C)=C1C ZZFNSPOSIYTYMY-INIZCTEOSA-N 0.000 claims 1
- CISPGQALPDRSRW-LBPRGKRZSA-N n-[(2s)-1-amino-3-(3-fluorophenyl)propan-2-yl]-4-(4-bromo-2-methylpyrazol-3-yl)-5-chlorothiophene-2-carboxamide Chemical compound CN1N=CC(Br)=C1C1=C(Cl)SC(C(=O)N[C@H](CN)CC=2C=C(F)C=CC=2)=C1 CISPGQALPDRSRW-LBPRGKRZSA-N 0.000 claims 1
- YHYPZMZELNQAFK-AWEZNQCLSA-N n-[(2s)-1-amino-3-(3-fluorophenyl)propan-2-yl]-4-(4-bromo-2-methylpyrazol-3-yl)-5-methylthiophene-2-carboxamide Chemical compound CC=1SC(C(=O)N[C@H](CN)CC=2C=C(F)C=CC=2)=CC=1C1=C(Br)C=NN1C YHYPZMZELNQAFK-AWEZNQCLSA-N 0.000 claims 1
- KFWBLBWXDWXKCD-AWEZNQCLSA-N n-[(2s)-1-amino-3-(3-fluorophenyl)propan-2-yl]-4-(4-chloro-2-methylpyrazol-3-yl)-5-ethylfuran-2-carboxamide Chemical compound CCC=1OC(C(=O)N[C@H](CN)CC=2C=C(F)C=CC=2)=CC=1C1=C(Cl)C=NN1C KFWBLBWXDWXKCD-AWEZNQCLSA-N 0.000 claims 1
- KQHQBDFPSAGKRW-AWEZNQCLSA-N n-[(2s)-1-amino-3-(3-fluorophenyl)propan-2-yl]-4-(4-chloro-2-methylpyrazol-3-yl)-5-ethylthiophene-2-carboxamide Chemical compound CCC=1SC(C(=O)N[C@H](CN)CC=2C=C(F)C=CC=2)=CC=1C1=C(Cl)C=NN1C KQHQBDFPSAGKRW-AWEZNQCLSA-N 0.000 claims 1
- VMCNYPGFXXLUPB-ZDUSSCGKSA-N n-[(2s)-1-amino-3-(3-fluorophenyl)propan-2-yl]-4-(4-chloro-2-methylpyrazol-3-yl)-5-methoxythiophene-2-carboxamide Chemical compound COC=1SC(C(=O)N[C@H](CN)CC=2C=C(F)C=CC=2)=CC=1C1=C(Cl)C=NN1C VMCNYPGFXXLUPB-ZDUSSCGKSA-N 0.000 claims 1
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- ZQCQJLKKLQUQLK-ZDUSSCGKSA-N n-[(2s)-1-amino-3-[3-(trifluoromethyl)phenyl]propan-2-yl]-4-(4-chloro-2-methylpyrazol-3-yl)-5-methoxythiophene-2-carboxamide Chemical compound COC=1SC(C(=O)N[C@H](CN)CC=2C=C(C=CC=2)C(F)(F)F)=CC=1C1=C(Cl)C=NN1C ZQCQJLKKLQUQLK-ZDUSSCGKSA-N 0.000 claims 1
- KEJLZUQXCVOZLV-AWEZNQCLSA-N n-[(2s)-1-amino-3-[3-(trifluoromethyl)phenyl]propan-2-yl]-4-(4-chloro-2-methylpyrazol-3-yl)-5-methylfuran-2-carboxamide Chemical compound CC=1OC(C(=O)N[C@H](CN)CC=2C=C(C=CC=2)C(F)(F)F)=CC=1C1=C(Cl)C=NN1C KEJLZUQXCVOZLV-AWEZNQCLSA-N 0.000 claims 1
- AHFDCWWPHSXBDL-AWEZNQCLSA-N n-[(2s)-1-amino-3-[3-(trifluoromethyl)phenyl]propan-2-yl]-4-(4-chloro-2-methylpyrazol-3-yl)-5-methylthiophene-2-carboxamide Chemical compound CC=1SC(C(=O)N[C@H](CN)CC=2C=C(C=CC=2)C(F)(F)F)=CC=1C1=C(Cl)C=NN1C AHFDCWWPHSXBDL-AWEZNQCLSA-N 0.000 claims 1
- ZHXRMZQWEMAYNM-AWEZNQCLSA-N n-[(2s)-1-amino-3-[3-(trifluoromethyl)phenyl]propan-2-yl]-5-chloro-4-(2,4-dimethylpyrazol-3-yl)furan-2-carboxamide Chemical compound C1=NN(C)C(C2=C(OC(=C2)C(=O)N[C@H](CN)CC=2C=C(C=CC=2)C(F)(F)F)Cl)=C1C ZHXRMZQWEMAYNM-AWEZNQCLSA-N 0.000 claims 1
- QDDOPJPUJRAYKK-AWEZNQCLSA-N n-[(2s)-1-amino-3-[3-(trifluoromethyl)phenyl]propan-2-yl]-5-chloro-4-(2,4-dimethylpyrazol-3-yl)thiophene-2-carboxamide Chemical compound C1=NN(C)C(C2=C(SC(=C2)C(=O)N[C@H](CN)CC=2C=C(C=CC=2)C(F)(F)F)Cl)=C1C QDDOPJPUJRAYKK-AWEZNQCLSA-N 0.000 claims 1
- MTULOTQQDCYFKJ-ZDUSSCGKSA-N n-[(2s)-1-amino-3-[3-(trifluoromethyl)phenyl]propan-2-yl]-5-chloro-4-(2-methylpyrazol-3-yl)furan-2-carboxamide Chemical compound CN1N=CC=C1C1=C(Cl)OC(C(=O)N[C@H](CN)CC=2C=C(C=CC=2)C(F)(F)F)=C1 MTULOTQQDCYFKJ-ZDUSSCGKSA-N 0.000 claims 1
- QVASFGSJLMUAAW-ZDUSSCGKSA-N n-[(2s)-1-amino-3-[3-(trifluoromethyl)phenyl]propan-2-yl]-5-chloro-4-(2-methylpyrazol-3-yl)thiophene-2-carboxamide Chemical compound CN1N=CC=C1C1=C(Cl)SC(C(=O)N[C@H](CN)CC=2C=C(C=CC=2)C(F)(F)F)=C1 QVASFGSJLMUAAW-ZDUSSCGKSA-N 0.000 claims 1
- VQUAYVYZPABEOE-ZDUSSCGKSA-N n-[(2s)-1-amino-3-[3-(trifluoromethyl)phenyl]propan-2-yl]-5-chloro-4-(4-chloro-2-ethylpyrazol-3-yl)thiophene-2-carboxamide Chemical compound CCN1N=CC(Cl)=C1C1=C(Cl)SC(C(=O)N[C@H](CN)CC=2C=C(C=CC=2)C(F)(F)F)=C1 VQUAYVYZPABEOE-ZDUSSCGKSA-N 0.000 claims 1
- LTFSVGYDSDUIQG-LBPRGKRZSA-N n-[(2s)-1-amino-3-[3-(trifluoromethyl)phenyl]propan-2-yl]-5-chloro-4-(4-chloro-2-methylpyrazol-3-yl)furan-2-carboxamide Chemical compound CN1N=CC(Cl)=C1C1=C(Cl)OC(C(=O)N[C@H](CN)CC=2C=C(C=CC=2)C(F)(F)F)=C1 LTFSVGYDSDUIQG-LBPRGKRZSA-N 0.000 claims 1
- MCOFQMJSPUIQPU-LBPRGKRZSA-N n-[(2s)-1-amino-3-[3-(trifluoromethyl)phenyl]propan-2-yl]-5-chloro-4-(4-chloro-2-methylpyrazol-3-yl)thiophene-2-carboxamide Chemical compound CN1N=CC(Cl)=C1C1=C(Cl)SC(C(=O)N[C@H](CN)CC=2C=C(C=CC=2)C(F)(F)F)=C1 MCOFQMJSPUIQPU-LBPRGKRZSA-N 0.000 claims 1
- VGINPUQIWPBEFL-HNNXBMFYSA-N n-[(2s)-1-amino-3-[3-(trifluoromethyl)phenyl]propan-2-yl]-5-methyl-4-(2-methylpyrazol-3-yl)thiophene-2-carboxamide Chemical compound CC=1SC(C(=O)N[C@H](CN)CC=2C=C(C=CC=2)C(F)(F)F)=CC=1C1=CC=NN1C VGINPUQIWPBEFL-HNNXBMFYSA-N 0.000 claims 1
- 201000008026 nephroblastoma Diseases 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 102000037979 non-receptor tyrosine kinases Human genes 0.000 claims 1
- 108091008046 non-receptor tyrosine kinases Proteins 0.000 claims 1
- 201000005443 oral cavity cancer Diseases 0.000 claims 1
- 230000002611 ovarian Effects 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 230000037361 pathway Effects 0.000 claims 1
- 229910052697 platinum Inorganic materials 0.000 claims 1
- 230000000861 pro-apoptotic effect Effects 0.000 claims 1
- 210000002307 prostate Anatomy 0.000 claims 1
- 230000008054 signal transmission Effects 0.000 claims 1
- 230000011664 signaling Effects 0.000 claims 1
- 201000011549 stomach cancer Diseases 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 201000003120 testicular cancer Diseases 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 201000002510 thyroid cancer Diseases 0.000 claims 1
- 206010044412 transitional cell carcinoma Diseases 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 201000005112 urinary bladder cancer Diseases 0.000 claims 1
- 201000005102 vulva cancer Diseases 0.000 claims 1
Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
- A61K31/4155—1,2-Diazoles non condensed and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
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- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/12—Ketones
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- A61K31/00—Medicinal preparations containing organic active ingredients
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
- A61K31/4178—1,3-Diazoles not condensed 1,3-diazoles and containing further heterocyclic rings, e.g. pilocarpine, nitrofurantoin
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4192—1,2,3-Triazoles
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4196—1,2,4-Triazoles
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
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- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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Claims (12)
1. Spoj Formule (I)
[image]
,
naznačen time što:
R41 se bira između: klora, etila, metila i metoksi;
R42 je
[image]
,
gdje je Q dušik, Y je -CH-, Z je -C(R48)-, a R30 se bira između metila i etila, gdje se R48 bira između: vodika, metila, klora i brom;
R43 je vodik;
R44 je -CH2-fenil, gdje je fenil supstituiran s jednim ili dva supstituenta, koje se bira između fluora i trifluormetila;
R45 je vodik;
R20 je vodik;
X se bira između O i S; i
n je 1;
ili njegova farmaceutski prihvatljiva sol.
2. Spoj u skladu s patentnim zahtjevom 1, naznačen time što ga se bira između:
N-((1S)-2-amino-1-{[2-(trifluormetil)fenil]metil}etil)-5-klor-4-(1-metil-1H-pirazol-5-il)-2-tiofenkarboksamida;
N-((1S)-2-amino-1-{[2-(trifluormetil)fenil]metil}etil)-4-(4-brom-1-metil-1H-pirazol-5-il)-5-metil-2-tiofenkarboksamida;
N-((1S)-2-amino-1-{[2-(trifluormetil)fenil]metil}etil)-4-{4-klor-1-metil-1H-pirazol-5-il)-5-metil-2-tiofenkarboksamida;
N-((1S)-2-amino-1-{[2-(trifluormetil)fenil]metil}etil)-5-klor-4-(4-klor-1-metil-1H-pirazol-5-il)-2-tiofenkarboksamida;
N-((1S)-2-amino-1-{[2-(trifluormetil)fenil]metil}etil)-4-(4-brom-1-metil-1H-pirazol-5-il)-5-klor-2-tiofenkarboksamida;
N-((1S)-2-amino-1-{[2-(trifluormetil)fenil]metil}etil)-5-metil-4-(1-metil-1H-pirazol-5-il)-2-tiofenkarboksamida;
N-((1S)-2-amino-1-{[2-(trifluormetil)fenil]metil}etil)-5-klor-4-(1-etil-1H-pirazol-5-il)-2-tiofenkarboksamida;
N-((1S)-2-amino-1-{[2-(trifluormetil)fenil]metil}etil)-5-klor-4-(1,4-dimetil-1H-pirazol-5-il)-2-tiofenkarboksamida;
N-{(1S)-2-amino-1-[(3-fluorfenil)metil]etil}-5-klor-4-(1-metil-1H-pirazol-5-il)-2-tiofenkarboksamida;
N-{(1S)-2-amino-1-[(3-fluorfenil)metil]etil}-5-klor-4-(4-klor-1-metil-1H-pirazol-5-il)-2-tiofenkarboksamida;
N-((1S)-2-amino-1-{[2-(trifluormetil)fenil]metil}etil)-5-etil-4-(1-metil-1H-pirazol-5-il)-2-tiofenkarboksamida;
N-((1S)-2-amino-1-{[2-(trifluormetil)fenil]metil}etil)-4-(1,4-dimetil-1H-pirazol-5-il)-5-metil-2-tiofenkarboksamida;
N-((1S)-2-amino-1-{[2-(trifluormetil)fenil]metil}etil)-4-(4-klor-1-metil-1H-pirazol-5-il)-5-etil-2-tiofenkarboksamida;
N-((1S)-2-amino-1-{[2-(trifluormetil)fenil]metil}etil)-4-(4-brom-1-metil-1H-pirazol-5-il)-5-etil-2-tiofenkarboksamida;
N-((1S)-2-amino-1-{[2-(trifluormetil)fenil]metil}etil)-4-(1,4-dimetil-1H-pirazol-5-il)-5-etil-2-tiofenkarboksamida;
N-((1S)-2-amino-1-{[2-(trifluormetil)fenil]metil}etil)-5-metil-4-(1-metil-1H-pirazol-5-il)-2-furankarboksamida;
N-((1S)-2-amino-1-{[2-(trifluormetil)fenil]metil}etil)-4-(4-brom-1-metil-1H-pirazol-5-il)-5-metil-2-furankarboksamida;
N-((1S)-2-amino-1-{[2-(trifluormetil)fenil]metil}etil)-4-(4-klor-1-metil-1H-pirazol-5-il)-5-metil-2-furankarboksamida;
N-((1S)-2-amino-1-{[2-(trifluormetil)fenil]metil}etil)-4-(1,4-dimetil-1H-pirazol-5-il)-5-metil-2-furankarboksamida;
N-{(1S)-2-amino-1-[(3-fluorfenil)metil]etil}-4-(4-klor-1-metil-1H-pirazol-5-il)-5-etil-2-tiofenkarboksamida;
N-{(1S)-2-amino-1-[(3-fluorfenil)metil]etil}-4-(1,4-dimetil-1H-pirazol-5-il)-5-etil-2-tiofenkarboksamida;
N-((1S)-2-amino-1-{[3-(trifluormetil)fenil]metil}etil)-4-(1,4-dimetil-1H-pirazol-5-il)-5-etil-2-tiofenkarboksamida;
N-((1S)-2-amino-1-{[2-(trifluormetil)fenil]metil}etil)-5-klor-4-(1-metil-1H-pirazol-5-il)-2-furankarboksamida;
N-((1S)-2-amino-1-{[2-(trifluormetil)fenil]metil}etil)-5-klor-4-(4-klor-1-metil-1H-pirazol-5-il)-2-furankarboksamida;
N-((1S)-2-amino-1-{[2-(trifluormetil)fenil]metil}etil)-4-(4-klor-1-metil-1H-pirazol-5-il)-5-etil-2-furankarboksamida;
N-{(1S)-2-amino-1-[(4-fluorfenil)metil]etil}-4-(4-klor-1-metil-1H-pirazol-5-il)-5-etil-2-furankarboksamida;
N-{(1S)-2-amino-1-[(3-fluorfenil)metil]etil}-4-(4-klor-1-metil-1H-pirazol-5-il)-5-etil-2-furankarboksamida;
N-{(1S)-2-amino-1-[(3-fluorfenil)metil]etil}-5-klor-4-(1-metil-1H-pirazol-5-il)-2-furankarboksamida;
N-{(1S)-2-amino-1-[(4-fluorfenil)metil]etil}-5-klor-4-(1-metil-1H-pirazol-5-il)-2-furankarboksamida;
N-((1S)-2-amino-1-{[3-(trifluormetil)fenil]metil}etil)-5-klor-4-(1-metil-1H-pirazol-5-il)-2-furankarboksamida;
N-{(1S)-2-amino-1-[(3-fluorfenil)metil]etil}-5-klor-4-(4-klor-1-metil-1H-pirazol-5-il)-2-furankarboksamida;
N-((1S)-2-amino-1-{[3-(trifluormetil)fenil]metil}etil)-5-klor-4-(4-klor-1-metil-1H-pirazol-5-il)-2-furankarboksamida;
N-{(1S)-2-amino-1-[(4-fluorfenil)metil]etil}-5-klor-4-(4-klor-1-metil-1H-pirazol-5-il)-2-furankarboksamida;
N-{(1S)-2-amino-1-[(3-fluorfenil)metil]etil}-5-klor-4-{1,4-dimetil-1H-pirazol-5-il)-2-furankarboksamida;
N-{(1S)-2-amino-1-[(4-fluorfenil)metil]etil}-5-klor-4-(1,4-dimetil-1H-pirazol-5-il)-2-furankarboksamida;
N-((1S)-2-amino-1-{[3-(trifluormetil)fenil]metil}etil)-5-klor-4-(1,4-dimetil-1H-pirazol-5-il)-2-furankarboksamida;
N-((1S)-2-amino-1-{[2-(trifluormetil)fenil]metil}etil)-5-klor-4-(1,4-dimetil-1H-pirazol-5-il)-2-furankarboksamida;
N-((1S)-2-amino-1-{[3-(trifluormetil)fenil]metil}etil)-5-metil-4-(1-metil-1H-pirazol-5-il)-2-tiofenkarboksamida;
N-{(1S)-2-amino-1-[(4-fluorfenil)metil]etil}-5-klor-4-(1-metil-1H-pirazol-5-il)-2-tiofenkarboksamida;
N-((1S)-2-amino-1-{[3-(trifluormetil)fenil]metil}etil)-5-klor-4-{1-metil-1H-pirazol-5-il)-2-tiofenkarboksamida;
N-{(1S)-2-amino-1-[(4-fluorfenil)metil]etil}-5-metil-4-(1-metil-1H-pirazol-5-il)-2-tiofenkarboksamida;
N-{(1S)-2-amino-1-[(3-fluorfenil)metil]etil}-5-metil-4-(1-metil-1H-pirazol-5-il)-2-tiofenkarboksamida;
N-((1S)-2-amino-1-{[3-(trifluormetil)fenil]metil}etil)-4-(4-klor-1-metil-1H-pirazol-5-il)-5-metil-2-tiofenkarboksamida;
N-{(1S)-2-amino-1-[(4-fluorfenil)metil]etil}-4-(4-brom-1-metil-1H-pirazol-5-il)-5-metil-2-tiofenkarboksamida;
N-{(1S)-2-amino-1-[(4-fluorfenil)metil]etil}-4-(4-klor-1-metil-1H-pirazol-5-il)-5-metil-2-tiofenkarboksamida;
N-{(1S)-2-amino-1-[(3-fluorfenil)metil]etil}-4-(4-klor-1-metil-1H-pirazol-5-il)-5-metil-2-tiofenkarboksamida;
N-{(1S)-2-amino-1-[(3-fluorfenil)metil]etil}-4-(4-brom-1-metil-1H-pirazol-5-il)-5-metil-2-tiofenkarboksamida;
N-((1S)-2-amino-1-{[3-(trifluormetil)fenil]metil}etil)-4-(4-brom-1-metil-1H-pirazol-5-il)-5-metil-2-tiofenkarboksamida;
N-((1S)-2-amino-1-{(3-(trifluormetil)fenil]metil}etil)-4-(1,4-dimetil-1H-pirazol-5-il)-5-metil-2-tiofenkarboksamida;
N-{(1S)-2-amino-1-[(3-fluorfenil)metil]etil}-4-(1,4-dimetil-1H-pirazol-5-il)-5-metil-2-tiofenkarboksamida;
N-{(1S)-2-amino-1-[(4-fluorfenil)metil]etil}-4-(1,4-dimetil-1H-pirazol-5-il)-5-metil-2-tiofenkarboksamida;
N-{(1S)-2-amino-1-[(3-fluorfenil)metil]etil}-4-(4-brom-1-metil-1H-pirazol-5-il)-5-klor-2-tiofenkarboksamida;
N-((1S)-2-amino-1-{[3-(trifluormetil)fenil]metil}etil)-5-klor-4-(4-klor-1-metil-1H-pirazol-5-il)-2-tiofenkarboksamida;
N-((1S)-2-amino-1-{[3-(trifluormetil)fenil]metil}etil)-4-(4-brom-1-metil-1H-pirazol-5-il)-5-klor-2-tiofenkarboksamida;
N-{(1S)-2-amino-1-[(4-fluorfenil)metil]etil}-4-(4-brom-1-metil-1H-pirazol-5-il)-5-klor-2-tiofenkarboksamida;
N-{(1S)-2-amino-1-[(4-fluorfenil)metil]etil}-5-klor-4-(4-klor-1-metil-1H-pirazol-5-il)-2-tiofenkarboksamida;
N-{(1S)-2-amino-1-[(2,5-difluorfenil)metil]etil}-4-(4-klor-1-metil-1H-pirazol-5-il)-5-metil-2-tiofenkarboksamida;
N-{(1S)-2-amino-1-[(2,5-difluorfenil)metil]etil}-5-metil-4-(1-metil-1H-pirazol-5-il)-2-tiofenkarboksamida;
N-{(1S)-2-amino-1-[(2,5-difluorfenil)metil]etil}-4-(1,4-dimetil-1H-pirazol-5-il)-5-metil-2-tiofenkarboksamida;
N-{(1S)-2-amino-1-[(2,5-difluorfenil)metil]etil}-5-klor-4-(4-klor-1-metil-1H-pirazol-5-il)-2-tiofenkarboksamida;
N-{(1S)-2-amino-1-[(2,5-difluorfenil)metil]etil}-5-klor-4-(1-metil-1H-pirazol-5-il)-2-tiofenkarboksamida;
N-{(1S)-2-amino-1-[(3-fluorfenil)metil]etil}-4-(4-klor-1-metil-1H-pirazol-5-il)-5-metil-2-furankarboksamida;
N-((1S)-2-amino-1-{[2-(trifluormetil)fenil]metil}etil)-5-(metiloksi)-4-(1-metil-1H-pirazol-5-il)-2-tiofenkarboksamida;
N-{(11S)-2-amino-1-[(4-fluorfenil)metil]etil}-4-(4-klor-1-metil-1H-pirazol-5-il)-5-metil-2-furankarboksamida;
N-((1S)-2-amino-1-{[3-(trifluormetil)fenil]metil}etil)-4-(4-klor-1-metil-1H-pirazol-5-il)-5-metil-2-furankarboksamida;
N-((1S)-2-amino-1-{[2-(trifluormetil)fenil]metil}etil)-4-(4-klor-1-metil-1H-pirazol-5-il-5-(metiloksi)-2-tiofenkarboksamida;
N-{(1S)-2-amino-1-[(2,5-difluorfenil)metil]etil}-5-klor-4-(1,4-dimetil-1H-pirazol-5-il)-2-tiofenkarboksamida;
N-{(1S)-2-amino-1-[(3-fluorfenil)metil]etil}-4-(4-klor-1-metil-1H-pirazol-5-il)-5-(metiloksi)-2-tiofenkarboksamida;
N-{(1S)-2-amino-1-[(4-fluorfenil)metil]etil}-4-(4-klor-1-metil-1H-pirazol-5-il)-5-(metiloksi)-2-tiofenkarboksamida;
N-((1S)-2-amino-1-{[3-(trifluormetil)fenil]metil}etil)-4-(4-klor-1-metil-1H-pirazol-5-il)-5-(metiloksi)-2-tiofenkarboksamida;
N-{(1S)-2-amino-1-[(4-fluorfenil)metil]etil}-4-(1,4-dimetil-1H-pirazol-5-il)-5-etil-2-tiofenkarboksamida;
N-{(1S)-2-amino-1-[(3,4-difluorfenil)metil]etil}-5-metil-4-(1-metil-1H-pirazol-5-il)-2-tiofenkarboksamida;
N-{(1S)-2-amino-1-[(3,4-difluorfenil)metil]etil}-4-(4-klor-1-metil-1H-pirazol-5-il)-5-metil-2-tiofenkarboksamida;
N-{(1S)-2-amino-1-[(3,4-difluorfenil)metil]etil}-5-klor-4-(1-metil-1H-pirazol-5-il)-2-tiofenkarboksamida;
N-{(1S)-2-amino-1-[(3,4-difluorfenil)metil]etil}-5-klor-4-(4-klor-1-metil-1H-pirazol-5-il)-2-tiofenkarboksamida;
N-{(1S)-2-amino-1-[(3,4-difluorfenil)metil]etil}-4-(1,4-dimetil-1H-pirazol-5-il)-5-metil-2-tiofenkarboksamida;
N-{(1S)-2-amino-1-[(3,4-difluorfenil)metil]etil}-5-klor-4-(4-klor-1-metil-1H-pirazol-5-il)-2-furankarboksamida;
N-{(1S)-2-amino-1-[(3,4-difluorfenil)metil]etil}-5-klor-4-(1-metil-1H-pirazol-5-il)-2-furankarboksamida;
N-{(1S)-2-amino-1-[(3,4-difluorfenil)metil]etil}-5-metil-4-(1-metil-1H-pirazol-5-il)-2-furankarboksamida;
N-{(1S)-2-amino-1-[(3,4-difluorfenil)metil]etil}-4-(4-klor-1-metil-1H-pirazol-5-il)-5-metil-2-furankarboksamida;
N-{(1S)-2-amino-1-[(3,4-difluorfenil)metil]etil}-5-klor-4-(1,4-dimetil-1H-pirazol-5-il)-2-furankarboksamida;
N-{(1S)-2-amino-1-[(3,4-difluorfenil)metil]etil}-4-(1,4-dimetil-1H-pirazol-5-il)-5-metil-2-furankarboksamida;
N-((1S)-2-amino-1-{[2-(trifluormetil)fenil]metil}etil)-5-klor-4-(4-klor-1-etil-1H-pirazol-5-il)-2-tiofenkarboksamida;
N-{(1S)-2-amino-1-[(3-fluorfenil)metil]etil}-5-klor-4-(4-klor-1-etil-1H-pirazol-5-il)-2-tiofenkarboksamida;
N-{(1S)-2-amino-1-[(4-fluorfenil)metil]etil}-5-klor-4-(4-klor-1-etil-1H-pirazol-5-il)-2-tiofenkarboksamida;
N-((1S)-2-amino-1-{[3-(trifluormetil)fenil]metil}etil)-5-klor-4-(4-klor-1-etil-1H-pirazol-5-il)-2-tiofenkarboksamida;
N-((1S)-2-amino-1-{[2-(trifluormetil)fenil]metil}etil)-5-klor-4-(1-etil-4-metil-1H-pirazol-5-il}-2-tiofenkarboksamida;
N-{(1S)-2-amino-1-[(3-fluorfenil)metil]etil}-5-klor-4-(1-etil-4-metil-1H-pirazol-5-il)-2-tiofenkarboksamida;
N-{(1S)-2-amino-1-[(3,4-difluorfenil)metil]etil}-5-klor-4-(1-etil-4-metil-1H-pirazol-5-il)-2-tiofenkarboksamida;
N-{(1S)-2-amino-1-[(3-fluorfenil)metil]etil}-5-klor-4-(1,4-dimetil-1H-pirazol-5-il)-2-tiofenkarboksamida;
N-((1S)-2-amino-1-{[3-(trifluormetil)fenil]metil}etil)-5-klor-4-(1,4-dimetil-1H-pirazol-5-il)-2-tiofenkarboksamida;
N-{(1S)-2-amino-1-[(4-fluorfenil)metil]etil}-5-klor-4-(1,4-dimetil-1H-pirazol-5-il)-2-tiofenkarboksamida;
N-{(1S)-2-amino-1-[(3,4-difluorfenil)metil]etil}-5-klor-4-(4-klor-1-etil-1H-pirazol-5-il)-2-tiofenkarboksamida;
N-{(1S)-2-amino-1-[(3,4-difluorfenil)metil]etil}-5-klor-4-(4-klor-1-etil-1H-pirazol-5-il)-2-furankarboksamida; i
N-{(1S)-2-amino-1-[(3,4-difluorfenil)metil]etil}-4-(4-klor-1-etil-1H-pirazol-5-il)-5-metil-2-furankarboksamida;
ili njihovih farmaceutski prihvatljivih soli.
3. Spoj u skladu s patentnim zahtjevom 1, naznačen time što ga se bira između:
N-{(1S)-2-amino-1-[(3-fluorfenil)metil]etil}-5-klor-4-(4-klor-1-metil-1H-pirazol-5-il)-2-tiofenkarboksamida;
N-{(1S)-2-amino-1-[(3-fluorfenil)metil]etil}-5-klor-4-(4-klor-1-metil-1H-pirazol-5-il)-2-furankarboksamida;
N-{(1S)-2-amino-1-[(3-fluorfenil)metil]etil}-4-(4-klor-1-metil-1H-pirazol-5-il)-5-metil-2-tiofenkarboksamida;
N-{(1S)-2-amino-1-[(3,4-difluorfenil)metil]etil}-5-klor-4-(4-klor-1-metil-1H-pirazol-5-il)-2-tiofenkarboksamida;
N-{(1S)-2-amino-1-[(3,4-difluorfenil)metil]etil}-5-klor-4-(4-klor-1-metil-1H-pirazol-5-il)-2-furankarboksamida;
ili njihovih farmaceutski prihvatljivih soli.
4. Spoj u skladu s patentnim zahtjevom 1, naznačen time što je:
N-{(1S)-2-amino-1-[(3-fluorfenil)metil]etil}-5-klor-4-(4-klor-1-metil-1H-pirazol-5-il)-2-tiofenkarboksamid;
ili njegova farmaceutski prihvatljiva sol.
5. Spoj u skladu s patentnim zahtjevom 1, naznačen time što je:
N-{(1S)-2-amino-1-[(3,4-difluorfenil)metil]etil}-5-klor-4-(4-klor-1-metil-1H-pirazol-5-il)-2-furankarboksamid;
ili njegova farmaceutski prihvatljiva sol.
6. Spoj u skladu s bilo kojim od patentnih zahtjeva 1 do 5, ili njegova farmaceutski prihvatljiva sol, naznačen time što je namijenjen upotrebi u terapiji.
7. Upotreba spoja u skladu s bilo kojim od patentnih zahtjeva 1 do 5, ili njegova farmaceutski prihvatljiva sol, naznačena time što je navedeni spoj namijenjen proizvodnji medikamenta za liječenje ili ublažavanje težine bolesti ili stanja, koje se bira između raka i artritisa.
8. Upotreba u skladu s patentnim zahtjevom 7, naznačena time što se navedeni rak bira između: raka na mozgu (glioma), glioblastoma, Bannayan-Zonaninog sindroma, Cowdenove bolesti, Lhermitte-Duclosove bolesti, raka dojke, upalnog raka dojke, Wilmsovog tumora, Ewingovog sarkoma, rabdomiosarkoma, ependimoma, meduloblastoma, raka debelog crijeva, glave i vrata, bubrega, pluća, jetre, melanoma, raka jajnika, gušterače, prostate, sarkoma, osteosarkoma, gigantocelularnog tumora kosti, raka štitnjače, leukemije limfoblastičnih T-stanica, kronične mijelogene leukemije, kronične limfocitne leukemije, leukemije vlasastih stanica, akutne limfoblastične leukemije, akutne mijelogene leukemije, kronične neutrofilne leukemije, akutne leukemije limfoblastičnih T-stanica, plazmacitoma, imunoblastične leukemije velikih stanica, leukemije stanica plašta, megakarioblastične leukemije uz multipli mijelom, multiplog mijeloma, akutne megakariocitne leukemije, promijelocitne leukemije, eritroleukemije, zloćudnog limfoma, Hodgkinovog limfoma, ne-Hodgkinovog limfoma, limfoma limfoblastičnih T-stanica, Burkittovog limfoma, follicular limfoma, neuroblastoma, raka mokraćnog mjehura, raka urotelija, raka pluća, raka vulve, raka vrata maternice, raka endometrija, raka na bubregu, mezotelioma, raka jednjaka, raka slinovnice, hepatocelularnog raka, raka želuca, raka nasofarinksa, raka u usnoj šupljini, raka usta, GIST (tumora gastrointestinalne strome) i raka testisa.
9. Upotreba u skladu s patentnim zahtjevom 8, naznačena time što se navedeni rak bira između: raka na mozgu (glioma), glioblastoma, Bannayan-Zonaninog sindroma, Cowdenove bolesti, Lhermitte-Duclosove bolesti, raka dojke, debelog crijeva, glave i vrata, bubrega, pluća, jetre, melanoma, raka jajnika, gušterače, prostate, sarkoma i raka štitnjače.
10. Farmaceutski pripravak, naznačen time što sadrži spoj u skladu s bilo kojim od patentnih zahtjeva 1 do 5, ili njegovu farmaceutski prihvatljivu sol, kao i farmaceutski prihvatljivu podlogu.
11. Farmaceutski pripravak u skladu s patentnim zahtjevom 10, naznačen time što dodatno sadrži najmanje jedno antineoplastično sredstvo.
12. Farmaceutski pripravak u skladu s patentnim zahtjevom 11, naznačen time što se najmanje jedno antineoplastično sredstvo bira iz skupine koju uglavnom čine antimikrotubulska sredstva, koordinacijski kompleksi platine, alkirajuća sredstva, antibiotička sredstva, inhibitori topoizomeraze II, antimetaboliti, inhibitori topoizomeraze I, hormoni i hormonski analozi, inhibitori puteva prijenosa signala; inhibitori angiogeneneze inhibiranjem nereceptorske tirozinske kinaze; imunoterapeutska sredstva; proapoptotska sredstva; te inhibitori signalizacije staničnog ciklusa.
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