JP2021167320A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2021167320A5 JP2021167320A5 JP2021101469A JP2021101469A JP2021167320A5 JP 2021167320 A5 JP2021167320 A5 JP 2021167320A5 JP 2021101469 A JP2021101469 A JP 2021101469A JP 2021101469 A JP2021101469 A JP 2021101469A JP 2021167320 A5 JP2021167320 A5 JP 2021167320A5
- Authority
- JP
- Japan
- Prior art keywords
- amino
- cancer
- pyridin
- group
- pyrazol
- 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.)
- Pending
Links
- 150000001875 compounds Chemical class 0.000 claims 40
- 150000003839 salts Chemical class 0.000 claims 35
- 239000008194 pharmaceutical composition Substances 0.000 claims 32
- 239000012453 solvate Substances 0.000 claims 32
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 29
- 206010028980 Neoplasm Diseases 0.000 claims 28
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 26
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 24
- 201000011510 cancer Diseases 0.000 claims 23
- -1 methyl- d3 group Chemical group 0.000 claims 19
- 229910052757 nitrogen Inorganic materials 0.000 claims 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 12
- 125000004430 oxygen atom Chemical group O* 0.000 claims 12
- 229910052799 carbon Inorganic materials 0.000 claims 11
- 150000001721 carbon Chemical group 0.000 claims 10
- 125000005843 halogen group Chemical group 0.000 claims 10
- 125000005842 heteroatom Chemical group 0.000 claims 10
- 125000004434 sulfur atom Chemical group 0.000 claims 10
- 125000002947 alkylene group Chemical group 0.000 claims 8
- 239000003795 chemical substances by application Substances 0.000 claims 8
- 239000007787 solid Substances 0.000 claims 8
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 6
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 6
- 125000002950 monocyclic group Chemical group 0.000 claims 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 6
- 239000004480 active ingredient Substances 0.000 claims 5
- 201000005787 hematologic cancer Diseases 0.000 claims 5
- 208000024200 hematopoietic and lymphoid system neoplasm Diseases 0.000 claims 5
- KJDZIQSQUKAYBX-UHFFFAOYSA-N methyl 2-amino-5-[3-amino-7-[1-(phosphonooxymethyl)pyrazol-4-yl]-[1,2]oxazolo[4,5-c]pyridin-4-yl]-4-fluorobenzoate Chemical compound NC1=C(C(=O)OC)C=C(C(=C1)F)C1=NC=C(C2=C1C(=NO2)N)C=2C=NN(C2)COP(=O)(O)O KJDZIQSQUKAYBX-UHFFFAOYSA-N 0.000 claims 5
- 206010009944 Colon cancer Diseases 0.000 claims 4
- 206010025323 Lymphomas Diseases 0.000 claims 4
- 229910019142 PO4 Inorganic materials 0.000 claims 4
- DEMVXGABKGFKCB-UHFFFAOYSA-N [4-[3-amino-4-[4-amino-5-(ethylcarbamoyl)-2-fluorophenyl]-[1,2]oxazolo[4,5-c]pyridin-7-yl]pyrazol-1-yl]methyl dihydrogen phosphate Chemical compound P(=O)(OCN1N=CC(=C1)C=1C2=C(C(=NC=1)C1=C(C=C(C(=C1)C(NCC)=O)N)F)C(=NO2)N)(O)O DEMVXGABKGFKCB-UHFFFAOYSA-N 0.000 claims 4
- 125000003277 amino group Chemical group 0.000 claims 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 4
- 230000002401 inhibitory effect Effects 0.000 claims 4
- 125000001620 monocyclic carbocycle group Chemical group 0.000 claims 4
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 4
- 239000010452 phosphate Substances 0.000 claims 4
- ZDQYTUBEMHLJFE-UHFFFAOYSA-N 1-[2-amino-5-[3-amino-7-(1H-pyrazol-4-yl)-[1,2]oxazolo[4,5-c]pyridin-4-yl]-4-fluorophenyl]ethanone Chemical compound NC1=C(C=C(C(=C1)F)C1=NC=C(C2=C1C(=NO2)N)C=2C=NNC2)C(C)=O ZDQYTUBEMHLJFE-UHFFFAOYSA-N 0.000 claims 3
- 239000002246 antineoplastic agent Substances 0.000 claims 3
- 229940041181 antineoplastic drug Drugs 0.000 claims 3
- 125000002993 cycloalkylene group Chemical group 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 229940079593 drug Drugs 0.000 claims 3
- 230000001024 immunotherapeutic effect Effects 0.000 claims 3
- CAAULPUQFIIOTL-UHFFFAOYSA-N methyl dihydrogen phosphate Chemical compound COP(O)(O)=O CAAULPUQFIIOTL-UHFFFAOYSA-N 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- 206010061424 Anal cancer Diseases 0.000 claims 2
- 208000007860 Anus Neoplasms Diseases 0.000 claims 2
- 206010004593 Bile duct cancer 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
- 208000032494 Clear cell adenocarcinoma of the ovary Diseases 0.000 claims 2
- 208000001333 Colorectal Neoplasms Diseases 0.000 claims 2
- 208000035473 Communicable disease Diseases 0.000 claims 2
- 208000000461 Esophageal Neoplasms Diseases 0.000 claims 2
- 201000001342 Fallopian tube cancer Diseases 0.000 claims 2
- 208000013452 Fallopian tube neoplasm Diseases 0.000 claims 2
- 208000022072 Gallbladder Neoplasms Diseases 0.000 claims 2
- 208000021309 Germ cell tumor Diseases 0.000 claims 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims 2
- 208000007766 Kaposi sarcoma Diseases 0.000 claims 2
- 208000032271 Malignant tumor of penis Diseases 0.000 claims 2
- 208000000172 Medulloblastoma Diseases 0.000 claims 2
- 208000034578 Multiple myelomas Diseases 0.000 claims 2
- 201000003793 Myelodysplastic syndrome Diseases 0.000 claims 2
- 208000001894 Nasopharyngeal Neoplasms Diseases 0.000 claims 2
- 206010061306 Nasopharyngeal cancer Diseases 0.000 claims 2
- 208000034176 Neoplasms, Germ Cell and Embryonal Diseases 0.000 claims 2
- 206010029260 Neuroblastoma 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
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims 2
- SBZOLQAHVRVDCI-UHFFFAOYSA-N P(=O)(OCN1N=CC(=C1)C=1C2=C(C(=NC=1)C1=C(C=C(C(=C1)S(=O)(=O)C)N)F)C(=NO2)N)(O)O Chemical compound P(=O)(OCN1N=CC(=C1)C=1C2=C(C(=NC=1)C1=C(C=C(C(=C1)S(=O)(=O)C)N)F)C(=NO2)N)(O)O SBZOLQAHVRVDCI-UHFFFAOYSA-N 0.000 claims 2
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims 2
- 208000000821 Parathyroid Neoplasms Diseases 0.000 claims 2
- 208000002471 Penile Neoplasms Diseases 0.000 claims 2
- 206010034299 Penile cancer Diseases 0.000 claims 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-L Phosphate ion(2-) Chemical compound OP([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-L 0.000 claims 2
- 206010035226 Plasma cell myeloma Diseases 0.000 claims 2
- 208000026149 Primary peritoneal carcinoma Diseases 0.000 claims 2
- 206010060862 Prostate cancer Diseases 0.000 claims 2
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 2
- 208000015634 Rectal Neoplasms Diseases 0.000 claims 2
- 208000006265 Renal cell carcinoma Diseases 0.000 claims 2
- 201000000582 Retinoblastoma Diseases 0.000 claims 2
- 206010039491 Sarcoma Diseases 0.000 claims 2
- 208000000453 Skin Neoplasms Diseases 0.000 claims 2
- 206010041067 Small cell lung cancer Diseases 0.000 claims 2
- 208000021712 Soft tissue sarcoma Diseases 0.000 claims 2
- 208000005718 Stomach Neoplasms Diseases 0.000 claims 2
- 208000024313 Testicular Neoplasms Diseases 0.000 claims 2
- 206010057644 Testis cancer Diseases 0.000 claims 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 2
- 208000024770 Thyroid neoplasm Diseases 0.000 claims 2
- 208000002495 Uterine Neoplasms Diseases 0.000 claims 2
- 206010047741 Vulval cancer Diseases 0.000 claims 2
- 208000004354 Vulvar Neoplasms Diseases 0.000 claims 2
- 201000005188 adrenal gland cancer Diseases 0.000 claims 2
- 208000024447 adrenal gland neoplasm Diseases 0.000 claims 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 201000011165 anus cancer Diseases 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 125000002619 bicyclic group Chemical group 0.000 claims 2
- 208000026900 bile duct neoplasm Diseases 0.000 claims 2
- 206010006007 bone sarcoma Diseases 0.000 claims 2
- 210000003169 central nervous system Anatomy 0.000 claims 2
- 208000006990 cholangiocarcinoma Diseases 0.000 claims 2
- 208000029742 colonic neoplasm Diseases 0.000 claims 2
- 208000035250 cutaneous malignant susceptibility to 1 melanoma Diseases 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 201000004101 esophageal cancer Diseases 0.000 claims 2
- 210000003236 esophagogastric junction Anatomy 0.000 claims 2
- WDFCXKMHINMQOK-UHFFFAOYSA-N ethyl 2-amino-5-[3-amino-7-[1-(phosphonooxymethyl)pyrazol-4-yl]-[1,2]oxazolo[4,5-c]pyridin-4-yl]-4-fluorobenzoate Chemical compound NC1=C(C(=O)OCC)C=C(C(=C1)F)C1=NC=C(C2=C1C(=NO2)N)C=2C=NN(C2)COP(=O)(O)O WDFCXKMHINMQOK-UHFFFAOYSA-N 0.000 claims 2
- 201000010175 gallbladder cancer Diseases 0.000 claims 2
- 206010017758 gastric cancer Diseases 0.000 claims 2
- 201000010536 head and neck cancer Diseases 0.000 claims 2
- 208000014829 head and neck neoplasm Diseases 0.000 claims 2
- 206010073071 hepatocellular carcinoma Diseases 0.000 claims 2
- 231100000844 hepatocellular carcinoma Toxicity 0.000 claims 2
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims 2
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims 2
- 208000032839 leukemia Diseases 0.000 claims 2
- 208000006178 malignant mesothelioma Diseases 0.000 claims 2
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims 2
- 201000005282 malignant pleural mesothelioma Diseases 0.000 claims 2
- 208000026045 malignant tumor of parathyroid gland Diseases 0.000 claims 2
- 201000001441 melanoma Diseases 0.000 claims 2
- 230000002071 myeloproliferative effect Effects 0.000 claims 2
- 201000011519 neuroendocrine tumor Diseases 0.000 claims 2
- 208000002154 non-small cell lung carcinoma Diseases 0.000 claims 2
- 201000001649 ovarian clear cell adenocarcinoma Diseases 0.000 claims 2
- 125000004043 oxo group Chemical group O=* 0.000 claims 2
- 201000002528 pancreatic cancer Diseases 0.000 claims 2
- 208000008443 pancreatic carcinoma Diseases 0.000 claims 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 2
- 206010038038 rectal cancer Diseases 0.000 claims 2
- 201000001275 rectum cancer Diseases 0.000 claims 2
- 201000000849 skin cancer Diseases 0.000 claims 2
- 208000000587 small cell lung carcinoma Diseases 0.000 claims 2
- 201000002314 small intestine cancer Diseases 0.000 claims 2
- 208000037959 spinal tumor Diseases 0.000 claims 2
- 206010041823 squamous cell carcinoma Diseases 0.000 claims 2
- 201000011549 stomach cancer Diseases 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 208000011580 syndromic disease Diseases 0.000 claims 2
- 201000003120 testicular cancer Diseases 0.000 claims 2
- 150000003536 tetrazoles Chemical class 0.000 claims 2
- 201000002510 thyroid cancer Diseases 0.000 claims 2
- 206010044412 transitional cell carcinoma Diseases 0.000 claims 2
- 150000003852 triazoles Chemical class 0.000 claims 2
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims 2
- 206010046766 uterine cancer Diseases 0.000 claims 2
- 206010046885 vaginal cancer Diseases 0.000 claims 2
- 208000013139 vaginal neoplasm Diseases 0.000 claims 2
- 201000005102 vulva cancer Diseases 0.000 claims 2
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 1
- LSTJLJYRJLFTJD-UHFFFAOYSA-N 1-[2-amino-5-[3-amino-7-(1H-pyrazol-4-yl)-[1,2]oxazolo[4,5-c]pyridin-4-yl]-4-fluorophenyl]butan-1-one Chemical compound NC1=C(C=C(C(=C1)F)C1=NC=C(C2=C1C(=NO2)N)C=2C=NNC2)C(CCC)=O LSTJLJYRJLFTJD-UHFFFAOYSA-N 0.000 claims 1
- LYOZDCBEZDXVSR-UHFFFAOYSA-N 1-[2-amino-5-[3-amino-7-(1H-pyrazol-4-yl)-[1,2]oxazolo[4,5-c]pyridin-4-yl]-4-fluorophenyl]propan-1-one Chemical compound NC1=C(C=C(C(=C1)F)C1=NC=C(C2=C1C(=NO2)N)C=2C=NNC2)C(CC)=O LYOZDCBEZDXVSR-UHFFFAOYSA-N 0.000 claims 1
- DOMUPAPZOLMKRZ-UHFFFAOYSA-N 1-[2-amino-5-[3-amino-7-(1H-pyrazol-4-yl)-[1,2]oxazolo[4,5-c]pyridin-4-yl]-4-hydroxyphenyl]ethanone Chemical compound NC1=C(C=C(C(=C1)O)C1=NC=C(C2=C1C(=NO2)N)C=2C=NNC2)C(C)=O DOMUPAPZOLMKRZ-UHFFFAOYSA-N 0.000 claims 1
- DTIOWIXJIMZWTL-UHFFFAOYSA-N 1-[2-amino-5-[3-amino-7-(1H-pyrazol-4-yl)-[1,2]oxazolo[4,5-c]pyridin-4-yl]phenyl]butan-1-one Chemical compound NC1=C(C=C(C=C1)C1=NC=C(C2=C1C(=NO2)N)C=2C=NNC2)C(CCC)=O DTIOWIXJIMZWTL-UHFFFAOYSA-N 0.000 claims 1
- UMUFWMJHSBRMIO-UHFFFAOYSA-N 1-[2-amino-5-[3-amino-7-(1H-pyrazol-4-yl)-[1,2]oxazolo[4,5-c]pyridin-4-yl]phenyl]ethanone Chemical compound NC1=C(C=C(C=C1)C1=NC=C(C2=C1C(=NO2)N)C=2C=NNC2)C(C)=O UMUFWMJHSBRMIO-UHFFFAOYSA-N 0.000 claims 1
- ZKAQPCMSICOAKT-UHFFFAOYSA-N 1-[2-amino-5-[3-amino-7-(1H-pyrazol-4-yl)-[1,2]oxazolo[4,5-c]pyridin-4-yl]phenyl]propan-1-one Chemical compound NC1=C(C=C(C=C1)C1=NC=C(C2=C1C(=NO2)N)C=2C=NNC2)C(CC)=O ZKAQPCMSICOAKT-UHFFFAOYSA-N 0.000 claims 1
- SKZIOYDQLATRFA-UHFFFAOYSA-N 1-[2-amino-5-[3-amino-7-(1H-pyrazol-4-yl)-[1,2]thiazolo[4,5-c]pyridin-4-yl]-4-fluorophenyl]ethanone Chemical compound NC1=C(C=C(C(=C1)F)C1=NC=C(C2=C1C(=NS2)N)C=2C=NNC2)C(C)=O SKZIOYDQLATRFA-UHFFFAOYSA-N 0.000 claims 1
- BGMWFYXYJZUNJA-UHFFFAOYSA-N 2-amino-5-[3-amino-7-(1H-pyrazol-4-yl)-[1,2]oxazolo[4,5-c]pyridin-4-yl]-4-chloro-N-ethylbenzamide Chemical compound NC1=C(C(=O)NCC)C=C(C(=C1)Cl)C1=NC=C(C2=C1C(=NO2)N)C=2C=NNC2 BGMWFYXYJZUNJA-UHFFFAOYSA-N 0.000 claims 1
- MJUUZZSMBBSHTP-UHFFFAOYSA-N 2-amino-5-[3-amino-7-(1H-pyrazol-4-yl)-[1,2]oxazolo[4,5-c]pyridin-4-yl]-4-fluoro-N-methylbenzamide Chemical compound NC1=C(C(=O)NC)C=C(C(=C1)F)C1=NC=C(C2=C1C(=NO2)N)C=2C=NNC2 MJUUZZSMBBSHTP-UHFFFAOYSA-N 0.000 claims 1
- HGUTWJDKLXVXBF-UHFFFAOYSA-N 2-amino-5-[3-amino-7-(1H-pyrazol-4-yl)-[1,2]oxazolo[4,5-c]pyridin-4-yl]-4-fluoro-N-propylbenzamide Chemical compound NC1=C(C(=O)NCCC)C=C(C(=C1)F)C1=NC=C(C2=C1C(=NO2)N)C=2C=NNC2 HGUTWJDKLXVXBF-UHFFFAOYSA-N 0.000 claims 1
- RVISIVQEGFHZGI-UHFFFAOYSA-N 2-amino-5-[3-amino-7-(1H-pyrazol-4-yl)-[1,2]oxazolo[4,5-c]pyridin-4-yl]-4-fluorobenzamide Chemical compound NC1=C(C(=O)N)C=C(C(=C1)F)C1=NC=C(C2=C1C(=NO2)N)C=2C=NNC2 RVISIVQEGFHZGI-UHFFFAOYSA-N 0.000 claims 1
- KYZZDINTLXUBRZ-UHFFFAOYSA-N 2-amino-5-[3-amino-7-(1H-pyrazol-4-yl)-[1,2]oxazolo[4,5-c]pyridin-4-yl]-4-fluorobenzoic acid Chemical compound NC1=C(C(=O)O)C=C(C(=C1)F)C1=NC=C(C2=C1C(=NO2)N)C=2C=NNC2 KYZZDINTLXUBRZ-UHFFFAOYSA-N 0.000 claims 1
- OKNUSGOSKGSQQK-UHFFFAOYSA-N 2-amino-5-[3-amino-7-(1H-pyrazol-4-yl)-[1,2]oxazolo[4,5-c]pyridin-4-yl]-N-ethyl-4-fluorobenzamide Chemical compound NC1=C(C(=O)NCC)C=C(C(=C1)F)C1=NC=C(C2=C1C(=NO2)N)C=2C=NNC2 OKNUSGOSKGSQQK-UHFFFAOYSA-N 0.000 claims 1
- VUFHPBPWOIBDGK-UHFFFAOYSA-N 2-amino-5-[3-amino-7-(1H-pyrazol-4-yl)-[1,2]oxazolo[4,5-c]pyridin-4-yl]-N-ethylbenzamide Chemical compound NC1=C(C(=O)NCC)C=C(C=C1)C1=NC=C(C2=C1C(=NO2)N)C=2C=NNC2 VUFHPBPWOIBDGK-UHFFFAOYSA-N 0.000 claims 1
- XDSWQNMGJJKWLP-UHFFFAOYSA-N 2-amino-5-[3-amino-7-(1H-pyrazol-4-yl)-[1,2]oxazolo[4,5-c]pyridin-4-yl]-N-methylbenzamide Chemical compound NC1=C(C(=O)NC)C=C(C=C1)C1=NC=C(C2=C1C(=NO2)N)C=2C=NNC2 XDSWQNMGJJKWLP-UHFFFAOYSA-N 0.000 claims 1
- PCCPHFKIFNKXAO-UHFFFAOYSA-N 2-amino-5-[3-amino-7-(1H-pyrazol-4-yl)-[1,2]oxazolo[4,5-c]pyridin-4-yl]-N-propylbenzamide Chemical compound NC1=C(C(=O)NCCC)C=C(C=C1)C1=NC=C(C2=C1C(=NO2)N)C=2C=NNC2 PCCPHFKIFNKXAO-UHFFFAOYSA-N 0.000 claims 1
- VYRSHRFJTVQAJU-UHFFFAOYSA-N 2-amino-5-[3-amino-7-(1H-pyrazol-4-yl)-[1,2]oxazolo[4,5-c]pyridin-4-yl]benzamide Chemical compound NC1=C(C(=O)N)C=C(C=C1)C1=NC=C(C2=C1C(=NO2)N)C=1C=NNC=1 VYRSHRFJTVQAJU-UHFFFAOYSA-N 0.000 claims 1
- HHJDAJHHWHTQJE-UHFFFAOYSA-N 2-hydroxyethyl 2-amino-5-[3-amino-7-(1H-pyrazol-4-yl)-[1,2]oxazolo[4,5-c]pyridin-4-yl]-4-fluorobenzoate Chemical compound NC1=C(C(=O)OCCO)C=C(C(=C1)F)C1=NC=C(C2=C1C(=NO2)N)C=2C=NNC2 HHJDAJHHWHTQJE-UHFFFAOYSA-N 0.000 claims 1
- YNTURPJHANIJQY-UHFFFAOYSA-N 4-(2-fluoro-5-methoxy-4-nitrophenyl)-7-(1H-pyrazol-4-yl)-[1,2]oxazolo[4,5-c]pyridin-3-amine Chemical compound FC1=C(C=C(C(=C1)[N+](=O)[O-])OC)C1=NC=C(C2=C1C(=NO2)N)C=2C=NNC2 YNTURPJHANIJQY-UHFFFAOYSA-N 0.000 claims 1
- WGZGWSNFTNFCFB-UHFFFAOYSA-N 4-(4-amino-2-chloro-5-methylsulfanylphenyl)-7-(1H-pyrazol-4-yl)-[1,2]oxazolo[4,5-c]pyridin-3-amine Chemical compound NC1=CC(=C(C=C1SC)C1=NC=C(C2=C1C(=NO2)N)C=2C=NNC2)Cl WGZGWSNFTNFCFB-UHFFFAOYSA-N 0.000 claims 1
- PPVADNNKDQPXSF-UHFFFAOYSA-N 4-(4-amino-2-fluoro-3-methoxyphenyl)-7-(1H-pyrazol-4-yl)-[1,2]oxazolo[4,5-c]pyridin-3-amine Chemical compound NC1=C(C(=C(C=C1)C1=NC=C(C2=C1C(=NO2)N)C=2C=NNC2)F)OC PPVADNNKDQPXSF-UHFFFAOYSA-N 0.000 claims 1
- PWLHWAARAJDKCT-UHFFFAOYSA-N 4-(4-amino-2-fluoro-5-methoxyphenyl)-7-(1H-pyrazol-4-yl)-[1,2]oxazolo[4,5-c]pyridin-3-amine Chemical compound NC1=CC(=C(C=C1OC)C1=NC=C(C2=C1C(=NO2)N)C=2C=NNC2)F PWLHWAARAJDKCT-UHFFFAOYSA-N 0.000 claims 1
- KTFVQPMFMICGKC-UHFFFAOYSA-N 4-(4-amino-2-fluoro-5-methoxyphenyl)-7-(1H-pyrazol-4-yl)-[1,2]oxazolo[5,4-c]pyridin-3-amine Chemical compound NC1=CC(=C(C=C1OC)C1=C2C(=C(N=C1)C=1C=NNC1)ON=C2N)F KTFVQPMFMICGKC-UHFFFAOYSA-N 0.000 claims 1
- FAOWAHOTVSCQEC-UHFFFAOYSA-N 4-(4-amino-2-fluoro-5-methoxyphenyl)-7-(5-methyl-1H-pyrazol-4-yl)-[1,2]oxazolo[4,5-c]pyridin-3-amine Chemical compound NC1=CC(=C(C=C1OC)C1=NC=C(C2=C1C(=NO2)N)C=2C(=NNC2)C)F FAOWAHOTVSCQEC-UHFFFAOYSA-N 0.000 claims 1
- VJJKTXNNGGUFTR-UHFFFAOYSA-N 4-(4-amino-2-fluoro-5-methylsulfanylphenyl)-7-(1H-pyrazol-4-yl)-[1,2]oxazolo[4,5-c]pyridin-3-amine Chemical compound NC1=CC(=C(C=C1SC)C1=NC=C(C2=C1C(=NO2)N)C=2C=NNC2)F VJJKTXNNGGUFTR-UHFFFAOYSA-N 0.000 claims 1
- INVFBBPUZZBJJD-UHFFFAOYSA-N 4-(4-amino-2-fluoro-5-methylsulfinylphenyl)-7-(1H-pyrazol-4-yl)-[1,2]oxazolo[4,5-c]pyridin-3-amine Chemical compound NC1=CC(=C(C=C1S(=O)C)C1=NC=C(C2=C1C(=NO2)N)C=2C=NNC2)F INVFBBPUZZBJJD-UHFFFAOYSA-N 0.000 claims 1
- NREUAAKBKNPNKX-UHFFFAOYSA-N 4-(4-amino-2-fluoro-5-methylsulfonylphenyl)-7-(1H-pyrazol-4-yl)-[1,2]oxazolo[4,5-c]pyridin-3-amine Chemical compound NC1=CC(=C(C=C1S(=O)(=O)C)C1=NC=C(C2=C1C(=NO2)N)C=2C=NNC2)F NREUAAKBKNPNKX-UHFFFAOYSA-N 0.000 claims 1
- KQOPQATWGFWENY-UHFFFAOYSA-N 4-(4-amino-3-methoxyphenyl)-7-(1H-pyrazol-4-yl)-[1,2]oxazolo[4,5-c]pyridin-3-amine Chemical compound NC1=C(C=C(C=C1)C1=NC=C(C2=C1C(=NO2)N)C=2C=NNC2)OC KQOPQATWGFWENY-UHFFFAOYSA-N 0.000 claims 1
- GZOSBWSAZZJQOM-UHFFFAOYSA-N 4-(4-amino-5-ethylsulfanyl-2-fluorophenyl)-7-(1H-pyrazol-4-yl)-[1,2]oxazolo[4,5-c]pyridin-3-amine Chemical compound NC1=CC(=C(C=C1SCC)C1=NC=C(C2=C1C(=NO2)N)C=2C=NNC2)F GZOSBWSAZZJQOM-UHFFFAOYSA-N 0.000 claims 1
- PWLHWAARAJDKCT-FIBGUPNXSA-N 4-[4-amino-2-fluoro-5-(trideuteriomethoxy)phenyl]-7-(1H-pyrazol-4-yl)-[1,2]oxazolo[4,5-c]pyridin-3-amine Chemical compound NC1=CC(=C(C=C1OC([2H])([2H])[2H])C1=NC=C(C2=C1C(=NO2)N)C=2C=NNC2)F PWLHWAARAJDKCT-FIBGUPNXSA-N 0.000 claims 1
- DCGYCUQIYSBJFO-UHFFFAOYSA-N 4-[4-amino-2-fluoro-5-(trifluoromethyl)phenyl]-7-(1H-pyrazol-4-yl)-[1,2]oxazolo[4,5-c]pyridin-3-amine Chemical compound NC1=CC(=C(C=C1C(F)(F)F)C1=NC=C(C2=C1C(=NO2)N)C=2C=NNC2)F DCGYCUQIYSBJFO-UHFFFAOYSA-N 0.000 claims 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims 1
- SJXTZINZZCIRAE-UHFFFAOYSA-N CC(C(C(N)=C1)=CC(C2=NC=C(C3=CN(C(OC)=O)N=C3)C3=C2C(N)=NO3)=C1F)=O Chemical compound CC(C(C(N)=C1)=CC(C2=NC=C(C3=CN(C(OC)=O)N=C3)C3=C2C(N)=NO3)=C1F)=O SJXTZINZZCIRAE-UHFFFAOYSA-N 0.000 claims 1
- FZCFRMHLFTUXTM-UHFFFAOYSA-N CC(N1N=CC(C(C2=C3C(N)=NO2)=CN=C3C(C=C(C(C)=O)C(N)=C2)=C2F)=C1)OC(N(C)C1=NC=CC=C1COC(CNC)=O)=O Chemical compound CC(N1N=CC(C(C2=C3C(N)=NO2)=CN=C3C(C=C(C(C)=O)C(N)=C2)=C2F)=C1)OC(N(C)C1=NC=CC=C1COC(CNC)=O)=O FZCFRMHLFTUXTM-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 1
- 208000001976 Endocrine Gland Neoplasms Diseases 0.000 claims 1
- 239000004471 Glycine Substances 0.000 claims 1
- 206010052399 Neuroendocrine tumour Diseases 0.000 claims 1
- 229940044665 STING agonist Drugs 0.000 claims 1
- MUFMPJMTEHXRAN-UHFFFAOYSA-N [4-[3-amino-4-[4-amino-2-chloro-5-(ethylcarbamoyl)phenyl]-[1,2]oxazolo[4,5-c]pyridin-7-yl]pyrazol-1-yl]methyl dihydrogen phosphate Chemical compound P(=O)(OCN1N=CC(=C1)C=1C2=C(C(=NC=1)C1=C(C=C(C(=C1)C(NCC)=O)N)Cl)C(=NO2)N)(O)O MUFMPJMTEHXRAN-UHFFFAOYSA-N 0.000 claims 1
- 230000008484 agonism Effects 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 210000000941 bile Anatomy 0.000 claims 1
- 201000009036 biliary tract cancer Diseases 0.000 claims 1
- 208000020790 biliary tract neoplasm Diseases 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 210000000750 endocrine system Anatomy 0.000 claims 1
- LTNQZWRIIQLCQY-UHFFFAOYSA-N ethyl 2-amino-5-[3-amino-7-(1H-pyrazol-4-yl)-[1,2]oxazolo[4,5-c]pyridin-4-yl]-4-fluorobenzoate Chemical compound NC1=C(C(=O)OCC)C=C(C(=C1)F)C1=NC=C(C2=C1C(=NO2)N)C=2C=NNC2 LTNQZWRIIQLCQY-UHFFFAOYSA-N 0.000 claims 1
- ZJXZSIYSNXKHEA-UHFFFAOYSA-N ethyl dihydrogen phosphate Chemical compound CCOP(O)(O)=O ZJXZSIYSNXKHEA-UHFFFAOYSA-N 0.000 claims 1
- 239000002955 immunomodulating agent Substances 0.000 claims 1
- 208000015181 infectious disease Diseases 0.000 claims 1
- 208000029559 malignant endocrine neoplasm Diseases 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- NUGRPZFDGUZEPW-UHFFFAOYSA-N methyl 2-amino-5-[3-amino-7-(1H-pyrazol-4-yl)-[1,2]oxazolo[4,5-c]pyridin-4-yl]-4-fluorobenzoate Chemical compound NC1=C(C(=O)OC)C=C(C(=C1)F)C1=NC=C(C2=C1C(=NO2)N)C=2C=NNC2 NUGRPZFDGUZEPW-UHFFFAOYSA-N 0.000 claims 1
- XUDGSMYKHCAIAO-UHFFFAOYSA-N methyl 2-amino-5-[3-amino-7-(1H-pyrazol-4-yl)-[1,2]oxazolo[4,5-c]pyridin-4-yl]benzoate Chemical compound NC1=C(C(=O)OC)C=C(C=C1)C1=NC=C(C2=C1C(=NO2)N)C=1C=NNC=1 XUDGSMYKHCAIAO-UHFFFAOYSA-N 0.000 claims 1
- RCIJMMSZBQEWKW-UHFFFAOYSA-N methyl propan-2-yl carbonate Chemical compound COC(=O)OC(C)C RCIJMMSZBQEWKW-UHFFFAOYSA-N 0.000 claims 1
- 208000016065 neuroendocrine neoplasm Diseases 0.000 claims 1
- 229940127084 other anti-cancer agent Drugs 0.000 claims 1
- LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 208000015347 renal cell adenocarcinoma Diseases 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2021503933A JPWO2021205631A1 (https=) | 2020-04-10 | 2020-04-10 | |
| JP2021503933 | 2020-04-10 | ||
| JP2021066254A JP6912016B1 (ja) | 2020-04-10 | 2021-04-09 | Ｓｔｉｎｇ作動化合物 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2021066254A Division JP6912016B1 (ja) | 2020-04-10 | 2021-04-09 | Ｓｔｉｎｇ作動化合物 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2021167320A JP2021167320A (ja) | 2021-10-21 |
| JP2021167320A5 true JP2021167320A5 (https=) | 2024-03-28 |
Family
ID=76969224
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2021066254A Active JP6912016B1 (ja) | 2020-04-10 | 2021-04-09 | Ｓｔｉｎｇ作動化合物 |
| JP2021101469A Pending JP2021167320A (ja) | 2020-04-10 | 2021-06-18 | Ｓｔｉｎｇ作動化合物 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2021066254A Active JP6912016B1 (ja) | 2020-04-10 | 2021-04-09 | Ｓｔｉｎｇ作動化合物 |
Country Status (1)
| Country | Link |
|---|---|
| JP (2) | JP6912016B1 (https=) |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002069061A (ja) * | 2000-08-30 | 2002-03-08 | Canon Inc | オキサゾール化合物及びそれを用いた有機発光素子 |
| ATE554087T1 (de) * | 2004-10-29 | 2012-05-15 | Abbott Lab | Neue kinaseinhibitoren |
| WO2015160636A1 (en) * | 2014-04-16 | 2015-10-22 | Merck Sharp & Dohme Corp. | Factor ixa inhibitors |
| KR102746352B1 (ko) * | 2014-08-13 | 2024-12-24 | 오클랜드 유니서비시즈 리미티드 | 트립토판 디옥시게나제 (ido1 및 tdo)의 억제제 및 치료에서 이들의 용도 |
| CN107849084B (zh) * | 2015-12-03 | 2021-09-14 | 葛兰素史密斯克莱知识产权发展有限公司 | 作为sting调节剂的环状嘌呤二核苷酸 |
| MX2020008265A (es) * | 2018-02-16 | 2020-09-21 | UCB Biopharma SRL | Derivados farmaceuticos del anillo heterobiciclico 6,5. |
| CN120004785A (zh) * | 2018-07-03 | 2025-05-16 | 诺华制药股份有限公司 | 用于治疗与sting活性有关的疾病的化合物和组合物 |
-
2021
- 2021-04-09 JP JP2021066254A patent/JP6912016B1/ja active Active
- 2021-06-18 JP JP2021101469A patent/JP2021167320A/ja active Pending
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| TWI869913B (zh) | 吡啶并[4,3-d]嘧啶化合物 | |
| ES3036496T3 (en) | Fused tricyclic ring derivatives as src homology-2 phosphatase inhibitors | |
| ES2819448T3 (es) | Tetrahidro-pirido[3,4-b]indoles como moduladores del receptor de estrógenos y usos de los mismos | |
| EP4129295A1 (en) | Pharmaceutical composition for prevention or treatment of cancers associated with kras mutation | |
| CN103748099B (zh) | 作为蛋白激酶抑制剂的大环化合物 | |
| KR20210075992A (ko) | Sting 작동 화합물 | |
| AU2016366680B2 (en) | Benzothiophene-based selective estrogen receptor downregulators | |
| EP2890698B1 (en) | Dioxino- and oxazin-[2,3-d]pyrimidine pi3k inhibitor compounds and methods of use | |
| RU2017145026A (ru) | Соединение, ингибирующее brk | |
| BR112012006807A2 (pt) | compostos da fórmula i, composição farmacêutica, composta por composto, método de tratamento de câncer em um mamífero, uso de um composto, kit para tratar um condição mediada por pi3k e processo para a preparação de um composto | |
| SG171765A1 (en) | Pyrazolopyridine pi3k inhibitor compounds and methods of use | |
| JP2017533223A (ja) | ユビキチン活性化酵素阻害物質及び化学療法剤の投与 | |
| KR20250100539A (ko) | 피리도[4,3-d]피리미딘 화합물 | |
| CN104513258B (zh) | 取代脲衍生物及其在药物中的应用 | |
| JP7479292B2 (ja) | 組み合わせ医薬として用いられるｅｚｈ１／２二重阻害剤を含有する医薬組成物 | |
| JP2021167320A5 (https=) | ||
| WO2011094260A2 (en) | Novel bifunctional metnase/intnase inhibitors and related compositions and methods of treatment of cancer | |
| CN114786674A (zh) | Ahr抑制剂和pd1抑制剂抗体的组合及其在癌症治疗中的用途 | |
| JP2008545803A5 (https=) | ||
| JPWO2021206158A5 (https=) | ||
| NZ774859B2 (en) | Sting agonistic compound | |
| WO2022169840A1 (en) | Combination of dual atm and dna-pk inhibitors and immunotherapeutic agents for use in cancer therapy | |
| KR20220167275A (ko) | 암 치료 방법 | |
| CN105461709B (zh) | 取代脲衍生物及其在药物中的应用 | |
| HK40071759A (en) | Combination of an ahr-inhibitor and an pd1-inhibitor antibody and its use in the treatment of cancer |