JP2019513734A5 - - Google Patents
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- JP2019513734A5 JP2019513734A5 JP2018552242A JP2018552242A JP2019513734A5 JP 2019513734 A5 JP2019513734 A5 JP 2019513734A5 JP 2018552242 A JP2018552242 A JP 2018552242A JP 2018552242 A JP2018552242 A JP 2018552242A JP 2019513734 A5 JP2019513734 A5 JP 2019513734A5
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- JP
- Japan
- Prior art keywords
- alkyl
- nhc
- halo
- alkoxy
- substituted
- 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.)
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- 125000005843 halogen group Chemical group 0.000 claims 31
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 20
- -1 amino, hydroxy Chemical group 0.000 claims 20
- 239000001257 hydrogen Substances 0.000 claims 20
- 229910052739 hydrogen Inorganic materials 0.000 claims 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 19
- 125000003831 tetrazolyl group Chemical group 0.000 claims 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 13
- 150000003839 salts Chemical class 0.000 claims 13
- 125000004429 atom Chemical group 0.000 claims 12
- 125000005334 azaindolyl group Chemical group N1N=C(C2=CC=CC=C12)* 0.000 claims 12
- 150000001875 compounds Chemical class 0.000 claims 12
- 125000004122 cyclic group Chemical group 0.000 claims 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 11
- 125000001041 indolyl group Chemical group 0.000 claims 11
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 10
- 125000003118 aryl group Chemical group 0.000 claims 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims 10
- 125000001072 heteroaryl group Chemical group 0.000 claims 10
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 9
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 8
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 8
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 8
- 125000003275 alpha amino acid group Chemical group 0.000 claims 7
- 239000008194 pharmaceutical composition Substances 0.000 claims 7
- 229920006395 saturated elastomer Polymers 0.000 claims 6
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims 5
- YBJHBAHKTGYVGT-ZKWXMUAHSA-N (+)-Biotin Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 0.000 claims 4
- OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 claims 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 3
- 229910052799 carbon Inorganic materials 0.000 claims 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 3
- 150000002431 hydrogen Chemical group 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- 208000035473 Communicable disease Diseases 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- 229960002685 biotin Drugs 0.000 claims 2
- 235000020958 biotin Nutrition 0.000 claims 2
- 239000011616 biotin Substances 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 230000005494 condensation Effects 0.000 claims 2
- 238000009833 condensation Methods 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 208000002154 non-small cell lung carcinoma Diseases 0.000 claims 2
- 125000004043 oxo group Chemical group O=* 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 125000003386 piperidinyl group Chemical group 0.000 claims 2
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims 2
- 229940046009 vitamin E Drugs 0.000 claims 2
- 239000011709 vitamin E Substances 0.000 claims 2
- MTAODLNXWYIKSO-UHFFFAOYSA-N 2-fluoropyridine Chemical compound FC1=CC=CC=N1 MTAODLNXWYIKSO-UHFFFAOYSA-N 0.000 claims 1
- 102000008096 B7-H1 Antigen Human genes 0.000 claims 1
- 108010074708 B7-H1 Antigen Proteins 0.000 claims 1
- 208000017897 Carcinoma of esophagus Diseases 0.000 claims 1
- 206010009944 Colon cancer Diseases 0.000 claims 1
- 208000001333 Colorectal Neoplasms Diseases 0.000 claims 1
- 208000002250 Hematologic Neoplasms Diseases 0.000 claims 1
- 101000914484 Homo sapiens T-lymphocyte activation antigen CD80 Proteins 0.000 claims 1
- 206010027476 Metastases Diseases 0.000 claims 1
- 206010033128 Ovarian cancer Diseases 0.000 claims 1
- 206010061535 Ovarian neoplasm Diseases 0.000 claims 1
- 206010060862 Prostate cancer Diseases 0.000 claims 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 1
- 208000006265 Renal cell carcinoma Diseases 0.000 claims 1
- 206010040070 Septic Shock Diseases 0.000 claims 1
- 208000000102 Squamous Cell Carcinoma of Head and Neck Diseases 0.000 claims 1
- 208000005718 Stomach Neoplasms Diseases 0.000 claims 1
- 102100027222 T-lymphocyte activation antigen CD80 Human genes 0.000 claims 1
- 241000700605 Viruses Species 0.000 claims 1
- 229930003427 Vitamin E Natural products 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- XTKDAFGWCDAMPY-UHFFFAOYSA-N azaperone Chemical group C1=CC(F)=CC=C1C(=O)CCCN1CCN(C=2N=CC=CC=2)CC1 XTKDAFGWCDAMPY-UHFFFAOYSA-N 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 230000000903 blocking effect Effects 0.000 claims 1
- 210000000481 breast Anatomy 0.000 claims 1
- 201000008275 breast carcinoma Diseases 0.000 claims 1
- 230000005907 cancer growth Effects 0.000 claims 1
- 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 1
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 claims 1
- 210000002249 digestive system Anatomy 0.000 claims 1
- 208000018554 digestive system carcinoma Diseases 0.000 claims 1
- 230000002708 enhancing effect Effects 0.000 claims 1
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 claims 1
- 206010017758 gastric cancer Diseases 0.000 claims 1
- 201000000459 head and neck squamous cell carcinoma Diseases 0.000 claims 1
- 206010073071 hepatocellular carcinoma Diseases 0.000 claims 1
- 231100000844 hepatocellular carcinoma Toxicity 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 230000028993 immune response Effects 0.000 claims 1
- 208000015181 infectious disease Diseases 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 230000003993 interaction Effects 0.000 claims 1
- 201000008443 lung non-squamous non-small cell carcinoma Diseases 0.000 claims 1
- 201000001441 melanoma Diseases 0.000 claims 1
- 230000009401 metastasis Effects 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 210000000496 pancreas Anatomy 0.000 claims 1
- 230000036303 septic shock Effects 0.000 claims 1
- 230000004936 stimulating effect Effects 0.000 claims 1
- 201000011549 stomach cancer Diseases 0.000 claims 1
- 238000005728 strengthening Methods 0.000 claims 1
- 125000001425 triazolyl group Chemical group 0.000 claims 1
- 235000019165 vitamin E Nutrition 0.000 claims 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201662318417P | 2016-04-05 | 2016-04-05 | |
| US62/318,417 | 2016-04-05 | ||
| US15/475,227 US10358463B2 (en) | 2016-04-05 | 2017-03-31 | Immunomodulators |
| US15/475,227 | 2017-03-31 | ||
| PCT/US2017/025677 WO2017176608A1 (en) | 2016-04-05 | 2017-04-03 | Macrocyclic inhibitors of the pd-1/pd-l1 and cd80/pd-l1 protein/protein interactions |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2019513734A JP2019513734A (ja) | 2019-05-30 |
| JP2019513734A5 true JP2019513734A5 (https=) | 2020-05-14 |
| JP7122255B2 JP7122255B2 (ja) | 2022-08-19 |
Family
ID=59960204
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018552242A Active JP7122255B2 (ja) | 2016-04-05 | 2017-04-03 | Ｐｄ－１／ｐｄ－ｌ１およびｃｄ８０／ｐｄ－ｌ１のタンパク質／タンパク質の相互作用の大環状阻害剤 |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US10358463B2 (https=) |
| EP (1) | EP3440097B1 (https=) |
| JP (1) | JP7122255B2 (https=) |
| KR (1) | KR102548798B1 (https=) |
| CN (1) | CN109311943A (https=) |
| AR (1) | AR108186A1 (https=) |
| AU (1) | AU2017246216A1 (https=) |
| BR (1) | BR112018070377A2 (https=) |
| CA (1) | CA3020300A1 (https=) |
| EA (1) | EA201892243A1 (https=) |
| ES (1) | ES2998042T3 (https=) |
| IL (1) | IL262126A (https=) |
| MA (1) | MA43774A (https=) |
| MX (1) | MX2018012039A (https=) |
| SG (1) | SG11201808678QA (https=) |
| TW (1) | TW201738260A (https=) |
| UY (1) | UY37194A (https=) |
| WO (1) | WO2017176608A1 (https=) |
Families Citing this family (87)
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| US9856292B2 (en) | 2014-11-14 | 2018-01-02 | Bristol-Myers Squibb Company | Immunomodulators |
| US9861680B2 (en) * | 2014-12-18 | 2018-01-09 | Bristol-Myers Squibb Company | Immunomodulators |
| US9944678B2 (en) * | 2014-12-19 | 2018-04-17 | Bristol-Myers Squibb Company | Immunomodulators |
| US10143746B2 (en) | 2016-03-04 | 2018-12-04 | Bristol-Myers Squibb Company | Immunomodulators |
| HRP20210644T8 (hr) | 2016-05-19 | 2021-06-25 | Bristol-Myers Squibb Company | Imunomodulatori za pet-snimanje |
| KR20230010826A (ko) | 2016-10-14 | 2023-01-19 | 프리시젼 바이오사이언시스 인코포레이티드 | B형 간염 바이러스 게놈 내의 인식 서열에 대해 특이적인 조작된 메가뉴클레아제 |
| KR102526034B1 (ko) * | 2016-11-07 | 2023-04-25 | 브리스톨-마이어스 스큅 컴퍼니 | 면역조정제 |
| EP3567049A4 (en) | 2016-12-28 | 2020-08-26 | Green Cross Lab Cell Corporation | CHEMERICAL ANTIGENIC RECEPTOR AND NATURAL KILLER CELLS EXPRESSING THE SAME |
| BR102018007822A2 (pt) | 2017-04-20 | 2018-11-06 | Gilead Sciences, Inc. | composto, métodos para inibir pd-1, pd-l1 e/ou interação de pd-1/pd-l1 e para tratamento de câncer, composição farmacêutica, e, kit para tratamento de ou prevenção de câncer ou uma doença ou condição |
| EP3642220A1 (en) * | 2017-06-23 | 2020-04-29 | Bristol-Myers Squibb Company | Immunomodulators acting as antagonists of pd-1 |
| CN111051332B (zh) | 2017-10-03 | 2024-09-06 | 百时美施贵宝公司 | 免疫调节剂 |
| US11649294B2 (en) | 2017-11-14 | 2023-05-16 | GC Cell Corporation | Anti-HER2 antibody or antigen-binding fragment thereof, and chimeric antigen receptor comprising same |
| KR102774451B1 (ko) | 2017-11-14 | 2025-02-28 | 앱클론(주) | 항-her2 항체 또는 그의 항원 결합 단편, 및 이를 포함하는 키메라 항원 수용체 |
| WO2019123339A1 (en) | 2017-12-20 | 2019-06-27 | Institute Of Organic Chemistry And Biochemistry Ascr, V.V.I. | 2'3' cyclic dinucleotides with phosphonate bond activating the sting adaptor protein |
| EP3728283B1 (en) | 2017-12-20 | 2023-11-22 | Institute of Organic Chemistry and Biochemistry ASCR, V.V.I. | 3'3' cyclic dinucleotides with phosphonate bond activating the sting adaptor protein |
| MX2020008138A (es) * | 2018-02-02 | 2020-10-19 | Eustralis Pharmaceuticals Ltd Trading As Pressura Neuro | Formulaciones parentales y usos de estas. |
| CR20200347A (es) | 2018-02-13 | 2020-09-23 | Gilead Sciences Inc | Inhibidores pd-1/pd-l1 |
| JP7050165B2 (ja) | 2018-02-26 | 2022-04-07 | ギリアード サイエンシーズ， インコーポレイテッド | Ｈｂｖ複製阻害剤としての置換ピロリジン化合物 |
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| US20190359645A1 (en) | 2018-05-03 | 2019-11-28 | Institute Of Organic Chemistry And Biochemistry Ascr, V.V.I. | 2'3'-cyclic dinucleotides comprising carbocyclic nucleotide |
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2017
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- 2017-04-03 EP EP17718218.5A patent/EP3440097B1/en active Active
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2018
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