JP2019530669A5 - - Google Patents
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- JP2019530669A5 JP2019530669A5 JP2019513067A JP2019513067A JP2019530669A5 JP 2019530669 A5 JP2019530669 A5 JP 2019530669A5 JP 2019513067 A JP2019513067 A JP 2019513067A JP 2019513067 A JP2019513067 A JP 2019513067A JP 2019530669 A5 JP2019530669 A5 JP 2019530669A5
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- JP
- Japan
- Prior art keywords
- alkyl
- compound according
- pharmaceutically acceptable
- item
- acceptable salt
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 125000000217 alkyl group Chemical group 0.000 claims description 538
- 150000001875 compounds Chemical class 0.000 claims description 161
- 125000005843 halogen group Chemical group 0.000 claims description 114
- 125000001153 fluoro group Chemical group F* 0.000 claims description 84
- 125000001424 substituent group Chemical group 0.000 claims description 75
- -1 Z is NR 19 Inorganic materials 0.000 claims description 58
- 125000000623 heterocyclic group Chemical group 0.000 claims description 56
- 125000003545 alkoxy group Chemical group 0.000 claims description 55
- 125000001072 heteroaryl group Chemical group 0.000 claims description 55
- 150000003839 salts Chemical class 0.000 claims description 34
- 125000003118 aryl group Chemical group 0.000 claims description 32
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 31
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims description 27
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 26
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 21
- 229910052760 oxygen Inorganic materials 0.000 claims description 20
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 18
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 17
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 15
- 229910052799 carbon Inorganic materials 0.000 claims description 14
- 125000001010 sulfinic acid amide group Chemical group 0.000 claims description 14
- 125000003342 alkenyl group Chemical group 0.000 claims description 13
- 125000000304 alkynyl group Chemical group 0.000 claims description 13
- 150000001540 azides Chemical class 0.000 claims description 13
- 229910052717 sulfur Inorganic materials 0.000 claims description 13
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 206010028980 Neoplasm Diseases 0.000 claims description 11
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 10
- 229940124530 sulfonamide Drugs 0.000 claims description 10
- 150000003456 sulfonamides Chemical class 0.000 claims description 10
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 8
- 125000006620 amino-(C1-C6) alkyl group Chemical group 0.000 claims description 8
- 208000035475 disorder Diseases 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- XCLXUGNKBSKVQE-UHFFFAOYSA-N (1z)-1-hydrazinylideneguanidine Chemical compound NN=NC(N)=N XCLXUGNKBSKVQE-UHFFFAOYSA-N 0.000 claims description 7
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 7
- 229910019142 PO4 Inorganic materials 0.000 claims description 7
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 7
- 125000004414 alkyl thio group Chemical group 0.000 claims description 7
- 201000011510 cancer Diseases 0.000 claims description 7
- 239000004202 carbamide Substances 0.000 claims description 7
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 7
- 239000010452 phosphate Substances 0.000 claims description 7
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims description 7
- LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 claims description 7
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 7
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 7
- 125000005309 thioalkoxy group Chemical group 0.000 claims description 7
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 7
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 6
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 5
- 206010009944 Colon cancer Diseases 0.000 claims description 5
- 125000004423 acyloxy group Chemical group 0.000 claims description 5
- 150000001408 amides Chemical class 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 208000029742 colonic neoplasm Diseases 0.000 claims description 5
- 125000001188 haloalkyl group Chemical group 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- PIGFYZPCRLYGLF-UHFFFAOYSA-N Aluminum nitride Chemical compound [Al]#N PIGFYZPCRLYGLF-UHFFFAOYSA-N 0.000 claims description 4
- 206010006187 Breast cancer Diseases 0.000 claims description 4
- 208000026310 Breast neoplasm Diseases 0.000 claims description 4
- 125000005041 acyloxyalkyl group Chemical group 0.000 claims description 4
- KWEDUNSJJZVRKR-UHFFFAOYSA-N carbononitridic azide Chemical compound [N-]=[N+]=NC#N KWEDUNSJJZVRKR-UHFFFAOYSA-N 0.000 claims description 4
- 238000010276 construction Methods 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 4
- 125000002950 monocyclic group Chemical group 0.000 claims description 4
- ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical compound [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 claims description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
- 208000003174 Brain Neoplasms Diseases 0.000 claims description 3
- 201000008808 Fibrosarcoma Diseases 0.000 claims description 3
- 206010016654 Fibrosis Diseases 0.000 claims description 3
- 208000008839 Kidney Neoplasms Diseases 0.000 claims description 3
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 3
- 206010033128 Ovarian cancer Diseases 0.000 claims description 3
- 206010061535 Ovarian neoplasm Diseases 0.000 claims description 3
- 208000018737 Parkinson disease Diseases 0.000 claims description 3
- 206010060862 Prostate cancer Diseases 0.000 claims description 3
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 3
- 206010038389 Renal cancer Diseases 0.000 claims description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 3
- 125000004104 aryloxy group Chemical group 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- 210000004556 brain Anatomy 0.000 claims description 3
- 208000015114 central nervous system disease Diseases 0.000 claims description 3
- 230000004761 fibrosis Effects 0.000 claims description 3
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 3
- 208000026278 immune system disease Diseases 0.000 claims description 3
- 208000027866 inflammatory disease Diseases 0.000 claims description 3
- 230000002757 inflammatory effect Effects 0.000 claims description 3
- 201000010982 kidney cancer Diseases 0.000 claims description 3
- 201000005202 lung cancer Diseases 0.000 claims description 3
- 208000020816 lung neoplasm Diseases 0.000 claims description 3
- 201000001441 melanoma Diseases 0.000 claims description 3
- 210000000653 nervous system Anatomy 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 208000019116 sleep disease Diseases 0.000 claims description 3
- 102100022464 5'-nucleotidase Human genes 0.000 claims description 2
- 208000003200 Adenoma Diseases 0.000 claims description 2
- 206010005003 Bladder cancer Diseases 0.000 claims description 2
- 206010005949 Bone cancer Diseases 0.000 claims description 2
- 208000018084 Bone neoplasm Diseases 0.000 claims description 2
- 206010008342 Cervix carcinoma Diseases 0.000 claims description 2
- 208000000461 Esophageal Neoplasms Diseases 0.000 claims description 2
- 208000017228 Gastrointestinal motility disease Diseases 0.000 claims description 2
- 101000678236 Homo sapiens 5'-nucleotidase Proteins 0.000 claims description 2
- 206010025323 Lymphomas Diseases 0.000 claims description 2
- 206010030155 Oesophageal carcinoma Diseases 0.000 claims description 2
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 2
- 208000002471 Penile Neoplasms Diseases 0.000 claims description 2
- 206010034299 Penile cancer Diseases 0.000 claims description 2
- 206010035226 Plasma cell myeloma Diseases 0.000 claims description 2
- 206010039491 Sarcoma Diseases 0.000 claims description 2
- 208000005718 Stomach Neoplasms Diseases 0.000 claims description 2
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims description 2
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 claims description 2
- 208000009956 adenocarcinoma Diseases 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 230000001413 cellular effect Effects 0.000 claims description 2
- 201000010881 cervical cancer Diseases 0.000 claims description 2
- 230000029087 digestion Effects 0.000 claims description 2
- 201000010099 disease Diseases 0.000 claims description 2
- 201000004101 esophageal cancer Diseases 0.000 claims description 2
- 206010017758 gastric cancer Diseases 0.000 claims description 2
- 201000010536 head and neck cancer Diseases 0.000 claims description 2
- 208000014829 head and neck neoplasm Diseases 0.000 claims description 2
- 201000010235 heart cancer Diseases 0.000 claims description 2
- 208000024348 heart neoplasm Diseases 0.000 claims description 2
- 230000002401 inhibitory effect Effects 0.000 claims description 2
- 208000023589 ischemic disease Diseases 0.000 claims description 2
- 208000032839 leukemia Diseases 0.000 claims description 2
- 201000007270 liver cancer Diseases 0.000 claims description 2
- 208000014018 liver neoplasm Diseases 0.000 claims description 2
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims description 2
- 210000001161 mammalian embryo Anatomy 0.000 claims description 2
- 125000005358 mercaptoalkyl group Chemical group 0.000 claims description 2
- 201000000050 myeloid neoplasm Diseases 0.000 claims description 2
- 210000000056 organ Anatomy 0.000 claims description 2
- 201000002528 pancreatic cancer Diseases 0.000 claims description 2
- 208000008443 pancreatic carcinoma Diseases 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 201000011549 stomach cancer Diseases 0.000 claims description 2
- 125000004963 sulfonylalkyl group Chemical group 0.000 claims description 2
- 230000002381 testicular Effects 0.000 claims description 2
- 210000000115 thoracic cavity Anatomy 0.000 claims description 2
- 230000002992 thymic effect Effects 0.000 claims description 2
- 201000005112 urinary bladder cancer Diseases 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 8
- 239000000203 mixture Substances 0.000 claims 3
- 230000004770 neurodegeneration Effects 0.000 claims 2
- 208000016285 Movement disease Diseases 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 210000000936 intestine Anatomy 0.000 claims 1
- 230000000302 ischemic effect Effects 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 74
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 38
- 239000001257 hydrogen Substances 0.000 description 24
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 18
- 125000005842 heteroatom Chemical group 0.000 description 18
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 18
- 125000004452 carbocyclyl group Chemical group 0.000 description 17
- 125000003831 tetrazolyl group Chemical group 0.000 description 16
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 description 10
- 125000003107 substituted aryl group Chemical group 0.000 description 8
- 150000001721 carbon Chemical group 0.000 description 7
- 125000002947 alkylene group Chemical group 0.000 description 6
- 150000002431 hydrogen Chemical class 0.000 description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 6
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 6
- 239000002246 antineoplastic agent Substances 0.000 description 5
- 229940127089 cytotoxic agent Drugs 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 4
- 125000001624 naphthyl group Chemical group 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- NWIBSHFKIJFRCO-WUDYKRTCSA-N Mytomycin Chemical compound C1N2C(C(C(C)=C(N)C3=O)=O)=C3[C@@H](COC(N)=O)[C@@]2(OC)[C@@H]2[C@H]1N2 NWIBSHFKIJFRCO-WUDYKRTCSA-N 0.000 description 3
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 3
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- 125000002541 furyl group Chemical group 0.000 description 3
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- ZHQRPIRGSWEALJ-UHFFFAOYSA-N 1-amino-4-(1-naphthalenylamino)-9,10-dioxo-2-anthracenesulfonic acid Chemical compound C1=CC=C2C(NC3=C4C(=O)C5=CC=CC=C5C(=O)C4=C(C(=C3)S(O)(=O)=O)N)=CC=CC2=C1 ZHQRPIRGSWEALJ-UHFFFAOYSA-N 0.000 description 2
- ZCQMYMXRGJWSHH-UHFFFAOYSA-N 1-amino-4-(4-aminoanilino)-9,10-dioxoanthracene-2-sulfonic acid Chemical compound C1=CC(N)=CC=C1NC1=CC(S(O)(=O)=O)=C(N)C2=C1C(=O)C1=CC=CC=C1C2=O ZCQMYMXRGJWSHH-UHFFFAOYSA-N 0.000 description 2
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- PTOAARAWEBMLNO-KVQBGUIXSA-N Cladribine Chemical compound C1=NC=2C(N)=NC(Cl)=NC=2N1[C@H]1C[C@H](O)[C@@H](CO)O1 PTOAARAWEBMLNO-KVQBGUIXSA-N 0.000 description 2
- 239000005411 L01XE02 - Gefitinib Substances 0.000 description 2
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- RJURFGZVJUQBHK-UHFFFAOYSA-N actinomycin D Natural products CC1OC(=O)C(C(C)C)N(C)C(=O)CN(C)C(=O)C2CCCN2C(=O)C(C(C)C)NC(=O)C1NC(=O)C1=C(N)C(=O)C(C)=C2OC(C(C)=CC=C3C(=O)NC4C(=O)NC(C(N5CCCC5C(=O)N(C)CC(=O)N(C)C(C(C)C)C(=O)OC4C)=O)C(C)C)=C3N=C21 RJURFGZVJUQBHK-UHFFFAOYSA-N 0.000 description 2
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- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 2
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- VSNHCAURESNICA-NJFSPNSNSA-N 1-oxidanylurea Chemical compound N[14C](=O)NO VSNHCAURESNICA-NJFSPNSNSA-N 0.000 description 1
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| IL304348B2 (en) | 2018-04-30 | 2024-08-01 | Oric Pharmaceuticals Inc | CD73 inhibitors |
| WO2019232319A1 (en) | 2018-05-31 | 2019-12-05 | Peloton Therapeutics, Inc. | Compositions and methods for inhibiting cd73 |
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| CN112638389A (zh) * | 2018-08-28 | 2021-04-09 | 江苏恒瑞医药股份有限公司 | Cd73抑制剂及其治疗用途 |
| MX2021002878A (es) | 2018-09-11 | 2021-08-16 | Risen Suzhou Pharma Tech Co Ltd | Inhibidores de cd73 y usos farmaceuticos de los mismos. |
| US11530234B2 (en) | 2018-09-11 | 2022-12-20 | Risen (Suzhou) Pharma Tech Co., Ltd. | CD73 inhibitors and pharmaceutical uses thereof |
| CN113164773B (zh) * | 2018-10-17 | 2025-03-21 | 廖细斌 | 6-巯基嘌呤核苷类似物 |
| WO2020190073A1 (ko) * | 2019-03-20 | 2020-09-24 | 한국화학연구원 | 신규한 아졸로피리미딘 헤테로고리 화합물을 유효 성분으로 함유하는 약제학적 조성물 |
| WO2020205538A1 (en) * | 2019-03-29 | 2020-10-08 | Eternity Bioscience Inc. | Cd73 inhibitors and therapeutic uses thereof |
| WO2020210938A1 (en) * | 2019-04-15 | 2020-10-22 | Bioardis Llc | Quinazoline derivatives as cd73 inhibitors |
| WO2020257429A1 (en) * | 2019-06-20 | 2020-12-24 | Calithera Biosciences, Inc. | Ectonucleotidase inhibitors and methods of use thereof |
| JP7557522B2 (ja) | 2019-07-16 | 2024-09-27 | オリック ファーマシューティカルズ，インク． | Ｃｄ７３阻害剤 |
| PL4051688T3 (pl) * | 2019-10-30 | 2025-09-22 | Oric Pharmaceuticals, Inc. | Inhibitory cd73 |
| AU2021341258A1 (en) * | 2020-09-08 | 2023-04-13 | Betta Pharmaceuticals Co., Ltd. | CD73 inhibitor and application thereof in medicine |
| CN114099698B (zh) * | 2021-11-26 | 2024-02-09 | 山东大学齐鲁医院 | 一种pH敏感脂质体及其制备方法与应用 |
| JP2025512384A (ja) | 2022-04-13 | 2025-04-17 | ギリアード サイエンシーズ， インコーポレイテッド | Ｔｒｏｐ－２発現がんを治療するための併用療法 |
| CN117430651B (zh) * | 2022-07-21 | 2026-03-10 | 武汉精准智药科技有限公司 | 单磷酸核苷类化合物及其制备方法 |
| CN115611954A (zh) * | 2022-12-19 | 2023-01-17 | 天津奥瑞芙生物医药有限公司 | 一种5′-o-(4,4′-二甲氧基三苯甲基)-核苷的制备方法 |
| WO2025137640A1 (en) | 2023-12-22 | 2025-06-26 | Gilead Sciences, Inc. | Azaspiro wrn inhibitors |
| WO2025162964A1 (en) | 2024-01-30 | 2025-08-07 | Institut National de la Santé et de la Recherche Médicale | Methods for the treatment of endometriosis |
Family Cites Families (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4172896A (en) | 1978-06-05 | 1979-10-30 | Dainippon Pharmaceutical Co., Ltd. | Methane-sulfonamide derivatives, the preparation thereof and composition comprising the same |
| KR960008669B1 (ko) | 1991-04-24 | 1996-06-28 | 야마사 쇼오유 가부시끼가이샤 | 1-β-D-아라비노푸라노실-(E)-5-(2-할로게노비닐) 우라실 유도체 |
| US5208327A (en) | 1991-12-18 | 1993-05-04 | Ortho Pharmaceutical Corporation | Intermediates useful in a synthesis of 2-chloro-2'-deoxyadenosine |
| GB9217295D0 (en) | 1992-08-14 | 1992-09-30 | Wellcome Found | Controlled released tablets |
| AU5449094A (en) | 1992-11-02 | 1994-05-24 | Affymax Technologies N.V. | Novel photoreactive protecting groups |
| US5358970A (en) | 1993-08-12 | 1994-10-25 | Burroughs Wellcome Co. | Pharmaceutical composition containing bupropion hydrochloride and a stabilizer |
| US5541231A (en) | 1993-07-30 | 1996-07-30 | Glaxo Wellcome Inc. | Stabilized Pharmaceutical |
| GB9315856D0 (en) | 1993-07-30 | 1993-09-15 | Wellcome Found | Stabilized pharmaceutical |
| US5635608A (en) | 1994-11-08 | 1997-06-03 | Molecular Probes, Inc. | α-carboxy caged compounds |
| TW528755B (en) | 1996-12-24 | 2003-04-21 | Glaxo Group Ltd | 2-(purin-9-yl)-tetrahydrofuran-3,4-diol derivatives |
| NL1005244C2 (nl) | 1997-02-10 | 1998-08-18 | Inst Voor Agrotech Onderzoek | Oppervlakte-actieve aminen en glycosiden. |
| DE69839355T2 (de) | 1997-07-29 | 2009-06-04 | Alcon Laboratories, Inc., Fort Worth | Ophthalmische Zusammensetzungen enthaltend Galaktomannanpolymere und Borat |
| AU2483599A (en) | 1998-01-29 | 1999-08-16 | Sepracor, Inc. | Pharmaceutical uses of optically pure (-)-bupropion |
| US8889112B2 (en) | 1999-09-16 | 2014-11-18 | Ocularis Pharma, Llc | Ophthalmic formulations including selective alpha 1 antagonists |
| WO2004000858A2 (en) | 2002-06-21 | 2003-12-31 | Merck & Co., Inc. | Nucleoside derivatives as inhibitors of rna-dependent rna viral polymerase |
| WO2004096233A2 (en) * | 2003-04-25 | 2004-11-11 | Gilead Sciences, Inc. | Nucleoside phosphonate conjugates |
| US6933289B2 (en) | 2003-07-01 | 2005-08-23 | Allergan, Inc. | Inhibition of irritating side effects associated with use of a topical ophthalmic medication |
| EP1654002B2 (en) | 2003-08-07 | 2014-01-29 | Allergan, Inc. | Compositions for delivery of therapeutics into the eyes |
| US20050059744A1 (en) | 2003-09-12 | 2005-03-17 | Allergan, Inc. | Methods and compositions for the treatment of pain and other alpha 2 adrenergic-mediated conditions |
| EP1860113A1 (en) | 2006-05-24 | 2007-11-28 | Rheinische Friedrich-Wilhelms-Universität Bonn | Ectonucleotidase inhibitors |
| WO2008011406A2 (en) | 2006-07-18 | 2008-01-24 | Anadys Pharmaceuticals, Inc. | Carbonate and carbamate prodrugs of thiazolo [4,5-d] pyrimidines |
| JP2011503084A (ja) | 2007-11-07 | 2011-01-27 | シェーリング コーポレイション | 新規の細胞周期チェックポイント調節剤およびこれらの調節剤とチェックポイント阻害剤との併用 |
| EP2070938A1 (en) | 2007-12-13 | 2009-06-17 | Heidelberg Pharma AG | Clofarabine dietherphospholipid derivatives |
| WO2011133871A2 (en) | 2010-04-22 | 2011-10-27 | Alnylam Pharmaceuticals, Inc. | 5'-end derivatives |
| WO2012006351A1 (en) | 2010-07-08 | 2012-01-12 | Life Technologies Corporation | In situ chemiluminescent substrates and assays |
| JP2014516947A (ja) | 2011-05-03 | 2014-07-17 | ライフ テクノロジーズ コーポレーション | フラッシュ・グロー型の１，２−ジオキセタン |
| US8883800B2 (en) | 2011-07-15 | 2014-11-11 | Boehringer Ingelheim International Gmbh | Substituted quinazolines, the preparation thereof and the use thereof in pharmaceutical compositions |
| SG10201913554YA (en) | 2011-12-22 | 2020-03-30 | Alios Biopharma Inc | Substituted nucleosides, nucleotides and analogs thereof |
| GB201220843D0 (en) | 2012-11-20 | 2013-01-02 | Univ College Cork Nat Univ Ie | Compound |
| MA39986A (fr) | 2014-04-25 | 2017-03-01 | Vitae Pharmaceuticals Inc | Dérivés de purine en tant qu'inhibiteurs de cd73 pour le traitement du cancer |
| HUE051986T2 (hu) | 2014-06-24 | 2021-04-28 | Janssen Biopharma Inc | Helyettesített nukleozidok, nukleotidek és analógjaik virális fertõzés kezelésére való alkalmazásra |
| AU2016301188A1 (en) | 2015-08-06 | 2018-02-15 | Chimerix, Inc. | Pyrrolopyrimidine nucleosides and analogs thereof useful as antiviral agents |
| SI3362461T1 (sl) | 2015-10-16 | 2022-05-31 | Modernatx, Inc. | Analogi kape MRNA z modificirano fosfatno povezavo |
| WO2017066782A1 (en) | 2015-10-16 | 2017-04-20 | Modernatx, Inc. | Hydrophobic mrna cap analogs |
| WO2017066791A1 (en) | 2015-10-16 | 2017-04-20 | Modernatx, Inc. | Sugar substituted mrna cap analogs |
| US10611790B2 (en) | 2015-11-02 | 2020-04-07 | Mitobridge, Inc. | Nicotinamide riboside and nicotinamide mononucleotide derivatives for use in the treatments of mitochondrial-related diseases |
| WO2017120508A1 (en) | 2016-01-08 | 2017-07-13 | Arcus Biosciences, Inc. | Modulators of 5'-nucleotidase, ecto and the use thereof |
| EP3510040A4 (en) * | 2016-09-09 | 2020-06-03 | Calithera Biosciences, Inc. | EKTONUCLEOTIDASE INHIBITORS AND METHOD FOR USE THEREOF |
| KR102638592B1 (ko) | 2016-12-22 | 2024-02-19 | 안텐진 테라퓨틱스 리미티드 | 엑토뉴클레오티다제 억제제 및 이의 용도 |
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- 2017-09-08 TW TW106130807A patent/TWI767937B/zh active
- 2017-09-08 US US15/699,109 patent/US10472364B2/en active Active
- 2017-09-08 JP JP2019513067A patent/JP7125144B2/ja active Active
- 2017-09-08 WO PCT/US2017/050659 patent/WO2018049145A1/en not_active Ceased
- 2017-09-08 CN CN201780068695.9A patent/CN110234656B/zh active Active
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2019
- 2019-09-27 US US16/585,195 patent/US11208414B2/en active Active
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