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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| WO2020190073A1 (ko) * | 2019-03-20 | 2020-09-24 | 한국화학연구원 | 신규한 아졸로피리미딘 헤테로고리 화합물을 유효 성분으로 함유하는 약제학적 조성물 |
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| EP4212524A4 (en) * | 2020-09-08 | 2024-08-28 | Betta Pharmaceuticals Co., Ltd | Cd73 inhibitor and application thereof in medicine |
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| CA3256033A1 (en) | 2022-04-13 | 2023-10-19 | Arcus Biosciences, Inc. | POLYTHERAPY FOR THE TREATMENT OF CANCERS EXPRESSING TOO MUCH-2 |
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| US20250230168A1 (en) | 2023-12-22 | 2025-07-17 | Gilead Sciences, Inc. | Azaspiro wrn inhibitors |
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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 |
| WO1992019638A1 (en) | 1991-04-24 | 1992-11-12 | Yamasa Shoyu Kabushiki Kaisha | 1-β-D-ARABINOFURANOSYL-(E)-5-(2-HALOGENOVINYL)-URACIL DERIVATIVE |
| US5208327A (en) | 1991-12-18 | 1993-05-04 | Ortho Pharmaceutical Corporation | Intermediates useful in a synthesis of 2-chloro-2'-deoxyadenosine |
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| WO1994010128A1 (en) | 1992-11-02 | 1994-05-11 | Affymax Technologies N.V. | Novel photoreactive protecting groups |
| US5541231A (en) | 1993-07-30 | 1996-07-30 | Glaxo Wellcome Inc. | Stabilized Pharmaceutical |
| US5358970A (en) | 1993-08-12 | 1994-10-25 | Burroughs Wellcome Co. | Pharmaceutical composition containing bupropion hydrochloride and a stabilizer |
| 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. |
| ATE250923T1 (de) | 1997-07-29 | 2003-10-15 | Alcon Lab Inc | Galaktomannanpolymere und borat enthaltende augenarzneimittel |
| EP1051167A1 (en) | 1998-01-29 | 2000-11-15 | 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 |
| US20070004669A1 (en) | 2002-06-21 | 2007-01-04 | Carroll Steven S | 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 |
| CA2534484A1 (en) | 2003-08-07 | 2005-02-17 | Allergan, Inc. | Compositions for delivery of therapeutics into the eyes and methods for making and using same |
| 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 |
| DE602007012881D1 (en) | 2006-07-18 | 2011-04-14 | Anadys Pharmaceuticals Inc | Carbonat- und carbamat-prodrugs von thiazolo ä4,5-dü-pyrimidinen |
| CN101903396A (zh) | 2007-11-07 | 2010-12-01 | 先灵公司 | 新的细胞周期关卡调节剂和它们与关卡激酶抑制剂的联合应用 |
| EP2070938A1 (en) | 2007-12-13 | 2009-06-17 | Heidelberg Pharma AG | Clofarabine dietherphospholipid derivatives |
| US9725479B2 (en) | 2010-04-22 | 2017-08-08 | Ionis Pharmaceuticals, Inc. | 5′-end derivatives |
| US10031142B2 (en) | 2010-07-08 | 2018-07-24 | Life Technologies Corporation | In situ chemiluminescent substrates and assays |
| KR101960113B1 (ko) | 2011-05-03 | 2019-03-19 | 라이프 테크놀로지스 코포레이션 | 섬광 및 백열광 １,２-디옥세탄들 |
| CA2841552C (en) | 2011-07-15 | 2020-06-23 | Boehringer Ingelheim International Gmbh | Substituted quinazolines, the preparation thereof and the use thereof in pharmaceutical compositions |
| PL2794627T3 (pl) | 2011-12-22 | 2019-04-30 | Alios Biopharma Inc | Podstawione nukleozydy, nukleotydy i ich analogi |
| GB201220843D0 (en) | 2012-11-20 | 2013-01-02 | Univ College Cork Nat Univ Ie | Compound |
| JP6657182B2 (ja) * | 2014-04-25 | 2020-03-04 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | 癌治療用のｃｄ７３阻害剤としてのプリン誘導体 |
| AU2015280248B2 (en) | 2014-06-24 | 2021-04-08 | Alios Biopharma, Inc. | Substituted nucleosides, nucleotides and analogs thereof |
| EP3331895B1 (en) * | 2015-08-06 | 2020-07-29 | Chimerix, Inc. | Pyrrolopyrimidine nucleosides and analogs thereof useful as antiviral agents |
| EP4086269A1 (en) | 2015-10-16 | 2022-11-09 | ModernaTX, Inc. | Mrna cap analogs with modified phosphate linkage |
| WO2017066791A1 (en) | 2015-10-16 | 2017-04-20 | Modernatx, Inc. | Sugar substituted mrna cap analogs |
| WO2017066782A1 (en) | 2015-10-16 | 2017-04-20 | Modernatx, Inc. | Hydrophobic mrna cap analogs |
| WO2017079195A1 (en) | 2015-11-02 | 2017-05-11 | Mitobridge, Inc. | Nicotinamide riboside and nicotinamide mononucleotide derivatives for use in the treatments of mitochondrial-related diseases |
| TWI744274B (zh) | 2016-01-08 | 2021-11-01 | 美商阿克思生物科學有限公司 | 胞外5'–核苷酸酶之調節劑及其用途 |
| EP3510040A4 (en) * | 2016-09-09 | 2020-06-03 | Calithera Biosciences, Inc. | EKTONUCLEOTIDASE INHIBITORS AND METHOD FOR USE THEREOF |
| EP3558998A4 (en) * | 2016-12-22 | 2020-06-10 | Calithera Biosciences, Inc. | ECTONUCLEOTIDASE INHIBITORS AND METHODS OF USE |
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2019
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