IL226739A - Macrocyclic Inhibitors for Phlebiviridae Viruses - Google Patents
Macrocyclic Inhibitors for Phlebiviridae VirusesInfo
- Publication number
- IL226739A IL226739A IL226739A IL22673913A IL226739A IL 226739 A IL226739 A IL 226739A IL 226739 A IL226739 A IL 226739A IL 22673913 A IL22673913 A IL 22673913A IL 226739 A IL226739 A IL 226739A
- Authority
- IL
- Israel
- Prior art keywords
- optionally substituted
- alkyl
- compound
- mmol
- aryl
- Prior art date
Links
- 239000003112 inhibitor Substances 0.000 title claims description 64
- 241000710781 Flaviviridae Species 0.000 title description 12
- 150000001875 compounds Chemical class 0.000 claims description 220
- 125000000217 alkyl group Chemical group 0.000 claims description 209
- 239000000203 mixture Substances 0.000 claims description 103
- 125000000623 heterocyclic group Chemical group 0.000 claims description 93
- 125000003107 substituted aryl group Chemical group 0.000 claims description 82
- 125000002947 alkylene group Chemical group 0.000 claims description 70
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 62
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 61
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- 125000003118 aryl group Chemical group 0.000 claims description 33
- 150000003839 salts Chemical class 0.000 claims description 31
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 28
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 28
- 125000001424 substituent group Chemical group 0.000 claims description 23
- 239000002777 nucleoside Substances 0.000 claims description 21
- 150000003833 nucleoside derivatives Chemical class 0.000 claims description 21
- 229910052799 carbon Inorganic materials 0.000 claims description 20
- 239000003814 drug Substances 0.000 claims description 18
- 239000008194 pharmaceutical composition Substances 0.000 claims description 18
- IWUCXVSUMQZMFG-AFCXAGJDSA-N Ribavirin Chemical compound N1=C(C(=O)N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 IWUCXVSUMQZMFG-AFCXAGJDSA-N 0.000 claims description 15
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 15
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- 229910052717 sulfur Inorganic materials 0.000 claims description 13
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 11
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims description 11
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- 108010050904 Interferons Proteins 0.000 claims description 10
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- 229940124597 therapeutic agent Drugs 0.000 claims description 9
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- 239000002773 nucleotide Substances 0.000 claims description 8
- 125000003729 nucleotide group Chemical group 0.000 claims description 8
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- HZCAHMRRMINHDJ-DBRKOABJSA-N ribavirin Natural products O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1N=CN=C1 HZCAHMRRMINHDJ-DBRKOABJSA-N 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 125000000304 alkynyl group Chemical group 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
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- 125000006557 (C2-C5) alkylene group Chemical group 0.000 claims description 3
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- 238000006243 chemical reaction Methods 0.000 description 103
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 68
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 51
- 229910052757 nitrogen Inorganic materials 0.000 description 49
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- 238000009472 formulation Methods 0.000 description 36
- 239000002904 solvent Substances 0.000 description 36
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 35
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 31
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 28
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 27
- 238000000034 method Methods 0.000 description 27
- 229910052739 hydrogen Inorganic materials 0.000 description 25
- 238000005481 NMR spectroscopy Methods 0.000 description 24
- 210000004027 cell Anatomy 0.000 description 24
- 150000002148 esters Chemical class 0.000 description 24
- 239000003039 volatile agent Substances 0.000 description 22
- 239000012044 organic layer Substances 0.000 description 21
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 20
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 19
- 239000012298 atmosphere Substances 0.000 description 19
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- 239000000741 silica gel Substances 0.000 description 16
- 229910002027 silica gel Inorganic materials 0.000 description 16
- 239000011734 sodium Substances 0.000 description 16
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 15
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- 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 14
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Classifications
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- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
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- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
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- C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
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Landscapes
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| AR091279A1 (es) * | 2012-06-08 | 2015-01-21 | Gilead Sciences Inc | Inhibidores macrociclicos de virus flaviviridae |
| SI2859009T1 (sl) * | 2012-06-08 | 2017-12-29 | Gilead Sciences, Inc. | Makrociklični inhibitorji flaviviridae virusov |
| US9440991B2 (en) * | 2013-12-23 | 2016-09-13 | Gilead Sciences, Inc. | Synthesis of an antiviral compound |
| AU2015318061B2 (en) | 2014-09-16 | 2018-05-17 | Gilead Sciences, Inc. | Solid forms of a toll-like receptor modulator |
| CN118286245A (zh) | 2014-12-26 | 2024-07-05 | 埃莫里大学 | N4-羟基胞苷和衍生物及与其相关的抗病毒用途 |
| KR102394917B1 (ko) | 2015-03-04 | 2022-05-09 | 길리애드 사이언시즈, 인코포레이티드 | 톨 유사 수용체 조정제 화합물 |
| JP2018525412A (ja) | 2015-08-26 | 2018-09-06 | ギリアード サイエンシーズ， インコーポレイテッド | 重水素化トール様受容体調節因子 |
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| CN109790143A (zh) | 2016-05-10 | 2019-05-21 | C4医药公司 | 用于靶蛋白降解的胺连接的c3-戊二酰亚胺降解决定子体 |
| BR102017010009A2 (pt) | 2016-05-27 | 2017-12-12 | Gilead Sciences, Inc. | Compounds for the treatment of hepatitis b virus infection |
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| US6124453A (en) | 1995-07-04 | 2000-09-26 | Novartis Ag | Macrolides |
| AR006514A1 (es) | 1995-07-04 | 1999-09-08 | Sandoz Ag | Un macrolido, sus usos, un proceso para producirlo, un aislado biologicamente puro capaz de producirlo, y una composicion farmaceutica quelo comprende |
| EP1893211B1 (en) * | 2005-06-17 | 2011-09-14 | Novartis AG | Use of sanglifehrin in hcv |
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