AR088109A1 - Metodo para preparar analogos nucleotidicos antivirales - Google Patents
Metodo para preparar analogos nucleotidicos antiviralesInfo
- Publication number
- AR088109A1 AR088109A1 ARP120103681A AR088109A1 AR 088109 A1 AR088109 A1 AR 088109A1 AR P120103681 A ARP120103681 A AR P120103681A AR 088109 A1 AR088109 A1 AR 088109A1
- Authority
- AR
- Argentina
- Prior art keywords
- formula
- compound
- diastereomerically pure
- phenoxyphosphinyl
- isopropoxycarbonyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 6
- 230000000840 anti-viral effect Effects 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 9
- 125000001475 halogen functional group Chemical group 0.000 abstract 2
- -1 9 - {(R) -2 - [((S) - {[(S) -1- (isopropoxycarbonyl) ethyl] amino} -phenoxyphosphinyl) methoxy] propyl} adenine compound Chemical class 0.000 abstract 1
- 229930024421 Adenine Natural products 0.000 abstract 1
- 229960000643 adenine Drugs 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 230000002140 halogenating effect Effects 0.000 abstract 1
- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 238000010956 selective crystallization Methods 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- LDEKQSIMHVQZJK-CAQYMETFSA-N tenofovir alafenamide Chemical compound O([P@@](=O)(CO[C@H](C)CN1C2=NC=NC(N)=C2N=C1)N[C@@H](C)C(=O)OC(C)C)C1=CC=CC=C1 LDEKQSIMHVQZJK-CAQYMETFSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
- C07F9/65616—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings containing the ring system having three or more than three double bonds between ring members or between ring members and non-ring members, e.g. purine or analogs
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
- C07F9/6509—Six-membered rings
- C07F9/6512—Six-membered rings having the nitrogen atoms in positions 1 and 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
- C07F9/65583—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system each of the hetero rings containing nitrogen as ring hetero atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Virology (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Métodos para aislar 9-{(R)-2-[((S)-{[(S)-1-(isopropoxicarbonil)etil]amino}-fenoxifosfinil)metoxi]propil}adenina compuesto de fórmula (1) y métodos para preparar compuestos relacionados, tiene propiedades antivirales. Reivindicación 1: Un método que comprende someter una solución que comprende: a) un solvente adecuado; b) una base adecuada; y c) 9-{(R)-2-[((R,S)-[(S)-1-(isopropoxicarbonil)etil]amino}fenoxifosfinil)metoxi]propil}adenina, a condiciones que proporcionan la cristalización selectiva de 9-{(R)-2-[((S)-{[(S)-1-(isopropoxicarbonil)etil]amino}fenxifosfinil)metoxi]propil}adenina. Reivindicación 9: Un método para preparar el compuesto de fórmula (2), donde X es halo, que es por lo menos aproximadamente 90% diastereoméricamente puro, que comprende tratar el compuesto de fórmula (3) con un agente halogenante adecuado bajo condiciones que proporcionan el compuesto de fórmula (2) que es por lo menos aproximadamente 90% diastereoméricamente puro. Reivindicación 14: Un método para preparar el compuesto de fórmula (4) que es el compuesto de fórmula (1) por lo menos aproximadamente 90% diastereoméricamente puro que comprende tratar el compuesto de fórmula (2) donde X es halo, que es por lo menos aproximadamente 90% diastereoméricamente puro, con la amina de fórmula (5) bajo condiciones que proporcionan el compuesto de fórmula (4) que es el compuesto de fórmula (1) por lo menos aproximadamente 90% diastereoméricamente puro.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161544950P | 2011-10-07 | 2011-10-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR088109A1 true AR088109A1 (es) | 2014-05-07 |
Family
ID=47297386
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP120103681 AR088109A1 (es) | 2011-10-07 | 2012-10-03 | Metodo para preparar analogos nucleotidicos antivirales |
Country Status (25)
| Country | Link |
|---|---|
| US (4) | US8664386B2 (es) |
| EP (2) | EP3333173B1 (es) |
| JP (2) | JP6190372B2 (es) |
| KR (3) | KR102033802B1 (es) |
| CN (4) | CN113264959A (es) |
| AR (1) | AR088109A1 (es) |
| AU (1) | AU2012319172B2 (es) |
| BR (1) | BR112014011340A2 (es) |
| CA (2) | CA2850466C (es) |
| CL (1) | CL2014000827A1 (es) |
| CO (1) | CO6940431A2 (es) |
| CR (1) | CR20140204A (es) |
| EA (1) | EA027086B1 (es) |
| EC (1) | ECSP14000074A (es) |
| ES (2) | ES2661705T3 (es) |
| HK (3) | HK1255222B (es) |
| IL (1) | IL231879B (es) |
| MX (1) | MX353064B (es) |
| PE (1) | PE20141160A1 (es) |
| PL (1) | PL3333173T3 (es) |
| PT (2) | PT2764002T (es) |
| SI (1) | SI3333173T1 (es) |
| TW (4) | TWI709567B (es) |
| UY (1) | UY34361A (es) |
| WO (1) | WO2013052094A2 (es) |
Families Citing this family (50)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PE20141328A1 (es) | 2011-08-16 | 2014-10-04 | Gilead Sciences Inc | Tenofovir alafenamida hemifumarato |
| SI3333173T1 (sl) | 2011-10-07 | 2019-08-30 | Gilead Sciences, Inc. | Postopki za pripravo analogov protivirusnega nukleotida |
| CN103665043B (zh) | 2012-08-30 | 2017-11-10 | 江苏豪森药业集团有限公司 | 一种替诺福韦前药及其在医药上的应用 |
| EP3004121A1 (en) | 2013-06-07 | 2016-04-13 | Cipla Limited | An efficient process for separation of diastereomers of 9-[(r)-2-[[(r,s)-[[(s)-1-(isopropoxycarbonyl)ethyl]amino]-phenoxyphosphinyl]methoxy]propyl]adenine |
| CN104628773B (zh) * | 2013-11-06 | 2018-10-23 | 杭州和泽医药科技有限公司 | (r)-9-[2-(磷酰苯酚基甲氧基)丙基]腺嘌呤的制备方法 |
| WO2015079455A2 (en) * | 2013-11-27 | 2015-06-04 | Laurus Labs Private Limited | A recycling process for preparing tenofovir alafenamide diastereomers |
| ES2842123T3 (es) * | 2014-01-14 | 2021-07-12 | Mylan Laboratories Ltd | Purificación de tenofovir alafenamida y sus intermedios |
| TWI660965B (zh) | 2014-01-15 | 2019-06-01 | 美商基利科學股份有限公司 | 泰諾福韋之固體形式 |
| WO2015161781A1 (zh) * | 2014-04-21 | 2015-10-29 | 四川海思科制药有限公司 | 一种核苷类似物及其中间体的制备方法 |
| CN105518012B (zh) * | 2014-06-25 | 2018-03-02 | 四川海思科制药有限公司 | 一种取代的氨基酸硫酯类化合物、其组合物及应用 |
| CN105399771B (zh) * | 2014-07-21 | 2020-11-24 | 江苏豪森药业集团有限公司 | 替诺福韦前药晶型及其制备方法和用途 |
| CN105646584B (zh) * | 2014-11-12 | 2018-09-28 | 四川海思科制药有限公司 | 替诺福韦艾拉酚胺富马酸盐晶型及其制备方法和用途 |
| CN104817593B (zh) * | 2015-04-27 | 2016-11-16 | 广州同隽医药科技有限公司 | 半富马酸替诺福韦艾拉酚胺关键中间体的合成工艺 |
| MD3331891T2 (ro) | 2015-08-05 | 2022-04-30 | Eisai R&D Man Co Ltd | Procedeu de obţinere a unui oligomer de fosforodiamidat substanțial diastereomeric pur, a unui oligomer de fosforodiamidat obţinut printr-un astfel de procedeu și a unei compoziții farmaceutice care conţine un astfel de oligomer de fosforodiamidat |
| TWI616452B (zh) * | 2015-08-26 | 2018-03-01 | Preparation method of nucleoside analog and intermediate thereof | |
| CN105330700A (zh) * | 2015-12-17 | 2016-02-17 | 中国药科大学 | 富马酸替诺福韦艾拉酚胺杂质的制备方法 |
| WO2017118928A1 (en) | 2016-01-06 | 2017-07-13 | Lupin Limited | Process for the separation of diastereomers of tenofovir alafenamide |
| CZ2016156A3 (cs) * | 2016-03-17 | 2017-09-27 | Zentiva, K.S. | Způsob přípravy diastereomerně čistého Tenofoviru Alafenamidu nebo jeho solí |
| CN107286190A (zh) * | 2016-04-13 | 2017-10-24 | 刘沛 | 核苷之烃氧基苄基氨基磷酸/膦酸酯衍生物的制备及其医药用途 |
| WO2017197036A1 (en) | 2016-05-10 | 2017-11-16 | C4 Therapeutics, Inc. | Spirocyclic degronimers for target protein degradation |
| WO2017197055A1 (en) | 2016-05-10 | 2017-11-16 | C4 Therapeutics, Inc. | Heterocyclic degronimers for target protein degradation |
| EP3455218A4 (en) | 2016-05-10 | 2019-12-18 | C4 Therapeutics, Inc. | C3 CARBON-BASED GLUTARIMIDE DEGRONIMERS FOR TARGET PROTEIN REDUCTION |
| CN106565785B (zh) * | 2016-11-09 | 2019-11-12 | 周雨恬 | 一种具有抗hbv/hiv活性的核苷氨基磷酸酯类化合物及其盐和用途 |
| CN106946935B (zh) * | 2017-04-28 | 2020-01-07 | 福建广生堂药业股份有限公司 | 一种非对映异构体核苷衍生物的制备方法 |
| US10590136B2 (en) * | 2017-10-04 | 2020-03-17 | Celgene Corporation | Processes for the preparation of cis-4-[2-{[(3S,4R)-3-fluorooxan-4-yl]amino}-8-(2,4,6-trichloroanilino)-9H-purin-9-yl]-1-methylcyclohexane-1-carboxamide |
| CN109942632B (zh) * | 2017-12-20 | 2021-08-31 | 上海博志研新药物研究有限公司 | 替诺福韦艾拉酚胺中间体的制备方法 |
| CN109942633B (zh) * | 2017-12-20 | 2021-08-31 | 上海新礼泰药业有限公司 | 替诺福韦艾拉酚胺中间体的制备方法 |
| CN110092803A (zh) * | 2018-01-31 | 2019-08-06 | 北京睿创康泰医药研究院有限公司 | 替诺福韦艾拉酚胺富马酸盐工艺杂质的制备及其应用 |
| CN108409788B (zh) * | 2018-03-12 | 2020-05-08 | 科兴生物制药股份有限公司 | 一种富马酸替诺福韦艾拉酚胺的制备方法 |
| CN110305163A (zh) * | 2018-03-27 | 2019-10-08 | 北京济美堂医药研究有限公司 | 替诺福韦艾拉酚胺半富马酸盐的制备方法 |
| CN108467410B (zh) * | 2018-04-09 | 2021-04-09 | 重庆三圣实业股份有限公司 | 一种taf中间体的制备方法及产品和应用 |
| CN108484672A (zh) * | 2018-05-23 | 2018-09-04 | 中国药科大学制药有限公司 | 磷丙替诺福韦的手性拆分方法 |
| CN108822149B (zh) * | 2018-06-01 | 2020-08-11 | 成都苑东生物制药股份有限公司 | 一种富马酸替诺福韦艾拉酚胺关键中间体的制备方法 |
| CN110283208B (zh) * | 2018-06-22 | 2022-07-08 | 南京济群医药科技股份有限公司 | 一种替诺福韦艾拉酚胺的手性拆分方法 |
| CN109081853A (zh) * | 2018-09-03 | 2018-12-25 | 南京正大天晴制药有限公司 | 一种磷丙替诺福韦有关物质的制备方法 |
| CN111484527A (zh) * | 2019-01-25 | 2020-08-04 | 上海清松制药有限公司 | 一种替诺福韦艾拉酚胺中间体的制备方法 |
| CN111943981A (zh) * | 2019-05-14 | 2020-11-17 | 博瑞生物医药泰兴市有限公司 | 一种磷丙替诺福韦的制备方法 |
| CN114409706B (zh) * | 2019-07-01 | 2023-11-28 | 上海医药工业研究院 | 一种苯基氢膦酸酯及其中间体的制备方法 |
| WO2021011891A1 (en) | 2019-07-18 | 2021-01-21 | Gilead Sciences, Inc. | Long-acting formulations of tenofovir alafenamide |
| CN112390824B (zh) * | 2019-08-19 | 2022-07-05 | 鲁南制药集团股份有限公司 | 一种替诺福韦艾拉酚胺中间体的制备方法 |
| CN110981911A (zh) * | 2019-10-08 | 2020-04-10 | 浙江车头制药股份有限公司 | 一种替诺福韦艾拉酚胺的制备方法 |
| CN111171076A (zh) * | 2019-12-26 | 2020-05-19 | 合肥启旸生物科技有限公司 | 一种替诺福韦二聚体的制备方法 |
| WO2021188959A1 (en) | 2020-03-20 | 2021-09-23 | Gilead Sciences, Inc. | Prodrugs of 4'-c-substituted-2-halo-2'-deoxyadenosine nucleosides and methods of making and using the same |
| KR20210125298A (ko) | 2020-04-08 | 2021-10-18 | 주식회사 파마코스텍 | 테노포비어 알라펜아미드 헤미타르트레이트의 신규한 제조방법 |
| CN116437958A (zh) | 2020-11-11 | 2023-07-14 | 吉利德科学公司 | 鉴定对采用gp120 CD4结合位点导向的抗体的疗法敏感的HIV患者的方法 |
| KR20220141457A (ko) | 2021-04-13 | 2022-10-20 | 경동제약 주식회사 | 신규 결정형의 테노포비어 알라펜아미드 말레산염 및 이를 포함하는 약제학적 조성물 |
| TW202400172A (zh) | 2022-04-06 | 2024-01-01 | 美商基利科學股份有限公司 | 橋聯三環胺甲醯基吡啶酮化合物及其用途 |
| US20240034724A1 (en) | 2022-07-01 | 2024-02-01 | Gilead Sciences, Inc. | Therapeutic compounds useful for the prophylactic or therapeutic treatment of an hiv virus infection |
| US20240083984A1 (en) | 2022-08-26 | 2024-03-14 | Gilead Sciences, Inc. | Dosing and scheduling regimen for broadly neutralizing antibodies |
| US20240226130A1 (en) | 2022-10-04 | 2024-07-11 | Gilead Sciences, Inc. | 4'-thionucleoside analogues and their pharmaceutical use |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100749160B1 (ko) * | 2000-07-21 | 2007-08-14 | 길리애드 사이언시즈, 인코포레이티드 | 포스포네이트 뉴클레오티드 유사체의 전구 약물의 제조방법 |
| US20050239054A1 (en) | 2002-04-26 | 2005-10-27 | Arimilli Murty N | Method and compositions for identifying anti-HIV therapeutic compounds |
| ATE505196T1 (de) | 2004-07-27 | 2011-04-15 | Gilead Sciences Inc | Nukleosid phosphonat konjugate als anti hiv mittel |
| ES2572001T3 (es) | 2006-03-29 | 2016-05-27 | Gilead Sciences Inc | Derivado de bisfurano antivírico como inhibidor de la proteasa del VIH e intermedios del mismo |
| WO2008005555A1 (en) * | 2006-07-07 | 2008-01-10 | Gilead Sciences, Inc. | Modulators of toll-like receptor 7 |
| EP2049547A2 (en) * | 2006-07-21 | 2009-04-22 | Gilead Sciences, Inc. | Aza-peptide protease inhibitors |
| BRPI0714880A2 (pt) * | 2006-07-24 | 2013-05-21 | Gilead Sciences Inc | inibidores da transcriptase reversa do hiv |
| US8354421B2 (en) * | 2007-06-29 | 2013-01-15 | Korea Research Insitute Of Chemical Technology | HIV reverse transcriptase inhibitors |
| PE20141328A1 (es) | 2011-08-16 | 2014-10-04 | Gilead Sciences Inc | Tenofovir alafenamida hemifumarato |
| SI3333173T1 (sl) * | 2011-10-07 | 2019-08-30 | Gilead Sciences, Inc. | Postopki za pripravo analogov protivirusnega nukleotida |
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2012
- 2012-10-03 SI SI201231626T patent/SI3333173T1/sl unknown
- 2012-10-03 US US13/573,666 patent/US8664386B2/en active Active
- 2012-10-03 KR KR1020147011619A patent/KR102033802B1/ko active IP Right Grant
- 2012-10-03 AR ARP120103681 patent/AR088109A1/es not_active Application Discontinuation
- 2012-10-03 CN CN202110408116.9A patent/CN113264959A/zh active Pending
- 2012-10-03 PT PT127980290T patent/PT2764002T/pt unknown
- 2012-10-03 UY UY34361A patent/UY34361A/es not_active Application Discontinuation
- 2012-10-03 CN CN201710365515.5A patent/CN107266498B/zh active Active
- 2012-10-03 KR KR1020207021316A patent/KR20200090975A/ko active Application Filing
- 2012-10-03 EP EP18153951.1A patent/EP3333173B1/en active Active
- 2012-10-03 CA CA2850466A patent/CA2850466C/en active Active
- 2012-10-03 ES ES12798029.0T patent/ES2661705T3/es active Active
- 2012-10-03 CN CN202311252160.0A patent/CN117343101A/zh active Pending
- 2012-10-03 WO PCT/US2012/000441 patent/WO2013052094A2/en active Application Filing
- 2012-10-03 ES ES18153951T patent/ES2746859T3/es active Active
- 2012-10-03 CA CA3042169A patent/CA3042169C/en active Active
- 2012-10-03 BR BR112014011340A patent/BR112014011340A2/pt unknown
- 2012-10-03 CN CN201280048965.7A patent/CN103842366B/zh active Active
- 2012-10-03 PT PT18153951T patent/PT3333173T/pt unknown
- 2012-10-03 JP JP2014534535A patent/JP6190372B2/ja active Active
- 2012-10-03 PL PL18153951T patent/PL3333173T3/pl unknown
- 2012-10-03 EA EA201490753A patent/EA027086B1/ru unknown
- 2012-10-03 AU AU2012319172A patent/AU2012319172B2/en active Active
- 2012-10-03 EP EP12798029.0A patent/EP2764002B1/en active Active
- 2012-10-03 TW TW108139308A patent/TWI709567B/zh active
- 2012-10-03 TW TW105126598A patent/TWI613211B/zh active
- 2012-10-03 TW TW101136508A patent/TWI557133B/zh active
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