JP2014530809A5 - - Google Patents
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- JP2014530809A5 JP2014530809A5 JP2014534535A JP2014534535A JP2014530809A5 JP 2014530809 A5 JP2014530809 A5 JP 2014530809A5 JP 2014534535 A JP2014534535 A JP 2014534535A JP 2014534535 A JP2014534535 A JP 2014534535A JP 2014530809 A5 JP2014530809 A5 JP 2014530809A5
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- JP
- Japan
- Prior art keywords
- compound
- treated
- halogenating agent
- solvent
- ethyl
- 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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- 238000000034 method Methods 0.000 claims description 37
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 24
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 18
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 claims description 15
- 229940125797 compound 12 Drugs 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 12
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 claims description 12
- 239000003795 chemical substances by application Substances 0.000 claims description 11
- 230000002140 halogenating effect Effects 0.000 claims description 11
- UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 claims description 10
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 claims description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- VCMJCVGFSROFHV-WZGZYPNHSA-N tenofovir disoproxil fumarate Chemical compound OC(=O)\C=C\C(O)=O.N1=CN=C2N(C[C@@H](C)OCP(=O)(OCOC(=O)OC(C)C)OCOC(=O)OC(C)C)C=NC2=C1N VCMJCVGFSROFHV-WZGZYPNHSA-N 0.000 claims description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical group ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 5
- GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 claims description 4
- ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 claims description 4
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 4
- 229940125758 compound 15 Drugs 0.000 claims description 4
- 229940126142 compound 16 Drugs 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 claims description 4
- 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 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- KYVBNYUBXIEUFW-UHFFFAOYSA-N 1,1,3,3-tetramethylguanidine Chemical compound CN(C)C(=N)N(C)C KYVBNYUBXIEUFW-UHFFFAOYSA-N 0.000 claims description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- WFPZOAOJEXDUGP-UHFFFAOYSA-N 2,5-dimethyl-3-piperazin-1-ylpyrazine Chemical compound CC1=CN=C(C)C(N2CCNCC2)=N1 WFPZOAOJEXDUGP-UHFFFAOYSA-N 0.000 claims description 2
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 claims description 2
- BTOJSYRZQZOMOK-UHFFFAOYSA-N 4-chloro-7-(4-methylphenyl)sulfonylpyrrolo[2,3-d]pyrimidine Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1C2=NC=NC(Cl)=C2C=C1 BTOJSYRZQZOMOK-UHFFFAOYSA-N 0.000 claims description 2
- 229930024421 Adenine Natural products 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 2
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 claims description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 2
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 claims description 2
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 2
- 229960000643 adenine Drugs 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- QEGCPIMZHQJQAO-UHFFFAOYSA-N bromo(triphenyl)-$l^{5}-phosphane Chemical class C=1C=CC=CC=1P(C=1C=CC=CC=1)(Br)C1=CC=CC=C1 QEGCPIMZHQJQAO-UHFFFAOYSA-N 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- AAHIAAMUDBLHHU-UHFFFAOYSA-N chloro(triphenyl)-$l^{5}-phosphane Chemical class C=1C=CC=CC=1P(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 AAHIAAMUDBLHHU-UHFFFAOYSA-N 0.000 claims description 2
- 239000013078 crystal Substances 0.000 claims description 2
- 229960004132 diethyl ether Drugs 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 claims description 2
- 229940011051 isopropyl acetate Drugs 0.000 claims description 2
- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 claims description 2
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 claims description 2
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 claims description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 claims description 2
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 229940090181 propyl acetate Drugs 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims description 2
- HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 claims description 2
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 claims description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 2
- MITGKKFYIJJQGL-UHFFFAOYSA-N 9-(4-chlorobenzoyl)-6-methylsulfonyl-2,3-dihydro-1H-carbazol-4-one Chemical compound ClC1=CC=C(C(=O)N2C3=CC=C(C=C3C=3C(CCCC2=3)=O)S(=O)(=O)C)C=C1 MITGKKFYIJJQGL-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- UURSXESKOOOTOV-UHFFFAOYSA-N dec-5-ene Chemical compound CCCCC=CCCCC UURSXESKOOOTOV-UHFFFAOYSA-N 0.000 claims 1
- OEBXWWBYZJNKRK-UHFFFAOYSA-N 1-methyl-2,3,4,6,7,8-hexahydropyrimido[1,2-a]pyrimidine Chemical compound C1CCN=C2N(C)CCCN21 OEBXWWBYZJNKRK-UHFFFAOYSA-N 0.000 description 2
- WCDLCPLAAKUJNY-UHFFFAOYSA-N 4-[4-[3-(1h-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidin-6-yl]phenyl]morpholine Chemical compound C1COCCN1C1=CC=C(C2=CN3N=CC(=C3N=C2)C2=CNN=C2)C=C1 WCDLCPLAAKUJNY-UHFFFAOYSA-N 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US61/544,950 | 2011-10-07 | ||
| PCT/US2012/000441 WO2013052094A2 (en) | 2011-10-07 | 2012-10-03 | Methods for preparing anti-viral nucleotide analogs |
| US201161544950P | 2014-04-11 | 2014-04-11 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017083047A Division JP2017160228A (ja) | 2011-10-07 | 2017-04-19 | 抗ウイルスヌクレオチド類似体を調製する方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2014530809A JP2014530809A (ja) | 2014-11-20 |
| JP2014530809A5 true JP2014530809A5 (enExample) | 2015-11-19 |
| JP6190372B2 JP6190372B2 (ja) | 2017-08-30 |
Family
ID=47297386
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014534535A Active JP6190372B2 (ja) | 2011-10-07 | 2012-10-03 | 抗ウイルスヌクレオチド類似体を調製する方法 |
| JP2017083047A Withdrawn JP2017160228A (ja) | 2011-10-07 | 2017-04-19 | 抗ウイルスヌクレオチド類似体を調製する方法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017083047A Withdrawn JP2017160228A (ja) | 2011-10-07 | 2017-04-19 | 抗ウイルスヌクレオチド類似体を調製する方法 |
Country Status (25)
| Country | Link |
|---|---|
| US (4) | US8664386B2 (enExample) |
| EP (2) | EP3333173B1 (enExample) |
| JP (2) | JP6190372B2 (enExample) |
| KR (3) | KR20200090975A (enExample) |
| CN (4) | CN113264959A (enExample) |
| AR (1) | AR088109A1 (enExample) |
| AU (3) | AU2012319172B2 (enExample) |
| BR (2) | BR112014011340A2 (enExample) |
| CA (2) | CA3042169C (enExample) |
| CL (1) | CL2014000827A1 (enExample) |
| CO (1) | CO6940431A2 (enExample) |
| CR (1) | CR20140204A (enExample) |
| EA (1) | EA027086B1 (enExample) |
| EC (1) | ECSP14000074A (enExample) |
| ES (2) | ES2746859T3 (enExample) |
| HK (1) | HK1255222B (enExample) |
| IL (1) | IL231879B (enExample) |
| MX (1) | MX353064B (enExample) |
| PE (1) | PE20141160A1 (enExample) |
| PL (1) | PL3333173T3 (enExample) |
| PT (2) | PT2764002T (enExample) |
| SI (1) | SI3333173T1 (enExample) |
| TW (4) | TWI689513B (enExample) |
| UY (1) | UY34361A (enExample) |
| WO (1) | WO2013052094A2 (enExample) |
Families Citing this family (67)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SMT201600476T1 (it) | 2011-08-16 | 2017-03-08 | Gilead Sciences Inc | Tenofovir alafenammide emifumarato |
| CN113264959A (zh) | 2011-10-07 | 2021-08-17 | 吉利德科学公司 | 制备抗病毒核苷酸类似物的方法 |
| CN107312039B (zh) | 2012-08-30 | 2019-06-25 | 江苏豪森药业集团有限公司 | 一种替诺福韦前药的制备方法 |
| WO2014195724A1 (en) * | 2013-06-07 | 2014-12-11 | 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 |
| WO2015107451A2 (en) | 2014-01-14 | 2015-07-23 | Mylan Laboratories Ltd. | Purification of tenofovir alafenamide and its intermediates |
| 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 |
| CN105531281B (zh) * | 2014-04-21 | 2017-12-15 | 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 |
| WO2015197006A1 (zh) * | 2014-06-25 | 2015-12-30 | 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 |
| CN108191913A (zh) * | 2014-11-12 | 2018-06-22 | 四川海思科制药有限公司 | 一种替诺福韦艾拉酚胺晶型a及其制备方法 |
| 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 |
| IL293066A (en) | 2015-08-05 | 2022-07-01 | Eisai R&D Man Co Ltd | Chiral reagents for the preparation of homogeneous oligomers |
| 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 |
| CN109562107A (zh) | 2016-05-10 | 2019-04-02 | C4医药公司 | 用于靶蛋白降解的杂环降解决定子体 |
| 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 |
| EP3455218A4 (en) | 2016-05-10 | 2019-12-18 | C4 Therapeutics, Inc. | C3 CARBON-BASED GLUTARIMIDE DEGRONIMERS FOR TARGET PROTEIN REDUCTION |
| EP4483875A3 (en) | 2016-05-10 | 2025-04-02 | C4 Therapeutics, Inc. | Spirocyclic degronimers for target protein degradation |
| 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 |
| CN118440096A (zh) | 2017-06-20 | 2024-08-06 | C4医药公司 | 用于蛋白降解的n/o-连接的降解决定子和降解决定子体 |
| EP3692041A1 (en) * | 2017-10-04 | 2020-08-12 | 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 |
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