CN104558035A - 一种替诺福韦前药的纯化方法 - Google Patents
一种替诺福韦前药的纯化方法 Download PDFInfo
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- CN104558035A CN104558035A CN201310499954.7A CN201310499954A CN104558035A CN 104558035 A CN104558035 A CN 104558035A CN 201310499954 A CN201310499954 A CN 201310499954A CN 104558035 A CN104558035 A CN 104558035A
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- tartaric acid
- dibenzoyl tartaric
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- 229940002612 prodrug Drugs 0.000 title abstract description 11
- 239000000651 prodrug Substances 0.000 title abstract description 11
- 238000000034 method Methods 0.000 title abstract description 10
- 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 title abstract description 6
- 229960004556 tenofovir Drugs 0.000 title abstract description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 58
- YONLFQNRGZXBBF-KBPBESRZSA-N (2s,3s)-2,3-dibenzoyloxybutanedioic acid Chemical compound O([C@H](C(=O)O)[C@H](OC(=O)C=1C=CC=CC=1)C(O)=O)C(=O)C1=CC=CC=C1 YONLFQNRGZXBBF-KBPBESRZSA-N 0.000 claims abstract description 24
- 239000000203 mixture Substances 0.000 claims abstract description 20
- 238000002425 crystallisation Methods 0.000 claims abstract description 8
- 230000008025 crystallization Effects 0.000 claims abstract description 8
- 239000003513 alkali Substances 0.000 claims abstract description 7
- 238000006386 neutralization reaction Methods 0.000 claims abstract 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 33
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 19
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 18
- 238000000746 purification Methods 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 12
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 8
- 239000012046 mixed solvent Substances 0.000 claims description 5
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 2
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- 239000000243 solution Substances 0.000 description 10
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- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- 239000000047 product Substances 0.000 description 6
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- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
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- 0 CC(C)OC(C(C)(C)N[P@@](CO[C@](C)C[n]1c2ncnc(N)c2nc1)(*c1ccccc1)=O)=O Chemical compound CC(C)OC(C(C)(C)N[P@@](CO[C@](C)C[n]1c2ncnc(N)c2nc1)(*c1ccccc1)=O)=O 0.000 description 2
- ORHSFGJQGPUCRR-RZCFMFBHSA-N CC(C)OC(C(C)(C)N[P@](CO[C@H](C)C[n]1c2ncnc(N)c2nc1)(Oc1ccccc1)=O)=O Chemical compound CC(C)OC(C(C)(C)N[P@](CO[C@H](C)C[n]1c2ncnc(N)c2nc1)(Oc1ccccc1)=O)=O ORHSFGJQGPUCRR-RZCFMFBHSA-N 0.000 description 2
- 229940126656 GS-4224 Drugs 0.000 description 2
- 241000725303 Human immunodeficiency virus Species 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- -1 nucleoside acids Chemical class 0.000 description 2
- 210000005105 peripheral blood lymphocyte Anatomy 0.000 description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
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- 238000011160 research Methods 0.000 description 2
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 2
- RQXRKAOQBXZNRN-UHFFFAOYSA-N CC(C)OC(C(C)(C)N)=O Chemical compound CC(C)OC(C(C)(C)N)=O RQXRKAOQBXZNRN-UHFFFAOYSA-N 0.000 description 1
- ORHSFGJQGPUCRR-LXAPUOBYSA-N CC(C)OC(C(C)(C)NP(CO[C@H](C)C[n]1c2ncnc(N)c2nc1)(Oc1ccccc1)=O)=O Chemical compound CC(C)OC(C(C)(C)NP(CO[C@H](C)C[n]1c2ncnc(N)c2nc1)(Oc1ccccc1)=O)=O ORHSFGJQGPUCRR-LXAPUOBYSA-N 0.000 description 1
- ORHSFGJQGPUCRR-JTJFVBHCSA-N CC(C)OC(C(C)(C)N[P@@](CO[C@H](C)C[n]1c2ncnc(N)c2nc1)(Oc1ccccc1)=O)=O Chemical compound CC(C)OC(C(C)(C)N[P@@](CO[C@H](C)C[n]1c2ncnc(N)c2nc1)(Oc1ccccc1)=O)=O ORHSFGJQGPUCRR-JTJFVBHCSA-N 0.000 description 1
- SGOIRFVFHAKUTI-ZCFIWIBFSA-N C[C@H](C[n]1c2ncnc(N)c2nc1)OCP(O)(O)=O Chemical compound C[C@H](C[n]1c2ncnc(N)c2nc1)OCP(O)(O)=O SGOIRFVFHAKUTI-ZCFIWIBFSA-N 0.000 description 1
- PWTYXWUCSNJVRJ-LLVKDONJSA-N C[C@H](C[n]1c2ncnc(N)c2nc1)OCP(O)(Pc1ccccc1)=O Chemical compound C[C@H](C[n]1c2ncnc(N)c2nc1)OCP(O)(Pc1ccccc1)=O PWTYXWUCSNJVRJ-LLVKDONJSA-N 0.000 description 1
- 208000030453 Drug-Related Side Effects and Adverse reaction Diseases 0.000 description 1
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- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 206010049287 Lipodystrophy acquired Diseases 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-L Phosphate ion(2-) Chemical compound OP([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-L 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 206010070863 Toxicity to various agents Diseases 0.000 description 1
- 208000036142 Viral infection Diseases 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
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- 231100000417 nephrotoxicity Toxicity 0.000 description 1
- 239000002777 nucleoside Substances 0.000 description 1
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- 239000012466 permeate Substances 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
- 125000005499 phosphonyl group Chemical group 0.000 description 1
- PTMHPRAIXMAOOB-UHFFFAOYSA-L phosphoramidate Chemical compound NP([O-])([O-])=O PTMHPRAIXMAOOB-UHFFFAOYSA-L 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000003419 rna directed dna polymerase inhibitor Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
Claims (7)
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
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CN201310499954.7A CN104558035B (zh) | 2013-10-22 | 2013-10-22 | 一种替诺福韦前药的纯化方法 |
HK15109525.8A HK1208869A1 (zh) | 2013-10-22 | 2015-09-29 | 種替諾福韋前藥的純化方法 |
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CN201310499954.7A CN104558035B (zh) | 2013-10-22 | 2013-10-22 | 一种替诺福韦前药的纯化方法 |
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CN104558035A true CN104558035A (zh) | 2015-04-29 |
CN104558035B CN104558035B (zh) | 2017-12-19 |
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HK (1) | HK1208869A1 (zh) |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN106699812A (zh) * | 2015-11-12 | 2017-05-24 | 江苏豪森药业集团有限公司 | 替诺福韦前药的制备和纯化方法 |
WO2017133517A1 (zh) * | 2016-02-03 | 2017-08-10 | 四川海思科制药有限公司 | 一种磷酰胺衍生物及制备方法和用途 |
CN107652191A (zh) * | 2017-11-24 | 2018-02-02 | 常州沃腾化工科技有限公司 | 一种文拉法辛中间体的纯化方法 |
US9908908B2 (en) | 2012-08-30 | 2018-03-06 | Jiangsu Hansoh Pharmaceutical Co., Ltd. | Tenofovir prodrug and pharmaceutical uses thereof |
CN109384814A (zh) * | 2017-08-14 | 2019-02-26 | 江苏豪森药业集团有限公司 | 新型替诺福韦前药的纯化方法 |
CN113501846A (zh) * | 2021-06-10 | 2021-10-15 | 江苏豪森药业集团有限公司 | 艾美酚胺替诺福韦半富马酸复合物、晶型及其制备方法和应用 |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0434450A2 (en) * | 1989-12-22 | 1991-06-26 | The Wellcome Foundation Limited | Therapeutic nucleosides |
CN102015739A (zh) * | 2008-02-20 | 2011-04-13 | 吉联亚科学股份有限公司 | 新的化合物以及用于治疗的方法 |
CN103193779A (zh) * | 2012-01-05 | 2013-07-10 | 成都弘达药业有限公司 | 一种右佐匹克隆的制备方法 |
CN103224467A (zh) * | 2013-05-17 | 2013-07-31 | 浙江万邦药业股份有限公司 | 一种(-)-石杉碱甲的制备方法 |
-
2013
- 2013-10-22 CN CN201310499954.7A patent/CN104558035B/zh active Active
-
2015
- 2015-09-29 HK HK15109525.8A patent/HK1208869A1/zh unknown
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0434450A2 (en) * | 1989-12-22 | 1991-06-26 | The Wellcome Foundation Limited | Therapeutic nucleosides |
CN102015739A (zh) * | 2008-02-20 | 2011-04-13 | 吉联亚科学股份有限公司 | 新的化合物以及用于治疗的方法 |
CN103193779A (zh) * | 2012-01-05 | 2013-07-10 | 成都弘达药业有限公司 | 一种右佐匹克隆的制备方法 |
CN103224467A (zh) * | 2013-05-17 | 2013-07-31 | 浙江万邦药业股份有限公司 | 一种(-)-石杉碱甲的制备方法 |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US9908908B2 (en) | 2012-08-30 | 2018-03-06 | Jiangsu Hansoh Pharmaceutical Co., Ltd. | Tenofovir prodrug and pharmaceutical uses thereof |
CN106699812A (zh) * | 2015-11-12 | 2017-05-24 | 江苏豪森药业集团有限公司 | 替诺福韦前药的制备和纯化方法 |
WO2017133517A1 (zh) * | 2016-02-03 | 2017-08-10 | 四川海思科制药有限公司 | 一种磷酰胺衍生物及制备方法和用途 |
CN109384814A (zh) * | 2017-08-14 | 2019-02-26 | 江苏豪森药业集团有限公司 | 新型替诺福韦前药的纯化方法 |
CN109384814B (zh) * | 2017-08-14 | 2022-04-29 | 江苏豪森药业集团有限公司 | 新型替诺福韦前药的纯化方法 |
CN107652191A (zh) * | 2017-11-24 | 2018-02-02 | 常州沃腾化工科技有限公司 | 一种文拉法辛中间体的纯化方法 |
CN113501846A (zh) * | 2021-06-10 | 2021-10-15 | 江苏豪森药业集团有限公司 | 艾美酚胺替诺福韦半富马酸复合物、晶型及其制备方法和应用 |
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Publication number | Publication date |
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CN104558035B (zh) | 2017-12-19 |
HK1208869A1 (zh) | 2016-03-18 |
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