CN104628582B - 一种去甲文拉法辛盐酸盐的制备方法 - Google Patents
一种去甲文拉法辛盐酸盐的制备方法 Download PDFInfo
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- CN104628582B CN104628582B CN201510045712.XA CN201510045712A CN104628582B CN 104628582 B CN104628582 B CN 104628582B CN 201510045712 A CN201510045712 A CN 201510045712A CN 104628582 B CN104628582 B CN 104628582B
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- CN
- China
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- conditions
- preparation
- hydrochloride
- under
- desmethylvenlafaxine
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 title claims abstract description 37
- 238000002360 preparation method Methods 0.000 title claims abstract description 18
- QYRYFNHXARDNFZ-UHFFFAOYSA-N venlafaxine hydrochloride Chemical compound [H+].[Cl-].C1=CC(OC)=CC=C1C(CN(C)C)C1(O)CCCCC1 QYRYFNHXARDNFZ-UHFFFAOYSA-N 0.000 claims abstract description 18
- 229960002416 venlafaxine hydrochloride Drugs 0.000 claims abstract description 18
- 230000017858 demethylation Effects 0.000 claims abstract description 11
- 238000010520 demethylation reaction Methods 0.000 claims abstract description 11
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 claims abstract description 10
- 229930182817 methionine Natural products 0.000 claims abstract description 10
- 239000003153 chemical reaction reagent Substances 0.000 claims abstract description 8
- 239000002253 acid Substances 0.000 claims abstract description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 27
- 238000006243 chemical reaction Methods 0.000 claims description 24
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 21
- 238000003756 stirring Methods 0.000 claims description 20
- 239000007789 gas Substances 0.000 claims description 15
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 15
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- 239000012043 crude product Substances 0.000 claims description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 10
- 239000012074 organic phase Substances 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 8
- 238000004821 distillation Methods 0.000 claims description 7
- 238000001035 drying Methods 0.000 claims description 7
- 239000000725 suspension Substances 0.000 claims description 7
- 239000000706 filtrate Substances 0.000 claims description 6
- 239000012065 filter cake Substances 0.000 claims description 5
- 239000000376 reactant Substances 0.000 claims description 5
- 230000006837 decompression Effects 0.000 claims description 4
- 239000012071 phase Substances 0.000 claims description 4
- 238000000746 purification Methods 0.000 claims 2
- 239000000126 substance Substances 0.000 abstract description 3
- 230000007613 environmental effect Effects 0.000 abstract description 2
- KYYIDSXMWOZKMP-UHFFFAOYSA-N O-desmethylvenlafaxine Chemical compound C1CCCCC1(O)C(CN(C)C)C1=CC=C(O)C=C1 KYYIDSXMWOZKMP-UHFFFAOYSA-N 0.000 description 9
- 238000000034 method Methods 0.000 description 6
- PNVNVHUZROJLTJ-UHFFFAOYSA-N venlafaxine Chemical class C1=CC(OC)=CC=C1C(CN(C)C)C1(O)CCCCC1 PNVNVHUZROJLTJ-UHFFFAOYSA-N 0.000 description 5
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 229960004688 venlafaxine Drugs 0.000 description 4
- -1 desmethylvenlafaxine Chemical compound 0.000 description 3
- 150000003840 hydrochlorides Chemical class 0.000 description 3
- 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 2
- 239000010941 cobalt Substances 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 2
- 229910052976 metal sulfide Inorganic materials 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- LHFKHAVGGJJQFF-UEOYEZOQSA-N Hydroxy-alpha-sanshool Chemical compound C\C=C\C=C\C=C/CC\C=C\C(=O)NCC(C)(C)O LHFKHAVGGJJQFF-UEOYEZOQSA-N 0.000 description 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000001335 demethylating effect Effects 0.000 description 1
- OBTIDFCSHQLONE-UHFFFAOYSA-N diphenylphosphane;lithium Chemical compound [Li].C=1C=CC=CC=1PC1=CC=CC=C1 OBTIDFCSHQLONE-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 239000004210 ether based solvent Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000005304 joining Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000001035 methylating effect Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims (6)
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CN201510045712.XA CN104628582B (zh) | 2015-01-29 | 2015-01-29 | 一种去甲文拉法辛盐酸盐的制备方法 |
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CN201510045712.XA CN104628582B (zh) | 2015-01-29 | 2015-01-29 | 一种去甲文拉法辛盐酸盐的制备方法 |
Publications (2)
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CN104628582A CN104628582A (zh) | 2015-05-20 |
CN104628582B true CN104628582B (zh) | 2016-08-24 |
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Families Citing this family (1)
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CN110041269A (zh) * | 2019-05-16 | 2019-07-23 | 海门瑞一医药科技有限公司 | 一种2-氯-5-羟基嘧啶的制备方法 |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA2368083A1 (en) * | 1999-04-06 | 2000-10-12 | Sepracor Inc. | Derivatives of venlafaxine and methods of preparing and using the same |
CN101857617A (zh) * | 2010-04-28 | 2010-10-13 | 中国海洋大学 | 喹唑啉类糖衍生物及其制备方法和应用 |
CN102164886A (zh) * | 2008-07-30 | 2011-08-24 | 基因里克斯(英国)有限公司 | 用于制备o-去甲文拉法辛的方法 |
WO2012046250A2 (en) * | 2010-10-08 | 2012-04-12 | Cadila Healthcare Limited | Polymorphic forms of o-desmethyl-venlafaxine succinate field of the invention |
-
2015
- 2015-01-29 CN CN201510045712.XA patent/CN104628582B/zh active Active
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA2368083A1 (en) * | 1999-04-06 | 2000-10-12 | Sepracor Inc. | Derivatives of venlafaxine and methods of preparing and using the same |
CN102164886A (zh) * | 2008-07-30 | 2011-08-24 | 基因里克斯(英国)有限公司 | 用于制备o-去甲文拉法辛的方法 |
CN101857617A (zh) * | 2010-04-28 | 2010-10-13 | 中国海洋大学 | 喹唑啉类糖衍生物及其制备方法和应用 |
WO2012046250A2 (en) * | 2010-10-08 | 2012-04-12 | Cadila Healthcare Limited | Polymorphic forms of o-desmethyl-venlafaxine succinate field of the invention |
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CN104628582A (zh) | 2015-05-20 |
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PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: A preparation method of norvenlafaxine hydrochloride Effective date of registration: 20211104 Granted publication date: 20160824 Pledgee: China Everbright Bank Ji'nan branch Pledgor: JINAN ASIA PHARMA TECH Co.,Ltd. Registration number: Y2021370000123 |
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Date of cancellation: 20230913 Granted publication date: 20160824 Pledgee: China Everbright Bank Ji'nan branch Pledgor: JINAN ASIA PHARMA TECH Co.,Ltd. Registration number: Y2021370000123 |
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PC01 | Cancellation of the registration of the contract for pledge of patent right | ||
PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: A method for preparing demethylated venlafaxine hydrochloride Granted publication date: 20160824 Pledgee: Huaxia Bank Co.,Ltd. Jinan Branch Pledgor: JINAN ASIA PHARMA TECH Co.,Ltd. Registration number: Y2024980022431 |
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