CN105985329A - 一种新的泊沙康唑化合物制备方法 - Google Patents
一种新的泊沙康唑化合物制备方法 Download PDFInfo
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- CN105985329A CN105985329A CN201510098058.9A CN201510098058A CN105985329A CN 105985329 A CN105985329 A CN 105985329A CN 201510098058 A CN201510098058 A CN 201510098058A CN 105985329 A CN105985329 A CN 105985329A
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- preparation
- compound
- posaconazole
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- dissolved
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- 229960001589 posaconazole Drugs 0.000 title claims abstract description 26
- -1 posaconazole compound Chemical class 0.000 title claims abstract description 21
- 238000002360 preparation method Methods 0.000 title claims abstract description 21
- 238000006243 chemical reaction Methods 0.000 claims abstract description 17
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 claims abstract description 14
- 150000001875 compounds Chemical class 0.000 claims abstract description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 38
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- 208000035126 Facies Diseases 0.000 claims description 10
- 238000001816 cooling Methods 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- 238000003756 stirring Methods 0.000 claims description 6
- 150000001298 alcohols Chemical group 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 2
- 238000010792 warming Methods 0.000 claims description 2
- 150000001350 alkyl halides Chemical class 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 10
- 239000003814 drug Substances 0.000 abstract description 5
- 229940079593 drug Drugs 0.000 abstract description 3
- 238000009776 industrial production Methods 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- RAGOYPUPXAKGKH-XAKZXMRKSA-N posaconazole Chemical class O=C1N([C@H]([C@H](C)O)CC)N=CN1C1=CC=C(N2CCN(CC2)C=2C=CC(OC[C@H]3C[C@@](CN4N=CN=C4)(OC3)C=3C(=CC(F)=CC=3)F)=CC=2)C=C1 RAGOYPUPXAKGKH-XAKZXMRKSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
- 239000012043 crude product Substances 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000006264 debenzylation reaction Methods 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 201000002909 Aspergillosis Diseases 0.000 description 3
- 208000036641 Aspergillus infections Diseases 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000000844 anti-bacterial effect Effects 0.000 description 3
- 238000004807 desolvation Methods 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 206010059866 Drug resistance Diseases 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- 229940088710 antibiotic agent Drugs 0.000 description 2
- 229940121375 antifungal agent Drugs 0.000 description 2
- 239000003429 antifungal agent Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 150000003852 triazoles Chemical class 0.000 description 2
- BQPPJGMMIYJVBR-UHFFFAOYSA-N (10S)-3c-Acetoxy-4.4.10r.13c.14t-pentamethyl-17c-((R)-1.5-dimethyl-hexen-(4)-yl)-(5tH)-Delta8-tetradecahydro-1H-cyclopenta[a]phenanthren Natural products CC12CCC(OC(C)=O)C(C)(C)C1CCC1=C2CCC2(C)C(C(CCC=C(C)C)C)CCC21C BQPPJGMMIYJVBR-UHFFFAOYSA-N 0.000 description 1
- OILXMJHPFNGGTO-UHFFFAOYSA-N (22E)-(24xi)-24-methylcholesta-5,22-dien-3beta-ol Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)C=CC(C)C(C)C)C1(C)CC2 OILXMJHPFNGGTO-UHFFFAOYSA-N 0.000 description 1
- RQOCXCFLRBRBCS-UHFFFAOYSA-N (22E)-cholesta-5,7,22-trien-3beta-ol Natural products C1C(O)CCC2(C)C(CCC3(C(C(C)C=CCC(C)C)CCC33)C)C3=CC=C21 RQOCXCFLRBRBCS-UHFFFAOYSA-N 0.000 description 1
- CHGIKSSZNBCNDW-UHFFFAOYSA-N (3beta,5alpha)-4,4-Dimethylcholesta-8,24-dien-3-ol Natural products CC12CCC(O)C(C)(C)C1CCC1=C2CCC2(C)C(C(CCC=C(C)C)C)CCC21 CHGIKSSZNBCNDW-UHFFFAOYSA-N 0.000 description 1
- XYTLYKGXLMKYMV-UHFFFAOYSA-N 14alpha-methylzymosterol Natural products CC12CCC(O)CC1CCC1=C2CCC2(C)C(C(CCC=C(C)C)C)CCC21C XYTLYKGXLMKYMV-UHFFFAOYSA-N 0.000 description 1
- FPTJELQXIUUCEY-UHFFFAOYSA-N 3beta-Hydroxy-lanostan Natural products C1CC2C(C)(C)C(O)CCC2(C)C2C1C1(C)CCC(C(C)CCCC(C)C)C1(C)CC2 FPTJELQXIUUCEY-UHFFFAOYSA-N 0.000 description 1
- OQMZNAMGEHIHNN-UHFFFAOYSA-N 7-Dehydrostigmasterol Natural products C1C(O)CCC2(C)C(CCC3(C(C(C)C=CC(CC)C(C)C)CCC33)C)C3=CC=C21 OQMZNAMGEHIHNN-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241000222122 Candida albicans Species 0.000 description 1
- 206010007134 Candida infections Diseases 0.000 description 1
- DNVPQKQSNYMLRS-NXVQYWJNSA-N Ergosterol Natural products CC(C)[C@@H](C)C=C[C@H](C)[C@H]1CC[C@H]2C3=CC=C4C[C@@H](O)CC[C@]4(C)[C@@H]3CC[C@]12C DNVPQKQSNYMLRS-NXVQYWJNSA-N 0.000 description 1
- 206010017533 Fungal infection Diseases 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- BKLIAINBCQPSOV-UHFFFAOYSA-N Gluanol Natural products CC(C)CC=CC(C)C1CCC2(C)C3=C(CCC12C)C4(C)CCC(O)C(C)(C)C4CC3 BKLIAINBCQPSOV-UHFFFAOYSA-N 0.000 description 1
- LOPKHWOTGJIQLC-UHFFFAOYSA-N Lanosterol Natural products CC(CCC=C(C)C)C1CCC2(C)C3=C(CCC12C)C4(C)CCC(C)(O)C(C)(C)C4CC3 LOPKHWOTGJIQLC-UHFFFAOYSA-N 0.000 description 1
- 102100021695 Lanosterol 14-alpha demethylase Human genes 0.000 description 1
- 101710146773 Lanosterol 14-alpha demethylase Proteins 0.000 description 1
- 208000031888 Mycoses Diseases 0.000 description 1
- CAHGCLMLTWQZNJ-UHFFFAOYSA-N Nerifoliol Natural products CC12CCC(O)C(C)(C)C1CCC1=C2CCC2(C)C(C(CCC=C(C)C)C)CCC21C CAHGCLMLTWQZNJ-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 150000001348 alkyl chlorides Chemical class 0.000 description 1
- 230000000843 anti-fungal effect Effects 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 201000003984 candidiasis Diseases 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 210000000170 cell membrane Anatomy 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- QBSJHOGDIUQWTH-UHFFFAOYSA-N dihydrolanosterol Natural products CC(C)CCCC(C)C1CCC2(C)C3=C(CCC12C)C4(C)CCC(C)(O)C(C)(C)C4CC3 QBSJHOGDIUQWTH-UHFFFAOYSA-N 0.000 description 1
- DNVPQKQSNYMLRS-SOWFXMKYSA-N ergosterol Chemical compound C1[C@@H](O)CC[C@]2(C)[C@H](CC[C@]3([C@H]([C@H](C)/C=C/[C@@H](C)C(C)C)CC[C@H]33)C)C3=CC=C21 DNVPQKQSNYMLRS-SOWFXMKYSA-N 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- CAHGCLMLTWQZNJ-RGEKOYMOSA-N lanosterol Chemical compound C([C@]12C)C[C@@H](O)C(C)(C)[C@H]1CCC1=C2CC[C@]2(C)[C@H]([C@H](CCC=C(C)C)C)CC[C@@]21C CAHGCLMLTWQZNJ-RGEKOYMOSA-N 0.000 description 1
- 229940058690 lanosterol Drugs 0.000 description 1
- 229940099075 noxafil Drugs 0.000 description 1
- 231100000915 pathological change Toxicity 0.000 description 1
- 230000036285 pathological change Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 208000037922 refractory disease Diseases 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
Abstract
Description
Claims (9)
Priority Applications (1)
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CN201510098058.9A CN105985329B (zh) | 2015-03-06 | 2015-03-06 | 一种新的泊沙康唑化合物制备方法 |
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CN201510098058.9A CN105985329B (zh) | 2015-03-06 | 2015-03-06 | 一种新的泊沙康唑化合物制备方法 |
Publications (2)
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CN105985329A true CN105985329A (zh) | 2016-10-05 |
CN105985329B CN105985329B (zh) | 2020-06-02 |
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CN201510098058.9A Active CN105985329B (zh) | 2015-03-06 | 2015-03-06 | 一种新的泊沙康唑化合物制备方法 |
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN106749207A (zh) * | 2016-11-22 | 2017-05-31 | 上海博志研新药物技术有限公司 | 一种泊沙康唑的制备方法 |
CN109970725A (zh) * | 2019-03-29 | 2019-07-05 | 武汉朗来科技发展有限公司 | 泊沙康唑的制备方法 |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102863431A (zh) * | 2011-07-05 | 2013-01-09 | 南京长澳医药科技有限公司 | 一种泊沙康唑的制备方法 |
-
2015
- 2015-03-06 CN CN201510098058.9A patent/CN105985329B/zh active Active
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102863431A (zh) * | 2011-07-05 | 2013-01-09 | 南京长澳医药科技有限公司 | 一种泊沙康唑的制备方法 |
Non-Patent Citations (1)
Title |
---|
华东理工大学有机化学教研组: "《有机合成中的保护基》", 31 October 2004, 华东理工大学出版社 * |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN106749207A (zh) * | 2016-11-22 | 2017-05-31 | 上海博志研新药物技术有限公司 | 一种泊沙康唑的制备方法 |
CN110590757A (zh) * | 2016-11-22 | 2019-12-20 | 上海博志研新药物技术有限公司 | 一种泊沙康唑的制备方法 |
CN109970725A (zh) * | 2019-03-29 | 2019-07-05 | 武汉朗来科技发展有限公司 | 泊沙康唑的制备方法 |
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Address after: 215123 Suzhou Industrial Park, Suzhou, Jiangsu, No. 388, Nanshui, 7 D, National Science and Technology Park, Nanshui University. Applicant after: SUZHOU LANXITE BIOTECHNOLOGY Co.,Ltd. Address before: 215123 Jiangsu Suzhou Industrial Park, No. 388, No. 7, D building, National Science and Technology Park, National University of Suzhou. Applicant before: SUZHOU LANXITE BIOTECHNOLOGY Co.,Ltd. |
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Application publication date: 20161005 Assignee: Suzhou ronghua Leasing Co.,Ltd. Assignor: SUZHOU LANXITE BIOTECHNOLOGY Co.,Ltd. Contract record no.: X2020320010026 Denomination of invention: A new preparation method of posaconazole Granted publication date: 20200602 License type: Exclusive License Record date: 20201201 |
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PE01 | Entry into force of the registration of the contract for pledge of patent right | ||
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Denomination of invention: A new preparation method of posaconazole Effective date of registration: 20201203 Granted publication date: 20200602 Pledgee: Suzhou ronghua Leasing Co.,Ltd. Pledgor: SUZHOU LANXITE BIOTECHNOLOGY Co.,Ltd. Registration number: Y2020320010214 |
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EC01 | Cancellation of recordation of patent licensing contract |
Assignee: Suzhou ronghua Leasing Co.,Ltd. Assignor: SUZHOU LANXITE BIOTECHNOLOGY Co.,Ltd. Contract record no.: X2020320010026 Date of cancellation: 20230901 |
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PC01 | Cancellation of the registration of the contract for pledge of patent right | ||
PC01 | Cancellation of the registration of the contract for pledge of patent right |
Date of cancellation: 20230901 Granted publication date: 20200602 Pledgee: Suzhou ronghua Leasing Co.,Ltd. Pledgor: SUZHOU LANXITE BIOTECHNOLOGY Co.,Ltd. Registration number: Y2020320010214 |