CN111712501A - 苯二氮卓衍生物盐酸盐与晶型、制备方法及其应用 - Google Patents
苯二氮卓衍生物盐酸盐与晶型、制备方法及其应用 Download PDFInfo
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- CN111712501A CN111712501A CN201980012858.0A CN201980012858A CN111712501A CN 111712501 A CN111712501 A CN 111712501A CN 201980012858 A CN201980012858 A CN 201980012858A CN 111712501 A CN111712501 A CN 111712501A
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- -1 Benzodiazepine derivative hydrochloride Chemical group 0.000 title claims abstract 7
- 239000013078 crystal Chemical group 0.000 title claims abstract 6
- 238000002360 preparation method Methods 0.000 title claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract 8
- 238000000034 method Methods 0.000 claims abstract 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract 7
- 150000001875 compounds Chemical class 0.000 claims abstract 3
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract 3
- 238000000634 powder X-ray diffraction Methods 0.000 claims 15
- 238000001228 spectrum Methods 0.000 claims 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 11
- 230000005855 radiation Effects 0.000 claims 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 5
- 235000001014 amino acid Nutrition 0.000 claims 5
- 125000003310 benzodiazepinyl group Chemical class N1N=C(C=CC2=C1C=CC=C2)* 0.000 claims 5
- 239000002904 solvent Substances 0.000 claims 5
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 4
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 3
- 150000001413 amino acids Chemical class 0.000 claims 3
- 238000002425 crystallisation Methods 0.000 claims 3
- 230000008025 crystallization Effects 0.000 claims 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 3
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims 2
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims 2
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 2
- 239000003513 alkali Substances 0.000 claims 2
- 229940043232 butyl acetate Drugs 0.000 claims 2
- 239000003759 ester based solvent Substances 0.000 claims 2
- 229940093499 ethyl acetate Drugs 0.000 claims 2
- 239000012458 free base Substances 0.000 claims 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims 2
- 238000001990 intravenous administration Methods 0.000 claims 2
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 claims 2
- 229940011051 isopropyl acetate Drugs 0.000 claims 2
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims 2
- 239000005453 ketone based solvent Substances 0.000 claims 2
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 claims 2
- 239000003960 organic solvent Substances 0.000 claims 2
- 229940090181 propyl acetate Drugs 0.000 claims 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims 2
- JETBVOLWZWPMKR-UHFFFAOYSA-N (1-carboxy-2-methylpropyl)azanium;chloride Chemical compound Cl.CC(C)C(N)C(O)=O JETBVOLWZWPMKR-UHFFFAOYSA-N 0.000 claims 1
- ILYVXUGGBVATGA-DKWTVANSSA-N (2s)-2-aminopropanoic acid;hydrochloride Chemical compound Cl.C[C@H](N)C(O)=O ILYVXUGGBVATGA-DKWTVANSSA-N 0.000 claims 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 1
- IVLXQGJVBGMLRR-UHFFFAOYSA-N 2-aminoacetic acid;hydron;chloride Chemical compound Cl.NCC(O)=O IVLXQGJVBGMLRR-UHFFFAOYSA-N 0.000 claims 1
- 206010002091 Anaesthesia Diseases 0.000 claims 1
- WTSQLDDJCMQWMI-UHFFFAOYSA-N C(C)(C)O.C(C)(=O)Cl Chemical compound C(C)(C)O.C(C)(=O)Cl WTSQLDDJCMQWMI-UHFFFAOYSA-N 0.000 claims 1
- YVCQXMGWDITGBQ-UHFFFAOYSA-N C(C)O.C(CC)(=O)Cl Chemical compound C(C)O.C(CC)(=O)Cl YVCQXMGWDITGBQ-UHFFFAOYSA-N 0.000 claims 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims 1
- BRHQRRBTAINFEC-UHFFFAOYSA-N acetyl chloride;ethanol Chemical compound CCO.CC(Cl)=O BRHQRRBTAINFEC-UHFFFAOYSA-N 0.000 claims 1
- KBRWCJQBIKIQLG-UHFFFAOYSA-N acetyl chloride;methanol Chemical compound OC.CC(Cl)=O KBRWCJQBIKIQLG-UHFFFAOYSA-N 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 238000001949 anaesthesia Methods 0.000 claims 1
- 230000037005 anaesthesia Effects 0.000 claims 1
- 230000003444 anaesthetic effect Effects 0.000 claims 1
- 229940053197 benzodiazepine derivative antiepileptics Drugs 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 229960001701 chloroform Drugs 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- DZGCGKFAPXFTNM-UHFFFAOYSA-N ethanol;hydron;chloride Chemical compound Cl.CCO DZGCGKFAPXFTNM-UHFFFAOYSA-N 0.000 claims 1
- 239000004210 ether based solvent Substances 0.000 claims 1
- 229960001269 glycine hydrochloride Drugs 0.000 claims 1
- FUKUFMFMCZIRNT-UHFFFAOYSA-N hydron;methanol;chloride Chemical compound Cl.OC FUKUFMFMCZIRNT-UHFFFAOYSA-N 0.000 claims 1
- AKPUJVVHYUHGKY-UHFFFAOYSA-N hydron;propan-2-ol;chloride Chemical compound Cl.CC(C)O AKPUJVVHYUHGKY-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 239000003208 petroleum Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
Images
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
- A61K31/551—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having two nitrogen atoms, e.g. dilazep
- A61K31/5513—1,4-Benzodiazepines, e.g. diazepam or clozapine
- A61K31/5517—1,4-Benzodiazepines, e.g. diazepam or clozapine condensed with five-membered rings having nitrogen as a ring hetero atom, e.g. imidazobenzodiazepines, triazolam
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P23/00—Anaesthetics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Epidemiology (AREA)
- Anesthesiology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
本发明提供具有如下式I的苯二氮卓类衍生物盐酸盐或其乙醇合物的晶体结构，
Description
PCT国内申请，说明书已公开。
Claims (18)
- PCT国内申请，权利要求书已公开。
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810151979 | 2018-02-13 | ||
| CN2018101519790 | 2018-02-13 | ||
| PCT/CN2019/074935 WO2019158075A1 (zh) | 2018-02-13 | 2019-02-13 | 苯二氮卓衍生物盐酸盐与晶型、制备方法及其应用 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN111712501A true CN111712501A (zh) | 2020-09-25 |
Family
ID=67618826
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201980012858.0A Pending CN111712501A (zh) | 2018-02-13 | 2019-02-13 | 苯二氮卓衍生物盐酸盐与晶型、制备方法及其应用 |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US11708368B2 (zh) |
| EP (1) | EP3753940B1 (zh) |
| JP (1) | JP7410036B2 (zh) |
| KR (1) | KR102647713B1 (zh) |
| CN (1) | CN111712501A (zh) |
| AU (1) | AU2019222052B2 (zh) |
| BR (1) | BR112020016323A2 (zh) |
| CA (1) | CA3090913C (zh) |
| EA (1) | EA202091927A1 (zh) |
| IL (1) | IL276611A (zh) |
| MX (1) | MX2020008465A (zh) |
| PH (1) | PH12020551217A1 (zh) |
| SG (1) | SG11202007733SA (zh) |
| WO (1) | WO2019158075A1 (zh) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114478535A (zh) * | 2020-10-23 | 2022-05-13 | 成都苑东生物制药股份有限公司 | 一种苯磺酸瑞马唑仑ii晶型的制备方法 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103347519A (zh) * | 2010-11-08 | 2013-10-09 | Paion英国有限公司 | 使用cns 7056(雷米马唑仑)镇静的给药方案 |
| WO2016011943A1 (zh) * | 2014-07-23 | 2016-01-28 | 李勤耕 | 新的苯并二氮杂䓬类衍生物及其用途 |
| CN107266452A (zh) * | 2016-04-08 | 2017-10-20 | 四川科伦药物研究院有限公司 | 苯并二氮杂*衍生物的盐及其晶体形式、制备方法和用途 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9911152D0 (en) | 1999-05-14 | 1999-07-14 | Glaxo Group Ltd | Short-acting benzodiazepines |
| KR20170091770A (ko) | 2006-07-10 | 2017-08-09 | 파이온 유케이 리미티드 | 속효형 벤조디아제핀 염 및 이의 중합체 형태 |
| CN102964349A (zh) | 2011-08-31 | 2013-03-13 | 江苏恒瑞医药股份有限公司 | 苯并二氮杂*衍生物的托西酸盐及其多晶型、它们的制备方法和用途 |
| EP3580219B1 (en) * | 2017-02-09 | 2022-04-13 | Assia Chemical Industries Ltd. | Process for the preparation of remimazolam and solid state forms of remimazolam salts |
-
2019
- 2019-02-13 WO PCT/CN2019/074935 patent/WO2019158075A1/zh unknown
- 2019-02-13 CN CN201980012858.0A patent/CN111712501A/zh active Pending
- 2019-02-13 AU AU2019222052A patent/AU2019222052B2/en active Active
- 2019-02-13 CA CA3090913A patent/CA3090913C/en active Active
- 2019-02-13 BR BR112020016323-6A patent/BR112020016323A2/pt unknown
- 2019-02-13 US US16/969,224 patent/US11708368B2/en active Active
- 2019-02-13 PH PH1/2020/551217A patent/PH12020551217A1/en unknown
- 2019-02-13 JP JP2020543143A patent/JP7410036B2/ja active Active
- 2019-02-13 EA EA202091927A patent/EA202091927A1/ru unknown
- 2019-02-13 EP EP19754326.7A patent/EP3753940B1/en active Active
- 2019-02-13 SG SG11202007733SA patent/SG11202007733SA/en unknown
- 2019-02-13 MX MX2020008465A patent/MX2020008465A/es unknown
- 2019-02-13 KR KR1020207026112A patent/KR102647713B1/ko active Active
-
2020
- 2020-08-10 IL IL276611A patent/IL276611A/en unknown
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103347519A (zh) * | 2010-11-08 | 2013-10-09 | Paion英国有限公司 | 使用cns 7056(雷米马唑仑)镇静的给药方案 |
| WO2016011943A1 (zh) * | 2014-07-23 | 2016-01-28 | 李勤耕 | 新的苯并二氮杂䓬类衍生物及其用途 |
| CN107266452A (zh) * | 2016-04-08 | 2017-10-20 | 四川科伦药物研究院有限公司 | 苯并二氮杂*衍生物的盐及其晶体形式、制备方法和用途 |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114478535A (zh) * | 2020-10-23 | 2022-05-13 | 成都苑东生物制药股份有限公司 | 一种苯磺酸瑞马唑仑ii晶型的制备方法 |
| CN114478535B (zh) * | 2020-10-23 | 2024-02-09 | 成都苑东生物制药股份有限公司 | 一种苯磺酸瑞马唑仑ii晶型的制备方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| US20210002283A1 (en) | 2021-01-07 |
| AU2019222052A1 (en) | 2020-09-17 |
| PH12020551217A1 (en) | 2021-04-19 |
| JP7410036B2 (ja) | 2024-01-09 |
| KR20200120935A (ko) | 2020-10-22 |
| AU2019222052B2 (en) | 2022-05-12 |
| MX2020008465A (es) | 2020-12-07 |
| BR112020016323A2 (pt) | 2020-12-15 |
| WO2019158075A1 (zh) | 2019-08-22 |
| JP2021514353A (ja) | 2021-06-10 |
| IL276611A (en) | 2020-09-30 |
| SG11202007733SA (en) | 2020-09-29 |
| US11708368B2 (en) | 2023-07-25 |
| KR102647713B1 (ko) | 2024-03-13 |
| EP3753940A4 (en) | 2021-12-22 |
| EP3753940B1 (en) | 2024-12-04 |
| EP3753940A1 (en) | 2020-12-23 |
| CA3090913A1 (en) | 2019-08-22 |
| EA202091927A1 (ru) | 2020-12-07 |
| CA3090913C (en) | 2024-01-02 |
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