EA201891259A1 - Способ получения алкилового эфира n-ретиноилцистеиновой кислоты - Google Patents
Способ получения алкилового эфира n-ретиноилцистеиновой кислотыInfo
- Publication number
- EA201891259A1 EA201891259A1 EA201891259A EA201891259A EA201891259A1 EA 201891259 A1 EA201891259 A1 EA 201891259A1 EA 201891259 A EA201891259 A EA 201891259A EA 201891259 A EA201891259 A EA 201891259A EA 201891259 A1 EA201891259 A1 EA 201891259A1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- acid
- alkyl ether
- homo
- homocysteic
- sistimine
- Prior art date
Links
- 239000002253 acid Substances 0.000 title abstract 9
- 150000005215 alkyl ethers Chemical class 0.000 title abstract 7
- 238000000034 method Methods 0.000 title abstract 3
- VBOQYPQEPHKASR-VKHMYHEASA-N L-homocysteic acid Chemical compound OC(=O)[C@@H](N)CCS(O)(=O)=O VBOQYPQEPHKASR-VKHMYHEASA-N 0.000 abstract 6
- 125000005907 alkyl ester group Chemical group 0.000 abstract 5
- XVOYSCVBGLVSOL-UHFFFAOYSA-N cysteic acid Chemical compound OC(=O)C(N)CS(O)(=O)=O XVOYSCVBGLVSOL-UHFFFAOYSA-N 0.000 abstract 3
- 239000007791 liquid phase Substances 0.000 abstract 3
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 abstract 2
- XVOYSCVBGLVSOL-REOHCLBHSA-N L-cysteic acid Chemical compound OC(=O)[C@@H](N)CS(O)(=O)=O XVOYSCVBGLVSOL-REOHCLBHSA-N 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 abstract 1
- SHGAZHPCJJPHSC-YCNIQYBTSA-N all-trans-retinoic acid Chemical compound OC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-YCNIQYBTSA-N 0.000 abstract 1
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 239000012071 phase Substances 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 229930002330 retinoic acid Natural products 0.000 abstract 1
- 229960003080 taurine Drugs 0.000 abstract 1
- 229960001727 tretinoin Drugs 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/04—Compounds containing oxirane rings containing only hydrogen and carbon atoms in addition to the ring oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
- C07C403/22—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
- C07C403/20—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by carboxyl groups or halides, anhydrides, or (thio)esters thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/32—Separation; Purification
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/38—Compounds containing oxirane rings with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D303/46—Compounds containing oxirane rings with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals by amide or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Furan Compounds (AREA)
- Epoxy Compounds (AREA)
Abstract
Способ получения производных N-ретиноиламиноалкансульфоновой кислоты, способ включает использование ретиноевой кислоты, хлорформиата, аминоалкансульфоновой кислоты, выбранной из группы, включающей цистеиновую кислоту и ее алкиловый эфир, цистеинсульфиновую кислоту и ее алкиловый эфир, гомоцистеиновую кислоту и ее алкиловый эфир, гомоцистеинсульфиновую кислоту и ее алкиловые эфиры, таурин и его производные, и органический растворитель и основание, смешивание указанных компонентов в основном при отсутствии окисляющих соединений, тем самым получение реакционной смеси, включающей, по меньшей мере, жидкую фазу, где жидкая фаза является одной фазой и производные N-ретиноиламиноалкансульфоновой кислоты образуются в указанной жидкой фазе.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE1551615 | 2015-12-09 | ||
| PCT/SE2016/051238 WO2017099662A1 (en) | 2015-12-09 | 2016-12-09 | Method for producing n-retinoylcysteic acid alkyl ester |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EA201891259A1 true EA201891259A1 (ru) | 2019-01-31 |
| EA037846B1 EA037846B1 (ru) | 2021-05-27 |
Family
ID=59013796
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EA201891259A EA037846B1 (ru) | 2015-12-09 | 2016-12-09 | Способ получения алкилового эфира n-ретиноилцистеиновой кислоты |
Country Status (21)
| Country | Link |
|---|---|
| US (2) | US10138204B2 (ru) |
| EP (1) | EP3386947B1 (ru) |
| JP (1) | JP7009012B2 (ru) |
| KR (1) | KR20180091851A (ru) |
| CN (2) | CN116444463A (ru) |
| AU (1) | AU2016365535B2 (ru) |
| BR (1) | BR112018011414B1 (ru) |
| CA (1) | CA3007624C (ru) |
| DK (1) | DK3386947T3 (ru) |
| EA (1) | EA037846B1 (ru) |
| ES (1) | ES2881882T3 (ru) |
| HK (1) | HK1258219A1 (ru) |
| LT (1) | LT3386947T (ru) |
| MX (1) | MX2018006894A (ru) |
| MY (1) | MY184709A (ru) |
| NZ (1) | NZ743639A (ru) |
| SG (1) | SG11201804826TA (ru) |
| SI (1) | SI3386947T1 (ru) |
| UA (1) | UA124338C2 (ru) |
| WO (1) | WO2017099662A1 (ru) |
| ZA (1) | ZA201804250B (ru) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110218168B (zh) * | 2018-03-02 | 2022-09-20 | 上海现代药物制剂工程研究中心有限公司 | 一种n-(全反式-视黄酰基)-l-半胱磺酸甲酯的钠盐的制备方法 |
| CN112239418B (zh) * | 2019-07-18 | 2023-07-07 | 上海现代药物制剂工程研究中心有限公司 | 视黄醇类化合物及其钠盐的制备方法 |
| US11072575B1 (en) * | 2020-09-19 | 2021-07-27 | Xi'an Taikomed Pharmaceutical Technology Co., Ltd. | Method of preparing a cinnamyl alcohol retinoic acid ester with antioxidant and antibacterial activities |
| US11401239B1 (en) | 2020-10-13 | 2022-08-02 | Fxi Inc. Limited | Process for converting disulfides to conversion products and process for producing cysteic acid |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3002545A1 (de) * | 1980-01-25 | 1981-07-30 | Basf Ag, 6700 Ludwigshafen | 5-amino-tetrazol-derivate von retinsaeuren, ihre herstellung und diese enthaltende pharmazeutische zubereitungen |
| SE0101702D0 (sv) * | 2001-05-15 | 2001-05-15 | Ardenia Investments Ltd | Novel potentiating compounds |
| SE0202311D0 (sv) * | 2002-07-23 | 2002-07-23 | Ardenia Investments Ltd | Novel compounds, cytotoxic preparations comprising said compounds, methods of manufacture of said preparations, as well as methods of treatment |
| EP1534672B1 (en) * | 2002-07-23 | 2013-05-01 | Ardenia Investments Ltd. | Retinol derivatives, their use in the treatment of cancer and for potentiating the efficacy of other cytotoxic agents |
| US7321064B1 (en) * | 2007-03-08 | 2008-01-22 | Cedarburg Pharmaceuticals, Inc. | Preparation of amides of retinoic acid via mixed anhydride and mixed carbonate intermediates |
-
2016
- 2016-12-09 ES ES16873468T patent/ES2881882T3/es active Active
- 2016-12-09 KR KR1020187017826A patent/KR20180091851A/ko active Search and Examination
- 2016-12-09 AU AU2016365535A patent/AU2016365535B2/en active Active
- 2016-12-09 JP JP2018530592A patent/JP7009012B2/ja active Active
- 2016-12-09 CN CN202310373566.8A patent/CN116444463A/zh active Pending
- 2016-12-09 SI SI201631233T patent/SI3386947T1/sl unknown
- 2016-12-09 EA EA201891259A patent/EA037846B1/ru unknown
- 2016-12-09 DK DK16873468.9T patent/DK3386947T3/da active
- 2016-12-09 CA CA3007624A patent/CA3007624C/en active Active
- 2016-12-09 CN CN201680071797.1A patent/CN108473421A/zh active Pending
- 2016-12-09 MY MYPI2018702173A patent/MY184709A/en unknown
- 2016-12-09 NZ NZ743639A patent/NZ743639A/en unknown
- 2016-12-09 WO PCT/SE2016/051238 patent/WO2017099662A1/en active Application Filing
- 2016-12-09 BR BR112018011414-6A patent/BR112018011414B1/pt active IP Right Grant
- 2016-12-09 UA UAA201807009A patent/UA124338C2/uk unknown
- 2016-12-09 SG SG11201804826TA patent/SG11201804826TA/en unknown
- 2016-12-09 LT LTEP16873468.9T patent/LT3386947T/lt unknown
- 2016-12-09 MX MX2018006894A patent/MX2018006894A/es unknown
- 2016-12-09 EP EP16873468.9A patent/EP3386947B1/en active Active
-
2018
- 2018-06-08 US US16/003,209 patent/US10138204B2/en active Active
- 2018-06-25 ZA ZA2018/04250A patent/ZA201804250B/en unknown
- 2018-10-31 US US16/176,215 patent/US10322996B2/en active Active
-
2019
- 2019-01-14 HK HK19100577.0A patent/HK1258219A1/zh unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BR112018011414A2 (pt) | 2018-11-27 |
| EP3386947A1 (en) | 2018-10-17 |
| MX2018006894A (es) | 2018-11-09 |
| ES2881882T3 (es) | 2021-11-30 |
| SI3386947T1 (sl) | 2021-11-30 |
| EA037846B1 (ru) | 2021-05-27 |
| US20180290973A1 (en) | 2018-10-11 |
| CA3007624C (en) | 2024-04-09 |
| HK1258219A1 (zh) | 2019-11-08 |
| US20190127322A1 (en) | 2019-05-02 |
| US10138204B2 (en) | 2018-11-27 |
| WO2017099662A1 (en) | 2017-06-15 |
| ZA201804250B (en) | 2019-04-24 |
| CA3007624A1 (en) | 2017-06-15 |
| DK3386947T3 (da) | 2021-08-09 |
| KR20180091851A (ko) | 2018-08-16 |
| CN116444463A (zh) | 2023-07-18 |
| NZ743639A (en) | 2022-07-01 |
| BR112018011414B1 (pt) | 2022-09-20 |
| AU2016365535B2 (en) | 2020-07-23 |
| LT3386947T (lt) | 2021-09-10 |
| UA124338C2 (uk) | 2021-09-01 |
| JP2019504005A (ja) | 2019-02-14 |
| EP3386947B1 (en) | 2021-05-19 |
| AU2016365535A1 (en) | 2018-07-12 |
| JP7009012B2 (ja) | 2022-01-25 |
| US10322996B2 (en) | 2019-06-18 |
| SG11201804826TA (en) | 2018-07-30 |
| MY184709A (en) | 2021-04-19 |
| EP3386947A4 (en) | 2019-05-15 |
| CN108473421A (zh) | 2018-08-31 |
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