BR112018011414A2 - método para produzir derivados de ácido n-retinoilaminoalcano sulfônico - Google Patents
método para produzir derivados de ácido n-retinoilaminoalcano sulfônicoInfo
- Publication number
- BR112018011414A2 BR112018011414A2 BR112018011414A BR112018011414A BR112018011414A2 BR 112018011414 A2 BR112018011414 A2 BR 112018011414A2 BR 112018011414 A BR112018011414 A BR 112018011414A BR 112018011414 A BR112018011414 A BR 112018011414A BR 112018011414 A2 BR112018011414 A2 BR 112018011414A2
- Authority
- BR
- Brazil
- Prior art keywords
- acid
- sulfonic acid
- producing
- liquid phase
- alkyl ester
- Prior art date
Links
- 150000003458 sulfonic acid derivatives Chemical class 0.000 title abstract 3
- 238000004519 manufacturing process Methods 0.000 title 1
- 125000005907 alkyl ester group Chemical group 0.000 abstract 4
- 239000007791 liquid phase Substances 0.000 abstract 3
- XVOYSCVBGLVSOL-UHFFFAOYSA-N cysteic acid Chemical compound OC(=O)C(N)CS(O)(=O)=O XVOYSCVBGLVSOL-UHFFFAOYSA-N 0.000 abstract 2
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 abstract 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 abstract 1
- VBOQYPQEPHKASR-VKHMYHEASA-N L-homocysteic acid Chemical compound OC(=O)[C@@H](N)CCS(O)(=O)=O VBOQYPQEPHKASR-VKHMYHEASA-N 0.000 abstract 1
- 239000002253 acid Substances 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
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 abstract 1
- 235000018417 cysteine Nutrition 0.000 abstract 1
- PDNJLMZEGXHSCU-UHFFFAOYSA-N homocysteine sulfinic acid Chemical compound OC(=O)C(N)CCS(O)=O PDNJLMZEGXHSCU-UHFFFAOYSA-N 0.000 abstract 1
- 239000000203 mixture Substances 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
trata-se de um método para produzir derivados de ácido nretinoilaminoalcano sulfônico, sendo que o método compreende fornecer ácido retinoico, cloroformato, ácido aminoalcanossulfônico selecionado a partir do grupo que consiste em ácido cisteico e éster alquílico do mesmo, ácido cisteína sulfínico e éster alquílico do mesmo, ácido homocisteico e éster alquílico do mesmo, ácido homocisteína sulfínico e ésteres alquílicos do mesmo, taurina e derivados dos mesmos, e um solvente orgânico, e uma base, misturar os ditos componentes sob ausência substancial de compostos de oxidação formando, desse modo, uma mistura de reação que compreende uma fase líquida, em que a fase líquida é uma fase e os derivados de ácido n-retinoilaminoalcano sulfônico são formados na dita fase líquida.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE1551615-6 | 2015-12-09 | ||
| 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 |
|---|---|
| BR112018011414A2 true BR112018011414A2 (pt) | 2018-11-27 |
| BR112018011414B1 BR112018011414B1 (pt) | 2022-09-20 |
Family
ID=59013796
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BR112018011414-6A BR112018011414B1 (pt) | 2015-12-09 | 2016-12-09 | Método para produzir derivados de ácido n-retinoilaminoalcano sulfônico |
Country Status (21)
| Country | Link |
|---|---|
| US (2) | US10138204B2 (pt) |
| EP (1) | EP3386947B1 (pt) |
| JP (1) | JP7009012B2 (pt) |
| KR (1) | KR20180091851A (pt) |
| CN (2) | CN116444463A (pt) |
| AU (1) | AU2016365535B2 (pt) |
| BR (1) | BR112018011414B1 (pt) |
| CA (1) | CA3007624C (pt) |
| DK (1) | DK3386947T3 (pt) |
| EA (1) | EA037846B1 (pt) |
| ES (1) | ES2881882T3 (pt) |
| HK (1) | HK1258219A1 (pt) |
| LT (1) | LT3386947T (pt) |
| MX (1) | MX2018006894A (pt) |
| MY (1) | MY184709A (pt) |
| NZ (1) | NZ743639A (pt) |
| SG (1) | SG11201804826TA (pt) |
| SI (1) | SI3386947T1 (pt) |
| UA (1) | UA124338C2 (pt) |
| WO (1) | WO2017099662A1 (pt) |
| ZA (1) | ZA201804250B (pt) |
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 DK DK16873468.9T patent/DK3386947T3/da active
- 2016-12-09 SI SI201631233T patent/SI3386947T1/sl unknown
- 2016-12-09 LT LTEP16873468.9T patent/LT3386947T/lt unknown
- 2016-12-09 MX MX2018006894A patent/MX2018006894A/es unknown
- 2016-12-09 KR KR1020187017826A patent/KR20180091851A/ko active Search and Examination
- 2016-12-09 CA CA3007624A patent/CA3007624C/en active Active
- 2016-12-09 EP EP16873468.9A patent/EP3386947B1/en active Active
- 2016-12-09 JP JP2018530592A patent/JP7009012B2/ja active Active
- 2016-12-09 EA EA201891259A patent/EA037846B1/ru unknown
- 2016-12-09 AU AU2016365535A patent/AU2016365535B2/en active Active
- 2016-12-09 ES ES16873468T patent/ES2881882T3/es active Active
- 2016-12-09 BR BR112018011414-6A patent/BR112018011414B1/pt active IP Right Grant
- 2016-12-09 CN CN202310373566.8A patent/CN116444463A/zh active Pending
- 2016-12-09 MY MYPI2018702173A patent/MY184709A/en unknown
- 2016-12-09 WO PCT/SE2016/051238 patent/WO2017099662A1/en active Application Filing
- 2016-12-09 CN CN201680071797.1A patent/CN108473421A/zh active Pending
- 2016-12-09 NZ NZ743639A patent/NZ743639A/en unknown
- 2016-12-09 SG SG11201804826TA patent/SG11201804826TA/en unknown
- 2016-12-09 UA UAA201807009A patent/UA124338C2/uk unknown
-
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 |
|---|---|
| ZA201804250B (en) | 2019-04-24 |
| BR112018011414B1 (pt) | 2022-09-20 |
| CN116444463A (zh) | 2023-07-18 |
| UA124338C2 (uk) | 2021-09-01 |
| JP2019504005A (ja) | 2019-02-14 |
| LT3386947T (lt) | 2021-09-10 |
| ES2881882T3 (es) | 2021-11-30 |
| US20190127322A1 (en) | 2019-05-02 |
| MY184709A (en) | 2021-04-19 |
| HK1258219A1 (zh) | 2019-11-08 |
| SG11201804826TA (en) | 2018-07-30 |
| EP3386947A4 (en) | 2019-05-15 |
| NZ743639A (en) | 2022-07-01 |
| SI3386947T1 (sl) | 2021-11-30 |
| AU2016365535A1 (en) | 2018-07-12 |
| CN108473421A (zh) | 2018-08-31 |
| CA3007624C (en) | 2024-04-09 |
| KR20180091851A (ko) | 2018-08-16 |
| CA3007624A1 (en) | 2017-06-15 |
| DK3386947T3 (da) | 2021-08-09 |
| MX2018006894A (es) | 2018-11-09 |
| US10138204B2 (en) | 2018-11-27 |
| EP3386947B1 (en) | 2021-05-19 |
| WO2017099662A1 (en) | 2017-06-15 |
| US10322996B2 (en) | 2019-06-18 |
| JP7009012B2 (ja) | 2022-01-25 |
| AU2016365535B2 (en) | 2020-07-23 |
| US20180290973A1 (en) | 2018-10-11 |
| EP3386947A1 (en) | 2018-10-17 |
| EA037846B1 (ru) | 2021-05-27 |
| EA201891259A1 (ru) | 2019-01-31 |
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