SG11201804826TA - Method for producing n-retinoylcysteic acid alkyl ester - Google Patents
Method for producing n-retinoylcysteic acid alkyl esterInfo
- Publication number
- SG11201804826TA SG11201804826TA SG11201804826TA SG11201804826TA SG11201804826TA SG 11201804826T A SG11201804826T A SG 11201804826TA SG 11201804826T A SG11201804826T A SG 11201804826TA SG 11201804826T A SG11201804826T A SG 11201804826TA SG 11201804826T A SG11201804826T A SG 11201804826TA
- Authority
- SG
- Singapore
- Prior art keywords
- acid
- international
- alkyl ester
- uppsala
- pct
- Prior art date
Links
- 239000002253 acid Substances 0.000 title abstract 5
- 125000005907 alkyl ester group Chemical group 0.000 title abstract 5
- 238000004519 manufacturing process Methods 0.000 title abstract 3
- 239000007791 liquid phase Substances 0.000 abstract 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 abstract 2
- 235000003332 Ilex aquifolium Nutrition 0.000 abstract 1
- 241000209027 Ilex aquifolium Species 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
- 241001170774 Maryna Species 0.000 abstract 1
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 abstract 1
- 235000018417 cysteine Nutrition 0.000 abstract 1
- 150000001945 cysteines Chemical class 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
- 238000000034 method Methods 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 230000008520 organization Effects 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 229960003080 taurine 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
INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property Organization International Bureau IIIIII Hit II EH DID IIIII DEEM II 11111111111111111111111111111111 RID IIII (10) International Publication Number WO 2017/099662 Al WIPO I PCT (43) International Publication Date 15 June 2017 (15.06.2017) (81) Designated States (unless otherwise indicated, for every kind of national protection available): AE, AG, AL, AM, AO, AT, AU, AZ, BA, BB, BG, BH, BN, BR, BW, BY, BZ, CA, CH, CL, CN, CO, CR, CU, CZ, DE, DJ, DK, DM, DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, HN, HR, HU, ID, IL, IN, IR, IS, JP, KE, KG, KB, KN, KP, KR, KW, KZ, LA, LC, LK, LR, LS, LU, LY, MA, MD, ME, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, OM, PA, PE, PG, PH, PL, PT, QA, RO, RS, RU, RW, SA, SC, SD, SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW. (84) Designated States (unless otherwise indicated, for every kind of regional protection available): ARIPO (BW, GH, GM, KE, LR, LS, MW, MZ, NA, RW, SD, SL, ST, SZ, TZ, UG, ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, RU, TJ, TM), European (AL, AT, BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, FR, GB, GR, HR, HU, IE, IS, IT, LT, LU, LV, MC, MK, MT, NL, NO, PL, PT, RO, RS, SE, SI, SK, SM, TR), OAPI (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, GW, KM, ML, MR, NE, SN, TD, TG). Published: (51) International Patent Classification: C07C 403/22 (2006.01) CO7C 309/23 (2006.01) C07C 30 9 / 1 8 (2006.01) CO7C 313/04 (2006.01) (21) International Application Number: PCT/SE2016/051238 (22) International Filing Date: 9 December 2016 (09.12.2016) (25) Filing Language: English (26) Publication Language: English (30) Priority Data: 1551615-6 9 December 2015 (09.12.2015) SE (71) Applicant: ARDENIA INVESTMENTS, LTD. [GB/GB]; 45 Welbeck Street, London WIG8DZ (GB). (72) Inventors; and (71) Applicants : BABROU, Dzianis [SE/SE]; Stigbergsplan 3, 75242 Uppsala (SE). BUDNIKAVA, Maryna [SE/SE]; Stigbergsplan 3, 75242 Uppsala (SE). BJORKLUND, Mi- kael [SE/SE]; Tingshogsgatan 9, 753 34 Uppsala (SE). ALEKSOV, Julian [SE/SE]; Karins All& 6, 181 44 Lid- ingo (SE). (74) Agent: BERGENSTRAHLE & PARTNERS STOCK- HOLM AB; P.O. Box 17704, 118 93 Stockholm (SE). with international search report (Art 21(3)) W O 20 17 /09966 2 Al (54) Title: METHOD FOR PRODUCING N-RETINOYLCYSTEIC ACID ALKYL ESTER (57) : A method for producing derivatives of N-retinoylaminoalkane sulfonic acid, the method comprising providing retino - ic acid, chloroformate, aminoalkanesulfonic acid selected from the group consisting of cysteic acidand alkyl ester thereof, cysteines - ulfmic acid and alkyl ester thereof, homocysteic acid and alkyl ester thereof, homocysteinesulfinic acid and alkyl esters thereof, taur - ine and derivatives thereof, and an organic solvent,and a base, mixing said components under substantial absence of oxidizing com - poundsthereby forming a reaction mixture comprising a liquid phase, wherein the liquid phase is one phaseand the derivatives of N- retinoylaminoalkane sulfonic acid are foiined in said liquid phase.
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 (1)
| Publication Number | Publication Date |
|---|---|
| SG11201804826TA true SG11201804826TA (en) | 2018-07-30 |
Family
ID=59013796
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SG11201804826TA SG11201804826TA (en) | 2015-12-09 | 2016-12-09 | Method for producing n-retinoylcysteic acid alkyl ester |
Country Status (21)
| Country | Link |
|---|---|
| US (2) | US10138204B2 (en) |
| EP (1) | EP3386947B1 (en) |
| JP (1) | JP7009012B2 (en) |
| KR (1) | KR20180091851A (en) |
| CN (2) | CN116444463A (en) |
| AU (1) | AU2016365535B2 (en) |
| BR (1) | BR112018011414B1 (en) |
| CA (1) | CA3007624C (en) |
| DK (1) | DK3386947T3 (en) |
| EA (1) | EA037846B1 (en) |
| ES (1) | ES2881882T3 (en) |
| HK (1) | HK1258219A1 (en) |
| LT (1) | LT3386947T (en) |
| MX (1) | MX2018006894A (en) |
| MY (1) | MY184709A (en) |
| NZ (1) | NZ743639A (en) |
| SG (1) | SG11201804826TA (en) |
| SI (1) | SI3386947T1 (en) |
| UA (1) | UA124338C2 (en) |
| WO (1) | WO2017099662A1 (en) |
| ZA (1) | ZA201804250B (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110218168B (en) * | 2018-03-02 | 2022-09-20 | 上海现代药物制剂工程研究中心有限公司 | Preparation method of sodium salt of N- (all-trans-retinoyl) -L-methyl cysteic acid |
| CN112239418B (en) * | 2019-07-18 | 2023-07-07 | 上海现代药物制剂工程研究中心有限公司 | Preparation method of retinol compound and sodium salt thereof |
| 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 (en) * | 1980-01-25 | 1981-07-30 | Basf Ag, 6700 Ludwigshafen | 5-AMINO-TETRAZOLE DERIVATIVES OF RETINIC ACIDS, THEIR PRODUCTION AND THE PHARMACEUTICAL PREPARATIONS CONTAINING THEM |
| SE0101702D0 (en) | 2001-05-15 | 2001-05-15 | Ardenia Investments Ltd | Novel potentiating compounds |
| WO2004009538A1 (en) * | 2002-07-23 | 2004-01-29 | Ardenia Investments Ltd. | Retinol derivatives, their use in the treatment of cancer and for potentiating the efficacy of other cytotoxic agents |
| SE0202311D0 (en) * | 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 |
| 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 NZ NZ743639A patent/NZ743639A/en unknown
- 2016-12-09 EP EP16873468.9A patent/EP3386947B1/en active Active
- 2016-12-09 LT LTEP16873468.9T patent/LT3386947T/en unknown
- 2016-12-09 ES ES16873468T patent/ES2881882T3/en active Active
- 2016-12-09 KR KR1020187017826A patent/KR20180091851A/en active Search and Examination
- 2016-12-09 JP JP2018530592A patent/JP7009012B2/en active Active
- 2016-12-09 CA CA3007624A patent/CA3007624C/en active Active
- 2016-12-09 WO PCT/SE2016/051238 patent/WO2017099662A1/en active Application Filing
- 2016-12-09 MX MX2018006894A patent/MX2018006894A/en unknown
- 2016-12-09 DK DK16873468.9T patent/DK3386947T3/en active
- 2016-12-09 SG SG11201804826TA patent/SG11201804826TA/en unknown
- 2016-12-09 UA UAA201807009A patent/UA124338C2/en unknown
- 2016-12-09 EA EA201891259A patent/EA037846B1/en unknown
- 2016-12-09 CN CN202310373566.8A patent/CN116444463A/en active Pending
- 2016-12-09 SI SI201631233T patent/SI3386947T1/en unknown
- 2016-12-09 BR BR112018011414-6A patent/BR112018011414B1/en active IP Right Grant
- 2016-12-09 MY MYPI2018702173A patent/MY184709A/en unknown
- 2016-12-09 CN CN201680071797.1A patent/CN108473421A/en active Pending
- 2016-12-09 AU AU2016365535A patent/AU2016365535B2/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/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP3386947B1 (en) | 2021-05-19 |
| CN116444463A (en) | 2023-07-18 |
| AU2016365535B2 (en) | 2020-07-23 |
| JP2019504005A (en) | 2019-02-14 |
| EP3386947A4 (en) | 2019-05-15 |
| EA037846B1 (en) | 2021-05-27 |
| CA3007624C (en) | 2024-04-09 |
| LT3386947T (en) | 2021-09-10 |
| US10138204B2 (en) | 2018-11-27 |
| SI3386947T1 (en) | 2021-11-30 |
| CA3007624A1 (en) | 2017-06-15 |
| ES2881882T3 (en) | 2021-11-30 |
| EP3386947A1 (en) | 2018-10-17 |
| AU2016365535A1 (en) | 2018-07-12 |
| HK1258219A1 (en) | 2019-11-08 |
| BR112018011414A2 (en) | 2018-11-27 |
| UA124338C2 (en) | 2021-09-01 |
| KR20180091851A (en) | 2018-08-16 |
| BR112018011414B1 (en) | 2022-09-20 |
| JP7009012B2 (en) | 2022-01-25 |
| NZ743639A (en) | 2022-07-01 |
| US20180290973A1 (en) | 2018-10-11 |
| WO2017099662A1 (en) | 2017-06-15 |
| DK3386947T3 (en) | 2021-08-09 |
| US20190127322A1 (en) | 2019-05-02 |
| CN108473421A (en) | 2018-08-31 |
| EA201891259A1 (en) | 2019-01-31 |
| US10322996B2 (en) | 2019-06-18 |
| ZA201804250B (en) | 2019-04-24 |
| MX2018006894A (en) | 2018-11-09 |
| MY184709A (en) | 2021-04-19 |
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