HRP20040207A2 - Ascorbic acid derivatives, methods of synthesis and pharmaceutical use thereof - Google Patents
Ascorbic acid derivatives, methods of synthesis and pharmaceutical use thereof Download PDFInfo
- Publication number
- HRP20040207A2 HRP20040207A2 HR20040207A HRP20040207A HRP20040207A2 HR P20040207 A2 HRP20040207 A2 HR P20040207A2 HR 20040207 A HR20040207 A HR 20040207A HR P20040207 A HRP20040207 A HR P20040207A HR P20040207 A2 HRP20040207 A2 HR P20040207A2
- Authority
- HR
- Croatia
- Prior art keywords
- lysine
- proline
- ascorbyl
- ascorbic acid
- polylysine
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 133
- 125000003289 ascorbyl group Chemical class [H]O[C@@]([H])(C([H])([H])O*)[C@@]1([H])OC(=O)C(O*)=C1O* 0.000 title claims description 7
- 230000015572 biosynthetic process Effects 0.000 title description 24
- 238000003786 synthesis reaction Methods 0.000 title description 22
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 474
- 229960005070 ascorbic acid Drugs 0.000 claims description 228
- 239000002211 L-ascorbic acid Substances 0.000 claims description 212
- 235000000069 L-ascorbic acid Nutrition 0.000 claims description 212
- 239000004472 Lysine Substances 0.000 claims description 176
- 150000000996 L-ascorbic acids Chemical class 0.000 claims description 141
- 235000018977 lysine Nutrition 0.000 claims description 99
- 125000003588 lysine group Chemical group [H]N([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 claims description 95
- 125000001500 prolyl group Chemical group [H]N1C([H])(C(=O)[*])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 89
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 87
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- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 claims description 58
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- 239000008194 pharmaceutical composition Substances 0.000 claims description 19
- LGBPWIAXPVUTMY-JLAZNSOCSA-N (2r)-3,4-dihydroxy-2-[(1s)-1-hydroxyethyl]-2h-furan-5-one Chemical compound C[C@H](O)[C@H]1OC(=O)C(O)=C1O LGBPWIAXPVUTMY-JLAZNSOCSA-N 0.000 claims description 17
- DGQAOZJEDXIMGQ-RAGRJFKESA-N N1[C@@H](CCC1)C(=O)O.N[C@@H](CCCCN)C(=O)O.O=C1C(O)=C(O)[C@H](O1)[C@@H](O)C Chemical compound N1[C@@H](CCC1)C(=O)O.N[C@@H](CCCCN)C(=O)O.O=C1C(O)=C(O)[C@H](O1)[C@@H](O)C DGQAOZJEDXIMGQ-RAGRJFKESA-N 0.000 claims description 14
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 14
- 239000003937 drug carrier Substances 0.000 claims description 13
- PFTMONKBZOUTNL-LBNWCAIBSA-N (5R)-5-amino-3,4-dihydroxy-5-[(1S)-1-hydroxyethyl]furan-2-one Chemical compound C[C@H](O)[C@@]1(N)OC(=O)C(O)=C1O PFTMONKBZOUTNL-LBNWCAIBSA-N 0.000 claims description 12
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Classifications
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- 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
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/62—Three oxygen atoms, e.g. ascorbic acid
-
- 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
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/32—Oxygen atoms
- C07D307/33—Oxygen atoms in position 2, the oxygen atom being in its keto or unsubstituted enol form
-
- 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
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/34—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
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- 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
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/365—Lactones
- A61K31/375—Ascorbic acid, i.e. vitamin C; Salts thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cosmetics (AREA)
- Furan Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US31485701P | 2001-08-24 | 2001-08-24 | |
| PCT/EP2002/009451 WO2003018568A2 (fr) | 2001-08-24 | 2002-08-23 | Nouveaux composes d'acide ascorbique, leurs procedes de synthese et leur utilisation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20040207A2 true HRP20040207A2 (en) | 2005-02-28 |
Family
ID=23221754
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20040207A HRP20040207A2 (en) | 2001-08-24 | 2004-03-02 | Ascorbic acid derivatives, methods of synthesis and pharmaceutical use thereof |
Country Status (19)
| Country | Link |
|---|---|
| US (2) | US6864284B2 (fr) |
| EP (3) | EP2241559A3 (fr) |
| JP (1) | JP4162593B2 (fr) |
| KR (1) | KR20040044472A (fr) |
| CN (3) | CN100378087C (fr) |
| BR (1) | BR0205944A (fr) |
| CA (1) | CA2458344A1 (fr) |
| HR (1) | HRP20040207A2 (fr) |
| HU (1) | HUP0600084A2 (fr) |
| IL (4) | IL155578A0 (fr) |
| MX (1) | MXPA04001655A (fr) |
| NO (1) | NO20031844L (fr) |
| NZ (3) | NZ542241A (fr) |
| PL (1) | PL373522A1 (fr) |
| RU (1) | RU2309152C2 (fr) |
| UA (1) | UA78223C2 (fr) |
| WO (2) | WO2003018568A2 (fr) |
| YU (1) | YU38103A (fr) |
| ZA (1) | ZA200304712B (fr) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20040067890A1 (en) * | 2002-10-04 | 2004-04-08 | Gupta Shyam K. | Ascorbic acid salts of organic bases with enhanced bioavailability for synergictic anti-aging and skin protective cosmetic compositions |
| EP1620419A4 (fr) * | 2003-04-21 | 2008-07-23 | Tagra Biotechnologies Ltd | Derives stabilises d'acide ascorbique |
| CN100346782C (zh) * | 2004-05-21 | 2007-11-07 | 北京京卫信康医药科技发展有限公司 | 一种含氨基酸的维生素c组合物 |
| KR100544159B1 (ko) * | 2004-07-14 | 2006-01-24 | 센양 뉴라이프 인더스트리알 코 엘티디 | 아스코르빌 테트라이소팔미테이트와 디팔미토일하이드록시프롤린을 함유한 나노 에멀젼 및 이를함유하는 화장료 조성물 |
| US20070002866A1 (en) * | 2005-06-29 | 2007-01-04 | Denso Corporation | Receive power priority flooding in mobile ad hoc networks |
| CA2642726C (fr) | 2006-02-21 | 2015-11-03 | Mary Kay, Inc. | Compositions de vitamine c stables |
| US20080188553A1 (en) * | 2007-02-06 | 2008-08-07 | Waheed M Roomi | Novel ascorbic acid compounds, methods of synthesis and application use thereof |
| FR2913686B1 (fr) * | 2007-03-14 | 2009-05-01 | Oreal | Nouveaux composes carbamates de vitamine c, compositions les comprenant, et utilisations |
| US8828960B2 (en) * | 2007-07-17 | 2014-09-09 | Idexx Laboratories, Inc. | Amino acid vitamin ester compositions for controlled delivery of pharmaceutically active compounds |
| EP3478259A4 (fr) * | 2016-06-29 | 2020-02-26 | Orasis Medical, Inc. | Conjugués acide ascorbique-acide aminé et leur utilisation dans la régulation d'écoulement de fluide |
| US11629169B2 (en) * | 2017-09-15 | 2023-04-18 | Kine Sciences Co., Ltd. | Use of peptides as therapeutic agent for autoimmune diseases and bone diseases |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1273989A (fr) * | 1960-09-09 | 1961-10-20 | Marbou | Procédé de préparation de l'ascorbate de lysine |
| US4424232A (en) * | 1982-05-19 | 1984-01-03 | Parkinson Richard W | Treatment of herpes simplex |
| US4518614A (en) * | 1982-11-04 | 1985-05-21 | Redken Laboratories, Inc. | Cosmetic preparation |
| JPS63190882A (ja) * | 1987-02-03 | 1988-08-08 | Nippon Haipotsukusu:Kk | アスコルビン酸誘導体及びそれを含有する皮膚脱色剤並びにその製造法 |
| FR2650180B1 (fr) * | 1989-07-31 | 1995-03-03 | Chisso Corp | Procede de production d'une feuille facilement soluble dans l'eau a base d'acide hyaluronique ou de hyaluronate et feuille ainsi obtenue |
| AU8416391A (en) * | 1990-06-04 | 1992-01-07 | Therapy 2000 | Reduction of cardiovascular vessel occlusions with ascorbate and lipoprotein (a) binding inhibitors |
| JPH04247011A (ja) * | 1991-02-04 | 1992-09-03 | Q P Corp | リン脂質系アスコルビン酸誘導体及び該誘導体を含む皮膚外用剤 |
| US5977073A (en) * | 1991-06-06 | 1999-11-02 | Life Sciences' Technologies, Inc. | Nutrient composition for treatment of immune disorders |
| JPH0666958A (ja) * | 1991-08-29 | 1994-03-11 | Masaki Yoshigaki | 目覚し時計の目覚し設定並びに目覚し音停止機構 |
| JPH0678560A (ja) * | 1992-08-26 | 1994-03-18 | Matsushita Electric Works Ltd | インバータ装置 |
| FR2715156B1 (fr) | 1994-01-20 | 1996-03-01 | Oreal | Mono-esters d'acide cinnamique ou de ses dérivés et de vitamine C, leur procédé de préparation et leur utilisation comme anti-oxydants dans des compositions cosmétiques, pharmaceutiques ou alimentaires. |
| US5626883A (en) * | 1994-04-15 | 1997-05-06 | Metagenics, Inc. | Ascorbic acid compositions providing enhanced human immune system activity |
| US5951990A (en) | 1995-05-15 | 1999-09-14 | Avon Products, Inc. | Ascorbyl-phosphoryl-cholesterol |
| US5607968A (en) | 1995-06-07 | 1997-03-04 | Avon Products, Inc. | Topical alkyl-2-O-L-ascorbyl-phosphates |
| FR2737971B1 (fr) | 1995-08-25 | 1997-11-14 | Lvmh Rech | Utilisation de la vitamine c ou de ses derives ou analogues pour stimuler la synthese de l'elastine cutanee |
| US6162419A (en) | 1996-11-26 | 2000-12-19 | Nicholas V. Perricone | Stabilized ascorbyl compositions |
| US5962517A (en) * | 1997-01-31 | 1999-10-05 | Murad; Howard | Pharmaceutical compositions and methods for treating acne |
| EP0891771A1 (fr) * | 1997-07-08 | 1999-01-20 | Health Now, Inc. | Compositions comprenant du lysine et d'ascorbate ou ses dérivés pour le traitement de troubles cardiovasculaires |
-
2002
- 2002-08-23 CN CNB2005101136870A patent/CN100378087C/zh not_active Expired - Fee Related
- 2002-08-23 PL PL02373522A patent/PL373522A1/xx unknown
- 2002-08-23 NZ NZ542241A patent/NZ542241A/en unknown
- 2002-08-23 BR BR0205944-4A patent/BR0205944A/pt not_active IP Right Cessation
- 2002-08-23 WO PCT/EP2002/009451 patent/WO2003018568A2/fr active Application Filing
- 2002-08-23 EP EP10006653.9A patent/EP2241559A3/fr not_active Withdrawn
- 2002-08-23 ZA ZA200304712A patent/ZA200304712B/en unknown
- 2002-08-23 JP JP2003523231A patent/JP4162593B2/ja not_active Expired - Fee Related
- 2002-08-23 CN CNB028030184A patent/CN100360514C/zh not_active Expired - Fee Related
- 2002-08-23 IL IL15557802A patent/IL155578A0/xx not_active IP Right Cessation
- 2002-08-23 CA CA002458344A patent/CA2458344A1/fr not_active Abandoned
- 2002-08-23 EP EP10006654.7A patent/EP2241560A3/fr not_active Withdrawn
- 2002-08-23 NZ NZ542240A patent/NZ542240A/en unknown
- 2002-08-23 KR KR10-2004-7002629A patent/KR20040044472A/ko not_active Application Discontinuation
- 2002-08-23 NZ NZ531430A patent/NZ531430A/en unknown
- 2002-08-23 RU RU2004108687/04A patent/RU2309152C2/ru not_active IP Right Cessation
- 2002-08-23 CN CNB2005101136885A patent/CN100361987C/zh not_active Expired - Fee Related
- 2002-08-23 MX MXPA04001655A patent/MXPA04001655A/es active IP Right Grant
- 2002-08-23 HU HU0600084A patent/HUP0600084A2/hu unknown
- 2002-08-23 EP EP02772197A patent/EP1423375A2/fr not_active Withdrawn
- 2002-08-23 US US10/226,588 patent/US6864284B2/en not_active Expired - Fee Related
- 2002-08-23 WO PCT/US2002/027060 patent/WO2003018000A1/fr not_active Application Discontinuation
- 2002-08-23 UA UA2004032169A patent/UA78223C2/uk unknown
- 2002-08-23 YU YU38103A patent/YU38103A/sh unknown
-
2003
- 2003-04-24 IL IL155578A patent/IL155578A/en unknown
- 2003-04-24 IL IL176524A patent/IL176524A0/en unknown
- 2003-04-24 NO NO20031844A patent/NO20031844L/no not_active Application Discontinuation
-
2004
- 2004-02-18 US US10/781,296 patent/US7230124B2/en not_active Expired - Fee Related
- 2004-03-02 HR HR20040207A patent/HRP20040207A2/hr not_active Application Discontinuation
-
2006
- 2006-06-22 IL IL176523A patent/IL176523A0/en unknown
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