HRP940646A2 - Water-soluble retinoids - Google Patents
Water-soluble retinoids Download PDFInfo
- Publication number
- HRP940646A2 HRP940646A2 HR9320610.0A HRP940646A HRP940646A2 HR P940646 A2 HRP940646 A2 HR P940646A2 HR P940646 A HRP940646 A HR P940646A HR P940646 A2 HRP940646 A2 HR P940646A2
- Authority
- HR
- Croatia
- Prior art keywords
- compound
- formula
- retinoic acid
- obtaining
- glucose
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 46
- 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 claims description 27
- 229930002330 retinoic acid Natural products 0.000 claims description 27
- 229960001727 tretinoin Drugs 0.000 claims description 24
- 235000000346 sugar Nutrition 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 20
- -1 Retinoic acid ester Chemical class 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 150000002772 monosaccharides Chemical group 0.000 claims description 11
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- 239000008103 glucose Substances 0.000 claims description 9
- 239000002537 cosmetic Substances 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
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- 125000001424 substituent group Chemical group 0.000 claims description 2
- 229910001413 alkali metal ion Inorganic materials 0.000 claims 1
- XAEXWGDKGUEINI-UHFFFAOYSA-N n,n-dimethylcarbamimidoyl chloride;hydrochloride Chemical compound [Cl-].C[N+](C)=C(N)Cl XAEXWGDKGUEINI-UHFFFAOYSA-N 0.000 claims 1
- 150000004492 retinoid derivatives Chemical class 0.000 claims 1
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- 229960005070 ascorbic acid Drugs 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 230000036952 cancer formation Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 231100000504 carcinogenesis Toxicity 0.000 description 1
- 230000032823 cell division Effects 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000012320 chlorinating reagent Substances 0.000 description 1
- 239000007857 degradation product Substances 0.000 description 1
- 238000001212 derivatisation Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 210000000981 epithelium Anatomy 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000004299 exfoliation Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- IXZISFNWUWKBOM-ARQDHWQXSA-N fructosamine Chemical compound NC[C@@]1(O)OC[C@@H](O)[C@@H](O)[C@@H]1O IXZISFNWUWKBOM-ARQDHWQXSA-N 0.000 description 1
- 229940080345 gamma-cyclodextrin Drugs 0.000 description 1
- 125000000457 gamma-lactone group Chemical group 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000000174 gluconic acid Substances 0.000 description 1
- 235000012208 gluconic acid Nutrition 0.000 description 1
- 229960002442 glucosamine Drugs 0.000 description 1
- 229940074050 glyceryl myristate Drugs 0.000 description 1
- 150000002337 glycosamines Chemical class 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- JBFYUZGYRGXSFL-UHFFFAOYSA-N imidazolide Chemical compound C1=C[N-]C=N1 JBFYUZGYRGXSFL-UHFFFAOYSA-N 0.000 description 1
- 230000003780 keratinization Effects 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 239000002502 liposome Substances 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- ZBOBHFDVBPNIDH-UHFFFAOYSA-N n'-methylethanimidamide;hydrochloride Chemical compound Cl.CNC(C)=N ZBOBHFDVBPNIDH-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 238000010606 normalization Methods 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 238000011458 pharmacological treatment Methods 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 230000009993 protective function Effects 0.000 description 1
- DCBSHORRWZKAKO-UHFFFAOYSA-N rac-1-monomyristoylglycerol Chemical compound CCCCCCCCCCCCCC(=O)OCC(O)CO DCBSHORRWZKAKO-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000003716 rejuvenation Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000001587 sorbitan monostearate Substances 0.000 description 1
- 235000011076 sorbitan monostearate Nutrition 0.000 description 1
- 229940035048 sorbitan monostearate Drugs 0.000 description 1
- 229950011392 sorbitan stearate Drugs 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000019635 sulfation Effects 0.000 description 1
- 238000005670 sulfation reaction Methods 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 231100000378 teratogenic Toxicity 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
- A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/67—Vitamins
- A61K8/671—Vitamin A; Derivatives thereof, e.g. ester of vitamin A acid, ester of retinol, retinol, retinal
-
- 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
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
- C07H13/04—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals attached to acyclic carbon atoms
- C07H13/06—Fatty acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/18—Acyclic radicals, substituted by carbocyclic rings
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Dermatology (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cosmetics (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9320610A GB2282596B (en) | 1993-10-06 | 1993-10-06 | Water-soluble retinoids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP940646A2 true HRP940646A2 (en) | 1997-04-30 |
Family
ID=10743103
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR9320610.0A HRP940646A2 (en) | 1993-10-06 | 1994-10-05 | Water-soluble retinoids |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US5780443A (fr) |
| EP (1) | EP0722451A1 (fr) |
| JP (1) | JPH09503499A (fr) |
| KR (1) | KR960704904A (fr) |
| AU (1) | AU687098B2 (fr) |
| BR (1) | BR9407758A (fr) |
| CZ (1) | CZ100896A3 (fr) |
| GB (1) | GB2282596B (fr) |
| HR (1) | HRP940646A2 (fr) |
| HU (1) | HUT74456A (fr) |
| IL (1) | IL111152A (fr) |
| WO (1) | WO1995009862A1 (fr) |
| ZA (1) | ZA947775B (fr) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU3627695A (en) * | 1994-09-30 | 1996-04-26 | Alcon Laboratories, Inc. | Use of retinoid glycosides in topical pharmaceutical compositions |
| EP1318784A1 (fr) * | 2000-09-11 | 2003-06-18 | Industria E Comércio de Cosméticos Natura Ltda. | Composition de vitamine c et/ou de vitamine a |
| FR2813789B1 (fr) * | 2000-09-11 | 2003-05-02 | Ind E Com De Cosmeticos Natura | Nouvelle composition cosmetique ou pharmaceutique comprenant une association de vitamine c et/ou avec un composant fucose, et utilisation de cette association en cosmetique ou pharmacie |
| US20040021483A1 (en) * | 2001-09-28 | 2004-02-05 | Brian Boles | Functional pathway configuration at a system/IC interface |
| US20060201531A1 (en) * | 2001-12-04 | 2006-09-14 | Brown Dale G | Methods for coating dental devices with sialagogue emulsions |
| JP5285201B2 (ja) * | 2002-09-25 | 2013-09-11 | 株式会社ナノエッグ | レチノイン酸ナノカプセル |
| ITMI20022745A1 (it) * | 2002-12-23 | 2004-06-24 | Coimex Scrl United Companies | Esteri misti dell'acido ialuronico ad attivita' citostatica e prodifferenziante e procedimento per la loro produzione. |
| JP4535238B2 (ja) * | 2004-03-17 | 2010-09-01 | 国立大学法人 香川大学 | プシコースのレチノイン酸エステル及びその製造方法 |
| US20160038593A1 (en) * | 2004-12-22 | 2016-02-11 | Nitto Denko Corporation | Drug carrier and drug carrier kit for inhibiting fibrosis |
| US20060237021A1 (en) * | 2005-04-21 | 2006-10-26 | Guay Gordon G | Methods and devices for rejuvenating skin |
| US20110081410A1 (en) * | 2005-06-28 | 2011-04-07 | St. Marianna University, School Ofmedicine | Therapeutic agent for local inflammation |
| KR101002795B1 (ko) | 2008-09-19 | 2010-12-21 | (주)더페이스샵 | 신규한 레티닐 아스코르베이트 화합물 및 그 제조방법 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4457918A (en) * | 1982-05-12 | 1984-07-03 | The General Hospital Corporation | Glycosides of vitamins A, E and K |
| CH661516A5 (de) * | 1983-12-08 | 1987-07-31 | Hoffmann La Roche | Phenylnonatetraenoylzuckerderivate. |
| LU87041A1 (fr) * | 1987-11-04 | 1989-06-14 | Oreal | Esters retinoiques de macrolides,leur procede de preparation et compositions pharmaceutiques et cosmetiques les contenant |
| FR2598420B1 (fr) * | 1986-05-06 | 1991-06-07 | Oreal | Nouveaux esters retinoiques d'antibiotiques, leur procede de preparation et compositions pharmaceutiques et cosmetiques les contenant |
| US5049664A (en) * | 1988-08-26 | 1991-09-17 | Sawai Pharmaceutical Co., Ltd. | Trehalose derivatives |
| FR2644460A1 (fr) * | 1989-03-16 | 1990-09-21 | Oreal | Esters retinoiques de d-desosamine, leur procede de preparation et leur utilisation en medecine humaine ou veterinaire et en cosmetique |
| AU618198B2 (en) * | 1989-05-22 | 1991-12-12 | Iowa State University Research Foundation Inc. | Water-soluble vitamin a preparations for application to the skin |
| CH684092A5 (de) * | 1992-04-21 | 1994-07-15 | Ciba Geigy Ag | Wasserlösliche Retinoide. |
-
1993
- 1993-10-06 GB GB9320610A patent/GB2282596B/en not_active Expired - Fee Related
-
1994
- 1994-09-24 WO PCT/EP1994/003187 patent/WO1995009862A1/fr not_active Application Discontinuation
- 1994-09-24 BR BR9407758A patent/BR9407758A/pt not_active Application Discontinuation
- 1994-09-24 AU AU78096/94A patent/AU687098B2/en not_active Ceased
- 1994-09-24 US US08/624,379 patent/US5780443A/en not_active Expired - Fee Related
- 1994-09-24 JP JP7510586A patent/JPH09503499A/ja active Pending
- 1994-09-24 HU HU9600884A patent/HUT74456A/hu unknown
- 1994-09-24 EP EP94928806A patent/EP0722451A1/fr not_active Withdrawn
- 1994-09-24 CZ CZ961008A patent/CZ100896A3/cs unknown
- 1994-09-24 KR KR1019960701755A patent/KR960704904A/ko not_active Application Discontinuation
- 1994-10-04 IL IL11115294A patent/IL111152A/en not_active IP Right Cessation
- 1994-10-05 HR HR9320610.0A patent/HRP940646A2/hr not_active Application Discontinuation
- 1994-10-05 ZA ZA947775A patent/ZA947775B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JPH09503499A (ja) | 1997-04-08 |
| KR960704904A (ko) | 1996-10-09 |
| AU687098B2 (en) | 1998-02-19 |
| GB9320610D0 (en) | 1993-11-24 |
| HUT74456A (en) | 1996-12-30 |
| AU7809694A (en) | 1995-05-01 |
| US5780443A (en) | 1998-07-14 |
| GB2282596A (en) | 1995-04-12 |
| WO1995009862A1 (fr) | 1995-04-13 |
| IL111152A0 (en) | 1994-12-29 |
| GB2282596B (en) | 1998-04-15 |
| CZ100896A3 (en) | 1996-10-16 |
| HU9600884D0 (en) | 1996-06-28 |
| ZA947775B (en) | 1995-05-17 |
| IL111152A (en) | 2001-03-19 |
| BR9407758A (pt) | 1997-03-04 |
| EP0722451A1 (fr) | 1996-07-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A1OB | Publication of a patent application | ||
| PNAN | Change of the applicant name, address/residence |
Owner name: CIBA SPECIALTY CHEMICALS HOLDING INC., CH |
|
| AIPI | Request for the grant of a patent on the basis of a substantive examination of a patent application | ||
| ODBI | Application refused |