BG62167B1 - Производни на аскорбинова киселина,методи за тяхното получаване и приложение - Google Patents

Производни на аскорбинова киселина,методи за тяхното получаване и приложение Download PDF

Info

Publication number: BG62167B1
Authority: BG; Bulgaria
Prior art keywords: group; ascorbic acid; general formula; formula; compounds
Prior art date: 1993-02-05

Application number

BG98438A

Other languages

Bulgarian (bg)

English (en)

Other versions

BG98438A (bg

Inventor

Bozidar Suskovic

Vanja Vela

Mira Buncic

Original Assignee

Pliva Farmaceutska,Kemijska,Prehrambena Ikozmeticka Industrija, Dionicko Drustvo

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1993-02-05

Filing date

1994-02-04

Publication date

1999-04-30

1994-02-04 Application filed by Pliva Farmaceutska,Kemijska,Prehrambena Ikozmeticka Industrija, Dionicko Drustvo filed Critical Pliva Farmaceutska,Kemijska,Prehrambena Ikozmeticka Industrija, Dionicko Drustvo

1994-09-30 Publication of BG98438A publication Critical patent/BG98438A/bg

1999-04-30 Publication of BG62167B1 publication Critical patent/BG62167B1/bg

Links

238000002360 preparation method Methods 0.000 title claims abstract description 13
238000000034 method Methods 0.000 title claims abstract description 11
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 16
238000005804 alkylation reaction Methods 0.000 claims abstract description 14
230000029936 alkylation Effects 0.000 claims abstract description 12
239000002253 acid Substances 0.000 claims abstract description 11
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 24
229910052757 nitrogen Inorganic materials 0.000 claims description 22
150000001875 compounds Chemical class 0.000 claims description 19
229910052739 hydrogen Inorganic materials 0.000 claims description 17
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 13
239000003054 catalyst Substances 0.000 claims description 12
125000003118 aryl group Chemical group 0.000 claims description 11
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
125000000217 alkyl group Chemical group 0.000 claims description 10
239000001257 hydrogen Substances 0.000 claims description 10
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 9
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
125000005842 heteroatom Chemical group 0.000 claims description 9
150000002391 heterocyclic compounds Chemical class 0.000 claims description 9
229910052760 oxygen Inorganic materials 0.000 claims description 9
239000001301 oxygen Substances 0.000 claims description 9
239000011593 sulfur Substances 0.000 claims description 9
229910052717 sulfur Inorganic materials 0.000 claims description 9
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 6
229910052799 carbon Inorganic materials 0.000 claims description 5
150000007513 acids Chemical class 0.000 claims description 4
239000012298 atmosphere Substances 0.000 claims description 4
229910052794 bromium Inorganic materials 0.000 claims description 4
239000000460 chlorine Substances 0.000 claims description 4
229910052736 halogen Inorganic materials 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 4
-1 heteroatom and R Chemical compound 0.000 claims description 4
LKVQNCTVFJZFIV-JLAZNSOCSA-N (2r)-2-[(1r)-2-bromo-1-hydroxyethyl]-3,4-dihydroxy-2h-furan-5-one Chemical compound BrC[C@H](O)[C@H]1OC(=O)C(O)=C1O LKVQNCTVFJZFIV-JLAZNSOCSA-N 0.000 claims description 3
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 claims description 3
229940073608 benzyl chloride Drugs 0.000 claims description 3
239000003638 chemical reducing agent Substances 0.000 claims description 3
229910000027 potassium carbonate Inorganic materials 0.000 claims description 3
150000003839 salts Chemical class 0.000 claims description 3
239000003963 antioxidant agent Substances 0.000 claims description 2
235000006708 antioxidants Nutrition 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
125000000753 cycloalkyl group Chemical group 0.000 claims description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
125000001246 bromo group Chemical group Br* 0.000 claims 2
125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 1
125000006702 (C1-C18) alkyl group Chemical group 0.000 claims 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
239000002246 antineoplastic agent Substances 0.000 claims 1
125000004429 atom Chemical group 0.000 claims 1
125000001309 chloro group Chemical group Cl* 0.000 claims 1
239000007789 gas Substances 0.000 claims 1
150000002367 halogens Chemical group 0.000 claims 1
239000000543 intermediate Substances 0.000 claims 1
229910052740 iodine Chemical group 0.000 claims 1
239000011630 iodine Chemical group 0.000 claims 1
229910052751 metal Inorganic materials 0.000 claims 1
239000002184 metal Substances 0.000 claims 1
MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical group CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 claims 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
125000002730 succinyl group Chemical group C(CCC(=O)*)(=O)* 0.000 claims 1
229960005070 ascorbic acid Drugs 0.000 abstract description 16
239000011668 ascorbic acid Substances 0.000 abstract description 16
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 abstract description 10
235000010323 ascorbic acid Nutrition 0.000 abstract description 5
238000005917 acylation reaction Methods 0.000 abstract description 4
150000003141 primary amines Chemical class 0.000 abstract description 4
150000003335 secondary amines Chemical class 0.000 abstract description 4
230000010933 acylation Effects 0.000 abstract description 2
159000000011 group IA salts Chemical class 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
239000000047 product Substances 0.000 description 19
239000000243 solution Substances 0.000 description 16
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
238000006243 chemical reaction Methods 0.000 description 15
CJXWKYPCFGUJDJ-LBNWCAIBSA-N (5R)-5-amino-5-[(1S)-1,2-dihydroxyethyl]-3,4-dihydroxyfuran-2-one Chemical class N[C@]1(C(=C(C(=O)O1)O)O)[C@@H](O)CO CJXWKYPCFGUJDJ-LBNWCAIBSA-N 0.000 description 13
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
239000011541 reaction mixture Substances 0.000 description 11
239000002904 solvent Substances 0.000 description 11
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 10
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 8
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
238000010898 silica gel chromatography Methods 0.000 description 7
239000003153 chemical reaction reagent Substances 0.000 description 6
239000002609 medium Substances 0.000 description 6
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 5
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
125000003277 amino group Chemical group 0.000 description 5
235000019253 formic acid Nutrition 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
230000002152 alkylating effect Effects 0.000 description 4
210000004027 cell Anatomy 0.000 description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 4
230000007935 neutral effect Effects 0.000 description 4
125000006239 protecting group Chemical group 0.000 description 4
230000001681 protective effect Effects 0.000 description 4
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 4
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical class NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
238000004440 column chromatography Methods 0.000 description 3
IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 3
210000002950 fibroblast Anatomy 0.000 description 3
238000001914 filtration Methods 0.000 description 3
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
239000006144 Dulbecco’s modiﬁed Eagle's medium Substances 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
150000000996 L-ascorbic acids Chemical class 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
125000002252 acyl group Chemical group 0.000 description 2
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
238000010531 catalytic reduction reaction Methods 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
239000002274 desiccant Substances 0.000 description 2
IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 2
239000008098 formaldehyde solution Substances 0.000 description 2
VGGRCVDNFAQIKO-UHFFFAOYSA-N formic anhydride Chemical compound O=COC=O VGGRCVDNFAQIKO-UHFFFAOYSA-N 0.000 description 2
HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 2
239000012299 nitrogen atmosphere Substances 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
238000006722 reduction reaction Methods 0.000 description 2
210000002966 serum Anatomy 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
238000003756 stirring Methods 0.000 description 2
UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
NWWNMEXBDCKKIG-JLAZNSOCSA-N (2R)-2-[(1S)-2-amino-1-hydroxyethyl]-3,4-dihydroxy-2H-furan-5-one Chemical class NC[C@H](O)[C@H]1OC(=O)C(O)=C1O NWWNMEXBDCKKIG-JLAZNSOCSA-N 0.000 description 1
125000004080 3-carboxypropanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C(O[H])=O 0.000 description 1
WSGYTJNNHPZFKR-UHFFFAOYSA-N 3-hydroxypropanenitrile Chemical compound OCCC#N WSGYTJNNHPZFKR-UHFFFAOYSA-N 0.000 description 1
FJDLVFSSTZOZIE-BQBZGAKWSA-N C(=O)[C@]([C@@]1(C(=C(C(=O)O1)O)O)N)(O)CO Chemical compound C(=O)[C@]([C@@]1(C(=C(C(=O)O1)O)O)N)(O)CO FJDLVFSSTZOZIE-BQBZGAKWSA-N 0.000 description 1
WJTXTQHVQGTUDT-CLTAVNFZSA-N CN[C@]1(C(=C(C(=O)O1)O)O)[C@@H](O)CO Chemical compound CN[C@]1(C(=C(C(=O)O1)O)O)[C@@H](O)CO WJTXTQHVQGTUDT-CLTAVNFZSA-N 0.000 description 1
208000031637 Erythroblastic Acute Leukemia Diseases 0.000 description 1
208000036566 Erythroleukaemia Diseases 0.000 description 1
206010023825 Laryngeal cancer Diseases 0.000 description 1
206010028980 Neoplasm Diseases 0.000 description 1
229930182555 Penicillin Natural products 0.000 description 1
JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
208000021841 acute erythroid leukemia Diseases 0.000 description 1
238000013019 agitation Methods 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
230000001093 anti-cancer Effects 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
208000019065 cervical carcinoma Diseases 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
UXTMROKLAAOEQO-UHFFFAOYSA-N chloroform;ethanol Chemical compound CCO.ClC(Cl)Cl UXTMROKLAAOEQO-UHFFFAOYSA-N 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
238000010511 deprotection reaction Methods 0.000 description 1
FHHZOYXKOICLGH-UHFFFAOYSA-N dichloromethane;ethanol Chemical compound CCO.ClCCl FHHZOYXKOICLGH-UHFFFAOYSA-N 0.000 description 1
150000002009 diols Chemical class 0.000 description 1
239000003814 drug Substances 0.000 description 1
125000004185 ester group Chemical group 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
208000021045 exocrine pancreatic carcinoma Diseases 0.000 description 1
ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 1
230000012010 growth Effects 0.000 description 1
210000005260 human cell Anatomy 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
238000002955 isolation Methods 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
201000005264 laryngeal carcinoma Diseases 0.000 description 1
239000007788 liquid Substances 0.000 description 1
210000001161 mammalian embryo Anatomy 0.000 description 1
239000000203 mixture Substances 0.000 description 1
208000008443 pancreatic carcinoma Diseases 0.000 description 1
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
229940049954 penicillin Drugs 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
238000004544 sputter deposition Methods 0.000 description 1
229960005322 streptomycin Drugs 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
210000004881 tumor cell Anatomy 0.000 description 1
230000004565 tumor cell growth Effects 0.000 description 1

Classifications

- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- 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
- C07D307/34—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
- C07D307/66—Nitrogen atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Public Health (AREA)
Epidemiology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Cosmetics (AREA)
Furan Compounds (AREA)
Anti-Oxidant Or Stabilizer Compositions (AREA)

BG98438A 1993-02-05 1994-02-04 Производни на аскорбинова киселина,методи за тяхното получаване и приложение BG62167B1 (bg)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
HR930131A HRP930131A2 (en)	1993-02-05	1993-02-05	Amino-ascorbic acid derivatives, process for the preparation and use thereof
JP6013667A JPH07101950A (ja)	1993-02-05	1994-02-07	アミノ−アスコルビン酸誘導体、その製造法及び用途

Publications (2)

Publication Number	Publication Date
BG98438A BG98438A (bg)	1994-09-30
BG62167B1 true BG62167B1 (bg)	1999-04-30

Family

ID=26316867

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BG98438A BG62167B1 (bg)	1993-02-05	1994-02-04	Производни на аскорбинова киселина,методи за тяхното получаване и приложение

Country Status (11)

Country	Link
EP (3)	EP0791587A1 (cs)
JP (1)	JPH07101950A (cs)
CN (1)	CN1099753A (cs)
BG (1)	BG62167B1 (cs)
CA (1)	CA2114970C (cs)
CZ (1)	CZ24594A3 (cs)
HR (1)	HRP930131A2 (cs)
HU (1)	HUT71606A (cs)
PL (1)	PL302144A1 (cs)
SI (1)	SI9400061A (cs)
SK (1)	SK12894A3 (cs)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN101107581B (zh)	2005-01-25	2010-08-18	松下电器产业株式会社	电源系统
KR101119027B1 (ko) *	2009-05-07	2012-03-14	(주)코스몰	아스코르빈산 유도체의 제조방법
JP2013230984A (ja) *	2010-08-19	2013-11-14	Seiwa Kasei Co Ltd	アスコルビン酸由来組成物、その製造方法、及び化粧料
WO2017095704A1 (en) *	2015-12-03	2017-06-08	3M Innovative Properties Company	Redox polymerizable composition with photolabile reducing agents
CN115260170B (zh) *	2021-04-30	2024-05-28	禾美生物科技(浙江)有限公司	抗坏血酸多肽衍生物及其制备方法和应用
CN114369075B (zh) *	2022-02-14	2023-09-29	河北乐开节能科技股份有限公司	利用2-酮基-l-古龙酸的水溶液一步制备vc结晶的方法

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2616351A1 (de) *	1975-05-03	1976-11-11	Hoffmann La Roche	Halogenderivate
US4504462A (en) *	1982-06-10	1985-03-12	Mallinckrodt, Inc.	Process for making a lyophilized product for use in skeletal imaging
US4440738A (en) *	1982-06-10	1984-04-03	Mallinckrodt, Inc.	Stable radiographic imaging agents
EP0446539A1 (en) *	1990-03-16	1991-09-18	Merrell Dow Pharmaceuticals Inc.	Novel ascorbic acid derivatives

1993
- 1993-02-05 HR HR930131A patent/HRP930131A2/xx not_active Application Discontinuation
1994
- 1994-02-04 HU HU9400325A patent/HUT71606A/hu unknown
- 1994-02-04 EP EP97106486A patent/EP0791587A1/en not_active Withdrawn
- 1994-02-04 PL PL94302144A patent/PL302144A1/xx unknown
- 1994-02-04 BG BG98438A patent/BG62167B1/bg unknown
- 1994-02-04 CZ CZ94245A patent/CZ24594A3/cs unknown
- 1994-02-04 SK SK128-94A patent/SK12894A3/sk unknown
- 1994-02-04 EP EP97106487A patent/EP0791588A1/en not_active Withdrawn
- 1994-02-04 EP EP94101742A patent/EP0609899A1/en not_active Withdrawn
- 1994-02-04 SI SI9400061A patent/SI9400061A/sl unknown
- 1994-02-04 CA CA002114970A patent/CA2114970C/en not_active Expired - Fee Related
- 1994-02-05 CN CN94102746A patent/CN1099753A/zh active Pending
- 1994-02-07 JP JP6013667A patent/JPH07101950A/ja active Pending

Also Published As

Publication number	Publication date
HUT71606A (en)	1996-01-29
SI9400061A (en)	1994-09-30
EP0791588A1 (en)	1997-08-27
HRP930131A2 (en)	1997-02-28
SK12894A3 (en)	1994-12-07
CA2114970A1 (en)	1994-08-06
EP0791587A1 (en)	1997-08-27
CA2114970C (en)	1999-06-22
CZ24594A3 (en)	1994-08-17
CN1099753A (zh)	1995-03-08
EP0609899A1 (en)	1994-08-10
PL302144A1 (en)	1994-08-08
HU9400325D0 (en)	1994-05-30
JPH07101950A (ja)	1995-04-18
BG98438A (bg)	1994-09-30

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