SK12894A3 - Aminoascorbes acid derivatives, method of preparation and their using - Google Patents

Aminoascorbes acid derivatives, method of preparation and their using Download PDF

Info

Publication number: SK12894A3
Authority: SK; Slovakia
Prior art keywords: group; formula; carbon atoms; hydrogen; benzyl
Prior art date: 1993-02-05

Application number

SK128-94A

Other languages

English (en)

Slovak (sk)

Inventor

Bozidar Suskovic

Vanja Vela

Mira Buncic

Original Assignee

Pliva Farmaceutiska Kemiska Pr

Ustrija 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

1994-12-07

1994-02-04 Application filed by Pliva Farmaceutiska Kemiska Pr, Ustrija Dionicko Drustvo filed Critical Pliva Farmaceutiska Kemiska Pr

1994-12-07 Publication of SK12894A3 publication Critical patent/SK12894A3/sk

Links

239000002253 acid Substances 0.000 title claims abstract description 16
238000000034 method Methods 0.000 title claims abstract description 12
238000002360 preparation method Methods 0.000 title claims abstract description 12
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 claims abstract description 28
238000005932 reductive alkylation reaction Methods 0.000 claims abstract description 9
150000001447 alkali salts Chemical class 0.000 claims abstract 2
229910052739 hydrogen Inorganic materials 0.000 claims description 41
239000001257 hydrogen Substances 0.000 claims description 41
125000004432 carbon atom Chemical group C* 0.000 claims description 33
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 28
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 25
150000001875 compounds Chemical class 0.000 claims description 25
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 25
125000000217 alkyl group Chemical group 0.000 claims description 12
239000003054 catalyst Substances 0.000 claims description 12
229910052717 sulfur Inorganic materials 0.000 claims description 11
125000003118 aryl group Chemical group 0.000 claims description 10
125000000623 heterocyclic group Chemical group 0.000 claims description 10
150000002431 hydrogen Chemical group 0.000 claims description 10
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 9
125000005842 heteroatom Chemical group 0.000 claims description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
229910052757 nitrogen Inorganic materials 0.000 claims description 9
239000011593 sulfur Substances 0.000 claims description 9
125000000753 cycloalkyl group Chemical group 0.000 claims description 7
125000003277 amino group Chemical group 0.000 claims description 6
239000012298 atmosphere Substances 0.000 claims description 6
125000001072 heteroaryl group Chemical group 0.000 claims description 6
125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
229910052760 oxygen Inorganic materials 0.000 claims description 6
239000001301 oxygen Substances 0.000 claims description 6
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
229910052794 bromium Inorganic materials 0.000 claims description 5
125000001246 bromo group Chemical group Br* 0.000 claims description 4
239000000460 chlorine Substances 0.000 claims description 4
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 4
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
239000003638 chemical reducing agent Substances 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 claims description 3
125000001309 chloro group Chemical group Cl* 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims description 3
-1 hydroxybenzotriazolyl Chemical group 0.000 claims description 3
229910052740 iodine Chemical group 0.000 claims description 3
125000004430 oxygen atom Chemical group O* 0.000 claims description 3
239000003963 antioxidant agent Substances 0.000 claims description 2
235000006708 antioxidants Nutrition 0.000 claims description 2
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
125000004080 3-carboxypropanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C(O[H])=O 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
230000003078 antioxidant effect Effects 0.000 claims 1
125000003289 ascorbyl group Chemical class [H]O[C@@]([H])(C([H])([H])O*)[C@@]1([H])OC(=O)C(O*)=C1O* 0.000 claims 1
239000000543 intermediate Substances 0.000 claims 1
239000002184 metal Substances 0.000 claims 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
238000006243 chemical reaction Methods 0.000 abstract description 11
238000005917 acylation reaction Methods 0.000 abstract description 8
238000005804 alkylation reaction Methods 0.000 abstract description 6
230000010933 acylation Effects 0.000 abstract description 4
229960005070 ascorbic acid Drugs 0.000 abstract description 4
239000011668 ascorbic acid Substances 0.000 abstract description 4
150000003335 secondary amines Chemical class 0.000 abstract description 3
230000029936 alkylation Effects 0.000 abstract description 2
150000003141 primary amines Chemical class 0.000 abstract description 2
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
239000000047 product Substances 0.000 description 22
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
239000000243 solution Substances 0.000 description 17
239000000203 mixture Substances 0.000 description 15
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
239000011541 reaction mixture Substances 0.000 description 12
230000002829 reductive effect Effects 0.000 description 11
238000010898 silica gel chromatography Methods 0.000 description 10
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 8
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 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 4
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
210000004027 cell Anatomy 0.000 description 4
239000003153 chemical reaction reagent Substances 0.000 description 4
235000019253 formic acid Nutrition 0.000 description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
230000007935 neutral effect Effects 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
125000006239 protecting group Chemical group 0.000 description 4
230000001603 reducing effect Effects 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
125000002252 acyl group Chemical group 0.000 description 3
238000001914 filtration Methods 0.000 description 3
VGGRCVDNFAQIKO-UHFFFAOYSA-N formic anhydride Chemical compound O=COC=O VGGRCVDNFAQIKO-UHFFFAOYSA-N 0.000 description 3
238000005984 hydrogenation reaction Methods 0.000 description 3
239000012299 nitrogen atmosphere Substances 0.000 description 3
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 3
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 3
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 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-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
150000000996 L-ascorbic acids Chemical class 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
150000001299 aldehydes Chemical class 0.000 description 2
235000010323 ascorbic acid Nutrition 0.000 description 2
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 2
229940073608 benzyl chloride Drugs 0.000 description 2
238000010531 catalytic reduction reaction Methods 0.000 description 2
IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 2
HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 2
238000002955 isolation Methods 0.000 description 2
238000001819 mass spectrum Methods 0.000 description 2
239000002609 medium Substances 0.000 description 2
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
238000006722 reduction reaction Methods 0.000 description 2
210000002966 serum Anatomy 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
HRTHQFHDMRLUSB-MHTLYPKNSA-N (2R)-2-[(1S)-2-(dimethylamino)-1-hydroxyethyl]-3,4-dihydroxy-2H-furan-5-one Chemical compound CN(C)C[C@H](O)[C@H]1OC(=O)C(O)=C1O HRTHQFHDMRLUSB-MHTLYPKNSA-N 0.000 description 1
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
ZKURJJPWUAUGMB-BBIVZNJYSA-N (2R)-3,4-dihydroxy-2-[(1S)-1-hydroxy-2-(methylamino)ethyl]-2H-furan-5-one Chemical compound CNC[C@@H]([C@@H]1C(=C(C(=O)O1)O)O)O ZKURJJPWUAUGMB-BBIVZNJYSA-N 0.000 description 1
CAJHTSKUXSJBTR-OXJNMPFZSA-N (5R)-5-(dibenzylamino)-5-[(1S)-1,2-dihydroxyethyl]-3,4-dihydroxyfuran-2-one Chemical compound C(C1=CC=CC=C1)N(CC1=CC=CC=C1)[C@]1(C(=C(C(=O)O1)O)O)[C@@H](O)CO CAJHTSKUXSJBTR-OXJNMPFZSA-N 0.000 description 1
WHWCAODEJYJNLH-RNHFCUEFSA-N (5R)-5-[(1S)-1,2-dihydroxyethyl]-5-(dimethylamino)-3,4-dihydroxyfuran-2-one Chemical compound CN(C)[C@]1(C(=C(C(=O)O1)O)O)[C@@H](O)CO WHWCAODEJYJNLH-RNHFCUEFSA-N 0.000 description 1
BMASIPCRBXGXIE-QPUJVOFHSA-N (5R)-5-[(1S)-1,2-dihydroxyethyl]-5-(dipropylamino)-3,4-dihydroxyfuran-2-one Chemical compound C(CC)N(CCC)[C@]1(C(=C(C(=O)O1)O)O)[C@@H](O)CO BMASIPCRBXGXIE-QPUJVOFHSA-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
201000009030 Carcinoma Diseases 0.000 description 1
241000689227 Cora <basidiomycete fungus> Species 0.000 description 1
208000031637 Erythroblastic Acute Leukemia Diseases 0.000 description 1
208000036566 Erythroleukaemia Diseases 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 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
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
208000021841 acute erythroid leukemia Diseases 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
230000003217 anti-cancerogenic effect Effects 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
244000309466 calf Species 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 1
210000003679 cervix uteri Anatomy 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000010511 deprotection reaction Methods 0.000 description 1
238000001514 detection method Methods 0.000 description 1
238000010828 elution Methods 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
230000001605 fetal effect Effects 0.000 description 1
239000008098 formaldehyde solution Substances 0.000 description 1
ULITUPMHIDVLLV-UHFFFAOYSA-N formonitrile;sodium Chemical compound [Na].N#C ULITUPMHIDVLLV-UHFFFAOYSA-N 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
229910052736 halogen Inorganic materials 0.000 description 1
210000005260 human cell Anatomy 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
201000005264 laryngeal carcinoma Diseases 0.000 description 1
210000000867 larynx Anatomy 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
210000000496 pancreas Anatomy 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
DHRLEVQXOMLTIM-UHFFFAOYSA-N phosphoric acid;trioxomolybdenum Chemical compound O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.OP(O)(O)=O DHRLEVQXOMLTIM-UHFFFAOYSA-N 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000007921 spray Substances 0.000 description 1
229960005322 streptomycin Drugs 0.000 description 1
239000000126 substance Substances 0.000 description 1
229910021653 sulphate ion 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)

SK128-94A 1993-02-05 1994-02-04 Aminoascorbes acid derivatives, method of preparation and their using SK12894A3 (en)

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 (1)

Publication Number	Publication Date
SK12894A3 true SK12894A3 (en)	1994-12-07

Family

ID=26316867

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK128-94A SK12894A3 (en)	1993-02-05	1994-02-04	Aminoascorbes acid derivatives, method of preparation and their using

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
CA2114970A1 (en)	1994-08-06
EP0791587A1 (en)	1997-08-27
CA2114970C (en)	1999-06-22
CZ24594A3 (en)	1994-08-17
BG62167B1 (bg)	1999-04-30
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

Publication	Publication Date	Title
Gibson et al.	1994	Selective removal of an N-BOC protecting group in the presence of a tert-butyl ester and other acid-sensitive groups
Sauers	1969	Dehydration of N-arylmaleamic acids with acetic anhydride
Greenberg et al.	1984	Structure and dynamics of Troeger's base and simple derivatives in acidic media
SU784783A3 (ru)	1980-11-30	Способ получени производных лейрозидина или их солей
IL295197B2 (en)	2023-05-01	Compounds to inhibit fibroblast activation protein
EP0277588A1 (en)	1988-08-10	Prolinal derivatives
Reinhold et al.	1968	Synthesis of L-. alpha.-methyldopa from asymmetric intermediates
SK12894A3 (en)	1994-12-07	Aminoascorbes acid derivatives, method of preparation and their using
Sakai et al.	1981	Synthesis and DNA binding of [3-[2'-(2-acetamidoethyl)-2, 4'-bithiazole-4-carboxamido] propyl] dimethylsulfonium chloride, a fragment of bleomycin A2
FI65998B (fi)	1984-04-30	Foerfarande foer framstaellning av nya farmakologiskt aktiva pyrrolyl-pyridazinaminderivat
GB2052484A (en)	1981-01-28	Epoxysuccinyl amino acid derivatives
IE46983B1 (en)	1983-11-16	Fluorinated amino acids
US20250145623A1 (en)	2025-05-08	Methods of preparation of heterocyclic compounds
US5627194A (en)	1997-05-06	Anti-viral guanidino-substituted compounds
RU2079489C1 (ru)	1997-05-20	Стабильные соли (+)-(1s,2r)-2[[n-(2-гидроксиамино-2-оксоэтил)-n-метиламино]-карбонил]циклогексан-1-карбоновой кислоты, способ их получения и фармацевтическая композиция
EP0137742B1 (en)	1986-09-17	Process for producing arginyl-p-nitroanilide
US5559251A (en)	1996-09-24	Derivatives of amino-ascorbic acid, the processes for their preparation and use
CA1196342A (en)	1985-11-05	Process for preparing benzylalcohol derivatives
JP2681369B2 (ja)	1997-11-26	ベンゾトリアゾール誘導体およびそれを含有するカルボン酸類分析用試薬
PT915858E (pt)	2000-12-29	Intermediarios para a preparacao de 2-imidazolina-5-onas
US4649222A (en)	1987-03-10	2-(substituted amino)-2-[2-hydroxy-2-alkyl (or phenyl)ethyl]tricyclo[3.3.1.13,7 ]decane hydrohalides
BG62520B1 (bg)	2000-01-31	Аналози на аргинина, притежаващи инхибираща активност върхуno-синтетазата
Dahlgren et al.	2002	Synthesis of potential thrombin inhibitors. Incorporation of tartaric acid templates as P2 proline mimetics
US5106846A (en)	1992-04-21	2,3-thiomorpholinedione-2-oxime derivatives and pharmaceutical compositions containing them
RU2126398C1 (ru)	1999-02-20	Производные аминоаскорбиновой кислоты, способы их получения и производные галоидаскорбиновой кислоты