IE49434B1 - Cyclic double hemiacetals of enediol compounds & compositions & methods for preparing and using same - Google Patents
Cyclic double hemiacetals of enediol compounds & compositions & methods for preparing and using sameInfo
- Publication number
- IE49434B1 IE49434B1 IE626/80A IE62680A IE49434B1 IE 49434 B1 IE49434 B1 IE 49434B1 IE 626/80 A IE626/80 A IE 626/80A IE 62680 A IE62680 A IE 62680A IE 49434 B1 IE49434 B1 IE 49434B1
- Authority
- IE
- Ireland
- Prior art keywords
- compound
- hydrogen
- aryl
- alkyl
- group
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 17
- -1 enediol compounds Chemical class 0.000 title claims description 35
- 238000000034 method Methods 0.000 title claims description 13
- 150000002373 hemiacetals Chemical class 0.000 title description 10
- 125000004122 cyclic group Chemical group 0.000 title description 8
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims abstract description 69
- 150000001875 compounds Chemical class 0.000 claims abstract description 52
- AIJULSRZWUXGPQ-UHFFFAOYSA-N Methylglyoxal Chemical compound CC(=O)C=O AIJULSRZWUXGPQ-UHFFFAOYSA-N 0.000 claims abstract description 46
- 229960005070 ascorbic acid Drugs 0.000 claims abstract description 37
- 239000002211 L-ascorbic acid Substances 0.000 claims abstract description 29
- 235000000069 L-ascorbic acid Nutrition 0.000 claims abstract description 29
- 239000001257 hydrogen Substances 0.000 claims abstract description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 21
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 18
- 125000003118 aryl group Chemical group 0.000 claims abstract description 17
- 150000002083 enediols Chemical class 0.000 claims abstract description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 7
- 230000001077 hypotensive effect Effects 0.000 claims abstract description 5
- ZNZYKNKBJPZETN-WELNAUFTSA-N Dialdehyde 11678 Chemical compound N1C2=CC=CC=C2C2=C1[C@H](C[C@H](/C(=C/O)C(=O)OC)[C@@H](C=C)C=O)NCC2 ZNZYKNKBJPZETN-WELNAUFTSA-N 0.000 claims abstract description 4
- 208000001953 Hypotension Diseases 0.000 claims abstract description 4
- 239000000824 cytostatic agent Substances 0.000 claims abstract description 4
- 230000001085 cytostatic effect Effects 0.000 claims abstract description 4
- 208000021822 hypotensive Diseases 0.000 claims abstract description 4
- 238000002156 mixing Methods 0.000 claims abstract description 4
- 230000000202 analgesic effect Effects 0.000 claims abstract description 3
- 125000005594 diketone group Chemical group 0.000 claims abstract description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 17
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 claims description 12
- 230000008569 process Effects 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- NBIBDIKAOBCFJN-UHFFFAOYSA-N 2,2-dihydroxy-1-phenylethanone Chemical compound OC(O)C(=O)C1=CC=CC=C1 NBIBDIKAOBCFJN-UHFFFAOYSA-N 0.000 claims description 6
- 229940015043 glyoxal Drugs 0.000 claims description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 4
- 150000001299 aldehydes Chemical class 0.000 claims description 4
- 239000011780 sodium chloride Substances 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 abstract description 19
- 201000011510 cancer Diseases 0.000 abstract description 15
- 238000011282 treatment Methods 0.000 abstract description 6
- 239000002904 solvent Substances 0.000 abstract description 5
- 230000002452 interceptive effect Effects 0.000 abstract description 3
- 239000012299 nitrogen atmosphere Substances 0.000 abstract description 3
- MWKAGZWJHCTVJY-UHFFFAOYSA-N 3-hydroxyoctadecan-2-one Chemical compound CCCCCCCCCCCCCCCC(O)C(C)=O MWKAGZWJHCTVJY-UHFFFAOYSA-N 0.000 abstract description 2
- 241001465754 Metazoa Species 0.000 abstract description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 19
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
- 239000011668 ascorbic acid Substances 0.000 description 9
- 210000004027 cell Anatomy 0.000 description 8
- 238000007912 intraperitoneal administration Methods 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 235000010323 ascorbic acid Nutrition 0.000 description 7
- 239000006184 cosolvent Substances 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 6
- 229910052740 iodine Inorganic materials 0.000 description 6
- 239000011630 iodine Substances 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 238000007254 oxidation reaction Methods 0.000 description 6
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 6
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 6
- 235000000346 sugar Nutrition 0.000 description 6
- 241000700159 Rattus Species 0.000 description 5
- 239000012736 aqueous medium Substances 0.000 description 5
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 5
- 230000003647 oxidation Effects 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 4
- 150000001241 acetals Chemical group 0.000 description 4
- 230000009471 action Effects 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 108090000623 proteins and genes Proteins 0.000 description 4
- 102000004169 proteins and genes Human genes 0.000 description 4
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 3
- 230000036772 blood pressure Effects 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 230000036461 convulsion Effects 0.000 description 3
- 238000004108 freeze drying Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 229960000905 indomethacin Drugs 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000004452 microanalysis Methods 0.000 description 3
- 229960005181 morphine Drugs 0.000 description 3
- 230000036407 pain Effects 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- FOYFCLRNMIJAGK-RXSVEWSESA-N (2r)-2-[(1s)-1,2-dihydroxyethyl]-3,4-dihydroxy-2h-furan-5-one;2-oxopropanal Chemical compound CC(=O)C=O.OC[C@H](O)[C@H]1OC(=O)C(O)=C1O FOYFCLRNMIJAGK-RXSVEWSESA-N 0.000 description 2
- YQBLQKZERMAVDO-UHFFFAOYSA-N 2-oxo-2-phenylacetaldehyde;hydrate Chemical class O.O=CC(=O)C1=CC=CC=C1 YQBLQKZERMAVDO-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 229930189936 Glyoxalase Natural products 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 206010067125 Liver injury Diseases 0.000 description 2
- XCOBLONWWXQEBS-KPKJPENVSA-N N,O-bis(trimethylsilyl)trifluoroacetamide Chemical compound C[Si](C)(C)O\C(C(F)(F)F)=N\[Si](C)(C)C XCOBLONWWXQEBS-KPKJPENVSA-N 0.000 description 2
- 206010030113 Oedema Diseases 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000004856 capillary permeability Effects 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000000875 corresponding effect Effects 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
- 229960001340 histamine Drugs 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 238000001802 infusion Methods 0.000 description 2
- 210000004185 liver Anatomy 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229940076279 serotonin Drugs 0.000 description 2
- PTLRDCMBXHILCL-UHFFFAOYSA-M sodium arsenite Chemical compound [Na+].[O-][As]=O PTLRDCMBXHILCL-UHFFFAOYSA-M 0.000 description 2
- 238000000967 suction filtration Methods 0.000 description 2
- 238000004448 titration Methods 0.000 description 2
- 230000003612 virological effect Effects 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- ONIKNECPXCLUHT-UHFFFAOYSA-N 2-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1Cl ONIKNECPXCLUHT-UHFFFAOYSA-N 0.000 description 1
- JIEOJTPICCAQTH-UHFFFAOYSA-N 2-cyclohexyl-2-oxoacetaldehyde Chemical compound O=CC(=O)C1CCCCC1 JIEOJTPICCAQTH-UHFFFAOYSA-N 0.000 description 1
- OFMBSIAKTAZWIE-UHFFFAOYSA-N 2-oxo-3-phenylpropanal Chemical compound O=CC(=O)CC1=CC=CC=C1 OFMBSIAKTAZWIE-UHFFFAOYSA-N 0.000 description 1
- FNSVXPWVFIJZFZ-UHFFFAOYSA-N 4,4-dihydroxy-3-oxobutanoic acid Chemical compound OC(O)C(=O)CC(O)=O FNSVXPWVFIJZFZ-UHFFFAOYSA-N 0.000 description 1
- 208000031261 Acute myeloid leukaemia Diseases 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- 201000009030 Carcinoma Diseases 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 229930182843 D-Lactic acid Natural products 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- JVTAAEKCZFNVCJ-UWTATZPHSA-N D-lactic acid Chemical compound C[C@@H](O)C(O)=O JVTAAEKCZFNVCJ-UWTATZPHSA-N 0.000 description 1
- WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 229930091371 Fructose Natural products 0.000 description 1
- 239000005715 Fructose Substances 0.000 description 1
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 206010020772 Hypertension 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
- 206010061218 Inflammation Diseases 0.000 description 1
- 108010009384 L-Iditol 2-Dehydrogenase Proteins 0.000 description 1
- 102000003855 L-lactate dehydrogenase Human genes 0.000 description 1
- 108700023483 L-lactate dehydrogenases Proteins 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 206010062575 Muscle contracture Diseases 0.000 description 1
- 208000033776 Myeloid Acute Leukemia Diseases 0.000 description 1
- 229910019567 Re Re Inorganic materials 0.000 description 1
- 208000006268 Sarcoma 180 Diseases 0.000 description 1
- 102100026974 Sorbitol dehydrogenase Human genes 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 102000003929 Transaminases Human genes 0.000 description 1
- 108090000340 Transaminases Proteins 0.000 description 1
- GLNADSQYFUSGOU-GPTZEZBUSA-J Trypan blue Chemical compound [Na+].[Na+].[Na+].[Na+].C1=C(S([O-])(=O)=O)C=C2C=C(S([O-])(=O)=O)C(/N=N/C3=CC=C(C=C3C)C=3C=C(C(=CC=3)\N=N\C=3C(=CC4=CC(=CC(N)=C4C=3O)S([O-])(=O)=O)S([O-])(=O)=O)C)=C(O)C2=C1N GLNADSQYFUSGOU-GPTZEZBUSA-J 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 230000009102 absorption Effects 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000006359 acetalization reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000005030 aluminium foil Substances 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 230000000840 anti-viral effect Effects 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 229940072107 ascorbate Drugs 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- WJAASTDRAAMYNK-UHFFFAOYSA-N benzyl carbamimidothioate;hydron;chloride Chemical compound Cl.NC(=N)SCC1=CC=CC=C1 WJAASTDRAAMYNK-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000036471 bradycardia Effects 0.000 description 1
- 208000006218 bradycardia Diseases 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 210000001715 carotid artery Anatomy 0.000 description 1
- 239000000679 carrageenan Substances 0.000 description 1
- 229920001525 carrageenan Polymers 0.000 description 1
- 229940113118 carrageenan Drugs 0.000 description 1
- 235000010418 carrageenan Nutrition 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000032823 cell division Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 210000000349 chromosome Anatomy 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 208000006111 contracture Diseases 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 230000002596 correlated effect Effects 0.000 description 1
- 238000011461 current therapy Methods 0.000 description 1
- 229940127089 cytotoxic agent Drugs 0.000 description 1
- 229940022769 d- lactic acid Drugs 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000035487 diastolic blood pressure Effects 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 150000002009 diols Chemical group 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000002900 effect on cell Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 150000002085 enols Chemical class 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 231100000234 hepatic damage Toxicity 0.000 description 1
- 231100000753 hepatic injury Toxicity 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 210000003405 ileum Anatomy 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- ICIWUVCWSCSTAQ-UHFFFAOYSA-M iodate Chemical compound [O-]I(=O)=O ICIWUVCWSCSTAQ-UHFFFAOYSA-M 0.000 description 1
- 210000004731 jugular vein Anatomy 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 230000003907 kidney function Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000008818 liver damage Effects 0.000 description 1
- 230000003908 liver function Effects 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- MXWHMTNPTTVWDM-NXOFHUPFSA-N mitoguazone Chemical compound NC(N)=N\N=C(/C)\C=N\N=C(N)N MXWHMTNPTTVWDM-NXOFHUPFSA-N 0.000 description 1
- 229960003539 mitoguazone Drugs 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 210000000929 nociceptor Anatomy 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000007248 oxidative elimination reaction Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 239000006069 physical mixture Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000002062 proliferating effect Effects 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000006916 protein interaction Effects 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000011514 reflex Effects 0.000 description 1
- 230000031539 regulation of cell division Effects 0.000 description 1
- 230000000284 resting effect Effects 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- DUIOPKIIICUYRZ-UHFFFAOYSA-N semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 description 1
- 150000007659 semicarbazones Chemical class 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 230000035488 systolic blood pressure Effects 0.000 description 1
- 238000010257 thawing Methods 0.000 description 1
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
- C07D319/12—1,4-Dioxanes; Hydrogenated 1,4-dioxanes not condensed with other rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pain & Pain Management (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/027,692 US4238500A (en) | 1979-04-06 | 1979-04-06 | Cyclic double hemiacetals of enediol compounds and compositions and methods for preparing and using same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE800626L IE800626L (en) | 1980-10-06 |
| IE49434B1 true IE49434B1 (en) | 1985-10-02 |
Family
ID=21839228
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE626/80A IE49434B1 (en) | 1979-04-06 | 1980-03-26 | Cyclic double hemiacetals of enediol compounds & compositions & methods for preparing and using same |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4238500A (cg-RX-API-DMAC10.html) |
| JP (1) | JPS5649375A (cg-RX-API-DMAC10.html) |
| AU (1) | AU521764B2 (cg-RX-API-DMAC10.html) |
| CA (1) | CA1167859A (cg-RX-API-DMAC10.html) |
| CH (1) | CH643550A5 (cg-RX-API-DMAC10.html) |
| DE (1) | DE3010947C2 (cg-RX-API-DMAC10.html) |
| DK (1) | DK150780A (cg-RX-API-DMAC10.html) |
| FR (1) | FR2453171A1 (cg-RX-API-DMAC10.html) |
| GB (1) | GB2061259B (cg-RX-API-DMAC10.html) |
| HU (1) | HU182119B (cg-RX-API-DMAC10.html) |
| IE (1) | IE49434B1 (cg-RX-API-DMAC10.html) |
| IT (1) | IT1141269B (cg-RX-API-DMAC10.html) |
| NL (1) | NL8001603A (cg-RX-API-DMAC10.html) |
| NO (1) | NO151621C (cg-RX-API-DMAC10.html) |
| SE (1) | SE448236B (cg-RX-API-DMAC10.html) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4518611A (en) * | 1983-04-04 | 1985-05-21 | National Foundation For Cancer Research, Inc. | 2-Furylbutyrolactone modulation of the immune system in mammals |
| EP0265508B1 (en) * | 1986-04-29 | 1992-08-26 | Theracel Corporation | Production and use of reaction product obtained from ascorbic acid with alpha,beta-unsaturated alicyclic ketone or vinyl aliphatic ketone |
| DE3826303A1 (de) * | 1988-08-03 | 1990-02-08 | Basf Ag | Verfahren zur herstellung cyclischer 6- bis 8-gliedriger vinylen-1,2-dioxyverbindungen |
| US6001347A (en) * | 1995-03-31 | 1999-12-14 | Emisphere Technologies, Inc. | Compounds and compositions for delivering active agents |
| US8163796B1 (en) | 2009-07-28 | 2012-04-24 | BioChemical Solutions, LLC | Treatment of cancer by oxidation-reduction potentiation of cancerostatic dicarbonyls |
| JP7685175B1 (ja) * | 2023-11-28 | 2025-05-29 | 株式会社成和化成 | アスコルビン酸誘導体及びそれらを配合した化粧料 |
| WO2025115272A1 (ja) * | 2023-11-28 | 2025-06-05 | 株式会社成和化成 | アスコルビン酸誘導体及びそれらを配合した化粧料 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3048598A (en) * | 1960-02-23 | 1962-08-07 | Miles Lab | Process for producing 2-hydrocarbon-2-dioxenes |
| US3555006A (en) * | 1967-06-15 | 1971-01-12 | Exxon Production Research Co | Polysaccharide polymer cyclic ketals |
| GB1270579A (en) * | 1968-08-17 | 1972-04-12 | Fuji Photo Film Co Ltd | Dihydroxy-1,4-dioxanes |
| BE759354A (fr) * | 1969-11-28 | 1971-04-30 | Fuji Photo Film Co Ltd | Preparation de dihydroxy-1,4-dioxannes |
| US4096321A (en) * | 1976-11-22 | 1978-06-20 | Hoffmann-La Roche Inc. | Process to produce oxazinomycin and intermediates |
| NL7904249A (nl) * | 1978-06-20 | 1979-12-27 | Cancer Res Nat Found | Nieuwe cyclische acetalen met cytostatische, bloed- drukverlagende en pijnstillende werking, werkwijze ter bereiding van deze verbindingen alsmede farmaceu- tische preparaten die een dergelijke verbinding bevat- ten. |
-
1979
- 1979-04-06 US US06/027,692 patent/US4238500A/en not_active Expired - Lifetime
-
1980
- 1980-03-05 CA CA000347029A patent/CA1167859A/en not_active Expired
- 1980-03-18 NL NL8001603A patent/NL8001603A/nl active Search and Examination
- 1980-03-21 DE DE3010947A patent/DE3010947C2/de not_active Expired
- 1980-03-26 IE IE626/80A patent/IE49434B1/en not_active IP Right Cessation
- 1980-04-01 NO NO800958A patent/NO151621C/no unknown
- 1980-04-01 AU AU57037/80A patent/AU521764B2/en not_active Ceased
- 1980-04-02 CH CH259280A patent/CH643550A5/de not_active IP Right Cessation
- 1980-04-02 SE SE8002549A patent/SE448236B/sv not_active IP Right Cessation
- 1980-04-03 HU HU80813A patent/HU182119B/hu not_active IP Right Cessation
- 1980-04-03 IT IT21166/80A patent/IT1141269B/it active
- 1980-04-04 JP JP4453080A patent/JPS5649375A/ja active Pending
- 1980-04-04 FR FR8007722A patent/FR2453171A1/fr active Granted
- 1980-04-08 GB GB8011339A patent/GB2061259B/en not_active Expired
- 1980-04-08 DK DK150780A patent/DK150780A/da not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| IT8021166A0 (it) | 1980-04-03 |
| IE800626L (en) | 1980-10-06 |
| DE3010947C2 (de) | 1986-08-07 |
| NL8001603A (nl) | 1980-10-08 |
| JPS5649375A (en) | 1981-05-02 |
| HU182119B (en) | 1983-12-28 |
| FR2453171A1 (fr) | 1980-10-31 |
| SE8002549L (sv) | 1980-10-07 |
| AU521764B2 (en) | 1982-04-29 |
| DE3010947A1 (de) | 1980-10-23 |
| FR2453171B1 (cg-RX-API-DMAC10.html) | 1983-04-08 |
| DK150780A (da) | 1980-10-07 |
| NO151621C (no) | 1985-05-08 |
| GB2061259B (en) | 1983-02-02 |
| IT1141269B (it) | 1986-10-01 |
| SE448236B (sv) | 1987-02-02 |
| NO151621B (no) | 1985-01-28 |
| NO800958L (no) | 1980-10-07 |
| AU5703780A (en) | 1980-10-09 |
| US4238500A (en) | 1980-12-09 |
| CH643550A5 (de) | 1984-06-15 |
| CA1167859A (en) | 1984-05-22 |
| GB2061259A (en) | 1981-05-13 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4452812A (en) | Organic complex of platinum, its preparation and its use for treating malignant tumors | |
| SU1475905A1 (ru) | Производные тиазолидин-4S-карбоновой кислоты, обладающие способностью защищать печень | |
| JPH0819111B2 (ja) | ２―ニトロイミダゾール誘導体及びこれを有効成分とする放射線増感剤 | |
| US4238500A (en) | Cyclic double hemiacetals of enediol compounds and compositions and methods for preparing and using same | |
| JPH051780B2 (cg-RX-API-DMAC10.html) | ||
| CN115850288B (zh) | 一种丝裂霉素c前体药物及其制备方法和应用 | |
| US4287205A (en) | Hypotensive and analgesic compounds and compositions and methods for using same | |
| US4424348A (en) | Methods of manufacture of nitrile-containing glucuronic acid conjugates | |
| JPS6260393B2 (cg-RX-API-DMAC10.html) | ||
| Burakevich et al. | Phenylfurazan oxide. Chemistry | |
| EP0739887A1 (fr) | Nouveaux composés cyclohexaniques, leur procédé de préparation et les compositions pharmaceutiques qui les contiennent | |
| Benson et al. | Nitrosation of 1-naphthyl N-methylcarbamate and related compounds as it was followed by oscillopolarography | |
| ZELINSKI et al. | Racemic 2-Hydroxymethyl-2, 3-dihydro-4H-pyran, a Model Carbohydrate1 | |
| SU1225487A3 (ru) | Способ получени 1,2-5,6-диангидро-3,4-бис-( @ -карбоксипропионил)-дульцита или его динатриевой соли | |
| US4942253A (en) | Polyhydroxybenzoic acid derivatives | |
| US4482568A (en) | Inhibition of alcohol metabolism by tetramethylene sulfoxides | |
| SU529601A1 (ru) | Производные триокситрет.бутиламида 4-(бис(2-хлорэтил) аминр) фенилуксусной кислоты,обладающие противоопухолевой активностью и способ их получени | |
| CA1142948A (en) | Cytostatic compounds and compositions and methods for preparing and using same | |
| Hortmann et al. | Azabicyclobutanes. Formation of an azabicyclo [1.1. 0] butane via irradiation of an allylic azide | |
| US4251515A (en) | Novel nitrosourea derivatives | |
| FI62283C (fi) | Foerfarande foer framstaellning av nya terapeutiskt anvaendbara n-2'-karboxifenyl-4-klorantranilsyraderivat | |
| Shasha et al. | O-(alkyl-and aryl-oxythiocarbonyl) sugar derivatives | |
| Yatsunami et al. | Photochemische Reaktionen. 98. Mitteilung. Photochemistry of N‐Acylimidazoles. III. Rates and Yields of N→ C Acyl Migration and of C (α)‐C (β) Cleavage of Acyl Side Chains | |
| Fodor et al. | The search for new cancerostatic agents | |
| SU540462A1 (ru) | 5,5-Дизамещенные 2-(4-бис-(2-хлорэтил)аминофенил)-1,3-диоксаны, обладающие противоопухолевой активностью |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Patent lapsed |