CA1167859A - Cyclic double hemiacetals of enediol compounds pocessing therapeutic properties and methods for preparation thereof - Google Patents
Cyclic double hemiacetals of enediol compounds pocessing therapeutic properties and methods for preparation thereofInfo
- Publication number
- CA1167859A CA1167859A CA000347029A CA347029A CA1167859A CA 1167859 A CA1167859 A CA 1167859A CA 000347029 A CA000347029 A CA 000347029A CA 347029 A CA347029 A CA 347029A CA 1167859 A CA1167859 A CA 1167859A
- Authority
- CA
- Canada
- Prior art keywords
- group
- ascorbic acid
- hydrogen
- methylglyoxal
- compound
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims abstract description 15
- 230000001225 therapeutic effect Effects 0.000 title claims 2
- -1 enediol compounds Chemical class 0.000 title description 31
- 150000002373 hemiacetals Chemical class 0.000 title description 9
- 125000004122 cyclic group Chemical group 0.000 title description 5
- 238000002360 preparation method Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 25
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 16
- 239000001257 hydrogen Substances 0.000 claims abstract description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 16
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 8
- MWKAGZWJHCTVJY-UHFFFAOYSA-N 3-hydroxyoctadecan-2-one Chemical compound CCCCCCCCCCCCCCCC(O)C(C)=O MWKAGZWJHCTVJY-UHFFFAOYSA-N 0.000 claims abstract description 4
- 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
- 125000005594 diketone group Chemical group 0.000 claims abstract description 4
- 150000002083 enediols Chemical class 0.000 claims abstract 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 claims description 68
- AIJULSRZWUXGPQ-UHFFFAOYSA-N Methylglyoxal Chemical compound CC(=O)C=O AIJULSRZWUXGPQ-UHFFFAOYSA-N 0.000 claims description 44
- 229960005070 ascorbic acid Drugs 0.000 claims description 39
- 239000002211 L-ascorbic acid Substances 0.000 claims description 30
- 235000000069 L-ascorbic acid Nutrition 0.000 claims description 30
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 claims description 17
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- 239000000376 reactant Substances 0.000 claims description 8
- 239000006184 cosolvent Substances 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 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
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 5
- 239000012736 aqueous medium Substances 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 abstract description 9
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- 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
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 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
- 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 (2)
| 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 |
| US27,692 | 1979-04-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1167859A true CA1167859A (en) | 1984-05-22 |
Family
ID=21839228
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000347029A Expired CA1167859A (en) | 1979-04-06 | 1980-03-05 | Cyclic double hemiacetals of enediol compounds pocessing therapeutic properties and methods for preparation thereof |
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 |
| IE49434B1 (en) | 1985-10-02 |
| 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 |
| GB2061259A (en) | 1981-05-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |