CA1128532A - 3,4-dihydroxy cinnamic aldehyde derivative, the production thereof, and medications - Google Patents
3,4-dihydroxy cinnamic aldehyde derivative, the production thereof, and medicationsInfo
- Publication number
- CA1128532A CA1128532A CA335,661A CA335661A CA1128532A CA 1128532 A CA1128532 A CA 1128532A CA 335661 A CA335661 A CA 335661A CA 1128532 A CA1128532 A CA 1128532A
- Authority
- CA
- Canada
- Prior art keywords
- acetone
- dihydroxy cinnamic
- cinnamic aldehyde
- residue
- amount
- 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
- 150000001853 cinnamic aldehyde derivatives Chemical class 0.000 title claims abstract description 12
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- 239000003814 drug Substances 0.000 title description 3
- 229940079593 drug Drugs 0.000 title description 3
- 238000002483 medication Methods 0.000 title 1
- 150000003839 salts Chemical class 0.000 claims abstract description 18
- KJPRLNWUNMBNBZ-QPJJXVBHSA-N (E)-cinnamaldehyde Chemical compound O=C\C=C\C1=CC=CC=C1 KJPRLNWUNMBNBZ-QPJJXVBHSA-N 0.000 claims abstract description 10
- AXMVYSVVTMKQSL-UHFFFAOYSA-N UNPD142122 Natural products OC1=CC=C(C=CC=O)C=C1O AXMVYSVVTMKQSL-UHFFFAOYSA-N 0.000 claims abstract description 10
- 229940117916 cinnamic aldehyde Drugs 0.000 claims abstract description 10
- KJPRLNWUNMBNBZ-UHFFFAOYSA-N cinnamic aldehyde Natural products O=CC=CC1=CC=CC=C1 KJPRLNWUNMBNBZ-UHFFFAOYSA-N 0.000 claims abstract description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 8
- OOCCDEMITAIZTP-QPJJXVBHSA-N (E)-cinnamyl alcohol Chemical compound OC\C=C\C1=CC=CC=C1 OOCCDEMITAIZTP-QPJJXVBHSA-N 0.000 claims abstract description 7
- OOCCDEMITAIZTP-UHFFFAOYSA-N allylic benzylic alcohol Natural products OCC=CC1=CC=CC=C1 OOCCDEMITAIZTP-UHFFFAOYSA-N 0.000 claims abstract description 7
- 240000007643 Phytolacca americana Species 0.000 claims abstract description 6
- 235000009074 Phytolacca americana Nutrition 0.000 claims abstract description 6
- 125000003158 alcohol group Chemical group 0.000 claims abstract description 4
- 238000006464 oxidative addition reaction Methods 0.000 claims abstract description 4
- LZLOFGMGFADIKQ-UHFFFAOYSA-N benzene;1,4-dioxane Chemical group C1COCCO1.C1=CC=CC=C1 LZLOFGMGFADIKQ-UHFFFAOYSA-N 0.000 claims abstract 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 62
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 21
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 19
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 16
- 239000000126 substance Substances 0.000 claims description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 12
- 235000013399 edible fruits Nutrition 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 10
- 239000000284 extract Substances 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 238000004440 column chromatography Methods 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 claims description 6
- 238000003756 stirring Methods 0.000 claims description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 5
- -1 allyl pyrocatechin Chemical compound 0.000 claims description 5
- 239000000376 reactant Substances 0.000 claims description 5
- 241000219506 Phytolacca Species 0.000 claims description 4
- 150000001299 aldehydes Chemical class 0.000 claims description 4
- XELZGAJCZANUQH-UHFFFAOYSA-N methyl 1-acetylthieno[3,2-c]pyrazole-5-carboxylate Chemical compound CC(=O)N1N=CC2=C1C=C(C(=O)OC)S2 XELZGAJCZANUQH-UHFFFAOYSA-N 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 239000003208 petroleum Substances 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- BNBQRQQYDMDJAH-UHFFFAOYSA-N benzodioxan Chemical group C1=CC=C2OCCOC2=C1 BNBQRQQYDMDJAH-UHFFFAOYSA-N 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 239000000463 material Substances 0.000 claims description 3
- 229910001923 silver oxide Inorganic materials 0.000 claims description 3
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 238000005406 washing Methods 0.000 claims 4
- 238000001914 filtration Methods 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 230000001590 oxidative effect Effects 0.000 claims 1
- 210000004185 liver Anatomy 0.000 abstract description 7
- 230000003647 oxidation Effects 0.000 abstract description 5
- 238000007254 oxidation reaction Methods 0.000 abstract description 5
- 230000001929 anti-hepatotoxic effect Effects 0.000 abstract description 3
- 230000000447 dimerizing effect Effects 0.000 abstract description 2
- 230000001225 therapeutic effect Effects 0.000 abstract description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 abstract 1
- OHQVJZXZOCBRIJ-UHFFFAOYSA-N Americanin Chemical compound C1=C(OC)C(OC)=CC=C1CC1C(CC=2C=C(OC)C(OC3C(C(OC(=O)C=CC=4C=C(O)C(O)=CC=4)C(O)C(CO)O3)O)=CC=2)C(=O)OC1 OHQVJZXZOCBRIJ-UHFFFAOYSA-N 0.000 description 12
- KPKZJLCSROULON-QKGLWVMZSA-N Phalloidin Chemical compound N1C(=O)[C@@H]([C@@H](O)C)NC(=O)[C@H](C)NC(=O)[C@H](C[C@@](C)(O)CO)NC(=O)[C@H](C2)NC(=O)[C@H](C)NC(=O)[C@@H]3C[C@H](O)CN3C(=O)[C@@H]1CSC1=C2C2=CC=CC=C2N1 KPKZJLCSROULON-QKGLWVMZSA-N 0.000 description 8
- 239000013543 active substance Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- SDDXIQONGFZHJH-UHFFFAOYSA-N Isoamericanin A Natural products OCC1OC2=CC=C(C=CC=O)C=C2OC1C1=CC=C(O)C(O)=C1 SDDXIQONGFZHJH-UHFFFAOYSA-N 0.000 description 6
- 108010003672 americanin Proteins 0.000 description 6
- 241000699670 Mus sp. Species 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 4
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 4
- 108010009711 Phalloidine Proteins 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000008194 pharmaceutical composition Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 125000006239 protecting group Chemical group 0.000 description 4
- 239000000829 suppository Substances 0.000 description 4
- MFYSUUPKMDJYPF-UHFFFAOYSA-N 2-[(4-methyl-2-nitrophenyl)diazenyl]-3-oxo-n-phenylbutanamide Chemical compound C=1C=CC=CC=1NC(=O)C(C(=O)C)N=NC1=CC=C(C)C=C1[N+]([O-])=O MFYSUUPKMDJYPF-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
- 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 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 2
- 235000011869 dried fruits Nutrition 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 229940116364 hard fat Drugs 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 2
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
- 239000001117 sulphuric acid Substances 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- HORQAOAYAYGIBM-UHFFFAOYSA-N 2,4-dinitrophenylhydrazine Chemical compound NNC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O HORQAOAYAYGIBM-UHFFFAOYSA-N 0.000 description 1
- 229910002012 Aerosil® Inorganic materials 0.000 description 1
- 235000019890 Amylum Nutrition 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 229920002307 Dextran Polymers 0.000 description 1
- 241000282414 Homo sapiens Species 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
- WVVOBOZHTQJXPB-UHFFFAOYSA-N N-anilino-N-nitronitramide Chemical compound [N+](=O)([O-])N(NC1=CC=CC=C1)[N+](=O)[O-] WVVOBOZHTQJXPB-UHFFFAOYSA-N 0.000 description 1
- 206010067482 No adverse event Diseases 0.000 description 1
- ATTZFSUZZUNHBP-UHFFFAOYSA-N Piperonyl sulfoxide Chemical compound CCCCCCCCS(=O)C(C)CC1=CC=C2OCOC2=C1 ATTZFSUZZUNHBP-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 241000786363 Rhampholeon spectrum Species 0.000 description 1
- 229920005654 Sephadex Polymers 0.000 description 1
- 239000012507 Sephadex™ Substances 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000005352 clarification Methods 0.000 description 1
- 239000000287 crude extract Substances 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000003640 drug residue Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- ZHNUHDYFZUAESO-UHFFFAOYSA-N formamide Substances NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000000727 fraction Substances 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 150000002337 glycosamines Chemical class 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 210000005229 liver cell Anatomy 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000012797 qualification Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229960001866 silicon dioxide Drugs 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 231100000765 toxin Toxicity 0.000 description 1
- 229960004418 trolamine Drugs 0.000 description 1
Classifications
-
- 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
- C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
- C07D319/16—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D319/20—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring with substituents attached to the hetero ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Gastroenterology & Hepatology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Steroid Compounds (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19782840467 DE2840467A1 (de) | 1978-09-16 | 1978-09-16 | 3,4-dihydroxizimtaldehydderivat, dessen herstellung und arzneimittel |
| DEP2840467.3 | 1978-09-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1128532A true CA1128532A (en) | 1982-07-27 |
Family
ID=6049691
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA335,661A Expired CA1128532A (en) | 1978-09-16 | 1979-09-14 | 3,4-dihydroxy cinnamic aldehyde derivative, the production thereof, and medications |
Country Status (18)
| Country | Link |
|---|---|
| JP (1) | JPS5559182A (cs) |
| AR (3) | AR221900A1 (cs) |
| AT (1) | AT367417B (cs) |
| BE (1) | BE878824A (cs) |
| CA (1) | CA1128532A (cs) |
| CS (3) | CS221522B2 (cs) |
| DE (1) | DE2840467A1 (cs) |
| ES (3) | ES8101578A1 (cs) |
| FR (1) | FR2436145A1 (cs) |
| GB (1) | GB2035300B (cs) |
| IT (1) | IT7925651A0 (cs) |
| LU (1) | LU81679A1 (cs) |
| NL (1) | NL7906881A (cs) |
| PL (1) | PL120977B1 (cs) |
| PT (1) | PT70177A (cs) |
| SE (1) | SE7907656L (cs) |
| SU (1) | SU925246A3 (cs) |
| ZA (1) | ZA794815B (cs) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2851919A1 (fr) * | 2003-03-03 | 2004-09-10 | Lmd | Lignanes utilisables comme inhibiteurs de cathepsines et leurs applications |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2428680C2 (de) * | 1974-06-14 | 1983-02-17 | Dr. Madaus & Co, 5000 Köln | 1-(2',4',6'-Trihydroxyphenyl)-propandion-(1,2)-Verbindungen, Verfahren zu deren Herstellung und Arzneimittel, die diese Verbindungen enthalten |
-
1978
- 1978-09-16 DE DE19782840467 patent/DE2840467A1/de not_active Withdrawn
-
1979
- 1979-09-11 ZA ZA00794815A patent/ZA794815B/xx unknown
- 1979-09-12 LU LU81679A patent/LU81679A1/de unknown
- 1979-09-12 IT IT7925651A patent/IT7925651A0/it unknown
- 1979-09-14 PT PT70177A patent/PT70177A/pt unknown
- 1979-09-14 FR FR7923013A patent/FR2436145A1/fr active Pending
- 1979-09-14 SE SE7907656A patent/SE7907656L/xx not_active Application Discontinuation
- 1979-09-14 AT AT0607979A patent/AT367417B/de not_active IP Right Cessation
- 1979-09-14 SU SU792811705A patent/SU925246A3/ru active
- 1979-09-14 CS CS814300A patent/CS221522B2/cs unknown
- 1979-09-14 CA CA335,661A patent/CA1128532A/en not_active Expired
- 1979-09-14 CS CS796224A patent/CS221521B2/cs unknown
- 1979-09-14 NL NL7906881A patent/NL7906881A/nl not_active Application Discontinuation
- 1979-09-14 CS CS814301A patent/CS221523B2/cs unknown
- 1979-09-15 ES ES484202A patent/ES8101578A1/es not_active Expired
- 1979-09-15 PL PL1979218339A patent/PL120977B1/pl unknown
- 1979-09-17 BE BE0/197176A patent/BE878824A/fr unknown
- 1979-09-17 AR AR278071A patent/AR221900A1/es active
- 1979-09-17 JP JP11800679A patent/JPS5559182A/ja active Pending
- 1979-09-17 GB GB7932131A patent/GB2035300B/en not_active Expired
-
1980
- 1980-01-31 ES ES488140A patent/ES488140A0/es active Granted
- 1980-01-31 ES ES488141A patent/ES8101580A1/es not_active Expired
-
1981
- 1981-02-25 AR AR284433A patent/AR226094A1/es active
- 1981-02-25 AR AR284432A patent/AR225070A1/es active
Also Published As
| Publication number | Publication date |
|---|---|
| DE2840467A1 (de) | 1980-03-20 |
| AR225070A1 (es) | 1982-02-15 |
| ES484202A0 (es) | 1980-12-16 |
| AT367417B (de) | 1982-07-12 |
| AR226094A1 (es) | 1982-05-31 |
| NL7906881A (nl) | 1980-03-18 |
| LU81679A1 (de) | 1980-01-24 |
| CS221522B2 (en) | 1983-04-29 |
| PL218339A1 (cs) | 1980-12-01 |
| CS221521B2 (en) | 1983-04-29 |
| ES8101579A1 (es) | 1980-12-16 |
| ATA607979A (de) | 1981-11-15 |
| SE7907656L (sv) | 1980-03-17 |
| ES8101578A1 (es) | 1980-12-16 |
| ES488140A0 (es) | 1980-12-16 |
| GB2035300B (en) | 1983-03-23 |
| PT70177A (de) | 1979-10-01 |
| BE878824A (fr) | 1980-03-17 |
| SU925246A3 (ru) | 1982-04-30 |
| FR2436145A1 (fr) | 1980-04-11 |
| ZA794815B (en) | 1980-10-29 |
| PL120977B1 (en) | 1982-04-30 |
| IT7925651A0 (it) | 1979-09-12 |
| CS221523B2 (en) | 1983-04-29 |
| ES488141A0 (es) | 1980-12-16 |
| JPS5559182A (en) | 1980-05-02 |
| ES8101580A1 (es) | 1980-12-16 |
| GB2035300A (en) | 1980-06-18 |
| AR221900A1 (es) | 1981-03-31 |
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