CH646682A5 - Acide tetramethyl-hexadecapentaenoique, procedes pour sa preparation et composition pharmaceutique contenant cet acide. - Google Patents
Acide tetramethyl-hexadecapentaenoique, procedes pour sa preparation et composition pharmaceutique contenant cet acide. Download PDFInfo
- Publication number
- CH646682A5 CH646682A5 CH231781A CH231781A CH646682A5 CH 646682 A5 CH646682 A5 CH 646682A5 CH 231781 A CH231781 A CH 231781A CH 231781 A CH231781 A CH 231781A CH 646682 A5 CH646682 A5 CH 646682A5
- Authority
- CH
- Switzerland
- Prior art keywords
- compound
- acid
- general formula
- formula
- tetramethyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 19
- 239000002253 acid Substances 0.000 title claims description 11
- 238000002360 preparation method Methods 0.000 title claims description 11
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 3
- -1 TETRAMETHYL-HEXADECAPENTAENOIC ACID Chemical compound 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 78
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 239000003153 chemical reaction reagent Substances 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 230000007062 hydrolysis Effects 0.000 claims description 6
- 238000006460 hydrolysis reaction Methods 0.000 claims description 6
- 230000000144 pharmacologic effect Effects 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 4
- UUBHZHZSIKRVIV-KCXSXWJSSA-N (2e,6e,10e)-3,7,11,15-tetramethylhexadeca-2,4,6,10,14-pentaenoic acid Chemical compound CC(C)=CCC\C(C)=C\CC\C(C)=C\C=C\C(\C)=C\C(O)=O UUBHZHZSIKRVIV-KCXSXWJSSA-N 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 238000007670 refining Methods 0.000 claims description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 22
- 230000003780 keratinization Effects 0.000 description 14
- 238000011282 treatment Methods 0.000 description 13
- 241000699670 Mus sp. Species 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 241000699666 Mus <mouse, genus> Species 0.000 description 8
- 208000017520 skin disease Diseases 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 235000019198 oils Nutrition 0.000 description 6
- 201000004384 Alopecia Diseases 0.000 description 5
- 201000010099 disease Diseases 0.000 description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
- 208000024963 hair loss Diseases 0.000 description 5
- 230000003676 hair loss Effects 0.000 description 5
- 238000011534 incubation Methods 0.000 description 5
- FPIPGXGPPPQFEQ-UHFFFAOYSA-N 13-cis retinol Natural products OCC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- FPIPGXGPPPQFEQ-BOOMUCAASA-N Vitamin A Natural products OC/C=C(/C)\C=C\C=C(\C)/C=C/C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-BOOMUCAASA-N 0.000 description 4
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 4
- 230000001093 anti-cancer Effects 0.000 description 4
- 210000004027 cell Anatomy 0.000 description 4
- 239000012295 chemical reaction liquid Substances 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 208000003154 papilloma Diseases 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 231100000820 toxicity test Toxicity 0.000 description 4
- 235000019155 vitamin A Nutrition 0.000 description 4
- 239000011719 vitamin A Substances 0.000 description 4
- 229940045997 vitamin a Drugs 0.000 description 4
- 206010011703 Cyanosis Diseases 0.000 description 3
- 206010028980 Neoplasm Diseases 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000000862 absorption spectrum Methods 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 201000011510 cancer Diseases 0.000 description 3
- 239000007937 lozenge Substances 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 238000001819 mass spectrum Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 208000002874 Acne Vulgaris Diseases 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- 206010020649 Hyperkeratosis Diseases 0.000 description 2
- 206010020915 Hypervitaminosis Diseases 0.000 description 2
- 201000004681 Psoriasis Diseases 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 206010000496 acne Diseases 0.000 description 2
- 239000002246 antineoplastic agent Substances 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 210000002919 epithelial cell Anatomy 0.000 description 2
- 125000004494 ethyl ester group Chemical group 0.000 description 2
- 201000006122 hypervitaminosis A Diseases 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229960001866 silicon dioxide Drugs 0.000 description 2
- 229940124597 therapeutic agent Drugs 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- IIMOCWXERPQCQP-UHFFFAOYSA-N 1-methyl-4-(3,7,11-trimethyldodeca-2,6,10-trienylsulfonyl)benzene Chemical compound CC(C)=CCCC(C)=CCCC(C)=CCS(=O)(=O)C1=CC=C(C)C=C1 IIMOCWXERPQCQP-UHFFFAOYSA-N 0.000 description 1
- HGFAGNRYCRACAH-UHFFFAOYSA-N 6,10,14-trimethylpentadeca-3,5,9,13-tetraen-2-one Chemical compound CC(C)=CCCC(C)=CCCC(C)=CC=CC(C)=O HGFAGNRYCRACAH-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 235000017060 Arachis glabrata Nutrition 0.000 description 1
- 244000105624 Arachis hypogaea Species 0.000 description 1
- 235000010777 Arachis hypogaea Nutrition 0.000 description 1
- 235000018262 Arachis monticola Nutrition 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 101150041968 CDC13 gene Proteins 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 208000002506 Darier Disease Diseases 0.000 description 1
- 206010012455 Dermatitis exfoliative Diseases 0.000 description 1
- 229920002153 Hydroxypropyl cellulose Polymers 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
- 208000001126 Keratosis Diseases 0.000 description 1
- 206010023369 Keratosis follicular Diseases 0.000 description 1
- 208000005775 Parakeratosis Diseases 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 241000101040 Pityriasis Species 0.000 description 1
- 208000006994 Precancerous Conditions Diseases 0.000 description 1
- 206010037575 Pustular psoriasis Diseases 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
- 238000007239 Wittig reaction Methods 0.000 description 1
- 230000000172 allergic effect Effects 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 208000010668 atopic eczema Diseases 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 230000007850 degeneration Effects 0.000 description 1
- OQKGPUSERILONW-CSKARUKUSA-N ethyl (e)-4-diethoxyphosphoryl-3-methylbut-2-enoate Chemical compound CCOC(=O)\C=C(/C)CP(=O)(OCC)OCC OQKGPUSERILONW-CSKARUKUSA-N 0.000 description 1
- JIPWHZOYUGYXFA-UHFFFAOYSA-N ethyl 4-bromo-3-methylbut-2-enoate Chemical compound CCOC(=O)C=C(C)CBr JIPWHZOYUGYXFA-UHFFFAOYSA-N 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000007902 hard capsule Substances 0.000 description 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
- 206010021198 ichthyosis Diseases 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 201000004607 keratosis follicularis Diseases 0.000 description 1
- 201000011486 lichen planus Diseases 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 201000010914 pustulosis of palm and sole Diseases 0.000 description 1
- 208000011797 pustulosis palmaris et plantaris Diseases 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- GGUBFICZYGKNTD-UHFFFAOYSA-N triethyl phosphonoacetate Chemical compound CCOC(=O)CP(=O)(OCC)OCC GGUBFICZYGKNTD-UHFFFAOYSA-N 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 229940100445 wheat starch Drugs 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- 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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/36—Carboxylic acids; Salts or anhydrides thereof
- A61K8/361—Carboxylic acids having more than seven carbon atoms in an unbroken chain; Salts or anhydrides thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/02—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
- C07C57/03—Monocarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
- C07C69/587—Monocarboxylic acid esters having at least two carbon-to-carbon double bonds
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4455880A JPS56140949A (en) | 1980-04-07 | 1980-04-07 | 3,7,11,15-tetramethyl-2,4,6,10,14-hexadecapentaenic acid |
| JP10442080A JPS5731615A (en) | 1980-07-31 | 1980-07-31 | Remedy for skin disease with keratinization |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH646682A5 true CH646682A5 (fr) | 1984-12-14 |
Family
ID=26384501
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH231781A CH646682A5 (fr) | 1980-04-07 | 1981-04-06 | Acide tetramethyl-hexadecapentaenoique, procedes pour sa preparation et composition pharmaceutique contenant cet acide. |
Country Status (11)
| Country | Link |
|---|---|
| AU (1) | AU537402B2 (ja) |
| CA (1) | CA1179370A (ja) |
| CH (1) | CH646682A5 (ja) |
| DE (1) | DE3113149A1 (ja) |
| DK (1) | DK158457C (ja) |
| ES (2) | ES8205190A1 (ja) |
| FR (1) | FR2479807A1 (ja) |
| GB (1) | GB2073750B (ja) |
| IT (1) | IT1194141B (ja) |
| NL (1) | NL191744C (ja) |
| SE (1) | SE447243B (ja) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS56140949A (en) * | 1980-04-07 | 1981-11-04 | Eisai Co Ltd | 3,7,11,15-tetramethyl-2,4,6,10,14-hexadecapentaenic acid |
| DE3163920D1 (en) * | 1980-12-24 | 1984-07-05 | Eisai Co Ltd | Pharmaceutical preparations comprising polyprenyl compounds, especially as anti-cancer agents, and pharmaceutical compositions for the prevention and treatment of cancer and skin diseases |
| JPS57106638A (en) * | 1980-12-24 | 1982-07-02 | Eisai Co Ltd | Conjugated polyprenylcarboxylic acid and its derivative |
| JPS58164508A (ja) * | 1982-03-26 | 1983-09-29 | Eisai Co Ltd | イソプレニルカルボン酸含有外用組成物 |
| JPS5973516A (ja) * | 1982-10-21 | 1984-04-25 | Eisai Co Ltd | 抗炎症剤 |
| JPS6160612A (ja) * | 1984-08-31 | 1986-03-28 | Eisai Co Ltd | 制癌効果増強剤 |
| IL107587A (en) * | 1993-11-12 | 1998-08-16 | Univ Ramot | Farnesyl geranyl or geranyl-geranyl derivatives pharmaceutical compositions containing them and methods for their preparation |
| US20050250671A1 (en) | 2000-04-24 | 2005-11-10 | Yoshihiro Shidoji | Activators of peroxisome proliferator-activated receptor |
| CN116041172A (zh) * | 2023-02-01 | 2023-05-02 | 宝鸡文理学院 | 一种神经酸的制备方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2171497A5 (en) * | 1972-02-02 | 1973-09-21 | Rhone Poulenc Sa | 1,5-dimethyl-1,5-hexadienylidene sulphone derivs - - intermediates for terpenes |
| JPS52131507A (en) * | 1976-04-24 | 1977-11-04 | Sankyo Co Ltd | Polyprenyl derivatives |
-
1981
- 1981-04-01 DE DE19813113149 patent/DE3113149A1/de active Granted
- 1981-04-01 NL NL8101630A patent/NL191744C/xx not_active IP Right Cessation
- 1981-04-01 GB GB8110160A patent/GB2073750B/en not_active Expired
- 1981-04-03 SE SE8102161A patent/SE447243B/sv not_active IP Right Cessation
- 1981-04-06 CH CH231781A patent/CH646682A5/fr not_active IP Right Cessation
- 1981-04-06 ES ES501124A patent/ES8205190A1/es not_active Expired
- 1981-04-06 DK DK155081A patent/DK158457C/da not_active IP Right Cessation
- 1981-04-06 FR FR8106874A patent/FR2479807A1/fr active Granted
- 1981-04-06 CA CA000374715A patent/CA1179370A/en not_active Expired
- 1981-04-07 AU AU69159/81A patent/AU537402B2/en not_active Ceased
- 1981-04-07 IT IT20967/81A patent/IT1194141B/it active
-
1982
- 1982-02-25 ES ES509913A patent/ES8304058A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| SE447243B (sv) | 1986-11-03 |
| DK158457B (da) | 1990-05-21 |
| FR2479807B1 (ja) | 1984-07-20 |
| NL191744C (nl) | 1996-06-04 |
| DK155081A (da) | 1981-10-08 |
| DK158457C (da) | 1990-10-08 |
| GB2073750B (en) | 1984-02-22 |
| NL8101630A (nl) | 1981-11-02 |
| ES501124A0 (es) | 1982-06-01 |
| ES509913A0 (es) | 1983-02-16 |
| ES8304058A1 (es) | 1983-02-16 |
| SE8102161L (sv) | 1981-10-08 |
| GB2073750A (en) | 1981-10-21 |
| IT8120967A0 (it) | 1981-04-07 |
| FR2479807A1 (fr) | 1981-10-09 |
| DE3113149A1 (de) | 1982-01-28 |
| CA1179370A (en) | 1984-12-11 |
| ES8205190A1 (es) | 1982-06-01 |
| AU6915981A (en) | 1981-10-15 |
| DE3113149C2 (ja) | 1988-11-10 |
| AU537402B2 (en) | 1984-06-21 |
| IT1194141B (it) | 1988-09-14 |
| NL191744B (nl) | 1996-02-01 |
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