DE2549783C3 - Triglyceride mit entzündungshemmender Wirkung - Google Patents
Triglyceride mit entzündungshemmender WirkungInfo
- Publication number
- DE2549783C3 DE2549783C3 DE2549783A DE2549783A DE2549783C3 DE 2549783 C3 DE2549783 C3 DE 2549783C3 DE 2549783 A DE2549783 A DE 2549783A DE 2549783 A DE2549783 A DE 2549783A DE 2549783 C3 DE2549783 C3 DE 2549783C3
- Authority
- DE
- Germany
- Prior art keywords
- chloride
- compound
- acid
- chloroform
- triglycerides
- 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
- 150000003626 triacylglycerols Chemical class 0.000 title claims description 10
- 230000003110 anti-inflammatory effect Effects 0.000 title description 9
- 239000002253 acid Substances 0.000 claims description 17
- 150000001875 compounds Chemical class 0.000 description 44
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 42
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 42
- -1 hydrocarbon radical Chemical class 0.000 description 18
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- 239000000203 mixture Substances 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- 229940121363 anti-inflammatory agent Drugs 0.000 description 12
- 239000002260 anti-inflammatory agent Substances 0.000 description 12
- 239000003208 petroleum Substances 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 11
- 206010030113 Oedema Diseases 0.000 description 11
- 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 11
- 238000000034 method Methods 0.000 description 11
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- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 description 10
- 239000007787 solid Substances 0.000 description 9
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- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 8
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 7
- 230000003902 lesion Effects 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
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- 150000002148 esters Chemical class 0.000 description 6
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- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
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- 125000004432 carbon atom Chemical group C* 0.000 description 5
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- 241000700159 Rattus Species 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 230000002496 gastric effect Effects 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
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- 206010053155 Epigastric discomfort Diseases 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 208000025865 Ulcer Diseases 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 239000008120 corn starch Substances 0.000 description 3
- 150000005690 diesters Chemical class 0.000 description 3
- FPAFDBFIGPHWGO-UHFFFAOYSA-N dioxosilane;oxomagnesium;hydrate Chemical compound O.[Mg]=O.[Mg]=O.[Mg]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O FPAFDBFIGPHWGO-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
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- 150000003254 radicals Chemical class 0.000 description 3
- 229910000033 sodium borohydride Inorganic materials 0.000 description 3
- 239000012279 sodium borohydride Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 3
- 231100000397 ulcer Toxicity 0.000 description 3
- MPPODKLDCLFLKT-UHFFFAOYSA-N (3-acetyloxy-2-hydroxypropyl) acetate Chemical compound CC(=O)OCC(O)COC(C)=O MPPODKLDCLFLKT-UHFFFAOYSA-N 0.000 description 2
- GFAZGHREJPXDMH-UHFFFAOYSA-N 1,3-dipalmitoylglycerol Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(O)COC(=O)CCCCCCCCCCCCCCC GFAZGHREJPXDMH-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 206010017788 Gastric haemorrhage Diseases 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 206010061218 Inflammation Diseases 0.000 description 2
- 206010022653 Intestinal haemorrhages Diseases 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- VFEKBHKRXKVKGN-UHFFFAOYSA-N arachidic acid-2-hydroxy-glycerol ester Natural products CCCCCCCCCCCCCCCCCCCC(=O)OCC(O)COC(=O)CCCCCCCCCCCCCCCCCCC VFEKBHKRXKVKGN-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 230000001684 chronic effect Effects 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
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- 239000000945 filler Substances 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 230000004054 inflammatory process Effects 0.000 description 2
- 210000004072 lung Anatomy 0.000 description 2
- 210000004324 lymphatic system Anatomy 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000006186 oral dosage form Substances 0.000 description 2
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 239000006187 pill Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 2
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
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- 238000012360 testing method Methods 0.000 description 2
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- NOBREYQKJREPES-MAZCIEHSSA-N (6z,9z,30z,33z)-19,19-dihydroxynonatriaconta-6,9,30,33-tetraene-18,20,22-trione Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(=O)CC(=O)C(O)(O)C(=O)CCCCCCC\C=C/C\C=C/CCCCC NOBREYQKJREPES-MAZCIEHSSA-N 0.000 description 1
- FBWMYSQUTZRHAT-HZJYTTRNSA-N (9z,12z)-octadeca-9,12-dienoyl chloride Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(Cl)=O FBWMYSQUTZRHAT-HZJYTTRNSA-N 0.000 description 1
- JCVDBGZISOFVOT-UHFFFAOYSA-N 1,3-di(dodecanoyloxy)propan-2-yl 6-acetyl-6-hydroxycyclohexa-2,4-diene-1-carboxylate Chemical compound CCCCCCCCCCCC(=O)OCC(COC(=O)CCCCCCCCCCC)OC(=O)C1C=CC=CC1(O)C(C)=O JCVDBGZISOFVOT-UHFFFAOYSA-N 0.000 description 1
- IBFZQZMCOFTZOV-UHFFFAOYSA-N 1,3-di(octanoyloxy)propan-2-yl 6-acetyl-6-hydroxycyclohexa-2,4-diene-1-carboxylate Chemical compound CCCCCCCC(=O)OCC(COC(=O)CCCCCCC)OC(=O)C1C=CC=CC1(O)C(C)=O IBFZQZMCOFTZOV-UHFFFAOYSA-N 0.000 description 1
- KBWFWZJNPVZRRG-UHFFFAOYSA-N 1,3-dibutyrin Chemical compound CCCC(=O)OCC(O)COC(=O)CCC KBWFWZJNPVZRRG-UHFFFAOYSA-N 0.000 description 1
- LYPGMYIQHDZFFD-MAZCIEHSSA-N 1,3-dilinoleoylglycerol Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(=O)OCC(O)COC(=O)CCCCCCC\C=C/C\C=C/CCCCC LYPGMYIQHDZFFD-MAZCIEHSSA-N 0.000 description 1
- UWSKGGCTSSBJET-UHFFFAOYSA-N 1-[6-(chloromethyl)-1-hydroxycyclohexa-2,4-dien-1-yl]ethanone Chemical compound CC(=O)C1(O)C=CC=CC1CCl UWSKGGCTSSBJET-UHFFFAOYSA-N 0.000 description 1
- CRXBFRGGWLHENH-UHFFFAOYSA-N 17,17-dihydroxypentatriacontane-16,18,20-trione Chemical compound CCCCCCCCCCCCCCCC(=O)CC(=O)C(O)(O)C(=O)CCCCCCCCCCCCCCC CRXBFRGGWLHENH-UHFFFAOYSA-N 0.000 description 1
- BVKFQEAERCHBTG-UHFFFAOYSA-N 17,18,19-trihydroxypentatriacontane-16,20-dione Chemical compound CCCCCCCCCCCCCCCC(=O)C(O)C(O)C(O)C(=O)CCCCCCCCCCCCCCC BVKFQEAERCHBTG-UHFFFAOYSA-N 0.000 description 1
- UGCNLCOVHWSWLA-UHFFFAOYSA-N 2-(6-methoxynaphthalen-1-yl)propanoyl chloride Chemical compound ClC(=O)C(C)C1=CC=CC2=CC(OC)=CC=C21 UGCNLCOVHWSWLA-UHFFFAOYSA-N 0.000 description 1
- 125000005273 2-acetoxybenzoic acid group Chemical group 0.000 description 1
- GNYWBJRDQHPSJL-UHFFFAOYSA-N 6-acetyl-6-hydroxycyclohexa-2,4-diene-1-carboxylic acid Chemical compound CC(=O)C1(O)C=CC=CC1C(O)=O GNYWBJRDQHPSJL-UHFFFAOYSA-N 0.000 description 1
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- HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 description 1
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- 230000000007 visual effect Effects 0.000 description 1
- 238000005406 washing 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
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D209/26—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with an acyl radical attached to the ring nitrogen atom
- C07D209/28—1-(4-Chlorobenzoyl)-2-methyl-indolyl-3-acetic acid, substituted in position 5 by an oxygen or nitrogen atom; Esters thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
- C11C3/04—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/521,727 US3988446A (en) | 1974-11-07 | 1974-11-07 | Glycerides with anti-inflammatory properties |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2549783A1 DE2549783A1 (de) | 1976-05-20 |
| DE2549783B2 DE2549783B2 (de) | 1979-06-07 |
| DE2549783C3 true DE2549783C3 (de) | 1980-03-20 |
Family
ID=24077893
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2549783A Expired DE2549783C3 (de) | 1974-11-07 | 1975-11-06 | Triglyceride mit entzündungshemmender Wirkung |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US3988446A (enExample) |
| JP (1) | JPS5165706A (enExample) |
| CA (1) | CA1067488A (enExample) |
| CH (1) | CH601167A5 (enExample) |
| DE (1) | DE2549783C3 (enExample) |
| DK (1) | DK154287C (enExample) |
| FR (1) | FR2290189A1 (enExample) |
| GB (1) | GB1490603A (enExample) |
| NL (1) | NL161499C (enExample) |
| SE (1) | SE425733B (enExample) |
| ZA (1) | ZA756196B (enExample) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4150125A (en) * | 1977-09-30 | 1979-04-17 | Abbott Laboratories | Triglyceride ester of phosphonoacetic acid having antiviral activity |
| US4178299A (en) * | 1978-03-27 | 1979-12-11 | Abbott Laboratories | Process for preparing 1,3-diacyl glycerols |
| JPS5935941B2 (ja) * | 1979-04-02 | 1984-08-31 | 株式会社資生堂 | 紫外線吸収剤 |
| CA1176644A (en) * | 1982-03-24 | 1984-10-23 | Neil E. Bateman | Pharmaceutical compound and process for the manufacture thereof |
| US4546197A (en) * | 1982-03-24 | 1985-10-08 | R. P. Scherer Corporation | Pharmaceutical composition and process for the manufacture thereof |
| US4607052A (en) * | 1983-04-15 | 1986-08-19 | Roussel-Uclaf | Triglycerides, dietetic and therapeutical applications and compositions containing them |
| US4701469A (en) * | 1983-04-15 | 1987-10-20 | Roussel Uclaf | Triglycerides, process for therapeutical applications and compositions containing them |
| AU7872491A (en) * | 1990-05-07 | 1991-11-27 | Vical, Inc. | Lipid prodrugs of salicylate and nonsteroidal anti-inflammatory drugs |
| CN1126987A (zh) * | 1994-04-19 | 1996-07-17 | 钟渊化学工业株式会社 | 三唑衍生物的制造方法 |
| GB0311081D0 (en) | 2003-05-14 | 2003-06-18 | Btg Internat Limted | Treatment of neurodegenerative conditions |
| WO2005018632A1 (en) | 2003-08-18 | 2005-03-03 | Btg International Limited | Treatment of neurodegenerative conditions |
| GB0425658D0 (en) * | 2004-11-22 | 2004-12-22 | Stanford Rook Ltd | Immunotherapeutic agent |
| JP5470672B2 (ja) * | 2004-12-09 | 2014-04-16 | コニカミノルタ株式会社 | セルロースエステルフィルムの製造方法 |
| GB0504362D0 (en) | 2005-03-02 | 2005-04-06 | Btg Int Ltd | Cytokine modulators |
| US20100104625A1 (en) * | 2007-02-16 | 2010-04-29 | Cornell University | Biodegradable compositions and materials |
| WO2018115984A1 (en) | 2016-12-19 | 2018-06-28 | Cellix Bio Private Limited | Compositions and methods for the treatment of inflammation |
| EP4262778A4 (en) * | 2020-12-21 | 2025-10-22 | Univ New York State Res Found | PENETRATING CRYOPROTECTIVE AGENTS AND METHODS OF MAKING AND USING THE SAME |
| CN112516129B (zh) * | 2021-01-09 | 2022-04-29 | 兰州大学 | 反式1,3-二亚油精在制备治疗胃癌药物、健胃药物、保健品和食品中的应用 |
| CN112500288B (zh) * | 2021-01-09 | 2023-02-03 | 兰州大学 | 一种反式1,3-二亚油精的制备方法 |
| CN112746854B (zh) * | 2021-02-22 | 2023-04-28 | 核工业井巷建设集团有限公司 | 一种适用于顶管机的防管节抱死的注浆结构和一种顶管机 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3119739A (en) * | 1961-05-03 | 1964-01-28 | Wanda L Campbell | Acetylmethyl-salicylate for pain relief |
| US3279990A (en) * | 1963-01-31 | 1966-10-18 | Jacobs Albert L | Carbohydrate esters of salicylic acid, their production and administration |
| GB1080470A (en) * | 1963-12-31 | 1967-08-23 | Merck & Co Inc | Indole derivatives |
| CH500973A (de) * | 1966-10-31 | 1970-12-31 | Ciba Geigy Ag | Verfahren zur Herstellung neuer Derivate von Phenylessigsäuren |
| US3468907A (en) * | 1967-04-10 | 1969-09-23 | Schering Corp | Glyceryl esters of alpha-(1-aroyl-3-indolyl)alkanoic acids |
| US3652609A (en) * | 1969-06-24 | 1972-03-28 | American Home Prod | 2-parachlorophenoxy-2-methylpropionic acid-fatty acid glycerides |
| US3644424A (en) * | 1969-10-16 | 1972-02-22 | Schering Corp | Glyceryl acetylsalicylate and its analgesic anti-inflammatory use |
| DE2004098B2 (de) * | 1970-01-30 | 1978-09-14 | Dynamit Nobel Ag, 5210 Troisdorf | Nichtspröde, partialesterfreie Suppositorienmassen und Verfahren zu deren Herstellung |
-
1974
- 1974-11-07 US US05/521,727 patent/US3988446A/en not_active Expired - Lifetime
-
1975
- 1975-09-30 CA CA236,743A patent/CA1067488A/en not_active Expired
- 1975-09-30 ZA ZA00756196A patent/ZA756196B/xx unknown
- 1975-10-02 GB GB40420/75A patent/GB1490603A/en not_active Expired
- 1975-10-22 NL NL7512376.A patent/NL161499C/xx not_active IP Right Cessation
- 1975-10-23 JP JP50126934A patent/JPS5165706A/ja active Granted
- 1975-10-24 FR FR7532694A patent/FR2290189A1/fr active Granted
- 1975-11-05 SE SE7512421A patent/SE425733B/xx not_active IP Right Cessation
- 1975-11-06 CH CH1437175A patent/CH601167A5/xx not_active IP Right Cessation
- 1975-11-06 DK DK499875A patent/DK154287C/da active
- 1975-11-06 DE DE2549783A patent/DE2549783C3/de not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| SE425733B (sv) | 1982-11-01 |
| FR2290189B1 (enExample) | 1980-11-21 |
| NL7512376A (nl) | 1976-05-11 |
| JPS568820B2 (enExample) | 1981-02-25 |
| SE7512421L (sv) | 1976-05-10 |
| DK154287B (da) | 1988-10-31 |
| DE2549783B2 (de) | 1979-06-07 |
| AU8541975A (en) | 1977-04-07 |
| ZA756196B (en) | 1976-09-29 |
| NL161499B (nl) | 1979-09-17 |
| DK499875A (da) | 1976-05-08 |
| CH601167A5 (enExample) | 1978-06-30 |
| GB1490603A (en) | 1977-11-02 |
| US3988446A (en) | 1976-10-26 |
| DE2549783A1 (de) | 1976-05-20 |
| DK154287C (da) | 1989-04-17 |
| JPS5165706A (en) | 1976-06-07 |
| FR2290189A1 (fr) | 1976-06-04 |
| CA1067488A (en) | 1979-12-04 |
| NL161499C (nl) | 1980-02-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |