CA1067488A - Glycerides with anti-inflammatory properties - Google Patents
Glycerides with anti-inflammatory propertiesInfo
- Publication number
- CA1067488A CA1067488A CA236,743A CA236743A CA1067488A CA 1067488 A CA1067488 A CA 1067488A CA 236743 A CA236743 A CA 236743A CA 1067488 A CA1067488 A CA 1067488A
- Authority
- CA
- Canada
- Prior art keywords
- compound
- indomethacoyl
- acyl
- whenever prepared
- prepared according
- 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
- 230000003110 anti-inflammatory effect Effects 0.000 title claims abstract description 21
- 125000005456 glyceride group Chemical group 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 46
- 238000000034 method Methods 0.000 claims abstract description 29
- 239000002253 acid Substances 0.000 claims abstract description 20
- 125000002252 acyl group Chemical group 0.000 claims abstract description 17
- -1 di-ester ketone Chemical class 0.000 claims abstract description 17
- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 claims abstract description 12
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerol Substances OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229940120503 dihydroxyacetone Drugs 0.000 claims abstract 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 claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 5
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract 2
- 239000000126 substance Substances 0.000 claims 7
- 239000002260 anti-inflammatory agent Substances 0.000 abstract description 10
- 229940124599 anti-inflammatory drug Drugs 0.000 abstract description 4
- 230000000694 effects Effects 0.000 abstract description 4
- 150000003626 triacylglycerols Chemical class 0.000 abstract description 4
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 36
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 34
- 229960001701 chloroform Drugs 0.000 description 17
- 239000000203 mixture Substances 0.000 description 17
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 238000002844 melting Methods 0.000 description 12
- 230000008018 melting Effects 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- 241001465754 Metazoa Species 0.000 description 10
- 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 9
- 239000003208 petroleum Substances 0.000 description 9
- 206010030113 Oedema Diseases 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
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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 7
- 229940121363 anti-inflammatory agent Drugs 0.000 description 7
- 230000007794 irritation Effects 0.000 description 7
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- 239000000463 material Substances 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 6
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 6
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 231100000418 oral toxicity Toxicity 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
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- 210000002784 stomach Anatomy 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
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- 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
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- 231100000397 ulcer Toxicity 0.000 description 3
- DMBAVJVECSKEPF-UHFFFAOYSA-N 1,3-dioctanoylglycerol Chemical compound CCCCCCCC(=O)OCC(O)COC(=O)CCCCCCC DMBAVJVECSKEPF-UHFFFAOYSA-N 0.000 description 2
- QDEOLQXBVGPPDR-UHFFFAOYSA-N 6-acetyl-6-hydroxycyclohexa-2,4-diene-1-carbonyl chloride Chemical compound CC(=O)C1(O)C=CC=CC1C(Cl)=O QDEOLQXBVGPPDR-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 206010017788 Gastric haemorrhage Diseases 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 206010061218 Inflammation Diseases 0.000 description 2
- 206010022653 Intestinal haemorrhages Diseases 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- ARHWPKZXBHOEEE-UHFFFAOYSA-N alclofenac Chemical compound OC(=O)CC1=CC=C(OCC=C)C(Cl)=C1 ARHWPKZXBHOEEE-UHFFFAOYSA-N 0.000 description 2
- 229960005142 alclofenac Drugs 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 230000001684 chronic effect Effects 0.000 description 2
- 150000005690 diesters Chemical class 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 230000004054 inflammatory process Effects 0.000 description 2
- 230000000968 intestinal effect Effects 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 230000000873 masking effect Effects 0.000 description 2
- 230000007935 neutral effect Effects 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
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
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- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 230000000007 visual effect Effects 0.000 description 2
- MPPODKLDCLFLKT-UHFFFAOYSA-N (3-acetyloxy-2-hydroxypropyl) acetate Chemical compound CC(=O)OCC(O)COC(C)=O MPPODKLDCLFLKT-UHFFFAOYSA-N 0.000 description 1
- KUVAEMGNHJQSMH-UHFFFAOYSA-N (3-dodecanoyloxy-2-hydroxypropyl) dodecanoate Chemical compound CCCCCCCCCCCC(=O)OCC(O)COC(=O)CCCCCCCCCCC KUVAEMGNHJQSMH-UHFFFAOYSA-N 0.000 description 1
- 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
- DZWSPILGFKEWHY-UHFFFAOYSA-N 1,3-di(hexadecanoyloxy)propan-2-yl 6-acetyl-6-hydroxycyclohexa-2,4-diene-1-carboxylate Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(COC(=O)CCCCCCCCCCCCCCC)OC(=O)C1C=CC=CC1(O)C(C)=O DZWSPILGFKEWHY-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
- GFAZGHREJPXDMH-UHFFFAOYSA-N 1,3-dipalmitoylglycerol Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(O)COC(=O)CCCCCCCCCCCCCCC GFAZGHREJPXDMH-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
- XQMPFCWHEKIBNV-UHFFFAOYSA-N 2-(6-methoxynaphthalen-1-yl)propanoic acid Chemical compound OC(=O)C(C)C1=CC=CC2=CC(OC)=CC=C21 XQMPFCWHEKIBNV-UHFFFAOYSA-N 0.000 description 1
- ZZBQRGHQSPLVIS-UHFFFAOYSA-N 2-[1-methyl-5-(4-methylphenyl)pyrrol-2-yl]acetic acid Chemical compound C1=CC(C)=CC=C1C1=CC=C(CC(O)=O)N1C ZZBQRGHQSPLVIS-UHFFFAOYSA-N 0.000 description 1
- GDAQMHVUFPUQDQ-UHFFFAOYSA-N 3-(6-methoxynaphthalen-1-yl)propanoyl chloride Chemical compound COC=1C=C2C=CC=C(C2=CC=1)CCC(=O)Cl GDAQMHVUFPUQDQ-UHFFFAOYSA-N 0.000 description 1
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- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- KEQUNHIAUQQPAC-UHFFFAOYSA-N Dihydroxyacetone (dimer) Chemical compound OCC1(O)COC(O)(CO)CO1 KEQUNHIAUQQPAC-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
- 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
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- 239000007916 tablet composition Substances 0.000 description 1
- FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 150000005691 triesters Chemical class 0.000 description 1
- 235000012431 wafers Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 235000019786 weight gain Nutrition 0.000 description 1
- 238000010626 work up procedure Methods 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 (1)
| Publication Number | Publication Date |
|---|---|
| CA1067488A true CA1067488A (en) | 1979-12-04 |
Family
ID=24077893
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA236,743A Expired CA1067488A (en) | 1974-11-07 | 1975-09-30 | Glycerides with anti-inflammatory properties |
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) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112746854A (zh) * | 2021-02-22 | 2021-05-04 | 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 |
Families Citing this family (19)
| 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 |
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
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112746854A (zh) * | 2021-02-22 | 2021-05-04 | 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 |
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 |
| NL161499C (nl) | 1980-02-15 |
| DE2549783C3 (de) | 1980-03-20 |
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