CH616911A5 - - Google Patents
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- Publication number
- CH616911A5 CH616911A5 CH17376A CH17376A CH616911A5 CH 616911 A5 CH616911 A5 CH 616911A5 CH 17376 A CH17376 A CH 17376A CH 17376 A CH17376 A CH 17376A CH 616911 A5 CH616911 A5 CH 616911A5
- Authority
- CH
- Switzerland
- Prior art keywords
- residue
- group
- acyl
- formula
- lower alkyl
- Prior art date
Links
- -1 alkaline earth metal carboxylate Chemical class 0.000 claims description 42
- 125000002252 acyl group Chemical group 0.000 claims description 31
- 150000001875 compounds Chemical class 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 10
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 10
- 150000002148 esters Chemical class 0.000 claims description 9
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
- 239000003513 alkali Substances 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 7
- 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 description 6
- 230000010933 acylation Effects 0.000 claims description 5
- 238000005917 acylation reaction Methods 0.000 claims description 5
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 5
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 4
- 229920005862 polyol Polymers 0.000 claims description 4
- 239000007858 starting material Substances 0.000 claims description 4
- 150000008065 acid anhydrides Chemical class 0.000 claims description 3
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 3
- 150000003077 polyols Chemical class 0.000 claims description 3
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- 125000001931 aliphatic group Chemical group 0.000 claims 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 4
- 125000004432 carbon atom Chemical group C* 0.000 claims 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 3
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- 125000003884 phenylalkyl group Chemical group 0.000 claims 3
- 150000003462 sulfoxides Chemical class 0.000 claims 3
- 125000003700 epoxy group Chemical group 0.000 claims 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 2
- WYFCZWSWFGJODV-MIANJLSGSA-N 4-[[(1s)-2-[(e)-3-[3-chloro-2-fluoro-6-(tetrazol-1-yl)phenyl]prop-2-enoyl]-5-(4-methyl-2-oxopiperazin-1-yl)-3,4-dihydro-1h-isoquinoline-1-carbonyl]amino]benzoic acid Chemical compound O=C1CN(C)CCN1C1=CC=CC2=C1CCN(C(=O)\C=C\C=1C(=CC=C(Cl)C=1F)N1N=NN=C1)[C@@H]2C(=O)NC1=CC=C(C(O)=O)C=C1 WYFCZWSWFGJODV-MIANJLSGSA-N 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- 125000003375 sulfoxide group Chemical group 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 51
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 42
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 39
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 34
- 239000000243 solution Substances 0.000 description 26
- 238000006243 chemical reaction Methods 0.000 description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 18
- 239000000047 product Substances 0.000 description 18
- HHLJUSLZGFYWKW-UHFFFAOYSA-N triethanolamine hydrochloride Chemical compound Cl.OCCN(CCO)CCO HHLJUSLZGFYWKW-UHFFFAOYSA-N 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
- 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 7
- 239000007864 aqueous solution Substances 0.000 description 7
- 230000006870 function Effects 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- TXCGAZHTZHNUAI-UHFFFAOYSA-N clofibric acid Chemical compound OC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 TXCGAZHTZHNUAI-UHFFFAOYSA-N 0.000 description 5
- 229960000367 inositol Drugs 0.000 description 5
- 239000001294 propane Substances 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- 230000001476 alcoholic effect Effects 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- JLWKPDBTSOFSTR-UHFFFAOYSA-N [3-[2-(4-chlorophenoxy)-2-methylpropanoyl]oxy-2-hydroxypropyl] 2-(4-chlorophenoxy)-2-methylpropanoate Chemical compound C=1C=C(Cl)C=CC=1OC(C)(C)C(=O)OCC(O)COC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 JLWKPDBTSOFSTR-UHFFFAOYSA-N 0.000 description 3
- 239000012230 colorless oil Substances 0.000 description 3
- 230000009993 protective function Effects 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- OODRWLGKUBMFLZ-UHFFFAOYSA-N 2-(4-chlorophenoxy)-2-methylpropanoyl chloride Chemical compound ClC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 OODRWLGKUBMFLZ-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- VVRFXEYVUZOYTI-UHFFFAOYSA-N [2-(4-chlorophenoxy)-2-methylpropanoyl] 2-(4-chlorophenoxy)-2-methylpropanoate Chemical compound C=1C=C(Cl)C=CC=1OC(C)(C)C(=O)OC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 VVRFXEYVUZOYTI-UHFFFAOYSA-N 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 125000003158 alcohol group Chemical group 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 150000007942 carboxylates Chemical class 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- CDAISMWEOUEBRE-UHFFFAOYSA-N scyllo-inosotol Natural products OC1C(O)C(O)C(O)C(O)C1O CDAISMWEOUEBRE-UHFFFAOYSA-N 0.000 description 2
- MAUQVQSXTOZPSX-UHFFFAOYSA-M sodium;2-(4-chlorophenoxy)-2-methylpropanoate Chemical compound [Na+].[O-]C(=O)C(C)(C)OC1=CC=C(Cl)C=C1 MAUQVQSXTOZPSX-UHFFFAOYSA-M 0.000 description 2
- 150000003460 sulfonic acids Polymers 0.000 description 2
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 230000009466 transformation Effects 0.000 description 2
- NLQMSBJFLQPLIJ-UHFFFAOYSA-N (3-methyloxetan-3-yl)methanol Chemical compound OCC1(C)COC1 NLQMSBJFLQPLIJ-UHFFFAOYSA-N 0.000 description 1
- ZOKHGHDRKCYWTH-UHFFFAOYSA-N 1,1-dichloropropan-2-ol Chemical compound CC(O)C(Cl)Cl ZOKHGHDRKCYWTH-UHFFFAOYSA-N 0.000 description 1
- IFDLXKQSUOWIBO-UHFFFAOYSA-N 1,3-dichloropropan-1-ol Chemical compound OC(Cl)CCCl IFDLXKQSUOWIBO-UHFFFAOYSA-N 0.000 description 1
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 1
- XXKJKUOEPZUGRS-UHFFFAOYSA-N 1-[6-(1,3-dichloropropoxymethyl)-1-hydroxycyclohexa-2,4-dien-1-yl]ethanone Chemical compound C(C)(=O)C1(C(COC(CCCl)Cl)C=CC=C1)O XXKJKUOEPZUGRS-UHFFFAOYSA-N 0.000 description 1
- VUSYFNXNYLAECV-UHFFFAOYSA-N 2,3-bis(chloromethyl)oxirane Chemical compound ClCC1OC1CCl VUSYFNXNYLAECV-UHFFFAOYSA-N 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N 2-propanol Substances CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
- BWKDAAFSXYPQOS-UHFFFAOYSA-N Benzaldehyde glyceryl acetal Chemical compound O1CC(O)COC1C1=CC=CC=C1 BWKDAAFSXYPQOS-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 229960001138 acetylsalicylic acid Drugs 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 210000001772 blood platelet Anatomy 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000003944 halohydrins Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- CDAISMWEOUEBRE-GPIVLXJGSA-N inositol Chemical compound O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@@H]1O CDAISMWEOUEBRE-GPIVLXJGSA-N 0.000 description 1
- 229960004592 isopropanol Drugs 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002924 oxiranes Chemical group 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 150000005691 triesters Chemical class 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C305/00—Esters of sulfuric acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/16—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by esterified hydroxyl radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
- C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
- C07D303/22—Ethers with hydroxy compounds containing no oxirane rings with monohydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
- C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
- C07D303/24—Ethers with hydroxy compounds containing no oxirane rings with polyhydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/18—Radicals substituted by singly bound oxygen or sulfur atoms
- C07D317/22—Radicals substituted by singly bound oxygen or sulfur atoms etherified
-
- 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
- C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
- C07D319/06—1,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/091—Esters of phosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (25)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH17376A CH616911A5 (de) | 1976-01-08 | 1976-01-08 | |
| FR7634925A FR2337552A1 (fr) | 1976-01-08 | 1976-11-19 | Esters mixtes de polyols, leur procede de preparation et medicaments renfermant ces esters |
| BE172528A BE848548A (fr) | 1976-01-08 | 1976-11-19 | Esters mixtes de polyols |
| GR52230A GR61818B (en) | 1976-01-08 | 1976-11-20 | Preparation process of mixed esters of polyols |
| YU02864/76A YU286476A (en) | 1976-01-08 | 1976-11-24 | Process for obtaining 2-(acetylsalicyloxy)-1,3-(p-chlorophenoxy-2-methylpropionyloxy)-propane |
| RO7688569A RO70355A (ro) | 1976-01-08 | 1976-11-26 | Procedeu pentru prepararea unui ester mixt de poliol |
| PT65894A PT65894B (fr) | 1976-01-08 | 1976-11-26 | Procede de preparation des esters mixtes de polyols |
| SE7613426A SE7613426L (sv) | 1976-01-08 | 1976-11-30 | Blandade estrar av polyoler |
| GB49963/76A GB1572035A (en) | 1976-01-08 | 1976-11-30 | Therapeutically active glycerol ester containing clofibryl- and 2-acetylsalicylgroups |
| ES453795A ES453795A1 (es) | 1976-01-08 | 1976-11-30 | Procedimiento de preparacion de esteres mixtos de poliol. |
| HU76LA899A HU178270B (en) | 1976-01-08 | 1976-12-01 | Process for producing mixed esters |
| CA267,026A CA1075708A (en) | 1976-01-08 | 1976-12-02 | Therapeutically active mixed esters of polyols |
| NL7613457A NL7613457A (nl) | 1976-01-08 | 1976-12-02 | Gemengde polyolesters. |
| IL51039A IL51039A0 (en) | 1976-01-08 | 1976-12-02 | Mixed polyol esters |
| DE19762654951 DE2654951A1 (de) | 1976-01-08 | 1976-12-03 | Gemischt veresterte polyole, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| US05/747,567 US4118583A (en) | 1976-01-08 | 1976-12-06 | Mixed esters of polyols |
| FI763529A FI763529A (de) | 1976-01-08 | 1976-12-08 | |
| BG7634871A BG27537A3 (en) | 1976-01-08 | 1976-12-09 | Method of obtaining of mixed polyolic esters |
| AT916676A AT349452B (de) | 1976-01-08 | 1976-12-10 | Verfahren zur herstellung von neuen gemischten estern von polyolen |
| CS768304A CS203994B2 (en) | 1976-01-08 | 1976-12-16 | Method of producing therapeutically active mixed esters of polyols |
| EG784/76A EG12290A (en) | 1976-01-08 | 1976-12-21 | Process for preparing of mixed of polyols |
| JP15351976A JPS5285139A (en) | 1976-01-08 | 1976-12-22 | Production of novel polyolester compound |
| DD7600196638A DD128400A5 (de) | 1976-01-08 | 1976-12-27 | Gemischt veresterte polyole,verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| PL1976194851A PL117246B1 (en) | 1976-01-08 | 1976-12-30 | Process for manufacturing novel mixedesters of polyhydric alcoholsykh spirtov |
| SU772435401A SU869556A3 (ru) | 1976-01-08 | 1977-01-07 | Способ получени 2-(ацетилсалицилокси)-1,3-ди-(п-хлорфенокси-2-метил-пропаноилокси)-пропана |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH17376A CH616911A5 (de) | 1976-01-08 | 1976-01-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH616911A5 true CH616911A5 (de) | 1980-04-30 |
Family
ID=4180922
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH17376A CH616911A5 (de) | 1976-01-08 | 1976-01-08 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4118583A (de) |
| AT (1) | AT349452B (de) |
| BE (1) | BE848548A (de) |
| CH (1) | CH616911A5 (de) |
| CS (1) | CS203994B2 (de) |
| HU (1) | HU178270B (de) |
| SU (1) | SU869556A3 (de) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4469704A (en) * | 1980-12-26 | 1984-09-04 | Ss Pharmaceutical Co., Ltd. | 2,3-Butanediol diester derivatives, process for producing the same, and an antiulcer drug containing the same |
| KR102622617B1 (ko) * | 2021-06-08 | 2024-01-08 | 명지대학교 산학협력단 | 신규한 글리세라이드 화합물 및 그의 제조방법 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE674556A (de) * | 1965-01-05 | 1966-06-30 |
-
1976
- 1976-01-08 CH CH17376A patent/CH616911A5/fr not_active IP Right Cessation
- 1976-11-19 BE BE172528A patent/BE848548A/xx unknown
- 1976-12-01 HU HU76LA899A patent/HU178270B/hu unknown
- 1976-12-06 US US05/747,567 patent/US4118583A/en not_active Expired - Lifetime
- 1976-12-10 AT AT916676A patent/AT349452B/de not_active IP Right Cessation
- 1976-12-16 CS CS768304A patent/CS203994B2/cs unknown
-
1977
- 1977-01-07 SU SU772435401A patent/SU869556A3/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| AT349452B (de) | 1979-04-10 |
| SU869556A3 (ru) | 1981-09-30 |
| US4118583A (en) | 1978-10-03 |
| BE848548A (fr) | 1977-03-16 |
| HU178270B (en) | 1982-04-28 |
| ATA916676A (de) | 1978-09-15 |
| CS203994B2 (en) | 1981-03-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |