IL44786A - Salts of 2-n-propyl 5-thiazolecarboxylic acid and pharmaceutical compositions containing same - Google Patents
Salts of 2-n-propyl 5-thiazolecarboxylic acid and pharmaceutical compositions containing sameInfo
- Publication number
- IL44786A IL44786A IL4478674A IL4478674A IL44786A IL 44786 A IL44786 A IL 44786A IL 4478674 A IL4478674 A IL 4478674A IL 4478674 A IL4478674 A IL 4478674A IL 44786 A IL44786 A IL 44786A
- Authority
- IL
- Israel
- Prior art keywords
- propyl
- salts
- pharmaceutical compositions
- compositions containing
- containing same
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 title description 4
- 239000008194 pharmaceutical composition Chemical class 0.000 title description 3
- IOSZDNOGOPHEPH-UHFFFAOYSA-N 2-propyl-1,3-thiazole-5-carboxylic acid Chemical class CCCC1=NC=C(C(O)=O)S1 IOSZDNOGOPHEPH-UHFFFAOYSA-N 0.000 title 1
- 239000004411 aluminium Substances 0.000 claims description 7
- 229910052782 aluminium Inorganic materials 0.000 claims description 7
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 6
- 229910052791 calcium Inorganic materials 0.000 claims description 6
- 239000011575 calcium Substances 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 4
- 239000000825 pharmaceutical preparation Substances 0.000 claims 3
- 239000004480 active ingredient Substances 0.000 claims 2
- 159000000013 aluminium salts Chemical class 0.000 claims 1
- 230000000055 hyoplipidemic effect Effects 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 239000007891 compressed tablet Substances 0.000 description 3
- 235000021588 free fatty acids Nutrition 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 2
- 230000001154 acute effect Effects 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 231100000636 lethal dose Toxicity 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- OSNIIMCBVLBNGS-UHFFFAOYSA-N 1-(1,3-benzodioxol-5-yl)-2-(dimethylamino)propan-1-one Chemical compound CN(C)C(C)C(=O)C1=CC=C2OCOC2=C1 OSNIIMCBVLBNGS-UHFFFAOYSA-N 0.000 description 1
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000002440 hepatic effect Effects 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 229940071462 oralone Drugs 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- LMHHRCOWPQNFTF-UHFFFAOYSA-N s-propan-2-yl azepane-1-carbothioate Chemical compound CC(C)SC(=O)N1CCCCCC1 LMHHRCOWPQNFTF-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
Classifications
-
- 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
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/003—Compounds containing elements of Groups 2 or 12 of the Periodic Table without C-Metal linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- 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
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/06—Aluminium compounds
- C07F5/069—Aluminium compounds without C-aluminium linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Cephalosporin Compounds (AREA)
- Medicinal Preparation (AREA)
Description
In Israel Patent 32616 there are described 2 carboxyllc acids their salts and their esters conforming to the general wherein R designates al kal i metal ammonium or an ai kyi group optionally substituted by phenyl 1 or 2 group or where and are lower ai kyi groups or 1s a saturated cycl ic ring optional ly by oxygen and represents a aikyi group containing from 3 to 12 carbon The present Invention relates to novel salts of and especially to calcium and to al uminium s 1 azol ecarbox 1 a te The novel compounds of the present Invention possess Interesting pharmaceutical They are characterized by a pronounced They can be used n as In the treatment of acute or hyper1 of aetheromatosls or hepatic or toxic steatoses and of dlc The present Invention relates also to pharmaceutical compositions containing the above defined novel compounds as active The novel pharmaceutical compositions can be administered by the buccal rectal or parenteral They may be used 1n the form of Injectable solutions or 1n tablet 1n the form of coated of Example Calcium One dissol ves 10 g of arboxy11c 1n 100 cm3 of ethanol and adds at whilst g of One heats at for one eliminates the Insoluble matter by filtration and adds 500 cm One keeps at for one One separates by filtration and obtains after calcium CX HX NX SX 17 Example aluminium carboxyl One takes to whilst agi a mixture of g of 1c acid and g of aluminium Isopropylate 1n 100 cm3 of ethanol at 95 One maintains at reflux for eighteen hours and cools the One concentrates under reduced pressure and obtains a white solid which one dissolves 1n methylene one thus 3 obtains a soluti on which one dilutes 1n 600 cm of One takes the solution obtained to for and then maintains at ambient temperature for hours One vacuum filters and after g of basic aluminium CX NX V Example aluminium t of aci d One maintains at for ve hours a mixture of g of 2 g of al uminium 3 i late and 15 cm of dimethyl One then leaves the solution obtained to stand for then pours 3 200 cm of One the precipitate mono washes it and dries One thus obtains al uminium salt of Example Preparation of compressed tablets One prepared compressed tablet of al uminium sal t of 500 Sufficient quantity of for a compressed tablet up to 750 mg of the magnesium Pharmacological Study of the Aluminium of Acid Determination of acute The acute toxicity was determined on groups of ten mice weighing to 22 The product was administered in the form of a suspension of carboxy cellulose Tween 1n Increasing The animals were maintained under supervision for 48 The mean lethal dose was determined graphically by the method of Miller and The lethal dose was found to be greater than 1000 Determination of Hypolipldaemic Determination of free fatty acids in Male of the Sprague Dawley weighing 180 to 200 were left to fast during 24 hours were given the product by the oral One hour after receiving the the animals were sacrificed and the free fatty acids were determined in the blood of The extraction of the free fatty acids was effected according to the modified Dole technique The plasma extract f eed of phospholipids was examined colori metrically by the automatic technique of The following results were Dosage decrease versus control 5 A clear effect of the product on the level of blood insufficientOCRQuality
Claims (7)
1. Calcium and Monobasic aluminium b1s-(2-n-propyl-5-thiazole-carboxylates).
2. Calcium bis-(2-n-propyl-5-th1azolecarboxylate).
3. Mono-basic aluminium b1s-(2-n-propyl-5-th1azolecarboxylate).
4. Pharmaceutical preparations comprising as active Ingredient a compound as claimed 1n any of claims 1 to 3.
5. A pharmaceutical preparation comprising as active Ingredient a compound as claimed in claim 2 or in claim 3.
6. pharmaceutical preparations having a hypolipidemic activity, substantially as hereinbefore described and with reference to the examples.
7. Calcium and mono-basic aluminium salts of 2-n-propyl-5-th1azol carboxylic add, substantially as hereinbefore described and with refeeeoce to the examples. Attorneys for Applicant
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7317070A FR2228483A2 (en) | 1973-05-11 | 1973-05-11 | Esters and salts of 2-propylthiazole-5-carboxylic acid - vasodilators and hypolipidaemics |
| FR7410277A FR2265370B2 (en) | 1974-03-26 | 1974-03-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IL44786A true IL44786A (en) | 1977-05-31 |
Family
ID=26217719
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL4478674A IL44786A (en) | 1973-05-11 | 1974-05-08 | Salts of 2-n-propyl 5-thiazolecarboxylic acid and pharmaceutical compositions containing same |
Country Status (11)
| Country | Link |
|---|---|
| JP (1) | JPS5030870A (en) |
| AR (2) | AR204990A1 (en) |
| CA (1) | CA1023367A (en) |
| CH (1) | CH602681A5 (en) |
| ES (1) | ES426123A2 (en) |
| GB (1) | GB1432919A (en) |
| HU (1) | HU168854B (en) |
| IE (1) | IE39262B1 (en) |
| IL (1) | IL44786A (en) |
| LU (1) | LU70025A1 (en) |
| NL (1) | NL7406356A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6084129U (en) * | 1983-11-10 | 1985-06-10 | ダイハツ工業株式会社 | Pressed parts loading device |
-
1974
- 1974-01-01 AR AR25365374A patent/AR204990A1/en active
- 1974-05-08 IL IL4478674A patent/IL44786A/en unknown
- 1974-05-08 HU HURO000779 patent/HU168854B/hu unknown
- 1974-05-09 LU LU70025A patent/LU70025A1/xx unknown
- 1974-05-09 ES ES426123A patent/ES426123A2/en not_active Expired
- 1974-05-10 CH CH646274A patent/CH602681A5/xx not_active IP Right Cessation
- 1974-05-10 NL NL7406356A patent/NL7406356A/xx not_active Application Discontinuation
- 1974-05-10 IE IE100374A patent/IE39262B1/en unknown
- 1974-05-10 CA CA199,737A patent/CA1023367A/en not_active Expired
- 1974-05-10 JP JP5141574A patent/JPS5030870A/ja active Pending
- 1974-05-13 GB GB2108874A patent/GB1432919A/en not_active Expired
-
1978
- 1978-04-25 AR AR25850978A patent/AR212497A1/en active
Also Published As
| Publication number | Publication date |
|---|---|
| AR212497A1 (en) | 1978-07-31 |
| AR204990A1 (en) | 1976-03-31 |
| LU70025A1 (en) | 1974-11-28 |
| CH602681A5 (en) | 1978-07-31 |
| IE39262B1 (en) | 1978-08-30 |
| ES426123A2 (en) | 1976-12-16 |
| CA1023367A (en) | 1977-12-27 |
| HU168854B (en) | 1976-07-28 |
| IE39262L (en) | 1974-11-11 |
| JPS5030870A (en) | 1975-03-27 |
| NL7406356A (en) | 1974-11-13 |
| GB1432919A (en) | 1976-04-22 |
| AU6879674A (en) | 1975-11-13 |
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