NO753158L - - Google Patents
Info
- Publication number
- NO753158L NO753158L NO753158A NO753158A NO753158L NO 753158 L NO753158 L NO 753158L NO 753158 A NO753158 A NO 753158A NO 753158 A NO753158 A NO 753158A NO 753158 L NO753158 L NO 753158L
- Authority
- NO
- Norway
- Prior art keywords
- carbon atoms
- acetylsalicylic acid
- hydrogen atom
- same
- alkyl group
- Prior art date
Links
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical class CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 claims description 23
- 229960001138 acetylsalicylic acid Drugs 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- 239000000243 solution Substances 0.000 description 14
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
- 229940068372 acetyl salicylate Drugs 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- ZIOBGZDFMKCKGZ-UHFFFAOYSA-N 2-amino-2-methylpropanamide Chemical compound CC(C)(N)C(N)=O ZIOBGZDFMKCKGZ-UHFFFAOYSA-N 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 4
- GQEXBJOPGJUKIL-UHFFFAOYSA-N 1-aminocyclohexane-1-carboxamide Chemical compound NC(=O)C1(N)CCCCC1 GQEXBJOPGJUKIL-UHFFFAOYSA-N 0.000 description 3
- OPSUSMMZNXNXKD-UHFFFAOYSA-N 2-(dimethylamino)-2-methylpropanamide Chemical compound CN(C)C(C)(C)C(N)=O OPSUSMMZNXNXKD-UHFFFAOYSA-N 0.000 description 3
- YTSVIBZGAFTNCI-UHFFFAOYSA-N 2-methyl-2-(methylamino)propanamide Chemical compound CNC(C)(C)C(N)=O YTSVIBZGAFTNCI-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- BEBCJVAWIBVWNZ-UHFFFAOYSA-N glycinamide Chemical compound NCC(N)=O BEBCJVAWIBVWNZ-UHFFFAOYSA-N 0.000 description 3
- XIMBESZRBTVIOD-UHFFFAOYSA-N piperidine-2-carboxamide Chemical compound NC(=O)C1CCCCN1 XIMBESZRBTVIOD-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- BSYNRYMUTXBXSQ-FOQJRBATSA-N 59096-14-9 Chemical compound CC(=O)OC1=CC=CC=C1[14C](O)=O BSYNRYMUTXBXSQ-FOQJRBATSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000001754 anti-pyretic effect Effects 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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
- C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Saccharide Compounds (AREA)
Description
Fremgangsmåte for fremstilling av nyeProcedure for manufacturing new ones
derivater av acetylsalicylsyre.derivatives of acetylsalicylic acid.
Foreliggende oppfinnelse angår en fremgangsmåte for fremstilling av nye derivater av acetylsalicylsyre med den generelle formel The present invention relates to a method for the production of new derivatives of acetylsalicylic acid with the general formula
der og R~som kan være like eller forskjellige hver angir et hydrogenatom eller en alkylgruppe inneholdende 1-4 karbonatomer, eventuelt substituert med en hydroksygruppe; der R^ where and R~ which may be the same or different each denotes a hydrogen atom or an alkyl group containing 1-4 carbon atoms, optionally substituted with a hydroxy group; where R^
og R^som kan være like eller forskjellige, hver angir et hydrogenatom eller en alkylgruppe inneholdende 1-4 karbonatomer, eller der R-, og R^sammen med det karbonatom til hvilket de er bundet danner en 5- eller 6-leddet mettet ring; der et av symbolene R1og R2og et av symbolene og R^and R^ which may be the same or different, each represents a hydrogen atom or an alkyl group containing 1-4 carbon atoms, or where R-, and R^ together with the carbon atom to which they are attached form a 5- or 6-membered saturated ring ; where one of the symbols R1 and R2 and one of the symbols and R^
sammen med de nitrogen- og karbonatomer til hvilke de er bundet kan danne en 5- eller 6-leddet, nitrogenholdig heterocyklisk ring; der R,_ og Rg som kan være like eller forskjellige, hver angir et hydrogenatom eller en alkylgruppe inneholdende 1-4 karbonatomer, eventuelt substituert med en hydroksygruppe; og der n er null eller 1. together with the nitrogen and carbon atoms to which they are attached may form a 5- or 6-membered, nitrogen-containing heterocyclic ring; where R,_ and Rg, which may be the same or different, each denote a hydrogen atom or an alkyl group containing 1-4 carbon atoms, optionally substituted with a hydroxy group; and where n is zero or 1.
De nye saltene av acetylsalicylsyre med formel-The new salts of acetylsalicylic acid with the formula
en I kan ifølge foreliggende oppfinnelse fremstilles ved at en base med den generelle formel a I can, according to the present invention, be prepared by a base with the general formula
der de forskjellige symboler har de ovenfor angitte betyd-ninger, omsettes med acetylsalicylsyre. where the various symbols have the above meanings, is reacted with acetylsalicylic acid.
Reaksjonen gjennomføres vanligvis i et organisk oppløsningsmiddel slik som en alkohol (metanol, etanol, isopropanol), en keton (aceton) eller en eter (dimetoksyetan) The reaction is usually carried out in an organic solvent such as an alcohol (methanol, ethanol, isopropanol), a ketone (acetone) or an ether (dimethoxyethane)
ved en temperatur nær 20°C. Det er spesielt hensiktsmessig å arbeide i vannfrie oppløsningsmidler. at a temperature close to 20°C. It is particularly appropriate to work in anhydrous solvents.
Reaksjonen kan også gjennomføres i vannholdig medium og den dannede forbindelse med formelen I kan isoleres etter konsentrering og lyofilisering av vannoppløsningen. The reaction can also be carried out in an aqueous medium and the formed compound of formula I can be isolated after concentration and lyophilization of the aqueous solution.
Saltene med formelen I kan eventuelt renses ved omkrystallisering i et organisk oppløsningsmiddel slik som etanol. The salts of the formula I can optionally be purified by recrystallization in an organic solvent such as ethanol.
De nye saltene med formelen I oppviser samme anti-inflammatoriske, analgetiske og antipyretiske egenskaper som acetylsalicylsyre samtidig som de oppviser en meget større vannoppløselighet og en meget mindre surhet. The new salts with the formula I exhibit the same anti-inflammatory, analgesic and antipyretic properties as acetylsalicylic acid, while at the same time exhibiting a much greater water solubility and a much lower acidity.
Disse spesielle egenskaper gjør at saltene tole-reres bedre i magesekken og er lettere å inngi enn acetylsalicylsyre. Det er fremfor alt en stor fordel at det, er mulig å oppnå injiserbare oppløsninger hvilke etter injisering tole-reres godt i vener og muskler. These special properties mean that the salts are better tolerated in the stomach and are easier to administer than acetylsalicylic acid. Above all, it is a great advantage that it is possible to obtain injectable solutions which, after injection, are well tolerated in veins and muscles.
De nye saltene med formelen I oppviser hos mus samme akutte giftighet som acetylsalicylsyre. The new salts with the formula I show the same acute toxicity in mice as acetylsalicylic acid.
Av spesiell interesse er de forbindelser med formelen I der symbolene R-^R2, R^, R^, R,_ og Rg hvilke kan være like eller forskjellige hver angir et hydrogenatom eller en alkylgruppe inneholdende 1-3 karbonatomer. Of particular interest are the compounds of the formula I in which the symbols R-^R2, R^, R^, R,_ and Rg, which may be the same or different, each denote a hydrogen atom or an alkyl group containing 1-3 carbon atoms.
Oppfinnelsen skal illustreres ved følgende eksempler. The invention shall be illustrated by the following examples.
Eksempel 1Example 1
Til en oppløsning av 32,4 g acetylsalicylsyre i 480 cm^ absolutt etanol settes en oppløsning av 18,4 g 2-amino-2-metylpropionamid i 420 cm absolutt etanol og man omrører i 30 minutter ved en temperatur nær 20°C. Peilingen separeres ved filtrering, vaskes på filteret med 270 cm absolutt etanol og tørkes deretter under et redusert trykk på 0,1 mm Hg, først i 18 timer ved en temperatur n.r 20°C og deretter i 1 time ved 60°C. Man oppnår herved 26,8 g acetylsalicylat_av 2-amino-2-metylpropionamid med et smeltepunkt på l40-l42°C. A solution of 18.4 g of 2-amino-2-methylpropionamide in 420 cm of absolute ethanol is added to a solution of 32.4 g of acetylsalicylic acid in 480 cm of absolute ethanol and the mixture is stirred for 30 minutes at a temperature close to 20°C. The bearing is separated by filtration, washed on the filter with 270 cm of absolute ethanol and then dried under a reduced pressure of 0.1 mm Hg, first for 18 hours at a temperature of 20°C and then for 1 hour at 60°C. This gives 26.8 g of acetylsalicylate of 2-amino-2-methylpropionamide with a melting point of 140-142°C.
2-amino-2-metylpropionamid kan fremstilles ifølge A. Davis i "J. Chem. Soc", 2419 (1951). 2-Amino-2-methylpropionamide can be prepared according to A. Davis in "J. Chem. Soc", 2419 (1951).
Eksempel 2Example 2
72,0 g acetylsalicylsyre oppløses ved 20°C i en oppløsning av 40,8 g 2-amino-2-metylpropionamid i 500 cm^ vann. Den oppnådde oppløsning filtreres og lyofiliseres deretter under et redusert trykk på 0,1 mm Hg i 42 timer. Det lyofiliserte produkt tørkes i nærvær av fosforpentoksyd under et redusert trykk på 0,1 mm Hg ved 20°C i 27 timer. Man oppnår herved 112,4 g acetylsalicylat av 2-amino-2-metylpropion-amid med et smeltepunkt på l4l-l42°C. 72.0 g of acetylsalicylic acid is dissolved at 20°C in a solution of 40.8 g of 2-amino-2-methylpropionamide in 500 cm^ of water. The obtained solution is filtered and then lyophilized under a reduced pressure of 0.1 mm Hg for 42 hours. The lyophilized product is dried in the presence of phosphorus pentoxide under a reduced pressure of 0.1 mm Hg at 20°C for 27 hours. This gives 112.4 g of acetylsalicylate of 2-amino-2-methylpropionamide with a melting point of 141-142°C.
Eksempel 5Example 5
Til en oppløsning av 16,2 g acetylsalicylsyre i 300 cm 3 vannfri isopropanol setter man en oppløsning av 10,1 g 2-metyl-2-metylaminopropionamid i 150 cm^ vannfri isopropanol og omrører i 30 minutter ved en temperatur nær 20°C. Den dannede felling separeres ved filtrering, vaskes med 80 cm^ vannfri isopropanol og tørkes deretter under et redusert trykk på 0,1 mm Hg, først i 20 timer ved en temperatur nær 20°C og deretter i 10 timer ved 50°C. Man oppnår herved 24,0 g acetylsalicylat av 2-metyl-2-metylaminopropionamid med et smeltepunkt på 148-150°C. To a solution of 16.2 g of acetylsalicylic acid in 300 cm 3 of anhydrous isopropanol, a solution of 10.1 g of 2-methyl-2-methylaminopropionamide in 150 cm 3 of anhydrous isopropanol is added and stirred for 30 minutes at a temperature close to 20°C. The precipitate formed is separated by filtration, washed with 80 cm 3 of anhydrous isopropanol and then dried under a reduced pressure of 0.1 mm Hg, first for 20 hours at a temperature close to 20°C and then for 10 hours at 50°C. This gives 24.0 g of acetylsalicylate of 2-methyl-2-methylaminopropionamide with a melting point of 148-150°C.
2-metyl-2-metylaminopropionamid kan fremstilles ifølge A. Pinchuk i "Zhur."Obshchéi"Khim.", 39, 583 (1969) 2-methyl-2-methylaminopropionamide can be prepared according to A. Pinchuk in "Zhur."Obshchéi"Khim.", 39, 583 (1969)
(Chem. Abstr. 71, 61300 k (1969)). (Chem. Abstr. 71, 61300 k (1969)).
Eksempel 4Example 4
Til en oppløsning av 7S21 g acetylsalicylsyre iTo a solution of 7S21 g acetylsalicylic acid i
80 cm^ vannfri etanol avkjølt til 2°C setter, man 2,96 g aminoacetamid og omrører i 20 minutter ved 2°C. Den dannede felling separeres ved filtrering, vaskes med 30 cm^ vannfri etanol og tørkes under et redusert trykk på 0,1 mm Hg ved eh temperatur nær 20°C i 18 timer. Man oppnår herved 9,12 g acetylsalicylat av aminoacetamid med smeltepunkt på 115°C. 80 cm^ of anhydrous ethanol cooled to 2°C are added, 2.96 g of aminoacetamide are added and stirred for 20 minutes at 2°C. The precipitate formed is separated by filtration, washed with 30 cc of anhydrous ethanol and dried under a reduced pressure of 0.1 mm Hg at a temperature close to 20°C for 18 hours. This gives 9.12 g of acetylsalicylate of aminoacetamide with a melting point of 115°C.
Aminoacetamidet kan fremstilles ifølge R.G. Jones, i "J. Am. Chem. Soc", 71, 79 (1949). The aminoacetamide can be prepared according to R.G. Jones, in "J. Am. Chem. Soc", 71, 79 (1949).
Eksempel 5Example 5
Man oppløser under omrøring 3,60 g acetylsalicylsyre og 3j03 g 1-ammocykloheksankarboksamid 1 15 cnr vannfri aceton. Man starter krystalliseringen og omrører i 20 minutter ved en temperatur nær 20°C. Peilingen separeres ved filtrering, vaskes med 15 cm^ vannfri aceton og tørkes under et redusert trykk på 0,1 mm Hg, først i 4 timer ved en temperatur nær 20°C og deretter i 2 timer ved 50°C. Man oppnår herved 5,07 g acetylsalicylat av 1-aminocykloheksankar-boksamid med et smeltepunkt på 127-129°C. While stirring, 3.60 g of acetylsalicylic acid and 3.03 g of 1-aminocyclohexanecarboxamide are dissolved in 1 15 cnr of anhydrous acetone. The crystallization is started and stirred for 20 minutes at a temperature close to 20°C. The bearing is separated by filtration, washed with 15 cm^ of anhydrous acetone and dried under a reduced pressure of 0.1 mm Hg, first for 4 hours at a temperature near 20°C and then for 2 hours at 50°C. This gives 5.07 g of acetylsalicylate of 1-aminocyclohexanecarboxamide with a melting point of 127-129°C.
1- aminocykloheksankarboksamidet kan fremstilles ifølge A. Pinchuk i "Zhur, Obshchei" .Khim. ", 37, 856 (1967) The 1-aminocyclohexanecarboxamide can be prepared according to A. Pinchuk in "Zhur, Obshchei".Khim. ", 37, 856 (1967)
(Chem. Abstr. _6_7, 108 169 j (1967)). (Chem. Abstr. _6_7, 108 169 j (1967)).
Eksempel 6Example 6
Til en oppløsning av 18,0 g acetylsalicylsyreFor a solution of 18.0 g of acetylsalicylic acid
i l60 cm absolutt etanol setter man en oppløsning av 13,0 g 2-dimetylamino-2-metylpropionamid i 50 cm 3 absolutt etanol og omrører i 50 minutter ved en temperatur på 8-10°C. Den dannede felling separeres ved filtrering, vaskes med 90 cm^ absolutt etanol og tørkes under et redusert trykk på 0,1 mm Hg, først i 18 timer ved en temperatur nær 20°C og deretter in 160 cm of absolute ethanol, a solution of 13.0 g of 2-dimethylamino-2-methylpropionamide is placed in 50 cm 3 of absolute ethanol and stirred for 50 minutes at a temperature of 8-10°C. The precipitate formed is separated by filtration, washed with 90 cm^ of absolute ethanol and dried under a reduced pressure of 0.1 mm Hg, first for 18 hours at a temperature close to 20°C and then
i 5 timer ved 57_58°C. Man oppnår herved 26,3 g acetylsalicylat av 2-dimetylamino-2-metylpropionamid med et smeltepunkt på 132-134°C. for 5 hours at 57_58°C. This gives 26.3 g of acetylsalicylate of 2-dimethylamino-2-methylpropionamide with a melting point of 132-134°C.
2- dimetylamino-2-metylpropionamidet kan fremstilles ifølge den fremgangsmåte som beskrives i det tyske patent nr. 2.246.728. The 2-dimethylamino-2-methylpropionamide can be prepared according to the method described in German patent no. 2,246,728.
Eksempel 7Example 7
Til en oppløsning av 27,0 g acetylsalicylsyre i 200 cm 3 absolutt etanol setter man en oppløsning av 19,0 g 2-karbamoylpiperidin i 250 cm^ absolutt etanol og omrører i 30 minutter ved en temperatur nær 20°C. Den dannede felling separeres ved filtrering, vaskes med 100 cm^ absolutt etanol og tørkes under et redusert trykk på 0,1 mm Hg, først i 15 timer ved en temperatur nær 20°C og deretter i 2 timer ved 50°C. To a solution of 27.0 g of acetylsalicylic acid in 200 cm 3 of absolute ethanol, a solution of 19.0 g of 2-carbamoylpiperidine in 250 cm 3 of absolute ethanol is added and stirred for 30 minutes at a temperature close to 20°C. The precipitate formed is separated by filtration, washed with 100 cm 3 absolute ethanol and dried under a reduced pressure of 0.1 mm Hg, first for 15 hours at a temperature close to 20°C and then for 2 hours at 50°C.
Man oppnår 4l,9 g acetylsalicylat av 2-karbamoylpiperidin med et smeltepunkt på 174-176°C. 41.9 g of acetylsalicylate of 2-carbamoylpiperidine with a melting point of 174-176°C is obtained.
2-karbamoylpiperidin kan fremstilles ifølge2-carbamoylpiperidine can be prepared according to
H. Fox i "J. Org. Chem.", 17, 542 (1952).H. Fox in "J. Org. Chem.", 17, 542 (1952).
Eksempel 8Example 8
Til en oppløsning av 24,1 g acetylsalicylsyre i 300 cm^ vannfri isopropanol setter man en oppløsning av 15,1 g A solution of 15.1 g is added to a solution of 24.1 g of acetylsalicylic acid in 300 cm^ of anhydrous isopropanol
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7431400A FR2285141A1 (en) | 1974-09-17 | 1974-09-17 | Water-soluble aminoalkanoamide salts of acetylsalicylic acid - with anti-inflammatory, analgesic and antipyretic activity (BE-16.3.76) |
| FR7520099A FR2315279A1 (en) | 1975-06-26 | 1975-06-26 | Water-soluble aminoalkanoamide salts of acetylsalicylic acid - with anti-inflammatory, analgesic and antipyretic activity (BE-16.3.76) |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO753158L true NO753158L (en) | 1976-03-18 |
Family
ID=26218517
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO753158A NO753158L (en) | 1974-09-17 | 1975-09-16 |
Country Status (13)
| Country | Link |
|---|---|
| JP (1) | JPS5161615A (en) |
| AT (1) | AT339886B (en) |
| AU (1) | AU8484975A (en) |
| CH (1) | CH593234A5 (en) |
| DE (1) | DE2541475A1 (en) |
| ES (1) | ES441029A1 (en) |
| FI (1) | FI752589A (en) |
| GB (1) | GB1476026A (en) |
| HU (1) | HU172524B (en) |
| IL (1) | IL48108A0 (en) |
| LU (1) | LU73412A1 (en) |
| NL (1) | NL7510622A (en) |
| NO (1) | NO753158L (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU185926B (en) * | 1979-09-27 | 1985-04-28 | Agostne Kahan | Process for preparing water soluble derivatives of non-steroid antiinflammatory compositions and pharmaceutical compositins containing such derivatives |
| JPS5742680A (en) * | 1980-08-29 | 1982-03-10 | Bago Sa Labor | Novel ester of substituted benzoic acid and manufacture |
-
1975
- 1975-09-09 NL NL7510622A patent/NL7510622A/en not_active Application Discontinuation
- 1975-09-15 AU AU84849/75A patent/AU8484975A/en not_active Expired
- 1975-09-15 HU HU75RO00000854A patent/HU172524B/en unknown
- 1975-09-16 JP JP50111023A patent/JPS5161615A/ja active Pending
- 1975-09-16 LU LU73412A patent/LU73412A1/xx unknown
- 1975-09-16 CH CH1197375A patent/CH593234A5/xx not_active IP Right Cessation
- 1975-09-16 NO NO753158A patent/NO753158L/no unknown
- 1975-09-16 IL IL48108A patent/IL48108A0/en unknown
- 1975-09-17 GB GB3823075A patent/GB1476026A/en not_active Expired
- 1975-09-17 DE DE19752541475 patent/DE2541475A1/en active Pending
- 1975-09-17 ES ES441029A patent/ES441029A1/en not_active Expired
- 1975-09-17 FI FI752589A patent/FI752589A/fi not_active Application Discontinuation
- 1975-09-17 AT AT713675A patent/AT339886B/en active
Also Published As
| Publication number | Publication date |
|---|---|
| HU172524B (en) | 1978-09-28 |
| JPS5161615A (en) | 1976-05-28 |
| AT339886B (en) | 1977-11-10 |
| CH593234A5 (en) | 1977-11-30 |
| ATA713675A (en) | 1977-03-15 |
| AU8484975A (en) | 1977-03-24 |
| GB1476026A (en) | 1977-06-10 |
| NL7510622A (en) | 1976-03-19 |
| IL48108A0 (en) | 1975-11-25 |
| LU73412A1 (en) | 1976-08-13 |
| DE2541475A1 (en) | 1976-03-25 |
| ES441029A1 (en) | 1977-03-01 |
| FI752589A (en) | 1976-03-18 |
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