JPS6215058B2 - - Google Patents
Info
- Publication number
- JPS6215058B2 JPS6215058B2 JP9807379A JP9807379A JPS6215058B2 JP S6215058 B2 JPS6215058 B2 JP S6215058B2 JP 9807379 A JP9807379 A JP 9807379A JP 9807379 A JP9807379 A JP 9807379A JP S6215058 B2 JPS6215058 B2 JP S6215058B2
- Authority
- JP
- Japan
- Prior art keywords
- ethyl alcohol
- aspirin
- salt
- basic amino
- solution
- 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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 90
- 235000019441 ethanol Nutrition 0.000 claims description 44
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 claims description 37
- 229960001138 acetylsalicylic acid Drugs 0.000 claims description 37
- 239000000243 solution Substances 0.000 claims description 21
- 150000001413 amino acids Chemical class 0.000 claims description 16
- 239000013078 crystal Substances 0.000 claims description 13
- 238000004519 manufacturing process Methods 0.000 claims description 9
- -1 amino acid salt Chemical class 0.000 claims description 7
- 239000007864 aqueous solution Substances 0.000 claims description 7
- 238000002156 mixing Methods 0.000 claims description 2
- BSYNRYMUTXBXSQ-FOQJRBATSA-N 59096-14-9 Chemical compound CC(=O)OC1=CC=CC=C1[14C](O)=O BSYNRYMUTXBXSQ-FOQJRBATSA-N 0.000 claims 1
- 238000000034 method Methods 0.000 description 25
- 150000003839 salts Chemical class 0.000 description 22
- 235000001014 amino acid Nutrition 0.000 description 17
- KDXKERNSBIXSRK-UHFFFAOYSA-N lysine Chemical compound NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 14
- 239000012528 membrane Substances 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 239000003795 chemical substances by application Substances 0.000 description 11
- 230000001376 precipitating effect Effects 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 230000001954 sterilising effect Effects 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 238000004659 sterilization and disinfection Methods 0.000 description 8
- DDRJAANPRJIHGJ-UHFFFAOYSA-N creatinine Chemical compound CN1CC(=O)NC1=N DDRJAANPRJIHGJ-UHFFFAOYSA-N 0.000 description 7
- JJBCTCGUOQYZHK-UHFFFAOYSA-N 2-acetyloxybenzoate;(5-amino-1-carboxypentyl)azanium Chemical class OC(=O)C(N)CCCC[NH3+].CC(=O)OC1=CC=CC=C1C([O-])=O JJBCTCGUOQYZHK-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 241000894006 Bacteria Species 0.000 description 4
- 241000233866 Fungi Species 0.000 description 4
- 238000005755 formation reaction Methods 0.000 description 4
- 230000036512 infertility Effects 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 3
- 239000004472 Lysine Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 229940109239 creatinine Drugs 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000003125 aqueous solvent Substances 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 239000012456 homogeneous solution Substances 0.000 description 2
- 238000009776 industrial production Methods 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000012266 salt solution Substances 0.000 description 2
- WPLOVIFNBMNBPD-ATHMIXSHSA-N subtilin Chemical compound CC1SCC(NC2=O)C(=O)NC(CC(N)=O)C(=O)NC(C(=O)NC(CCCCN)C(=O)NC(C(C)CC)C(=O)NC(=C)C(=O)NC(CCCCN)C(O)=O)CSC(C)C2NC(=O)C(CC(C)C)NC(=O)C1NC(=O)C(CCC(N)=O)NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C1NC(=O)C(=C/C)/NC(=O)C(CCC(N)=O)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)CNC(=O)C(NC(=O)C(NC(=O)C2NC(=O)CNC(=O)C3CCCN3C(=O)C(NC(=O)C3NC(=O)C(CC(C)C)NC(=O)C(=C)NC(=O)C(CCC(O)=O)NC(=O)C(NC(=O)C(CCCCN)NC(=O)C(N)CC=4C5=CC=CC=C5NC=4)CSC3)C(C)SC2)C(C)C)C(C)SC1)CC1=CC=CC=C1 WPLOVIFNBMNBPD-ATHMIXSHSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 206010010774 Constipation Diseases 0.000 description 1
- 235000019766 L-Lysine Nutrition 0.000 description 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical compound OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 description 1
- 229930064664 L-arginine Natural products 0.000 description 1
- 235000014852 L-arginine Nutrition 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000006229 amino acid addition Effects 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000004042 decolorization Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 235000020776 essential amino acid Nutrition 0.000 description 1
- 239000003797 essential amino acid Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 210000004051 gastric juice Anatomy 0.000 description 1
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 1
- 230000002631 hypothermal effect Effects 0.000 description 1
- 210000002011 intestinal secretion Anatomy 0.000 description 1
- 230000002475 laxative effect Effects 0.000 description 1
- 235000018977 lysine Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9807379A JPS5622748A (en) | 1979-08-02 | 1979-08-02 | Preparation of acetyl salicylate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9807379A JPS5622748A (en) | 1979-08-02 | 1979-08-02 | Preparation of acetyl salicylate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5622748A JPS5622748A (en) | 1981-03-03 |
| JPS6215058B2 true JPS6215058B2 (fr) | 1987-04-06 |
Family
ID=14210163
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP9807379A Granted JPS5622748A (en) | 1979-08-02 | 1979-08-02 | Preparation of acetyl salicylate |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5622748A (fr) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ITMI20121144A1 (it) * | 2012-06-28 | 2013-12-29 | Dipharma Francis Srl | Procedimento per la preparazione di un sale di un farmaco antinfiammatorio non steroideo |
-
1979
- 1979-08-02 JP JP9807379A patent/JPS5622748A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5622748A (en) | 1981-03-03 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| FI65441C (fi) | Foerfarande foer framstaellning av inklusionskomplex av cyklodextrin och indometacin | |
| JPS5923313B2 (ja) | （＋）カテキンの水溶性複塩およびその製造方法 | |
| KR900001422B1 (ko) | 5-클로로-3-(2-테노일)-2-옥신돌-1-카복스아미드의 무수 결정성 나트륨 염 | |
| EP0755398B1 (fr) | Procede de resolution de l'etodolac a l'aide de derives de la glucamine | |
| JPS638354A (ja) | ジアセチルライン塩及び関節炎の治療におけるそれらの使用 | |
| EP0067666B1 (fr) | Sels de composés microbicides de naphtyridine et quinoléine et leur préparation | |
| KR960003327B1 (ko) | 디클로페낙과 환상 유기염기와의 염 및 이를 함유한 약학적 조성물 | |
| CN112552196A (zh) | 一种制备赖氨匹林的方法 | |
| FR2491072A1 (fr) | Nouveaux derives de la lincomycine | |
| US5206265A (en) | Iron citrate complex, process for its production, and its pharmaceutical | |
| JPS63201187A (ja) | ４−チアゾリジンカルボン酸誘導体、その製造法および医薬品組成物 | |
| JPS6215058B2 (fr) | ||
| PT93571B (pt) | Processo para a preparacao do acido (s)-7-(3-amino-1-pirrolidinil)-1-ciclopropil -6-fluoro-1,4-dihidro-4-oxo-1,8-naftiridino-3-carboxilico e de composicoes farmaceuticas que o contem | |
| CN111647006B (zh) | 头孢噻肟钠药物制剂及治疗包括伤寒和副伤寒的沙门菌感染适应症 | |
| US2756226A (en) | Acid-stable penicillins | |
| US3839317A (en) | Digoxin complexes | |
| US5254728A (en) | Complexes containing S(+)-phenyl alkanoic acids and α-hydroxyalkanoic | |
| US3360549A (en) | Ornithine aspartate and a process for its preparation | |
| Jacobson | ALFALFA SAPONIN. ALFALFA INVESTIGATION VII. | |
| DK171235B1 (da) | Krystallinsk (5R,6S)-2-carbamoyloxymethyl-6-[(IR)-hydroxyethyl]-2-penemcarboxylsyre, fremgangsmåde til fremstilling heraf, samt farmaceutisk præparat indeholdende syren | |
| US2641609A (en) | Therapeutic compound and method of preparing the same | |
| JPS6366821B2 (fr) | ||
| JPH0315632B2 (fr) | ||
| US3888916A (en) | Amantadine salt of 16,16-dimethyl-pge' 2 | |
| JPH0673085A (ja) | デカプラニン塩溶液および結晶デカプラニン塩ならびにそれらの調製方法 |