JPS6153349B2 - - Google Patents
Info
- Publication number
- JPS6153349B2 JPS6153349B2 JP56125880A JP12588081A JPS6153349B2 JP S6153349 B2 JPS6153349 B2 JP S6153349B2 JP 56125880 A JP56125880 A JP 56125880A JP 12588081 A JP12588081 A JP 12588081A JP S6153349 B2 JPS6153349 B2 JP S6153349B2
- Authority
- JP
- Japan
- Prior art keywords
- thiadiazole
- reaction
- acid
- thiol
- amino
- 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
- 125000003277 amino group Chemical group 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- -1 5-substituted-1,3,4-thiadiazole-2-thiols Chemical class 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 23
- 238000006243 chemical reaction Methods 0.000 description 14
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 238000010908 decantation Methods 0.000 description 5
- 238000007363 ring formation reaction Methods 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- YNNGZCVDIREDDK-UHFFFAOYSA-N aminocarbamodithioic acid Chemical compound NNC(S)=S YNNGZCVDIREDDK-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000010511 deprotection reaction Methods 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000006228 supernatant Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 150000003573 thiols Chemical class 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- JLAMDELLBBZOOX-UHFFFAOYSA-N 3h-1,3,4-thiadiazole-2-thione Chemical class SC1=NN=CS1 JLAMDELLBBZOOX-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- OTCCIMWXFLJLIA-UHFFFAOYSA-N N-acetyl-DL-aspartic acid Natural products CC(=O)NC(C(O)=O)CC(O)=O OTCCIMWXFLJLIA-UHFFFAOYSA-N 0.000 description 2
- OTCCIMWXFLJLIA-BYPYZUCNSA-N N-acetyl-L-aspartic acid Chemical compound CC(=O)N[C@H](C(O)=O)CC(O)=O OTCCIMWXFLJLIA-BYPYZUCNSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 238000006640 acetylation reaction Methods 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- JHCKVPVXWBVGDI-UHFFFAOYSA-N hydrazine;dihydrate Chemical compound O.O.NN JHCKVPVXWBVGDI-UHFFFAOYSA-N 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- NBNQOWVYEXFQJC-UHFFFAOYSA-N 2-sulfanyl-3h-thiadiazole Chemical compound SN1NC=CS1 NBNQOWVYEXFQJC-UHFFFAOYSA-N 0.000 description 1
- NJSRYBIBUXBNSW-UHFFFAOYSA-N 3-azaniumyl-4-oxo-4-phenylmethoxybutanoate Chemical compound OC(=O)CC(N)C(=O)OCC1=CC=CC=C1 NJSRYBIBUXBNSW-UHFFFAOYSA-N 0.000 description 1
- RBVFLRAWKORMNY-UHFFFAOYSA-N 4-(2-sulfanylidene-3h-1,3,4-thiadiazol-5-yl)butanoic acid Chemical compound OC(=O)CCCC1=NN=C(S)S1 RBVFLRAWKORMNY-UHFFFAOYSA-N 0.000 description 1
- 229930186147 Cephalosporin Natural products 0.000 description 1
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 1
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- 125000003047 N-acetyl group Chemical group 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- HEMHJVSKTPXQMS-DYCDLGHISA-M Sodium hydroxide-d Chemical compound [Na+].[2H][O-] HEMHJVSKTPXQMS-DYCDLGHISA-M 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 235000001014 amino acid Nutrition 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 235000003704 aspartic acid Nutrition 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 229940124587 cephalosporin Drugs 0.000 description 1
- 150000001780 cephalosporins Chemical class 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000010446 mirabilite Substances 0.000 description 1
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- RSIJVJUOQBWMIM-UHFFFAOYSA-L sodium sulfate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])(=O)=O RSIJVJUOQBWMIM-UHFFFAOYSA-L 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP56125880A JPS5829780A (ja) | 1981-08-13 | 1981-08-13 | ５−置換アルキル−１，３，４−チアジアゾ−ル−２−チオ−ル |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP56125880A JPS5829780A (ja) | 1981-08-13 | 1981-08-13 | ５−置換アルキル−１，３，４−チアジアゾ−ル−２−チオ−ル |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5829780A JPS5829780A (ja) | 1983-02-22 |
| JPS6153349B2 true JPS6153349B2 (xx) | 1986-11-17 |
Family
ID=14921203
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP56125880A Granted JPS5829780A (ja) | 1981-08-13 | 1981-08-13 | ５−置換アルキル−１，３，４−チアジアゾ−ル−２−チオ−ル |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5829780A (xx) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0522130D0 (en) | 2005-10-31 | 2005-12-07 | Angeletti P Ist Richerche Bio | Therapeutic compounds |
-
1981
- 1981-08-13 JP JP56125880A patent/JPS5829780A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5829780A (ja) | 1983-02-22 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4940793A (en) | Pharmacologically active piperazino derivatives | |
| JPS5834474B2 (ja) | チアゾリジン誘導体の製造法 | |
| JP4048119B2 (ja) | ２−（４−クロロベンゾイルアミノ）−３−［２（１ｈ）−キノールリノン−４−イル］プロピオン酸の製造方法 | |
| CA1106838A (en) | 6-(2,3-dihydro-5-benzofuranyl) acetamido penicillin derivatives | |
| US3962272A (en) | 1h-tetrazole-1-acetate esters and acids and process therefor | |
| SU576948A3 (ru) | Способ получени производных цефалоспорановой кислоты или их солей | |
| JP3163361B2 (ja) | ５−アルキルヒダントイン誘導体の製造法 | |
| JPS6153349B2 (xx) | ||
| JPS6332073B2 (xx) | ||
| JPS6150941B2 (xx) | ||
| JPH0791304B2 (ja) | セフェムプロドラッグエステルの新規製造法 | |
| JPH0520425B2 (xx) | ||
| KR100208297B1 (ko) | 신규한 세펨 유도체의 제조방법 | |
| JPH10195064A (ja) | ５−アミノ−１，２，４−チアジアゾール酢酸誘導体（シン異性体）の製造方法 | |
| SU1757471A3 (ru) | Способ получени производных L-аланил-L-пролина или их фармацевтически приемлемых солей | |
| HU194560B (en) | Process for producing alkali salt of /3s/-3-square bracket opened-figure bracket opened-/2-protected amino-4-thiazolyl/-acetyl-figure bracket closed -amino-square bracket closed-4-alkyl-2-oxo-1-azetidinyl-sulfonic acid | |
| EP0003847A1 (en) | Biphenylylglycine derivatives and their salts with bases | |
| KR810001695B1 (ko) | 테레프탈산아미드 유도체의 제법 | |
| JP2767295B2 (ja) | インドール―３―カルボニトリル化合物の製造方法 | |
| JPH08176128A (ja) | チアゾール酢酸の製造方法 | |
| JPS6338023B2 (xx) | ||
| KR0176014B1 (ko) | 세팔로스포린 유도체의 제조방법 | |
| JPH0527617B2 (xx) | ||
| SU503517A3 (ru) | Способ получени производных индолилуксусной кислоты или их солей | |
| SU596166A3 (ru) | Способ получени производных тиазола или их аддитивных солей с минеральными кислотами или органическими сульфокислотами |