JPS6348870B2 - - Google Patents
Info
- Publication number
- JPS6348870B2 JPS6348870B2 JP60046700A JP4670085A JPS6348870B2 JP S6348870 B2 JPS6348870 B2 JP S6348870B2 JP 60046700 A JP60046700 A JP 60046700A JP 4670085 A JP4670085 A JP 4670085A JP S6348870 B2 JPS6348870 B2 JP S6348870B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- mercaptotetrazole
- solution
- thiol
- crystals
- 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
- XOHZHMUQBFJTNH-UHFFFAOYSA-N 1-methyl-2h-tetrazole-5-thione Chemical compound CN1N=NN=C1S XOHZHMUQBFJTNH-UHFFFAOYSA-N 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 9
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 8
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 239000001569 carbon dioxide Substances 0.000 claims description 4
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 230000003301 hydrolyzing effect Effects 0.000 claims description 2
- 150000002900 organolithium compounds Chemical class 0.000 claims description 2
- 150000007970 thio esters Chemical class 0.000 claims description 2
- 150000003573 thiols Chemical class 0.000 claims description 2
- 239000000243 solution Substances 0.000 description 20
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
- 239000013078 crystal Substances 0.000 description 17
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 7
- 239000002002 slurry Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- -1 tetrazole compounds Chemical class 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- UOTQEHLQKASWQO-UHFFFAOYSA-N 2-(5-sulfanylidene-2h-tetrazol-1-yl)acetic acid Chemical compound OC(=O)CN1N=NN=C1S UOTQEHLQKASWQO-UHFFFAOYSA-N 0.000 description 4
- 125000002252 acyl group Chemical group 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002024 ethyl acetate extract Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- JAAIPIWKKXCNOC-UHFFFAOYSA-N 1h-tetrazol-1-ium-5-thiolate Chemical compound SC1=NN=NN1 JAAIPIWKKXCNOC-UHFFFAOYSA-N 0.000 description 2
- RDHBKRQOSVEWGC-UHFFFAOYSA-N 2-(2h-tetrazol-5-ylsulfanyl)butanoic acid Chemical compound CCC(C(O)=O)SC1=NN=NN1 RDHBKRQOSVEWGC-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 239000003242 anti bacterial agent Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- VYPDUQYOLCLEGS-UHFFFAOYSA-M sodium;2-ethylhexanoate Chemical compound [Na+].CCCCC(CC)C([O-])=O VYPDUQYOLCLEGS-UHFFFAOYSA-M 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- GSQBIOQCECCMOQ-UHFFFAOYSA-N β-alanine ethyl ester Chemical compound CCOC(=O)CCN GSQBIOQCECCMOQ-UHFFFAOYSA-N 0.000 description 2
- LZIZWPKCGUKIGH-UHFFFAOYSA-N 2-(2h-tetrazol-5-yl)propanoic acid Chemical compound OC(=O)C(C)C=1N=NNN=1 LZIZWPKCGUKIGH-UHFFFAOYSA-N 0.000 description 1
- ZAWYIVQSOZFTHM-UHFFFAOYSA-N 2-(2h-tetrazol-5-ylsulfanyl)decanoic acid Chemical compound CCCCCCCCC(C(O)=O)SC1=NN=NN1 ZAWYIVQSOZFTHM-UHFFFAOYSA-N 0.000 description 1
- PTNXHTWBYIQRQT-UHFFFAOYSA-N 2-(2h-tetrazol-5-ylsulfanyl)heptanoic acid Chemical compound CCCCCC(C(O)=O)SC1=NN=NN1 PTNXHTWBYIQRQT-UHFFFAOYSA-N 0.000 description 1
- MYNKWTVOTSWCSE-UHFFFAOYSA-N 2-(2h-tetrazol-5-ylsulfanyl)hexanoic acid Chemical compound CCCCC(C(O)=O)SC1=NN=NN1 MYNKWTVOTSWCSE-UHFFFAOYSA-N 0.000 description 1
- LESZCGLMDCLIHC-UHFFFAOYSA-N 2-(2h-tetrazol-5-ylsulfanyl)nonanoic acid Chemical compound CCCCCCCC(C(O)=O)SC1=NN=NN1 LESZCGLMDCLIHC-UHFFFAOYSA-N 0.000 description 1
- QPBAGFQPADYDBB-UHFFFAOYSA-N 2-(2h-tetrazol-5-ylsulfanyl)octanoic acid Chemical compound CCCCCCC(C(O)=O)SC1=NN=NN1 QPBAGFQPADYDBB-UHFFFAOYSA-N 0.000 description 1
- CTXRELZEQZUMNY-UHFFFAOYSA-N 2-(2h-tetrazol-5-ylsulfanyl)pentanoic acid Chemical compound CCCC(C(O)=O)SC1=NN=NN1 CTXRELZEQZUMNY-UHFFFAOYSA-N 0.000 description 1
- VBWYAKMJWHGBIV-UHFFFAOYSA-N 2-(2h-tetrazol-5-ylsulfanyl)propanoic acid Chemical compound OC(=O)C(C)SC1=NN=NN1 VBWYAKMJWHGBIV-UHFFFAOYSA-N 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
- 239000006286 aqueous extract Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical compound OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- UPTRONYNXNYITM-UHFFFAOYSA-N ethyl 3-isothiocyanatopropanoate Chemical compound CCOC(=O)CCN=C=S UPTRONYNXNYITM-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000004820 halides Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- ACMLBODZYHZSRU-UHFFFAOYSA-N sodium;2-(5-sulfanylidene-2h-tetrazol-1-yl)acetic acid Chemical compound [Na].[Na].OC(=O)CN1NN=NC1=S ACMLBODZYHZSRU-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C265/00—Derivatives of isocyanic acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/24—Radicals substituted by 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)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Cephalosporin Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US50299174A | 1974-09-03 | 1974-09-03 | |
| US502991 | 1974-09-03 | ||
| US590971 | 1990-10-01 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60222470A JPS60222470A (ja) | 1985-11-07 |
| JPS6348870B2 true JPS6348870B2 (de) | 1988-09-30 |
Family
ID=24000311
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60046699A Granted JPS60222489A (ja) | 1974-09-03 | 1985-03-11 | ７−アミノセフエム化合物の製法 |
| JP60046700A Granted JPS60222470A (ja) | 1974-09-03 | 1985-03-11 | １−カルボキシルアルキル−５−メルカプトテトラゾ−ルの製法 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60046699A Granted JPS60222489A (ja) | 1974-09-03 | 1985-03-11 | ７−アミノセフエム化合物の製法 |
Country Status (14)
| Country | Link |
|---|---|
| JP (2) | JPS60222489A (de) |
| AT (3) | AT349140B (de) |
| AU (1) | AU503240B2 (de) |
| BE (1) | BE832725A (de) |
| BG (1) | BG27753A3 (de) |
| CH (1) | CH623330A5 (de) |
| CS (3) | CS202056B2 (de) |
| CY (1) | CY1120A (de) |
| GB (1) | GB1525626A (de) |
| HK (1) | HK45081A (de) |
| KE (1) | KE3157A (de) |
| MY (1) | MY8200111A (de) |
| SU (2) | SU691094A3 (de) |
| ZA (1) | ZA755543B (de) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4093723A (en) | 1976-05-19 | 1978-06-06 | Smithkline Corporation | 7-Acyl-3-(sulfonic acid and sulfamoyl substituted tetrazolyl thiomethyl) cephalosporins |
| US4082912A (en) | 1976-06-30 | 1978-04-04 | Bristol-Myers Company | Certain 7-acylamido-3-(2-carboxyalkyl-2,3-dihydro-s-triazolo[4,3-b]pyridazin-3-on-6-ylmethyl)-3-cephem-4-carboxylic acids their salts and easily hydrolyzed esters |
| US4278670A (en) * | 1976-07-12 | 1981-07-14 | Smithkline Corporation | 7-Alpha-oxyiminoacylcephalosporins |
| US4066762A (en) * | 1976-07-12 | 1978-01-03 | Smithkline Corporation | Derivatives of 7-(2-substituted-2-hydroxyiminoacetamido)-3-(1-substituted tetrazol-5-ylthiomethyl-3-cephem-4-carboxylic acid |
| US4117125A (en) | 1977-06-24 | 1978-09-26 | Smithkline Corporation | 7-Acylamino-3-[1-[2-(carboxymethylamino]ethyl) tetrazol-5-ylthiomethyl]-3-cephem-4-carboxylic acids |
| DK225179A (da) | 1978-06-22 | 1979-12-23 | Chugai Pharmaceutical Co Ltd | Fremgangsmaade til fremstilling af cephalosporinderivater |
| JPH01300075A (ja) * | 1988-05-25 | 1989-12-04 | Tokyo Seimitsu Hatsujo Kk | 流動体注入装置 |
-
1975
- 1975-08-25 BE BE159447A patent/BE832725A/xx not_active IP Right Cessation
- 1975-08-29 ZA ZA00755543A patent/ZA755543B/xx unknown
- 1975-09-01 BG BG7736219A patent/BG27753A3/xx active Active
- 1975-09-02 AT AT676475A patent/AT349140B/de not_active IP Right Cessation
- 1975-09-02 CY CY1120A patent/CY1120A/xx unknown
- 1975-09-02 AU AU84469/75A patent/AU503240B2/en not_active Expired
- 1975-09-02 CH CH1134575A patent/CH623330A5/de not_active IP Right Cessation
- 1975-09-02 GB GB36079/75A patent/GB1525626A/en not_active Expired
- 1975-09-03 CS CS755997A patent/CS202056B2/cs unknown
- 1975-09-03 SU SU752170664A patent/SU691094A3/ru active
-
1976
- 1976-08-10 SU SU762388313A patent/SU685157A3/ru active
-
1977
- 1977-06-07 CS CS773751A patent/CS202058B2/cs unknown
- 1977-06-07 CS CS773750A patent/CS202057B2/cs unknown
- 1977-10-10 AT AT723377A patent/AT348520B/de not_active IP Right Cessation
-
1978
- 1978-04-24 AT AT294178A patent/AT349638B/de not_active IP Right Cessation
-
1981
- 1981-08-25 KE KE3157A patent/KE3157A/xx unknown
- 1981-09-03 HK HK450/81A patent/HK45081A/xx unknown
-
1982
- 1982-12-30 MY MY111/82A patent/MY8200111A/xx unknown
-
1985
- 1985-03-11 JP JP60046699A patent/JPS60222489A/ja active Granted
- 1985-03-11 JP JP60046700A patent/JPS60222470A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| SU685157A3 (ru) | 1979-09-05 |
| CS202058B2 (en) | 1980-12-31 |
| ATA723377A (de) | 1978-07-15 |
| CH623330A5 (en) | 1981-05-29 |
| JPS60222489A (ja) | 1985-11-07 |
| MY8200111A (en) | 1982-12-31 |
| HK45081A (en) | 1981-09-11 |
| CS202056B2 (en) | 1980-12-31 |
| BG27753A3 (en) | 1979-12-12 |
| BE832725A (fr) | 1976-02-25 |
| AT349638B (de) | 1979-04-10 |
| CS202057B2 (en) | 1980-12-31 |
| SU691094A3 (ru) | 1979-10-05 |
| ZA755543B (en) | 1976-07-28 |
| AT348520B (de) | 1979-02-26 |
| KE3157A (en) | 1981-09-18 |
| AU8446975A (en) | 1977-03-10 |
| CY1120A (en) | 1981-12-04 |
| JPS6135200B2 (de) | 1986-08-12 |
| JPS60222470A (ja) | 1985-11-07 |
| ATA676475A (de) | 1978-08-15 |
| GB1525626A (en) | 1978-09-20 |
| ATA294178A (de) | 1978-09-15 |
| AU503240B2 (en) | 1979-08-30 |
| AT349140B (de) | 1979-03-26 |
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