JPS60258186A - ７−アミノ−３−置換チオメチルセフエム−４−カルボン酸類の製造法 - Google Patents
７−アミノ−３−置換チオメチルセフエム−４−カルボン酸類の製造法Info
- Publication number
- JPS60258186A JPS60258186A JP11478084A JP11478084A JPS60258186A JP S60258186 A JPS60258186 A JP S60258186A JP 11478084 A JP11478084 A JP 11478084A JP 11478084 A JP11478084 A JP 11478084A JP S60258186 A JPS60258186 A JP S60258186A
- Authority
- JP
- Japan
- Prior art keywords
- acid
- compound
- amino
- methane
- substituted
- 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.)
- Granted
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- 239000002253 acid Substances 0.000 claims abstract description 27
- 150000001875 compounds Chemical class 0.000 claims abstract description 18
- -1 7-aminocephalosporanic acid compound Chemical class 0.000 claims abstract description 16
- 150000003839 salts Chemical class 0.000 claims abstract description 15
- 239000003960 organic solvent Substances 0.000 claims abstract description 11
- 125000000962 organic group Chemical group 0.000 claims abstract description 4
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims description 20
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 18
- OPUAWDUYWRUIIL-UHFFFAOYSA-N methanedisulfonic acid Chemical compound OS(=O)(=O)CS(O)(=O)=O OPUAWDUYWRUIIL-UHFFFAOYSA-N 0.000 claims description 4
- NARPMWPOFWHFDX-UHFFFAOYSA-N methanetrisulfonic acid Chemical compound OS(=O)(=O)C(S(O)(=O)=O)S(O)(=O)=O NARPMWPOFWHFDX-UHFFFAOYSA-N 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000001550 cephem group Chemical group 0.000 claims 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract description 15
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 abstract description 10
- 230000000694 effects Effects 0.000 abstract description 5
- 229940098779 methanesulfonic acid Drugs 0.000 abstract description 5
- 238000000034 method Methods 0.000 abstract description 5
- 230000003115 biocidal effect Effects 0.000 abstract 1
- 150000001782 cephems Chemical group 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 23
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- HSHGZXNAXBPPDL-HZGVNTEJSA-N 7beta-aminocephalosporanic acid Chemical compound S1CC(COC(=O)C)=C(C([O-])=O)N2C(=O)[C@@H]([NH3+])[C@@H]12 HSHGZXNAXBPPDL-HZGVNTEJSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 238000004128 high performance liquid chromatography Methods 0.000 description 6
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 5
- 235000011114 ammonium hydroxide Nutrition 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 238000007796 conventional method Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000002699 waste material Substances 0.000 description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical class OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- XOHZHMUQBFJTNH-UHFFFAOYSA-N 1-methyl-2h-tetrazole-5-thione Chemical compound CN1N=NN=C1S XOHZHMUQBFJTNH-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- GGZHVNZHFYCSEV-UHFFFAOYSA-N 1-Phenyl-5-mercaptotetrazole Chemical compound SC1=NN=NN1C1=CC=CC=C1 GGZHVNZHFYCSEV-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- PWDHVOLKXYHEQF-UHFFFAOYSA-N C=CC(Cl)Cl.Cl Chemical compound C=CC(Cl)Cl.Cl PWDHVOLKXYHEQF-UHFFFAOYSA-N 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000000278 alkyl amino alkyl group Chemical group 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000004103 aminoalkyl group Chemical group 0.000 description 1
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 125000004181 carboxyalkyl group Chemical group 0.000 description 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- WVPKAWVFTPWPDB-UHFFFAOYSA-N dichlorophosphinic acid Chemical compound OP(Cl)(Cl)=O WVPKAWVFTPWPDB-UHFFFAOYSA-N 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- CNTIXUGILVWVHR-UHFFFAOYSA-N diphosphoryl chloride Chemical compound ClP(Cl)(=O)OP(Cl)(Cl)=O CNTIXUGILVWVHR-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- JYCLGQPRXBMNET-UHFFFAOYSA-N methanedisulfonic acid Chemical compound S(=O)(=O)(O)CS(=O)(=O)O.C(S(=O)(=O)O)S(=O)(=O)O JYCLGQPRXBMNET-UHFFFAOYSA-N 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- NEJJLKBZUWDRPI-UHFFFAOYSA-N n-(diethylaminooxy)-n-ethylethanamine Chemical group CCN(CC)ON(CC)CC NEJJLKBZUWDRPI-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- MCSAJNNLRCFZED-UHFFFAOYSA-N nitroethane Chemical compound CC[N+]([O-])=O MCSAJNNLRCFZED-UHFFFAOYSA-N 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- SBOJXQVPLKSXOG-UHFFFAOYSA-N o-amino-hydroxylamine Chemical group NON SBOJXQVPLKSXOG-UHFFFAOYSA-N 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
Landscapes
- Cephalosporin Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11478084A JPS60258186A (ja) | 1984-06-04 | 1984-06-04 | ７−アミノ−３−置換チオメチルセフエム−４−カルボン酸類の製造法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11478084A JPS60258186A (ja) | 1984-06-04 | 1984-06-04 | ７−アミノ−３−置換チオメチルセフエム−４−カルボン酸類の製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60258186A true JPS60258186A (ja) | 1985-12-20 |
| JPH0361674B2 JPH0361674B2 (enrdf_load_stackoverflow) | 1991-09-20 |
Family
ID=14646494
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP11478084A Granted JPS60258186A (ja) | 1984-06-04 | 1984-06-04 | ７−アミノ−３−置換チオメチルセフエム−４−カルボン酸類の製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60258186A (enrdf_load_stackoverflow) |
-
1984
- 1984-06-04 JP JP11478084A patent/JPS60258186A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0361674B2 (enrdf_load_stackoverflow) | 1991-09-20 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPS6339869A (ja) | アミノチアゾリル酢酸の新規なオキシム誘導体及びその製造法 | |
| JP3751880B2 (ja) | 高純度セフポドキシムプロキセチルの製造方法 | |
| JPS597717B2 (ja) | セフアロスポリン誘導体およびその製造法 | |
| JPS60258186A (ja) | ７−アミノ−３−置換チオメチルセフエム−４−カルボン酸類の製造法 | |
| JPH0454674B2 (enrdf_load_stackoverflow) | ||
| JP3086310B2 (ja) | ３−アシルアミノ−６−フェニルオキシ−７−アルキルスルホニルアミノ−４ｈ−１−ベンゾピラン−４−オン誘導体またはその塩の製造法 | |
| NO831057L (no) | Fremgangsmaate for fremstilling av lett hydrolyserbare estere som nedbrytes in vivo til beta-laktam-antibiotika og beta-laktamase-inhibitoren penicillansyre-sulfon | |
| CA1236089A (en) | Ceftazidime | |
| US20040242864A1 (en) | Process for the preparation of crystalline cefuroxime axetil | |
| JPH072750B2 (ja) | ６−Ｄ−α−（４−エチル−２，３−ジオクソ−１−ピペラジノカルボニルアミノ）−フエニルアセトアミド−ペニシラン酸の製造方法 | |
| CA2408853A1 (en) | Process | |
| WO2005035539A1 (ja) | ペニシリン結晶及びその製造法 | |
| JP2003511455A (ja) | ７−アミノ−３−メトキシメチル−３−セフェム−４−カルボン酸の製造方法 | |
| JP3235914B2 (ja) | ４，５−ジクロロフタル酸又はその塩の製造方法 | |
| US7476760B2 (en) | Purification and production methods of 1-aminocyclopropanecarboxylic acid | |
| AU581541B2 (en) | Method of preparing 6-betahalopenicillanic acids | |
| JP3089373B2 (ja) | ２−メルカプト−フェノチアジンの製造方法 | |
| EP0106369B1 (en) | Purification of ceforanide | |
| JPS6123198B2 (enrdf_load_stackoverflow) | ||
| KR101170192B1 (ko) | 1,2-벤즈이속사졸-3-메탄술폰아미드의 원-포트 제조방법 | |
| KR20010073096A (ko) | 옥사졸 화합물의 제조방법 | |
| JPS6372693A (ja) | ペニシラノイルオキシペニシラナ−ト類の製造の改良方法 | |
| SU635870A3 (ru) | Способ получени производных оксадиазолина | |
| KR800000863B1 (ko) | 세펨 유도체의 제조방법 | |
| JP2601708B2 (ja) | Ｎ―アルカノイルシステインの製造方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |