JP2006507289A5 - - Google Patents
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- JP2006507289A5 JP2006507289A5 JP2004547902A JP2004547902A JP2006507289A5 JP 2006507289 A5 JP2006507289 A5 JP 2006507289A5 JP 2004547902 A JP2004547902 A JP 2004547902A JP 2004547902 A JP2004547902 A JP 2004547902A JP 2006507289 A5 JP2006507289 A5 JP 2006507289A5
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- JP
- Japan
- Prior art keywords
- group
- formula
- compound
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- Prior art date
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- 238000000034 method Methods 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 6
- QNJLADIWFYPULV-NQPNHJOESA-N (6r)-4-(chloromethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-en-8-one Chemical class C1=CC(CCl)S[C@@H]2CC(=O)N21 QNJLADIWFYPULV-NQPNHJOESA-N 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 2
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 8
- 150000001875 compounds Chemical class 0.000 claims 7
- 239000002904 solvent Chemical class 0.000 claims 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 6
- 239000002585 base Chemical class 0.000 claims 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 4
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims 4
- 239000002253 acid Substances 0.000 claims 4
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- 239000012320 chlorinating reagent Substances 0.000 claims 3
- 229910052751 metal Inorganic materials 0.000 claims 3
- 239000002184 metal Substances 0.000 claims 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims 2
- 229910021529 ammonia Inorganic materials 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- -1 aryl sulfinic acids Chemical class 0.000 claims 2
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 claims 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 2
- 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000002927 2-methoxybenzyl group Chemical group [H]C1=C([H])C([H])=C(C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 claims 1
- 239000005695 Ammonium acetate Substances 0.000 claims 1
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 claims 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 claims 1
- SKVCFOFOWALKJJ-UHFFFAOYSA-L [Ag+2].CC1=CC=C(S([O-])=O)C=C1.CC1=CC=C(S([O-])=O)C=C1 Chemical compound [Ag+2].CC1=CC=C(S([O-])=O)C=C1.CC1=CC=C(S([O-])=O)C=C1 SKVCFOFOWALKJJ-UHFFFAOYSA-L 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 229940043376 ammonium acetate Drugs 0.000 claims 1
- 235000019257 ammonium acetate Nutrition 0.000 claims 1
- 239000001099 ammonium carbonate Substances 0.000 claims 1
- 235000012501 ammonium carbonate Nutrition 0.000 claims 1
- 150000003863 ammonium salts Chemical class 0.000 claims 1
- 229910000019 calcium carbonate Inorganic materials 0.000 claims 1
- 235000010216 calcium carbonate Nutrition 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- ZJAIXMWQDVXMLZ-UHFFFAOYSA-L copper;4-methylbenzenesulfinate Chemical compound [Cu+2].CC1=CC=C(S([O-])=O)C=C1.CC1=CC=C(S([O-])=O)C=C1 ZJAIXMWQDVXMLZ-UHFFFAOYSA-L 0.000 claims 1
- JHCPRMVDOCTAMG-UHFFFAOYSA-L copper;benzenesulfinate Chemical compound [Cu+2].[O-]S(=O)C1=CC=CC=C1.[O-]S(=O)C1=CC=CC=C1 JHCPRMVDOCTAMG-UHFFFAOYSA-L 0.000 claims 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims 1
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 claims 1
- 125000000532 dioxanyl group Chemical group 0.000 claims 1
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 claims 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 239000011736 potassium bicarbonate Substances 0.000 claims 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 claims 1
- 235000015497 potassium bicarbonate Nutrition 0.000 claims 1
- 229910000027 potassium carbonate Inorganic materials 0.000 claims 1
- 235000011181 potassium carbonates Nutrition 0.000 claims 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 claims 1
- 238000007363 ring formation reaction Methods 0.000 claims 1
- 229910000029 sodium carbonate Inorganic materials 0.000 claims 1
- 235000017550 sodium carbonate Nutrition 0.000 claims 1
- KHDBMTLGTSGEEG-UHFFFAOYSA-M sodium;2-methylbenzenesulfinate Chemical compound [Na+].CC1=CC=CC=C1S([O-])=O KHDBMTLGTSGEEG-UHFFFAOYSA-M 0.000 claims 1
- BUUPQKDIAURBJP-UHFFFAOYSA-N sulfinic acid Chemical compound OS=O BUUPQKDIAURBJP-UHFFFAOYSA-N 0.000 claims 1
- 150000003455 sulfinic acids Chemical class 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- 0 C*(C)C(*(N=C1O)I)=NC1=O Chemical compound C*(C)C(*(N=C1O)I)=NC1=O 0.000 description 4
- 229930186147 Cephalosporin Natural products 0.000 description 2
- 239000003242 anti bacterial agent Substances 0.000 description 2
- 229940088710 antibiotic agent Drugs 0.000 description 2
- 229940124587 cephalosporin Drugs 0.000 description 2
- 150000001780 cephalosporins Chemical class 0.000 description 2
- APVGDPSJTZERQC-UHFFFAOYSA-N CCC1(CCCC1)C#C Chemical compound CCC1(CCCC1)C#C APVGDPSJTZERQC-UHFFFAOYSA-N 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN808CH2002 | 2002-11-01 | ||
| PCT/IB2003/004721 WO2004039813A1 (en) | 2002-11-01 | 2003-10-23 | An improved process for the preparation of chloro methyl cephem derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2006507289A JP2006507289A (ja) | 2006-03-02 |
| JP2006507289A5 true JP2006507289A5 (enrdf_load_stackoverflow) | 2006-12-21 |
Family
ID=35561711
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004547902A Pending JP2006507289A (ja) | 2002-11-01 | 2003-10-23 | 改良されたクロロメチルセフェム誘導体調製方法 |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JP2006507289A (enrdf_load_stackoverflow) |
| KR (1) | KR20050087791A (enrdf_load_stackoverflow) |
| CN (1) | CN1315841C (enrdf_load_stackoverflow) |
| AU (1) | AU2003269416A1 (enrdf_load_stackoverflow) |
| WO (1) | WO2004039813A1 (enrdf_load_stackoverflow) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1666483B1 (en) * | 2003-09-09 | 2011-08-17 | Nippon Chemical Industrial Company Limited | Process for producing 3-chloromethyl-3-cephem derivative |
| CN101260116A (zh) * | 2008-04-21 | 2008-09-10 | 湖南有色凯铂生物药业有限公司 | 7-苯乙酰胺-3-氯甲基-4-头孢烷酸对甲氧苄酯的合成方法 |
| CN102344459B (zh) * | 2011-07-27 | 2014-08-06 | 山西新天源医药化工有限公司 | 一种头孢中间体gcle的制备方法 |
| CN102643294B (zh) * | 2012-04-18 | 2014-11-26 | 山东普洛得邦医药有限公司 | 一种头孢母核中间体的制备方法 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IE35152B1 (en) * | 1969-08-26 | 1975-11-26 | Glaxo Lab Ltd | Improvements in or relating to cephalosporin compounds |
| NL7411505A (nl) * | 1973-09-06 | 1975-03-10 | Rhone Poulenc Sa | Werkwijze voor de bereiding en toepassing van nieuwe 7-trichlooraceetamido-3-desacetoxy-cefa- losporanzuurpreparaten. |
| AU498131B2 (en) * | 1974-02-26 | 1979-02-15 | Ciba-Geigy Ag | Production of cephems by cyclization |
| GB2099817B (en) * | 1981-04-10 | 1985-05-15 | Otsuka Kagaku Yakuhin | Azetidinone derivatives and process for the preparation of the same |
| JPS5874689A (ja) * | 1981-10-29 | 1983-05-06 | Otsuka Chem Co Ltd | ３−クロロメチル−３−セフエム誘導体の製造法 |
| JPS6043340B2 (ja) * | 1981-04-10 | 1985-09-27 | 大塚化学薬品株式会社 | 塩素化アゼチジノン誘導体及びその製造法 |
| JPS59164771A (ja) * | 1983-03-10 | 1984-09-17 | Otsuka Chem Co Ltd | 塩素化アゼチジノン誘導体の製造方法 |
| JPS60115562A (ja) * | 1983-11-28 | 1985-06-22 | Otsuka Chem Co Ltd | アゼチジノン誘導体の製造法 |
| JPS60237061A (ja) * | 1984-05-08 | 1985-11-25 | Otsuka Chem Co Ltd | アゼチジノン誘導体の製造法 |
| DE3933934A1 (de) * | 1989-10-03 | 1991-04-11 | Bayer Ag | Verfahren zur herstellung von 7-amino-3-((z)-1-propen-1-yl)-3-cephem-4-carbonsaeure |
| JP3224279B2 (ja) * | 1992-07-27 | 2001-10-29 | 大塚化学株式会社 | セフエム化合物の製造法 |
| JP4157177B2 (ja) * | 1997-06-04 | 2008-09-24 | 大塚化学ホールディングス株式会社 | ３−アルケニルセフェム化合物の製造法 |
-
2003
- 2003-10-23 AU AU2003269416A patent/AU2003269416A1/en not_active Abandoned
- 2003-10-23 WO PCT/IB2003/004721 patent/WO2004039813A1/en active Application Filing
- 2003-10-23 CN CNB2003801023937A patent/CN1315841C/zh not_active Expired - Fee Related
- 2003-10-23 KR KR1020057007694A patent/KR20050087791A/ko not_active Withdrawn
- 2003-10-23 JP JP2004547902A patent/JP2006507289A/ja active Pending
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