CS203927B2 - Process for preparing 1-oxadethiacephalosporines - Google Patents
Process for preparing 1-oxadethiacephalosporines Download PDFInfo
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- CS203927B2 CS203927B2 CS785485A CS548578A CS203927B2 CS 203927 B2 CS203927 B2 CS 203927B2 CS 785485 A CS785485 A CS 785485A CS 548578 A CS548578 A CS 548578A CS 203927 B2 CS203927 B2 CS 203927B2
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- 238000004519 manufacturing process Methods 0.000 title description 3
- -1 p-hydroxyphenyl Chemical group 0.000 claims abstract description 84
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 31
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- 238000000034 method Methods 0.000 claims abstract description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 3
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- 238000002360 preparation method Methods 0.000 claims description 3
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- 238000002329 infrared spectrum Methods 0.000 description 7
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- ZFXVRMSLJDYJCH-UHFFFAOYSA-N calcium magnesium Chemical compound [Mg].[Ca] ZFXVRMSLJDYJCH-UHFFFAOYSA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 150000001844 chromium Chemical class 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 125000006182 dimethyl benzyl group Chemical group 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 125000006277 halobenzyl group Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000002054 inoculum Substances 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Chemical class 0.000 description 1
- HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 description 1
- 229940095102 methyl benzoate Drugs 0.000 description 1
- 125000006178 methyl benzyl group Chemical group 0.000 description 1
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000006502 nitrobenzyl group Chemical group 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 125000006501 nitrophenyl group Chemical group 0.000 description 1
- 239000012434 nucleophilic reagent Substances 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000006201 parenteral dosage form Substances 0.000 description 1
- 150000002960 penicillins Chemical class 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 125000005633 phthalidyl group Chemical group 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 125000005374 siloxide group Chemical group 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 125000003638 stannyl group Chemical group [H][Sn]([H])([H])* 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 125000005039 triarylmethyl group Chemical group 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical class [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D505/00—Heterocyclic compounds containing 5-oxa-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. oxacephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
-
- 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
-
- 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
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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cephalosporin Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP52102261A JPS609718B2 (ja) | 1977-08-25 | 1977-08-25 | チアジアゾリルチオセフアロスポリン類縁抗生物質 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS203927B2 true CS203927B2 (en) | 1981-03-31 |
Family
ID=14322642
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS785485A CS203927B2 (en) | 1977-08-25 | 1978-08-22 | Process for preparing 1-oxadethiacephalosporines |
Country Status (34)
| Country | Link |
|---|---|
| US (1) | US4201782A (en, 2012) |
| JP (1) | JPS609718B2 (en, 2012) |
| AR (1) | AR220539A1 (en, 2012) |
| AT (1) | AT361121B (en, 2012) |
| AU (1) | AU517618B2 (en, 2012) |
| BE (1) | BE869955A (en, 2012) |
| BG (1) | BG34338A3 (en, 2012) |
| CA (1) | CA1101417A (en, 2012) |
| CH (1) | CH637396A5 (en, 2012) |
| CS (1) | CS203927B2 (en, 2012) |
| DD (1) | DD137230A5 (en, 2012) |
| DE (1) | DE2837264A1 (en, 2012) |
| DK (1) | DK372878A (en, 2012) |
| ES (1) | ES472817A1 (en, 2012) |
| FI (1) | FI65432C (en, 2012) |
| FR (1) | FR2401165A1 (en, 2012) |
| GB (1) | GB1576796A (en, 2012) |
| GR (1) | GR70260B (en, 2012) |
| HU (1) | HU177900B (en, 2012) |
| IE (1) | IE47630B1 (en, 2012) |
| IL (1) | IL55429A0 (en, 2012) |
| IT (1) | IT1118098B (en, 2012) |
| MX (1) | MX5328E (en, 2012) |
| NL (1) | NL190554C (en, 2012) |
| NO (1) | NO782866L (en, 2012) |
| NZ (1) | NZ188173A (en, 2012) |
| PH (1) | PH17508A (en, 2012) |
| PL (1) | PL110656B1 (en, 2012) |
| PT (1) | PT68434A (en, 2012) |
| RO (1) | RO75070A (en, 2012) |
| SE (1) | SE452010B (en, 2012) |
| SU (1) | SU812182A3 (en, 2012) |
| YU (1) | YU43999B (en, 2012) |
| ZA (1) | ZA784753B (en, 2012) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4259485A (en) * | 1979-04-24 | 1981-03-31 | Eli Lilly And Company | Crystallization process |
| FR2494279A1 (fr) * | 1980-11-20 | 1982-05-21 | Rhone Poulenc Ind | Nouvelles oxacephalosporines, leur preparation et les medicaments qui les contiennent |
| EP0112049B1 (en) * | 1982-12-14 | 1987-09-09 | Beecham Group Plc | Process for the preparation of beta-lactam compounds |
| JPS60123490A (ja) * | 1983-12-07 | 1985-07-02 | Shionogi & Co Ltd | マロニルオキサセフェムカルボン酸誘導体 |
| US6013835A (en) * | 1995-06-07 | 2000-01-11 | Hfm International, Inc. | Method and apparatus for preparing purified terephthalic acid |
| US6197794B1 (en) | 1998-01-08 | 2001-03-06 | Celltech Therapeutics Limited | Phenylalanine derivatives |
| US6329372B1 (en) | 1998-01-27 | 2001-12-11 | Celltech Therapeutics Limited | Phenylalanine derivatives |
| JP2002504534A (ja) | 1998-02-26 | 2002-02-12 | セルテック・セラピューティクス・リミテッド | α４インテグリンの阻害剤としてのフェニルアラニン誘導体 |
| GB9805655D0 (en) | 1998-03-16 | 1998-05-13 | Celltech Therapeutics Ltd | Chemical compounds |
| US6521626B1 (en) | 1998-03-24 | 2003-02-18 | Celltech R&D Limited | Thiocarboxamide derivatives |
| GB9811159D0 (en) | 1998-05-22 | 1998-07-22 | Celltech Therapeutics Ltd | Chemical compounds |
| GB9811969D0 (en) | 1998-06-03 | 1998-07-29 | Celltech Therapeutics Ltd | Chemical compounds |
| GB9812088D0 (en) | 1998-06-05 | 1998-08-05 | Celltech Therapeutics Ltd | Chemical compounds |
| GB9814414D0 (en) | 1998-07-03 | 1998-09-02 | Celltech Therapeutics Ltd | Chemical compounds |
| GB9821061D0 (en) | 1998-09-28 | 1998-11-18 | Celltech Therapeutics Ltd | Chemical compounds |
| GB9821222D0 (en) | 1998-09-30 | 1998-11-25 | Celltech Therapeutics Ltd | Chemical compounds |
| GB9821406D0 (en) * | 1998-10-01 | 1998-11-25 | Celltech Therapeutics Ltd | Chemical compounds |
| GB9825652D0 (en) | 1998-11-23 | 1999-01-13 | Celltech Therapeutics Ltd | Chemical compounds |
| US6518283B1 (en) | 1999-05-28 | 2003-02-11 | Celltech R&D Limited | Squaric acid derivatives |
| US6534513B1 (en) | 1999-09-29 | 2003-03-18 | Celltech R&D Limited | Phenylalkanoic acid derivatives |
| US6455539B2 (en) | 1999-12-23 | 2002-09-24 | Celltech R&D Limited | Squaric acid derivates |
| DE60130910T2 (de) | 2000-04-17 | 2008-07-10 | Ucb Pharma, S.A. | Enamin-derivate als zell-adhäsionsmoleküle |
| US6545013B2 (en) | 2000-05-30 | 2003-04-08 | Celltech R&D Limited | 2,7-naphthyridine derivatives |
| US6403608B1 (en) | 2000-05-30 | 2002-06-11 | Celltech R&D, Ltd. | 3-Substituted isoquinolin-1-yl derivatives |
| US6740654B2 (en) | 2000-07-07 | 2004-05-25 | Celltech R & D Limited | Squaric acid derivatives |
| US6649756B2 (en) * | 2000-07-13 | 2003-11-18 | Wyeth, Five Giralda Farms | Process improvement in the preparation of (4r, 5s, 6s)-3-[[(2r,3r)-2-[[[(s)-2-amino-3-methyl-1-oxobutyl]amino]methyl]tetrahydro-3-furanyl]thio]-6-[(r)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid |
| AU2001275724A1 (en) | 2000-08-02 | 2002-02-13 | Celltech R&D Limited | 3-substituted isoquinolin-1-yl derivatives |
| CN102827191B (zh) * | 2012-09-24 | 2015-03-11 | 浙江东邦药业有限公司 | 一种氧头孢类化合物的制备方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL178005C (nl) * | 1972-11-06 | 1986-01-02 | Merck & Co Inc | Werkwijze voor het bereiden van een farmaceutisch preparaat met antibacteriele werking, alsmede werkwijze ter bereiding van een cefalosporine-antibioticum. |
| US4045438A (en) * | 1975-10-24 | 1977-08-30 | Yeda Research And Development Co. Ltd. | Cephalosporin antibiotics |
| US4031083A (en) * | 1975-10-24 | 1977-06-21 | Yeda Research And Development Co., Ltd. | Cephalosporin antibiotics |
| FR2361114A1 (fr) * | 1975-11-12 | 1978-03-10 | Shionogi & Co | Procede de preparation d'analogues de cephalosporine a propriete antibacterienne et nouveaux produits ainsi obtenus |
| CA1085392A (en) * | 1976-03-25 | 1980-09-09 | Masayuki Narisada | Arylmalonamido-1-oxadethiacephalosporins |
-
1977
- 1977-08-25 JP JP52102261A patent/JPS609718B2/ja not_active Expired
-
1978
- 1978-04-28 GB GB17007/78A patent/GB1576796A/en not_active Expired
- 1978-08-17 PT PT68434A patent/PT68434A/pt unknown
- 1978-08-17 NZ NZ188173A patent/NZ188173A/xx unknown
- 1978-08-21 ZA ZA00784753A patent/ZA784753B/xx unknown
- 1978-08-21 CA CA309,705A patent/CA1101417A/en not_active Expired
- 1978-08-22 CS CS785485A patent/CS203927B2/cs unknown
- 1978-08-23 AR AR273406A patent/AR220539A1/es active
- 1978-08-23 DD DD78207438A patent/DD137230A5/xx unknown
- 1978-08-23 IE IE1703/78A patent/IE47630B1/en not_active IP Right Cessation
- 1978-08-23 MX MX787347U patent/MX5328E/es unknown
- 1978-08-23 NO NO782866A patent/NO782866L/no unknown
- 1978-08-24 US US05/936,506 patent/US4201782A/en not_active Expired - Lifetime
- 1978-08-24 BE BE190057A patent/BE869955A/xx not_active IP Right Cessation
- 1978-08-24 FR FR7824595A patent/FR2401165A1/fr active Granted
- 1978-08-24 IT IT68975/78A patent/IT1118098B/it active
- 1978-08-24 ES ES472817A patent/ES472817A1/es not_active Expired
- 1978-08-24 DK DK372878A patent/DK372878A/da not_active Application Discontinuation
- 1978-08-24 FI FI782586A patent/FI65432C/fi not_active IP Right Cessation
- 1978-08-24 AU AU39238/78A patent/AU517618B2/en not_active Expired
- 1978-08-24 IL IL7855429A patent/IL55429A0/xx not_active IP Right Cessation
- 1978-08-24 SE SE7808950A patent/SE452010B/sv not_active IP Right Cessation
- 1978-08-25 PL PL1978209215A patent/PL110656B1/pl unknown
- 1978-08-25 GR GR57086A patent/GR70260B/el unknown
- 1978-08-25 YU YU2028/78A patent/YU43999B/xx unknown
- 1978-08-25 CH CH899678A patent/CH637396A5/de not_active IP Right Cessation
- 1978-08-25 BG BG040749A patent/BG34338A3/xx unknown
- 1978-08-25 PH PH21699A patent/PH17508A/en unknown
- 1978-08-25 SU SU782652750A patent/SU812182A3/ru active
- 1978-08-25 HU HU78SI1644A patent/HU177900B/hu not_active IP Right Cessation
- 1978-08-25 RO RO7895037A patent/RO75070A/ro unknown
- 1978-08-25 AT AT620378A patent/AT361121B/de not_active IP Right Cessation
- 1978-08-25 DE DE19782837264 patent/DE2837264A1/de active Granted
- 1978-08-25 NL NLAANVRAGE7808802,A patent/NL190554C/xx not_active IP Right Cessation
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