LU82423A1 - Procede perfectionne pour la preparation de cephalosporines substituees en position 3,produits obtenus par ce procede et produits intermediaires pour la mise en oeuvre du procede - Google Patents
Procede perfectionne pour la preparation de cephalosporines substituees en position 3,produits obtenus par ce procede et produits intermediaires pour la mise en oeuvre du procede Download PDFInfo
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- LU82423A1 LU82423A1 LU82423A LU82423A LU82423A1 LU 82423 A1 LU82423 A1 LU 82423A1 LU 82423 A LU82423 A LU 82423A LU 82423 A LU82423 A LU 82423A LU 82423 A1 LU82423 A1 LU 82423A1
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- 238000000034 method Methods 0.000 title claims description 26
- 238000002360 preparation method Methods 0.000 title claims description 8
- 229940124587 cephalosporin Drugs 0.000 title claims description 7
- 239000000047 product Substances 0.000 title description 35
- 239000013067 intermediate product Substances 0.000 title description 5
- 229930186147 Cephalosporin Natural products 0.000 title description 3
- HOKIDJSKDBPKTQ-GLXFQSAKSA-N cephalosporin C Chemical group S1CC(COC(=O)C)=C(C(O)=O)N2C(=O)[C@@H](NC(=O)CCC[C@@H](N)C(O)=O)[C@@H]12 HOKIDJSKDBPKTQ-GLXFQSAKSA-N 0.000 title 1
- -1 phenoxymethyl group Chemical group 0.000 claims description 211
- 125000004432 carbon atom Chemical group C* 0.000 claims description 38
- 150000001875 compounds Chemical class 0.000 claims description 30
- 239000003153 chemical reaction reagent Substances 0.000 claims description 17
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- 125000006239 protecting group Chemical group 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 150000002085 enols Chemical class 0.000 claims description 12
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 claims description 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 8
- 229910052698 phosphorus Inorganic materials 0.000 claims description 8
- 239000011574 phosphorus Substances 0.000 claims description 8
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 7
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- 125000002252 acyl group Chemical group 0.000 claims description 6
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- 230000002140 halogenating effect Effects 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
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- 238000005658 halogenation reaction Methods 0.000 claims description 4
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- 125000004122 cyclic group Chemical group 0.000 description 1
- MAWOHFOSAIXURX-UHFFFAOYSA-N cyclopentylcyclopentane Chemical group C1CCCC1C1CCCC1 MAWOHFOSAIXURX-UHFFFAOYSA-N 0.000 description 1
- ONYHPQJRXORCDD-UHFFFAOYSA-N dibromophosphoryloxybenzene Chemical compound BrP(Br)(=O)OC1=CC=CC=C1 ONYHPQJRXORCDD-UHFFFAOYSA-N 0.000 description 1
- VZUNXXUSMINMCM-UHFFFAOYSA-N dibromophosphoryloxymethane Chemical compound COP(Br)(Br)=O VZUNXXUSMINMCM-UHFFFAOYSA-N 0.000 description 1
- 125000004915 dibutylamino group Chemical group C(CCC)N(CCCC)* 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- IBDMRHDXAQZJAP-UHFFFAOYSA-N dichlorophosphorylbenzene Chemical compound ClP(Cl)(=O)C1=CC=CC=C1 IBDMRHDXAQZJAP-UHFFFAOYSA-N 0.000 description 1
- UQIVUJHGORLRNH-UHFFFAOYSA-N dichlorophosphoryloxycyclopentane Chemical compound ClP(Cl)(=O)OC1CCCC1 UQIVUJHGORLRNH-UHFFFAOYSA-N 0.000 description 1
- FCYHXMMAKHJFJB-UHFFFAOYSA-N dichlorophosphoryloxycyclopropane Chemical compound ClP(Cl)(=O)OC1CC1 FCYHXMMAKHJFJB-UHFFFAOYSA-N 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- VLNZUSMTOFYNPS-UHFFFAOYSA-N diethylphosphorylformonitrile Chemical compound CCP(=O)(CC)C#N VLNZUSMTOFYNPS-UHFFFAOYSA-N 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- ZLFRSWXVVWXYET-UHFFFAOYSA-N dimethylphosphorylformonitrile Chemical compound CP(C)(=O)C#N ZLFRSWXVVWXYET-UHFFFAOYSA-N 0.000 description 1
- HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 1
- QLZHNIAADXEJJP-UHFFFAOYSA-L dioxido-oxo-phenyl-$l^{5}-phosphane Chemical compound [O-]P([O-])(=O)C1=CC=CC=C1 QLZHNIAADXEJJP-UHFFFAOYSA-L 0.000 description 1
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 1
- MKRTXPORKIRPDG-UHFFFAOYSA-N diphenylphosphoryl azide Chemical compound C=1C=CC=CC=1P(=O)(N=[N+]=[N-])C1=CC=CC=C1 MKRTXPORKIRPDG-UHFFFAOYSA-N 0.000 description 1
- XKNOLTAFGYHTDD-UHFFFAOYSA-N diphenylphosphorylformonitrile Chemical compound C=1C=CC=CC=1P(C#N)(=O)C1=CC=CC=C1 XKNOLTAFGYHTDD-UHFFFAOYSA-N 0.000 description 1
- 125000004914 dipropylamino group Chemical group C(CC)N(CCC)* 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 125000006627 ethoxycarbonylamino group Chemical group 0.000 description 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 125000004970 halomethyl group Chemical group 0.000 description 1
- 125000005059 halophenyl group Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 229940095102 methyl benzoate Drugs 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 125000006502 nitrobenzyl group Chemical group 0.000 description 1
- 125000006501 nitrophenyl group Chemical group 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 230000001012 protector Effects 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
- 239000012429 reaction media Substances 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cephalosporin Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7915929 | 1979-05-08 | ||
| GB7915929 | 1979-05-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| LU82423A1 true LU82423A1 (fr) | 1982-01-20 |
Family
ID=10505015
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LU82423A LU82423A1 (fr) | 1979-05-08 | 1980-05-05 | Procede perfectionne pour la preparation de cephalosporines substituees en position 3,produits obtenus par ce procede et produits intermediaires pour la mise en oeuvre du procede |
Country Status (33)
| Country | Link |
|---|---|
| US (1) | US4301280A (pl) |
| EP (1) | EP0019401B1 (pl) |
| JP (1) | JPS55151589A (pl) |
| KR (1) | KR840000484B1 (pl) |
| AR (1) | AR226430A1 (pl) |
| AT (1) | AT369746B (pl) |
| AU (1) | AU540210B2 (pl) |
| BE (1) | BE883101A (pl) |
| BG (1) | BG36633A3 (pl) |
| CA (1) | CA1148938A (pl) |
| CH (1) | CH647526A5 (pl) |
| CS (1) | CS219919B2 (pl) |
| DD (1) | DD150613A5 (pl) |
| DE (1) | DE3067099D1 (pl) |
| DK (1) | DK171892B1 (pl) |
| EG (1) | EG14897A (pl) |
| ES (1) | ES491248A0 (pl) |
| FI (1) | FI75170C (pl) |
| FR (1) | FR2456112A1 (pl) |
| GR (1) | GR68417B (pl) |
| HU (1) | HU184753B (pl) |
| IE (1) | IE49786B1 (pl) |
| IL (1) | IL59991A (pl) |
| IT (1) | IT1188934B (pl) |
| LU (1) | LU82423A1 (pl) |
| NZ (1) | NZ193619A (pl) |
| PH (1) | PH15984A (pl) |
| PL (1) | PL121466B1 (pl) |
| PT (1) | PT71186B (pl) |
| RO (1) | RO81342B (pl) |
| SU (1) | SU1042619A3 (pl) |
| YU (1) | YU121180A (pl) |
| ZA (1) | ZA802718B (pl) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0133670A3 (de) * | 1983-08-09 | 1985-12-18 | Bayer Ag | Verfahren zur Herstellung von 7-Acylamino-3-hydrocy-cephem-4-carbonsäuren und 7-Acylamino-3-hydroxy-1-de-thia-1-oxacephem-4-carbonsäuren |
| US5604222A (en) * | 1993-12-27 | 1997-02-18 | Lupin Laboratories, Ltd. | Method for the preparation of 2-chloro sulfinyl azetidinones |
| US5578721A (en) * | 1994-07-11 | 1996-11-26 | Lupin Laboratories Limited | Process for preparation of 3-exomethylene cepham sulfoxide esters |
| CN111647638A (zh) * | 2020-04-17 | 2020-09-11 | 江苏正泰药业有限公司 | 一种7-anca的制备工艺 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1136132A (en) * | 1975-02-17 | 1982-11-23 | Teruji Tsuji | Cyclization to form cephem ring and intermediates therefor |
| JPS609516B2 (ja) * | 1975-03-07 | 1985-03-11 | 塩野義製薬株式会社 | セフエム骨格の環化製法 |
| JPS51105051A (pl) * | 1975-02-21 | 1976-09-17 | Shionogi Seiyaku Kk | |
| JPS5214789A (en) * | 1975-07-22 | 1977-02-03 | Shionogi & Co Ltd | Process for preparing 3-substiuted cephem compounds by ring closure |
| JPS5858355B2 (ja) * | 1976-01-01 | 1983-12-24 | 塩野義製薬株式会社 | オキソチアゾリノアゼチジニルハロブテン酸類 |
| US4226986A (en) * | 1979-02-01 | 1980-10-07 | Eli Lilly And Company | Process for halogenation of β-lactam compounds |
-
1980
- 1980-04-09 CA CA000349470A patent/CA1148938A/en not_active Expired
- 1980-05-01 US US06/145,531 patent/US4301280A/en not_active Expired - Lifetime
- 1980-05-02 GR GR61834A patent/GR68417B/el unknown
- 1980-05-02 AU AU58042/80A patent/AU540210B2/en not_active Expired
- 1980-05-02 BE BE6/47157A patent/BE883101A/fr not_active IP Right Cessation
- 1980-05-02 DE DE8080301457T patent/DE3067099D1/de not_active Expired
- 1980-05-02 PH PH23978A patent/PH15984A/en unknown
- 1980-05-02 EP EP80301457A patent/EP0019401B1/en not_active Expired
- 1980-05-05 LU LU82423A patent/LU82423A1/fr unknown
- 1980-05-05 NZ NZ193619A patent/NZ193619A/xx unknown
- 1980-05-05 DK DK196580A patent/DK171892B1/da not_active IP Right Cessation
- 1980-05-05 RO RO101039A patent/RO81342B/ro unknown
- 1980-05-05 AT AT0238980A patent/AT369746B/de not_active IP Right Cessation
- 1980-05-05 FR FR8009957A patent/FR2456112A1/fr active Granted
- 1980-05-05 IL IL59991A patent/IL59991A/xx unknown
- 1980-05-05 PT PT71186A patent/PT71186B/pt unknown
- 1980-05-06 JP JP5985980A patent/JPS55151589A/ja active Granted
- 1980-05-06 CH CH3509/80A patent/CH647526A5/fr not_active IP Right Cessation
- 1980-05-06 HU HU801102A patent/HU184753B/hu unknown
- 1980-05-06 IT IT48597/80A patent/IT1188934B/it active
- 1980-05-06 FI FI801452A patent/FI75170C/fi not_active IP Right Cessation
- 1980-05-06 ZA ZA00802718A patent/ZA802718B/xx unknown
- 1980-05-06 IE IE926/80A patent/IE49786B1/en not_active IP Right Cessation
- 1980-05-07 AR AR280923A patent/AR226430A1/es active
- 1980-05-07 BG BG047661A patent/BG36633A3/xx not_active Expired
- 1980-05-07 YU YU01211/80A patent/YU121180A/xx unknown
- 1980-05-07 DD DD80220942A patent/DD150613A5/de unknown
- 1980-05-07 CS CS803210A patent/CS219919B2/cs unknown
- 1980-05-07 EG EG282/80A patent/EG14897A/xx active
- 1980-05-07 SU SU802920001A patent/SU1042619A3/ru active
- 1980-05-07 ES ES491248A patent/ES491248A0/es active Granted
- 1980-05-08 KR KR1019800001826A patent/KR840000484B1/ko active
- 1980-05-08 PL PL1980224114A patent/PL121466B1/pl unknown
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