GB1570095A - 7-aminocephalosporin intermediates - Google Patents
7-aminocephalosporin intermediates Download PDFInfo
- Publication number
- GB1570095A GB1570095A GB19863/79A GB1986379A GB1570095A GB 1570095 A GB1570095 A GB 1570095A GB 19863/79 A GB19863/79 A GB 19863/79A GB 1986379 A GB1986379 A GB 1986379A GB 1570095 A GB1570095 A GB 1570095A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- compound according
- compound
- formula
- salt
- 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
- 239000000543 intermediate Substances 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 12
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 8
- -1 methoxybenzyl Chemical group 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 4
- JAAIPIWKKXCNOC-UHFFFAOYSA-N 1h-tetrazol-1-ium-5-thiolate Chemical compound SC1=NN=NN1 JAAIPIWKKXCNOC-UHFFFAOYSA-N 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
- 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 claims description 2
- CWRVKFFCRWGWCS-UHFFFAOYSA-N Pentrazole Chemical compound C1CCCCC2=NN=NN21 CWRVKFFCRWGWCS-UHFFFAOYSA-N 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 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 2
- 230000001681 protective effect Effects 0.000 claims description 2
- 125000006000 trichloroethyl group Chemical group 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- IKWLIQXIPRUIDU-ZCFIWIBFSA-N (6r)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound OC(=O)C1=CCS[C@@H]2CC(=O)N12 IKWLIQXIPRUIDU-ZCFIWIBFSA-N 0.000 claims 1
- 101100494773 Caenorhabditis elegans ctl-2 gene Proteins 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 claims 1
- VGGRCVDNFAQIKO-UHFFFAOYSA-N formic anhydride Chemical compound O=COC=O VGGRCVDNFAQIKO-UHFFFAOYSA-N 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- 229930186147 Cephalosporin Natural products 0.000 description 2
- YGBFLZPYDUKSPT-MRVPVSSYSA-N cephalosporanic acid Chemical compound S1CC(COC(=O)C)=C(C(O)=O)N2C(=O)C[C@H]21 YGBFLZPYDUKSPT-MRVPVSSYSA-N 0.000 description 2
- 229940124587 cephalosporin Drugs 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001780 cephalosporins Chemical class 0.000 description 1
- 150000001782 cephems Chemical class 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000006501 nitrophenyl group Chemical group 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
- A61K31/542—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame ortho- or peri-condensed with heterocyclic ring systems
- A61K31/545—Compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins, cefaclor, or cephalexine
-
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/14—Compounds having a nitrogen atom directly attached in position 7
- C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
- C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
- C07D501/24—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with hydrocarbon radicals, substituted by hetero atoms or hetero rings, attached in position 3
- C07D501/36—Methylene radicals, substituted by sulfur atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Communicable Diseases (AREA)
- Epidemiology (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 |
|---|---|---|---|
| US62716475A | 1975-10-30 | 1975-10-30 | |
| US66583776A | 1976-03-11 | 1976-03-11 | |
| US05/704,142 US4118491A (en) | 1976-03-11 | 1976-07-12 | 7-Acyl-3-(sulfaminoalkyl substituted tetrazolylthiomethyl)cephalosporins, antibacterial compositions containing them and methods of treating bacterial infections with them |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1570095A true GB1570095A (en) | 1980-06-25 |
Family
ID=27417417
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB19863/79A Expired GB1570095A (en) | 1975-10-30 | 1976-10-26 | 7-aminocephalosporin intermediates |
| GB19786/79A Expired GB1570094A (en) | 1975-10-30 | 1976-10-26 | Substituted tetrazole-5-thiols |
| GB44441/76A Expired GB1570093A (en) | 1975-10-30 | 1976-10-26 | Cephalosporins |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB19786/79A Expired GB1570094A (en) | 1975-10-30 | 1976-10-26 | Substituted tetrazole-5-thiols |
| GB44441/76A Expired GB1570093A (en) | 1975-10-30 | 1976-10-26 | Cephalosporins |
Country Status (17)
| Country | Link |
|---|---|
| JP (1) | JPS6053026B2 (enExample) |
| AT (1) | AT353957B (enExample) |
| AU (1) | AU505141B2 (enExample) |
| CA (1) | CA1071188A (enExample) |
| CH (1) | CH627757A5 (enExample) |
| DE (1) | DE2649545A1 (enExample) |
| DK (1) | DK463176A (enExample) |
| ES (1) | ES452769A1 (enExample) |
| FI (1) | FI60868C (enExample) |
| FR (3) | FR2361896A1 (enExample) |
| GB (3) | GB1570095A (enExample) |
| GR (1) | GR61667B (enExample) |
| IE (1) | IE44393B1 (enExample) |
| IL (3) | IL50546A (enExample) |
| LU (1) | LU76092A1 (enExample) |
| NL (1) | NL7612010A (enExample) |
| SE (3) | SE435291B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT383811B (de) * | 1983-09-22 | 1987-08-25 | Biochemie Gmbh | Verfahren zur herstellung von monoalkalisalzen von 7-amino-3-cephem-4-carbonsaeurederivaten |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4117123A (en) * | 1977-06-09 | 1978-09-26 | Smithkline Corporation | 7-Acylamino-3-[1-(2-sulfamidoethyl)tetrazol-5-ylthiomethyl]-3-cephem-4-carboxylic acids |
| US4717531A (en) * | 1983-09-23 | 1988-01-05 | Westinghouse Electric Corp. | Fuel transfer system upender using translation drive |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR207752A1 (es) * | 1973-03-30 | 1976-10-29 | Fujisawa Pharmaceutical Co | Procedimiento para obtener acidos 7-amino-sustituido-3-tiometilsustituido-3-cefem-4-carboxilicos |
| NL7414119A (nl) * | 1973-10-31 | 1975-05-02 | Fujisawa Pharmaceutical Co | Werkwijze ter bereiding van 1h-tetrazool-5-thiol- derivaten en 1-gesubstitueerde 1h-tetrazool- -5-thiolen. |
| GB1449420A (en) * | 1973-11-26 | 1976-09-15 | Sankyo Co | 7alpha-methoxycephalosporing derivatives |
| NZ176206A (en) * | 1973-12-25 | 1978-03-06 | Takeda Chemical Industries Ltd | Cephalosporins |
| 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 |
-
1976
- 1976-09-23 IL IL50546A patent/IL50546A/xx unknown
- 1976-09-28 SE SE7610722A patent/SE435291B/xx not_active IP Right Cessation
- 1976-09-28 SE SE8006413A patent/SE452621B/sv not_active IP Right Cessation
- 1976-09-30 CA CA262,347A patent/CA1071188A/en not_active Expired
- 1976-10-14 DK DK463176A patent/DK463176A/da not_active Application Discontinuation
- 1976-10-14 AU AU18702/76A patent/AU505141B2/en not_active Ceased
- 1976-10-21 FR FR7631723A patent/FR2361896A1/fr active Granted
- 1976-10-26 GB GB19863/79A patent/GB1570095A/en not_active Expired
- 1976-10-26 FI FI763044A patent/FI60868C/fi not_active IP Right Cessation
- 1976-10-26 GB GB19786/79A patent/GB1570094A/en not_active Expired
- 1976-10-26 GB GB44441/76A patent/GB1570093A/en not_active Expired
- 1976-10-27 ES ES452769A patent/ES452769A1/es not_active Expired
- 1976-10-27 IE IE2377/76A patent/IE44393B1/en unknown
- 1976-10-28 LU LU76092A patent/LU76092A1/xx unknown
- 1976-10-29 GR GR52030A patent/GR61667B/el unknown
- 1976-10-29 JP JP51131157A patent/JPS6053026B2/ja not_active Expired
- 1976-10-29 DE DE19762649545 patent/DE2649545A1/de not_active Ceased
- 1976-10-29 CH CH1369576A patent/CH627757A5/de not_active IP Right Cessation
- 1976-10-29 AT AT807276A patent/AT353957B/de not_active IP Right Cessation
- 1976-10-29 NL NL7612010A patent/NL7612010A/xx not_active Application Discontinuation
-
1977
- 1977-03-22 FR FR7708505A patent/FR2337720A1/fr active Granted
- 1977-03-22 FR FR7708504A patent/FR2351982A1/fr active Granted
-
1979
- 1979-02-28 IL IL56757A patent/IL56757A0/xx unknown
- 1979-02-28 IL IL56758A patent/IL56758A0/xx unknown
-
1980
- 1980-09-12 SE SE8006414A patent/SE437025B/sv not_active IP Right Cessation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT383811B (de) * | 1983-09-22 | 1987-08-25 | Biochemie Gmbh | Verfahren zur herstellung von monoalkalisalzen von 7-amino-3-cephem-4-carbonsaeurederivaten |
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4053468A (en) | Process for preparing 7-oxo cephalosporins and 6-oxo penicillins | |
| DE2736471C2 (enExample) | ||
| US4091227A (en) | Protected α-amino-α-ureido(thioureido)phenylacetic acids | |
| DE2852538C2 (enExample) | ||
| DE3244457A1 (de) | Verfahren zur herstellung von 3-alkoxymethylcephalosporinderivaten | |
| DE2730377A1 (de) | 7-beta-(2-oxyimino-2-arylacetamido)- cephalosporine | |
| GB2071654A (en) | Hydroxamic acid derivatives of 7-(2-amino-4-thiazolyl)oximino cephalosporins | |
| GB1570095A (en) | 7-aminocephalosporin intermediates | |
| DE2428139A1 (de) | Cephalosporine, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneipraeparate | |
| GB1580482A (en) | 7-amino-3-(sulphoalkyl-1,3,4-oxadiazol-2-yl)-thiomethyl-3-cephem-4-carboxylic acid derivatives | |
| SE7907320L (sv) | 3,7-disubstituerade 3-cefem-4-karboxylsyraforeningar och forfaranden for deras framstellning | |
| US3965099A (en) | Cephalosporin esters with antibacterial activity | |
| US4131734A (en) | 7β-Acyloxy-3-heterocyclicthiomethyl cephalosporins | |
| GB2047245A (en) | Process for preparing penicillin sulphoxides | |
| GB1589883A (en) | 7-aminocephalosporin derivatives | |
| EP0023045B1 (en) | Imidazolecarboxylic acid derivatives of penicillins and cephalosporins | |
| GB1358027A (en) | Alpha-amino-rho-hydroxyphenylacetamidocephalosporins | |
| US3957770A (en) | Substituted acetamidocephalosporins | |
| CA1104560A (en) | Pyrrole cephalosporin derivatives | |
| EP0000285B1 (en) | 7-acylamino-3-((3-(carboxymethyl) thio-1 h-1,2,4-triazol-5-yl) thiomethyl)-3-cephem-4-carboxylic acid derivatives, processes for their preparation and compositions containing them | |
| IE44395B1 (en) | 7-aminocephalosporin intermediates | |
| US3998818A (en) | Trifluoroethylmercapto, -sulfinyl or -sulfonyl acetamidocephalosporins | |
| CA1071621A (en) | Process for preparing 7-aminocephalosporanic acid derivatives | |
| US3998819A (en) | Trifluoroethyl-mercapto, -sulfinyl or -sulfonyl acetamidocephalosporins | |
| US4218564A (en) | 7β-Hydroxy-3-heterocyclicthio-methyl cephalosporin intermediates |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |