ES457174A1 - Arylmalonamido (1)-oxa-dethia-cephalosporins - for use as broad-spectrum antibacterial agents - Google Patents
Arylmalonamido (1)-oxa-dethia-cephalosporins - for use as broad-spectrum antibacterial agentsInfo
- Publication number
- ES457174A1 ES457174A1 ES457174A ES457174A ES457174A1 ES 457174 A1 ES457174 A1 ES 457174A1 ES 457174 A ES457174 A ES 457174A ES 457174 A ES457174 A ES 457174A ES 457174 A1 ES457174 A1 ES 457174A1
- Authority
- ES
- Spain
- Prior art keywords
- cephalosporins
- oxa
- dethia
- arylmalonamido
- broad
- 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
- 229940124587 cephalosporin Drugs 0.000 title abstract 3
- 239000003242 anti bacterial agent Substances 0.000 title 1
- -1 3-thienyl phenyl Chemical group 0.000 abstract 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 2
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 abstract 1
- 241000894006 Bacteria Species 0.000 abstract 1
- 229930186147 Cephalosporin Natural products 0.000 abstract 1
- 241000589516 Pseudomonas Species 0.000 abstract 1
- 230000000844 anti-bacterial effect Effects 0.000 abstract 1
- 150000001780 cephalosporins Chemical class 0.000 abstract 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 abstract 1
- WWYDYZMNFQIYPT-UHFFFAOYSA-N ru78191 Chemical compound OC(=O)C(C(O)=O)C1=CC=CC=C1 WWYDYZMNFQIYPT-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- 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
- A61K31/535—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 oxygen as the ring hetero atoms, e.g. 1,2-oxazines
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
-
- 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
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)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Cephalosporin Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
New 1-oxa-dethia-cephalosporins are of formula (I) (where Ar is 2- or 3-thienyl phenyl, p-hydroxyphenyl or p-acyloxyphenyl COB, and COB2 are COOH or protected carboxy Het is u-methyltetrazol-5-yl (MT), opt. protected 1-carboxymethyltetrazol-5-yl (CMT) or 2-methyl-1, 3, 4-thiadiazol-5-yl (MTD) Y is H or MeO with the provido that Het must be MT when Y is MeO). (I) have 4-8 times the antibacterial activity of the corresp. true cephalosporins, esp. against Gram. neg. bacteria (including resistant Pseudomonas strains), and have better stability than known 1-oxa-dethiacephalosporins. A typical cpd. is diphenylmethyl 7 beta-(beta-phenyl-alpha-diphenylmethoxycarbonylacetamido)-3-(-1-t- hiomethyl)-1-oxadethia-3-cephem-4-carboxylate. In an example, this is prepd. by reacting the corresp. 7-amino cpd. with monodiphenylmethyl phenylmalonate.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3340176A JPS52122386A (en) | 1976-03-25 | 1976-03-25 | Cephalosporin analogous compounds as antibacterials |
| JP5029576A JPS52133997A (en) | 1976-04-30 | 1976-04-30 | Cephalosporin antibiotics |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES457174A1 true ES457174A1 (en) | 1978-08-16 |
Family
ID=26372085
Family Applications (5)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES457174A Expired ES457174A1 (en) | 1976-03-25 | 1977-03-24 | Arylmalonamido (1)-oxa-dethia-cephalosporins - for use as broad-spectrum antibacterial agents |
| ES469287A Expired ES469287A1 (en) | 1976-03-25 | 1978-04-28 | Arylmalonamido (1)-oxa-dethia-cephalosporins - for use as broad-spectrum antibacterial agents |
| ES469284A Expired ES469284A1 (en) | 1976-03-25 | 1978-04-28 | A procedure for preparing arilmalonamido-1-oxadestiacefalosporinas. (Machine-translation by Google Translate, not legally binding) |
| ES469285A Expired ES469285A1 (en) | 1976-03-25 | 1978-04-28 | Arylmalonamido (1)-oxa-dethia-cephalosporins - for use as broad-spectrum antibacterial agents |
| ES469286A Expired ES469286A1 (en) | 1976-03-25 | 1978-04-28 | Arylmalonamido (1)-oxa-dethia-cephalosporins - for use as broad-spectrum antibacterial agents |
Family Applications After (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES469287A Expired ES469287A1 (en) | 1976-03-25 | 1978-04-28 | Arylmalonamido (1)-oxa-dethia-cephalosporins - for use as broad-spectrum antibacterial agents |
| ES469284A Expired ES469284A1 (en) | 1976-03-25 | 1978-04-28 | A procedure for preparing arilmalonamido-1-oxadestiacefalosporinas. (Machine-translation by Google Translate, not legally binding) |
| ES469285A Expired ES469285A1 (en) | 1976-03-25 | 1978-04-28 | Arylmalonamido (1)-oxa-dethia-cephalosporins - for use as broad-spectrum antibacterial agents |
| ES469286A Expired ES469286A1 (en) | 1976-03-25 | 1978-04-28 | Arylmalonamido (1)-oxa-dethia-cephalosporins - for use as broad-spectrum antibacterial agents |
Country Status (19)
| Country | Link |
|---|---|
| AR (1) | AR224606A1 (en) |
| BG (1) | BG31074A3 (en) |
| CY (1) | CY1158A (en) |
| DD (1) | DD129792A5 (en) |
| DE (1) | DE2713370C2 (en) |
| DK (1) | DK161331C (en) |
| ES (5) | ES457174A1 (en) |
| GR (1) | GR61146B (en) |
| HK (1) | HK46882A (en) |
| HU (1) | HU172720B (en) |
| IE (1) | IE44794B1 (en) |
| IL (1) | IL51743A (en) |
| MX (1) | MX4348E (en) |
| NO (2) | NO158505C (en) |
| NZ (1) | NZ183687A (en) |
| PT (1) | PT66346B (en) |
| RO (2) | RO71742A (en) |
| SE (1) | SE443143B (en) |
| YU (2) | YU44038B (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1557552A (en) * | 1977-02-15 | 1979-12-12 | Shionogi & Co | 1 oxadethiacepham compounds |
| US4252953A (en) * | 1979-05-01 | 1981-02-24 | Eli Lilly And Company | Antibiotic crystalline epimer |
| JPS60123490A (en) * | 1983-12-07 | 1985-07-02 | Shionogi & Co Ltd | Malonyloxacephem carboxylic acid derivative |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL178005C (en) * | 1972-11-06 | 1986-01-02 | Merck & Co Inc | METHOD FOR PREPARING A PHARMACEUTICAL PREPARATION WITH ANTIBACTERIAL ACTION, AND METHOD FOR PREPARING A CEPHALOSPORINE ANTIBIOTIC. |
| US3962232A (en) * | 1973-11-05 | 1976-06-08 | Eli Lilly And Company | 7-methoxycephalosporins |
| GB1449420A (en) * | 1973-11-26 | 1976-09-15 | Sankyo Co | 7alpha-methoxycephalosporing derivatives |
-
1977
- 1977-03-23 SE SE7703325A patent/SE443143B/en not_active IP Right Cessation
- 1977-03-23 GR GR53086A patent/GR61146B/en unknown
- 1977-03-23 CY CY1158A patent/CY1158A/en unknown
- 1977-03-23 NO NO771023A patent/NO158505C/en unknown
- 1977-03-24 IE IE622/77A patent/IE44794B1/en not_active IP Right Cessation
- 1977-03-24 NZ NZ183687A patent/NZ183687A/en unknown
- 1977-03-24 DK DK131277A patent/DK161331C/en not_active IP Right Cessation
- 1977-03-24 HU HU77SI00001565A patent/HU172720B/en not_active IP Right Cessation
- 1977-03-24 RO RO7789781A patent/RO71742A/en unknown
- 1977-03-24 RO RO7799076A patent/RO78228A/en unknown
- 1977-03-24 DD DD7700198053A patent/DD129792A5/en unknown
- 1977-03-24 PT PT66346A patent/PT66346B/en unknown
- 1977-03-24 BG BG035796A patent/BG31074A3/en unknown
- 1977-03-24 ES ES457174A patent/ES457174A1/en not_active Expired
- 1977-03-25 AR AR266992A patent/AR224606A1/en active
- 1977-03-25 DE DE2713370A patent/DE2713370C2/en not_active Expired - Lifetime
- 1977-03-25 MX MX775582U patent/MX4348E/en unknown
- 1977-03-25 IL IL51743A patent/IL51743A/en unknown
-
1978
- 1978-04-28 ES ES469287A patent/ES469287A1/en not_active Expired
- 1978-04-28 ES ES469284A patent/ES469284A1/en not_active Expired
- 1978-04-28 ES ES469285A patent/ES469285A1/en not_active Expired
- 1978-04-28 ES ES469286A patent/ES469286A1/en not_active Expired
-
1982
- 1982-11-11 HK HK468/82A patent/HK46882A/en unknown
-
1983
- 1983-08-23 YU YU1737/83A patent/YU44038B/en unknown
- 1983-08-23 YU YU1738/83A patent/YU44039B/en unknown
-
1986
- 1986-05-28 NO NO862107A patent/NO862107L/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IE44794L (en) | 1977-09-25 |
| IL51743A (en) | 1980-10-26 |
| DK161331C (en) | 1991-12-09 |
| ES469285A1 (en) | 1979-09-16 |
| BG31074A3 (en) | 1981-10-15 |
| SE7703325L (en) | 1977-09-26 |
| CY1158A (en) | 1983-01-28 |
| NZ183687A (en) | 1979-01-11 |
| PT66346A (en) | 1977-04-01 |
| IE44794B1 (en) | 1982-04-07 |
| ES469286A1 (en) | 1979-09-16 |
| YU173783A (en) | 1983-12-31 |
| NO862107L (en) | 1977-09-27 |
| MX4348E (en) | 1982-04-05 |
| NO158505B (en) | 1988-06-13 |
| RO71742A (en) | 1982-02-26 |
| ES469284A1 (en) | 1978-11-16 |
| GR61146B (en) | 1978-09-27 |
| NO158505C (en) | 1988-09-21 |
| DE2713370C2 (en) | 1994-04-21 |
| NO771023L (en) | 1977-09-27 |
| YU44039B (en) | 1990-02-28 |
| RO78228A (en) | 1982-02-01 |
| YU44038B (en) | 1990-02-28 |
| HU172720B (en) | 1978-11-28 |
| DD129792A5 (en) | 1978-02-08 |
| AR224606A1 (en) | 1981-12-30 |
| ES469287A1 (en) | 1979-09-16 |
| SE443143B (en) | 1986-02-17 |
| DK161331B (en) | 1991-06-24 |
| DE2713370A1 (en) | 1977-09-29 |
| YU173883A (en) | 1983-12-31 |
| PT66346B (en) | 1978-08-16 |
| HK46882A (en) | 1982-11-19 |
| DK131277A (en) | 1977-09-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FD1A | Patent lapsed |
Effective date: 19981103 |