IE38916L - 3-halo-cephalosporins - Google Patents
3-halo-cephalosporinsInfo
- Publication number
- IE38916L IE38916L IE740357A IE35774A IE38916L IE 38916 L IE38916 L IE 38916L IE 740357 A IE740357 A IE 740357A IE 35774 A IE35774 A IE 35774A IE 38916 L IE38916 L IE 38916L
- Authority
- IE
- Ireland
- Prior art keywords
- hydrogen
- thienyl
- amino
- methyl
- compounds
- Prior art date
Links
Classifications
-
- 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
-
- 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
- C07D501/02—Preparation
- C07D501/04—Preparation from compounds already containing the ring or condensed ring systems, e.g. by dehydrogenation of the ring, by introduction, elimination or modification of substituents
-
- 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
- C07D501/59—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3 with hetero atoms directly attached in position 3
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)
- Cephalosporin Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1458293 3-Halocephalosporins ELI LILLY & CO 22 Feb 1974 [23 Feb 1973] 8096/74 Heading C2C The invention comprises compounds of formula wherein R is hydrogen or an acyl group R<SP>1</SP>CO, where R<SP>1</SP> is (i) C 1 -C 6 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 cyanoalkyl, phenyl, methylphenyl, hydroxyphenyl, halophenyl, nitrophenyl, aminophenyl, methoxyphenyl, 5 - amino - 5- carboxybutyl, or a 5 - substituted - amino - 5- carboxybutyl ester group where A is diphenylmethyl, p-nitrobenzyl, pmethoxybenzyl, benzyl, t - butyl or 2,2,2- trichloroethyl, and A<SP>1</SP> is C 2 -C 4 alkanoyl, C 2 -C 4 haloalkanoyl, benzoyl, halobenzoyl, 2,4 - dinitrophenyl, or phthaloyl; (ii) where a and a<SP>1</SP> independently are hydrogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, halogen, hydroxy, nitro, amino or carboxy; Z is O or S; and m is 0 or 1; (iii) PCH(Q) where P is 2-thienyl, 3-thienyl, phenyl or a substituted phenyl group a(a<SP>1</SP>)C 6 H 3 where a and a<SP>1</SP> are as defined above, Q is hydroxy, formyloxy, acetoxy, carboxy, or sulpho; (iv) PC(:NOY) where P has the same meaning as defined above and Y is hydrogen, methyl or acetyl; (v) R<SP>11</SP>CH 2 where R<SP>11</SP> is 2-thienyl, 3-thienyl, 2-furyl, 2- oxazolyl, 2-thiazolyl, or 1-tetrazolyl; (vi) where a, a<SP>1</SP>, Z and m have the same meanings as defined above; R 1 is hydrogen, benzyl, pmethoxybenzyl, p-nitrobenzyl, diphenylmethyl, 2,2,2 - trichloroethyl, t - butyl, or a pharmaceutically acceptable ester radical (C 1-4 alkyl) CO 2 CH 2 and X is fluoro, chloro, or bromo; and when R 1 is hydrogen the non-toxic pharmaceutically acceptable salts thereof. These compounds may be prepared by (1) hydrogenolysis of nitrobenzyl esters to give the acids, (2) N-acylation, or conversely N-deacylation, (3) halogenating the 3-position in the 3-hydroxy or 3-methylsulphonyloxy cephem analogues, (4) (in case vi) reducing with H 2 (Raney Ni) the analogues where R<SP>1</SP> is 3-(aryl, aryloxy or arylthio)methyl - 1,2,4 - oxadiazolin - 5 - on - 4 - yl methyl. Starting materials otherwise prepared (by N - deacetylation) are the analogous 7 - amino- 3-methylenecepham compounds. Therapeutic compositions for parenteral administration comprise compounds of the above formula, in which R is acyl and R 1 is H or (C 1-4 alkanoyloxy)methyl, which are active against both gram-positive and gram-negative organisms.
[GB1458293A]
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US33541473A | 1973-02-23 | 1973-02-23 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE38916L true IE38916L (en) | 1974-08-23 |
| IE38916B1 IE38916B1 (en) | 1978-06-21 |
Family
ID=23311677
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE00357/74A IE38916B1 (en) | 1973-02-23 | 1974-02-22 | O-halo cephalosporins |
Country Status (34)
| Country | Link |
|---|---|
| JP (4) | JPS612677B2 (en) |
| AR (3) | AR208068A1 (en) |
| AT (1) | AT333952B (en) |
| BE (1) | BE811494A (en) |
| BG (1) | BG22404A3 (en) |
| BR (1) | BR7401385D0 (en) |
| CA (1) | CA1032532A (en) |
| CH (1) | CH594686A5 (en) |
| CS (1) | CS189625B2 (en) |
| CY (1) | CY1042A (en) |
| DD (1) | DD110277A5 (en) |
| DE (1) | DE2408686C2 (en) |
| ES (1) | ES423532A1 (en) |
| FI (1) | FI63240C (en) |
| FR (1) | FR2218878B1 (en) |
| GB (1) | GB1458293A (en) |
| GT (1) | GT197432132A (en) |
| HK (1) | HK19980A (en) |
| HU (1) | HU167749B (en) |
| IE (1) | IE38916B1 (en) |
| IL (1) | IL44263A (en) |
| KE (1) | KE3026A (en) |
| MW (1) | MW574A1 (en) |
| MY (1) | MY8100023A (en) |
| NL (1) | NL181010C (en) |
| NO (2) | NO148376C (en) |
| OA (1) | OA04688A (en) |
| PH (1) | PH14014A (en) |
| PL (1) | PL88714B1 (en) |
| RO (1) | RO64595A (en) |
| SE (1) | SE411211B (en) |
| YU (2) | YU36971B (en) |
| ZA (1) | ZA741190B (en) |
| ZM (1) | ZM3674A1 (en) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT342197B (en) * | 1975-02-20 | 1978-03-28 | Ciba Geigy Ag | NEW PROCESS FOR PRODUCING 3-CEPHEM CONNECTIONS |
| CH622802A5 (en) * | 1975-08-20 | 1981-04-30 | Ciba Geigy Ag | |
| IE45158B1 (en) * | 1976-08-16 | 1982-06-30 | Lilly Co Eli | 3-chloro-cephem synthesis |
| PH17188A (en) * | 1977-03-14 | 1984-06-14 | Fujisawa Pharmaceutical Co | New cephem and cepham compounds and their pharmaceutical compositions and method of use |
| JPS62112053U (en) * | 1985-12-27 | 1987-07-16 | ||
| JPH0676861B2 (en) * | 1988-05-24 | 1994-09-28 | リンナイ株式会社 | Control device for hot air heater |
| IT1255458B (en) * | 1992-05-11 | 1995-11-02 | Col Marco Da | PROCEDURE FOR THE PREPARATION OF HALOGENATED BETA-LACTAMIC DERIVATIVES |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2265798C2 (en) * | 1971-06-24 | 1985-09-26 | Fujisawa Pharmaceutical Co., Ltd., Osaka | Process for the preparation of oxoazetidine derivatives |
-
1974
- 1974-01-01 AR AR256545A patent/AR208068A1/en active
- 1974-02-21 AT AT142474A patent/AT333952B/en not_active IP Right Cessation
- 1974-02-22 FR FR7406154A patent/FR2218878B1/fr not_active Expired
- 1974-02-22 NL NLAANVRAGE7402486,A patent/NL181010C/en not_active IP Right Cessation
- 1974-02-22 MW MW5/74*UA patent/MW574A1/en unknown
- 1974-02-22 DE DE2408686A patent/DE2408686C2/en not_active Expired
- 1974-02-22 GT GT197432132A patent/GT197432132A/en unknown
- 1974-02-22 DD DD176752A patent/DD110277A5/xx unknown
- 1974-02-22 IL IL44263A patent/IL44263A/en unknown
- 1974-02-22 BG BG025871A patent/BG22404A3/en unknown
- 1974-02-22 SE SE7402414A patent/SE411211B/en not_active IP Right Cessation
- 1974-02-22 BE BE1005740A patent/BE811494A/en not_active IP Right Cessation
- 1974-02-22 CA CA193,238A patent/CA1032532A/en not_active Expired
- 1974-02-22 IE IE00357/74A patent/IE38916B1/en unknown
- 1974-02-22 ZA ZA00741190A patent/ZA741190B/en unknown
- 1974-02-22 FI FI526/74A patent/FI63240C/en active
- 1974-02-22 ZM ZM36/74A patent/ZM3674A1/en unknown
- 1974-02-22 HU HUEI527A patent/HU167749B/hu unknown
- 1974-02-22 CY CY1042A patent/CY1042A/en unknown
- 1974-02-22 ES ES423532A patent/ES423532A1/en not_active Expired
- 1974-02-22 YU YU0463/74A patent/YU36971B/en unknown
- 1974-02-22 NO NO740607A patent/NO148376C/en unknown
- 1974-02-22 AR AR252494A patent/AR200908A1/en active
- 1974-02-22 BR BR1385/74A patent/BR7401385D0/en unknown
- 1974-02-22 GB GB809674A patent/GB1458293A/en not_active Expired
- 1974-02-23 JP JP49021871A patent/JPS612677B2/ja not_active Expired
- 1974-02-23 RO RO7477795A patent/RO64595A/en unknown
- 1974-02-23 PL PL1974169033A patent/PL88714B1/en unknown
- 1974-02-23 OA OA55127A patent/OA04688A/en unknown
- 1974-02-25 CH CH265474A patent/CH594686A5/xx not_active IP Right Cessation
- 1974-02-25 CS CS741377A patent/CS189625B2/en unknown
- 1974-11-15 AR AR256546A patent/AR201709A1/en active
-
1977
- 1977-02-11 PH PH19444A patent/PH14014A/en unknown
-
1979
- 1979-08-10 NO NO792609A patent/NO792609L/en unknown
-
1980
- 1980-02-27 KE KE3026A patent/KE3026A/en unknown
- 1980-04-11 YU YU0998/80A patent/YU37347B/en unknown
- 1980-04-17 HK HK199/80A patent/HK19980A/en unknown
-
1981
- 1981-02-20 JP JP2533281A patent/JPS56138194A/en active Granted
- 1981-02-20 JP JP2533381A patent/JPS56138195A/en active Granted
- 1981-02-20 JP JP2533181A patent/JPS56138193A/en active Granted
- 1981-12-30 MY MY23/81A patent/MY8100023A/en unknown
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