GB976225A - Carbocycloxyalkyl cephalosporins - Google Patents
Carbocycloxyalkyl cephalosporinsInfo
- Publication number
- GB976225A GB976225A GB32192/62A GB3219262A GB976225A GB 976225 A GB976225 A GB 976225A GB 32192/62 A GB32192/62 A GB 32192/62A GB 3219262 A GB3219262 A GB 3219262A GB 976225 A GB976225 A GB 976225A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compounds
- product
- nuclei
- acyl derivative
- amino
- 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
- 229930186147 Cephalosporin Natural products 0.000 title abstract 3
- 229940124587 cephalosporin Drugs 0.000 title abstract 3
- 150000001780 cephalosporins Chemical class 0.000 title abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 5
- 125000002252 acyl group Chemical group 0.000 abstract 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- 125000004423 acyloxy group Chemical group 0.000 abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- 125000001302 tertiary amino group Chemical group 0.000 abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 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 abstract 1
- 108010013043 Acetylesterase Proteins 0.000 abstract 1
- 241000207199 Citrus Species 0.000 abstract 1
- 102100036617 Monoacylglycerol lipase ABHD2 Human genes 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 230000010933 acylation Effects 0.000 abstract 1
- 238000005917 acylation reaction Methods 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 150000001450 anions Chemical class 0.000 abstract 1
- 239000003242 anti bacterial agent Substances 0.000 abstract 1
- 229940088710 antibiotic agent Drugs 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 230000003115 biocidal effect Effects 0.000 abstract 1
- 150000001768 cations Chemical class 0.000 abstract 1
- 235000020971 citrus fruits Nutrition 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 125000004981 cycloalkylmethyl group Chemical group 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 125000001624 naphthyl group Chemical group 0.000 abstract 1
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 231100000252 nontoxic Toxicity 0.000 abstract 1
- 230000003000 nontoxic effect Effects 0.000 abstract 1
- 159000000001 potassium salts Chemical class 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 238000006467 substitution reaction Methods 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cephalosporin Compounds (AREA)
Abstract
Relates to antibiotic substances of the class represented by the formula <FORM:0976225/C1/1> wherein R1, taken alone, is -OH, C1-C8 acyloxy, or tertiary-amino; R2 is -OH when R1 is -OH; R2 is -OH when R1 is C1-C8 acyloxy; R2 is -O- when R1 is tertiary-amino; R1 and R2, when taken together, are -O-; R3 is C1-C4 alkylene; and R4 is benzyl, naphthyl, naphthyl-methyl, C4-C6 cycloalkyl or C4-C6 cycloalkylmethyl or a substitution product thereof containing at least one substituent consisting of halogen, nitro, trifluoromethyl, C1-C4 alkyl, or C1-C2 alkoxy; and the pharmaceutically acceptable salts, esters and amides thereof. The antibiotics may be prepared by acylation of the appropriate 7-amino compound with the appropriate acylating agent or by acylating 7-aminocephalosporanic acid with the appropriate acylating agent and then (a) heating the product with acidified water to form the corresponding acyl derivative of the nuclei of cephalosporin Cc compounds, (b) treating the product with citrus acetyl esterase to form the corresponding acyl derivative of the nuclei of desacetylcephalosporin C compounds or (c) refluxing the product in solution to form the corresponding acyl derivative of the nuclei of cephalosporin Ca compounds. The Specification includes many examples of compounds of the above formula and specific examples describe the production of the potassium salts of 7-benzyloxy- and 7-b -naphthoxy-acetamidocephalosporanic acid. Non-toxic derivatives of compounds of the above formula may be prepared by combining them with pharmaceutically acceptable cations, anions, alcohols, ammonia or amines. Specification 810,196 is referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US133339A US3222363A (en) | 1961-08-23 | 1961-08-23 | Carbocycloxyalkyl cephalosporins |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB976225A true GB976225A (en) | 1964-11-25 |
Family
ID=22458125
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB32192/62A Expired GB976225A (en) | 1961-08-23 | 1962-08-22 | Carbocycloxyalkyl cephalosporins |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US3222363A (en) |
| BR (1) | BR6242366D0 (en) |
| FR (1) | FR1605106A (en) |
| GB (1) | GB976225A (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3324118A (en) * | 1965-12-27 | 1967-06-06 | Lilly Co Eli | Phenalkylmercaptomethyl cephalosporins |
| US3522250A (en) * | 1968-10-15 | 1970-07-28 | American Home Prod | Derivatives of 7-aminocephalosporanic acid |
| GB1547165A (en) * | 1975-08-15 | 1979-06-06 | Beecham Group Ltd | 3-carbamoylbenzyl and 3-(carbamoylpyridylmethyl)-cephems |
| US4198504A (en) * | 1978-11-02 | 1980-04-15 | Bristol-Myers Company | [3-(Pyridinium)-7-(naphthyiridinyl carbonylamino)acetamido]cephalosporanic acid derivatives |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE593777A (en) * | ||||
| US2941995A (en) * | 1957-08-02 | 1960-06-21 | Beecham Res Lab | Recovery of solid 6-aminopenicillanic acid |
-
1961
- 1961-08-23 US US133339A patent/US3222363A/en not_active Expired - Lifetime
-
1962
- 1962-08-22 GB GB32192/62A patent/GB976225A/en not_active Expired
- 1962-08-23 FR FR1605106D patent/FR1605106A/en not_active Expired
- 1962-08-23 BR BR142366/62A patent/BR6242366D0/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR1605106A (en) | 1973-03-16 |
| US3222363A (en) | 1965-12-07 |
| BR6242366D0 (en) | 1973-07-12 |
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