GB1065517A - 7-(substituted propionamido) cephalosporanic acid and derivatives thereof - Google Patents
7-(substituted propionamido) cephalosporanic acid and derivatives thereofInfo
- Publication number
- GB1065517A GB1065517A GB1096165A GB1096165A GB1065517A GB 1065517 A GB1065517 A GB 1065517A GB 1096165 A GB1096165 A GB 1096165A GB 1096165 A GB1096165 A GB 1096165A GB 1065517 A GB1065517 A GB 1065517A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compounds
- propionamido
- cephalosporanic acid
- substituted
- imidazolinium
- 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
- 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 title abstract 3
- -1 propionamido Chemical group 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 5
- 229910052736 halogen Inorganic materials 0.000 abstract 3
- 150000002367 halogens Chemical class 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- ANFXTILBDGTSEG-UHFFFAOYSA-N 1-methyl-4,5-dihydroimidazole Chemical group CN1CCN=C1 ANFXTILBDGTSEG-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 abstract 2
- 150000002431 hydrogen Chemical group 0.000 abstract 2
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical group C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 abstract 2
- PFZCOWLKXHIVII-UHFFFAOYSA-N pyridin-1-ium-1-amine Chemical group N[N+]1=CC=CC=C1 PFZCOWLKXHIVII-UHFFFAOYSA-N 0.000 abstract 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 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000000129 anionic group Chemical group 0.000 abstract 1
- 239000004599 antimicrobial Substances 0.000 abstract 1
- 125000005129 aryl carbonyl group Chemical group 0.000 abstract 1
- 150000001768 cations Chemical class 0.000 abstract 1
- 125000003106 haloaryl group Chemical group 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 125000004999 nitroaryl group Chemical group 0.000 abstract 1
- 231100000252 nontoxic Toxicity 0.000 abstract 1
- 230000003000 nontoxic effect Effects 0.000 abstract 1
- 235000019260 propionic acid Nutrition 0.000 abstract 1
- JBDKINLIWFKAQO-UHFFFAOYSA-N pyridin-1-ium-1-yl acetate Chemical group CC(=O)O[N+]1=CC=CC=C1 JBDKINLIWFKAQO-UHFFFAOYSA-N 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical group C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 abstract 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical class 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 abstract 1
- 150000003839 salts Chemical class 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
-
- 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
-
- 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)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Cephalosporin Compounds (AREA)
Abstract
A 7-(substituted propionamido) cephalosporanic acid or derivative has the formula <FORM:1065517/C2/1> wherein R1 is aryl, arylcarbonyl, five-membered heterocyclic, haloaryl, nitroaryl, haloarylcarbonyl or nitroarylcarbonyl; R2 and R3 are each hydrogen or halogen or aryl; one of R4 and R5 is a halogen and the other is hydrogen, halogen or alkoxy (C1- 6); R6 is acetoxy, pyridinium, amino-pyridinium, imidazolinium or methyl-imidazolinium; M is hydrogen, a pharmaceutically acceptable non-toxic cation or an anionic charge. The compounds are prepared by reacting 7-amino-cephalosporanic acid or the appropriate derivative with a substituted propionic acid of formula <FORM:1065517/C2/2> or a reactive derivative thereof, wherein R1 to R5 have the above meanings; and, if desired, forming a salt. Compounds of Formula I where R6 is acetoxy may be converted to compounds where R6 is pyridinium, aminopyridinium, imidazolinium or methylimidazolinium by treatment with the appropriate base, e.g. pyridine. A typical compound is 7-(2,3-dichloro-3-phenyl-propionamido) cephalosporanic acid. The compounds are antimicrobial agents.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1427564 | 1964-03-14 | ||
| JP4212764 | 1964-07-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1065517A true GB1065517A (en) | 1967-04-19 |
Family
ID=26350189
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1096165A Expired GB1065517A (en) | 1964-03-14 | 1965-03-15 | 7-(substituted propionamido) cephalosporanic acid and derivatives thereof |
Country Status (3)
| Country | Link |
|---|---|
| FR (1) | FR5395M (en) |
| GB (1) | GB1065517A (en) |
| SE (1) | SE329164B (en) |
-
1965
- 1965-03-13 FR FR9155A patent/FR5395M/fr not_active Expired
- 1965-03-15 GB GB1096165A patent/GB1065517A/en not_active Expired
- 1965-03-15 SE SE334965A patent/SE329164B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE1545795A1 (en) | 1969-12-11 |
| SE329164B (en) | 1970-10-05 |
| FR5395M (en) | 1967-09-25 |
| DE1545795B2 (en) | 1975-07-17 |
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