GB1082962A - Derivatives of 7-aminocephalosporanic acid - Google Patents
Derivatives of 7-aminocephalosporanic acidInfo
- Publication number
- GB1082962A GB1082962A GB2128463A GB2128463A GB1082962A GB 1082962 A GB1082962 A GB 1082962A GB 2128463 A GB2128463 A GB 2128463A GB 2128463 A GB2128463 A GB 2128463A GB 1082962 A GB1082962 A GB 1082962A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- compound
- carboxylate
- hydrogen
- compounds
- 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
- HSHGZXNAXBPPDL-HZGVNTEJSA-N 7beta-aminocephalosporanic acid Chemical class S1CC(COC(=O)C)=C(C([O-])=O)N2C(=O)[C@@H]([NH3+])[C@@H]12 HSHGZXNAXBPPDL-HZGVNTEJSA-N 0.000 title abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 10
- 229910052739 hydrogen Chemical group 0.000 abstract 5
- 239000001257 hydrogen Chemical group 0.000 abstract 5
- -1 7 - phenyl - acetamidoceph - 3 - em - 3 - ylmethyl Chemical group 0.000 abstract 4
- 125000002252 acyl group Chemical group 0.000 abstract 4
- 125000003545 alkoxy group Chemical group 0.000 abstract 4
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 4
- 238000002360 preparation method Methods 0.000 abstract 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 3
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 2
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 abstract 2
- 125000004414 alkyl thio group Chemical group 0.000 abstract 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 2
- 125000001589 carboacyl group Chemical group 0.000 abstract 2
- 125000004181 carboxyalkyl group Chemical group 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 229910052736 halogen Chemical group 0.000 abstract 2
- 150000002367 halogens Chemical group 0.000 abstract 2
- 150000002431 hydrogen Chemical group 0.000 abstract 2
- 125000001841 imino group Chemical group [H]N=* 0.000 abstract 2
- HOKIDJSKDBPKTQ-GLXFQSAKSA-N Cephalosporin C Natural products S1CC(COC(=O)C)=C(C(O)=O)N2C(=O)[C@@H](NC(=O)CCC[C@@H](N)C(O)=O)[C@@H]12 HOKIDJSKDBPKTQ-GLXFQSAKSA-N 0.000 abstract 1
- 229930182555 Penicillin Natural products 0.000 abstract 1
- 108010087702 Penicillinase Proteins 0.000 abstract 1
- 241000295644 Staphylococcaceae Species 0.000 abstract 1
- 239000004098 Tetracycline Substances 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 239000003242 anti bacterial agent Substances 0.000 abstract 1
- 229940088710 antibiotic agent Drugs 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- 239000002775 capsule Substances 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 abstract 1
- HOKIDJSKDBPKTQ-GLXFQSAKSA-M cephalosporin C(1-) Chemical compound S1CC(COC(=O)C)=C(C([O-])=O)N2C(=O)[C@@H](NC(=O)CCC[C@@H]([NH3+])C([O-])=O)[C@@H]12 HOKIDJSKDBPKTQ-GLXFQSAKSA-M 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 239000006071 cream Substances 0.000 abstract 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 abstract 1
- XMHIUKTWLZUKEX-UHFFFAOYSA-N hexacosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O XMHIUKTWLZUKEX-UHFFFAOYSA-N 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 238000002347 injection Methods 0.000 abstract 1
- 239000007924 injection Substances 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 239000006210 lotion Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 239000012038 nucleophile Substances 0.000 abstract 1
- 239000002674 ointment Substances 0.000 abstract 1
- 229950009506 penicillinase Drugs 0.000 abstract 1
- 150000002960 penicillins Chemical class 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000003826 tablet Substances 0.000 abstract 1
- 235000019364 tetracycline Nutrition 0.000 abstract 1
- 150000003522 tetracyclines Chemical class 0.000 abstract 1
- 229940040944 tetracyclines Drugs 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
- 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
- C07D501/38—Methylene radicals, substituted by nitrogen atoms; Lactams thereof with the 2-carboxyl group; Methylene radicals substituted by nitrogen-containing hetero rings attached by the ring nitrogen atom; Quaternary compounds thereof
-
- 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
- C07D501/38—Methylene radicals, substituted by nitrogen atoms; Lactams thereof with the 2-carboxyl group; Methylene radicals substituted by nitrogen-containing hetero rings attached by the ring nitrogen atom; Quaternary compounds thereof
- C07D501/42—Methylene radicals, substituted by nitrogen atoms; Lactams thereof with the 2-carboxyl group; Methylene radicals substituted by nitrogen-containing hetero rings attached by the ring nitrogen atom; Quaternary compounds thereof with the 7-amino radical acylated by an araliphatic carboxylic acid
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Cephalosporin Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2128463A GB1082962A (en) | 1963-05-28 | 1963-05-28 | Derivatives of 7-aminocephalosporanic acid |
| NL646403229A NL140243B (nl) | 1963-05-28 | 1964-03-25 | Werkwijze ter bereiding van 7-((gesubstitueerde) fenylacetylamino)-3-(1-pyridylmethyl)-3-cefem-4-carbonzuurderivaten. |
| DE19641445831 DE1445831C3 (de) | 1963-05-28 | 1964-03-26 | 7-Phenylacetamido-cephalosporansäurederivate, Verfahren zu deren Herstellung und pharmazeutische Formulierungen |
| ES298060A ES298060A1 (es) | 1963-05-28 | 1964-03-26 | Un procedimiento para la producción de compuestos antibióticos |
| BE645868D BE645868A (enrdf_load_stackoverflow) | 1963-05-28 | 1964-03-27 | |
| FR968974A FR4201M (enrdf_load_stackoverflow) | 1963-05-28 | 1964-03-27 | |
| FR968973A FR1524027A (fr) | 1963-05-28 | 1964-03-27 | Dérivés de l'acide 7-aminocéphalosporanique et leur procédé de préparation |
| AT271664A AT261110B (de) | 1963-05-28 | 1964-03-27 | Verfahren zur Herstellung neuer Derivate der 7 Aminocephalosporansäure |
| CH405664A CH515274A (de) | 1963-05-28 | 1964-03-31 | Verfahren zur Herstellung neuer Derivate der 7-Amino-cephalosporansäure mit antibiotischer Wirkung |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2128463A GB1082962A (en) | 1963-05-28 | 1963-05-28 | Derivatives of 7-aminocephalosporanic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1082962A true GB1082962A (en) | 1967-09-13 |
Family
ID=10160300
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2128463A Expired GB1082962A (en) | 1963-05-28 | 1963-05-28 | Derivatives of 7-aminocephalosporanic acid |
Country Status (7)
| Country | Link |
|---|---|
| AT (1) | AT261110B (enrdf_load_stackoverflow) |
| BE (1) | BE645868A (enrdf_load_stackoverflow) |
| CH (1) | CH515274A (enrdf_load_stackoverflow) |
| ES (1) | ES298060A1 (enrdf_load_stackoverflow) |
| FR (1) | FR4201M (enrdf_load_stackoverflow) |
| GB (1) | GB1082962A (enrdf_load_stackoverflow) |
| NL (1) | NL140243B (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4012382A (en) * | 1974-06-05 | 1977-03-15 | Daniel Bouzard | α-Amino and α-formyl-α-(p-acyloxyphenyl)acetamidocephalosporanic acid derivatives |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3118732A1 (de) * | 1981-05-12 | 1982-12-02 | Hoechst Ag, 6000 Frankfurt | Cephalosporinderivate und verfahren zu ihrer herstellung |
-
1963
- 1963-05-28 GB GB2128463A patent/GB1082962A/en not_active Expired
-
1964
- 1964-03-25 NL NL646403229A patent/NL140243B/xx unknown
- 1964-03-26 ES ES298060A patent/ES298060A1/es not_active Expired
- 1964-03-27 BE BE645868D patent/BE645868A/xx unknown
- 1964-03-27 AT AT271664A patent/AT261110B/de active
- 1964-03-27 FR FR968974A patent/FR4201M/fr not_active Expired
- 1964-03-31 CH CH405664A patent/CH515274A/de not_active IP Right Cessation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4012382A (en) * | 1974-06-05 | 1977-03-15 | Daniel Bouzard | α-Amino and α-formyl-α-(p-acyloxyphenyl)acetamidocephalosporanic acid derivatives |
Also Published As
| Publication number | Publication date |
|---|---|
| ES298060A1 (es) | 1964-09-01 |
| NL140243B (nl) | 1973-11-15 |
| CH515274A (de) | 1971-11-15 |
| NL6403229A (enrdf_load_stackoverflow) | 1964-11-30 |
| DE1445831B2 (de) | 1976-04-08 |
| BE645868A (enrdf_load_stackoverflow) | 1964-09-28 |
| FR4201M (enrdf_load_stackoverflow) | 1966-06-06 |
| DE1445831A1 (de) | 1969-05-22 |
| AT261110B (de) | 1968-04-10 |
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