GB1442993A - Penicillin and cephalosporin r-sulphoxides - Google Patents
Penicillin and cephalosporin r-sulphoxidesInfo
- Publication number
- GB1442993A GB1442993A GB3359672A GB3359672A GB1442993A GB 1442993 A GB1442993 A GB 1442993A GB 3359672 A GB3359672 A GB 3359672A GB 3359672 A GB3359672 A GB 3359672A GB 1442993 A GB1442993 A GB 1442993A
- Authority
- GB
- United Kingdom
- Prior art keywords
- sulphoxides
- cephalosporin
- group
- penicillin
- oxidation
- 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 7
- 229940124587 cephalosporin Drugs 0.000 title abstract 7
- 229930182555 Penicillin Natural products 0.000 title abstract 6
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 title abstract 5
- 150000001780 cephalosporins Chemical class 0.000 title abstract 5
- 229940049954 penicillin Drugs 0.000 title abstract 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 3
- 125000003277 amino group Chemical group 0.000 abstract 3
- 239000000203 mixture Substances 0.000 abstract 3
- 230000003647 oxidation Effects 0.000 abstract 3
- 238000007254 oxidation reaction Methods 0.000 abstract 3
- 150000007513 acids Chemical class 0.000 abstract 2
- -1 cephalosporin compounds Chemical class 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 abstract 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 abstract 1
- ATTZFSUZZUNHBP-UHFFFAOYSA-N Piperonyl sulfoxide Chemical group CCCCCCCCS(=O)C(C)CC1=CC=C2OCOC2=C1 ATTZFSUZZUNHBP-UHFFFAOYSA-N 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 125000004423 acyloxy group Chemical group 0.000 abstract 1
- 230000000844 anti-bacterial effect Effects 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 239000000969 carrier Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- GNBHRKFJIUUOQI-UHFFFAOYSA-N fluorescein Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 GNBHRKFJIUUOQI-UHFFFAOYSA-N 0.000 abstract 1
- 201000011243 gastrointestinal stromal tumor Diseases 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- 230000001678 irradiating effect Effects 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- CXKWCBBOMKCUKX-UHFFFAOYSA-M methylene blue Chemical compound [Cl-].C1=CC(N(C)C)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 CXKWCBBOMKCUKX-UHFFFAOYSA-M 0.000 abstract 1
- 229960000907 methylthioninium chloride Drugs 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 230000000269 nucleophilic effect Effects 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 150000002960 penicillins Chemical class 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 abstract 1
- 229940043267 rhodamine b Drugs 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000007858 starting material Substances 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
- C07D501/02—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
-
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/429—Thiazoles condensed with heterocyclic ring systems
- A61K31/43—Compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula, e.g. penicillins, penems
-
- 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
- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D499/04—Preparation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D499/21—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring with a nitrogen atom directly attached in position 6 and a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2
- C07D499/44—Compounds with an amino radical acylated by carboxylic acids, attached in position 6
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)
- Peptides Or Proteins (AREA)
- Cephalosporin Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3359672A GB1442993A (en) | 1972-07-18 | 1972-07-18 | Penicillin and cephalosporin r-sulphoxides |
| FR7326172A FR2192805B1 (enrdf_load_stackoverflow) | 1972-07-18 | 1973-07-17 | |
| NL7309918A NL7309918A (enrdf_load_stackoverflow) | 1972-07-18 | 1973-07-17 | |
| AT626873A AT341665B (de) | 1972-07-18 | 1973-07-17 | Verfahren zur herstellung von neuen r-sulfoxyden von 7-amino-cephalosporansauren |
| JP8242073A JPS4980089A (enrdf_load_stackoverflow) | 1972-07-18 | 1973-07-17 | |
| DE19732336344 DE2336344A1 (de) | 1972-07-18 | 1973-07-17 | Penicillin- und cephalosporin-rsulfoxide, ihre salze und ester, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| HUGI000193 HU170698B (enrdf_load_stackoverflow) | 1972-07-18 | 1973-07-17 | |
| US05/633,006 US4075337A (en) | 1972-07-18 | 1975-11-18 | Methods of combatting bacterial infections in warm-blooded animal with cephalsporin R-sulfoxide |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3359672A GB1442993A (en) | 1972-07-18 | 1972-07-18 | Penicillin and cephalosporin r-sulphoxides |
| GB4872072 | 1972-10-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1442993A true GB1442993A (en) | 1976-07-21 |
Family
ID=26261933
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3359672A Expired GB1442993A (en) | 1972-07-18 | 1972-07-18 | Penicillin and cephalosporin r-sulphoxides |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS4980089A (enrdf_load_stackoverflow) |
| AT (1) | AT341665B (enrdf_load_stackoverflow) |
| DE (1) | DE2336344A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2192805B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1442993A (enrdf_load_stackoverflow) |
| HU (1) | HU170698B (enrdf_load_stackoverflow) |
| NL (1) | NL7309918A (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0017419A1 (en) * | 1979-03-26 | 1980-10-15 | Eli Lilly And Company | Process for preparing penicillin sulfoxides |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6019316B2 (ja) * | 1976-01-29 | 1985-05-15 | 塩野義製薬株式会社 | ペニシリンオキシド |
| DE2716677C2 (de) * | 1977-04-15 | 1985-10-10 | Hoechst Ag, 6230 Frankfurt | Cephemderivate und Verfahren zu ihrer Herstellung |
| JPS58986A (ja) * | 1981-05-07 | 1983-01-06 | Fujisawa Pharmaceut Co Ltd | セフェム化合物 |
| EP0496739A1 (en) * | 1989-10-16 | 1992-08-05 | Akzo Nobel N.V. | Conversion of penicillins and cephalosporins to 1-(s)-sulfoxides |
-
1972
- 1972-07-18 GB GB3359672A patent/GB1442993A/en not_active Expired
-
1973
- 1973-07-17 DE DE19732336344 patent/DE2336344A1/de active Pending
- 1973-07-17 JP JP8242073A patent/JPS4980089A/ja active Pending
- 1973-07-17 NL NL7309918A patent/NL7309918A/xx unknown
- 1973-07-17 FR FR7326172A patent/FR2192805B1/fr not_active Expired
- 1973-07-17 AT AT626873A patent/AT341665B/de not_active IP Right Cessation
- 1973-07-17 HU HUGI000193 patent/HU170698B/hu unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0017419A1 (en) * | 1979-03-26 | 1980-10-15 | Eli Lilly And Company | Process for preparing penicillin sulfoxides |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2192805B1 (enrdf_load_stackoverflow) | 1976-09-03 |
| ATA626873A (de) | 1977-06-15 |
| AT341665B (de) | 1978-02-27 |
| DE2336344A1 (de) | 1974-03-14 |
| NL7309918A (enrdf_load_stackoverflow) | 1974-01-22 |
| FR2192805A1 (enrdf_load_stackoverflow) | 1974-02-15 |
| HU170698B (enrdf_load_stackoverflow) | 1977-08-28 |
| JPS4980089A (enrdf_load_stackoverflow) | 1974-08-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |