GB1368234A - Thiosubstituted szetidinones and other antibiotic precursors - Google Patents
Thiosubstituted szetidinones and other antibiotic precursorsInfo
- Publication number
- GB1368234A GB1368234A GB5228670A GB5228670A GB1368234A GB 1368234 A GB1368234 A GB 1368234A GB 5228670 A GB5228670 A GB 5228670A GB 5228670 A GB5228670 A GB 5228670A GB 1368234 A GB1368234 A GB 1368234A
- Authority
- GB
- United Kingdom
- Prior art keywords
- group
- formula
- aliphatic
- araliphatic
- 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
- 230000003115 biocidal effect Effects 0.000 title abstract 2
- 239000002243 precursor Substances 0.000 title 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 9
- 150000001875 compounds Chemical class 0.000 abstract 8
- 125000003118 aryl group Chemical group 0.000 abstract 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 4
- 125000002252 acyl group Chemical group 0.000 abstract 3
- 239000003153 chemical reaction reagent Substances 0.000 abstract 3
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 239000003638 chemical reducing agent Substances 0.000 abstract 2
- 238000006894 reductive elimination reaction Methods 0.000 abstract 2
- -1 sulphonyloxy group Chemical group 0.000 abstract 2
- SCVJRXQHFJXZFZ-KVQBGUIXSA-N 2-amino-9-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3h-purine-6-thione Chemical compound C1=2NC(N)=NC(=S)C=2N=CN1[C@H]1C[C@H](O)[C@@H](CO)O1 SCVJRXQHFJXZFZ-KVQBGUIXSA-N 0.000 abstract 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 239000005864 Sulphur Substances 0.000 abstract 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-N Thiophosphoric acid Chemical class OP(O)(S)=O RYYWUUFWQRZTIU-UHFFFAOYSA-N 0.000 abstract 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract 1
- 125000004442 acylamino group Chemical group 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical class O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 abstract 1
- 239000002585 base Substances 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 239000004202 carbamide Substances 0.000 abstract 1
- 238000005868 electrolysis reaction Methods 0.000 abstract 1
- 125000004185 ester group Chemical group 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 150000004678 hydrides Chemical class 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 229910052740 iodine Inorganic materials 0.000 abstract 1
- 239000011630 iodine Substances 0.000 abstract 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 abstract 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 1
- 239000012038 nucleophile Substances 0.000 abstract 1
- 238000007248 oxidative elimination reaction Methods 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 abstract 1
- 229910052716 thallium Inorganic materials 0.000 abstract 1
- BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 abstract 1
- 150000003556 thioamides Chemical class 0.000 abstract 1
- 150000003567 thiocyanates Chemical class 0.000 abstract 1
- 150000003573 thiols Chemical class 0.000 abstract 1
- 150000004764 thiosulfuric acid derivatives Chemical class 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
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/06—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D205/08—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams
- C07D205/09—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams with a sulfur atom directly attached in position 4
- C07D205/095—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams with a sulfur atom directly attached in position 4 and with a nitrogen atom directly attached in position 3
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cephalosporin Compounds (AREA)
Priority Applications (13)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB5228670A GB1368234A (en) | 1970-11-03 | 1970-11-03 | Thiosubstituted szetidinones and other antibiotic precursors |
| BE770730A BE770730A (fr) | 1970-11-03 | 1971-07-30 | Nouveaux composes intermediaires pour la synthese de cephalosporines, penicillines et antibiotiques analogues |
| CH1129671A CH589622A5 (enrdf_load_stackoverflow) | 1970-11-03 | 1971-07-30 | |
| ES393804A ES393804A1 (es) | 1970-11-03 | 1971-07-30 | Un procedimiento para la preparacion de compuestos semisin-teticos utilizados en la produccion de cefalosporinas, pe- nicilinas y compuestos antibioticos relacionados en betalac-tama. |
| NL7110615A NL7110615A (enrdf_load_stackoverflow) | 1970-11-03 | 1971-07-30 | |
| DE19712138320 DE2138320A1 (de) | 1970-11-03 | 1971-07-30 | Chemische Verbindungen |
| AU31846/71A AU475747B2 (en) | 1970-11-03 | 1971-07-30 | Thiosubstituted azetidinones |
| FR7128116A FR2112411B1 (enrdf_load_stackoverflow) | 1970-11-03 | 1971-07-30 | |
| ES419264A ES419264A1 (es) | 1970-11-03 | 1973-10-02 | Un procedimiento para la preparacion de derivados de azeti-din-2-ona. |
| AT746374A AT339912B (de) | 1970-11-03 | 1974-09-16 | Verfahren zur herstellung von neuen azetidinverbindungen |
| SE7414854A SE7414854L (enrdf_load_stackoverflow) | 1970-11-03 | 1974-11-26 | |
| CH1129671A CH586675A5 (enrdf_load_stackoverflow) | 1970-11-03 | 1976-03-22 | |
| US05/726,425 US4174318A (en) | 1970-11-03 | 1976-09-22 | Alkylative cleavage of azetidinone disulfides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB5228670A GB1368234A (en) | 1970-11-03 | 1970-11-03 | Thiosubstituted szetidinones and other antibiotic precursors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1368234A true GB1368234A (en) | 1974-09-25 |
Family
ID=10463345
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5228670A Expired GB1368234A (en) | 1970-11-03 | 1970-11-03 | Thiosubstituted szetidinones and other antibiotic precursors |
Country Status (9)
| Country | Link |
|---|---|
| AU (1) | AU475747B2 (enrdf_load_stackoverflow) |
| BE (1) | BE770730A (enrdf_load_stackoverflow) |
| CH (2) | CH589622A5 (enrdf_load_stackoverflow) |
| DE (1) | DE2138320A1 (enrdf_load_stackoverflow) |
| ES (2) | ES393804A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2112411B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1368234A (enrdf_load_stackoverflow) |
| NL (1) | NL7110615A (enrdf_load_stackoverflow) |
| SE (1) | SE7414854L (enrdf_load_stackoverflow) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4115383A (en) | 1976-02-23 | 1978-09-19 | Eli Lilly And Company | Alkoxycarbonyl-ethylthio-azetidinones and process for their preparation |
| US4147864A (en) | 1975-02-20 | 1979-04-03 | Ciba-Geigy Corporation | Process for the manufacture of 7β-amino-3-cephem-3-ol-4 carboxylic acid compounds |
| US4288366A (en) | 1976-02-23 | 1981-09-08 | Snamprogetti, S.P.A. | Method of preparation of 5,6-dehydropenicillins |
| US4301278A (en) | 1974-02-26 | 1981-11-17 | Ciba-Geigy Corporation | Process for the manufacture of enol derivatives |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE789021A (fr) * | 1971-09-21 | 1973-03-20 | Glaxo Lab Ltd | Procede de preparation d'azetidin-2-ones |
| BE794659A (fr) * | 1972-01-28 | 1973-07-30 | Glaxo Lab Ltd | Procede de preparation de composes intermediaires pour l'obtention d'antibiotiques de type beta-lactame |
-
1970
- 1970-11-03 GB GB5228670A patent/GB1368234A/en not_active Expired
-
1971
- 1971-07-30 NL NL7110615A patent/NL7110615A/xx not_active Application Discontinuation
- 1971-07-30 DE DE19712138320 patent/DE2138320A1/de not_active Withdrawn
- 1971-07-30 BE BE770730A patent/BE770730A/xx unknown
- 1971-07-30 ES ES393804A patent/ES393804A1/es not_active Expired
- 1971-07-30 FR FR7128116A patent/FR2112411B1/fr not_active Expired
- 1971-07-30 CH CH1129671A patent/CH589622A5/xx not_active IP Right Cessation
- 1971-07-30 AU AU31846/71A patent/AU475747B2/en not_active Expired
-
1973
- 1973-10-02 ES ES419264A patent/ES419264A1/es not_active Expired
-
1974
- 1974-11-26 SE SE7414854A patent/SE7414854L/xx unknown
-
1976
- 1976-03-22 CH CH1129671A patent/CH586675A5/xx not_active IP Right Cessation
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4301278A (en) | 1974-02-26 | 1981-11-17 | Ciba-Geigy Corporation | Process for the manufacture of enol derivatives |
| US4147864A (en) | 1975-02-20 | 1979-04-03 | Ciba-Geigy Corporation | Process for the manufacture of 7β-amino-3-cephem-3-ol-4 carboxylic acid compounds |
| US4115383A (en) | 1976-02-23 | 1978-09-19 | Eli Lilly And Company | Alkoxycarbonyl-ethylthio-azetidinones and process for their preparation |
| US4288366A (en) | 1976-02-23 | 1981-09-08 | Snamprogetti, S.P.A. | Method of preparation of 5,6-dehydropenicillins |
| US4353825A (en) | 1976-02-23 | 1982-10-12 | Snamprogetti, S.P.A. | 5,6-Dehydropenicillins |
Also Published As
| Publication number | Publication date |
|---|---|
| BE770730A (fr) | 1972-01-31 |
| FR2112411A1 (enrdf_load_stackoverflow) | 1972-06-16 |
| FR2112411B1 (enrdf_load_stackoverflow) | 1975-11-28 |
| SE7414854L (enrdf_load_stackoverflow) | 1974-11-26 |
| CH586675A5 (enrdf_load_stackoverflow) | 1977-04-15 |
| NL7110615A (enrdf_load_stackoverflow) | 1972-05-05 |
| DE2138320A1 (de) | 1972-05-04 |
| AU475747B2 (en) | 1976-09-02 |
| ES419264A1 (es) | 1976-11-01 |
| CH589622A5 (enrdf_load_stackoverflow) | 1977-07-15 |
| AU3184671A (en) | 1973-02-01 |
| ES393804A1 (es) | 1974-07-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| 48S | Specification amended (sect. 8/1949) | ||
| 49R | Reference inserted (sect. 9/1949) | ||
| PCNP | Patent ceased through non-payment of renewal fee |