IE43845L - 4-thia-1-azabicyclo [4.2.0] oct-2-ene derivatives - Google Patents
4-thia-1-azabicyclo [4.2.0] oct-2-ene derivativesInfo
- Publication number
- IE43845L IE43845L IE760972A IE97276A IE43845L IE 43845 L IE43845 L IE 43845L IE 760972 A IE760972 A IE 760972A IE 97276 A IE97276 A IE 97276A IE 43845 L IE43845 L IE 43845L
- Authority
- IE
- Ireland
- Prior art keywords
- formula
- compounds
- protective group
- meaning stated
- substituents
- Prior art date
Links
- FGCQMZBYJKQGRL-UHFFFAOYSA-N 4-thia-1-azabicyclo[4.2.0]oct-2-ene Chemical class C1=CSCC2CCN21 FGCQMZBYJKQGRL-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 6
- 125000006239 protecting group Chemical group 0.000 abstract 4
- 230000008030 elimination Effects 0.000 abstract 3
- 238000003379 elimination reaction Methods 0.000 abstract 3
- 125000001424 substituent group Chemical group 0.000 abstract 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 2
- 241000894006 Bacteria Species 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 230000006181 N-acylation Effects 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000005042 acyloxymethyl group Chemical group 0.000 abstract 1
- 239000003242 anti bacterial agent Substances 0.000 abstract 1
- 229940088710 antibiotic agent Drugs 0.000 abstract 1
- 230000031709 bromination Effects 0.000 abstract 1
- 238000005893 bromination reaction Methods 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
- 125000005997 bromomethyl group Chemical group 0.000 abstract 1
- 150000001735 carboxylic acids Chemical class 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 239000003999 initiator Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
-
- 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
-
- 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
-
- 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
- C07D205/085—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 nitrogen atom directly attached in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D263/36—One oxygen atom
- C07D263/38—One oxygen atom attached in position 2
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Cephalosporin Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Compounds of the formula I in which R and E have the meaning stated in Claim 1 are antibiotics which are effective against Gram-positive and Gram-negative bacteria. They are prepared by N-acylation of compounds of the formula II in which R<2> is hydrogen or a carboxyl protective group with compounds of the formula RX' in which X' has the meaning stated in Claim 1, and elimination of any carboxyl protective group present. During the reaction, intermediate protection of the sensitive substituents present in the radical R is also possible. The carboxylic acids of the formula II in which E is bromomethyl are prepared by bromination of compounds of the formula IV-b in which the substituents have the meaning stated in Claim 25 with a compound which provides bromine free radicals in the presence of an initiator which provides free radicals, with subsequent elimination of the amino protective group, or if E in the formula IV-b is a lower alkanoyloxymethyl group, by reaction of a compound of the formula VIII in which the substituents have the meaning stated in Claim 29 with a salt of a lower alkanecarboxylic acid and subsequent elimination of the amino protective group. <IMAGE>
[GB1553429A]
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IE189/81A IE43846B1 (en) | 1975-05-05 | 1976-05-05 | Azetidine compounds |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US57422575A | 1975-05-05 | 1975-05-05 | |
| US62668675A | 1975-10-29 | 1975-10-29 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE43845L true IE43845L (en) | 1976-11-05 |
| IE43845B1 IE43845B1 (en) | 1981-06-17 |
Family
ID=27076332
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE972/76A IE43845B1 (en) | 1975-05-05 | 1976-05-05 | 4-thia-1-azabicyclo/4.2.0/oct-2-ene derivatives |
Country Status (11)
| Country | Link |
|---|---|
| JP (1) | JPS51136694A (en) |
| AU (1) | AU500636B2 (en) |
| CH (3) | CH623331A5 (en) |
| DE (1) | DE2619458A1 (en) |
| DK (1) | DK194776A (en) |
| ES (3) | ES447577A1 (en) |
| FR (2) | FR2324639A1 (en) |
| GB (2) | GB1553429A (en) |
| IE (1) | IE43845B1 (en) |
| LU (1) | LU74873A1 (en) |
| NL (1) | NL7604797A (en) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4122086A (en) * | 1977-07-26 | 1978-10-24 | Smithkline Corporation | Isopenicillins |
| FR2505840A1 (en) * | 1981-05-13 | 1982-11-19 | Roussel Uclaf | NOVEL PRODUCTS DERIVED FROM 2-AMINO THIAZOLYL 2-OXYIMINO ACETAMIDO BICYCLO-OCTENE CARBOXYLIC ACID, PROCESS FOR PREPARING THEM AND THEIR APPLICATION AS MEDICAMENTS |
| FR2552089B2 (en) * | 1981-05-13 | 1985-10-25 | Roussel Uclaf | NOVEL PRODUCTS DERIVED FROM 2-AMINO THIAZOLYL ACID 2-OXYIMINO ACETAMIDO BICYCLO-OCTENE CARBOXYLIC, THEIR PREPARATION PROCESS AND THEIR APPLICATION AS MEDICAMENTS |
| CA1262128A (en) * | 1981-08-27 | 1989-10-03 | Christian N. Hubschwerlen | .beta.-lactams |
| FR2538389B2 (en) * | 1981-10-23 | 1986-05-16 | Roussel Uclaf | NEW PRODUCTS DERIVED FROM 3-AMINO 2-OXO AZETIDINE-1-SULFAMIC ACID, NEW PROCESS FOR THE PREPARATION OF OPTICALLY ACTIVE PRODUCTS, APPLICATION OF NEW PRODUCTS AS MEDICAMENTS AND PRODUCTS NECESSARY FOR THEIR PREPARATION |
| FR2558467B2 (en) * | 1981-10-23 | 1987-03-20 | Roussel Uclaf | NEW PRODUCT DERIVED FROM 3-AMINO 2-OXO AZETIDINE 1-SULPHAMIC ACID, ITS PREPARATION PROCESS, ITS USE AS A MEDICAMENT AND AN INTERMEDIATE PRODUCT NECESSARY FOR ITS PREPARATION |
| FR2515182B1 (en) * | 1981-10-23 | 1986-05-09 | Roussel Uclaf | NOVEL PRODUCTS DERIVED FROM 3-AMINO 2-OXO AZETIDINE 1-SULFAMIC ACID, THEIR PREPARATION PROCESS, THEIR APPLICATION AS MEDICAMENTS AND THE INTERMEDIATE PRODUCTS NECESSARY FOR THEIR PREPARATION |
| JPS6036458A (en) * | 1983-08-08 | 1985-02-25 | Sumitomo Chem Co Ltd | Method for producing β-lactam derivatives |
| FR2559486B1 (en) * | 1984-02-13 | 1988-02-12 | Roussel Uclaf | NOVEL DERIVATIVES OF 1-DETHIA 2-THIA CEPHALOSPORANIC ACID, PROCESS FOR THEIR PREPARATION AND THEIR APPLICATION AS MEDICAMENTS |
| FR2586020B2 (en) * | 1985-08-09 | 1988-10-14 | Roussel Uclaf | NOVEL DERIVATIVES OF 1-DETHIA 2-THIA CEPHALOSPORANIC ACID, PROCESS FOR THEIR PREPARATION, THEIR APPLICATION AS MEDICAMENTS AND THE PHARMACEUTICAL COMPOSITIONS CONTAINING THEM |
| FR2588867B1 (en) * | 1985-10-23 | 1988-12-09 | Roussel Uclaf | NOVEL PRODUCTS DERIVED FROM THE 3-AMINO 2-OXO AZETIDINE SERIES, THEIR PREPARATION PROCESS AND THEIR APPLICATION |
| FR2610630B2 (en) * | 1987-02-06 | 1989-05-26 | Roussel Uclaf | NOVEL DERIVATIVES OF 1-DETHIA 2-THIA CEPHALOSPORANIC ACID, PROCESS FOR THEIR PREPARATION, THEIR USE AS MEDICAMENTS AND THE PHARMACEUTICAL COMPOSITIONS CONTAINING THEM |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2046823A1 (en) * | 1970-09-23 | 1972-03-30 | Farbwerke Hoechst AG vormals Meister Lucius & Brüning, 6000 Frankfurt | New azetidinones (2) and processes for their preparation |
-
1976
- 1976-04-30 DK DK194776A patent/DK194776A/en not_active Application Discontinuation
- 1976-05-03 DE DE19762619458 patent/DE2619458A1/en not_active Withdrawn
- 1976-05-03 LU LU74873A patent/LU74873A1/xx unknown
- 1976-05-04 FR FR7613251A patent/FR2324639A1/en active Granted
- 1976-05-04 JP JP51051226A patent/JPS51136694A/en active Pending
- 1976-05-04 CH CH557276A patent/CH623331A5/en not_active IP Right Cessation
- 1976-05-04 ES ES447577A patent/ES447577A1/en not_active Expired
- 1976-05-05 AU AU13669/76A patent/AU500636B2/en not_active Ceased
- 1976-05-05 IE IE972/76A patent/IE43845B1/en unknown
- 1976-05-05 GB GB15246/76A patent/GB1553429A/en not_active Expired
- 1976-05-05 NL NL7604797A patent/NL7604797A/en not_active Application Discontinuation
- 1976-05-05 GB GB991/79A patent/GB1553430A/en not_active Expired
- 1976-09-21 FR FR7628304A patent/FR2313362A1/en active Granted
-
1977
- 1977-07-14 ES ES460722A patent/ES460722A1/en not_active Expired
- 1977-07-14 ES ES460746A patent/ES460746A1/en not_active Expired
-
1980
- 1980-05-14 CH CH379380A patent/CH627475A5/en not_active IP Right Cessation
- 1980-05-14 CH CH379280A patent/CH624670A5/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| ES447577A1 (en) | 1977-12-01 |
| ES460722A1 (en) | 1978-05-01 |
| DE2619458A1 (en) | 1976-11-18 |
| CH623331A5 (en) | 1981-05-29 |
| NL7604797A (en) | 1976-11-09 |
| CH624670A5 (en) | 1981-08-14 |
| FR2324639A1 (en) | 1977-04-15 |
| LU74873A1 (en) | 1977-01-12 |
| ES460746A1 (en) | 1978-10-01 |
| DK194776A (en) | 1976-11-06 |
| IE43845B1 (en) | 1981-06-17 |
| FR2313362B1 (en) | 1979-03-23 |
| AU500636B2 (en) | 1979-05-31 |
| JPS51136694A (en) | 1976-11-26 |
| GB1553429A (en) | 1979-09-26 |
| FR2313362A1 (en) | 1976-12-31 |
| AU1366976A (en) | 1977-11-10 |
| CH627475A5 (en) | 1982-01-15 |
| FR2324639B1 (en) | 1978-11-03 |
| GB1553430A (en) | 1979-09-26 |
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