IE36638L - Preparing cephalosporins from penicillanic sulphoxides - Google Patents
Preparing cephalosporins from penicillanic sulphoxidesInfo
- Publication number
- IE36638L IE36638L IE721136A IE113672A IE36638L IE 36638 L IE36638 L IE 36638L IE 721136 A IE721136 A IE 721136A IE 113672 A IE113672 A IE 113672A IE 36638 L IE36638 L IE 36638L
- Authority
- IE
- Ireland
- Prior art keywords
- sulphoxide
- penicillin
- alkyl
- group
- optionally substituted
- Prior art date
Links
- 229930186147 Cephalosporin Natural products 0.000 title 1
- 229940124587 cephalosporin Drugs 0.000 title 1
- 150000001780 cephalosporins Chemical class 0.000 title 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical class 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 abstract 6
- ATTZFSUZZUNHBP-UHFFFAOYSA-N Piperonyl sulfoxide Chemical compound CCCCCCCCS(=O)C(C)CC1=CC=C2OCOC2=C1 ATTZFSUZZUNHBP-UHFFFAOYSA-N 0.000 abstract 5
- 229930182555 Penicillin Natural products 0.000 abstract 4
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 4
- 229940049954 penicillin Drugs 0.000 abstract 4
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 229910052799 carbon Inorganic materials 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- -1 triethylsilyl Chemical class 0.000 abstract 2
- 125000000026 trimethylsilyl group Chemical class [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 abstract 2
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 abstract 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 229910003691 SiBr Inorganic materials 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 239000005864 Sulphur Substances 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 201000011243 gastrointestinal stromal tumor Diseases 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 150000002431 hydrogen Chemical class 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 235000019371 penicillin G benzathine Nutrition 0.000 abstract 1
- 229940056360 penicillin g Drugs 0.000 abstract 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 abstract 1
- 125000005544 phthalimido group Chemical group 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 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
- C07D501/08—Preparation by forming the ring or condensed ring systems
- C07D501/10—Preparation by forming the ring or condensed ring systems from compounds containing the penicillin ring system
-
- 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)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- Molecular Biology (AREA)
- Cephalosporin Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
1409415 Silyl derivatives of penicillin sulphoxides GIST-BROCADES NV 15 Aug 1972 [17 Aug 1971 21 Dec 1971] 38637/71 and 59516/71 Heading C3S [Also in Division C2] Compounds IX in which R 1 is hydrogen or a group linked to the nitrogen atom by carbon or sulphur, R 2 is hydrogen, C 1-6 alkyl or phenyl-C 1-6 alkyl or NR 1 R 2 represents an optionally substituted heterocyclic group and R 3 is the group R 4 R 5 R 6 Si- (where R 4 , R 5 and R 6 each is C 1-6 alkyl optionally substituted by Cl or CN, C 5-3 cycloalkyl phenyl, phenyl-C 1-2 alkyl, C 1-6 alkoxy optionally substituted by Cl or MeO, C 1-6 alkylthio, phenoxy, phenoxy-C 1-2 alkoxy, halogen or 6-substituted-amino-penicillenic-sulphoxide-3-carbonyloxy or R 4 and R 5 together with Si form a ring or R 4 and R 6 together represent O or S) are prepared by reacting the corresponding acid with a compound capable of introducing the R 3 group. Compounds IX prepared are the trimethylsilyl and triethylsilyl derivatives of benzylpenicillin sulphoxide; the trimethylsilyl derivatives of 2-ethoxy naphthyl penicillin sulphoxide phthalimido penicillin sulphoxide, and benzenesulpho-amidomethyl penicillin sulphoxide and the compound formed by the reaction of SiBr 4 with benzyl penicillin sulphoxide.
[GB1409415A]
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3863771 | 1971-08-17 | ||
| GB5951671A GB1409415A (en) | 1971-08-17 | 1971-12-21 | Penicillin sulphoxides and their use in preparing delta3-7- substituted amino-descetoxy-cephalosporins |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE36638L true IE36638L (en) | 1973-02-17 |
| IE36638B1 IE36638B1 (en) | 1977-01-19 |
Family
ID=26263869
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE1136/72A IE36638B1 (en) | 1971-08-17 | 1972-08-15 | Penicillin sulphoxides and their use in preparing delta 3-7-substituted amino-desacetoxycephalosporins |
Country Status (25)
| Country | Link |
|---|---|
| JP (1) | JPS5438117B2 (en) |
| AR (1) | AR193426A1 (en) |
| AT (1) | AT336181B (en) |
| BE (1) | BE787618A (en) |
| CA (1) | CA1014146A (en) |
| CH (1) | CH576982A5 (en) |
| CS (1) | CS197212B2 (en) |
| DD (1) | DD100263A5 (en) |
| DE (2) | DE2240224C3 (en) |
| DK (1) | DK142174B (en) |
| ES (1) | ES405883A1 (en) |
| FI (1) | FI58643C (en) |
| FR (1) | FR2150785B1 (en) |
| GB (1) | GB1409415A (en) |
| HU (1) | HU169534B (en) |
| IE (1) | IE36638B1 (en) |
| IL (1) | IL40143A (en) |
| LU (1) | LU65904A1 (en) |
| NL (1) | NL177597C (en) |
| NO (2) | NO144153C (en) |
| PH (2) | PH13845A (en) |
| RO (1) | RO63401A (en) |
| SE (1) | SE404927B (en) |
| SU (1) | SU500754A3 (en) |
| YU (1) | YU39899B (en) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2222094A1 (en) * | 1972-05-05 | 1973-11-15 | Hoechst Ag | PROCESS FOR THE PRODUCTION OF AMINOACETIDINONES |
| GB1472866A (en) * | 1974-06-12 | 1977-05-11 | Farmaceutici Italia | Cephalosporins and intermediates therefor |
| GB1467355A (en) * | 1974-08-07 | 1977-03-16 | Lepetit Spa | Preparation of 6-aminopenicillanic acid 7-aminocephalospo ranic acid and derivatives thereof |
| ES431585A1 (en) * | 1974-11-02 | 1976-11-16 | Gema Sa | Process for the conversion of 6-aminopenicillanic acid (6-APA) in 7-aminodesacetoxycephalosporanic acid (7-ADCA) |
| PL94023B1 (en) * | 1974-12-18 | 1977-07-30 | Politechnika Gdanska | |
| GB1472864A (en) * | 1975-04-05 | 1977-05-11 | Farmaceutici Italia | Method of preparing cephalosporins |
| US4008231A (en) * | 1975-09-15 | 1977-02-15 | Eli Lilly And Company | Preparation of 3-methoxymethylcephalosporins |
| IT1063088B (en) * | 1976-06-01 | 1985-02-11 | Dobfar Spa | AZETIDINONIC DERIVATIVES AND PROCEDURE FOR THE PREPARATION OF CEPHALOSPORINE |
| US4426520A (en) | 1978-04-03 | 1984-01-17 | Bristol-Myers Company | 3-Carbamoyloxy-cepham-4-carboxylic acid derivatives |
| US4518773A (en) * | 1978-04-03 | 1985-05-21 | Bristol-Myers Company | "3-Carbamoyloxy cephalosporins" |
| US4310459A (en) * | 1978-04-03 | 1982-01-12 | Bristol-Myers Company | Process for producing carbamoyl substituted penams and carbamoyl substituted cephams from penicillin sulfoxide esters |
| US4322347A (en) | 1978-04-03 | 1982-03-30 | Bristol-Myers Company | 2-Carbamoyloxymethyl-penicillin derivatives |
| IT1124802B (en) * | 1979-10-29 | 1986-05-14 | Dobfar Spa | BORONATED DERIVATIVES OF 6-PENICILLANIC ACID AND PROCEDURE FOR THEIR PREPARATION |
| US4374982A (en) | 1979-11-07 | 1983-02-22 | Bristol-Myers Company | Cepham compounds |
| JPS5716006A (en) * | 1980-07-03 | 1982-01-27 | Mitsui Toatsu Chem Inc | Suspension polymerization of vinyl chloride |
-
0
- BE BE787618D patent/BE787618A/en not_active IP Right Cessation
-
1971
- 1971-12-21 GB GB5951671A patent/GB1409415A/en not_active Expired
-
1972
- 1972-08-03 SU SU1817032A patent/SU500754A3/en active
- 1972-08-15 IE IE1136/72A patent/IE36638B1/en unknown
- 1972-08-15 PH PH13802A patent/PH13845A/en unknown
- 1972-08-16 CH CH1216172A patent/CH576982A5/xx not_active IP Right Cessation
- 1972-08-16 IL IL40143A patent/IL40143A/en unknown
- 1972-08-16 DD DD165088A patent/DD100263A5/xx unknown
- 1972-08-16 FI FI2271/72A patent/FI58643C/en active
- 1972-08-16 CA CA149,545A patent/CA1014146A/en not_active Expired
- 1972-08-16 ES ES405883A patent/ES405883A1/en not_active Expired
- 1972-08-16 FR FR7229365A patent/FR2150785B1/fr not_active Expired
- 1972-08-16 DE DE2240224A patent/DE2240224C3/en not_active Expired
- 1972-08-16 AR AR243595A patent/AR193426A1/en active
- 1972-08-16 NO NO2942/72A patent/NO144153C/en unknown
- 1972-08-16 LU LU65904A patent/LU65904A1/xx unknown
- 1972-08-16 DK DK406072AA patent/DK142174B/en not_active IP Right Cessation
- 1972-08-16 YU YU2100/72A patent/YU39899B/en unknown
- 1972-08-16 SE SE7210625A patent/SE404927B/en unknown
- 1972-08-16 AT AT704072A patent/AT336181B/en not_active IP Right Cessation
- 1972-08-16 RO RO7200071975A patent/RO63401A/en unknown
- 1972-08-16 HU HUGI178A patent/HU169534B/hu unknown
- 1972-08-16 DE DE2264648*A patent/DE2264648A1/en active Pending
- 1972-08-16 JP JP8204972A patent/JPS5438117B2/ja not_active Expired
- 1972-08-16 CS CS725688A patent/CS197212B2/en unknown
- 1972-08-17 NL NLAANVRAGE7211213,A patent/NL177597C/en not_active IP Right Cessation
-
1973
- 1973-05-30 NO NO2262/73A patent/NO144152C/en unknown
-
1977
- 1977-12-06 PH PH20519A patent/PH15675A/en unknown
Also Published As
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