IE39344L - 7ó-alkoxy cephalosporanates and corresponding¹penicillanates - Google Patents
7ó-alkoxy cephalosporanates and corresponding¹penicillanatesInfo
- Publication number
- IE39344L IE39344L IE740556A IE55674A IE39344L IE 39344 L IE39344 L IE 39344L IE 740556 A IE740556 A IE 740556A IE 55674 A IE55674 A IE 55674A IE 39344 L IE39344 L IE 39344L
- Authority
- IE
- Ireland
- Prior art keywords
- butyl
- benzyl
- benzylideneamino
- reacted
- amino
- Prior art date
Links
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 abstract 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 3
- FOIXSVOLVBLSDH-UHFFFAOYSA-N Silver ion Chemical compound [Ag+] FOIXSVOLVBLSDH-UHFFFAOYSA-N 0.000 abstract 2
- 125000002252 acyl group Chemical group 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000005233 alkylalcohol group Chemical group 0.000 abstract 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 abstract 2
- 238000000354 decomposition reaction Methods 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- 238000006467 substitution reaction Methods 0.000 abstract 2
- 229930186147 Cephalosporin Natural products 0.000 abstract 1
- 229930182555 Penicillin Chemical class 0.000 abstract 1
- 229940124587 cephalosporin Drugs 0.000 abstract 1
- 150000001780 cephalosporins Chemical class 0.000 abstract 1
- 150000002148 esters Chemical group 0.000 abstract 1
- 150000003840 hydrochlorides Chemical class 0.000 abstract 1
- 230000002452 interceptive effect Effects 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- BQPIGGFYSBELGY-UHFFFAOYSA-N mercury(2+) Chemical compound [Hg+2] BQPIGGFYSBELGY-UHFFFAOYSA-N 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 abstract 1
- 150000002960 penicillins Chemical class 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- 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)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
1439898 Alkoxy-substituted cephalosporins and penicillins SMITHKLINE CORP 12 March 1974 [15 March 1973] 10871/74 Heading C2C A compound of the formula wherein R is hydrogen or acyl; R<SP>1</SP> is C 1-6 alkyl; Z is R<SP>2</SP> is hydrogen, or an easily removable ester protecting group; and A is a non-interfering group, is prepared (a) when R is H, by treating a compound of the formula wherein R<SP>3</SP> is C 1-6 alkyl, with a C 1-6 alkyl alcohol in the presence of a mercuric or silver ion in a compatible solvent at a temperature and for a length of time to cause substitution without decomposition, or (b) when R is acyl, treating a compound of the formula with a C 1-6 alkyl alcohol in the presence of a silver ion in a compatible solvent at a temperature and for a length of time to cause substitution without significant decomposition. Preparation of intermediates is described as follows: t-butyl 7#-benzylideneamino-desacetoxycephalosporanate is reacted with methyl methanethiosulphate and NaH to give t-butyl 7# - benzylideneamine - 7α - methylthiodesacetoxycephalosporanate which is treated with HC1 to form t-butyl 7#-amino-7α-methylthiodesacetoxycephalosporanate and its HCl salt; t-butyl 7#-aminocephalosporanate and benzaldehyde are reacted to form t-butyl 7#- benzylideneaminocephalosporanate which is reacted as above to form t-butyl 7#-benzylideneamino - 7α - methylthiocephalosporanate which is converted to t-butyl 7#-amino-7α- methylthiocephalosporanate; benzyl 6#- aminopenicillanate is similarly converted to benzyl 6# - benzylideneaminopenicillanate; benzyl 6# - benzylideneamino - 6α - methylthiopenicillanate; benzyl 6# - amino - 6α- methylthiopenicillanate and its p-toluenesulphonic acid salt.
[GB1439898A]
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US34142673A | 1973-03-15 | 1973-03-15 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE39344L true IE39344L (en) | 1974-09-15 |
| IE39344B1 IE39344B1 (en) | 1978-09-27 |
Family
ID=23337520
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE556/74A IE39344B1 (en) | 1973-03-15 | 1974-03-14 | Method of preparing substituted cephalosporins and penicillins |
Country Status (8)
| Country | Link |
|---|---|
| JP (2) | JPS6046116B2 (en) |
| BE (1) | BE811314A (en) |
| CH (1) | CH605976A5 (en) |
| DE (1) | DE2412598C2 (en) |
| FR (1) | FR2221455B1 (en) |
| GB (1) | GB1439898A (en) |
| IE (1) | IE39344B1 (en) |
| NL (1) | NL7403515A (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4165429A (en) * | 1976-06-28 | 1979-08-21 | Yamanouchi Pharmaceutical Co., Ltd. | 7α-METHOXY-CEPHALOSPORANIC ACID DERIVATIVES |
| ZA80905B (en) * | 1979-03-01 | 1981-02-25 | Beecham Group Ltd | Penicillin derivatives |
| JO1395B1 (en) * | 1981-07-10 | 1986-11-30 | بيتشام جروب بي ال سي | Process for the preparation of penam derivatives |
| JO1228B1 (en) * | 1982-01-22 | 1985-04-20 | بيتشام جروب بي ال سي | Process for the preparation of penam derivatives |
| JPS6372698U (en) * | 1986-10-28 | 1988-05-16 |
-
1974
- 1974-02-20 BE BE141163A patent/BE811314A/en not_active IP Right Cessation
- 1974-03-06 CH CH316374A patent/CH605976A5/xx not_active IP Right Cessation
- 1974-03-12 GB GB1087174A patent/GB1439898A/en not_active Expired
- 1974-03-13 JP JP49029571A patent/JPS6046116B2/en not_active Expired
- 1974-03-14 FR FR7408669A patent/FR2221455B1/fr not_active Expired
- 1974-03-14 IE IE556/74A patent/IE39344B1/en unknown
- 1974-03-15 NL NL7403515A patent/NL7403515A/xx not_active Application Discontinuation
- 1974-03-15 DE DE2412598A patent/DE2412598C2/en not_active Expired
-
1981
- 1981-08-18 JP JP56130035A patent/JPS585199B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2221455A1 (en) | 1974-10-11 |
| JPS6046116B2 (en) | 1985-10-14 |
| BE811314A (en) | 1974-08-20 |
| FR2221455B1 (en) | 1978-07-07 |
| JPS585199B2 (en) | 1983-01-29 |
| DE2412598A1 (en) | 1974-09-26 |
| NL7403515A (en) | 1974-09-17 |
| JPS5775985A (en) | 1982-05-12 |
| CH605976A5 (en) | 1978-10-13 |
| JPS49125390A (en) | 1974-11-30 |
| DE2412598C2 (en) | 1983-06-16 |
| GB1439898A (en) | 1976-06-16 |
| IE39344B1 (en) | 1978-09-27 |
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