IE33557L - Penicillins and cephalosporins - Google Patents
Penicillins and cephalosporinsInfo
- Publication number
- IE33557L IE33557L IE127169A IE127169A IE33557L IE 33557 L IE33557 L IE 33557L IE 127169 A IE127169 A IE 127169A IE 127169 A IE127169 A IE 127169A IE 33557 L IE33557 L IE 33557L
- Authority
- IE
- Ireland
- Prior art keywords
- residue
- acylamino
- penicillin
- electrophilic group
- give
- Prior art date
Links
- 229930182555 Penicillin Natural products 0.000 title abstract 5
- 229930186147 Cephalosporin Natural products 0.000 title 1
- 229940124587 cephalosporin Drugs 0.000 title 1
- 150000001780 cephalosporins Chemical class 0.000 title 1
- 150000002960 penicillins Chemical class 0.000 title 1
- 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 abstract 4
- 125000004442 acylamino group Chemical group 0.000 abstract 4
- 229940049954 penicillin Drugs 0.000 abstract 4
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 150000001408 amides Chemical group 0.000 abstract 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 2
- 125000005036 alkoxyphenyl group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
- 125000004122 cyclic group Chemical group 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
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 125000001624 naphthyl group Chemical group 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 abstract 1
- -1 sulphonamido Chemical group 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cephalosporin Compounds (AREA)
Abstract
Penicillin and cephalosporim derivs. M3A. Compds. (I) and (II) are of formula: (Where R' is an amide residue for a known natura or synthetic penicillin or cephalosposin, haloimide or alkoxy-imido derivs. of such an amide residue or amino. R18 is Me, HOCH2, N-pyridinium methyl or alkanocyl-methyl X is an electrophilic group, Y is an electrophilic group or a non-electrophilic group or X and Y together form a cyclic electrophilic group esp. a group: (where R16 and R17 are H, halogen, alkyl, alkoxy, phenyl phenylalkyl, alkoxyphenyl, aryl, heterocyclyl, CF3, NO2 dialkylamino, sulphonamido, carbalkoxy, CN, alkylthio, alkylsulphonyl or together with the benzene ring form a naphthyl residue). They are prepd. by reacting a penicillin or caphalosporin or a carboxylic acid deriv. thereof with an amine to form the 2-amide, then opt. reacting this with PCl5 and a base to form. (I) or (II) R' = haloimide residue, then with an alkanol to form (I) or (II) R' =alkoxy imido residue, hydrolysing to give (I) or (II) R' = NH2 and opt. acylating to give (I) or (II) R' = acylamino (different from the starting acylamino residue. (I) or (II) R' = acylamino (different from the starting acylamino residue). The process may be extended to include the hydrolysis of (I) or (II) to give the parent penicillin or sephalasporin.
[FR2018219A1]
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US76009068A | 1968-09-16 | 1968-09-16 | |
| GB4418468 | 1968-09-17 | ||
| US84378369A | 1969-07-22 | 1969-07-22 | |
| US84384169A | 1969-07-22 | 1969-07-22 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE33557L true IE33557L (en) | 1970-03-17 |
| IE33557B1 IE33557B1 (en) | 1974-08-07 |
Family
ID=27448973
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE127169A IE33557B1 (en) | 1968-09-16 | 1969-09-10 | Penicillin and cephalosporin derivatives and their preparation |
Country Status (11)
| Country | Link |
|---|---|
| AT (2) | AT318137B (en) |
| BE (1) | BE738929A (en) |
| CH (2) | CH535790A (en) |
| DE (1) | DE1946089A1 (en) |
| FR (1) | FR2018219A1 (en) |
| HU (1) | HU169474B (en) |
| IE (1) | IE33557B1 (en) |
| IL (1) | IL32964A (en) |
| IT (1) | IT1043789B (en) |
| NL (1) | NL6914029A (en) |
| SE (1) | SE388860B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| YU42533B (en) * | 1980-07-28 | 1988-10-31 | Pliva Pharm & Chem Works | Process for preparing penicilin n-acyl amides |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3177203A (en) * | 1961-12-08 | 1965-04-06 | Hoffmann La Roche | Penicillin derivatives |
| GB1061566A (en) * | 1962-12-04 | 1967-03-15 | Lepetit Spa | Phenoxymethyl penicillins |
| BE628493A (en) * | 1963-02-15 | |||
| BE628494A (en) * | 1963-02-15 | |||
| US3301811A (en) * | 1963-10-28 | 1967-01-31 | Bristol Myers Co | Nu-hydroxypenicillin amides |
| FR1394820A (en) * | 1964-02-13 | 1965-04-09 | Ciba Geigy | New process for the preparation of amino compounds, in particular 7-amino-cephalosporanic acid |
-
1969
- 1969-09-08 IL IL3296469Q patent/IL32964A/en unknown
- 1969-09-10 IE IE127169A patent/IE33557B1/en unknown
- 1969-09-11 DE DE19691946089 patent/DE1946089A1/en active Pending
- 1969-09-15 CH CH1392069A patent/CH535790A/en not_active IP Right Cessation
- 1969-09-15 HU HUAE000304 patent/HU169474B/hu unknown
- 1969-09-15 AT AT872569A patent/AT318137B/en not_active IP Right Cessation
- 1969-09-15 AT AT796771A patent/AT319467B/en not_active IP Right Cessation
- 1969-09-15 CH CH279972A patent/CH552009A/en not_active IP Right Cessation
- 1969-09-16 FR FR6931525A patent/FR2018219A1/en active Granted
- 1969-09-16 BE BE738929D patent/BE738929A/xx not_active IP Right Cessation
- 1969-09-16 NL NL6914029A patent/NL6914029A/xx not_active Application Discontinuation
- 1969-09-16 IT IT2212969A patent/IT1043789B/en active
- 1969-09-16 SE SE1275369A patent/SE388860B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE1946089A1 (en) | 1970-04-23 |
| IT1043789B (en) | 1980-02-29 |
| BE738929A (en) | 1970-03-16 |
| SE388860B (en) | 1976-10-18 |
| IE33557B1 (en) | 1974-08-07 |
| FR2018219B1 (en) | 1973-12-21 |
| HU169474B (en) | 1976-12-28 |
| AT319467B (en) | 1974-12-27 |
| CH535790A (en) | 1973-04-15 |
| CH552009A (en) | 1974-07-31 |
| AT318137B (en) | 1974-09-25 |
| IL32964A (en) | 1974-05-16 |
| FR2018219A1 (en) | 1970-05-29 |
| NL6914029A (en) | 1970-03-18 |
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