GB1008468A - N-substituted 6-amino penicillanic acids - Google Patents
N-substituted 6-amino penicillanic acidsInfo
- Publication number
- GB1008468A GB1008468A GB1104562A GB1104562A GB1008468A GB 1008468 A GB1008468 A GB 1008468A GB 1104562 A GB1104562 A GB 1104562A GB 1104562 A GB1104562 A GB 1104562A GB 1008468 A GB1008468 A GB 1008468A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- aminopenicillanic
- hydrogen
- group
- product
- 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
- 239000002253 acid Substances 0.000 title abstract 3
- 150000007513 acids Chemical class 0.000 title abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 6
- NGHVIOIJCVXTGV-ALEPSDHESA-N 6-aminopenicillanic acid Chemical compound [O-]C(=O)[C@H]1C(C)(C)S[C@@H]2[C@H]([NH3+])C(=O)N21 NGHVIOIJCVXTGV-ALEPSDHESA-N 0.000 abstract 4
- NGHVIOIJCVXTGV-UHFFFAOYSA-N 6beta-amino-penicillanic acid Natural products OC(=O)C1C(C)(C)SC2C(N)C(=O)N21 NGHVIOIJCVXTGV-UHFFFAOYSA-N 0.000 abstract 4
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 abstract 4
- 229910052739 hydrogen Inorganic materials 0.000 abstract 4
- 239000001257 hydrogen Substances 0.000 abstract 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract 2
- 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 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 230000007062 hydrolysis Effects 0.000 abstract 2
- 238000006460 hydrolysis reaction Methods 0.000 abstract 2
- 239000012454 non-polar solvent Substances 0.000 abstract 2
- QWFRRFLKWRIKSZ-UHFFFAOYSA-N truxillic acid Chemical compound OC(=O)C1C(C=2C=CC=CC=2)C(C(O)=O)C1C1=CC=CC=C1 QWFRRFLKWRIKSZ-UHFFFAOYSA-N 0.000 abstract 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 abstract 1
- VMZCDNSFRSVYKQ-UHFFFAOYSA-N 2-phenylacetyl chloride Chemical compound ClC(=O)CC1=CC=CC=C1 VMZCDNSFRSVYKQ-UHFFFAOYSA-N 0.000 abstract 1
- 229910002621 H2PtCl6 Inorganic materials 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 abstract 1
- 150000008065 acid anhydrides Chemical class 0.000 abstract 1
- 230000010933 acylation Effects 0.000 abstract 1
- 238000005917 acylation reaction Methods 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical group 0.000 abstract 1
- 150000002431 hydrogen Chemical group 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 abstract 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 abstract 1
- 239000012948 isocyanate Substances 0.000 abstract 1
- 150000002513 isocyanates Chemical class 0.000 abstract 1
- 150000002540 isothiocyanates Chemical class 0.000 abstract 1
- 150000002561 ketenes Chemical class 0.000 abstract 1
- 229910052763 palladium Inorganic materials 0.000 abstract 1
- 229940049954 penicillin Drugs 0.000 abstract 1
- 229940056360 penicillin g Drugs 0.000 abstract 1
- 229910052710 silicon Inorganic materials 0.000 abstract 1
- 239000010703 silicon Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/10—Compounds having one or more C—Si linkages containing nitrogen having a Si-N linkage
-
- 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
N - substituted 6 - aminopenicillanic acids are prepared by reacting 6-aminopenicillanic acid with silylating agents of general formula <FORM:1008468/C3/1> wherein R1,R2 and R3 which may be the same or different are alkyl or aryl groups and X is hydrogen, halogen, the group -NH-Si(R1)(R2)(R3) or the group -N=(R4)(R5) wherein R4 and R5\t which may be the same or different are hydrogen or alkyl groups. Preferably the reaction takes place in a non-proton active non-polar solvent and, in the absence of a proton active compound, at temperatures between room temperature and the boiling point of the silylating agent. Specified silylating agents are trialkylchlorosilanes, used in the presence of ammonia, and trialkylsilanes which are used in the presence of a catalyst, e.g. palladium or H2PtCl6. The examples describe the reaction of 6-aminopenicillanic acid with an excess of hexamethyldisilazane to give N-trimethylsilyl-6-aminopenicillanic acid trimethylsilyl ester.ALSO:Derivatives of 6-aminopenicillanic acid are prepared by reacting 6-aminopenicillanic acid with silylating agents of general formula <FORM:1008468/C2/1> wherein R1, R2 and R3 which may be the sam or different are alkyl or aryl groups and X is hydrogen; the group -NH-Si(R1)(R2)(R3) or the group -N(R4)(R5), wherein R4 and R5, which may be the same or different are hydrogen or alkyl groups, dissolving the product in excess of the silylating agent or in a non-polar solvent, acylating the silylated product and then removing the silicon containing groups by hydrolysis. Specified acylating agents are acid halides, acid anhydrides, ketenes, iso-cyanates and isothiocyanates. Acylation can take place in excess of the silylating agent without isolating the silylated 6-aminopenicillanic acid. Preferably an acid chloride is used in presence of a compound capable of fixing hydrogen chloride. In the examples, a solution of N-trimethylsilyl-6-aminopenicillanic acid trimethylsilyl ester in hexamethyldisilazane is reacted with (1) phenylacetic acid chloride in the presence of triethylamine at room temperature to 40 DEG C.; hydrolysis of the product with water giving penicillin G; and (2) truxillic acid chloride in the presence of triethylamine. The product was converted into truxillic acid-di-penicillin by exposure to the moisture in the air.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB0061834 | 1961-03-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1008468A true GB1008468A (en) | 1965-10-27 |
Family
ID=6973349
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1104562A Expired GB1008468A (en) | 1961-03-23 | 1962-03-22 | N-substituted 6-amino penicillanic acids |
Country Status (5)
| Country | Link |
|---|---|
| CH (1) | CH423782A (en) |
| DE (1) | DE1420981C3 (en) |
| DK (1) | DK130590B (en) |
| GB (1) | GB1008468A (en) |
| SE (1) | SE372535B (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4181656A (en) | 1976-01-15 | 1980-01-01 | Glaxo Group Limited | Manufacture of semi-synthetic penicillin antibiotics |
| US4182709A (en) * | 1976-01-15 | 1980-01-08 | Glaxo Group Limited | Manufacture of semi-synthetic penicillin antibiotics |
| US4240960A (en) * | 1979-03-19 | 1980-12-23 | Bristol-Myers Company | Trimethylsilyl substituted penicillins |
| US4278600A (en) | 1979-03-19 | 1981-07-14 | Bristol-Myers Company | Production of penicillins |
| US4310458A (en) | 1979-03-19 | 1982-01-12 | Bristol-Myers Company | Production of penicillins |
| US4351766A (en) * | 1979-07-12 | 1982-09-28 | Bristol-Myers Company | Production of penicillins |
| US7230097B2 (en) | 2003-03-10 | 2007-06-12 | Lupin Ltd. | Process for preparation of 7-[α-Amino (4-hydroxyphenyl) acetamido]-3-substituted-3-cephem-4-carboxylic acid |
-
1961
- 1961-03-23 DE DE19611420981 patent/DE1420981C3/en not_active Expired
-
1962
- 1962-03-14 CH CH306162A patent/CH423782A/en unknown
- 1962-03-22 GB GB1104562A patent/GB1008468A/en not_active Expired
- 1962-03-23 SE SE327362A patent/SE372535B/xx unknown
- 1962-03-23 DK DK134762A patent/DK130590B/en unknown
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4181656A (en) | 1976-01-15 | 1980-01-01 | Glaxo Group Limited | Manufacture of semi-synthetic penicillin antibiotics |
| US4182709A (en) * | 1976-01-15 | 1980-01-08 | Glaxo Group Limited | Manufacture of semi-synthetic penicillin antibiotics |
| US4240960A (en) * | 1979-03-19 | 1980-12-23 | Bristol-Myers Company | Trimethylsilyl substituted penicillins |
| US4278600A (en) | 1979-03-19 | 1981-07-14 | Bristol-Myers Company | Production of penicillins |
| US4310458A (en) | 1979-03-19 | 1982-01-12 | Bristol-Myers Company | Production of penicillins |
| US4351766A (en) * | 1979-07-12 | 1982-09-28 | Bristol-Myers Company | Production of penicillins |
| US7230097B2 (en) | 2003-03-10 | 2007-06-12 | Lupin Ltd. | Process for preparation of 7-[α-Amino (4-hydroxyphenyl) acetamido]-3-substituted-3-cephem-4-carboxylic acid |
| US7427692B2 (en) | 2003-03-10 | 2008-09-23 | Lupin Ltd. | Process for preparation of 7-[α-amino (4-hydroxyphenyl) acetamido]-3-substituted-3-cephem-4-carboxylic acid |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1420981A1 (en) | 1969-05-29 |
| SE372535B (en) | 1974-12-23 |
| DK130590B (en) | 1975-03-10 |
| DE1420981C3 (en) | 1976-01-02 |
| DK130590C (en) | 1975-08-11 |
| CH423782A (en) | 1966-11-15 |
| DE1420981B2 (en) | 1975-05-15 |
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