CH423782A - Verfahren zur Herstellung von Derivaten der 6-Aminopenicillansäure - Google Patents
Verfahren zur Herstellung von Derivaten der 6-AminopenicillansäureInfo
- Publication number
- CH423782A CH423782A CH306162A CH306162A CH423782A CH 423782 A CH423782 A CH 423782A CH 306162 A CH306162 A CH 306162A CH 306162 A CH306162 A CH 306162A CH 423782 A CH423782 A CH 423782A
- Authority
- CH
- Switzerland
- Prior art keywords
- aminopenicillanic acid
- formula
- acid
- compound
- trialkylsilyl
- Prior art date
Links
- NGHVIOIJCVXTGV-ALEPSDHESA-N 6-aminopenicillanic acid Chemical class [O-]C(=O)[C@H]1C(C)(C)S[C@@H]2[C@H]([NH3+])C(=O)N21 NGHVIOIJCVXTGV-ALEPSDHESA-N 0.000 title claims description 28
- 238000000034 method Methods 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title claims description 8
- NGHVIOIJCVXTGV-UHFFFAOYSA-N 6beta-amino-penicillanic acid Natural products OC(=O)C1C(C)(C)SC2C(N)C(=O)N21 NGHVIOIJCVXTGV-UHFFFAOYSA-N 0.000 claims description 24
- 150000001875 compounds Chemical class 0.000 claims description 22
- 239000002253 acid Substances 0.000 claims description 13
- 238000005917 acylation reaction Methods 0.000 claims description 10
- 230000010933 acylation Effects 0.000 claims description 8
- 239000011541 reaction mixture Substances 0.000 claims description 7
- 150000007513 acids Chemical class 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 238000003776 cleavage reaction Methods 0.000 claims description 2
- 230000007017 scission Effects 0.000 claims description 2
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 8
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Natural products 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 description 5
- -1 acyl radical Chemical class 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 4
- 239000012454 non-polar solvent Substances 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
- 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 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 229940056360 penicillin g Drugs 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000010703 silicon Substances 0.000 description 3
- 238000006884 silylation reaction Methods 0.000 description 3
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 229930182555 Penicillin Natural products 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 150000002960 penicillins Chemical class 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- LPHDUZQZGZACHZ-UHFFFAOYSA-N 1-(2,2-diphenylethenyl)piperidine;hydrochloride Chemical compound Cl.C1CCCCN1C=C(C=1C=CC=CC=1)C1=CC=CC=C1 LPHDUZQZGZACHZ-UHFFFAOYSA-N 0.000 description 1
- VMZCDNSFRSVYKQ-UHFFFAOYSA-N 2-phenylacetyl chloride Chemical compound ClC(=O)CC1=CC=CC=C1 VMZCDNSFRSVYKQ-UHFFFAOYSA-N 0.000 description 1
- 229910002621 H2PtCl6 Inorganic materials 0.000 description 1
- 241000295644 Staphylococcaceae Species 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000001263 acyl chlorides Chemical class 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 125000003460 beta-lactamyl group Chemical group 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- RBHJBMIOOPYDBQ-UHFFFAOYSA-N carbon dioxide;propan-2-one Chemical compound O=C=O.CC(C)=O RBHJBMIOOPYDBQ-UHFFFAOYSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 150000002561 ketenes Chemical class 0.000 description 1
- 150000003951 lactams Chemical group 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB0061834 | 1961-03-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH423782A true CH423782A (de) | 1966-11-15 |
Family
ID=6973349
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH306162A CH423782A (de) | 1961-03-23 | 1962-03-14 | Verfahren zur Herstellung von Derivaten der 6-Aminopenicillansäure |
Country Status (5)
| Country | Link |
|---|---|
| CH (1) | CH423782A (da) |
| DE (1) | DE1420981C3 (da) |
| DK (1) | DK130590B (da) |
| GB (1) | GB1008468A (da) |
| SE (1) | SE372535B (da) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4182709A (en) * | 1976-01-15 | 1980-01-08 | Glaxo Group Limited | Manufacture of semi-synthetic penicillin antibiotics |
| US4181656A (en) | 1976-01-15 | 1980-01-01 | 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/de not_active Expired
-
1962
- 1962-03-14 CH CH306162A patent/CH423782A/de 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/da unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK130590C (da) | 1975-08-11 |
| DK130590B (da) | 1975-03-10 |
| GB1008468A (en) | 1965-10-27 |
| DE1420981B2 (de) | 1975-05-15 |
| DE1420981A1 (de) | 1969-05-29 |
| DE1420981C3 (de) | 1976-01-02 |
| SE372535B (da) | 1974-12-23 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2758937C2 (da) | ||
| DE2759033C2 (de) | Verfahren zur Herstellung von 4-Hydroxypyrrolidin-2-on-1-ylalkylcarbonsäureamiden | |
| CH507970A (de) | Verfahren zur Herstellung neuer desacylierter mehrkerniger Indole sowie deren Verwendung | |
| DE3544601C2 (da) | ||
| DE1302847C2 (de) | Verfahren zur herstellung von alphaaminobenzylpenicillin | |
| DE1923624B2 (de) | Verfahren zur Herstellung von Penicillinen | |
| DE1420981C3 (de) | Verfahren zur Herstellung von 6-Acylaminopenicillansäuren | |
| CH649992A5 (de) | Verfahren zur herstellung von n-chlorcarbonyllactamen. | |
| DE1156809B (de) | Verfahren zur Herstellung von Cyanalkylfluorsilanen | |
| DE1770855C3 (de) | Verfahren zur Herstellung von N-Trialkylsilyl-6-aminopenicillansäuretrialkylsilylestern. Ausscheidung aus: 1420981 | |
| AT267051B (de) | Verfahren zur Herstellung von neuen N-Acyl-6-aminopenicillansäuren | |
| DE3142401A1 (de) | Aprosamin-derivate und diese verbindungen enthaltende arzneimittel | |
| EP0021391A1 (de) | Phosphonoameisensäurehydrazide, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Arzneimittel | |
| DE1445015C3 (de) | Verfahren zur Herstellung von Derivaten der 6-Aminopenicillansäure | |
| DE1292664B (de) | 1, 2, 3, 5, 6-Pentathiacycloheptan, Verfahren zu dessen Herstellung und Verwendung | |
| DE1645938A1 (de) | Verfahren zur Herstellung von 6-Aminopenicillansaeureestern | |
| DE1770858A1 (de) | Verfahren zur Herstellung von 6-Acylaminopenicillansaeuren | |
| DE1645949C3 (de) | 6-aminopenicillansaeureester und verfahren zu deren herstellung | |
| DE1770858C3 (de) | Verfahren zur Herstellung von e-Acylaminopenicillansäuren | |
| DE2014801A1 (de) | Verfahren zur Herstellung von Malonsäurenitrilderivaten | |
| CH628635A5 (en) | Process for the preparation of semisynthetic penicillin antibiotics | |
| DE1768860A1 (de) | Verfahren zur Herstellung von mono- und polyfunktionellen Derivaten der Kohlensaeure | |
| DE1445015B2 (de) | Verfahren zur Herstellung von Derivaten der 6-Aminopenicillansäure | |
| DE1035136B (de) | Verfahren zur Dehydrochlorierung von Chloralkylchlorsilanen | |
| CH421110A (de) | Verfahren zur Herstellung von Aminosäurederivaten |