CH525237A - Verfahren zur Herstellung von Penicillinen - Google Patents
Verfahren zur Herstellung von PenicillinenInfo
- Publication number
- CH525237A CH525237A CH570868A CH570868A CH525237A CH 525237 A CH525237 A CH 525237A CH 570868 A CH570868 A CH 570868A CH 570868 A CH570868 A CH 570868A CH 525237 A CH525237 A CH 525237A
- Authority
- CH
- Switzerland
- Prior art keywords
- phenyl
- benzylpenicillin
- salts
- alkoxy
- hydrolysis
- Prior art date
Links
- 229930182555 Penicillin Natural products 0.000 title claims abstract description 11
- 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 title abstract description 22
- 229940049954 penicillin Drugs 0.000 title abstract description 4
- 230000000844 anti-bacterial effect Effects 0.000 title abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 15
- 150000003839 salts Chemical class 0.000 claims abstract description 14
- 231100000252 nontoxic Toxicity 0.000 claims abstract description 9
- 230000003000 nontoxic effect Effects 0.000 claims abstract description 9
- 125000002541 furyl group Chemical group 0.000 claims abstract description 3
- 125000001544 thienyl group Chemical group 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 12
- 230000007062 hydrolysis Effects 0.000 claims description 11
- 238000006460 hydrolysis reaction Methods 0.000 claims description 11
- 150000002960 penicillins Chemical class 0.000 claims description 11
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 9
- 229910021538 borax Inorganic materials 0.000 claims description 8
- 235000010339 sodium tetraborate Nutrition 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
- 125000005140 aralkylsulfonyl group Chemical group 0.000 claims description 4
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 claims description 4
- 125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000002619 bicyclic group Chemical group 0.000 claims description 2
- 125000006371 dihalo methyl group Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical group [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 claims description 2
- 125000002950 monocyclic group Chemical group 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000004953 trihalomethyl group Chemical group 0.000 claims description 2
- BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 230000001419 dependent effect Effects 0.000 claims 1
- 229940056360 penicillin g Drugs 0.000 abstract description 29
- 235000019371 penicillin G benzathine Nutrition 0.000 abstract description 10
- 150000001412 amines Chemical class 0.000 abstract description 4
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 abstract description 3
- 150000003863 ammonium salts Chemical class 0.000 abstract description 3
- 150000001875 compounds Chemical class 0.000 abstract description 3
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 3
- BWLUMTFWVZZZND-UHFFFAOYSA-N Dibenzylamine Chemical compound C=1C=CC=CC=1CNCC1=CC=CC=C1 BWLUMTFWVZZZND-UHFFFAOYSA-N 0.000 abstract description 2
- 241000589516 Pseudomonas Species 0.000 abstract description 2
- JVVXZOOGOGPDRZ-SLFFLAALSA-N [(1R,4aS,10aR)-1,4a-dimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthren-1-yl]methanamine Chemical compound NC[C@]1(C)CCC[C@]2(C)C3=CC=C(C(C)C)C=C3CC[C@H]21 JVVXZOOGOGPDRZ-SLFFLAALSA-N 0.000 abstract description 2
- UPABQMWFWCMOFV-UHFFFAOYSA-N benethamine Chemical compound C=1C=CC=CC=1CNCCC1=CC=CC=C1 UPABQMWFWCMOFV-UHFFFAOYSA-N 0.000 abstract description 2
- JUHORIMYRDESRB-UHFFFAOYSA-N benzathine Chemical compound C=1C=CC=CC=1CNCCNCC1=CC=CC=C1 JUHORIMYRDESRB-UHFFFAOYSA-N 0.000 abstract description 2
- 208000015181 infectious disease Diseases 0.000 abstract description 2
- 229910052751 metal Inorganic materials 0.000 abstract description 2
- 239000002184 metal Substances 0.000 abstract description 2
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 abstract description 2
- 229960004919 procaine Drugs 0.000 abstract description 2
- 125000005270 trialkylamine group Chemical group 0.000 abstract description 2
- -1 araloxy Chemical group 0.000 description 24
- 229960003669 carbenicillin Drugs 0.000 description 16
- 239000000243 solution Substances 0.000 description 15
- 238000004816 paper chromatography Methods 0.000 description 11
- 159000000000 sodium salts Chemical class 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- 239000007787 solid Substances 0.000 description 9
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 229920006395 saturated elastomer Polymers 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 239000004328 sodium tetraborate Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- FPPNZSSZRUTDAP-UWFZAAFLSA-N carbenicillin Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)C(C(O)=O)C1=CC=CC=C1 FPPNZSSZRUTDAP-UWFZAAFLSA-N 0.000 description 3
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 125000004104 aryloxy group Chemical group 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 125000006678 phenoxycarbonyl group Chemical group 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- OHKOGUYZJXTSFX-KZFFXBSXSA-N ticarcillin Chemical compound C=1([C@@H](C(O)=O)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)C=CSC=1 OHKOGUYZJXTSFX-KZFFXBSXSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- YJLUBHOZZTYQIP-UHFFFAOYSA-N 2-[5-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-1,3,4-oxadiazol-2-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1=NN=C(O1)CC(=O)N1CC2=C(CC1)NN=N2 YJLUBHOZZTYQIP-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 239000006286 aqueous extract Substances 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 150000003952 β-lactams Chemical class 0.000 description 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cephalosporin Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1770267A GB1197973A (en) | 1967-04-18 | 1967-04-18 | Penicillins |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH525237A true CH525237A (de) | 1972-07-15 |
Family
ID=10099714
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH570868A CH525237A (de) | 1967-04-18 | 1968-04-18 | Verfahren zur Herstellung von Penicillinen |
Country Status (11)
| Country | Link |
|---|---|
| JP (1) | JPS5118434B1 (forum.php) |
| AT (1) | AT283591B (forum.php) |
| BE (1) | BE713868A (forum.php) |
| CH (1) | CH525237A (forum.php) |
| DK (1) | DK132796C (forum.php) |
| ES (1) | ES352849A1 (forum.php) |
| FI (1) | FI51813C (forum.php) |
| FR (1) | FR1560842A (forum.php) |
| GB (1) | GB1197973A (forum.php) |
| IE (1) | IE32038B1 (forum.php) |
| NL (1) | NL6805524A (forum.php) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2635477A1 (de) * | 1975-08-20 | 1977-03-03 | Beecham Group Ltd | Verfahren zur herstellung fester, praktisch reiner natrium- und kaliumsalze der clavulansaeure |
| US4598074A (en) * | 1982-10-15 | 1986-07-01 | Beecham Group P.L.C. | β-lactam antibiotics |
-
1967
- 1967-04-18 GB GB1770267A patent/GB1197973A/en not_active Expired
-
1968
- 1968-04-10 IE IE42268A patent/IE32038B1/xx unknown
- 1968-04-16 FR FR1560842D patent/FR1560842A/fr not_active Expired
- 1968-04-17 DK DK170368A patent/DK132796C/da active
- 1968-04-17 ES ES352849A patent/ES352849A1/es not_active Expired
- 1968-04-17 AT AT372468A patent/AT283591B/de not_active IP Right Cessation
- 1968-04-18 FI FI107268A patent/FI51813C/fi active
- 1968-04-18 BE BE713868D patent/BE713868A/xx unknown
- 1968-04-18 JP JP2611868A patent/JPS5118434B1/ja active Pending
- 1968-04-18 CH CH570868A patent/CH525237A/de not_active IP Right Cessation
- 1968-04-18 NL NL6805524A patent/NL6805524A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES352849A1 (es) | 1969-08-01 |
| BE713868A (forum.php) | 1968-10-18 |
| DK132796B (da) | 1976-02-09 |
| FR1560842A (forum.php) | 1969-03-21 |
| GB1197973A (en) | 1970-07-08 |
| DE1770225B2 (de) | 1976-03-25 |
| IE32038B1 (en) | 1973-03-21 |
| DK132796C (da) | 1976-07-12 |
| JPS5118434B1 (forum.php) | 1976-06-09 |
| DE1770225A1 (de) | 1971-10-07 |
| FI51813B (forum.php) | 1976-12-31 |
| AT283591B (de) | 1970-08-10 |
| IE32038L (en) | 1968-10-18 |
| NL6805524A (forum.php) | 1968-10-21 |
| FI51813C (fi) | 1977-04-12 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE3212900C2 (forum.php) | ||
| CH633558A5 (de) | Verfahren zur herstellung neuer cephalosporinderivate. | |
| DE1295558B (de) | ª-Carboxybenzyl- und ª-Carboxythienylmethylpenicilline und Verfahren zu ihrer Herstellung | |
| DE2324272A1 (de) | 3-methylencephalosporine | |
| CH525237A (de) | Verfahren zur Herstellung von Penicillinen | |
| DE1670222C3 (de) | a-(Benzyloxycarbonyl)-thienyunethylpenicilline und deren Salze, Verfahren zu deren Herstellung und diese Verbindungen enthaltende antibakterielle Mittel | |
| DE2145354C3 (de) | Thioester und Verfahren zu ihrer Herstellung | |
| DE1289053B (de) | ª‡-Hydroxy-2-thienylmethyl-penicilline und Verfahren zur ihrer Herstellung | |
| DE2033090C3 (de) | deren Herstellung | |
| CH498865A (de) | Verfahren zur Herstellung von Derivaten der 7-Aminocephalosporansäure | |
| DE1770225C3 (de) | Verfahren zur Herstellung von Penicillinen | |
| DE2841363C2 (forum.php) | ||
| AT226366B (de) | Verfahren zur Herstellung von neuen Penicillinderivaten | |
| AT229487B (de) | Verfahren zur Herstellung von neuen antibakteriellen Mitteln | |
| DE1595980C3 (de) | Phosphorsäureester des 4H-m-Dioxinoeckige Klammer auf 4,5-c eckige Klammer zu -pyridins, deren Herstellung und Verwendung | |
| AT259132B (de) | Verfahren zur Herstellung von neuen Penicillinderivaten | |
| DE1670378C (de) | Verfahren zur Herstellung des Salzes aus4-n-Butyl-3,5-dioxo-l,2-diphenylpyrazolidin und dem beta-Diäthylamino-äthylamid der p-Chlorphenoxyessigsäure | |
| DE69915498T2 (de) | 3-(hydroxymethyl)chromen-4-one und verfahren zu deren herstellung | |
| AT368510B (de) | Verfahren zur herstellung von neuen 3-phosphonocarbamoyloxymethylcephalosporinverbindungen | |
| AT267749B (de) | Verfahren zur Herstellung von neuen Penicillinderivaten und zu deren allfälliger Rückführung in die gereinigten Ausgangspenicilline | |
| AT275036B (de) | Verfahren zur Herstellung von neuen Derivaten der 7-Aminocephalosporansäure | |
| CH403766A (de) | Verfahren zur Herstellung von Penicillinen | |
| CH417598A (de) | Verfahren zur Herstellung von Penicillinen | |
| CH401976A (de) | Verfahren zur Herstellung von Penicillinderivaten | |
| CH477475A (de) | Verfahren zur Herstellung von neuen Derivaten der 6-Amino-penicillansäure |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |