DE1795537A1 - Penicilline mit einer geschuetzten Aminogruppe,deren Salze und Verfahren zu ihrer Herstellung - Google Patents
Penicilline mit einer geschuetzten Aminogruppe,deren Salze und Verfahren zu ihrer HerstellungInfo
- Publication number
- DE1795537A1 DE1795537A1 DE19661795537 DE1795537A DE1795537A1 DE 1795537 A1 DE1795537 A1 DE 1795537A1 DE 19661795537 DE19661795537 DE 19661795537 DE 1795537 A DE1795537 A DE 1795537A DE 1795537 A1 DE1795537 A1 DE 1795537A1
- Authority
- DE
- Germany
- Prior art keywords
- penicillins
- salts
- carboxylic acid
- amino group
- protected amino
- 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.)
- Pending
Links
- 150000003839 salts Chemical class 0.000 title claims description 13
- 229930182555 Penicillin Natural products 0.000 title claims description 10
- 150000002960 penicillins Chemical class 0.000 title claims description 10
- 125000003277 amino group Chemical group 0.000 title claims description 8
- 238000000034 method Methods 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 159000000000 sodium salts Chemical class 0.000 claims description 4
- 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 claims description 3
- 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 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 150000008064 anhydrides Chemical class 0.000 claims description 2
- 150000001718 carbodiimides Chemical class 0.000 claims description 2
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 239000013067 intermediate product Substances 0.000 claims 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 239000000203 mixture Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 240000008415 Lactuca sativa Species 0.000 description 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 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 235000012045 salad Nutrition 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 1
- XXQGYGJZNMSSFD-UHFFFAOYSA-N 2-[2-(dimethylcarbamoyl)phenoxy]acetic acid Chemical compound CN(C)C(=O)C1=CC=CC=C1OCC(O)=O XXQGYGJZNMSSFD-UHFFFAOYSA-N 0.000 description 1
- 241001136792 Alle Species 0.000 description 1
- 102100022443 CXADR-like membrane protein Human genes 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical class [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- BWLUMTFWVZZZND-UHFFFAOYSA-N Dibenzylamine Chemical compound C=1C=CC=CC=1CNCC1=CC=CC=C1 BWLUMTFWVZZZND-UHFFFAOYSA-N 0.000 description 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical class 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 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical class [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 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 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Chemical class 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical class [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000011575 calcium Chemical class 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- RBKMMJSQKNKNEV-RITPCOANSA-N penicillanic acid Chemical compound OC(=O)[C@H]1C(C)(C)S[C@@H]2CC(=O)N21 RBKMMJSQKNKNEV-RITPCOANSA-N 0.000 description 1
- 235000019371 penicillin G benzathine Nutrition 0.000 description 1
- 229940056360 penicillin g Drugs 0.000 description 1
- 239000011591 potassium Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 229960004919 procaine Drugs 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000012048 reactive intermediate Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000005270 trialkylamine group Chemical group 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
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/195—Antibiotics
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Polymers & Plastics (AREA)
- Animal Husbandry (AREA)
- Zoology (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cephalosporin Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB11464/65A GB1066107A (en) | 1965-03-18 | 1965-03-18 | Process for the preparation of penicillins |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1795537A1 true DE1795537A1 (de) | 1972-01-13 |
Family
ID=9986731
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19661670058 Pending DE1670058A1 (de) | 1965-03-18 | 1966-03-14 | Verfahren zur Herstellung von Aminoacylpenicillinen |
| DE19661795537 Pending DE1795537A1 (de) | 1965-03-18 | 1966-03-14 | Penicilline mit einer geschuetzten Aminogruppe,deren Salze und Verfahren zu ihrer Herstellung |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19661670058 Pending DE1670058A1 (de) | 1965-03-18 | 1966-03-14 | Verfahren zur Herstellung von Aminoacylpenicillinen |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3372158A (OSRAM) |
| AT (1) | AT274234B (OSRAM) |
| BE (1) | BE677991A (OSRAM) |
| BR (1) | BR6677623D0 (OSRAM) |
| CH (1) | CH464928A (OSRAM) |
| DE (2) | DE1670058A1 (OSRAM) |
| GB (1) | GB1066107A (OSRAM) |
| NL (1) | NL6603044A (OSRAM) |
| SE (1) | SE328891B (OSRAM) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2985648A (en) * | 1958-10-06 | 1961-05-23 | Doyle Frank Peter | Alpha-aminobenzylpenicillins |
-
1965
- 1965-03-18 GB GB11464/65A patent/GB1066107A/en not_active Expired
-
1966
- 1966-03-04 US US531738A patent/US3372158A/en not_active Expired - Lifetime
- 1966-03-08 NL NL6603044A patent/NL6603044A/xx unknown
- 1966-03-08 BR BR177623/66A patent/BR6677623D0/pt unknown
- 1966-03-10 CH CH348866A patent/CH464928A/de unknown
- 1966-03-14 DE DE19661670058 patent/DE1670058A1/de active Pending
- 1966-03-14 DE DE19661795537 patent/DE1795537A1/de active Pending
- 1966-03-15 SE SE03427/66A patent/SE328891B/xx unknown
- 1966-03-16 AT AT248166A patent/AT274234B/de active
- 1966-03-17 BE BE677991D patent/BE677991A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL6603044A (OSRAM) | 1966-09-19 |
| DE1670058A1 (de) | 1970-11-05 |
| BE677991A (OSRAM) | 1966-09-19 |
| GB1066107A (en) | 1967-04-19 |
| CH464928A (de) | 1968-11-15 |
| BR6677623D0 (pt) | 1973-09-11 |
| SE328891B (OSRAM) | 1970-09-28 |
| AT274234B (de) | 1969-09-10 |
| US3372158A (en) | 1968-03-05 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1670218A1 (de) | Neue Penicilline und Verfahren zu ihrer Herstellung | |
| DE2147023A1 (de) | Verfahren zur herstellung von 1htetrazol-verbindungen | |
| DE1670523A1 (de) | Verfahren zur Herstellung neuer substituierter Aminopyridine | |
| DE1966974A1 (de) | Dimethylformiminiumhalogensulfit- n-halogenide, verfahren zu deren herstellung sowie deren verwendung | |
| DE2308305A1 (de) | Verfahren zur herstellung von 4-hydroxy-3-(5-methyl-3-isoxazolylcarbamoyl)2-methyl-2h-1,2-benzothiazin-1,1-dioxid | |
| DE2225149C2 (de) | Oxofurylesterderivate der 6-(ą-Aminophenylacetamido)penicillansäure, Verfahren zu deren Herstellung und ihre Verwendung | |
| DE1795537A1 (de) | Penicilline mit einer geschuetzten Aminogruppe,deren Salze und Verfahren zu ihrer Herstellung | |
| DE1545897A1 (de) | Verfahren zur Acylierung von Verbindungen der Cephalosporinreihe | |
| DE1470070B1 (de) | Verfahren zur Herstellung von Benzimidazolderivaten | |
| DE2166561A1 (de) | 6-aminopenicillansulfoxidsilylester | |
| DE1795868C3 (de) | Verfahren zur Herstellung von 7-Aminocephalosporansäure aus Cephalosporin C oder seinen Salzen in Gegenwart von Silylierungsmitteln | |
| DE1211156B (de) | Verfahren zur Herstellung von ungesaettigten Sulfonsaeurebetainen durch Umsetzen eines tertiaeren Amins mit einem Sulton | |
| DE2605563A1 (de) | Verfahren zur herstellung von d-penicillamin und substituierten 3-pyrazolin- 5-onen | |
| DE2240442A1 (de) | Verfahren zur herstellung von aminopenicillinen | |
| AT271723B (de) | Verfahren zur Herstellung von neuen Derivaten der 6-Aminopenicillansäure | |
| AT311974B (de) | Verfahren zur Herstellung neuer Sulfanilamide | |
| DE1670677C (de) | Verfahren zur Herstellung von 3,1-Benzothiazinen | |
| AT234695B (de) | Verfahren zur Herstellung von neuen 4-Chinazolinonen | |
| AT233173B (de) | Verfahren zur Herstellung neuer Äther | |
| AT314081B (de) | Verfahren zur Herstellung von Penicillinen | |
| AT258910B (de) | Verfahren zur Herstellung von Benzo-dihydro-thiadiazin-Derivaten | |
| DE1545608A1 (de) | Neue Penicilline und Verfahren zu ihrer Herstellung | |
| DE1470083C (de) | Cinnamylpenicilline und Verfahren zu ihrer Herstellung | |
| DE1595980C3 (de) | Phosphorsäureester des 4H-m-Dioxinoeckige Klammer auf 4,5-c eckige Klammer zu -pyridins, deren Herstellung und Verwendung | |
| DE820735C (de) | Verfahren zur Herstellung von Harnstoffderivaten |