GB1246495A - Penicillins and their production - Google Patents
Penicillins and their productionInfo
- Publication number
- GB1246495A GB1246495A GB59874/68A GB5987468A GB1246495A GB 1246495 A GB1246495 A GB 1246495A GB 59874/68 A GB59874/68 A GB 59874/68A GB 5987468 A GB5987468 A GB 5987468A GB 1246495 A GB1246495 A GB 1246495A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- formula
- acid
- penicillin
- penicillins
- 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
- 229930182555 Penicillin Natural products 0.000 title abstract 6
- 150000002960 penicillins Chemical class 0.000 title abstract 4
- 125000000217 alkyl group Chemical group 0.000 abstract 7
- 125000003118 aryl group Chemical group 0.000 abstract 4
- 125000000623 heterocyclic group Chemical group 0.000 abstract 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 3
- 125000005842 heteroatom Chemical group 0.000 abstract 3
- 150000003839 salts Chemical class 0.000 abstract 3
- AVKUERGKIZMTKX-YXLKDIQASA-N (2s,5r)-6-[(2-amino-2-phenylacetyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid Chemical compound C1([C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)NC(=O)C(N)C1=CC=CC=C1 AVKUERGKIZMTKX-YXLKDIQASA-N 0.000 abstract 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-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
- 239000002253 acid Substances 0.000 abstract 2
- 229910052799 carbon Inorganic materials 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 231100000252 nontoxic Toxicity 0.000 abstract 2
- 230000003000 nontoxic effect Effects 0.000 abstract 2
- 229940049954 penicillin Drugs 0.000 abstract 2
- 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 1
- 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 1
- KNIUHBNRWZGIQQ-UHFFFAOYSA-N 7-diethoxyphosphinothioyloxy-4-methylchromen-2-one Chemical compound CC1=CC(=O)OC2=CC(OP(=S)(OCC)OCC)=CC=C21 KNIUHBNRWZGIQQ-UHFFFAOYSA-N 0.000 abstract 1
- 241000283690 Bos taurus Species 0.000 abstract 1
- 239000004471 Glycine Substances 0.000 abstract 1
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 abstract 1
- 241001465754 Metazoa Species 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- -1 acyl isothiocyanate Chemical class 0.000 abstract 1
- 239000000654 additive Substances 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- OJKZEZMAPKWHTG-UHFFFAOYSA-N bis(2h-triazol-4-yl)methanone Chemical compound C=1NN=NC=1C(=O)C1=CNN=N1 OJKZEZMAPKWHTG-UHFFFAOYSA-N 0.000 abstract 1
- 150000001718 carbodiimides Chemical class 0.000 abstract 1
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000004122 cyclic group Chemical group 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 230000004151 fermentation Effects 0.000 abstract 1
- 238000000855 fermentation Methods 0.000 abstract 1
- 208000004396 mastitis Diseases 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical class OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 abstract 1
- 239000005051 trimethylchlorosilane Substances 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1,246,495. Penicillins. FARBENFABRIKEN BAYER A.G. 17 Dec., 1968 [18 Dec., 1967], No. 59874/68. Heading C2A. Novel penicillins of the general formula wherein R 1 is a nitrile radical or an acyl radical of 1-26 carbon atoms including the carboxyl carbon atom; R 2 is H, alkyl, alkyl substituted or interrupted by a heteroatom, a cycloaliphatic, aromatic or araliphatic moiety or a heterocycle; R 3 is H, alkyl, alkyl substituted or interrupted by a heteroatom, a cycloaliphatic. aromatic or araliphatic moiety or a heterocycle, or R 2 and R 3 are linked to form a cyclo. aliphatic or heterocyclic ring having 3-7 ring members, which ring may bear substituents or may have at least one other ring system fused thereto; the carbon atom marked with an asterisk being symmetrical or assymmetrical; and the pharmaceutically acceptable non-toxic salts thereof, are prepared by reacting a penicillin having one of the formulµ or salts thereof wherein R 4 , R 5 and R 6 are alkyl, aralkyl, cycloalkyl or aryl, with an acyl isothiocyanate of formula or with an N-acyl-dithiocarbamic acid derivative of the general formula wherein R 7 is alkyl, alkyl substituted or interrupted by a heteroatom, a cycloaliphatic, aromatic or araliphatic moiety or a heterocycle; or by reacting a compound of the formula or a salt or derivative thereof with an acid of formula or a functional derivative thereof in the presence of a carbodiimide, a carbonyl-diimidazole or a carbonyl-ditriazole; or by fermentation of 6-APA with glycine, glycollic acid or thioglycollic acid derivatives of an acid of the formula wherein A is -NH-, -O- or -S-. The intermediate disilylated D(-)-α-aminobenzyl penicillin is prepared by forming a solution of dried D(-)-α-aminobenzyl penicillin and triethylamine in dichloromethane and treating with trimethyl chlorosilane. Pharmaceutical compositions comprise, as active ingredient, a novel penicillin as above defined and a non-toxic diluent or carrier. The compositions may be in various forms for internal or external use. The compositions may be in dosage unit form. The novel penicillins may also be used as additives to animal fodder and as agents for the treatment of cattle mastitis.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19671670963 DE1670963A1 (en) | 1967-12-10 | 1967-12-18 | New penicillins |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1246495A true GB1246495A (en) | 1971-09-15 |
Family
ID=5686356
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB59874/68A Expired GB1246495A (en) | 1967-12-18 | 1968-12-17 | Penicillins and their production |
Country Status (11)
| Country | Link |
|---|---|
| AT (1) | AT283593B (en) |
| BE (1) | BE725663A (en) |
| BR (1) | BR6804940D0 (en) |
| CH (1) | CH535789A (en) |
| CS (1) | CS155195B2 (en) |
| DK (1) | DK133433C (en) |
| FR (2) | FR1601138A (en) |
| GB (1) | GB1246495A (en) |
| IL (1) | IL31275A (en) |
| NL (1) | NL6818057A (en) |
| SE (1) | SE373587B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105859746A (en) * | 2016-03-22 | 2016-08-17 | 江西富祥药业股份有限公司 | Synthesis method for aspoxicillin |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2218340B1 (en) * | 1973-02-16 | 1978-09-29 | Rhone Poulenc Ind |
-
1968
- 1968-12-02 CH CH1803168A patent/CH535789A/en not_active IP Right Cessation
- 1968-12-11 AT AT1206568A patent/AT283593B/en not_active IP Right Cessation
- 1968-12-16 NL NL6818057A patent/NL6818057A/xx unknown
- 1968-12-16 IL IL31275A patent/IL31275A/en unknown
- 1968-12-17 DK DK617468A patent/DK133433C/en active
- 1968-12-17 GB GB59874/68A patent/GB1246495A/en not_active Expired
- 1968-12-17 SE SE6817283A patent/SE373587B/en unknown
- 1968-12-18 CS CS858968A patent/CS155195B2/cs unknown
- 1968-12-18 BE BE725663D patent/BE725663A/xx unknown
- 1968-12-18 FR FR1601138D patent/FR1601138A/fr not_active Expired
- 1968-12-18 BR BR204940/68A patent/BR6804940D0/en unknown
-
1969
- 1969-03-18 FR FR183292A patent/FR8263M/fr not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105859746A (en) * | 2016-03-22 | 2016-08-17 | 江西富祥药业股份有限公司 | Synthesis method for aspoxicillin |
Also Published As
| Publication number | Publication date |
|---|---|
| SE373587B (en) | 1975-02-10 |
| IL31275A (en) | 1973-02-28 |
| BE725663A (en) | 1969-06-18 |
| DK133433C (en) | 1976-10-11 |
| FR8263M (en) | 1970-10-19 |
| IL31275A0 (en) | 1969-02-27 |
| CS155195B2 (en) | 1974-05-30 |
| BR6804940D0 (en) | 1973-03-20 |
| DK133433B (en) | 1976-05-17 |
| CH535789A (en) | 1973-04-15 |
| FR1601138A (en) | 1970-08-10 |
| NL6818057A (en) | 1969-06-20 |
| AT283593B (en) | 1970-08-10 |
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