GB1392850A - Penicillin compounds their production and their medicinal use - Google Patents
Penicillin compounds their production and their medicinal useInfo
- Publication number
- GB1392850A GB1392850A GB4870072A GB4870072A GB1392850A GB 1392850 A GB1392850 A GB 1392850A GB 4870072 A GB4870072 A GB 4870072A GB 4870072 A GB4870072 A GB 4870072A GB 1392850 A GB1392850 A GB 1392850A
- Authority
- GB
- United Kingdom
- Prior art keywords
- radical
- formula
- general formula
- acid
- compound
- 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
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
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/30—Oxygen or sulfur atoms
- C07D233/32—One oxygen atom
- C07D233/38—One oxygen atom with acyl radicals or hetero atoms directly attached to ring nitrogen atoms
Abstract
1392850 Penicillins and intermediates therefor BAYER AG 23 Oct 1972 [23 Oct 1971 25 March 1972] 48700/71 Heading C2C Penicillins of the general formula or their salts in which C* is a carbon atom constituting a centre of chirality; A is a radical of one of the general formulµ (in which general formulµ X is Y is Q 1 is or a radical of formula and Q 2 is a radical of formula wherein R is a straight-chain or branched alkyl radical with up to 5 carbon atoms; R 1 is a hydrogen atom or an alkyl, cycloalkyl, alkenyl or cycloalkenyl radical with up to 10 carbon atoms, or a vinyl, arylvinyl, mono-, di- or trihalo C 1-6 alkyl radical, or an H 2 N-, R-NH-, (R) 2 =N-, aryl -NH-, or aryl C 1-6 alkylamino radical or an alkoxy*, or aralkoxy* radical with up to 8 carbon atoms, or a cycloalkoxy* radical with up to 7 carbon atoms, or an aryloxy*, R-O-V-, R-S-V-, (R) 2 =N-CO-V- or a radical of formulµ V is a divalent organic radical with 1 to 3 carbon atoms; n is 0, 1, or 2; R 2 and R 3 which may be the same or different are each a hydrogen atom or an alkyl or alkenyl radical having up to 8 carbon atoms or a vinyl, allyl or propenyl radical, or a cycloalkyl or cycloalkenyl radical having up to 6 carbon atoms, or a mono-, di-, or tri-halogeno C 1-6 alkyl or aryl radical; R 4 , R 5 and R 6 which may be the same or different are each a hydrogen, nitro, nitrile, (R) 2 =N-, (R) 2 = N-CO-, R-CO-NH-, R-O-CO-, R-CO-O-, R, R-O, H 2 N-SO 2 -, chlorine, bromine, iodine, fluorine or trifluoromethyl radical; and G is a hydrogen atom. or a radical R; with the proviso that the meanings marked* are only available if X is not an -SO 2 - radical); Z is a - CO- or -SO- radical; and B is a radical of the general formula in which R 7 , Rs and R 9 are identical or different radicals selected from hydrogen, halogen, R-, R-O-, R-S-, R-SO-, R-SO 2 -, nitro(R 2 )=N-, R-CO-NH-, HO, and radicals and R is as above defined; and in which above general formulµ the arrow in the divalent linkage member ##Q2 means that the linkage of two atoms by the two free valencies of this linking member is not free to take place in either direction but only in the manner indicated by the arrow are prepared by (i) producing a reactive intermediate by reacting a carboxylic acid, a carboxylic acid salt, or a carboxylic acid silyl or hemisilyl ester of the general formulµ in an aqueous or anhydrous organic solvent when a compound of general formula a or b is reacted, or in an anhydrous inert organic solvent free of hydroxyl groups when a compound of general formula c or d is reacted, at - 70 to + 30 C., with either (a) a compound of one of the following general formulµ or (b) with a reaction product produced by the reaction of a compound of the general formula with about 1 mol. equivalent of thionyl chloride in an inert anhydrous organic solvent in the presence of at least one mol. equivalent of an organic base acting as an acid-acceptor at a temperature within the range - 40 to + 25 C.; the reaction product being reacted without prior isolation in the presence of a further mol. equivalent of a base, with about 1 mol. equivalent of the acid of formula (a), or in the presence of 0-1 mol. equivalent of a base, with about 1 mol. equivalent of a compound of formula b, c or d, at a temperature of - 40 to + 30 C., whereby the reactive intermediate produced is of the general formula (c) (only available for carboxylic acids of formula a) with about 1 mol. equivalent of a carbodiimide in a diluent and in the presence of about 1 mol. equivalent of a compound of Formula XIX whereby the reactive intermediate produced is of the general Formula XX the diluent being anhydrous and free of hydroxyl groups if a compound of the general formula is to be used in step (ii); and (ii) reacting the reactive intermediate with 6-aminopenicillanic acid of the general formula or silyl or disilyl-6-aminopenicillanic acid of Formula XXI and XXII in a solvent in the presence of a base when 6-aminopenicillanic acid is used, or in an anhydrous solvent free of hydroxyl groups when a compound of the Formula XXI or XXII is used, at a temperature in the range of - 70 to 50 C., to produce the desired penicillin compound, wherein Me<SP>n(+)</SP> is a cation of an n-valent alkali metal or alkaline earth metal or an aluminium cation; R 10 , R 11 and R 12 are the same or different C 1-6 alkyl radicals, R 13 can have any of the meanings given for R and can also be a phenyl radical; R 14 is a -(CH 2 ) 4 -, -(CH 2 ) 5 - or -(CH 2 ) 2 -O-(CH 2 ) 2 , radical; the groups U which can be the same or different are -C # N or -CO-O-C 1-6 alkyl radicals; and W is a halogen atom). Penicillins of the above general formula wherein B is as above defined except that it is not cyclohexadienyl and in which R 7 , R 8 and R 9 which may be the same or different, are each a hydrogen, halogen, R-, R-O-, R-S-, R-SO-, R-SO 2 -, nitro, (R) 2 =N, R-CO-NH, HO or R-CO-O- radical, R being as above defined, provided that when two of R 7 , R 8 and R 9 are hydrogen the other cannot be hydroxyl, and that all three of R 7 , R 8 and R 9 cannot at once be hydrogen, are stated to be novel. The carboxylic acids of formula (a) can be obtained from the amino acids of the general formula by reaction with compounds of the general formula A-Z-W(e), (in which A, B, Q 1 , Q 2 , R 1 , R 2 , X, Y, Z, C* and W are as defined above). Compounds of formulµ (e), (f), (g), (h) and (i) are prepared by conventional methods. Pharmaceutical compositions having antibacterial activity useful in human and veterinary medicine comprise the above penicillins and a carrier. The compositions may be administered orally, parenterally, rectally or topically in conventional pharmaceutical forms. The following starting materials are prepared; α[(3 - methyl - sulphonyl - imidazolidin - 2 - on- 1 - yl)carbonylamino] - phenylacetic acid, -4 - chloro - phenyl acetic acid, and -α- thienyl - (2) - acetic acid and 2,6 - dichlorophenyl acetic acids; α[(3-acetyl-imidazolidin- 2 - on - 1 - yl)carbonylamino] - phenyl acetic acid, -4 - chloro - phenylacetic acid, 4 - mothylphenyl acetic acid, -α - thienyl - (2) - acetic acid, 2,6 - dichloro - phenyl acetic acids, α - [(3 - ethylsulphonyl - imidazolidin - 2 - on- 1 - yl) carbonylamino] - phenyl acetic acid and -p - chlorophenyl acetic acid; and α[(3- methoxy carbonyl - imidazolidin - 2 - on - 1- yl) carbonylamino] - 4 - chlorophenylacetic and α-thienyl (2)-acetic acids.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE2152968A DE2152968A1 (en) | 1971-10-23 | 1971-10-23 | NEW PENICILLIN |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1392850A true GB1392850A (en) | 1975-04-30 |
Family
ID=5823252
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB4870072A Expired GB1392850A (en) | 1971-10-23 | 1972-10-23 | Penicillin compounds their production and their medicinal use |
Country Status (32)
Country | Link |
---|---|
JP (2) | JPS5538955B2 (en) |
AR (1) | AR196634A1 (en) |
AT (1) | AT321462B (en) |
BE (1) | BE790441A (en) |
BG (1) | BG19376A3 (en) |
CA (1) | CA1012531A (en) |
CH (1) | CH591496A5 (en) |
CS (1) | CS186766B2 (en) |
CY (1) | CY948A (en) |
DD (1) | DD106045B3 (en) |
DE (1) | DE2152968A1 (en) |
DK (1) | DK138855C (en) |
EG (1) | EG11092A (en) |
ES (1) | ES407852A1 (en) |
FI (1) | FI57108C (en) |
FR (1) | FR2157909B1 (en) |
GB (1) | GB1392850A (en) |
HK (1) | HK15378A (en) |
HU (1) | HU166539B (en) |
IE (1) | IE37096B1 (en) |
IL (1) | IL40627A (en) |
KE (1) | KE2825A (en) |
LU (1) | LU66333A1 (en) |
NL (1) | NL7214255A (en) |
NO (1) | NO143908C (en) |
PH (1) | PH10000A (en) |
PL (1) | PL89072B1 (en) |
RO (1) | RO60671A (en) |
SE (1) | SE401186B (en) |
SU (1) | SU522802A3 (en) |
YU (1) | YU36179B (en) |
ZA (1) | ZA727474B (en) |
Families Citing this family (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3983105A (en) * | 1971-10-23 | 1976-09-28 | Bayer Aktiengesellschaft | Penicillins |
US3974141A (en) * | 1971-10-23 | 1976-08-10 | Bayer Aktiengesellschaft | Penicillins |
NL175419C (en) * | 1971-10-23 | 1984-11-01 | Bayer Ag | METHOD FOR PREPARING OR MANUFACTURING ANTIBIOTIC ACTIVE PHARMACEUTICAL PREPARATIONS AND METHOD FOR PREPARING ANTIBIOTIC ACTIVE ALPHA-SUBSTITUTED 6- (ALFA- (3-ACYLUREIDO) -PETYL-ACIDYL-ACIDYL-ACIDYL) |
US3978056A (en) * | 1971-10-23 | 1976-08-31 | Bayer Aktiengesellschaft | Penicillins |
US4009272A (en) * | 1971-10-23 | 1977-02-22 | Bayer Aktiengesellschaft | Penicillins |
US3974142A (en) * | 1971-10-23 | 1976-08-10 | Bayer Aktiengesellschaft | Penicillins |
US3972869A (en) * | 1971-10-23 | 1976-08-03 | Bayer Aktiengesellschaft | Penicillins |
US3972870A (en) * | 1971-10-23 | 1976-08-03 | Bayer Aktiengesellschaft | Penicillins |
GB1462421A (en) * | 1973-12-14 | 1977-01-26 | Pfizer | 6-a-amidino-and -'midoylaminoalkanoylamino aracylamino-penicillanic acids and their preparation |
GB1486349A (en) * | 1974-11-28 | 1977-09-21 | Bayer Ag | Beta-lactam antibiotics process for their preparation and their use as medicaments |
JPS5852996B2 (en) * | 1975-03-25 | 1983-11-26 | バイエル・アクチエンゲゼルシヤフト | Beta-lactams and antibacterial agents |
DE2658905A1 (en) * | 1976-12-24 | 1978-10-19 | Bayer Ag | BETA-LACTAM-ANTIBIOTICA, METHOD FOR MANUFACTURING IT AND ITS USE AS A MEDICINAL PRODUCT |
GB1584400A (en) * | 1976-12-24 | 1981-02-11 | Bayer Ag | (2-oxo-imidazoliden-1-yl(carbonylamino)-acetamido-cephalosporins and penicillins |
DE2810083A1 (en) | 1978-03-08 | 1979-09-20 | Bayer Ag | BETA-LACTAM COMPOUNDS |
DE2817228A1 (en) * | 1978-04-20 | 1979-10-31 | Bayer Ag | PROCESS FOR MANUFACTURING SEMI-SYNTHETIC BETA-LACTAMANTIBIOTICS |
JP7122236B2 (en) * | 2018-11-28 | 2022-08-19 | 東京エレクトロン株式会社 | Inspection device, maintenance method and program |
-
0
- BE BE790441D patent/BE790441A/en not_active IP Right Cessation
-
1971
- 1971-10-23 DE DE2152968A patent/DE2152968A1/en active Pending
-
1972
- 1972-10-12 SU SU1839116A patent/SU522802A3/en active
- 1972-10-17 RO RO197272545A patent/RO60671A/ro unknown
- 1972-10-17 PH PH14019A patent/PH10000A/en unknown
- 1972-10-19 HU HUBA2816A patent/HU166539B/hu not_active IP Right Cessation
- 1972-10-19 FI FI2898/72A patent/FI57108C/en active
- 1972-10-19 CS CS7200007049A patent/CS186766B2/en unknown
- 1972-10-19 BG BG21666A patent/BG19376A3/xx unknown
- 1972-10-19 DD DD72166351A patent/DD106045B3/en unknown
- 1972-10-20 ZA ZA727474A patent/ZA727474B/en unknown
- 1972-10-20 DK DK523372A patent/DK138855C/en not_active IP Right Cessation
- 1972-10-20 IL IL7240627A patent/IL40627A/en unknown
- 1972-10-20 AT AT901172A patent/AT321462B/en not_active IP Right Cessation
- 1972-10-20 IE IE1423/72A patent/IE37096B1/en unknown
- 1972-10-20 SE SE7213593A patent/SE401186B/en unknown
- 1972-10-20 LU LU66333A patent/LU66333A1/xx unknown
- 1972-10-20 NL NL7214255A patent/NL7214255A/xx not_active Application Discontinuation
- 1972-10-20 CA CA154,339A patent/CA1012531A/en not_active Expired
- 1972-10-20 CH CH1531972A patent/CH591496A5/xx not_active IP Right Cessation
- 1972-10-21 JP JP10490372A patent/JPS5538955B2/ja not_active Expired
- 1972-10-21 JP JP47104904A patent/JPS4849911A/ja active Pending
- 1972-10-21 ES ES407852A patent/ES407852A1/en not_active Expired
- 1972-10-21 PL PL1972158393A patent/PL89072B1/pl unknown
- 1972-10-21 EG EG438/72A patent/EG11092A/en active
- 1972-10-23 GB GB4870072A patent/GB1392850A/en not_active Expired
- 1972-10-23 NO NO723809A patent/NO143908C/en unknown
- 1972-10-23 CY CY948A patent/CY948A/en unknown
- 1972-10-23 YU YU2638/72A patent/YU36179B/en unknown
- 1972-10-23 FR FR7237484A patent/FR2157909B1/fr not_active Expired
- 1972-10-23 AR AR244771A patent/AR196634A1/en active
-
1978
- 1978-03-14 KE KE2825A patent/KE2825A/en unknown
- 1978-03-16 HK HK153/78A patent/HK15378A/en unknown
Also Published As
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PS | Patent sealed [section 19, patents act 1949] | ||
PCNP | Patent ceased through non-payment of renewal fee | ||
PE20 | Patent expired after termination of 20 years |