FR2100682B1 - - Google Patents

Info

Publication number
FR2100682B1
FR2100682B1 FR7118933A FR7118933A FR2100682B1 FR 2100682 B1 FR2100682 B1 FR 2100682B1 FR 7118933 A FR7118933 A FR 7118933A FR 7118933 A FR7118933 A FR 7118933A FR 2100682 B1 FR2100682 B1 FR 2100682B1
Authority
FR
France
Prior art keywords
group
lower
lower alkyl
formulμ
carbon atoms
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
Application number
FR7118933A
Other versions
FR2100682A1 (en
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer AG
Original Assignee
Bayer AG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority to DE19702025415 priority Critical patent/DE2025415C3/de
Priority to DE19712104579 priority patent/DE2104579C3/de
Application filed by Bayer AG filed Critical Bayer AG
Publication of FR2100682A1 publication Critical patent/FR2100682A1/fr
Application granted granted Critical
Publication of FR2100682B1 publication Critical patent/FR2100682B1/fr
Application status is Expired legal-status Critical

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D261/00Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
    • C07D261/02Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
    • C07D261/06Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
    • C07D261/10Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members 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
    • C07D261/18Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C275/00Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C275/46Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups containing any of the groups, X being a hetero atom, Y being any atom, e.g. acylureas
    • C07C275/58Y being a hetero atom
    • C07C275/60Y being an oxygen atom, e.g. allophanic acids
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D233/00Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/04Heterocyclic 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
    • C07D233/28Heterocyclic 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
    • C07D233/30Oxygen or sulfur atoms
    • C07D233/32One oxygen atom
    • C07D233/38One oxygen atom with acyl radicals or hetero atoms directly attached to ring nitrogen atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D333/00Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulfur
    • C07D333/06Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulfur with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/24Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D333/00Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulfur
    • C07D333/26Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulfur 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
    • C07D333/38Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00Compounds containing elements of Groups 4 or 14 of the Periodic System
    • C07F7/02Silicon compounds
    • C07F7/08Compounds having one or more C—Si linkages
    • C07F7/10Compounds having one or more C—Si linkages containing nitrogen having a Si-N linkage

Abstract

1301962 Ureido penicillins BAYER AG 25 May 1971 [25 May 1970 1 Feb 1971 3 Feb 1971] 16881/71 Heading C2A The invention comprises penicillins of the general Formula (I) in which general formula A is a group having one of the general formulµ (2), (3) or (4) in which formulµ X is a hydrogen atom or an alkyl, alkenyl, cycloalkyl or cycloalkenyl group with up to ten carbon atoms, or a vinyl, arylvinyl, mono-, di- or tri-haloalkyl, alkyamino, dialkylamino, monoarylamino, arylalkylamino or aryloxy group or an alkoxy or aryloxy group, or an alkoxy or aryloxy group with up to 8 carbon atoms, or a cycloalkoxy group with up to 7 carbon atoms, or a group having one of the general formulµ (lower alkyl)-O-V-, (lower alkyl)-S-V-, N#C-V-,(lower alkyl)-O-CO-V- or in which formulµ V is a bivalent organic radical with 1 to 3 carbon atoms, lower alkyl groups have up to six carbon atoms; n is 0, 1 or 2 and R 1 , R 2 and R 3 may be the same or different and are each hydrogen, chlorine, bromine, iodine or fluorine, nitro, nitrile, di(lower alkyl)amino, di(lower alkyl)ammo-carbonyl, lower alkanoylamino, lower alkoxy carbonyl, lower alkanoyloxy, lower alkyl, lower alkoxy, sulphamyl or trifluoromethyl; Y is an alkyl, alkenyl, cycloalkyl or cycloalkenyl group with up to 10 carbon atoms, or a vinyl, propenyl, mono-, di- or tri-halo (lower alkyl) aryl or heterocyclic group, or an aralkyl group with up to 8-carbon atoms; #Z- is a divalent group having one of the formulµ in which formulµ n is 3, 4 or 5 and the arrow # means that the two free valencies of the group Z are not arbitrarily joined to the N and C atoms of the group (3) but are oriented as indicated by the arrow. Q is a divalent group, B is a group having one of the general formulµ in which formulµ R 4 , R 5 and R 6 may be the same or different and are each hydrogen, halogen, lower alkyl, lower alkoxy, lower alkylthio, lower alkylthionyl, lower alkylsulphonyl, nitro, di(lower alkyl) amino, lower alkanoylamino, hydroxy, or lower alkanoyloxy and in which the chirality centre C*can have either of the two possible R and S stereoisomeric configurations or can be a mixture of these two diastereosiomers. The invention also comprises salts of the above penicillins. A process for the production of penicillins of Formula (I) comprises reacting 6-amino-penicillanic acid or a compound of the general formula (46) or (47) in which R 7 , R 8 and R 9 are the same or different alkyl groups having up to 6 carbon atoms, at a temperature of -30‹ C. to +50‹ C. with a carboxylic acid of general formula If compounds of formula (46) or (47) are used, the reaction is carried out in an anhydrous solvent which is free of hydroxyl groups, with or without a base, and if 6-aminopenicillanic acid is used, the reaction is carried out in a solvent in the presence of a base. Various modifications of the process are described. Antibiotically active pharmaceutical compositions, which contain as active ingredient at least one penicillin of Formula (I) or a pharmaceutically acceptable salt thereof, have been prepared. Such compositions also contain a pharmaceutically acceptable carrier which may be solid or liquid. These compositions may be adapted for parenteral or oral administration and may be prepared in dosage unit form.
FR7118933A 1970-05-25 1971-05-25 Expired FR2100682B1 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
DE19702025415 DE2025415C3 (en) 1970-05-25 1970-05-25
DE19712104579 DE2104579C3 (en) 1971-02-01 1971-02-01

Publications (2)

Publication Number Publication Date
FR2100682A1 FR2100682A1 (en) 1972-03-24
FR2100682B1 true FR2100682B1 (en) 1975-01-17

Family

ID=25759180

Family Applications (1)

Application Number Title Priority Date Filing Date
FR7118933A Expired FR2100682B1 (en) 1970-05-25 1971-05-25

Country Status (26)

Country Link
JP (1) JPS55390B1 (en)
AT (1) AT306924B (en)
BE (1) BE767648A (en)
BG (1) BG23753A3 (en)
CA (1) CA932722A (en)
CH (1) CH571524A5 (en)
CS (1) CS185564B2 (en)
CY (1) CY830A (en)
DD (1) DD91496B3 (en)
DK (1) DK134438C (en)
EG (1) EG10490A (en)
ES (4) ES391533A1 (en)
FI (1) FI54485C (en)
FR (1) FR2100682B1 (en)
GB (1) GB1301962A (en)
IE (1) IE35404B1 (en)
IL (1) IL36904A (en)
KE (1) KE2591A (en)
LU (1) LU63204A1 (en)
NL (1) NL172659C (en)
NO (1) NO141759C (en)
PH (1) PH12110A (en)
RO (1) RO59290A (en)
SE (1) SE395895B (en)
SU (1) SU420181A3 (en)
YU (1) YU35889B (en)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2260118C2 (en) * 1972-12-08 1982-06-03 Bayer Ag, 5090 Leverkusen, De
DE2354219A1 (en) * 1973-10-30 1975-05-07 Bayer Ag Beta-lactam antibiotics, a process for their production and their use as medicines
GB1486349A (en) * 1974-11-28 1977-09-21 Bayer Ag Beta-lactam antibiotics process for their preparation and their use as medicaments
GB1584400A (en) * 1976-12-24 1981-02-11 Bayer Ag (2-oxo-imidazoliden-1-yl(carbonylamino)-acetamido-cephalosporins and penicillins
KR860000300B1 (en) * 1983-12-19 1986-03-31 김승호 Process for preparing acylureide penicillin derivatives

Also Published As

Publication number Publication date
FI54485B (en) 1978-08-31
IE35404L (en) 1971-11-25
BG23753A3 (en) 1977-10-12
LU63204A1 (en) 1971-09-01
CH571524A5 (en) 1976-01-15
NO141759B (en) 1980-01-28
YU129671A (en) 1981-02-28
YU35889B (en) 1981-08-31
NL7107176A (en) 1971-11-29
IL36904A (en) 1975-11-25
JPS55390B1 (en) 1980-01-08
BE767648A (en) 1971-11-25
GB1301962A (en) 1973-01-04
IL36904D0 (en) 1971-07-28
NL172659C (en) 1983-10-03
FI54485C (en) 1978-12-11
SE395895B (en) 1977-08-29
ES411674A1 (en) 1976-01-01
SU420181A3 (en) 1974-03-15
ES391533A1 (en) 1974-08-01
RO59290A (en) 1976-03-15
AT306924B (en) 1973-04-25
KE2591A (en) 1976-01-09
CA932722A (en) 1973-08-28
DD91496A5 (en) 1972-07-20
IE35404B1 (en) 1976-02-04
DK134438C (en) 1977-05-31
ES411676A1 (en) 1976-01-01
NO141759C (en) 1980-05-07
FR2100682A1 (en) 1972-03-24
DK134438B (en) 1976-11-08
CA932722A1 (en)
CY830A (en) 1976-03-19
ES411675A1 (en) 1976-01-01
NL172659B (en) 1983-05-02
DD91496B3 (en) 1988-01-27
CS185564B2 (en) 1978-10-31
BE767648A1 (en)
PH12110A (en) 1978-11-02
EG10490A (en) 1976-08-31

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Legal Events

Date Code Title Description
CD Change of name or company name
ST Notification of lapse