IL40628A - Alpha-(substituted ureido)derivatives of benzyl-,hydroxybenzyl-and cyclohexadienylmethyl penicillins,their preparation and pharmaceutical compositions or feed additives containing them - Google Patents

Alpha-(substituted ureido)derivatives of benzyl-,hydroxybenzyl-and cyclohexadienylmethyl penicillins,their preparation and pharmaceutical compositions or feed additives containing them

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Publication number
IL40628A
IL40628A IL7240628A IL4062872A IL40628A IL 40628 A IL40628 A IL 40628A IL 7240628 A IL7240628 A IL 7240628A IL 4062872 A IL4062872 A IL 4062872A IL 40628 A IL40628 A IL 40628A
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compound
radical
general formula
compounds
general
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IL7240628A
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IL40628A0 (en
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Bayer Ag
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Publication of IL40628A publication Critical patent/IL40628A/en

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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D239/00Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/06Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D239/08Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine 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 directly attached in position 2
    • C07D239/10Oxygen or sulfur atoms
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P21/00Drugs for disorders of the muscular or neuromuscular system
    • A61P21/06Anabolic agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04Antibacterial agents
    • 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
    • C07D275/00Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
    • C07D275/02Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings
    • 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 sulphur atom
    • 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 sulphur atom 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
    • C07D333/30Hetero atoms other than halogen
    • C07D333/34Sulfur atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D499/00Heterocyclic 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
    • 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 Table
    • 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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Oncology (AREA)
  • Communicable Diseases (AREA)
  • Endocrinology (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Neurology (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Fodder In General (AREA)

Abstract

1392849 Penicillins BAYER AG 23 Oct 1972 [23 Oct 1971 22 Nov 1971 25 March 1972 25 July 1972] 48699/72 Heading C2C [Also in Division C3] 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 or 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 , R 8 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-, OH, and radicals and R is as above defined; and in which above general formulµ the arrow in the divalent linkage member ##Q 2 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 reacting a 6-amino-penicillanic acid derivative of the general formula or a product of the condensation of such a derivative with a carbonyl compound 'of formula or a silyl or disilyl derivative of the derivative of the general formulµ respectively is reacted with a compound of the general formula A-Z-W, in an anhydrous or aqueous solvent in the presence of a base, when a compound of general Formulae XIV and XV is reacted, and in an anhydrous solvent free of hydroxyl groups, with or without a base, when a compound of the general Formulµ XVI and XVII is reacted, at a temperature of - 50‹ to + 50‹ C. (wherein A, C*, G, Q 1 , Q 2 , R 1 , R 2 , X, Y, Z and B are as above defined and R 10 , R 11 and R 12 , which can be the same or different are C 1-6 alkyl and W is halogen, azide or Compounds of the above general formula wherein B is phenyl, cyclohexadienyl or hydroxyphenyl are stated to be novel. Compounds of the formula A-Z-W, and Formulµ XVIII and XIX 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 also prepared: 3 - acetyl - 3 - (N - methylaminocarbonyl}-, 3 - methoxy - carbonyl, 3 - methylsulphonyl-, 3 - aminocarbonyl-, 3 - dimethylaminocarbonyl-, 3 - isopropoxycarbonyl-, 3 - pyrrolidyl - N- carbonyl-, 3 - piperidyl - N - carbonyl-, 3- phenylaminocarbonyl-, 3 - phenoxycarbonyl-, 3- benzoyl-, 3-furoyl-, 3-butyryl-, -, 3-formyl- 3 - pivaloyl-, 3 - cyclohexyloxycarbonyl-, 3- ethane - sulphonyl-, 3 - propionyl-, 3 - benzenesulphonyl-, 3 - methane - sulphonyl - aminocarbonyl- and 3 - thienyl - 2 - sulphonyl - imidazolidine - 1 - carbonyl chloride and the corresponding N - substituted - imidazolidin - 2- ones; 2 - chlorosulphonylthiophene; 1 - methanesulphonyl - 3 - chlorocarbonyl - 4 or -5 - methylimidazolidine - 2 - one and 1 - methanesulphonyl- 4- or 5 - methylimidazolid - 2 - one; 4 - methylimidazolidin - 2 - one; 1 - chlorocarbonyl - 2- methylsulphonylamino- and 2 - tosylamino - 4,5- dihydroimidazoles; 1 - (methylaminocarbonyl)- 3 - ethoxycarbonyl - guanidine and its N- nitroso derivative, N (1,1 -dioxo-isothiazolidin-2- yl] - carbonyl] - N - methyl - carbamic acid chloride; N - mesyl - N<SP>1</SP> - chlorocarbonylurea; 3- acetyl-, 3 - formyl-, 3 - mesyl-, and 3 - phenyl sulphonyl-, 1 - chlorocarbonyl - 2 - oxo - 1,3- diazacyclohexanes and their 1 -unsubstituted derivatives. [GB1392849A]

Claims (1)

1. CLAIMS i Compounds which are penicillins of the general formula their in which is a carbon atom constituting a centre of and is one of the following a radical of the general formula x V in which is hydrogen if X is lower lower lower alkoxy X is lower cycloalkoxy X is X is C lower alkyl thiazolyl lower alkyl lowe carbonylamino CO or and is and which are optionall substituted by lower or a radical of the general formula in which is lower alkyl or lower or 124 a radical of the general formula in which is lower a radical of the general formula in which is lower alkyl lower is X is GO or and Y is or B is hydroxyphenyl or 1 The compounds according to claim in which A is 0 The compounds according to claim in which A is The compounds according to claim in which A is 125 The compounds according to claim 1 in which A is 0 The compounds according to claim in which A is The compounds according to claim in which A is The compounds according to claim in which A is 0 The compounds according to claim in which A is 1 in which A is The compounds according to any of claims 1 to in which is a phenyl 12 The according to any of claims 1 to in which B is 13 The compounds according to any of claims 1 to in which B is The compounds according to any of claims 1 to which is in the 16 0 1 130 39 or ylami Compounds according to Claim 1 which are hereinbefore specifically mentioned in the other than those according to any of claims 17 to 133 A process for the production of a compound according to any of Claims 1 to 51 and also of similar compounds claimed in copending Application in which a acid derivative of the general formula or a product of the condensation of such a derivative with a carbonyl the said product having the general 0 or a silyl or disilyl derivative of the said the general respectively is reacted with a compound of the general formula in an anhydrous or aqueous in the presence of a when a compound of the general formula II III is and in an anhydrous solvent free of hydro yl with or without a when a compound of the general formula IV or V is at a temperature in the range of to which general formulae Y and Z are as defined in any of claims 1 to G is hydrogen or a straight or branched group or are each an alkyl group with up to 6 Carbon is a or NO A process according to claim which the reaction is carried out at a pH in the range to I A process accordin to claim in which the said pH is between nd A process according to claim in which the s id d A process according to any of Claims 52 to 55 in which the reaction is carried out at a temperature between 0 and A process according to any of Claims 52 to 56 in which is a chlorine A process according to any of Claims 52 to 57 in which a compound formula II or III is reacted in the presence of a the said base being triethylamine or A process according to any of Claims 52 to 57 in which a compound of the general formula IV or V is reacted in the presence of a the said base being a secondary or tertiary A process according to Claim substantially as hereinbefore described in any of the Compounds according to Claim 1 whenever produced by the process of any of Claims 52 to A composition containing as an active ingredient a compound according to any of Claims 1 to 51 or in admixture with a solid or liquified gaseous diluent or in admixture with a liquid diluent other than a solvent o molecular weight less than 200 except in the presence of a A pharmaceutical composition containing as an active ingredient a compound according to any of Claims 1 to 51 or in the form of a sterile or isotonic aqueous A according to Claim 62 or 63 containing from to 95 of active by A composition according to Claim 63 or 64 in which the said compound a compound according to Claim 10 or 38 to A compsition according to Claim 63 or 64 in which the said compound is a compound according to Claim to A pharmaceutical composition according to Claim 62 or substantially as hereinbefore described or specifically A medicament in dosage unit form comprising a compound according to an of Claims 1 to 51 or 61 either alone or in admixture with a A medicament in the form of ampoules or suppositories comprising a compound according to any of Claims 1 to 51 or either alone or in admixture with a A medicament according to Claim 68 or in which the said compound is a compound according to Claim 10 or 38 to A medicament according to Claim 68 or in which the said compound is a compound according Claim 46 to A medicament according to any of Claims 68 or substantially as hereinbefore described or specifically A method of combatting bacterial infections in animals which comprises administering to the animals an active compound according to any of Claims 1 to 51 or either alone or in admixture with a diluent or in the form of a medicament according to Claim 68 or method according to Claim in which the active compound is administered in an amount of 25000 to of body A method according to Claim 73 or 74 in which the active compound is a compound aceording to Claim 10 or 38 to A method according to Claim 73 or 74 in which the is a compound aceording to Claim 46 to according to Claim 73 substantially as hereinbefore specifically described or An animal comprising a nutritious material and a compound according to any of Claims 1 to 51 or An animal feedstuff comprising a nutritious material and a compound according to Claim 10 or 38 to An animal feedstuff comprising a nutritious material and a compound according to 46 to insufficientOCRQuality
IL7240628A 1971-10-23 1972-10-20 Alpha-(substituted ureido)derivatives of benzyl-,hydroxybenzyl-and cyclohexadienylmethyl penicillins,their preparation and pharmaceutical compositions or feed additives containing them IL40628A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE2152967A DE2152967C3 (en) 1971-10-23 1971-10-23 Acylureidopenicillins

Publications (2)

Publication Number Publication Date
IL40628A0 IL40628A0 (en) 1972-12-29
IL40628A true IL40628A (en) 1976-08-31

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JP (2) JPS57843B2 (en)
AR (1) AR195805A1 (en)
AT (1) AT320152B (en)
BE (1) BE790440A (en)
BG (2) BG21609A3 (en)
CA (1) CA1019323A (en)
CH (1) CH579089A5 (en)
CS (1) CS188883B2 (en)
CY (1) CY947A (en)
DD (1) DD106044B3 (en)
DE (1) DE2152967C3 (en)
DK (1) DK134992C (en)
EG (1) EG10826A (en)
ES (1) ES407851A1 (en)
FI (1) FI56839C (en)
FR (1) FR2157908B1 (en)
GB (1) GB1392849A (en)
HK (1) HK18578A (en)
HU (1) HU167986B (en)
IE (1) IE37123B1 (en)
IL (1) IL40628A (en)
KE (1) KE2824A (en)
LU (1) LU66332A1 (en)
NO (1) NO143909C (en)
PH (1) PH9893A (en)
PL (2) PL89056B1 (en)
RO (2) RO60670A (en)
SE (1) SE412236B (en)
SU (1) SU527139A3 (en)
YU (1) YU264072A (en)
ZA (1) ZA727473B (en)

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CA2735764C (en) 2008-09-02 2016-06-14 Ortho-Mcneil-Janssen Pharmaceuticals, Inc. 3-azabicyclo[3.1.0]hexyl derivatives as modulators of metabotropic glutamate receptors
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IE37123B1 (en) 1977-05-11
CA1019323A (en) 1977-10-18
JPS55391B2 (en) 1980-01-08
ZA727473B (en) 1973-07-25
SU527139A3 (en) 1976-08-30
FI56839B (en) 1979-12-31
HU167986B (en) 1976-02-28
GB1392849A (en) 1975-04-30
JPS57843B2 (en) 1982-01-08
DE2152967A1 (en) 1973-05-03
FR2157908A1 (en) 1973-06-08
EG10826A (en) 1976-12-31
DE2152967B2 (en) 1981-02-19
DK134992B (en) 1977-02-21
BG20813A3 (en) 1975-12-20
FR2157908B1 (en) 1976-03-19
CH579089A5 (en) 1976-08-31
DD106044A5 (en) 1974-05-20
IL40628A0 (en) 1972-12-29
PH9893A (en) 1976-06-08
RO60670A (en) 1976-10-15
BG21609A3 (en) 1976-07-20
AR195805A1 (en) 1973-11-09
KE2824A (en) 1978-04-07
SE412236B (en) 1980-02-25
NO143909B (en) 1981-01-26
IE37123L (en) 1973-04-23
JPS4849787A (en) 1973-07-13
PL89056B1 (en) 1976-10-30
YU264072A (en) 1982-06-18
FI56839C (en) 1980-04-10
DE2152967C3 (en) 1981-11-19
AU4806472A (en) 1974-04-26
HK18578A (en) 1978-04-14
BE790440A (en) 1973-04-24
CS188883B2 (en) 1979-03-30
RO63066A (en) 1978-06-15
AT320152B (en) 1975-01-27
NO143909C (en) 1981-05-06
LU66332A1 (en) 1973-01-23
CY947A (en) 1978-06-23
DK134992C (en) 1977-07-18
DD106044B3 (en) 1990-07-18
PL93574B1 (en) 1977-06-30
JPS4849910A (en) 1973-07-14
ES407851A1 (en) 1975-10-01

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