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 themInfo
- 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
- Authority
- IL
- Israel
- Prior art keywords
- compound
- radical
- general formula
- compounds
- general
- Prior art date
Links
- 229930182555 Penicillin Natural products 0.000 title claims abstract 5
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract 4
- -1 benzyl- Chemical class 0.000 title abstract 15
- 239000003674 animal food additive Substances 0.000 title 1
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 46
- 125000000217 alkyl group Chemical group 0.000 claims abstract 8
- 239000003814 drug Substances 0.000 claims abstract 7
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 5
- 239000001257 hydrogen Substances 0.000 claims abstract 4
- 150000002960 penicillins Chemical class 0.000 claims abstract 4
- 229910052799 carbon Inorganic materials 0.000 claims abstract 3
- 239000000203 mixture Substances 0.000 claims abstract 3
- 239000002904 solvent Substances 0.000 claims abstract 3
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 2
- 229910052801 chlorine Inorganic materials 0.000 claims abstract 2
- 239000000460 chlorine Substances 0.000 claims abstract 2
- 230000005494 condensation Effects 0.000 claims abstract 2
- 238000009833 condensation Methods 0.000 claims abstract 2
- 125000000000 cycloalkoxy group Chemical group 0.000 claims abstract 2
- 125000004464 hydroxyphenyl group Chemical group 0.000 claims abstract 2
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims 14
- 241001465754 Metazoa Species 0.000 claims 5
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 3
- 239000003085 diluting agent Substances 0.000 claims 3
- 239000000463 material Substances 0.000 claims 3
- 235000008935 nutritious Nutrition 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 239000004480 active ingredient Substances 0.000 claims 2
- 208000035143 Bacterial infection Diseases 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 241000282320 Panthera leo Species 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 208000022362 bacterial infectious disease Diseases 0.000 claims 1
- 150000001721 carbon Chemical group 0.000 claims 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 239000000829 suppository Substances 0.000 claims 1
- 150000003254 radicals Chemical class 0.000 abstract 11
- 125000004432 carbon atom Chemical group C* 0.000 abstract 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 5
- DWEQVNFWAKJCEY-UHFFFAOYSA-N 4-methylimidazolidin-2-one Chemical compound CC1CNC(=O)N1 DWEQVNFWAKJCEY-UHFFFAOYSA-N 0.000 abstract 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 abstract 2
- 229920002554 vinyl polymer Polymers 0.000 abstract 2
- AFQRORBLVJQAMT-UHFFFAOYSA-N 2-oxo-1,3-diazinane-1-carbonyl chloride Chemical class ClC(=O)N1CCCNC1=O AFQRORBLVJQAMT-UHFFFAOYSA-N 0.000 abstract 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 abstract 1
- YBHQFWGIKIVSPP-UHFFFAOYSA-N 2-sulfonyl-3-thiophen-3-ylimidazolidine-1-carbonyl chloride Chemical compound S1C=C(C=C1)N1C(N(CC1)C(=O)Cl)=S(=O)=O YBHQFWGIKIVSPP-UHFFFAOYSA-N 0.000 abstract 1
- NGHVIOIJCVXTGV-ALEPSDHESA-N 6-aminopenicillanic acid Chemical class [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
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 abstract 1
- WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 abstract 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 230000000844 anti-bacterial effect Effects 0.000 abstract 1
- 239000003125 aqueous solvent Substances 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 150000005840 aryl radicals Chemical class 0.000 abstract 1
- 125000003609 aryl vinyl group Chemical group 0.000 abstract 1
- 125000004104 aryloxy group Chemical group 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- 150000001540 azides Chemical group 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 150000001728 carbonyl compounds Chemical class 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 238000007796 conventional method Methods 0.000 abstract 1
- 125000003678 cyclohexadienyl group Chemical group C1(=CC=CCC1)* 0.000 abstract 1
- SJQHUFPQIIXJKK-UHFFFAOYSA-N ethyl (ne)-n-[amino-(methylcarbamoylamino)methylidene]carbamate Chemical compound CCOC(=O)NC(=N)NC(=O)NC SJQHUFPQIIXJKK-UHFFFAOYSA-N 0.000 abstract 1
- 229910052731 fluorine Inorganic materials 0.000 abstract 1
- 239000011737 fluorine Substances 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 abstract 1
- WYWMMZFTXGQLCR-UHFFFAOYSA-N n-(4,5-dihydro-1h-imidazol-2-yl)-4-methylbenzenesulfonamide Chemical class C1=CC(C)=CC=C1S(=O)(=O)NC1=NCCN1 WYWMMZFTXGQLCR-UHFFFAOYSA-N 0.000 abstract 1
- 150000002825 nitriles Chemical class 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- VNNLHYZDXIBHKZ-UHFFFAOYSA-N thiophene-2-sulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CS1 VNNLHYZDXIBHKZ-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/06—Heterocyclic 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
- C07D239/08—Heterocyclic 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
- C07D239/10—Oxygen or sulfur atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/06—Anabolic agents
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
- C07D275/02—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic 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
- C07D333/26—Heterocyclic 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
- C07D333/30—Hetero atoms other than halogen
- C07D333/34—Sulfur atoms
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/10—Compounds having one or more C—Si linkages containing nitrogen having a Si-N linkage
Landscapes
- 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
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 |
Family
ID=5823251
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL7240628A IL40628A (en) | 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 |
Country Status (31)
| Country | Link |
|---|---|
| JP (2) | JPS55391B2 (en) |
| AR (1) | AR195805A1 (en) |
| AT (1) | AT320152B (en) |
| BE (1) | BE790440A (en) |
| BG (2) | BG20813A3 (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) |
Families Citing this family (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3978056A (en) * | 1971-10-23 | 1976-08-31 | Bayer Aktiengesellschaft | Penicillins |
| US3972869A (en) * | 1971-10-23 | 1976-08-03 | Bayer Aktiengesellschaft | Penicillins |
| US3983105A (en) * | 1971-10-23 | 1976-09-28 | Bayer Aktiengesellschaft | Penicillins |
| US3974142A (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) |
| US4009272A (en) * | 1971-10-23 | 1977-02-22 | Bayer Aktiengesellschaft | Penicillins |
| US3974141A (en) * | 1971-10-23 | 1976-08-10 | Bayer Aktiengesellschaft | Penicillins |
| US3972870A (en) * | 1971-10-23 | 1976-08-03 | Bayer Aktiengesellschaft | Penicillins |
| DE2258973A1 (en) * | 1972-12-01 | 1974-06-06 | Bayer Ag | PENICILLIN, THE METHOD FOR MANUFACTURING IT AND THEIR USE AS A MEDICINAL PRODUCT |
| JPS587637B2 (en) * | 1973-12-27 | 1983-02-10 | 住友化学工業株式会社 | Shinkipenicillin no Seihou |
| DE2407715C2 (en) * | 1974-02-18 | 1982-12-02 | Bayer Ag, 5090 Leverkusen | Cephalosporins, processes for their production, as well as pharmaceuticals |
| IL47168A (en) * | 1974-05-09 | 1979-07-25 | Toyama Chemical Co Ltd | Mono or dioxo piperazino(thio)carbonylamino derivatives ofpenicillins and cephalosporins and process for producing the same |
| DE2525541C2 (en) * | 1975-06-07 | 1984-01-12 | Bayer Ag, 5090 Leverkusen | β-lactam antibiotics, processes for their preparation and pharmaceuticals containing them |
| DE2810083A1 (en) | 1978-03-08 | 1979-09-20 | Bayer Ag | BETA-LACTAM COMPOUNDS |
| GB0420722D0 (en) * | 2004-09-17 | 2004-10-20 | Addex Pharmaceuticals Sa | Novel allosteric modulators |
| EP1780213A1 (en) * | 2005-10-27 | 2007-05-02 | 3M Innovative Properties Company | Silicon-urea-azolides, their preparation and use in the preparation of silicones with isocyanate terminal groups |
| AR059898A1 (en) | 2006-03-15 | 2008-05-07 | Janssen Pharmaceutica Nv | DERIVATIVES OF 3-CIANO-PIRIDONA 1,4-DISUSTITUTED AND ITS USE AS ALLOSTERIC MODULATORS OF MGLUR2 RECEIVERS |
| TW200900065A (en) | 2007-03-07 | 2009-01-01 | Janssen Pharmaceutica Nv | 3-cyano-4-(4-pyridinyloxy-phenyl)-pyridin-2-one derivatives |
| TW200845978A (en) | 2007-03-07 | 2008-12-01 | Janssen Pharmaceutica Nv | 3-cyano-4-(4-tetrahydropyran-phenyl)-pyridin-2-one derivatives |
| NZ584152A (en) | 2007-09-14 | 2011-11-25 | Ortho Mcneil Janssen Pharm | 1,3-disubstituted 4-(aryl-x-phenyl)-1h-pyridin-2-ones |
| PT2203439E (en) | 2007-09-14 | 2011-02-11 | Ortho Mcneil Janssen Pharm | 1`,3`-disubstituted-4-phenyl-3,4,5,6-tetrahydro-2h, 1`h-ý1, 4`¨bipyridinyl-2`-ones |
| JP5433579B2 (en) | 2007-09-14 | 2014-03-05 | ジャンセン ファーマシューティカルズ， インコーポレイテッド． | 1,3-disubstituted-4-phenyl-1H-pyridin-2-one |
| MX2010005110A (en) | 2007-11-14 | 2010-09-09 | Ortho Mcneil Janssen Pharm | Imidazo[1,2-a]pyridine derivatives and their use as positive allosteric modulators of mglur2 receptors. |
| BRPI0918055A2 (en) | 2008-09-02 | 2015-12-01 | Addex Pharmaceuticals Sa | 3-azabicyclo [3,1,0] hexyl derivatives as metabotropic glutamate receptor modulators. |
| CA2738849C (en) | 2008-10-16 | 2016-06-28 | Addex Pharma S.A. | Indole and benzomorpholine derivatives as modulators of metabotropic glutamate receptors |
| JP5690277B2 (en) | 2008-11-28 | 2015-03-25 | ジャンセン ファーマシューティカルズ， インコーポレイテッド． | Indole and benzoxazine derivatives as modulators of metabotropic glutamate receptors |
| NZ596078A (en) | 2009-05-12 | 2013-06-28 | Janssen Pharmaceuticals Inc | 1,2,4-TRIAZOLO [4,3-a] PYRIDINE DERIVATIVES AND THEIR USE FOR THE TREATMENT OR PREVENTION OF NEUROLOGICAL AND PSYCHIATRIC DISORDERS |
| MY153913A (en) | 2009-05-12 | 2015-04-15 | Janssen Pharmaceuticals Inc | 7-aryl-1,2,4-triazolo[4,3-a]pyridine derivatives and their use as positive allosteric modulators of mglur2 receptors |
| CN102439015B (en) | 2009-05-12 | 2015-05-13 | 杨森制药有限公司 | 1,2,4-triazolo[4,3-a]pyridine derivatives and their use as positive allosteric modulators of mglur2 receptors |
| EP2440523A4 (en) * | 2009-06-10 | 2014-03-19 | Chongxi Yu | High penetration compositions or prodrugs of antimicrobials and antimicrobial-related compounds |
| US8993591B2 (en) | 2010-11-08 | 2015-03-31 | Janssen Pharmaceuticals, Inc. | 1,2,4-triazolo[4,3-a] pyridine derivatives and their use as positive allosteric modulators of MGLUR2 receptors |
| US9271967B2 (en) | 2010-11-08 | 2016-03-01 | Janssen Pharmaceuticals, Inc. | 1,2,4-triazolo[4,3-a]pyridine derivatives and their use as positive allosteric modulators of mGluR2 receptors |
| CA2814998C (en) | 2010-11-08 | 2019-10-29 | Janssen Pharmaceuticals, Inc. | 1,2,4-triazolo[4,3-a]pyridine derivatives and their use as positive allosteric modulators of mglur2 receptors |
| JO3368B1 (en) | 2013-06-04 | 2019-03-13 | Janssen Pharmaceutica Nv | 6,7-DIHYDROPYRAZOLO[1,5-a]PYRAZIN-4(5H)-ONE COMPOUNDS AND THEIR USE AS NEGATIVE ALLOSTERIC MODULATORS OF MGLUR2 RECEPTORS |
| JO3367B1 (en) | 2013-09-06 | 2019-03-13 | Janssen Pharmaceutica Nv | 1,2,4-TRIAZOLO[4,3-a]PYRIDINE COMPOUNDS AND THEIR USE AS POSITIVE ALLOSTERIC MODULATORS OF MGLUR2 RECEPTORS |
| ME03518B (en) | 2014-01-21 | 2020-04-20 | Janssen Pharmaceutica Nv | Combinations comprising positive allosteric modulators or orthosteric agonists of metabotropic glutamatergic receptor subtype 2 and their use |
| SI3096790T1 (en) | 2014-01-21 | 2019-11-29 | Janssen Pharmaceutica Nv | Combinations comprising positive allosteric modulators or orthosteric agonists of metabotropic glutamatergic receptor subtype 2 and their use |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1770620A1 (en) * | 1968-06-12 | 1971-11-11 | Bayer Ag | New penicillins |
-
0
- BE BE790440D patent/BE790440A/xx not_active IP Right Cessation
-
1971
- 1971-10-23 DE DE2152967A patent/DE2152967C3/en not_active Expired
-
1972
- 1972-10-12 SU SU1839113A patent/SU527139A3/en active
- 1972-10-17 RO RO197272544A patent/RO60670A/ro unknown
- 1972-10-17 RO RO197285500A patent/RO63066A/en unknown
- 1972-10-17 PH PH14018A patent/PH9893A/en unknown
- 1972-10-19 BG BG024757A patent/BG20813A3/en unknown
- 1972-10-19 CS CS727048A patent/CS188883B2/en unknown
- 1972-10-19 FI FI2897/72A patent/FI56839C/en active
- 1972-10-19 HU HUBA2815A patent/HU167986B/hu not_active IP Right Cessation
- 1972-10-19 BG BG021665A patent/BG21609A3/en unknown
- 1972-10-19 DD DD72166352A patent/DD106044B3/en unknown
- 1972-10-20 CA CA154,338A patent/CA1019323A/en not_active Expired
- 1972-10-20 ZA ZA727473A patent/ZA727473B/en unknown
- 1972-10-20 SE SE7213592A patent/SE412236B/en unknown
- 1972-10-20 LU LU66332A patent/LU66332A1/xx unknown
- 1972-10-20 DK DK522172A patent/DK134992C/en active
- 1972-10-20 AT AT901072A patent/AT320152B/en not_active IP Right Cessation
- 1972-10-20 CH CH1531272A patent/CH579089A5/xx not_active IP Right Cessation
- 1972-10-20 IE IE1422/72A patent/IE37123B1/en unknown
- 1972-10-20 IL IL7240628A patent/IL40628A/en unknown
- 1972-10-21 PL PL1972158392A patent/PL89056B1/pl unknown
- 1972-10-21 EG EG437/72A patent/EG10826A/en active
- 1972-10-21 PL PL1972183057A patent/PL93574B1/pl unknown
- 1972-10-21 JP JP10490172A patent/JPS55391B2/ja not_active Expired
- 1972-10-21 JP JP10490272A patent/JPS57843B2/ja not_active Expired
- 1972-10-21 ES ES407851A patent/ES407851A1/en not_active Expired
- 1972-10-23 FR FR7237482A patent/FR2157908B1/fr not_active Expired
- 1972-10-23 NO NO723810A patent/NO143909C/en unknown
- 1972-10-23 AR AR244770A patent/AR195805A1/en active
- 1972-10-23 CY CY947A patent/CY947A/en unknown
- 1972-10-23 GB GB4869972A patent/GB1392849A/en not_active Expired
- 1972-10-23 YU YU02640/72A patent/YU264072A/en unknown
-
1978
- 1978-03-14 KE KE2824A patent/KE2824A/en unknown
- 1978-04-04 HK HK185/78A patent/HK18578A/en unknown
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