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1. 发明授权

US4801705A 2-oxo-1-(((substituted sulfonyl)amino)-carbonyl)azetidines 失效
标题翻译： 2-氧代-1 - （（（取代的磺酰基）氨基） - 羰基）氮杂环丁烷
公开(公告)号：US4801705A
公开(公告)日：1989-01-31
申请号：US877599
申请日：1986-06-23
申请人： Hermann Breuer , Jakob-Matthias Drossard , Peter H. Ermann , Henner Straub , Uwe D. Treuner
发明人： Hermann Breuer , Jakob-Matthias Drossard , Peter H. Ermann , Henner Straub , Uwe D. Treuner
IPC分类号： A61K31/395 , A61K31/397 , A61K31/495 , A61P31/04 , C07D205/08 , C07D205/085 , C07D403/12 , C07D417/12 , C07D417/14 , A61K31/415
CPC分类号： C07D417/12 , C07D417/14
摘要： Antibacterial activity is exhibited by .beta.-lactams having a 3-acylamino substituent and having in the 1-position an activating group of the formula ##STR1## wherein R is

2. 发明授权

US4762922A 2-oxo-1-[[(substituted sulfonyl)amino]-carbonyl]azetidines 失效
标题翻译： 2-氧代-1 - [[（取代的磺酰基）氨基]羰基]氮杂环丁烷
公开(公告)号：US4762922A
公开(公告)日：1988-08-09
申请号：US70286
申请日：1987-07-01
申请人： Hermann Breuer , Uwe D. Treuner
发明人： Hermann Breuer , Uwe D. Treuner
IPC分类号： C07D401/14 , A61K31/44 , A61K31/4427 , A61P31/04 , C07D401/12 , C07D417/14 , A61K31/395 , A61K31/425
CPC分类号： C07D401/12 , C07D417/14
摘要： Antibacterial activity is exhibited by 2-azetidinones having a 3-acylamino substituent and having an activating group in the 1-position of the formula ##STR1## wherein R is ##STR2## A.sub.1 is --NH-- or ##STR3## A.sub.2 is ##STR4## or --CH.dbd.CH--.
摘要翻译：具有3-酰基氨基取代基的2-氮杂环丁酮和具有式Ia的1位的具有活化基团的抗菌活性表现为其中R为“IMA”或“IMA”> A1为-NH-或 A2 是 + TR 或-CH = CH-。

3. 发明授权

US4127716A 3-HETEROTHIOMETHYL UREIDO CEPHALOSPORINS 失效
标题翻译： 3-HETEROTHOMETHYL UREIDO CEPHALOSPORINS
公开(公告)号：US4127716A
公开(公告)日：1978-11-28
申请号：US764134
申请日：1977-02-02
申请人： Hermann Breuer , Uwe D. Treuner
发明人： Hermann Breuer , Uwe D. Treuner
IPC分类号： C07D307/54 , C07D333/24 , C07D501/36 , C07D501/56 , A61K31/545 , C07D501/54
CPC分类号： C07D333/24 , C07D307/54
摘要： L-Isomer compounds of the formula ##STR1## wherein R.sub.1 is phenyl, thienyl or furyl; R.sub.4 represents certain heterocyclic groups; R.sub.3 is hydrogen, lower alkyl, phenyl-lower alkyl, substituted phenyl-lower alkyl, diphenyl-lower alkyl, tri(lower alkyl)stannyl, tri(lower alkyl)silyl, a salt forming ion, or the group ##STR2## wherein R is lower alkyl, phenyl, phenyl-lower alkyl, or substituted phenyl and phenyl-lower alkyl are disclosed. These compounds are useful as antibacterial agents.
摘要翻译：其中R1是苯基，噻吩基或呋喃基的式（Ⅰ）的L-异构体化合物; R4表示某些杂环基; R3是氢，低级烷基，苯基 - 低级烷基，取代的苯基 - 低级烷基，二苯基 - 低级烷基，三（低级烷基）甲锡烷基，三（低级烷基）甲硅烷基，成盐离子或基团，其中R 是低级烷基，苯基，苯基 - 低级烷基或取代的苯基和苯基 - 低级烷基。这些化合物可用作抗菌剂。

4. 发明授权

US4100345A 3-(Carbamoyl)pyridino derivatives of 7a-methoxy ureidocephalosporins 失效
标题翻译： 7-甲氧基脲基头孢菌素的3-（氨基甲酰基）吡啶衍生物
公开(公告)号：US4100345A
公开(公告)日：1978-07-11
申请号：US761914
申请日：1977-01-24
申请人： Hermann Breuer , Uwe D. Treuner
发明人： Hermann Breuer , Uwe D. Treuner
IPC分类号： C07D333/24 , C07D501/38 , C07D501/44 , C07D501/40
CPC分类号： C07D333/24
摘要： Ureido cephalosporin derivatives of the formula ##STR1## wherein R.sub.1 is hydrogen or methoxy; R.sub.2 is hydrogen or lower alkyl; R.sub.3 is hydrogen, lower alkyl, cycloalkyl, cycloalkenyl, cycloalkadienyl, phenyl, phenyl-lower alkyl, substituted phenyl, substituted phenyl-lower alkyl; or certain heterocyclic groups; are disclosed. These compounds are useful as antibacterial agents.
摘要翻译：其中R1是氢或甲氧基的式“IMAGE”的脲基头孢菌素衍生物; R2是氢或低级烷基; R3是氢，低级烷基，环烷基，环烯基，环链二烯基，苯基，苯基 - 低级烷基，取代的苯基，取代的苯基 - 低级烷基; 或某些杂环基团; 被披露。这些化合物可用作抗菌剂。

5. 发明授权

US4093801A [[[(2,4-Dioxo-1-imidazolidinyl)amino]carbonyl]amino]-acetylcephalosporin derivatives 失效
标题翻译： {8 {8（2,4-二氧代-1-咪唑啉基）氨基{9羰基{9氨基{9-乙酰头孢菌素衍生物
公开(公告)号：US4093801A
公开(公告)日：1978-06-06
申请号：US819648
申请日：1977-07-27
申请人： Hermann Breuer , Uwe D. Treuner
发明人： Hermann Breuer , Uwe D. Treuner
IPC分类号： A61K31/545 , A61K31/546 , A61P31/04 , C07D233/80 , C07D333/24 , C07D501/20 , C07D501/36 , C07D501/34 , C07D501/46
CPC分类号： C07D333/24 , C07D233/80
摘要： [[[(2,4-Dioxo-1-imidazolidinyl)amino]carbonyl]amino]-acetylcephalosporin derivatives having the formula ##STR1## wherein R is hydrogen, lower alkyl, phenyl-lower alkyl, diphenyl-lower alkyl, tri(lower alkyl)silyl, trihaloethyl, a salt forming ion, or the group ##STR2## R.sub.1 is hydrogen or methoxy; R.sub.2, R.sub.3 and R.sub.5 each is hydrogen or lower alkyl; R.sub.4 is hydrogen, lower alkyl, cyclo-lower alkyl, cyclo-lower alkenyl, cyclo-lower alkadienyl, phenyl, phenyl-lower alkyl, substitutted phenyl, substituted phenyl-lower alkyl, or certain heterocyclic groups; R.sub.6 is lower alkyl; and X is hydrogen, lower alkanoyloxy, ##STR3## or certain heterothio groups; are useful as antibacterial agents.
摘要翻译：具有下式的[[[（2,4-二氧代-1-咪唑烷基）氨基]羰基]氨基] - 乙酰头孢菌素衍生物其中R是氢，低级烷基，苯基 - 低级烷基，二苯基 - 低级烷基，三（低级）烷基）甲硅烷基，三卤代乙基，成盐离子，或基团R 1是氢或甲氧基; R2，R3和R5各自为氢或低级烷基; R4是氢，低级烷基，环低级烷基，环低级烯基，环低级亚烷基，苯基，苯基 - 低级烷基，取代的苯基，取代的苯基 - 低级烷基或某些杂环基; R6是低级烷基; X是氢，低级烷酰氧基，或者某些杂硫基; 作为抗菌剂是有用的。

6. 发明授权

US4088815A 3-Heterothio-7-ureido cephalosporins 失效
标题翻译： 3-异硫脲-7-脲基头孢菌素
公开(公告)号：US4088815A
公开(公告)日：1978-05-09
申请号：US664795
申请日：1976-03-08
申请人： Hermann Breuer , Uwe D. Treuner
发明人： Hermann Breuer , Uwe D. Treuner
IPC分类号： C07D213/55 , C07D333/24 , C07D501/36
CPC分类号： C07D333/24 , C07D213/55
摘要： Compounds of the formula ##STR1## wherein R.sub.1 is hydrogen, lower alkyl, cycloalkyl, cycloalkenyl, cycloalkadienyl, phenyl, phenyl-lower alkyl and substituted phenyl and phenyl-lower alkyl; R.sub.2 is hydrogen or lower alkyl; R.sub.3 is hydrogen, lower alkyl, phenyl-lower alkyl, substituted phenyl-lower alkyl, diphenyl-lower alkyl, tri(lower alkyl)stannyl, tri(lower alkyl)silyl, a salt forming ion, or the group ##STR2## wherein R is lower alkyl, phenyl, phenyl-lower alkyl, or substituted phenyl and phenyl-lower alkyl; and R.sub.4 represents certain heterocyclic groups are disclosed. These compounds are useful as antibacterial agents.
摘要翻译：其中R 1是氢，低级烷基，环烷基，环烯基，环烷二烯基，苯基，苯基 - 低级烷基和取代的苯基和苯基 - 低级烷基; R2是氢或低级烷基; R3是氢，低级烷基，苯基 - 低级烷基，取代的苯基 - 低级烷基，二苯基 - 低级烷基，三（低级烷基）甲锡烷基，三（低级烷基）甲硅烷基，成盐离子或基团，其中R 是低级烷基，苯基，苯基 - 低级烷基或取代的苯基和苯基 - 低级烷基; 并且R4表示某些杂环基。这些化合物可用作抗菌剂。

7. 发明授权

US4087423A Pyrazolo[4,3-e][1,2,4]triazolo[4,3-c]pyridines 失效
标题翻译：吡唑并{8,43-e {9 {8 1,2,4 {9三唑并{8,3,3-c {9吡啶
公开(公告)号：US4087423A
公开(公告)日：1978-05-02
申请号：US817282
申请日：1977-07-20
申请人： Uwe D. Treuner , Hermann Breuer
发明人： Uwe D. Treuner , Hermann Breuer
IPC分类号： A61K31/505 , A61K31/535 , A61P29/00 , C07D231/38 , C07D487/04 , C07D487/14
CPC分类号： C07D231/38 , C07D487/04 , C07D487/14 , Y10S514/87
摘要： New pyrazolo[4,3-e][1,2,4]triazolo[4,3-c]pyrimidines have the general formula ##STR1## They are useful as antiinflammatory agents.

8. 发明授权

US4028354A Alkenyl and alkinylureido cephalosporins 失效
标题翻译：烯基和炔基脲基头孢菌素
公开(公告)号：US4028354A
公开(公告)日：1977-06-07
申请号：US664467
申请日：1976-03-08
申请人： Hermann Breuer , Uwe D. Treuner
发明人： Hermann Breuer , Uwe D. Treuner
IPC分类号： C07D501/36
CPC分类号： C07D501/36
摘要： Alkenyl and alkinylureido cephalosporins of the formula ##STR1## wherein R is hydrogen, lower alkyl, phenyl-lower alkyl, diphenyl-lower alkyl, tri(lower alkyl)silyl, trihaloethyl, a salt forming ion, or the group ##STR2## R.sub.1 is hydrogen or methoxy; R.sub.2 is lower alkenyl or lower alkinyl, R.sub.3 is hydrogen or lower alkyl; R.sub.4 is hydrogen, lower alkyl, cycloalkyl, cycloalkenyl, cycloalkadienyl, phenyl, phenyl-lower alkyl, substituted phenyl, substituted phenyl-lower alkyl, or certain heterocyclic groups; R.sub.5 is hydrogen or lower alkyl; R.sub.6 is lower alkyl; and X is hydrogen, lower alkanoyloxy, ##STR3## or certain heterothio groups; are disclosed. These compounds are useful as antibacterial agents.
摘要翻译：其中R是氢，低级烷基，苯基 - 低级烷基，二苯基 - 低级烷基，三（低级烷基）甲硅烷基，三卤代乙基，成盐离子或基团R1的烯基和炔基脲基头孢菌素氢或甲氧基; R2是低级烯基或低级炔基，R3是氢或低级烷基; R4是氢，低级烷基，环烷基，环烯基，环链二烯基，苯基，苯基 - 低级烷基，取代的苯基，取代的苯基 - 低级烷基或某些杂环基; R5是氢或低级烷基; R6是低级烷基; X是氢，低级烷酰氧基，或者某些杂硫基; 被披露。这些化合物可用作抗菌剂。

9. 发明授权

US3996217A 3-Triazolylthio derivatives of ureido cephalosporins 失效
标题翻译：脲基头孢菌素的3-三唑基硫代衍生物
公开(公告)号：US3996217A
公开(公告)日：1976-12-07
申请号：US611040
申请日：1975-09-08
申请人： Hermann Breuer , Uwe D. Treuner
发明人： Hermann Breuer , Uwe D. Treuner
IPC分类号： C07D501/28 , A61K31/545 , A61K31/546 , A61P31/04 , C07D333/24 , C07D501/32 , C07D501/36 , C07D501/57 , C07D501/24
CPC分类号： C07D333/24
摘要： Ureido cephalosporin derivatives of the formula ##STR1## wherein R is hydrogen, lower alkyl, phenyl-lower alkyl, diphenyllower alkyl, tri(lower alkyl)silyl, trihaloethyl, a salt forming ion, or the group ##STR2## R.sub.1 is hydrogen, lower alkyl, cycloalkyl, cycloalkenyl, cycloalkadienyl, phenyl, phenyl-lower alkyl, substituted phenyl or phenyl-lower alkyl, or certain heterocyclic groups; R.sub.2 is hydrogen or lower alkyl; R.sub.3 is hydrogen or methoxy; R.sub.4 is triazolyl or substituted triazolyl; R.sub.5 is hydrogen or lower alkyl; R.sub.6 is lower alkyl, phenyl, or phenyl-lower alkyl; are disclosed. These compounds are useful as antibacterial agents.
摘要翻译：其中R为氢，低级烷基，苯基 - 低级烷基，二苯基低级烷基，三（低级烷基）甲硅烷基，三卤代乙基，成盐离子或基团R 1的氢原子，头孢菌素衍生物为下式烷基，环烷基，环烯基，环烷二烯基，苯基，苯基 - 低级烷基，取代的苯基或苯基 - 低级烷基或某些杂环基; R2是氢或低级烷基; R3是氢或甲氧基; R4是三唑基或取代的三唑基; R5是氢或低级烷基; R6是低级烷基，苯基或苯基 - 低级烷基; 被披露。这些化合物可用作抗菌剂。

10. 发明授权

US3991051A [(Oxyalkyl)thioacetyl]cephalosporin derivatives 失效
标题翻译： {8（氧烷基）硫代乙酰基{9头孢菌素衍生物
公开(公告)号：US3991051A
公开(公告)日：1976-11-09
申请号：US573676
申请日：1975-05-01
申请人： Hermann Breuer , Uwe D. Treuner
发明人： Hermann Breuer , Uwe D. Treuner
IPC分类号： C07D501/20 , C07D501/28 , C07D501/32
CPC分类号： C07C323/00
摘要： [(Oxyalkyl)thioacetyl] cephalosporin derivatives having the formula ##EQU1## wherein R is hydrogen, lower alkyl, phenyl-lower alkyl, tri(lower alkyl)silyl, a salt forming ion, or the group ##EQU2## R.sub.1 is hydrogen, lower alkyl, phenyl, thienyl or furyl; R.sub.2 and R.sub.6 each is hydrogen or lower alkyl; R.sub.3 and R.sub.5 each is lower alkyl, phenyl or phenyl-lower alkyl; and R.sub.4 is hydrogen, hydroxy, lower alkanoyloxy, lower alkoxy or lower alkylthio; are useful as antimicrobial agents.SUMMARY OF THE INVENTIONThis invention relates to new [(oxyalkyl)thioacetyl]cephalosporin derivatives having the formula ##STR1##R represents hydrogen, lower alkyl, phenyl-lower alkyl, tri(lower alkyl)silyl, a salt forming ion or the group ##STR2## R.sub.1 represents hydrogen, lower alkyl, phenyl, thienyl or furyl; R.sub.2 and R.sub.6 each represents hydrogen or lower alkyl; R.sub.3 and R.sub.5 each represents lower alkyl, phenyl or phenyl-lower alkyl; and R.sub.4 represents hydrogen, hydroxy, lower alkanoyloxy, lower alkoxy or lower alkylthio.The especially preferred members within each group are as follows: R is hydrogen, alkali metal, diphenylmethyl or ##STR3## especially hydrogen, pivaloyloxy, sodium or potassium; R.sub.1 is hydrogen or phenyl; R.sub.2 is hydrogen; R.sub.3 is lower alkyl, especially methyl; R.sub.4 is hydrogen or acetoxy; and R.sub.5 is methyl or t-butyl.DETAILED DESCRIPTION OF THE INVENTIONThe various groups represented by the symbols have the meanings defined below and these definitions are retained throughout this specification.The lower alkyl groups are the straight and branched chain hydrocarbon groups in the series from methyl to heptyl, the C.sub.1 to C.sub.4 groups and especially methyl and ethyl being generally preferred. The lower alkoxy and lower alkylthio groups are of the same type and the same preferences apply.The lower alkanoyloxy groups represented by R.sub.4 include the acyl radicals of lower fatty acids containing alkyl radicals of the type described above, e.g., acetoxy, propionoxy, butyryloxy, etc., the C.sub.1 to C.sub.4 members being preferred and acetoxy being especially preferred.The phenyl-lower alkyl radicals include a phenyl ring attached to a lower alkyl group of the kind described above like benzyl and phenethyl as well as those containing two phenyl groups such as diphenylmethyl.The salt forming ions represented by R are metal ions, e.g., alkali metal ions such as sodium or potassium, alkaline earth metal ions such as calcium or magnesium or an amine salt ion, e.g., a (lower alkyl)amine like methylamine or triethylamine.The new [(oxyalkyl)thioacetyl)cephalosporin derivatives of this invention are produced by reacting a 7-aminocephalosporanic acid compound, e.g., 7-aminocephalosporanic acid (7-ACA), 7-amino-3-desacetoxycephalosporanic acid (7-ADCA) and other derivatives, having the formula ##STR4## or derivatives thereof with an [(oxyalkyl)thio]acetic acid of the formula ##STR5## or an acid halide, anhydride including mixed anhydrides, activated esters or the like.The derivatives of II referred to include, for example, the triethylamine derivative, benzhydryl ester or the like. The acid halide of III is preferably the chloride. Coupling agents like dicyclohexylcarbodiimide or the like can also be used.A preferred method is the reaction between the 7-aminocephalosporanic acid compound and the [(oxyalkyl)-thio]acetic acid, for example, by dissolving or suspending the latter in an inert organic solvent such as chloroform, tetrahydrofuran, methylene chloride, dioxane, benzene or the like, and adding, at a reduced temperature of about 0.degree. to -20.degree. C about an equimolar amount of the 7-ACA or 7-ADCA compound, preferably in the form of its diphenylmethyl ester, in the presence of an activating compound such as dicyclohexylcarbodiimide. The product of the reaction is then isolated by conventional procedures, e.g., by filtration and concentration or evaporation of the solvent. The diphenylmethyl ester is converted to the free acid, e.g., with trifluoroacetic acid and anisole. Any of the salts can then be produced by conventional treatment, e.g., with potassium ethyl hexanoate, sodium bicarbonate or the like.Another preferred method involves the reaction of a 7-aminocephalosporanic acid compound with the acid halide of the [(oxyalkyl)thio]acetic acid in aqueous alkaline medium.When R is the acyloxymethyl group ##STR6## this group may be introduced into the 7-aminocephalosporanic acid moiety prior to the reaction with the [(oxyalkyl)thio]-acetic acid or derivative by treatment with one to two moles of a halomethyl ester of the formula ##STR7## wherein hal is halogen, preferably chlorine or bromine, in an inert organic solvent such as dimethylformamide, acetone, dioxane, benzene or the like, at about ambient temperature or below.The [(oxyalkyl)thio]acetic acid of formula III is produced by reacting a mercaptoacetic acid of the formula ##STR8## with a halogenated compound of the formula ##STR9## in the presence of a base like triethylamine in a solvent like tetrahydrofuran and then hydrolyzing the ester formed in the process.Alternatively, when the acid halide is used to react with the 7-aminocephalosporanic acid compound, an alkoxide R.sub.3 -OMe (wherein Me is a metal like sodium or potassium) is made to react with a haloester of the formula ##STR10## to obtain the intermediate of the formula ##STR11##Treatment with a base, e.g., an alkali metal hydroxide like potassium hydroxide, converts the ester to a salt which is then converted to the acid chloride with a halogenating agent like oxalyl chloride.Further process details are provided in the illustrative examples.Certain of the compounds of this invention may exist in different optically active forms. The various stereoisomeric forms as well as the racemic mixtures are within the scope of the invention.The compounds of this invention have a broad spectrum of antibacterial activity against both gram positive and gram negative organisms such as Staphylococcus aureus, Salmonella schottmuelleri, Pseudomonas aeruginosa, Proteus vulgaris, Escherichia coli and Streptococcus pyrogenes. They can be used as antibacterial agents to combat infections due to organisms such as those named above, and in general may be utilized in a manner similar to cephradine and other cephalosporins. For example, a compound of formula I or a physiologically acceptable salt thereof can be used in various animal species in an amount of about 1 to 150 mg/kg, daily, orally or parenterally, in single or two to four divided doses to treat infections of bacterial origin, e.g., 7.0 mg/kg is used in mice.Up to about 600 mg. of a compound of formula I or a physiologically acceptable salt thereof is incorporated in an oral dosage form such as tablets, capsules or elixirs or in an injectable form in a sterile aqueous vehicle prepared according to conventional pharmaceutical practice.
摘要翻译：具有下式的[（氧代烷基）硫代乙酰基]头孢菌素衍生物：R 2 R 3 S || R 3 -O-CH-S-CH-CO-NH-CH-CHCH 2 || C-NC-CH 2 -R 4平行角OC | C-OR 其中R是氢，低级烷基，苯基 - 低级烷基，三（低级烷基）甲硅烷基，成盐离子或基团R6O |平行-CH-OC-R5; R 1是氢，低级烷基，苯基，噻吩基或呋喃基; R2和R6各自为氢或低级烷基; R3和R5各自为低级烷基，苯基或苯基 - 低级烷基; 和R4是氢，羟基，低级烷酰氧基，低级烷氧基或低级烷硫基; 作为抗微生物剂是有用的。

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