GB1119334A - Para-substituted phenylacetic acids, aldehydes and alocohols and their derivatives - Google Patents

Para-substituted phenylacetic acids, aldehydes and alocohols and their derivatives

Info

Publication number
GB1119334A
GB1119334A GB4951765A GB4951765A GB1119334A GB 1119334 A GB1119334 A GB 1119334A GB 4951765 A GB4951765 A GB 4951765A GB 4951765 A GB4951765 A GB 4951765A GB 1119334 A GB1119334 A GB 1119334A
Authority
GB
United Kingdom
Prior art keywords
lower alkyl
phenyl
alkyl
free acids
cooh
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
GB4951765A
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.)
Merck and Co Inc
Original Assignee
Merck and Co Inc
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
Application filed by Merck and Co Inc filed Critical Merck and Co Inc
Publication of GB1119334A publication Critical patent/GB1119334A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
    • C07D213/46—Oxygen atoms
    • C07D213/50—Ketonic radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/55—Acids; Esters
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen 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
    • C07D213/61—Halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • 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
    • C07D333/06—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
    • C07D333/16—Radicals substituted by singly bound hetero atoms other than halogen by oxygen atoms
    • 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
    • C07D333/06—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/22—Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom
    • 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
    • C07D333/06—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Pyridine Compounds (AREA)

Abstract

Compounds of the general formula <FORM:1119334/C2/1> (wherein Het represents a thienyl, furyl, pyridyl, thiazolyl, oxazolyl, isoxazolyl, pyrazolyl or imidazolyl radical, R1 represents H or a lower alkyl, alkenyl, alkynyl or haloalkyl radical and R2 represents H, or R1 and R2 together represent a methylene, C2- 5 alkylidene or ethylene radical, R3 and R4 each represent a halogen atom or a lower alkyl, alkylthio, alkylsulphonyl or alkanoylamino, trihalomethyl, SH, NH2, di-(lower alkyl)-amino, CN, NO2, CONH2, di-(lower alkyl)-carbamoyl, di-(lower alkyl)-sulphamoyl, phenyl, acetyl, trifluoroacetyl or trifluoro-methylthio radical, n and m are each 0,1 or 2, X represents COOH; COOM where M is an equivalent of a pharmaceutically non-toxic cation; COOR111 where R111 is lower alkyl, alkenyl or alkynyl, C3- 6 cycloalkyl, aralkyl, morpholinoalkyl, phenyl, (lower alkanoylamino-phenyl, carboxyphenyl, carbamoylphenyl, mono- or poly-(lower alkoxy)-lower alkyl, lower polyhydroxyalkyl or di-(lower alkyl)-amino-lower alkyl; CONY1Y11 where Y1 and Y11 are each H, lower alkyl, mono- or poly-hydroxy-lower alkyl, phenyl-lower alkyl, phenyl, (lower alkoxy)-phenyl, halophenyl, trifluoro-methylphenyl, cyclohexyl, carboxymethyl, 1-carboxy-3-carbamoylpropyl, N, N-di - (lower alkyl) - carbamoylmethyl, N, N-di-(lower alkyl)-amino-lower alkyl, N-(lower alkyl)-pyrrolidyl or N-(lower alkyl)-pyrrolidyl-lower alkyl or Y1 and Y11 jointly form with N amorpho ino, 1-piperazinyl, 4-loweralkyl-1-piperazinyl, 4 - phenyl - 1 - piperazinyl, 4 - (b -hydroxyethyl) - 1 - piperazinyl, 1 - pyrrolidinyl or piperidino radical; CHO; CH2OH; CH2OR6 where R6 is alkyl, alkenyl, aralkyl or alkoxyalkyl or CH(OR7)2 where R7 is alkyl, and the term "lower" means "containing not more than 5 carbon atoms, excluding those in any functional groups such as CO, OCO, COOH, CN or CONH2" are prepared by the following methods: (I) for free acids (X = COOH) wherein R1 = R2 = H, carrying out the following process: <FORM:1119334/C2/2> (wherein R3 and R4 each represent halogen, NO2, di-(lower alkyl)- sulphamoyl, di-(lower alkyl)-carbamoyl, trihalomethyl, lower alkyl, acetyl, trifluoroacetyl, trifluoromethylthio or phenyl); (II) for free acids (X = COOH) wherein R1 and R2 are jointly methylene C2- 5 alkylidene or ethylene, carrying out the following process: <FORM:1119334/C2/3> (wherein neither R3 nor R4 may represent NO2, CN, CONH2 or alkanoylamino); (III) for free acids (X = COOH) wherein R1 is lower alkyl, alkenyl, alkynyl or haloalkyl and R2 is H, carrying out the following process <FORM:1119334/C2/4> (wherein R3 and R4 each represent halogen, NO2, lower alkyl, alkylthio or alkylsulphonyl, di-(lower alkyl) - sulphamoyl, trihalomethyl, phenyl-lower alkyl, di - (lower alkyl) - carbamoyl, acetyl, trifluoroacetyl or trifluoromethylthio); (IV) for free acids (X = COOH) wherein R1 is lower alkyl and R2 is H, hydrogenating the corresponding compounds wherein R1 and R2 are jointly methylene or C2- 5 alkylidene and wherein R3 and R4 are restricted as in (II); (V) after any of the foregoing processes, introducing further desired substituents by one or more of the following steps: nitration; reduction of NO2 to NH2; dialkylating or alkanoylating NH2; replacing NH2 by SH or CN by diazotization and reaction of the diazonium salt with a C1- 5 alkyl xanthate under alkaline conditions or with cuprous cyanide; alkylating SH; oxidizing S-Alkyl to SO2-Alkyl; subjecting SH to the process SH-->SO3H-->SO2Cl-->SO2N(Alkyl)2; acid hydrolysis of CN to CONH2; (VI) for salts (X = COOM), reacting the free acids with inorganic or organic bases containing pharmaceutically nontoxic cations; (VII) for esters (X = COOR111), omitting the hydrolysis step in certain of the foregoing processes, or esterifying the free acids with R111OH; (VIII) for amides (X = CONY1Y11), amidating the free acids with HNY1Y11; (IX) for aldehydes (X = CHO), benzylating any R3 or R4 substituents containing active H in the free acids, converting them to their acid halides, and reducing these (with simultaneous removal of any benzyl groups) by means of H2 in the presence of BaSO4/Pd and quinoline or of an alkali or alkaline-earth metal tri-t-butoxy aluminium hydride; (X) for acetals (X = CH(OR7)2), reacting the aldehydes with a C1- 5 alkanol in the presence of at least a catalytic amount of a strong acid; (XI) for alcohols (X = CH2OH), reducing the corresponding acids with an alkali or alkaline-earth metal aluminium hydride; (XII) for ethers (X = CH2OR6), reacting the alcohols with a strongly basic condensing agent and with an alkyl, alkenyl, aralkyl or alkoxyalky halide. Starting materials.-The preparation of the starting materials for processes (I) and II) is described, the following compounds being among those formed in the course of these preparations: 2 - (4 - amino - and 4 - cyano - 2 - chlorophenyl) - thiophene, - furan, - thiazole, - pyrazole and - isoxazole; ethyl 4 - (2-, 3-and 4 - pyridyl) - 3 - chlorobenzoate; 2 - phenyl-, 2 - p - nitrophenyl-, 2 - p - aminophenyl- and 2 - p - cyano-phenyl - 6 - chloropyridine; 21 - chloro - 41 - nitro - 2 - chloroacetophenone: 4 - (2 - chloro - 4 - nitrophenyl) - thiazole, -oxazole, -imidazole, -pyrazole and isoxazole; 4 - p - nitrophenyloxazole; 2 - methyl - 4 - chloro- 4 - nitrophenyl) - imidazole; 4 - p - nitrophenylpyrazole; 2 - chloro - 4 - nitrophenyl b -chlorovinyl ketone; 4 - p - nitrophenyl-isoxazole. Pharmaceutical compositions, having antiinflammatory, activity, comprise the compounds of the invention (other than those having an a -C3- 5 alkylidene substituent) together with nontoxic diluents, carriers or coatings.
GB4951765A 1964-11-27 1965-11-22 Para-substituted phenylacetic acids, aldehydes and alocohols and their derivatives Expired GB1119334A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US41442864A 1964-11-27 1964-11-27

Publications (1)

Publication Number Publication Date
GB1119334A true GB1119334A (en) 1968-07-10

Family

ID=23641410

Family Applications (1)

Application Number Title Priority Date Filing Date
GB4951765A Expired GB1119334A (en) 1964-11-27 1965-11-22 Para-substituted phenylacetic acids, aldehydes and alocohols and their derivatives

Country Status (4)

Country Link
BR (1) BR6574940D0 (en)
DE (1) DE1595964A1 (en)
FR (2) FR1479252A (en)
GB (1) GB1119334A (en)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2345276A1 (en) * 1972-09-07 1974-04-25 Rhone Poulenc Sa NEW PHENYL ACID AND PHENYLPROPIONIC ACID DERIVATIVES, THEIR PRODUCTION AND THE COMPOSITIONS THAT CONTAIN THEM
JPS5481260A (en) * 1977-11-21 1979-06-28 Toyama Chem Co Ltd 2-4-(3-methyl-2-thienyl)phenyl propionic acid, its nontoxic salt and antiphlogistics, analgesics, and antirheumatics containing them
US4226878A (en) * 1978-06-13 1980-10-07 Kissei Pharmaceutical Co., Ltd. Imidazole derivative
US4230719A (en) * 1977-11-21 1980-10-28 Toyama Chemical Co., Ltd. Novel 2-[4-(3-methyl-2-thienyl)phenyl]propionic acid and pharmaceutically acceptable salt thereof and method for treating symptoms of inflammation and pain
US4239901A (en) * 1976-10-14 1980-12-16 Byk Gulden Lomberg Chemische Fabrik Gmbh Pyrazol-1-ylphenylacetic acids
US4271170A (en) 1978-12-28 1981-06-02 Ono Pharmaceutical Co., Ltd., Pyridine derivatives
GB2181728A (en) * 1985-10-21 1987-04-29 Indian Drugs & Pharma 4-(3-Thienyl)phenylalkanoic acids and derivatives and process for their preparation

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1795036A1 (en) * 1968-08-01 1972-01-20 Merck Patent Gmbh p-Aminoarylalkanol derivatives and processes for their preparation
DE1900585A1 (en) * 1969-01-07 1970-10-15 Merck Patent Gmbh p-Aminoarylalkanal derivatives and processes for their preparation
JPS5572167A (en) * 1978-11-27 1980-05-30 Dainippon Pharmaceut Co Ltd Pyridylaminophenylacetic acid derivative and its preparation

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2345276A1 (en) * 1972-09-07 1974-04-25 Rhone Poulenc Sa NEW PHENYL ACID AND PHENYLPROPIONIC ACID DERIVATIVES, THEIR PRODUCTION AND THE COMPOSITIONS THAT CONTAIN THEM
US4239901A (en) * 1976-10-14 1980-12-16 Byk Gulden Lomberg Chemische Fabrik Gmbh Pyrazol-1-ylphenylacetic acids
JPS5481260A (en) * 1977-11-21 1979-06-28 Toyama Chem Co Ltd 2-4-(3-methyl-2-thienyl)phenyl propionic acid, its nontoxic salt and antiphlogistics, analgesics, and antirheumatics containing them
US4230719A (en) * 1977-11-21 1980-10-28 Toyama Chemical Co., Ltd. Novel 2-[4-(3-methyl-2-thienyl)phenyl]propionic acid and pharmaceutically acceptable salt thereof and method for treating symptoms of inflammation and pain
JPS563327B2 (en) * 1977-11-21 1981-01-24
US4226878A (en) * 1978-06-13 1980-10-07 Kissei Pharmaceutical Co., Ltd. Imidazole derivative
US4271170A (en) 1978-12-28 1981-06-02 Ono Pharmaceutical Co., Ltd., Pyridine derivatives
GB2181728A (en) * 1985-10-21 1987-04-29 Indian Drugs & Pharma 4-(3-Thienyl)phenylalkanoic acids and derivatives and process for their preparation
GB2181728B (en) * 1985-10-21 1990-01-24 Indian Drugs & Pharma 4-(3-thienyl)phenylalkanoic acids and derivatives and process for their preparation

Also Published As

Publication number Publication date
FR1479252A (en) 1967-05-05
BR6574940D0 (en) 1973-08-07
DE1595964A1 (en) 1970-03-12
FR5664M (en) 1968-01-02

Similar Documents

Publication Publication Date Title
EP0316594B1 (en) Aminomethyl oxooxazolidinyl ethenylbenzene derivatives useful as antibacterial agents
GB1119334A (en) Para-substituted phenylacetic acids, aldehydes and alocohols and their derivatives
US4977173A (en) Aminomethyl oxooxazolidinyl ethenylbenzene derivatives useful as antibacterial agents
DE69615058T2 (en) METALLOPROTEINASE INHIBITORS
GB1116434A (en) Biphenylyl-substituted aliphatic aldehydes and their acetals
JP2004517813A5 (en)
ES455089A1 (en) Oxime derivatives of 7-aminothiazolylacetamido-cephalosporanic acid processes for preparing them and pharmaceutical compositions incorporating them
US4364956A (en) 5-Substituted pyranone compounds and their use as pharmaceuticals to treat an immediate hypersensitivity condition
IL154110A0 (en) Oxazolyl-arylpropionic acid derivatives and their use as ppar agonists
HU191523B (en) Process for preparing new phenethanol-amine derivatives
GB1154345A (en) Substituted p-Cyclohexylphenylacetic Acids and their Derivatives, and Reduction Products
US2767173A (en) Bactericidal and fungicidal compounds
CA1128517A (en) Disulfide compounds
EP2114913A1 (en) Thiophene derivatives useful as ocular hypotensive agents
JPH03190872A (en) Novel thiophene derivative
GB1119130A (en) Phenylthioalkyltetrazoles and a process for the preparation thereof
JPH01242577A (en) Antarthritic isoquisazole-4-carboximide
ES487175A1 (en) Process for preparation of piperidyl-indoles
GB1067965A (en) Penicillins, esters, amides and salts thereof
JPS5540628A (en) Novel hydroxamic acid compound, its preparation, and medicine containing the same
US4410542A (en) Disulfide compounds
JP2004527530A5 (en)
US3124588A (en) Z-acylamtoo-s-nitrothiazole
US2845432A (en) Benzamido and acetamido 4-amino-3-isoxazolidones and alkylated derivatives
US3465000A (en) Basic esters of certain substituted isoxazole-4-carboxylic acids