CH534138A - Aralkyl thioamino acids - anti-inflammatory - Google Patents

Aralkyl thioamino acids - anti-inflammatory

Info

Publication number
CH534138A
CH534138A CH1113468A CH1113468A CH534138A CH 534138 A CH534138 A CH 534138A CH 1113468 A CH1113468 A CH 1113468A CH 1113468 A CH1113468 A CH 1113468A CH 534138 A CH534138 A CH 534138A
Authority
CH
Switzerland
Prior art keywords
alkyl
cpds
alkenyl
alkanoyl
alkylamino
Prior art date
Application number
CH1113468A
Other languages
German (de)
Inventor
Shen Tsung-Ying
Lyn Walford Gordon
Peter Jr Dorn Conrad
Original Assignee
Merck & 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 & Co Inc filed Critical Merck & Co Inc
Publication of CH534138A publication Critical patent/CH534138A/en

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D295/00Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/08Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
    • C07D295/084Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/088Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C319/00Preparation of thiols, sulfides, hydropolysulfides or polysulfides
    • C07C319/14Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
    • C07C319/20Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides by reactions not involving the formation of sulfide groups
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D213/00Heterocyclic 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
    • C07D213/02Heterocyclic 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
    • C07D213/04Heterocyclic 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
    • C07D213/24Heterocyclic 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
    • C07D213/28Radicals substituted by singly-bound oxygen or sulphur atoms
    • C07D213/32Sulfur atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D233/00Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D233/72Two oxygen atoms, e.g. hydantoin
    • C07D233/76Two oxygen atoms, e.g. hydantoin with substituted hydrocarbon radicals attached to the third ring carbon atom
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D307/00Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/04Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D307/10Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/14Radicals substituted by nitrogen atoms not forming part of a nitro radical
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D317/00Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/44Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/46Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D317/48Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
    • C07D317/50Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
    • C07D317/56Radicals substituted by sulfur atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D333/00Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/14Radicals substituted by singly bound hetero atoms other than halogen
    • C07D333/18Radicals substituted by singly bound hetero atoms other than halogen by sulfur atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pyridine Compounds (AREA)
  • Manufacture And Refinement Of Metals (AREA)
  • Saccharide Compounds (AREA)

Abstract

Process for cpds. of formula (I), and some cpds. (I): R = H, halogen, SH, CN, SO2alkyl, SO alkyl, alkanoyl, CF3CO, haloalkyl, SO2NH2, SO2N(alkyl)2, CONH2, CON(alkyl)2, OH, S-alkyl, O-alkyl, anisyl, Ph, NO2, phenethyl, alkyl, OCH2O, PhNH-, PhN(alkyl)-, alkylphenyl, N(alkyl)2, cyclohenyl, PhO, NH2, NHacyl, NHalkyl, or alkenyl. R may be substd. by Ph or naphthyl. R2 = OH, O-alkyl, O-alkenyl, O-alkynyl, cyclopropyl-methyloxy, alkoxyalkoxy, polyalkoxyalkoxy, dialkyl-aminoalkoxy, piperidinoalkoxy, 1-pyrrolidenylalkoxy, morpholinoalkoxy, 1-alkyl-2-pyrolidinyalkoxy, 1-alkyl-2-piperidino-alkoxy, N'-alkyl-N-piperazinyl-alkoxy, PhO, p-alkanoylaminophenoxy, phenylalkoxy, carbamylphenoxy, tetrahydrofurfuryloxy, dialkylamino-cyclohexyloxy, NH2, NHalkyl, N(alkyl)2, glucosamino, glycosylamino, alkenylamino, phenylalkylamino, haloanilino, 1-alkylpiperidinyl-2-alkylamino, tetrahydrofuryfurylamino, 1,2,5,6-tetrahydropyridino, morpholino, N'-alkyl-N-piperazinyl, piperazino, N-phenylpiperazino, piperidino, benzylamino, PhNH2, alkoxyanilino, NH(cycloalkyl), pyrrolidino, N-hydroxyalkylpiperazino, N, N-dialkylcarbamyl-alkylamino-, N, N-dialkylaminoalkylamino, 1-alkyl-pyrrolidino 2-alkylamino, N-carbobenzyloxyalkylamino, or a group OZ, where Z is a cation or the acyl portion of I(R2=OH). R',R3,R7=H, alkyl or Ph; R4,R5 = H, alkyl, alkanoyl, Ph, or guanyl if R5=H; R6,R8 = H, alkyl, alkenyl, Ph or -naphthyl opt. substd. by R, thienyl, pyridyl. Cpds. (I) are new provided that (a) if R6 and R8 = Ph, at least 1 of R, R', R3, R4, R5, R7 is not = H, and R2 is as above. (b) If R8 = Ph, at least one of R', R3, R4, R5, R6, R7, is not = H when R=H or Oalkyl and is any a single substit. (c) If R8 = H, and R=H, Hal, Oalkyl, NO2, or alkenyl, and is a single substit., then at least one of R', R3, R4, R5, R6, R7 is not = H. (d) If R4 = alkanoyl, at least one of R, R', R3, R5, R6, R7 is not = H, while R2 is as above and R8=H. Also the corr. cpds. III, IV, V, and process for II.
CH1113468A 1967-07-26 1968-07-25 Aralkyl thioamino acids - anti-inflammatory CH534138A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US65604167A 1967-07-26 1967-07-26
US72835168A 1968-05-10 1968-05-10

Publications (1)

Publication Number Publication Date
CH534138A true CH534138A (en) 1973-02-28

Family

ID=27097099

Family Applications (1)

Application Number Title Priority Date Filing Date
CH1113468A CH534138A (en) 1967-07-26 1968-07-25 Aralkyl thioamino acids - anti-inflammatory

Country Status (12)

Country Link
JP (1) JPS5019543B1 (en)
BE (1) BE718559A (en)
CH (1) CH534138A (en)
DE (1) DE1768964A1 (en)
ES (4) ES356488A1 (en)
FR (2) FR7960M (en)
GB (1) GB1191042A (en)
IE (1) IE32515B1 (en)
IL (1) IL30369A (en)
NL (1) NL144484B (en)
NO (1) NO124205B (en)
SE (1) SE364040B (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10045831A1 (en) * 2000-09-14 2002-04-04 Gruenenthal Gmbh Anticonvulsant, anxiolytic and especially analgesic medicaments, comprising new or known beta-thio-alpha-aminoacid compounds having strong affinity for gabapentin binding site
US6846843B2 (en) 2000-09-14 2005-01-25 Gruenenthal Gmbh β-thioamino acids

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE733993A (en) * 1968-06-14 1969-12-03
US4315031A (en) * 1977-09-01 1982-02-09 Science Union Et Cie Thiosubstituted amino acids
FR2434149A1 (en) * 1978-06-22 1980-03-21 Parcor NEW L-CYSTEIN DERIVATIVES
US4246263A (en) * 1979-10-15 1981-01-20 Pfizer Inc. Antiinflammatory and immunoregulatory pyrimidines, their method of use and pharmaceutical compositions
DE3303344A1 (en) * 1983-02-02 1984-08-02 Hoechst Ag, 6230 Frankfurt METHOD FOR PRODUCING N-ALKYLATED AMINO ACIDS AND THEIR ESTERS
US9074553B2 (en) 2010-12-29 2015-07-07 Ford Global Technologies, Llc Cylinder block assembly

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10045831A1 (en) * 2000-09-14 2002-04-04 Gruenenthal Gmbh Anticonvulsant, anxiolytic and especially analgesic medicaments, comprising new or known beta-thio-alpha-aminoacid compounds having strong affinity for gabapentin binding site
US6846843B2 (en) 2000-09-14 2005-01-25 Gruenenthal Gmbh β-thioamino acids

Also Published As

Publication number Publication date
ES356488A1 (en) 1970-04-01
NL6809834A (en) 1969-01-28
BE718559A (en) 1969-01-27
GB1191042A (en) 1970-05-06
DE1768964A1 (en) 1972-01-27
JPS5019543B1 (en) 1975-07-08
IL30369A (en) 1973-08-29
ES372357A1 (en) 1972-01-16
FR1586146A (en) 1970-02-13
NO124205B (en) 1972-03-20
FR7960M (en) 1970-06-01
IE32515B1 (en) 1973-09-05
IE32515L (en) 1969-01-26
ES372358A1 (en) 1971-10-16
IL30369A0 (en) 1968-09-26
ES372359A1 (en) 1971-10-16
SE364040B (en) 1974-02-11
NL144484B (en) 1975-01-15

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Legal Events

Date Code Title Description
PL Patent ceased