IE33153L - Tertiary amino acids - Google Patents

Tertiary amino acids

Info

Publication number
IE33153L
IE33153L IE690397A IE39769A IE33153L IE 33153 L IE33153 L IE 33153L IE 690397 A IE690397 A IE 690397A IE 39769 A IE39769 A IE 39769A IE 33153 L IE33153 L IE 33153L
Authority
IE
Ireland
Prior art keywords
formula
group
compound
reacting
acid
Prior art date
Application number
IE690397A
Other versions
IE33153B1 (en
Original Assignee
Ciba Geigy
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 Ciba Geigy filed Critical Ciba Geigy
Publication of IE33153L publication Critical patent/IE33153L/en
Publication of IE33153B1 publication Critical patent/IE33153B1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D207/24—Oxygen or sulfur atoms
    • C07D207/26—2-Pyrrolidones
    • C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
    • C07D207/27—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
    • C07C205/56—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups bound to carbon atoms of six-membered aromatic rings and carboxyl groups bound to acyclic carbon atoms of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D207/20—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D207/36—Oxygen or sulfur atoms
    • C07D207/40—2,5-Pyrrolidine-diones
    • C07D207/404—2,5-Pyrrolidine-diones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. succinimide
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/44—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members
    • C07D207/444—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5
    • C07D207/448—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. maleimide
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/46—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with hetero atoms directly attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/44—Iso-indoles; Hydrogenated iso-indoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/44—Iso-indoles; Hydrogenated iso-indoles
    • C07D209/46—Iso-indoles; Hydrogenated iso-indoles with an oxygen atom in position 1
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/44—Iso-indoles; Hydrogenated iso-indoles
    • C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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
    • C07D211/40—Oxygen atoms
    • C07D211/42—Oxygen atoms attached in position 3 or 5
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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
    • C07D211/40—Oxygen atoms
    • C07D211/44—Oxygen atoms attached in position 4
    • C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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, directly attached to ring carbon atoms
    • C07D211/78—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • 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
    • C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
    • C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems 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 carbon atoms of the nitrogen-containing ring
    • C07D217/24—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic 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
    • C07D295/16—Heterocyclic 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 acylated on ring nitrogen atoms
    • C07D295/18—Heterocyclic 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 acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic 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
    • C07D295/16—Heterocyclic 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 acylated on ring nitrogen atoms
    • C07D295/18—Heterocyclic 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 acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
    • C07D295/182—Radicals derived from carboxylic acids
    • C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
    • 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
    • C07D307/56—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 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
    • C07D307/66—Nitrogen atoms

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pain & Pain Management (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Rheumatology (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Hydrogenated Pyridines (AREA)
  • Pyrrole Compounds (AREA)

Abstract

1,268,831. α(Cyclicaminophenyl) - aliphatic carboxylic acids. CIBA-GEIGY A.G. 26 March, 1969 [27 March, 1968; 3 Sept., 1968; 13 Jan., 1969], No. 15859/69. Heading C2C. Novel compounds of Formula I in which R 1 represents a hydrogen atom or a lower alkyl, cycloalkyl or cycloalkyl-lower alkyl group; Ph represents a phenylene radical or a phenylene radical substituted by one or more of the same or different substituents selected from lower alkyl, free hydroxy, free mercapto, lower alkoxy, lower alkylmercapto, halogeno, trifluoromethyl, nitro and amino groups; and A represents a lower alkylene or lower alkenylene radical that is unsubstituted or substituted by one or more of the same or different substituents selected from lower alkyl, hydroxy, mercapto, lower alkoxy, lower alkanoyloxy, lower alkylmercapto, halogeno and oxo groups; provided that R 1 represents a cycloalkyl or cycloalkyllower alkyl group, and/or A represents a lower alkenylene radical which may be substituted as defined above; and the functional acid and amino derivatives i.e. esters, amides, thioamides, morpholides, nitriles, hydroxamic acids, ammonium and metal salts, N-oxides, lower alkyl or phenyl lower alkyl, quaternary ammonium compounds and acid addition salts, ("lower" above and hereinafter denotes groups or compounds containing up to 7 carbon atoms) are prepared (a) by reacting a compound of Formula II in which A has the meaning given for Formula I and X 1 represents a grouping of the formula -CH(R 1 )-Y 1 , in which Y 1 represents an alkali metal atom, a halogeno-magnesium group or a reactive, esterified or etherified hydroxyl group, with a reactive derivative of carbonic acid or of formic acid, not more than one of the reactants containing a metal atom; or (b) oxidizing in a compound of the Formula II in which X 1 represents a grouping of the formula -CH(R 1 )-Y 2 , in which Y 2 represents a hydroxymethyl or borylmethyl group, a formyl group or a 1-lower alkenyl or lower alkenoyl group, the group represented by Y 2 ; or (c) reacting a compound of the Formula II in which X 1 represents a grouping of the formula -CH(R 1 )-Y 2 , in which Y 2 represents an ammonium group, with a metal cyanide; or (d) decarbonylating a compound of the Formula II in which X 1 represents a grouping of the formula -CH(R 1 )-Y 2 , in which Y 2 represents a carboxycarbonyl group; or (e) reacting a compound of the Formula II in which X 1 represents an acetyl group, with sulphur in the presence of ammonia or a primary or secondary amine; or (f) reacting a compound of the Formula II in which X 1 represents a halogeno-carbonyl group, with an R 1 -diazo compound and rearranging it by hydrolysis, alcoholysis, ammonolysis or aminolysis; or (g) reacting a compound of the Formula II in which X 1 represents a 1-lower alkenyl group, with carbon monoxide and water under acidic conditions; or (h) decarboxylating a compound of the Formula II in which X 1 represents a free or functionally converted grouping of the formula -C(R 0 )(R 1 )-C(=O)-OH, in which R 0 represents a carboxy group; or (j) converting in a compound of the Formula II, in which X 1 represents a free or functionally converted grouping of the formula or of the formula -C(=R 1 <SP>0</SP>)-C(=O)-OH, in which R‹ represents a free or reactive esterified hydroxyl group, and R 1 <SP>0</SP> represents a lower alkylidene or cycloalkylidene group, the group represented by R‹ into a hydrogen atom or the group represented by R 1 <SP>0</SP> into a group represented by R 1 , by reduction; or (k) reacting a compound of the Formula II in which X 1 represents a hydrogen atom or a metal atom or a metal grouping, with a reactive ester of a glycolic acid compound of the formula or a functional acid derivative thereof, in which Y 3 represents a reactive, esterified hydroxyl group; or (m) reacting a compound of the formula or a functional acid derivative thereof, in which X 2 represents a reactive esterified hydroxyl group, with a secondary amine of the formula AN-H or an alkali metal derivative thereof, or (n) reacting a compound of the Formula III in which X 2 represents a primary amino group, with a reactive esterified glycol of the formula HO-A-OH; and, if desired, converting an acid or amine group into the required derivative or a resulting derivative into the free acid and, if desired, reacting a compound of Formula I where R 1 is H with a metal and then a reactive ester of an alcohol R 1 OH, and if desired, followed by salt formation and/or resolution. α-Cyclopropyl-α-(4-piperidinophenyl) acetaldehyde is prepared by action of p-toluenesulphonic acid on 1-cyclopropyl-1-(4-piperidinophenyl)-ethylene oxide which is obtained from 4-piperidinophenyl cyclopropyl ketone by action of a reagent prepared from sodium hydride and trimethyl sulphonium iodide in dimethylsulphoxide. Pharmaceutical compositions having antiinflammatory activity and in conventional forms for enteral or parenteral administration comprise an above novel compound and a carrier therefor. [GB1268831A]
IE397/69A 1968-03-27 1969-03-25 Tertiary amino acids,process for their manufacture and compositions containing them IE33153B1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US71634768A 1968-03-27 1968-03-27
US75713668A 1968-09-03 1968-09-03
US79086369A 1969-01-13 1969-01-13

Publications (2)

Publication Number Publication Date
IE33153L true IE33153L (en) 1969-09-27
IE33153B1 IE33153B1 (en) 1974-04-03

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IE397/69A IE33153B1 (en) 1968-03-27 1969-03-25 Tertiary amino acids,process for their manufacture and compositions containing them

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JP (1) JPS5330712B1 (en)
AR (7) AR192560A1 (en)
AT (8) AT291241B (en)
BE (1) BE730520A (en)
BG (3) BG20340A3 (en)
CH (11) CH563989A5 (en)
CS (8) CS153511B2 (en)
CY (1) CY809A (en)
DE (1) DE1913743A1 (en)
DK (1) DK145226C (en)
FI (1) FI52579C (en)
FR (1) FR2004827A1 (en)
GB (1) GB1268831A (en)
IE (1) IE33153B1 (en)
IL (1) IL31861A (en)
KE (1) KE2542A (en)
MY (1) MY7500152A (en)
NL (1) NL162647C (en)
NO (1) NO132199C (en)
OA (1) OA03609A (en)
PH (1) PH12640A (en)
PL (1) PL74820B1 (en)
RO (4) RO61382A (en)
SE (1) SE382812B (en)
SU (4) SU459886A3 (en)
YU (3) YU39926B (en)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2025518A1 (en) * 1969-06-05 1970-12-10
DE2013376A1 (en) * 1970-03-20 1971-10-07 Merck Patent Gmbh Substituted phenylacetic acids and processes for their preparation

Also Published As

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CS153508B2 (en) 1974-02-25
RO61382A (en) 1976-10-15
IL31861A0 (en) 1969-05-28
AR192699A1 (en) 1973-03-14
PL74820B1 (en) 1974-12-31
CH559755A5 (en) 1975-03-14
FR2004827A1 (en) 1969-12-05
SU421191A3 (en) 1974-03-25
NL162647B (en) 1980-01-15
DE1913743A1 (en) 1969-11-20
CS153511B2 (en) 1974-02-25
MY7500152A (en) 1975-12-31
RO64901A (en) 1979-08-15
AT291239B (en) 1971-07-12
RO66269A (en) 1979-03-15
CS153505B2 (en) 1974-02-25
BG20339A3 (en) 1975-11-05
AT287685B (en) 1971-02-10
IL31861A (en) 1974-03-14
FI52579C (en) 1977-10-10
NL6903273A (en) 1969-09-30
AT291241B (en) 1971-07-12
NO132199C (en) 1975-10-08
YU39653B (en) 1985-03-20
SU428600A3 (en) 1974-05-15
SU419029A3 (en) 1974-03-05
AT291235B (en) 1971-07-12
YU200174A (en) 1982-06-30
FI52579B (en) 1977-06-30
AT291234B (en) 1971-07-12
CH563984A5 (en) 1975-07-15
SE382812B (en) 1976-02-16
CH566990A5 (en) 1975-09-30
CH563985A5 (en) 1975-07-15
NL162647C (en) 1980-06-16
AT291242B (en) 1971-07-12
YU200074A (en) 1982-06-30
SU459886A3 (en) 1975-02-05
CS153510B2 (en) 1974-02-25
CS153506B2 (en) 1974-02-25
KE2542A (en) 1975-07-25
RO66273A (en) 1981-08-17
CY809A (en) 1976-12-01
NO132199B (en) 1975-06-23
CS153503B2 (en) 1974-02-25
CH563986A5 (en) 1975-07-15
DK145226B (en) 1982-10-11
DK145226C (en) 1983-03-28
BG20340A3 (en) 1975-11-05
CH563381A5 (en) 1975-06-30
AR193024A1 (en) 1973-03-30
CH554859A (en) 1974-10-15
AR192864A1 (en) 1973-03-21
CS153504B2 (en) 1974-02-25
YU149975A (en) 1982-06-30
CS153502B2 (en) 1974-02-25
AR192560A1 (en) 1973-02-28
JPS5330712B1 (en) 1978-08-29
AT291240B (en) 1971-07-12
YU39926B (en) 1985-06-30
CH563988A5 (en) 1975-07-15
IE33153B1 (en) 1974-04-03
AR193194A1 (en) 1973-04-11
BG20567A3 (en) 1975-12-05
GB1268831A (en) 1972-03-29
AR194569A1 (en) 1973-07-31
CH563983A5 (en) 1975-07-15
YU39532B (en) 1984-12-31
OA03609A (en) 1971-03-30
AT291237B (en) 1971-07-12
CH563989A5 (en) 1975-07-15
BE730520A (en) 1969-09-26
CH566991A5 (en) 1975-09-30
PH12640A (en) 1979-07-05
AR193025A1 (en) 1973-03-30

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