IE38402B1 - Aroyl-substituted phenylacetic acid derivatives - Google Patents

Aroyl-substituted phenylacetic acid derivatives

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Publication number
IE38402B1
IE38402B1 IE1896/73A IE189673A IE38402B1 IE 38402 B1 IE38402 B1 IE 38402B1 IE 1896/73 A IE1896/73 A IE 1896/73A IE 189673 A IE189673 A IE 189673A IE 38402 B1 IE38402 B1 IE 38402B1
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IE
Ireland
Prior art keywords
formula
compound
alkyl
thienyl
group
Prior art date
Application number
IE1896/73A
Other versions
IE38402L (en
Original Assignee
Janssen Pharmaceutica Nv
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Publication date
Application filed by Janssen Pharmaceutica Nv filed Critical Janssen Pharmaceutica Nv
Publication of IE38402L publication Critical patent/IE38402L/en
Publication of IE38402B1 publication Critical patent/IE38402B1/en

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    • 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
    • C07D333/28—Halogen atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/38—Heterocyclic compounds having sulfur as a ring hetero atom
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • 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
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/004—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with organometalhalides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/08—Preparation of carboxylic acids or their salts, halides or anhydrides from nitriles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/76—Unsaturated compounds containing keto groups
    • C07C59/84—Unsaturated compounds containing keto groups containing six membered aromatic rings
    • 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
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/02—Heterocyclic compounds containing six-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
    • C07D309/08—Heterocyclic compounds containing six-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 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
    • C07D309/10—Oxygen atoms
    • C07D309/12—Oxygen atoms only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D317/16—Radicals substituted by halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D317/18—Radicals substituted by singly bound oxygen or sulfur atoms
    • C07D317/20—Free hydroxyl or mercaptan
    • 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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Rheumatology (AREA)
  • Pain & Pain Management (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pyridine Compounds (AREA)
  • Heterocyclic Compounds Containing Sulfur Atoms (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Thiazole And Isothizaole Compounds (AREA)

Abstract

1446239 Aroyl-substituted-phenyl acetic acid derivatives JANSSEN PHARMACEUTICA NV 24 Oct 1973 [24 Oct 1972 10 Sept 1973] 49580/73 Heading C2C Novel compounds of the Formula I ArCO is an aroyl-substituent the Ar function of which is a 2-thienyl, 5-alkyl-2-thienyl, 5-halo-2- thienyl, 2 - naphthyl or 3 - pyridyl group, said ArCO being in the meta- or para-position relative to the acetic acid function; R is a hydrogen atom, a halogen atom or an alkyl group, provided that when said R is a halogen atom or an alkyl group, then R 1 is a hydrogen atom and said ArCO is in the aforementioned para-position, and provided that when said R is a halogen atom, then said Ar is a 2-thienyl, 5- alkyl-2-thienyl or 5-halo-2-thienyl group; R 1 is a hydrogen atom, a halogen atom or an alkyl group, provided that, when said R 1 is a halogen atom or an alkyl group, then R is a hydrogenatom and said ArCO is in the aforementioned meta position, and provided that when said R 1 is a halogen atom, then said Ar is a 2-thienyl, 5- alkyl-2-thienyl or 5-halo-2-thienyl group; R 2 is a hydrogen atom, an allyl or alkyl group; R 3 is a hydrogen atom or an alkyl group, provided that when said R 2 is an allyl group, then said R 3 is a hydrogen atom; R 2 and R 3 may also form together an alkylene bridge, having from 2 to 5 carbon atoms; Y is a hydroxy, alkoxy, having from 1 to 8 carbon atoms; dialkylamino-alkyloxy, or an amino containing group which is an amino, anilino, halo-substituted anilino, alkylanilino, alkyloxyanilino, piperidino, 2 - hydroxyethylamino, 2 - (2 - thiazolinyl)-amino or hydroxyamino group, wherein unless otherwise stated alkyl groups contain from 1 to 5 carbon atoms, may be prepared by (1) hydrolysing a compound of the Formula IV to produce a compound of the Formula Ia (b) hydrolysing a compound of the Formula VI (c) subjecting a compound of the Formula XVIa to a Willgerodt reaction in the presence of sulphur and morpholine to form a compound of the Formula Id (d) subjecting a compound XVIa to a modified Willgerodt in the presence of rhodamine to prepare a compound of the Formula Ie (e) mono or dialkylating free acids or esters of the Formula I in which one or both of R 2 and R 3 are hydrogen to introduce alkyl groups at R 2 and R 3 (f) reacting a compound of the Formula XXI with ArH under Friedel-Crafts conditions to prepare a compound of the Formula Ij (g) hydrolysing and decarboxylating a compound of the Formula XXIII to produce a free acid of the Formula I in which R 3 is hydrogen, (h) reacting a compound of the Formula XXX with ArCOCl under Friedel-Crafts conditions to yield a free acid of the Formula I, optionally followed by esterification or amidation of compounds I in which Y is hydroxy and/or hydrolysis to form the free acid and/or forming salts thereof. Intermediates of the Formula IV are prepared by reacting ArH with a halobenzoyl chloride in a Friedel-Crafts reaction to form a halophenylarylketone which is reacted with a diethyl malonate derivative in the presence of strong base to yield the required compound. Nitriles of the Formula VI are prepared by reacting ArH with an alkyl benzoyl chloride in a Friedel-Crafts reaction to form an alkylphenylketone; which is brominated under free radical conditions to form a bromoalkylphenylarylketone which is converted to the cyanoalkylphenylarylketone and optionally when the alkyl is -CH 2 -, mono or dimethylating the methylene group. Several α - chloroalkylphenyl - 2 - thienylketones are prepared by reacting an appropriate bromo benzonitrile with an alkylmagnesium halide to form a bromophenylalkylketone which is reacted with ethylene glycol to form a 2- bromphenyl - 2 - alkyl - 1,3 - dioxolane which is reacted with magnesium and then 2-thenonitrile and the intermediate ketimine hydrolysed to form a 2-thenoylphenylalkylketone which is reduced to a α-hydroxyalkylphenyl-2-thienylketone which is chlorinated to give the required compound. Several p(α - hydroxyalkyl)phenyl- 2 - thienylketones are prepared by reacting a p-(α-hydroxyalkyl)bromobenzene with 2H-3,4-dihydropyran to form a 2 - (p - bromo - benzyloxy) - tetrahydropyran which yields the required compound on reaction with magnesium and then 2-thio phenecarbonitrile. Pharmaceutical compositions of the compounds I with the usual excipients show antiinflammatory activity and inhibit platelet aggregation when administered orally or parenterally. [GB1446239A]
IE1896/73A 1972-10-24 1973-10-23 Aroyl-substituted phenylacetic acid derivatives IE38402B1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US30007972A 1972-10-24 1972-10-24
US39587773A 1973-09-10 1973-09-10

Publications (2)

Publication Number Publication Date
IE38402L IE38402L (en) 1974-04-24
IE38402B1 true IE38402B1 (en) 1978-03-01

Family

ID=26971576

Family Applications (1)

Application Number Title Priority Date Filing Date
IE1896/73A IE38402B1 (en) 1972-10-24 1973-10-23 Aroyl-substituted phenylacetic acid derivatives

Country Status (24)

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JP (2) JPS5940811B2 (en)
AT (1) AT333269B (en)
BE (1) BE806389A (en)
BG (1) BG25209A3 (en)
CA (1) CA1007643A (en)
CH (1) CH597219A5 (en)
CS (1) CS183719B2 (en)
DD (1) DD110044A5 (en)
DE (1) DE2353357C2 (en)
DK (1) DK154899C (en)
ES (1) ES419871A1 (en)
FI (1) FI66369C (en)
FR (1) FR2203635B1 (en)
GB (1) GB1446239A (en)
HU (1) HU168046B (en)
IE (1) IE38402B1 (en)
IL (1) IL43570A (en)
LU (1) LU68666A1 (en)
NL (1) NL179583C (en)
NO (1) NO141651C (en)
PH (1) PH12124A (en)
SE (1) SE403911B (en)
SU (1) SU719490A3 (en)
YU (1) YU37106B (en)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IT1036466B (en) * 1975-07-08 1979-10-30 Sigurta Farmaceutici Spa PROCESS FOR THE PREPARATION OF DERIVATIVES OF ALPHA PHENYLPROPIONIC ACID
FR2374033A1 (en) * 1976-12-16 1978-07-13 Rhone Poulenc Ind Thienothienylcarbonyl-phenyl-alkanoic acids - for use as analgesics, antipyretics, antithrombotics and antiinflammatory agents
FR2345148A1 (en) * 1976-03-24 1977-10-21 Lipha NEW SUBSTITUTE PROPIONIC ACID, PREPARATION AND APPLICATION
GB1569404A (en) * 1977-04-22 1980-06-11 Soc D Etudes Prod Chimique (2-isopropyl-4-(2'-theonyl)-5-methyl) phenoxy acetic acid
GB2030131B (en) * 1978-09-12 1982-12-22 Taiyo Pharma Ind Process for producing 2-(4-(2-thienyl-carbonyl) phenyl) propionic acid
JPS5538339A (en) * 1978-09-12 1980-03-17 Taiyo Yakuhin Kogyo Kk Preparation of 2- 4-(2-thienylcarbonyl)phenyl propionic acid
JPS5538340A (en) * 1978-09-12 1980-03-17 Taiyo Yakuhin Kogyo Kk Preparation of 2- 4-(2-thienylcarbonyl)phenyl propionic acid
JPS5825675B2 (en) * 1979-02-02 1983-05-28 財団法人相模中央化学研究所 ketal derivative
JPS5823873B2 (en) * 1979-02-02 1983-05-18 財団法人相模中央化学研究所 Method for producing substituted phenylacetic acid derivatives
ES479300A1 (en) * 1979-04-04 1979-07-01 Cusi Lab An alpha-methyl-4(2'-thienyl-carbonyl)phenyl acetic acid derivative, process for its preparation and its pharmaceutical use.
EP0046337A3 (en) * 1980-08-20 1982-09-15 Imperial Chemical Industries Plc Triazole compounds, a process for preparing them, their use as plant and pharmaceutical fungicides and as plant growth regulators and compositions containing them
CA2023954C (en) * 1989-10-17 1999-05-04 Hiroyuki Nohira Process for the optical resolution of 2-(3-benzoyl) phenylpropionic acid
JP6290947B2 (en) * 2016-02-05 2018-03-07 テックフィールズ バイオケム カンパニー リミテッド Positively charged water-soluble prodrugs of aryl- and heteroarylpropionic acids with very fast skin permeability

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1226344A (en) * 1967-07-31 1971-03-24
FR2113760A1 (en) * 1970-11-10 1972-06-30 Roussel Uclaf 5-Arylcarbonyl-3(or 4)-methylthien-2-yl alkanoic acids and esters - with antiinflammatory and analgesic activity

Also Published As

Publication number Publication date
BE806389A (en) 1974-04-23
JPS4993346A (en) 1974-09-05
PH12124A (en) 1978-11-07
DK154899C (en) 1989-05-29
CH597219A5 (en) 1978-03-31
FR2203635B1 (en) 1977-09-09
ATA900773A (en) 1976-03-15
DE2353357A1 (en) 1974-05-09
IE38402L (en) 1974-04-24
DD110044A5 (en) 1974-12-05
BG25209A3 (en) 1978-08-10
SU719490A3 (en) 1980-02-29
GB1446239A (en) 1976-08-18
LU68666A1 (en) 1974-01-03
CA1007643A (en) 1977-03-29
DK154899B (en) 1989-01-02
ES419871A1 (en) 1976-08-01
AU6176573A (en) 1975-04-24
IL43570A0 (en) 1974-03-14
NL179583C (en) 1986-10-01
JPS5940811B2 (en) 1984-10-03
FI66369B (en) 1984-06-29
NL7314629A (en) 1974-04-26
NO141651B (en) 1980-01-07
FI66369C (en) 1984-10-10
YU37106B (en) 1984-08-31
AT333269B (en) 1976-11-10
CS183719B2 (en) 1978-07-31
JPS5865243A (en) 1983-04-18
FR2203635A1 (en) 1974-05-17
NO141651C (en) 1980-04-16
JPS5938237B2 (en) 1984-09-14
HU168046B (en) 1976-02-28
IL43570A (en) 1977-05-31
SE403911B (en) 1978-09-11
YU275973A (en) 1982-06-18
DE2353357C2 (en) 1982-04-01

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