ES419871A1 - Aroyl-substituted phenylacetic acid derivatives - Google Patents

Aroyl-substituted phenylacetic acid derivatives

Info

Publication number
ES419871A1
ES419871A1 ES419871A ES419871A ES419871A1 ES 419871 A1 ES419871 A1 ES 419871A1 ES 419871 A ES419871 A ES 419871A ES 419871 A ES419871 A ES 419871A ES 419871 A1 ES419871 A1 ES 419871A1
Authority
ES
Spain
Prior art keywords
formula
group
compound
lower alkyl
thienyl
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
ES419871A
Other languages
Spanish (es)
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.)
Janssen Pharmaceutica NV
Original Assignee
Janssen Pharmaceutica NV
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 Janssen Pharmaceutica NV filed Critical Janssen Pharmaceutica NV
Publication of ES419871A1 publication Critical patent/ES419871A1/en
Expired legal-status Critical Current

Links

Classifications

    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (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

A procedure for the preparation of a derivative of an aroyl-α-R2, α-R3-phenylacetic acid of the formula: **(See formula)** where ArCO is an aroyl substituent whose Ar function is a member selected from the group consisting of 2-thienyl, 5-lower-alkyl-2-thienyl, 5-halo-2-thienyl, 2-naphthyl and 3-pyridyl, said ArCO at the meta or para positions with respect to acetic acid function; R is a member selected from the group consisting of hydrogen, halogen, and lower alkyl, with the proviso that when R is halogen or lower alkyl, then ArCO is in the aforementioned para position and when R is halogen, then Ar is 2 -thienyl, 5-lower (alkyl) -2-thienyl or 5-halo-2-thienyl; R2 is a member selected from the group consisting of hydrogen, allyl, and lower alkyl; R3 is a member selected from the group consisting of hydrogen and lower alkyl, with the proviso that when R3 is lower alkyl, then R2 is lower alkyl; Y is a member selected from the group consisting of hydroxy, alkoxy, 1 to 8 carbon atoms, dialkyl (lower) aminoalkyl (lower) oxy, and amino radicals of the class consisting of amino, anilino, haloanilino, lower alkyl anilino, lower alkyl oxyanilino, piperidino, hydroxyethylamino, 2- (2-thiazolinyl) amino or hydroxylamino; whose procedure is characterized by: (a) hydrolyze a compound of the formula: **(See formula)** preferably under alkaline hydrolysis conditions to prepare a compound of formula: **(See formula)** and, if desired, esterifying said compound by known esterification methods to prepare a compound of formula, **(See formula)** wherein R4 is alkyl or dialkyl (lower) aminoalkyl (lower) and, if desired, converting said compound of formula I-a to the halide of the acid of formula **(See formula)** and further, if desired, replace the OR4 group of said compound or the halide in compound (V) with an amino group or a substituted amino group, using known methods or, if desired, rent the α-carbon by known methods, or if desired, solving, by conventional methods, the stereochemical (+) or (-) isomers from the compounds of formula (I). (Machine-translation by Google Translate, not legally binding)
ES419871A 1972-10-24 1973-10-23 Aroyl-substituted phenylacetic acid derivatives Expired ES419871A1 (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 (1)

Publication Number Publication Date
ES419871A1 true ES419871A1 (en) 1976-08-01

Family

ID=26971576

Family Applications (1)

Application Number Title Priority Date Filing Date
ES419871A Expired ES419871A1 (en) 1972-10-24 1973-10-23 Aroyl-substituted phenylacetic acid derivatives

Country Status (24)

Country Link
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
JPS5538340A (en) * 1978-09-12 1980-03-17 Taiyo Yakuhin Kogyo Kk Preparation of 2- 4-(2-thienylcarbonyl)phenyl propionic acid
JPS5538339A (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
IL43570A (en) 1977-05-31
JPS4993346A (en) 1974-09-05
LU68666A1 (en) 1974-01-03
YU37106B (en) 1984-08-31
BG25209A3 (en) 1978-08-10
NO141651C (en) 1980-04-16
DE2353357C2 (en) 1982-04-01
NL179583C (en) 1986-10-01
JPS5940811B2 (en) 1984-10-03
IE38402B1 (en) 1978-03-01
FI66369C (en) 1984-10-10
DD110044A5 (en) 1974-12-05
CA1007643A (en) 1977-03-29
NL7314629A (en) 1974-04-26
NO141651B (en) 1980-01-07
CS183719B2 (en) 1978-07-31
IL43570A0 (en) 1974-03-14
AU6176573A (en) 1975-04-24
YU275973A (en) 1982-06-18
FR2203635A1 (en) 1974-05-17
DK154899B (en) 1989-01-02
SU719490A3 (en) 1980-02-29
DE2353357A1 (en) 1974-05-09
FR2203635B1 (en) 1977-09-09
IE38402L (en) 1974-04-24
GB1446239A (en) 1976-08-18
SE403911B (en) 1978-09-11
ATA900773A (en) 1976-03-15
JPS5865243A (en) 1983-04-18
CH597219A5 (en) 1978-03-31
HU168046B (en) 1976-02-28
DK154899C (en) 1989-05-29
PH12124A (en) 1978-11-07
BE806389A (en) 1974-04-23
AT333269B (en) 1976-11-10
JPS5938237B2 (en) 1984-09-14
FI66369B (en) 1984-06-29

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