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GB1316312A - Tertiary aminoacids process for their manufacture and compositions containing them - Google Patents

Tertiary aminoacids process for their manufacture and compositions containing them

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Publication number
GB1316312A
GB1316312A GB3337570A GB3337570A GB1316312A GB 1316312 A GB1316312 A GB 1316312A GB 3337570 A GB3337570 A GB 3337570A GB 3337570 A GB3337570 A GB 3337570A GB 1316312 A GB1316312 A GB 1316312A
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United Kingdom
Prior art keywords
formula
group
compound
free
ester
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
GB3337570A
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.)
Novartis AG
Original Assignee
Ciba Geigy AG
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
Priority claimed from CH1383169A external-priority patent/CH577480A5/en
Application filed by Ciba Geigy AG filed Critical Ciba Geigy AG
Publication of GB1316312A publication Critical patent/GB1316312A/en
Expired legal-status Critical Current

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Classifications

    • 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
    • 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
    • C07D211/02—Preparation by ring-closure or hydrogenation
    • 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
    • C07D211/70—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • 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
    • C07D211/74—Oxygen atoms
    • 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
    • C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
    • C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
    • C07D217/04—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

1316312 α(p - Tertiaryaminophenyl)- akanoic acids and derivatives CIBA GEIGY AG 9 July 1970 [18 July 1969 8 Sept 1969 12 Sept 1969 3 Feb 1970 25 May 1970] 33375/70 Addition to 1268831 Heading C2C Novel compounds of Formula I in which A N- represents an unsubstituted or substituted bicyclic alkenyleneamino group with 5 or 6 members in each ring and with from 1 to 3 double bonds in the ring system, Ph represents an unsubstituted or substituted phenylene radical, R 1 represents a hydrogen atom or a lower alkyl group, and R 2 represents a hydrogen atom or a lower alkyl, lower alkenyl, unsubstituted or lower alkyl-substituted cyclealkyl, unsubstituted or lower alkyl-substituted cycloalkenyl, cycloalkyl-lower alkyl or cycloalkenyl lower alkyl group or an ester, amide, thioamide, nitrile or hydroxamic acid of such an acid, are prepared by one of the following methods: (a) a compound of Formula II wherein X 1 represents a hydrogen atom, is reacted with a compound of the formula Y 1 -C(R 1 )(R 2 )-C(=O)-OH (IIb), in which Y 1 stands for a free or reactive esterified hydroxy group, or a salt, ester, amide, thioamide, nitrile or hydroxamic acid thereof, or (b) a compound of the Formula II, in which X 1 represents a metal radical, is reacted with a compound of the formula (IIb), in which Y 1 stands for a reactive esterified hydroxy group, or a salt, ester, amide, thioamide, nitrile or hydroxamic acid thereof, or (c) a compound of the Formula II, in which X 1 represents a reactive esterified hydroxy group, is reacted with a compound of the formula Y 1 -C(R 1 )(R 2 )-C(=O)-OH (IIb), in which Y 1 stands for a metal radical, or an ester, amide, thioamide, nitrile or hydroxamic acid thereof, or (d) a compound of the Formula II, in which X 1 represents the group of the formula -C(R 1 )(R 2 )-Y 2 (IIc), in which Y 2 stands for a metal radical, is reacted with a metal-free, reactive derivative of carbonic or formic acid, or (e) a compound of the Formula II, in which X 1 represents the group of the formula (IIc), in which Y 2 stands for an unsubstituted or substituted ammonium group, is reacted with a reactive metal-containing derivative of carbonic or formic acid, or (f) a compound of the Formula II, in which X 1 represents the group of the formula -C(R 1 )(R 2 )-Y 2 (IIc), in which Y 2 stands for a free or reactive, functionally converted hydroxy group, is reacted with a reactive metal-containing derivative of carbonic or formic acid, or (g) a compound of the Formula II, in which X 1 represents the group of the formula -C(R 1 )(R 2 )-Y 2 (IIc), in which Y 2 stands for a free, esterified or salified hydroxy group, or represents a 1-lower alkenyl radical is reacted with carbon monoxide, or (h) in a compound of the Formula II, in which X 1 represents the group of the formula (IId) in which Y 3 stands for a methyl, hydroxymethyl, borylmethyl, hydroxyimino methyl, formyl, 1-lower alkenyl, 1-lower alkynyl, 1,2- dihydroxy-lower alkyl group, an acyl group or a free or functionally modified carboxy carbonyl group, Y 3 is converted into a free, esterified, amidated or thioamidated carboxyl group or a cyano group or hydroxamic acid by oxidation or rearrangement, or (i) in a compound of the Formula II, in which X 1 represents the group of the formula -C(R 1 )(R 2 )-Y 3 , in which Y 3 stands for a free or esterified carboxycarbonyl group, Y 3 is converted into a free or esterified carboxy group by oxidation or decarbonylation, or (j) a compound of the Formula II, in which X 1 represents a group of the formula -C(R 1 or R 2 ) (Y 4 )-C(=O)-OH (IIf) or of the formula -C(=Y 5 )-C(=O)-OH (IIg), in which Y 4 represents a free or reactive esterified or etherified hydroxy or free or reactive esterified or etherified mercapto group, and Y 6 represents a lower alkylidene, cycloalkylidene or cycloalkyl-lower alkylidene group or an oxo group or a free or ketalized thio group, or a corresponding ester, amide, thioamide or nitrile or a corresponding quaternary ortho or para-quinone methide of such compound is treated with catalytically activated or electrolytically generated hydrogen or with a chemical reducing agent, if desired, in the presence of a desulphurizing agent, or (k) a compound of the Formula II, in which X 1 represents the group of the formula -C(R 1 or R 2 ) (Y 4 )-C(=O)-OH (IIf), in which Y 4 represents a carboxy group, or an ester, amide, thioamide, nitrile or hydroxamic acid thereof is decarboxylated by pyrolysis, or (1) a compound of the Formula II, in which X 1 represents a group of the formula -C(R 1 or R 2 ) (Y 4 )-C( = O)-OH (IIf), in which Y 4 represents an acyl group, or an ester, amide, thioamide, nitrile or hydroxamic acid is subjected to #- keto-acid splitting by treatment with a strongly alkaline agent, or (m) a compound of the Formula II, in which X 1 represents an acetyl group, is treated with sulphur in the presence of ammonia or a primary or secondary amine, or (n) a compound of the Formula II, in which X 1 represents a group of the formula (IIh) is subjected to hydrolysis, alcoholysis, ammonolysis or aminolysis, (o) a compound of the Formula II, in which X 1 represents a group of the formula -C(=O)-C(R 1 )(R 2 )-Hal (IIi), in which Hal stands for a halogen atom, is treated with a strongly alkaline agent or with a soluble silver salt, or (p) a compound of the Formula III or an ester, amide, thioamide, nitrile or hydroxamic acid thereof, is reacted with a compound of the formula A N-Y 6 (IIIa), one of the radicals X 2 and Y 6 representing a hydrogen atom or a metal group and the other a free or reactive esterified hydroxy group, or (q) a compound of the Formula III or an ester, an amide, a thioamide, nitrile or hydroxamic acid thereof, in which X 2 represents a primary, secondary or tertiary amino group, is reacted with an amine of the formula A N-H, or (r) a compound of the Formula III, in which X 2 represents a primary amino group, or an ester, amide, thioamide, nitrile or hydroxamic acid thereof, is reacted with a compound of the formula HO-A-OH (IIIb) or with a reactive derivative thereof or with a corresponding dehydrated compound thereof, or (s) a compound of the Formula III, in which X 2 represents a radical of the formula A 0 N- which stands for a bicyclic alkyleneamino group having 5 or 6 ring members in each ring, and which group contains one or more of the same or different substituents selected from hydroxy, mercapto, amino, ammonium, hydrazino and hydrazono groups and functionally converted groups corresponding to these or an ester, amide, thioamide, nitrile or hydroxamic acid thereof, is dehydrated, dehydrosulphidated, deaminated or pyrolysed, a resulting compound is converted within the scope defined into another compound of this invention, and/or, if desired, a resulting free compound is converted into a salt or a resulting salt into a free compound, and/or, if desired, a resulting mixture of isomers is resolved into the individual isomers. Examples relate to α[4-(2- isoindolin - yl) - phenyl]acetic or propionic acids and their ethyl esters, α-[4-(2-isoindolinyl)- 3 - chlorophenyl] propionic acid and its ethyl ester, ethyl α - [4- (1,3 - dioxo - 1,2,3,4 - tetrahydro - 2 - isoquinolinyl) - phenyl] - acetate ethyl α - [3 - chloro - 4 - (1,3 - dioxo - 2 - isoindolinyl) - phenyl] - propionate and α[ - 3- chloro - 4 - (1 - oxo - 2 - isoindolinyl) - phenyl]- propionic acid and its ethyl ester. Intermediates prepared are ethyl 4-aminophenyl acetate ethyl α-(4-nitrophenyl)-propionate, ethyl α - (4 - aminophenyl) - propionate, ethyl α - (4 - acetamidophenyl) - propionate, ethyl α- (3 - chloro - 4 - acetamidophenyl) - propionate, ethyl α - (4 - amino - 3 - chlorophenyl) - propionate, ethyl α - (4 - acetamidophenyl) - acetate, diethyl α - (3 - chloro - 4 - nitrophenyl) - α - methylmalonate and diethyl α - (3 - chloro - 4 - aminophenyl) - α -methyl-malonate. Pharmaceutical compositions in conventional forms for enteral, parenteral or topical administration and having anti-inflammatory analgesic and antifungal activity comprise an above novel compound and a carrier or diluent.
GB3337570A 1968-03-27 1970-07-09 Tertiary aminoacids process for their manufacture and compositions containing them Expired GB1316312A (en)

Applications Claiming Priority (8)

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
US84324469A 1969-07-18 1969-07-18
US85615469A 1969-09-08 1969-09-08
CH1383169A CH577480A5 (en) 1969-07-18 1969-09-12 Alpha-aminophenyl aliphatic carboxylic acids - useful as anti-inflammatory agents, analgesics and anti-mycotics
US840670A 1970-02-03 1970-02-03
US4043670A 1970-05-25 1970-05-25

Publications (1)

Publication Number Publication Date
GB1316312A true GB1316312A (en) 1973-05-09

Family

ID=27570387

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3337570A Expired GB1316312A (en) 1968-03-27 1970-07-09 Tertiary aminoacids process for their manufacture and compositions containing them

Country Status (4)

Country Link
BE (1) BE753600R (en)
FR (1) FR2059527B2 (en)
GB (1) GB1316312A (en)
NL (1) NL170852C (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4266069A (en) 1979-12-19 1981-05-05 The Upjohn Company Processes for the preparation of hydratropic acids and esters
EP0032620A1 (en) * 1979-12-19 1981-07-29 The Upjohn Company Process for preparing therapeutic 2-arylpropionic acids and esters, and novel arylmethylmalonate esters
US4324904A (en) 1979-12-19 1982-04-13 The Upjohn Company Processes for the preparation of hydratropic acids and esters
US5561151A (en) * 1992-03-13 1996-10-01 Sepracor Inc. Antipyretic and analgesic methods of using optically pure R-etodolac

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2371924A1 (en) 1976-11-30 1978-06-23 Lipha SUBSTITUTE ARYL-ALIPHATIC ACIDS

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH500973A (en) * 1966-10-31 1970-12-31 Ciba Geigy Ag Process for the preparation of new derivatives of phenylacetic acids

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4266069A (en) 1979-12-19 1981-05-05 The Upjohn Company Processes for the preparation of hydratropic acids and esters
EP0032620A1 (en) * 1979-12-19 1981-07-29 The Upjohn Company Process for preparing therapeutic 2-arylpropionic acids and esters, and novel arylmethylmalonate esters
US4324904A (en) 1979-12-19 1982-04-13 The Upjohn Company Processes for the preparation of hydratropic acids and esters
JPH02223542A (en) * 1979-12-19 1990-09-05 Upjohn Co:The Preparation of hydroatropic acid derivative and ester thereof
US5561151A (en) * 1992-03-13 1996-10-01 Sepracor Inc. Antipyretic and analgesic methods of using optically pure R-etodolac

Also Published As

Publication number Publication date
FR2059527A2 (en) 1971-06-04
NL170852B (en) 1982-08-02
BE753600R (en) 1971-01-18
NL170852C (en) 1983-01-03
NL7009387A (en) 1971-01-20
FR2059527B2 (en) 1975-10-31

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