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GB1291386A - Improvements in or relating to 2-(6'-substituted-2'-naphthyl) propionic acid derivatives and salts thereof - Google Patents

Improvements in or relating to 2-(6'-substituted-2'-naphthyl) propionic acid derivatives and salts thereof

Info

Publication number
GB1291386A
GB1291386A GB2764/70A GB276470A GB1291386A GB 1291386 A GB1291386 A GB 1291386A GB 2764/70 A GB2764/70 A GB 2764/70A GB 276470 A GB276470 A GB 276470A GB 1291386 A GB1291386 A GB 1291386A
Authority
GB
United Kingdom
Prior art keywords
naphthyl
compound
methoxy
methyl
propionic acid
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
GB2764/70A
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.)
Roche Palo Alto LLC
Original Assignee
Roche Palo Alto LLC
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 Roche Palo Alto LLC filed Critical Roche Palo Alto LLC
Publication of GB1291386A publication Critical patent/GB1291386A/en
Expired legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • 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
    • C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
    • C07C45/46—Friedel-Crafts reactions
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
    • C07C49/687—Unsaturated compounds containing a keto groups being part of a ring containing halogen
    • C07C49/697—Unsaturated compounds containing a keto groups being part of a ring containing halogen containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
    • C07C49/753—Unsaturated compounds containing a keto groups being part of a ring containing ether groups, groups, groups, or groups
    • C07C49/755—Unsaturated compounds containing a keto groups being part of a ring containing ether groups, groups, groups, or groups a keto group being part of a condensed ring system with two or three rings, at least one ring being a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
    • C07C51/305—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with sulfur or sulfur-containing compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/42—Separation; Purification; Stabilisation; Use of additives
    • C07C51/487—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to chemical modification
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/30—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings
    • C07C57/38—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings polycyclic
    • C07C57/40—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings polycyclic containing condensed ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/30—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings
    • C07C57/42—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings having unsaturation outside the rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/46—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings and other rings, e.g. cyclohexylphenylacetic acid
    • C07C57/50—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings and other rings, e.g. cyclohexylphenylacetic acid containing condensed ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/52—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen
    • C07C57/58—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/52—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen
    • C07C57/58—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings
    • C07C57/60—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings having unsaturation outside the rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/52—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen
    • C07C57/62—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings and other rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/64—Acyl halides
    • C07C57/72—Acyl halides containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/64—Acyl halides
    • C07C57/76—Acyl halides containing halogen outside the carbonyl halide groups
    • 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
    • C07C59/42—Unsaturated compounds containing hydroxy or O-metal groups
    • C07C59/48—Unsaturated compounds containing hydroxy or O-metal groups containing six-membered aromatic rings
    • 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
    • C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
    • C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
    • 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
    • C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
    • C07C59/72—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings and other rings
    • 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
    • C07C59/74—Unsaturated compounds containing —CHO groups
    • 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
    • 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
    • C07C59/90—Unsaturated compounds containing keto groups containing singly bound oxygen-containing groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C63/00—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings
    • C07C63/33—Polycyclic acids
    • C07C63/337—Polycyclic acids with carboxyl groups bound to condensed ring systems
    • C07C63/34—Polycyclic acids with carboxyl groups bound to condensed ring systems containing two condensed rings

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

1291386 Salts and resolved optical isomers of 2 - (6<SP>1</SP> - substituted - 2<SP>1</SP>- naphthyl) propionic acids SYNTEX CORP 20 Jan 1970 [24 March 1969] 2764/70 Addition to 1211134 Heading C2C Novel compounds of the Formula I wherein one of R<SP>1</SP> and R<SP>2</SP> is hydrogen and the other is methyl or difluoromethyl; R<SP>3</SP> is methyl, ethyl, isopropyl, cyclopropyl, trifluoromethyl, vinyl, ethynyl, fluoro, chloro, methoxy, methoxymethyloxy, difluoromethoxy, methyl thio, methoxymethyl thio or difluoromethyl thio, either in the form of a mixture of d- and lisomers or resolved isomers of the salts with magnesium, ammonium, R 3 N, ethanolamine, methyl glucamine or ethylenediamine, where R is C 1-6 alkyl except ethyl, monocyclic aralkyl or monocyclic aryl or in the form of the resolved d- and l-forms of the free acid or additionally the sodium, potassium, calcium, aluminium, 2-(diethylamino)ethanol, 2 - (dimethylamino)- ethanol, argurine, lysine, caffeine, procaine and triethylamine salts with the proviso in the latter case that when the compound is in the form of the free acid and the other of R<SP>1</SP> and R<SP>2</SP> is methyl, R<SP>3</SP> is cyclopropyl, vinyl, ethynyl, methoxymethyloxy or methoxylmethyl thio may be prepared by either or both of the steps (a) resolving a compound of the Formula I to obtain a d- or l-isomer and (b) reacting a compound I with a base to form the corresponding salt; and optionally one or more of the following steps; (c) hydrolysis of an ester of a compound I, (d) decarboxylation of a 2-(6<SP>1</SP>-substituted-2<SP>1</SP>- naphthyl) - 2 difluoromethyl malonic acid, (e) etherification of compound I in which R<SP>3</SP> is hydroxy or thiol or (f) dehydrobrominating a 2 - [6<SP>1</SP> - (1,2 - dibromoethyl) - 2<SP>1</SP> - naphthyl propionic acid to yield a 2-(6<SP>1</SP>-ethylnyl-2<SP>1</SP>-naphthyl) propionic acid, (g) fluorinating a compound I in which R<SP>3</SP> is CH 3 S or CH 3 O to R<SP>3</SP>=CF 2 HS or CF 2 HO; (h) fluorinating I in which R<SP>3</SP> is CH 3 - to CF 3 via the trichloro compound, (i) oxidizing I in which R<SP>3</SP> is CH 3 CHOH to CH 3 CO; (j) #- methylating a naphthalene acetic ester. The intermediate 2-(6<SP>1</SP>-methoxy-2<SP>1</SP>-naphthyl) acetic acid may be prepared by Friedel-Crafts acetylation of 2-methoxynaphthalene to form 2 - acetyl - 6 - methoxy naphthalene which is converted by a Willgerodt reaction to the required intermediate. The intermediate diethyl 2-(6<SP>1</SP>-methoxy-2<SP>1</SP>- naphthyl) - 2 - difluoromethylmalonate may be - prepared from 2 - (6<SP>1</SP> - methoxy - 2<SP>1</SP>- naphthyl) acetic acid by esterification followed by treatment with diethyl carbonate in strong base. The intermediate 2 - [61 - (1,2 - dibromoethyl)- 2<SP>1</SP>-naphthyl propionic acid may be formed by brominating 2 - (6<SP>1</SP>- vinyl - 2<SP>1</SP> - naphthyl) - propionic acid. Pharmaceutical compositions of the compounds I show anti-inflammatory and antipyretic activity when administered orally or parenterally with the usual excipients.
GB2764/70A 1969-03-24 1970-01-20 Improvements in or relating to 2-(6'-substituted-2'-naphthyl) propionic acid derivatives and salts thereof Expired GB1291386A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US81001469A 1969-03-24 1969-03-24

Publications (1)

Publication Number Publication Date
GB1291386A true GB1291386A (en) 1972-10-04

Family

ID=25202752

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2764/70A Expired GB1291386A (en) 1969-03-24 1970-01-20 Improvements in or relating to 2-(6'-substituted-2'-naphthyl) propionic acid derivatives and salts thereof

Country Status (15)

Country Link
JP (1) JPS5011910B1 (en)
AU (1) AU1006270A (en)
BE (1) BE747812A (en)
BR (1) BR6915470D0 (en)
CA (1) CA960668A (en)
CH (3) CH536803A (en)
DE (1) DE2005454A1 (en)
ES (1) ES377393A2 (en)
FR (1) FR2035827B1 (en)
GB (1) GB1291386A (en)
HK (1) HK27176A (en)
IL (1) IL33646A (en)
MY (1) MY7600048A (en)
NL (1) NL7004193A (en)
NO (1) NO126859B (en)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0007116A1 (en) * 1978-07-19 1980-01-23 Syntex Pharmaceuticals International Limited Method for resolving racemic 6-methoxy-alpha-methyl-2-naphthalene acetic acid into its enantiomers and resolving medium
GB2154233A (en) * 1984-02-16 1985-09-04 Stabil Bioterapico Farmachim Aluminium salts of arylalkanoic acids and pharmaceutical compositions containing them
EP0204911A2 (en) * 1985-04-18 1986-12-17 ALFA WASSERMANN S.p.A. A new process for the optical resolution of racemic mixtures of alpha-naphthylpropionic acids
GB2235449A (en) * 1989-08-24 1991-03-06 Univ Southampton Dinuclear complexes and methods of preparing optical fibres therefrom
MD921G2 (en) * 1992-11-10 1998-10-31 Laboratorios Menarini S.A. Arylpropionic derivatives, process for preparation and the pharmaceutical composition on base thereof
WO2003099293A1 (en) * 2002-05-23 2003-12-04 Danmarks Farmaceutiske Universitet Pharmacologically active salts
WO2020159676A1 (en) * 2019-01-29 2020-08-06 Bayer Healthcare Llc Topical gel compositions of naproxen

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5350819U (en) * 1976-10-05 1978-04-28
DE2935776A1 (en) * 1979-09-05 1981-04-16 Theodor Prof. Dr. 4400 Münster Eckert Indomethacin, naproxen and diclofenac salts - with organic bases, esp. di:ethylamine, tri:ethanol-amine or tri:ethylamine
AT370721B (en) * 1981-02-24 1983-04-25 Ciba Geigy Ag METHOD FOR PRODUCING NEW SALTS OF 2- (2,6-DICHLORANILINO) -PHENYLACETIC ACID, THE
IT1196356B (en) * 1984-12-05 1988-11-16 Pavese Ist Biochim SOLUBLE SALT WITH ANTI-INFLAMMATORY ACTIVITY, PROCEDURE FOR ITS PREPARATION AND PHARMACEUTICAL FORMS CONTAINING THE SAME
IT1207994B (en) * 1986-01-03 1989-06-01 Therapicon Srl WATER SOLUBLE SALTS OF ANTI-INFLAMMATORY AND ANALGESIC ADAPTITY COMPOUNDS, THEIR PREPARATION AND USE IN PHARMACEUTICAL COMPOSITIONS.
US7166641B2 (en) * 2002-10-02 2007-01-23 Yung Shin Pharmaceutical Industrial Co., Ltd. Pharmaceutically acceptable salts containing local anesthetic and anti-inflammatory activities and methods for preparing the same

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU425947B2 (en) * 1968-07-12 1972-07-10 Syntex Corporation 5- substituted and 5- and 6- substituted 2- naphthyl acetic acid derivatives and compositions and methods of preparation thereof

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0007116A1 (en) * 1978-07-19 1980-01-23 Syntex Pharmaceuticals International Limited Method for resolving racemic 6-methoxy-alpha-methyl-2-naphthalene acetic acid into its enantiomers and resolving medium
GB2154233A (en) * 1984-02-16 1985-09-04 Stabil Bioterapico Farmachim Aluminium salts of arylalkanoic acids and pharmaceutical compositions containing them
EP0204911A2 (en) * 1985-04-18 1986-12-17 ALFA WASSERMANN S.p.A. A new process for the optical resolution of racemic mixtures of alpha-naphthylpropionic acids
EP0204911A3 (en) * 1985-04-18 1988-08-03 Alfa Chemicals Italiana S.P.A. A new process for the optical resolution of racemic mixtures of alpha-naphthylpropionic acids
GB2235449A (en) * 1989-08-24 1991-03-06 Univ Southampton Dinuclear complexes and methods of preparing optical fibres therefrom
MD921G2 (en) * 1992-11-10 1998-10-31 Laboratorios Menarini S.A. Arylpropionic derivatives, process for preparation and the pharmaceutical composition on base thereof
WO2003099293A1 (en) * 2002-05-23 2003-12-04 Danmarks Farmaceutiske Universitet Pharmacologically active salts
WO2020159676A1 (en) * 2019-01-29 2020-08-06 Bayer Healthcare Llc Topical gel compositions of naproxen

Also Published As

Publication number Publication date
ES377393A2 (en) 1972-09-16
BR6915470D0 (en) 1973-03-13
CA960668A (en) 1975-01-07
NO126859B (en) 1973-04-02
MY7600048A (en) 1976-12-31
CH536803A (en) 1973-05-15
IL33646A0 (en) 1970-02-19
AU1006270A (en) 1971-07-08
IL33646A (en) 1973-04-30
HK27176A (en) 1976-05-21
FR2035827B1 (en) 1974-09-20
FR2035827A1 (en) 1970-12-24
DE2005454A1 (en) 1970-10-15
CH559162A5 (en) 1975-02-28
CH559161A5 (en) 1975-02-28
NL7004193A (en) 1970-09-28
BE747812A (en) 1970-08-31
JPS5011910B1 (en) 1975-05-07

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
732 Registration of transactions, instruments or events in the register (sect. 32/1977)
732 Registration of transactions, instruments or events in the register (sect. 32/1977)
PE20 Patent expired after termination of 20 years