CH670631A5 - Prodn. of antiinflammatory 4-naphthyl-2-butanone deriv. - Google Patents

Prodn. of antiinflammatory 4-naphthyl-2-butanone deriv. Download PDF

Info

Publication number: CH670631A5
Authority: CH; Switzerland
Prior art keywords: formula; naphthyl; compound; hydrogenation; methoxy
Prior art date: 1986-02-15

Application number

CH54187A

Other languages

German (de)

English (en)

Inventor

Erol Ali Faruk

Original Assignee

Beecham Group Plc

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.)

1986-02-15

Filing date

1987-02-13

Publication date

1989-06-30

1987-02-13 Application filed by Beecham Group Plc filed Critical Beecham Group Plc

1989-06-30 Publication of CH670631A5 publication Critical patent/CH670631A5/de

Links

VEYCCHNUJNXSRR-UHFFFAOYSA-N 4-naphthalen-1-ylbutan-2-one Chemical compound C1=CC=C2C(CCC(=O)C)=CC=CC2=C1 VEYCCHNUJNXSRR-UHFFFAOYSA-N 0.000 title 1
230000003110 anti-inflammatory effect Effects 0.000 title 1
238000005984 hydrogenation reaction Methods 0.000 claims abstract description 9
239000003054 catalyst Substances 0.000 claims abstract description 7
239000003960 organic solvent Substances 0.000 claims abstract description 4
150000003839 salts Chemical class 0.000 claims abstract description 3
229910052736 halogen Inorganic materials 0.000 claims abstract 2
150000002367 halogens Chemical class 0.000 claims abstract 2
150000001875 compounds Chemical class 0.000 claims description 18
238000000034 method Methods 0.000 claims description 11
125000006239 protecting group Chemical group 0.000 claims description 10
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 9
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 6
159000000000 sodium salts Chemical class 0.000 claims description 6
238000002360 preparation method Methods 0.000 claims description 4
238000011065 in-situ storage Methods 0.000 claims description 3
229910052763 palladium Inorganic materials 0.000 claims description 3
BLXXJMDCKKHMKV-UHFFFAOYSA-N Nabumetone Chemical compound C1=C(CCC(C)=O)C=CC2=CC(OC)=CC=C21 BLXXJMDCKKHMKV-UHFFFAOYSA-N 0.000 abstract description 6
238000009903 catalytic hydrogenation reaction Methods 0.000 abstract description 4
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 7
239000000047 product Substances 0.000 description 7
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
239000000203 mixture Substances 0.000 description 5
239000000243 solution Substances 0.000 description 5
KDDYYAXVVDTNND-UHFFFAOYSA-N 1-(5-bromo-6-methoxynaphthalen-2-yl)ethanone Chemical compound C1=C(C(C)=O)C=CC2=C(Br)C(OC)=CC=C21 KDDYYAXVVDTNND-UHFFFAOYSA-N 0.000 description 4
LUZDYPLAQQGJEA-UHFFFAOYSA-N 2-Methoxynaphthalene Chemical compound C1=CC=CC2=CC(OC)=CC=C21 LUZDYPLAQQGJEA-UHFFFAOYSA-N 0.000 description 4
229960000583 acetic acid Drugs 0.000 description 4
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
229910052794 bromium Inorganic materials 0.000 description 4
-1 hydrocarbon esters Chemical class 0.000 description 4
238000003756 stirring Methods 0.000 description 4
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
230000010933 acylation Effects 0.000 description 3
238000005917 acylation reaction Methods 0.000 description 3
150000002168 ethanoic acid esters Chemical class 0.000 description 3
239000003208 petroleum Substances 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
239000004215 Carbon black (E152) Substances 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
239000012346 acetyl chloride Substances 0.000 description 2
239000002585 base Substances 0.000 description 2
238000009835 boiling Methods 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
239000012043 crude product Substances 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
239000012312 sodium hydride Substances 0.000 description 2
229910000104 sodium hydride Inorganic materials 0.000 description 2
XNIGURFWNPLWJM-UHFFFAOYSA-N 1-bromo-2-methoxynaphthalene Chemical compound C1=CC=CC2=C(Br)C(OC)=CC=C21 XNIGURFWNPLWJM-UHFFFAOYSA-N 0.000 description 1
PKQIDSVLSKFZQC-UHFFFAOYSA-N 3-oxobutanal Chemical compound CC(=O)CC=O PKQIDSVLSKFZQC-UHFFFAOYSA-N 0.000 description 1
QIOHYCZTLPXUFR-UHFFFAOYSA-N 4-(5-bromo-6-methoxynaphthalen-2-yl)-4-hydroxybut-3-en-2-one Chemical compound C1=C(C(O)=CC(C)=O)C=CC2=C(Br)C(OC)=CC=C21 QIOHYCZTLPXUFR-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
238000005863 Friedel-Crafts acylation reaction Methods 0.000 description 1
238000005727 Friedel-Crafts reaction Methods 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
239000003377 acid catalyst Substances 0.000 description 1
239000003929 acidic solution Substances 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
125000005907 alkyl ester group Chemical group 0.000 description 1
229940121363 anti-inflammatory agent Drugs 0.000 description 1
239000002260 anti-inflammatory agent Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000012267 brine Substances 0.000 description 1
239000001273 butane Chemical class 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
238000006555 catalytic reaction Methods 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000006482 condensation reaction Methods 0.000 description 1
238000011109 contamination Methods 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
239000000463 material Substances 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical class CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Chemical class CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
238000006722 reduction reaction Methods 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
229910052723 transition metal Inorganic materials 0.000 description 1
150000003624 transition metals Chemical class 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/255—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing ether groups, groups, groups, or 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
- 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
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/65—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CH54187A 1986-02-15 1987-02-13 Prodn. of antiinflammatory 4-naphthyl-2-butanone deriv. CH670631A5 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB868603766A GB8603766D0 (en)	1986-02-15	1986-02-15	Process

Publications (1)

Publication Number	Publication Date
CH670631A5 true CH670631A5 (en)	1989-06-30

Family

ID=10593122

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH54187A CH670631A5 (en)	1986-02-15	1987-02-13	Prodn. of antiinflammatory 4-naphthyl-2-butanone deriv.

Country Status (8)

Country	Link
JP (1)	JPS62215545A (da)
CH (1)	CH670631A5 (da)
DK (1)	DK74987A (da)
ES (1)	ES2004876A6 (da)
GB (1)	GB8603766D0 (da)
GR (1)	GR870253B (da)
NL (1)	NL8700353A (da)
SE (1)	SE8700589L (da)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0792860A1 (en) *	1996-02-21	1997-09-03	ALFA CHEMICALS ITALIANA S.p.A.	Process for the synthesis of nabumetone

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5756851A (en) *	1996-10-21	1998-05-26	Albemarle Corporation	Production of nabumetone or precursors thereof

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB2014993B (en) *	1977-11-03	1982-05-12	Beecham Group Ltd	Chemical compounds
JPS6045621B2 (ja) *	1978-01-27	1985-10-11	ビ−チヤム・グル−プ・リミテツド	ブタノン誘導体の製造方法

1986
- 1986-02-15 GB GB868603766A patent/GB8603766D0/en active Pending
1987
- 1987-02-13 NL NL8700353A patent/NL8700353A/nl not_active Application Discontinuation
- 1987-02-13 DK DK74987A patent/DK74987A/da not_active Application Discontinuation
- 1987-02-13 ES ES8700370A patent/ES2004876A6/es not_active Expired
- 1987-02-13 GR GR870253A patent/GR870253B/el unknown
- 1987-02-13 SE SE8700589A patent/SE8700589L/xx not_active Application Discontinuation
- 1987-02-13 CH CH54187A patent/CH670631A5/de not_active IP Right Cessation
- 1987-02-14 JP JP3229087A patent/JPS62215545A/ja active Pending

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0792860A1 (en) *	1996-02-21	1997-09-03	ALFA CHEMICALS ITALIANA S.p.A.	Process for the synthesis of nabumetone

Also Published As

Publication number	Publication date
GB8603766D0 (en)	1986-03-19
NL8700353A (nl)	1987-09-01
GR870253B (en)	1987-06-16
JPS62215545A (ja)	1987-09-22
DK74987A (da)	1987-08-16
DK74987D0 (da)	1987-02-13
SE8700589D0 (sv)	1987-02-13
ES2004876A6 (es)	1989-02-16
SE8700589L (sv)	1987-08-16

Legal Events

Date	Code	Title	Description
1996-10-15	PL	Patent ceased

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DE3010195A1 (de)	1980-10-02	Verfahren zur herstellung von 2,5-bis(2,2,2-trifluoraethoxy)-n- (2-piperidylmethyl)benzamid
DE68911171T2 (de)	1994-04-07	Flüssigkristall-Verbindungen mit Fluoroalkylradikalen.
DE3006685C2 (de)	1982-09-09	3-Brom-4-fluorbenzonitril und Verfahren zur Herstellung eines substituierten 3-Brom-4-fluorbenzols
CH670631A5 (en)	1989-06-30	Prodn. of antiinflammatory 4-naphthyl-2-butanone deriv.
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CH642370A5 (en)	1984-04-13	Process for the preparation of imidazo[2,1-a]isoindoles
DE2257867A1 (de)	1974-06-06	Verfahren zur herstellung von indolderivaten
DE2164662A1 (de)	1972-07-27	Indanderivate und Verfahren zu ihrer Herstellung
EP0002719B1 (de)	1981-06-24	Verfahren zur Herstellung von 3-Pyridazonen
DE69515729T2 (de)	2000-10-26	Verfahren zur Synthese von Halogenalkylferrocenen
DE69702831T2 (de)	2001-04-05	Verfahren zur Reinigung von Ketosäuren
EP0014478A1 (de)	1980-08-20	Verfahren zur Herstellung von Alkyl-4,10-dihydro-10-oxo-thieno-(3,2-c)-(1)-benzoxepin-8-acetat
AT229320B (de)	1963-09-10	Verfahren zur Herstellung von 3-Methoxy-2-sulfanilamidopyrazin
DE1643945C3 (de)	1978-03-23	Verfahren zur Herstellung von a, a-disubstituierten «-Amino- «"-halogenketonen und deren Saureadditionssalzen
DE2139084B2 (de)	1978-06-29	Verfahren zur Herstellung von 4,4-Diphenyl-piperidinen
EP0941987A1 (de)	1999-09-15	Verfahren zur Herstellung von 2-Amino-4,5,3',4'-tetramethoxybenzophenon
AT226707B (de)	1963-04-10	Verfahren zur Herstellung von neuen 11b-Benzo-(a)-chinolizinderivaten
AT257057B (de)	1967-09-25	Verfahren zur Herstellung von Bis-[4-hydroxymethyl-5-hydroxy-6-methyl-pyridyl-(3)-methyl]-disulfid
AT234698B (de)	1964-07-10	Verfahren zur Herstellung von 4-Sulfanilamido-2,6-di-nieder-alkoxy-pyrimidinen
EP0229593B1 (de)	1991-10-16	Verfahren zur Herstellung von 4,4'-Stilbendialdehyden
DE1768644C (de)		Verfahren zur Herstellung von Acrylophenonen
DE1545661A1 (de)	1969-08-07	Verfahren zur Herstellung von neuen Chinolizidin-Derivaten
DE4108119A1 (de)	1992-09-17	Verfahren zur herstellung von 4'-chlor-2-((3-(10,11-dihydro-5h-dibenz(b,f)azepin-5-yl)propyl) methylaminno) acetophenon und seiner salze, die stabilisierungseiner salze, hierbei erhaeltliche produkte und pharmmazeutische zubereitungen, die diese enthalten
CH631434A5 (en)	1982-08-13	Process for preparing secondary amides of dichloroacetic acid

CH670631A5 - Prodn. of antiinflammatory 4-naphthyl-2-butanone deriv. - Google Patents

Info

Links

Classifications

Landscapes

Applications Claiming Priority (1)

Publications (1)

Family

ID=10593122

Family Applications (1)

Country Status (8)

Cited By (1)

Families Citing this family (1)

Family Cites Families (2)

Cited By (1)

Also Published As

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