CH670083A5 - antiinflammatory 4-naphthyl-2-butanone deriv. prodn. - Google Patents

antiinflammatory 4-naphthyl-2-butanone deriv. prodn. Download PDF

Info

Publication number: CH670083A5
Authority: CH; Switzerland
Prior art keywords: carbon atoms; formula; hydrogenation; naphthyl; group
Prior art date: 1986-02-15

Application number

CH53887A

Other languages

German (de)

English (en)

Inventor

Carl John Rose

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

1989-05-12

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

1989-05-12 Publication of CH670083A5 publication Critical patent/CH670083A5/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
HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 claims abstract description 12
238000005984 hydrogenation reaction Methods 0.000 claims abstract description 7
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 4
230000003197 catalytic effect Effects 0.000 claims abstract description 4
-1 p-methoxybenzyl Chemical group 0.000 claims abstract description 4
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims abstract 2
238000000034 method Methods 0.000 claims description 17
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 14
125000004432 carbon atom Chemical group C* 0.000 claims description 13
150000001875 compounds Chemical class 0.000 claims description 10
239000003054 catalyst Substances 0.000 claims description 8
239000001257 hydrogen Substances 0.000 claims description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
238000002360 preparation method Methods 0.000 claims description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 4
125000004185 ester group Chemical group 0.000 claims description 4
229910052736 halogen Inorganic materials 0.000 claims description 4
150000002367 halogens Chemical group 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 3
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
229910052763 palladium Inorganic materials 0.000 claims description 3
239000007868 Raney catalyst Substances 0.000 claims description 2
229910000564 Raney nickel Inorganic materials 0.000 claims description 2
125000003342 alkenyl group Chemical group 0.000 claims description 2
238000009905 homogeneous catalytic hydrogenation reaction Methods 0.000 claims description 2
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims 1
239000003795 chemical substances by application Substances 0.000 claims 1
239000003960 organic solvent Substances 0.000 claims 1
150000002148 esters Chemical group 0.000 abstract description 3
125000000896 monocarboxylic acid group Chemical group 0.000 abstract 2
BLXXJMDCKKHMKV-UHFFFAOYSA-N Nabumetone Chemical compound C1=C(CCC(C)=O)C=CC2=CC(OC)=CC=C21 BLXXJMDCKKHMKV-UHFFFAOYSA-N 0.000 abstract 1
238000009901 transfer hydrogenation reaction Methods 0.000 abstract 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
238000010992 reflux Methods 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 5
239000002904 solvent Substances 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
150000002431 hydrogen Chemical class 0.000 description 3
230000008018 melting Effects 0.000 description 3
238000002844 melting Methods 0.000 description 3
239000000203 mixture Substances 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
238000004880 explosion Methods 0.000 description 2
239000007789 gas Substances 0.000 description 2
125000001624 naphthyl group Chemical group 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
239000007787 solid Substances 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
125000006281 4-bromobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Br)C([H])([H])* 0.000 description 1
125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 1
VZBLASFLFFMMCM-UHFFFAOYSA-N 6-methoxynaphthalene-2-carbaldehyde Chemical compound C1=C(C=O)C=CC2=CC(OC)=CC=C21 VZBLASFLFFMMCM-UHFFFAOYSA-N 0.000 description 1
WDJHALXBUFZDSR-UHFFFAOYSA-N Acetoacetic acid Natural products CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
WOWBFOBYOAGEEA-UHFFFAOYSA-N diafenthiuron Chemical compound CC(C)C1=C(NC(=S)NC(C)(C)C)C(C(C)C)=CC(OC=2C=CC=CC=2)=C1 WOWBFOBYOAGEEA-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
238000004809 thin layer chromatography Methods 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
- C07C45/61—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
- C07C45/67—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 isomerisation; by change of size of the carbon skeleton
- C07C45/673—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 isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton
- C07C45/676—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 isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton by elimination of carboxyl 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)

CH53887A 1986-02-15 1987-02-13 antiinflammatory 4-naphthyl-2-butanone deriv. prodn. CH670083A5 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB868603772A GB8603772D0 (en)	1986-02-15	1986-02-15	Process

Publications (1)

Publication Number	Publication Date
CH670083A5 true CH670083A5 (en)	1989-05-12

Family

ID=10593128

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH53887A CH670083A5 (en)	1986-02-15	1987-02-13	antiinflammatory 4-naphthyl-2-butanone deriv. prodn.

Country Status (8)

Country	Link
JP (1)	JPS62195342A (da)
CH (1)	CH670083A5 (da)
DK (1)	DK75287A (da)
ES (1)	ES2004522A6 (da)
GB (1)	GB8603772D0 (da)
GR (1)	GR870256B (da)
NL (1)	NL8700356A (da)
SE (1)	SE465925B (da)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0267734B1 (en) *	1986-11-11	1994-01-26	Zeneca Limited	Chemical compounds
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
AT344152B (de) *	1975-01-08	1978-07-10	Beecham Group Ltd	Verfahren zur herstellung von neuen naphthalinderivaten
EP0003074B1 (en) *	1978-01-07	1981-04-15	Beecham Group Plc	Process for the preparation of 4-(6-methoxy-2-naphthyl)butan-2-one and 2-acetyl-3-(6-methoxy-2-naphthyl) propenoic acid esters

1986
- 1986-02-15 GB GB868603772A patent/GB8603772D0/en active Pending
1987
- 1987-02-13 SE SE8700592A patent/SE465925B/sv unknown
- 1987-02-13 NL NL8700356A patent/NL8700356A/nl not_active Application Discontinuation
- 1987-02-13 DK DK75287A patent/DK75287A/da unknown
- 1987-02-13 GR GR870256A patent/GR870256B/el unknown
- 1987-02-13 CH CH53887A patent/CH670083A5/de not_active IP Right Cessation
- 1987-02-13 ES ES8700373A patent/ES2004522A6/es not_active Expired
- 1987-02-14 JP JP3229387A patent/JPS62195342A/ja active Pending

Also Published As

Publication number	Publication date
DK75287A (da)	1987-08-16
DK75287D0 (da)	1987-02-13
SE465925B (sv)	1991-11-18
GB8603772D0 (en)	1986-03-19
NL8700356A (nl)	1987-09-01
GR870256B (en)	1987-06-16
SE8700592L (sv)	1987-08-16
JPS62195342A (ja)	1987-08-28
SE8700592D0 (sv)	1987-02-13
ES2004522A6 (es)	1989-01-16

Legal Events

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

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