CH670084A5 - Prodn. of antiinflammatory 4-naphthyl-2-butanone deriv. - Google Patents

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

Info

Publication number: CH670084A5
Authority: CH; Switzerland
Prior art keywords: formula; compound; iii; naphthyl; reaction
Prior art date: 1986-02-15

Application number

CH53687A

Other languages

German (de)

English (en)

Inventor

Richard Keith Anderson

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 CH670084A5 publication Critical patent/CH670084A5/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
BLXXJMDCKKHMKV-UHFFFAOYSA-N Nabumetone Chemical compound C1=C(CCC(C)=O)C=CC2=CC(OC)=CC=C21 BLXXJMDCKKHMKV-UHFFFAOYSA-N 0.000 claims abstract description 7
238000005903 acid hydrolysis reaction Methods 0.000 claims abstract description 6
229910052783 alkali metal Inorganic materials 0.000 claims abstract description 4
150000001340 alkali metals Chemical class 0.000 claims abstract description 4
125000000217 alkyl group Chemical group 0.000 claims abstract description 3
229910052736 halogen Inorganic materials 0.000 claims abstract description 3
150000002367 halogens Chemical group 0.000 claims abstract description 3
150000001875 compounds Chemical class 0.000 claims description 21
238000000034 method Methods 0.000 claims description 16
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
238000006243 chemical reaction Methods 0.000 claims description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
238000002360 preparation method Methods 0.000 claims description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 claims description 3
239000000460 chlorine Substances 0.000 claims description 3
229910052744 lithium Inorganic materials 0.000 claims description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 2
UJOQSHCJYVRZKJ-UHFFFAOYSA-N 3-(1,3-benzoxazol-2-yl)-7-(diethylamino)chromen-2-one Chemical compound C1=CC=C2OC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 UJOQSHCJYVRZKJ-UHFFFAOYSA-N 0.000 claims 1
102100024516 F-box only protein 5 Human genes 0.000 claims 1
101001052797 Homo sapiens F-box only protein 5 Proteins 0.000 claims 1
239000003960 organic solvent Substances 0.000 claims 1
-1 6-methoxy-2-naphthylmethyl halide Chemical class 0.000 abstract 1
JIQXKYSNGXUDJU-UHFFFAOYSA-N propan-2-ylidenehydrazine Chemical compound CC(C)=NN JIQXKYSNGXUDJU-UHFFFAOYSA-N 0.000 abstract 1
150000007857 hydrazones Chemical class 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
RHUYHJGZWVXEHW-UHFFFAOYSA-N 1,1-Dimethyhydrazine Chemical compound CN(C)N RHUYHJGZWVXEHW-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
238000011065 in-situ storage Methods 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
229960004270 nabumetone Drugs 0.000 description 2
JYLGKVDVIPITQM-UHFFFAOYSA-N 2-(chloromethyl)-6-methoxynaphthalene Chemical compound C1=C(CCl)C=CC2=CC(OC)=CC=C21 JYLGKVDVIPITQM-UHFFFAOYSA-N 0.000 description 1
208000025747 Rheumatic disease Diseases 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
230000002917 arthritic effect Effects 0.000 description 1
244000309464 bull Species 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
230000000552 rheumatic effect Effects 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
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/72—Hydrazones
- 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
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/516—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of nitrogen-containing compounds to >C = O groups
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

CH53687A 1986-02-15 1987-02-13 Prodn. of antiinflammatory 4-naphthyl-2-butanone deriv. CH670084A5 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB868603778A GB8603778D0 (en)	1986-02-15	1986-02-15	Chemical process

Publications (1)

Publication Number	Publication Date
CH670084A5 true CH670084A5 (en)	1989-05-12

Family

ID=10593134

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH53687A CH670084A5 (en)	1986-02-15	1987-02-13	Prodn. of antiinflammatory 4-naphthyl-2-butanone deriv.

Country Status (8)

Country	Link
JP (1)	JPS62195344A (da)
CH (1)	CH670084A5 (da)
DK (1)	DK75487A (da)
ES (1)	ES2004879A6 (da)
GB (1)	GB8603778D0 (da)
GR (1)	GR870258B (da)
NL (1)	NL8700358A (da)
SE (1)	SE465926B (da)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0361067A1 (de) *	1988-09-01	1990-04-04	Bayer Ag	Disubstituierte Naphthaline, Verfahren zur Herstellung sowie deren herbizide Verwendung
EP2860169A3 (en) *	2009-04-17	2015-10-21	Centro De Neurociencias De Cuba	Method for obtaining novel derivatives of naphtalene for the in vivo diagnosis of Alzheimer's disease

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4943579A (en) *	1987-10-06	1990-07-24	The United States Of America As Represented By The Secretary Of The Department Of Health And Human Services	Water soluble prodrugs of camptothecin
US5756851A (en) *	1996-10-21	1998-05-26	Albemarle Corporation	Production of nabumetone or precursors thereof

1986
- 1986-02-15 GB GB868603778A patent/GB8603778D0/en active Pending
1987
- 1987-02-13 ES ES8700375A patent/ES2004879A6/es not_active Expired
- 1987-02-13 DK DK75487A patent/DK75487A/da unknown
- 1987-02-13 CH CH53687A patent/CH670084A5/de not_active IP Right Cessation
- 1987-02-13 GR GR870258A patent/GR870258B/el unknown
- 1987-02-13 NL NL8700358A patent/NL8700358A/nl not_active Application Discontinuation
- 1987-02-13 SE SE8700594A patent/SE465926B/sv unknown
- 1987-02-14 JP JP3229587A patent/JPS62195344A/ja active Pending

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0361067A1 (de) *	1988-09-01	1990-04-04	Bayer Ag	Disubstituierte Naphthaline, Verfahren zur Herstellung sowie deren herbizide Verwendung
US5108489A (en) *	1988-09-01	1992-04-28	Bayer Aktiengesellschaft	Herbicidal disubstituted naphthalenes
EP2860169A3 (en) *	2009-04-17	2015-10-21	Centro De Neurociencias De Cuba	Method for obtaining novel derivatives of naphtalene for the in vivo diagnosis of Alzheimer's disease

Also Published As

Publication number	Publication date
GB8603778D0 (en)	1986-03-19
SE8700594D0 (sv)	1987-02-13
NL8700358A (nl)	1987-09-01
DK75487A (da)	1987-08-16
SE465926B (sv)	1991-11-18
SE8700594L (sv)	1987-08-16
ES2004879A6 (es)	1989-02-16
JPS62195344A (ja)	1987-08-28
DK75487D0 (da)	1987-02-13
GR870258B (en)	1987-06-16

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Legal Events

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