JPH0733345B2 - 化合物の製造方法 - Google Patents

化合物の製造方法

Info

Publication number: JPH0733345B2
Authority: JP; Japan
Prior art keywords: methoxy; naphthyl; methyllithium; formula; metal derivative
Prior art date: 1986-02-15
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 - Lifetime

Application number

JP3229487A

Other languages

English (en)

Japanese (ja)

Other versions

JPS62195343A (ja

Inventor

シドニー・エドワード・カーランダー

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.)

SmithKline Beecham Ltd

Original Assignee

SmithKline Beecham Ltd

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

1987-02-14

Publication date

1995-04-12

1987-02-14 Application filed by SmithKline Beecham Ltd filed Critical SmithKline Beecham Ltd

1987-08-28 Publication of JPS62195343A publication Critical patent/JPS62195343A/ja

1995-04-12 Publication of JPH0733345B2 publication Critical patent/JPH0733345B2/ja

2010-04-12 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 title claims description 8
238000004519 manufacturing process Methods 0.000 title claims description 7
229910052751 metal Inorganic materials 0.000 claims description 9
239000002184 metal Substances 0.000 claims description 9
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
-1 alkali metal salt Chemical class 0.000 claims description 5
238000000034 method Methods 0.000 claims description 5
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 4
BLXXJMDCKKHMKV-UHFFFAOYSA-N Nabumetone Chemical compound C1=C(CCC(C)=O)C=CC2=CC(OC)=CC=C21 BLXXJMDCKKHMKV-UHFFFAOYSA-N 0.000 claims description 4
238000006243 chemical reaction Methods 0.000 claims description 4
229910003002 lithium salt Inorganic materials 0.000 claims description 4
159000000002 lithium salts Chemical class 0.000 claims description 4
235000019260 propionic acid Nutrition 0.000 claims description 4
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 4
238000010992 reflux Methods 0.000 claims description 3
229910052783 alkali metal Inorganic materials 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
150000002367 halogens Chemical class 0.000 claims description 2
IHLVCKWPAMTVTG-UHFFFAOYSA-N lithium;carbanide Chemical compound [Li+].[CH3-] IHLVCKWPAMTVTG-UHFFFAOYSA-N 0.000 claims 3
239000003960 organic solvent Substances 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
239000000047 product Substances 0.000 description 6
DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 5
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
239000012043 crude product Substances 0.000 description 2
239000000203 mixture Substances 0.000 description 2
229960004270 nabumetone Drugs 0.000 description 2
239000002904 solvent Substances 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
LWOTXBQKJLOAOZ-UHFFFAOYSA-N 1-(6-methoxynaphthalen-2-yl)propan-1-one Chemical compound C1=C(OC)C=CC2=CC(C(=O)CC)=CC=C21 LWOTXBQKJLOAOZ-UHFFFAOYSA-N 0.000 description 1
LUZDYPLAQQGJEA-UHFFFAOYSA-N 2-Methoxynaphthalene Chemical compound C1=CC=CC2=CC(OC)=CC=C21 LUZDYPLAQQGJEA-UHFFFAOYSA-N 0.000 description 1
238000005727 Friedel-Crafts reaction Methods 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
238000005672 Willgerodt-Kindler rearrangement reaction Methods 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000002917 arthritic effect Effects 0.000 description 1
229940045348 brown mixture Drugs 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
125000002346 iodo group Chemical group I* 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
MCSAJNNLRCFZED-UHFFFAOYSA-N nitroethane Chemical compound CC[N+]([O-])=O MCSAJNNLRCFZED-UHFFFAOYSA-N 0.000 description 1
RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1

Classifications

- 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
- C07C45/004—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with organometalhalides
- 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
- 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
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Engineering & Computer Science (AREA)
Oil, Petroleum & Natural Gas (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

JP3229487A 1986-02-15 1987-02-14 化合物の製造方法 Expired - Lifetime JPH0733345B2 (ja)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB868603777A GB8603777D0 (en)	1986-02-15	1986-02-15	Chemical process
GB8603777		1986-02-15

Publications (2)

Publication Number	Publication Date
JPS62195343A JPS62195343A (ja)	1987-08-28
JPH0733345B2 true JPH0733345B2 (ja)	1995-04-12

Family

ID=10593133

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP3229487A Expired - Lifetime JPH0733345B2 (ja)	1986-02-15	1987-02-14	化合物の製造方法

Country Status (8)

Country	Link
JP (1)	JPH0733345B2 (da)
CH (1)	CH670082A5 (da)
DK (1)	DK75387A (da)
ES (1)	ES2004224A6 (da)
GB (1)	GB8603777D0 (da)
GR (1)	GR870257B (da)
NL (1)	NL8700357A (da)
SE (1)	SE8700593L (da)

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 (1)

* 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

1986
- 1986-02-15 GB GB868603777A patent/GB8603777D0/en active Pending
1987
- 1987-02-13 GR GR870257A patent/GR870257B/el unknown
- 1987-02-13 CH CH53787A patent/CH670082A5/de not_active IP Right Cessation
- 1987-02-13 ES ES8700374A patent/ES2004224A6/es not_active Expired
- 1987-02-13 SE SE8700593A patent/SE8700593L/xx not_active Application Discontinuation
- 1987-02-13 DK DK75387A patent/DK75387A/da not_active Application Discontinuation
- 1987-02-13 NL NL8700357A patent/NL8700357A/nl not_active Application Discontinuation
- 1987-02-14 JP JP3229487A patent/JPH0733345B2/ja not_active Expired - Lifetime

Also Published As

Publication number	Publication date
ES2004224A6 (es)	1988-12-16
SE8700593L (sv)	1987-08-16
SE8700593D0 (sv)	1987-02-13
JPS62195343A (ja)	1987-08-28
CH670082A5 (en)	1989-05-12
GR870257B (en)	1987-06-16
DK75387A (da)	1987-08-16
GB8603777D0 (en)	1986-03-19
DK75387D0 (da)	1987-02-13
NL8700357A (nl)	1987-09-01

Publication	Publication Date	Title
JP3145824B2 (ja)	2001-03-12	新規な２−シアノ−３−ヒドロキシエナミド、それらの製造法、それらを含有する製薬組成物及びそれらの薬剤としての使用
EP0026928B1 (en)	1984-01-25	3,4-diarylisoxazol-5-acetic acid compounds, process for preparing the same, and pharmaceuticals containing the same
JPH0348181B2 (da)	1991-07-23
JP2004043482A (ja)	2004-02-12	カルボン酸誘導体
JP2005501841A (ja)	2005-01-20	複素環式ペンタレン誘導体の製造方法
JPH05208978A (ja)	1993-08-20	１，２−ジヒドロ−３Ｈ−ピロロ〔１，２−α〕ピロール−１−カルボン酸エステルの５位のアロイル化方法
US4173709A (en)	1979-11-06	Process for the preparation of dextrorotatory 2-phenoxypropionic acid derivatives
JPH0222059B2 (da)	1990-05-17
US3186999A (en)	1965-06-01	Isothiazole derivatives
JPH0733345B2 (ja)	1995-04-12	化合物の製造方法
JP3450827B2 (ja)	2003-09-29	置換２−ベンゾ［ｂ］チオフェンカルボン酸およびそれらの塩の合成方法
US5041640A (en)	1991-08-20	Process for mono-, di-, trisubstituted acetic acids
JP2005508964A (ja)	2005-04-07	組織−選択性エストロゲンの生成のための価値ある中間生成物としての酸素−置換されたベンゾシクロへプテンの合成
US4008269A (en)	1977-02-15	Phenylacetic acids
US5233082A (en)	1993-08-03	Method of making 3-hydroxy-2,4,5-trifluorobenzoic acid
JP3012705B2 (ja)	2000-02-28	（２−ヒドロキシフェニル）酢酸の製造方法
HK45783A (en)	1983-10-28	Process for preparing thiazoles
JPS638954B2 (da)	1988-02-25
BROWN et al.	1962	The synthesis of some substituted 5-bromopentylamine hydrobromides
JPS5821626B2 (ja)	1983-05-02	チカンサクサンユウドウタイノセイゾウホウ
CA1037061A (en)	1978-08-22	ORTHO-HYDROXY-.omega.-(METHYLSULFINYL)ACETONAPHTHONES AND PROCESS FOR PRODUCING SAME
CA1137997A (en)	1982-12-21	Process for making 4-aroyl-substituted phenoxyacetic acids
JP2660330B2 (ja)	1997-10-08	チオフェン誘導体及びその製造方法
KR860001312B1 (ko)	1986-09-13	말론산 유도체의 제조방법
JPH07285926A (ja)	1995-10-31	クロロアルキルスルホニルクロリドの製造方法