JPH0242826B2 - - Google Patents

Info

Publication number: JPH0242826B2
Authority: JP; Japan
Prior art keywords: compound; acetic acid; general formula; phenylthiophenyl; acid
Prior art date: 1980-12-23
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

JP55181247A

Other languages

English (en)

Japanese (ja)

Other versions

JPS57106656A (en

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.)

1980-12-23

Filing date

1980-12-23

Publication date

1990-09-26

1980-12-23 Application filed filed Critical

1980-12-23 Priority to JP18124780A priority Critical patent/JPS57106656A/ja

1982-07-02 Publication of JPS57106656A publication Critical patent/JPS57106656A/ja

1990-09-26 Publication of JPH0242826B2 publication Critical patent/JPH0242826B2/ja

Status Granted legal-status Critical Current

Links

UOCQATUFLPHRNG-UHFFFAOYSA-N 2-phenyl-2-phenylsulfanylacetic acid Chemical class C=1C=CC=CC=1C(C(=O)O)SC1=CC=CC=C1 UOCQATUFLPHRNG-UHFFFAOYSA-N 0.000 claims description 5
JMIYLNQBNSEKAO-UHFFFAOYSA-N 2-(2-phenylsulfanylphenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC=C1SC1=CC=CC=C1 JMIYLNQBNSEKAO-UHFFFAOYSA-N 0.000 claims 1
150000001875 compounds Chemical class 0.000 description 20
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
238000000034 method Methods 0.000 description 7
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-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
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
239000002253 acid Substances 0.000 description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
-1 dibenzothiepine propionic acid derivative Chemical class 0.000 description 3
238000007363 ring formation reaction Methods 0.000 description 3
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
UUFQTNFCRMXOAE-UHFFFAOYSA-N 1-methylmethylene Chemical compound C[CH] UUFQTNFCRMXOAE-UHFFFAOYSA-N 0.000 description 2
GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 2
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
UTFSPWRTXCDUIJ-UHFFFAOYSA-N 3-fluoro-4-(trifluoromethoxy)phenol Chemical compound OC1=CC=C(OC(F)(F)F)C(F)=C1 UTFSPWRTXCDUIJ-UHFFFAOYSA-N 0.000 description 2
101100167062 Caenorhabditis elegans chch-3 gene Proteins 0.000 description 2
101150065749 Churc1 gene Proteins 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
102100038239 Protein Churchill Human genes 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
MUXFZBHBYYYLTH-UHFFFAOYSA-N Zaltoprofen Chemical compound O=C1CC2=CC(C(C(O)=O)C)=CC=C2SC2=CC=CC=C21 MUXFZBHBYYYLTH-UHFFFAOYSA-N 0.000 description 2
239000003513 alkali Substances 0.000 description 2
230000003110 anti-inflammatory effect Effects 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
238000004440 column chromatography Methods 0.000 description 2
239000012043 crude product Substances 0.000 description 2
239000013078 crystal Substances 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
229920000137 polyphosphoric acid Polymers 0.000 description 2
238000010992 reflux Methods 0.000 description 2
238000003756 stirring Methods 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
206010030113 Oedema Diseases 0.000 description 1
241000700159 Rattus Species 0.000 description 1
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
229960001138 acetylsalicylic acid Drugs 0.000 description 1
230000007059 acute toxicity Effects 0.000 description 1
231100000403 acute toxicity Toxicity 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
230000000202 analgesic effect Effects 0.000 description 1
230000001760 anti-analgesic effect Effects 0.000 description 1
229940121363 anti-inflammatory agent Drugs 0.000 description 1
239000002260 anti-inflammatory agent Substances 0.000 description 1
SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-UHFFFAOYSA-N 0.000 description 1
229940113118 carrageenan Drugs 0.000 description 1
235000010418 carrageenan Nutrition 0.000 description 1
229920001525 carrageenan Polymers 0.000 description 1
239000000679 carrageenan Substances 0.000 description 1
239000007810 chemical reaction solvent Substances 0.000 description 1
125000004185 ester group Chemical group 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
229960000905 indomethacin Drugs 0.000 description 1
238000009776 industrial production Methods 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
238000002955 isolation Methods 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
125000002560 nitrile group Chemical group 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
238000011403 purification operation Methods 0.000 description 1
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 description 1
239000002994 raw material Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000000630 rising effect Effects 0.000 description 1
239000000243 solution Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
125000004325 thiepin-2-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C(*)S1 0.000 description 1
238000005406 washing Methods 0.000 description 1
UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 1

Landscapes

Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

JP18124780A 1980-12-23 1980-12-23 Phenylthiophenylacetic acid derivative Granted JPS57106656A (en)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP18124780A JPS57106656A (en)	1980-12-23	1980-12-23	Phenylthiophenylacetic acid derivative

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP18124780A JPS57106656A (en)	1980-12-23	1980-12-23	Phenylthiophenylacetic acid derivative

Publications (2)

Publication Number	Publication Date
JPS57106656A JPS57106656A (en)	1982-07-02
JPH0242826B2 true JPH0242826B2 (da)	1990-09-26

Family

ID=16097360

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP18124780A Granted JPS57106656A (en)	1980-12-23	1980-12-23	Phenylthiophenylacetic acid derivative

Country Status (1)

Country	Link
JP (1)	JPS57106656A (da)

Citations (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5553282A (en) *	1978-10-17	1980-04-18	Nippon Chemiphar Co Ltd	Dibenzothiepin derivative and its preparation

1980
- 1980-12-23 JP JP18124780A patent/JPS57106656A/ja active Granted

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5553282A (en) *	1978-10-17	1980-04-18	Nippon Chemiphar Co Ltd	Dibenzothiepin derivative and its preparation

Also Published As

Publication number	Publication date
JPS57106656A (en)	1982-07-02

Publication	Publication Date	Title
NO140977B (no)	1979-09-10	Analogifremgangsmaate til fremstilling av terapeutisk aktive 2-amino-1,4-dihydropyridiner
DK149230B (da)	1986-03-24	Analogifremgangsmaade til fremstilling af 5-benzoyl-6-hydroxy-indan-1-carboxylsyrederivater eller farmaceutisk acceptable salte deraf
SU479290A3 (ru)	1975-07-30	Способ получени 2-(фурилметил)-6,7бензоморфанов
JPH0432063B2 (da)	1992-05-28
JP2000327603A (ja)	2000-11-28	プロピオン酸誘導体の製造方法
US4568762A (en)	1986-02-04	4-Methyl-2-oxo-cyclopentylidene acetic acid and esters thereof
JPH0129793B2 (da)	1989-06-14
EP0142754A2 (en)	1985-05-29	2-Substituted-benzoic acid imidazoles, process for preparing them and pharmaceutical compositions containing them
KR100330609B1 (ko)	2002-11-22	3-이속사졸카복실산의 제조방법
JPH0242826B2 (da)	1990-09-26
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EP1673365A1 (en)	2006-06-28	Process for the preparation of z-flupentixol
JP3207018B2 (ja)	2001-09-10	ベンジルコハク酸誘導体の製造方法およびその製造中間体
JP2549997B2 (ja)	1996-10-30	新規ハロケタール化合物
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
JPH0522709B2 (da)	1993-03-30
BE858864A (fr)	1978-01-16	Nouveaux esters d'acides phenyl- et pyridine-3-carboxylique et procede permettant leur preparation
JP2612161B2 (ja)	1997-05-21	ジベンゾチエピン誘導体の製造法
US5142091A (en)	1992-08-25	α, β-unsaturated ketones and ketoxime derivatives
HUT58734A (en)	1992-03-30	Optical separating process for producing 3r/3-carboxy-benzyl/-6-/5-fluoro-2-benzothiazolyl/-methoxy-4r-chromanol
JPH0124782B2 (da)	1989-05-15
JPS644508B2 (da)	1989-01-25
JPS6363543B2 (da)	1988-12-07
KR100699457B1 (ko)	2007-03-27	디벤조티에핀 유도체 및 그 중간체의 제조방법
FR2472571A1 (fr)	1981-07-03	Procede pour la preparation de derives d'esters halogeno-vincaminiques et halogeno-apovincaminiques