FI63396C - Foerfarande foer framstaellning av pao gallavsoendringen verkande /2-isopropyl-4-(2-tenoyl-5-metyl/-fenoxiaettiksyra - Google Patents

Foerfarande foer framstaellning av pao gallavsoendringen verkande /2-isopropyl-4-(2-tenoyl-5-metyl/-fenoxiaettiksyra Download PDF

Info

Publication number: FI63396C
Authority: FI; Finland
Prior art keywords: isopropyl; methyl; verkande; tenoyl; phenoxyethyxide
Prior art date: 1977-04-22

Application number

FI781100A

Other languages

English (en)

Finnish (fi)

Other versions

FI63396B (fi

FI781100A7 (fi

Inventor

Andre Esanu

Original Assignee

Soc D Etudes Prod Chimique

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.)

1977-04-22

Filing date

1978-04-11

Publication date

1983-06-10

1978-04-11 Application filed by Soc D Etudes Prod Chimique filed Critical Soc D Etudes Prod Chimique

1978-10-23 Publication of FI781100A7 publication Critical patent/FI781100A7/fi

1983-02-28 Application granted granted Critical

1983-02-28 Publication of FI63396B publication Critical patent/FI63396B/fi

1983-06-10 Publication of FI63396C publication Critical patent/FI63396C/fi

Links

150000001875 compounds Chemical class 0.000 claims description 15
238000000034 method Methods 0.000 claims description 5
PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 claims description 3
150000002576 ketones Chemical class 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
238000010992 reflux Methods 0.000 claims description 3
239000002904 solvent Substances 0.000 claims description 3
230000003301 hydrolyzing effect Effects 0.000 claims description 2
241000700159 Rattus Species 0.000 description 8
HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
210000000941 bile Anatomy 0.000 description 4
238000002474 experimental method Methods 0.000 description 4
238000003756 stirring Methods 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
-1 alkali metal salt Chemical class 0.000 description 3
238000001990 intravenous administration Methods 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
FKJIJBSJQSMPTI-CAOXKPNISA-M sodium;(4r)-4-[(5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-3,7,12-trioxo-1,2,4,5,6,8,9,11,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]pentanoate Chemical compound [Na+].C1CC(=O)C[C@H]2CC(=O)[C@H]3[C@@H]4CC[C@H]([C@@H](CCC([O-])=O)C)[C@@]4(C)C(=O)C[C@@H]3[C@]21C FKJIJBSJQSMPTI-CAOXKPNISA-M 0.000 description 3
QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
235000012000 cholesterol Nutrition 0.000 description 2
125000004494 ethyl ester group Chemical group 0.000 description 2
230000029142 excretion Effects 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
239000000203 mixture Substances 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
108090000623 proteins and genes Proteins 0.000 description 2
102000004169 proteins and genes Human genes 0.000 description 2
MGSRCZKZVOBKFT-UHFFFAOYSA-N thymol Chemical compound CC(C)C1=CC=C(C)C=C1O MGSRCZKZVOBKFT-UHFFFAOYSA-N 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
206010002091 Anaesthesia Diseases 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
239000005844 Thymol Substances 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
230000037005 anaesthesia Effects 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
238000002955 isolation Methods 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
231100001231 less toxic Toxicity 0.000 description 1
238000005259 measurement Methods 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
230000028327 secretion Effects 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
229960000790 thymol Drugs 0.000 description 1
231100000820 toxicity test Toxicity 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/22—Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Engineering & Computer Science (AREA)
Gastroenterology & Hepatology (AREA)
Life Sciences & Earth Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Steroid Compounds (AREA)
Medicinal Preparation (AREA)

FI781100A 1977-04-22 1978-04-11 Foerfarande foer framstaellning av pao gallavsoendringen verkande /2-isopropyl-4-(2-tenoyl-5-metyl/-fenoxiaettiksyra FI63396C (fi)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB1678977		1977-04-22
GB16789/77A GB1569404A (en)	1977-04-22	1977-04-22	(2-isopropyl-4-(2'-theonyl)-5-methyl) phenoxy acetic acid

Publications (3)

Publication Number	Publication Date
FI781100A7 FI781100A7 (fi)	1978-10-23
FI63396B FI63396B (fi)	1983-02-28
FI63396C true FI63396C (fi)	1983-06-10

Family

ID=10083695

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
FI781100A FI63396C (fi)	1977-04-22	1978-04-11	Foerfarande foer framstaellning av pao gallavsoendringen verkande /2-isopropyl-4-(2-tenoyl-5-metyl/-fenoxiaettiksyra

Country Status (29)

Country	Link
US (2)	US4346100A (fr)
JP (1)	JPS53132555A (fr)
AR (1)	AR215300A1 (fr)
AT (1)	AT359487B (fr)
AU (1)	AU518054B2 (fr)
BE (1)	BE865422A (fr)
CA (1)	CA1109886A (fr)
CH (1)	CH629795A5 (fr)
DE (1)	DE2817399C3 (fr)
DK (1)	DK174578A (fr)
EG (1)	EG13312A (fr)
ES (1)	ES469022A1 (fr)
FI (1)	FI63396C (fr)
FR (2)	FR2387976A1 (fr)
GB (1)	GB1569404A (fr)
HK (1)	HK66580A (fr)
IE (1)	IE46803B1 (fr)
IN (1)	IN147778B (fr)
LU (1)	LU79345A1 (fr)
MX (1)	MX4992E (fr)
MY (1)	MY8100237A (fr)
NL (1)	NL171583C (fr)
NO (1)	NO147449C (fr)
NZ (1)	NZ186912A (fr)
OA (1)	OA05940A (fr)
PH (1)	PH13547A (fr)
PT (1)	PT67919B (fr)
SE (1)	SE425606B (fr)
ZA (1)	ZA781746B (fr)

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
BE757001A (fr) *	1969-10-10	1971-03-16	Cerpha	Derives heterocycliques d'acides phenoxy acetique et leur preparation
CA1007643A (en) *	1972-10-24	1977-03-29	Janssen Pharmaceutica Naamloze Vennootschap	Aroyl-substituted phenylacetic acid derivatives
US3958004A (en) *	1974-04-23	1976-05-18	Merck & Co., Inc.	Phenoxyacetic acid derivatives as uricosuric agents
US3969508A (en) *	1974-11-27	1976-07-13	Smithkline Corporation	Lowering the concentration of plasma triglycerides
JPS5195049A (en) *	1975-02-12	1976-08-20		* ********so*notsu***************************************nino
US4017632A (en) *	1975-10-22	1977-04-12	Centre European De Recherches Pharmacologiques C.E.R.P.H.A.	Phenoxyacetic acid derivatives
FR2342726A1 (fr) *	1976-02-18	1977-09-30	Smithkline Corp	Nouvelles compositions diuretiques
US4115402A (en) *	1977-06-17	1978-09-19	Merck & Co., Inc.	2,3-Dichloro-4-[(substituted-sulfonyl)-phenoxy]-acetic acids

1977
- 1977-04-22 GB GB16789/77A patent/GB1569404A/en not_active Expired
1978
- 1978-03-28 ZA ZA00781746A patent/ZA781746B/xx unknown
- 1978-03-29 CH CH334178A patent/CH629795A5/fr not_active IP Right Cessation
- 1978-03-29 BE BE186354A patent/BE865422A/fr not_active IP Right Cessation
- 1978-03-30 IN IN233/DEL/78A patent/IN147778B/en unknown
- 1978-03-31 LU LU79345A patent/LU79345A1/fr unknown
- 1978-04-06 AT AT244178A patent/AT359487B/de not_active IP Right Cessation
- 1978-04-07 NL NLAANVRAGE7803728,A patent/NL171583C/xx not_active IP Right Cessation
- 1978-04-07 NZ NZ186912A patent/NZ186912A/xx unknown
- 1978-04-11 AU AU34970/78A patent/AU518054B2/en not_active Expired
- 1978-04-11 FI FI781100A patent/FI63396C/fi not_active IP Right Cessation
- 1978-04-11 EG EG249/78A patent/EG13312A/xx active
- 1978-04-14 OA OA56470A patent/OA05940A/fr unknown
- 1978-04-17 US US05/897,287 patent/US4346100A/en not_active Expired - Lifetime
- 1978-04-19 CA CA301,502A patent/CA1109886A/fr not_active Expired
- 1978-04-19 PT PT67919A patent/PT67919B/pt unknown
- 1978-04-20 FR FR7811642A patent/FR2387976A1/fr active Granted
- 1978-04-20 JP JP4598478A patent/JPS53132555A/ja active Granted
- 1978-04-20 DK DK174578A patent/DK174578A/da not_active Application Discontinuation
- 1978-04-20 FR FR7811641A patent/FR2387651A1/fr active Granted
- 1978-04-20 DE DE2817399A patent/DE2817399C3/de not_active Expired
- 1978-04-20 SE SE7804526A patent/SE425606B/sv unknown
- 1978-04-21 MX MX787033U patent/MX4992E/es unknown
- 1978-04-21 NO NO781402A patent/NO147449C/no unknown
- 1978-04-21 IE IE797/78A patent/IE46803B1/en unknown
- 1978-04-21 ES ES469022A patent/ES469022A1/es not_active Expired
- 1978-04-24 PH PH21041A patent/PH13547A/en unknown
- 1978-05-09 AR AR272092A patent/AR215300A1/es active
1979
- 1979-11-21 US US06/097,037 patent/US4254162A/en not_active Expired - Lifetime
1980
- 1980-11-20 HK HK665/80A patent/HK66580A/xx unknown
1981
- 1981-12-30 MY MY237/81A patent/MY8100237A/xx unknown

Also Published As

Publication number	Publication date
AT359487B (de)	1980-11-10
FR2387976B1 (fr)	1980-08-29
IN147778B (fr)	1980-06-28
MY8100237A (en)	1981-12-31
US4346100A (en)	1982-08-24
MX4992E (es)	1983-01-31
CH629795A5 (fr)	1982-05-14
ATA244178A (de)	1980-04-15
AU518054B2 (en)	1981-09-10
EG13312A (en)	1981-03-31
HK66580A (en)	1980-11-28
IE46803B1 (en)	1983-09-21
SE7804526L (sv)	1978-10-23
NO147449C (no)	1983-04-13
DK174578A (da)	1979-01-04
OA05940A (fr)	1981-06-30
NL171583C (nl)	1983-04-18
CA1109886A (fr)	1981-09-29
DE2817399B2 (de)	1979-09-27
FI63396B (fi)	1983-02-28
FR2387651A1 (fr)	1978-11-17
PH13547A (en)	1980-06-26
NO147449B (no)	1983-01-03
ZA781746B (en)	1979-03-28
FR2387976A1 (fr)	1978-11-17
DE2817399A1 (de)	1978-10-26
FR2387651B1 (fr)	1980-08-29
ES469022A1 (es)	1978-11-16
US4254162A (en)	1981-03-03
PT67919A (en)	1978-05-01
IE780797L (en)	1978-10-22
FI781100A7 (fi)	1978-10-23
JPS53132555A (en)	1978-11-18
AR215300A1 (es)	1979-09-28
AU3497078A (en)	1979-10-18
NL171583B (nl)	1982-11-16
NO781402L (no)	1978-10-24
PT67919B (en)	1979-11-14
NL7803728A (nl)	1978-10-24
SE425606B (sv)	1982-10-18
LU79345A1 (fr)	1978-07-13
GB1569404A (en)	1980-06-11
BE865422A (fr)	1978-07-17
NZ186912A (en)	1979-06-19
JPS5426533B2 (fr)	1979-09-04
DE2817399C3 (de)	1980-06-19

Legal Events

Date	Code	Title	Description
2004-08-31	MM	Patent lapsed	Owner name: SOCIETE D'ETUDES DE PRODUITS CHIMIQUES

Publication	Publication Date	Title
JP2919030B2 (ja)	1999-07-12	キノン誘導体
US3784697A (en)	1974-01-08	Pharmaceutical composition containing phenoxyalkane-carboxylic acids,salts and esters thereof
JPS6089474A (ja)	1985-05-20	モルフイナン誘導体，その製造方法，及び該化合物を含有する抗腫瘍剤
FR2554719A1 (fr)	1985-05-17	Medicaments a base de nouveaux derives de la vinyl-6 furo-(3,4-c)-pyridine
CA1212380A (fr)	1986-10-07	Procede de preparation de nouveaux derives de thieno (2,3-b) pyrrole
JPS58206581A (ja)	1983-12-01	ピロガロ−ルの新規な環置換誘導体
EP0000200B1 (fr)	1982-03-24	N-Amidino-3,5-diamino-6-substitué-2-pyrazinecarboxamides et procédé pour leur préparation
EP0071935B1 (fr)	1985-11-13	Composés du 1-phényl-2-aminocarbonylindole, procédé de préparation et intermédiaires et médicaments contenant ces composés
JPS63135351A (ja)	1988-06-07	グリチルレチン酸誘導体、その製法及び該化合物を有効成分とする抗潰瘍剤
US4699925A (en)	1987-10-13	Biphenylylpropionic acid derivative and pharmaceutical composition containing the same
JPH0150698B2 (fr)	1989-10-31
EP0006789A1 (fr)	1980-01-09	Composés bis (aryloxyalcanecarboxyliques), leur préparation et leur utilisation en thérapeutique
FI63396C (fi)	1983-06-10	Foerfarande foer framstaellning av pao gallavsoendringen verkande /2-isopropyl-4-(2-tenoyl-5-metyl/-fenoxiaettiksyra
DD201792A5 (de)	1983-08-10	Verfahren zur herstellung der 2,3,4,5-tetrahydro-1-benzoxepin-3,5-dion-derivate
JPH0710863B2 (ja)	1995-02-08	エーテル化若しくはエステル化しうるジヒドロキシ基により位置２で置換された４―ｏｈキノリンカルボン酸の新規の誘導体、その製造方法、及び医薬としてのその使用
EP0058009A1 (fr)	1982-08-18	Dérivés de benzanilide et composés pharmaceutiques les contenant
GB1561153A (en)	1980-02-13	Process for the preparation of thiochroman derivatives
EP0026675B1 (fr)	1984-03-14	Acides 1-azaxanthone-3-carboxyliques, leur préparation et compositions pharmaceutiques les contenant
KR800001566B1 (ko)	1980-12-28	페녹시 초산 유도체의 제조방법
Khan et al.	1978	Synthesis of 3-substituted 1, 4-benzodiazepine-2-ones
US5508280A (en)	1996-04-16	5H-Dibenzo (A,D) cycloheptenes as muscarinic receptor antagonists
US3914343A (en)	1975-10-21	Phosphoric acid esters of 5-(2-aminoethoxy)-carvacrols
JPS62103017A (ja)	1987-05-13	抗肝炎剤
GB1579839A (en)	1980-11-26	Chlorophenoxybenzene derivatives
US2064945A (en)	1936-12-22	Pyridine derivatives and process of making the same