NL8204061A - Derivaten van 4-fenyl-4-oxo-2-buteenzuur en zouten daarvan als geneesmiddel en farmaceutische preparaten op basis daarvan. - Google Patents

Derivaten van 4-fenyl-4-oxo-2-buteenzuur en zouten daarvan als geneesmiddel en farmaceutische preparaten op basis daarvan. Download PDF

Info

Publication number: NL8204061A
Authority: NL; Netherlands
Prior art keywords: formula; hydrogen atom; oxo; phenyl; salts
Prior art date: 1981-10-22

Application number

NL8204061A

Other languages

English (en)

Dutch (nl)

Original Assignee

Roussel Uclaf

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.)

1981-10-22

Filing date

1982-10-21

Publication date

1983-05-16

1982-10-21 Application filed by Roussel Uclaf filed Critical Roussel Uclaf

1983-05-16 Publication of NL8204061A publication Critical patent/NL8204061A/nl

Links

239000000825 pharmaceutical preparation Substances 0.000 title claims description 5
PLPDHGOODMBBGN-UHFFFAOYSA-N 4-oxo-4-phenylbut-2-enoic acid Chemical class OC(=O)C=CC(=O)C1=CC=CC=C1 PLPDHGOODMBBGN-UHFFFAOYSA-N 0.000 title 1
229940126601 medicinal product Drugs 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 27
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
239000003814 drug Substances 0.000 claims description 13
125000000217 alkyl group Chemical group 0.000 claims description 9
-1 amine salts Chemical class 0.000 claims description 9
229910052783 alkali metal Inorganic materials 0.000 claims description 8
150000001340 alkali metals Chemical class 0.000 claims description 8
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 8
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 7
150000001342 alkaline earth metals Chemical class 0.000 claims description 7
125000004432 carbon atom Chemical group C* 0.000 claims description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
239000002253 acid Substances 0.000 claims description 3
238000000034 method Methods 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
150000007513 acids Chemical class 0.000 claims description 2
239000004480 active ingredient Substances 0.000 claims 1
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 26
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
241001465754 Metazoa Species 0.000 description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
239000000243 solution Substances 0.000 description 7
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
230000008018 melting Effects 0.000 description 6
238000002844 melting Methods 0.000 description 6
239000000203 mixture Substances 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
239000007788 liquid Substances 0.000 description 5
150000003839 salts Chemical class 0.000 description 5
241000700159 Rattus Species 0.000 description 4
230000002496 gastric effect Effects 0.000 description 4
239000000047 product Substances 0.000 description 4
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
229920002472 Starch Polymers 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
230000000767 anti-ulcer Effects 0.000 description 3
239000002775 capsule Substances 0.000 description 3
230000027119 gastric acid secretion Effects 0.000 description 3
235000019359 magnesium stearate Nutrition 0.000 description 3
FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical class O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 3
239000000546 pharmaceutical excipient Substances 0.000 description 3
239000007787 solid Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
239000008107 starch Substances 0.000 description 3
235000019698 starch Nutrition 0.000 description 3
238000003756 stirring Methods 0.000 description 3
210000002784 stomach Anatomy 0.000 description 3
239000000454 talc Substances 0.000 description 3
229910052623 talc Inorganic materials 0.000 description 3
TXFPEBPIARQUIG-UHFFFAOYSA-N 4'-hydroxyacetophenone Chemical compound CC(=O)C1=CC=C(O)C=C1 TXFPEBPIARQUIG-UHFFFAOYSA-N 0.000 description 2
ZOIRMVZWDRLJPI-UHFFFAOYSA-N 4-oxobut-2-enoic acid Chemical compound OC(=O)C=CC=O ZOIRMVZWDRLJPI-UHFFFAOYSA-N 0.000 description 2
KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
206010020601 Hyperchlorhydria Diseases 0.000 description 2
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
208000007107 Stomach Ulcer Diseases 0.000 description 2
208000025865 Ulcer Diseases 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
230000000694 effects Effects 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
210000004051 gastric juice Anatomy 0.000 description 2
HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
239000008101 lactose Substances 0.000 description 2
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
230000036269 ulceration Effects 0.000 description 2
PWMWNFMRSKOCEY-UHFFFAOYSA-N 1-Phenyl-1,2-ethanediol Chemical compound OCC(O)C1=CC=CC=C1 PWMWNFMRSKOCEY-UHFFFAOYSA-N 0.000 description 1
244000215068 Acacia senegal Species 0.000 description 1
229910002012 Aerosil® Inorganic materials 0.000 description 1
206010002091 Anaesthesia Diseases 0.000 description 1
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
229920000084 Gum arabic Polymers 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
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
208000008469 Peptic Ulcer Diseases 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
241000656145 Thyrsites atun Species 0.000 description 1
230000003187 abdominal effect Effects 0.000 description 1
239000000205 acacia gum Substances 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
230000007059 acute toxicity Effects 0.000 description 1
231100000403 acute toxicity Toxicity 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
230000037005 anaesthesia Effects 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
150000001555 benzenes Chemical class 0.000 description 1
238000009835 boiling Methods 0.000 description 1
159000000007 calcium salts Chemical class 0.000 description 1
239000001768 carboxy methyl cellulose Substances 0.000 description 1
235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
239000008112 carboxymethyl-cellulose Substances 0.000 description 1
235000013339 cereals Nutrition 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
229940110456 cocoa butter Drugs 0.000 description 1
235000019868 cocoa butter Nutrition 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
230000001120 cytoprotective effect Effects 0.000 description 1
239000012024 dehydrating agents‎ Substances 0.000 description 1
125000005265 dialkylamine group Chemical group 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
230000029087 digestion Effects 0.000 description 1
210000002249 digestive system Anatomy 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
239000008298 dragée Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
210000003238 esophagus Anatomy 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000003925 fat Substances 0.000 description 1
235000019197 fats Nutrition 0.000 description 1
210000001156 gastric mucosa Anatomy 0.000 description 1
231100000029 gastro-duodenal ulcer Toxicity 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
239000008187 granular material Substances 0.000 description 1
239000012535 impurity Substances 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
230000003902 lesion Effects 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
MOOYVEVEDVVKGD-UHFFFAOYSA-N oxaldehydic acid;hydrate Chemical compound O.OC(=O)C=O MOOYVEVEDVVKGD-UHFFFAOYSA-N 0.000 description 1
239000012071 phase Substances 0.000 description 1
235000020004 porter Nutrition 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
238000011084 recovery Methods 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229940100486 rice starch Drugs 0.000 description 1
239000000523 sample Substances 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
238000001665 trituration Methods 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
238000005303 weighing Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/76—Unsaturated compounds containing keto groups
- C07C59/84—Unsaturated compounds containing keto groups containing six membered aromatic rings
- 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
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/76—Unsaturated compounds containing keto groups
- C07C59/90—Unsaturated compounds containing keto groups containing singly bound oxygen-containing groups

Landscapes

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

NL8204061A 1981-10-22 1982-10-21 Derivaten van 4-fenyl-4-oxo-2-buteenzuur en zouten daarvan als geneesmiddel en farmaceutische preparaten op basis daarvan. NL8204061A (nl)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
IT8149548A IT1210582B (it)	1981-10-22	1981-10-22	Derivati di acido 4-fenil-4-ossobuten-2-oico dotati di proprieta'farmacologiche e composizioni farmaceutiche che li contengono
IT4954881		1981-10-22

Publications (1)

Publication Number	Publication Date
NL8204061A true NL8204061A (nl)	1983-05-16

Family

ID=11270992

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL8204061A NL8204061A (nl)	1981-10-22	1982-10-21	Derivaten van 4-fenyl-4-oxo-2-buteenzuur en zouten daarvan als geneesmiddel en farmaceutische preparaten op basis daarvan.

Country Status (12)

Country	Link
US (1)	US4473583A (fr)
JP (1)	JPS5883620A (fr)
BE (1)	BE894766A (fr)
CA (1)	CA1181340A (fr)
CH (1)	CH654289A5 (fr)
DE (1)	DE3239189A1 (fr)
FR (1)	FR2515038B1 (fr)
GB (1)	GB2108385B (fr)
IT (1)	IT1210582B (fr)
LU (1)	LU84429A1 (fr)
NL (1)	NL8204061A (fr)
SE (1)	SE455420B (fr)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2515037A1 (fr) *	1981-10-22	1983-04-29	Roussel Uclaf	A titre de medicaments, certains derives mono-substitues de l'acide 4-phenyl 4-oxo buten-2-oique, ainsi que les compositions les renfermant
IT1169783B (it) *	1983-08-25	1987-06-03	Roussel Maestretti Spa	Derivati dell' acido 4-fenil 4-osso-buten 2-oico, loro procedimento di preparazione e loro applicazione come prodotti medicinali
DE3338953A1 (de) *	1983-10-27	1985-05-09	Henkel KGaA, 4000 Düsseldorf	Verwendung von korrosionsinhibitoren in waessrigen systemen
NZ211490A (en) *	1984-03-23	1988-10-28	Commw Scient Ind Res Org	Deuterated compounds and arthropodicidal compositions
IT1190340B (it) *	1986-06-06	1988-02-16	Roussel Maestretti Spa	Derivati dell'acido 4-fenil 4-osso 2-butenoico,loro procedimento di preparazione e loro impiego come prodotti medicinali
JPH04235142A (ja) *	1991-01-09	1992-08-24	Kanegafuchi Chem Ind Co Ltd	トランス−β−アロイルアクリル酸エステル類の製造法
KR101005969B1 (ko) *	2002-05-15	2011-01-05	메이지 세이까 가부시끼가이샤	4-페닐-4-옥소-2-부텐산 에스테르 유도체의 제조방법

Family Cites Families (21)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB588108A (en) *	1944-10-23	1947-05-14	Roche Products Ltd	Manufacture of bacteriostatic substances
US2532579A (en) *	1946-08-06	1950-12-05	Du Pont	Pest control compositions containing beta-acyl acrylates
US2562208A (en) *	1947-04-14	1951-07-31	Schering Corp	Fungistatic composition
US2795554A (en) *	1952-04-21	1957-06-11	Monsanto Chemicals	Antiseptic soap composition
DE1282644B (de) *	1962-09-08	1968-11-14	Hoechst Ag	Verfahren zur Herstellung von ungesaettigten ª€-Ketocarbonsaeureestern
NL6717403A (fr) *	1966-12-30	1968-07-01
GR37790B (el) *	1966-12-30	1969-07-15	F. Hoffmann - La Roche & Co. Aktiengesellschaft	Μεθοδος δια την παρασκευην παραγωγων του αρουλακρυλικου οξεος.
DE2047806A1 (en) *	1970-09-29	1972-04-06	Dr Karl Thomae GmbH, 7950 Biberach	3-aroyl-acrylic acids - pharmaceutical intermediates prepd from acetophenones and glyoxylic acid derivs
DE2103749A1 (en) *	1971-01-27	1972-08-10	Dr. Karl Thomae GmbH, 7951 Biberach	3-acyl-acrylic acids prepn - from a ketone and glyoxylic acid (deriv)
DE2116293A1 (de) *	1971-04-02	1972-10-19	Cassella Farbwerke Mainkur Ag, 6000 Frankfurt	Ketonderivate und Verfahren zu ihrer Herstellung
US3753997A (en) *	1971-06-07	1973-08-21	A Ash	Trifluoromethly substituted-2,6-diphenyl-4-pyridyl carbinolamine antimalarials
BE788749A (fr) *	1971-09-13	1973-03-13	Takeda Chemical Industries Ltd	Acide 3-(benzoyl trisubstitue)-propionique et son procede de preparation
US4017517A (en) *	1971-09-13	1977-04-12	Takeda Chemical Industries, Ltd.	2-(Trisubstituted benzoyl)-propionic acid and a method for the production thereof
BE795893A (fr) *	1972-02-28	1973-06-18	Unicler	Derives de (methylene dioxy-3,4 phenyl)-1 dimethyl-4,4 pentene-1, leur preparation et leur application en therrapeutique
GB1392100A (en) *	1972-09-13	1975-04-23	Beecham Group Ltd	Insecticides
CH591415A5 (en) *	1972-09-13	1977-09-15	Takeda Chemical Industries Ltd	3-(Tri-substd. benzoyl) propionic acids - as relaxants or spasmolytics for the gall bladder
FR2270856B1 (fr) *	1974-01-17	1978-07-21	Screen
US3953463A (en) *	1974-03-06	1976-04-27	The United States Of America As Represented By The Secretary Of The Army	2-Aryl-6-trifluoromethyl-4-pyridyl-carbinolamine antimalarials
US3940404A (en) *	1974-03-06	1976-02-24	The United States Of America As Represented By The Secretary Of The Army	2-Substituted phenyl-6-trifluoromethyl-4-pyridyl-carbinolamines
FR2265409A1 (en) *	1974-03-25	1975-10-24	Fabre Sa Pierre	4-Oxo-4-phenyl-2-methyl(ene)-butyric acid derivs. - analgesics, antiinflammatories and hypocholesterolemiants
JPS5536434A (en) *	1978-09-07	1980-03-14	Sankyo Co Ltd	4-phenyl-4-oxo-2-butenoic acid derivative and its preparation

1981
- 1981-10-22 IT IT8149548A patent/IT1210582B/it active
1982
- 1982-10-15 SE SE8205868A patent/SE455420B/sv not_active IP Right Cessation
- 1982-10-20 US US06/435,463 patent/US4473583A/en not_active Expired - Fee Related
- 1982-10-21 CA CA000413905A patent/CA1181340A/fr not_active Expired
- 1982-10-21 CH CH6133/82A patent/CH654289A5/fr not_active IP Right Cessation
- 1982-10-21 LU LU84429A patent/LU84429A1/fr unknown
- 1982-10-21 NL NL8204061A patent/NL8204061A/nl not_active Application Discontinuation
- 1982-10-21 FR FR8217621A patent/FR2515038B1/fr not_active Expired
- 1982-10-21 BE BE0/209295A patent/BE894766A/fr not_active IP Right Cessation
- 1982-10-22 GB GB08230214A patent/GB2108385B/en not_active Expired
- 1982-10-22 JP JP57184810A patent/JPS5883620A/ja active Pending
- 1982-10-22 DE DE19823239189 patent/DE3239189A1/de not_active Withdrawn

Also Published As

Publication number	Publication date
DE3239189A1 (de)	1983-05-05
JPS5883620A (ja)	1983-05-19
FR2515038A1 (fr)	1983-04-29
GB2108385A (en)	1983-05-18
IT1210582B (it)	1989-09-14
FR2515038B1 (fr)	1985-08-23
CH654289A5 (fr)	1986-02-14
BE894766A (fr)	1983-04-21
LU84429A1 (fr)	1983-06-13
SE8205868D0 (sv)	1982-10-15
US4473583A (en)	1984-09-25
IT8149548A0 (it)	1981-10-22
SE8205868L (sv)	1983-04-23
GB2108385B (en)	1985-07-03
CA1181340A (fr)	1985-01-22
SE455420B (sv)	1988-07-11

Legal Events

Date	Code	Title	Description
1985-01-01	A85	Still pending on 85-01-01
1989-12-01	BV	The patent application has lapsed

Publication	Publication Date	Title
EP0203957B1 (fr)	1990-03-14	Acides 2-hydroxybenzene acetique 5-(phenylazo-3,5-substitué), leurs sels et lactones, et les compositions pharmaceutiques des dits acides, sels et lactones
US4247706A (en)	1981-01-27	Dibenzothiepin derivatives and a process for producing the same
NL8204061A (nl)	1983-05-16	Derivaten van 4-fenyl-4-oxo-2-buteenzuur en zouten daarvan als geneesmiddel en farmaceutische preparaten op basis daarvan.
SE451838B (sv)	1987-11-02	Substituerade 4-fenyl-4-oxo-2-butensyraderivat till anvendning som lekemedel samt farmaceutisk komposition innehallande dessa
NL8204062A (nl)	1983-05-16	Derivaten van 4-fenyl-4-oxo-2-buteenzuur en zouten daarvan, farmaceutische preparaten op basis daarvan en werkwijze voor het bereiden van een en ander.
HU186857B (en)	1985-10-28	Process for the production of new phenylaliphatic carboxilic acid derivatives
FR2540109A1 (fr)	1984-08-03	Imino-2 pyrrolidines, leur procede de preparation et leurs applications en therapeutique
JPS6072843A (ja)	1985-04-24	４−フエニル−４−オキソ−２−ブテン酸の新誘導体、それらの製造法、薬剤としての使用及びそれらを含む組成物
US4816472A (en)	1989-03-28	Derivatives of 19,20-Bis-nor-prostanoic acid with antiulcer and anorectic activity, process for their preparation and pharmaceutical compositions thereof
US4867737A (en)	1989-09-19	Derivatives of 4-phenyl-4-oxo-2-butenoic acid their preparation process, their use as medicaments and compositions containing them
US3923996A (en)	1975-12-02	3-Substituted-oxindoles in compositions and methods of treating obesity
JPH0227325B2 (fr)	1990-06-15
US4093627A (en)	1978-06-06	3-[(4-Chromanylidene)amino]-2-oxazolidinones
JPS6324498B2 (fr)	1988-05-20
US4454155A (en)	1984-06-12	Pharmaceutical compositions containing a mono-substituted derivative of 4-phenyl-4-oxobuten-2-oic acid, and methods of using them in treating gastric and gastroduodenal ailments
US4436752A (en)	1984-03-13	Treatment of gastric and gastro-duodenal disorders with derivatives of phenyl aliphatic carboxylic acids
US3954984A (en)	1976-05-04	Triazolocycloalkylthiadiazine derivatives
LU86706A1 (fr)	1987-07-24	Nouveaux derives du benzo(4,5)cyclohepta(1,2-b)thiophene,leur preparation et leur utilisation comme medicaments
HU180589B (en)	1983-03-28	Process for producing dihydronicotinic acid derivatives
US3444298A (en)	1969-05-13	Method for preventing rhinovirus infections with 3-(3-hydroxy-3-methylbutyl-amino) - 5 - methyl - 5h - as - triazino(5,6-b) indole
NL8204060A (nl)	1983-05-16	Derivaten van 4-fenyl-4-oxo-2-buteenzuur en zouten daarvan, farmaceutische preparaten op basis daarvan, en werkwijze voor het bereiden van een en ander.
JPS5862161A (ja)	1983-04-13	アミノメチル−１ｈ−インド−ル−４−メタノ−ルの新誘導体及びそれらの塩、これらの製造方法及び中間体、これらの薬剤としての使用並びにこれを含有する組成物
JPH03106870A (ja)	1991-05-07	共役γ―オキシブテノライド化合物およびこれを有効成分とする抗潰瘍剤
JPS6241689B2 (fr)	1987-09-04
DK151029B (da)	1987-10-12	Analogifremgangsmaade til fremstilling af thiadiazoltetrahydroisoquinolinforbindelser eller syreadditionssalte deraf