SE455420B - Anvendning av 4-fenyl-4-oxo-butensyraderivat for framstellning av ett lekemedel for behandling av magakommor och gastroduodenala akommor i samband med hyperaciditet - Google Patents

Anvendning av 4-fenyl-4-oxo-butensyraderivat for framstellning av ett lekemedel for behandling av magakommor och gastroduodenala akommor i samband med hyperaciditet

Info

Publication number: SE455420B
Authority: SE; Sweden
Prior art keywords: formula; compounds; oxo; phenyl; gastric
Prior art date: 1981-10-22

Application number

SE8205868A

Other languages

English (en)

Swedish (sv)

Other versions

SE8205868L (sv

SE8205868D0 (sv

Inventor

M Bianchi

F Barzaghi

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

1982-10-15

Publication date

1988-07-11

1982-10-15 Application filed by Roussel Uclaf filed Critical Roussel Uclaf

1982-10-15 Publication of SE8205868D0 publication Critical patent/SE8205868D0/xx

1983-04-23 Publication of SE8205868L publication Critical patent/SE8205868L/

1988-07-11 Publication of SE455420B publication Critical patent/SE455420B/sv

Links

230000002496 gastric effect Effects 0.000 title claims description 4
206010020601 Hyperchlorhydria Diseases 0.000 title claims description 3
238000002360 preparation method Methods 0.000 title description 3
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
208000002874 Acne Vulgaris Diseases 0.000 title 1
206010000496 acne Diseases 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 13
239000003814 drug Substances 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
210000002784 stomach Anatomy 0.000 claims description 6
239000003513 alkali Substances 0.000 claims description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
230000003248 secreting effect Effects 0.000 claims description 4
PLPDHGOODMBBGN-VOTSOKGWSA-N (e)-4-oxo-4-phenylbut-2-enoic acid Chemical compound OC(=O)\C=C\C(=O)C1=CC=CC=C1 PLPDHGOODMBBGN-VOTSOKGWSA-N 0.000 claims description 3
208000008469 Peptic Ulcer Diseases 0.000 claims description 3
-1 amine salts Chemical class 0.000 claims description 3
231100000029 gastro-duodenal ulcer Toxicity 0.000 claims description 3
208000007882 Gastritis Diseases 0.000 claims description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 1
206010017886 Gastroduodenal ulcer Diseases 0.000 claims 1
150000001412 amines Chemical class 0.000 claims 1
125000004429 atom Chemical group 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
230000001681 protective effect Effects 0.000 claims 1
239000000047 product Substances 0.000 description 17
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
241001465754 Metazoa Species 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
239000000203 mixture Substances 0.000 description 8
239000000243 solution Substances 0.000 description 7
241000700159 Rattus Species 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
238000000034 method Methods 0.000 description 6
239000000546 pharmaceutical excipient Substances 0.000 description 5
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
239000007903 gelatin capsule Substances 0.000 description 4
HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 4
239000007787 solid Substances 0.000 description 4
239000002904 solvent Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
208000027418 Wounds and injury Diseases 0.000 description 3
230000000767 anti-ulcer Effects 0.000 description 3
230000000694 effects Effects 0.000 description 3
235000019359 magnesium stearate Nutrition 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
235000019698 starch Nutrition 0.000 description 3
239000000454 talc Substances 0.000 description 3
229910052623 talc Inorganic materials 0.000 description 3
PLPDHGOODMBBGN-SREVYHEPSA-N (z)-4-oxo-4-phenylbut-2-enoic acid Chemical compound OC(=O)\C=C/C(=O)C1=CC=CC=C1 PLPDHGOODMBBGN-SREVYHEPSA-N 0.000 description 2
TXFPEBPIARQUIG-UHFFFAOYSA-N 4'-hydroxyacetophenone Chemical compound CC(=O)C1=CC=C(O)C=C1 TXFPEBPIARQUIG-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
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
231100000111 LD50 Toxicity 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
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-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
206010052428 Wound Diseases 0.000 description 2
239000002253 acid Substances 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
208000035475 disorder Diseases 0.000 description 2
229940079593 drug Drugs 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
210000004051 gastric juice Anatomy 0.000 description 2
239000008103 glucose Substances 0.000 description 2
239000008101 lactose Substances 0.000 description 2
FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
239000008107 starch Substances 0.000 description 2
LQCBGQDCRBYBMK-AATRIKPKSA-N (e)-4-(4-hydroxyphenyl)-4-oxobut-2-enoic acid Chemical compound OC(=O)\C=C\C(=O)C1=CC=C(O)C=C1 LQCBGQDCRBYBMK-AATRIKPKSA-N 0.000 description 1
HPTXPPRVSKJCMZ-UHFFFAOYSA-N 2-(4-methylphenyl)-4-oxobut-2-enoic acid Chemical compound CC1=CC=C(C(=CC=O)C(O)=O)C=C1 HPTXPPRVSKJCMZ-UHFFFAOYSA-N 0.000 description 1
BLMRYSUYNBNSJA-UHFFFAOYSA-N 2-methyl-4-oxo-4-phenylbut-2-enoic acid Chemical compound OC(=O)C(C)=CC(=O)C1=CC=CC=C1 BLMRYSUYNBNSJA-UHFFFAOYSA-N 0.000 description 1
MXDYOAKQTRLNIB-UHFFFAOYSA-N 2-methylidene-4-oxo-4-phenylbutanoic acid Chemical compound OC(=O)C(=C)CC(=O)C1=CC=CC=C1 MXDYOAKQTRLNIB-UHFFFAOYSA-N 0.000 description 1
244000215068 Acacia senegal Species 0.000 description 1
229910002012 Aerosil® Inorganic materials 0.000 description 1
229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
208000012895 Gastric disease Diseases 0.000 description 1
229920000084 Gum arabic Polymers 0.000 description 1
206010019909 Hernia Diseases 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
208000007107 Stomach Ulcer Diseases 0.000 description 1
208000025865 Ulcer Diseases 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
PJWSWBRTZKODSD-UHFFFAOYSA-N acetic acid;benzene;ethyl acetate Chemical compound CC(O)=O.CCOC(C)=O.C1=CC=CC=C1 PJWSWBRTZKODSD-UHFFFAOYSA-N 0.000 description 1
230000007059 acute toxicity Effects 0.000 description 1
231100000403 acute toxicity Toxicity 0.000 description 1
230000001262 anti-secretory effect Effects 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
238000009835 boiling Methods 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
229940110456 cocoa butter Drugs 0.000 description 1
235000019868 cocoa butter Nutrition 0.000 description 1
238000001816 cooling Methods 0.000 description 1
230000006378 damage Effects 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
239000012024 dehydrating agents‎ Substances 0.000 description 1
230000029087 digestion Effects 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000003925 fat Substances 0.000 description 1
235000019197 fats Nutrition 0.000 description 1
235000013305 food Nutrition 0.000 description 1
210000001156 gastric mucosa Anatomy 0.000 description 1
210000001035 gastrointestinal tract Anatomy 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
239000008187 granular material Substances 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000012535 impurity Substances 0.000 description 1
230000001939 inductive effect Effects 0.000 description 1
208000014674 injury Diseases 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229940126601 medicinal product Drugs 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
210000001187 pylorus Anatomy 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
229940100486 rice starch Drugs 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
230000028327 secretion Effects 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000000829 suppository Substances 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
238000004448 titration Methods 0.000 description 1
230000036269 ulceration Effects 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
238000010792 warming Methods 0.000 description 1
238000005303 weighing Methods 0.000 description 1
238000009736 wetting 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)

SE8205868A 1981-10-22 1982-10-15 Anvendning av 4-fenyl-4-oxo-butensyraderivat for framstellning av ett lekemedel for behandling av magakommor och gastroduodenala akommor i samband med hyperaciditet SE455420B (sv)

Applications Claiming Priority (1)

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

Publications (3)

Publication Number	Publication Date
SE8205868D0 SE8205868D0 (sv)	1982-10-15
SE8205868L SE8205868L (sv)	1983-04-23
SE455420B true SE455420B (sv)	1988-07-11

Family

ID=11270992

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SE8205868A SE455420B (sv)	1981-10-22	1982-10-15	Anvendning av 4-fenyl-4-oxo-butensyraderivat for framstellning av ett lekemedel for behandling av magakommor och gastroduodenala akommor i samband med hyperaciditet

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
AU2003231469A1 (en) *	2002-05-15	2003-12-02	Meiji Seika Kaisha, Ltd.	Process for producing 4-phenyl-4-oxo-2-butenoic ester derivative

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 BE BE0/209295A patent/BE894766A/fr not_active IP Right Cessation
- 1982-10-21 FR FR8217621A patent/FR2515038B1/fr not_active Expired
- 1982-10-21 NL NL8204061A patent/NL8204061A/nl not_active Application Discontinuation
- 1982-10-21 CA CA000413905A patent/CA1181340A/fr not_active Expired
- 1982-10-21 LU LU84429A patent/LU84429A1/fr unknown
- 1982-10-21 CH CH6133/82A patent/CH654289A5/fr not_active IP Right Cessation
- 1982-10-22 GB GB08230214A patent/GB2108385B/en not_active Expired
- 1982-10-22 DE DE19823239189 patent/DE3239189A1/de not_active Withdrawn
- 1982-10-22 JP JP57184810A patent/JPS5883620A/ja active Pending

Also Published As

Publication number	Publication date
DE3239189A1 (de)	1983-05-05
JPS5883620A (ja)	1983-05-19
NL8204061A (nl)	1983-05-16
SE8205868L (sv)	1983-04-23
SE8205868D0 (sv)	1982-10-15
LU84429A1 (fr)	1983-06-13
BE894766A (fr)	1983-04-21
US4473583A (en)	1984-09-25
CH654289A5 (fr)	1986-02-14
FR2515038B1 (fr)	1985-08-23
FR2515038A1 (fr)	1983-04-29
GB2108385A (en)	1983-05-18
IT8149548A0 (it)	1981-10-22
GB2108385B (en)	1985-07-03
IT1210582B (it)	1989-09-14
CA1181340A (fr)	1985-01-22

Legal Events

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Title

Description

1995-01-31

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IL30394A (en)	1973-08-29	Phenylacetic acid derivatives
WO1996039133A1 (fr)	1996-12-12	Nouvelles 2-amino-3'-4'-methylene-dioxypropiophenones n-substituees
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