DE2711585A1 - 2-ANGLE CLIP ON 4-THENOYL (3 ') PHENYL ANGLE CLIP ON PROPIONIC ACID AND ITS SALTS, PROCESS FOR THEIR MANUFACTURING AND MEDICINAL PRODUCTS CONTAINING THEM - Google Patents
2-ANGLE CLIP ON 4-THENOYL (3 ') PHENYL ANGLE CLIP ON PROPIONIC ACID AND ITS SALTS, PROCESS FOR THEIR MANUFACTURING AND MEDICINAL PRODUCTS CONTAINING THEMInfo
- Publication number
- DE2711585A1 DE2711585A1 DE19772711585 DE2711585A DE2711585A1 DE 2711585 A1 DE2711585 A1 DE 2711585A1 DE 19772711585 DE19772711585 DE 19772711585 DE 2711585 A DE2711585 A DE 2711585A DE 2711585 A1 DE2711585 A1 DE 2711585A1
- Authority
- DE
- Germany
- Prior art keywords
- thenoyl
- propionic acid
- salts
- acid
- phenyl7
- Prior art date
- 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.)
- Withdrawn
Links
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
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Rheumatology (AREA)
- Pharmacology & Pharmacy (AREA)
- Pain & Pain Management (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Description
(3')-pheny!/-propionsäure der Formel(3 ') - pheny! / - propionic acid of the formula
CH - COOH (I)CH - COOH (I)
IlIl
CH,CH,
Die Verbindung besitzt ein asymmetrisches Kohlenstoffatom und kann aufgrund dieser Tatsache nach dem Fachmann bekannten Methoden aufgetrennt werden, insbesondere durch Kristallisation der mit einer optisch aktiven organischen Base erhaltenen Salze. Die erhaltenen aktiven Formen stellen einen Bestandteil dieser Erfindung dar.The compound has an asymmetric carbon atom and can on the basis of this fact be separated by methods known to the person skilled in the art, in particular by crystallization the salts obtained with an optically active organic base. The active forms obtained constitute an ingredient of this invention.
Gleichermaßen sind die mit einer organischen oder mineralischen, d.h. anorganischen Base erhaltenen Salze, die in der Humanmedizin brauchbar sind, Teil der Erfindung.Likewise, the salts obtained with an organic or mineral, i.e. inorganic base are those used in human medicine are useful, part of the invention.
Man kann diese Säure durch alkalische Hydrolyse von 2-Methyl-2-^4-thenoyl-(3')-phenyl7-äthylmalonat der FormelThis acid can be obtained by alkaline hydrolysis of 2-methyl-2- ^ 4-thenoyl- (3 ') - phenyl7-ethylmalonate the formula
'( )\ ,CÜCX:2H5 '() \ , CÜCX: 2 H 5
(ID COOC2H5 (ID COOC 2 H 5
und Decarboxylierung herstellen.and produce decarboxylation.
Diese Zwischenverbindung ist neu und stellt einen Teil der Erfindung dar. Man erhält sie vorzugsweise durch AlkylierungThis intermediate compound is new and forms part of the invention. It is preferably obtained by alkylation
709839/0895709839/0895
von Fluorphenylthenylmethanon mit 2-Methyl-äthylmalonat in ei nem aprotischen dipolaren Lösungsmittel in Gegenwart einer starken Base.of fluorophenylthenylmethanone with 2-methyl ethyl malonate in egg nem aprotic dipolar solvent in the presence of a strong base.
Das Fluorphenylthenylmethanon der FormelThe fluorophenylthenyl methanone of the formula
(III)(III)
ist ebenfalls ein neues Zwischenprodukt, das einen Teil der Erfindung darstellt. Man kann es durch Kondensation von Thenoyl-(3')-chlorid mit Fluorbenzol unter den Bedingungen der Friedel-Crafts-Reaktion erhalten.is also a new intermediate that forms part of the invention. One can do it by condensation of Thenoyl (3 ') chloride with fluorobenzene under the conditions the Friedel-Crafts reaction.
Außerdem hat sich 2-/4-Thenoyl-(31)-pheny!/-propionsäure als besonders interessant als Analgetikum, entzündungshemmendes Mittel und Mittel gegen eine Vereinigung von Blutplättchen erwiesen.In addition, 2- / 4-thenoyl- (3 1 ) -pheny! / -Propionic acid has proven to be of particular interest as an analgesic, anti-inflammatory agent, and antiplatelet agent.
Die analgetische Aktivität zeigt sich bei dem Essigsäuretest mit der Maus (Methode von Siegmund, modifiziert nach Koster, Anderson und Debeer) . Die ED1.,-. (aktive Dosis ^0 ) in mg/kg liegt bei 9 für 2-^4-Thenoyl-(3')-pheny!/-propionsäure, Aspirin (Acetylsalizylsäure) hat in diesem Test einen ED50" Wert von 130, Pyramidon (Phenyldimethylaminodimethylpyrazolon) einen ED5 -Wert von 32 und Pethidin (l-Methyl-4-phenyl-hexahydroisonikotinsäureäthylester-hydrochlorid) einen ED5Q-WertThe analgesic activity is shown in the acetic acid test with the mouse (Siegmund method, modified from Koster, Anderson and Debeer). The ED 1. , -. (active dose ^ 0 ) in mg / kg is 9 for 2- ^ 4-thenoyl- (3 ') - pheny! / - propionic acid, aspirin (acetylsalicylic acid) has an ED 50 "value of 130 in this test, pyramidon ( Phenyldimethylaminodimethylpyrazolone) an ED 5 value of 32 and pethidine (1-methyl-4-phenyl-hexahydroisonicotinic acid ethyl ester hydrochloride) an ED 5Q value
17# 709839/089 5 17 # 709839/089 5
Die entzündungshemir.ende Aktivität, die unter anderen Methoden mit dem Carrageninödemtest bei der Ratte bestimmt wird (Winter et al., Proc.Soc.Exp. Biol. Med., 1972 III, Seiten 544 - 547), erwies sich als ausgezeichnet. Der ED~0-Wert (aktive Dosis 3_) in mg/kg der 2-^4-Thenoyl-(31)-pheny !/-propionsäure liegt bei 5, der Wert für Phenylbutazon (l,2-Diphenyl-3,5-dioxo-4-nbutylpyrazolidin) bei 50 und der für Pyramidon bei 82.The anti-inflammatory activity, which is determined among other methods with the carrageenin edema test in rats (Winter et al., Proc.Soc.Exp. Biol. Med., 1972 III, pages 544-547), proved to be excellent. The ED ~ 0 value (active dose 3 _) in mg / kg of 2- ^ 4-thenoyl- (3 1 ) -pheny! / - propionic acid is 5, the value for phenylbutazone (1,2-diphenyl-3 , 5-dioxo-4-n-butylpyrazolidine) at 50 and that for pyramidone at 82.
Bei der Hemmung des durch UV-Strahlung hervorgerufenen Erythems beim Meerschweinchen (CV. Winder, J. Wax, V. Butt et al.. Arch, Ind. Pharm. , 1958, Seiten 116 bis 261) zeigt sich die 2-^4-Thenoyl-(31)-phenyl/-propionsäure als 30 mal so aktiv wie das Aspirin. Bei 5 mg/kg ist der Schutz des Tieres vollständig, und dies liegt in der gleichen Größenordnung wie bei Indomethazin (1-(4-Chlorbenzoyl)-5-methoxy-2-methyl-3-indolessigsäure) oder bei Ketoprofen (2-(3*-ßenzoylphenyl)-propionsäure).In the inhibition of erythema caused by UV radiation in guinea pigs (CV. Winder, J. Wax, V. Butt et al. Arch, Ind. Pharm., 1958, pages 116 to 261), the 2- ^ 4- Thenoyl- (3 1 ) -phenyl / -propionic acid than 30 times as active as the aspirin. At 5 mg / kg the protection of the animal is complete, and this is in the same order of magnitude as indomethazine (1- (4-chlorobenzoyl) -5-methoxy-2-methyl-3-indolacetic acid) or ketoprofen (2- ( 3 * -ßenzoylphenyl) propionic acid).
Die 2-^4-Thenoyl-(3')-phenyl7~propionsäure besitzt die Eigenschaf tt in vitro und in vivo die Vereinigung von Blutplättchen des Kaninchenplasmas zu hemmen, die durch Adenosin-5-diphosphat (ADP) und Collagen induziert wird. Die zur Darstellung dieser pharmakologischen Eigenschaft benutzte Methode beruht auf der Beschreibung von Born (Journal of Physiology, 1962) und bedient sich eines Agregometers nach Mustard. Man drückt das Ergebnis als einen Koeffizienten aus, der aus einem Vergleich der kleinsten aktiven Konzentration (in MiEomol) des Standards mit der kleinsten aktiven Konzentration des ProduktsThe 2- ^ 4-thenoyl (3 ') - has phenyl7 ~ propionic the natural sheep t t in vitro and in vivo the association of platelets of rabbit plasma to inhibit induced by adenosine-5-diphosphate (ADP) and collagen. The method used to illustrate this pharmacological property is based on the description by Born (Journal of Physiology, 1962) and uses a Mustard agregometer. The result is expressed as a coefficient obtained by comparing the smallest active concentration (in MiEomol) of the standard with the smallest active concentration of the product
709839/0895709839/0895
resultiert (man nennt aktive Konzentration jene Konzentration, die eine Hemmung der \fereinigurij gleich wie oder größer als
50% herbeiführt).results (active concentration is called that concentration which results in an inhibition of \ fereinigurij equal to or greater than
50%).
ADP CollagenADP collagen
Aspirin 1Aspirin 1
Phenergan (10-(2-Dimethylaminopropyl)-phenothiazin) 1Phenergan (10- (2-dimethylaminopropyl) -phenothiazine) 1
2-^4-Thenoyl-(3')-2- ^ 4-thenoyl- (3 ') -
phenyl7~propionsäure 4 6Ophenyl7 ~ propionic acid 4 6O
Die pharmazeutischen Zusammensetzungen, die als Wirkstoff
die Verbindung nach der Erfindung enthalten, sei es als
Säure, sei es als organisches oder mineralisches, d. h. anorganisches Salz, können in der Form von Pastillen, Tabletten,
Gelees, Dragees, wässrigen Suspensionen, injizierbaren Lösungen, Aerosolen, Sirupen und analogen Arzneimittelformen
vorliegen. Die Pastillen oder Tabletten können gegebenenfalls durch eine Lackierung mit einem Cellulosederivat magenresistent
gemacht werden.The pharmaceutical compositions that act as an active ingredient
contain the compound according to the invention, either as
Acids, whether as an organic or mineral, ie inorganic salt, can be in the form of troches, tablets, jellies, coated tablets, aqueous suspensions, injectable solutions, aerosols, syrups and analogous drug forms. The pastilles or tablets can optionally be made stomach-resistant by coating with a cellulose derivative.
Die pharmazeutischen Präparate, die als Wirkstoff die Säure nach der Erfindung und einen physiologisch verträglichen pharmazeutischen, festen oder flüssigen Träger oder ein solches Verdünnungsmittel enthalten, gestatten eine tägliche Verabreichung von Dosen des Wirkstoffes im Bereich von 20 bis lOOO mg.The pharmaceutical preparations containing the acid according to the invention and a physiologically compatible pharmaceutical, containing solid or liquid carriers or such a diluent permit daily administration of doses of the active ingredient ranging from 20 to 1,000 mg.
709839/0895709839/0895
Das folgende Beispiel dient der Erläuterung des Verfahrens zur Herstellung der neuen Säure nach der Erfindung.The following example serves to illustrate the process for the preparation of the new acid according to the invention.
Stufe 1step 1
^4-Fluorphenyl-thenyl-(31)-methanon_/ (Formel III)^ 4-fluorophenyl-thenyl- (3 1 ) -methanon_ / (formula III)
, MG = 206,17, MW = 206.17
Zu einer Lösung von 42,5 g (0,29 Mol) 3-Thiophencarbonylchlorid in 315 ml Fluorbenzol setzt man unter Rühren und Kühlen in einem Eisbad 57 g (0,42 Mol) wasserfreies Aluminiumchlorid in kleinen Anteilen zu. Die Reaktion ist leicht exotherm, und die Temperatur steigt bis auf 10°C. Man hält 45 min auf 6O°c, dann 15 min unter Rückflußbedingungen. Man kühlt und gießt in Eiswasser. Man extrahiert mit Chloroform. Man wäscht die organische Phase mit einer 5%igen Natriumbicarbonatlösung und trocknet über Na2SO.. Nach dem Verdampfen des Lösungsmittels und dem Destillieren am Vakuum erhält man 18,3 g (Ausbeute 30%). Kp. _ _,- m = 125 bis 130 C, F. = 57 g (0.42 mol) of anhydrous aluminum chloride are added in small portions to a solution of 42.5 g (0.29 mol) of 3-thiophene carbonyl chloride in 315 ml of fluorobenzene with stirring and cooling in an ice bath. The reaction is slightly exothermic and the temperature rises to 10 ° C. The mixture is kept at 60 ° C. for 45 minutes, then under reflux conditions for 15 minutes. It is cooled and poured into ice water. Extract with chloroform. The organic phase is washed with a 5% strength sodium bicarbonate solution and dried over Na 2 SO .. After evaporation of the solvent and distillation in vacuo, 18.3 g are obtained (yield 30%). Kp. _ _, - m = 125 to 130 C, F. =
KJ $ λ, D IuIu KJ $ λ, D IuIu
74°C (aus Hexan).74 ° C (from hexane).
IR: /■ 1660 cm""1 IR: / ■ 1660 cm "" 1
C=OC = O
Jtufe_2Jtufe_2
2-Methyl-2-^4-thenoyl-(3')-phenyl7-diäthylmalonat (Formel II) C19H20O5S, MG - 360,35.2-methyl-2- ^ 4-thenoyl- (3 ') - phenyl7-diethylmalonate (Formula II) C 19 H 20 O 5 S, MW - 360.35.
709839/0895709839/0895
Zu 4 g einer 50%igen (0,083 Mol) Suspension von Natriumhydrid in 83 ml frisch destilliertem Hexamethylphosphorotriamid setzt man Tropfen für Tropfen bei Raumtemperatur 14,4 g (0,083 Mol) 2-Methyl-diäthylmalonat au. Die Reaktion ist leicht exotherm. Man setzt nun in kleinen Anteilen 17,1 g (0,083 Mol) (4-Fluorphenyl)-thienyl-(3')-methanon zu. Man hält 10 Stunden auf IQO C . Sodann verdünnt man mit 300 ml Benzol, wäscht man mit H3O und trocknet über Na3SO4. Nach dem Verdampfen des Lösungsmittels und dem Destillieren am Vakuum erhält man ein gelbes öl.14.4 g (0.083 mol) of 2-methyl diethyl malonate are added drop by drop at room temperature to 4 g of a 50% strength (0.083 mol) suspension of sodium hydride in 83 ml of freshly distilled hexamethylphosphorotriamide. The reaction is slightly exothermic. 17.1 g (0.083 mol) of (4-fluorophenyl) thienyl (3 ') methanone are now added in small portions. It is held at IQO C for 10 hours. It is then diluted with 300 ml of benzene, washed with H 3 O and dried over Na 3 SO 4 . After evaporation of the solvent and distillation in vacuo, a yellow oil is obtained.
Gewicht: 12,1 g (Ausbeute 40,6%), Kp. Λ . = 19O-2OO°C.Weight: 12.1 g (yield 40.6%), boiling point Λ . = 19O-2OO ° C.
0,4 mm0.4 mm
IR: γ* 1660 cm (Keton)
C = O ,IR: γ * 1660 cm (ketone)
C = O,
1750 cm (Ester)
= 01750 cm (ester)
= 0
NMR (CCl.) :
4NMR (CCl.):
4th
of (ppm) : 6 Protonen bei 1,25 (Triplett, J=) cps) of (ppm): 6 protons at 1.25 (triplet, J =) cps)
3 Protonen bei 1,95 (Singulett)3 protons at 1.95 (singlet)
4 Protonen bei 4,3 (Quartett, J=7 cps) 7 Protonen von 7,3 bis 8 (Massiv)4 protons at 4.3 (quartet, J = 7 cps) 7 protons from 7.3 to 8 (massive)
Stufe 3level 3
2-^4-Thenoyl-(31)-phenyl/-propionsäure (Formel I) 12O3S, MG = 260,302- ^ 4-Thenoyl- (3 1 ) -phenyl / -propionic acid (Formula I) 12 O 3 S, MW = 260.30
12,1 g (3,3 χ lo"2 Mol) 2-Methyl-2-/4-thenoyl-(31)-phenyl?·12.1 g (3.3 χ lo " 2 mol) 2-methyl-2- / 4-thenoyl- (3 1 ) -phenyl? ·
709839/0895709839/0895
diäthylmalonat und 80 ml einer 5%igen wässrigen Sodalösung werden 6 Stunden unter Rückflußbedingungen gehalten. Nach dem Abkühlen und Waschen der Lösung mit Benzol wird die wässrige Phase mit HCl (1/2) angesäuert. Das gebildete öl wird mit Chloroform extrahiert. Nach dem Trocknen über Na2SO. und dem Verdampfen des Lösungsmittels erhält man 9g eines dicken Öls, das sich kristallisieren läßt. Man erhält 3,4 g eines weißen Feststoffes:Diethyl malonate and 80 ml of a 5% strength aqueous soda solution are kept under reflux conditions for 6 hours. After cooling and washing the solution with benzene, the aqueous phase is acidified with HCl (1/2). The oil formed is extracted with chloroform. After drying over Na 2 SO. and evaporation of the solvent gives 9 g of a thick oil which crystallizes. 3.4 g of a white solid are obtained:
F.= 99 - 105°C (>—0—( ) Ausbeute: 39,5% C=OF. = 99 - 105 ° C (> —0— () Yield: 39.5% C = O
IR :/ : 1650 cm"1 (Keton)
Λ C=O ,IR: /: 1650 cm " 1 (ketone)
Λ C = O,
: 1730 cm (Säure): 1730 cm (acid)
C=OC = O
709839/0895709839/0895
Claims (3)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7608470A FR2345148A1 (en) | 1976-03-24 | 1976-03-24 | NEW SUBSTITUTE PROPIONIC ACID, PREPARATION AND APPLICATION |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2711585A1 true DE2711585A1 (en) | 1977-09-29 |
Family
ID=9170850
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19772711585 Withdrawn DE2711585A1 (en) | 1976-03-24 | 1977-03-17 | 2-ANGLE CLIP ON 4-THENOYL (3 ') PHENYL ANGLE CLIP ON PROPIONIC ACID AND ITS SALTS, PROCESS FOR THEIR MANUFACTURING AND MEDICINAL PRODUCTS CONTAINING THEM |
Country Status (26)
| Country | Link |
|---|---|
| JP (1) | JPS52139057A (en) |
| AR (1) | AR212262A1 (en) |
| AT (1) | AT358026B (en) |
| AU (1) | AU2351877A (en) |
| BE (1) | BE852463A (en) |
| CA (1) | CA1102343A (en) |
| CH (1) | CH597220A5 (en) |
| CS (1) | CS199667B2 (en) |
| DD (1) | DD128778A5 (en) |
| DE (1) | DE2711585A1 (en) |
| DK (1) | DK128077A (en) |
| ES (1) | ES457112A1 (en) |
| FR (1) | FR2345148A1 (en) |
| GB (1) | GB1517688A (en) |
| HU (1) | HU176990B (en) |
| IE (1) | IE44660B1 (en) |
| IL (1) | IL51720A0 (en) |
| IT (1) | IT1115272B (en) |
| MX (1) | MX4565E (en) |
| NL (1) | NL7703215A (en) |
| NO (1) | NO771033L (en) |
| OA (1) | OA06109A (en) |
| SE (1) | SE7703317L (en) |
| SU (1) | SU657748A3 (en) |
| YU (1) | YU65377A (en) |
| ZA (1) | ZA771724B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3537768A1 (en) * | 1985-10-21 | 1987-04-30 | Indian Drugs & Pharma | NEW 4- (3-THIENYL) PHENYL ALCANCARBONIC ACIDS AND THEIR DERIVATIVES AS AN INFLAMMATORY AND ANTIARTHRITIC MEDICINAL PRODUCTS |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2030131B (en) * | 1978-09-12 | 1982-12-22 | Taiyo Pharma Ind | Process for producing 2-(4-(2-thienyl-carbonyl) phenyl) propionic acid |
| EP0046337A3 (en) * | 1980-08-20 | 1982-09-15 | Imperial Chemical Industries Plc | Triazole compounds, a process for preparing them, their use as plant and pharmaceutical fungicides and as plant growth regulators and compositions containing them |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1007643A (en) * | 1972-10-24 | 1977-03-29 | Janssen Pharmaceutica Naamloze Vennootschap | Aroyl-substituted phenylacetic acid derivatives |
-
1976
- 1976-03-24 FR FR7608470A patent/FR2345148A1/en active Granted
-
1977
- 1977-03-11 YU YU00653/77A patent/YU65377A/en unknown
- 1977-03-15 AT AT176577A patent/AT358026B/en not_active IP Right Cessation
- 1977-03-15 BE BE175792A patent/BE852463A/en not_active IP Right Cessation
- 1977-03-17 DE DE19772711585 patent/DE2711585A1/en not_active Withdrawn
- 1977-03-18 CS CS771807A patent/CS199667B2/en unknown
- 1977-03-21 CA CA274,355A patent/CA1102343A/en not_active Expired
- 1977-03-21 IT IT7721461A patent/IT1115272B/en active
- 1977-03-22 IL IL51720A patent/IL51720A0/en unknown
- 1977-03-22 CH CH359977A patent/CH597220A5/xx not_active IP Right Cessation
- 1977-03-22 ZA ZA00771724A patent/ZA771724B/en unknown
- 1977-03-23 MX MX775559U patent/MX4565E/en unknown
- 1977-03-23 NO NO771033A patent/NO771033L/en unknown
- 1977-03-23 SE SE7703317A patent/SE7703317L/en unknown
- 1977-03-23 AU AU23518/77A patent/AU2351877A/en not_active Expired
- 1977-03-23 DK DK128077A patent/DK128077A/en not_active Application Discontinuation
- 1977-03-23 ES ES457112A patent/ES457112A1/en not_active Expired
- 1977-03-23 GB GB12327/77A patent/GB1517688A/en not_active Expired
- 1977-03-23 SU SU772462808A patent/SU657748A3/en active
- 1977-03-23 IE IE616/77A patent/IE44660B1/en unknown
- 1977-03-23 HU HU77LI310A patent/HU176990B/en unknown
- 1977-03-24 NL NL7703215A patent/NL7703215A/en not_active Application Discontinuation
- 1977-03-24 DD DD7700198055A patent/DD128778A5/en unknown
- 1977-03-24 AR AR266969A patent/AR212262A1/en active
- 1977-03-24 JP JP3164377A patent/JPS52139057A/en active Pending
- 1977-03-28 OA OA56120A patent/OA06109A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3537768A1 (en) * | 1985-10-21 | 1987-04-30 | Indian Drugs & Pharma | NEW 4- (3-THIENYL) PHENYL ALCANCARBONIC ACIDS AND THEIR DERIVATIVES AS AN INFLAMMATORY AND ANTIARTHRITIC MEDICINAL PRODUCTS |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1517688A (en) | 1978-07-12 |
| HU176990B (en) | 1981-06-28 |
| CS199667B2 (en) | 1980-07-31 |
| AT358026B (en) | 1980-08-11 |
| JPS52139057A (en) | 1977-11-19 |
| IE44660L (en) | 1977-09-24 |
| DD128778A5 (en) | 1977-12-07 |
| IL51720A0 (en) | 1977-05-31 |
| IT1115272B (en) | 1986-02-03 |
| NO771033L (en) | 1977-09-27 |
| DK128077A (en) | 1977-09-25 |
| OA06109A (en) | 1981-06-30 |
| IE44660B1 (en) | 1982-02-10 |
| ES457112A1 (en) | 1978-03-01 |
| SE7703317L (en) | 1977-09-25 |
| SU657748A3 (en) | 1979-04-15 |
| AU2351877A (en) | 1978-09-28 |
| FR2345148B1 (en) | 1978-10-20 |
| FR2345148A1 (en) | 1977-10-21 |
| AR212262A1 (en) | 1978-06-15 |
| MX4565E (en) | 1982-06-17 |
| BE852463A (en) | 1977-09-15 |
| YU65377A (en) | 1983-01-21 |
| CH597220A5 (en) | 1978-03-31 |
| ZA771724B (en) | 1978-02-22 |
| CA1102343A (en) | 1981-06-02 |
| ATA176577A (en) | 1980-01-15 |
| NL7703215A (en) | 1977-09-27 |
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