BE875186A - 2-(2-thenoylthio)-propionyglycine, procede pour sa preparation et compositions pharmaceutiques la contenant - Google Patents

2-(2-thenoylthio)-propionyglycine, procede pour sa preparation et compositions pharmaceutiques la contenant

Info

Publication number: BE875186A
Authority: BE; Belgium
Prior art keywords: emi; compound; pharmaceutical compositions; thenoylthio; animals
Prior art date: 1978-04-11

Application number

BE0/194293A

Other languages

English (en)

French (fr)

Original Assignee

Mediolanum Farmaceutici Srl

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.)

1978-04-11

Filing date

1979-03-29

Publication date

1979-07-16

1979-03-29 Application filed by Mediolanum Farmaceutici Srl filed Critical Mediolanum Farmaceutici Srl

1979-07-16 Publication of BE875186A publication Critical patent/BE875186A/fr

Links

238000000034 method Methods 0.000 title claims description 7
239000008194 pharmaceutical composition Substances 0.000 title claims description 7
238000002360 preparation method Methods 0.000 title description 3
230000008569 process Effects 0.000 title description 3
-1 2-THENOYLTHIO Chemical class 0.000 title 1
239000000829 suppository Substances 0.000 claims description 8
230000000510 mucolytic effect Effects 0.000 claims description 7
239000000443 aerosol Substances 0.000 claims description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 6
230000001154 acute effect Effects 0.000 claims description 5
231100000566 intoxication Toxicity 0.000 claims description 5
230000035987 intoxication Effects 0.000 claims description 5
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 4
230000000694 effects Effects 0.000 claims description 4
239000006188 syrup Substances 0.000 claims description 4
235000020357 syrup Nutrition 0.000 claims description 4
208000019423 liver disease Diseases 0.000 claims description 3
229910000027 potassium carbonate Inorganic materials 0.000 claims description 3
150000003839 salts Chemical class 0.000 claims description 3
239000004471 Glycine Substances 0.000 claims description 2
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 claims description 2
239000012736 aqueous medium Substances 0.000 claims description 2
230000001684 chronic effect Effects 0.000 claims description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 2
229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
238000002560 therapeutic procedure Methods 0.000 claims description 2
150000001875 compounds Chemical class 0.000 description 42
238000011282 treatment Methods 0.000 description 23
241001465754 Metazoa Species 0.000 description 18
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 15
GSAJFWKHLRVDRB-UHFFFAOYSA-N 2-amino-3-sulfanylidenepentanoic acid Chemical compound CCC(=S)C(N)C(O)=O GSAJFWKHLRVDRB-UHFFFAOYSA-N 0.000 description 11
241000700159 Rattus Species 0.000 description 11
JNYSEDHQJCOWQU-UHFFFAOYSA-N stepronin Chemical compound OC(=O)CNC(=O)C(C)SC(=O)C1=CC=CS1 JNYSEDHQJCOWQU-UHFFFAOYSA-N 0.000 description 10
229940079593 drug Drugs 0.000 description 8
239000003814 drug Substances 0.000 description 8
238000005303 weighing Methods 0.000 description 8
YTGJWQPHMWSCST-UHFFFAOYSA-N Tiopronin Chemical compound CC(S)C(=O)NCC(O)=O YTGJWQPHMWSCST-UHFFFAOYSA-N 0.000 description 7
108010058907 Tiopronin Proteins 0.000 description 7
QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 6
230000034994 death Effects 0.000 description 6
231100000517 death Toxicity 0.000 description 6
230000001681 protective effect Effects 0.000 description 6
159000000000 sodium salts Chemical class 0.000 description 6
239000000126 substance Substances 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
241000700198 Cavia Species 0.000 description 5
208000005374 Poisoning Diseases 0.000 description 5
230000004075 alteration Effects 0.000 description 5
231100000567 intoxicating Toxicity 0.000 description 5
230000002673 intoxicating effect Effects 0.000 description 5
238000007912 intraperitoneal administration Methods 0.000 description 5
210000004072 lung Anatomy 0.000 description 5
229960002523 mercuric chloride Drugs 0.000 description 5
LWJROJCJINYWOX-UHFFFAOYSA-L mercury dichloride Chemical compound Cl[Hg]Cl LWJROJCJINYWOX-UHFFFAOYSA-L 0.000 description 5
231100000572 poisoning Toxicity 0.000 description 5
230000000607 poisoning effect Effects 0.000 description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
241000699670 Mus sp. Species 0.000 description 4
230000000740 bleeding effect Effects 0.000 description 4
206010006451 bronchitis Diseases 0.000 description 4
238000004040 coloring Methods 0.000 description 4
238000002474 experimental method Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
238000002844 melting Methods 0.000 description 4
239000004296 sodium metabisulphite Substances 0.000 description 4
235000010262 sodium metabisulphite Nutrition 0.000 description 4
239000000243 solution Substances 0.000 description 4
238000012453 sprague-dawley rat model Methods 0.000 description 4
238000012360 testing method Methods 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
PWKSKIMOESPYIA-BYPYZUCNSA-N L-N-acetyl-Cysteine Chemical compound CC(=O)N[C@@H](CS)C(O)=O PWKSKIMOESPYIA-BYPYZUCNSA-N 0.000 description 3
206010036790 Productive cough Diseases 0.000 description 3
229960004308 acetylcysteine Drugs 0.000 description 3
239000002585 base Substances 0.000 description 3
239000012153 distilled water Substances 0.000 description 3
238000011156 evaluation Methods 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
230000006872 improvement Effects 0.000 description 3
239000000546 pharmaceutical excipient Substances 0.000 description 3
208000024794 sputum Diseases 0.000 description 3
210000003802 sputum Anatomy 0.000 description 3
238000012800 visualization Methods 0.000 description 3
108010082126 Alanine transaminase Proteins 0.000 description 2
241000282472 Canis lupus familiaris Species 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
206010011224 Cough Diseases 0.000 description 2
201000003883 Cystic fibrosis Diseases 0.000 description 2
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
229920000084 Gum arabic Polymers 0.000 description 2
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
229920005372 Plexiglas® Polymers 0.000 description 2
241000978776 Senegalia senegal Species 0.000 description 2
229930006000 Sucrose Natural products 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
239000000205 acacia gum Substances 0.000 description 2
235000010489 acacia gum Nutrition 0.000 description 2
230000009471 action Effects 0.000 description 2
230000004913 activation Effects 0.000 description 2
230000007059 acute toxicity Effects 0.000 description 2
231100000403 acute toxicity Toxicity 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
239000002775 capsule Substances 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
230000002349 favourable effect Effects 0.000 description 2
238000009472 formulation Methods 0.000 description 2
230000002443 hepatoprotective effect Effects 0.000 description 2
208000015181 infectious disease Diseases 0.000 description 2
230000002458 infectious effect Effects 0.000 description 2
230000001788 irregular Effects 0.000 description 2
210000004185 liver Anatomy 0.000 description 2
239000000203 mixture Substances 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
210000002345 respiratory system Anatomy 0.000 description 2
229940081974 saccharin Drugs 0.000 description 2
235000019204 saccharin Nutrition 0.000 description 2
239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000005720 sucrose Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
208000011580 syndromic disease Diseases 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
QIQITDHWZYEEPA-UHFFFAOYSA-N thiophene-2-carbonyl chloride Chemical compound ClC(=O)C1=CC=CS1 QIQITDHWZYEEPA-UHFFFAOYSA-N 0.000 description 2
KPZGRMZPZLOPBS-UHFFFAOYSA-N 1,3-dichloro-2,2-bis(chloromethyl)propane Chemical compound ClCC(CCl)(CCl)CCl KPZGRMZPZLOPBS-UHFFFAOYSA-N 0.000 description 1
208000030090 Acute Disease Diseases 0.000 description 1
102100036475 Alanine aminotransferase 1 Human genes 0.000 description 1
208000009079 Bronchial Spasm Diseases 0.000 description 1
206010053582 Bronchopneumopathy Diseases 0.000 description 1
206010006482 Bronchospasm Diseases 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
206010011416 Croup infectious Diseases 0.000 description 1
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
208000000059 Dyspnea Diseases 0.000 description 1
206010013975 Dyspnoeas Diseases 0.000 description 1
229920002683 Glycosaminoglycan Polymers 0.000 description 1
206010067125 Liver injury Diseases 0.000 description 1
VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
QGMRQYFBGABWDR-UHFFFAOYSA-M Pentobarbital sodium Chemical compound [Na+].CCCC(C)C1(CC)C(=O)NC(=O)[N-]C1=O QGMRQYFBGABWDR-UHFFFAOYSA-M 0.000 description 1
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
208000005392 Spasm Diseases 0.000 description 1
150000001263 acyl chlorides Chemical class 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
239000003708 ampul Substances 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
230000006399 behavior Effects 0.000 description 1
230000008033 biological extinction Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000008280 blood Substances 0.000 description 1
210000004369 blood Anatomy 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
238000006243 chemical reaction Methods 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
230000007665 chronic toxicity Effects 0.000 description 1
231100000160 chronic toxicity Toxicity 0.000 description 1
201000010549 croup Diseases 0.000 description 1
239000000686 essence Substances 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000019634 flavors Nutrition 0.000 description 1
230000004907 flux Effects 0.000 description 1
230000004927 fusion Effects 0.000 description 1
230000002496 gastric effect Effects 0.000 description 1
230000002489 hematologic effect Effects 0.000 description 1
231100000234 hepatic damage Toxicity 0.000 description 1
230000002440 hepatic effect Effects 0.000 description 1
229960001340 histamine Drugs 0.000 description 1
PPZMYIBUHIPZOS-UHFFFAOYSA-N histamine dihydrochloride Chemical compound Cl.Cl.NCCC1=CN=CN1 PPZMYIBUHIPZOS-UHFFFAOYSA-N 0.000 description 1
229960000645 histamine hydrochloride Drugs 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
150000002632 lipids Chemical class 0.000 description 1
230000008818 liver damage Effects 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
210000003097 mucus Anatomy 0.000 description 1
230000021332 multicellular organism growth Effects 0.000 description 1
229940105631 nembutal Drugs 0.000 description 1
238000010606 normalization Methods 0.000 description 1
230000009965 odorless effect Effects 0.000 description 1
239000007968 orange flavor Substances 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000004926 polymethyl methacrylate Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
230000004800 psychological effect Effects 0.000 description 1
230000001698 pyrogenic effect Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
239000013558 reference substance Substances 0.000 description 1
238000004062 sedimentation Methods 0.000 description 1
210000002966 serum Anatomy 0.000 description 1
230000007958 sleep Effects 0.000 description 1
230000004622 sleep time Effects 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
210000000952 spleen Anatomy 0.000 description 1
238000013112 stability test Methods 0.000 description 1
238000010186 staining Methods 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
238000003860 storage Methods 0.000 description 1
230000009967 tasteless effect Effects 0.000 description 1
QERYCTSHXKAMIS-UHFFFAOYSA-N thiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-N 0.000 description 1
231100000820 toxicity test Toxicity 0.000 description 1
230000002110 toxicologic effect Effects 0.000 description 1
231100000027 toxicology Toxicity 0.000 description 1
210000003437 trachea Anatomy 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
- C07D333/26—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/10—Expectorants

Landscapes

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

BE0/194293A 1978-04-11 1979-03-29 2-(2-thenoylthio)-propionyglycine, procede pour sa preparation et compositions pharmaceutiques la contenant BE875186A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
IT22175/78A IT1095386B (it)	1978-04-11	1978-04-11	2-(2-tenciltio)-propionilglicina,metodo per la sua preparazione e composizioni farmaceutiche che la contengono

Publications (1)

Publication Number	Publication Date
BE875186A true BE875186A (fr)	1979-07-16

Family

ID=11192601

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BE0/194293A BE875186A (fr)	1978-04-11	1979-03-29	2-(2-thenoylthio)-propionyglycine, procede pour sa preparation et compositions pharmaceutiques la contenant

Country Status (3)

Country	Link
JP (1)	JPS60166614A (2)
BE (1)	BE875186A (2)
IT (1)	IT1095386B (2)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH027608U (2) *	1988-06-29	1990-01-18

1978
- 1978-04-11 IT IT22175/78A patent/IT1095386B/it active
1979
- 1979-03-29 BE BE0/194293A patent/BE875186A/fr not_active IP Right Cessation
1985
- 1985-01-11 JP JP60003926A patent/JPS60166614A/ja active Granted

Also Published As

Publication number	Publication date
JPS6136808B2 (2)	1986-08-20
JPS60166614A (ja)	1985-08-29
IT1095386B (it)	1985-08-10
IT7822175A0 (it)	1978-04-11

Legal Events

Date

Code

Title

Description

1999-01-01

RE20

Patent expired

Owner name: MEDIOLANUM FARMACEUTICI S.R.L.

Effective date: 19990329

Publication	Publication Date	Title
FR2523124A1 (fr)	1983-09-16	Nouveau derive de l'acide 2-(p-isobutylphenyl) propionique, son procede de preparation et son application en therapeutique
MC1959A1 (fr)	1989-06-30	Composes chimiques,procede pour les preparer,formulations pharmaceutiques les contenant et leurs utilisations
CA1121825A (en)	1982-04-13	2-(2-thenoylthio)-propionylglycine: method for its preparation and pharmaceutical formulations containing said compound
FR2522501A1 (fr)	1983-09-09	Isothiosemicarbazones antivirales et leur utilisation pour prevenir une infection fongique
CH670448A5 (2)	1989-06-15
FR2495145A1 (fr)	1982-06-04	A-(3,4,5-trimethoxybenzoylthio) propionylglycine, son procede de preparation et compositions pharmaceutiques la contenant
CA1100493A (fr)	1981-05-05	Procede de preparation de nouveaux derives de la 11- desoxy prostaglandine f.sub.2
BE875186A (fr)	1979-07-16	2-(2-thenoylthio)-propionyglycine, procede pour sa preparation et compositions pharmaceutiques la contenant
BE882889A (fr)	1980-08-18	Sel de lysine de l'acide meta-benzoyl-hydratropique, son procede de preparation et compositions pharmaceutiques en contenant
FR2491761A1 (fr)	1982-04-16	Derives de l'adenosine a activite anti-inflammatoire et analgesique et compositions therapeutiques qui les contiennent en tant que principe actif
FR2489318A1 (fr)	1982-03-05	Sel d'acide((1-benzyl-1h-indazol-3-yl)oxy)acetique avec la lysine
FR2651230A1 (fr)	1991-03-01	Derives de la 5-amino-1,2,3,4 tetrahydro-acridine et applications comme medicaments.
FR2472387A1 (fr)	1981-07-03	Compositions pharmaceutiques pour le traitement de l'oedeme pulmonaire aigu, de certains etats de choc et de l'hyperfibrinolyse
EP0228978A1 (fr)	1987-07-15	Compositions à usage thérapeutique comprenant des composés organo-siliciés
KR850000210B1 (ko)	1985-03-06	옥사졸린의 제조방법
FR2518537A1 (fr)	1983-06-24	Nouveaux derives de l'acide phenylacetique, leur preparation et compositions les contenant
EP0368758B1 (fr)	1994-07-20	Le cystéate de zinc, sa préparation et ses applications pharmaceutiques et cosmétologiques
FR2472565A1 (fr)	1981-07-03	N-((isopropyl-4 methyl-2 phenyl-1 pyrazolone-5 yl-3)methyl) acetoxy-2 benzamide, procede pour le preparer et medicaments qui le contiennent
CA1080233A (fr)	1980-06-24	Procede de preparation de nouveaux derives de l'oxadiazole et de leurs sels
CA1189526A (fr)	1985-06-25	Procede de preparation de nouveaux derives amines de l'acide 4-phenyl 4-oxo 2-butenoique et de leurs sels
EP0022737B1 (fr)	1982-06-09	Imines dérivées de l'amino-5 benzodioxole-1,3 utiles comme médicaments et leur préparation
LU83775A1 (fr)	1983-09-01	Derives de naphtyridine,leur preparation et leur application en therapeutique
LU83081A1 (fr)	1981-09-10	Compositions antitumeurs
CH652386A5 (fr)	1985-11-15	Derives d'acides phenyl aliphatique carboxyliques comme medicaments.
FR2512015A1 (fr)	1983-03-04	Sels de l'acide 2-oxo-1,5-pentane dioique, leur procede de fabrication et medicaments renfermant ces sels