LU84245A1 - Esters de 2-thenoylmercaptopropionylglycine avec des hydroxybenzenes substitutes, leur procede de preparation et compositions pharmaceutiques en contenant - Google Patents

Esters de 2-thenoylmercaptopropionylglycine avec des hydroxybenzenes substitutes, leur procede de preparation et compositions pharmaceutiques en contenant Download PDF

Info

Publication number: LU84245A1
Authority: LU; Luxembourg
Prior art keywords: group; glycyloxy; namely; thénoylmercaptopropionyl; benzoate
Prior art date: 1981-07-02

Application number

LU84245A

Other languages

English (en)

French (fr)

Original Assignee

Sigma Tau Ind Farmaceuti

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.)

1981-07-02

Filing date

1982-06-30

Publication date

1983-01-20

1982-06-30 Application filed by Sigma Tau Ind Farmaceuti filed Critical Sigma Tau Ind Farmaceuti

1983-01-20 Publication of LU84245A1 publication Critical patent/LU84245A1/fr

Links

OIJKSYBUWMYGCW-UHFFFAOYSA-N 2-[3-(thiophene-2-carbonylsulfanyl)propanoylamino]acetic acid Chemical class OC(=O)CNC(=O)CCSC(=O)C1=CC=CS1 OIJKSYBUWMYGCW-UHFFFAOYSA-N 0.000 title claims description 11
238000000034 method Methods 0.000 title claims description 10
238000002360 preparation method Methods 0.000 title claims description 8
150000005204 hydroxybenzenes Chemical class 0.000 title claims description 6
239000008194 pharmaceutical composition Substances 0.000 title claims description 5
-1 p-acetamidophenyl group Chemical group 0.000 claims description 19
150000002148 esters Chemical class 0.000 claims description 17
239000004480 active ingredient Substances 0.000 claims description 8
125000004432 carbon atom Chemical group C* 0.000 claims description 7
230000000510 mucolytic effect Effects 0.000 claims description 7
125000000217 alkyl group Chemical group 0.000 claims description 6
150000008064 anhydrides Chemical class 0.000 claims description 6
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 4
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 4
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
239000000546 pharmaceutical excipient Substances 0.000 claims description 4
229960003742 phenol Drugs 0.000 claims description 4
235000010232 propyl p-hydroxybenzoate Nutrition 0.000 claims description 3
239000004405 propyl p-hydroxybenzoate Substances 0.000 claims description 3
QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 claims description 2
125000005429 oxyalkyl group Chemical group 0.000 claims 3
UDEWPOVQBGFNGE-UHFFFAOYSA-N benzoic acid n-propyl ester Natural products CCCOC(=O)C1=CC=CC=C1 UDEWPOVQBGFNGE-UHFFFAOYSA-N 0.000 claims 2
XSIFPSYPOVKYCO-UHFFFAOYSA-N butyl benzoate Chemical compound CCCCOC(=O)C1=CC=CC=C1 XSIFPSYPOVKYCO-UHFFFAOYSA-N 0.000 claims 2
OLXYLDUSSBULGU-UHFFFAOYSA-N methyl pyridine-4-carboxylate Chemical compound COC(=O)C1=CC=NC=C1 OLXYLDUSSBULGU-UHFFFAOYSA-N 0.000 claims 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
230000003110 anti-inflammatory effect Effects 0.000 claims 1
229910052799 carbon Inorganic materials 0.000 claims 1
229940095102 methyl benzoate Drugs 0.000 claims 1
YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 claims 1
150000001875 compounds Chemical class 0.000 description 28
239000000243 solution Substances 0.000 description 18
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 15
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 14
241001465754 Metazoa Species 0.000 description 9
230000000694 effects Effects 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 8
230000001886 ciliary effect Effects 0.000 description 8
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
206010011224 Cough Diseases 0.000 description 7
230000028327 secretion Effects 0.000 description 7
LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 description 6
239000000203 mixture Substances 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
206010036790 Productive cough Diseases 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
210000003802 sputum Anatomy 0.000 description 5
208000024794 sputum Diseases 0.000 description 5
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
PWKSKIMOESPYIA-BYPYZUCNSA-N L-N-acetyl-Cysteine Chemical compound CC(=O)N[C@@H](CS)C(O)=O PWKSKIMOESPYIA-BYPYZUCNSA-N 0.000 description 4
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
229960004308 acetylcysteine Drugs 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
239000003172 expectorant agent Substances 0.000 description 4
HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 4
229940001584 sodium metabisulfite Drugs 0.000 description 4
235000010262 sodium metabisulphite Nutrition 0.000 description 4
238000003756 stirring Methods 0.000 description 4
239000000829 suppository Substances 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000000443 aerosol Substances 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
239000012895 dilution Substances 0.000 description 3
238000010790 dilution Methods 0.000 description 3
239000012153 distilled water Substances 0.000 description 3
230000003419 expectorant effect Effects 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
239000007787 solid Substances 0.000 description 3
239000000126 substance Substances 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 2
241000700198 Cavia Species 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
229960001413 acetanilide Drugs 0.000 description 2
230000007059 acute toxicity Effects 0.000 description 2
231100000403 acute toxicity Toxicity 0.000 description 2
238000010171 animal model Methods 0.000 description 2
239000003480 eluent Substances 0.000 description 2
210000000981 epithelium Anatomy 0.000 description 2
238000001914 filtration Methods 0.000 description 2
229960001867 guaiacol Drugs 0.000 description 2
238000004128 high performance liquid chromatography Methods 0.000 description 2
238000000338 in vitro Methods 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
230000004899 motility Effects 0.000 description 2
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
150000007530 organic bases Chemical class 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
239000000047 product Substances 0.000 description 2
CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 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
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000006188 syrup Substances 0.000 description 2
235000020357 syrup Nutrition 0.000 description 2
238000004809 thin layer chromatography Methods 0.000 description 2
229930192474 thiophene Natural products 0.000 description 2
210000003437 trachea Anatomy 0.000 description 2
FSCGLKWYHHSLST-UHFFFAOYSA-N 2-(3-sulfanylpropanoylamino)acetic acid Chemical compound OC(=O)CNC(=O)CCS FSCGLKWYHHSLST-UHFFFAOYSA-N 0.000 description 1
PJFNNMFXEVADGK-UHFFFAOYSA-N 2-hydroxy-n-phenylacetamide Chemical compound OCC(=O)NC1=CC=CC=C1 PJFNNMFXEVADGK-UHFFFAOYSA-N 0.000 description 1
FJKROLUGYXJWQN-UHFFFAOYSA-M 4-hydroxybenzoate Chemical compound OC1=CC=C(C([O-])=O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-M 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
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
241000283973 Oryctolagus cuniculus Species 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
108010058907 Tiopronin Proteins 0.000 description 1
OUCXYSRPMBQONT-UHFFFAOYSA-N acetamide;phenol Chemical compound CC(N)=O.OC1=CC=CC=C1 OUCXYSRPMBQONT-UHFFFAOYSA-N 0.000 description 1
125000006295 amino methylene group Chemical group [H]N(*)C([H])([H])* 0.000 description 1
239000003708 ampul Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
230000037396 body weight Effects 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000002775 capsule Substances 0.000 description 1
FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
235000008504 concentrate Nutrition 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 1
235000018417 cysteine Nutrition 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
230000007794 irritation Effects 0.000 description 1
231100000636 lethal dose Toxicity 0.000 description 1
XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 1
239000007788 liquid Substances 0.000 description 1
125000000896 monocarboxylic acid group Chemical group 0.000 description 1
229940066491 mucolytics Drugs 0.000 description 1
210000003097 mucus Anatomy 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
239000007968 orange flavor Substances 0.000 description 1
YBPAYPRLUDCSEY-UHFFFAOYSA-N p-hydroxyphenylacetoamide Natural products NC(=O)CC1=CC=C(O)C=C1 YBPAYPRLUDCSEY-UHFFFAOYSA-N 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
235000020030 perry Nutrition 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
230000029058 respiratory gaseous exchange Effects 0.000 description 1
210000002345 respiratory system Anatomy 0.000 description 1
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical class OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 1
239000012265 solid product Substances 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
239000007921 spray Substances 0.000 description 1
239000008174 sterile solution Substances 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
229960004402 tiopronin Drugs 0.000 description 1
210000005062 tracheal ring Anatomy 0.000 description 1
238000005303 weighing Methods 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
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/10—Expectorants
- 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)
Public Health (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Rheumatology (AREA)
Pain & Pain Management (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Pulmonology (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)
Heterocyclic Compounds Containing Sulfur Atoms (AREA)

LU84245A 1981-07-02 1982-06-30 Esters de 2-thenoylmercaptopropionylglycine avec des hydroxybenzenes substitutes, leur procede de preparation et compositions pharmaceutiques en contenant LU84245A1 (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
IT4880781		1981-07-02
IT48807/81A IT1143209B (it)	1981-07-02	1981-07-02	Esteri della 2-tenoilmercaptopropionil glicina con idrossibenzeni sostituiti procedimento per la loro preparazione e composizioni farmaceutiche che li contengono

Publications (1)

Publication Number	Publication Date
LU84245A1 true LU84245A1 (fr)	1983-01-20

Family

ID=11268648

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
LU84245A LU84245A1 (fr)	1981-07-02	1982-06-30	Esters de 2-thenoylmercaptopropionylglycine avec des hydroxybenzenes substitutes, leur procede de preparation et compositions pharmaceutiques en contenant

Country Status (19)

Country	Link
US (1)	US4472424A (da)
JP (1)	JPS5810577A (da)
KR (1)	KR860001311B1 (da)
AT (1)	ATA255682A (da)
BE (1)	BE893712A (da)
CA (1)	CA1198735A (da)
CH (1)	CH651035A5 (da)
DE (1)	DE3224824A1 (da)
DK (1)	DK153760C (da)
ES (1)	ES8306369A1 (da)
FR (1)	FR2508907A1 (da)
GB (1)	GB2102797B (da)
GR (1)	GR76187B (da)
IE (1)	IE53190B1 (da)
IL (1)	IL66190A0 (da)
IT (1)	IT1143209B (da)
LU (1)	LU84245A1 (da)
NL (1)	NL8202658A (da)
SE (1)	SE8204116L (da)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IT1241415B (it) *	1990-03-05	1994-01-14	Yason Srl	Derivato dell'acido s-(2-tenoil)-tiolattico ad attivita' farmacologica
US5114963A (en) *	1991-03-13	1992-05-19	Medicis Corporation	Method of reducing serum levels of lipoprotein(A)
WO2002016832A1 (en) *	2000-08-18	2002-02-28	Hokko Sohgoh Kaihatsu K.K.	Floor heater, thermal siphon heat pipe, and method of manufacturing heat pipe

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA1121825A (en) *	1978-04-11	1982-04-13	Franco Bolasco	2-(2-thenoylthio)-propionylglycine: method for its preparation and pharmaceutical formulations containing said compound
IT1111384B (it) *	1978-12-21	1986-01-13	Sigma Tau Ind Farmaceuti	Guaiacil esteri di derivati dello acido mercaptopropionico procedimento per la loro preparazione e loro uso terapeutico
IT1149884B (it) *	1980-06-03	1986-12-10	Btb Ind Chimica	Prozedimento per la preparazione della n-(2-tenoil)tiopropionil)-glicina
IT1148890B (it) *	1980-07-22	1986-12-03	Neopharmed Spa	Derivato della teonil tiopropionil glicina e procedimento per la sua preparazione
IE52884B1 (en) *	1981-05-11	1988-03-30	Sigma Tau Ind Farmaceuti	2-methoxyphenyl esters of n-substituted amino acids, their preparation and pharmaceutical use

1981
- 1981-07-02 IT IT48807/81A patent/IT1143209B/it active
1982
- 1982-06-22 IE IE1483/82A patent/IE53190B1/en unknown
- 1982-06-24 US US06/391,741 patent/US4472424A/en not_active Expired - Fee Related
- 1982-06-25 CA CA000405966A patent/CA1198735A/en not_active Expired
- 1982-06-28 CH CH3964/82A patent/CH651035A5/it not_active IP Right Cessation
- 1982-06-28 GB GB08218672A patent/GB2102797B/en not_active Expired
- 1982-06-30 JP JP57114775A patent/JPS5810577A/ja active Pending
- 1982-06-30 BE BE0/208501A patent/BE893712A/fr not_active IP Right Cessation
- 1982-06-30 LU LU84245A patent/LU84245A1/fr unknown
- 1982-06-30 KR KR8202936A patent/KR860001311B1/ko not_active Expired
- 1982-06-30 DK DK294982A patent/DK153760C/da not_active IP Right Cessation
- 1982-07-01 AT AT0255682A patent/ATA255682A/de not_active Application Discontinuation
- 1982-07-01 GR GR68614A patent/GR76187B/el unknown
- 1982-07-01 NL NL8202658A patent/NL8202658A/nl not_active Application Discontinuation
- 1982-07-01 ES ES514456A patent/ES8306369A1/es not_active Expired
- 1982-07-01 IL IL66190A patent/IL66190A0/xx unknown
- 1982-07-02 FR FR8211684A patent/FR2508907A1/fr active Granted
- 1982-07-02 DE DE19823224824 patent/DE3224824A1/de not_active Ceased
- 1982-07-02 SE SE8204116A patent/SE8204116L/xx not_active Application Discontinuation

Also Published As

Publication number	Publication date
JPS5810577A (ja)	1983-01-21
IE53190B1 (en)	1988-08-17
DK153760C (da)	1989-01-09
DE3224824A1 (de)	1983-01-27
FR2508907A1 (fr)	1983-01-07
ATA255682A (de)	1990-05-15
NL8202658A (nl)	1983-02-01
DK294982A (da)	1983-01-03
DK153760B (da)	1988-08-29
ES514456A0 (es)	1983-06-01
KR860001311B1 (ko)	1986-09-13
CH651035A5 (it)	1985-08-30
BE893712A (fr)	1982-10-18
CA1198735A (en)	1985-12-31
ES8306369A1 (es)	1983-06-01
IE821483L (en)	1983-01-02
GB2102797A (en)	1983-02-09
IL66190A0 (en)	1982-11-30
US4472424A (en)	1984-09-18
SE8204116L (sv)	1983-01-03
IT8148807A0 (it)	1981-07-02
KR840000235A (ko)	1984-02-18
SE8204116D0 (sv)	1982-07-02
GR76187B (da)	1984-08-03
IT1143209B (it)	1986-10-22
FR2508907B1 (da)	1984-12-28
GB2102797B (en)	1985-01-30

Publication	Publication Date	Title
EP0318377B1 (fr)	1993-08-25	Nouveaux composés énantiomères dérivés d'amino-acides, leur procédé de préparation et leurs applications thérapeutiques
EP0046707B1 (fr)	1986-07-30	Dérivés de l'acide amino-4 butyrique et les médicaments, actifs notamment sur le système nerveux central, en contenant
FR2522324A1 (fr)	1983-09-02	Pyrrole-acetamides, leur procede de preparation et composition therapeutique les contenant
EP0012639A2 (fr)	1980-06-25	Nouveaux dérivés de l'acide 3-quinoléine carboxylique, leur procédé de préparation, leur application comme médicament et les compositions pharmaceutiques les renfermant
FR2527204A1 (fr)	1983-11-25	Nouveaux composes utiles comme medicaments anti-allergiques et procede et intermediaires pour leur separation
LU84090A1 (fr)	1983-04-13	Nouveaux derives d'acides phenyl aliphatique carboxyliques,leur preparation,leur application comme medicaments et les compositions les renfermant
EP0134179B1 (fr)	1988-09-28	Nouveaux dérivés de l'acide 4-phényl 4-oxo-buten 2-oique, leur procédé de préparation, des médicaments et des compositions les renfermant
EP0133176B1 (fr)	1986-09-03	Composition pharmaceutique ou vétérinaire destinée à combattre des troubles ischémiques cardiaques
LU84062A1 (fr)	1982-07-08	Esters de mercaptoacyl-carnitines,procede pour leur preparation et leurs utilisations therapeutiques,notamment dans le traitement des intoxications et des brulures et en tant qu'agents mucolytiques
FR2556721A1 (fr)	1985-06-21	Nouveaux derives de o-mercaptopropanamide d'o amino-acides, leur procede de preparation, leur application comme medicaments et les compositions les renfermant
FR2526792A1 (fr)	1983-11-18	Derives d'aletheine utiles pour le traitement des lesions hepatiques
FR2508907A1 (fr)	1983-01-07	Esters d'hydroxybenzenes substitues de 2-thenoylmercaptopropionylglycine utiles notamment comme mucolytiques, procede pour leur preparation et compositions pharmaceutiques les contenant
CH615673A5 (da)	1980-02-15
FR2584070A1 (fr)	1987-01-02	Nouveaux derives de l'hydroxy alkoxy 4-phenyl propyl indole, leurs sels, procede et intermediaires de preparation, application a titre de medicaments et compositions les renfermant.
CA1271197A (fr)	1990-07-03	Procede de preparation de derives du 4-phenylpropyl indole
EP0082040B1 (fr)	1986-01-15	Dérivés de diaza-3,7a cyclohepta(j,k)fluorènes, leur préparation et leur application en thérapeutique
EP0012072A2 (fr)	1980-06-11	Bêta-lactones dérivées de l'acide 2-hydroxy cyclopentane carboxylique, procédé pour leur préparation et compositions pharmaceutiques les renfermant
LU84061A1 (fr)	1982-07-08	Mercapto-acyl-carnitines,leur procede de preparation et compositions pharmaceutiques en contenant
FR2517672A1 (fr)	1983-06-10	Thioalcanoyl-carnitines, procede pour leur preparation et composition pharmaceutique les contenant
FR2640139A1 (fr)	1990-06-15	Application de benzamides substitues comme gastromoteurs
EP0275221B1 (fr)	1991-04-17	Nouveaux dérivés du N-(1H-indol 4-yl) benzamide ainsi que leurs sels, leur application à titre de médicaments et les compositions les renfermant
LU84142A1 (fr)	1982-09-13	Esters 2-methoxyphenyliques d'amino-acides n-substitues,procede pour leur preparation et compositions pharmaceutiques les contenant
CA1080233A (fr)	1980-06-24	Procede de preparation de nouveaux derives de l'oxadiazole et de leurs sels
EP0161172A1 (fr)	1985-11-13	Dérivés d'acide n-(phenylmethylthio-3 oxo-1 propyl)-aminoacétique, leur préparation et leur application en thérapeutique
CH674204A5 (da)	1990-05-15