LU84142A1 - Esters 2-methoxyphenyliques d'amino-acides n-substitues,procede pour leur preparation et compositions pharmaceutiques les contenant - Google Patents

Esters 2-methoxyphenyliques d'amino-acides n-substitues,procede pour leur preparation et compositions pharmaceutiques les contenant Download PDF

Info

Publication number: LU84142A1
Authority: LU; Luxembourg
Prior art keywords: formula; methoxyphenyl; compound; ester; pharmaceutical compositions
Prior art date: 1981-05-11

Application number

LU84142A

Other languages

English (en)

French (fr)

Inventor

Claudio Cavazza

Massimo Carloni

Maria Teresa Ramacci

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.)

1981-05-11

Filing date

1982-05-11

Publication date

1982-09-13

1981-05-11 Priority claimed from IT21620/81A external-priority patent/IT1137577B/it

1981-05-15 Priority claimed from IT48485/81A external-priority patent/IT1170975B/it

1982-05-11 Application filed by Sigma Tau Ind Farmaceuti filed Critical Sigma Tau Ind Farmaceuti

1982-09-13 Publication of LU84142A1 publication Critical patent/LU84142A1/fr

Links

-1 2-METHOXYPHENYL Chemical class 0.000 title claims description 35
239000008194 pharmaceutical composition Substances 0.000 title claims description 12
238000000034 method Methods 0.000 title description 14
230000008569 process Effects 0.000 title description 7
238000002360 preparation method Methods 0.000 title description 5
150000001875 compounds Chemical class 0.000 claims description 50
125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 15
230000000694 effects Effects 0.000 claims description 13
150000002148 esters Chemical class 0.000 claims description 13
LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 claims description 11
230000000510 mucolytic effect Effects 0.000 claims description 8
PWKSKIMOESPYIA-BYPYZUCNSA-N L-N-acetyl-Cysteine Chemical compound CC(=O)N[C@@H](CS)C(O)=O PWKSKIMOESPYIA-BYPYZUCNSA-N 0.000 claims description 6
229960004308 acetylcysteine Drugs 0.000 claims description 6
239000000443 aerosol Substances 0.000 claims description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 4
230000000954 anitussive effect Effects 0.000 claims description 4
239000000460 chlorine Substances 0.000 claims description 4
QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims description 3
235000004279 alanine Nutrition 0.000 claims description 3
229960001867 guaiacol Drugs 0.000 claims description 3
239000006188 syrup Substances 0.000 claims description 3
235000020357 syrup Nutrition 0.000 claims description 3
VHBNOXBGFQQNSF-YFKPBYRVSA-N (2r)-2-acetamido-3-(carboxymethylsulfanyl)propanoic acid Chemical compound CC(=O)N[C@H](C(O)=O)CSCC(O)=O VHBNOXBGFQQNSF-YFKPBYRVSA-N 0.000 claims description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
239000004471 Glycine Substances 0.000 claims description 2
230000003213 activating effect Effects 0.000 claims description 2
229940124584 antitussives Drugs 0.000 claims description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
229910052794 bromium Inorganic materials 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical compound C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 claims description 2
239000011630 iodine Substances 0.000 claims description 2
229910052740 iodine Inorganic materials 0.000 claims description 2
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 2
239000000829 suppository Substances 0.000 claims description 2
125000000896 monocarboxylic acid group Chemical group 0.000 claims 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
239000004480 active ingredient Substances 0.000 claims 1
125000003545 alkoxy group Chemical group 0.000 claims 1
125000000217 alkyl group Chemical group 0.000 claims 1
125000004429 atom Chemical group 0.000 claims 1
239000003795 chemical substances by application Substances 0.000 claims 1
229910052739 hydrogen Inorganic materials 0.000 claims 1
239000001257 hydrogen Substances 0.000 claims 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
239000000243 solution Substances 0.000 description 20
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
UGNJYFMADWVIOT-UHFFFAOYSA-N (2-methoxyphenyl) 2-aminoacetate Chemical compound COC1=CC=CC=C1OC(=O)CN UGNJYFMADWVIOT-UHFFFAOYSA-N 0.000 description 15
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
239000000203 mixture Substances 0.000 description 10
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
230000028327 secretion Effects 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 7
239000002904 solvent Substances 0.000 description 7
JOCRHSHXHVVIFS-UHFFFAOYSA-N thiophene-2-carbothioic s-acid Chemical compound SC(=O)C1=CC=CS1 JOCRHSHXHVVIFS-UHFFFAOYSA-N 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
239000002253 acid Substances 0.000 description 6
235000001014 amino acid Nutrition 0.000 description 6
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
OROGSEYTTFOCAN-DNJOTXNNSA-N codeine Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC OROGSEYTTFOCAN-DNJOTXNNSA-N 0.000 description 6
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
230000001886 ciliary effect Effects 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
GBFLZEXEOZUWRN-VKHMYHEASA-N S-carboxymethyl-L-cysteine Chemical compound OC(=O)[C@@H](N)CSCC(O)=O GBFLZEXEOZUWRN-VKHMYHEASA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
YTGJWQPHMWSCST-UHFFFAOYSA-N Tiopronin Chemical compound CC(S)C(=O)NCC(O)=O YTGJWQPHMWSCST-UHFFFAOYSA-N 0.000 description 4
150000001413 amino acids Chemical class 0.000 description 4
238000000338 in vitro Methods 0.000 description 4
230000005764 inhibitory process Effects 0.000 description 4
238000007912 intraperitoneal administration Methods 0.000 description 4
239000000047 product Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
241000283973 Oryctolagus cuniculus Species 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
241000700159 Rattus Species 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
229960004126 codeine Drugs 0.000 description 3
230000008030 elimination Effects 0.000 description 3
238000003379 elimination reaction Methods 0.000 description 3
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 3
239000003172 expectorant agent Substances 0.000 description 3
238000009472 formulation Methods 0.000 description 3
OROGSEYTTFOCAN-UHFFFAOYSA-N hydrocodone Natural products C1C(N(CCC234)C)C2C=CC(O)C3OC2=C4C1=CC=C2OC OROGSEYTTFOCAN-UHFFFAOYSA-N 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
KXHUVWDIKYRVPQ-UHFFFAOYSA-N 2-(thiophene-2-carbonylsulfanyl)propanoic acid Chemical compound OC(=O)C(C)SC(=O)C1=CC=CS1 KXHUVWDIKYRVPQ-UHFFFAOYSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
241000700198 Cavia Species 0.000 description 2
206010011224 Cough Diseases 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
OKJIRPAQVSHGFK-UHFFFAOYSA-N N-acetylglycine Chemical compound CC(=O)NCC(O)=O OKJIRPAQVSHGFK-UHFFFAOYSA-N 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
230000009471 action Effects 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
125000006295 amino methylene group Chemical group [H]N(*)C([H])([H])* 0.000 description 2
150000008064 anhydrides Chemical class 0.000 description 2
239000002585 base Substances 0.000 description 2
238000010586 diagram Methods 0.000 description 2
NJDNXYGOVLYJHP-UHFFFAOYSA-L disodium;2-(3-oxido-6-oxoxanthen-9-yl)benzoate Chemical compound [Na+].[Na+].[O-]C(=O)C1=CC=CC=C1C1=C2C=CC(=O)C=C2OC2=CC([O-])=CC=C21 NJDNXYGOVLYJHP-UHFFFAOYSA-L 0.000 description 2
239000012153 distilled water Substances 0.000 description 2
239000003814 drug Substances 0.000 description 2
230000003419 expectorant effect Effects 0.000 description 2
238000001727 in vivo Methods 0.000 description 2
239000007788 liquid Substances 0.000 description 2
LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
239000011591 potassium Substances 0.000 description 2
125000006239 protecting group Chemical group 0.000 description 2
230000002685 pulmonary effect Effects 0.000 description 2
HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 2
229940001584 sodium metabisulfite Drugs 0.000 description 2
235000010262 sodium metabisulphite Nutrition 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
239000007787 solid Substances 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
238000004809 thin layer chromatography Methods 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
QERYCTSHXKAMIS-UHFFFAOYSA-N thiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-N 0.000 description 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
DRMOCHGNKTXIBF-UHFFFAOYSA-N 2-(2-methoxyanilino)acetic acid Chemical compound COC1=CC=CC=C1NCC(O)=O DRMOCHGNKTXIBF-UHFFFAOYSA-N 0.000 description 1
XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
TVEXGJYMHHTVKP-UHFFFAOYSA-N 6-oxabicyclo[3.2.1]oct-3-en-7-one Chemical compound C1C2C(=O)OC1C=CC2 TVEXGJYMHHTVKP-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 1
DHMQDGOQFOQNFH-UHFFFAOYSA-M Aminoacetate Chemical compound NCC([O-])=O DHMQDGOQFOQNFH-UHFFFAOYSA-M 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
208000014181 Bronchial disease Diseases 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 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
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
KTHDTJVBEPMMGL-VKHMYHEASA-N N-acetyl-L-alanine Chemical compound OC(=O)[C@H](C)NC(C)=O KTHDTJVBEPMMGL-VKHMYHEASA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 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
UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
108010058907 Tiopronin Proteins 0.000 description 1
230000007059 acute toxicity Effects 0.000 description 1
231100000403 acute toxicity Toxicity 0.000 description 1
150000001263 acyl chlorides Chemical class 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
230000003110 anti-inflammatory effect Effects 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
125000001797 benzyl group Chemical class [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
230000037396 body weight Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 1
210000000845 cartilage Anatomy 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
HSPYGHDTVQJUDE-LURJTMIESA-N dacisteine Chemical compound CC(=O)N[C@H](C(O)=O)CSC(C)=O HSPYGHDTVQJUDE-LURJTMIESA-N 0.000 description 1
239000012895 dilution Substances 0.000 description 1
238000010790 dilution Methods 0.000 description 1
229940079593 drug Drugs 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
239000003480 eluent Substances 0.000 description 1
230000007071 enzymatic hydrolysis Effects 0.000 description 1
238000006047 enzymatic hydrolysis reaction Methods 0.000 description 1
210000000981 epithelium Anatomy 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000007927 intramuscular injection Substances 0.000 description 1
238000010255 intramuscular injection Methods 0.000 description 1
210000004072 lung Anatomy 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
230000004899 motility Effects 0.000 description 1
229940066491 mucolytics Drugs 0.000 description 1
210000004877 mucosa Anatomy 0.000 description 1
210000003097 mucus Anatomy 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
230000007170 pathology Effects 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
150000003112 potassium compounds Chemical class 0.000 description 1
DPLVEEXVKBWGHE-UHFFFAOYSA-N potassium sulfide Chemical compound [S-2].[K+].[K+] DPLVEEXVKBWGHE-UHFFFAOYSA-N 0.000 description 1
VNQMVHFKIQKMAV-UHFFFAOYSA-M potassium;methanethioate Chemical compound [K+].[O-]C=S VNQMVHFKIQKMAV-UHFFFAOYSA-M 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
230000001698 pyrogenic effect Effects 0.000 description 1
210000002345 respiratory system Anatomy 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 1
GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003860 storage Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
239000003826 tablet Substances 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
QIQITDHWZYEEPA-UHFFFAOYSA-N thiophene-2-carbonyl chloride Chemical compound ClC(=O)C1=CC=CS1 QIQITDHWZYEEPA-UHFFFAOYSA-N 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
230000032258 transport Effects 0.000 description 1
JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 0.000 description 1
230000010415 tropism Effects 0.000 description 1
238000005303 weighing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
- 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

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Plural Heterocyclic Compounds (AREA)

LU84142A 1981-05-11 1982-05-11 Esters 2-methoxyphenyliques d'amino-acides n-substitues,procede pour leur preparation et compositions pharmaceutiques les contenant LU84142A1 (fr)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
IT21620/81A IT1137577B (it)	1981-05-11	1981-05-11	Composto ad attivita' broncosecretolitica e antitussigena,procedimenti per la sua preparazione e relative composizioni farmaceutiche
IT2162081		1981-05-11
IT48485/81A IT1170975B (it)	1981-05-15	1981-05-15	Esteri del guaiacolo con amminoacidi n-sostituiti procedimento per la loro preparazione e composizioni farmaceutiche che li contengono
IT4848581		1981-05-15

Publications (1)

Publication Number	Publication Date
LU84142A1 true LU84142A1 (fr)	1982-09-13

Family

ID=26327948

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
LU84142A LU84142A1 (fr)	1981-05-11	1982-05-11	Esters 2-methoxyphenyliques d'amino-acides n-substitues,procede pour leur preparation et compositions pharmaceutiques les contenant

Country Status (17)

Country	Link
US (1)	US4405638A (da)
KR (1)	KR890000486B1 (da)
AR (1)	AR231722A1 (da)
AT (1)	ATA183182A (da)
CA (1)	CA1196924A (da)
CH (1)	CH655095A5 (da)
DE (1)	DE3216986A1 (da)
DK (1)	DK154210C (da)
ES (1)	ES8307717A1 (da)
FR (1)	FR2505329B1 (da)
GB (1)	GB2100723B (da)
IE (1)	IE52884B1 (da)
KE (1)	KE3521A (da)
LU (1)	LU84142A1 (da)
NL (1)	NL8201820A (da)
NO (1)	NO160779C (da)
SE (1)	SE453391B (da)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IT1143209B (it) *	1981-07-02	1986-10-22	Sigma Tau Ind Farmaceuti	Esteri della 2-tenoilmercaptopropionil glicina con idrossibenzeni sostituiti procedimento per la loro preparazione e composizioni farmaceutiche che li contengono
US4623651A (en)	1985-10-15	1986-11-18	Merrell Dow Pharmaceuticals Inc.	Cardiotonic heterocyclocarbonyl- and acetyl-thiazolones
US4927939A (en) *	1985-10-15	1990-05-22	Merrell Dow Pharmaceuticals	Cardiotonic aroylthiazolones
US4762849A (en) *	1985-10-15	1988-08-09	Merrell Dow Pharmaceuticals Inc.	Cardiotonic alkanoylthiazolones

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4108886A (en) *	1977-03-11	1978-08-22	E. R. Squibb & Sons, Inc.	Thiopropanoylamino acid derivatives
CA1121825A (en) *	1978-04-11	1982-04-13	Franco Bolasco	2-(2-thenoylthio)-propionylglycine: method for its preparation and pharmaceutical formulations containing said compound
FR2430945A2 (fr) *	1978-07-12	1980-02-08	Chauvin Blache Lab	Nouveaux derives de la cysteine, leur procede de fabrication et leur application en therapeutique
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
US4279842A (en) *	1979-07-26	1981-07-21	Houston Systems Manufacturing Co., Inc.	Air diffuser assembly

1982
- 1982-04-27 IE IE987/82A patent/IE52884B1/en unknown
- 1982-04-29 US US06/372,985 patent/US4405638A/en not_active Expired - Fee Related
- 1982-04-30 CH CH2643/82A patent/CH655095A5/it not_active IP Right Cessation
- 1982-04-30 GB GB08212624A patent/GB2100723B/en not_active Expired
- 1982-05-03 NL NL8201820A patent/NL8201820A/nl not_active Application Discontinuation
- 1982-05-06 DE DE19823216986 patent/DE3216986A1/de not_active Ceased
- 1982-05-07 AR AR289337A patent/AR231722A1/es active
- 1982-05-07 FR FR8207986A patent/FR2505329B1/fr not_active Expired
- 1982-05-10 KR KR8202030A patent/KR890000486B1/ko not_active Expired
- 1982-05-10 ES ES512769A patent/ES8307717A1/es not_active Expired
- 1982-05-10 AT AT0183182A patent/ATA183182A/de not_active Application Discontinuation
- 1982-05-10 CA CA000402568A patent/CA1196924A/en not_active Expired
- 1982-05-10 NO NO821545A patent/NO160779C/no unknown
- 1982-05-11 SE SE8202962A patent/SE453391B/sv not_active IP Right Cessation
- 1982-05-11 DK DK210882A patent/DK154210C/da not_active IP Right Cessation
- 1982-05-11 LU LU84142A patent/LU84142A1/fr unknown
1985
- 1985-04-04 KE KE3521A patent/KE3521A/xx unknown

Also Published As

Publication number	Publication date
KE3521A (en)	1985-05-03
DE3216986A1 (de)	1982-11-25
SE453391B (sv)	1988-02-01
NO821545L (no)	1982-11-12
DK210882A (da)	1982-11-12
ES512769A0 (es)	1983-08-01
DK154210B (da)	1988-10-24
KR890000486B1 (ko)	1989-03-18
GB2100723B (en)	1985-01-09
NO160779C (no)	1989-05-31
AR231722A1 (es)	1985-02-28
CA1196924A (en)	1985-11-19
NO160779B (no)	1989-02-20
NL8201820A (nl)	1982-12-01
GB2100723A (en)	1983-01-06
CH655095A5 (it)	1986-03-27
DK154210C (da)	1989-03-13
FR2505329B1 (fr)	1986-04-25
ATA183182A (de)	1990-05-15
KR830010051A (ko)	1983-12-24
US4405638A (en)	1983-09-20
SE8202962D0 (sv)	1982-05-11
FR2505329A1 (fr)	1982-11-12
IE820987L (en)	1982-11-11
IE52884B1 (en)	1988-03-30
ES8307717A1 (es)	1983-08-01
SE8202962L (sv)	1982-11-12

Publication	Publication Date	Title
CH651561A5 (fr)	1985-09-30	Derives des nor-tropane et granatane et leur procede de preparation.
CH619463A5 (da)	1980-09-30
EP0459887A1 (fr)	1991-12-04	Dérivés N-pyrazolyl-ortho-dialkyl-benzamide doués d'activité anticonvulsivante, procédé de préparation et composition pharmaceutique
EP0021940B1 (fr)	1983-01-19	Nouveaux dérivés aminés du benzothiazole, leur procédé de préparation et leur application en thérapeutique
EP0173597B1 (fr)	1989-12-27	Nouveaux éther-oxydes dérivés de cyclopropylphénols
LU84142A1 (fr)	1982-09-13	Esters 2-methoxyphenyliques d'amino-acides n-substitues,procede pour leur preparation et compositions pharmaceutiques les contenant
CA1265803A (fr)	1990-02-13	Amides substitues, leur preparation et les medicaments qui les contiennent
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
EP0169755B1 (fr)	1990-05-09	Nouveaux dérivés de l'acide 4-hydroxy 3-quinoléine carboxylique subsititués en 2 par une fonction aminée, leur préparation, leur application comme médicaments, les compositions les renfermant et les intermédiaires nouveaux obtenus
FR2559151A1 (fr)	1985-08-09	Derives de l'arginine et sels d'addition d'acides correspondants pharmaceutiquement acceptables et compositions pharmaceutiques les contenant
FR2460934A1 (fr)	1981-01-30	Derives d'isoquinoleine contenant du soufre, procedes pour leur preparation et compositions pharmaceutiques les contenant
EP0294258A1 (fr)	1988-12-07	Dérivés d'hydrazine, procédé d'obtention et compositions pharmaceutiques les contenant
FR2550530A1 (fr)	1985-02-15	Derives 2',4'-difluoro-4-hydroxy-(1,1'-biphenyl)-3-carboxyliques de la n-acetyl-cysteine et s-carboxymethyl-cysteine a activite anti-inflammatoire et mucolytique, leur procede de preparation et compositions pharmaceutiques correspondantes
FR2610627A1 (fr)	1988-08-12	Sels cristallins de l'acide (3s(z))-2(((1-(2-amino-4-thiazolyl)-2-((2,2-dimethyl-4-oxo-1-(sulfo-oxy)-3-azetidinyl)amino)-2-oxoethylidene)-amino)oxy)acetique, a action therapeutique
CA1125743A (fr)	1982-06-15	Derives d'amino-3-cardenolides, procede pour leur preparation, et medicaments les contenant
CH410900A (fr)	1966-04-15	Procédé de préparation de nouvelles moutardes à l'azote
FR2518542A1 (fr)	1983-06-24	Dipeptides comportant un residu methionine et ayant un effet de protection pour le foie
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
EP0022022B1 (fr)	1983-05-11	Nouveaux dérivés acylés de la taurine et leurs sels et procédé pour leur préparation
CH618977A5 (da)	1980-08-29
BE876466A (fr)	1979-11-23	Derive de l'acide penicillanique et son procede de preparation
BE503348A (da)
FR2556592A1 (fr)	1985-06-21	Compositions pharmaceutiques contenant des derives de l'acide campho-methylidene cinnamique
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
FR2462434A1 (fr)	1981-02-13	Nouveaux derives de benzo(b)furanne et compositions pharmaceutiques contenant ces derives