NL8201820A - 2-methoxyfenylesters van n-gesubstitueerde aminozuren, een werkwijze voor hun bereiding en farmaceutica die deze verbindingen bevatten. - Google Patents

2-methoxyfenylesters van n-gesubstitueerde aminozuren, een werkwijze voor hun bereiding en farmaceutica die deze verbindingen bevatten. Download PDF

Info

Publication number: NL8201820A
Authority: NL; Netherlands
Prior art keywords: formula; compound; methoxyphenyl; methoxyphenyl ester; thenoylthio
Prior art date: 1981-05-11

Application number

NL8201820A

Other languages

English (en)

Dutch (nl)

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

1982-05-03

Publication date

1982-12-01

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

1982-05-03 Application filed by Sigma Tau Ind Farmaceuti filed Critical Sigma Tau Ind Farmaceuti

1982-12-01 Publication of NL8201820A publication Critical patent/NL8201820A/nl

Links

150000001875 compounds Chemical class 0.000 title claims description 50
-1 2-METHOXYPHENYL Chemical class 0.000 title claims description 37
238000000034 method Methods 0.000 title description 9
238000002360 preparation method Methods 0.000 title description 8
125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 11
239000003814 drug Substances 0.000 claims description 10
150000002148 esters Chemical class 0.000 claims description 10
230000000510 mucolytic effect Effects 0.000 claims description 8
239000000460 chlorine Substances 0.000 claims description 5
239000000443 aerosol Substances 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
230000000954 anitussive effect Effects 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 claims description 3
239000007788 liquid Substances 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 3
239000006188 syrup Substances 0.000 claims description 3
235000020357 syrup Nutrition 0.000 claims description 3
JOCRHSHXHVVIFS-UHFFFAOYSA-N thiophene-2-carbothioic s-acid Chemical compound SC(=O)C1=CC=CS1 JOCRHSHXHVVIFS-UHFFFAOYSA-N 0.000 claims description 3
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-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
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
230000003213 activating effect Effects 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
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
229910052740 iodine Inorganic materials 0.000 claims description 2
239000011630 iodine Substances 0.000 claims description 2
KTHDTJVBEPMMGL-GSVOUGTGSA-N n-acetylalanine Chemical compound OC(=O)[C@@H](C)NC(C)=O KTHDTJVBEPMMGL-GSVOUGTGSA-N 0.000 claims description 2
230000003248 secreting effect Effects 0.000 claims description 2
239000000829 suppository Substances 0.000 claims description 2
239000005977 Ethylene Substances 0.000 claims 1
239000013543 active substance Substances 0.000 claims 1
125000003545 alkoxy group Chemical group 0.000 claims 1
125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims 1
238000002347 injection Methods 0.000 claims 1
239000007924 injection Substances 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
239000000825 pharmaceutical preparation Substances 0.000 claims 1
239000000243 solution Substances 0.000 description 20
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
230000000694 effects Effects 0.000 description 13
150000001413 amino acids Chemical class 0.000 description 8
LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 description 8
230000028327 secretion Effects 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 7
239000000203 mixture Substances 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 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
239000002904 solvent Substances 0.000 description 6
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
235000001014 amino acid Nutrition 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
206010011224 Cough Diseases 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
GBFLZEXEOZUWRN-VKHMYHEASA-N S-carboxymethyl-L-cysteine Chemical compound OC(=O)[C@@H](N)CSCC(O)=O GBFLZEXEOZUWRN-VKHMYHEASA-N 0.000 description 4
229960004308 acetylcysteine Drugs 0.000 description 4
238000000338 in vitro Methods 0.000 description 4
238000007912 intraperitoneal administration Methods 0.000 description 4
238000003756 stirring Methods 0.000 description 4
DHMQDGOQFOQNFH-UHFFFAOYSA-M Aminoacetate Chemical compound NCC([O-])=O DHMQDGOQFOQNFH-UHFFFAOYSA-M 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-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
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
239000003172 expectorant agent Substances 0.000 description 3
150000002366 halogen compounds Chemical class 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
239000000047 product Substances 0.000 description 3
DRMOCHGNKTXIBF-UHFFFAOYSA-N 2-(2-methoxyanilino)acetic acid Chemical compound COC1=CC=CC=C1NCC(O)=O DRMOCHGNKTXIBF-UHFFFAOYSA-N 0.000 description 2
241000700198 Cavia Species 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
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
239000004471 Glycine Substances 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
YTGJWQPHMWSCST-UHFFFAOYSA-N Tiopronin Chemical compound CC(S)C(=O)NCC(O)=O YTGJWQPHMWSCST-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
150000008064 anhydrides Chemical class 0.000 description 2
230000000903 blocking effect Effects 0.000 description 2
230000001886 ciliary effect Effects 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
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 2
230000003419 expectorant effect Effects 0.000 description 2
229960001867 guaiacol Drugs 0.000 description 2
210000004072 lung Anatomy 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 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
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
239000000126 substance 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
QIQITDHWZYEEPA-UHFFFAOYSA-N thiophene-2-carbonyl chloride Chemical compound ClC(=O)C1=CC=CS1 QIQITDHWZYEEPA-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
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 1
IBMQOXRRXKZDPO-UHFFFAOYSA-N 2-methyl-3-oxo-3-thiophen-2-ylpropanethioic s-acid Chemical compound SC(=O)C(C)C(=O)C1=CC=CS1 IBMQOXRRXKZDPO-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
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
125000003860 C1-C20 alkoxy group Chemical group 0.000 description 1
LAHIGVLOYVUJPD-UHFFFAOYSA-N COC1=CC=CC=C1CC(C(=O)OC(=O)CN)Cl Chemical compound COC1=CC=CC=C1CC(C(=O)OC(=O)CN)Cl LAHIGVLOYVUJPD-UHFFFAOYSA-N 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
108090000371 Esterases Proteins 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
241000283986 Lepus Species 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
206010036790 Productive cough Diseases 0.000 description 1
108010077895 Sarcosine Proteins 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 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
WREOTYWODABZMH-DTZQCDIJSA-N [[(2r,3s,4r,5r)-3,4-dihydroxy-5-[2-oxo-4-(2-phenylethoxyamino)pyrimidin-1-yl]oxolan-2-yl]methoxy-hydroxyphosphoryl] phosphono hydrogen phosphate Chemical compound O[C@@H]1[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)O[C@H]1N(C=C\1)C(=O)NC/1=N\OCCC1=CC=CC=C1 WREOTYWODABZMH-DTZQCDIJSA-N 0.000 description 1
230000002378 acidificating effect Effects 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
125000000217 alkyl group Chemical group 0.000 description 1
125000006295 amino methylene group Chemical group [H]N(*)C([H])([H])* 0.000 description 1
230000003110 anti-inflammatory effect Effects 0.000 description 1
229940124584 antitussives Drugs 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
239000002585 base Substances 0.000 description 1
230000037396 body weight Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
210000000621 bronchi Anatomy 0.000 description 1
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
229940125758 compound 15 Drugs 0.000 description 1
229940125782 compound 2 Drugs 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000013058 crude material Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 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
239000012895 dilution Substances 0.000 description 1
238000010790 dilution Methods 0.000 description 1
ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical compound C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
229940079593 drug Drugs 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
239000003480 eluent Substances 0.000 description 1
125000004185 ester group Chemical group 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 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
230000003779 hair growth Effects 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
238000010255 intramuscular injection Methods 0.000 description 1
239000007927 intramuscular injection Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
239000012046 mixed solvent 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
230000007935 neutral effect Effects 0.000 description 1
238000000655 nuclear magnetic resonance spectrum 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
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 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
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
230000000241 respiratory effect Effects 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical compound C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 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
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000007787 solid Substances 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
239000005720 sucrose Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
230000002110 toxicologic effect Effects 0.000 description 1
231100000027 toxicology Toxicity 0.000 description 1
210000005062 tracheal ring Anatomy 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
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

Landscapes

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)

NL8201820A 1981-05-11 1982-05-03 2-methoxyfenylesters van n-gesubstitueerde aminozuren, een werkwijze voor hun bereiding en farmaceutica die deze verbindingen bevatten. NL8201820A (nl)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
IT2162081		1981-05-11
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
IT4848581		1981-05-15
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

Publications (1)

Publication Number	Publication Date
NL8201820A true NL8201820A (nl)	1982-12-01

Family

ID=26327948

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL8201820A NL8201820A (nl)	1981-05-11	1982-05-03	2-methoxyfenylesters van n-gesubstitueerde aminozuren, een werkwijze voor hun bereiding en farmaceutica die deze verbindingen bevatten.

Country Status (17)

Country	Link
US (1)	US4405638A (de)
KR (1)	KR890000486B1 (de)
AR (1)	AR231722A1 (de)
AT (1)	ATA183182A (de)
CA (1)	CA1196924A (de)
CH (1)	CH655095A5 (de)
DE (1)	DE3216986A1 (de)
DK (1)	DK154210C (de)
ES (1)	ES512769A0 (de)
FR (1)	FR2505329B1 (de)
GB (1)	GB2100723B (de)
IE (1)	IE52884B1 (de)
KE (1)	KE3521A (de)
LU (1)	LU84142A1 (de)
NL (1)	NL8201820A (de)
NO (1)	NO160779C (de)
SE (1)	SE453391B (de)

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
US4762849A (en) *	1985-10-15	1988-08-09	Merrell Dow Pharmaceuticals Inc.	Cardiotonic alkanoylthiazolones
US4927939A (en) *	1985-10-15	1990-05-22	Merrell Dow Pharmaceuticals	Cardiotonic aroylthiazolones
US4623651A (en)	1985-10-15	1986-11-18	Merrell Dow Pharmaceuticals Inc.	Cardiotonic heterocyclocarbonyl- and acetyl-thiazolones

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 FR FR8207986A patent/FR2505329B1/fr not_active Expired
- 1982-05-07 AR AR289337A patent/AR231722A1/es active
- 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
- 1982-05-10 ES ES512769A patent/ES512769A0/es active Granted
- 1982-05-10 KR KR8202030A patent/KR890000486B1/ko not_active Expired
- 1982-05-11 DK DK210882A patent/DK154210C/da not_active IP Right Cessation
- 1982-05-11 LU LU84142A patent/LU84142A1/fr unknown
- 1982-05-11 SE SE8202962A patent/SE453391B/sv not_active IP Right Cessation
1985
- 1985-04-04 KE KE3521A patent/KE3521A/xx unknown

Also Published As

Publication number	Publication date
SE8202962L (sv)	1982-11-12
KR890000486B1 (ko)	1989-03-18
AR231722A1 (es)	1985-02-28
CA1196924A (en)	1985-11-19
SE8202962D0 (sv)	1982-05-11
FR2505329A1 (fr)	1982-11-12
US4405638A (en)	1983-09-20
KE3521A (en)	1985-05-03
LU84142A1 (fr)	1982-09-13
ATA183182A (de)	1990-05-15
IE820987L (en)	1982-11-11
GB2100723A (en)	1983-01-06
NO821545L (no)	1982-11-12
NO160779B (no)	1989-02-20
DE3216986A1 (de)	1982-11-25
ES8307717A1 (es)	1983-08-01
GB2100723B (en)	1985-01-09
CH655095A5 (it)	1986-03-27
IE52884B1 (en)	1988-03-30
DK210882A (da)	1982-11-12
FR2505329B1 (fr)	1986-04-25
DK154210C (da)	1989-03-13
SE453391B (sv)	1988-02-01
DK154210B (da)	1988-10-24
NO160779C (no)	1989-05-31
ES512769A0 (es)	1983-08-01
KR830010051A (ko)	1983-12-24

Legal Events

Date	Code	Title
1985-01-01	A85	Still pending on 85-01-01
1986-01-02	BA	A request for search or an international-type search has been filed
1986-01-02	BB	A search report has been drawn up
1986-06-02	BC	A request for examination has been filed
1991-01-02	BV	The patent application has lapsed

Publication	Publication Date	Title
SU820659A3 (ru)	1981-04-07	Способ получени производных 4-амино- 5-АлКилСульфОНилОАНизАМидОВ, иХ СОлЕй,ОКиСЕй, лЕВО- и пРАВОВРАщАющиХизОМЕРОВ /иХ ВАРиАНТы/
US20060160875A1 (en)	2006-07-20	Matrix metalloproteinase inhibitors
NL8004021A (nl)	1981-01-15	Bloeddruk-verlagende amideverbindingen.
FR2530626A1 (fr)	1984-01-27	Composes de carbostyryle
JPS6011917B2 (ja)	1985-03-28	新規なセファロスポリン化合物
DE69000364T2 (de)	1993-05-06	Von benzocyclischen oder benzoheterocyclischen saeuren abgeleitete sulfonamide, ihre herstellung und ihre anwendung in der heilkunde.
HU211680A9 (en)	1995-12-28	Pyrazolopyridine compounds which have useful pharmaceutical utility
US20080227858A1 (en)	2008-09-18	Inhibitors of matrix metalloproteinase
JPH04234844A (ja)	1992-08-24	新規化合物の３−アミノ−２−オキソアゼチジン誘導体及びそれらの製造法
KR100198183B1 (ko)	1999-06-15	퀴논기를 함유하는 티아졸리딘 화합물, 이의 제조방법 및 치료용도
US20060135785A1 (en)	2006-06-22	Alpha-phenyl acetanilide derivatives having an acat inhibiting activity and the therapeutic application thereof
DD282691A5 (de)	1990-09-19	Verfahren zur herstellung von cephalosporin
NL8201820A (nl)	1982-12-01	2-methoxyfenylesters van n-gesubstitueerde aminozuren, een werkwijze voor hun bereiding en farmaceutica die deze verbindingen bevatten.
KR20120007566A (ko)	2012-01-20	기질 금속단백분해효소 억제제
WO1992009574A2 (en)	1992-06-11	Poly-aminopyrrolecarboxamido derivatives, processes for their preparation and pharmaceutical compositions containing them
CS226020B2 (en)	1984-03-19	Method of preparing pyridine and pyrimidine derivatives
US4521538A (en)	1985-06-04	Ester of the 1-methyl-5-p-toluoylpyrrole-2-acetic acid having antiinflammatory, mucolytic and antitussive properties, process for its preparation and pharmaceutical compositions containing them
US7019009B2 (en)	2006-03-28	Acyl derivatives of 5-(2-(4-(1,2 benzisothiazole-3-yl)-1-piperazinyl)ethyl)-6-chloro-1,3-dihydro-2h-indol-2-one having neuroleptic activity
PT92890A (pt)	1990-07-31	Processo para a preparacao de derivados de cefalosporina e de composicoes farmaceuticas que os contem
BE893073A (nl)	1982-08-30	2-methoxyfenylesters van n-gesubstitueerde aminozuren, een werkwijze voor hun bereiding en farmaceutica die deze verbinding bevatten
CA1037467A (en)	1978-08-29	7-(.alpha.-(2-AMINOMETHYL-1-CYCLOHEXENYL AND 1,4-CYCLOHEXADIENYL)-ACETAMIDO)-3-HETEROCYCLICTHIOMETHYL-3-CEPHEM-4-CARBOXYLIC ACIDS AND DERIVATIVES THEREOF
KR840000520B1 (ko)	1984-04-17	N-(디에틸아미노에틸)-2-알콕시벤즈 아미드류의 제조방법
FR2581996A1 (fr)	1986-11-21	Nouveaux derives 6-substitues de 6h-dibenzo(b, d)thiopyranne utiles notamment immunomodulateurs et antiviraux et leur preparation
JPH06345722A (ja)	1994-12-20	チオアセタール誘導体
JPH09249628A (ja)	1997-09-22	フェノール誘導体