SK279258B6 - (-)-1-(4'-amino-3'-kyanofenyl)-2-izopropylaminoeta - Google Patents
(-)-1-(4'-amino-3'-kyanofenyl)-2-izopropylaminoeta Download PDFInfo
- Publication number
- SK279258B6 SK279258B6 SK1292-91A SK129291A SK279258B6 SK 279258 B6 SK279258 B6 SK 279258B6 SK 129291 A SK129291 A SK 129291A SK 279258 B6 SK279258 B6 SK 279258B6
- Authority
- SK
- Slovakia
- Prior art keywords
- isopropylaminoethanol
- cyanophenyl
- amino
- dibenzoyl
- cimaterol
- Prior art date
Links
- BUXRLJCGHZZYNE-UHFFFAOYSA-N 2-amino-5-[1-hydroxy-2-(propan-2-ylamino)ethyl]benzonitrile Chemical class CC(C)NCC(O)C1=CC=C(N)C(C#N)=C1 BUXRLJCGHZZYNE-UHFFFAOYSA-N 0.000 title claims abstract description 37
- 150000003839 salts Chemical class 0.000 title claims abstract description 34
- 238000000034 method Methods 0.000 title claims abstract description 24
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 5
- 238000002360 preparation method Methods 0.000 title claims abstract description 4
- 239000000654 additive Chemical class 0.000 title abstract description 5
- 230000000996 additive effect Effects 0.000 title abstract description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 48
- 239000002253 acid Substances 0.000 claims abstract description 16
- YONLFQNRGZXBBF-KBPBESRZSA-N (2s,3s)-2,3-dibenzoyloxybutanedioic acid Chemical compound O([C@H](C(=O)O)[C@H](OC(=O)C=1C=CC=CC=1)C(O)=O)C(=O)C1=CC=CC=C1 YONLFQNRGZXBBF-KBPBESRZSA-N 0.000 claims abstract description 6
- 239000004480 active ingredient Substances 0.000 claims description 40
- 239000000203 mixture Substances 0.000 claims description 31
- 241001465754 Metazoa Species 0.000 claims description 20
- 150000001875 compounds Chemical class 0.000 claims description 19
- 238000004519 manufacturing process Methods 0.000 claims description 11
- YONLFQNRGZXBBF-ZIAGYGMSSA-N (2r,3r)-2,3-dibenzoyloxybutanedioic acid Chemical compound O([C@@H](C(=O)O)[C@@H](OC(=O)C=1C=CC=CC=1)C(O)=O)C(=O)C1=CC=CC=C1 YONLFQNRGZXBBF-ZIAGYGMSSA-N 0.000 claims description 7
- -1 (+) - O Chemical class 0.000 claims description 6
- 238000002425 crystallisation Methods 0.000 claims description 4
- 230000008025 crystallization Effects 0.000 claims description 4
- 230000001737 promoting effect Effects 0.000 claims description 4
- 230000003287 optical effect Effects 0.000 claims description 3
- 208000008589 Obesity Diseases 0.000 claims description 2
- 201000009961 allergic asthma Diseases 0.000 claims description 2
- 208000006673 asthma Diseases 0.000 claims description 2
- 206010006451 bronchitis Diseases 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 235000020824 obesity Nutrition 0.000 claims description 2
- 230000000414 obstructive effect Effects 0.000 claims description 2
- 206010061218 Inflammation Diseases 0.000 claims 1
- 208000002193 Pain Diseases 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 230000004054 inflammatory process Effects 0.000 claims 1
- 230000002685 pulmonary effect Effects 0.000 claims 1
- 229950010971 cimaterol Drugs 0.000 abstract description 38
- 239000000126 substance Substances 0.000 abstract description 7
- 238000000926 separation method Methods 0.000 abstract description 3
- 201000010099 disease Diseases 0.000 abstract 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 1
- 239000007952 growth promoter Substances 0.000 abstract 1
- 230000001148 spastic effect Effects 0.000 abstract 1
- 235000002639 sodium chloride Nutrition 0.000 description 23
- 239000004615 ingredient Substances 0.000 description 22
- FEWJPZIEWOKRBE-JCYAYHJZSA-M L-tartrate(1-) Chemical compound OC(=O)[C@H](O)[C@@H](O)C([O-])=O FEWJPZIEWOKRBE-JCYAYHJZSA-M 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 230000000694 effects Effects 0.000 description 11
- 238000002844 melting Methods 0.000 description 11
- 230000008018 melting Effects 0.000 description 11
- 239000003826 tablet Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 229920002261 Corn starch Polymers 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 235000010469 Glycine max Nutrition 0.000 description 6
- 244000068988 Glycine max Species 0.000 description 6
- 239000013543 active substance Substances 0.000 description 6
- 239000008120 corn starch Substances 0.000 description 6
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- 240000008042 Zea mays Species 0.000 description 5
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 5
- 239000008298 dragée Substances 0.000 description 5
- 239000003925 fat Substances 0.000 description 5
- 229910052500 inorganic mineral Inorganic materials 0.000 description 5
- 235000013372 meat Nutrition 0.000 description 5
- 235000010755 mineral Nutrition 0.000 description 5
- 239000011707 mineral Substances 0.000 description 5
- 239000000829 suppository Substances 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 235000013343 vitamin Nutrition 0.000 description 5
- 239000011782 vitamin Substances 0.000 description 5
- 229940088594 vitamin Drugs 0.000 description 5
- 229930003231 vitamin Natural products 0.000 description 5
- IVWWFWFVSWOTLP-YVZVNANGSA-N (3'as,4r,7'as)-2,2,2',2'-tetramethylspiro[1,3-dioxolane-4,6'-4,7a-dihydro-3ah-[1,3]dioxolo[4,5-c]pyran]-7'-one Chemical compound C([C@@H]1OC(O[C@@H]1C1=O)(C)C)O[C@]21COC(C)(C)O2 IVWWFWFVSWOTLP-YVZVNANGSA-N 0.000 description 4
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 4
- 241000283690 Bos taurus Species 0.000 description 4
- 241000283973 Oryctolagus cuniculus Species 0.000 description 4
- 241000282887 Suidae Species 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- 230000003454 betamimetic effect Effects 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- 235000013312 flour Nutrition 0.000 description 4
- 238000001990 intravenous administration Methods 0.000 description 4
- 235000013379 molasses Nutrition 0.000 description 4
- 238000003307 slaughter Methods 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 235000016068 Berberis vulgaris Nutrition 0.000 description 3
- 241000335053 Beta vulgaris Species 0.000 description 3
- 208000009079 Bronchial Spasm Diseases 0.000 description 3
- 235000007340 Hordeum vulgare Nutrition 0.000 description 3
- 240000005979 Hordeum vulgare Species 0.000 description 3
- 241000283903 Ovis aries Species 0.000 description 3
- 241000209140 Triticum Species 0.000 description 3
- 235000021307 Triticum Nutrition 0.000 description 3
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 125000002252 acyl group Chemical group 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- 210000004369 blood Anatomy 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
- 230000000052 comparative effect Effects 0.000 description 3
- 235000005822 corn Nutrition 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000002178 crystalline material Substances 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 235000021588 free fatty acids Nutrition 0.000 description 3
- 235000019359 magnesium stearate Nutrition 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 3
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 3
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 3
- 229920001592 potato starch Polymers 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000006188 syrup Substances 0.000 description 3
- 235000020357 syrup Nutrition 0.000 description 3
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 2
- 241000251468 Actinopterygii Species 0.000 description 2
- 241000272517 Anseriformes Species 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- 208000014181 Bronchial disease Diseases 0.000 description 2
- 206010006482 Bronchospasm Diseases 0.000 description 2
- 241000282472 Canis lupus familiaris Species 0.000 description 2
- 241000282326 Felis catus Species 0.000 description 2
- 241000287828 Gallus gallus Species 0.000 description 2
- GXCLVBGFBYZDAG-UHFFFAOYSA-N N-[2-(1H-indol-3-yl)ethyl]-N-methylprop-2-en-1-amine Chemical compound CN(CCC1=CNC2=C1C=CC=C2)CC=C GXCLVBGFBYZDAG-UHFFFAOYSA-N 0.000 description 2
- 241001494479 Pecora Species 0.000 description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 2
- 230000007059 acute toxicity Effects 0.000 description 2
- 231100000403 acute toxicity Toxicity 0.000 description 2
- 210000001789 adipocyte Anatomy 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- 239000003674 animal food additive Substances 0.000 description 2
- 229960000686 benzalkonium chloride Drugs 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 2
- 102000012740 beta Adrenergic Receptors Human genes 0.000 description 2
- 108010079452 beta Adrenergic Receptors Proteins 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 235000019688 fish Nutrition 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 239000007943 implant Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000012417 linear regression Methods 0.000 description 2
- 230000002366 lipolytic effect Effects 0.000 description 2
- 235000009973 maize Nutrition 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 244000144977 poultry Species 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000003380 propellant Substances 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 210000002027 skeletal muscle Anatomy 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 229960001367 tartaric acid Drugs 0.000 description 2
- 239000011975 tartaric acid Substances 0.000 description 2
- 235000002906 tartaric acid Nutrition 0.000 description 2
- 239000008215 water for injection Substances 0.000 description 2
- PZNPLUBHRSSFHT-RRHRGVEJSA-N 1-hexadecanoyl-2-octadecanoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCCCC(=O)O[C@@H](COP([O-])(=O)OCC[N+](C)(C)C)COC(=O)CCCCCCCCCCCCCCC PZNPLUBHRSSFHT-RRHRGVEJSA-N 0.000 description 1
- 241000972773 Aulopiformes Species 0.000 description 1
- 241000271566 Aves Species 0.000 description 1
- BJDFYLUYYXGVFW-HOTGVXAUSA-N C1(=C(C=CC=C1)OC([C@@H](O)[C@H](O)C(=O)OC1=C(C=CC=C1)C)=O)C Chemical compound C1(=C(C=CC=C1)OC([C@@H](O)[C@H](O)C(=O)OC1=C(C=CC=C1)C)=O)C BJDFYLUYYXGVFW-HOTGVXAUSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 241000283707 Capra Species 0.000 description 1
- 241000252229 Carassius auratus Species 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- 241000700112 Chinchilla Species 0.000 description 1
- 241000938605 Crocodylia Species 0.000 description 1
- 241000270722 Crocodylidae Species 0.000 description 1
- 235000019750 Crude protein Nutrition 0.000 description 1
- 241000252233 Cyprinus carpio Species 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 241000283086 Equidae Species 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 235000019687 Lamb Nutrition 0.000 description 1
- 241000283986 Lepus Species 0.000 description 1
- 235000019759 Maize starch Nutrition 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 240000003183 Manihot esculenta Species 0.000 description 1
- 235000016735 Manihot esculenta subsp esculenta Nutrition 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 241000772415 Neovison vison Species 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 241000286209 Phasianidae Species 0.000 description 1
- 241000287530 Psittaciformes Species 0.000 description 1
- 241000287231 Serinus Species 0.000 description 1
- 241000270295 Serpentes Species 0.000 description 1
- 235000019764 Soybean Meal Nutrition 0.000 description 1
- 206010043376 Tetanus Diseases 0.000 description 1
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 1
- 229960004373 acetylcholine Drugs 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 230000001773 anti-convulsant effect Effects 0.000 description 1
- 230000002921 anti-spasmodic effect Effects 0.000 description 1
- 235000013871 bee wax Nutrition 0.000 description 1
- 239000012166 beeswax Substances 0.000 description 1
- WURBFLDFSFBTLW-UHFFFAOYSA-N benzil Chemical group C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-UHFFFAOYSA-N 0.000 description 1
- 235000013361 beverage Nutrition 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 210000003678 bronchial smooth muscle cell Anatomy 0.000 description 1
- 230000001813 broncholytic effect Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 235000008504 concentrate Nutrition 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- 229910000397 disodium phosphate Inorganic materials 0.000 description 1
- 235000019800 disodium phosphate Nutrition 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000003651 drinking water Substances 0.000 description 1
- 235000020188 drinking water Nutrition 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000013401 experimental design Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 230000004968 inflammatory condition Effects 0.000 description 1
- 229940041682 inhalant solution Drugs 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- 244000144972 livestock Species 0.000 description 1
- 150000002689 maleic acids Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 210000000754 myometrium Anatomy 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 210000004879 pulmonary tissue Anatomy 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 235000019515 salmon Nutrition 0.000 description 1
- 210000002374 sebum Anatomy 0.000 description 1
- 210000002363 skeletal muscle cell Anatomy 0.000 description 1
- 210000002460 smooth muscle Anatomy 0.000 description 1
- 239000004455 soybean meal Substances 0.000 description 1
- 239000008347 soybean phospholipid Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 210000003699 striated muscle Anatomy 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000000153 supplemental effect Effects 0.000 description 1
- 239000002511 suppository base Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 235000013619 trace mineral Nutrition 0.000 description 1
- 239000011573 trace mineral Substances 0.000 description 1
- 230000002618 waking effect Effects 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 235000015099 wheat brans Nutrition 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/275—Nitriles; Isonitriles
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/111—Aromatic compounds
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K50/00—Feeding-stuffs specially adapted for particular animals
- A23K50/30—Feeding-stuffs specially adapted for particular animals for swines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/275—Nitriles; Isonitriles
- A61K31/277—Nitriles; Isonitriles having a ring, e.g. verapamil
-
- 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
-
- 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
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/02—Muscle relaxants, e.g. for tetanus or cramps
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/58—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton
- C07C255/59—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton the carbon skeleton being further substituted by singly-bound oxygen atoms
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Polymers & Plastics (AREA)
- Epidemiology (AREA)
- Food Science & Technology (AREA)
- Pulmonology (AREA)
- Zoology (AREA)
- Animal Husbandry (AREA)
- Pain & Pain Management (AREA)
- Birds (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Diabetes (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Reproductive Health (AREA)
- Child & Adolescent Psychology (AREA)
- Immunology (AREA)
- Rheumatology (AREA)
- Urology & Nephrology (AREA)
- Endocrinology (AREA)
- Neurosurgery (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4014252A DE4014252A1 (de) | 1990-05-04 | 1990-05-04 | Enantiomerentrennung von cimaterol, (-)-cimaterol und dessen verwendung als arzneimittel oder als leistungsfoerderer |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK279258B6 true SK279258B6 (sk) | 1998-08-05 |
Family
ID=6405664
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK1292-91A SK279258B6 (sk) | 1990-05-04 | 1991-05-03 | (-)-1-(4'-amino-3'-kyanofenyl)-2-izopropylaminoeta |
Country Status (27)
| Country | Link |
|---|---|
| US (4) | US5248695A (cs) |
| EP (2) | EP0589488B1 (cs) |
| JP (1) | JP2944777B2 (cs) |
| KR (1) | KR0183024B1 (cs) |
| AR (1) | AR247728A1 (cs) |
| AT (2) | ATE158277T1 (cs) |
| AU (1) | AU645313B2 (cs) |
| BG (1) | BG60743B1 (cs) |
| CA (1) | CA2041818C (cs) |
| CZ (1) | CZ286389B6 (cs) |
| DE (3) | DE4014252A1 (cs) |
| DK (2) | DK0455155T3 (cs) |
| ES (2) | ES2075255T3 (cs) |
| FI (1) | FI109600B (cs) |
| GR (2) | GR3017064T3 (cs) |
| HU (1) | HU214335B (cs) |
| ID (1) | ID966B (cs) |
| IE (2) | IE80651B1 (cs) |
| IL (1) | IL98030A (cs) |
| NO (1) | NO174803B (cs) |
| NZ (1) | NZ238032A (cs) |
| PT (1) | PT97544B (cs) |
| RU (1) | RU2002737C1 (cs) |
| SG (1) | SG45439A1 (cs) |
| SK (1) | SK279258B6 (cs) |
| TW (1) | TW197415B (cs) |
| ZA (1) | ZA913337B (cs) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4014252A1 (de) * | 1990-05-04 | 1991-11-07 | Boehringer Ingelheim Vetmed | Enantiomerentrennung von cimaterol, (-)-cimaterol und dessen verwendung als arzneimittel oder als leistungsfoerderer |
| GB9107196D0 (en) * | 1991-04-05 | 1991-05-22 | Sandoz Ag | Improvements in or relating to organic compounds |
| GB2289842B (en) * | 1991-04-05 | 1996-01-31 | Sepracor Inc | Improved use of ß2 bronchodilator drugs |
| AU2247997A (en) * | 1996-01-29 | 1997-08-20 | Savor, Evelyn P. | Method of treating undesired uterine contractions using optically pure R-or RR-isomers of adrenergic beta-2 agonists |
| EP1787529A3 (en) * | 1997-04-30 | 2009-11-18 | Courage Corporation Pty Ltd. | Composition and methods using an eutomer |
| NZ500250A (en) | 1997-04-30 | 2001-03-30 | Bridge Pharma Inc | Adrenergic beta-2 agonist eutomers, feed compositions and use for increasing muscle and decreasing fat |
| ZA994264B (en) | 1998-07-01 | 2000-01-25 | Warner Lambert Co | Stereoisomers with high affinity for adrenergic receptors. |
| RU2201420C2 (ru) * | 1998-11-03 | 2003-03-27 | Новартис Аг | Нитрилы дипептидов |
| US7232837B2 (en) | 1999-06-29 | 2007-06-19 | Mcneil-Ppc, Inc. | Stereoisomers with high affinity for adrenergic receptors |
| JP2003533448A (ja) * | 2000-04-27 | 2003-11-11 | ベーリンガー インゲルハイム ファルマ ゲゼルシャフト ミット ベシュレンクテル ハフツング ウント コンパニー コマンディトゲゼルシャフト | 新規持続性ベータ擬似剤、その製造方法及びその医薬としての使用 |
| US20030162459A1 (en) * | 2002-02-27 | 2003-08-28 | Osbon Robert Lindsay | Method for producing a nonwoven fabric with enhanced characteristics |
| US20040235922A1 (en) * | 2003-05-15 | 2004-11-25 | Baile Clifton A. | Compositions and methods for inducing adipose tissue cell death |
| ATE380027T1 (de) * | 2003-09-09 | 2007-12-15 | Fumapharm Ag | Verwendung von fumarsäure-derivaten zur behandlung von herzinsuffizienz und asthma |
| SG124283A1 (en) * | 2004-03-24 | 2006-08-30 | Trusted Hub Ltd | Document signature method & system |
| JP5021621B2 (ja) * | 2005-04-13 | 2012-09-12 | アスション ファーマ エー／エス | 皮膚の結合組織病を治療するためのβ−２アドレナリン受容体作動薬 |
| WO2006128180A2 (en) * | 2005-05-27 | 2006-11-30 | Children's Medical Center Corporation | Methods for the treatment of disease |
| US20090305225A1 (en) * | 2005-06-13 | 2009-12-10 | Galbraith Richard A | Inhibition of Creatine Uptake to Promote Weight Loss |
| RU2408014C2 (ru) * | 2009-03-10 | 2010-12-27 | Государственное образовательное учреждение высшего профессионального образования "Российский государственный медицинский университет им. Н.И. Пирогова Министерства здравоохранения и социального развития Российской Федерации" | Способ прогнозирования преждевременных родов инфекционного генеза |
| BR112015011897B1 (pt) | 2012-12-03 | 2021-11-03 | Pfizer Inc | Compostos moduladores seletivos do receptor de andrógeno e seu uso |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL136601C (cs) * | 1967-06-15 | |||
| US4119710A (en) * | 1972-12-18 | 1978-10-10 | Boehringer Ingelheim Gmbh | Bronchospasmolytic 1-(p-amino-phenyl)-2-amino-ethanols-(1) and salts |
| US4407819A (en) * | 1980-08-25 | 1983-10-04 | American Cyanamid Company | Phenylethanolamine derivatives and acid addition salts thereof for the depression of fat deposition in warm blooded animals |
| US4814350A (en) * | 1986-09-10 | 1989-03-21 | American Cyanamid Company | Method of treating diabetes with 5-[1-hydroxy-2-(isopropylamino)ethyl]anthranilonitrile |
| US4792546A (en) * | 1986-12-05 | 1988-12-20 | American Cyanamid Company | Method for increasing weight gains and reducing deposition of fat in animals |
| DE4014252A1 (de) * | 1990-05-04 | 1991-11-07 | Boehringer Ingelheim Vetmed | Enantiomerentrennung von cimaterol, (-)-cimaterol und dessen verwendung als arzneimittel oder als leistungsfoerderer |
-
1990
- 1990-05-04 DE DE4014252A patent/DE4014252A1/de not_active Withdrawn
-
1991
- 1991-04-26 AT AT93117935T patent/ATE158277T1/de not_active IP Right Cessation
- 1991-04-26 ES ES91106774T patent/ES2075255T3/es not_active Expired - Lifetime
- 1991-04-26 DE DE59108853T patent/DE59108853D1/de not_active Expired - Fee Related
- 1991-04-26 DE DE59105957T patent/DE59105957D1/de not_active Expired - Fee Related
- 1991-04-26 DK DK91106774.2T patent/DK0455155T3/da active
- 1991-04-26 SG SG1996008586A patent/SG45439A1/en unknown
- 1991-04-26 EP EP93117935A patent/EP0589488B1/de not_active Expired - Lifetime
- 1991-04-26 EP EP91106774A patent/EP0455155B1/de not_active Expired - Lifetime
- 1991-04-26 AT AT91106774T patent/ATE124932T1/de not_active IP Right Cessation
- 1991-04-26 ES ES93117935T patent/ES2109412T3/es not_active Expired - Lifetime
- 1991-04-26 DK DK93117935.2T patent/DK0589488T3/da active
- 1991-04-29 AU AU76111/91A patent/AU645313B2/en not_active Ceased
- 1991-04-30 US US07/693,760 patent/US5248695A/en not_active Expired - Fee Related
- 1991-05-01 TW TW080103440A patent/TW197415B/zh active
- 1991-05-02 IL IL9803091A patent/IL98030A/en not_active IP Right Cessation
- 1991-05-02 PT PT97544A patent/PT97544B/pt not_active IP Right Cessation
- 1991-05-02 JP JP3100832A patent/JP2944777B2/ja not_active Expired - Fee Related
- 1991-05-02 KR KR1019910007085A patent/KR0183024B1/ko not_active Expired - Fee Related
- 1991-05-03 NZ NZ238032A patent/NZ238032A/en unknown
- 1991-05-03 CZ CS19911292A patent/CZ286389B6/cs not_active IP Right Cessation
- 1991-05-03 ZA ZA913337A patent/ZA913337B/xx unknown
- 1991-05-03 SK SK1292-91A patent/SK279258B6/sk unknown
- 1991-05-03 NO NO911746A patent/NO174803B/no not_active IP Right Cessation
- 1991-05-03 IE IE950792A patent/IE80651B1/en not_active IP Right Cessation
- 1991-05-03 IE IE150791A patent/IE69017B1/en not_active IP Right Cessation
- 1991-05-03 AR AR91319603A patent/AR247728A1/es active
- 1991-05-03 BG BG94342A patent/BG60743B1/bg unknown
- 1991-05-03 CA CA002041818A patent/CA2041818C/en not_active Expired - Fee Related
- 1991-05-03 HU HU911502A patent/HU214335B/hu not_active IP Right Cessation
- 1991-05-03 FI FI912151A patent/FI109600B/fi not_active IP Right Cessation
- 1991-12-18 RU SU915010409A patent/RU2002737C1/ru not_active IP Right Cessation
-
1992
- 1992-01-31 ID IDP198592A patent/ID966B/id unknown
-
1993
- 1993-06-23 US US08/081,996 patent/US5292753A/en not_active Expired - Fee Related
- 1993-12-14 US US08/166,584 patent/US5395957A/en not_active Expired - Lifetime
-
1994
- 1994-11-29 US US08/346,105 patent/US5648386A/en not_active Expired - Fee Related
-
1995
- 1995-08-09 GR GR950402190T patent/GR3017064T3/el unknown
-
1997
- 1997-12-02 GR GR970403196T patent/GR3025547T3/el unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| SK279258B6 (sk) | (-)-1-(4'-amino-3'-kyanofenyl)-2-izopropylaminoeta | |
| EP0026298B1 (en) | Method for promoting growth and reducing fat in animals using phenylethanolamine derivatives | |
| EP0117647B1 (en) | Improvements in or relating to phenethanolamines | |
| US4287201A (en) | Anovulatory method and chicken feed compositions | |
| JPS61227557A (ja) | ５‐フルオロベンゾニトリル誘導体類およびそれらの製薬学的に許容可能な酸付加塩類 | |
| US5393774A (en) | Phenylethanolamines, pharmaceutical compositions containing these compounds and process for preparing them | |
| KR20020059730A (ko) | 가축 생산성 개선을 위한 아릴옥시 프로판올아민 | |
| US4734437A (en) | Growth promotion | |
| CS236477B2 (cs) | Prostředek vhodný pro povzbuzení rychlosti růstu a pro snížení ukládání tuku u teplokrevných zvířat |