CZ288151B6 - Natural form of N-[4-[5-(cyclopentyloxycarbonyl)amino-1-methylindol-3-ylmethyl]-3-methoxybenzoyl]-2-methylbenzenesulfonamide, process of its preparation and pharmaceutical preparations in which it is comprised - Google Patents
Natural form of N-[4-[5-(cyclopentyloxycarbonyl)amino-1-methylindol-3-ylmethyl]-3-methoxybenzoyl]-2-methylbenzenesulfonamide, process of its preparation and pharmaceutical preparations in which it is comprised Download PDFInfo
- Publication number
- CZ288151B6 CZ288151B6 CS19913758A CS375891A CZ288151B6 CZ 288151 B6 CZ288151 B6 CZ 288151B6 CS 19913758 A CS19913758 A CS 19913758A CS 375891 A CS375891 A CS 375891A CZ 288151 B6 CZ288151 B6 CZ 288151B6
- Authority
- CZ
- Czechia
- Prior art keywords
- ylmethyl
- methoxybenzoyl
- cyclopentyloxycarbonyl
- methylbenzenesulfonamide
- amino
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 10
- YEEZWCHGZNKEEK-UHFFFAOYSA-N Zafirlukast Chemical compound COC1=CC(C(=O)NS(=O)(=O)C=2C(=CC=CC=2)C)=CC=C1CC(C1=C2)=CN(C)C1=CC=C2NC(=O)OC1CCCC1 YEEZWCHGZNKEEK-UHFFFAOYSA-N 0.000 title claims abstract description 8
- 238000002360 preparation method Methods 0.000 title abstract description 12
- 239000000825 pharmaceutical preparation Substances 0.000 title abstract 2
- 239000000843 powder Substances 0.000 claims abstract description 19
- 239000008188 pellet Substances 0.000 claims abstract description 15
- 238000002329 infrared spectrum Methods 0.000 claims abstract description 9
- 238000001228 spectrum Methods 0.000 claims abstract description 9
- 238000002441 X-ray diffraction Methods 0.000 claims abstract description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 27
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 14
- 239000000463 material Substances 0.000 claims description 12
- 239000002245 particle Substances 0.000 claims description 12
- 239000008194 pharmaceutical composition Substances 0.000 claims description 12
- 229940071648 metered dose inhaler Drugs 0.000 claims description 11
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 6
- 239000012159 carrier gas Substances 0.000 claims description 5
- -1 cyclopentyloxycarbonyl Chemical group 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- 150000002617 leukotrienes Chemical class 0.000 claims description 5
- 239000004338 Dichlorodifluoromethane Substances 0.000 claims description 4
- 235000019404 dichlorodifluoromethane Nutrition 0.000 claims description 4
- 238000001704 evaporation Methods 0.000 claims description 4
- 230000008020 evaporation Effects 0.000 claims description 4
- 239000007789 gas Substances 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 4
- DDMOUSALMHHKOS-UHFFFAOYSA-N 1,2-dichloro-1,1,2,2-tetrafluoroethane Chemical compound FC(F)(Cl)C(F)(F)Cl DDMOUSALMHHKOS-UHFFFAOYSA-N 0.000 claims description 3
- 229940087091 dichlorotetrafluoroethane Drugs 0.000 claims description 3
- 230000000694 effects Effects 0.000 claims description 3
- LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 claims description 2
- 229940042935 dichlorodifluoromethane Drugs 0.000 claims description 2
- 229940029284 trichlorofluoromethane Drugs 0.000 claims description 2
- 230000003042 antagnostic effect Effects 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 29
- 229940125904 compound 1 Drugs 0.000 description 19
- 239000000443 aerosol Substances 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 8
- 238000009472 formulation Methods 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000003860 storage Methods 0.000 description 6
- 229940112141 dry powder inhaler Drugs 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 238000000634 powder X-ray diffraction Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products 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 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 239000008101 lactose Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000005096 rolling process Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 206010014824 Endotoxic shock Diseases 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 239000005909 Kieselgur Substances 0.000 description 2
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 2
- 239000005642 Oleic acid Substances 0.000 description 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 206010040070 Septic Shock Diseases 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- PRXRUNOAOLTIEF-ADSICKODSA-N Sorbitan trioleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCC\C=C/CCCCCCCC)[C@H]1OC[C@H](O)[C@H]1OC(=O)CCCCCCC\C=C/CCCCCCCC PRXRUNOAOLTIEF-ADSICKODSA-N 0.000 description 2
- 239000004147 Sorbitan trioleate Substances 0.000 description 2
- 206010044541 Traumatic shock Diseases 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical class CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 2
- 208000006673 asthma Diseases 0.000 description 2
- 208000010668 atopic eczema Diseases 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- 238000005469 granulation Methods 0.000 description 2
- 230000003179 granulation Effects 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 210000004072 lung Anatomy 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 2
- 239000008108 microcrystalline cellulose Substances 0.000 description 2
- 229940016286 microcrystalline cellulose Drugs 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 235000019337 sorbitan trioleate Nutrition 0.000 description 2
- 229960000391 sorbitan trioleate Drugs 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- KAWBUBSCEUJHPU-KVVVOXFISA-N (Z)-octadec-9-enoic acid trichloro(fluoro)methane Chemical compound FC(Cl)(Cl)Cl.CCCCCCCC\C=C/CCCCCCCC(O)=O KAWBUBSCEUJHPU-KVVVOXFISA-N 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- YCMLQMDWSXFTIF-UHFFFAOYSA-N 2-methylbenzenesulfonimidic acid Chemical compound CC1=CC=CC=C1S(N)(=O)=O YCMLQMDWSXFTIF-UHFFFAOYSA-N 0.000 description 1
- CAFQYJIFRCXAAT-UHFFFAOYSA-N 3-[3-methoxy-4-[(1-methyl-5-nitroindol-3-yl)methyl]benzoyl]-2-methylbenzenesulfonamide Chemical compound C=1C=C(CC=2C3=CC(=CC=C3N(C)C=2)[N+]([O-])=O)C(OC)=CC=1C(=O)C1=CC=CC(S(N)(=O)=O)=C1C CAFQYJIFRCXAAT-UHFFFAOYSA-N 0.000 description 1
- 208000035285 Allergic Seasonal Rhinitis Diseases 0.000 description 1
- 229910001369 Brass Inorganic materials 0.000 description 1
- GUNSGVQHBXUMAF-UHFFFAOYSA-N CN(C)C1=NC=CC=C1.CN1C=C(C2=CC(=CC=C12)[N+](=O)[O-])CC1=C(C=C(C(=O)C=2C(=C(C=CC2)S(=O)(=O)N)C)C=C1)OC Chemical compound CN(C)C1=NC=CC=C1.CN1C=C(C2=CC(=CC=C12)[N+](=O)[O-])CC1=C(C=C(C(=O)C=2C(=C(C=CC2)S(=O)(=O)N)C)C=C1)OC GUNSGVQHBXUMAF-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 206010053567 Coagulopathies Diseases 0.000 description 1
- 206010012438 Dermatitis atopic Diseases 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 208000019693 Lung disease Diseases 0.000 description 1
- 201000004681 Psoriasis Diseases 0.000 description 1
- 206010039085 Rhinitis allergic Diseases 0.000 description 1
- 230000000172 allergic effect Effects 0.000 description 1
- 201000010105 allergic rhinitis Diseases 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 201000008937 atopic dermatitis Diseases 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000010951 brass Substances 0.000 description 1
- 206010006451 bronchitis Diseases 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 230000035602 clotting Effects 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- ZFQCRLNKHHXELH-UHFFFAOYSA-N cyclopentyl carbonochloridate Chemical compound ClC(=O)OC1CCCC1 ZFQCRLNKHHXELH-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 231100000284 endotoxic Toxicity 0.000 description 1
- 230000002346 endotoxic effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 208000027866 inflammatory disease Diseases 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- DMPXTRBUJIRVOO-UHFFFAOYSA-N methyl 3-methoxy-4-[(1-methyl-5-nitroindol-3-yl)methyl]benzoate Chemical compound COC1=CC(C(=O)OC)=CC=C1CC1=CN(C)C2=CC=C([N+]([O-])=O)C=C12 DMPXTRBUJIRVOO-UHFFFAOYSA-N 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical class CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
- 239000006199 nebulizer Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 229960002969 oleic acid Drugs 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000008506 pathogenesis Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000007873 sieving Methods 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000003506 spasmogen Substances 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 230000008728 vascular permeability Effects 0.000 description 1
- 230000002455 vasospastic effect Effects 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D209/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with an alkyl or cycloalkyl radical attached to the ring nitrogen atom
-
- 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
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Pulmonology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Immunology (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB909027018A GB9027018D0 (en) | 1990-12-12 | 1990-12-12 | Heterocyclic compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS375891A3 CS375891A3 (en) | 1992-06-17 |
| CZ288151B6 true CZ288151B6 (en) | 2001-05-16 |
Family
ID=10686919
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS19913758A CZ288151B6 (en) | 1990-12-12 | 1991-12-11 | Natural form of N-[4-[5-(cyclopentyloxycarbonyl)amino-1-methylindol-3-ylmethyl]-3-methoxybenzoyl]-2-methylbenzenesulfonamide, process of its preparation and pharmaceutical preparations in which it is comprised |
Country Status (28)
| Country | Link |
|---|---|
| US (1) | US5294636A (enExample) |
| EP (1) | EP0490649B1 (enExample) |
| JP (1) | JP2650807B2 (enExample) |
| KR (1) | KR100194479B1 (enExample) |
| CN (2) | CN1032469C (enExample) |
| AP (1) | AP286A (enExample) |
| AT (1) | ATE145199T1 (enExample) |
| AU (1) | AU656344B2 (enExample) |
| CA (1) | CA2056067C (enExample) |
| CZ (1) | CZ288151B6 (enExample) |
| DE (1) | DE69123123T2 (enExample) |
| DK (1) | DK0490649T3 (enExample) |
| ES (1) | ES2094797T3 (enExample) |
| FI (1) | FI101296B1 (enExample) |
| GB (2) | GB9027018D0 (enExample) |
| GR (1) | GR3021605T3 (enExample) |
| HK (1) | HK81497A (enExample) |
| HU (2) | HU213109B (enExample) |
| IE (1) | IE914316A1 (enExample) |
| IL (1) | IL100090A (enExample) |
| MX (1) | MX9102475A (enExample) |
| MY (1) | MY108629A (enExample) |
| NZ (1) | NZ240940A (enExample) |
| PH (1) | PH30041A (enExample) |
| RU (1) | RU2107682C1 (enExample) |
| SK (1) | SK279018B6 (enExample) |
| TW (1) | TW222264B (enExample) |
| ZA (1) | ZA919772B (enExample) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK0455596T3 (da) * | 1990-05-04 | 1994-11-28 | Ciba Geigy Ag | Substituerede indoler |
| IL100091A (en) * | 1990-12-12 | 1998-08-16 | Zeneca Ltd | Pharmaceutical compositions containing a physical form of n-[4-[5-(cyclopentyloxycarbonyl)amino-1-methyl indol-3-yl-methyl]-2-methylbenzenesulpho-namide and process for their preparation |
| GB9119001D0 (en) * | 1991-09-05 | 1991-10-23 | Ici Plc | Pharmaceutical agents |
| GR1001368B (el) * | 1992-10-08 | 1993-10-29 | Ici Plc | Φαρμακευτικοί φορείς. |
| DE4235133A1 (de) * | 1992-10-19 | 1994-04-21 | Bayer Ag | Kristallines (R)-(-)-2-Cycloheptyl-N-methylsulfonyl-[4-(2-chinolinyl-methoxy)-phenyl]-acetamid |
| JP3732508B2 (ja) * | 1993-10-01 | 2006-01-05 | アストラ・アクチエボラーグ | 粉末状薬剤の製造方法 |
| IS1736B (is) | 1993-10-01 | 1999-12-30 | Astra Ab | Aðferð og tæki sem stuðla að aukinni samloðun agna |
| GB9723985D0 (en) * | 1997-11-14 | 1998-01-14 | Zeneca Ltd | Pharmaceutical compositions |
| GB9726735D0 (en) * | 1997-12-18 | 1998-02-18 | Zeneca Ltd | Pharmaceutical compositions |
| GB9900339D0 (en) * | 1999-01-09 | 1999-02-24 | Zeneca Ltd | Chemical compounds |
| GB0003305D0 (en) * | 2000-02-15 | 2000-04-05 | Zeneca Ltd | Pyrimidine derivatives |
| IL139243A0 (en) * | 2000-10-24 | 2001-11-25 | Internat Specialty Products Is | Ethanolate of zafirlukast, process for manufacture and pharmaceutical compositions thereof |
| TWI353979B (en) * | 2002-04-10 | 2011-12-11 | Nippon Zoki Pharmaceutical Co | Novel crystal form of 5-hydroxy-1-methylhydantoin |
| US20090317476A1 (en) * | 2003-07-31 | 2009-12-24 | Robinson Cynthia B | Combination of dehydroepiandrosterone or dehydroepiandrosterone-sulfate with a leukotriene receptor antagonist for treatment of asthma or chronic obstructive pulmonary disease |
| US20050026882A1 (en) * | 2003-07-31 | 2005-02-03 | Robinson Cynthia B. | Combination of dehydroepiandrosterone or dehydroepiandrosterone-sulfate with a leukotriene receptor antagonist for treatment of asthma or chronic obstructive pulmonary disease |
| US20050113410A1 (en) * | 2003-11-03 | 2005-05-26 | Mark Tawa | Pharmaceutical salts of zafirlukast |
| JP2008531721A (ja) * | 2005-03-03 | 2008-08-14 | エラン・ファルマ・インターナショナル・リミテッド | 複素環式アミド誘導体のナノ粒子状組成物 |
| US20070197467A1 (en) * | 2006-02-06 | 2007-08-23 | Srinivasulu Rangineni | Zafirlukast compositions |
| US20090012146A1 (en) * | 2007-07-02 | 2009-01-08 | Giridhar Reddy Buggana | Solubility-enhanced pharmaceutical compositions comprising zafirlukast |
| US20090191183A1 (en) * | 2007-07-30 | 2009-07-30 | Auspex Pharmaceuticals, Inc. | Substituted indoles |
| TWI469965B (zh) * | 2008-12-22 | 2015-01-21 | Ono Pharmaceutical Co | 乙炔基吲哚化合物 |
| WO2014012954A1 (en) | 2012-07-18 | 2014-01-23 | Takeda Gmbh | Treatment of partly controlled or uncontrolled severe asthma |
| CN103396353B (zh) * | 2013-08-23 | 2015-05-20 | 海南通用三洋药业有限公司 | 一种扎鲁司特无定型态及其制备方法 |
| WO2015110394A1 (en) | 2014-01-22 | 2015-07-30 | Takeda Gmbh | Treatment of partly controlled or uncontrolled severe asthma with a pde4 inhibitor (and in combination with a leukotriene modifier) |
| PT109030B (pt) * | 2015-12-15 | 2019-09-25 | Hovione Farmaciência, S.A. | Preparação de partículas inaláveis de zafirlucaste |
| CA3052071A1 (en) | 2017-01-30 | 2018-08-02 | Western New England University | Thiol isomerases inhibitors and use thereof |
| JP2024521736A (ja) | 2021-05-19 | 2024-06-04 | クエルシス ファーマ エージー | 筋萎縮性側索硬化症の治療に使用するためのケルセチン含有組成物 |
| US20250275936A1 (en) | 2022-05-06 | 2025-09-04 | Quercis Pharma AG | Method for treating cancers and neurological diseases using quercetin-containing compositions |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4161516A (en) * | 1975-07-25 | 1979-07-17 | Fisons Limited | Composition for treating airway disease |
| GB8607294D0 (en) * | 1985-04-17 | 1986-04-30 | Ici America Inc | Heterocyclic amide derivatives |
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1990
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PD00 | Pending as of 2000-06-30 in czech republic | ||
| MM4A | Patent lapsed due to non-payment of fee |
Effective date: 20051211 |