EA017483B1 - Стабильная кристаллическая соль 1-азабицикло[2.2.2]окт-3-илового сложного эфира (r)-3-фторфенил-3,4,5-трифторбензилкарбаминовой кислоты - Google Patents
Стабильная кристаллическая соль 1-азабицикло[2.2.2]окт-3-илового сложного эфира (r)-3-фторфенил-3,4,5-трифторбензилкарбаминовой кислоты Download PDFInfo
- Publication number
- EA017483B1 EA017483B1 EA201070651A EA201070651A EA017483B1 EA 017483 B1 EA017483 B1 EA 017483B1 EA 201070651 A EA201070651 A EA 201070651A EA 201070651 A EA201070651 A EA 201070651A EA 017483 B1 EA017483 B1 EA 017483B1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- compound
- salt
- disease
- tartrate
- crystalline
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 title claims abstract description 37
- UXZDMXYRRQJIBJ-IBGZPJMESA-N [(3r)-1-azabicyclo[2.2.2]octan-3-yl] n-(3-fluorophenyl)-n-[(3,4,5-trifluorophenyl)methyl]carbamate Chemical compound FC1=CC=CC(N(CC=2C=C(F)C(F)=C(F)C=2)C(=O)O[C@@H]2C3CCN(CC3)C2)=C1 UXZDMXYRRQJIBJ-IBGZPJMESA-N 0.000 title abstract 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 23
- 201000010099 disease Diseases 0.000 claims abstract description 12
- 239000003814 drug Substances 0.000 claims abstract description 11
- 206010046543 Urinary incontinence Diseases 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 72
- -1 1-azabicyclo [2.2.2] oct-3-yl Chemical group 0.000 claims description 21
- 239000002253 acid Substances 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 12
- 239000011975 tartaric acid Substances 0.000 claims description 11
- 239000008194 pharmaceutical composition Substances 0.000 claims description 10
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 9
- 230000001575 pathological effect Effects 0.000 claims description 7
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 5
- 206010020853 Hypertonic bladder Diseases 0.000 claims description 4
- 208000009722 Overactive Urinary Bladder Diseases 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 208000020629 overactive bladder Diseases 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 29
- 239000002904 solvent Substances 0.000 description 21
- 229940095064 tartrate Drugs 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 239000006260 foam Substances 0.000 description 17
- 239000007787 solid Substances 0.000 description 15
- 239000010410 layer Substances 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- 239000003921 oil Substances 0.000 description 12
- 235000019198 oils Nutrition 0.000 description 12
- 239000008186 active pharmaceutical agent Substances 0.000 description 11
- 229920000642 polymer Polymers 0.000 description 9
- 239000000843 powder Substances 0.000 description 8
- 239000003826 tablet Substances 0.000 description 8
- 239000000725 suspension Substances 0.000 description 7
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 239000002775 capsule Substances 0.000 description 6
- 239000003086 colorant Substances 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 239000003755 preservative agent Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 229940079593 drug Drugs 0.000 description 5
- 235000003599 food sweetener Nutrition 0.000 description 5
- 239000012458 free base Substances 0.000 description 5
- 239000008187 granular material Substances 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 239000002304 perfume Substances 0.000 description 5
- 239000003765 sweetening agent Substances 0.000 description 5
- 239000000080 wetting agent Substances 0.000 description 5
- 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 4
- 239000002250 absorbent Substances 0.000 description 4
- 230000002745 absorbent Effects 0.000 description 4
- 239000003463 adsorbent Substances 0.000 description 4
- 239000011230 binding agent Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000000113 differential scanning calorimetry Methods 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 239000007884 disintegrant Substances 0.000 description 4
- 239000003623 enhancer Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000000314 lubricant Substances 0.000 description 4
- 239000004014 plasticizer Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 235000002906 tartaric acid Nutrition 0.000 description 4
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 3
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 238000005079 FT-Raman Methods 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 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
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 239000002346 layers by function Substances 0.000 description 3
- 239000007937 lozenge Substances 0.000 description 3
- 230000014759 maintenance of location Effects 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- 210000004379 membrane Anatomy 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 210000000214 mouth Anatomy 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 230000005855 radiation Effects 0.000 description 3
- 238000001179 sorption measurement Methods 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- NLAVHUUABUFSIG-UHFFFAOYSA-N 3,4,5-trifluorobenzaldehyde Chemical compound FC1=CC(C=O)=CC(F)=C1F NLAVHUUABUFSIG-UHFFFAOYSA-N 0.000 description 2
- QZVQQUVWFIZUBQ-UHFFFAOYSA-N 3-fluoroaniline Chemical compound NC1=CC=CC(F)=C1 QZVQQUVWFIZUBQ-UHFFFAOYSA-N 0.000 description 2
- 235000019489 Almond oil Nutrition 0.000 description 2
- 244000144725 Amygdalus communis Species 0.000 description 2
- 235000011437 Amygdalus communis Nutrition 0.000 description 2
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 238000001237 Raman spectrum Methods 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 235000020224 almond Nutrition 0.000 description 2
- 239000008168 almond oil Substances 0.000 description 2
- 239000000227 bioadhesive Substances 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 2
- 239000007957 coemulsifier Substances 0.000 description 2
- 239000000356 contaminant Substances 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 238000011067 equilibration Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 230000014509 gene expression Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000003906 humectant Substances 0.000 description 2
- 150000002466 imines Chemical class 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 150000002632 lipids Chemical class 0.000 description 2
- CETVQRFGPOGIQJ-UHFFFAOYSA-N lithium;hexane Chemical compound [Li+].CCCCC[CH2-] CETVQRFGPOGIQJ-UHFFFAOYSA-N 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000004530 micro-emulsion Substances 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 238000000646 scanning calorimetry Methods 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 239000008137 solubility enhancer Substances 0.000 description 2
- WSWCOQWTEOXDQX-MQQKCMAXSA-N sorbic acid group Chemical group C(\C=C\C=C\C)(=O)O WSWCOQWTEOXDQX-MQQKCMAXSA-N 0.000 description 2
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical compound C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- PMVSDNDAUGGCCE-TYYBGVCCSA-L Ferrous fumarate Chemical compound [Fe+2].[O-]C(=O)\C=C\C([O-])=O PMVSDNDAUGGCCE-TYYBGVCCSA-L 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 235000001018 Hibiscus sabdariffa Nutrition 0.000 description 1
- 235000019501 Lemon oil Nutrition 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 235000019502 Orange oil Nutrition 0.000 description 1
- 235000005291 Rumex acetosa Nutrition 0.000 description 1
- 240000007001 Rumex acetosella Species 0.000 description 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
- 208000025609 Urogenital disease Diseases 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000001055 chewing effect Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 230000005595 deprotonation Effects 0.000 description 1
- 238000010537 deprotonation reaction Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000007908 dry granulation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000003974 emollient agent Substances 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000007902 hard capsule Substances 0.000 description 1
- 238000000589 high-performance liquid chromatography-mass spectrometry Methods 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 229940011051 isopropyl acetate Drugs 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- 239000010501 lemon oil Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000027939 micturition Effects 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000008177 pharmaceutical agent Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 239000003223 protective agent Substances 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 235000003513 sheep sorrel Nutrition 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 150000003509 tertiary alcohols Chemical class 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 238000005550 wet granulation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
- C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
-
- 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
-
- 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
- A61P13/10—Drugs for disorders of the urinary system of the bladder
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/12—Antidiuretics, e.g. drugs for diabetes insipidus
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Diabetes (AREA)
- Urology & Nephrology (AREA)
- Hematology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP07384038A EP2065385A1 (en) | 2007-11-28 | 2007-11-28 | Stable crystalline salt of (R)-3-fluorophenyl-3,4,5-trifluorobenzylcarbamic acid 1-azabiciyclo [2.2.2]oct-3-yl ester |
| PCT/EP2008/010012 WO2009068253A2 (en) | 2007-11-28 | 2008-11-26 | Stable crystalline salt of (r)-3-fluorophenyl-3,4,5-trifluorobenzylcarbamic acid 1-azabicyclo [2.2.2]oct-yl ester |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EA201070651A1 EA201070651A1 (ru) | 2010-12-30 |
| EA017483B1 true EA017483B1 (ru) | 2012-12-28 |
Family
ID=39401152
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EA201070651A EA017483B1 (ru) | 2007-11-28 | 2008-11-26 | Стабильная кристаллическая соль 1-азабицикло[2.2.2]окт-3-илового сложного эфира (r)-3-фторфенил-3,4,5-трифторбензилкарбаминовой кислоты |
Country Status (18)
| Country | Link |
|---|---|
| US (2) | US8492402B2 (enExample) |
| EP (2) | EP2065385A1 (enExample) |
| JP (1) | JP5336509B2 (enExample) |
| KR (1) | KR101557832B1 (enExample) |
| CN (1) | CN101925600B (enExample) |
| AU (1) | AU2008329181B2 (enExample) |
| BR (1) | BRPI0819607A2 (enExample) |
| CA (1) | CA2706565C (enExample) |
| DK (1) | DK2220082T3 (enExample) |
| EA (1) | EA017483B1 (enExample) |
| ES (1) | ES2498819T3 (enExample) |
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| MX (1) | MX2010005850A (enExample) |
| NZ (1) | NZ585833A (enExample) |
| PL (1) | PL2220082T3 (enExample) |
| UA (1) | UA102083C2 (enExample) |
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Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2002228015B2 (en) | 2000-12-22 | 2007-08-23 | Almirall, S.A. | Quinuclidine carbamate derivatives and their use as M3 antagonists |
| JP5745283B2 (ja) † | 2010-02-12 | 2015-07-08 | ファイザー・インク | ８−フルオロ−２−｛４−［（メチルアミノ）メチル］フェニル｝−１，３，４，５−テトラヒドロ−６Ｈ−アゼピノ［５，４，３−ｃｄ］インドール−６−オンの塩および多形体 |
| KR101978364B1 (ko) | 2017-06-15 | 2019-05-14 | 크리스탈지노믹스(주) | 알킬카바모일 나프탈렌일옥시 옥테노일 하이드록시아마이드 또는 그 유도체의 약학적으로 허용 가능한 염 및 그 제조방법 |
| KR102678356B1 (ko) * | 2018-10-29 | 2024-06-26 | 씨지인바이츠 주식회사 | 알킬카바모일 나프탈렌일옥시 옥테노일 하이드록시아마이드 인산염, 타르타르산염 또는 이들의 조합을 포함하는 약제학적 조성물 및 그 제조방법 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998054166A1 (en) * | 1997-05-30 | 1998-12-03 | Astra Aktiebolag | A new salt |
| EP1300407A1 (en) * | 2000-06-27 | 2003-04-09 | Laboratorios S.A.L.V.A.T., S.A. | Carbamates derived from arylalkylamines |
| WO2003053966A2 (en) * | 2001-12-20 | 2003-07-03 | Laboratorios S.A.L.V.A.T., S.A. | 1-alkyl-1-azoniabicyclo [2.2.2] octane carbamate derivatives and their use as muscarinic receptor antagonists |
| WO2004000840A2 (en) * | 2002-06-21 | 2003-12-31 | Almirall Prodesfarma Ag | Quinuclidine derivatives and pharmaceutical compositions containing the same |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2002228015B2 (en) * | 2000-12-22 | 2007-08-23 | Almirall, S.A. | Quinuclidine carbamate derivatives and their use as M3 antagonists |
| ES2246170B1 (es) * | 2004-07-29 | 2007-04-01 | Almirall Prodesfarma, S.A. | Nuevo procedimiento para preparar derivados de carbamato de quinuclidinio. |
-
2007
- 2007-11-28 EP EP07384038A patent/EP2065385A1/en not_active Withdrawn
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2008
- 2008-11-26 WO PCT/EP2008/010012 patent/WO2009068253A2/en not_active Ceased
- 2008-11-26 EA EA201070651A patent/EA017483B1/ru not_active IP Right Cessation
- 2008-11-26 DK DK08854867.2T patent/DK2220082T3/da active
- 2008-11-26 PL PL08854867T patent/PL2220082T3/pl unknown
- 2008-11-26 MX MX2010005850A patent/MX2010005850A/es active IP Right Grant
- 2008-11-26 CA CA2706565A patent/CA2706565C/en not_active Expired - Fee Related
- 2008-11-26 ES ES08854867.2T patent/ES2498819T3/es active Active
- 2008-11-26 UA UAA201007997A patent/UA102083C2/uk unknown
- 2008-11-26 NZ NZ585833A patent/NZ585833A/en not_active IP Right Cessation
- 2008-11-26 EP EP08854867.2A patent/EP2220082B1/en not_active Not-in-force
- 2008-11-26 CN CN2008801254506A patent/CN101925600B/zh not_active Expired - Fee Related
- 2008-11-26 US US12/744,493 patent/US8492402B2/en not_active Expired - Fee Related
- 2008-11-26 AU AU2008329181A patent/AU2008329181B2/en not_active Ceased
- 2008-11-26 BR BRPI0819607A patent/BRPI0819607A2/pt not_active IP Right Cessation
- 2008-11-26 JP JP2010535281A patent/JP5336509B2/ja not_active Expired - Fee Related
- 2008-11-28 KR KR1020107013939A patent/KR101557832B1/ko not_active Expired - Fee Related
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2010
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- 2010-05-27 IL IL206032A patent/IL206032A/en not_active IP Right Cessation
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2013
- 2013-02-08 US US13/763,063 patent/US8871787B2/en not_active Expired - Fee Related
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998054166A1 (en) * | 1997-05-30 | 1998-12-03 | Astra Aktiebolag | A new salt |
| EP1300407A1 (en) * | 2000-06-27 | 2003-04-09 | Laboratorios S.A.L.V.A.T., S.A. | Carbamates derived from arylalkylamines |
| WO2003053966A2 (en) * | 2001-12-20 | 2003-07-03 | Laboratorios S.A.L.V.A.T., S.A. | 1-alkyl-1-azoniabicyclo [2.2.2] octane carbamate derivatives and their use as muscarinic receptor antagonists |
| WO2004000840A2 (en) * | 2002-06-21 | 2003-12-31 | Almirall Prodesfarma Ag | Quinuclidine derivatives and pharmaceutical compositions containing the same |
Non-Patent Citations (1)
| Title |
|---|
| LIAN-FENG HUANG AND WEI-QIN TONG: "Impact of solid state properties on developability assessment of drug candidates" AVANCED DRUG DELIVERY REVIEWS, vol. 56, 2004, - 2004 pages 321-334, XP002481481 page 323, column 2, lines 25-29 - page 328, paragraph 5 * |
Also Published As
| Publication number | Publication date |
|---|---|
| EP2220082B1 (en) | 2014-06-25 |
| MX2010005850A (es) | 2010-09-03 |
| ES2498819T3 (es) | 2014-09-25 |
| KR101557832B1 (ko) | 2015-10-06 |
| DK2220082T3 (da) | 2014-10-06 |
| NZ585833A (en) | 2011-05-27 |
| JP2011504890A (ja) | 2011-02-17 |
| EP2220082A2 (en) | 2010-08-25 |
| HK1144192A1 (en) | 2011-02-02 |
| EA201070651A1 (ru) | 2010-12-30 |
| AU2008329181A1 (en) | 2009-06-04 |
| US20110207769A1 (en) | 2011-08-25 |
| WO2009068253A2 (en) | 2009-06-04 |
| US8871787B2 (en) | 2014-10-28 |
| CA2706565C (en) | 2015-04-28 |
| PL2220082T3 (pl) | 2014-12-31 |
| CN101925600A (zh) | 2010-12-22 |
| CA2706565A1 (en) | 2009-06-04 |
| KR20100103532A (ko) | 2010-09-27 |
| AU2008329181B2 (en) | 2012-03-29 |
| BRPI0819607A2 (pt) | 2015-10-13 |
| WO2009068253A3 (en) | 2009-08-13 |
| JP5336509B2 (ja) | 2013-11-06 |
| UA102083C2 (uk) | 2013-06-10 |
| EP2065385A1 (en) | 2009-06-03 |
| IL206032A (en) | 2014-07-31 |
| US20140051721A1 (en) | 2014-02-20 |
| ZA201003718B (en) | 2011-08-31 |
| IL206032A0 (en) | 2010-11-30 |
| CN101925600B (zh) | 2013-01-09 |
| US8492402B2 (en) | 2013-07-23 |
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