ES2350330T3 - Tratamiento de la hiperactividad del músculo liso con (r)-oxibutinina y (r)-desetiloxibutinina. - Google Patents
Tratamiento de la hiperactividad del músculo liso con (r)-oxibutinina y (r)-desetiloxibutinina. Download PDFInfo
- Publication number
- ES2350330T3 ES2350330T3 ES00941235T ES00941235T ES2350330T3 ES 2350330 T3 ES2350330 T3 ES 2350330T3 ES 00941235 T ES00941235 T ES 00941235T ES 00941235 T ES00941235 T ES 00941235T ES 2350330 T3 ES2350330 T3 ES 2350330T3
- Authority
- ES
- Spain
- Prior art keywords
- butynyl
- cyclohexylphenylglycolate
- pharmaceutically acceptable
- salt
- solvate
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired - Lifetime
Links
- 208000013403 hyperactivity Diseases 0.000 title abstract description 10
- 210000003205 muscle Anatomy 0.000 title description 3
- XIQVNETUBQGFHX-UHFFFAOYSA-N Ditropan Chemical compound C=1C=CC=CC=1C(O)(C(=O)OCC#CCN(CC)CC)C1CCCCC1 XIQVNETUBQGFHX-UHFFFAOYSA-N 0.000 claims abstract description 34
- 229960005434 oxybutynin Drugs 0.000 claims abstract description 31
- 230000000694 effects Effects 0.000 claims abstract description 9
- 206010046543 Urinary incontinence Diseases 0.000 claims abstract description 8
- 208000002551 irritable bowel syndrome Diseases 0.000 claims abstract description 4
- 150000003839 salts Chemical class 0.000 claims description 30
- 239000012453 solvate Substances 0.000 claims description 22
- BFYKETJZYOOFEP-UHFFFAOYSA-N 2-[2-but-1-ynyl-4-(diethylamino)cyclohexyl]-2-hydroxy-2-phenylacetic acid Chemical compound CCC#CC1CC(N(CC)CC)CCC1C(O)(C(O)=O)C1=CC=CC=C1 BFYKETJZYOOFEP-UHFFFAOYSA-N 0.000 claims description 11
- KQMFBMUCMLKXTL-UHFFFAOYSA-N CCC#CC1CC(CCC1C(C2=CC=CC=C2)(C(=O)O)O)NCC Chemical compound CCC#CC1CC(CCC1C(C2=CC=CC=C2)(C(=O)O)O)NCC KQMFBMUCMLKXTL-UHFFFAOYSA-N 0.000 claims description 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 7
- 230000002526 effect on cardiovascular system Effects 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- 230000002411 adverse Effects 0.000 claims description 5
- 230000003001 depressive effect Effects 0.000 claims description 3
- 230000002035 prolonged effect Effects 0.000 claims description 3
- 230000004899 motility Effects 0.000 claims 4
- 210000001035 gastrointestinal tract Anatomy 0.000 claims 2
- 230000000994 depressogenic effect Effects 0.000 claims 1
- SNIBJKHIKIIGPR-UHFFFAOYSA-N N-desethyloxybutynin Chemical compound C=1C=CC=CC=1C(O)(C(=O)OCC#CCNCC)C1CCCCC1 SNIBJKHIKIIGPR-UHFFFAOYSA-N 0.000 abstract description 16
- 210000002460 smooth muscle Anatomy 0.000 abstract description 10
- 238000000034 method Methods 0.000 abstract description 9
- 210000003932 urinary bladder Anatomy 0.000 abstract description 8
- 230000001078 anti-cholinergic effect Effects 0.000 abstract description 3
- 230000002496 gastric effect Effects 0.000 abstract description 3
- 230000002048 spasmolytic effect Effects 0.000 abstract description 3
- 230000001404 mediated effect Effects 0.000 abstract 1
- 230000003389 potentiating effect Effects 0.000 abstract 1
- 208000024891 symptom Diseases 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 23
- 239000003826 tablet Substances 0.000 description 13
- 239000000203 mixture Substances 0.000 description 11
- 239000003814 drug Substances 0.000 description 10
- 229940079593 drug Drugs 0.000 description 9
- 230000004044 response Effects 0.000 description 8
- 210000001519 tissue Anatomy 0.000 description 7
- 239000004480 active ingredient Substances 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- YTRNSQPXEDGWMR-UHFFFAOYSA-N alpha-Cyclohexylmandelic acid Chemical compound C=1C=CC=CC=1C(O)(C(=O)O)C1CCCCC1 YTRNSQPXEDGWMR-UHFFFAOYSA-N 0.000 description 5
- 239000004615 ingredient Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 230000001022 anti-muscarinic effect Effects 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 230000008602 contraction Effects 0.000 description 4
- 239000002552 dosage form Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- -1 Diethylamino-2-butynyl-cyclohexylphenylglycolate Chemical compound 0.000 description 3
- 102000014415 Muscarinic acetylcholine receptor Human genes 0.000 description 3
- 108050003473 Muscarinic acetylcholine receptor Proteins 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000005557 antagonist Substances 0.000 description 3
- 230000000968 intestinal effect Effects 0.000 description 3
- 239000003446 ligand Substances 0.000 description 3
- 239000002207 metabolite Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- XIQVNETUBQGFHX-QFIPXVFZSA-N (R)-oxybutynin Chemical compound C1([C@](O)(C(=O)OCC#CCN(CC)CC)C=2C=CC=CC=2)CCCCC1 XIQVNETUBQGFHX-QFIPXVFZSA-N 0.000 description 2
- YUQHJYNNXUESDG-UHFFFAOYSA-N 2-[3-[2-but-1-ynyl-4-(diethylamino)cyclohexyl]-2-hydroxyphenyl]acetic acid Chemical compound CCC#CC1CC(N(CC)CC)CCC1C1=CC=CC(CC(O)=O)=C1O YUQHJYNNXUESDG-UHFFFAOYSA-N 0.000 description 2
- NARXAACCVUBQLR-UHFFFAOYSA-N 4-chloro-n,n-diethylbut-2-yn-1-amine Chemical compound CCN(CC)CC#CCCl NARXAACCVUBQLR-UHFFFAOYSA-N 0.000 description 2
- 241000700199 Cavia porcellus Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 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 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 2
- 239000008116 calcium stearate Substances 0.000 description 2
- 235000013539 calcium stearate Nutrition 0.000 description 2
- AIXAANGOTKPUOY-UHFFFAOYSA-N carbachol Chemical compound [Cl-].C[N+](C)(C)CCOC(N)=O AIXAANGOTKPUOY-UHFFFAOYSA-N 0.000 description 2
- 238000011260 co-administration Methods 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 208000035475 disorder Diseases 0.000 description 2
- 238000002565 electrocardiography Methods 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 210000000232 gallbladder Anatomy 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 210000003734 kidney Anatomy 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 239000000463 material Substances 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
- 238000000465 moulding Methods 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 239000006187 pill Substances 0.000 description 2
- 102000005962 receptors Human genes 0.000 description 2
- 108020003175 receptors Proteins 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- ZKNJEOBYOLUGKJ-ALCCZGGFSA-N (z)-2-propylpent-2-enoic acid Chemical group CCC\C(C(O)=O)=C\CC ZKNJEOBYOLUGKJ-ALCCZGGFSA-N 0.000 description 1
- UPHOPMSGKZNELG-UHFFFAOYSA-N 2-hydroxynaphthalene-1-carboxylic acid Chemical class C1=CC=C2C(C(=O)O)=C(O)C=CC2=C1 UPHOPMSGKZNELG-UHFFFAOYSA-N 0.000 description 1
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
- KZVUMBNNPRQXQQ-UHFFFAOYSA-N CCC#CC1CC(CCC1C2=CC=CC=C2OC(=O)CO)NCC Chemical compound CCC#CC1CC(CCC1C2=CC=CC=C2OC(=O)CO)NCC KZVUMBNNPRQXQQ-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- 108010009685 Cholinergic Receptors Proteins 0.000 description 1
- 208000017667 Chronic Disease Diseases 0.000 description 1
- 102000013975 Delayed Rectifier Potassium Channels Human genes 0.000 description 1
- 108010050556 Delayed Rectifier Potassium Channels Proteins 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-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
- 206010021639 Incontinence Diseases 0.000 description 1
- 208000000913 Kidney Calculi Diseases 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 208000006550 Mydriasis Diseases 0.000 description 1
- 206010029148 Nephrolithiasis Diseases 0.000 description 1
- 102000019315 Nicotinic acetylcholine receptors Human genes 0.000 description 1
- 108050006807 Nicotinic acetylcholine receptors Proteins 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 208000001871 Tachycardia Diseases 0.000 description 1
- GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 description 1
- 208000018452 Torsade de pointes Diseases 0.000 description 1
- 208000002363 Torsades de Pointes Diseases 0.000 description 1
- 208000005946 Xerostomia Diseases 0.000 description 1
- 102000034337 acetylcholine receptors Human genes 0.000 description 1
- 230000036982 action potential Effects 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 239000000556 agonist Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- 230000002921 anti-spasmodic effect Effects 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 229960004754 astemizole Drugs 0.000 description 1
- GXDALQBWZGODGZ-UHFFFAOYSA-N astemizole Chemical compound C1=CC(OC)=CC=C1CCN1CCC(NC=2N(C3=CC=CC=C3N=2)CC=2C=CC(F)=CC=2)CC1 GXDALQBWZGODGZ-UHFFFAOYSA-N 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 210000000941 bile Anatomy 0.000 description 1
- 210000000013 bile duct Anatomy 0.000 description 1
- 230000027455 binding Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 235000011148 calcium chloride Nutrition 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 235000010980 cellulose Nutrition 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 210000001072 colon Anatomy 0.000 description 1
- 208000030499 combat disease Diseases 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 239000007891 compressed tablet Substances 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000013270 controlled release Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- WZHCOOQXZCIUNC-UHFFFAOYSA-N cyclandelate Chemical compound C1C(C)(C)CC(C)CC1OC(=O)C(O)C1=CC=CC=C1 WZHCOOQXZCIUNC-UHFFFAOYSA-N 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000001934 delay Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 229940099170 ditropan Drugs 0.000 description 1
- 206010013781 dry mouth Diseases 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- XIQVNETUBQGFHX-JOCHJYFZSA-N esoxybutynin Chemical compound C1([C@@](O)(C(=O)OCC#CCN(CC)CC)C=2C=CC=CC=2)CCCCC1 XIQVNETUBQGFHX-JOCHJYFZSA-N 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-N ethanesulfonic acid Chemical class CCS(O)(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-N 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 239000003979 granulating agent Substances 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 238000011597 hartley guinea pig Methods 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 210000004731 jugular vein Anatomy 0.000 description 1
- 230000003907 kidney function Effects 0.000 description 1
- 238000012417 linear regression Methods 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
- 230000027939 micturition Effects 0.000 description 1
- 239000007932 molded tablet Substances 0.000 description 1
- 235000019799 monosodium phosphate Nutrition 0.000 description 1
- 210000000715 neuromuscular junction Anatomy 0.000 description 1
- 230000009871 nonspecific binding Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 229960002016 oxybutynin chloride Drugs 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 239000002287 radioligand Substances 0.000 description 1
- 230000033764 rhythmic process Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 239000007909 solid dosage form Substances 0.000 description 1
- 230000009870 specific binding Effects 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000012066 statistical methodology Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000006794 tachycardia Effects 0.000 description 1
- 229960000351 terfenadine Drugs 0.000 description 1
- 229960005383 terodiline Drugs 0.000 description 1
- UISARWKNNNHPGI-UHFFFAOYSA-N terodiline Chemical compound C=1C=CC=CC=1C(CC(C)NC(C)(C)C)C1=CC=CC=C1 UISARWKNNNHPGI-UHFFFAOYSA-N 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- 210000003437 trachea Anatomy 0.000 description 1
- 208000003663 ventricular fibrillation Diseases 0.000 description 1
- 206010047302 ventricular tachycardia Diseases 0.000 description 1
- 230000035899 viability Effects 0.000 description 1
- 230000002747 voluntary effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/216—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acids having aromatic rings, e.g. benactizyne, clofibrate
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/06—Anti-spasmodics, e.g. drugs for colics, esophagic dyskinesia
-
- 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
- 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
- A61P13/02—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
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Urology & Nephrology (AREA)
- Virology (AREA)
- Pulmonology (AREA)
- Molecular Biology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Immunology (AREA)
- Emergency Medicine (AREA)
- Epidemiology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/US2000/015515 WO2001093683A1 (en) | 2000-06-07 | 2000-06-07 | Treating smooth muscle hyperactivity with (r)-oxybutynin and (r)- desethyloxybutynin |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2350330T3 true ES2350330T3 (es) | 2011-01-21 |
Family
ID=21741461
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES00941235T Expired - Lifetime ES2350330T3 (es) | 2000-06-07 | 2000-06-07 | Tratamiento de la hiperactividad del músculo liso con (r)-oxibutinina y (r)-desetiloxibutinina. |
Country Status (9)
| Country | Link |
|---|---|
| EP (1) | EP1286591B1 (https=) |
| JP (1) | JP5684964B2 (https=) |
| CN (3) | CN1454054A (https=) |
| AT (1) | ATE483459T1 (https=) |
| AU (2) | AU2000255966B2 (https=) |
| CA (1) | CA2378754A1 (https=) |
| DE (1) | DE60045082D1 (https=) |
| ES (1) | ES2350330T3 (https=) |
| WO (1) | WO2001093683A1 (https=) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005516992A (ja) * | 2001-12-21 | 2005-06-09 | ブリッジ ファーマ、インコーポレイテッド | オキシブチニンの非心律動異常惹起性代謝物 |
| EP1424079A1 (en) * | 2002-11-27 | 2004-06-02 | Boehringer Ingelheim International GmbH | Combination of a beta-3-receptor agonist and of a reuptake inhibitor of serotonin and/or norepinephrine |
| ATE361101T1 (de) * | 2004-08-24 | 2007-05-15 | Nutricia Nv | Nahrungszusammensetzung die unverdauliche oligosaccharide enthält |
| US8920392B2 (en) | 2009-05-05 | 2014-12-30 | Watson Laboratories, Inc. | Method for treating overactive bladders and a device for storage and administration of topical oxybutynin compositions |
| KR20190060879A (ko) | 2011-03-02 | 2019-06-03 | 제롬 쉔타그 | 단독으로 또는 c형 간염 바이러스 감염과 결합되는 간 지방증의 치료를 위한 조성물, 방법 및 진단 |
| US10117881B2 (en) | 2011-06-03 | 2018-11-06 | Signpath Pharma, Inc. | Protective effect of DMPC, DMPG, DMPC/DMPG, LYSOPG and LYSOPC against drugs that cause channelopathies |
| US12004868B2 (en) | 2011-06-03 | 2024-06-11 | Signpath Pharma Inc. | Liposomal mitigation of drug-induced inhibition of the cardiac IKr channel |
| US10349884B2 (en) | 2011-06-03 | 2019-07-16 | Sighpath Pharma Inc. | Liposomal mitigation of drug-induced inhibition of the cardiac ikr channel |
| WO2012167212A2 (en) | 2011-06-03 | 2012-12-06 | Signpath Pharma Inc. | Liposomal mitigation of drug-induced long qt syndrome and potassium delayed-rectifier current |
| US10238602B2 (en) | 2011-06-03 | 2019-03-26 | Signpath Pharma, Inc. | Protective effect of DMPC, DMPG, DMPC/DMPG, LysoPG and LysoPC against drugs that cause channelopathies |
| US10449193B2 (en) | 2011-06-03 | 2019-10-22 | Signpath Pharma Inc. | Protective effect of DMPC, DMPG, DMPC/DMPG, lysoPG and lysoPC against drugs that cause channelopathies |
| US20160151321A1 (en) | 2012-11-13 | 2016-06-02 | Dinesh C. Patel | Methods for the treatment of sialorrhea |
| US20140135392A1 (en) * | 2012-11-13 | 2014-05-15 | NeuRx Pharmaceuticals LLC | Methods for the treatment of sialorrhea |
| CN103169660B (zh) * | 2013-04-15 | 2015-04-08 | 石正国 | 一种制备高包封率的利巴韦林脂质体口服乳 |
| JP6895252B2 (ja) * | 2013-12-18 | 2021-06-30 | サインパス ファルマ, インク.Signpath Pharma, Inc. | 心筋ｉｋｒチャネルの薬剤誘発性阻害のリポソームによる軽減 |
| JP2017516813A (ja) | 2014-06-03 | 2017-06-22 | サインパス ファルマ, インク.Signpath Pharma, Inc. | チャネル病を引き起こす薬物に対するｄｍｐｃ、ｄｍｐｇ、ｄｍｐｃ／ｄｍｐｇ、ｅｇｐｇ、ｌｙｓｏｐｇ及びｌｙｓｏｐｃの防御効果 |
| KR102638618B1 (ko) | 2016-04-27 | 2024-02-21 | 사인패스 파마 인코포레이티드 | 약물 유발된 방실 차단의 방지 |
| CA3177654A1 (en) | 2020-05-05 | 2021-11-11 | Dennis MOLNAR | Polymorphic forms of (r)-oxybutynin hydrochloride |
| TW202207952A (zh) * | 2020-07-03 | 2022-03-01 | 愛爾蘭商普候克斯根有限公司 | 病毒感染 |
| CN117396460A (zh) * | 2021-05-04 | 2024-01-12 | 爱普宁公司(特拉华) | (r)-奥昔布宁d-苹果酸盐的固体形式 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4008269A (en) * | 1970-05-05 | 1977-02-15 | William H. Rorer, Inc. | Phenylacetic acids |
| IT1231237B (it) * | 1987-09-21 | 1991-11-26 | Angeli Inst Spa | Derivati eterociclici |
| US5677346A (en) * | 1995-01-31 | 1997-10-14 | Sepracor, Inc. | Treating urinary incontinence using (S)-desethyloxybutynin |
| US5973182A (en) * | 1998-10-22 | 1999-10-26 | Sepracor Inc. | Carbonate Intermediates useful in the preparation of optically active cyclohexylphenylglycolate esters |
-
2000
- 2000-06-07 CA CA002378754A patent/CA2378754A1/en not_active Abandoned
- 2000-06-07 WO PCT/US2000/015515 patent/WO2001093683A1/en not_active Ceased
- 2000-06-07 DE DE60045082T patent/DE60045082D1/de not_active Expired - Lifetime
- 2000-06-07 ES ES00941235T patent/ES2350330T3/es not_active Expired - Lifetime
- 2000-06-07 AT AT00941235T patent/ATE483459T1/de not_active IP Right Cessation
- 2000-06-07 AU AU2000255966A patent/AU2000255966B2/en not_active Expired
- 2000-06-07 CN CN00819623A patent/CN1454054A/zh active Pending
- 2000-06-07 JP JP2002501260A patent/JP5684964B2/ja not_active Expired - Fee Related
- 2000-06-07 EP EP00941235A patent/EP1286591B1/en not_active Expired - Lifetime
- 2000-06-07 AU AU5596600A patent/AU5596600A/xx active Pending
- 2000-06-07 CN CNA2007101418683A patent/CN101108176A/zh active Pending
-
2003
- 2003-05-16 CN CN03131438A patent/CN1451388A/zh active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| ATE483459T1 (de) | 2010-10-15 |
| CA2378754A1 (en) | 2001-12-13 |
| JP2003535110A (ja) | 2003-11-25 |
| AU5596600A (en) | 2001-12-17 |
| DE60045082D1 (de) | 2010-11-18 |
| CN101108176A (zh) | 2008-01-23 |
| AU2000255966A1 (en) | 2002-03-07 |
| EP1286591A1 (en) | 2003-03-05 |
| EP1286591B1 (en) | 2010-10-06 |
| WO2001093683A1 (en) | 2001-12-13 |
| AU2000255966B2 (en) | 2005-03-24 |
| EP1286591A4 (en) | 2007-04-04 |
| CN1451388A (zh) | 2003-10-29 |
| JP5684964B2 (ja) | 2015-03-18 |
| CN1454054A (zh) | 2003-11-05 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| ES2350330T3 (es) | Tratamiento de la hiperactividad del músculo liso con (r)-oxibutinina y (r)-desetiloxibutinina. | |
| CA2257121C (en) | Methods and compositions for treating urinary incontinence using optically pure (s)-oxybutynin | |
| US6310103B1 (en) | S(−)-tolterodine in the treatment of urinary and gastrointestinal disorders | |
| ES2237110T3 (es) | Uso de (+)-norcisaprida opticamente pura para tratar el sindrome del intestino irritable. | |
| Watabiki et al. | Amelioration of neuropathic pain by novel transient receptor potential vanilloid 1 antagonist AS1928370 in rats without hyperthermic effect | |
| US6123961A (en) | Treating urinary incontinence with (R)-desethyloxybutynin and (R)-oxybutynin | |
| PT806948E (pt) | Tratamento de incontinencia urinaria utilizando (s)-oxibutinina e (s)-desetiloxibutinina | |
| TW200808696A (en) | Alpha-aminoamide derivatives useful in the treatment of cognitive disorders | |
| JP2010514696A (ja) | 心血管症状の低減 | |
| UA78679C2 (en) | Agent for treating myocardial diseases associated with hypertrophy and pharmaceutical compositions | |
| EP3057589B1 (en) | (s)-pirlindole or its pharmaceutically acceptable salts for use in medicine | |
| RU2128650C1 (ru) | (S)-α-ФЕНИЛ-2-ПИРИДИНЭТАНАМИН И ЕГО СОЛЬ С НЕОРГАНИЧЕСКИМИ КИСЛОТАМИ, СПОСОБ ИХ ПОЛУЧЕНИЯ, ЛЕКАРСТВЕННЫЙ ПРЕПАРАТ НА ИХ ОСНОВЕ И СПОСОБ ЛЕЧЕНИЯ СУДОРОГ | |
| ES2237117T3 (es) | Uso de (-)norcisaprida opticamente pura en el tratamiento del sindrome del intestino irritable. | |
| JP2000513722A (ja) | 平滑筋鎮痙剤、それらを含有する組成物およびその使用方法 | |
| US20160151347A1 (en) | Pharmaceutical compounds | |
| US20030027856A1 (en) | Tolterodine metabolites | |
| JP2012176958A (ja) | （ｒ）−オキシブチニンおよび（ｒ）−デスエチルオキシブチニンによる平滑筋機能亢進の処置 | |
| RU2806869C2 (ru) | Применение мавоглуранта при снижении употребления алкоголя или при предупреждении рецидива употребления алкоголя | |
| KR100476550B1 (ko) | (s)-옥시부티닌과(s)-데스에틸옥시부티닌을이용한요실금치료 | |
| WO1998001125A2 (en) | Dextrorotatory isomers of oxybutynin and desethyloxybutynin in the treatment of gastrointestinal hyperactivity | |
| Zwieten | of Hypertension | |
| EP1455776A1 (en) | A non-arrhythmogenic metabolite of oxybutynin | |
| MXPA97005820A (en) | The use of (s) -oxibutinin and (s) -desetiloxibutinin in the preparation of compositions for the treatment of urinary incontinence, the compositions obtained and the procedure for preparing desetiloxibitin |