TW200800175A

TW200800175A - New beta-agonists, methods for the preparation thereof and their use as pharmaceutical compositions

New beta-agonists, methods for the preparation thereof and their use as pharmaceutical compositions Download PDF

Info

Publication number: TW200800175A
Authority: TW; Taiwan
Prior art keywords: phenyl; butyl; methyl; group; ethylamino
Prior art date: 2005-10-28

Application number

TW095139865A

Other languages

English (en)

Chinese (zh)

Inventor

Thomas Trieselmann

Bradford S Hamilton

Matthew R Netherton

Rainer Walter

Marco Santagostino

Original Assignee

Boehringer Ingelheim Int

Priority date

2005-10-28

Filing date

2006-10-27

Publication date

2008-01-01

2006-10-27 Application filed by Boehringer Ingelheim Int filed Critical Boehringer Ingelheim Int

2008-01-01 Publication of TW200800175A publication Critical patent/TW200800175A/zh

Links

239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 15
238000000034 method Methods 0.000 title claims abstract description 11
238000002360 preparation method Methods 0.000 title claims description 11
229940125388 beta agonist Drugs 0.000 title abstract 2
150000001875 compounds Chemical class 0.000 claims abstract description 98
239000000203 mixture Substances 0.000 claims abstract description 72
150000003839 salts Chemical class 0.000 claims abstract description 37
239000000651 prodrug Substances 0.000 claims abstract description 11
229940002612 prodrug Drugs 0.000 claims abstract description 11
239000012453 solvate Substances 0.000 claims abstract description 11
150000004677 hydrates Chemical class 0.000 claims abstract description 8
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 189
-1 bis-(c^-alkyl)-amino Chemical group 0.000 claims description 115
125000000217 alkyl group Chemical group 0.000 claims description 75
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 39
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 31
229910052731 fluorine Inorganic materials 0.000 claims description 30
OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 30
UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 29
239000011737 fluorine Substances 0.000 claims description 29
239000002253 acid Substances 0.000 claims description 28
239000000460 chlorine Substances 0.000 claims description 28
125000004432 carbon atom Chemical group C* 0.000 claims description 27
229910052801 chlorine Inorganic materials 0.000 claims description 27
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 23
239000000126 substance Substances 0.000 claims description 19
125000001424 substituent group Chemical group 0.000 claims description 19
238000006243 chemical reaction Methods 0.000 claims description 18
239000003795 chemical substances by application Substances 0.000 claims description 16
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 16
239000013543 active substance Substances 0.000 claims description 14
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
235000019253 formic acid Nutrition 0.000 claims description 12
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 11
125000001246 bromo group Chemical group Br* 0.000 claims description 11
150000001412 amines Chemical group 0.000 claims description 10
125000003277 amino group Chemical group 0.000 claims description 10
239000005711 Benzoic acid Substances 0.000 claims description 9
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 9
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 9
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 9
239000007789 gas Substances 0.000 claims description 9
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 9
HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 8
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
238000011282 treatment Methods 0.000 claims description 8
125000003545 alkoxy group Chemical group 0.000 claims description 7
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 7
GYSCBCSGKXNZRH-UHFFFAOYSA-N 1-benzothiophene-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=CC2=C1 GYSCBCSGKXNZRH-UHFFFAOYSA-N 0.000 claims description 6
125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 6
125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 6
239000000546 pharmaceutical excipient Substances 0.000 claims description 6
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 5
230000000694 effects Effects 0.000 claims description 5
239000003112 inhibitor Substances 0.000 claims description 5
238000000926 separation method Methods 0.000 claims description 5
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
235000010233 benzoic acid Nutrition 0.000 claims description 4
150000002148 esters Chemical class 0.000 claims description 4
230000000638 stimulation Effects 0.000 claims description 4
125000004900 1,1-dimethylpropylamino group Chemical group CC(CC)(C)N* 0.000 claims description 3
125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
COYPLDIXZODDDL-UHFFFAOYSA-N 3h-benzimidazole-5-carboxylic acid Chemical compound OC(=O)C1=CC=C2N=CNC2=C1 COYPLDIXZODDDL-UHFFFAOYSA-N 0.000 claims description 3
239000005632 Capric acid (CAS 334-48-5) Substances 0.000 claims description 3
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 3
108091027076 Spiegelmer Proteins 0.000 claims description 3
125000004429 atom Chemical group 0.000 claims description 3
239000000969 carrier Substances 0.000 claims description 3
GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 claims description 3
239000000796 flavoring agent Substances 0.000 claims description 3
210000004185 liver Anatomy 0.000 claims description 3
125000004076 pyridyl group Chemical group 0.000 claims description 3
229940122502 Cholesterol absorption inhibitor Drugs 0.000 claims description 2
101710204865 Tyrosine-protein phosphatase 1 Proteins 0.000 claims description 2
230000001800 adrenalinergic effect Effects 0.000 claims description 2
125000006242 amine protecting group Chemical group 0.000 claims description 2
239000003472 antidiabetic agent Substances 0.000 claims description 2
239000003524 antilipemic agent Substances 0.000 claims description 2
239000012965 benzophenone Substances 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
210000003296 saliva Anatomy 0.000 claims description 2
125000001544 thienyl group Chemical group 0.000 claims description 2
150000003573 thiols Chemical class 0.000 claims description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims 2
LLAPDLPYIYKTGQ-UHFFFAOYSA-N 1-aminoethyl Chemical group C[CH]N LLAPDLPYIYKTGQ-UHFFFAOYSA-N 0.000 claims 1
LMECSJDYYXMVPG-UHFFFAOYSA-N 2-morpholin-4-ylethyl decanoate Chemical compound CCCCCCCCCC(=O)OCCN1CCOCC1 LMECSJDYYXMVPG-UHFFFAOYSA-N 0.000 claims 1
235000014787 Vitis vinifera Nutrition 0.000 claims 1
240000006365 Vitis vinifera Species 0.000 claims 1
125000004171 alkoxy aryl group Chemical group 0.000 claims 1
229940127003 anti-diabetic drug Drugs 0.000 claims 1
230000003579 anti-obesity Effects 0.000 claims 1
125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims 1
125000003395 phenylethylamino group Chemical group [H]N(*)C([H])([H])C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
150000007524 organic acids Chemical class 0.000 abstract description 5
150000007522 mineralic acids Chemical class 0.000 abstract description 4
235000005985 organic acids Nutrition 0.000 abstract 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 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 147
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 107
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 105
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 75
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 69
235000019439 ethyl acetate Nutrition 0.000 description 69
239000011541 reaction mixture Substances 0.000 description 65
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 64
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 52
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 49
239000000243 solution Substances 0.000 description 41
239000012071 phase Substances 0.000 description 34
229910021529 ammonia Inorganic materials 0.000 description 30
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 26
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 24
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 24
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
235000019000 fluorine Nutrition 0.000 description 24
239000012074 organic phase Substances 0.000 description 23
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
238000001704 evaporation Methods 0.000 description 22
230000008020 evaporation Effects 0.000 description 22
239000003208 petroleum Substances 0.000 description 21
238000003818 flash chromatography Methods 0.000 description 20
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 18
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
229920006395 saturated elastomer Polymers 0.000 description 18
239000002585 base Substances 0.000 description 17
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 16
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 16
230000002441 reversible effect Effects 0.000 description 15
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 14
239000001257 hydrogen Substances 0.000 description 14
229910052739 hydrogen Inorganic materials 0.000 description 14
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
238000003756 stirring Methods 0.000 description 14
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 13
239000007787 solid Substances 0.000 description 13
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 13
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 12
238000000746 purification Methods 0.000 description 12
229910052938 sodium sulfate Inorganic materials 0.000 description 12
235000011152 sodium sulphate Nutrition 0.000 description 12
239000007864 aqueous solution Substances 0.000 description 11
UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 11
239000002904 solvent Substances 0.000 description 11
229960000583 acetic acid Drugs 0.000 description 10
239000005457 ice water Substances 0.000 description 10
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
125000003118 aryl group Chemical group 0.000 description 9
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 9
239000000052 vinegar Substances 0.000 description 9
235000021419 vinegar Nutrition 0.000 description 9
239000008346 aqueous phase Substances 0.000 description 8
201000010099 disease Diseases 0.000 description 8
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
235000011187 glycerol Nutrition 0.000 description 8
238000004128 high performance liquid chromatography Methods 0.000 description 8
229910052943 magnesium sulfate Inorganic materials 0.000 description 8
235000019341 magnesium sulphate Nutrition 0.000 description 8
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 8
239000011780 sodium chloride Substances 0.000 description 8
KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 7
229920002261 Corn starch Polymers 0.000 description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 7
239000008120 corn starch Substances 0.000 description 7
125000001153 fluoro group Chemical group F* 0.000 description 7
125000004435 hydrogen atom Chemical group [H]* 0.000 description 7
229910000027 potassium carbonate Inorganic materials 0.000 description 7
239000012279 sodium borohydride Substances 0.000 description 7
229910000033 sodium borohydride Inorganic materials 0.000 description 7
206010061218 Inflammation Diseases 0.000 description 6
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 6
208000008589 Obesity Diseases 0.000 description 6
125000003342 alkenyl group Chemical group 0.000 description 6
239000012298 atmosphere Substances 0.000 description 6
125000000623 heterocyclic group Chemical group 0.000 description 6
150000002431 hydrogen Chemical class 0.000 description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
239000008101 lactose Substances 0.000 description 6
235000019359 magnesium stearate Nutrition 0.000 description 6
235000020824 obesity Nutrition 0.000 description 6
229920001296 polysiloxane Polymers 0.000 description 6
239000000843 powder Substances 0.000 description 6
235000017557 sodium bicarbonate Nutrition 0.000 description 6
229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
239000003826 tablet Substances 0.000 description 6
125000000304 alkynyl group Chemical group 0.000 description 5
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
238000004587 chromatography analysis Methods 0.000 description 5
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 5
RGXWDWUGBIJHDO-UHFFFAOYSA-N ethyl decanoate Chemical compound CCCCCCCCCC(=O)OCC RGXWDWUGBIJHDO-UHFFFAOYSA-N 0.000 description 5
125000001072 heteroaryl group Chemical group 0.000 description 5
230000004054 inflammatory process Effects 0.000 description 5
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 5
230000027939 micturition Effects 0.000 description 5
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
235000000346 sugar Nutrition 0.000 description 5
239000000454 talc Substances 0.000 description 5
229910052623 talc Inorganic materials 0.000 description 5
208000001072 type 2 diabetes mellitus Diseases 0.000 description 5
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
JJLBUHXIKHYZIX-UHFFFAOYSA-N 6,6,6-trifluorohexanoic acid Chemical compound OC(=O)CCCCC(F)(F)F JJLBUHXIKHYZIX-UHFFFAOYSA-N 0.000 description 4
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
208000002193 Pain Diseases 0.000 description 4
KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 4
239000007868 Raney catalyst Substances 0.000 description 4
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 4
229910000564 Raney nickel Inorganic materials 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
208000025865 Ulcer Diseases 0.000 description 4
210000001789 adipocyte Anatomy 0.000 description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
229910052794 bromium Inorganic materials 0.000 description 4
125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 4
MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 4
125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
125000005070 decynyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C#C* 0.000 description 4
PBWZKZYHONABLN-UHFFFAOYSA-N difluoroacetic acid Chemical compound OC(=O)C(F)F PBWZKZYHONABLN-UHFFFAOYSA-N 0.000 description 4
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
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WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 4
238000009472 formulation Methods 0.000 description 4
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
238000001727 in vivo Methods 0.000 description 4
239000007937 lozenge Substances 0.000 description 4
206010029446 nocturia Diseases 0.000 description 4
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 4
239000012312 sodium hydride Substances 0.000 description 4
229910000104 sodium hydride Inorganic materials 0.000 description 4
NKWCGTOZTHZDHB-UHFFFAOYSA-N 1h-imidazol-1-ium-4-carboxylate Chemical compound OC(=O)C1=CNC=N1 NKWCGTOZTHZDHB-UHFFFAOYSA-N 0.000 description 3
FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 3
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 3
206010004446 Benign prostatic hyperplasia Diseases 0.000 description 3
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 3
206010020751 Hypersensitivity Diseases 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
208000004403 Prostatic Hyperplasia Diseases 0.000 description 3
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
229920002472 Starch Polymers 0.000 description 3
206010046543 Urinary incontinence Diseases 0.000 description 3
PQLVXDKIJBQVDF-UHFFFAOYSA-N acetic acid;hydrate Chemical compound O.CC(O)=O PQLVXDKIJBQVDF-UHFFFAOYSA-N 0.000 description 3
150000001335 aliphatic alkanes Chemical class 0.000 description 3
208000026935 allergic disease Diseases 0.000 description 3
230000007815 allergy Effects 0.000 description 3
235000011114 ammonium hydroxide Nutrition 0.000 description 3
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