SK18152000A3 - Cyklopentanóndihydropyridínové zlúčeniny účinné ako látky otvárajúce draslíkové kanály - Google Patents

Cyklopentanóndihydropyridínové zlúčeniny účinné ako látky otvárajúce draslíkové kanály Download PDF

Info

Publication number: SK18152000A3
Authority: SK; Slovakia
Prior art keywords: group; hydrogen; compound; alkyl; haloalkyl
Prior art date: 1999-03-04

Application number

SK1815-2000A

Other languages

English (en)

Slovak (sk)

Inventor

William A. Carroll

Yiyuan Chen

Irene Drizin

James F. Kerwin

Jimmie L. Moore

Original Assignee

Abbott Laboratories

Priority date (The priority date 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 date listed.)

1999-03-04

Filing date

2000-03-06

Publication date

2001-06-11

2000-03-06 Application filed by Abbott Laboratories filed Critical Abbott Laboratories

2001-06-11 Publication of SK18152000A3 publication Critical patent/SK18152000A3/sk

Links

229940127315 Potassium Channel Openers Drugs 0.000 title abstract 2
LSMFPLJDAZPVTN-UHFFFAOYSA-N cyclopentanone;1,2-dihydropyridine Chemical class C1NC=CC=C1.O=C1CCCC1 LSMFPLJDAZPVTN-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 162
238000000034 method Methods 0.000 claims abstract description 66
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 24
201000010099 disease Diseases 0.000 claims abstract description 15
241000124008 Mammalia Species 0.000 claims abstract description 8
125000000217 alkyl group Chemical group 0.000 claims description 95
-1 3-Cyanophenyl Chemical group 0.000 claims description 88
239000001257 hydrogen Substances 0.000 claims description 70
229910052739 hydrogen Inorganic materials 0.000 claims description 70
125000001188 haloalkyl group Chemical group 0.000 claims description 45
125000003118 aryl group Chemical group 0.000 claims description 37
150000002148 esters Chemical class 0.000 claims description 35
150000002431 hydrogen Chemical class 0.000 claims description 35
239000000651 prodrug Substances 0.000 claims description 30
229940002612 prodrug Drugs 0.000 claims description 30
150000003839 salts Chemical class 0.000 claims description 30
150000001408 amides Chemical class 0.000 claims description 26
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 25
125000003545 alkoxy group Chemical group 0.000 claims description 25
125000001072 heteroaryl group Chemical group 0.000 claims description 25
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 25
239000003814 drug Substances 0.000 claims description 20
125000004093 cyano group Chemical group *C#N 0.000 claims description 19
125000003342 alkenyl group Chemical group 0.000 claims description 18
125000000304 alkynyl group Chemical group 0.000 claims description 16
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 16
125000002102 aryl alkyloxo group Chemical group 0.000 claims description 15
229910052736 halogen Inorganic materials 0.000 claims description 15
150000002367 halogens Chemical group 0.000 claims description 15
239000008194 pharmaceutical composition Substances 0.000 claims description 14
125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 13
125000001424 substituent group Chemical group 0.000 claims description 13
206010046543 Urinary incontinence Diseases 0.000 claims description 12
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 12
125000000262 haloalkenyl group Chemical group 0.000 claims description 12
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 12
125000004043 oxo group Chemical group O=* 0.000 claims description 12
125000005020 hydroxyalkenyl group Chemical group 0.000 claims description 11
239000003937 drug carrier Substances 0.000 claims description 10
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 9
208000035475 disorder Diseases 0.000 claims description 9
125000001475 halogen functional group Chemical group 0.000 claims description 9
125000001054 5 membered carbocyclic group Chemical group 0.000 claims description 8
206010020772 Hypertension Diseases 0.000 claims description 8
208000019695 Migraine disease Diseases 0.000 claims description 8
208000002193 Pain Diseases 0.000 claims description 8
208000003782 Raynaud disease Diseases 0.000 claims description 8
208000012322 Raynaud phenomenon Diseases 0.000 claims description 8
208000006673 asthma Diseases 0.000 claims description 8
206010015037 epilepsy Diseases 0.000 claims description 8
230000004770 neurodegeneration Effects 0.000 claims description 8
125000004008 6 membered carbocyclic group Chemical group 0.000 claims description 7
208000030814 Eating disease Diseases 0.000 claims description 7
208000019454 Feeding and Eating disease Diseases 0.000 claims description 7
235000014632 disordered eating Nutrition 0.000 claims description 7
201000001881 impotence Diseases 0.000 claims description 7
206010027599 migraine Diseases 0.000 claims description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 6
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 6
IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 6
KJGVZJAJZFXQMD-UHFFFAOYSA-N 4-(3-bromo-4-fluorophenyl)-2-methyl-5-oxo-1,4,6,7-tetrahydrocyclopenta[b]pyridine-3-carboxylic acid Chemical compound C1CC(=O)C2=C1NC(C)=C(C(O)=O)C2C1=CC=C(F)C(Br)=C1 KJGVZJAJZFXQMD-UHFFFAOYSA-N 0.000 claims description 4
FNQJDLTXOVEEFB-UHFFFAOYSA-N 1,2,3-benzothiadiazole Chemical compound C1=CC=C2SN=NC2=C1 FNQJDLTXOVEEFB-UHFFFAOYSA-N 0.000 claims description 3
SLLFVLKNXABYGI-UHFFFAOYSA-N 1,2,3-benzoxadiazole Chemical compound C1=CC=C2ON=NC2=C1 SLLFVLKNXABYGI-UHFFFAOYSA-N 0.000 claims description 3
BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 claims description 3
MJTLRFUTIRQWLQ-UHFFFAOYSA-N 8-(3-chloro-4-fluorophenyl)-2,3,4,5,6,8-hexahydrodicyclopenta[1,3-b:1',3'-f]pyridine-1,7-dione Chemical compound C1=C(Cl)C(F)=CC=C1C1C(C(=O)CC2)=C2NC2=C1C(=O)CC2 MJTLRFUTIRQWLQ-UHFFFAOYSA-N 0.000 claims description 3
239000005964 Acibenzolar-S-methyl Substances 0.000 claims description 3
RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 claims description 3
239000002243 precursor Substances 0.000 claims description 3
229930192474 thiophene Natural products 0.000 claims description 3
AWBOSXFRPFZLOP-UHFFFAOYSA-N 2,1,3-benzoxadiazole Chemical compound C1=CC=CC2=NON=C21 AWBOSXFRPFZLOP-UHFFFAOYSA-N 0.000 claims description 2
125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 2
SLTFHEPYCGQTPP-UHFFFAOYSA-N 8-(4-chloro-3-nitrophenyl)-2,3,4,5,6,8-hexahydrodicyclopenta[1,3-b:1',3'-f]pyridine-1,7-dione Chemical compound C1=C(Cl)C([N+](=O)[O-])=CC(C2C3=C(CCC3=O)NC3=C2C(CC3)=O)=C1 SLTFHEPYCGQTPP-UHFFFAOYSA-N 0.000 claims description 2
FCQFDLWFVCIFCV-UHFFFAOYSA-N 8-(4-fluoro-3-iodophenyl)-2,3,4,5,6,8-hexahydrodicyclopenta[1,3-b:1',3'-f]pyridine-1,7-dione Chemical compound C1=C(I)C(F)=CC=C1C1C(C(=O)CC2)=C2NC2=C1C(=O)CC2 FCQFDLWFVCIFCV-UHFFFAOYSA-N 0.000 claims description 2
TUWBBBXRNALSQT-UHFFFAOYSA-N 9-(3-bromo-4-fluorophenyl)-5,6,7,9-tetrahydro-4h-cyclopenta[b]quinoline-1,8-dione Chemical compound C1=C(Br)C(F)=CC=C1C1C(C(=O)CCC2)=C2NC2=C1C(=O)C=C2 TUWBBBXRNALSQT-UHFFFAOYSA-N 0.000 claims description 2
150000003536 tetrazoles Chemical class 0.000 claims description 2
PEWHDFYAXIMXEH-UHFFFAOYSA-N 8-(3-bromo-4-fluorophenyl)-2,3,4,5,6,8-hexahydrodicyclopenta[1,3-b:1',3'-f]pyridine-1,7-dione Chemical compound C1=C(Br)C(F)=CC=C1C1C(C(=O)CC2)=C2NC2=C1C(=O)CC2 PEWHDFYAXIMXEH-UHFFFAOYSA-N 0.000 claims 1
239000000203 mixture Substances 0.000 abstract description 35
102000004257 Potassium Channel Human genes 0.000 abstract description 14
108020001213 potassium channel Proteins 0.000 abstract description 14
230000001668 ameliorated effect Effects 0.000 abstract 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 78
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 57
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 46
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 34
235000019441 ethanol Nutrition 0.000 description 29
125000004925 dihydropyridyl group Chemical class N1(CC=CC=C1)* 0.000 description 28
150000001299 aldehydes Chemical class 0.000 description 27
239000007787 solid Substances 0.000 description 27
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 23
229910021529 ammonia Inorganic materials 0.000 description 23
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
239000002904 solvent Substances 0.000 description 20
125000003710 aryl alkyl group Chemical group 0.000 description 19
LOGSONSNCYTHPS-UHFFFAOYSA-N cyclopentane-1,3-dione Chemical compound O=C1CCC(=O)C1 LOGSONSNCYTHPS-UHFFFAOYSA-N 0.000 description 19
238000006243 chemical reaction Methods 0.000 description 18
LSROXAYPMFICCA-UHFFFAOYSA-N 3-aminocyclopent-2-en-1-one Chemical compound NC1=CC(=O)CC1 LSROXAYPMFICCA-UHFFFAOYSA-N 0.000 description 17
239000000243 solution Substances 0.000 description 17
229940079593 drug Drugs 0.000 description 16
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
210000004027 cell Anatomy 0.000 description 14
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 13
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 13
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 13
238000010438 heat treatment Methods 0.000 description 13
239000002253 acid Substances 0.000 description 12
230000008602 contraction Effects 0.000 description 12
MCFZBCCYOPSZLG-UHFFFAOYSA-N cyclopent-4-ene-1,3-dione Chemical compound O=C1CC(=O)C=C1 MCFZBCCYOPSZLG-UHFFFAOYSA-N 0.000 description 12
235000019439 ethyl acetate Nutrition 0.000 description 12
238000001727 in vivo Methods 0.000 description 11
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 10
230000000694 effects Effects 0.000 description 10
238000009472 formulation Methods 0.000 description 10
239000000546 pharmaceutical excipient Substances 0.000 description 10
230000004044 response Effects 0.000 description 10
210000001519 tissue Anatomy 0.000 description 10
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
238000010521 absorption reaction Methods 0.000 description 9
125000004448 alkyl carbonyl group Chemical group 0.000 description 9
231100000252 nontoxic Toxicity 0.000 description 9
230000003000 nontoxic effect Effects 0.000 description 9
238000002360 preparation method Methods 0.000 description 9
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 8
USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 8
239000005695 Ammonium acetate Substances 0.000 description 8
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 8
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
235000019257 ammonium acetate Nutrition 0.000 description 8
229940043376 ammonium acetate Drugs 0.000 description 8
239000000908 ammonium hydroxide Substances 0.000 description 8
235000011114 ammonium hydroxide Nutrition 0.000 description 8
HQMRIBYCTLBDAK-UHFFFAOYSA-M bis(2-methylpropyl)alumanylium;chloride Chemical compound CC(C)C[Al](Cl)CC(C)C HQMRIBYCTLBDAK-UHFFFAOYSA-M 0.000 description 8
239000000872 buffer Substances 0.000 description 8
125000004432 carbon atom Chemical group C* 0.000 description 8
239000003795 chemical substances by application Substances 0.000 description 8
239000002552 dosage form Substances 0.000 description 8
239000002502 liposome Substances 0.000 description 8
239000012528 membrane Substances 0.000 description 8
229910052757 nitrogen Inorganic materials 0.000 description 8
239000000843 powder Substances 0.000 description 8
239000003586 protic polar solvent Substances 0.000 description 8
239000000126 substance Substances 0.000 description 8
239000000725 suspension Substances 0.000 description 8
YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical compound C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 description 7
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 7
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 7
239000000556 agonist Substances 0.000 description 7
125000004414 alkyl thio group Chemical group 0.000 description 7
125000000753 cycloalkyl group Chemical group 0.000 description 7
238000003818 flash chromatography Methods 0.000 description 7
150000002374 hemiaminals Chemical class 0.000 description 7
239000007788 liquid Substances 0.000 description 7
239000000047 product Substances 0.000 description 7
239000011780 sodium chloride Substances 0.000 description 7
229910052717 sulfur Chemical group 0.000 description 7
239000011593 sulfur Chemical group 0.000 description 7
238000012360 testing method Methods 0.000 description 7
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
229920002472 Starch Polymers 0.000 description 6
125000004453 alkoxycarbonyl group Chemical group 0.000 description 6
150000001735 carboxylic acids Chemical class 0.000 description 6
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 6
238000002347 injection Methods 0.000 description 6
239000007924 injection Substances 0.000 description 6
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
239000002609 medium Substances 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
239000000741 silica gel Substances 0.000 description 6
229910002027 silica gel Inorganic materials 0.000 description 6
235000019698 starch Nutrition 0.000 description 6
DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 5
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 5
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
125000005196 alkyl carbonyloxy group Chemical group 0.000 description 5
125000004644 alkyl sulfinyl group Chemical group 0.000 description 5
125000004390 alkyl sulfonyl group Chemical group 0.000 description 5
229910052786 argon Inorganic materials 0.000 description 5
125000004104 aryloxy group Chemical group 0.000 description 5
239000012298 atmosphere Substances 0.000 description 5
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 5
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 5
239000002775 capsule Substances 0.000 description 5
239000000969 carrier Substances 0.000 description 5
238000000576 coating method Methods 0.000 description 5
125000004966 cyanoalkyl group Chemical group 0.000 description 5
125000004438 haloalkoxy group Chemical group 0.000 description 5
239000008101 lactose Substances 0.000 description 5
239000003921 oil Substances 0.000 description 5
235000019198 oils Nutrition 0.000 description 5
125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 5
239000006187 pill Substances 0.000 description 5
229920001223 polyethylene glycol Polymers 0.000 description 5
239000004036 potassium channel stimulating agent Substances 0.000 description 5
239000003755 preservative agent Substances 0.000 description 5
239000003826 tablet Substances 0.000 description 5
PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 4
LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-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
241000282412 Homo Species 0.000 description 4
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 4
229930006000 Sucrose Natural products 0.000 description 4
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 4
239000004480 active ingredient Substances 0.000 description 4
230000008901 benefit Effects 0.000 description 4
239000012043 crude product Substances 0.000 description 4
239000003599 detergent Substances 0.000 description 4
239000000945 filler Substances 0.000 description 4
239000008103 glucose Substances 0.000 description 4
150000002430 hydrocarbons Chemical group 0.000 description 4
239000003701 inert diluent Substances 0.000 description 4
150000002632 lipids Chemical class 0.000 description 4
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 4
NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 4
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
239000012071 phase Substances 0.000 description 4
239000000523 sample Substances 0.000 description 4
210000002460 smooth muscle Anatomy 0.000 description 4
239000011734 sodium Substances 0.000 description 4
239000007921 spray Substances 0.000 description 4
239000008107 starch Substances 0.000 description 4
239000005720 sucrose Substances 0.000 description 4
239000000454 talc Substances 0.000 description 4
235000012222 talc Nutrition 0.000 description 4
229910052623 talc Inorganic materials 0.000 description 4
FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 4
239000001993 wax Substances 0.000 description 4
HVAUUPRFYPCOCA-AREMUKBSSA-N 2-O-acetyl-1-O-hexadecyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCCOC[C@@H](OC(C)=O)COP([O-])(=O)OCC[N+](C)(C)C HVAUUPRFYPCOCA-AREMUKBSSA-N 0.000 description 3
125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 3
ZZMRPOAHZITKBV-UHFFFAOYSA-N 3-aminocyclohex-2-en-1-one Chemical compound NC1=CC(=O)CCC1 ZZMRPOAHZITKBV-UHFFFAOYSA-N 0.000 description 3
FAHZIKXYYRGSHF-UHFFFAOYSA-N 3-bromo-4-fluorobenzaldehyde Chemical compound FC1=CC=C(C=O)C=C1Br FAHZIKXYYRGSHF-UHFFFAOYSA-N 0.000 description 3
229920001817 Agar Polymers 0.000 description 3
241000416162 Astragalus gummifer Species 0.000 description 3
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BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
238000011200 topical administration Methods 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
125000005208 trialkylammonium group Chemical group 0.000 description 1
150000003852 triazoles Chemical class 0.000 description 1
210000003708 urethra Anatomy 0.000 description 1
230000002485 urinary effect Effects 0.000 description 1
229940070710 valerate Drugs 0.000 description 1
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
230000002792 vascular Effects 0.000 description 1
230000000304 vasodilatating effect Effects 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
235000019871 vegetable fat Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
238000012795 verification Methods 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000011787 zinc oxide Substances 0.000 description 1
235000014692 zinc oxide Nutrition 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/10—Drugs for genital or sexual disorders; Contraceptives for impotence
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- 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
- A61P9/12—Antihypertensives
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
- C07C45/298—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups with manganese derivatives
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/06—Ring systems of three rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Neurosurgery (AREA)
Neurology (AREA)
Biomedical Technology (AREA)
Pulmonology (AREA)
Endocrinology (AREA)
Hospice & Palliative Care (AREA)
Psychiatry (AREA)
Pain & Pain Management (AREA)
Gynecology & Obstetrics (AREA)
Cardiology (AREA)
Reproductive Health (AREA)
Heart & Thoracic Surgery (AREA)
Urology & Nephrology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Other In-Based Heterocyclic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pyridine Compounds (AREA)

SK1815-2000A 1999-03-04 2000-03-06 Cyklopentanóndihydropyridínové zlúčeniny účinné ako látky otvárajúce draslíkové kanály SK18152000A3 (sk)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US09/262,441 US6518279B2 (en)	1999-03-04	1999-03-04	Cyclopentanone dihydropyridine compounds useful as potassium channel openers
PCT/US2000/005828 WO2000051986A1 (en)	1999-03-04	2000-03-06	Cyclopentanone dihydropyridine compounds useful as potassium channel openers

Publications (1)

Publication Number	Publication Date
SK18152000A3 true SK18152000A3 (sk)	2001-06-11

Family

ID=22997528

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK1815-2000A SK18152000A3 (sk)	1999-03-04	2000-03-06	Cyklopentanóndihydropyridínové zlúčeniny účinné ako látky otvárajúce draslíkové kanály

Country Status (20)

Country	Link
US (1)	US6518279B2 (no)
EP (1)	EP1075466A1 (no)
JP (1)	JP2003517454A (no)
KR (1)	KR20010043295A (no)
CN (1)	CN1318053A (no)
AR (1)	AR028987A1 (no)
AU (1)	AU3616800A (no)
BG (1)	BG104999A (no)
BR (1)	BR0005189A (no)
CA (1)	CA2330541A1 (no)
CO (1)	CO5150208A1 (no)
HU (1)	HUP0102895A3 (no)
IL (1)	IL139140A0 (no)
MX (1)	MXPA00010790A (no)
NO (1)	NO20005570D0 (no)
PL (1)	PL343883A1 (no)
SK (1)	SK18152000A3 (no)
TR (1)	TR200003202T1 (no)
WO (1)	WO2000051986A1 (no)
ZA (1)	ZA200005798B (no)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6265417B1 (en)	1997-12-18	2001-07-24	Abbott Laboratories	Potassium channel openers
US6593335B1 (en)	1997-12-18	2003-07-15	Abbott Laboratories	Potassium channel openers
AU2001282744A1 (en) *	2000-08-02	2002-02-13	Astrazeneca Ab	Process for asymmetric synthesis of substituted 1,4-dihydropyridines
US20030045449A1 (en) *	2001-08-15	2003-03-06	Pfizer, Inc.	Pharmaceutical combinations for the treatment of neurodegenerative diseases
US20030199578A1 (en) *	2002-04-19	2003-10-23	Turner Sean C.	Naphthalene amides as potassium channel openers
DE602007003697D1 (de)	2006-02-10	2010-01-21	Janssen Pharmaceutica Nv	Ffner
CA2752603C (en)	2009-02-18	2016-04-05	Bayer Pharma Aktiengesellschaft	Bi- and tricyclic indazole-substituted 1,4-dihydropyridine derivatives and uses thereof
WO2021253180A1 (en) *	2020-06-15	2021-12-23	Novartis Ag	Methyl (r) -2- (fluoromethyl) -5-oxo-4-phenyl-4, 5, 6, 7-tetrahydro-1h-cyclopenta [b] pyridine-3-carboxylate and methyl (r) -2- (fluoromethyl) -5-oxo-4-phenyl-1, 4, 5, 7-tetrahydrofuro [3, 4-b] pyridine-3-carboxylate as cav1.2 activators
US11939316B1 (en)	2023-11-06	2024-03-26	King Faisal University	9-(6-flouro-2-hydroxyouinolin-3-yl)-10-(2-hydroxyethyl)-3,6-diphenyl-3,4,6,7,9,10-hexhydroacridine-1,8(2h,5h)-dione as an antimicrobial compound
US11970478B1 (en)	2023-11-16	2024-04-30	King Faisal University	9-(2-hydroxyquinolin-3-yl)-10-(2-hydroxyethyl)-3,3,6,6-tetramethyl-3,4,6,7,9,10-hexahydroacridine1,8(2H,5H)-dione as an antimicrobial compound

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2003148A1 (de)	1970-01-24	1971-07-29	Bayer Ag	Neue 1,4-Dihydropyridinderivate
DE3447170A1 (de)	1984-12-22	1986-07-03	Bayer Ag, 5090 Leverkusen	Mischung unterschiedlicher dihydropyridine, verfahren zu ihrer herstellung sowie ihre verwendung in arzneimitteln
GB8716971D0 (en)	1987-07-17	1987-08-26	Pfizer Ltd	Therapeutic agents
GB8907401D0 (en)	1989-04-01	1989-05-17	Pfizer Ltd	Therapeutic agents
JP3285963B2 (ja)	1991-10-21	2002-05-27	インペリアル・ケミカル・インダストリーズ・ピーエルシー	治療剤
GB9220570D0 (en)	1991-10-21	1992-11-11	Ici Plc	Therapeutic agent
GB9318935D0 (en)	1992-10-20	1993-10-27	Zeneca Ltd	Heterocyclic derivatives
DE4313690A1 (de)	1993-04-27	1994-11-03	Bayer Ag	Kondensierte Chinolyl-dihydropyridine, Verfahren zu ihrer Herstellung und ihre Verwendung in Arzneimitteln
JP2002508354A (ja)	1997-12-18	2002-03-19	アボット・ラボラトリーズ	カリウムチャンネル開放剤

1999
- 1999-03-04 US US09/262,441 patent/US6518279B2/en not_active Expired - Fee Related
2000
- 2000-03-01 CO CO00014719A patent/CO5150208A1/es unknown
- 2000-03-02 AR ARP000100931A patent/AR028987A1/es not_active Application Discontinuation
- 2000-03-06 BR BR0005189-6A patent/BR0005189A/pt not_active IP Right Cessation
- 2000-03-06 IL IL13914000A patent/IL139140A0/xx unknown
- 2000-03-06 MX MXPA00010790A patent/MXPA00010790A/es unknown
- 2000-03-06 CA CA002330541A patent/CA2330541A1/en not_active Abandoned
- 2000-03-06 HU HU0102895A patent/HUP0102895A3/hu unknown
- 2000-03-06 SK SK1815-2000A patent/SK18152000A3/sk unknown
- 2000-03-06 JP JP2000602213A patent/JP2003517454A/ja not_active Withdrawn
- 2000-03-06 CN CN00800760A patent/CN1318053A/zh active Pending
- 2000-03-06 EP EP00914832A patent/EP1075466A1/en not_active Withdrawn
- 2000-03-06 AU AU36168/00A patent/AU3616800A/en not_active Abandoned
- 2000-03-06 WO PCT/US2000/005828 patent/WO2000051986A1/en not_active Ceased
- 2000-03-06 TR TR2000/03202T patent/TR200003202T1/xx unknown
- 2000-03-06 PL PL00343883A patent/PL343883A1/xx not_active Application Discontinuation
- 2000-03-06 KR KR1020007012257A patent/KR20010043295A/ko not_active Withdrawn
- 2000-10-18 ZA ZA200005798A patent/ZA200005798B/en unknown
- 2000-11-03 NO NO20005570A patent/NO20005570D0/no not_active Application Discontinuation
- 2000-11-28 BG BG104999A patent/BG104999A/xx unknown

Also Published As

Publication number	Publication date
US6518279B2 (en)	2003-02-11
TR200003202T1 (tr)	2001-08-21
KR20010043295A (ko)	2001-05-25
WO2000051986A1 (en)	2000-09-08
HUP0102895A2 (hu)	2001-12-28
NO20005570L (no)	2000-11-03
NO20005570D0 (no)	2000-11-03
IL139140A0 (en)	2001-11-25
MXPA00010790A (es)	2002-06-04
CN1318053A (zh)	2001-10-17
AR028987A1 (es)	2003-06-04
AU3616800A (en)	2000-09-21
US20020007065A1 (en)	2002-01-17
BG104999A (en)	2001-10-31
HUP0102895A3 (en)	2002-01-28
CA2330541A1 (en)	2000-09-08
JP2003517454A (ja)	2003-05-27
BR0005189A (pt)	2001-01-09
EP1075466A1 (en)	2001-02-14
ZA200005798B (en)	2002-01-18
PL343883A1 (en)	2001-09-10
CO5150208A1 (es)	2002-04-29

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EP1611133B1 (en)	2010-07-07	Condensed n-heterocyclic compound and use thereoff as crf receptor antagonist
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KR100814599B1 (ko)	2008-03-17	신경퇴행성 장애 치료용 이미다졸 화합물
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JPH06505715A (ja)	1994-06-30	化合物
KR20050083918A (ko)	2005-08-26	Ｇｓｋ-3베타 억제제로서의 피리다지논 유도체
AU716435B2 (en)	2000-02-24	Novel indole-2,3-dione-3-oxime derivatives
SK12332003A3 (sk)	2004-04-06	Tiohydantoíny a ich použitie na liečenie cukrovky
KR970005302B1 (ko)	1997-04-15	이미다조피린딘 혈소판 활성 인자/히스타민(paf/h₁)길항제
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US6518279B2 (en)	2003-02-11	Cyclopentanone dihydropyridine compounds useful as potassium channel openers
TW202440553A (zh)	2024-10-16	作為at2r拮抗劑的雜環化合物
CA2560080A1 (en)	2005-09-22	Solifenacin-containing composition
WO2005115984A2 (en)	2005-12-08	Large conductance calcium-activitated k channel opener
JPS60214778A (ja)	1985-10-28	Ν置換３，４−ジヒドロピリミジン誘導体ならびにその製造法および用途
CN114478537B (zh)	2024-02-02	环酰胺并环化合物及其医药用途
CA1330663C (en)	1994-07-12	Thiazolidinedione derivatives
SK5242001A3 (en)	2001-12-03	Pyrano-, piperidino- and thiopyrano compounds and methods of use
CZ20004428A3 (cs)	2001-05-16	Cyklopentanon dihydropyridinové sloučeniny užitečné jako látky otevírající draslíkové kanály
US6274587B1 (en)	2001-08-14	Tricyclic dihydropyrimidine potassium channel openers
US7057047B2 (en)	2006-06-06	Methods for making 2-(7-chloro-1,8-naphthyridine-2-yl)-3-(5-methyl-2oxo-hexyl)-1-isoidolinone
US5475114A (en)	1995-12-12	Pyrazolotriazole derivatives
HU191597B (en)	1987-03-30	Process for producing of 2-/2-indalin/-imadazoline preparates and medical preparates consisting of such substances
JPS6377875A (ja)	1988-04-08	ヘテロ環式置換インドリノン、その製法並びにこれを含有する心臓−及び循環系疾患治療剤