MXPA00009938A - Compuestos farmaceuticamente activos. - Google Patents

Info

Publication number

MXPA00009938A

MXPA00009938A MXPA00009938A MXPA00009938A MXPA00009938A MX PA00009938 A MXPA00009938 A MX PA00009938A MX PA00009938 A MXPA00009938 A MX PA00009938A MX PA00009938 A MXPA00009938 A MX PA00009938A MX PA00009938 A MXPA00009938 A MX PA00009938A

Authority

MX

Mexico

Prior art keywords

alkyl

group

aryl

optionally substituted

compound

Prior art date

1999-10-11

Links

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• Global Dossier
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• 150000001875 compounds Chemical class 0.000 title claims abstract description 291
• ZOOGRGPOEVQQDX-UUOKFMHZSA-N 3',5'-cyclic GMP Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=C(NC2=O)N)=C2N=C1 ZOOGRGPOEVQQDX-UUOKFMHZSA-N 0.000 claims abstract description 34
• 230000005764 inhibitory process Effects 0.000 claims abstract description 7
• 238000011321 prophylaxis Methods 0.000 claims abstract description 4
• 238000009109 curative therapy Methods 0.000 claims abstract description 3
• 101100189582 Dictyostelium discoideum pdeD gene Proteins 0.000 claims abstract 2
• 101150098694 PDE5A gene Proteins 0.000 claims abstract 2
• 102100029175 cGMP-specific 3',5'-cyclic phosphodiesterase Human genes 0.000 claims abstract 2
• 125000000217 alkyl group Chemical group 0.000 claims description 180
• 125000003118 aryl group Chemical group 0.000 claims description 98
• -1 Het3 Chemical group 0.000 claims description 86
• 229910052739 hydrogen Inorganic materials 0.000 claims description 74
• 125000001424 substituent group Chemical group 0.000 claims description 73
• 238000006243 chemical reaction Methods 0.000 claims description 69
• 125000005843 halogen group Chemical group 0.000 claims description 65
• 239000000203 mixture Substances 0.000 claims description 65
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 47
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 40
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 36
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 26
• 229910052757 nitrogen Inorganic materials 0.000 claims description 21
• 229910052799 carbon Inorganic materials 0.000 claims description 19
• 125000000623 heterocyclic group Chemical group 0.000 claims description 16
• 239000003814 drug Substances 0.000 claims description 14
• UFZNZKGKBWOSJG-UHFFFAOYSA-N purin-2-one Chemical compound O=C1N=CC2=NC=NC2=N1 UFZNZKGKBWOSJG-UHFFFAOYSA-N 0.000 claims description 14
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 12
• 238000009472 formulation Methods 0.000 claims description 12
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
• 229910052760 oxygen Inorganic materials 0.000 claims description 12
• 239000001301 oxygen Chemical group 0.000 claims description 12
• 125000005842 heteroatom Chemical group 0.000 claims description 11
• 238000007363 ring formation reaction Methods 0.000 claims description 11
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 10
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 9
• 239000011593 sulfur Substances 0.000 claims description 9
• 229910052717 sulfur Inorganic materials 0.000 claims description 9
• 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 8
• 241001465754 Metazoa Species 0.000 claims description 8
• 229920006395 saturated elastomer Polymers 0.000 claims description 8
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 6
• 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 6
• 206010057671 Female sexual dysfunction Diseases 0.000 claims description 6
• 201000001881 impotence Diseases 0.000 claims description 6
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
• 230000001568 sexual effect Effects 0.000 claims description 5
• 208000010228 Erectile Dysfunction Diseases 0.000 claims description 4
• 239000003085 diluting agent Substances 0.000 claims description 4
• 230000004064 dysfunction Effects 0.000 claims description 4
• CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 4
• 150000004703 alkoxides Chemical group 0.000 claims description 3
• 230000029936 alkylation Effects 0.000 claims description 3
• 238000005804 alkylation reaction Methods 0.000 claims description 3
• 238000010511 deprotection reaction Methods 0.000 claims description 3
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
• 239000008177 pharmaceutical agent Substances 0.000 claims description 3
• 125000005750 substituted cyclic group Chemical group 0.000 claims description 3
• 239000003981 vehicle Substances 0.000 claims description 3
• 206010024419 Libido decreased Diseases 0.000 claims description 2
• 208000006262 Psychological Sexual Dysfunctions Diseases 0.000 claims description 2
• 208000027520 Somatoform disease Diseases 0.000 claims description 2
• 239000002671 adjuvant Substances 0.000 claims description 2
• 208000017020 hypoactive sexual desire disease Diseases 0.000 claims description 2
• 208000027753 pain disease Diseases 0.000 claims description 2
• 239000008194 pharmaceutical composition Substances 0.000 claims description 2
• 230000037007 arousal Effects 0.000 claims 1
• 230000008030 elimination Effects 0.000 claims 1
• 238000003379 elimination reaction Methods 0.000 claims 1
• 238000004519 manufacturing process Methods 0.000 claims 1
• ZOOGRGPOEVQQDX-UHFFFAOYSA-N cyclic GMP Natural products O1C2COP(O)(=O)OC2C(O)C1N1C=NC2=C1NC(N)=NC2=O ZOOGRGPOEVQQDX-UHFFFAOYSA-N 0.000 abstract description 32
• 102000004861 Phosphoric Diester Hydrolases Human genes 0.000 abstract description 4
• 108090001050 Phosphoric Diester Hydrolases Proteins 0.000 abstract description 4
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 128
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 57
• 238000002360 preparation method Methods 0.000 description 56
• 239000000243 solution Substances 0.000 description 56
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 50
• 230000002829 reductive effect Effects 0.000 description 40
• 238000000034 method Methods 0.000 description 39
• 150000003839 salts Chemical class 0.000 description 35
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
• ZMXDDKWLCZADIW-UHFFFAOYSA-N Vilsmeier-Haack reagent Natural products CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
• 239000007787 solid Substances 0.000 description 23
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 20
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
• 235000019439 ethyl acetate Nutrition 0.000 description 20
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 19
• 102100024085 Alpha-aminoadipic semialdehyde dehydrogenase Human genes 0.000 description 19
• 101710135349 Venom phosphodiesterase Proteins 0.000 description 19
• 239000002904 solvent Substances 0.000 description 19
• 239000002585 base Substances 0.000 description 18
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
• 239000002253 acid Substances 0.000 description 17
• 238000010992 reflux Methods 0.000 description 17
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
• 238000004440 column chromatography Methods 0.000 description 16
• 239000011541 reaction mixture Substances 0.000 description 16
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
• 239000000741 silica gel Substances 0.000 description 15
• 229910002027 silica gel Inorganic materials 0.000 description 15
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
• 241000282414 Homo sapiens Species 0.000 description 14
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
• 238000010828 elution Methods 0.000 description 11
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
• 230000015572 biosynthetic process Effects 0.000 description 10
• 125000006239 protecting group Chemical group 0.000 description 10
• 238000005481 NMR spectroscopy Methods 0.000 description 9
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
• 230000000694 effects Effects 0.000 description 9
• 239000010410 layer Substances 0.000 description 9
• 239000012453 solvate Substances 0.000 description 9
• 238000003786 synthesis reaction Methods 0.000 description 9
• 238000011282 treatment Methods 0.000 description 9
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 8
• 238000007796 conventional method Methods 0.000 description 8
• 239000012043 crude product Substances 0.000 description 8
• 239000002552 dosage form Substances 0.000 description 8
• 229940079593 drug Drugs 0.000 description 8
• 239000003112 inhibitor Substances 0.000 description 8
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 8
• 235000019341 magnesium sulphate Nutrition 0.000 description 8
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 7
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 7
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 7
• 125000004432 carbon atom Chemical group C* 0.000 description 7
• 239000003054 catalyst Substances 0.000 description 7
• 239000003153 chemical reaction reagent Substances 0.000 description 7
• 239000000543 intermediate Substances 0.000 description 7
• 239000000546 pharmaceutical excipient Substances 0.000 description 7
• 239000012312 sodium hydride Substances 0.000 description 7
• 229910000104 sodium hydride Inorganic materials 0.000 description 7
• 239000000725 suspension Substances 0.000 description 7
• 229920000858 Cyclodextrin Polymers 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
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
• XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 6
• 239000000284 extract Substances 0.000 description 6
• 150000004820 halides Chemical class 0.000 description 6
• 238000004128 high performance liquid chromatography Methods 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
• 239000002480 mineral oil Substances 0.000 description 6
• 235000010446 mineral oil Nutrition 0.000 description 6
• 230000003389 potentiating effect Effects 0.000 description 6
• 239000002244 precipitate Substances 0.000 description 6
• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
• KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 5
• WGCYRFWNGRMRJA-UHFFFAOYSA-N 1-ethylpiperazine Chemical compound CCN1CCNCC1 WGCYRFWNGRMRJA-UHFFFAOYSA-N 0.000 description 5
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
• 241000124008 Mammalia Species 0.000 description 5
• PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 5
• 229940124639 Selective inhibitor Drugs 0.000 description 5
• 229920002472 Starch Polymers 0.000 description 5
• 229960000583 acetic acid Drugs 0.000 description 5
• 239000012267 brine Substances 0.000 description 5
• 239000003795 chemical substances by application Substances 0.000 description 5
• 238000005859 coupling reaction Methods 0.000 description 5
• 125000004122 cyclic group Chemical group 0.000 description 5
• 239000006185 dispersion Substances 0.000 description 5
• 239000000706 filtrate Substances 0.000 description 5
• 238000001640 fractional crystallisation Methods 0.000 description 5
• 125000000524 functional group Chemical group 0.000 description 5
• 230000000155 isotopic effect Effects 0.000 description 5
• NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 5
• 239000012071 phase Substances 0.000 description 5
• 229920001223 polyethylene glycol Polymers 0.000 description 5
• 239000000843 powder Substances 0.000 description 5
• 230000009467 reduction Effects 0.000 description 5
• 235000017557 sodium bicarbonate Nutrition 0.000 description 5
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
• 229940032147 starch Drugs 0.000 description 5
• 239000008107 starch Substances 0.000 description 5
• 235000019698 starch Nutrition 0.000 description 5
• 239000000758 substrate Substances 0.000 description 5
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 4
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
• OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
• 238000004458 analytical method Methods 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
• 239000011575 calcium Substances 0.000 description 4
• 239000002775 capsule Substances 0.000 description 4
• 238000004587 chromatography analysis Methods 0.000 description 4
• PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 4
• SPBWMYPZWNFWES-UHFFFAOYSA-N disodium;azanylidyneoxidanium;iron(2+);pentacyanide;dihydrate Chemical compound O.O.[Na+].[Na+].[Fe+2].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].[O+]#N SPBWMYPZWNFWES-UHFFFAOYSA-N 0.000 description 4
• 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 4
• 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 4
• 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 4
• UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 4
• 238000000338 in vitro Methods 0.000 description 4
• 239000008101 lactose Substances 0.000 description 4
• 231100000252 nontoxic Toxicity 0.000 description 4
• 230000003000 nontoxic effect Effects 0.000 description 4
• 239000012074 organic phase Substances 0.000 description 4
• 235000019271 petrolatum Nutrition 0.000 description 4
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
• 239000000651 prodrug Substances 0.000 description 4
• 229940002612 prodrug Drugs 0.000 description 4
• WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 4
• 150000003180 prostaglandins Chemical class 0.000 description 4
• UYLWKSJTHLRFBX-UHFFFAOYSA-N purin-6-one Chemical compound O=C1N=CN=C2N=CN=C12 UYLWKSJTHLRFBX-UHFFFAOYSA-N 0.000 description 4
• LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
• 229940083618 sodium nitroprusside Drugs 0.000 description 4
• UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 4
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
• WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
• OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
• 229920002785 Croscarmellose sodium Polymers 0.000 description 3
• 102000004190 Enzymes Human genes 0.000 description 3
• 108090000790 Enzymes Proteins 0.000 description 3
• 108010010803 Gelatin Proteins 0.000 description 3
• 241000282412 Homo Species 0.000 description 3
• 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 3
• 229910002651 NO3 Inorganic materials 0.000 description 3
• NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 3
• 241000283973 Oryctolagus cuniculus Species 0.000 description 3
• 229940123333 Phosphodiesterase 5 inhibitor Drugs 0.000 description 3
• 239000002202 Polyethylene glycol Substances 0.000 description 3
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
• DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 3
• 230000003213 activating effect Effects 0.000 description 3
• 239000000443 aerosol Substances 0.000 description 3
• 239000000556 agonist Substances 0.000 description 3
• 102000004305 alpha Adrenergic Receptors Human genes 0.000 description 3
• 108090000861 alpha Adrenergic Receptors Proteins 0.000 description 3
• 239000007864 aqueous solution Substances 0.000 description 3
• 238000003556 assay Methods 0.000 description 3
• 125000004429 atom Chemical group 0.000 description 3
• XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 3
• 229910052791 calcium Inorganic materials 0.000 description 3
• 239000000460 chlorine Substances 0.000 description 3
• 229910052801 chlorine Inorganic materials 0.000 description 3
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
• 230000008878 coupling Effects 0.000 description 3
• 238000010168 coupling process Methods 0.000 description 3
• UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 3
• XEYBRNLFEZDVAW-ARSRFYASSA-N dinoprostone Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O XEYBRNLFEZDVAW-ARSRFYASSA-N 0.000 description 3
• 229960002986 dinoprostone Drugs 0.000 description 3
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
• 229940088598 enzyme Drugs 0.000 description 3
• 239000000499 gel Substances 0.000 description 3
• 239000008273 gelatin Substances 0.000 description 3
• 229920000159 gelatin Polymers 0.000 description 3
• 235000019322 gelatine Nutrition 0.000 description 3
• 235000011852 gelatine desserts Nutrition 0.000 description 3
• 239000004615 ingredient Substances 0.000 description 3
• 235000019359 magnesium stearate Nutrition 0.000 description 3
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
• 239000006199 nebulizer Substances 0.000 description 3
• 239000002674 ointment Substances 0.000 description 3
• 230000003287 optical effect Effects 0.000 description 3
• 229940094443 oxytocics prostaglandins Drugs 0.000 description 3
• 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 3
• 229910052763 palladium Inorganic materials 0.000 description 3
• 238000007911 parenteral administration Methods 0.000 description 3
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