MXPA03005990A

MXPA03005990A - Compuestos farmaceuticalmente activos.

Compuestos farmaceuticalmente activos.

Info

Publication number: MXPA03005990A
Authority: MX; Mexico
Prior art keywords: alkyl; het; aryl; optionally substituted; terminated
Prior art date: 2001-03-28

Application number

MXPA03005990A

Other languages

English (en)

Spanish (es)

Inventor

Ian Kemp Mark

Original Assignee

Pfizer

Priority date

2001-03-28

Filing date

2002-03-19

Publication date

2005-02-14

2002-03-19 Application filed by Pfizer filed Critical Pfizer

2005-02-14 Publication of MXPA03005990A publication Critical patent/MXPA03005990A/es

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 379
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 28
125000004122 cyclic group Chemical group 0.000 claims abstract description 10
230000005764 inhibitory process Effects 0.000 claims abstract description 8
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 3
101150098694 PDE5A gene Proteins 0.000 claims abstract 3
102100029175 cGMP-specific 3',5'-cyclic phosphodiesterase Human genes 0.000 claims abstract 3
125000000217 alkyl group Chemical group 0.000 claims description 215
125000003118 aryl group Chemical group 0.000 claims description 129
125000001424 substituent group Chemical group 0.000 claims description 95
PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 90
239000000203 mixture Chemical group 0.000 claims description 83
125000005843 halogen group Chemical group 0.000 claims description 67
-1 C ^ -e-aryl alkyl Chemical group 0.000 claims description 62
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 58
125000004093 cyano group Chemical group *C#N 0.000 claims description 57
229910052757 nitrogen Inorganic materials 0.000 claims description 53
238000000034 method Methods 0.000 claims description 47
125000000623 heterocyclic group Chemical group 0.000 claims description 44
125000004433 nitrogen atom Chemical group N* 0.000 claims description 39
150000003839 salts Chemical class 0.000 claims description 39
229910052739 hydrogen Inorganic materials 0.000 claims description 35
229910052799 carbon Inorganic materials 0.000 claims description 34
239000003814 drug Substances 0.000 claims description 19
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 15
239000012453 solvate Substances 0.000 claims description 15
229910052760 oxygen Inorganic materials 0.000 claims description 14
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 13
239000001301 oxygen Chemical group 0.000 claims description 13
239000000651 prodrug Substances 0.000 claims description 13
229940002612 prodrug Drugs 0.000 claims description 13
229910052717 sulfur Inorganic materials 0.000 claims description 11
238000011282 treatment Methods 0.000 claims description 11
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 10
238000009472 formulation Methods 0.000 claims description 10
125000005842 heteroatom Chemical group 0.000 claims description 10
102200001405 rs377584435 Human genes 0.000 claims description 10
239000011593 sulfur Chemical group 0.000 claims description 10
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
241001465754 Metazoa Species 0.000 claims description 8
125000002877 alkyl aryl group Chemical group 0.000 claims description 7
229910052736 halogen Inorganic materials 0.000 claims description 6
150000002367 halogens Chemical class 0.000 claims description 6
206010057671 Female sexual dysfunction Diseases 0.000 claims description 5
239000003085 diluting agent Substances 0.000 claims description 5
201000001881 impotence Diseases 0.000 claims description 5
230000004064 dysfunction Effects 0.000 claims description 4
230000001568 sexual effect Effects 0.000 claims description 4
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 3
208000010228 Erectile Dysfunction Diseases 0.000 claims description 3
125000000753 cycloalkyl group Chemical group 0.000 claims description 3
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 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
239000008177 pharmaceutical agent Substances 0.000 claims description 3
239000002671 adjuvant Substances 0.000 claims description 2
239000008194 pharmaceutical composition Substances 0.000 claims description 2
CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
WPZJDIVDMOQXNJ-UHFFFAOYSA-N 2-(5-acetyl-2-butoxypyridin-3-yl)-7-ethyl-5-(morpholin-4-ylmethyl)-1h-imidazo[5,1-f][1,2,4]triazin-4-one Chemical compound CCCCOC1=NC=C(C(C)=O)C=C1C(NC1=O)=NN2C1=C(CN1CCOCC1)N=C2CC WPZJDIVDMOQXNJ-UHFFFAOYSA-N 0.000 claims 1
206010011953 Decreased activity Diseases 0.000 claims 1
208000021663 Female sexual arousal disease Diseases 0.000 claims 1
208000030047 Sexual desire disease Diseases 0.000 claims 1
208000027520 Somatoform disease Diseases 0.000 claims 1
208000027753 pain disease Diseases 0.000 claims 1
102000004861 Phosphoric Diester Hydrolases Human genes 0.000 abstract description 24
108090001050 Phosphoric Diester Hydrolases Proteins 0.000 abstract description 24
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 108
238000002360 preparation method Methods 0.000 description 70
238000006243 chemical reaction Methods 0.000 description 65
239000000243 solution Substances 0.000 description 61
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 53
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 38
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
102100024085 Alpha-aminoadipic semialdehyde dehydrogenase Human genes 0.000 description 34
238000010992 reflux Methods 0.000 description 34
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 33
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 29
ZOOGRGPOEVQQDX-UHFFFAOYSA-N cyclic GMP Natural products O1C2COP(O)(=O)OC2C(O)C1N1C=NC2=C1NC(N)=NC2=O ZOOGRGPOEVQQDX-UHFFFAOYSA-N 0.000 description 26
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 25
235000019439 ethyl acetate Nutrition 0.000 description 25
239000007787 solid Substances 0.000 description 25
241000282414 Homo sapiens Species 0.000 description 24
239000002904 solvent Substances 0.000 description 24
238000005481 NMR spectroscopy Methods 0.000 description 22
239000003112 inhibitor Substances 0.000 description 22
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 20
238000004895 liquid chromatography mass spectrometry Methods 0.000 description 20
239000003921 oil Substances 0.000 description 20
235000019198 oils Nutrition 0.000 description 20
230000002829 reductive effect Effects 0.000 description 20
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 18
101150041968 CDC13 gene Proteins 0.000 description 17
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 17
101710135349 Venom phosphodiesterase Proteins 0.000 description 17
238000004440 column chromatography Methods 0.000 description 17
239000012043 crude product Substances 0.000 description 17
238000000132 electrospray ionisation Methods 0.000 description 17
239000000284 extract Substances 0.000 description 17
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
239000002585 base Substances 0.000 description 14
239000000047 product Substances 0.000 description 14
229940079593 drug Drugs 0.000 description 13
239000011734 sodium Substances 0.000 description 13
239000002253 acid Substances 0.000 description 12
239000011541 reaction mixture Substances 0.000 description 12
239000007832 Na2SO4 Substances 0.000 description 11
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 11
230000015572 biosynthetic process Effects 0.000 description 11
229910052938 sodium sulfate Inorganic materials 0.000 description 11
235000011152 sodium sulphate Nutrition 0.000 description 11
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 10
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
239000002552 dosage form Substances 0.000 description 10
125000006239 protecting group Chemical group 0.000 description 10
108090000028 Neprilysin Proteins 0.000 description 9
102000003729 Neprilysin Human genes 0.000 description 9
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
239000000556 agonist Substances 0.000 description 9
230000000694 effects Effects 0.000 description 9
239000000543 intermediate Substances 0.000 description 9
229910052708 sodium Inorganic materials 0.000 description 9
235000017557 sodium bicarbonate Nutrition 0.000 description 9
229910000030 sodium bicarbonate Inorganic materials 0.000 description 9
238000003786 synthesis reaction Methods 0.000 description 9
UZKWTJUDCOPSNM-UHFFFAOYSA-N 1-ethenoxybutane Chemical compound CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 8
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
229940124639 Selective inhibitor Drugs 0.000 description 8
239000003153 chemical reaction reagent Substances 0.000 description 8
238000007796 conventional method Methods 0.000 description 8
238000000338 in vitro Methods 0.000 description 8
239000000546 pharmaceutical excipient Substances 0.000 description 8
239000012047 saturated solution Substances 0.000 description 8
239000000725 suspension Substances 0.000 description 8
229920000858 Cyclodextrin Polymers 0.000 description 7
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 7
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
150000001408 amides Chemical class 0.000 description 7
239000012267 brine Substances 0.000 description 7
230000003389 potentiating effect Effects 0.000 description 7
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 7
UUUHXMGGBIUAPW-UHFFFAOYSA-N 1-[1-[2-[[5-amino-2-[[1-[5-(diaminomethylideneamino)-2-[[1-[3-(1h-indol-3-yl)-2-[(5-oxopyrrolidine-2-carbonyl)amino]propanoyl]pyrrolidine-2-carbonyl]amino]pentanoyl]pyrrolidine-2-carbonyl]amino]-5-oxopentanoyl]amino]-3-methylpentanoyl]pyrrolidine-2-carbon Chemical compound C1CCC(C(=O)N2C(CCC2)C(O)=O)N1C(=O)C(C(C)CC)NC(=O)C(CCC(N)=O)NC(=O)C1CCCN1C(=O)C(CCCN=C(N)N)NC(=O)C1CCCN1C(=O)C(CC=1C2=CC=CC=C2NC=1)NC(=O)C1CCC(=O)N1 UUUHXMGGBIUAPW-UHFFFAOYSA-N 0.000 description 6
QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 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
101710151321 Melanostatin Proteins 0.000 description 6
102400000064 Neuropeptide Y Human genes 0.000 description 6
108090000882 Peptidyl-Dipeptidase A Proteins 0.000 description 6
102000004270 Peptidyl-Dipeptidase A Human genes 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
239000008346 aqueous phase Substances 0.000 description 6
150000001732 carboxylic acid derivatives Chemical class 0.000 description 6
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
150000002148 esters Chemical class 0.000 description 6
238000005755 formation reaction Methods 0.000 description 6
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 6
239000010410 layer 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
URPYMXQQVHTUDU-OFGSCBOVSA-N nucleopeptide y Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(N)=O)NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](C)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)CNC(=O)[C@H]1N(CCC1)C(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCCN)NC(=O)[C@H](CO)NC(=O)[C@H]1N(CCC1)C(=O)[C@@H](N)CC=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 URPYMXQQVHTUDU-OFGSCBOVSA-N 0.000 description 6
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
239000000758 substrate Substances 0.000 description 6
QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 6
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 5
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 5
229940126062 Compound A Drugs 0.000 description 5
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 5
241000124008 Mammalia Species 0.000 description 5
108010003205 Vasoactive Intestinal Peptide Proteins 0.000 description 5
102000055135 Vasoactive Intestinal Peptide Human genes 0.000 description 5
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 5
238000009838 combustion analysis Methods 0.000 description 5
239000003480 eluent Substances 0.000 description 5
230000000155 isotopic effect Effects 0.000 description 5
230000004060 metabolic process Effects 0.000 description 5
230000003228 microsomal effect Effects 0.000 description 5
125000003386 piperidinyl group Chemical group 0.000 description 5
229920001223 polyethylene glycol Polymers 0.000 description 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
229910052725 zinc Inorganic materials 0.000 description 5
239000011701 zinc Substances 0.000 description 5
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
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 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
NYHBQMYGNKIUIF-UUOKFMHZSA-N Guanosine Chemical compound C1=NC=2C(=O)NC(N)=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O NYHBQMYGNKIUIF-UUOKFMHZSA-N 0.000 description 4
241000282412 Homo Species 0.000 description 4
LQZMLBORDGWNPD-UHFFFAOYSA-N N-iodosuccinimide Chemical compound IN1C(=O)CCC1=O LQZMLBORDGWNPD-UHFFFAOYSA-N 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
229920002472 Starch Polymers 0.000 description 4
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 4
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 4
150000001263 acyl chlorides Chemical class 0.000 description 4
239000000443 aerosol Substances 0.000 description 4
150000001299 aldehydes Chemical class 0.000 description 4
102000004305 alpha Adrenergic Receptors Human genes 0.000 description 4
108090000861 alpha Adrenergic Receptors Proteins 0.000 description 4
229910021529 ammonia Inorganic materials 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
125000002393 azetidinyl group Chemical group 0.000 description 4
239000002775 capsule Substances 0.000 description 4
NKLCNNUWBJBICK-UHFFFAOYSA-N dess–martin periodinane Chemical compound C1=CC=C2I(OC(=O)C)(OC(C)=O)(OC(C)=O)OC(=O)C2=C1 NKLCNNUWBJBICK-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
238000004090 dissolution Methods 0.000 description 4
238000010828 elution Methods 0.000 description 4
FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 4
125000000524 functional group Chemical group 0.000 description 4
235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 4
239000001866 hydroxypropyl methyl cellulose Substances 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
125000002883 imidazolyl group Chemical group 0.000 description 4
238000001727 in vivo Methods 0.000 description 4
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 4
239000008101 lactose Substances 0.000 description 4
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical group [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
125000002757 morpholinyl group Chemical group 0.000 description 4
239000012038 nucleophile Substances 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
235000019271 petrolatum Nutrition 0.000 description 4
239000012071 phase Substances 0.000 description 4
239000000843 powder Substances 0.000 description 4
150000003180 prostaglandins Chemical class 0.000 description 4
125000003226 pyrazolyl group Chemical group 0.000 description 4
125000004076 pyridyl group Chemical group 0.000 description 4
229940083618 sodium nitroprusside Drugs 0.000 description 4
239000008107 starch Substances 0.000 description 4
229940032147 starch Drugs 0.000 description 4
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