MXPA06003877A - Derivados de fenilpiperazin cicloalcanol y metodos de su uso. - Google Patents

Info

Publication number

MXPA06003877A

MXPA06003877A MXPA06003877A MXPA06003877A MXPA06003877A MX PA06003877 A MXPA06003877 A MX PA06003877A MX PA06003877 A MXPA06003877 A MX PA06003877A MX PA06003877 A MXPA06003877 A MX PA06003877A MX PA06003877 A MXPA06003877 A MX PA06003877A

Authority

MX

Mexico

Prior art keywords

piperazin

ylethyl

chlorophenyl

cyclobutanol

subject

Prior art date

2003-10-14

Links

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• 238000000034 method Methods 0.000 title claims abstract description 64
• YZTJYBJCZXZGCT-UHFFFAOYSA-N phenylpiperazine Chemical compound C1CNCCN1C1=CC=CC=C1 YZTJYBJCZXZGCT-UHFFFAOYSA-N 0.000 title abstract description 5
• 208000002193 Pain Diseases 0.000 claims abstract description 56
• 230000036407 pain Effects 0.000 claims abstract description 48
• 208000024891 symptom Diseases 0.000 claims abstract description 39
• 230000001457 vasomotor Effects 0.000 claims abstract description 29
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 28
• 239000000203 mixture Substances 0.000 claims abstract description 28
• 208000035475 disorder Diseases 0.000 claims abstract description 27
• 201000001880 Sexual dysfunction Diseases 0.000 claims abstract description 16
• 231100000872 sexual dysfunction Toxicity 0.000 claims abstract description 16
• 206010008874 Chronic Fatigue Syndrome Diseases 0.000 claims abstract description 10
• 208000029766 myalgic encephalomeyelitis/chronic fatigue syndrome Diseases 0.000 claims abstract description 10
• 230000002496 gastric effect Effects 0.000 claims abstract description 9
• 208000024714 major depressive disease Diseases 0.000 claims abstract description 9
• 208000032131 Diabetic Neuropathies Diseases 0.000 claims abstract description 8
• 206010066218 Stress Urinary Incontinence Diseases 0.000 claims abstract description 4
• 150000001875 compounds Chemical class 0.000 claims description 118
• -1 methylenedioxy Chemical group 0.000 claims description 101
• 150000003839 salts Chemical class 0.000 claims description 41
• 125000004432 carbon atom Chemical group C* 0.000 claims description 36
• 125000000217 alkyl group Chemical group 0.000 claims description 22
• 208000001640 Fibromyalgia Diseases 0.000 claims description 17
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 16
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 14
• 125000000623 heterocyclic group Chemical group 0.000 claims description 14
• KTHXBEHDVMTNOH-UHFFFAOYSA-N cyclobutanol Chemical compound OC1CCC1 KTHXBEHDVMTNOH-UHFFFAOYSA-N 0.000 claims description 12
• 229910052757 nitrogen Inorganic materials 0.000 claims description 11
• 230000009103 reabsorption Effects 0.000 claims description 10
• 229910052799 carbon Inorganic materials 0.000 claims description 9
• 229910052739 hydrogen Inorganic materials 0.000 claims description 9
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
• 239000001257 hydrogen Substances 0.000 claims description 8
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
• 206010046543 Urinary incontinence Diseases 0.000 claims description 6
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
• REBCRUZAHKPPJG-UHFFFAOYSA-N 1-[1-(4-bromophenyl)-2-piperazin-1-ylethyl]cyclobutan-1-ol Chemical compound C1CNCCN1CC(C=1C=CC(Br)=CC=1)C1(O)CCC1 REBCRUZAHKPPJG-UHFFFAOYSA-N 0.000 claims description 5
• MCGGADLCNVOIBI-UHFFFAOYSA-N 1-[2-piperazin-1-yl-1-[3-(trifluoromethyl)phenyl]ethyl]cyclobutan-1-ol Chemical compound C1CNCCN1CC(C=1C=C(C=CC=1)C(F)(F)F)C1(O)CCC1 MCGGADLCNVOIBI-UHFFFAOYSA-N 0.000 claims description 5
• 125000003545 alkoxy group Chemical group 0.000 claims description 5
• 229910052736 halogen Inorganic materials 0.000 claims description 5
• 150000002367 halogens Chemical class 0.000 claims description 5
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 5
• PZQVDLYPNAADGQ-UHFFFAOYSA-N 1-[1-(3-chlorophenyl)-2-piperazin-1-ylethyl]cyclohexan-1-ol Chemical compound C1CNCCN1CC(C=1C=C(Cl)C=CC=1)C1(O)CCCCC1 PZQVDLYPNAADGQ-UHFFFAOYSA-N 0.000 claims description 4
• KZMYISUBTLBMKL-UHFFFAOYSA-N 1-[2-(4-methylpiperazin-1-yl)-1-[3-(trifluoromethyl)phenyl]ethyl]cyclobutan-1-ol Chemical compound C1CN(C)CCN1CC(C1(O)CCC1)C1=CC=CC(C(F)(F)F)=C1 KZMYISUBTLBMKL-UHFFFAOYSA-N 0.000 claims description 4
• 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 4
• 125000005843 halogen group Chemical group 0.000 claims description 4
• LBHZTGKCTKOYTN-UHFFFAOYSA-N 1-[1-(2-fluorophenyl)-2-piperazin-1-ylethyl]cyclohexan-1-ol Chemical compound C1CNCCN1CC(C=1C(=CC=CC=1)F)C1(O)CCCCC1 LBHZTGKCTKOYTN-UHFFFAOYSA-N 0.000 claims description 3
• SIMGTBMOANUZIG-NNJIEVJOSA-N 1-[1-(3-chlorophenyl)-2-[(3r)-3-methylpiperazin-1-yl]ethyl]cyclohexan-1-ol Chemical compound C1CN[C@H](C)CN1CC(C1(O)CCCCC1)C1=CC=CC(Cl)=C1 SIMGTBMOANUZIG-NNJIEVJOSA-N 0.000 claims description 3
• HPBLUEOXHZOXFX-UHFFFAOYSA-N 1-[1-(4-chlorophenyl)-2-piperazin-1-ylethyl]cyclobutan-1-ol Chemical compound C1CNCCN1CC(C=1C=CC(Cl)=CC=1)C1(O)CCC1 HPBLUEOXHZOXFX-UHFFFAOYSA-N 0.000 claims description 3
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
• 206010029216 Nervousness Diseases 0.000 claims description 3
• 206010041250 Social phobia Diseases 0.000 claims description 3
• 125000004423 acyloxy group Chemical group 0.000 claims description 3
• 239000003937 drug carrier Substances 0.000 claims description 3
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
• 208000019116 sleep disease Diseases 0.000 claims description 3
• PZQVDLYPNAADGQ-KRWDZBQOSA-N 1-[(1r)-1-(3-chlorophenyl)-2-piperazin-1-ylethyl]cyclohexan-1-ol Chemical compound OC1([C@@H](CN2CCNCC2)C=2C=C(Cl)C=CC=2)CCCCC1 PZQVDLYPNAADGQ-KRWDZBQOSA-N 0.000 claims description 2
• PZQVDLYPNAADGQ-QGZVFWFLSA-N 1-[(1s)-1-(3-chlorophenyl)-2-piperazin-1-ylethyl]cyclohexan-1-ol Chemical compound OC1([C@H](CN2CCNCC2)C=2C=C(Cl)C=CC=2)CCCCC1 PZQVDLYPNAADGQ-QGZVFWFLSA-N 0.000 claims description 2
• QFIJRJZGJBEPSZ-UHFFFAOYSA-N 1-[1-(2-bromophenyl)-2-piperazin-1-ylethyl]cyclohexan-1-ol Chemical compound C1CNCCN1CC(C=1C(=CC=CC=1)Br)C1(O)CCCCC1 QFIJRJZGJBEPSZ-UHFFFAOYSA-N 0.000 claims description 2
• BLTKKNKJEHRTJP-UHFFFAOYSA-N 1-[1-(2-fluorophenyl)-2-piperazin-1-ylethyl]cyclobutan-1-ol Chemical compound C1CNCCN1CC(C=1C(=CC=CC=1)F)C1(O)CCC1 BLTKKNKJEHRTJP-UHFFFAOYSA-N 0.000 claims description 2
• IAXITOGKMSXBJM-UHFFFAOYSA-N 1-[1-(3-bromo-4-methoxyphenyl)-2-piperazin-1-ylethyl]cyclooctan-1-ol Chemical compound C1=C(Br)C(OC)=CC=C1C(C1(O)CCCCCCC1)CN1CCNCC1 IAXITOGKMSXBJM-UHFFFAOYSA-N 0.000 claims description 2
• DGBKDBRUKWAZBY-UHFFFAOYSA-N 1-[1-(3-bromophenyl)-2-(4-methylpiperazin-1-yl)ethyl]cyclooctan-1-ol Chemical compound C1CN(C)CCN1CC(C1(O)CCCCCCC1)C1=CC=CC(Br)=C1 DGBKDBRUKWAZBY-UHFFFAOYSA-N 0.000 claims description 2
• OBYMFFTYBMFUTN-UHFFFAOYSA-N 1-[1-(3-bromophenyl)-2-piperazin-1-ylethyl]cyclobutan-1-ol Chemical compound C1CNCCN1CC(C=1C=C(Br)C=CC=1)C1(O)CCC1 OBYMFFTYBMFUTN-UHFFFAOYSA-N 0.000 claims description 2
• HHRVKAJJFQQGMY-UHFFFAOYSA-N 1-[1-(3-bromophenyl)-2-piperazin-1-ylethyl]cycloheptan-1-ol Chemical compound C1CNCCN1CC(C=1C=C(Br)C=CC=1)C1(O)CCCCCC1 HHRVKAJJFQQGMY-UHFFFAOYSA-N 0.000 claims description 2
• QIEWQGGMPRNSTF-UHFFFAOYSA-N 1-[1-(3-bromophenyl)-2-piperazin-1-ylethyl]cyclohexan-1-ol Chemical compound C1CNCCN1CC(C=1C=C(Br)C=CC=1)C1(O)CCCCC1 QIEWQGGMPRNSTF-UHFFFAOYSA-N 0.000 claims description 2
• CZRBZQHNTQGFDV-UHFFFAOYSA-N 1-[1-(3-bromophenyl)-2-piperazin-1-ylethyl]cyclooctan-1-ol Chemical compound C1CNCCN1CC(C=1C=C(Br)C=CC=1)C1(O)CCCCCCC1 CZRBZQHNTQGFDV-UHFFFAOYSA-N 0.000 claims description 2
• DHGBPKXIJTZIQH-UHFFFAOYSA-N 1-[1-(3-bromophenyl)-2-piperazin-1-ylethyl]cyclopentan-1-ol Chemical compound C1CNCCN1CC(C=1C=C(Br)C=CC=1)C1(O)CCCC1 DHGBPKXIJTZIQH-UHFFFAOYSA-N 0.000 claims description 2
• ZFQGQANQGWASIE-UHFFFAOYSA-N 1-[1-(3-chlorophenyl)-2-(4-methylpiperazin-1-yl)ethyl]cyclooctan-1-ol Chemical compound C1CN(C)CCN1CC(C1(O)CCCCCCC1)C1=CC=CC(Cl)=C1 ZFQGQANQGWASIE-UHFFFAOYSA-N 0.000 claims description 2
• SIMGTBMOANUZIG-BUSXIPJBSA-N 1-[1-(3-chlorophenyl)-2-[(3s)-3-methylpiperazin-1-yl]ethyl]cyclohexan-1-ol Chemical compound C1CN[C@@H](C)CN1CC(C1(O)CCCCC1)C1=CC=CC(Cl)=C1 SIMGTBMOANUZIG-BUSXIPJBSA-N 0.000 claims description 2
• GNFBWBLHLHVEHI-UHFFFAOYSA-N 1-[1-(3-chlorophenyl)-2-piperazin-1-ylethyl]cycloheptan-1-ol Chemical compound C1CNCCN1CC(C=1C=C(Cl)C=CC=1)C1(O)CCCCCC1 GNFBWBLHLHVEHI-UHFFFAOYSA-N 0.000 claims description 2
• DIMZLFDDDJZTNC-UHFFFAOYSA-N 1-[1-(3-chlorophenyl)-2-piperazin-1-ylethyl]cyclooctan-1-ol Chemical compound C1CNCCN1CC(C=1C=C(Cl)C=CC=1)C1(O)CCCCCCC1 DIMZLFDDDJZTNC-UHFFFAOYSA-N 0.000 claims description 2
• BDZIOTCFFYFCSB-UHFFFAOYSA-N 1-[1-(3-chlorophenyl)-2-piperazin-1-ylethyl]cyclopentan-1-ol Chemical compound C1CNCCN1CC(C=1C=C(Cl)C=CC=1)C1(O)CCCC1 BDZIOTCFFYFCSB-UHFFFAOYSA-N 0.000 claims description 2
• APZLULIMMIJDAY-UHFFFAOYSA-N 1-[1-(3-fluorophenyl)-2-(4-methylpiperazin-1-yl)ethyl]cyclobutan-1-ol Chemical compound C1CN(C)CCN1CC(C1(O)CCC1)C1=CC=CC(F)=C1 APZLULIMMIJDAY-UHFFFAOYSA-N 0.000 claims description 2
• QWUVCZDEMPCCJX-UHFFFAOYSA-N 1-[1-(3-fluorophenyl)-2-piperazin-1-ylethyl]cyclobutan-1-ol Chemical compound C1CNCCN1CC(C=1C=C(F)C=CC=1)C1(O)CCC1 QWUVCZDEMPCCJX-UHFFFAOYSA-N 0.000 claims description 2
• PIBZTCVMCNNFRR-UHFFFAOYSA-N 1-[1-(3-fluorophenyl)-2-piperazin-1-ylethyl]cyclohexan-1-ol Chemical compound C1CNCCN1CC(C=1C=C(F)C=CC=1)C1(O)CCCCC1 PIBZTCVMCNNFRR-UHFFFAOYSA-N 0.000 claims description 2
• ZNOWPRXCOCARHQ-UHFFFAOYSA-N 1-[1-(4-bromophenyl)-2-(4-methylpiperazin-1-yl)ethyl]cyclobutan-1-ol Chemical compound C1CN(C)CCN1CC(C1(O)CCC1)C1=CC=C(Br)C=C1 ZNOWPRXCOCARHQ-UHFFFAOYSA-N 0.000 claims description 2
• WZKIGEMCGDZHTR-UHFFFAOYSA-N 1-[1-(4-bromophenyl)-2-piperazin-1-ylethyl]cyclohexan-1-ol Chemical compound C1CNCCN1CC(C=1C=CC(Br)=CC=1)C1(O)CCCCC1 WZKIGEMCGDZHTR-UHFFFAOYSA-N 0.000 claims description 2
• KHWNQEDSMGUKSX-UHFFFAOYSA-N 1-[1-(4-chlorophenyl)-2-piperazin-1-ylethyl]cyclohexan-1-ol Chemical compound C1CNCCN1CC(C=1C=CC(Cl)=CC=1)C1(O)CCCCC1 KHWNQEDSMGUKSX-UHFFFAOYSA-N 0.000 claims description 2
• UZVBARIHCIAPAS-UHFFFAOYSA-N 1-[1-(4-fluorophenyl)-2-(4-methylpiperazin-1-yl)ethyl]cyclobutan-1-ol Chemical compound C1CN(C)CCN1CC(C1(O)CCC1)C1=CC=C(F)C=C1 UZVBARIHCIAPAS-UHFFFAOYSA-N 0.000 claims description 2
• JMKKGNSMJRPWLW-UHFFFAOYSA-N 1-[1-(4-fluorophenyl)-2-piperazin-1-ylethyl]cyclobutan-1-ol Chemical compound C1CNCCN1CC(C=1C=CC(F)=CC=1)C1(O)CCC1 JMKKGNSMJRPWLW-UHFFFAOYSA-N 0.000 claims description 2
• 208000019901 Anxiety disease Diseases 0.000 claims description 2
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• OPAKGKQKMQGOGL-UHFFFAOYSA-N 1-[1-(3,4-dichlorophenyl)-2-piperazin-1-ylethyl]cyclohexan-1-ol Chemical compound C1CNCCN1CC(C=1C=C(Cl)C(Cl)=CC=1)C1(O)CCCCC1 OPAKGKQKMQGOGL-UHFFFAOYSA-N 0.000 claims 1
• 150000001721 carbon Chemical group 0.000 claims 1
• XCIXKGXIYUWCLL-UHFFFAOYSA-N cyclopentanol Chemical compound OC1CCCC1 XCIXKGXIYUWCLL-UHFFFAOYSA-N 0.000 claims 1
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• 210000004027 cell Anatomy 0.000 description 33
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• 239000000243 solution Substances 0.000 description 27
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• 230000000694 effects Effects 0.000 description 22
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