MXPA06003880A - Derivados de n-heterociclo substituido y metodos de uso. - Google Patents
Derivados de n-heterociclo substituido y metodos de uso.Info
- Publication number
- MXPA06003880A MXPA06003880A MXPA06003880A MXPA06003880A MXPA06003880A MX PA06003880 A MXPA06003880 A MX PA06003880A MX PA06003880 A MXPA06003880 A MX PA06003880A MX PA06003880 A MXPA06003880 A MX PA06003880A MX PA06003880 A MXPA06003880 A MX PA06003880A
- Authority
- MX
- Mexico
- Prior art keywords
- ethyl
- cyclohexanol
- dichlorohydrate
- phenyl
- chlorophenyl
- Prior art date
Links
- 238000011282 treatment Methods 0.000 title claims abstract description 32
- 230000000407 monoamine reuptake Effects 0.000 title abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 169
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 70
- 208000002193 Pain Diseases 0.000 claims abstract description 57
- 230000036407 pain Effects 0.000 claims abstract description 49
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 44
- 208000024891 symptom Diseases 0.000 claims abstract description 43
- 239000000203 mixture Substances 0.000 claims abstract description 42
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 33
- 230000001457 vasomotor Effects 0.000 claims abstract description 33
- 208000035475 disorder Diseases 0.000 claims abstract description 32
- 208000001640 Fibromyalgia Diseases 0.000 claims abstract description 23
- 201000001880 Sexual dysfunction Diseases 0.000 claims abstract description 18
- 231100000872 sexual dysfunction Toxicity 0.000 claims abstract description 18
- 230000002265 prevention Effects 0.000 claims abstract description 17
- 239000003814 drug Substances 0.000 claims abstract description 16
- 125000001544 thienyl group Chemical group 0.000 claims abstract description 15
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims abstract description 14
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 14
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 14
- 206010008874 Chronic Fatigue Syndrome Diseases 0.000 claims abstract description 13
- 125000002541 furyl group Chemical group 0.000 claims abstract description 13
- 208000029766 myalgic encephalomeyelitis/chronic fatigue syndrome Diseases 0.000 claims abstract description 13
- 230000002496 gastric effect Effects 0.000 claims abstract description 12
- 125000001041 indolyl group Chemical group 0.000 claims abstract description 12
- 125000000168 pyrrolyl group Chemical group 0.000 claims abstract description 12
- 208000032131 Diabetic Neuropathies Diseases 0.000 claims abstract description 11
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims abstract description 11
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 claims abstract description 11
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims abstract description 11
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 11
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 claims abstract description 11
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 claims abstract description 10
- 208000024714 major depressive disease Diseases 0.000 claims abstract description 10
- 208000012902 Nervous system disease Diseases 0.000 claims abstract description 9
- 206010066218 Stress Urinary Incontinence Diseases 0.000 claims abstract description 8
- 125000001424 substituent group Chemical group 0.000 claims abstract description 8
- 238000004519 manufacturing process Methods 0.000 claims abstract description 4
- -1 methylenedioxy, benzyloxy Chemical group 0.000 claims description 1172
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 319
- 150000001875 compounds Chemical class 0.000 claims description 160
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 133
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims description 97
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 94
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 74
- 238000006243 chemical reaction Methods 0.000 claims description 69
- 238000000034 method Methods 0.000 claims description 66
- 125000000217 alkyl group Chemical group 0.000 claims description 60
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 60
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 56
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims description 55
- AQAFFYMEIWJBCK-UHFFFAOYSA-N chloro hypochlorite cyclohexanol Chemical compound O(Cl)Cl.C1(CCCCC1)O AQAFFYMEIWJBCK-UHFFFAOYSA-N 0.000 claims description 54
- 150000003839 salts Chemical class 0.000 claims description 52
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 42
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 38
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 29
- 229910052799 carbon Inorganic materials 0.000 claims description 26
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 22
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 21
- 125000001072 heteroaryl group Chemical group 0.000 claims description 18
- 229910052717 sulfur Inorganic materials 0.000 claims description 18
- 125000005843 halogen group Chemical group 0.000 claims description 17
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 16
- 125000000304 alkynyl group Chemical group 0.000 claims description 14
- 125000003342 alkenyl group Chemical group 0.000 claims description 13
- 230000009103 reabsorption Effects 0.000 claims description 13
- BUCJHJXFXUZJHL-UHFFFAOYSA-N 1-ethylcyclohexan-1-ol Chemical compound CCC1(O)CCCCC1 BUCJHJXFXUZJHL-UHFFFAOYSA-N 0.000 claims description 12
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 9
- 125000000109 phenylethoxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])O* 0.000 claims description 9
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims description 9
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 9
- 150000003462 sulfoxides Chemical class 0.000 claims description 9
- 125000004423 acyloxy group Chemical group 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 150000002825 nitriles Chemical class 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- 206010046543 Urinary incontinence Diseases 0.000 claims description 7
- 125000004981 cycloalkylmethyl group Chemical group 0.000 claims description 7
- 125000005186 naphthyloxy group Chemical group C1(=CC=CC2=CC=CC=C12)O* 0.000 claims description 7
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 6
- VDPDOGLTRRKDGH-IRXDYDNUSA-N 1-[(1r)-2-[(3s)-3-aminopyrrolidin-1-yl]-1-(3-chlorophenyl)ethyl]cyclohexan-1-ol Chemical compound C1[C@@H](N)CCN1C[C@H](C1(O)CCCCC1)C1=CC=CC(Cl)=C1 VDPDOGLTRRKDGH-IRXDYDNUSA-N 0.000 claims description 5
- QLKWRIGUCSZESY-UHFFFAOYSA-N 1-[2-(4-aminopiperidin-1-yl)-1-[3-(trifluoromethyl)phenyl]ethyl]cyclohexan-1-ol Chemical compound C1CC(N)CCN1CC(C1(O)CCCCC1)C1=CC=CC(C(F)(F)F)=C1 QLKWRIGUCSZESY-UHFFFAOYSA-N 0.000 claims description 5
- IEXBVULLLOHJQX-TZHYSIJRSA-N 1-[2-[(3r)-3-aminopyrrolidin-1-yl]-1-[3-(trifluoromethyl)phenyl]ethyl]cyclohexan-1-ol Chemical compound C1[C@H](N)CCN1CC(C1(O)CCCCC1)C1=CC=CC(C(F)(F)F)=C1 IEXBVULLLOHJQX-TZHYSIJRSA-N 0.000 claims description 5
- PRZFZENFKPQGSQ-OWJIYDKWSA-N 1-[2-[(3s)-3-aminopyrrolidin-1-yl]-1-(4-phenylmethoxyphenyl)ethyl]cyclohexan-1-ol Chemical compound C1[C@@H](N)CCN1CC(C1(O)CCCCC1)C(C=C1)=CC=C1OCC1=CC=CC=C1 PRZFZENFKPQGSQ-OWJIYDKWSA-N 0.000 claims description 5
- MXDJTZKBLFUFPI-UHFFFAOYSA-N 1-[1-(3,4-dichlorophenyl)-2-[4-(methylamino)piperidin-1-yl]ethyl]cyclohexan-1-ol Chemical compound C1CC(NC)CCN1CC(C1(O)CCCCC1)C1=CC=C(Cl)C(Cl)=C1 MXDJTZKBLFUFPI-UHFFFAOYSA-N 0.000 claims description 4
- UWSOQSJDOBRLEZ-UHFFFAOYSA-N 1-[2-(4-pyrrolidin-1-ylpiperidin-1-yl)-1-[3-(trifluoromethyl)phenyl]ethyl]cyclohexan-1-ol Chemical compound C1CC(N2CCCC2)CCN1CC(C=1C=C(C=CC=1)C(F)(F)F)C1(O)CCCCC1 UWSOQSJDOBRLEZ-UHFFFAOYSA-N 0.000 claims description 4
- OZCFQEAODNUEQP-PYUWXLGESA-N 1-[2-[(3r)-3-aminopiperidin-1-yl]-1-[3-(trifluoromethoxy)phenyl]ethyl]cyclohexan-1-ol Chemical compound C1[C@H](N)CCCN1CC(C1(O)CCCCC1)C1=CC=CC(OC(F)(F)F)=C1 OZCFQEAODNUEQP-PYUWXLGESA-N 0.000 claims description 4
- PRZFZENFKPQGSQ-LETIRJCYSA-N 1-[2-[(3r)-3-aminopyrrolidin-1-yl]-1-(4-phenylmethoxyphenyl)ethyl]cyclohexan-1-ol Chemical compound C1[C@H](N)CCN1CC(C1(O)CCCCC1)C(C=C1)=CC=C1OCC1=CC=CC=C1 PRZFZENFKPQGSQ-LETIRJCYSA-N 0.000 claims description 4
- XHVULMOUPAEUNC-HMTLIYDFSA-N 1-[2-[(3s)-3-aminopyrrolidin-1-yl]-1-(3-chloro-4-phenylmethoxyphenyl)ethyl]cyclohexan-1-ol Chemical compound C1[C@@H](N)CCN1CC(C1(O)CCCCC1)C(C=C1Cl)=CC=C1OCC1=CC=CC=C1 XHVULMOUPAEUNC-HMTLIYDFSA-N 0.000 claims description 4
- IKRRMRWHRBSRTL-MYJWUSKBSA-N 1-[2-[(3s)-3-aminopyrrolidin-1-yl]-1-[3-(trifluoromethoxy)phenyl]ethyl]cyclohexan-1-ol Chemical compound C1[C@@H](N)CCN1CC(C1(O)CCCCC1)C1=CC=CC(OC(F)(F)F)=C1 IKRRMRWHRBSRTL-MYJWUSKBSA-N 0.000 claims description 4
- IEXBVULLLOHJQX-BHWOMJMDSA-N 1-[2-[(3s)-3-aminopyrrolidin-1-yl]-1-[3-(trifluoromethyl)phenyl]ethyl]cyclohexan-1-ol Chemical compound C1[C@@H](N)CCN1CC(C1(O)CCCCC1)C1=CC=CC(C(F)(F)F)=C1 IEXBVULLLOHJQX-BHWOMJMDSA-N 0.000 claims description 4
- NZFWFIRHBIOPMU-UHFFFAOYSA-N ClOCl.NC1CCN(CC1)CC(C1=CC=CC2=CC=CC=C12)C1(CCC1)O Chemical compound ClOCl.NC1CCN(CC1)CC(C1=CC=CC2=CC=CC=C12)C1(CCC1)O NZFWFIRHBIOPMU-UHFFFAOYSA-N 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 claims description 4
- 208000022170 stress incontinence Diseases 0.000 claims description 4
- DLVAMEAVPFFMGU-OYKVQYDMSA-N 1-[1-(3-chlorophenyl)-2-[(3s)-3-(dimethylamino)pyrrolidin-1-yl]ethyl]cyclohexan-1-ol Chemical compound C1[C@@H](N(C)C)CCN1CC(C1(O)CCCCC1)C1=CC=CC(Cl)=C1 DLVAMEAVPFFMGU-OYKVQYDMSA-N 0.000 claims description 3
- TXCJJEGCTKWDGZ-UHFFFAOYSA-N 1-[1-(3-chlorophenyl)-2-[4-(dimethylamino)piperidin-1-yl]ethyl]cyclohexan-1-ol Chemical compound C1CC(N(C)C)CCN1CC(C1(O)CCCCC1)C1=CC=CC(Cl)=C1 TXCJJEGCTKWDGZ-UHFFFAOYSA-N 0.000 claims description 3
- SEXGOJJMJYSDDB-UHFFFAOYSA-N 1-[2-(1-hydroxycyclohexyl)-2-[3-(trifluoromethoxy)phenyl]ethyl]piperidin-4-ol Chemical compound C1CC(O)CCN1CC(C1(O)CCCCC1)C1=CC=CC(OC(F)(F)F)=C1 SEXGOJJMJYSDDB-UHFFFAOYSA-N 0.000 claims description 3
- WXTDXCCEOAQFOA-UHFFFAOYSA-N 1-[2-(4-aminopiperidin-1-yl)-1-(6-methoxynaphthalen-2-yl)ethyl]cyclohexan-1-ol Chemical compound C1=CC2=CC(OC)=CC=C2C=C1C(C1(O)CCCCC1)CN1CCC(N)CC1 WXTDXCCEOAQFOA-UHFFFAOYSA-N 0.000 claims description 3
- RQNUHONIICWYKY-UHFFFAOYSA-N 1-[2-(4-aminopiperidin-1-yl)-1-[4-(trifluoromethoxy)phenyl]ethyl]cyclobutan-1-ol Chemical compound C1CC(N)CCN1CC(C1(O)CCC1)C1=CC=C(OC(F)(F)F)C=C1 RQNUHONIICWYKY-UHFFFAOYSA-N 0.000 claims description 3
- FBQYAQUOZBBVOX-UHFFFAOYSA-N 1-[2-(4-aminopiperidin-1-yl)-1-[4-(trifluoromethoxy)phenyl]ethyl]cyclohexan-1-ol Chemical compound C1CC(N)CCN1CC(C1(O)CCCCC1)C1=CC=C(OC(F)(F)F)C=C1 FBQYAQUOZBBVOX-UHFFFAOYSA-N 0.000 claims description 3
- ITRDPYOXHPOVBA-UHFFFAOYSA-N 1-[2-(4-morpholin-4-ylpiperidin-1-yl)-1-[3-(trifluoromethoxy)phenyl]ethyl]cyclohexan-1-ol Chemical compound C1CC(N2CCOCC2)CCN1CC(C=1C=C(OC(F)(F)F)C=CC=1)C1(O)CCCCC1 ITRDPYOXHPOVBA-UHFFFAOYSA-N 0.000 claims description 3
- NAKNQHNRCTUEDV-UHFFFAOYSA-N 1-[2-(4-piperidin-1-ylpiperidin-1-yl)-1-[3-(trifluoromethyl)phenyl]ethyl]cyclohexan-1-ol Chemical compound C1CC(N2CCCCC2)CCN1CC(C=1C=C(C=CC=1)C(F)(F)F)C1(O)CCCCC1 NAKNQHNRCTUEDV-UHFFFAOYSA-N 0.000 claims description 3
- GRUFFMWQWDEIDS-UHFFFAOYSA-N 1-[2-(4-piperidin-1-ylpiperidin-1-yl)-1-[4-(trifluoromethoxy)phenyl]ethyl]cyclohexan-1-ol Chemical compound C1CC(N2CCCCC2)CCN1CC(C=1C=CC(OC(F)(F)F)=CC=1)C1(O)CCCCC1 GRUFFMWQWDEIDS-UHFFFAOYSA-N 0.000 claims description 3
- XRZWFMOJPNIYOX-WTQRLHSKSA-N 1-[2-[(3r)-3-aminopiperidin-1-yl]-1-(3-chloro-4-phenylmethoxyphenyl)ethyl]cyclohexan-1-ol Chemical compound C1[C@H](N)CCCN1CC(C1(O)CCCCC1)C(C=C1Cl)=CC=C1OCC1=CC=CC=C1 XRZWFMOJPNIYOX-WTQRLHSKSA-N 0.000 claims description 3
- IKRRMRWHRBSRTL-LDCVWXEPSA-N 1-[2-[(3r)-3-aminopyrrolidin-1-yl]-1-[3-(trifluoromethoxy)phenyl]ethyl]cyclohexan-1-ol Chemical compound C1[C@H](N)CCN1CC(C1(O)CCCCC1)C1=CC=CC(OC(F)(F)F)=C1 IKRRMRWHRBSRTL-LDCVWXEPSA-N 0.000 claims description 3
- ZSEXILAFGNBAHS-VQCQRNETSA-N 1-[2-[(3r)-3-aminopyrrolidin-1-yl]-1-naphthalen-2-ylethyl]cyclohexan-1-ol Chemical compound C1[C@H](N)CCN1CC(C1(O)CCCCC1)C1=CC=C(C=CC=C2)C2=C1 ZSEXILAFGNBAHS-VQCQRNETSA-N 0.000 claims description 3
- DLDRVDRDOQTYDC-LFQPHHBNSA-N 1-[2-[(3s)-3-(methylamino)pyrrolidin-1-yl]-1-(4-phenylmethoxyphenyl)ethyl]cyclohexan-1-ol Chemical compound C1[C@@H](NC)CCN1CC(C1(O)CCCCC1)C(C=C1)=CC=C1OCC1=CC=CC=C1 DLDRVDRDOQTYDC-LFQPHHBNSA-N 0.000 claims description 3
- SETGGCQMMSSMPN-ZENAZSQFSA-N 1-[2-[(3s)-3-(methylamino)pyrrolidin-1-yl]-1-[3-(trifluoromethyl)phenyl]ethyl]cyclohexan-1-ol Chemical compound C1[C@@H](NC)CCN1CC(C1(O)CCCCC1)C1=CC=CC(C(F)(F)F)=C1 SETGGCQMMSSMPN-ZENAZSQFSA-N 0.000 claims description 3
- XRZWFMOJPNIYOX-NQCNTLBGSA-N 1-[2-[(3s)-3-aminopiperidin-1-yl]-1-(3-chloro-4-phenylmethoxyphenyl)ethyl]cyclohexan-1-ol Chemical compound C1[C@@H](N)CCCN1CC(C1(O)CCCCC1)C(C=C1Cl)=CC=C1OCC1=CC=CC=C1 XRZWFMOJPNIYOX-NQCNTLBGSA-N 0.000 claims description 3
- OZCFQEAODNUEQP-ATNAJCNCSA-N 1-[2-[(3s)-3-aminopiperidin-1-yl]-1-[3-(trifluoromethoxy)phenyl]ethyl]cyclohexan-1-ol Chemical compound C1[C@@H](N)CCCN1CC(C1(O)CCCCC1)C1=CC=CC(OC(F)(F)F)=C1 OZCFQEAODNUEQP-ATNAJCNCSA-N 0.000 claims description 3
- JMWOULRKXZWPMR-UHFFFAOYSA-N ClC=1C=C(C=CC1)C(CN1CCC(CC1)NC)C1CCCCCC1.ClOCl Chemical compound ClC=1C=C(C=CC1)C(CN1CCC(CC1)NC)C1CCCCCC1.ClOCl JMWOULRKXZWPMR-UHFFFAOYSA-N 0.000 claims description 3
- TYNGCXNUDYYIDP-UHFFFAOYSA-N ClOCl.ClC=1C=C(C=CC1)C(CN1CCC(CC1)NC)C1CCCCC1 Chemical compound ClOCl.ClC=1C=C(C=CC1)C(CN1CCC(CC1)NC)C1CCCCC1 TYNGCXNUDYYIDP-UHFFFAOYSA-N 0.000 claims description 3
- PGMLAYXVXVKFKM-UHFFFAOYSA-N ClOCl.NC1CCN(CC1)CC(C1=CC(=CC=C1)Cl)C(CCC)(CCC)O Chemical compound ClOCl.NC1CCN(CC1)CC(C1=CC(=CC=C1)Cl)C(CCC)(CCC)O PGMLAYXVXVKFKM-UHFFFAOYSA-N 0.000 claims description 3
- QGPDHIWRCZBIOV-UHFFFAOYSA-N ClOCl.NC1CCN(CC1)CC(C1=CC(=CC=C1)Cl)C1(CC2CCCCC2CC1)O Chemical compound ClOCl.NC1CCN(CC1)CC(C1=CC(=CC=C1)Cl)C1(CC2CCCCC2CC1)O QGPDHIWRCZBIOV-UHFFFAOYSA-N 0.000 claims description 3
- 206010029216 Nervousness Diseases 0.000 claims description 3
- 206010041250 Social phobia Diseases 0.000 claims description 3
- 230000002152 alkylating effect Effects 0.000 claims description 3
- 125000000068 chlorophenyl group Chemical group 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000003386 piperidinyl group Chemical group 0.000 claims description 3
- 208000019116 sleep disease Diseases 0.000 claims description 3
- IAWXIOLZWOAIRG-NDEPHWFRSA-N 1-[(1r)-1-(6-methoxynaphthalen-2-yl)-2-(4-piperidin-1-ylpiperidin-1-yl)ethyl]cyclohexan-1-ol Chemical compound C([C@@H](C1=CC2=CC=C(C=C2C=C1)OC)C1(O)CCCCC1)N(CC1)CCC1N1CCCCC1 IAWXIOLZWOAIRG-NDEPHWFRSA-N 0.000 claims description 2
- MBVYZDRQJYTINU-HSZRJFAPSA-N 1-[(1s)-2-(4-piperidin-1-ylpiperidin-1-yl)-1-[3-(trifluoromethoxy)phenyl]ethyl]cyclohexan-1-ol Chemical compound OC1([C@H](CN2CCC(CC2)N2CCCCC2)C=2C=C(OC(F)(F)F)C=CC=2)CCCCC1 MBVYZDRQJYTINU-HSZRJFAPSA-N 0.000 claims description 2
- DCOXRBWGYKLYDY-JOCHJYFZSA-N 1-[(1s)-2-(4-pyrrolidin-1-ylpiperidin-1-yl)-1-[3-(trifluoromethoxy)phenyl]ethyl]cyclohexan-1-ol Chemical compound OC1([C@H](CN2CCC(CC2)N2CCCC2)C=2C=C(OC(F)(F)F)C=CC=2)CCCCC1 DCOXRBWGYKLYDY-JOCHJYFZSA-N 0.000 claims description 2
- VDPDOGLTRRKDGH-DLBZAZTESA-N 1-[(1s)-2-[(3s)-3-aminopyrrolidin-1-yl]-1-(3-chlorophenyl)ethyl]cyclohexan-1-ol Chemical compound C1[C@@H](N)CCN1C[C@@H](C1(O)CCCCC1)C1=CC=CC(Cl)=C1 VDPDOGLTRRKDGH-DLBZAZTESA-N 0.000 claims description 2
- AWBKQEAFRBCNRO-UHFFFAOYSA-N 1-[1-(3-chloro-4-methoxyphenyl)-2-(4-piperidin-1-ylpiperidin-1-yl)ethyl]cyclohexan-1-ol Chemical compound C1=C(Cl)C(OC)=CC=C1C(C1(O)CCCCC1)CN1CCC(N2CCCCC2)CC1 AWBKQEAFRBCNRO-UHFFFAOYSA-N 0.000 claims description 2
- FSKRAXWGFULMLI-UHFFFAOYSA-N 1-[1-(3-chloro-4-phenylmethoxyphenyl)-2-(4-methoxypiperidin-1-yl)ethyl]cyclohexan-1-ol Chemical compound C1CC(OC)CCN1CC(C1(O)CCCCC1)C(C=C1Cl)=CC=C1OCC1=CC=CC=C1 FSKRAXWGFULMLI-UHFFFAOYSA-N 0.000 claims description 2
- KPAARXAICMKLFT-IKOFQBKESA-N 1-[1-(3-chloro-4-phenylmethoxyphenyl)-2-[(3r)-3-(dimethylamino)piperidin-1-yl]ethyl]cyclohexan-1-ol Chemical compound C1[C@H](N(C)C)CCCN1CC(C1(O)CCCCC1)C(C=C1Cl)=CC=C1OCC1=CC=CC=C1 KPAARXAICMKLFT-IKOFQBKESA-N 0.000 claims description 2
- IAWXIOLZWOAIRG-UHFFFAOYSA-N 1-[1-(6-methoxynaphthalen-2-yl)-2-(4-piperidin-1-ylpiperidin-1-yl)ethyl]cyclohexan-1-ol Chemical compound C1=CC2=CC(OC)=CC=C2C=C1C(C1(O)CCCCC1)CN(CC1)CCC1N1CCCCC1 IAWXIOLZWOAIRG-UHFFFAOYSA-N 0.000 claims description 2
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- KUJKJKLMBYPJIK-UHFFFAOYSA-N tert-butyl 4-[2-(5-chloro-1-benzothiophen-3-yl)-2-(1-hydroxycyclohexyl)ethyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1CC(C1(O)CCCCC1)C1=CSC2=CC=C(Cl)C=C12 KUJKJKLMBYPJIK-UHFFFAOYSA-N 0.000 description 1
- WTABKISVXPHCSF-UHFFFAOYSA-N tert-butyl 4-[2-(5-chlorothiophen-3-yl)-2-(1-hydroxycyclohexyl)ethyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1CC(C1(O)CCCCC1)C1=CSC(Cl)=C1 WTABKISVXPHCSF-UHFFFAOYSA-N 0.000 description 1
- KPHFFCRRYZHCBA-UHFFFAOYSA-N tert-butyl 4-[2-[1-[tert-butyl(dimethyl)silyl]indol-3-yl]-2-(1-hydroxycyclohexyl)acetyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1C(=O)C(C1(O)CCCCC1)C1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12 KPHFFCRRYZHCBA-UHFFFAOYSA-N 0.000 description 1
- OSUUXLGMFJMNLE-UHFFFAOYSA-N tert-butyl 4-[2-[3-(4-chlorophenyl)phenyl]-2-(1-hydroxycyclohexyl)ethyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1CC(C1(O)CCCCC1)C1=CC=CC(C=2C=CC(Cl)=CC=2)=C1 OSUUXLGMFJMNLE-UHFFFAOYSA-N 0.000 description 1
- JPAJGSNOKRPRKG-UHFFFAOYSA-N tert-butyl 4-[2-[4-(2-cyanophenyl)phenyl]-2-(1-hydroxycyclohexyl)ethyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1CC(C1(O)CCCCC1)C1=CC=C(C=2C(=CC=CC=2)C#N)C=C1 JPAJGSNOKRPRKG-UHFFFAOYSA-N 0.000 description 1
- HRSXHKPUMHJEAI-UHFFFAOYSA-N tert-butyl 4-[2-[4-(3,4-dichlorophenyl)phenyl]-2-(1-hydroxycyclobutyl)ethyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1CC(C1(O)CCC1)C1=CC=C(C=2C=C(Cl)C(Cl)=CC=2)C=C1 HRSXHKPUMHJEAI-UHFFFAOYSA-N 0.000 description 1
- VYUUJWCGAKEYJC-UHFFFAOYSA-N tert-butyl 4-[2-[4-(3-chlorophenyl)phenyl]-2-(1-hydroxycyclobutyl)ethyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1CC(C1(O)CCC1)C1=CC=C(C=2C=C(Cl)C=CC=2)C=C1 VYUUJWCGAKEYJC-UHFFFAOYSA-N 0.000 description 1
- HHUXIDJJHIRZBQ-UHFFFAOYSA-N tert-butyl 4-[2-[4-(3-cyanophenyl)phenyl]-2-(1-hydroxycyclohexyl)ethyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1CC(C1(O)CCCCC1)C1=CC=C(C=2C=C(C=CC=2)C#N)C=C1 HHUXIDJJHIRZBQ-UHFFFAOYSA-N 0.000 description 1
- ZPYLADGUWFOTGJ-UHFFFAOYSA-N tert-butyl 4-[2-[4-ethoxy-3-(trifluoromethoxy)phenyl]-2-(1-hydroxycyclohexyl)ethyl]piperazine-1-carboxylate Chemical compound C1=C(OC(F)(F)F)C(OCC)=CC=C1C(C1(O)CCCCC1)CN1CCN(C(=O)OC(C)(C)C)CC1 ZPYLADGUWFOTGJ-UHFFFAOYSA-N 0.000 description 1
- LFKDJXLFVYVEFG-UHFFFAOYSA-N tert-butyl carbamate Chemical compound CC(C)(C)OC(N)=O LFKDJXLFVYVEFG-UHFFFAOYSA-N 0.000 description 1
- 150000008027 tertiary esters Chemical class 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 230000000542 thalamic effect Effects 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000004797 therapeutic response Effects 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- QNMBSXGYAQZCTN-UHFFFAOYSA-N thiophen-3-ylboronic acid Chemical compound OB(O)C=1C=CSC=1 QNMBSXGYAQZCTN-UHFFFAOYSA-N 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000012549 training Methods 0.000 description 1
- 230000032258 transport Effects 0.000 description 1
- 230000000472 traumatic effect Effects 0.000 description 1
- 238000011269 treatment regimen Methods 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- QIWRFOJWQSSRJZ-UHFFFAOYSA-N tributyl(ethenyl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C=C QIWRFOJWQSSRJZ-UHFFFAOYSA-N 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 206010044652 trigeminal neuralgia Diseases 0.000 description 1
- FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 210000000626 ureter Anatomy 0.000 description 1
- 230000024883 vasodilation Effects 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
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- 239000001993 wax Substances 0.000 description 1
- BLGXFZZNTVWLAY-SCYLSFHTSA-N yohimbine Chemical compound C1=CC=C2C(CCN3C[C@@H]4CC[C@H](O)[C@@H]([C@H]4C[C@H]33)C(=O)OC)=C3NC2=C1 BLGXFZZNTVWLAY-SCYLSFHTSA-N 0.000 description 1
- 229960000317 yohimbine Drugs 0.000 description 1
- AADVZSXPNRLYLV-UHFFFAOYSA-N yohimbine carboxylic acid Natural products C1=CC=C2C(CCN3CC4CCC(C(C4CC33)C(O)=O)O)=C3NC2=C1 AADVZSXPNRLYLV-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
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| US7517899B2 (en) * | 2004-03-30 | 2009-04-14 | Wyeth | Phenylaminopropanol derivatives and methods of their use |
| ATE484509T1 (de) | 2004-08-02 | 2010-10-15 | Glaxo Group Ltd | Antibakterielle mittel |
| WO2007067575A2 (en) * | 2005-12-05 | 2007-06-14 | Wyeth | Process for preparing substituted aryl cycloalkanol derivatives |
| US7994190B2 (en) | 2006-11-01 | 2011-08-09 | Bristol-Myers Squibb Company | Modulators of glucocorticoid receptor, AP-1, and/or NF-κB activity and use thereof |
| UY32858A (es) | 2009-08-31 | 2011-03-31 | Abbott Healthcare Products Bv | Derivados de (tio)morfolina como moduladores de sip |
| JP5752691B2 (ja) | 2009-09-29 | 2015-07-22 | グラクソ グループ リミテッドGlaxo Group Limited | 新規化合物 |
| JP6209720B2 (ja) | 2010-02-02 | 2017-10-11 | エージェンシー フォー サイエンス,テクノロジー アンド リサーチ | 官能化された防汚化合物及びその使用 |
| TW201206893A (en) * | 2010-07-09 | 2012-02-16 | Abbott Healthcare Products Bv | Bisaryl (thio) morpholine derivatives as S1P modulators |
| TWI522361B (zh) | 2010-07-09 | 2016-02-21 | 艾伯維公司 | 作為s1p調節劑的稠合雜環衍生物 |
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| US4826844A (en) * | 1987-09-30 | 1989-05-02 | American Home Products Corporation | Substituted 1-(aralkyl-piperazinoalkyl) cycloalkanols |
| ATE114467T1 (de) | 1990-06-01 | 1994-12-15 | Merrell Dow Pharma | (+)-alpha-(2,3 dimethoxyphenyl)-1-(2- (fluorophenyl)ethyl>-4-piperidinmethanol. |
| US5502047A (en) * | 1993-03-22 | 1996-03-26 | Kavey; Neil B. | Treatment for insomnia |
| CZ296263B6 (cs) | 1996-03-25 | 2006-02-15 | Eli Lilly And Company | Farmaceutická kompozice pro lécení bolesti a jejípouzití |
| KR20010015918A (ko) | 1998-03-02 | 2001-02-26 | 피터 지. 스트링거 | 안면홍조를 감소시키기 위한 플루옥세틴 히드로클로라이드 |
| ES2305606T3 (es) | 1999-04-06 | 2008-11-01 | Sepracor Inc. | Succinato de o-desmetilvenlafaxina. |
| TW564247B (en) * | 1999-04-08 | 2003-12-01 | Akzo Nobel Nv | Bicyclic heteraromatic compound |
| JP2003503450A (ja) * | 1999-07-01 | 2003-01-28 | ファルマシア・アンド・アップジョン・カンパニー | 高選択的ノルエピネフリン再取込みインヒビターおよびその使用方法 |
| AU6640800A (en) * | 1999-08-11 | 2001-03-05 | Vermeer Manufacturing Company | Automated lubricant dispensing system and method for a horizontal directional drilling machine |
| AU2001279294A1 (en) * | 2000-07-06 | 2002-01-21 | Neurogen Corporation | Melanin concentrating hormone receptor ligands |
| DE60119047D1 (de) | 2000-08-31 | 2006-06-01 | Pfizer | Phenoxyphenylheterozyklen als Serotonin-Wiederaufnahmehemmer |
| DE60122015T2 (de) | 2000-10-13 | 2006-11-23 | Neurosearch A/S | Behandlung affektiver störungen durch kombinierte wirkung eines nikotinischen rezeptoragonisten und einer monoaminergischen substanz |
| ATE369330T1 (de) | 2001-02-12 | 2007-08-15 | Wyeth Corp | O-desmethyl-venlafaxine succinat salz |
| US6557831B2 (en) * | 2001-03-05 | 2003-05-06 | Erwin Industries, Inc. | Fence bracket |
| EP1383495A1 (en) | 2001-03-29 | 2004-01-28 | Eli Lilly And Company | Duloxetine for treatment of hot flashes |
| GB0108046D0 (en) | 2001-03-30 | 2001-05-23 | Astrazeneca Ab | Chemical compounds |
| EP1266659A1 (en) | 2001-06-11 | 2002-12-18 | Pantarhei Bioscience B.V. | Pyridoxal in combination with serotonin re-uptake inhibitor for the treatment of hot flushes |
| US20040259850A1 (en) | 2001-10-31 | 2004-12-23 | Alves Stephen E. | Method for treating or preventing symptoms of hormonal variation including hot flashes |
| US6602911B2 (en) | 2001-11-05 | 2003-08-05 | Cypress Bioscience, Inc. | Methods of treating fibromyalgia |
| SE0103818D0 (sv) * | 2001-11-15 | 2001-11-15 | Astrazeneca Ab | Chemical compounds |
| CA2476218A1 (en) | 2002-02-08 | 2003-08-14 | President And Fellows Of Harvard College | Therapeutic compounds |
| PL223471B1 (pl) | 2002-03-15 | 2016-10-31 | Cypress Bioscience Inc | Kompozycja farmaceutyczna zawierająca milnacypran do stosowania w leczeniu zespołu nadwrażliwości jelita grubego |
| TW200402289A (en) * | 2002-05-17 | 2004-02-16 | Wyeth Corp | Methods of treating gastrointestinary and genitourinary pain disorders |
| CA2495452A1 (en) | 2002-08-14 | 2004-02-26 | Pharmacia & Upjohn Company Llc | Use of reboxetine for the treatment of hot flashes |
| US20040180879A1 (en) * | 2002-10-15 | 2004-09-16 | Deecher Darlene Coleman | Novel method of treating vasomotor symptoms |
| US20040152710A1 (en) * | 2002-10-15 | 2004-08-05 | Deecher Darlene Coleman | Use of norepinephrine reuptake modulators for preventing and treating vasomotor symptoms |
| US7345096B2 (en) * | 2002-10-15 | 2008-03-18 | Wyeth | Use of norepinephrine reuptake modulators for preventing and treating vasomotor symptoms |
-
2004
- 2004-10-12 US US10/962,971 patent/US7550485B2/en not_active Expired - Fee Related
- 2004-10-13 KR KR1020067007312A patent/KR20070026326A/ko not_active Withdrawn
- 2004-10-13 WO PCT/US2004/033732 patent/WO2005037279A1/en not_active Ceased
- 2004-10-13 CA CA002540191A patent/CA2540191A1/en not_active Abandoned
- 2004-10-13 AT AT04794958T patent/ATE400273T1/de not_active IP Right Cessation
- 2004-10-13 EP EP04794958A patent/EP1673084B1/en not_active Expired - Lifetime
- 2004-10-13 MX MXPA06003880A patent/MXPA06003880A/es active IP Right Grant
- 2004-10-13 JP JP2006535619A patent/JP2007508395A/ja active Pending
- 2004-10-13 DE DE602004014955T patent/DE602004014955D1/de not_active Expired - Fee Related
- 2004-10-13 TW TW093131002A patent/TW200526619A/zh unknown
- 2004-10-13 BR BRPI0415294-8A patent/BRPI0415294A/pt not_active IP Right Cessation
- 2004-10-13 AU AU2004281746A patent/AU2004281746A1/en not_active Withdrawn
- 2004-10-14 PA PA20048615001A patent/PA8615001A1/es unknown
- 2004-10-14 AR ARP040103715A patent/AR046283A1/es unknown
- 2004-10-14 PE PE2004000995A patent/PE20050440A1/es not_active Application Discontinuation
-
2006
- 2006-03-21 IL IL174472A patent/IL174472A0/en unknown
- 2006-04-12 EC EC2006006506A patent/ECSP066506A/es unknown
-
2009
- 2009-05-18 US US12/467,594 patent/US20090227585A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| JP2007508395A (ja) | 2007-04-05 |
| IL174472A0 (en) | 2006-08-01 |
| KR20070026326A (ko) | 2007-03-08 |
| ECSP066506A (es) | 2006-10-10 |
| US20050187251A1 (en) | 2005-08-25 |
| TW200526619A (en) | 2005-08-16 |
| PA8615001A1 (es) | 2005-08-10 |
| PE20050440A1 (es) | 2005-07-25 |
| WO2005037279A1 (en) | 2005-04-28 |
| AU2004281746A1 (en) | 2005-04-28 |
| DE602004014955D1 (de) | 2008-08-21 |
| BRPI0415294A (pt) | 2006-12-19 |
| US7550485B2 (en) | 2009-06-23 |
| ATE400273T1 (de) | 2008-07-15 |
| AR046283A1 (es) | 2005-11-30 |
| CA2540191A1 (en) | 2005-04-28 |
| EP1673084A1 (en) | 2006-06-28 |
| EP1673084B1 (en) | 2008-07-09 |
| US20090227585A1 (en) | 2009-09-10 |
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