JP2007517855A5 - - Google Patents
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- Publication number
- JP2007517855A5 JP2007517855A5 JP2006548459A JP2006548459A JP2007517855A5 JP 2007517855 A5 JP2007517855 A5 JP 2007517855A5 JP 2006548459 A JP2006548459 A JP 2006548459A JP 2006548459 A JP2006548459 A JP 2006548459A JP 2007517855 A5 JP2007517855 A5 JP 2007517855A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- alkoxy
- pharmaceutically acceptable
- acceptable salt
- phenyl
- Prior art date
- Legal status (The legal status 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 status listed.)
- Abandoned
Links
- 150000001875 compounds Chemical class 0.000 claims description 23
- 125000003118 aryl group Chemical group 0.000 claims description 10
- -1 het Chemical group 0.000 claims description 10
- 125000000623 heterocyclic group Chemical group 0.000 claims description 8
- 125000005842 heteroatom Chemical group 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims 52
- 150000003839 salts Chemical class 0.000 claims 18
- 125000003545 alkoxy group Chemical group 0.000 claims 16
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims 8
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 7
- 125000005843 halogen group Chemical group 0.000 claims 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 7
- 125000001424 substituent group Chemical group 0.000 claims 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 5
- 208000035475 disorder Diseases 0.000 claims 5
- 239000008194 pharmaceutical composition Substances 0.000 claims 5
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 4
- 229960002748 norepinephrine Drugs 0.000 claims 4
- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 claims 4
- 229940076279 serotonin Drugs 0.000 claims 4
- 125000001054 5 membered carbocyclic group Chemical group 0.000 claims 3
- 125000004008 6 membered carbocyclic group Chemical group 0.000 claims 3
- 241000124008 Mammalia Species 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 230000002485 urinary effect Effects 0.000 claims 3
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 2
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 2
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 2
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims 2
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims 2
- 208000001640 Fibromyalgia Diseases 0.000 claims 2
- 208000002193 Pain Diseases 0.000 claims 2
- 206010046543 Urinary incontinence Diseases 0.000 claims 2
- 206010036596 premature ejaculation Diseases 0.000 claims 2
- WARUECLCXNMKJR-UHFFFAOYSA-N 1-[1-(2-fluorophenyl)-2-[2-(trifluoromethoxy)phenyl]ethyl]piperazine Chemical compound FC1=CC=CC=C1C(N1CCNCC1)CC1=CC=CC=C1OC(F)(F)F WARUECLCXNMKJR-UHFFFAOYSA-N 0.000 claims 1
- LRKGVRWKYSKWQW-UHFFFAOYSA-N 1-[1-(3-fluorophenyl)-2-[2-(trifluoromethoxy)phenyl]ethyl]piperazine Chemical compound FC1=CC=CC(C(CC=2C(=CC=CC=2)OC(F)(F)F)N2CCNCC2)=C1 LRKGVRWKYSKWQW-UHFFFAOYSA-N 0.000 claims 1
- SQSFWPVYWBTHEX-UHFFFAOYSA-N 1-[1-(4-fluorophenyl)-2-[2-(trifluoromethoxy)phenyl]ethyl]piperazine Chemical compound C1=CC(F)=CC=C1C(N1CCNCC1)CC1=CC=CC=C1OC(F)(F)F SQSFWPVYWBTHEX-UHFFFAOYSA-N 0.000 claims 1
- GYZLMHZBYPNULH-UHFFFAOYSA-N 1-[1-phenyl-2-[2-(trifluoromethoxy)phenyl]ethyl]piperazine Chemical compound FC(F)(F)OC1=CC=CC=C1CC(C=1C=CC=CC=1)N1CCNCC1 GYZLMHZBYPNULH-UHFFFAOYSA-N 0.000 claims 1
- LRNIUFGVSNVUDQ-UHFFFAOYSA-N 1-[2-(2-chloro-6-fluorophenyl)-1-phenylethyl]piperazine Chemical compound FC1=CC=CC(Cl)=C1CC(C=1C=CC=CC=1)N1CCNCC1 LRNIUFGVSNVUDQ-UHFFFAOYSA-N 0.000 claims 1
- SDLVJPBOBLQFEW-UHFFFAOYSA-N 1-[2-(2-chlorophenyl)-1-phenylethyl]piperazine Chemical compound ClC1=CC=CC=C1CC(C=1C=CC=CC=1)N1CCNCC1 SDLVJPBOBLQFEW-UHFFFAOYSA-N 0.000 claims 1
- CVFBVSUFNWOPLD-UHFFFAOYSA-N 1-[2-(2-ethoxyphenyl)-1-phenylethyl]piperazine Chemical compound CCOC1=CC=CC=C1CC(C=1C=CC=CC=1)N1CCNCC1 CVFBVSUFNWOPLD-UHFFFAOYSA-N 0.000 claims 1
- PFTJCYRHNKTTTO-UHFFFAOYSA-N 1-[2-(2-methoxyphenyl)-1-phenylethyl]piperazine Chemical compound COC1=CC=CC=C1CC(C=1C=CC=CC=1)N1CCNCC1 PFTJCYRHNKTTTO-UHFFFAOYSA-N 0.000 claims 1
- VCVDPONUNCPTCQ-UHFFFAOYSA-N 1-[2-[2-(difluoromethoxy)phenyl]-1-phenylethyl]piperazine Chemical compound FC(F)OC1=CC=CC=C1CC(C=1C=CC=CC=1)N1CCNCC1 VCVDPONUNCPTCQ-UHFFFAOYSA-N 0.000 claims 1
- 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 239000011630 iodine Substances 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 125000005561 phenanthryl group Chemical group 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
- 229910052725 zinc Inorganic materials 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000002883 imidazolyl group Chemical group 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 125000002785 azepinyl group Chemical group 0.000 description 1
- 125000003310 benzodiazepinyl group Chemical group N1N=C(C=CC2=C1C=CC=C2)* 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- 125000004622 benzoxazinyl group Chemical group O1NC(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 125000002576 diazepinyl group Chemical group N1N=C(C=CC=C1)* 0.000 description 1
- 125000000532 dioxanyl group Chemical group 0.000 description 1
- 125000005879 dioxolanyl group Chemical group 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 125000002632 imidazolidinyl group Chemical group 0.000 description 1
- 125000002636 imidazolinyl group Chemical group 0.000 description 1
- 125000004857 imidazopyridinyl group Chemical group N1C(=NC2=C1C=CC=N2)* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003072 pyrazolidinyl group Chemical group 0.000 description 1
- 125000002755 pyrazolinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000001422 pyrrolinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000005308 thiazepinyl group Chemical group S1N=C(C=CC=C1)* 0.000 description 1
- 125000002769 thiazolinyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000005505 thiomorpholino group Chemical group 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0400699A GB0400699D0 (en) | 2004-01-13 | 2004-01-13 | Novel compounds |
| US54555404P | 2004-02-17 | 2004-02-17 | |
| PCT/IB2005/000016 WO2005068447A1 (en) | 2004-01-13 | 2005-01-03 | Piperazine derivatives which exhibit activity as serotonin and noradrenaline re-upatke inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2007517855A JP2007517855A (ja) | 2007-07-05 |
| JP2007517855A5 true JP2007517855A5 (https=) | 2008-02-07 |
Family
ID=34796817
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006548459A Abandoned JP2007517855A (ja) | 2004-01-13 | 2005-01-03 | セロトニン及びノルアドレナリン再取込み阻害剤としての活性を示すピペラジン誘導体 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US20070105870A1 (https=) |
| EP (1) | EP1716129A1 (https=) |
| JP (1) | JP2007517855A (https=) |
| BR (1) | BRPI0506844A (https=) |
| CA (1) | CA2553289A1 (https=) |
| WO (1) | WO2005068447A1 (https=) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010014744A1 (en) * | 2008-07-29 | 2010-02-04 | The Scripps Research Institute | Inhibitors of hepatitis c virus infection |
| NZ592543A (en) | 2008-11-14 | 2013-02-22 | Theravance Inc | 4-[2-(2-fluorophenoxymethyl)phenyl]piperidine compounds |
| US8778949B2 (en) * | 2010-01-11 | 2014-07-15 | Theravance Biopharma R&D Ip, Llc | 1-(2-phenoxymethylphenyl)piperazine compounds |
| JP5769348B2 (ja) * | 2010-03-22 | 2015-08-26 | セラヴァンス バイオファーマ アール＆ディー アイピー， エルエルシー | １−（２−フェノキシメチルヘテロアリール）ピペリジン化合物および１−（２−フェノキシメチルヘテロアリール）ピペラジン化合物 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4162316A (en) * | 1975-03-12 | 1979-07-24 | Dainippon Pharmaceutical Co., Ltd. | 1-Substituted-4-(1,2-diphenylethyl)piperazine derivatives and compositions containing the same |
| US5561152A (en) * | 1987-08-14 | 1996-10-01 | Merrell Pharmaceuticals Inc. | Antidepressants |
-
2005
- 2005-01-03 JP JP2006548459A patent/JP2007517855A/ja not_active Abandoned
- 2005-01-03 US US10/586,029 patent/US20070105870A1/en not_active Abandoned
- 2005-01-03 EP EP05702187A patent/EP1716129A1/en not_active Withdrawn
- 2005-01-03 BR BRPI0506844-4A patent/BRPI0506844A/pt not_active IP Right Cessation
- 2005-01-03 CA CA002553289A patent/CA2553289A1/en not_active Abandoned
- 2005-01-03 WO PCT/IB2005/000016 patent/WO2005068447A1/en not_active Ceased
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