JP2009504792A5 - - Google Patents
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- Publication number
- JP2009504792A5 JP2009504792A5 JP2008527371A JP2008527371A JP2009504792A5 JP 2009504792 A5 JP2009504792 A5 JP 2009504792A5 JP 2008527371 A JP2008527371 A JP 2008527371A JP 2008527371 A JP2008527371 A JP 2008527371A JP 2009504792 A5 JP2009504792 A5 JP 2009504792A5
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- phenyl
- azabicyclo
- trifluoromethyl
- 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.)
- Ceased
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- 150000001875 compounds Chemical class 0.000 claims 27
- 125000000217 alkyl group Chemical group 0.000 claims 10
- 150000003839 salts Chemical class 0.000 claims 8
- 125000001475 halogen functional group Chemical group 0.000 claims 6
- 125000003545 alkoxy group Chemical group 0.000 claims 5
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- CGKRKSGJVCQFTK-PKOBYXMFSA-N (1s,5r)-3-[3-(4-methylpyrimidin-2-yl)sulfanylpropyl]-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hexane Chemical compound CC1=CC=NC(SCCCN2C[C@]3(C[C@H]3C2)C=2C=CC(=CC=2)C(F)(F)F)=N1 CGKRKSGJVCQFTK-PKOBYXMFSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 208000028017 Psychotic disease Diseases 0.000 claims 2
- 208000027418 Wounds and injury Diseases 0.000 claims 2
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims 2
- 230000006378 damage Effects 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 229960003638 dopamine Drugs 0.000 claims 2
- 208000014674 injury Diseases 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 206010036596 premature ejaculation Diseases 0.000 claims 2
- 201000000980 schizophrenia Diseases 0.000 claims 2
- 239000000126 substance Substances 0.000 claims 2
- KZZMXZCKGYEMKT-QFBILLFUSA-N (1s,5r)-1-[4-(trifluoromethyl)phenyl]-3-[4-[4-(trifluoromethyl)pyrimidin-2-yl]butyl]-3-azabicyclo[3.1.0]hexane Chemical compound C1=CC(C(F)(F)F)=CC=C1[C@@]1(CN(CCCCC=2N=C(C=CN=2)C(F)(F)F)C2)[C@H]2C1 KZZMXZCKGYEMKT-QFBILLFUSA-N 0.000 claims 1
- AMHYHLYKORMNDZ-FUHWJXTLSA-N (1s,5r)-3-(3-pyrimidin-2-ylsulfanylpropyl)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hexane Chemical compound C1=CC(C(F)(F)F)=CC=C1[C@@]1(CN(CCCSC=2N=CC=CN=2)C2)[C@H]2C1 AMHYHLYKORMNDZ-FUHWJXTLSA-N 0.000 claims 1
- SIEIBHJJHHYTLA-SQJMNOBHSA-N (1s,5r)-3-[3-[4-(4-methoxyphenyl)pyrimidin-2-yl]sulfanylpropyl]-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hexane Chemical compound C1=CC(OC)=CC=C1C1=CC=NC(SCCCN2C[C@]3(C[C@H]3C2)C=2C=CC(=CC=2)C(F)(F)F)=N1 SIEIBHJJHHYTLA-SQJMNOBHSA-N 0.000 claims 1
- IBXVEILMSYFEPN-WIOPSUGQSA-N (1s,5r)-3-[4-(4-phenylpyrimidin-2-yl)butyl]-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hexane Chemical compound C1=CC(C(F)(F)F)=CC=C1[C@@]1(CN(CCCCC=2N=C(C=CN=2)C=2C=CC=CC=2)C2)[C@H]2C1 IBXVEILMSYFEPN-WIOPSUGQSA-N 0.000 claims 1
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims 1
- CTHIVCAACHDHCW-GUYCJALGSA-N 2-[3-[(1r,5r)-1-[5-(trifluoromethyl)pyridin-2-yl]-3-azabicyclo[3.1.0]hexan-3-yl]propylsulfanyl]-1h-pyrimidin-6-one Chemical compound OC1=CC=NC(SCCCN2C[C@]3(C[C@H]3C2)C=2N=CC(=CC=2)C(F)(F)F)=N1 CTHIVCAACHDHCW-GUYCJALGSA-N 0.000 claims 1
- CEJBUIVOVOGUQI-UGSOOPFHSA-N 2-[3-[(1s,5r)-1-[2-fluoro-4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hexan-3-yl]propylsulfanyl]-1h-pyrimidin-6-one Chemical compound FC1=CC(C(F)(F)F)=CC=C1[C@@]1(CN(CCCSC=2NC=CC(=O)N=2)C2)[C@H]2C1 CEJBUIVOVOGUQI-UGSOOPFHSA-N 0.000 claims 1
- IAQCBWBUFTVZAL-MAUKXSAKSA-N 2-[3-[(1s,5r)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hexan-3-yl]propoxy]-1h-pyrimidin-6-one Chemical compound C1=CC(C(F)(F)F)=CC=C1[C@@]1(CN(CCCOC=2NC=CC(=O)N=2)C2)[C@H]2C1 IAQCBWBUFTVZAL-MAUKXSAKSA-N 0.000 claims 1
- DVRYLRCIQOGJMT-QFBILLFUSA-N 2-[4-[(1s,5r)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hexan-3-yl]butyl]-1h-pyrimidin-6-one Chemical compound OC1=CC=NC(CCCCN2C[C@]3(C[C@H]3C2)C=2C=CC(=CC=2)C(F)(F)F)=N1 DVRYLRCIQOGJMT-QFBILLFUSA-N 0.000 claims 1
- -1 3-{(1S, 5R) -1- [4- (1-methylethyl) phenyl] -3-azabicyclo [3.1.0] hex-3-yl} propyl Chemical group 0.000 claims 1
- CPHFGEKHOGOYAY-MAUKXSAKSA-N 6-[3-[(1s,5r)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hexan-3-yl]propylsulfanyl]-1h-pyrimidin-2-one Chemical compound C1=CC(C(F)(F)F)=CC=C1[C@@]1(CN(CCCSC2=NC(=O)NC=C2)C2)[C@H]2C1 CPHFGEKHOGOYAY-MAUKXSAKSA-N 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 150000002431 hydrogen Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical compound OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 claims 1
- 230000001105 regulatory effect Effects 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0517191.3A GB0517191D0 (en) | 2005-08-22 | 2005-08-22 | Compounds |
| PCT/EP2006/008201 WO2007022934A2 (en) | 2005-08-22 | 2006-08-18 | Azabicyclo (3, 1, 0) hexan derivatives useful as modulators of dopamine d3 receptors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2009504792A JP2009504792A (ja) | 2009-02-05 |
| JP2009504792A5 true JP2009504792A5 (US07928230-20110419-C00030.png) | 2009-10-01 |
Family
ID=35098097
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008527371A Ceased JP2009504792A (ja) | 2005-08-22 | 2006-08-18 | 化合物 |
Country Status (8)
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2070922B1 (en) * | 2004-02-23 | 2011-08-17 | Glaxo Group Limited | Azabicyclo(3.1.0) hexane derivatives useful as modulators of dopamine D3 receptors |
| US20070043100A1 (en) | 2005-08-16 | 2007-02-22 | Hagen Eric J | Novel polymorphs of azabicyclohexane |
| GB0507602D0 (en) * | 2005-04-14 | 2005-05-18 | Glaxo Group Ltd | Compounds |
| GB0507601D0 (en) * | 2005-04-14 | 2005-05-18 | Glaxo Group Ltd | Compounds |
| US7807698B2 (en) * | 2005-06-14 | 2010-10-05 | Glaxo Group Limited | Azabicyclo[3.1.0]hexane derivatives as modulators of the dopamine D3 receptor |
| GB0512099D0 (en) * | 2005-06-14 | 2005-07-20 | Glaxo Group Ltd | Compounds |
| KR101733180B1 (ko) | 2005-07-27 | 2017-05-08 | 뉴로반스, 인크. | 신규 1-아릴-3-아자바이사이클로［3.1.0］헥산：제조 방법 및 신경 정신 질환 치료를 위한 용도 |
| GB0517187D0 (en) * | 2005-08-22 | 2005-09-28 | Glaxo Group Ltd | Compounds |
| GB0517175D0 (en) * | 2005-08-22 | 2005-09-28 | Glaxo Group Ltd | Compounds |
| DE602006018152D1 (de) * | 2005-08-22 | 2010-12-23 | Glaxo Group Ltd | Triazolderivate als modulatoren von dopamin-d3-rezeptoren |
| GB0517193D0 (en) * | 2005-08-22 | 2005-09-28 | Glaxo Group Ltd | Novel use |
| US8222266B2 (en) * | 2006-04-03 | 2012-07-17 | Glaxo Group Limited | Azabicyclo [3.1.0] hexyl derivatives as modulators of dopamine D3 receptors |
| US7727988B2 (en) * | 2006-04-03 | 2010-06-01 | Glaxo Group Limited | Azabicyclo[3.1.0]hex-3-yl}alkyl)pyrimidinedione |
| DE602007012531D1 (de) | 2006-04-03 | 2011-03-31 | Glaxo Group Ltd | Azabicycloä3.1.0ühexanderivate als modulatoren von dopamin-d3-rezeptoren |
| US20080045725A1 (en) | 2006-04-28 | 2008-02-21 | Murry Jerry A | Process For The Synthesis of (+) And (-)-1-(3,4-Dichlorophenyl)-3-Azabicyclo[3.1.0]Hexane |
| US8138377B2 (en) | 2006-11-07 | 2012-03-20 | Dov Pharmaceutical, Inc. | Arylbicyclo[3.1.0]hexylamines and methods and compositions for their preparation and use |
| US20090069374A1 (en) * | 2007-06-06 | 2009-03-12 | Phil Skolnick | Novel 1-Heteroaryl-3-Azabicyclo[3.1.0]Hexanes, Methods For Their Preparation And Their Use As Medicaments |
| US9133159B2 (en) * | 2007-06-06 | 2015-09-15 | Neurovance, Inc. | 1-heteroaryl-3-azabicyclo[3.1.0]hexanes, methods for their preparation and their use as medicaments |
| GB0719234D0 (en) * | 2007-10-02 | 2007-11-14 | Glaxo Group Ltd | Novel compounds |
| GB0719235D0 (en) * | 2007-10-02 | 2007-11-14 | Glaxo Group Ltd | Novel compounds |
| US8906913B2 (en) | 2009-06-26 | 2014-12-09 | Panacea Biotec Limited | Azabicyclohexanes |
| US8957254B2 (en) | 2009-07-06 | 2015-02-17 | Solvay Sa | Process for chemical synthesis from an alkenone made from a halogenated precursor |
| US20140206740A1 (en) | 2011-07-30 | 2014-07-24 | Neurovance, Inc. | Use Of (1R,5S)-(+)-(Napthalen-2-yl)-3-Azabicyclo[3.1.0]Hexane In The Treatment Of Conditions Affected By Monoamine Neurotransmitters |
| JP6183053B2 (ja) * | 2012-08-22 | 2017-08-23 | 宇部興産株式会社 | テトラヒドロピラニルピリミジン化合物の製造方法 |
| US11447484B2 (en) | 2018-01-26 | 2022-09-20 | Shionogi & Co., Ltd. | Cyclic compound having dopamine D3 receptor antagonistic effect |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI244481B (en) * | 1998-12-23 | 2005-12-01 | Pfizer | 3-azabicyclo[3.1.0]hexane derivatives useful in therapy |
| CA2428844A1 (en) | 2000-11-14 | 2002-05-23 | Michael Stewart Hadley | Tetrahydrobenzazepine derivatives useful as modulators of dopamine d3 receptors (antipsychotic agents) |
| DK1440059T3 (da) | 2001-10-22 | 2008-07-14 | Pfizer Prod Inc | 3-azabicyclo(3.1.0)hexanderivater som opioidreceptorantagonister |
| EP2070922B1 (en) | 2004-02-23 | 2011-08-17 | Glaxo Group Limited | Azabicyclo(3.1.0) hexane derivatives useful as modulators of dopamine D3 receptors |
| GB0507601D0 (en) * | 2005-04-14 | 2005-05-18 | Glaxo Group Ltd | Compounds |
| GB0507602D0 (en) * | 2005-04-14 | 2005-05-18 | Glaxo Group Ltd | Compounds |
| GB0507680D0 (en) | 2005-04-15 | 2005-05-25 | Glaxo Group Ltd | Compounds |
| US7807698B2 (en) | 2005-06-14 | 2010-10-05 | Glaxo Group Limited | Azabicyclo[3.1.0]hexane derivatives as modulators of the dopamine D3 receptor |
| GB0512099D0 (en) * | 2005-06-14 | 2005-07-20 | Glaxo Group Ltd | Compounds |
| GB0517193D0 (en) | 2005-08-22 | 2005-09-28 | Glaxo Group Ltd | Novel use |
| GB0517187D0 (en) | 2005-08-22 | 2005-09-28 | Glaxo Group Ltd | Compounds |
| GB0517175D0 (en) | 2005-08-22 | 2005-09-28 | Glaxo Group Ltd | Compounds |
| DE602006018152D1 (de) | 2005-08-22 | 2010-12-23 | Glaxo Group Ltd | Triazolderivate als modulatoren von dopamin-d3-rezeptoren |
| US7727988B2 (en) | 2006-04-03 | 2010-06-01 | Glaxo Group Limited | Azabicyclo[3.1.0]hex-3-yl}alkyl)pyrimidinedione |
| GB0616574D0 (en) | 2006-08-21 | 2006-09-27 | Glaxo Group Ltd | Compounds |
-
2005
- 2005-08-22 GB GBGB0517191.3A patent/GB0517191D0/en not_active Ceased
-
2006
- 2006-08-18 JP JP2008527371A patent/JP2009504792A/ja not_active Ceased
- 2006-08-18 DE DE602006006850T patent/DE602006006850D1/de active Active
- 2006-08-18 AT AT06791594T patent/ATE431345T1/de not_active IP Right Cessation
- 2006-08-18 EP EP06791594A patent/EP1926723B1/en active Active
- 2006-08-18 WO PCT/EP2006/008201 patent/WO2007022934A2/en active Application Filing
- 2006-08-18 ES ES06791594T patent/ES2327162T3/es active Active
- 2006-08-18 US US12/064,123 patent/US7745458B2/en not_active Expired - Fee Related
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