JP2010527370A5 - - Google Patents
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- Publication number
- JP2010527370A5 JP2010527370A5 JP2010508533A JP2010508533A JP2010527370A5 JP 2010527370 A5 JP2010527370 A5 JP 2010527370A5 JP 2010508533 A JP2010508533 A JP 2010508533A JP 2010508533 A JP2010508533 A JP 2010508533A JP 2010527370 A5 JP2010527370 A5 JP 2010527370A5
- Authority
- JP
- Japan
- Prior art keywords
- formula
- amine
- compound
- indazol
- group
- 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.)
- Withdrawn
Links
- 150000001875 compounds Chemical class 0.000 claims 21
- 150000003839 salts Chemical class 0.000 claims 11
- 125000001072 heteroaryl group Chemical group 0.000 claims 10
- 125000003118 aryl group Chemical group 0.000 claims 8
- 229910052739 hydrogen Inorganic materials 0.000 claims 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims 7
- 238000000034 method Methods 0.000 claims 7
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 6
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 6
- 125000006239 protecting group Chemical group 0.000 claims 5
- 229910052799 carbon Inorganic materials 0.000 claims 4
- -1 cycloheteroalkyl Chemical group 0.000 claims 4
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 125000005842 heteroatom Chemical group 0.000 claims 4
- 239000000203 mixture Substances 0.000 claims 4
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 3
- 125000004429 atom Chemical group 0.000 claims 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 2
- 125000002619 bicyclic group Chemical group 0.000 claims 2
- 125000004122 cyclic group Chemical group 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 125000001624 naphthyl group Chemical group 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 238000007363 ring formation reaction Methods 0.000 claims 2
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 claims 2
- 125000003107 substituted aryl group Chemical group 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- JRLYNJLTUMIKJZ-MRXNPFEDSA-N (3r)-1-(1-methyl-3-naphthalen-1-ylsulfonylindazol-5-yl)pyrrolidin-3-amine Chemical compound C=1C=C2N(C)N=C(S(=O)(=O)C=3C4=CC=CC=C4C=CC=3)C2=CC=1N1CC[C@@H](N)C1 JRLYNJLTUMIKJZ-MRXNPFEDSA-N 0.000 claims 1
- QNVKMRYWPVDPHU-GOSISDBHSA-N (3r)-1-(3-naphthalen-1-ylsulfonyl-1-propan-2-ylindazol-5-yl)pyrrolidin-3-amine Chemical compound C=1C=C2N(C(C)C)N=C(S(=O)(=O)C=3C4=CC=CC=C4C=CC=3)C2=CC=1N1CC[C@@H](N)C1 QNVKMRYWPVDPHU-GOSISDBHSA-N 0.000 claims 1
- OPTAOWZLDMSBKX-OAHLLOKOSA-N (3r)-1-(3-naphthalen-1-ylsulfonyl-2h-indazol-5-yl)pyrrolidin-3-amine Chemical compound C1[C@H](N)CCN1C1=CC=C(NN=C2S(=O)(=O)C=3C4=CC=CC=C4C=CC=3)C2=C1 OPTAOWZLDMSBKX-OAHLLOKOSA-N 0.000 claims 1
- UGOLTQIWMDMFNL-LJQANCHMSA-N (3r)-1-[1-(2-methylpropyl)-3-naphthalen-1-ylsulfonylindazol-5-yl]pyrrolidin-3-amine Chemical compound C=1C=C2N(CC(C)C)N=C(S(=O)(=O)C=3C4=CC=CC=C4C=CC=3)C2=CC=1N1CC[C@@H](N)C1 UGOLTQIWMDMFNL-LJQANCHMSA-N 0.000 claims 1
- MDLROMSYVSSBDC-GFCCVEGCSA-N (3r)-1-[3-(benzenesulfonyl)-2h-indazol-5-yl]pyrrolidin-3-amine Chemical compound C1[C@H](N)CCN1C1=CC=C(NN=C2S(=O)(=O)C=3C=CC=CC=3)C2=C1 MDLROMSYVSSBDC-GFCCVEGCSA-N 0.000 claims 1
- ADEIHMYSULIEAK-GOSISDBHSA-N (3r)-n,n-dimethyl-1-(3-naphthalen-1-ylsulfonyl-2h-indazol-5-yl)pyrrolidin-3-amine Chemical compound C1[C@H](N(C)C)CCN1C1=CC=C(NN=C2S(=O)(=O)C=3C4=CC=CC=C4C=CC=3)C2=C1 ADEIHMYSULIEAK-GOSISDBHSA-N 0.000 claims 1
- OPTAOWZLDMSBKX-HNNXBMFYSA-N (3s)-1-(3-naphthalen-1-ylsulfonyl-2h-indazol-5-yl)pyrrolidin-3-amine Chemical compound C1[C@@H](N)CCN1C1=CC=C(NN=C2S(=O)(=O)C=3C4=CC=CC=C4C=CC=3)C2=C1 OPTAOWZLDMSBKX-HNNXBMFYSA-N 0.000 claims 1
- MDLROMSYVSSBDC-LBPRGKRZSA-N (3s)-1-[3-(benzenesulfonyl)-2h-indazol-5-yl]pyrrolidin-3-amine Chemical compound C1[C@@H](N)CCN1C1=CC=C(NN=C2S(=O)(=O)C=3C=CC=CC=3)C2=C1 MDLROMSYVSSBDC-LBPRGKRZSA-N 0.000 claims 1
- ADEIHMYSULIEAK-SFHVURJKSA-N (3s)-n,n-dimethyl-1-(3-naphthalen-1-ylsulfonyl-2h-indazol-5-yl)pyrrolidin-3-amine Chemical compound C1[C@@H](N(C)C)CCN1C1=CC=C(NN=C2S(=O)(=O)C=3C4=CC=CC=C4C=CC=3)C2=C1 ADEIHMYSULIEAK-SFHVURJKSA-N 0.000 claims 1
- PEENLCMAOCPFKF-UHFFFAOYSA-N 1-(3-naphthalen-1-ylsulfonyl-2h-indazol-5-yl)azetidin-3-amine Chemical compound C1C(N)CN1C1=CC=C(NN=C2S(=O)(=O)C=3C4=CC=CC=C4C=CC=3)C2=C1 PEENLCMAOCPFKF-UHFFFAOYSA-N 0.000 claims 1
- LCVVWJNRODQABK-UHFFFAOYSA-N 1-(3-naphthalen-1-ylsulfonyl-2h-indazol-5-yl)piperidin-4-amine Chemical compound C1CC(N)CCN1C1=CC=C(NN=C2S(=O)(=O)C=3C4=CC=CC=C4C=CC=3)C2=C1 LCVVWJNRODQABK-UHFFFAOYSA-N 0.000 claims 1
- OYOYEIIOGFLVQY-UHFFFAOYSA-N 1-(3-naphthalen-2-ylsulfonyl-2h-indazol-5-yl)piperidin-4-amine Chemical compound C1CC(N)CCN1C1=CC=C(NN=C2S(=O)(=O)C=3C=C4C=CC=CC4=CC=3)C2=C1 OYOYEIIOGFLVQY-UHFFFAOYSA-N 0.000 claims 1
- QFZPYOASMMLHOZ-UHFFFAOYSA-N 1-[3-(3-chlorophenyl)sulfonyl-2h-indazol-5-yl]piperidin-4-amine Chemical compound C1CC(N)CCN1C1=CC=C(NN=C2S(=O)(=O)C=3C=C(Cl)C=CC=3)C2=C1 QFZPYOASMMLHOZ-UHFFFAOYSA-N 0.000 claims 1
- SYPGYFXCMLCVHY-UHFFFAOYSA-N 1-[3-(4-methylnaphthalen-1-yl)sulfonyl-2h-indazol-5-yl]piperidin-4-amine Chemical compound C12=CC=CC=C2C(C)=CC=C1S(=O)(=O)C(C1=C2)=NNC1=CC=C2N1CCC(N)CC1 SYPGYFXCMLCVHY-UHFFFAOYSA-N 0.000 claims 1
- CVYWFPZSGMNWAR-UHFFFAOYSA-N 1-[3-(4-propan-2-ylphenyl)sulfonyl-2h-indazol-5-yl]piperidin-4-amine Chemical compound C1=CC(C(C)C)=CC=C1S(=O)(=O)C1=NNC2=CC=C(N3CCC(N)CC3)C=C12 CVYWFPZSGMNWAR-UHFFFAOYSA-N 0.000 claims 1
- LTWJNOFKAYZXFU-UHFFFAOYSA-N 1-[3-(5-chloronaphthalen-1-yl)sulfonyl-2h-indazol-5-yl]piperidin-4-amine Chemical compound C1CC(N)CCN1C1=CC=C(NN=C2S(=O)(=O)C=3C4=CC=CC(Cl)=C4C=CC=3)C2=C1 LTWJNOFKAYZXFU-UHFFFAOYSA-N 0.000 claims 1
- UFSKSPXGURYXLU-UHFFFAOYSA-N 1-[3-(benzenesulfonyl)-2h-indazol-5-yl]azetidin-3-amine Chemical compound C1C(N)CN1C1=CC=C(NN=C2S(=O)(=O)C=3C=CC=CC=3)C2=C1 UFSKSPXGURYXLU-UHFFFAOYSA-N 0.000 claims 1
- DDJYYJIWIYUTRV-UHFFFAOYSA-N 3-sulfonylindazole Chemical group C1=CC=C2C(=S(=O)=O)N=NC2=C1 DDJYYJIWIYUTRV-UHFFFAOYSA-N 0.000 claims 1
- 108091005435 5-HT6 receptors Proteins 0.000 claims 1
- 208000007848 Alcoholism Diseases 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 208000019901 Anxiety disease Diseases 0.000 claims 1
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims 1
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 208000016285 Movement disease Diseases 0.000 claims 1
- 206010057852 Nicotine dependence Diseases 0.000 claims 1
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims 1
- 208000018737 Parkinson disease Diseases 0.000 claims 1
- 208000025569 Tobacco Use disease Diseases 0.000 claims 1
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 208000015114 central nervous system disease Diseases 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 208000010877 cognitive disease Diseases 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 206010015037 epilepsy Diseases 0.000 claims 1
- 150000002366 halogen compounds Chemical class 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 208000015122 neurodegenerative disease Diseases 0.000 claims 1
- 229910052763 palladium Inorganic materials 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- OAHKWDDSKCRNFE-UHFFFAOYSA-N phenylmethanesulfonyl chloride Chemical compound ClS(=O)(=O)CC1=CC=CC=C1 OAHKWDDSKCRNFE-UHFFFAOYSA-N 0.000 claims 1
- 201000000980 schizophrenia Diseases 0.000 claims 1
- 235000010344 sodium nitrate Nutrition 0.000 claims 1
- 239000004317 sodium nitrate Substances 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US93018607P | 2007-05-15 | 2007-05-15 | |
| PCT/US2008/063507 WO2008144299A1 (en) | 2007-05-15 | 2008-05-13 | 5- (aminoazacyclyl) -3-sulfonyl-lh- indazoles as 5-hydroxytryptamine- 6 ligands for the treatment of cns disorders |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2010527370A JP2010527370A (ja) | 2010-08-12 |
| JP2010527370A5 true JP2010527370A5 (enExample) | 2011-06-30 |
Family
ID=39618919
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010508533A Withdrawn JP2010527370A (ja) | 2007-05-15 | 2008-05-13 | Ｃｎｓ疾患治療のための５−ヒドロキシトリプタミン−６リガンドとしての５−（アミノアザシクリル）−３−スルホニル−１ｈ−インダゾール |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US7939520B2 (enExample) |
| EP (1) | EP2158195A1 (enExample) |
| JP (1) | JP2010527370A (enExample) |
| CA (1) | CA2685318A1 (enExample) |
| CL (1) | CL2008001413A1 (enExample) |
| PA (1) | PA8780701A1 (enExample) |
| PE (1) | PE20090250A1 (enExample) |
| TW (1) | TW200908962A (enExample) |
| WO (1) | WO2008144299A1 (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105541693B (zh) | 2014-07-08 | 2018-10-16 | 广东东阳光药业有限公司 | 芳杂环类衍生物及其在药物上的应用 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9818916D0 (en) | 1998-08-28 | 1998-10-21 | Smithkline Beecham Plc | Use |
| WO2004074243A2 (en) | 2003-02-14 | 2004-09-02 | Wyeth | Heterocyclyl-3-sulfonylindazoles as 5-hydroxytryptamine-6 ligands |
| WO2007032833A1 (en) | 2005-08-15 | 2007-03-22 | Wyeth | Azinyl-3-sulfonylindazole derivatives as 5-hydroxytryptamine-6 ligands |
-
2008
- 2008-05-13 EP EP08780660A patent/EP2158195A1/en not_active Withdrawn
- 2008-05-13 JP JP2010508533A patent/JP2010527370A/ja not_active Withdrawn
- 2008-05-13 WO PCT/US2008/063507 patent/WO2008144299A1/en not_active Ceased
- 2008-05-13 US US12/119,837 patent/US7939520B2/en not_active Expired - Fee Related
- 2008-05-13 CA CA002685318A patent/CA2685318A1/en not_active Abandoned
- 2008-05-14 PE PE2008000837A patent/PE20090250A1/es not_active Application Discontinuation
- 2008-05-14 PA PA20088780701A patent/PA8780701A1/es unknown
- 2008-05-14 CL CL200801413A patent/CL2008001413A1/es unknown
- 2008-05-15 TW TW097117865A patent/TW200908962A/zh unknown
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