JP2005504058A - 疾患の治療のための置換ヘテロアリール−7−アザ[2.2.1]ビシクロヘプタン - Google Patents
疾患の治療のための置換ヘテロアリール−7−アザ[2.2.1]ビシクロヘプタン Download PDFInfo
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- JP2005504058A JP2005504058A JP2003523245A JP2003523245A JP2005504058A JP 2005504058 A JP2005504058 A JP 2005504058A JP 2003523245 A JP2003523245 A JP 2003523245A JP 2003523245 A JP2003523245 A JP 2003523245A JP 2005504058 A JP2005504058 A JP 2005504058A
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- JP
- Japan
- Prior art keywords
- azabicyclo
- hept
- carboxamide
- thiophene
- furan
- 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
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- 150000003839 salts Chemical class 0.000 claims abstract description 34
- 125000000217 alkyl group Chemical group 0.000 claims description 149
- -1 and R 2 is H Chemical group 0.000 claims description 127
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- 125000001424 substituent group Chemical group 0.000 claims description 111
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 108
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 46
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- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 8
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- 229910052720 vanadium Inorganic materials 0.000 claims description 7
- 229910052727 yttrium Inorganic materials 0.000 claims description 7
- CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 claims description 6
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- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 125000001072 heteroaryl group Chemical group 0.000 claims description 5
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- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 4
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- ZQMWCOZHPBMYAF-ADEWGFFLSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-5-(2-chloropyridin-4-yl)oxythiophene-2-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(S1)=CC=C1OC1=CC=NC(Cl)=C1 ZQMWCOZHPBMYAF-ADEWGFFLSA-N 0.000 claims description 4
- WUXDEGQWSFVUQG-ADEWGFFLSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-5-(2-chloropyridin-4-yl)sulfanylthiophene-2-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(S1)=CC=C1SC1=CC=NC(Cl)=C1 WUXDEGQWSFVUQG-ADEWGFFLSA-N 0.000 claims description 4
- GKBVLMXIZUSZBS-DVVUODLYSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-5-(2-fluoropyridin-3-yl)-1,3-oxazole-2-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(O1)=NC=C1C1=CC=CN=C1F GKBVLMXIZUSZBS-DVVUODLYSA-N 0.000 claims description 4
- XDPIBQXANRUEHV-VHDGCEQUSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-5-(4-cyanophenoxy)thiophene-2-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(S1)=CC=C1OC1=CC=C(C#N)C=C1 XDPIBQXANRUEHV-VHDGCEQUSA-N 0.000 claims description 4
- UFINMAAKGKATOZ-GRYCIOLGSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-5-(5-chloropyridin-2-yl)oxythiophene-2-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(S1)=CC=C1OC1=CC=C(Cl)C=N1 UFINMAAKGKATOZ-GRYCIOLGSA-N 0.000 claims description 4
- PZTVZRXNNPIOKU-KXUCPTDWSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-5-(5-chlorothiophen-2-yl)thiophene-2-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(S1)=CC=C1C1=CC=C(Cl)S1 PZTVZRXNNPIOKU-KXUCPTDWSA-N 0.000 claims description 4
- CHVHKCKUGONQEE-GRYCIOLGSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-5-(5-methylthiophen-2-yl)thiophene-2-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(S1)=CC=C1C1=CC=C(C)S1 CHVHKCKUGONQEE-GRYCIOLGSA-N 0.000 claims description 4
- OFRJLKOCLIZDSV-ADEWGFFLSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-5-(6-chloropyridin-3-yl)oxythiophene-2-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(S1)=CC=C1OC1=CC=C(Cl)N=C1 OFRJLKOCLIZDSV-ADEWGFFLSA-N 0.000 claims description 4
- YNXCSYUXPRVOIE-ADEWGFFLSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-5-(6-chloropyridin-3-yl)sulfanylthiophene-2-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(S1)=CC=C1SC1=CC=C(Cl)N=C1 YNXCSYUXPRVOIE-ADEWGFFLSA-N 0.000 claims description 4
- KKLYYHDOLZFJDX-GRYCIOLGSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-5-thiophen-3-ylthiophene-2-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(S1)=CC=C1C=1C=CSC=1 KKLYYHDOLZFJDX-GRYCIOLGSA-N 0.000 claims description 4
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 4
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims description 3
- 208000017194 Affective disease Diseases 0.000 claims description 3
- 125000002619 bicyclic group Chemical group 0.000 claims description 3
- AMUUSWWYGANZEX-HZSPNIEDSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-5-(2-cyanophenoxy)thiophene-2-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(S1)=CC=C1OC1=CC=CC=C1C#N AMUUSWWYGANZEX-HZSPNIEDSA-N 0.000 claims description 3
- UECFPTCBHAOQAZ-VHDGCEQUSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-5-(3-cyanophenoxy)thiophene-2-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(S1)=CC=C1OC1=CC=CC(C#N)=C1 UECFPTCBHAOQAZ-VHDGCEQUSA-N 0.000 claims description 3
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 3
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- NJFJAFHSODSMRG-FRRDWIJNSA-N 5-(4-aminophenyl)-n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-1,3-thiazole-2-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(S1)=NC=C1C1=CC=C(N)C=C1 NJFJAFHSODSMRG-FRRDWIJNSA-N 0.000 claims description 2
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- SIDHKDSUFJDOHE-KXUCPTDWSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-5-(5-methoxy-1,3-thiazol-2-yl)thiophene-2-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(S1)=CC=C1C1=NC=C(OC)S1 SIDHKDSUFJDOHE-KXUCPTDWSA-N 0.000 claims description 2
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- GZFBJASITXTOOO-KWCYVHTRSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-5-[3-(trifluoromethylsulfonylamino)phenyl]furan-2-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(O1)=CC=C1C1=CC=CC(NS(=O)(=O)C(F)(F)F)=C1 GZFBJASITXTOOO-KWCYVHTRSA-N 0.000 claims description 2
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- DFDKAUDXIZNBLC-KWCYVHTRSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-5-[3-(trifluoromethylsulfonylamino)phenyl]thiophene-2-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(S1)=CC=C1C1=CC=CC(NS(=O)(=O)C(F)(F)F)=C1 DFDKAUDXIZNBLC-KWCYVHTRSA-N 0.000 claims description 2
- FVWCHPSMRQWTMA-KWCYVHTRSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-5-[3-[(2,2,2-trifluoroacetyl)amino]phenoxy]thiophene-2-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(S1)=CC=C1OC1=CC=CC(NC(=O)C(F)(F)F)=C1 FVWCHPSMRQWTMA-KWCYVHTRSA-N 0.000 claims description 2
- RGXLNCAPSHFXEW-KWCYVHTRSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-5-[3-[(2,2,2-trifluoroacetyl)amino]phenyl]sulfanylthiophene-2-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(S1)=CC=C1SC1=CC=CC(NC(=O)C(F)(F)F)=C1 RGXLNCAPSHFXEW-KWCYVHTRSA-N 0.000 claims description 2
- NIAUKDPKZICYTB-HZSPNIEDSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-5-[3-[(2,2,2-trifluoroacetyl)amino]phenyl]thiophene-2-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(S1)=CC=C1C1=CC=CC(NC(=O)C(F)(F)F)=C1 NIAUKDPKZICYTB-HZSPNIEDSA-N 0.000 claims description 2
- VNGFMSIDWADLIV-KWCYVHTRSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-5-[3-[(2,2-difluoroacetyl)amino]phenoxy]thiophene-2-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(S1)=CC=C1OC1=CC=CC(NC(=O)C(F)F)=C1 VNGFMSIDWADLIV-KWCYVHTRSA-N 0.000 claims description 2
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- NSFKRPAYAWHJJU-FGTMMUONSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-5-[4-(5-methylfuran-2-yl)phenyl]furan-2-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(O1)=CC=C1C(C=C1)=CC=C1C1=CC=C(C)O1 NSFKRPAYAWHJJU-FGTMMUONSA-N 0.000 claims description 2
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- VZMMFLIIAXFAFI-KWCYVHTRSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-5-[4-(trifluoromethoxy)phenyl]furan-2-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(O1)=CC=C1C1=CC=C(OC(F)(F)F)C=C1 VZMMFLIIAXFAFI-KWCYVHTRSA-N 0.000 claims description 2
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- JQMLZPFGPGOZFL-GJMOJQLCSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-5-chlorothiophene-2-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C1=CC=C(Cl)S1 JQMLZPFGPGOZFL-GJMOJQLCSA-N 0.000 claims description 2
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- ZXRWGWCNEFUQFC-FKTZTGRPSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-5-cyanothiophene-2-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C1=CC=C(C#N)S1 ZXRWGWCNEFUQFC-FKTZTGRPSA-N 0.000 claims description 2
- YJHYIDUHKFBJEH-VHDGCEQUSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-5-methoxy-4-phenylthiophene-2-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(SC=1OC)=CC=1C1=CC=CC=C1 YJHYIDUHKFBJEH-VHDGCEQUSA-N 0.000 claims description 2
- SJVIZNRGXIFLBH-HRDYMLBCSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-5-methoxythiophene-2-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C1=CC=C(OC)S1 SJVIZNRGXIFLBH-HRDYMLBCSA-N 0.000 claims description 2
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Classifications
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- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
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Landscapes
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- Hospice & Palliative Care (AREA)
- Nutrition Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US31485101P | 2001-08-24 | 2001-08-24 | |
| US31477301P | 2001-08-24 | 2001-08-24 | |
| US31476801P | 2001-08-24 | 2001-08-24 | |
| US31477201P | 2001-08-24 | 2001-08-24 | |
| US38871202P | 2002-06-14 | 2002-06-14 | |
| PCT/US2002/021326 WO2003018585A1 (en) | 2001-08-24 | 2002-08-14 | Substituted-heteroaryl-7-aza[2.2.1]bicycloheptanes for the treatment of disease |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2005504058A true JP2005504058A (ja) | 2005-02-10 |
| JP2005504058A5 JP2005504058A5 (enExample) | 2006-01-05 |
Family
ID=27540993
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003523245A Abandoned JP2005504058A (ja) | 2001-08-24 | 2002-08-14 | 疾患の治療のための置換ヘテロアリール−7−アザ[2.2.1]ビシクロヘプタン |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US6562816B2 (enExample) |
| EP (1) | EP1419161A1 (enExample) |
| JP (1) | JP2005504058A (enExample) |
| BR (1) | BR0212101A (enExample) |
| CA (1) | CA2458375A1 (enExample) |
| WO (1) | WO2003018585A1 (enExample) |
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|---|---|---|---|---|
| JP2007533621A (ja) * | 2003-09-19 | 2007-11-22 | ソルベイ・フアーマシユーチカルズ・ベー・ブイ | カンナビノイド受容体調整剤としてのチアゾール誘導体 |
| JP2011524349A (ja) * | 2008-06-13 | 2011-09-01 | バイエル・クロツプサイエンス・アクチエンゲゼルシヤフト | 殺有害生物剤としての新規ヘテロ芳香族アミド及びチオアミド |
| WO2013161871A1 (ja) * | 2012-04-25 | 2013-10-31 | 興和株式会社 | Tlr阻害作用を有するチオフェン誘導体 |
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| BR0212123A (pt) * | 2001-08-24 | 2004-07-20 | Upjohn Co | 7-aza[2.2.1]biciclo-heptanos substituìdos com arila para o tratamento de doenças |
| DE10164139A1 (de) | 2001-12-27 | 2003-07-10 | Bayer Ag | 2-Heteroarylcarbonsäureamide |
| US20040138269A1 (en) * | 2002-10-11 | 2004-07-15 | Sugen, Inc. | Substituted pyrroles as kinase inhibitors |
| WO2004039366A1 (en) * | 2002-11-01 | 2004-05-13 | Pharmacia & Upjohn Company Llc | Nicotinic acetylcholine agonists in the treatment of glaucoma and retinal neuropathy |
| JP4750421B2 (ja) * | 2002-12-06 | 2011-08-17 | ノース ショア−ロング アイランド ジュ−イッシュ リサ−チ インスティチュ−ト | α7受容体結合コリン作動性アゴニストを用いる炎症の阻害 |
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| GB0302094D0 (en) | 2003-01-29 | 2003-02-26 | Pharmagene Lab Ltd | EP4 receptor antagonists |
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| US8316104B2 (en) | 2005-11-15 | 2012-11-20 | California Institute Of Technology | Method and apparatus for collaborative system |
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| SA08290475B1 (ar) | 2007-08-02 | 2013-06-22 | Targacept Inc | (2s، 3r)-n-(2-((3-بيردينيل)ميثيل)-1-آزا بيسيكلو[2، 2، 2]أوكت-3-يل)بنزو فيوران-2-كربوكساميد، وصور أملاحه الجديدة وطرق استخدامه |
| JP5718053B2 (ja) | 2007-08-27 | 2015-05-13 | ヘリコン・セラピューティクス・インコーポレーテッド | 治療用イソオキサゾール化合物 |
| WO2009098282A1 (en) * | 2008-02-06 | 2009-08-13 | Novasaid Ab | Low molecular weight 2,5-disubstituted thiophene derivatives and use thereof in therapy |
| CA2638573C (en) * | 2008-04-30 | 2013-03-12 | Universiteit Gent | Substituted 7-azabicyclo[2.2.1]heptyl derivatives useful for making pharmaceutical compositions |
| US8389561B2 (en) * | 2008-04-30 | 2013-03-05 | Universiteit Gent | Substituted 7-azabicyclo[2.2.1]heptyl derivatives useful for making pharmaceutical compositions |
| EP2296471A4 (en) | 2008-05-15 | 2012-03-14 | Univ Toledo | MUSCARIC ACID AGONISTS AS COGNITIVE ENHANCERS |
| WO2009152392A2 (en) * | 2008-06-11 | 2009-12-17 | University Of Toledo | Muscarinic agonists for neurological disorders and methods of making the same |
| TW201031664A (en) | 2009-01-26 | 2010-09-01 | Targacept Inc | Preparation and therapeutic applications of (2S,3R)-N-2-((3-pyridinyl)methyl)-1-azabicyclo[2.2.2]oct-3-yl)-3,5-difluorobenzamide |
| US8809365B2 (en) | 2009-11-04 | 2014-08-19 | Universiteit Gent | 1-substituted 2-azabicyclo [3.1.1] heptyl derivatives useful as nicotinic acetylcholine receptor modulators for treating neurologic disorders |
| CN103221411B (zh) | 2010-05-17 | 2016-05-11 | 富瑞姆制药公司 | (R)-7-氯-N-(奎宁环-3-基)苯并[b]噻吩-2-甲酰胺盐酸盐单水合物的晶型 |
| ES2603032T3 (es) * | 2010-07-15 | 2017-02-23 | Bayer Intellectual Property Gmbh | Compuestos de 3-piridil-heteroarilcarboxamida como pesticidas |
| KR101928505B1 (ko) * | 2011-01-28 | 2018-12-12 | 에스케이바이오팜 주식회사 | 피리돈 유도체 및 이를 포함하는 약학적 조성물 |
| WO2012149524A1 (en) | 2011-04-29 | 2012-11-01 | The University Of Toledo | Muscarinic agonists as enhancers of working memory and cognitive flexibility |
| US8946432B2 (en) | 2011-07-05 | 2015-02-03 | Lupin Limited | Biaryl derivatives as nAChR modulators |
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| EP3534899B1 (en) | 2016-11-03 | 2022-06-01 | Corvus Pharmaceuticals, Inc. | Compounds and methods for modulating interleukin-2-inducible t-cell kinase |
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-
2002
- 2002-08-14 US US10/218,772 patent/US6562816B2/en not_active Expired - Fee Related
- 2002-08-14 CA CA002458375A patent/CA2458375A1/en not_active Abandoned
- 2002-08-14 BR BR0212101-8A patent/BR0212101A/pt not_active IP Right Cessation
- 2002-08-14 JP JP2003523245A patent/JP2005504058A/ja not_active Abandoned
- 2002-08-14 WO PCT/US2002/021326 patent/WO2003018585A1/en not_active Ceased
- 2002-08-14 EP EP02759115A patent/EP1419161A1/en not_active Withdrawn
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007533621A (ja) * | 2003-09-19 | 2007-11-22 | ソルベイ・フアーマシユーチカルズ・ベー・ブイ | カンナビノイド受容体調整剤としてのチアゾール誘導体 |
| JP2011524349A (ja) * | 2008-06-13 | 2011-09-01 | バイエル・クロツプサイエンス・アクチエンゲゼルシヤフト | 殺有害生物剤としての新規ヘテロ芳香族アミド及びチオアミド |
| JP2014224128A (ja) * | 2008-06-13 | 2014-12-04 | バイエル・クロップサイエンス・アーゲーBayer Cropscience Ag | 殺有害生物剤としての新規ヘテロ芳香族アミド及びチオアミド |
| JP2015205902A (ja) * | 2008-06-13 | 2015-11-19 | バイエル・クロップサイエンス・アクチェンゲゼルシャフト | 殺有害生物剤としての新規ヘテロ芳香族アミド及びチオアミド |
| WO2013161871A1 (ja) * | 2012-04-25 | 2013-10-31 | 興和株式会社 | Tlr阻害作用を有するチオフェン誘導体 |
Also Published As
| Publication number | Publication date |
|---|---|
| US6562816B2 (en) | 2003-05-13 |
| US20030069290A1 (en) | 2003-04-10 |
| WO2003018585A1 (en) | 2003-03-06 |
| CA2458375A1 (en) | 2003-03-06 |
| BR0212101A (pt) | 2004-08-24 |
| EP1419161A1 (en) | 2004-05-19 |
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