ZA200505880B - Treatment of diseases with alpha-7 nACh receptor full agonists - Google Patents
Treatment of diseases with alpha-7 nACh receptor full agonists Download PDFInfo
- Publication number
- ZA200505880B ZA200505880B ZA200505880A ZA200505880A ZA200505880B ZA 200505880 B ZA200505880 B ZA 200505880B ZA 200505880 A ZA200505880 A ZA 200505880A ZA 200505880 A ZA200505880 A ZA 200505880A ZA 200505880 B ZA200505880 B ZA 200505880B
- Authority
- ZA
- South Africa
- Prior art keywords
- substituted
- azabicyclo
- carboxamide
- alkyl
- oct
- Prior art date
Links
- 239000000556 agonist Substances 0.000 title claims description 25
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims description 13
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- 108050006807 Nicotinic acetylcholine receptors Proteins 0.000 title description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 79
- 125000001188 haloalkyl group Chemical group 0.000 claims description 58
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 50
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 45
- -1 -ORj Chemical group 0.000 claims description 35
- 102000015296 acetylcholine-gated cation-selective channel activity proteins Human genes 0.000 claims description 20
- 108040006409 acetylcholine-gated cation-selective channel activity proteins Proteins 0.000 claims description 20
- 125000003118 aryl group Chemical group 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 15
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- UZVGSSNIUNSOFA-UHFFFAOYSA-N dibenzofuran-1-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O UZVGSSNIUNSOFA-UHFFFAOYSA-N 0.000 claims description 3
- IQQNMLSLUVURHZ-UHFFFAOYSA-N furo[2,3-c]pyridine-5-carboxamide Chemical compound C1=NC(C(=O)N)=CC2=C1OC=C2 IQQNMLSLUVURHZ-UHFFFAOYSA-N 0.000 claims description 3
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- WECKJONDRAUFDD-ZDUSSCGKSA-N N-[(3R)-1-azabicyclo[2.2.2]octan-3-yl]-4-chlorobenzamide Chemical group C1=CC(Cl)=CC=C1C(=O)N[C@@H]1C(CC2)CCN2C1 WECKJONDRAUFDD-ZDUSSCGKSA-N 0.000 claims description 2
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- IPKZCLGGYKRDES-UHFFFAOYSA-N n-(1-azabicyclo[2.2.2]octan-3-yl)furo[2,3-c]pyridine-5-carboxamide Chemical compound C1N(CC2)CCC2C1NC(=O)C(N=C1)=CC2=C1OC=C2 IPKZCLGGYKRDES-UHFFFAOYSA-N 0.000 claims description 2
- MJEICMZGYNFOGL-ADEWGFFLSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-methylfuro[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1OC=C2C MJEICMZGYNFOGL-ADEWGFFLSA-N 0.000 claims description 2
- ZLYNXTYFPVYJKB-ZDUSSCGKSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-1,3-benzothiazole-6-carboxamide Chemical compound C1=C2N=CSC2=CC(C(N[C@@H]2C3CCN(CC3)C2)=O)=C1 ZLYNXTYFPVYJKB-ZDUSSCGKSA-N 0.000 claims description 2
- GTDDJGZNXMIDBO-AWEZNQCLSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-2-methyl-1,3-benzoxazole-5-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=CC=C(OC(C)=N2)C2=C1 GTDDJGZNXMIDBO-AWEZNQCLSA-N 0.000 claims description 2
- RVXVUHMZGCOXHD-AWEZNQCLSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-2-methylfuro[2,3-c]pyridine-5-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=NC=C(OC(C)=C2)C2=C1 RVXVUHMZGCOXHD-AWEZNQCLSA-N 0.000 claims description 2
- YCSBGDZYEYEBHT-ZDUSSCGKSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-3-chlorofuro[2,3-c]pyridine-5-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=NC=C2OC=C(Cl)C2=C1 YCSBGDZYEYEBHT-ZDUSSCGKSA-N 0.000 claims description 2
- JHRRADCVOUYBLD-KRWDZBQOSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]dibenzothiophene-2-carboxamide Chemical compound C1=CC=C2C3=CC(C(N[C@@H]4C5CCN(CC5)C4)=O)=CC=C3SC2=C1 JHRRADCVOUYBLD-KRWDZBQOSA-N 0.000 claims description 2
- NJNIZJCRCANYGV-ZDUSSCGKSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]thieno[2,3-c]pyridine-5-carboxamide Chemical compound N([C@@H]1C2CCN(CC2)C1)C(=O)C(N=C1)=CC2=C1SC=C2 NJNIZJCRCANYGV-ZDUSSCGKSA-N 0.000 claims description 2
- FSWJILNACZEMQN-AWEZNQCLSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]thieno[3,4-c]pyridine-6-carboxamide Chemical compound C=1C2=CSC=C2C=NC=1C(=O)N[C@@H]1C(CC2)CCN2C1 FSWJILNACZEMQN-AWEZNQCLSA-N 0.000 claims description 2
- CDQRPYYOVWJPET-UFBFGSQYSA-N n-[(3r,4s)-1-azabicyclo[2.2.1]heptan-3-yl]-3-chlorofuro[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1CN2CC[C@]1(C2)[H])C(=O)C(N=C1)=CC2=C1OC=C2Cl CDQRPYYOVWJPET-UFBFGSQYSA-N 0.000 claims description 2
- ZCHLHQVYHFPHIF-VXGBXAGGSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-3-methylfuro[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1)=CC2=C1OC=C2C ZCHLHQVYHFPHIF-VXGBXAGGSA-N 0.000 claims description 2
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- CZXIPBIBWCODNX-UHFFFAOYSA-N thieno[2,3-c]pyridine-5-carboxamide Chemical compound C1=NC(C(=O)N)=CC2=C1SC=C2 CZXIPBIBWCODNX-UHFFFAOYSA-N 0.000 claims description 2
- TUPZWIXDHKKDRH-UHFFFAOYSA-N thieno[3,2-c]pyridine-6-carboxamide Chemical compound C1=NC(C(=O)N)=CC2=C1C=CS2 TUPZWIXDHKKDRH-UHFFFAOYSA-N 0.000 claims description 2
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- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 70
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- 125000004093 cyano group Chemical group *C#N 0.000 claims 4
- VFGUCKRRIWUMQR-UHFFFAOYSA-N [1,3]dioxolo[4,5-c]pyridine-6-carboxamide Chemical compound O1COC=2C=NC(=CC=21)C(=O)N VFGUCKRRIWUMQR-UHFFFAOYSA-N 0.000 claims 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
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- LSGKMZLPZFPAIN-UHFFFAOYSA-N 1h-indole-3-carboxamide Chemical compound C1=CC=C2C(C(=O)N)=CNC2=C1 LSGKMZLPZFPAIN-UHFFFAOYSA-N 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
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- AMRWFRQVCKJNSX-BONVTDFDSA-N n-[(2s,3r)-2-methyl-1-azabicyclo[2.2.2]octan-3-yl]furo[2,3-c]pyridine-5-carboxamide Chemical compound C1CC2CCN1[C@@H](C)[C@@H]2NC(=O)C(N=C1)=CC2=C1OC=C2 AMRWFRQVCKJNSX-BONVTDFDSA-N 0.000 claims 2
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Applications Claiming Priority (1)
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| US44180103P | 2003-01-22 | 2003-01-22 |
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| DE10164139A1 (de) | 2001-12-27 | 2003-07-10 | Bayer Ag | 2-Heteroarylcarbonsäureamide |
| GB0220581D0 (en) | 2002-09-04 | 2002-10-09 | Novartis Ag | Organic Compound |
| US7429664B2 (en) * | 2002-09-25 | 2008-09-30 | Memory Pharmaceuticals Corporation | Indazoles, benzothiazoles, and benzoisothiazoles, and preparation and uses thereof |
| EP1603585A2 (en) | 2003-03-14 | 2005-12-14 | Bristol-Myers Squibb Company | Polynucleotide encoding a novel human g-protein coupled receptor variant of hm74, hgprbmy74 |
| GB0310867D0 (en) * | 2003-05-12 | 2003-06-18 | Novartis Ag | Organic compounds |
| BRPI0508771A (pt) * | 2004-03-25 | 2007-08-14 | Memory Pharm Corp | indazóis, benzotiazóis, benzoisotiazóis, benzisoxazóis, e a preparação e usos dos mesmos |
| PE20060437A1 (es) | 2004-06-18 | 2006-06-08 | Novartis Ag | COMPUESTOS AZA-BICICLONONANOS COMO LIGANDOS COLINERGICOS DE nAChR |
| GB0415746D0 (en) | 2004-07-14 | 2004-08-18 | Novartis Ag | Organic compounds |
| US8106066B2 (en) | 2005-09-23 | 2012-01-31 | Memory Pharmaceuticals Corporation | Indazoles, benzothiazoles, benzoisothiazoles, benzisoxazoles, pyrazolopyridines, isothiazolopyridines, and preparation and uses thereof |
| KR20080048550A (ko) * | 2005-09-23 | 2008-06-02 | 메모리 파마슈티칼스 코포레이션 | 인다졸, 벤조티아졸, 벤조이소티아졸, 벤즈이속사졸,피라졸로피리딘, 이소티아졸로피리딘, 및 이들의 제법 및용도 |
| GB0521508D0 (en) | 2005-10-21 | 2005-11-30 | Novartis Ag | Organic compounds |
| GB0525672D0 (en) | 2005-12-16 | 2006-01-25 | Novartis Ag | Organic compounds |
| GB0525673D0 (en) | 2005-12-16 | 2006-01-25 | Novartis Ag | Organic compounds |
| US8076350B2 (en) | 2006-12-22 | 2011-12-13 | Abbott Laboratories | Spirocyclic azaadamantane derivatives and methods of use |
| SI3029039T1 (en) | 2010-05-17 | 2018-04-30 | Forum Pharmaceuticals Inc. | Pharmaceutical formulations containing crystalline forms of (R) -7-chloro-N- (quinuclidin-3-yl) benzo (b) thiophene-2-carboxamide hydrochloride monohydrate |
| WO2012177263A1 (en) | 2011-06-24 | 2012-12-27 | Intra-Cellular Therapies, Inc. | Compounds and methods of prophylaxis and treatment regarding nictonic receptor antagonists |
| CN102558139B (zh) * | 2011-12-30 | 2013-12-25 | 南京工业大学 | 一种合成3，4-噻吩二甲醛的方法 |
| WO2013169646A1 (en) | 2012-05-08 | 2013-11-14 | Envivo Pharmaceuticals, Inc. | Methods of maintaining, treating or improving cognitive function |
| US9708348B2 (en) | 2014-10-03 | 2017-07-18 | Infinity Pharmaceuticals, Inc. | Trisubstituted bicyclic heterocyclic compounds with kinase activities and uses thereof |
| US10919914B2 (en) | 2016-06-08 | 2021-02-16 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
| US11491150B2 (en) | 2017-05-22 | 2022-11-08 | Intra-Cellular Therapies, Inc. | Organic compounds |
| JP7212781B2 (ja) | 2018-12-19 | 2023-01-25 | ディスアーム セラピューティクス， インコーポレイテッド | 神経保護剤と組み合わせたｓａｒｍ１の阻害剤 |
| WO2021092275A1 (en) * | 2019-11-06 | 2021-05-14 | Children’S National Medical Center | Methods and compositions for the prevention and treatment of ischemia reperfusion injury and infection |
| CN111233873B (zh) * | 2020-01-20 | 2023-01-24 | 潍坊医学院 | 甲基牛扁亭在制备抑制白血病细胞及白血病干细胞增殖并诱导其分化药物中的应用 |
| CN111732558B (zh) * | 2020-07-31 | 2021-02-26 | 南昌大学 | 一种合成1-氮杂二环[2,2,1]庚烷及其衍生物的方法 |
| CN112625057B (zh) * | 2020-12-25 | 2022-12-09 | 山东金城柯瑞化学有限公司 | 3-羟基-4-((三甲基甲硅烷基)乙炔基)苯甲酸甲酯的合成方法 |
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| US20010021380A1 (en) * | 1999-04-19 | 2001-09-13 | Pluenneke John D. | Soluble tumor necrosis factor receptor treatment of medical disorders |
| SE0000540D0 (sv) * | 2000-02-18 | 2000-02-18 | Astrazeneca Ab | New compounds |
| US6599916B2 (en) * | 2000-08-21 | 2003-07-29 | Pharmacia & Upjohn Company | Quinuclidine-substituted heteroaryl moieties for treatment of disease |
| WO2002017358A2 (en) * | 2000-08-21 | 2002-02-28 | Pharmacia & Upjohn Company | Quinuclidine-substituted heteroaryl moieties for treatment of disease (nicotinic acetylcholine receptor antagonists) |
| AU2001282910A1 (en) * | 2000-08-21 | 2002-03-04 | Pharmacia And Upjohn Company | Quinuclidine-substituted heteroaryl moieties for treatment of disease (nicotinic) acetylcholine receptor ligands |
| PE20021019A1 (es) * | 2001-04-19 | 2002-11-13 | Upjohn Co | Grupos azabiciclicos sustituidos |
| AR036041A1 (es) * | 2001-06-12 | 2004-08-04 | Upjohn Co | Compuestos aromaticos heterociclicos sustituidos con quinuclidina y composiciones farmaceuticas que los contienen |
| AR036040A1 (es) * | 2001-06-12 | 2004-08-04 | Upjohn Co | Compuestos de heteroarilo multiciclicos sustituidos con quinuclidinas y composiciones farmaceuticas que los contienen |
| US20030008892A1 (en) * | 2001-07-09 | 2003-01-09 | Pfizer Inc. | Pharmaceutical composition and method of modulating cholinergic function in a mammal |
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- 2004-01-12 EP EP04701414A patent/EP1587511A2/en not_active Withdrawn
- 2004-01-12 CN CNA2004800078299A patent/CN1764456A/zh active Pending
- 2004-01-12 AU AU2004206107A patent/AU2004206107A1/en not_active Abandoned
- 2004-01-12 BR BR0406834-3A patent/BRPI0406834A/pt not_active IP Right Cessation
- 2004-01-12 KR KR1020057013589A patent/KR20050092777A/ko not_active Application Discontinuation
- 2004-01-12 CA CA002513433A patent/CA2513433A1/en not_active Abandoned
- 2004-01-12 WO PCT/IB2004/000115 patent/WO2004064836A2/en not_active Application Discontinuation
- 2004-01-12 JP JP2005518724A patent/JP2006515023A/ja active Pending
- 2004-01-20 TW TW093101642A patent/TW200425893A/zh unknown
- 2004-01-21 US US10/761,914 patent/US20060019984A1/en not_active Abandoned
-
2005
- 2005-07-21 ZA ZA200505880A patent/ZA200505880B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CN1764456A (zh) | 2006-04-26 |
| WO2004064836A3 (en) | 2004-12-23 |
| US20060019984A1 (en) | 2006-01-26 |
| CA2513433A1 (en) | 2004-08-05 |
| JP2006515023A (ja) | 2006-05-18 |
| EP1587511A2 (en) | 2005-10-26 |
| TW200425893A (en) | 2004-12-01 |
| PL378026A1 (pl) | 2006-02-20 |
| AU2004206107A1 (en) | 2004-08-05 |
| MXPA05007689A (es) | 2005-09-30 |
| BRPI0406834A (pt) | 2005-12-27 |
| WO2004064836A2 (en) | 2004-08-05 |
| KR20050092777A (ko) | 2005-09-22 |
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