JP2004527562A5 - - Google Patents
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- Publication number
- JP2004527562A5 JP2004527562A5 JP2002585437A JP2002585437A JP2004527562A5 JP 2004527562 A5 JP2004527562 A5 JP 2004527562A5 JP 2002585437 A JP2002585437 A JP 2002585437A JP 2002585437 A JP2002585437 A JP 2002585437A JP 2004527562 A5 JP2004527562 A5 JP 2004527562A5
- Authority
- JP
- Japan
- Prior art keywords
- formula
- physiologically acceptable
- compound
- solvate
- acceptable salt
- 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.)
- Granted
Links
- 150000003839 salts Chemical class 0.000 claims 16
- 150000001875 compounds Chemical class 0.000 claims 14
- 239000012453 solvate Substances 0.000 claims 14
- -1 1-azabicyclo [2.2.2] oct-3-yl Chemical group 0.000 claims 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims 5
- 125000004432 carbon atom Chemical group C* 0.000 claims 4
- 239000003814 drug Substances 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims 2
- 102000019315 Nicotinic acetylcholine receptors Human genes 0.000 claims 2
- 108050006807 Nicotinic acetylcholine receptors Proteins 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 claims 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 239000003446 ligand Substances 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims 2
- 125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 claims 1
- SPFWHUJSJQVRMB-UHFFFAOYSA-N 2-[2-(4-methylpiperazin-1-yl)ethyl]-6h-pyrrolo[3,2-e][1,3]benzoxazole Chemical compound C1CN(C)CCN1CCC(O1)=NC2=C1C=CC1=C2C=CN1 SPFWHUJSJQVRMB-UHFFFAOYSA-N 0.000 claims 1
- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- AJRVPWOPYOKQDN-UHFFFAOYSA-N 8-(1-azabicyclo[2.2.2]octan-3-yl)-2-(2-imidazol-1-ylethyl)-6h-pyrrolo[3,2-e][1,3]benzoxazole Chemical compound N=1C(C=2C(C3C4CCN(CC4)C3)=CNC=2C=C2)=C2OC=1CCN1C=CN=C1 AJRVPWOPYOKQDN-UHFFFAOYSA-N 0.000 claims 1
- FBERXFHTIIVDCZ-UHFFFAOYSA-N 8-(1-azabicyclo[2.2.2]octan-3-yl)-2-(thiophen-2-ylmethyl)-6h-pyrrolo[3,2-e][1,3]benzoxazole Chemical compound N=1C(C=2C(C3C4CCN(CC4)C3)=CNC=2C=C2)=C2OC=1CC1=CC=CS1 FBERXFHTIIVDCZ-UHFFFAOYSA-N 0.000 claims 1
- ZNJKKGYLILLJRG-UHFFFAOYSA-N 8-(1-azabicyclo[2.2.2]octan-3-yl)-2-[(5-methoxy-1h-indol-3-yl)methyl]-6h-pyrrolo[3,2-e][1,3]benzoxazole Chemical compound C1N(CC2)CCC2C1C1=CNC2=C1C(N=C(O1)CC3=CNC4=CC=C(C=C43)OC)=C1C=C2 ZNJKKGYLILLJRG-UHFFFAOYSA-N 0.000 claims 1
- CHGLCUWMBUYUCI-UHFFFAOYSA-N 8-(1-methylpiperidin-4-yl)-2-propyl-6h-pyrrolo[3,2-e][1,3]benzoxazole Chemical compound O1C(CCC)=NC(C2=3)=C1C=CC=3NC=C2C1CCN(C)CC1 CHGLCUWMBUYUCI-UHFFFAOYSA-N 0.000 claims 1
- PXYFHCRZTJGCCR-UHFFFAOYSA-N 8-piperidin-4-yl-2-(thiophen-2-ylmethyl)-6h-pyrrolo[3,2-e][1,3]benzoxazole Chemical compound N=1C(C=2C(C3CCNCC3)=CNC=2C=C2)=C2OC=1CC1=CC=CS1 PXYFHCRZTJGCCR-UHFFFAOYSA-N 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 208000000103 Anorexia Nervosa Diseases 0.000 claims 1
- 208000019901 Anxiety disease Diseases 0.000 claims 1
- 208000032841 Bulimia Diseases 0.000 claims 1
- 206010006550 Bulimia nervosa Diseases 0.000 claims 1
- 206010010904 Convulsion Diseases 0.000 claims 1
- 206010012289 Dementia Diseases 0.000 claims 1
- 208000030814 Eating disease Diseases 0.000 claims 1
- 208000019454 Feeding and Eating disease Diseases 0.000 claims 1
- 208000023105 Huntington disease Diseases 0.000 claims 1
- 208000009829 Lewy Body Disease Diseases 0.000 claims 1
- 201000002832 Lewy body dementia Diseases 0.000 claims 1
- 206010057852 Nicotine dependence Diseases 0.000 claims 1
- 208000018737 Parkinson disease Diseases 0.000 claims 1
- 206010036618 Premenstrual syndrome Diseases 0.000 claims 1
- 208000028017 Psychotic disease Diseases 0.000 claims 1
- 208000007271 Substance Withdrawal Syndrome Diseases 0.000 claims 1
- 208000025569 Tobacco Use disease Diseases 0.000 claims 1
- 208000000323 Tourette Syndrome Diseases 0.000 claims 1
- 208000016620 Tourette disease Diseases 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims 1
- 230000006399 behavior Effects 0.000 claims 1
- 125000004197 benzothien-3-yl group Chemical group [H]C1=C(*)C2=C([H])C([H])=C([H])C([H])=C2S1 0.000 claims 1
- 125000002619 bicyclic group Chemical group 0.000 claims 1
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims 1
- 235000010290 biphenyl Nutrition 0.000 claims 1
- 239000004305 biphenyl Substances 0.000 claims 1
- 230000006931 brain damage Effects 0.000 claims 1
- 231100000874 brain damage Toxicity 0.000 claims 1
- 208000029028 brain injury Diseases 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 235000014632 disordered eating Nutrition 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 208000013403 hyperactivity Diseases 0.000 claims 1
- 206010027175 memory impairment Diseases 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 230000004770 neurodegeneration Effects 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 239000007800 oxidant agent Substances 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims 1
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 201000000980 schizophrenia Diseases 0.000 claims 1
- 230000000862 serotonergic effect Effects 0.000 claims 1
- 229940076279 serotonin Drugs 0.000 claims 1
- 230000002295 serotoninergic effect Effects 0.000 claims 1
- 125000004192 tetrahydrofuran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 231100000167 toxic agent Toxicity 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10121217A DE10121217A1 (de) | 2001-04-30 | 2001-04-30 | 6H-Oxazolo[4,5-e]indol-Derivate als nikotinische Acetylcholinrezeptor Liganden und/oder serotonerge Liganden |
| PCT/EP2002/003784 WO2002088139A1 (en) | 2001-04-30 | 2002-04-05 | 6h-oxazolo[4,5-e]indole derivatives as nicotinic acetylcholine receptor ligands and/or serotonergic ligands |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2004527562A JP2004527562A (ja) | 2004-09-09 |
| JP2004527562A5 true JP2004527562A5 (https=) | 2005-12-22 |
| JP4485746B2 JP4485746B2 (ja) | 2010-06-23 |
Family
ID=7683302
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002585437A Expired - Fee Related JP4485746B2 (ja) | 2001-04-30 | 2002-04-05 | ニコチン性アセチルコリンレセプターリガンドおよび／またはセロトニン作動性リガンドとしての６Ｈ−オキサゾロ［４，５−ｅ］インドール誘導体 |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US7291633B2 (https=) |
| EP (1) | EP1392699B1 (https=) |
| JP (1) | JP4485746B2 (https=) |
| AR (1) | AR033267A1 (https=) |
| AT (1) | ATE291026T1 (https=) |
| AU (1) | AU2002257752B2 (https=) |
| CA (1) | CA2445835C (https=) |
| CZ (1) | CZ20033194A3 (https=) |
| DE (2) | DE10121217A1 (https=) |
| ES (1) | ES2239226T3 (https=) |
| HU (1) | HUP0304034A2 (https=) |
| SK (1) | SK14482003A3 (https=) |
| WO (1) | WO2002088139A1 (https=) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10121217A1 (de) * | 2001-04-30 | 2002-10-31 | Merck Patent Gmbh | 6H-Oxazolo[4,5-e]indol-Derivate als nikotinische Acetylcholinrezeptor Liganden und/oder serotonerge Liganden |
| AU2003227522A1 (en) * | 2002-05-30 | 2003-12-19 | Neurosearch A/S | 3-substituted quinuclidines and their use |
| WO2005041957A1 (en) * | 2003-10-29 | 2005-05-12 | Pfizer Products Inc. | Oxindole derivatives and their use as phosphodiesterase type 2 inhibitors |
| US9125900B2 (en) * | 2005-09-14 | 2015-09-08 | University Of The Witwatersrand, Johannesburg | Pharmaceutical composition |
| JP6321662B2 (ja) | 2012-10-12 | 2018-05-09 | ザ ブロード インスティテュート, インコーポレーテッドThe Broad Institute, Inc. | Ｇｓｋ３阻害剤およびその使用の方法 |
| SG11201509371XA (en) * | 2013-05-24 | 2015-12-30 | Nestec Sa | Pathway specific markers for diagnosing irritable bowel syndrome |
| US11203601B2 (en) * | 2017-04-05 | 2021-12-21 | The Broad Institute, Inc. | Tricyclic compounds as glycogen synthase kinase 3 (GSK3) inhibitors and uses thereof |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2073340C (en) | 1990-01-11 | 1997-05-20 | Hakan Vilhelm Wikstrom | Centrally acting 6,7,8,9-tetrahydro-3h-benz(e)indole heterocyclics |
| TW263508B (https=) * | 1991-02-12 | 1995-11-21 | Pfizer | |
| EP0773942A1 (en) | 1994-07-26 | 1997-05-21 | Pfizer Inc. | 4-indole derivatives as serotonin agonists and antagonists |
| US6548530B1 (en) * | 1995-10-03 | 2003-04-15 | The Scripps Research Institute | CBI analogs of CC-1065 and the duocarmycins |
| ES2199553T3 (es) | 1998-03-09 | 2004-02-16 | H.Lundbeck A/S | Indoles sustituidos con 5-heteroarilo. |
| DE10045112A1 (de) | 2000-09-11 | 2002-03-21 | Merck Patent Gmbh | Verwendung von Indolderivaten zur Behandlung von Erkrankungen des zentralen Nervensystems |
| DE10121217A1 (de) * | 2001-04-30 | 2002-10-31 | Merck Patent Gmbh | 6H-Oxazolo[4,5-e]indol-Derivate als nikotinische Acetylcholinrezeptor Liganden und/oder serotonerge Liganden |
-
2001
- 2001-04-30 DE DE10121217A patent/DE10121217A1/de not_active Withdrawn
-
2002
- 2002-04-05 CA CA2445835A patent/CA2445835C/en not_active Expired - Fee Related
- 2002-04-05 DE DE60203283T patent/DE60203283T2/de not_active Expired - Lifetime
- 2002-04-05 ES ES02727527T patent/ES2239226T3/es not_active Expired - Lifetime
- 2002-04-05 AT AT02727527T patent/ATE291026T1/de not_active IP Right Cessation
- 2002-04-05 WO PCT/EP2002/003784 patent/WO2002088139A1/en not_active Ceased
- 2002-04-05 US US10/476,306 patent/US7291633B2/en not_active Expired - Fee Related
- 2002-04-05 HU HU0304034A patent/HUP0304034A2/hu unknown
- 2002-04-05 JP JP2002585437A patent/JP4485746B2/ja not_active Expired - Fee Related
- 2002-04-05 SK SK1448-2003A patent/SK14482003A3/sk unknown
- 2002-04-05 CZ CZ20033194A patent/CZ20033194A3/cs unknown
- 2002-04-05 EP EP02727527A patent/EP1392699B1/en not_active Expired - Lifetime
- 2002-04-05 AU AU2002257752A patent/AU2002257752B2/en not_active Ceased
- 2002-04-26 AR ARP020101530A patent/AR033267A1/es not_active Application Discontinuation
-
2007
- 2007-10-30 US US11/928,961 patent/US7741343B2/en not_active Expired - Fee Related
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