NO330338B1 - Indolylalkylaminderivater, fremgangsmater for deres fremstilling samt anvendelse derav - Google Patents
Indolylalkylaminderivater, fremgangsmater for deres fremstilling samt anvendelse derav Download PDFInfo
- Publication number
- NO330338B1 NO330338B1 NO20043100A NO20043100A NO330338B1 NO 330338 B1 NO330338 B1 NO 330338B1 NO 20043100 A NO20043100 A NO 20043100A NO 20043100 A NO20043100 A NO 20043100A NO 330338 B1 NO330338 B1 NO 330338B1
- Authority
- NO
- Norway
- Prior art keywords
- sulfonyl
- indol
- chloroimidazo
- thiazol
- formula
- Prior art date
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- 238000002360 preparation method Methods 0.000 title description 28
- 238000000034 method Methods 0.000 title description 15
- 150000001875 compounds Chemical class 0.000 claims description 97
- 108091005435 5-HT6 receptors Proteins 0.000 claims description 20
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 17
- QUSNBJAOOMFDIB-UHFFFAOYSA-N monoethyl amine Natural products CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 17
- -1 imidazo[2,1-b][1,3]thiazolyl Chemical group 0.000 claims description 16
- 229910052736 halogen Inorganic materials 0.000 claims description 15
- 150000002367 halogens Chemical class 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 14
- 125000001424 substituent group Chemical group 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 210000003169 central nervous system Anatomy 0.000 claims description 11
- 239000002904 solvent Substances 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 150000001412 amines Chemical class 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000006239 protecting group Chemical group 0.000 claims description 8
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 8
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical group C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 claims description 5
- RBQGKSWYSQGVDV-UHFFFAOYSA-N imidazo[2,1-b][1,3]benzothiazole Chemical group C1=CC=C2N3C=CN=C3SC2=C1 RBQGKSWYSQGVDV-UHFFFAOYSA-N 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- BAVYZALUXZFZLV-UHFFFAOYSA-N mono-methylamine Natural products NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 5
- 125000002757 morpholinyl group Chemical group 0.000 claims description 5
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 5
- 125000004193 piperazinyl group Chemical group 0.000 claims description 5
- 125000003386 piperidinyl group Chemical group 0.000 claims description 5
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- 201000000980 schizophrenia Diseases 0.000 claims description 3
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- YWQKKENICVJTCQ-SNVBAGLBSA-N (2r)-1-[1-(6-chloroimidazo[2,1-b][1,3]thiazol-5-yl)sulfonylindol-3-yl]propan-2-amine Chemical compound C1=CC=C2C(C[C@H](N)C)=CN(S(=O)(=O)C=3N4C=CSC4=NC=3Cl)C2=C1 YWQKKENICVJTCQ-SNVBAGLBSA-N 0.000 claims description 2
- YWQKKENICVJTCQ-JTQLQIEISA-N (2s)-1-[1-(6-chloroimidazo[2,1-b][1,3]thiazol-5-yl)sulfonylindol-3-yl]propan-2-amine Chemical compound C1=CC=C2C(C[C@@H](N)C)=CN(S(=O)(=O)C=3N4C=CSC4=NC=3Cl)C2=C1 YWQKKENICVJTCQ-JTQLQIEISA-N 0.000 claims description 2
- YWQKKENICVJTCQ-UHFFFAOYSA-N 1-[1-(6-chloroimidazo[2,1-b][1,3]thiazol-5-yl)sulfonylindol-3-yl]propan-2-amine Chemical compound C1=CC=C2C(CC(N)C)=CN(S(=O)(=O)C=3N4C=CSC4=NC=3Cl)C2=C1 YWQKKENICVJTCQ-UHFFFAOYSA-N 0.000 claims description 2
- YOLHSBHQHDKVKV-UHFFFAOYSA-N 2-[1-(2,6-dichloroimidazo[2,1-b][1,3]thiazol-5-yl)sulfonylindol-3-yl]-n,n-dimethylethanamine Chemical compound C1=CC=C2C(CCN(C)C)=CN(S(=O)(=O)C=3N4C=C(Cl)SC4=NC=3Cl)C2=C1 YOLHSBHQHDKVKV-UHFFFAOYSA-N 0.000 claims description 2
- LNHFREBIWKCIRV-UHFFFAOYSA-N 2-[1-(2,6-dichloroimidazo[2,1-b][1,3]thiazol-5-yl)sulfonylindol-3-yl]-n-methylethanamine Chemical compound C1=CC=C2C(CCNC)=CN(S(=O)(=O)C=3N4C=C(Cl)SC4=NC=3Cl)C2=C1 LNHFREBIWKCIRV-UHFFFAOYSA-N 0.000 claims description 2
- ZLTNDESBMHSTIP-UHFFFAOYSA-N 2-[1-(2-chloroimidazo[2,1-b][1,3]benzothiazol-1-yl)sulfonylindol-3-yl]-n,n-dimethylethanamine Chemical compound C1=CC=C2N3C(S(=O)(=O)N4C=C(C5=CC=CC=C54)CCN(C)C)=C(Cl)N=C3SC2=C1 ZLTNDESBMHSTIP-UHFFFAOYSA-N 0.000 claims description 2
- FKKDYQNRMHHVHU-UHFFFAOYSA-N 2-[1-(2-chloroimidazo[2,1-b][1,3]benzothiazol-1-yl)sulfonylindol-3-yl]-n-methylethanamine Chemical compound C1=CC=C2N3C(S(=O)(=O)N4C=C(C5=CC=CC=C54)CCNC)=C(Cl)N=C3SC2=C1 FKKDYQNRMHHVHU-UHFFFAOYSA-N 0.000 claims description 2
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- YEOFNCNSWIZMLD-UHFFFAOYSA-N 2-[1-(6-chloroimidazo[2,1-b][1,3]thiazol-5-yl)sulfonyl-5-fluoroindol-3-yl]ethanamine Chemical compound C1=C(F)C=C2C(CCN)=CN(S(=O)(=O)C=3N4C=CSC4=NC=3Cl)C2=C1 YEOFNCNSWIZMLD-UHFFFAOYSA-N 0.000 claims description 2
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- GHHGZAWPOONRTQ-UHFFFAOYSA-N 2-[1-(6-chloroimidazo[2,1-b][1,3]thiazol-5-yl)sulfonyl-5-phenylmethoxyindol-3-yl]ethanamine Chemical compound C1=C2C(CCN)=CN(S(=O)(=O)C=3N4C=CSC4=NC=3Cl)C2=CC=C1OCC1=CC=CC=C1 GHHGZAWPOONRTQ-UHFFFAOYSA-N 0.000 claims description 2
- OEQVUTVOBPGNKI-UHFFFAOYSA-N 2-[1-(6-chloroimidazo[2,1-b][1,3]thiazol-5-yl)sulfonyl-6-fluoroindol-3-yl]ethanamine Chemical compound FC1=CC=C2C(CCN)=CN(S(=O)(=O)C=3N4C=CSC4=NC=3Cl)C2=C1 OEQVUTVOBPGNKI-UHFFFAOYSA-N 0.000 claims description 2
- HDNIRYDNLLIRSX-UHFFFAOYSA-N 2-[1-(6-chloroimidazo[2,1-b][1,3]thiazol-5-yl)sulfonyl-6-methylindol-3-yl]ethanamine Chemical compound CC1=CC=C2C(CCN)=CN(S(=O)(=O)C=3N4C=CSC4=NC=3Cl)C2=C1 HDNIRYDNLLIRSX-UHFFFAOYSA-N 0.000 claims description 2
- XBGSJMLHRXOGME-UHFFFAOYSA-N 2-[1-(6-chloroimidazo[2,1-b][1,3]thiazol-5-yl)sulfonyl-7-methylindol-3-yl]ethanamine Chemical compound CC1=CC=CC2=C1N(S(=O)(=O)C=1N3C=CSC3=NC=1Cl)C=C2CCN XBGSJMLHRXOGME-UHFFFAOYSA-N 0.000 claims description 2
- KMICQOVIJQCBMW-UHFFFAOYSA-N 2-[1-(6-chloroimidazo[2,1-b][1,3]thiazol-5-yl)sulfonylindol-3-yl]-n,n-dimethylethanamine Chemical compound C1=CC=C2C(CCN(C)C)=CN(S(=O)(=O)C=3N4C=CSC4=NC=3Cl)C2=C1 KMICQOVIJQCBMW-UHFFFAOYSA-N 0.000 claims description 2
- MQZGKLOUZNZXFQ-UHFFFAOYSA-N 2-[5-chloro-1-(2,6-dichloroimidazo[2,1-b][1,3]thiazol-5-yl)sulfonylindol-3-yl]ethanamine Chemical compound C1=C(Cl)C=C2C(CCN)=CN(S(=O)(=O)C=3N4C=C(Cl)SC4=NC=3Cl)C2=C1 MQZGKLOUZNZXFQ-UHFFFAOYSA-N 0.000 claims description 2
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- OUTQWUFBUULQHO-UHFFFAOYSA-N 6-chloro-5-[3-(2-piperidin-1-ylethyl)indol-1-yl]sulfonylimidazo[2,1-b][1,3]thiazole Chemical compound ClC=1N=C2SC=CN2C=1S(=O)(=O)N(C1=CC=CC=C11)C=C1CCN1CCCCC1 OUTQWUFBUULQHO-UHFFFAOYSA-N 0.000 claims description 2
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- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 150000003461 sulfonyl halides Chemical class 0.000 description 1
- 230000006103 sulfonylation Effects 0.000 description 1
- 238000005694 sulfonylation reaction Methods 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000007885 tablet disintegrant Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Psychiatry (AREA)
- Psychology (AREA)
- Pain & Pain Management (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Indole Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US34290701P | 2001-12-20 | 2001-12-20 | |
| PCT/US2002/040217 WO2003053433A1 (en) | 2001-12-20 | 2002-12-17 | Indolylalkylamine derivatives as 5-hydroxytryptamine-6 ligands |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO20043100L NO20043100L (no) | 2004-08-26 |
| NO330338B1 true NO330338B1 (no) | 2011-03-28 |
Family
ID=23343804
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20043100A NO330338B1 (no) | 2001-12-20 | 2004-07-19 | Indolylalkylaminderivater, fremgangsmater for deres fremstilling samt anvendelse derav |
Country Status (30)
| Country | Link |
|---|---|
| US (2) | US6770642B2 (hu) |
| EP (1) | EP1455779B1 (hu) |
| JP (1) | JP4335684B2 (hu) |
| KR (1) | KR100985140B1 (hu) |
| CN (1) | CN1309385C (hu) |
| AR (1) | AR037906A1 (hu) |
| AT (1) | ATE335477T1 (hu) |
| AU (1) | AU2002357270B2 (hu) |
| BR (1) | BR0215222A (hu) |
| CA (1) | CA2470863C (hu) |
| CO (1) | CO5590924A2 (hu) |
| CY (1) | CY1105705T1 (hu) |
| DE (1) | DE60213856T2 (hu) |
| DK (1) | DK1455779T3 (hu) |
| EC (1) | ECSP045156A (hu) |
| ES (1) | ES2269827T3 (hu) |
| HK (1) | HK1065949A1 (hu) |
| HU (1) | HUP0402640A3 (hu) |
| IL (1) | IL162243A0 (hu) |
| MX (1) | MXPA04005889A (hu) |
| NO (1) | NO330338B1 (hu) |
| NZ (1) | NZ533666A (hu) |
| PL (1) | PL210413B1 (hu) |
| PT (1) | PT1455779E (hu) |
| RU (1) | RU2309157C2 (hu) |
| SI (1) | SI1455779T1 (hu) |
| TW (1) | TWI254705B (hu) |
| UA (1) | UA78536C2 (hu) |
| WO (1) | WO2003053433A1 (hu) |
| ZA (1) | ZA200405731B (hu) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR0115262A (pt) * | 2000-11-09 | 2003-08-12 | Mitsui Chemicals Inc | Derivados de amina opticamente ativos e processo de preparação destes |
| TW200301251A (en) * | 2001-12-20 | 2003-07-01 | Wyeth Corp | Azaindolylalkylamine derivatives as 5-hydroxytryptamine-6 ligands |
| JP2006528186A (ja) * | 2003-07-23 | 2006-12-14 | ワイス | ５−ヒドロキシトリプタミン−６リガンドとしてのスルホニルジヒドロベンゾイミダゾロン化合物 |
| US20050032873A1 (en) * | 2003-07-30 | 2005-02-10 | Wyeth | 3-Amino chroman and 2-amino tetralin derivatives |
| JP2007500701A (ja) * | 2003-07-31 | 2007-01-18 | ワイス | ５−ヒドロキシトリプタミン−６リガンドとしてのｎ−スルホニルヘテロシクロピロリルアルキルアミン化合物 |
| AU2004261667A1 (en) * | 2003-08-01 | 2005-02-10 | Genelabs Technologies, Inc. | Bicyclic imidazol derivatives against Flaviviridae |
| CA2552106C (en) * | 2004-01-02 | 2011-10-11 | Suven Life Sciences Limited | Novel indeno[2,1a]indenes and isoindol[2,1-a]indoles |
| PE20060303A1 (es) * | 2004-06-23 | 2006-05-19 | Wyeth Corp | Metabolitos de indolilalquilamina como ligandos de 5-hidroxitriptamina-6 |
| BRPI0519036A2 (pt) * | 2004-12-14 | 2008-12-23 | Wyeth Corp | mÉtodo para o tratamento de um paciente acometido por uma doenÇa neuro-degenerativa; composiÇço farmacÊutica para tratar uma doenÇa neuro-degenerativa; e uso de um agonista 5-ht6 ou de um agonista 5-ht6 |
| CN101103026A (zh) * | 2005-01-14 | 2008-01-09 | 健亚生物科技公司 | 用于治疗病毒感染的吲哚衍生物 |
| EP1953153A1 (en) * | 2007-01-31 | 2008-08-06 | Laboratorios del Dr. Esteve S.A. | Heterocyclyl-substituted sulfonamides for the treatment of cognitive or food ingestion related disorders |
| US20080318941A1 (en) * | 2007-05-24 | 2008-12-25 | Memory Pharmaceuticals Corporation | 4' substituted compounds having 5-ht6 receptor affinity |
| DE602007012683D1 (de) * | 2007-07-19 | 2011-04-07 | Esteve Labor Dr | Substituierte Tetrahydro-Chinolinsulfonamidverbindungen, ihre Herstellung und ihre Verwendung als Medikamente |
| EP2053052A1 (en) * | 2007-10-23 | 2009-04-29 | Laboratorios del Dr. Esteve S.A. | Process for the preparation of 6-substituted imidazo[2,1-b]thiazole-5-sulfonyl halide |
| EP2231160B1 (en) * | 2007-12-04 | 2013-08-14 | Merck Sharp & Dohme Corp. | Tryptamine sulfonamides as 5-ht6 antagonists |
| WO2009082268A2 (ru) | 2007-12-21 | 2009-07-02 | Alla Chem, Llc | ЛИГАНДЫ α-АДРЕНОЦЕПТОРОВ, ДОПАМИНОВЫХ, ГИСТАМИНОВЫХ, ИМИДАЗОЛИНОВЫХ И СЕРОТОНИНОВЫХ РЕЦЕПТОРОВ И ИХ ПРИМЕНЕНИЕ |
| US20100016297A1 (en) * | 2008-06-24 | 2010-01-21 | Memory Pharmaceuticals Corporation | Alkyl-substituted 3' compounds having 5-ht6 receptor affinity |
| US20100022581A1 (en) * | 2008-07-02 | 2010-01-28 | Memory Pharmaceuticals Corporation | Pyrrolidine-substituted azaindole compounds having 5-ht6 receptor affinity |
| US20100029629A1 (en) * | 2008-07-25 | 2010-02-04 | Memory Pharmaceuticals Corporation | Acyclic compounds having 5-ht6 receptor affinity |
| US20100056531A1 (en) * | 2008-08-22 | 2010-03-04 | Memory Pharmaceuticals Corporation | Alkyl-substituted 3' compounds having 5-ht6 receptor affinity |
| CN104725295B (zh) | 2013-12-20 | 2019-05-24 | 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 |
| ES2898965T3 (es) | 2014-08-29 | 2022-03-09 | Chdi Foundation Inc | Sondas de formación de imágenes de la proteína Huntingtina |
| US10907197B2 (en) * | 2014-08-29 | 2021-02-02 | Chdi Foundation, Inc. | Probes for imaging huntingtin protein |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5545644A (en) | 1990-10-15 | 1996-08-13 | Pfizer Inc. | Indole derivatives |
| US6194410B1 (en) | 1998-03-11 | 2001-02-27 | Hoffman-La Roche Inc. | Pyrazolopyrimidine and pyrazolines and process for preparation thereof |
| US6133287A (en) | 1998-03-24 | 2000-10-17 | Allelix Biopharmaceuticals Inc. | Piperidine-indole compounds having 5-HT6 affinity |
| GB9820113D0 (en) * | 1998-09-15 | 1998-11-11 | Merck Sharp & Dohme | Therapeutic agents |
| US6403808B1 (en) | 1999-12-10 | 2002-06-11 | Virginia Commonwealth University | Selective 5-HT6 receptor ligands |
| DK1204662T3 (da) * | 1999-08-12 | 2004-10-04 | Nps Allelix Corp | Azaindoler med serotoninreceptoraffinitet |
| WO2001032660A1 (en) * | 1999-11-05 | 2001-05-10 | Nps Allelix Corp. | Compounds having 5-ht6 receptor antagonist activity |
| WO2001034146A1 (en) * | 1999-11-08 | 2001-05-17 | Smithkline Beecham Corporation | Novel anti-infectives |
-
2002
- 2002-12-17 EP EP02805601A patent/EP1455779B1/en not_active Expired - Lifetime
- 2002-12-17 BR BR0215222-3A patent/BR0215222A/pt not_active Application Discontinuation
- 2002-12-17 SI SI200230401T patent/SI1455779T1/sl unknown
- 2002-12-17 DK DK02805601T patent/DK1455779T3/da active
- 2002-12-17 WO PCT/US2002/040217 patent/WO2003053433A1/en active IP Right Grant
- 2002-12-17 DE DE60213856T patent/DE60213856T2/de not_active Expired - Lifetime
- 2002-12-17 KR KR1020047009606A patent/KR100985140B1/ko not_active IP Right Cessation
- 2002-12-17 UA UA20040705919A patent/UA78536C2/uk unknown
- 2002-12-17 HU HU0402640A patent/HUP0402640A3/hu unknown
- 2002-12-17 ES ES02805601T patent/ES2269827T3/es not_active Expired - Lifetime
- 2002-12-17 AT AT02805601T patent/ATE335477T1/de active
- 2002-12-17 CA CA2470863A patent/CA2470863C/en not_active Expired - Fee Related
- 2002-12-17 NZ NZ533666A patent/NZ533666A/xx not_active IP Right Cessation
- 2002-12-17 MX MXPA04005889A patent/MXPA04005889A/es active IP Right Grant
- 2002-12-17 CN CNB028281721A patent/CN1309385C/zh not_active Expired - Fee Related
- 2002-12-17 JP JP2003554190A patent/JP4335684B2/ja not_active Expired - Fee Related
- 2002-12-17 AU AU2002357270A patent/AU2002357270B2/en not_active Ceased
- 2002-12-17 PT PT02805601T patent/PT1455779E/pt unknown
- 2002-12-17 PL PL370711A patent/PL210413B1/pl not_active IP Right Cessation
- 2002-12-17 IL IL16224302A patent/IL162243A0/xx unknown
- 2002-12-17 RU RU2004122129/04A patent/RU2309157C2/ru not_active IP Right Cessation
- 2002-12-18 TW TW091136490A patent/TWI254705B/zh active
- 2002-12-18 AR ARP020104951A patent/AR037906A1/es unknown
- 2002-12-19 US US10/323,369 patent/US6770642B2/en not_active Expired - Fee Related
-
2004
- 2004-04-20 US US10/828,014 patent/US7022701B2/en not_active Expired - Fee Related
- 2004-06-15 CO CO04055771A patent/CO5590924A2/es not_active Application Discontinuation
- 2004-06-16 EC EC2004005156A patent/ECSP045156A/es unknown
- 2004-07-19 ZA ZA200405731A patent/ZA200405731B/en unknown
- 2004-07-19 NO NO20043100A patent/NO330338B1/no not_active IP Right Cessation
- 2004-11-10 HK HK04108844A patent/HK1065949A1/xx not_active IP Right Cessation
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2006
- 2006-10-13 CY CY20061101474T patent/CY1105705T1/el unknown
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| MM1K | Lapsed by not paying the annual fees |