ZA200605434B - 1-Benzyl-5-piperazin-1-yl-3,4 dihydro-1H-quinazolin-2-one derivatives and the respective 1H-benzo(1,2,6)thiadiazine-2,2-dioxide and 1,4-dihydro-benzo(D) (1,3)oxazin-2-one derivatives as modulators of the 5-hydroxytryptamine receptor (5-HT) for the treatment of diseases of the central nervous system - Google Patents
1-Benzyl-5-piperazin-1-yl-3,4 dihydro-1H-quinazolin-2-one derivatives and the respective 1H-benzo(1,2,6)thiadiazine-2,2-dioxide and 1,4-dihydro-benzo(D) (1,3)oxazin-2-one derivatives as modulators of the 5-hydroxytryptamine receptor (5-HT) for the treatment of diseases of the central nervous system Download PDFInfo
- Publication number
- ZA200605434B ZA200605434B ZA200605434A ZA200605434A ZA200605434B ZA 200605434 B ZA200605434 B ZA 200605434B ZA 200605434 A ZA200605434 A ZA 200605434A ZA 200605434 A ZA200605434 A ZA 200605434A ZA 200605434 B ZA200605434 B ZA 200605434B
- Authority
- ZA
- South Africa
- Prior art keywords
- dihydro
- piperazin
- compound
- benzyl
- quinazolin
- Prior art date
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims description 26
- 201000010099 disease Diseases 0.000 title claims description 19
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- XCXVPQAXJPZYNW-UHFFFAOYSA-N 1h-2$l^{6},1,3-benzothiadiazine 2,2-dioxide Chemical compound C1=CC=C2C=NS(=O)(=O)NC2=C1 XCXVPQAXJPZYNW-UHFFFAOYSA-N 0.000 title description 7
- 210000003169 central nervous system Anatomy 0.000 title description 4
- SYZIUAAQNFJPJY-UHFFFAOYSA-N 1,4-dihydro-3,1-benzoxazin-2-one Chemical class C1=CC=C2COC(=O)NC2=C1 SYZIUAAQNFJPJY-UHFFFAOYSA-N 0.000 title description 3
- 108091032151 5-hydroxytryptamine receptor family Proteins 0.000 title description 3
- 102000014630 G protein-coupled serotonin receptor activity proteins Human genes 0.000 title description 3
- QDEHEDMGJOKOIM-UHFFFAOYSA-N 1-benzyl-5-piperazin-1-yl-3,4-dihydroquinazolin-2-one Chemical class O=C1NCC2=C(N3CCNCC3)C=CC=C2N1CC1=CC=CC=C1 QDEHEDMGJOKOIM-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 113
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- 125000000217 alkyl group Chemical group 0.000 claims description 84
- 229910052739 hydrogen Inorganic materials 0.000 claims description 74
- 239000001257 hydrogen Substances 0.000 claims description 74
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 57
- 125000005843 halogen group Chemical group 0.000 claims description 43
- 125000003545 alkoxy group Chemical group 0.000 claims description 34
- 125000001188 haloalkyl group Chemical group 0.000 claims description 28
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
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- 125000004429 atom Chemical group 0.000 claims description 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 15
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- 125000001072 heteroaryl group Chemical group 0.000 claims description 12
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
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- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 6
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 6
- JZFICWYCTCCINF-UHFFFAOYSA-N Thiadiazin Chemical compound S=C1SC(C)NC(C)N1CCN1C(=S)SC(C)NC1C JZFICWYCTCCINF-UHFFFAOYSA-N 0.000 claims description 6
- 125000002252 acyl group Chemical group 0.000 claims description 6
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- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 6
- AVRPFRMDMNDIDH-UHFFFAOYSA-N 1h-quinazolin-2-one Chemical compound C1=CC=CC2=NC(O)=NC=C21 AVRPFRMDMNDIDH-UHFFFAOYSA-N 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 5
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 4
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 4
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Classifications
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
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- C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
- C07D265/12—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems
- C07D265/14—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D265/18—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with hetero atoms directly attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/15—Six-membered rings
- C07D285/16—Thiadiazines; Hydrogenated thiadiazines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
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- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Neurology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Psychiatry (AREA)
- Psychology (AREA)
- Pain & Pain Management (AREA)
- Anesthesiology (AREA)
- Hospice & Palliative Care (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US53708004P | 2004-01-16 | 2004-01-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200605434B true ZA200605434B (en) | 2008-02-27 |
Family
ID=34794441
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200605434A ZA200605434B (en) | 2004-01-16 | 2006-06-30 | 1-Benzyl-5-piperazin-1-yl-3,4 dihydro-1H-quinazolin-2-one derivatives and the respective 1H-benzo(1,2,6)thiadiazine-2,2-dioxide and 1,4-dihydro-benzo(D) (1,3)oxazin-2-one derivatives as modulators of the 5-hydroxytryptamine receptor (5-HT) for the treatment of diseases of the central nervous system |
Country Status (19)
| Country | Link |
|---|---|
| US (2) | US7196087B2 (es) |
| EP (1) | EP1708713B1 (es) |
| JP (1) | JP4533391B2 (es) |
| KR (1) | KR100843053B1 (es) |
| CN (1) | CN1909909B (es) |
| AR (1) | AR047958A1 (es) |
| AT (1) | ATE388712T1 (es) |
| AU (1) | AU2005205016B2 (es) |
| BR (1) | BRPI0506909A (es) |
| CA (1) | CA2552681A1 (es) |
| CO (1) | CO5700763A2 (es) |
| DE (1) | DE602005005298T2 (es) |
| ES (1) | ES2302174T3 (es) |
| IL (1) | IL176631A0 (es) |
| NO (1) | NO20062791L (es) |
| RU (1) | RU2006129464A (es) |
| TW (1) | TW200530222A (es) |
| WO (1) | WO2005067933A1 (es) |
| ZA (1) | ZA200605434B (es) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2359725T3 (es) * | 2004-09-30 | 2011-05-26 | F. Hoffmann-La Roche Ag | Composiciones y métodos para el tratamiento de trastornos cognitivos. |
| US7713954B2 (en) * | 2004-09-30 | 2010-05-11 | Roche Palo Alto Llc | Compositions and methods for treating cognitive disorders |
| EP1836183A2 (en) * | 2004-12-13 | 2007-09-26 | Galileo Pharmaceuticals, Inc. | Spiro derivatives as lipoxygenase inhibitors |
| JP2009501184A (ja) * | 2005-07-13 | 2009-01-15 | エフ．ホフマン−ラ ロシュ アーゲー | ５−ｈｔ６、５−ｈｔ２４としてのベンゾイミダゾール誘導体 |
| KR100817538B1 (ko) * | 2006-07-05 | 2008-03-27 | 한국화학연구원 | 신규 치환된―１ｈ―퀴나졸린―２,４―디온 유도체, 이의제조방법 및 이를 함유하는 약학적 조성물 |
| JP5256202B2 (ja) * | 2006-09-11 | 2013-08-07 | エム・エス・ディー・オス・ベー・フェー | キナゾリノンおよびイソキノリノンアセトアミド誘導体 |
| US7718652B2 (en) | 2006-12-12 | 2010-05-18 | Wyeth Llc | Substituted benzothiadiazinedioxide derivatives and methods of their use |
| JP2011524383A (ja) * | 2008-06-20 | 2011-09-01 | ロッタファルム・ソシエタ・ペル・アチオニ | ６−１ｈ−イミダゾ−キナゾリンおよびキノリン誘導体、新規ｍａｏ阻害剤およびイミダゾリンレセプターリガンド |
| US8044047B2 (en) | 2008-09-08 | 2011-10-25 | Hoffman-La Roche Inc. | 5-substituted benzoxazines |
| JP2013526590A (ja) | 2010-05-21 | 2013-06-24 | シェンヅェン サルブリス ファーマシューティカルズ カンパニー リミテッド | 縮環キナゾリン誘導体及びその使用 |
| WO2018093818A1 (en) * | 2016-11-15 | 2018-05-24 | Temple University-Of The Commonwealth System Of Higher Education | Novel modulators of the 5-hydroxytryptamine receptor 7 and their method of use |
| MX2022004736A (es) * | 2019-10-21 | 2022-07-27 | Alairion Inc | Derivados de acido 3-(4-(11h-dibenzo [b, e] [1, 4] azepin-6-il)piperazin-1-il)- y 3-(4- dibenzo [b, f] [1, 4] oxazepin/tiazepin/diazepin-11-il)piperazin-1-il)propanoico como moduladores de los receptores h1 y 5-ht2a para el tratamiento de los trastornos del sue?o. |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3642791A (en) * | 1969-08-13 | 1972-02-15 | Sandoz Ag | Morpholino-1-substituted-2(1h)-quinazolinones |
| JPS5271483A (en) * | 1975-12-11 | 1977-06-14 | Sumitomo Chem Co Ltd | Synthesis of 2(1h)-quinazolinone derivatives |
| CN1015459B (zh) * | 1985-06-06 | 1992-02-12 | 田边制药株式会社 | 喹唑啉酮化合物的制备方法 |
| GR1000821B (el) * | 1988-11-22 | 1993-01-25 | Tanabe Seiyaku Co | Μεθοδος παραγωγης παραγωγων κιναζολινονης. |
| WO1998018781A2 (en) | 1996-10-28 | 1998-05-07 | Versicor, Inc. | Fused 2,4-pyrimidinedione combinatorial libraries, their preparation and the use of fused 2,4-pyrimidinediones derivatives as antimicrobial agents |
| WO1998042688A1 (fr) | 1997-03-26 | 1998-10-01 | Sumitomo Pharmaceuticals Co., Ltd. | Derives de 4-arylmethylene-1,4-dihydro-2h-azine |
| US6331538B1 (en) | 1997-10-28 | 2001-12-18 | Warner-Lambert Company | 7-substituted quinazolin-2,4-diones useful as antibacterial agents |
| AU2074699A (en) * | 1998-01-26 | 1999-08-09 | Yamanouchi Pharmaceutical Co., Ltd. | Novel benzene-fused heterocyclic derivatives or salts thereof |
| ATE286883T1 (de) * | 1999-11-05 | 2005-01-15 | Smithkline Beecham Plc | Isochinolin und chinazolinderivate mit kombinierter 5ht1a, 5ht1b und 5ht1d rezeptor aktivität |
| EP1248624A4 (en) | 1999-11-23 | 2003-01-22 | Smithkline Beecham Corp | 3,4-DIHYDRO- (1H) -CHIRAZOLINE-2-ONES AND THE USE THEREOF AS CSBP / P38 KINASE INHIBITORS |
| AU2525701A (en) | 1999-12-14 | 2001-06-25 | Sanofi-Synthelabo | Derivatives of quinazolinedione phthalimide, preparations thereof and their therapeutic uses |
| EP1345603A4 (en) * | 2000-12-20 | 2004-09-08 | Merck & Co Inc | P38 KINASE INHIBITORS (HALO-BENZO CARBONYL) HETEROCYCLO- FUSIONNES PHENYL |
| US6998408B2 (en) * | 2001-03-23 | 2006-02-14 | Bristol-Myers Squibb Pharma Company | 6-5, 6-6, or 6-7 Heterobicycles as factor Xa inhibitors |
| KR20040010709A (ko) * | 2001-06-15 | 2004-01-31 | 에프. 호프만-라 로슈 아게 | 5-ｈｔ6 수용체 친화력을 갖는 4-피페라지닐인돌 유도체 |
| GB0203804D0 (en) * | 2002-02-18 | 2002-04-03 | Glaxo Group Ltd | Compounds |
| RS51042B (sr) * | 2002-05-13 | 2010-10-31 | F. Hoffmann-La Roche Ag. | Derivati benzoksazina kao 5-ht6 modulatori i njihove primene |
-
2005
- 2005-01-07 JP JP2006548231A patent/JP4533391B2/ja not_active Expired - Fee Related
- 2005-01-07 AT AT05700747T patent/ATE388712T1/de active
- 2005-01-07 RU RU2006129464/04A patent/RU2006129464A/ru unknown
- 2005-01-07 CN CN2005800026123A patent/CN1909909B/zh not_active Expired - Fee Related
- 2005-01-07 ES ES05700747T patent/ES2302174T3/es active Active
- 2005-01-07 EP EP05700747A patent/EP1708713B1/en active Active
- 2005-01-07 AU AU2005205016A patent/AU2005205016B2/en not_active Ceased
- 2005-01-07 WO PCT/EP2005/000095 patent/WO2005067933A1/en active IP Right Grant
- 2005-01-07 BR BRPI0506909-2A patent/BRPI0506909A/pt not_active IP Right Cessation
- 2005-01-07 DE DE602005005298T patent/DE602005005298T2/de active Active
- 2005-01-07 CA CA002552681A patent/CA2552681A1/en not_active Abandoned
- 2005-01-07 KR KR1020067014320A patent/KR100843053B1/ko not_active IP Right Cessation
- 2005-01-13 AR ARP050100106A patent/AR047958A1/es not_active Application Discontinuation
- 2005-01-13 TW TW094101029A patent/TW200530222A/zh unknown
- 2005-01-14 US US11/035,506 patent/US7196087B2/en not_active Expired - Fee Related
-
2006
- 2006-06-15 NO NO20062791A patent/NO20062791L/no not_active Application Discontinuation
- 2006-06-29 IL IL176631A patent/IL176631A0/en unknown
- 2006-06-30 ZA ZA200605434A patent/ZA200605434B/en unknown
- 2006-07-13 CO CO06068258A patent/CO5700763A2/es not_active Application Discontinuation
-
2007
- 2007-02-07 US US11/703,424 patent/US7365063B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JP2007517826A (ja) | 2007-07-05 |
| AR047958A1 (es) | 2006-03-15 |
| KR20060126720A (ko) | 2006-12-08 |
| CO5700763A2 (es) | 2006-11-30 |
| AU2005205016A1 (en) | 2005-07-28 |
| TW200530222A (en) | 2005-09-16 |
| EP1708713A1 (en) | 2006-10-11 |
| NO20062791L (no) | 2006-08-01 |
| US20070149510A1 (en) | 2007-06-28 |
| IL176631A0 (en) | 2006-10-31 |
| DE602005005298D1 (de) | 2008-04-24 |
| WO2005067933A1 (en) | 2005-07-28 |
| DE602005005298T2 (de) | 2009-03-12 |
| US7196087B2 (en) | 2007-03-27 |
| JP4533391B2 (ja) | 2010-09-01 |
| KR100843053B1 (ko) | 2008-07-01 |
| US20050165001A1 (en) | 2005-07-28 |
| BRPI0506909A (pt) | 2007-05-29 |
| ES2302174T3 (es) | 2008-07-01 |
| EP1708713B1 (en) | 2008-03-12 |
| ATE388712T1 (de) | 2008-03-15 |
| CN1909909B (zh) | 2010-12-15 |
| US7365063B2 (en) | 2008-04-29 |
| RU2006129464A (ru) | 2008-02-27 |
| CA2552681A1 (en) | 2005-07-28 |
| AU2005205016B2 (en) | 2010-07-15 |
| CN1909909A (zh) | 2007-02-07 |
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