HUP0500332A2 - Helyettesített 2-pirimidinil-6,7,8,9-tetrahidropirimido[1,2-a]-pirimidin-4-on és 7-piridinil-2,3-dihidroimidazo[1,2-a]-pirimidin-5 (1H)-on-származékok, alkalmazásuk és az ezeket tartalmazó gyógyszerkészítmények - Google Patents
Helyettesített 2-pirimidinil-6,7,8,9-tetrahidropirimido[1,2-a]-pirimidin-4-on és 7-piridinil-2,3-dihidroimidazo[1,2-a]-pirimidin-5 (1H)-on-származékok, alkalmazásuk és az ezeket tartalmazó gyógyszerkészítményekInfo
- Publication number
- HUP0500332A2 HUP0500332A2 HU0500332A HUP0500332A HUP0500332A2 HU P0500332 A2 HUP0500332 A2 HU P0500332A2 HU 0500332 A HU0500332 A HU 0500332A HU P0500332 A HUP0500332 A HU P0500332A HU P0500332 A2 HUP0500332 A2 HU P0500332A2
- Authority
- HU
- Hungary
- Prior art keywords
- group
- atom
- ring
- alkyl group
- optionally substituted
- Prior art date
Links
- JOQYRATWFVJNPN-UHFFFAOYSA-N 2-pyrimidin-2-yl-1,6,7,8-tetrahydropyrimido[1,2-a]pyrimidin-4-one Chemical class N1=C2NCCCN2C(=O)C=C1C1=NC=CC=N1 JOQYRATWFVJNPN-UHFFFAOYSA-N 0.000 title 1
- BUOYBEPCJMUPNV-UHFFFAOYSA-N 7-pyrimidin-2-yl-3,8-dihydro-2h-imidazo[1,2-a]pyrimidin-5-one Chemical class N1=C2NCCN2C(=O)C=C1C1=NC=CC=N1 BUOYBEPCJMUPNV-UHFFFAOYSA-N 0.000 title 1
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 9
- 229910052799 carbon Inorganic materials 0.000 abstract 5
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 239000003814 drug Substances 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 2
- 230000003449 preventive effect Effects 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 125000004434 sulfur atom Chemical group 0.000 abstract 2
- 230000001225 therapeutic effect Effects 0.000 abstract 2
- 208000024827 Alzheimer disease Diseases 0.000 abstract 1
- 101150053721 Cdk5 gene Proteins 0.000 abstract 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 1
- 206010028980 Neoplasm Diseases 0.000 abstract 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 1
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 abstract 1
- 230000002159 abnormal effect Effects 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 125000001769 aryl amino group Chemical group 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 201000011510 cancer Diseases 0.000 abstract 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 229940079593 drug Drugs 0.000 abstract 1
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 abstract 1
- 125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 125000002883 imidazolyl group Chemical group 0.000 abstract 1
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 abstract 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 abstract 1
- 125000001624 naphthyl group Chemical group 0.000 abstract 1
- 230000004770 neurodegeneration Effects 0.000 abstract 1
- 208000015122 neurodegenerative disease Diseases 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 abstract 1
- 125000000714 pyrimidinyl group Chemical group 0.000 abstract 1
- 150000008318 pyrimidones Chemical class 0.000 abstract 1
- 125000000168 pyrrolyl group Chemical group 0.000 abstract 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 abstract 1
- 125000003375 sulfoxide group Chemical group 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical group C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 abstract 1
Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- 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
- C07D487/04—Ortho-condensed systems
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- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
- A61K31/551—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having two nitrogen atoms, e.g. dilazep
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Abstract
A találmány az (I) általános képletű pirimidonszármazékokra vagy sóiravonatkozik, a képletben X jelentése két hidrogénatom, kénatom,oxigénatom vagy egy 1-2 szénatomos alkilcsoport és egy hidrogénatom; Yjelentése vegyértékkötés, eteniléncsoport, etiniléncsoport,oxigénatom, kénatom, szulfonilcsoport, szulfoxidcsoport,karbonilcsoport, nitrogénatom, amely adott esetben helyettesített;vagy metiléncsoport, amely adott esetben helyettesített; R1 jelentésepirimidincsoport, amely adott esetben helyettesített; R2 jelentése 1-6szénatomos alkilcsoport, amely adott esetben 6-10 szénatomosariloxicsoporttal vagy 6-10 szénatomos arilaminocsoporttalhelyettesített; 3-6 szénatomos cikloalkilcsoport, 1-4 szénatomosalkiltiocsoport, 1-4 szénatomos alkoxicsoport, 1-2 szénatomosperhalogénezett alkilcsoport, 1-3 szénatomos halogénezettalkilcsoport, feniltiocsoport, benzilcsoport, benzolgyűrű, indángyűrű,5,6,7,8-tetrahidronaftalingyűrű, naftalingyűrű, piridingyűrű,pirrolgyűrű, tioféngyűrű, furángyűrű vagy imidazolgyűrű; R3 és R4jelentése egymástól függetlenül hidrogénatom, 1-6 szénatomosalkilcsoport, hidroxilcsoport, 1-4 szénatomos alkoxicsoport vagyhalogénatom; R5 jelentése hidrogénatom, 1-6 szénatomos alkilcsoportvagy halogénatom, amikor m értéke 0, p értéke 1, 2 vagy 3, amikor mértéke 1, p értéke 0, 1 vagy 2, amikor m értéke 2, p értéke 0 vagy 1,és n értéke 0, 1, 2 vagy 3. A találmány gyógyszerre is vonatkozik,amely hatóanyagként a fenti származékot vagy sóját tartalmazza, ésamely a GSK3b vagy a GSK3b és cdk5/p25 abnormális aktivitása általokozott neurodegeneratív betegség, például Alzheimer-betegség megelőzőés/vagy terápiás kezelésére alkalmazható. Az (I) általános képletűvegyületek alkalamzhatók rákok megelőző és/vagy terápiás kezelésérealkalmas gyógyszer előállítására is. Ó
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP01402431A EP1295884A1 (en) | 2001-09-21 | 2001-09-21 | 2-pyrimidinyl-6,7,8,9-tetrahydropyrimido[1,2-a]Pyrimidin-4-one and 7-Pyrimidinyl-2,3-Dihydroimidazo[1,2-a]Pyrimidin-5(1H)one derivatives |
EP02290488A EP1340760A1 (en) | 2002-02-28 | 2002-02-28 | Substituted 2-pyrimidinyl-6,7,8,9-tetrahydropyrimido[1,2-a]pyrimidin-4-one and 7-pyrimidinyl-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1H)one derivatives |
PCT/EP2002/011127 WO2003027115A1 (en) | 2001-09-21 | 2002-09-19 | Substituted 2-pyrimidinyl-6,7,8,9-tetrahydropyrimido[1,2-a]pyrimidin-4-one and 7-pyrimidinyl-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1h)one derivatives for neurodegenerative disorders |
Publications (2)
Publication Number | Publication Date |
---|---|
HUP0500332A2 true HUP0500332A2 (hu) | 2005-07-28 |
HUP0500332A3 HUP0500332A3 (en) | 2009-12-28 |
Family
ID=26077255
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
HU0500332A HUP0500332A3 (en) | 2001-09-21 | 2002-09-19 | Substituted 2-pyrimidinyl-6,7,8,9-tetrahydropyrimido[1,2-a]pyrimidin-4-one and 7-pyrimidinyl-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1h)-one derivatives, their use and pharmaceutical compositions containing them |
Country Status (24)
Country | Link |
---|---|
US (2) | US7388005B2 (hu) |
EP (1) | EP1430056B1 (hu) |
JP (2) | JP4570361B2 (hu) |
KR (1) | KR100868840B1 (hu) |
CN (1) | CN1247586C (hu) |
AR (1) | AR036599A1 (hu) |
AT (1) | ATE307815T1 (hu) |
AU (1) | AU2002342798C1 (hu) |
BR (1) | BR0212904A (hu) |
CA (1) | CA2457952C (hu) |
CY (1) | CY1105553T1 (hu) |
DE (1) | DE60206946T2 (hu) |
DK (1) | DK1430056T3 (hu) |
EA (2) | EA009456B1 (hu) |
ES (1) | ES2250721T3 (hu) |
HK (1) | HK1091495A1 (hu) |
HU (1) | HUP0500332A3 (hu) |
IL (2) | IL160397A0 (hu) |
MX (1) | MXPA04002632A (hu) |
NO (1) | NO329566B1 (hu) |
NZ (1) | NZ531244A (hu) |
PL (1) | PL370535A1 (hu) |
SI (1) | SI1430056T1 (hu) |
WO (1) | WO2003027115A1 (hu) |
Families Citing this family (30)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1454909B1 (en) * | 2003-03-07 | 2008-08-20 | Sanofi Aventis | 8'-pyridinyl-dihydrospiro (cycloalkyl) -pyrimido (1,2-a) pyrimidin-6-one and 8'-pyrimidinyl-dihydrospiro (cycloalkyl) pyrimido (1,2-a) pyrimidin-6 derivatives -one and their use against neurodegenerative diseases |
EP1557417B1 (en) * | 2003-12-19 | 2007-03-07 | Sanofi-Aventis | Substituted 8'-pyri(mi)dinyl-dihydrospiro-[cycloalkylamine]-pyrimido[1,2-a] pyrimidin-6-one derivatives |
ATE393157T1 (de) | 2004-01-22 | 2008-05-15 | Amgen Inc | Substituierte heterocyclische verbindungen und anwendungsverfahren |
CN101198609A (zh) * | 2005-06-14 | 2008-06-11 | 先灵公司 | 天冬氨酰基蛋白酶抑制剂 |
CA2620333A1 (en) | 2005-08-26 | 2007-03-01 | Braincells, Inc. | Neurogenesis by muscarinic receptor modulation |
EP2258359A3 (en) | 2005-08-26 | 2011-04-06 | Braincells, Inc. | Neurogenesis by muscarinic receptor modulation with sabcomelin |
EP2377530A3 (en) | 2005-10-21 | 2012-06-20 | Braincells, Inc. | Modulation of neurogenesis by PDE inhibition |
WO2007053596A1 (en) | 2005-10-31 | 2007-05-10 | Braincells, Inc. | Gaba receptor mediated modulation of neurogenesis |
US20100216734A1 (en) | 2006-03-08 | 2010-08-26 | Braincells, Inc. | Modulation of neurogenesis by nootropic agents |
JP2009536669A (ja) | 2006-05-09 | 2009-10-15 | ブレインセルス,インコーポレイティド | アンジオテンシン調節による神経新生 |
US20100184806A1 (en) | 2006-09-19 | 2010-07-22 | Braincells, Inc. | Modulation of neurogenesis by ppar agents |
EP1939187A1 (en) * | 2006-12-20 | 2008-07-02 | Sanofi-Aventis | Substituted heteroaryl pyridopyrimidone derivatives |
EP1992624A1 (en) * | 2007-05-16 | 2008-11-19 | Sanofi-Aventis | Heteroarylamide pyrimidone compounds |
EP1992621A1 (en) | 2007-05-16 | 2008-11-19 | Sanofi-Aventis | Heteroarylamide-substituted pyrimidone derivatives for the treatment of neurodegenerative diseases |
EP1992620A1 (en) * | 2007-05-16 | 2008-11-19 | Sanofi-Aventis | Arylamide pyrimidone derivatives for the treatment of neurodegenerative diseases |
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US3865836A (en) * | 1972-12-08 | 1975-02-11 | Janssen Pharmaceutica Nv | Bicyclic imidazoles |
SU600143A1 (ru) * | 1976-12-06 | 1978-03-30 | Ордена Трудового Красного Знамени Институт Органического Синтеза Ан Латвийской Сср | Способ получени гетероциклических систем, содержащих бормзамещенный имидазол |
JPS63216886A (ja) * | 1987-03-05 | 1988-09-09 | Sumitomo Chem Co Ltd | ピリミドピリミジン誘導体およびその製造法 |
JP2862958B2 (ja) * | 1990-06-09 | 1999-03-03 | 三協化学株式会社 | 感熱転写記録用色素 |
US6153618A (en) * | 1996-10-11 | 2000-11-28 | Chiron Corporation | Inhibitors of glycogen synthase 3 kinase |
IL130181A0 (en) * | 1996-12-05 | 2000-06-01 | Amgen Inc | Substituted pyrimidone and pyridone compounds and methods of use |
NZ506417A (en) * | 1998-02-17 | 2003-05-30 | Tularik Inc | Anti-viral pyrimidine derivatives |
ATE303383T1 (de) * | 1999-12-17 | 2005-09-15 | Chiron Corp | Bizyklische inhibitoren von glycogen synthase kinase 3 |
FR2804959B1 (fr) | 2000-02-15 | 2006-04-28 | Centre Nat Rech Scient | Utilisation de derives de paullones pour la fabrication de medicaments |
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