EA007737B1 - ГЕТЕРОАРИЛЗАМЕЩЕННЫЕ ПРОИЗВОДНЫЕ 2-ПИРИДИНИЛ- И 2-ПИРИМИДИНИЛ-6,7,8,9-ТЕТРАГИДРОПИРИМИДО[1,2-a]ПИРИМИДИН-4-ОНА - Google Patents
ГЕТЕРОАРИЛЗАМЕЩЕННЫЕ ПРОИЗВОДНЫЕ 2-ПИРИДИНИЛ- И 2-ПИРИМИДИНИЛ-6,7,8,9-ТЕТРАГИДРОПИРИМИДО[1,2-a]ПИРИМИДИН-4-ОНА Download PDFInfo
- Publication number
- EA007737B1 EA007737B1 EA200400936A EA200400936A EA007737B1 EA 007737 B1 EA007737 B1 EA 007737B1 EA 200400936 A EA200400936 A EA 200400936A EA 200400936 A EA200400936 A EA 200400936A EA 007737 B1 EA007737 B1 EA 007737B1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- pyrimidin
- tetrahydropyrimido
- ylmethyl
- pyridin
- dimethyl
- Prior art date
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- DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical class O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 title claims description 64
- 150000003839 salts Chemical class 0.000 claims abstract description 46
- 239000003814 drug Substances 0.000 claims abstract description 29
- 150000008318 pyrimidones Chemical class 0.000 claims abstract description 24
- 238000011282 treatment Methods 0.000 claims abstract description 24
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 23
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 21
- 239000004480 active ingredient Substances 0.000 claims abstract description 20
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 20
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 19
- 125000005843 halogen group Chemical group 0.000 claims abstract description 18
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- 125000005842 heteroatom Chemical group 0.000 claims abstract description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 10
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 9
- 125000004434 sulfur atom Chemical group 0.000 claims abstract description 9
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 116
- -1 benzofuran-2-ylmethyl Chemical group 0.000 claims description 59
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 31
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- LCKCIHLNWFCXLK-UHFFFAOYSA-N 1,4,7,8-tetrahydropyrimido[1,2-a]pyrimidin-6-one Chemical compound N1C=CCN2C(=O)CCN=C21 LCKCIHLNWFCXLK-UHFFFAOYSA-N 0.000 claims description 10
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- 125000004429 atom Chemical group 0.000 claims description 4
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- CSIYPJQZODIRND-UHFFFAOYSA-N 1-[2-(1h-indol-3-yl)ethyl]-7-pyridin-4-yl-2,3-dihydroimidazo[1,2-a]pyrimidin-5-one Chemical compound N1=C2N(CCC=3C4=CC=CC=C4NC=3)CCN2C(=O)C=C1C1=CC=NC=C1 CSIYPJQZODIRND-UHFFFAOYSA-N 0.000 claims description 3
- YOBYLQSAZIBJKW-UHFFFAOYSA-N 1-[3-(1h-indol-3-yl)propyl]-7-pyridin-4-yl-2,3-dihydroimidazo[1,2-a]pyrimidin-5-one Chemical compound N1=C2N(CCCC=3C4=CC=CC=C4NC=3)CCN2C(=O)C=C1C1=CC=NC=C1 YOBYLQSAZIBJKW-UHFFFAOYSA-N 0.000 claims description 3
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical compound OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 claims description 3
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- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
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- AKYVTEJEWKKJOO-UHFFFAOYSA-N 9-[(5-fluoro-8-methoxy-3,4-dihydro-2h-chromen-2-yl)methyl]-8-methyl-2-pyrimidin-4-yl-7,8-dihydro-6h-pyrimido[1,2-a]pyrimidin-4-one Chemical compound O1C=2C(OC)=CC=C(F)C=2CCC1CN1C(C)CCN(C(C=2)=O)C1=NC=2C1=CC=NC=N1 AKYVTEJEWKKJOO-UHFFFAOYSA-N 0.000 claims description 2
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- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 2
- 208000028683 bipolar I disease Diseases 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 claims 2
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Classifications
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
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- 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
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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
-
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- 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
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Landscapes
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP02290486A EP1348708A1 (en) | 2002-02-28 | 2002-02-28 | Heteroaryl 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 |
| EP02290485A EP1340758A1 (en) | 2002-02-28 | 2002-02-28 | Heteroaryl substituted 2-pyridinyl-6,7,8,9-tetrahydropyrimido[1,2-a]pyrimidin-4-one and 7-pyridinyl-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1H)one derivatives |
| PCT/EP2003/002651 WO2003072579A1 (en) | 2002-02-28 | 2003-02-26 | HETEROARYL SUBSTITUTED 2-PYRIDINYL AND 2-PYRIMIDINYL -6,7,8,9- TETRAHYDROPYRIMIDO[1,2-a] PYRIMIDIN-4-ONE DERIVATIVES |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EA200400936A1 EA200400936A1 (ru) | 2005-02-24 |
| EA007737B1 true EA007737B1 (ru) | 2006-12-29 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EA200400936A EA007737B1 (ru) | 2002-02-28 | 2003-02-26 | ГЕТЕРОАРИЛЗАМЕЩЕННЫЕ ПРОИЗВОДНЫЕ 2-ПИРИДИНИЛ- И 2-ПИРИМИДИНИЛ-6,7,8,9-ТЕТРАГИДРОПИРИМИДО[1,2-a]ПИРИМИДИН-4-ОНА |
Country Status (22)
| Country | Link |
|---|---|
| US (2) | US7232827B2 (enExample) |
| EP (1) | EP1480983B1 (enExample) |
| JP (1) | JP4458851B2 (enExample) |
| KR (1) | KR101030629B1 (enExample) |
| CN (1) | CN1315832C (enExample) |
| AR (1) | AR038619A1 (enExample) |
| AT (1) | ATE309247T1 (enExample) |
| AU (1) | AU2003221500B9 (enExample) |
| BR (1) | BR0308109A (enExample) |
| CA (1) | CA2474823C (enExample) |
| DE (1) | DE60302221T2 (enExample) |
| DK (1) | DK1480983T3 (enExample) |
| EA (1) | EA007737B1 (enExample) |
| ES (1) | ES2250883T3 (enExample) |
| IL (1) | IL163287A (enExample) |
| MX (1) | MXPA04008364A (enExample) |
| NO (1) | NO329805B1 (enExample) |
| NZ (1) | NZ534466A (enExample) |
| PL (1) | PL372465A1 (enExample) |
| SI (1) | SI1480983T1 (enExample) |
| TW (1) | TWI303637B (enExample) |
| WO (1) | WO2003072579A1 (enExample) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1454910A1 (en) | 2003-03-07 | 2004-09-08 | Sanofi-Synthelabo | Substituted pyrimidinyl-2-(diaza-bicyclo-alkyl)-pyrimidone derivatives |
| DK1603910T3 (da) | 2003-03-07 | 2009-11-23 | Sanofi Aventis | Substituerede 2-(diazabicykloalkyl)-pyrimidon-derivater |
| 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 |
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| US20100216734A1 (en) | 2006-03-08 | 2010-08-26 | Braincells, Inc. | Modulation of neurogenesis by nootropic agents |
| EP2021000A2 (en) | 2006-05-09 | 2009-02-11 | Braincells, Inc. | Neurogenesis by modulating angiotensin |
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| PL2448940T3 (pl) * | 2009-07-02 | 2014-10-31 | Sanofi Sa | Pochodne 6,7,8,9-tetrahydro-pirymido{1,2-a} pirymidyn-4-onu, ich wytwarzanie i zastosowanie farmaceutyczne |
| KR101745028B1 (ko) | 2009-07-02 | 2017-06-08 | 사노피 | 신규 ２,３-디히드로-１ｈ-이미다조（１,２-ａ）피리미딘-５-온 유도체, 그의 제조법 및 그의 제약 용도 |
| FR2947551B1 (fr) * | 2009-07-02 | 2012-05-18 | Sanofi Aventis | Nouveaux derives de 1,2,3,4-tetrahydro-pyrimido{1,2-a)pyrimidin-6-one, leur preparation et leur utilisation pharmaceutique comme inhibiteurs de phosphorylation d'akt (pkb) |
| FR2947550B1 (fr) * | 2009-07-02 | 2012-05-18 | Sanofi Aventis | Nouveaux derives de 2,3-dihydro-1h-imidazo{1,2-a}pyrimidin-5-one, leur preparation et leur utilisation pharmaceutique comme inhibiteurs de phosphorylation d'akt (pkb) |
| CN102715186A (zh) * | 2012-06-15 | 2012-10-10 | 王学权 | 一种增效除草组合物 |
| FR2992314B1 (fr) | 2012-06-22 | 2015-10-16 | Sanofi Sa | Nouveaux derives de 2,3-dihydro-1h-imidazo{1,2-a}pyrimidin-5-one et 1,2,3,4-tetrahydro-pyrimido{1,2-a}pyrimidin-6-one comportant une morpholine substituee, leur preparation et leur utilisation pharmaceutique |
| BR112016022519A8 (pt) * | 2014-04-01 | 2018-03-06 | Pfizer | cromeno e 1,1a,2,7b-tetra-hidrociclopropa[c]cromeno piridopirazinadionas como moduladores de gama-secretase |
| WO2015155738A2 (en) | 2014-04-09 | 2015-10-15 | Christopher Rudd | Use of gsk-3 inhibitors or activators which modulate pd-1 or t-bet expression to modulate t cell immunity |
| ES2968804T3 (es) * | 2017-05-24 | 2024-05-14 | Abbisko Therapeutics Co Ltd | Derivado de azaarilo, método de preparación del mismo y uso farmacéutico del mismo |
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| JP2002514195A (ja) * | 1996-12-05 | 2002-05-14 | アムジエン・インコーポレーテツド | 置換ピリミジン化合物およびそれの使用 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2000018758A1 (en) * | 1998-09-25 | 2000-04-06 | Mitsubishi Chemical Corporation | Pyrimidone derivatives |
| WO2002018386A1 (en) * | 2000-09-01 | 2002-03-07 | Sanofi-Synthelabo | 2-PYRIDINYL-6,7,8,9-TETRAHYDROPYRIMIDO[1,2-a]PYRIMIDIN-4-ONE AND 7-PYRIDINYL-2,3-DIHYDROIMIDAZO[1,2-a]PYRIMIDIN-5(1H)ONE DERIVATI VES |
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