AR035111A1 - Procedimiento para preparar un compuesto de pirimidinona - Google Patents
Procedimiento para preparar un compuesto de pirimidinonaInfo
- Publication number
- AR035111A1 AR035111A1 ARP020103037A ARP020103037A AR035111A1 AR 035111 A1 AR035111 A1 AR 035111A1 AR P020103037 A ARP020103037 A AR P020103037A AR P020103037 A ARP020103037 A AR P020103037A AR 035111 A1 AR035111 A1 AR 035111A1
- Authority
- AR
- Argentina
- Prior art keywords
- formula
- compound
- alkyl
- organic solvent
- inert organic
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title abstract 3
- -1 pyrimidinone compound Chemical class 0.000 abstract 4
- 239000003960 organic solvent Substances 0.000 abstract 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 2
- 125000001054 5 membered carbocyclic group Chemical group 0.000 abstract 2
- YCIPQJTZJGUXND-UHFFFAOYSA-N Aglaia odorata Alkaloid Natural products C1=CC(OC)=CC=C1C1(C(C=2C(=O)N3CCCC3=NC=22)C=3C=CC=CC=3)C2(O)C2=C(OC)C=C(OC)C=C2O1 YCIPQJTZJGUXND-UHFFFAOYSA-N 0.000 abstract 2
- 150000001412 amines Chemical class 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 238000004519 manufacturing process Methods 0.000 abstract 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 abstract 1
- 125000004008 6 membered carbocyclic group Chemical group 0.000 abstract 1
- 125000003341 7 membered heterocyclic group Chemical group 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- PPYPHCLFWPCGAU-UHFFFAOYSA-N methyl 2-(trifluoromethylsulfonyloxy)acetate Chemical compound COC(=O)COS(=O)(=O)C(F)(F)F PPYPHCLFWPCGAU-UHFFFAOYSA-N 0.000 abstract 1
- 150000004702 methyl esters Chemical class 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 125000000714 pyrimidinyl group Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/56—One oxygen atom and one sulfur atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Un procedimiento para preparar un compuesto de pirimidinona de fórmula (1) en la que: Ra y Rb juntos son (CH2)n donde n es 3 ó 4, para formar, con los átomos de carbono del anillo de pirimidina a los que están unidos, un anillo carbocíclico de 5 ó 6 miembros condensado; R1 es fenilo opcionalmente sustituido por halógeno; que comprende: (a) hacer reaccionar un compuesto de fórmula (2) en la que R1, Ra y Rb son como se definen para la fórmula (1), o uno de sus derivados protegidos, con un agente sililante en un disolvente orgánico inerte, en presencia de un catalizador no acuoso; (b) tratar el producto de la etapa (a) anterior con éster metílico de ácido (trifluorometanosulfoniloxi)-acético en un disolvente orgánico inerte; y (c) la hidrólisis básica del éster metílico resultante de la etapa (b). Un procedimiento para preparar un compuesto de pirimidinona final de fórmula (3) en la que: Ra y Rb junto con los átomos de carbono del anillo de pririmidina a los que están unidos forman un anillo carbocíclico de 5 miembros condensado; R1 es 4-fluorofenilo; R2 es alquilo C1-3 sustituido por NR5R6; o R2 es Het-alquilo(C0-2) en el que Het es un anillo heterocíclico de 5 a 7 miembros que contiene N y en el que N puede estar sustituido por alquilo C1-6; R3 y R4 forman un resto de 4-(4-trifluorometilfenil)fenilo; y R5 y R6, que pueden ser iguales o diferentes, se seleccionan cada uno de hidrógeno o alquilo C1-6; que comprende: (a) hacer reaccionar un compuesto de fórmula (1), útil como intermediario, en la que R1, Ra y Rb son como se definen para la fórmula (3), o uno de sus derivados protegidos, con una amina de fórmula (4) en la que R2, R3 y R4 son como se definen para la fórmula (3), en un disolvente orgánico inerte en presencia de tetrafluoroborato de O-benzotriazol-1-il-N,N,N',N'-tetrametiluronio (TBTU) y una base de amina.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0119795.3A GB0119795D0 (en) | 2001-08-14 | 2001-08-14 | Novel process |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR035111A1 true AR035111A1 (es) | 2004-04-14 |
Family
ID=9920363
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP020103037A AR035111A1 (es) | 2001-08-14 | 2002-08-12 | Procedimiento para preparar un compuesto de pirimidinona |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US7232902B2 (es) |
| EP (1) | EP1456183B1 (es) |
| JP (1) | JP4386723B2 (es) |
| AR (1) | AR035111A1 (es) |
| AT (1) | ATE323683T1 (es) |
| AU (1) | AU2002333415A1 (es) |
| DE (1) | DE60210816T2 (es) |
| ES (1) | ES2260503T3 (es) |
| GB (1) | GB0119795D0 (es) |
| HU (1) | HUP0401296A3 (es) |
| PL (1) | PL368870A1 (es) |
| TW (1) | TW591019B (es) |
| WO (1) | WO2003016287A2 (es) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0208280D0 (en) * | 2002-04-10 | 2002-05-22 | Glaxo Group Ltd | Novel compounds |
| SI21507A (sl) | 2003-05-16 | 2004-12-31 | LEK farmacevtska dru�ba d.d. | Postopek za pripravo spojin z ace inhibitornim delovanjem |
| US7705005B2 (en) * | 2006-10-13 | 2010-04-27 | Glaxo Group Limited | Bicyclic heteroaromatic compounds |
| US20080090851A1 (en) * | 2006-10-13 | 2008-04-17 | Colin Andrew Leach | Bicyclic Heteroaromatic Compounds |
| US20080090852A1 (en) * | 2006-10-13 | 2008-04-17 | Colin Andrew Leach | Bicyclic Heteroaromatic Compounds |
| CN101687009A (zh) | 2007-05-11 | 2010-03-31 | 宾夕法尼亚大学理事会 | 治疗皮肤溃疡的方法 |
| US8962633B2 (en) | 2007-05-11 | 2015-02-24 | Thomas Jefferson University | Methods of treatment and prevention of metabolic bone diseases and disorders |
| KR101730290B1 (ko) | 2007-05-11 | 2017-04-25 | 토마스 제퍼슨 유니버시티 | 신경변성 질환 및 장애의 치료 및 예방 방법 |
| US8637524B2 (en) | 2009-07-28 | 2014-01-28 | Auspex Pharmaceuticals, Inc | Pyrimidinone inhibitors of lipoprotein-associated phospholipase A2 |
| TW201209043A (en) * | 2010-05-17 | 2012-03-01 | Glaxo Group Ltd | Novel processes |
| KR101861883B1 (ko) | 2010-12-06 | 2018-05-28 | 글락소 그룹 리미티드 | Lp-PLA₂에 의해 매개되는 질환 또는 상태의 치료에 사용하기 위한 피리미디논 화합물 |
| ES2847883T3 (es) | 2010-12-17 | 2021-08-04 | Glaxo Group Ltd | Uso de inhibidores de LP-PLA2 en el tratamiento y prevención de enfermedades oculares |
| WO2012129792A1 (zh) * | 2011-03-30 | 2012-10-04 | 中国科学院上海药物研究所 | 嘧啶酮类化合物、其制备方法及药物组合物和用途 |
| CN103619831B (zh) | 2011-06-27 | 2016-05-04 | 中国科学院上海药物研究所 | 唑类杂环化合物、其制备方法、药物组合物和用途 |
| CA2842965A1 (en) | 2011-07-27 | 2013-01-31 | Glaxo Group Limited | 2,3-dihydroimidazo[1,2-c] pyrimidin-5(1h)-one compounds use as lp-pla2 inhibitors |
| AR087309A1 (es) | 2011-07-27 | 2014-03-12 | Glaxo Group Ltd | Compuesto heterociclico de anillos condensados sustituido, composicion farmaceutica que lo comprende y su uso para la fabricacion de un medicamento para el tratamiento de enfermedades neurogenerativas y aterosclerosis |
| CN102924290A (zh) * | 2012-09-25 | 2013-02-13 | 同济大学 | 一种darapladib中间体的合成方法 |
| MX2015009633A (es) | 2013-01-25 | 2015-11-30 | Glaxosmithkline Ip Dev Ltd | Inhibidores de fosfolipasa a2 asociada con lipoproteinas basados en 2,3-dihidroimidazol[1,2-c] pirimidin-5(1h)-ona. |
| EP2948456A4 (en) | 2013-01-25 | 2016-09-14 | Glaxosmithkline Ip Dev Ltd | BICYCLIC PYRIMIDONE COMPOUNDS AS LP-PLA2 INHIBITORS |
| US9296755B2 (en) | 2013-01-25 | 2016-03-29 | Glaxosmithkline Intellectual Property Development Limited | 3,4-dihydro-1H-pyrimido[1,6-a]pyrimidin-6(2H)-one compounds and their therapeutic applications |
| WO2015087239A1 (en) | 2013-12-11 | 2015-06-18 | Ranbaxy Laboratories Limited | Processes for the preparation of darapladib and its intermediates |
| WO2015092687A2 (en) | 2013-12-17 | 2015-06-25 | Ranbaxy Laboratories Limited | Process for the purification of darapladib |
| WO2016012917A1 (en) | 2014-07-22 | 2016-01-28 | Glaxosmithkline Intellectual Property Development Limited | 1,2,3,5-tetrahydroimidazo[1,2-c]pyrimidine derivatives useful in the treatment of diseases and disorders mediated by lp-pla2 |
| WO2016012916A1 (en) | 2014-07-22 | 2016-01-28 | Glaxosmithkline Intellectual Property Development Limited | 1,2,3,5-tetrahydroimidazo[1,2-c]pyrimidine derivatives useful in the treatment of diseases and disorders mediated by lp-pla2 |
| EP4056571A4 (en) | 2019-11-09 | 2024-01-24 | Shanghai Simr Biotechnology Co., Ltd. | Tricyclic dihydroimidazopyrimidone derivative, preparation method therefor, pharmaceutical composition and use thereof |
| CN115304620A (zh) | 2021-05-07 | 2022-11-08 | 上海赛默罗生物科技有限公司 | 嘧啶酮衍生物、其制备方法、药物组合物和用途 |
| WO2025015951A1 (zh) | 2023-07-17 | 2025-01-23 | 上海枢境生物科技有限公司 | 双环[5,6]咪唑嘧啶酮类衍生物、其制备方法和应用 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK1263740T3 (da) | 2000-02-16 | 2006-11-13 | Smithkline Beecham Plc | Pyrimidin-4-on-derivat som LDL-PLA2-inhibitor |
-
2001
- 2001-08-14 GB GBGB0119795.3A patent/GB0119795D0/en not_active Ceased
-
2002
- 2002-08-12 TW TW091118058A patent/TW591019B/zh not_active IP Right Cessation
- 2002-08-12 AR ARP020103037A patent/AR035111A1/es unknown
- 2002-08-13 PL PL02368870A patent/PL368870A1/xx not_active Application Discontinuation
- 2002-08-13 EP EP02794787A patent/EP1456183B1/en not_active Expired - Lifetime
- 2002-08-13 US US10/485,972 patent/US7232902B2/en not_active Expired - Fee Related
- 2002-08-13 DE DE60210816T patent/DE60210816T2/de not_active Expired - Lifetime
- 2002-08-13 AT AT02794787T patent/ATE323683T1/de not_active IP Right Cessation
- 2002-08-13 ES ES02794787T patent/ES2260503T3/es not_active Expired - Lifetime
- 2002-08-13 JP JP2003521213A patent/JP4386723B2/ja not_active Expired - Fee Related
- 2002-08-13 WO PCT/EP2002/009067 patent/WO2003016287A2/en not_active Ceased
- 2002-08-13 HU HU0401296A patent/HUP0401296A3/hu unknown
- 2002-08-13 AU AU2002333415A patent/AU2002333415A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| ATE323683T1 (de) | 2006-05-15 |
| WO2003016287A2 (en) | 2003-02-27 |
| US7232902B2 (en) | 2007-06-19 |
| JP4386723B2 (ja) | 2009-12-16 |
| ES2260503T3 (es) | 2006-11-01 |
| HUP0401296A3 (en) | 2004-11-29 |
| EP1456183B1 (en) | 2006-04-19 |
| HUP0401296A2 (hu) | 2004-10-28 |
| AU2002333415A1 (en) | 2003-03-03 |
| DE60210816T2 (de) | 2006-10-05 |
| GB0119795D0 (en) | 2001-10-03 |
| PL368870A1 (en) | 2005-04-04 |
| EP1456183A2 (en) | 2004-09-15 |
| DE60210816D1 (de) | 2006-05-24 |
| WO2003016287A3 (en) | 2003-10-16 |
| JP2005502660A (ja) | 2005-01-27 |
| US20040242875A1 (en) | 2004-12-02 |
| TW591019B (en) | 2004-06-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FB | Suspension of granting procedure |