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8'-氯5'-羟基-1'H-螺[环己烷-1,4'-喹唑啉]-2'(3'H)-酮 | 460346-10-5

分子结构分类

有机化合物 - 有机杂环化合物 - 二氮杂萘

中文名称

8'-氯5'-羟基-1'H-螺[环己烷-1,4'-喹唑啉]-2'(3'H)-酮

中文别名

——

英文名称

8-chloro-5-hydroxy-spiro[1,3-dihydroquinazoline-4,1'-cyclohexane]-2-one

英文别名

8'-chloro-5'-hydroxy-1'H-spiro[cyclohexane-1,4'-quinazolin]-2'(3'H)-one；8-chloro-5-hydroxyspiro[1,3-dihydroquinazoline-4,1'-cyclohexane]-2-one

8'-氯5'-羟基-1'H-螺[环己烷-1,4'-喹唑啉]-2'(3'H)-酮化学式

CAS

460346-10-5

化学式

C₁₃H₁₅ClN₂O₂

mdl

——

分子量

266.727

InChiKey

DHMOUHKNWPAATO-UHFFFAOYSA-N

BEILSTEIN

——

EINECS

——

物化性质

沸点：

415.6±45.0 °C(Predicted)
密度：

1.41±0.1 g/cm3(Predicted)

计算性质

辛醇/水分配系数(LogP)：

2.4
重原子数：

18
可旋转键数：

0
环数：

3.0
sp3杂化的碳原子比例：

0.46
拓扑面积：

61.4
氢给体数：

3
氢受体数：

2

上下游信息

上游原料

中文名称	英文名称	CAS号	化学式	分子量
——	8-chloro-5-methoxy-spiro[1,3-dihydroquinazoline-4,1'-cyclohexane]-2-one	460346-02-5	C₁₄H₁₇ClN₂O₂	280.754

下游产品

中文名称	英文名称	CAS号	化学式	分子量
——	8′-chloro-5′-(2-hydroxyethoxy)-2′,3′-dihydro-1′H-spiro[cyclohexane-1,4′-quinazoline]-2′-one	460346-28-5	C₁₅H₁₉ClN₂O₃	310.78
——	5-(2-Aminoethoxy)-8-chlorospiro[1,3-dihydroquinazoline-4,1'-cyclohexane]-2-one	——	C₁₅H₂₀ClN₃O₂	309.796
——	2-(8-Chloro-2-oxospiro[1,3-dihydroquinazoline-4,1'-cyclohexane]-5-yl)oxyacetonitrile	460346-31-0	C₁₅H₁₆ClN₃O₂	305.764
——	5-[2-(2-Aminoethoxy)ethoxy]-8-chlorospiro[1,3-dihydroquinazoline-4,1'-cyclohexane]-2-one	——	C₁₇H₂₄ClN₃O₃	353.849
——	8-Chloro-5-[2-(methylamino)ethoxy]spiro[1,3-dihydroquinazoline-4,1'-cyclohexane]-2-one	——	C₁₆H₂₂ClN₃O₂	323.823
——	8'-chloro-5'-([methylthio]methoxy)-1'H-spiro[cyclohexane-1,4'-quinazolin]-2'(3'H)-one	——	C₁₅H₁₉ClN₂O₂S	326.847
——	2-(8-Chloro-2-oxospiro[1,3-dihydroquinazoline-4,1'-cyclohexane]-5-yl)oxyacetic acid	——	C₁₅H₁₇ClN₂O₄	324.764
——	Ethyl 2-(8-chloro-2-oxospiro[1,3-dihydroquinazoline-4,1'-cyclohexane]-5-yl)oxyacetate	460346-22-9	C₁₇H₂₁ClN₂O₄	352.818
——	8-Chloro-5-[2-hydroxy-3-(methylamino)propoxy]spiro[1,3-dihydroquinazoline-4,1'-cyclohexane]-2-one	——	C₁₇H₂₄ClN₃O₃	353.849
——	8-chloro-5-(2H-tetrazol-5-ylmethoxy)spiro[1,3-dihydroquinazoline-4,1'-cyclohexane]-2-one	——	C₁₅H₁₇ClN₆O₂	348.792
——	Ethyl 2-[2-(8-chloro-2-oxospiro[1,3-dihydroquinazoline-4,1'-cyclohexane]-5-yl)oxyethylamino]acetate	460346-60-5	C₁₉H₂₆ClN₃O₄	395.886
——	8-Chloro-5-[2-(oxan-2-yloxy)ethoxy]spiro[1,3-dihydroquinazoline-4,1'-cyclohexane]-2-one	460346-27-4	C₂₀H₂₇ClN₂O₄	394.898
——	3-[(8-chloro-2-oxospiro[1,3-dihydroquinazoline-4,1'-cyclohexane]-5-yl)oxymethyl]-4H-1,2,4-oxadiazol-5-one	——	C₁₆H₁₇ClN₄O₄	364.788
——	(8'-chloro-2'-oxo-2',3'-dihydro-1'H-spiro[cyclohexane-1,4'-quinazolin]-5'-yl)-trifluoromethanesulfonate	1086424-40-9	C₁₄H₁₄ClF₃N₂O₄S	398.79
——	{2-[(8'-chloro-2'-oxo-2',3'-dihydro-1'H-spiro[cyclohexane-1,4'-quinazolin]-5'-yl)oxy]-3-fluorophenyl}acetonitrile	1086424-98-7	C₂₁H₁₉ClFN₃O₂	399.852
——	8'-chloro-5'-[2-(chloromethyl)-6-fluorophenoxy]-1'H-spiro[cyclohexane-1,4'-quinazolin]-2'(3'H)-one	1086424-96-5	C₂₀H₁₉Cl₂FN₂O₂	409.287
——	2-{(8'-chloro-2'-oxo-2',3'-dihydro-1'H-spiro[cyclohexane-1,4'-quinazolin]-5'-yl)oxy}-3-fluorobenzonitrile	1086424-45-4	C₂₀H₁₇ClFN₃O₂	385.825
——	8'-chloro-5'-[2-fluoro-6-(hydroxymethyl)phenoxy]-1'H-spiro[cyclohexane-1,4'-quinazolin]-2'(3'H)-one	1086424-94-3	C₂₀H₂₀ClFN₂O₃	390.842
——	{2-[(8'-chloro-2'-oxo-2',3'-dihydro-1'H-spiro[cyclohexane-1,4'-quinazolin]-5'-yl)oxy]-3-fluorophenyl}acetic acid	1086424-35-2	C₂₁H₂₀ClFN₂O₄	418.852
——	2-{(8'-chloro-2'-oxo-2',3'-dihydro-1'H-spiro[cyclohexane-1,4'-quinazolin]-5'-yl)oxy}-3-fluorobenzecarboximidohydrazide	1086424-70-5	C₂₀H₂₁ClFN₅O₂	417.87
——	2-[(8'-chloro-2'-oxo-2',3'-dihydro-1'H-spiro[cyclohexane-1,4'-quinazolin]-5'-yl)oxy]-3-fluoro-N-hydroxybenzenecarboximidamide	1086425-06-0	C₂₀H₂₀ClFN₄O₃	418.855
——	2-{(8'-chloro-2'-oxo-2',3'-dihydro-1'H-spiro[cyclohexane-1,4'-quinazolin]-5'-yl)oxy}-3-fluorobenzoic acid	1086424-19-2	C₂₀H₁₈ClFN₂O₄	404.825
——	methyl 2-{(8'-chloro-2'-oxo-2',3'-dihydro-1'H-spiro[cyclohexane-1,4'-quinazolin]-5'-yl)oxy}-3-fluorobenzoate	1086424-39-6	C₂₁H₂₀ClFN₂O₄	418.852
——	2-[(8'-chloro-2'-oxo-2',3'-dihydro-1'H-spiro[cyclohexane-1,4'-quinazolin]-5'-yl)oxy]-3-fluoro-N-(methylsulfonyl)benzamide	1086424-33-0	C₂₁H₂₁ClFN₃O₅S	481.932
——	8'-chloro-5'-[2-fluoro-6-(2H-tetrazol-5-yl)phenoxy]-1'H-spiro[cyclohexane-1,4'-quinazolin]-2'(3'H)-one	1086424-23-8	C₂₀H₁₈ClFN₆O₂	428.853
——	8'-chloro-5'-[2-fluoro-6-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)phenoxy]-1'H-spiro[cyclohexane-1,4'-quinazolin]-2'(3'H)-one	1086424-31-8	C₂₁H₁₈ClFN₄O₄	444.85
——	8'-chloro-5'-[2-fluoro-6-(5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)phenoxy]-1'H-spiro[cyclohexane-1,4'-quinazolin]-2'(3'H)-one	1086424-32-9	C₂₁H₁₉ClFN₅O₃	443.865
——	4-(8'-chloro-2'-methylene-2',3'-dihydro-1'H-spiro[cyclohexane-1,4'-quinazolin]-5'-yl)-2-fluorobenzaldehyde	1086424-43-2	C₂₀H₁₈ClFN₂O₂	372.827
——	4-(8'-chloro-2'-methylene-2',3'-dihydro-1'H-spiro[cyclohexane-1,4'-quinazolin]-5'-yl)-2-fluorobenzoic acid	1086424-16-9	C₂₀H₁₈ClFN₂O₃	388.826
——	5-[(8'-chloro-2'-oxo-2',3'-dihydro-1'H-spiro[cyclohexane-1,4'-quinazolin]-5'-yl)]-2-fluorobenzoic acid	1086424-14-7	C₂₀H₁₈ClFN₂O₃	388.826
——	8'-chloro-5'-[4-fluoro-3-(2H-tetrazol-5-yl)phenyl]-1'H-spiro[cyclohexane-1,4'-quinazolin]-2'(3'H)-one	1086424-17-0	C₂₀H₁₈ClFN₆O	412.854

反应信息

作为反应物：

描述：

8'-氯5'-羟基-1'H-螺[环己烷-1,4'-喹唑啉]-2'(3'H)-酮在 sodium hydroxide 、盐酸羟胺、 potassium carbonate 作用下，以乙醇、 N,N-二甲基甲酰胺为溶剂，生成 (Z)-2-((8'-chloro-2'-oxo-2',3'-dihydro-1'H-spiro[cyclohexane-1,4'-quinazolin]-5'-yl)oxy)-N'-hydroxyacetimidamide

参考文献：

名称：

Spiroquinazolinones as novel, potent, and selective PDE7 inhibitors. Part 2: Optimization of 5,8-disubstituted derivatives

摘要：

The optimization of 5,8-disubstituted spirocyclohexane-quinazolinones into potent, selective, soluble PDE7 inhibitors with acceptable in vivo pharmacokinetic parameters is presented. (C) 2004 Elsevier Ltd. All rights reserved.

DOI：

10.1016/j.bmcl.2004.07.010
作为产物：

描述：

2-氯-5-甲氧基苯胺盐酸盐在 Eaton's reagent 、氢溴酸、溶剂黄146 作用下，以水为溶剂，反应 100.0h，生成 8'-氯5'-羟基-1'H-螺[环己烷-1,4'-喹唑啉]-2'(3'H)-酮

参考文献：

名称：

[EN] SUBSTITUTED BENZOXAZOLE AND BENZOFURAN COMPOUNDS AS PDE7 INHIBITORS
[FR] COMPOSÉS DE BENZOXAZOLE ET DE BENZOFURANE SUBSTITUÉS UTILISÉS EN TANT QU'INHIBITEURS DE PDE7

摘要：

式（I）中的取代苯并噁唑和苯并呋喃化学实体：其中，V、W、X、Y、Z和m可以具有本文描述的任何值，以及包含这些化学实体的组合物；制备它们的方法；以及它们在广泛的方法中的应用，包括代谢和反应动力学研究；检测和成像技术；放射性治疗；以及治疗一个或多个疾病，包括神经、认知、免疫和炎症性疾病，以及涉及PDE7或环核苷酸信号的其他状况和疾病。

公开号：

WO2019014305A1

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文献信息

New spirocondensed quinazolinones and their use as phosphodiesterase inhibitors

申请人：Warner-Lambert Company LLC

公开号：EP1400244A1

公开（公告）日：2004-03-24

The invention relates to compounds of formula (I) wherein R1, R2 and m are as defined in the description, their use as medicament, pharmaceutical compositions containing them and a process for their preparation. These compounds act as Phosphodiesterase inhibitors and inhibit in particular PDE-7.

本发明涉及式（I）中R1、R2和m的化合物，其中R1、R2和m的定义如描述中所定义，它们作为药物的用途，含有它们的药物组合物以及它们的制备方法。这些化合物作为磷酸二酯酶抑制剂，特别是抑制PDE-7。
Spirocondensed quinazolinones and their use as phosphodiesterase inhibitors

申请人：——

公开号：US20040106631A1

公开（公告）日：2004-06-03

The invention relates to compounds of formula (I) 1 wherein R 1 , R 2 and m are as defined in the description, their use as medicament, pharmaceutical compositions containing them and a process for their preparation.

本发明涉及式(I)1的化合物，其中R1、R2和m如描述中定义的，它们的用途作为药物、含有它们的制药组合物以及它们的制备方法。
Spirocyclic Derivatives

申请人：Rawson J. David

公开号：US20070129388A1

公开（公告）日：2007-06-07

The invention provides compounds of formula (I): wherein: m is 0, 1 or 2; X is O, S or N—CN; R is F, Cl or CN; A is a C 3-6 cycloalkylene group optionally substituted with a C 1-4 alkyl group; and B is a single bond or a C 1-2 alkylene group; or a pharmaceutically acceptable salt, solvate, polymorph or prodrug thereof. The compounds are PDE7 inhibitors and have a number of therapeutic applications, particularly in the treatment of pain, especially neuropathic pain.

该发明提供了式（I）的化合物：其中：m为0、1或2；X为O、S或N—CN；R为F、Cl或CN；A为C3-6环烷基，可选择地取代为C1-4烷基；B为单键或C1-2烷基；或其药学上可接受的盐、溶剂化物、多晶形或前药。这些化合物是PDE7抑制剂，具有许多治疗应用，特别是在疼痛治疗方面，尤其是神经病理性疼痛的治疗。
USE OF PDE7 INHIBITORS FOR THE TREATMENT OF NEUROPATHIC PAIN

申请人：Cox Peter

公开号：US20090111837A1

公开（公告）日：2009-04-30

The present invention relates to the use of a phosphodiesterase 7 (PDE7) inhibitor in the manufacture of a medicament for the treatment of neuropathic pain and to a method of treating neuropathic pain using an inhibitor of PDE7.

本发明涉及使用磷酸二酯酶7（PDE7）抑制剂制造治疗神经病理性疼痛药物以及使用PDE7抑制剂治疗神经病理性疼痛的方法。
[EN] SPIROCYCLIC QUINAZOLINE DERIVATIVES AND THEIR USE AS PDE7 INHIBITORS<br/>[FR] DÉRIVÉS SPIROCYCLIQUES

申请人：PFIZER LTD

公开号：WO2008142550A9

公开（公告）日：2010-02-11