3,3-二甲基-2-氧代-2,3-二氢-1H-吲哚-6-羧酸 | 127267-57-6

• 物质功能分类: 医药中间体 - 杂环化合物 - 吲哚类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: 3,3-二甲基-2-氧代-2,3-二氢-1H-吲哚-6-羧酸
• 英文名称: 3,3-dimethyl-2-oxo-2,3-dihydro-1H-indole-6-carboxylic acid
• 英文别名: 3,3-dimethyl-2-oxoindoline-6-carboxylic acid；3,3-dimethyl-2-oxoindolin-6-carboxylic acid；3,3-dimethyl-2,3-dihydro-2-oxo-(1H)-6-indolecarboxylic acid；3,3-dimethyl-2-oxo-1H-indole-6-carboxylic acid
• CAS: 127267-57-6
• 化学式: C₁₁H₁₁NO₃
• 分子量: 205.213
• InChiKey: ARPWLTXDPCHBLE-UHFFFAOYSA-N

物化性质

• 熔点：
  295-300 °C (decomp)
• 沸点：
  407.7±45.0 °C(Predicted)
• 密度：
  1.266±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,3-二甲基-2-氧代-2,3-二氢-1H-吲哚-6-羧酸 在 manganese(IV) oxide 、 锂硼氢 、 硫酸 、 potassium carbonate 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 98.0h， 生成 6-(2-chlorooxazol-5-yl)-3,3-dimethylindolin-2-one
  参考文献：
  名称：

  [EN] INDOLIN-2-ONE AND 1,3-DIHYDRO-PYRROLO[3,2-c]PYRIDIN-2-ONE DERIVATIVES
  [FR] DÉRIVÉS D'INDOLIN-2-ONE ET DE 1,3-DIHYDRO-PYRROLO[3,2-C]PYRIDIN-2-ONE

  摘要：

  本发明涉及一般式(I)的吲哚啉-2-酮和1,3-二氢吡咯并[3,2-c]吡啶-2-酮衍生物，其中Ar1是苯基、吡啶基或嘧啶基；Ar2是含有2个或3个N、O或S杂原子的5或6元杂芳基团；R1是氢、低碳基、卤素或低烷氧基；R2是氢或低碳基；R3是氢、低碳基、低碳基取代的羟基、环烷基、氧杂环丙烯基、吡啶基、咪唑基、吡唑基、嘧啶基，这些环可能被低碳基取代，或者是-(CH2)3-S(O)2-环丙基；X是CH或N；n为1或2；以及其药学上可接受的盐、消旋混合物、对映体和/或光学异构体和/或立体异构体，用于治疗某些中枢神经系统疾病，包括精神病（正性症状和负性症状）、精神分裂症、物质滥用、酒精和药物成瘾、强迫症、认知障碍、双相情感障碍、情绪障碍、重度抑郁症、治疗难治性抑郁症、焦虑症、阿尔茨海默病、自闭症、帕金森病、慢性疼痛、边缘性人格障碍、睡眠障碍、慢性疲劳综合征、僵硬、关节炎中的抗炎作用和平衡问题。

  公开号：

  WO2015177110A1
• 作为产物：
  描述：

  6-溴-3,3-二甲基-2,3-二氢-1H-吲哚-2-酮 在 盐酸 、 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 水 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 100.0 ℃ 、1.03 MPa 条件下， 反应 34.0h， 生成 3,3-二甲基-2-氧代-2,3-二氢-1H-吲哚-6-羧酸
  参考文献：
  名称：

  [EN] INDOLIN-2-ONE OR PYRROLO-PYRIDIN/PYRIMIDIN-2-ONE DERIVATIVES
  [FR] DÉRIVÉS INDOLIN-2-ONE OU PYRROLO-PYRIDIN/PYRIMIDIN-2-ONE

  摘要：

  本发明涉及通式（I）中的2-氧代-2,3-二氢吲哚，其中Ar是一个杂环烃基，含有一个、两个或三个杂原子，选自N、S或O；R1是氢、低碳基、卤素、氨基、二甲胺基、氰基、被卤素取代的低碳基、被羟基取代的低碳基、CH(OH)CF3、（CH2）o-低碳醚、环烷基（可选地被CF3取代）、或杂环烷基（可选地被低碳基取代）；R2是氢、低碳基、（CH2）o-环烷基、（CH2）o-O-环烷基、（CH2）o-低碳醚、被卤素取代的（CH2）o-低碳醚、（CH2）o-杂环烷基（可选地被低碳基取代）、（CH2）o-S(O)2-环烷基、被一个或两个羟基取代的低碳基、被一个或两个低碳醚取代的低碳基、（CH2）o-S(O)2-低碳基、被卤素或CH2CH(OH)CF3取代的低碳基；R3是卤素或低碳基；X是CH或N；X1是CH或N；n是1或2；o是0、1、2或3；m是0、1或2；虚线是键或非键；以及其在药学上可接受的盐、消旋混合物、或其相应的对映体和/或光学异构体和/或立体异构体。这些化合物可用于治疗某些中枢神经系统障碍，包括精神病（阳性和阴性症状）、精神分裂症、物质滥用、酒精和药物成瘾、强迫症、认知障碍、双相情感障碍、情绪障碍、重性抑郁症、治疗难治性抑郁症、焦虑障碍、阿尔茨海默病、自闭症、帕金森病、慢性疼痛、边缘人格障碍、睡眠障碍、慢性疲劳综合征、僵硬、关节炎的抗炎作用和平衡问题。

  公开号：

  WO2014202493A1

文献信息

• SPIROPIPERIDINE DERIVATIVES
  申请人：Bissantz Caterina

  公开号：US20080153861A1

  公开（公告）日：2008-06-26

  The present invention is concerned with novel spiro-piperidine derivatives as V1a receptor antagonists, their manufacture, pharmaceutical compositions containing them and their use for the treatment of anxiety and depressive disorders and other diseases. The compounds of present invention are described with formula (I) wherein R 1 to R 5 , R 5 ′, R 7 to R 9 , R 7 ′, R 8 ′, X and Y are as defined in the specification.

  本发明涉及作为V1a受体拮抗剂的新颖螺环哌啶衍生物，其制备方法，含有它们的药物组合物以及它们用于治疗焦虑和抑郁症等疾病的用途。本发明的化合物用式(I)描述如下： 其中R1至R5，R5'，R7至R9，R7'，R8'，X和Y如规范中定义。
• [EN] INDOLIN-2-ONE OR PYRROLO-PYRIDIN-2-ONE DERIVATIVES<br/>[FR] DÉRIVÉS D'INDOLIN-2-ONE OU DE PYRROLOPYRIDIN-2-ONE
  申请人：HOFFMANN LA ROCHE

  公开号：WO2015197567A1

  公开（公告）日：2015-12-30

  The present invention is concerned with 2-oxo-2,3-dihydro-indoles of general formula (I) wherein Ar1 is phenyl or a five or six membered heteroaryl group, containing one, two or three heteroatoms, selected from N, S or O, wherein the N-heteroatom in the heteroaryl group may be oxidized to N+-(O-); R1 is lower alkyl, halogen, cyano or cycloalkyl; Ar2 is a five or six membered heteroaryl group, containing one, two, three or four heteroatoms, selected from N, S or O, wherein the N-heteroatom in the heteroaryl group may be oxidized to N+-(O-), or is benzo[b]thiophenyl; R2 is hydrogen, lower alkyl, halogen, cyano, lower alkyl substituted by hydroxyl, lower alkyl substituted by halogen, lower alkyl substituted by amino, lower alkyl substituted by alkoxy, lower alkyl substituted by amide, or is cycloalkyl; X is CH or N; n is 1 or 2; m is 1 or 2; as well as with a pharmaceutically acceptable salt thereof, with a racemic mixture, or with its corresponding enantiomer and/or optical isomer and/or stereoisomer thereof. The compounds may be used in the treatment of CNS diseases related to positive (psychosis) and negative symptoms of schizophrenia, substance abuse, alcohol and drug addiction, obsessive-compulsive disorders, cognitive impairment, bipolar disorders, mood disorders, major depression, treatment resistant depression, anxiety disorders, Alzheimer's disease, autism, Parkinson's disease, chronic pain, borderline personality disorder, neurodegenerative disease, sleep disturbances, chronic fatigue syndrome, stiffness, inflammatory disease, asthma, Huntington's disease, ADHD, amyotrophic lateral sclerosis, epilepsy, effects in arthritis, autoimmune disease, viral and fungal infections, cardiovascular diseases, ophthalmology and inflammatory retinal diseases and balance problems.

  本发明涉及一般式（I）的2-氧代-2,3-二氢吲哚，其中Ar1为苯基或含有一个、两个或三个异原子（N、S或O）的五元或六元杂环芳基，其中杂环芳基中的N-异原子可以被氧化为N+-(O-)；R1为低碳基、卤素、氰基或环烷基；Ar2为含有一个、两个、三个或四个异原子（N、S或O）的五元或六元杂环芳基，其中杂环芳基中的N-异原子可以被氧化为N+-(O-)，或者为苯并[ｂ]噻吩基；R2为氢、低碳基、卤素、氰基、被羟基取代的低碳基、被卤素取代的低碳基、被氨基取代的低碳基、被烷氧基取代的低碳基、被酰胺取代的低碳基，或者为环烷基；X为CH或N；n为1或2；m为1或2；以及其药学上可接受的盐、消旋体混合物、或其对映体和/或光学异构体和/或立体异构体。这些化合物可用于治疗与精神病（精神病）、精神分裂症的阳性和阴性症状、物质滥用、酒精和药物成瘾、强迫症、认知障碍、躁郁症、情感障碍、重度抑郁症、治疗难治性抑郁症、焦虑障碍、阿尔茨海默病、自闭症、帕金森病、慢性疼痛、边缘人格障碍、神经退行性疾病、睡眠障碍、慢性疲劳综合征、僵硬、炎症性疾病、哮喘、亨廷顿病、注意力缺陷多动障碍、肌萎缩侧索硬化症、癫痫、关节炎作用、自身免疫疾病、病毒和真菌感染、心血管疾病、眼科学和炎症性视网膜疾病以及平衡问题相关的中枢神经系统疾病的治疗。
• 2-bicyclobenzimidazoles, processes for their preparation and medicaments
  申请人：Boehringer Mannheim GmbH

  公开号：US05414088A1

  公开（公告）日：1995-05-09

  The invention concerns compounds of formula I ##STR1## where R.sup.1 is hydrogen, C.sub.1 -C.sub.6 -alkyl, C.sub.2 -C.sub.6 -alkenyl or C.sub.3 -C.sub.7 -cycloalkyl, R.sup.2 is C.sub.1 -C.sub.6 -alkyl, C.sub.2 -C.sub.6 -alkenyl, cyano, carboxy [carbonyl substituted by hydroxyl], C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkoxy, amino, C.sub.1 -C.sub.6 -alkylamino, di-C.sub.1 -C.sub.6 -alkylamino or hydrazino or R.sup.1 and R.sup.2 together are C.sub.2 -C.sub.6 -alkylidene or C.sub.3 -C.sub.6 -cycloalkylidene or R.sup.1 and R.sup.2, together with the carbon atoms to which they are attached, form a C.sub.3 -C.sub.7 -spirocycle, n is 0 or 1, R.sup.3 is hydrogen, C.sub.1 -C.sub.8 -alkyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.2 -C.sub.6 -alkynyl, C.sub.3 -C.sub.7 -cycloalkyl, benzyl, carboxy-C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkyloxycarbonyl-C.sub.1 -C.sub.6 -alkyl or di-C.sub.1 -C.sub.6 -alkyloxophosphinyl-C.sub.1 -C.sub.6 -alkyl and R.sup.4 -R.sup. 6 are as in the specification. These compounds of formula I serve for the preparation of medicaments to inhibit erythrocyte and thrombocyte aggregation. Therefore, these compounds are useful for the treatment of diseases where these aggregations occur such as arterial occlusive or ischaemic conditions, venous insufficiency or diabetes mellitus.

  本发明涉及式I的化合物：##STR1## 其中R1为氢、C1-C6烷基、C2-C6烯基或C3-C7环烷基，R2为C1-C6烷基、C2-C6烯基、氰基、羧基[羟基取代的羰基]、C1-C6烷氧基、氨基、C1-C6烷基氨基、二C1-C6烷基氨基或肼基，或R1和R2一起为C2-C6烷基亚甲基或C3-C6环烷基亚甲基，或者R1和R2连同它们所连接的碳原子形成C3-C7螺环，n为0或1，R3为氢、C1-C8烷基、C2-C6烯基、C2-C6炔基、C3-C7环烷基、苄基、羧基-C1-C6烷基、C1-C6烷氧羰基-C1-C6烷基或二C1-C6烷氧基膦酰基-C1-C6烷基，R4-R6如说明书所述。这些式I的化合物用于制备药物，以抑制红细胞和血小板聚集。因此，这些化合物对于治疗这些聚集发生的疾病非常有用，例如动脉闭塞性或缺血性疾病、静脉不全或糖尿病。
• Bicyclic carboxamides, compositions containing same and use thereof
  申请人：Boehringer Mannheim GmbH

  公开号：US05019587A1

  公开（公告）日：1991-05-28

  The present invention provides compounds of the general formula (I) which inhibit the aggregation of erythrocytes or thrombocytes ##STR1## wherein A is hydrogen or C.sub.1 -C.sub.6 -alkyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.2 -C.sub.6 -alkynyl, benzyl or C.sub.3 -C.sub.7 -cycloalkyl radical, B is hydrogen, R.sub.1 is a C.sub.1 -C.sub.6 -alkyl, C.sub.2 -C.sub.6 -alkenyl or C.sub.3 -C.sub.7 -cycloalkyl radical, R.sub.2 is a C.sub.1 -C.sub.6 -alkyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.3 -C.sub.7 -cycloalkyl, C.sub.1 -C.sub.6 -alkylcarbonyl, C.sub.1 -C.sub.6 -alkoxycarbonyl, aminocarbonyl or hydrazinocarbonyl radical, or R.sub.1 and R.sub.2, together with the carbon atom to which they are attached, form a C.sub.3 -C.sub.7 -cycloalkyl ring, n is 0, X is a valency bond or a C.sub.1 -C.sub.6 -alkylene radical, R.sub.3 is a carbocyclic aromatic ring, which may be substituted; and the tautomers, optically-active forms and physiologically acceptable salts thereof with organic and inorganic acids.

  本发明提供了通式（I）的化合物，其抑制红细胞或血小板的聚集 ##STR1## 其中A为氢或C.sub.1-C.sub.6-烷基，C.sub.2-C.sub.6-烯基，C.sub.2-C.sub.6-炔基，苄基或C.sub.3-C.sub.7-环烷基，B为氢，R.sub.1为C.sub.1-C.sub.6-烷基，C.sub.2-C.sub.6-烯基或C.sub.3-C.sub.7-环烷基，R.sub.2为C.sub.1-C.sub.6-烷基，C.sub.2-C.sub.6-烯基，C.sub.3-C.sub.7-环烷基，C.sub.1-C.sub.6-烷基羰基，C.sub.1-C.sub.6-烷氧羰基，氨基羰基或肼氨基羰基基团，或R.sub.1和R.sub.2与它们连接的碳原子一起形成C.sub.3-C.sub.7-环烷基，n为0，X为一个价键或C.sub.1-C.sub.6-亚烷基基团，R.sub.3为一个碳环芳香环，可以被取代；以及其与有机和无机酸的互变异构体，光学活性形式和生理上可接受的盐。
• INDOLIN-2-ONE OR PYRROLO-PYRIDIN/PYRIMIDIN-2-ONE DERIVATIVES
  申请人：Hoffmann-La Roche Inc.

  公开号：US20160095844A1

  公开（公告）日：2016-04-07

  The present invention is concerned with 2-oxo-2,3-dihydro-indoles of general formula wherein Ar is a 6-membered heteroaryl group, containing one or two N-atoms, which are the groups, pyridinyl, pyrimidinyl, pyridazinyl, or a 5-membered heteroaryl group containing from 1 to 3 heteroatoms, selected from N, S or O, which groups are imidazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadazolyl, isoxazolyl, oxazolyl, 1,3,4-thiadiazolyl or pyrazolyl; R 1 is hydrogen, lower alkyl, halogen, amino, dimethylamino, cyano, lower alkyl substituted by halogen, lower alkyl substituted by hydroxy, CH(OH)CF 3 , (CH 2 ) o -lower alkoxy, cycloalkyl optionally substituted by CF 3 , or heterocycloalkyl optionally substituted by lower alkyl; R 2 is hydrogen, lower alkyl, (CH 2 ) o -cycloalkyl, (CH 2 ) o —O-cycloalkyl, (CH 2 ) o -lower alkoxy, CH 2 ) o -lower alkoxy substituted by halogen, (CH 2 ) o -heterocycloalkyl optionally substituted by lower alkyl, (CH 2 ) o —S(O) 2 -cycloalkyl, lower alkyl substituted by one or two hydroxy, lower alkyl substituted by one or two lower alkoxy, (CH 2 ) o —S(O) 2 -lower alkyl, lower alkyl substituted by halogen or CH 2 CH(OH)CF 3 ; R 3 is halogen or lower alkyl; X is CH or N; X 1 is CH or N; n is 1 or 2; is 0, 1, 2 or 3; m is 0, 1 or 2; and the dotted line indicates a bond may or may not be present; or, a pharmaceutically acceptable salts thereof, with a racemic mixture, or with its corresponding enantiomer and/or optical isomer and/or stereoisomer thereof The compounds may be used for the treatment of certain central nervous system disorders which are positive (psychosis) and negative symptoms of schizophrenia, substance abuse, alcohol and drug addiction, obsessive-compulsive disorders, cognitive impairment, bipolar disorders, mood disorders, major depression, treatment resistant depression, anxiety disorders, Alzheimer's disease, autism, Parkinson's disease, chronic pain, borderline personality disorder, sleep disturbances, chronic fatigue syndrome, stiffness, antiinflammatory effects in arthritis and balance problems.

  本发明涉及一般式为的2-氧代-2,3-二氢吲哚，其中Ar是6元杂环芳基基团，含有一个或两个N原子，该基团为吡啶基，嘧啶基，吡嗪基或含有1至3个杂原子的5元杂环芳基基团，所述杂原子选自N，S或O，该基团为咪唑基，1,2,4-噁二唑基，1,3,4-噁二唑基，异噁唑基，噁唑基，1,3,4-噻二唑基或吡唑基；R1为氢，低碳基，卤素，氨基，二甲氨基，氰基，低碳基取代的卤素，低碳基取代的羟基，CH（OH）CF3，（CH2）o-低碳基氧基，环烷基（可选）取代CF3或杂环烷基（可选）取代低碳基；R2为氢，低碳基，（CH2）o-环烷基，（CH2）o—O-环烷基，（CH2）o-低碳基氧基，（CH2）o-低碳基取代的卤素，（CH2）o-杂环烷基（可选）取代低碳基，（CH2）o—S（O）2-环烷基，低碳基取代1或2个羟基，低碳基取代1或2个低碳基氧基，（CH2）o—S（O）2-低碳基，低碳基取代卤素或CH2CH（OH）CF3；R3为卤素或低碳基；X为CH或N；X1为CH或N；n为1或2；为0,1,2或3；m为0,1或2；虚线表示可能存在或不存在键；或其药学上可接受的盐，与外消旋混合物或其对应的对映体和/或光学异构体和/或立体异构体一起使用。这些化合物可用于治疗某些中枢神经系统紊乱，包括精神病（阳性症状）和阴性症状的精神分裂症，物质滥用，酒精和药物成瘾，强迫症，认知障碍，双相障碍，情绪障碍，重度抑郁症，治疗难治性抑郁症，焦虑症，阿尔茨海默病，自闭症，帕金森病，慢性疼痛，边缘人格障碍，睡眠障碍，慢性疲劳综合症，僵硬，关节炎的抗炎作用和平衡问题的治疗。