4-丙酰氧基-4-苯基-N-甲基哌啶 | 13147-09-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 中文名称: 4-丙酰氧基-4-苯基-N-甲基哌啶
• 英文名称: 3-demethylprodine
• 英文别名: 1-methyl-4-phenyl-4-propionyloxypiperidine；1-methyl-4-phenyl-4-propionoxypiperidine；1-methyl-4-phenyl-4-propionyloxy-piperidine；propionic acid-(1-methyl-4-phenyl-[4]piperidyl ester)；Propionsaeure-(1-methyl-4-phenyl-[4]piperidylester)；β-D,L-1,3-Dimethyl-4-phenylpropionoxo-piperidin；Desmethylprodine；(1-methyl-4-phenylpiperidin-4-yl) propanoate
• CAS: 13147-09-6
• 化学式: C₁₅H₂₁NO₂
• 分子量: 247.337
• InChiKey: BCQMRZRAWHNSBF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-丙酰氧基-4-苯基-N-甲基哌啶 在 双氧水 、 三氟乙酸酐 作用下， 以 甲醇 为溶剂， 反应 52.33h， 生成 1,2,5,6-tetrahydro-1-methyl-4-phenyl-2-pyridine carbonitrile
  参考文献：
  名称：

  Groutas, W.C.; Essawi, M.; Portoghese, P.S., Synthetic Communications, 1980, vol. 10, # 7, p. 495 - 502

  摘要：

  DOI：
• 作为产物：
  描述：

  N-甲基-4-哌啶酮 在 丙酮 、 苯 作用下， 生成 4-丙酰氧基-4-苯基-N-甲基哌啶
  参考文献：
  名称：

  Jensen; Lundquist, Dansk Tidsskrift for Farmaci, 1943, vol. 17, p. 173,180

  摘要：

  DOI：

文献信息

• METHODS AND COMPOSITIONS FOR PREVENTING OPIOID ABUSE
  申请人：Waterville Valley Technologies, Inc.

  公开号：US20160326182A1

  公开（公告）日：2016-11-10

  Abuse-resistant opioid compounds, drug delivery systems, pharmaceutical compositions comprising an opioid covalently bound to a chemical moiety are provided. Methods of delivering an active ingredient to a subject and methods of preventing opioid abuse are also provided.

  提供了耐滥用的阿片类化合物、药物输送系统、含有阿片类药物与化学基团共价结合的制药组合物。还提供了将活性成分输送给受试者的方法以及预防阿片类药物滥用的方法。
• [EN] AN OPIOID FOR USE TO REDUCE AND/OR TREAT DRUG ADDICTION<br/>[FR] OPIOÏDE DESTINÉ À ÊTRE UTILISÉ POUR RÉDUIRE ET/OU TRAITER LA PHARMACODÉPENDANCE
  申请人：VERSI GROUP LLC

  公开号：WO2018204163A1

  公开（公告）日：2018-11-08

  The present invention relates to a method of treating drug addiction and reducing dependence or tolerance on a dependence-inducing opiate drug, wherein the method comprises administering to a subject a compound having the structure of formula (I): having the IUPAC name of (-)3-((S)-((2S,5R)-4-allyl-2,5-dimethyl-l-piperazinyl)(3-thienyl)methyl)phenol, or pharmaceutically acceptable esters or salts thereof, wherein the compound has activity on the mu, delta and kappa opioid receptors thereby providing added analgesia with an improved therapeutic index and reduced risk of respiratory depression.

  本发明涉及一种治疗药物成瘾、减少对诱导依赖的鸦片类药物的依赖或耐受性的方法，其中该方法包括向受试者施用具有以下公式（I）结构的化合物：(-)3-((S)-((2S,5R)-4-烯丙基-2,5-二甲基-1-哌嗪基)(3-噻吩基)甲基)苯酚的IUPAC名称，或其药学上可接受的酯或盐，化合物对mu、delta和kappa阿片受体具有活性，从而提供具有改善的治疗指数和减少呼吸抑制风险的附加镇痛作用。
• Shiga toxin B-subunit as a vector for tumor diagnosis and drug delivery to Gb3 expressing tumors
  申请人：Johannes Ludger

  公开号：US20060008475A1

  公开（公告）日：2006-01-12

  The invention relates to new compounds for cancer therapy or diagnosis and to the use of a non-toxic B subunit of Shiga toxin mutant as a vector for diagnostic products or drugs in over-expressing Gb3 receptor cells, such compounds having the following formula: STxB-Z(n)-Cys-Y(m)-T wherein—STxB is the Shiga Toxin B subunit or a functional equivalent thereof, —Z(n) wherein n is 0 or 1, Z is an amino-acid residue devoid of sulfydryl groups, or is a polypeptide, —T is a molecule linked by a covalent bound to the S part of Cys, selected from: agents for in vivo diagnosis, cytotoxic agents, prodrugs, or enzymes for the conversion of a prodrug to a drug, —Y(m) wherein m is 0 or 1, Y is a linker between T and Cys, which is either cleavable or not cleavable for the release of T after the internalization of the hybrid compound into cells.

  该发明涉及用于癌症治疗或诊断的新化合物，并且涉及使用Shiga毒素突变体的非毒性B亚单位作为诊断产品或药物的载体，用于过度表达Gb3受体细胞中的化合物，该化合物具有以下公式：STxB-Z（n）-Cys-Y（m）-T，其中- STxB是Shiga毒素B亚单位或其功能等效物，-Z（n）其中n为0或1，Z是不含巯基的氨基酸残基或多肽，-T是与Cys的S部分通过共价键连接的分子，选择自：体内诊断剂，细胞毒性剂，前药或用于将前药转化为药物的酶，-Y（m）其中m为0或1，Y是T和Cys之间的连接物，可以被裂解或不被裂解以在混合化合物内部化后释放T。
• N-OXIDE AND/OR DI-N-OXIDE DERIVATIVES OF DOPAMINE RECEPTOR STABILIZERS/MODULATORS DISPLAYING IMPROVED CARDIOVASCULAR SIDE-EFFECTS PROFILES
  申请人：Wikström Håkan V.

  公开号：US20100105736A1

  公开（公告）日：2010-04-29

  A compound having the general formula wherein A is selected from the group consisting of to the formation of a compound of the general formula (1) and a compound of the general formula (2) respectively, and pharmaceutically acceptable salts thereof, wherein R 1 is a member selected from the group consisting of CF 3 , OSO 2 CF 3 , OSO 2 CH 3 , SOR 4 , SO 2 R 4 , COR 4 , CN, OR 4 , NO 2 , CONHR 4 , 3-thiophene, 2-thiophene, 3-furane, 2-furane, F, Cl, Br and I, wherein R 4 is as defined below; R 2 is a member selected from the group consisting of H, F, Cl, Br, I, CN, CF 3 , CH 3 , OCH 3 , OH, NH 2 , SO m CF 3 , O(CH 2 ) m CF 3 , SO 2 N(R 4 ) 2 , CH═NOR 4 , COCOOR 4 , COCOON(R 4 ) 2 , (C 1 -C 8 )alkyl, (C 3 -C 8 )cykloalkyl, CH 2 OR 4 , CH 2 (R 4 ) 2 , NR 4 SO 2 CF 3 , NO 2 , at phenyl at positions 2, 4, 5 or 6, wherein x and R 4 are as defined below; R 3 is a member selected from the group consisting of hydrogen, CF 3 , CH 2 CF 3 , (C 1 -C 8 )alkyl, (C 3 -C 8 )cykloalkyl, (C 4 -C 9 )cycloalkylmethyl, (C 2 -C 8 )alkenyl, (C 2 -C 8 )alkynyl, 3,3,3-tri-fluoropropyl, 4,4,4-trifluorobutyl, CH 2 SCH 3 , CH 2 CH 2 OCH 3 , CH 2 CH 2 CH 2 F, CH 2 CF 3 , phenylethyl, 2-thiopheneethyl and 3-thiopheneethyl; R 4 is a member selected from the group consisting of hydrogen, CF 3 , CH 2 CF 3 , (C 1 -C 8 )alkyl, (C 3 -C 8 )cycloalkyl, (C 4 -C 9 )cycloalkylmethyl, (C 2 -C 8 )alkenyl, (C 2 -C 8 )alkynyl, 3,3,3-trifluoropropyl, 4,4,4-trifluorobutyl, 2-tetrahydrofurane and 3-tetrahydrofurane; X is selected from the group consisting of N and sp 3 -hybridized C; Y is selected from the group consisting of O and, when R 3 represents H, OH; Z is selected from the group consisting of H and OH when X is sp 3 -hybridized C or Z represents O or an electronic lone-pair when X is N; the dashed line represents a bond when X is sp 2 -hybridized C or is absent when X is N; m is an integer 1 or 2; n is an integer 1-3; provided that when n in Formula 1 is 2, R 1 is SO 2 CH 3 and R 2 is H R 3 does not represent n-propyl. The invention also relates to a pharmaceutical preparation containing said compound, the use of said compound for the manufacture of a pharmaceutical composition and a method for the treatment of a disorder in the central nervous system of a patient using said compound.

  一种具有通式的化合物， 其中A选自以下组： 至形成通式（1）的化合物和通式（2）的化合物， 以及其药学上可接受的盐， 其中R1是从以下组中选择的成员：CF3，OSO2 ，OSO2 ，SOR4，SO2R4，COR4，CN，OR4，NO2，CONHR4，3-噻吩，2-噻吩，3-呋喃，2-呋喃，F，Cl，Br和I，其中R4如下所定义； R2是从以下组中选择的成员：H，F，Cl，Br，I，CN， ，CH3，O ，OH，NH2，SOm ，O（CH2）m ，SO2N（R4）2，CH═NOR4，COCOOR4，COCOON（R4）2，（C1-C8）烷基，（C3-C8）环烷基， OR4， （R4）2，NR4SO2 ， ，在苯基的2,4,5或6位置，其中x和R4如下所定义； R3是从以下组中选择的成员：氢， ， ，（C1-C8）烷基，（C3-C8）环烷基，（C4-C9）环烷基甲基，（C2-C8）烯基，（C2-C8）炔基，3,3,3-三氟丙基，4,4,4-三氟丁基， S ， O ， F， ，苯乙基，2-噻吩乙基和3-噻吩乙基； R4是从以下组中选择的成员：氢， ， ，（C1-C8）烷基，（C3-C8）环烷基，（C4-C9）环烷基甲基，（C2-C8）烯基，（C2-C8）炔基，3,3,3-三氟丙基，4,4,4-三氟丁基，2-四氢呋喃和3-四氢呋喃； X选自以下组：N和sp3-杂化C； Y选自以下组：O和当R3表示H时，OH； Z选自以下组：当X为sp2-杂化C或X为N时，表示键，或当X为N时，表示O或电子孤对； 虚线表示键，当X为sp2-杂化C时，或当X为N时，表示不存在； m是1或2的整数； n是1-3的整数； 但是，当通式1中的n为2时，R1为SO2 ，R2为H，R3不表示正丙基。 本发明还涉及含有该化合物的药物制剂，使用该化合物制造药物组成物的用途以及使用该化合物治疗患者中枢神经系统疾病的方法。
• Shiga toxin B-subunit as a vector for tumor diagnosis and drug delivery to GB3 expressing tumors
  申请人：Institut Curie

  公开号：US07981400B2

  公开（公告）日：2011-07-19

  The invention relates to new compounds for cancer therapy or diagnosis and more specifically to the use of a non-toxic B subunit of Shiga toxin mutant as a vector for diagnostic products or drugs in over-expressing Gb3 receptor cells, such compounds having the following formula: STxB-Z(n)-Cys-Y(m)-T wherein STxB is the Shiga Toxin B subunit or a functional equivalent thereof, Z(n) wherein n is 0 or 1 and when n is 1, Z is an amino-acid residue devoid of sulfhydryl group, or is a polypeptide, Cys is the amino-acid residue for Cysteine, T is a molecule linked by a covalent bound to the S part of Cys, selected in a group comprising: agents for in vivo diagnosis, cytotoxic agents, prodrugs, or enzymes for the conversion of a prodrug to a drug, Y(m) wherein m is 0 or 1 and when m is 1, Y is a linker between T and Cys, said linker being either cleavable or not cleavable for the release of T after the internalization of the hybrid compound into said cells.

  本发明涉及新的化合物，用于癌症治疗或诊断，更具体地说，使用非毒性的Shiga毒素突变体B亚单位作为诊断产品或药物的载体，用于过度表达Gb3受体细胞，该化合物具有以下公式：STxB-Z（n）-Cys-Y（m）-T，其中STxB是Shiga毒素B亚单位或其功能等效物，Z（n）其中n为0或1，当n为1时，Z是缺乏硫醇基的氨基酸残基，或者是多肽，Cys是半胱氨酸的氨基酸残基，T是通过共价键连接到Cys的S部分的分子，选择在以下组中：用于体内诊断的试剂，细胞毒性试剂，前药或将前药转化为药物的酶，Y（m）其中m为0或1，当m为1时，Y是T和Cys之间的连接剂，该连接剂可以被裂解或不可被裂解，以在将混合化合物内部化到所述细胞后释放T。