公开(公告)号：US20130150450A1

公开(公告)日：2013-06-13

申请号：US13620761

申请日：2012-09-15

Applicant: Edward Holson ,  Florence F. Wagner ,  G. Patrick Stahly

Inventor： Edward Holson ,  Florence F. Wagner ,  G. Patrick Stahly

IPC: C07C233/80

CPC classification number: C07C233/80 ,  A61K31/167 ,  C07B2200/13 ,  C07C231/12 ,  C07C237/42

Abstract: Novel solid forms of tacedinaline (4-(acetylamino)-N-(2-aminophenyl)benzamide), including crystalline tacedinaline Forms A, B, and D, a novel crystalline tacedinaline TFA salt, and amorphous tacedinaline, are disclosed. Pharmaceutical compositions comprising crystalline tacedinaline Forms A, B, and D, the novel crystalline tacedinaline TFA salt, and/or amorphous tacedinaline, and methods of treating various conditions by administering those novel solid forms, are also disclosed.

公开(公告)号：US5008417A

公开(公告)日：1991-04-16

申请号：US525827

申请日：1990-05-21

Applicant: G. Patrick Stahly

Inventor： G. Patrick Stahly

IPC: C07F7/22 ,  C07F7/30 ,  C07F9/50 ,  C07F9/53

CPC classification number: C07F7/30 ,  C07F7/2212 ,  C07F9/5022 ,  C07F9/5325

Abstract: A process for the haloalkylation of certain tin, phosphorus and germanium halides is disclosed. The process is carried out typically in a halocarbon solvent at temperatures of less than 0.degree. C. using as the haloalkylating reagent an admixture of a haloalkyl halide and tris(lower alkylamino)phosphine.

Abstract translation: 公开了某些锡，磷和锗卤化物的卤代烷基化方法。 该方法通常在卤代烃溶剂中在低于0℃的温度下进行，使用卤代烷基化试剂作为卤代烷基卤化物和三（低级烷基氨基）膦的混合物。

公开(公告)号：US4999429A

公开(公告)日：1991-03-12

申请号：US435666

申请日：1989-11-13

Applicant: G. Patrick Stahly

Inventor： G. Patrick Stahly

IPC: C07B39/00 ,  C07C17/361 ,  C07C45/67 ,  C07C49/80 ,  C07D307/38

CPC classification number: C07D307/38 ,  C07B39/00 ,  C07C17/361 ,  C07C45/673 ,  C07C49/80

Abstract: Aryl difluoromethyl sulfone adds to aldehydes under phase transfer conditions to give novel substituted alcohols of the general formulaRCH(OH)CF.sub.2 SO.sub.2 Ar (I)wherein R is an aryl, cycloaliphatic, sec- or tert-aliphatic, or heterocyclic group and Ar is an aryl group. The substituted alcohols of formula I are of particular utility as intermediates in the synthesis of a variety of useful end products. For example, the products of formula I may be utilized in desulfonylation reactions, oxidation reactions and fluorination reactions.

Abstract translation: 芳基二氟甲基砜在相转移条件下加入醛，得到通式为RCH（OH）CF 2 SO 2 Ar（I）的新型取代的醇，其中R是芳基，脂环族，仲或叔脂族或杂环基，Ar是芳基 组。 式I的取代的醇在合成各种有用的最终产物中特别有用。 例如，式I的产物可用于脱磺酰化反应，氧化反应和氟化反应。

公开(公告)号：US4804774A

公开(公告)日：1989-02-14

申请号：US177151

申请日：1988-04-04

Applicant: G. Patrick Stahly

Inventor： G. Patrick Stahly

IPC: C07C39/24 ,  C07C39/38 ,  C07C45/62 ,  C07C45/67 ,  C07C49/497 ,  C07C49/713 ,  C07C49/747 ,  C07F7/08 ,  C07F7/18 ,  C07F7/10

CPC classification number: C07F7/188 ,  C07C39/24 ,  C07C39/38 ,  C07C45/62 ,  C07C45/673 ,  C07C49/497 ,  C07C49/713 ,  C07C49/747 ,  C07F7/0818 ,  C07C2103/26

Abstract: Quinones may be perfluoroalkylated by means of perfluoroalkyltrihydrocarbyl silane using trialkylphosphites or hexahydrocarbylphosphorous triamides, or both as catalysts. The reaction --which is conducted under essentially anhydrous conditions, preferably in a suitable liquid phase reaction medium, most preferably a dipolar aprotic solvent--results in the formation of gem-disubstituted cyclohexadienones in which the gem substituents are a perfluoroalkyl group and a trihydrocarbylsiloxy group. These gem-disubstituted compounds in turn can be readily converted to perfluoroalkyl substituted aromatics, thus circumventing the traditional need for photochlorination followed by halogen exchange using hydrogen fluoride as a means of preparing perfluoroalkyl aromatic compounds.

Abstract translation: 醌类可以使用三烷基亚磷酸酯或六烃基磷酸三酰胺或全部作为催化剂通过全氟烷基三烃基硅烷全氟烷基化。 在基本上无水条件下，优选在合适的液相反应介质，最优选偶极非质子溶剂中进行的反应导致形成偕二取代的环己二烯酮，其中偕基取代基是全氟烷基和三烃基甲硅烷氧基。 甲基二取代的化合物又可以容易地转化为全氟烷基取代的芳族化合物，从而避免了光氯化的传统需要，随后使用氟化氢进行卤素交换作为制备全氟烷基芳族化合物的手段。

公开(公告)号：US4710581A

公开(公告)日：1987-12-01

申请号：US783419

申请日：1985-10-03

Applicant: G. Patrick Stahly ,  Barbara C. Stahly

Inventor： G. Patrick Stahly ,  Barbara C. Stahly

IPC: C07C205/56 ,  C07C79/46

CPC classification number: C07C201/12 ,  C07C201/16

Abstract: Halonitroarylacetic acid esters are prepared by reacting a halonitroaromatic compound with an alpha,alpha-disubstituted acetic acid ester in an inert solvent and in the presence of a base. The halonitroarylacetic acid esters formed by the process can be readily converted into derivatives, such as pharmaceuticals.

Abstract translation: 卤代四芳基乙酸酯通过卤代硝基芳族化合物与α，α-二取代的乙酸酯在惰性溶剂中和在碱的存在下反应来制备。 通过该方法形成的卤代硝酰基乙酸酯可以容易地转化为衍生物，例如药物。

公开(公告)号：US4582947A

公开(公告)日：1986-04-15

申请号：US705903

申请日：1985-02-26

Applicant: G. Patrick Stahly

Inventor： G. Patrick Stahly

IPC: C07C205/20 ,  C07C79/22 ,  C07C79/24

CPC classification number: C07C201/12

Abstract: 2,6-Dihydrocarbyl-4-(nitroaryl)phenols are prepared by reacting (1) a nitroaromatic compound bearing a displaceable substituent selected from nitro and phenylsulfonyl on a ring carbon which is adjacent to, or separated by two ring atoms from, the ring carbon bearing the nitro substituent with (2) a 2,6-dihydrocarbylphenol selected from 2,6-di-t-butyl- , 2,6-di-t-amyl-, 2-t-butyl-6-isopropyl-, and 2,6-diphenylphenols having a replaceable hydrogen in the 4-position in an inert solvent and in the presence of a strong base. The preferred nitroaromatic compounds are 1,2- and 1,4-dinitrobenzenes, 1-nitro-2-phenylsulfonylbenzenes, and 1-nitro-4-phenylsulfonylbenzenes; and a preferred phenol is 2,6-di-t-butylphenol.

Abstract translation: 2,6-二烃基-4-（硝基芳基）苯酚是通过使（1）含有选自硝基和苯基磺酰基的可置换取代基的硝基芳族化合物与环上相邻或由两个环原子分开的环碳 带有硝基取代基的碳与（2）选自2,6-二叔丁基，2,6-二叔戊基，2-叔丁基-6-异丙基， 和在惰性溶剂中和在强碱存在下在4-位上具有可置换氢的2,6-二苯基苯酚。 优选的硝基芳族化合物是1,2-和1,4-二硝基苯，1-硝基-2-苯基磺酰基苯和1-硝基-4-苯基磺酰基苯; 优选的苯酚是2,6-二叔丁基苯酚。

公开(公告)号：US4502996A

公开(公告)日：1985-03-05

申请号：US452615

申请日：1982-12-23

Applicant: G. Patrick Stahly

Inventor： G. Patrick Stahly

IPC: C07C255/32 ,  C07C121/50

CPC classification number: C07C255/00

Abstract: Halonitroarylacetonitriles are prepared by reacting a halonitroaromatic compound wherein the halo substituent has an atomic number of at least 17 with an alpha,alpha-disubstituted acetonitrile in an inert solvent and in the presence of a base so that the nitrile undergoes a nucleophilic substitution on an unsubstituted ring carbon of the halonitroaromatic compound during which an alpha-substituent functions as a leaving group. The halonitroarylacetonitriles formed by the process can be readily converted into derivatives, such as pharmaceuticals.

Abstract translation: 卤代四芳基乙腈通过卤代卤代芳族化合物制备，其中卤素取代基具有至少17的原子序数与α，α-二取代的乙腈在惰性溶剂中并在碱的存在下反应，使腈在未取代的基团上进行亲核取代 卤代硝基芳族化合物的环碳，其中α-取代基用作离去基团。 通过该方法形成的卤代四芳基乙腈可以容易地转化为衍生物，例如药物。

公开(公告)号：US4502995A

公开(公告)日：1985-03-05

申请号：US452518

申请日：1982-12-23

Applicant: Barbara C. Stahly ,  G. Patrick Stahly

Inventor： Barbara C. Stahly ,  G. Patrick Stahly

IPC: C07C63/33 ,  C07C255/32 ,  C07C121/50

CPC classification number: C07C255/00

Abstract: Fluoronitrolarylacetonitriles are prepared by reacting a fluoronitroaromatic compound having a nitro substituent, at least one fluoro substituent, and at least one replaceable hydrogen on (1) a benzene ring bearing at least one other innocuous substituent, (2) a heterocyclic aromatic ring, or (3) a carbocyclic aromatic ring of a polycyclic ring structure with an alpha,alpha-disubstituted acetonitrile in an inert solvent and in the presence of a base so that the nitrile undergoes a nucleophilic substitution on an unsubstituted ring carbon of the fluoronitroaromatic compound during which an alpha-substituent functions as a leaving group.

Abstract translation: 氟化芳基芳基乙腈通过在（1）含有至少一个其他无害取代基的苯环上反应具有硝基取代基的氟代芳基化合物，至少一个氟取代基和至少一个可取代的氢，（2）杂环芳族环或（ 3）具有α，α-二取代的乙腈的多环环结构的碳环芳环在惰性溶剂中并在碱的存在下，使得腈在氟代芳族化合物的未取代的环碳上经历亲核取代，其中 α-取代基用作离去基团。

公开(公告)号：US4476315A

公开(公告)日：1984-10-09

申请号：US452616

申请日：1982-12-23

Applicant: G. Patrick Stahly ,  Barbara C. Stahly

Inventor： G. Patrick Stahly ,  Barbara C. Stahly

IPC: C07C205/56 ,  C07C79/46

CPC classification number: C07C201/12 ,  C07C201/16 ,  C07C227/04 ,  C07C253/30 ,  C07C67/317

Abstract: Nitroarylacetic acid esters are prepared by reacting a nitroaromatic compound which is devoid of halogen on the aromatic ring carrying a nitro group with an alpha,alpha-disubstituted acetic acid ester in an inert solvent and in the presence of a base so that the ester undergoes a nucleophilic substitution on an unsubstituted ring carbon of the nitroaromatic compound during which an alpha-substituent functions as a leaving group. Nitrobenzene acetic acids and their esters are useful intermediates for the synthesis of pharmaceuticals.

Abstract translation: 硝基芳基乙酸酯通过在惰性溶剂中和在碱的存在下使含有硝基的芳环上的无卤素的硝基芳族化合物与α，α-二取代的乙酸酯反应来制备，使得酯经历 在其中α取代基用作离去基团的硝基芳族化合物的未取代环碳上的亲核取代。 硝基苯乙酸及其酯是合成药物的有用中间体。

公开(公告)号：US08691875B2

公开(公告)日：2014-04-08

申请号：US13620772

申请日：2012-09-15

Applicant: Edward Holson ,  Florence F. Wagner ,  G. Patrick Stahly

Inventor： Edward Holson ,  Florence F. Wagner ,  G. Patrick Stahly

IPC: A61K31/167 ,  C07C237/40 ,  A61P25/28 ,  A61P25/00 ,  A61P25/18 ,  A61P25/22 ,  A61P25/30

CPC classification number: C07C233/80 ,  A61K31/167 ,  C07B2200/13 ,  C07C231/12 ,  C07C237/42

Abstract: Novel solid forms of tacedinaline (4-(acetylamino)-N-(2-aminophenyl)benzamide), including crystalline tacedinaline Forms A, B, and D, a novel crystalline tacedinaline TFA salt, and amorphous tacedinaline, are disclosed. Pharmaceutical compositions comprising crystalline tacedinaline Forms A, B, and D, the novel crystalline tacedinaline TFA salt, and/or amorphous tacedinaline, and methods of treating various conditions by administering those novel solid forms, are also disclosed.

Abstract translation: 披露了一种新型固体形式的tacedinaline（4-（乙酰氨基）-N-（2-氨基苯基）苯甲酰胺），包括结晶的tacedinaline形式A，B和D，一种新型结晶的tacedineine TFA盐和无定形tacedinaline。 还公开了包含结晶哌啶酮A，B和D的药物组合物，新型结晶哌啶盐酸盐TFA盐和/或无定形泼尼汀，以及通过施用这些新型固体形式治疗各种病症的方法。