cas 106261-48-7, 4-(4-Methylpiperazin-1-ylmethyl)benzoic acid

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Discovery and Structural Optimization of 4-(Aminomethyl)benzamides as Potent Entry Inhibitors of Ebola and Marburg Virus Infections
The recent Ebola epidemics in West Africa underscore the great need for effective and practical therapies for future Ebola virus outbreaks. We have discovered a new series of remarkably potent small molecule inhibitors of Ebola virus entry. These 4-(aminomethyl)benzamide-based inhibitors are also effective against Marburg virus. Synthetic routes to these compounds allowed for the preparation of a wide variety of structures, including a conformationally restrained subset of indolines (compounds 41-50). Compounds 20, 23, 32, 33, and 35 are superior inhibitors of Ebola (Mayinga) and Marburg (Angola) infectious viruses. Representative compounds (20, 32, and 35) have shown good metabolic stability in plasma and liver microsomes (rat and human), and 32 did not inhibit CYP3A4 nor CYP2C9. These 4-(aminomethyl)benzamides are suitable for further optimization as inhibitors of filovirus entry, with the potential to be developed as therapeutic agents for the treatment and control of Ebola virus infections.
Gaisina, Irina N.,Peet, Norton P.,Wong, Letitia,Schafer, Adam M.,Cheng, Han,Anantpadma, Manu,Davey, Robert A.,Thatcher, Gregory R. J.,Rong, Lijun
p. 7211 - 7225
(2020)
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A practical synthesis of 4-[(4-methylpiperazin-1-yl)methyl]benzoic acid - The key precursor toward imatinib
A simple and efficient in situ synthesis of 4-[(4-methylpiperazin-1-yl) methyl]benzoic acid through direct reductive alkylation of 1-methylpiperazine in the presence of triacetoxy sodium borohydride in 95-99% yields is elaborated. The process is easy to scale-up for the large-scale synthesis of 4-[(4-methylpiperazin-1-yl)methyl]benzoic acid as the key synthetic intermediate of imatinib. This method was used for the synthesis of benzyl derivatives of heterocyclic amines in 87-90% yields.
Koroleva, Elena V.,Kadutskii, Aleksey P.,Farina, Alexander V.,Ignatovich, Janna V.,Ermolinskaya, Anastasiya L.,Gusak, Klaudiya N.,Kalinichenko, Elena N.
p. 5056 - 5058
(2012)
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Application of N-substituted (aminomethyl)benzoate strategy in design of scutellarein derivatives with improved Caco-2 cell permeability and in vitro antioxidative activity
A series of 4′-N-substituted (aminomethyl)benzoate derivatives of scutellarein were designed and synthesized. Evaluation of their physiochemical properties showed that the designed target compounds 5a-e exhibit higher chemical stability and aqueous solubility than scutellarin and scutellarein. The permeability (Papp AP to BL) of 5c-e in Caco-2 cells were 2.8, 8.1, and 12.6 times higher than that of scutellarin and 1.3, 4.1, and 6.0 times higher than that of scutellarein; especially, 5e had the highest Papp AP to BL value (7.19 ± 0.31 × 10-6 cm/s) and the lowest ER (Papp BL to AP/Papp AP to BL) value of 0.17. In vitro antioxidative evaluation results revealed that 5e could protect against H2O2-induced PC12 cells' oxidative damage by attenuating mitochondrial membrane potential loss and decreasing H2O2-induced reactive oxygen species (ROS) production.
Dai, Ze-Qin,Su, Hang,Luo, Min,Ou, Yu,Fu, Xiao-Zhong,Dong, Yong-Xi,Cha, Yu-Feng,Zhang, Shun,Huang, Yong,Wang, Yong-Lin
p. 1959 - 1965
(2015)
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C-3 NOVEL TRITERPENONE WITH C-17 REVERSE AMIDE DERIVATIVES AS HIV INHIBITORS
The present invention relates to C-3 novel triterpenone with C-17 reverse amide compounds of Formula (I); and pharmaceutically acceptable salts thereof, wherein ring Formula (II), R1, R2, R3, R4, R5, R6, R7, 'n' and 'm' are as defined in Formula (I). The invention also relates to C-3 novel triterpenone with C-17 reverse amide derivatives, related compounds, and pharmaceutical compositions useful for the therapeutic treatment of viral diseases and particularly HIV mediated diseases.
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Page/Page column 49

(2018/03/06)

N-phenyl-2-pyrimidine-amine derivatives
The present invention relates to novel amides and a process for preparing these amides.
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Page/Page column 13-14

(2017/03/14)

Combination of 4-anilinoquinazoline, arylurea and tertiary amine moiety to discover novel anticancer agents
In present study, 4-anilinoquinazolines scaffold, arylurea and tertiary amine moiety were combined to design, synthesize gefitinib analogs and discover novel anticancer agents. A series of 4-anilinoquinazoline derivatives (1, 2, 3 and 4) bearing arylurea and tertiary amine moiety at its 6-position were synthesized. Their antiproliferative activities in vitro were evaluated via MTT assay against A431 cell and A549 cell. The SAR of the title compounds was discussed. The compounds 2d, 2i and 2j with potent antiproliferative activities were evaluated their inhibitory activity against EGFR-TK. Compound 2j displayed potent inhibitory activity against EGFR-TK. In addition, compound 2j, at 50 mg/kg, can completely inhibit cancer growth in established nude mouse A549 xenograft model in vivo. These results suggest that the 4-anilinoquinazoline derivatives bearing diarylurea and tertiary amino moiety at its 6-position can serve as anticancer agents and EGFR inhibitors.
Zuo, Sai-Jie,Zhang, Sai,Mao, Shuai,Xie, Xiao-Xiao,Xiao, Xue,Xin, Min-Hnag,Xuan, Wei,He, Yuan-Yuan,Cao, Yong-Xiao,Zhang, San-Qi
p. 179 - 190
(2015/12/31)

COMPOSITIONS AND METHODS FOR INHIBITING KINASES
The present invention provides compounds for the prevention or treatment of cancer or a bacterial or viral infection. Additionally, the present invention provides compositions and methods for using these compounds and compositions in the prevention or treatment of cancer or a bacterial or viral infection in a subject.
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Page/Page column 33; 35

(2016/11/14)

PROTEIN KINASE INHIBITORS
The present invention relates to compounds of the following formula (I) and/or the pharmaceutically acceptable addition salts, solvates, enantiomers, diastereoisomers thereof, as well as mixtures thereof. The subject matter of the present invention thus also includes the preparation of compounds of formula (I), their uses, in particular in the inhibition of protein kinases which are implicated for example in numerous diseases such as cancers or immune system disorders.
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Page/Page column 43-44

(2014/07/21)

AZAINDOLE DERIVATIVES AS MULTI KINASE INHIBITORS
The present invention relates to compounds of the following formula (I) and/or the pharmaceutically acceptable addition salts, solvates, enantiomers, diastereoisomers thereof, as well as mixtures thereof. The subject matter of the present invention thus also includes the preparation of compounds of formula (I), their uses, in particular in the inhibition of protein kinases which are implicated for example in numerous diseases such as cancers or immune system disorders.
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Page/Page column 48-49

(2014/07/21)

Preparative synthesis of heterocyclic and aromatic N-benzyl amines
A simple and highly efficient procedure has been proposed for the synthesis of heterocyclic and aromatic N-benzyl amines via reductive amination of substituted aromatic aldehydes in the presence of sodium tetrahydridoborate- acetic acid system generating reactive sodium triacetoxyhydridoborate.
Koroleva,Gusak,Ermolinskaya,Ignatovich
p. 563 - 567
(2013/06/26)

Novel method for preparing imatinib base
The present invention relates to a novel method for preparing an imatinib base, and more particularly to a method for preparing an imatinib base, which comprises reacting 4-(4-methyl-piperazinomethyl)-benzoic acid with a 2,2'-dibenzothiazolyl disulfide derivative in the presence of a phosphine derivative to prepare a novel thioester compound and preparing an imatinib base using the thioester compound as a reaction intermediate. In addition, the invention provides a novel thioester compound, which is used in the preparation of imatinib base, and a preparation method thereof. Ultimately, the invention provides a method of preparing the imatinib base in an economic manner and in high yield and purity and is expected to be used in the commercial production of large amounts of the imatinib base.
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Page/Page column 11

(2012/12/14)

METHOD FOR PRODUCING IMATINIB BASE
The present invention relates to a novel method for preparing an imatinib base, and more particularly to a method for preparing an imatinib base, which comprises reacting 4-(4-methyl-piperazinomethyl)-benzoic acid with a 2,2′-dibenzothiazolyl disulfide derivative in the presence of a phosphine derivative to prepare a novel thioester compound and preparing an imatinib base using the thioester compound as a reaction intermediate. In addition, the invention provides a novel thioester compound, which is used in the preparation of imatinib base, and a preparation method thereof. Ultimately, the invention provides a method of preparing the imatinib base in an economic manner and in high yield and purity and is expected to be used in the commercial production of large amounts of the imatinib base.
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Page/Page column 9-10

(2013/02/28)

FLUORO-SUBSTITUTED COMPOUNDS AS KINASE INHIBITORS AND METHODS OF USE THEREOF
The present invention provides for novel compounds of Formula I and pharmaceutically acceptable salts and solvates thereof which have kinase inhibitor activity. The present invention further provides for pharmaceutical compositions comprising the same as well as methods of treating and preventing a Bcr-Abl, c-Kit or PDGF-R mediated disorder for which one or more kinase inhibitor is indicated, including neoplasia such as chronic myelogenous leukemia or gastrointestinal stromal tumors. The present invention also provides for processes of making the compounds of Formula I, including salts and solvates thereof, and pharmaceutical compositions comprising the same.
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Page/Page column 25

(2011/02/24)

Synthesis of new amides of the N-methylpiperazine series
New carboxylic acid amides containing an N-methylpiperazine fragment were synthesized by reactions of 1-methylpiperazine or 3- and 4-(4-methylpiperazin-1- ylmethyl)aniline with 4-chlorobenzoyl chloride and of 4-methyl-3-nitroaniline with 4-(4-methylpiperazin-1-ylmethyl)benzoyl chloride or benzotriazol-1-yl 4-(4-methylpiperazin-1-ylmethyl)benzoate. 4-Chloro-N-[4-(4-methylpiperazin-1- ylmethyl)phenyl]benzamide reacted with imidazole, quinolin-5-amine, and 2-methylquinolin-5-amine to give substituted 4-amino-N-[4-(4- methylpiperazin-1-ylmethyl)phenyl]benzamides. 4-Methyl-3-nitrophenyl-4- methylpiperazin-1-yl-substituted benzamides were reduced with hydrazine hydrate over Raney nickel to obtain N-(3-amino-4-methylphenyl)-4- (4-methylpiperazin-1- ylmethyl)benzamide as key intermediate in the synthesis of antileukemic agent imatinib and its isomer with alternative position of the amide group, 4-[(3-amino-4-methylphenylamino)methyl]phenyl- (4-methylpiperazin-1-yl)} methanone. Pleiades Publishing, Ltd., 2011.
Koroleva,Gusak,Ignatovich,Ermolinskaya
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p. 1556 - 1563
(2012/03/09)

Hydrazinopyrimidines as cysteine protease inhibitors
Substituted heteroaryl nitrile derivatives of Formula I, processes for their preparation, pharmaceutical compositions comprising such compounds and use of the compounds as cysteine protease inhibitors are provided.
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Page/Page column 36-37

(2008/12/04)

PURINES AS CYSTEINE PROTEASE INHIBITORS
Substituted heteroaryl nitrile derivatives of Formula I, processes for their preparation, pharmaceutical compositions comprising such compounds and use of the compounds as cysteine protease inhibitors are provided.
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Page/Page column 48

(2008/12/07)

Process for the preparation of imatinib
The present invention provides process for the preparation of Imatinib and Imatinib salts, including processes that prepare intermediates for the production of Imatinib.
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Page/Page column 7

(2008/06/13)

Interaction of secondary amines with aromatic aldehydes-efficient method for synthesis of the functionalized heterocyclic amines
A method is proposed for the benzylation of secondary heterocyclic amines with functionalized derivatives of benzaldehyde in the presence of formic acid under conditions close to amination according to the Leuckart-Wallach reaction.
Ignatovich,Gusak,Chernikhova,Kozlov,Koroleva
p. 1540 - 1543
(2008/09/20)

NOVEL CYSTEINE PROTEASE INHIBITORS
Substituted heteroaryl nitrile derivatives of Formula (I), processes for their preparation, pharmaceutical compositions comprising such compounds and use of the compounds as cysteine protease inhibitors are provided.
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Page/Page column 48

(2010/11/26)

2,4-SUBSTITUTED PYRIMIDINES AS CYSTEINE PROTEASE INHIBITORS
Substituted heteroaryl nitrile derivatives of Formula (I) processes for their preparation, pharmaceutical compositions comprising such compounds and use of the compounds as cysteine protease inhibitors are provided.
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Page/Page column 56

(2010/10/20)

THIOPHENE HETEROARYL AMINES
The present invention relates to thiophene heteroaryl amines and their pharmaceutically acceptable salts that modulate the activity of protein kinases and therefore are expected to be useful in the prevention and treatment of protein kinase related cellular disorders such as cancer. Formula (I).
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Page/Page column 36

(2010/02/14)

PYRIDINE DERIVATIVES USEFUL FOR INHIBITING SODIUM/CALCIUM EXCHANGE SYSTEM
Therapeutically active compounds of formula (I) or (II) wherein X is -O-, -CH2- or -C(O)-; Z is -CHR12- or a valence bond; Y is -CH2-, -C(O)-, CH(OR13)-, -O-, -S-; provided that in case Z is a valence bond, Y is not C(O); the dashed line representing an optional double bond in which case Z is -CR12- -and Y is -CH2-, -C(O)- or -CH(OR10)- (in formula II) or -CH- (in formula I); R2 and R3 are independently H, lower alkyl, lower alkoxy, -NO2, halogen, -CF3, -OH, benzyloxy or a group of formula (IIIa). R1 is H, CN, halogen, -CONH2, -COOR15, CH2NR15R18, NHC(O)R5, NHCH2R5, NHR20, NR21R22, NHC(NH)NHCH3 or, in case the compound is of formula (II) wherein the optional double bond exists or in case R2 or R3 is benzyloxy or a group of formula (IIIa) or in case the pyridine ring of formula (I) or (II) is attached to the oxygen atom in 3-, 4- or 5-position, R1 can also be -NO2 or NR16R17; R4 is H, -NO2, CN, halogen, -CONH2, -COOR15, -CH2NR15R18, -NR16R17, NHC(O)R5 or -NHC(NH)NHCH3; R5 is alkyl substituted with 1-3 substituents selected from the group consisting of halogen, amino and hydroxy, or carboxyalkyl, in which the alkyl portion is optionally substituted with 1-3 substituents selected from the group consisting of halogen, amino and hydroxyl, -CHR6NR,R8 or one of the following groups: formula (IVa), (IVb), (IVc), (IVd), (IVe), and pharmaceutically acceptable salts and esters thereof. The compounds are potent inhibitors of Na+/Ca2+ exchange mechanism.
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Page 74

(2008/06/13)