34637-41-7

Usage

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 27, p. 119, 1990 DOI: 10.1002/jhet.5570270201

InChI:InChI=1/C9H6Cl2N2/c10-5-8-12-7-4-2-1-3-6(7)9(11)13-8/h1-4H,5H2

Upstream product

• 107-14-2 chloroacetonitrile 
• 1885-29-6 anthranilic acid nitrile 
• 87-25-2 2-ethoxycarbonylaniline 
• 118-92-3 anthranilic acid 
• 3817-05-8 2-(chloromethyl)quinazolin-4-ol 
• 3817-05-8 2-(chloromethyl)quinazolin-4(3H)-one 

Downstream Products

• 863654-21-1 2-(chloromethyl)-N-phenylquinazoline-4-amine 
• 6148-18-1 2-chloromethylquinazoline 
• 1093985-86-4 2-(aminomethyl)-N-phenylquinazolin-4-amine 
• 1093985-85-3 2-(azidomethyl)-N-phenylquinazolin-4-amine 
• 1093982-84-3 4-chloro-N-((4-(pyrrolidin-1-yl)quinazolin-2-yl)methyl)benzamide 
• 1093616-98-8 N-((4-(phenylamino)quinazolin-2-yl)methyl)naphthalene-1-sulfonamide 
• 1093982-82-1 1-(2,4-dichlorophenyl)-3-((4-(pyrrolidin-1-yl)quinazolin-2-yl)methyl)urea 
• 1093985-40-0 N-phenyl-2-((phenylamino)methyl)quinazolin-4-amine 

Relevant academic research and scientific papers

Selective inhibitors of fibroblast activation protein (FAP) with a xanthine scaffold

Fibroblast activation protein (FAP) is a serine protease that is selectively expressed in many diseases involving activated stroma, including cancer, arthritis and hepatic and pulmonary fibrosis. FAP is closely related to dipeptidyl peptidase IV (DPPIV), of which many inhibitors are known and several are marketed as drugs. One of these is the xanthine derivative linagliptin. In a broad literature screen amongst reported DPPIV inhibitors, linagliptin was the only druglike compound identified that possessed significant FAP potency. Hence, this compound served as a starting point for a SAR study that aimed to identify structural determinants that selectively increase FAP-potency of linagliptin analogues. By investigating the influence of the substitution pattern on N1, N7 and C8 of the xanthine scaffold, we managed to decouple DPPIV and FAP potency and identified the first selective xanthine-based FAP inhibitors with low micromolar potency. Furthermore, these compounds are the only known FAP-inhibitors that do not rely on a warhead functionality to obtain potencies in this range.

AROMATIC NITROGEN-CONTAINING 6-MEMBERED RING COMPOUNDS AND THEIR USE

The present invention provides aromatic nitrogen-containing 6-membered ring compounds having execellent PDE10 inhibitory activity. The present invention relates to an aromatic nitrogen-containing 6-membered ring compound represented by the following formula [I0] or a pharmaceutically acceptable salt thereof, a method for preparing the same, and use of said compounds for PDE10 inhibitors, and a pharmaceutical composition comprising said compounds as an active ingredient: Formula [I0] wherein: X1, X2 and X3 each independently are N or CH, and at least two of X1, X2 and X3 are N; A is *-CH=CH-, *-C(Alk)=CH-, *-CH2-CH2- or *-O-CH2- (* is a bond with R1); Alk is a lower alkyl group; Ring B is an optionally substituted nitrogen-containing aliphatic heterocyclic group; R1 is an optionally substituted nitrogen-containing heterocyclic group, a nitrogen-containing heterocyclic moiety of which is a moiety selected from the group consisting of quinoxalinyl, quinolyl, isoquinolyl, quinazolinyl, pyrazinyl, pyrimidinyl and a moiety thereof fused with a 5 to 6-membered aliphatic ring thereto; Y0 is a group selected from the group consisting of the following (1) to (5): (1) an optionally substituted phenyl or an optionally substituted aromatic monocyclic 5 to 6-membered heterocyclic group; (2) an optionally substituted aminocarbonyl; (3) an optionally substituted amino lower alkyl; (4) -O-R2 wherein R2 is hydrogen, an optionally substituted lower alkyl, lower cycloalkyl, aliphatic monocyclic 5 to 6-membered heterocyclic group, or Formula [AA]; (5) mono- or di-substituted amino; provided that, when Y0 is mono- or di-substituted amino, the nitrogen-containing heterocyclic moiety of R1 is not quinoxalinyl or quinolyl.

PHARMACEUTICAL COMPOUNDS AS INHIBITORS OF CELL PROLIFERATION AND THE USE THEREOF

Disclosed are compounds of Formula I effective as cytotoxic agents. The compounds of this invention are useful in the treatment of a variety of clinical conditions in which uncontrolled growth and spread of abnormal cells occurs.

PHARMACEUTICAL COMPOUNDS AS CYTOTOXIC AGENTS AND THE USE THEREOF

Disclosed are compounds effective as cytotoxic agents. The compounds of this invention are useful in the treatment of a variety of clinical conditions in which uncontrolled growth and spread of abnormal cells occurs.

Discovery of N-(4-methoxyphenyl)-N,2-dimethylquinazolin-4-amine, a potent apoptosis inducer and efficacious anticancer agent with high blood brain barrier penetration

As a continuation of our structure-activity relationship (SAR) studies on 4-anilinoquinazolines as potent apoptosis inducers and to identify anticancer development candidates, we explored the replacement of the 2-Cl group in our lead compound 2-chloro-N-(4-methoxyphenyl)-N-methylquinazolin-4-amine (6b, EP128265, MPI-0441138) by other functional groups. This SAR study and lead optimization resulted in the identification of N-(4-methoxyphenyl)-N,2- dimethylquinazolin-4-amine (6h, EP128495, MPC-6827) as an anticancer clinical candidate. Compound 6h was found to be a potent apoptosis inducer with EC 50 of 2 nM in our cell-based apoptosis induction assay. It also has excellent blood brain barrier penetration, and is highly efficacious in human MX-1 breast and other mouse xenograft cancer models.

AMINOQUINAZOLINE CANNABINOID RECEPTOR MODULATORS FOR TREATMENT OF DISEASE

The present invention relates to compounds and methods useful as modulators of CB2 for the treatment or prevention of disease states including, but not limited to pain, autoimmune disease, malabsorption syndrome, pulmonary disease, osteoporosis, muscle spasm in cancer, neuromuscular disorder, and atherosclerosis progression.

Synthesis and antihyperlipidemic activity of some novel condensed 2-chloroalkyl-4-chloro/hydroxy-5,6-disubstituted pyrimidines

Synthesis and antihyperlipidemic activity of a series of novel condensed 2-chloroalkyl-4-chloro/hydroxy-5,6-di-substituted pyrimidines are described. The design of these compounds is based on the earlier QSAR study on the antihyperlipidemic 2-substituted

METHOD OF TREATING BRAIN CANCER

Disclosed are 4-arylamino-quinazolines and analogs thereof effective as activators of caspases and inducers of apoptosis. The compounds of this invention are useful in the treatment of a variety of clinical conditions in which uncontrolled growth and spread of abnormal cells occurs, and in particular to the use of these compounds in treating brain cancer.

COMPOUNDS AND THERAPEUTICAL USE THEREOF

Disclosed are 4-arylamino-quinazolines and analogs thereof effective as activators of caspases and inducers of apoptosis. The compounds of this invention are useful in the treatment of a variety of clinical conditions in which uncontrolled growth and spread of abnormal cells occurs.

4-aminoquinazoline derivatives

The compounds of the formula: STR1 wherein R1, Y, A, R4, n, Z, CyB, R3, and m are defined in the specification.