885500-38-9

Basic information

• Product Name: 4-(4-Chlorobenzyl)piperidin-4-amine dihydrochloride
• Synonyms: 4-(4-Chlorobenzyl)piperidin-4-amine dihydrochloride
• CAS NO: 885500-38-9
• Molecular Formula: C12H19Cl3N2
• Molecular Weight: 297.655
• Mol File: 885500-38-9.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: 4-(4-Chlorobenzyl)piperidin-4-amine dihydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(4-Chlorobenzyl)piperidin-4-amine dihydrochloride(885500-38-9)
• EPA Substance Registry System: 4-(4-Chlorobenzyl)piperidin-4-amine dihydrochloride(885500-38-9)

Safety Data

• Hazardous Substances Data: 885500-38-9(Hazardous Substances Data)

Upstream product

• 741687-06-9 1-tert-butyl 4-methyl 4-benzylpiperidine-1,4-dicarboxylate 
• 167263-11-8 N-tert-butyloxycarbonyl-4-benzylpiperidine-4-carboxylic acid 
• 741687-09-2 tert-butyl 4-amino-4-benzylpiperidine-1-carboxylate 
• 104-83-6 1-Chloro-4-(chloromethyl)benzene 
• 885500-37-8 4-(4-chlorobenzyl)piperidine-1,4-dicarboxylic acid 1-tert-butyl ester 4-methyl ester 
• 885653-43-0 4-(4-chlorobenzyl)-piperidin-4-ylamine 
• 956460-41-6 C₁₇H₂₅ClN₂O₂ 
• 887129-20-6 C₂₂H₃₃ClN₂O₄ 
• 956460-42-7 C₂₂H₃₃ClN₂O₄ 
• 170284-71-6 1-(tert-butoxycarbonyl)-4-(4-chlorobenzyl)piperidine-4-carboxylic acid 

Relevant articles and documents

Discovery of 4-amino-l-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4- carboxamides as selective, orally active inhibitors of protein kinase B (Akt)

Protein kinase B (PKB or Akt) is an important component of intracellular signaling pathways regulating growth and survival. Signaling through PKB is frequently deregulated in cancer, and inhibitors of PKB therefore have potential as antitumor agents. The optimization of lipophilic substitution within a series of 4-benzyl-l-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidin-4-amines provided ATP-competitive, nanomolar inhibitors with up to 150-fold selectivity for inhibition of PKB over the closely related kinase PKA. Although active in cellular assays, compounds containing 4-amino-4-benzylpiperidines underwent metabolism in vivo, leading to rapid clearance and low oral bioavailability. Variation of the linker group between the piperidine and the lipophilic substituent identified 4-amino-l-(7H-pyrrolo[2,3-d]-pyrimidin-4-yl)piperidine-4- carboxamides as potent and orally bioavailable inhibitors of PKB. Representative compounds modulated biomarkers of signaling through PKB in vivo and strongly inhibited the growth of human tumor xenografts in nude mice at well-tolerated doses.

PHARMACEUTICAL COMPOUNDS

The invention provides a compound of the formula (I) or salts, solvates, tautomers or N-oxides thereof, wherein T is N or CR5; J1-J2 is N=C(R6), (R7)C=N, (R8)N-C(O), (R8)2C-C(O), N=N or (R7)C=C(R6); E is a monocyclic carbocyclic or heterocyclic group of 5 or 6 ring members, the heterocyclic group containing up to 3 heteroatoms selected from O, N and S; Q1 is a bond or a saturated C1-3 hydrocarbon linker group, one of the carbon atoms in the linker group being optionally be replaced by an oxygen or nitrogen atom, or an adjacent pair of carbon atoms may be replaced by CONRq or NRqCO where Rq is hydrogen or methyl, or Rq is a C1-4 alkylene chain linked to R1 or a carbon atom of Q1 to form a cyclic moiety; and wherein the carbon atoms of the linker group Q1 may optionally bear one or more substituents selected from fluorine and hydroxy; Q2 is a bond or a saturated hydrocarbon linker group containing from 1 to 3 carbon atoms, wherein one of the carbon atoms in the linker group may optionally be replaced by an oxygen or nitrogen atom; and wherein the carbon atoms of the linker group may optionally bear one or more substituents selected from fluorine and hydroxy, provided that the hydroxy group when present is not located at a carbon atom α with respect to the G group; and provided that when E is aryl or heteroaryl, then Q2 is other than a bond; G is hydrogen, NR2R3, OH or SH provided that when E is aryl or heteroaryl and Q2 is a bond, then G is hydrogen; R1 is hydrogen or an aryl or heteroaryl group, with the proviso that when R1 is hydrogen and G is NR2R3, then Q2 is a bond; and R2, R3, R4, R6 and R8 are as defined in the claims, wherein the compound is for use in: (a) the treatment or prophylaxis of a disease or condition in which the modulation (e.g. inhibition) of ROCK kinase or protein kinase P70S6K is indicated; and/or (b) the treatment of a subject or patient population in which the modulation (e.g. inhibition) of ROCK kinase or protein kinase P70S6K is indicated.

PHARMACEUTICAL COMPOUNDS

Compounds of the formula (I), and salts, solvates, tautomers and N-oxide thereof; wherein TG is selected from groups (1) and (2): wherein the asterisk (*) represents the point of attachment of the group E to the group X; Rla is an optionally substituted aryl or heteroaryl group; Rlb is hydrogen or a group Rla; X is an optionally substituted bicyclic heterocyclic group having 8 to 12 ring members of which up to 5 are heteroatoms selected from O, N and S; and A, E, R2, R3, R4, Q1 and Q2 are as defined in the claims; provided that when E is aryl or heteroaryl, then Q2 is other than a bond; and further provided that the moiety (a) is other than a group (BG1) or (BG2); wherein (BGl) and (BG2) are each optionally substituted; T is N or CRZ; J1-J2 is selected from N=C(RZ), (RZ)C=N, (RZ)N-C(O), (RZ)2C-C(O), N=N and (RZ)C=C(R6); J4 -J3 is a group N=C(RZ) or a group (RZ)N-CO; and RZ is hydrogen or a substituent. The compounds of the formula (I) have PKA and PKB kinase inhibiting activity and are useful in the treatment of cancers.