21888-98-2 Usage
Originator
Tremblex,Brocades,Italy,1981
Uses
Anticholinergic.
Manufacturing Process
400 parts glacial acetic acid are cooled to 10°C to 20°C. Then there are added
first dropwise 300 parts concentrated sulfuric acid followed by portionwise
addition of 50 parts dl-1-benzyl-4-(1,3-dicyano-1-phenylpropyl)-piperidine
hydrochloride at the same temperature. After the addition is complete, the
whole is heated to 125°C in the course of 15 to 20 minutes. This temperature
is then maintained for 10 minutes. After cooling, the reaction mixture is poured into ice, alkalized with NH4OH at a temperature < 20°C and extracted
with chloroform. The chloroform layer is first washed twice with a K2CO3 5%
solution, and then washed twice with water, dried over MgSO4, filtered and
evaporated. The residue is dissolved in a mixture of 320 parts acetone and
600 parts diisopropylether, filtered and HCl gas is introduced into the filtrate.
The solid hydrochloride is filtered off and dried, to yield 43 parts less pure lbenzyl-4-(2.6-dioxo-3-phenyl-3-piperidyl)-piperidine hydrochloride, melting
point 283°C to 294°C.A sample of 4 parts is recrystallized from a boiling mixture of 80 parts
isopropanol, 40 parts methanol and 500 parts water. The whole is filtered and
after cooling the filtrate overnight at -20°C, 1-benzyl-4-(2,6-dioxo-3phenyl-3-
piperidyl)-piperidine hydrochloride is obtained, melting point 299°C to
301.5°C, as a white amorphous powder.The dextro-isomer may be separated via the dextro-camphorsulfonate of the
base.
Therapeutic Function
Anticholinergic (ophthalmic)
Check Digit Verification of cas no
The CAS Registry Mumber 21888-98-2 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,1,8,8 and 8 respectively; the second part has 2 digits, 9 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 21888-98:
(7*2)+(6*1)+(5*8)+(4*8)+(3*8)+(2*9)+(1*8)=142
142 % 10 = 2
So 21888-98-2 is a valid CAS Registry Number.
InChI:InChI=1/C23H26N2O2/c26-21-11-14-23(22(27)24-21,19-9-5-2-6-10-19)20-12-15-25(16-13-20)17-18-7-3-1-4-8-18/h1-10,20H,11-17H2,(H,24,26,27)/t23-/m0/s1
21888-98-2Relevant articles and documents
PIPERIDINE DERIVATIVES AS CXCR3 RECEPTOR ANTAGONISTS
-
Page/Page column 65, (2008/06/13)
The present invention relates to a compound of formula (I), aN-oxide thereof, a pharmaceutically acceptable salt thereof, a stereochemically isomeric form thereof or a solvate thereof, wherein X represents N or CH; Y and Z each independently represent C(=O) or CH2 provided that at least one of Y and Z represents C(=O); R1 represents CH(R4)-aryl or CH(R4)-heteroaryl; R2 represents aryl2 or heteroaryl; R3 represents hydrogen; C1-4alkylcarbonyl; C1-6alkyl optionally substituted with C1-6alkyloxy, C1-6alkylthio, C1-6alkyloxycarbonyl or aryl1 ; provided that when Y and Z each represent C(=O), X represents CH, R3 represents hydrogen, R4 represents hydrogen, and R2 represents unsubstituted pyridyl or phenyl optionally substituted with one halo or with one C1-4alkyloxy or with one or two C1-4alkyl, then aryl in the definition of R1 is other than phenyl substituted with one halo or with one or two C1-4alkyl; and provided that when Y and Z each represent C(=O), X represents CH, R3 represents hydrogen, and R2 represents unsubstituted pyridyl or phenyl optionally substituted with one halo or with one C1-4alkyloxy or with one or two C1-4alkyl, then heteroaryl in the definit ion of R1 is other than unsubstituted thienyl or unsubstituted pyridyl. The present invention also relates to the use of a compound of formula (I) for the manufacture of a medicament for preventing or treating a disease mediated through activation of the CXCR3 receptor; to processes for preparing the compounds of formula (I) and pharmaceutical compositions comprising them.
