7-phenyl-1, 4-diazepane compounds, process for their preparation, and pharmaceutical compositions containing them
First Claim
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1. A compound corresponding to the formula I:
- ##STR47## wherein R1 is hydrogen or lower alkyl,R2 is hydrogen, lower alkyl, lower alkoxy, halogen or trifluoromethyl, andR3 is hydrogen, lower alkyl, lower alkoxy, halogen or trifluoromethyl, orR2 and R3 together are alkylenedioxy with 1 to 2 carbon atoms, bonded to adjacent carbon atoms of the phenyl ring,R4 is hydrogen, lower alkyl, lower alkoxy, halogen or trifluoromethyl, andR5 is hydrogen, lower alkyl, lower alkoxy, halogen or trifluoromethyl, orR4 and R5 together are alkylenedioxy with 1 to 2 carbon atoms, bonded to adjacent carbon atoms of the phenyl ring,R6 is lower alkyl, halogen or trifluoromethyl,R7 is lower alkyl, halogen or trifluoromethyl,A is a --(CH2)n -- group in which n represents an integer from 1 to 3, or an --NH--(CH2)m -- group in which m represents an integer from 2 to 3, andB is an alkylene chain with 1 to 3 carbon atoms, optionally substituted by lower alkyl,or a pharmaceutically acceptable acid addition salt thereof.
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Abstract
Neurokinin-antagonistic compounds corresponding to formula I: ##STR1## in which R1 is hydrogen or lower alkyl,
R2 is hydrogen, lower alkyl, lower alkoxy, halogen or trifluoromethyl, and
R3 is hydrogen, lower alkyl, lower alkoxy, halogen or trifluoromethyl, or
R2 and R3 together are alkylenedioxy with 1 to 2 carbon atoms, bonded to adjacent carbon atoms of the phenyl ring,
R4 is hydrogen, lower alkyl, lower alkoxy, halogen or trifluoromethyl, and
R5 is hydrogen, lower alkyl, lower alkoxy, halogen or trifluoromethyl, or
R4 and R5 together are alkylenedioxy with 1 to 2 carbon atoms, bonded to adjacent carbon atoms of the phenyl ring,
R6 is lower alkyl, halogen or trifluoromethyl,
R7 is lower alkyl, halogen or trifluoromethyl,
A is a --(CH2)n -- group in which n represents an integer from 1 to 3, or an --NH--(CH2)m -- group in which m represents an integer from 2 to 3, and
B is an alkylene chain with 1 to 3 carbon atoms optionally substituted by lower alkyl,
and physiologically acceptable salts thereof and processes for the preparation of these compounds.
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Citations
6 Claims
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1. A compound corresponding to the formula I:
- ##STR47## wherein R1 is hydrogen or lower alkyl,
R2 is hydrogen, lower alkyl, lower alkoxy, halogen or trifluoromethyl, and R3 is hydrogen, lower alkyl, lower alkoxy, halogen or trifluoromethyl, or R2 and R3 together are alkylenedioxy with 1 to 2 carbon atoms, bonded to adjacent carbon atoms of the phenyl ring, R4 is hydrogen, lower alkyl, lower alkoxy, halogen or trifluoromethyl, and R5 is hydrogen, lower alkyl, lower alkoxy, halogen or trifluoromethyl, or R4 and R5 together are alkylenedioxy with 1 to 2 carbon atoms, bonded to adjacent carbon atoms of the phenyl ring, R6 is lower alkyl, halogen or trifluoromethyl, R7 is lower alkyl, halogen or trifluoromethyl, A is a --(CH2)n -- group in which n represents an integer from 1 to 3, or an --NH--(CH2)m -- group in which m represents an integer from 2 to 3, and B is an alkylene chain with 1 to 3 carbon atoms, optionally substituted by lower alkyl, or a pharmaceutically acceptable acid addition salt thereof. - View Dependent Claims (2, 3, 4, 5)
- ##STR47## wherein R1 is hydrogen or lower alkyl,
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6. A process for preparing a compound corresponding to the formula I:
- ##STR48## wherein R1 is hydrogen or lower alkyl,
R2 is hydrogen, lower alkyl, lower alkoxy, halogen or trifluoromethyl, and R3 is hydrogen, lower alkyl, lower alkoxy, halogen or trifluoromethyl, or R2 and R3 together are alkylenedioxy with 1 to 2 carbon atoms, bonded to adjacent carbon atoms of the phenyl ring, R4 is hydrogen, lower alkyl, lower alkoxy, halogen or trifluoromethyl, and R5 is hydrogen, lower alkyl, lower alkoxy, halogen or trifluoromethyl, or R4 and R5 together are alkylenedioxy with 1 to 2 carbon atoms, bonded to adjacent carbon atoms of the phenyl ring, R6 is lower alkyl, halogen or trifluoromethyl, R7 is lower alkyl, halogen or trifluoromethyl, A is a --(CH2)n -- group in which n represents an integer from 1 to 3, or an --NH--(CH2)m -- group in which m represents an integer from 2 to 3, and B is an alkylene chain with 1 to 3 carbon atoms, optionally substituted by lower alkyl, or a pharmaceutically acceptable acid addition salt thereof, said process comprising the steps of; a) to prepare a compound of Formula I, reacting a compound of formula IIa;
##STR49## wherein R2, R3, R4, R5, A and B have the above meanings and R101 represents lower alkyl or an amino protective group, with a compound of formula III;
##STR50## wherein R6 and R7 have the above meanings, and cleaving off any amino protective group R101, orb) to prepare a compound of formula Ia, ##STR51## wherein R1, R2, R3, R4, R5, R6, R7, B and n have the above meanings, reacting a compound of formula IV;
##STR52## wherein R4, R5, R6 and R7 have the above meanings, with a compound of formula V;
##STR53## wherein R101, R2, R3, B and n have the above meanings, and cleaving off any amino protective group R101, orc) to prepare a compound of formula Ib;
##STR54## wherein R1, R2, R3, R4, R5, R6, R7, B and m have the above meanings, reacting a compound of Formula IV with a compound of formula VI, ##STR55## wherein R101, R2, R3, B and m have the above meanings, and cleaving off any amino protective group R101, ord) to prepare a compound of Formula I, reacting a compound of formula VIII;
##STR56## wherein R4, R5, R6, R7 and A have the above meanings and X represents a cleavable leaving group, with a compound of formula IXa;
##STR57## wherein R1, R2, R3 and B have the above meanings, or e) to prepare a compound of Formula I, reacting a compound of formula X;
##STR58## wherein R1, R4, R5, R6, R7 and A have the above meanings, under conditions of reductive alkylation with a compound of formula XIa;
##STR59## wherein R2 and R3 have the above meanings and B1 represents a bond or an alkylene chain with 1 to 2 carbon atoms, optionally substituted by lower alkyl, or with a compound of formula XIb;
##STR60## wherein R2, R3, B1 and X have the above meanings, and optionally alkylating a resulting compound of Formula I wherein R1 is hydrogen to form a compound of Formula I wherein R1 is lower alkyl, or optionally converting a resulting compound of Formula I into an acid addition salt thereof or converting an acid addition salt into a free compound of Formula I.
- ##STR48## wherein R1 is hydrogen or lower alkyl,
Specification
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Current AssigneeSolvay Pharmaceuticals GmbH (Abbvie Incorporated)
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Original AssigneeSolvay Pharmaceuticals GmbH (Abbvie Incorporated)
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InventorsBielenberg, Gerhard-Wilhelm, Peck, Michael, Ziegler, Dieter, David, Samuel, Brueckner, Reinhard, Antel, Jochen, Eeckhout, Christian
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Primary Examiner(s)Shah, Mukund J.
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Assistant Examiner(s)COLEMAN, BRENDA LIBBY
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Application NumberUS09/141,312Time in Patent Office572 DaysField of Search514/218, 540/575US Class Current514/218CPC Class CodesA61P 1/00 Drugs for disorders of the ...A61P 1/08 for nausea, cinetosis or ve...A61P 1/12 AntidiarrhoealsA61P 29/00 Non-central analgesic, anti...A61P 43/00 Drugs for specific purposes...C07D 243/08 not condensed with other ringsY02P 20/55 Design of synthesis routes,...
