EP0288640A1
Expired / Lapsed
EP
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6,11-Dihydro-11-(4-piperidylidene)-5H-benzo[5,6]cyclohepta-[1,2-b]pyridines and compositions and methods of use
Assignee: Merck Sharp & Dohme LLC
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Filing: 1987-10-22
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Granted: —
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Expires: 2007-10-22
Abstract
Abstract Derivatives of 6,11-dihydro-11-(4-piperidylidene)-5 H -benzo[5,6]cyclohepta[1,2-b]pyridine, and pharmaceutically acceptable salts and solvates thereof are disclosed, which possess anti-allergic activity, making them effective as anti-allergic compounds. Methods for preparing and using the compounds are also described.
Inventors
- 👤 John J. Piwinsky
- 👤 Michael John Green
- 👤 Ashit Kumar Ganguly
- 👤 Jesse Kwok-Keung Wong
- 👤 Bernard Katchen
- 👤 Jeffrey Abbott Cramer
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-11-04 09:00
CPC Classifications
C; C07; C07D; C07D401/00; C07D401/02; C07D401/04; A; A61; A61P; A61P37/00; A61P37/08; A61P43/00
Claims Analysis
Total Claims: 18
Claim 1
Independent Claim
224 words
A compound represented by structural formula I: or a pharmaceutically acceptable salt or solvate thereof, wherein: R represents H or alkyl, such that (1) when R represents alkyl, at least one of A and B represents a substituent group selected from H and OR¹, H and OC(O)R¹, =NOR¹ or -O-(CH₂) n -O-, and the other may represent H₂ or one of the above listed substituent groups; W, X, Y and Z may be the same or different and each independently represents H, halo, alkyl, -CF₃, -NO₂, -OC(O)R¹, -SR¹, -OR¹, -CO₂R¹ or -N(R¹)₂; R¹ is H, alkyl or aryl and in N(R¹)₂, R¹ can be alkanediyl, and n is 2, 3 or 4, and (2) when R represents H, A or B may be the same or different and each independently represents H₂, H and OR¹, H and OC(O)R¹, =O, =NOR¹ or -O-(CH₂) n -O-; W, X, Y and Z may be the same or different and each independently represents H, halo, alkyl, -CF₃, -NO₂, -OC(O)R¹, -SR¹, -OR¹ or -CO₂R¹ or -N(R¹)₂, with the provisos that when A and B both represent H₂, W is OR¹ and R¹ is H, and when A or B represents =O, at least one of W, X, Y and Z represents halo, alkyl, -CF₃, -NO₂, -OC(O)R¹, -SR¹, -OR¹, -CO₂R¹ or -N(R¹)₂; and R¹ and n are as defined above.
Claim 2
Dependent Claim
224 words
A compound represented by structural formula I: or a pharmaceutically acceptable salt or solvate thereof, wherein: R represents H or alkyl, such that (1) when R represents alkyl, at least one of A and B represents a substituent group selected from H and OR¹, H and OC(O)R¹, =NOR¹ or -O-(CH₂) n -O-, and the other may represent H₂ or one of the above listed substituent groups; W, X, Y and Z may be the same or different and each independently represents H, halo, alkyl, -CF₃, -NO₂, -OC(O)R¹, -SR¹, -OR¹, -CO₂R¹ or -N(R¹)₂; R¹ is H, alkyl or aryl and in N(R¹)₂, R¹ can be alkanediyl, and n is 2, 3 or 4, and (2) when R represents H, A or B may be the same or different and each independently represents H₂, H and OR¹, H and OC(O)R¹, =O, =NOR¹ or -O-(CH₂) n -O-; W, X, Y and Z may be the same or different and each independently represents H, halo, alkyl, -CF₃, -NO₂, -OC(O)R¹, -SR¹, -OR¹ or -CO₂R¹ or -N(R¹)₂, with the provisos that when A and B both represent H₂, W is OR¹ and R¹ is H, and when A or B represents =O, at least one of W, X, Y and Z represents halo, alkyl, -CF₃, -NO₂, -OC(O)R¹, -SR¹, -OR¹, -CO₂R¹ or -N(R¹)₂; and R¹ and n are as defined above.
Claim 3
Dependent Claim
87 words
A compound as defined in claim 1 wherein R represents alkyl; at least one of A and B represents a substituent group selected from H and OR¹, H and OC(O)R¹, =NOR¹ or -O-(CH₂) n -O-, and the other may represent H₂ or one of the above listed substituent groups; W, X, Y and Z may be the same or different and each independently represents H, halo, alkyl, -CF₃, -NO₂, -OC(O)R¹, -SR¹, -CO₂R¹ or -N(R¹)₂; R¹ is H, alkyl or aryl and n is 2, 3 or 4.
Claim 4
Dependent Claim
113 words
A compound as defined in claim 1 wherein R represents H; A or B may be the same or different and each independently represents H₂, H and OR¹, H and OC(O)R¹, =O, =NOR¹ or -O-(CH₂) n -O-; W, X, Y and Z may be the same or different and each independently represents H, halo, alkyl, -CF₃, -NO₂, -OC(O)R¹, -SR¹, -OR¹ or -CO₂R¹ or -N(R¹)₂ with the provisos that when A and B both represent H₂, W is -OH, and when A or B represents =O, at least one of W, X, Y and Z represents halo, alkyl, -CF₃, -NO₂, -OC(O)R¹, -SR¹, -OR¹, -CO₂R¹ or -N(R¹)₂, and R¹ and n are as previously defined.
Claim 5
Dependent Claim
12 words
A compound as defined in claim 2 wherein R represents lower alkyl.
Claim 6
Dependent Claim
35 words
A compound as defined in any of claims 1-4 above wherein one of A and B is H₂ and the other of A and B represents H- and OC(O)R¹, =O, =NOR¹ or -O-(CH₂) n O-.
Claim 7
Dependent Claim
22 words
A compound as defined in any of claims 1-5 above wherein at least one of A and B represents H and OR¹.
Claim 8
Dependent Claim
20 words
A compound as defined in any of claims 1-6 above wherein A and B represent H₂, and W represents OR¹.
Claim 9
Dependent Claim
14 words
A compound as defined in any of claims 1-7 above wherein R¹ represents H.
Claim 10
Dependent Claim
26 words
A compound as defined in any of claims 1-8 above wherein W, X, Y and Z independently represent H, halo, alkyl, -CF₃, SR¹, -OR¹ or N(R¹)₂.
Claim 11
Dependent Claim
20 words
A compound as defined in any of claims 1-9 above wherein at least one of Y and Z represents halo.
Claim 12
Dependent Claim
17 words
A compound as defined in any of claims 1-10 above wherein W represents OR¹ at position 3.
Claim 13
Dependent Claim
20 words
A compound as defined in claim 1 having the following name: 8-chloro-11-[4-piperidylidene]-5,11-dihydro-6H-benzo[5,6]cyclohepta[1,2-b]pyridin-6-one; 6-hydroxy-8-chloro-11-[4-piperidylidene]-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridine; 8-chloro-6-hydroxyimino-11-[1-methyl-4-piperidylidine]-6H-benzo[5,6]cyclohepta[1,2-b]pyridine; 8-chloro-11-[1-methyl-4-piperidylidene]-5,11-dihydro-6H-benzo[5,6]-cyclohepta[1,2-b]pyridin-6-ol; 8-chloro-11-[1-methyl-4-piperidylidene]-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridin-6-ol; 8-chloro-11-[4-piperidylidene]-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridin-5-one; 5-hydroxy-8-chloro-11-(4-piperidylidene)-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridine; or 3-hydroxy-8-chloro-11-|4-piperidylidene]-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridine.
Claim 14
Dependent Claim
17 words
A pharmaceutical composition which comprises a compound of claim 1 in combination with a pharmaceutically acceptable carrier.
Claim 15
Independent Claim
19 words
A method of making a pharmaceutical composition comprising mixing a compound of formula I with a pharmaceutically acceptable carrier.
Claim 16
Independent Claim
19 words
A method of making a pharmaceutical composition comprising mixing a compound of formula I with a pharmaceutically acceptable carrier.
Claim 17
Dependent Claim
20 words
The use of a compound as claimed in claim 1 for the preparation of a pharmaceutical composition for anti-allergy application.
Claim 18
Dependent Claim
99 words
A process for producing a compound having structural formula I as defined in Claim 1 characterised by: a) decarboxylating a compound of the structure where R b is alkyl, or aryl; b) reducing the keto compound at the keto group, c) dealkylating a compound of the structure where R a is alkyl; or d) oral dosing a human and/or monkey with 8-chloro-6,11-dihydro-11-(1-ethoxycarbonyl-4-piperidylidene)- 5 H-benzo [5,6]cyclohepta[1,2-b]pyridine and isolating from the respective human and/or monkey urine; which processes may further comprise the step of converting one functional group of a compound of formula I into another functional group of formula I.
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