US5202324A
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Imidazopyridazines
Assignee: Takeda Pharmaceutical Co Ltd
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Filing: 1990-01-31
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Granted: 1993-04-13
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Expires: 2010-01-31
Abstract
Abstract The imidazo[1,2-b]pyridazine compounds of the formula: ##STR1## wherein R 1 is a hydrogen or halogen atom, or a lower alkyl group optionally having substituent(s), R 2 and R 3 are, independently, a hydrogen atom, a lower alkyl group optionally having substituent(s), a cycloalkyl group or a phenyl group optionally having substituent(s) or R 2 and R 3 together with the adjacent nitrogen atom to which they bond may form a heterocyclic ring optionally having substituent(s), X is an oxygen atom or S(O) n (n=0 to 2), Alk is a straight or branched chain alkylene group containing 1-10 carbon atoms and optionally having substituent(s), or their pharmaceutically acceptable salts which possess antiallergic, anti-inflammatory and anti-PAF activities, and their production and use.
Inventors
- 👤 Akio Miyake
- 👤 Masaaki Kuwahara
- 👤 Hisashi Kuriki
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 02:05
CPC Classifications
C; C07; C07D; C07D487/00; C07D487/02; C07D487/04
Claims Analysis
Total Claims: 21
Claim 1
Independent Claim
270 words
An imidazo[1,2-b]pyridazine compound of the formula (I): ##STR45## wherein R 1 is a hydrogen or halogen atom, or a lower alkyl group optionally having substituent(s) selected from the group consisting of hydroxy, amino, a mono-lower alkylamino, a lower alkoxy and a halogen, R 2 and R 3 are, independently, a hydrogen atom, a lower alkyl group optionally having substituent(s) as above, a cyclo alkyl group or a phenyl group optionally having substituent(s) selected from the group consisting of amino, a mono- or di-lower alkylamino, a lower alkoxy and a halogen, or R 2 and R 3 together with the adjacent nitrogen atom to which they bond may form a 4 to 7 membered heterocyclic ring having at least one nitrogen atom and optionally oxygen and/or sulfur atoms and optionally having substituent(s) selected from the group consisting of hydroxy, amino, mono- or di-lower alkylamino, lower alkoxy and a halogen, X is an oxygen atom or S(O) n (n=0 to 2), Alk is a straight or branched chain alkylene group containing 1-10 carbon atoms and optionally having substituent(s) selected from the group consisting of hydroxy, amino, a halogen, phenyl, benzyl, a mono-lower alkylamino, a lower alkoxy or a heterocycle, provided that X should be an oxygen atom when R 1 is a hydrogen atom, one of R 2 and R 3 is a hydrogen and the remaining one is a hydrogen atom, one of R 2 and R 3 is a hydrogen and the remaining one is a hydrogen atom or a lower alkyl group and Alk is a straight chain alkylene group containing 2-4 carbon atoms, or its pharmaceutically acceptable salt.
Claim 2
Dependent Claim
270 words
An imidazo[1,2-b]pyridazine compound of the formula (I): ##STR45## wherein R 1 is a hydrogen or halogen atom, or a lower alkyl group optionally having substituent(s) selected from the group consisting of hydroxy, amino, a mono-lower alkylamino, a lower alkoxy and a halogen, R 2 and R 3 are, independently, a hydrogen atom, a lower alkyl group optionally having substituent(s) as above, a cyclo alkyl group or a phenyl group optionally having substituent(s) selected from the group consisting of amino, a mono- or di-lower alkylamino, a lower alkoxy and a halogen, or R 2 and R 3 together with the adjacent nitrogen atom to which they bond may form a 4 to 7 membered heterocyclic ring having at least one nitrogen atom and optionally oxygen and/or sulfur atoms and optionally having substituent(s) selected from the group consisting of hydroxy, amino, mono- or di-lower alkylamino, lower alkoxy and a halogen, X is an oxygen atom or S(O) n (n=0 to 2), Alk is a straight or branched chain alkylene group containing 1-10 carbon atoms and optionally having substituent(s) selected from the group consisting of hydroxy, amino, a halogen, phenyl, benzyl, a mono-lower alkylamino, a lower alkoxy or a heterocycle, provided that X should be an oxygen atom when R 1 is a hydrogen atom, one of R 2 and R 3 is a hydrogen and the remaining one is a hydrogen atom, one of R 2 and R 3 is a hydrogen and the remaining one is a hydrogen atom or a lower alkyl group and Alk is a straight chain alkylene group containing 2-4 carbon atoms, or its pharmaceutically acceptable salt.
Claim 3
Dependent Claim
98 words
A compound of claim, 1 in which R 1 is substituted at the 2 position of imidazo[1,2-b]pyridazine ring and is a hydrogen atom or a lower alkyl group, R 2 and R 3 are, independently, a hydrogen atom, a lower alkyl group optionally having substituent(s), a cycloalkyl group or a phenyl group optionally having substituent(s) or R 2 and R 3 together with the adjacent nitrogen atom to which they bond may form a heterocyclic ring optionally having substituent(s), X is an oxygen or sulfur atom and Alk is a straight chain alkylene group containing 1-6 carbon atoms.
Claim 4
Dependent Claim
92 words
A compound of claim 1 in which (i) R 1 is a lower alkyl group substituted at the 3 position of an imidazo [1,2-b]pyridazine ring, or (ii) R 1 is a lower alkyl group having substituent(s) or a halogen atom, or (iii) X is SO or SO 2 , or (iv) Alk is a straight chain alkylene group containing 1-6 carbon atoms and having substituent(s), a straight chain alkylene group containing 7-10 carbon atoms and optionally having substituent(s) or a branched chain alkylene group containing 2-10 carbon atoms and optionally having substituent(s).
Claim 5
Dependent Claim
13 words
A compound of claim 1 in which R 1 is a hydrogen atom.
Claim 6
Dependent Claim
12 words
A compound of claim 1 in which X is an oxygen atom.
Claim 7
Dependent Claim
18 words
A compound of claim 1 in which Alk is a branched chain alkylene group having 2-6 carbon atoms.
Claim 8
Dependent Claim
16 words
A compound of claim 1 in which R 2 and R 3 are a hydrogen atom.
Claim 9
Dependent Claim
20 words
A compound of claim 1 in which Alk is a branched chain alkylene group having 4 or 5 carbon atoms.
Claim 10
Dependent Claim
31 words
A compound of claim 1 which is a compound of the formula: ##STR46## wherein Alk 1 is a straight or branched chain alkylene group containing 1-6 carbon atoms, or its salt.
Claim 11
Dependent Claim
38 words
A compound of claim 1 which is a compound of the formula: ##STR47## wherein Alk 2 is a branched chain alkylene group containing 2-6 carbon atoms and X 1 is an oxygen or sulfur atom, or its salt.
Claim 12
Dependent Claim
40 words
A compound of claim 1 which is a compound of the formula: ##STR48## wherein Alk 3 is a straight or branched chain alkylene group containing 3-5 carbon atoms, and X 1 is an oxygen or sulfur atom, or its salt.
Claim 13
Dependent Claim
30 words
A compound of claim 1 in which the lower alkyl group optionally having substituent(s) is an alkyl group containing 1-6 carbon atoms which is not substituted or substituted by hydroxy.
Claim 14
Dependent Claim
18 words
A compound of claim 1 in which the cycloalkyl group is a cycloalkyl group containing 3-6 carbon atoms.
Claim 15
Dependent Claim
34 words
A compound of claim 1 in which the phenyl group optionally having substituent(s) is a phenyl group which is not substituted or substituted by one to three of a halogen or a lower alkoxy.
Claim 16
Dependent Claim
18 words
A compound of claim 1 in which the heterocyclic ring is a 4 to 7 membered heterocyclic ring.
Claim 17
Dependent Claim
11 words
A compound of claim 1 which is 6-[(2,2-dimethyl-3-sulfamoylpropyl)oxy]imidazo[1,2-b]pyridazine or its salt.
Claim 18
Dependent Claim
12 words
A compound of claim 1 which is 6-[(2, -methyl-3-sulfamoylpropyl)thio]imidazo[1,2-b]pyridazine or its salt.
Claim 19
Dependent Claim
174 words
A method of treating asthma which comprises administering a therapeutically effective amount of a compound of the formula (I'): ##STR49## wherein R 1 is a hydrogen or halogen atom, or a lower alkyl group optionally having substituent(s) as defined in claim 1, R 2 and R 3 are, independently, a hydrogen atom, a lower alkyl group optionally having substituent(s) as defined in claim 1, a cycloalkyl group or a phenyl group optionally having substituent(s) as defined in claim 1 or R 2 and R 3 together with the adjacent nitrogen atom to which they bond may form a 4 to 7 membered heterocyclic ring having at least one nitrogen atom and optionally oxygen and/or sulfur atoms and optionally having substituent(s) as defined in claim 1, X is an oxygen atom or S(O) n (n=0 to 2), Alk is a straight or branched chain alkylene group containing 1-10 carbon atoms and optionally having substituent(s) as defined in claim 1, or its pharmaceutically acceptable salt, optionally together with a pharmaceutically acceptable carrier or diluent, to mammals.
Claim 20
Dependent Claim
16 words
A method of treating asthma according to claim 18, wherein the compound (I') is 6-(3-sulfamoylpropylthio) imidazo[1,2-b]pyridazine.
Claim 21
Dependent Claim
32 words
An antiasthmatic composition which comprises an effective anti-asthmatic amount of a compound of the formula (I) claimed in claim 1 or its pharmaceutically acceptable salt and a pharmaceutically acceptable carrier or diluent.
References Cited (Backward Citations)
GB1135893A
Cited
DE2820938A1
Cited
US4330543A
Cited
US4353903A
Cited
JPS5840489A
Cited
US4464372A
Cited
EP0164252A2
Cited
EP0185346A2
Cited
EP0203271A2
Cited
EP0225522A1
Cited
EP0238070A2
Cited
WO1989001478A1
Cited
EP0305093A1
Cited
US5145850A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1996-04-12 | 1996-10-12 | 1997-04-13 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2000-04-12 | 2000-10-12 | 2001-04-13 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2004-04-12 | 2004-10-12 | 2005-04-13 | $7700.00 | Window Closed / Lapsed |