US4667032A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Phenothiazone derivatives and analogs
Assignee: Merck Frosst Canada and Co
•
Filing: 1985-10-10
•
Granted: 1987-05-19
•
Expires: 2005-10-10
Abstract
Abstract Phenothiazone derivatives and analogs thereof, pharmaceutical compositions and methods of treatment are disclosed. These compounds are useful as inhibitors of mammalian leukotriene biosynthesis. As such, these compounds are useful therapeutic agents for treating allergic conditions, asthma, cardiovascular disorders and inflammation.
Inventors
- 👤 Cheuk K. Lau
- 👤 Christiane Yoakim
- 👤 Joshua Rokach
- 👤 Rejean Fortin
- 👤 Yvan Guindon
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-27 06:31
CPC Classifications
C; C07; C07D; C07D293/00; C07D293/10; A; A61; A61K; A61K31/00; A61K31/33; A61K31/395; A61K31/495; A61K31/535; A61K31/54; C07C; C07C46/00; C07C46/02; C07C46/06; C07D241/00; C07D241/36; C07D241/38; C07D241/46; C07D265/00; C07D265/28; C07D265/34; C07D265/38; C07D279/00; C07D279/10; C07D279/14; C07D279/18; C07D279/34; C07D279/36
Claims Analysis
Total Claims: 25
Claim 1
Independent Claim
620 words
The compounds of the Formula: ##STR63## wherein the substituents are: ______________________________________
Y R.sub.a R.sub.b R.sub.c
______________________________________
S H SCH.sub.3 H
S H H SCF.sub.3
S H H CHO
S H H COCF.sub.3
S H H H
S H H H
S H H H
S H H H
S H H H
S H H H
S H H Cl
S H H Cl
S H H Cl
S H H Cl
S H H Cl
S H Obenzyl Cl
S H OEt Cl
S H OEt Cl
S CH.sub.3 H Cl
S H CH.sub.3 Cl
S H OMe Br
S H OMe Cl
S H OEt Br
S H OEt Cl
S H OMe Cl
S H OMe H
O H OMe Br
O H OMe Cl
S H OMe Br
SO.sub.2
H H OH
SO.sub.2
H OMe OH
SO.sub.2
OMe OMe Me
SO.sub.2
H H OMe
SO.sub.2
H OMe OMe
S OCH.sub.3 OCH.sub.3 Me
S H H COCH.sub.3
S OCH.sub.3 H Br
S OCH.sub.3 Cl Cl
S OCH.sub.3 H Cl
S H
##STR64## H
S H
##STR65## Br
SO.sub.2
H OCH.sub.3 OH
SO.sub.2
NHPr H NHPr
SO.sub.2
##STR66## H
##STR67##
SO.sub.2
H OCH.sub.3
##STR68##
SO.sub.2
H OCH.sub.3 Br
S NHPr H NHPr
S NHPr H NHPr
S H NHPr NHPr
S H NHPr NHPr
S H OCH.sub.3 NH.sub.2
S H OCH.sub.3 NHPr
SO.sub.2
H OCH.sub.3 NHPr
O OCH.sub.3 H Cl
O OCH.sub.3 H Br
O NHPr H NHPr
SO.sub.2
H OCH.sub.3 CN
SO.sub.2
H OCH.sub.3 NHCH.sub.2 CO.sub.2 R
SO.sub.2
H OCH.sub.3 Sn-Bu
SO.sub.2
H OCH.sub.3 CH.sub.2 CO.sub.2 R
SO.sub.2
H OCH.sub.3 SO.sub.2 CH.sub.3
S H Sn-Bu H
S H H Sn-Bu
S H CH.sub.3 Sn-Bu
S H OMe Br
S H OMe Br
S H OMe Br
S H OMe Br
S H OMe Br
S H OMe Br
S H OMe Br
S H OMe Br
______________________________________
R.sub.d
R.sub.e R.sub.f R.sub.g
______________________________________
H H H H
H H H H
H H H H
H H H H
H SCH.sub.3 H H
H CO.sub.2 CH.sub.3
H H
H CO.sub.2 H H H
H CHO H H
H CONH.sub.2 H H
H CH.sub.2 OH H H
H Co.sub.2 Me H H
H CO.sub.2 H H H
H CHO H H
H COHN.sub.2 H H
H CH.sub.2 OH H H
H H H H
H F H H
H CH.sub.3 H H
H CH.sub.3 H H
H CH.sub.3 H H
H OMe H H
H OMe H H
H OEt H H
H OEt H H
H OEt H H
H SMe H H
H OMe H H
H OMe H H
H Me H H
H H H H
H OMe H H
H H H H
H H H H
H OMe H H
H H H H
H H H H
H OCH.sub.3 H H
H OCH.sub.3 H H
H OCH.sub.3 H H
H OCH.sub.3 H H
H OCH.sub.3 H H
H OCH.sub.3 H H
H H H H
H H H H
H OCH.sub.3 H H
H OCH.sub.3 H H
H H H H
H OCH.sub.3 H H
H H H H
H OCH.sub.3 H H
H OCH.sub.3 H H
H OCH.sub.3 H H
H OCH.sub.3 H H
H OCH.sub.3 H H
H OCH.sub.3 H H
H H H H
H OCH.sub.3 H H
H OCH.sub.3 H H
H OCH.sub.3 H H
H OCH.sub.3 H H
H OCH.sub.3 H H
H H H H
H H H H
H H H H
H CF.sub.3 H H
H F H H
H Cl H H
H Br H H
H NMe.sub.2 H H
H SMe H H
H SO.sub.2 Me H H
H Ph H H
and R is H or C.sub.2 to C.sub.4 alkyl.
______________________________________
Claim 2
Dependent Claim
620 words
The compounds of the Formula: ##STR63## wherein the substituents are: ______________________________________
Y R.sub.a R.sub.b R.sub.c
______________________________________
S H SCH.sub.3 H
S H H SCF.sub.3
S H H CHO
S H H COCF.sub.3
S H H H
S H H H
S H H H
S H H H
S H H H
S H H H
S H H Cl
S H H Cl
S H H Cl
S H H Cl
S H H Cl
S H Obenzyl Cl
S H OEt Cl
S H OEt Cl
S CH.sub.3 H Cl
S H CH.sub.3 Cl
S H OMe Br
S H OMe Cl
S H OEt Br
S H OEt Cl
S H OMe Cl
S H OMe H
O H OMe Br
O H OMe Cl
S H OMe Br
SO.sub.2
H H OH
SO.sub.2
H OMe OH
SO.sub.2
OMe OMe Me
SO.sub.2
H H OMe
SO.sub.2
H OMe OMe
S OCH.sub.3 OCH.sub.3 Me
S H H COCH.sub.3
S OCH.sub.3 H Br
S OCH.sub.3 Cl Cl
S OCH.sub.3 H Cl
S H
##STR64## H
S H
##STR65## Br
SO.sub.2
H OCH.sub.3 OH
SO.sub.2
NHPr H NHPr
SO.sub.2
##STR66## H
##STR67##
SO.sub.2
H OCH.sub.3
##STR68##
SO.sub.2
H OCH.sub.3 Br
S NHPr H NHPr
S NHPr H NHPr
S H NHPr NHPr
S H NHPr NHPr
S H OCH.sub.3 NH.sub.2
S H OCH.sub.3 NHPr
SO.sub.2
H OCH.sub.3 NHPr
O OCH.sub.3 H Cl
O OCH.sub.3 H Br
O NHPr H NHPr
SO.sub.2
H OCH.sub.3 CN
SO.sub.2
H OCH.sub.3 NHCH.sub.2 CO.sub.2 R
SO.sub.2
H OCH.sub.3 Sn-Bu
SO.sub.2
H OCH.sub.3 CH.sub.2 CO.sub.2 R
SO.sub.2
H OCH.sub.3 SO.sub.2 CH.sub.3
S H Sn-Bu H
S H H Sn-Bu
S H CH.sub.3 Sn-Bu
S H OMe Br
S H OMe Br
S H OMe Br
S H OMe Br
S H OMe Br
S H OMe Br
S H OMe Br
S H OMe Br
______________________________________
R.sub.d
R.sub.e R.sub.f R.sub.g
______________________________________
H H H H
H H H H
H H H H
H H H H
H SCH.sub.3 H H
H CO.sub.2 CH.sub.3
H H
H CO.sub.2 H H H
H CHO H H
H CONH.sub.2 H H
H CH.sub.2 OH H H
H Co.sub.2 Me H H
H CO.sub.2 H H H
H CHO H H
H COHN.sub.2 H H
H CH.sub.2 OH H H
H H H H
H F H H
H CH.sub.3 H H
H CH.sub.3 H H
H CH.sub.3 H H
H OMe H H
H OMe H H
H OEt H H
H OEt H H
H OEt H H
H SMe H H
H OMe H H
H OMe H H
H Me H H
H H H H
H OMe H H
H H H H
H H H H
H OMe H H
H H H H
H H H H
H OCH.sub.3 H H
H OCH.sub.3 H H
H OCH.sub.3 H H
H OCH.sub.3 H H
H OCH.sub.3 H H
H OCH.sub.3 H H
H H H H
H H H H
H OCH.sub.3 H H
H OCH.sub.3 H H
H H H H
H OCH.sub.3 H H
H H H H
H OCH.sub.3 H H
H OCH.sub.3 H H
H OCH.sub.3 H H
H OCH.sub.3 H H
H OCH.sub.3 H H
H OCH.sub.3 H H
H H H H
H OCH.sub.3 H H
H OCH.sub.3 H H
H OCH.sub.3 H H
H OCH.sub.3 H H
H OCH.sub.3 H H
H H H H
H H H H
H H H H
H CF.sub.3 H H
H F H H
H Cl H H
H Br H H
H NMe.sub.2 H H
H SMe H H
H SO.sub.2 Me H H
H Ph H H
and R is H or C.sub.2 to C.sub.4 alkyl.
______________________________________
Claim 3
Dependent Claim
60 words
A compound of claim 1 wherein the substituents are: ______________________________________
Y R.sub.a R.sub.b R.sub.c
R.sub.d
R.sub.e
R.sub.f
R.sub.g
______________________________________
S H OMe Br H OMe H H
S H OMe Cl H OMe H H
S H OEt Br H OEt H H
S H OEt Cl H OEt H H
S H OMe Cl H OEt H H.
______________________________________
Claim 4
Dependent Claim
44 words
A compound of claim 1 wherein the substituents are: ______________________________________
Y R.sub.a R.sub.b R.sub.c
R.sub.d
R.sub.e
R.sub.f
R.sub.g
______________________________________
S OCH.sub.3
H Br H OCH.sub.3
H H
S OCH.sub.3
Cl Cl H OCH.sub.3
H H
S OCH.sub.3
H Cl H OCH.sub.3
H H.
______________________________________
Claim 5
Dependent Claim
36 words
A compound of claim 1 wherein the substituents are: ______________________________________
Y R.sub.a R.sub.b R.sub.c
R.sub.d
R.sub.e
R.sub.f
R.sub.g
______________________________________
O H OMe Br H OMe H H
O H OMe Cl H OMe H H.
______________________________________
Claim 6
Dependent Claim
36 words
A compound of claim 1 wherein the substituents are: ______________________________________
Y R.sub.a R.sub.b R.sub.c
R.sub.d
R.sub.e
R.sub.f
R.sub.g
______________________________________
O OCH.sub.3
H Cl H OCH.sub.3
H H
O OCH.sub.3
H Br H OCH.sub.3
H H.
______________________________________
Claim 7
Dependent Claim
85 words
A compound of claim 1 wherein the substituents are: ______________________________________
Y R.sub.a R.sub.b R.sub.c
R.sub.d
R.sub.e
R.sub.f
R.sub.g
______________________________________
S H SCH.sub.3
H H H H H
S H H H H SCH.sub.3
H H
S H OMe H H SMe H H
S H S--n-Bu H H H H H
S H H S--n-Bu
H H H H
S H CH.sub.3 S--n-Bu
H H H H
S H OMe Br H SMe H H
S H OMe Br H SO.sub.2 Me
H H.
______________________________________
Claim 8
Dependent Claim
82 words
A compound of claim 1 wherein the substituents are: ______________________________________
Y R.sub.a
R.sub.b R.sub.c R.sub.d
R.sub.e
R.sub.f
R.sub.g
______________________________________
S H H H H CO.sub.2 CH.sub.3
H H
S H H H H CO.sub.2 H
H H
S H H H H CONH.sub.2
H H
S H H Cl H CO.sub.2 Me
H H
S H H Cl H CO.sub.2 H
H H
S H H Cl H CONH.sub.2
H H
SO.sub.2
H OCH.sub.3
CH.sub.2 CO.sub.2 R
H OCH.sub.3
H H.
______________________________________
Claim 9
Dependent Claim
52 words
A compound of claim 1 wherein the substituents are: __________________________________________________________________________
Y R.sub.a R.sub.b R.sub.c R.sub.d
R.sub.e
R.sub.f
R.sub.g
__________________________________________________________________________
S H
##STR69##
H H OCH.sub.3
H H
S H
##STR70##
Br H OCH.sub.3
H H
SO.sub.2
##STR71##
H
##STR72##
H H H H
SO.sub.2
H OCH.sub.3
##STR73##
H OCH.sub.3
H H.
__________________________________________________________________________
Claim 10
Dependent Claim
46 words
A compound of claim 1 wherein the substituents are: ______________________________________
Y R.sub.a
R.sub.b R.sub.c R.sub.d
R.sub.e
R.sub.f
R.sub.g
______________________________________
S H OCH.sub.3
NH.sub.2 H OCH.sub.3
H H
S H OCH.sub.3
NHPr H OCH.sub.3
H H
SO.sub.2
H OCH.sub.3
NHCH.sub.2 CO.sub.2 R
H OCH.sub.3
H H.
______________________________________
Claim 11
Dependent Claim
54 words
A compound of claim 1 wherein the substituents are: ______________________________________
Y R.sub.a
R.sub.b R.sub.c
R.sub.d
R.sub.e R.sub.f
R.sub.g
______________________________________
S H H H H CHO H H
S H H H H CH.sub.2 OH
H H
S H H Cl H CHO H H
S H H Cl H CH.sub.2 OH
H H.
______________________________________
Claim 12
Dependent Claim
60 words
A compound of claim 1 wherein the substituents are: ______________________________________
Y R.sub.a R.sub.b R.sub.c
R.sub.d
R.sub.e
R.sub.f
R.sub.g
______________________________________
S NHPr H NHPr H H H H
S NHPr H NHPr H OCH.sub.3
H H
S H NHPr NHPr H H H H
S H NHPr NHPr H OCH.sub.3
H H
O NHPr H NHPr H H H H.
______________________________________
Claim 13
Dependent Claim
92 words
A compound of claim 1 wherein the substituents are: ______________________________________
Y R.sub.a R.sub.b R.sub.c
R.sub.d
R.sub.e
R.sub.f
R.sub.g
______________________________________
S H OEt Cl H F H H
S H OEt Cl H CH.sub.3
H H
S H OMe Br H Me H H
S H OMe Br H CF.sub.3
H H
S H OMe Br H F H H
S H OMe Br H Cl H H
S H OMe Br H Br H H
S H OMe Br H NMe.sub.2
H H
S H OMe Br H Ph H H.
______________________________________
Claim 14
Dependent Claim
117 words
A compound of claim 1 wherein the substituents are: ______________________________________
Y R.sub.a R.sub.b R.sub.c
R.sub.d
R.sub.e
R.sub.f
R.sub.g
______________________________________
SO.sub.2
H H OH H H H H
SO.sub.2
H OMe OH H OMe H H
SO.sub.2
OMe OMe Me H H H H
SO.sub.2
H H OMe H H H H
SO.sub.2
H OMe OMe H OMe H H
SO.sub.2
H OCH.sub.3
OH H OCH.sub.3
H H
SO.sub.2
NHPr H NHPr H H H H
SO.sub.2
H OCH.sub.3
Br H OCH.sub.3
H H
SO.sub.2
H OCH.sub.3
NHPr H OCH.sub.3
H H
SO.sub.2
H OCH.sub.3
CN H OCH.sub.3
H H
SO.sub.2
H OCH.sub.3
S--n-Bu
H OCH.sub.3
H H
SO.sub.2
H OCH.sub.3
SO.sub.2 CH.sub.3
H OCH.sub.3
H H.
______________________________________
Claim 15
Dependent Claim
76 words
A compound of claim 1 wherein the substituents are: ______________________________________
Y R.sub.a R.sub.b R.sub.c R.sub.d
R.sub.e
R.sub.f
R.sub.g
______________________________________
S H H CHO H H H H
S H H COCF.sub.3
H H H H
S H C--benzyl Cl H H H H
S CH.sub.3
H Cl H CH.sub.3
H H
S H CH.sub.3 Cl H CH.sub.3
H H
S OCH.sub.3
OCH.sub.3 Me H H H H
S H H COCH.sub.3
H H H H.
______________________________________
Claim 16
Dependent Claim
8 words
The compound of claim 1 which is: 4-bromo-2,7-dimethoxy-3H-phenothiazin-3-one.
Claim 17
Dependent Claim
8 words
The compound of claim 1 which is: 4-chloro-2,7-dimethoxy-3H-phenothiazin-3-one.
Claim 18
Dependent Claim
8 words
The compound of claim 1 which is: 4-bromo-2,7-diethoxy-3H-phenothiazin-3-one.
Claim 19
Dependent Claim
8 words
The compound of claim 1 which is: 4-chloro-2,7-diethoxy-3H-phenothiazin-3-one.
Claim 20
Dependent Claim
8 words
The compound of claim 1 which is: 4-bromo-2,7-dimethoxy-3H-phenoxazin-3-one.
Claim 21
Dependent Claim
8 words
The compound of claim 1 which is: 4-chloro-2,7-dimethoxy-3H-phenoxazin-3-one.
Claim 22
Dependent Claim
37 words
The compounds of the formula: ##STR74## wherein the substituents are: ______________________________________
R.sub.a R.sub.b R.sub.c R.sub.d
______________________________________
t-Bu t-Bu H H
t-Bu t-Bu F H
t-Bu t-Bu Me H
t-Bu t-Bu SMe H
t-Bu t-Bu H OMe.
______________________________________
Claim 23
Dependent Claim
37 words
The compounds of the formula: ##STR74## wherein the substituents are: ______________________________________
R.sub.a R.sub.b R.sub.c R.sub.d
______________________________________
t-Bu t-Bu H H
t-Bu t-Bu F H
t-Bu t-Bu Me H
t-Bu t-Bu SMe H
t-Bu t-Bu H OMe.
______________________________________
Claim 24
Dependent Claim
5 words
The compounds: 2-S-glutathionyl-3H-phenothiazin-3-one; and 4-chloro-2-S-glutathionyl-phenothiazin-3-one.
Claim 25
Dependent Claim
5 words
The compounds: 2-S-glutathionyl-3H-phenothiazin-3-one; and 4-chloro-2-S-glutathionyl-phenothiazin-3-one.
References Cited (Backward Citations)
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US3598123A
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US3630200A
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US3845770A
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1990-05-18 | 1990-11-17 | 1991-05-19 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1994-05-18 | 1994-11-17 | 1995-05-19 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1998-05-18 | 1998-11-17 | 1999-05-19 | $7700.00 | Window Closed / Lapsed |