US4666907A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Phenothiazine and derivatives and analogs and use as leukotriene biosynthesis inhibitors
Assignee: Merck Frosst Canada and Co
•
Filing: 1986-09-26
•
Granted: 1987-05-19
•
Expires: 2006-09-26
Abstract
Abstract Phenothiazine derivatives and analogs thereof having the Formula I are useful as inhibitors of the biosynthesis of mammalian leukotrienes. As such, these compounds are useful therapeutic agents for treating allergic conditions, asthma, cardiovascular disorders and inflammation, and are useful as cytoprotective agents. ##STR1##
Inventors
- 👤 Rejean Fortin
- 👤 Cheuk K. Lau
- 👤 Yvan Guindon
- 👤 Joshua Rokach
- 👤 Christiane Yoakim
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 03:24
CPC Classifications
C; C07; C07D; C07D265/00; C07D265/28; C07D265/34; C07D265/38; C07D279/00; C07D279/10; C07D279/14; C07D279/18; C07D279/20; C07D279/22; C07D279/30; C07D279/34; C07D293/00; C07D293/10
Claims Analysis
Total Claims: 22
Claim 1
Independent Claim
1094 words
The compounds having the Formula: ##STR87## wherein the substituents are: ______________________________________
Compound X R.sup.1 R.sup.2
R.sup.3
______________________________________
3 S Me 4-Cl H
8 S Ac 4-Cl H
9 S Ac 4-Cl H
27 S Ac H 4-Cl
28 S Ac H 4-Cl
29 S Me H 4-Cl
30 S H H 2-OEt
32 SO.sub.2
H H H
33 SO.sub.2
H H 4-Cl
34 SO.sub.2
H H 4-Cl
39 S H 1-OMe 2-OMe
40 S H 1-OMe 2-OMe
41 SO.sub.2
H 1-OMe 2-OMe
43 S H 1-OH 2-C(Me).sub.3
49 SO H 1-OMe 2-OMe
50 SO H 1-OMe 2-OMe
51 SO.sub.2
H 1-OMe 2-OMe
52 S H 2-OMe 3-OH
53 S H 2-OMe 3-OH
54 S H 2-OMe 3-OAc
55 S H 2-OMe 3-OAc
56 SO.sub.2
H 2-OMe 3-OH
58 SO.sub.2
H 2-OMe 3-OAc
59 O Ac 2-OMe 3-OH
60 O Ac 2-OMe 3-OAc
61 O CO.sub.2 CH(Me)OAc
2-OMe 3-OH
62 O CO.sub.2 CH(Me)OAc
2-OMe 3-OAc
63 S H 2-OMe 3-OH
64 S H 2-OMe 3-OAc
65 S H 2-OMe 3-OH
66 S H 2-OMe 3-OAc
67 SO H 2-OMe 3-OAc
68 SO.sub.2
H 2-OMe 3-OH
69 SO.sub.2
H 2-OMe 3-OAc
70 S Ac 2-OMe 4-Br
71 S Ac 2-OMe 4-Cl
72 S Ac 2-OMe 4-F
73 S Ac 2-OMe 4-I
74 S Ac 2-OMe 4-CF.sub.3
75 S Ac 2-OMe 4-CN
76 S Ac 2-OEt 4-Br
77 S Ac 2-OEt 4-Cl
78 S Ac 2-OMe 4-Br
79 S Ac 2-OMe 4-Cl
80 S Ac 2-OMe 4-F
81 S Ac 2-OEt 4-Br
82 S Ac 2-OEt 4-Cl
83 S Ac 2-OEt 4-F
84 S Ac 2-OEt 4-CF.sub.3
85 S H 2-OMe 4-Br
86 S H 2-OMe 4-Cl
87 S H 2-OMe 4-F
88 S H 2-OMe 4-CF.sub.3
89 S H 2-OMe 4-Br
90 S H 2-OMe 4-Br
91 S H 2-OMe 4-Br
92 S H 2-OMe 4-Br
93 S Ac 2-OMe 4-Br
94 S Ac 2-OMe 4-Br
95 S Ac 2-OMe 4-Br
96 S Ac 2-OMe 4-Cl
97 S CH.sub.2 OAc 2-OMe 4-Br
98 S CH.sub.2 OAc 2-OMe 4-Cl
99 S CH.sub.2 OAc 2-OMe 4-Br
100 S CH.sub.2 OAc 2-OMe 4-Br
101 S CH.sub.2 OAc 2-OMe 4-Br
102 S CH.sub.3 2-OMe 4-Br
103 S CH.sub.3 2-OMe 4-Br
104 S CH.sub.3 2-OMe 4-Cl
105 S Me 2-OMe 4-F
106 S Me 2-OMe 4-CF.sub.3
107 S CH(Me)OAc 2-OMe 4-Br
108 S CH(Me)OCOC(Me).sub.3
2-OMe 4-Br
109 S CH(Me)OAc 2-OMe 4-Cl
110 S CH(Me)OAc 2-OMe 4-F
111 S CH(Me)OAc 2-OMe 4-CF.sub.3
112 S H 2-OMe 4-Br
113 S H 2-OMe 4-Br
114 S H 2-OMe 4-Br
115 S H 2-OMe 4-Cl
116 S CO.sub.2 Me 2-OMe 4-Br
117 S CO.sub.2 Et 2-OMe 4-Br
118 S CO.sub.2 CH(Me)OAc
2-OMe 4-Br
119 S CO.sub.2 CH(Me)OAc
2-OMe 4-Cl
120 S CO.sub.2 CH(Me)OAc
2-OMe 4-F
121 S CO.sub.2 CH(Me)OAc
2-OMe 4-Br
122 S CO.sub.2 CH(Me)OAc
2-OMe 4-Br
123 S Ac 2-OMe 4-Br
124 S Ac 2-OMe 4-Cl
125 S Me 2-OMe 4-Br
126 S H 2-OMe 4-Br
127 S CH(Me)OAc 4-Cl H
128 SO.sub.2
Ac 4-Cl H
129 SO.sub.2
Ac 4-Cl H
130 S Ac 2-OEt 4-Cl
131 S Ac 2-OEt 4-Cl
132 S Ac 2-OMe 4-Br
133 S Ac 2-OMe 4-Br
134 SO.sub.2
Ac 2-OMe 4-Br
135 SO.sub.2
Ac 2-OMe 4-Br
136 SO.sub.2
CO.sub.2 CH(Me)OAc
2-OMe 4-Br
137 S
##STR88## H 4-Br
138 S H 2-OMe 4-I
139 S H 2-OMe 4-CN
140 S H 2-OEt 4-Br
141 S H 2-OEt 4-Cl
142 S H 2-OMe 4-Br
143 S H 2-OMe 4-Cl
144 S H 2-OMe 4-F
145 S H 2-OEt 4-Br
146 S H 2-OEt 4-Cl
147 S H 2-OEt 4-F
148 S H 2-OEt 4-CF.sub.3
149 S H 2-Cl 3-Ac
150 S H 2-OMe H
151 SO H 2-OMe H
______________________________________
Compound R.sup.4 R.sup.5 T
______________________________________
3 H H 3-OMe
8 H H 3-OAc
9 H H 3-OH
27 7-F H 3-OMe
28 7-F H 3-OH
29 7-F H 3-OMe
30 4-Cl H 3-OH
32 H H 3-OAc
33 H H 3-OAc
34 H H 3-OH
39 4-Me H 3-OH
40 4-Me H 3-OAc
41 4-Me H 3-OH
43 H 4-C(Me).sub.3 H
49 4-Me H 3-OH
50 4-Me H 3-OAc
51 4-Me H 3-OAc
52 4-Br 7-OMe H
53 4-Cl 7-OMe H
54 4-Br 7-OMe H
55 4-Cl 7-OMe H
56 4-Br 7-OMe H
58 4-Br 7-OMe H
59 4-Br 7-OMe H
60 4-Br 7-OMe H
61 4-Br 7-OMe H
62 4-Br 7-OMe H
63 4-Br 7-Me H
64 4-Br 7-Me H
65 4-Br 7-F H
66 4-Br 7-F H
67 4-Br 7-OMe H
68 H 7-OMe H
69 H 7-OMe H
70 7-OMe H 3-OAc
71 7-OMe H 3-OAc
72 7-OMe H 3-OAc
73 7-OMe H 3-OAc
74 7-OMe H 3-OAc
75 7-OMe H 3-OAc
76 7-OEt H 3-OAc
77 7-OEt H 3-OAc
78 7-OEt H 3-OAc
79 7-OEt H 3-OAc
80 7-OEt H 3-OAc
81 7-OMe H 3-OAc
82 7-OMe H 3-OAc
83 7-OMe H 3-OAc
84 7-OMe H 3-OAc
85 7-OMe H 3-OH
86 7-OMe H 3-OH
87 7-OMe H 3-OH
88 7-OMe H 3-OH
89 7-OMe H 3-OAc
90 7-OMe H 3-OBz
91 7-OMe H 3-OCOCHMe.sub.2
92 7-OMe 3-OCH.sub.2 CO.sub.2 H
H
93 7-OMe H 3-OBz
94 7-OMe H 3-OMe
95 7-OMe 3-OCH.sub.2 CO.sub.2 H
H
96 7-OMe 3-OCH.sub.2 CO.sub.2 H
H
97 7-OMe H 3-OH
98 7-OMe H 3-OH
99 7-OMe H 3-OAc
100 7-OMe H 3-OBz
101 7-OMe H 3-OMe
102 7-OMe H 3-OH
103 7-OMe H 3-OAc
104 7-OMe H 3-OH
105 7-OMe H 3-OH
106 7-OMe H 3-OH
107 7-OMe H 3-OH
108 7-OMe H 3-OH
109 7-OMe H 3-OH
110 7-OMe H 3-OH
111 7-OMe H 3-OH
112 7-OMe 3-OCO.sub.2 Me H
113 7-OMe 3-OCO.sub.2 Et H
114 7-OMe 3-OCO.sub.2 CH(Me)OAc
H
115 7-OMe 3-OCO.sub.2 CH(Me)OAC
H
116 7-OMe H 3-OH
117 7-OMe H 3-OH
118 7-OMe H 3-OH
119 7-OMe H 3-OH
120 7-OMe H 3-OH
121 7-OMe H 3-OAc
122 7-OMe 3-OCO.sub.2 CH(Me)OAc
H
123 7-OMe H 3-OH
124 7-OMe H 3-OH
125 7-OMe H 3-OMe
126 7-OMe H 3-OMe
127 H H 3-OAc
128 H H 3-OH
129 H H 3-OAc
130 H H 3-OH
131 H H 3-OAc
132 7-OH H 3-OH
133 7-OAc H 3-OH
134 7-OMe H 3-OH
135 7-OMe H 3-OAc
136 7-OMe H 3-OH
137 7-OMe 2-OMe 3-OH
138 7-OMe H 3-OH
139 7-OMe H 3-OH
140 7-OEt H 3-OH
141 7-OEt H 3-OH
142 7-OEt H 3-OH
143 7-OEt H 3-OH
144 7-OEt H 3-OH
145 7-OMe H 3-OH
146 7-OMe H 3-OH
147 7-OMe H 3-OH
148 7-OMe H 3-OH
149 7-Ac H H
150 7-OMe H 3-OAc
151 7-OMe H 3-OAc
______________________________________
Claim 2
Dependent Claim
1094 words
The compounds having the Formula: ##STR87## wherein the substituents are: ______________________________________
Compound X R.sup.1 R.sup.2
R.sup.3
______________________________________
3 S Me 4-Cl H
8 S Ac 4-Cl H
9 S Ac 4-Cl H
27 S Ac H 4-Cl
28 S Ac H 4-Cl
29 S Me H 4-Cl
30 S H H 2-OEt
32 SO.sub.2
H H H
33 SO.sub.2
H H 4-Cl
34 SO.sub.2
H H 4-Cl
39 S H 1-OMe 2-OMe
40 S H 1-OMe 2-OMe
41 SO.sub.2
H 1-OMe 2-OMe
43 S H 1-OH 2-C(Me).sub.3
49 SO H 1-OMe 2-OMe
50 SO H 1-OMe 2-OMe
51 SO.sub.2
H 1-OMe 2-OMe
52 S H 2-OMe 3-OH
53 S H 2-OMe 3-OH
54 S H 2-OMe 3-OAc
55 S H 2-OMe 3-OAc
56 SO.sub.2
H 2-OMe 3-OH
58 SO.sub.2
H 2-OMe 3-OAc
59 O Ac 2-OMe 3-OH
60 O Ac 2-OMe 3-OAc
61 O CO.sub.2 CH(Me)OAc
2-OMe 3-OH
62 O CO.sub.2 CH(Me)OAc
2-OMe 3-OAc
63 S H 2-OMe 3-OH
64 S H 2-OMe 3-OAc
65 S H 2-OMe 3-OH
66 S H 2-OMe 3-OAc
67 SO H 2-OMe 3-OAc
68 SO.sub.2
H 2-OMe 3-OH
69 SO.sub.2
H 2-OMe 3-OAc
70 S Ac 2-OMe 4-Br
71 S Ac 2-OMe 4-Cl
72 S Ac 2-OMe 4-F
73 S Ac 2-OMe 4-I
74 S Ac 2-OMe 4-CF.sub.3
75 S Ac 2-OMe 4-CN
76 S Ac 2-OEt 4-Br
77 S Ac 2-OEt 4-Cl
78 S Ac 2-OMe 4-Br
79 S Ac 2-OMe 4-Cl
80 S Ac 2-OMe 4-F
81 S Ac 2-OEt 4-Br
82 S Ac 2-OEt 4-Cl
83 S Ac 2-OEt 4-F
84 S Ac 2-OEt 4-CF.sub.3
85 S H 2-OMe 4-Br
86 S H 2-OMe 4-Cl
87 S H 2-OMe 4-F
88 S H 2-OMe 4-CF.sub.3
89 S H 2-OMe 4-Br
90 S H 2-OMe 4-Br
91 S H 2-OMe 4-Br
92 S H 2-OMe 4-Br
93 S Ac 2-OMe 4-Br
94 S Ac 2-OMe 4-Br
95 S Ac 2-OMe 4-Br
96 S Ac 2-OMe 4-Cl
97 S CH.sub.2 OAc 2-OMe 4-Br
98 S CH.sub.2 OAc 2-OMe 4-Cl
99 S CH.sub.2 OAc 2-OMe 4-Br
100 S CH.sub.2 OAc 2-OMe 4-Br
101 S CH.sub.2 OAc 2-OMe 4-Br
102 S CH.sub.3 2-OMe 4-Br
103 S CH.sub.3 2-OMe 4-Br
104 S CH.sub.3 2-OMe 4-Cl
105 S Me 2-OMe 4-F
106 S Me 2-OMe 4-CF.sub.3
107 S CH(Me)OAc 2-OMe 4-Br
108 S CH(Me)OCOC(Me).sub.3
2-OMe 4-Br
109 S CH(Me)OAc 2-OMe 4-Cl
110 S CH(Me)OAc 2-OMe 4-F
111 S CH(Me)OAc 2-OMe 4-CF.sub.3
112 S H 2-OMe 4-Br
113 S H 2-OMe 4-Br
114 S H 2-OMe 4-Br
115 S H 2-OMe 4-Cl
116 S CO.sub.2 Me 2-OMe 4-Br
117 S CO.sub.2 Et 2-OMe 4-Br
118 S CO.sub.2 CH(Me)OAc
2-OMe 4-Br
119 S CO.sub.2 CH(Me)OAc
2-OMe 4-Cl
120 S CO.sub.2 CH(Me)OAc
2-OMe 4-F
121 S CO.sub.2 CH(Me)OAc
2-OMe 4-Br
122 S CO.sub.2 CH(Me)OAc
2-OMe 4-Br
123 S Ac 2-OMe 4-Br
124 S Ac 2-OMe 4-Cl
125 S Me 2-OMe 4-Br
126 S H 2-OMe 4-Br
127 S CH(Me)OAc 4-Cl H
128 SO.sub.2
Ac 4-Cl H
129 SO.sub.2
Ac 4-Cl H
130 S Ac 2-OEt 4-Cl
131 S Ac 2-OEt 4-Cl
132 S Ac 2-OMe 4-Br
133 S Ac 2-OMe 4-Br
134 SO.sub.2
Ac 2-OMe 4-Br
135 SO.sub.2
Ac 2-OMe 4-Br
136 SO.sub.2
CO.sub.2 CH(Me)OAc
2-OMe 4-Br
137 S
##STR88## H 4-Br
138 S H 2-OMe 4-I
139 S H 2-OMe 4-CN
140 S H 2-OEt 4-Br
141 S H 2-OEt 4-Cl
142 S H 2-OMe 4-Br
143 S H 2-OMe 4-Cl
144 S H 2-OMe 4-F
145 S H 2-OEt 4-Br
146 S H 2-OEt 4-Cl
147 S H 2-OEt 4-F
148 S H 2-OEt 4-CF.sub.3
149 S H 2-Cl 3-Ac
150 S H 2-OMe H
151 SO H 2-OMe H
______________________________________
Compound R.sup.4 R.sup.5 T
______________________________________
3 H H 3-OMe
8 H H 3-OAc
9 H H 3-OH
27 7-F H 3-OMe
28 7-F H 3-OH
29 7-F H 3-OMe
30 4-Cl H 3-OH
32 H H 3-OAc
33 H H 3-OAc
34 H H 3-OH
39 4-Me H 3-OH
40 4-Me H 3-OAc
41 4-Me H 3-OH
43 H 4-C(Me).sub.3 H
49 4-Me H 3-OH
50 4-Me H 3-OAc
51 4-Me H 3-OAc
52 4-Br 7-OMe H
53 4-Cl 7-OMe H
54 4-Br 7-OMe H
55 4-Cl 7-OMe H
56 4-Br 7-OMe H
58 4-Br 7-OMe H
59 4-Br 7-OMe H
60 4-Br 7-OMe H
61 4-Br 7-OMe H
62 4-Br 7-OMe H
63 4-Br 7-Me H
64 4-Br 7-Me H
65 4-Br 7-F H
66 4-Br 7-F H
67 4-Br 7-OMe H
68 H 7-OMe H
69 H 7-OMe H
70 7-OMe H 3-OAc
71 7-OMe H 3-OAc
72 7-OMe H 3-OAc
73 7-OMe H 3-OAc
74 7-OMe H 3-OAc
75 7-OMe H 3-OAc
76 7-OEt H 3-OAc
77 7-OEt H 3-OAc
78 7-OEt H 3-OAc
79 7-OEt H 3-OAc
80 7-OEt H 3-OAc
81 7-OMe H 3-OAc
82 7-OMe H 3-OAc
83 7-OMe H 3-OAc
84 7-OMe H 3-OAc
85 7-OMe H 3-OH
86 7-OMe H 3-OH
87 7-OMe H 3-OH
88 7-OMe H 3-OH
89 7-OMe H 3-OAc
90 7-OMe H 3-OBz
91 7-OMe H 3-OCOCHMe.sub.2
92 7-OMe 3-OCH.sub.2 CO.sub.2 H
H
93 7-OMe H 3-OBz
94 7-OMe H 3-OMe
95 7-OMe 3-OCH.sub.2 CO.sub.2 H
H
96 7-OMe 3-OCH.sub.2 CO.sub.2 H
H
97 7-OMe H 3-OH
98 7-OMe H 3-OH
99 7-OMe H 3-OAc
100 7-OMe H 3-OBz
101 7-OMe H 3-OMe
102 7-OMe H 3-OH
103 7-OMe H 3-OAc
104 7-OMe H 3-OH
105 7-OMe H 3-OH
106 7-OMe H 3-OH
107 7-OMe H 3-OH
108 7-OMe H 3-OH
109 7-OMe H 3-OH
110 7-OMe H 3-OH
111 7-OMe H 3-OH
112 7-OMe 3-OCO.sub.2 Me H
113 7-OMe 3-OCO.sub.2 Et H
114 7-OMe 3-OCO.sub.2 CH(Me)OAc
H
115 7-OMe 3-OCO.sub.2 CH(Me)OAC
H
116 7-OMe H 3-OH
117 7-OMe H 3-OH
118 7-OMe H 3-OH
119 7-OMe H 3-OH
120 7-OMe H 3-OH
121 7-OMe H 3-OAc
122 7-OMe 3-OCO.sub.2 CH(Me)OAc
H
123 7-OMe H 3-OH
124 7-OMe H 3-OH
125 7-OMe H 3-OMe
126 7-OMe H 3-OMe
127 H H 3-OAc
128 H H 3-OH
129 H H 3-OAc
130 H H 3-OH
131 H H 3-OAc
132 7-OH H 3-OH
133 7-OAc H 3-OH
134 7-OMe H 3-OH
135 7-OMe H 3-OAc
136 7-OMe H 3-OH
137 7-OMe 2-OMe 3-OH
138 7-OMe H 3-OH
139 7-OMe H 3-OH
140 7-OEt H 3-OH
141 7-OEt H 3-OH
142 7-OEt H 3-OH
143 7-OEt H 3-OH
144 7-OEt H 3-OH
145 7-OMe H 3-OH
146 7-OMe H 3-OH
147 7-OMe H 3-OH
148 7-OMe H 3-OH
149 7-Ac H H
150 7-OMe H 3-OAc
151 7-OMe H 3-OAc
______________________________________
Claim 3
Dependent Claim
250 words
The following compounds of Formula I of claim 1: __________________________________________________________________________
Compound
X R.sup.1 R.sup.2
R.sup.3
R.sup.4
R.sup.5 T
__________________________________________________________________________
3 S Me 4-Cl
H H H 3-OMe
8 S Ac 4-Cl
H H H 3-OAc
9 S Ac 4-Cl
H H H 3-OH
32 SO.sub.2
H H H H H 3-OAc
33 SO.sub.2
H H 4-Cl
H H 3-OAc
34 SO.sub.2
H H 4-Cl
H H 3-OH
41 SO.sub.2
H 1-OMe
2-OMe
4-Me
H 3-OH
59 O Ac 2-OMe
3-OH
4-Br
7-OMe H
60 O Ac 2-OMe
3-OAc
4-Br
7-OMe H
61 O CO.sub.2 CH(Me)OAc
2-OMe
3-OH
4-Br
7-OMe H
70 S Ac 2-OMe
4-Br
7-OMe
H 3-OAc
71 S Ac 2-OMe
4-Cl
7-OMe
H 3-OAc
114 S H 2-OMe
4-Br
7-OMe
3-OCO.sub.2 CH(Me)OAc
H
118 S CO.sub.2 CH(Me)OAc
2-OMe
4-Br
7-OMe
H 3-OH
119 S CO.sub.2 CH(Me)OAc
2-OMe
4-Cl
7-OMe
H 3-OH
121 S CO.sub.2 CH(Me)OAc
2-OMe
4-Br
7-OMe
H 3-OAc
123 S Ac 2-OMe
4-Br
7-OMe
H 3-OH
127 S CH(Me)OAc
4-Cl
H H H 3-OAc
128 SO.sub.2
Ac 4-Cl
H H H 3-OH
129 SO.sub.2
Ac 4-Cl
H H H 3-OAc
130 S Ac 2-OEt
4-Cl
H H 3-OH
131 S Ac 2-OEt
4-Cl
H H 3-OAc
132 S Ac 2-OMe
4-Br
7-OH
H 3-OH
133 S Ac 2-OMe
4-Br
7-OAc
H 3-OH
134 SO.sub.2
Ac 2-OMe
4-Br
7-OMe
H 3-OH
135 SO.sub.2
Ac 2-OMe
4-Br
7-OMe
H 3-OAc
136 SO.sub.2
CO.sub.2 CH(Me)OAc
2-OMe
4-Br
7-OMe
H 3-OH
137 S
##STR89##
H 4-Br
7-OMe
2-OMe 3-OH
__________________________________________________________________________
Claim 4
Dependent Claim
79 words
The following compounds of Formula I of claim 2: __________________________________________________________________________
Compound
X R.sup.1 R.sup.2
R.sup.3
R.sup.4
R.sup.5
T
__________________________________________________________________________
70 S Ac 2-OMe
4-Br
7-OMe
H 3-OAc
71 S Ac 2-OMe
4-Cl
7-OMe
H 3-OAc
118 S CO.sub.2 CH(Me)OAc
2-OMe
4-Br
7-OMe
H 3-OH
119 S CO.sub.2 CH(Me)OAc
2-OMe
4-Cl
7-OMe
H 3-OH
121 S CO.sub.2 CH(Me)OAc
2-OMe
4-Br
7-OMe
H 3-OAc
123 S Ac 2-OMe
4-Br
7-OMe
H 3-OH
137 S
##STR90##
H 4-Br
7-OMe
2-OMe
3-OH
__________________________________________________________________________
Claim 5
Dependent Claim
121 words
Compounds according to claim 1 having the formula: ______________________________________
##STR91##
R.sup.1 R.sup.2 R.sup.3
______________________________________
H Br OH
H Cl OH
H F OH
H CF.sub.3 OH
H Br OAc
H Br OCOPh
H Br OCOCHMe.sub.2
H Br OCH.sub.2 CO.sub.2 H
Ac Br OAc
Ac Cl OAc
Ac Br OCOPh
Ac Br OMe
Ac Br OCH.sub.2 CO.sub.2 H
Ac Cl OCH.sub.2 CO.sub.2 H
CH.sub.2 OAc Br OH
CH.sub.2 OAc Cl OH
CH.sub.2 OAc Br OAc
CH.sub.2 OAc Br OCOPh
CH.sub.2 OAc Br OMe
CH.sub.3 Br OH
CH.sub.3 Br OAc
CH.sub.3 Cl OH
CH.sub.3 F OH
CH.sub.3 CF.sub.3 OH
CH(CH.sub.3)OAc Br OH
CH(CH.sub.3)OCOC(CH.sub.3).sub.3
Br OH
CH(CH.sub.3)OAc Cl OH
CH(CH.sub.3)OAc F OH
CH(CH.sub.3)OAc CF.sub.3 OH
CO.sub.2 CH(Me)OAc Br OH
CO.sub.2 CH(Me)OAc Br OAc
______________________________________
Claim 6
Dependent Claim
60 words
Compounds according to claim 1 having the formula: ______________________________________
##STR92##
R.sup.2 R.sup.3 R.sup.5
______________________________________
Br OMe OMe
Cl OMe OMe
F OMe OMe
I OMe OMe
CF.sub.3 OMe OMe
CN OMe OMe
Br OEt OEt
Cl OEt OEt
Br OMe OEt
Cl OMe OEt
F OMe OEt
Br OEt OMe
Cl OEt OMe
F OEt OMe
CF.sub.3 OEt OMe
______________________________________
Claim 7
Dependent Claim
5 words
3-acetoxy-10-acetyl-4-bromo-2,7-dimethoxy-10H-phenothiazine, according to claim 1.
Claim 8
Dependent Claim
5 words
10-(1-acetoxyethoxycarbonyl)-4-bromo-2,7-dimethoxy-3-hydroxy-10H-phenothiazine, according to claim 1.
Claim 9
Dependent Claim
5 words
3-Acetoxy-10-acetyl-4-chloro-2,7-dimethoxy-10H-phenothiazine, according to claim 1.
Claim 10
Dependent Claim
5 words
4-Bromo-2,7-dimethoxy-3-hydroxy-10-(1-pivaloyloxyethoxycarbonyl)-10H-phenothiazine, according to claim 1.
Claim 11
Dependent Claim
5 words
3-Hydroxy-10-(1-acetoxyethoxycarbonyl)-4-chloro-2,7-dimethoxy-10H-phenothiazine, according to claim 1.
Claim 12
Dependent Claim
5 words
3-Acetoxy-10-(1-acetoxyethoxycarbonyl)-4-bromo-2,7-dimethoxy-10H-phenothiazine, according to claim 1.
Claim 13
Dependent Claim
5 words
3-Hydroxy-10-acetyl-4-bromo-2,7-dimethoxy-10H-phenothiazine, according to claim 1.
Claim 14
Dependent Claim
25 words
A pharmaceutical composition for inhibiting leukotriene biosynthesis or action in mammals containing a pharmaceutical carrier and an effective amount of a compound of claim 1.
Claim 15
Dependent Claim
250 words
A composition of claim 13 wherein the compound is: __________________________________________________________________________
Compound
X R.sup.1 R.sup.2
R.sup.3
R.sup.4
R.sup.5 T
__________________________________________________________________________
3 S Me 4-Cl
H H H 3-OMe
8 S Ac 4-Cl
H H H 3-OAc
9 S Ac 4-Cl
H H H 3-OH
32 SO.sub.2
H H H H H 3-OAc
33 SO.sub.2
H H 4-Cl
H H 3-OAc
34 SO.sub.2
H H 4-Cl
H H 3-OH
41 SO.sub.2
H 1-OMe
2-OMe
4-Me
H 3-OH
59 O Ac 2-OMe
3-OH
4-Br
7-OMe H
60 O Ac 2-OMe
3-OAc
4-Br
7-OMe H
61 O CO.sub.2 CH(Me)OAc
2-OMe
3-OH
4-Br
7-OMe H
70 S Ac 2-OMe
4-Br
7-OMe
H 3-OAc
71 S Ac 2-OMe
4-Cl
7-OMe
H 3-OAc
114 S H 2-OMe
4-Br
7-OMe
3-OCO.sub.2 CH(Me)OAc
H
118 S CO.sub.2 CH(Me)OAc
2-OMe
4-Br
7-OMe
H 3-OH
119 S CO.sub.2 CH(Me)OAc
2-OMe
4-Cl
7-OMe
H 3-OH
121 S CO.sub.2 CH(Me)OAc
2-OMe
4-Br
7-OMe
H 3-OAc
123 S Ac 2-OMe
4-Br
7-OMe
H 3-OH
127 S CH(Me)OAc
4-Cl
H H H 3-OAc
128 SO.sub.2
Ac 4-Cl
H H H 3-OH
129 SO.sub.2
Ac 4-Cl
H H H 3-OAc
130 S Ac 2-OEt
4-Cl
H H 3-OH
131 S Ac 2-OEt
4-Cl
H H 3-OAc
132 S Ac 2-OMe
4-Br
7-OH
H 3-OH
133 S Ac 2-OMe
4-Br
7-OAc
H 3-OH
134 SO.sub.2
Ac 2-OMe
4-Br
7-OMe
H 3-OH
135 SO.sub.2
Ac 2-OMe
4-Br
7-OMe
H 3-OAc
136 SO.sub.2
CO.sub.2 CH(Me)OAc
2-OMe
4-Br
7-OMe
H 3-OH
137 S
##STR93##
H 4-Br
7-OMe
2-OMe 3-OH
__________________________________________________________________________
Claim 16
Dependent Claim
67 words
A composition of claim 13 wherein the compound is: ______________________________________
70 S Ac 2-OMe 4-Br 7-OMe H 3-OAc
71 S Ac 2-OMe 4-Cl 7-OMe H 3-OAc
118 S CO.sub.2 CH(Me)OAc
2-OMe 4-Br 7-OMe H 3-OH
119 S CO.sub.2 CH(Me)OAc
2-OMe 4-Cl 7-OMe H 3-OH
121 S CO.sub.2 CH(Me)OAc
2-OMe 4-Br 7-OMe H 3-OAc
123 S Ac 2-OMe 4-Br 7-OMe H 3-OH
##STR94## H4-Br 7-OMe 2-OMe 3-OH
______________________________________
Claim 17
Dependent Claim
125 words
A composition of claim 13 wherein the compound is of the formula: ______________________________________
##STR95##
R.sup.1 R.sup.2 R.sup.3
______________________________________
H Br OH
H Cl OH
H F OH
H CF.sub.3 OH
H Br OAc
H Br OCOPh
H Br OCOCHMe.sub.2
H Br OCH.sub.2 CO.sub.2 H
Ac Br OAc
Ac Cl OAc
Ac Br OCOPh
Ac Br OMe
Ac Br OCH.sub.2 CO.sub.2 H
Ac Cl OCH.sub.2 CO.sub.2 H
CH.sub.2 OAc Br OH
CH.sub.2 OAc Cl OH
CH.sub.2 OAc Br OAc
CH.sub.2 OAc Br OCOPh
CH.sub.2 OAc Br OMe
CH.sub.3 Br OH
CH.sub.3 Br OAc
CH.sub.3 Cl OH
CH.sub.3 F OH
CH.sub.3 CF.sub.3 OH
CH(CH.sub.3)OAc Br OH
CH(CH.sub.3)OCOC(CH.sub.3).sub.3
Br OH
CH(CH.sub.3)OAc Cl OH
CH(CH.sub.3)OAc F OH
CH(CH.sub.3)OAc CF.sub.3 OH
CO.sub.2 CH(Me)OAc Br OH
CO.sub.2 CH(Me)OAc Br OAc
______________________________________
Claim 18
Dependent Claim
64 words
A composition of claim 13 wherein the compound is of the formula: ______________________________________
##STR96##
R.sup.2 R.sup.3
R.sup.5
______________________________________
Br OMe OMe
Cl OMe OMe
F OMe OMe
I OMe OMe
CF.sub.3 OMe OMe
CN OMe OMe
Br OEt OEt
Cl OEt OEt
Br OMe OEt
Cl OMe OEt
F OMe OEt
Br OEt OMe
Cl OEt OMe
F OEt OMe
CF.sub.3 OEt OMe
______________________________________
Claim 19
Dependent Claim
10 words
A composition of claim 13 wherein the compound is 3-acetoxy-10-acetyl-4-bromo-2,7-dimethoxy-10H-phenothiazine.
Claim 20
Dependent Claim
10 words
A composition of claim 13 wherein the compound is 10-(1-acetoxyethoxycarbonyl)-4-bromo-2,7-dimethoxy-3-hydroxy-10H-phenothiazine.
Claim 21
Dependent Claim
10 words
A composition of claim 13 wherein the compound is 3-Acetoxy-10-(1-acetoxyethoxycarbonyl)-4-bromo-2,7-dimethoxy-10H-phenothiazine.
Claim 22
Dependent Claim
10 words
A composition of claim 13 wherein the compound is 3-Hydroxy-10-acetyl-4-bromo-2,7-dimethoxy-10H-phenothiazine.
References Cited (Backward Citations)
US3000885A
Cited
US3450698A
Cited
US3471482A
Cited
US3591692A
Cited
GB1300486A
Cited
US4148885A
Cited
US3961055A
Cited
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 |