US4393075A
Expired / Lapsed
US
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Quinone compounds and their use in suppressing the production of SRS-A in mammals
Assignee: Takeda Pharmaceutical Co Ltd
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Filing: 1981-03-26
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Granted: 1983-07-12
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Expires: 2001-03-26
Abstract
Abstract New quinone compounds of the formula: <IMAGE> wherein R1 is methyl or methoxy, or the two R1 groups jointly represent -CH=CH-CH=CH-; X is -CH=CH- or -C=C-; Y1 is hydrogen, hydroxyl, carboxyl, cyano, acyloxy or -COZ in which Z is amino which may be substituted; m is zero or an integer of 1 to 3; n is zero or an integer of 1 to 10; n' is an integer of 1 to 5; k is an integer of 1 to 3; and when k is 2 or 3, n' is optionally variable within the range of 1 to 5 in each occurrence of the -X-(CH2)n' group; and their hydroquinone forms and salts, have useful physiological activities such as antiasthmatic, antiallergic and bloodpressure decreasing activities.
Inventors
- 👤 Shinji Terao
- 👤 Mitsuru Shiraishi
- 👤 Yoshitaka Maki
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 17:22
CPC Classifications
C; C07; C07D; C07D295/00; C07D295/16; C07D295/18; C07D295/182; C07D295/185; C07C; C07C43/00; C07C43/02; C07C43/20; C07C43/225; C07C43/23; C07C45/00; C07C45/27; C07C45/29; C07C46/00; C07C46/02; C07C46/06; C07C47/00; C07C47/20; C07C47/277; C07C50/00; C07C50/02; C07C50/06; C07C50/10; C07C50/14; C07C50/26; C07C50/28; C07C50/32; C07C59/00; C07C59/40; C07C59/58; C07C59/64; C07C66/00; C07D307/00; C07D307/02; C07D307/04; C07D307/10; C07D307/12; C07D309/00; C07D309/02; C07D309/08; C07D309/10; C07D309/12
Claims Analysis
Total Claims: 19
Claim 1
Independent Claim
105 words
A compound of the formula: ##STR129## wherein R 1 is methyl or methoxy, or the two R 1 groups jointly represent --CH═CH--CH═CH--, X is --CH═CH-- or --C.tbd.C--, Y 1 is hydroxyl, m is zero or an integer of 1 to 3, n is zero or an integer of 1 to 10, n' is an integer of 1 to 5, k is an integer of 1 to 3, and when k is 2 or 3, n' is optionally variable within the range of 1 to 5 in each occurrence of the --X--(CH 2 ) n' group, or its hydroquinone form, or a pharmaceutically acceptable salt thereof.
Claim 2
Dependent Claim
105 words
A compound of the formula: ##STR129## wherein R 1 is methyl or methoxy, or the two R 1 groups jointly represent --CH═CH--CH═CH--, X is --CH═CH-- or --C.tbd.C--, Y 1 is hydroxyl, m is zero or an integer of 1 to 3, n is zero or an integer of 1 to 10, n' is an integer of 1 to 5, k is an integer of 1 to 3, and when k is 2 or 3, n' is optionally variable within the range of 1 to 5 in each occurrence of the --X--(CH 2 ) n' group, or its hydroquinone form, or a pharmaceutically acceptable salt thereof.
Claim 3
Dependent Claim
9 words
The compound according to claim 1, which is 2,3-dimethoxy-5-methyl-6-(9-hydroxynon-5-ynyl)-1,4-benzoquinone.
Claim 4
Dependent Claim
9 words
The compound according to claim 1, which is 2,3,5-trimethyl-6-(12-hydroxy-5,10-dodecadiynyl)-1,4-benzoquinone.
Claim 5
Dependent Claim
9 words
The compound according to claim 1, which is 2,3-dimethoxy-5-methyl-6-(12-hydroxy-5,10-dodecadiynyl)-1,4-benzoquinone.
Claim 6
Dependent Claim
9 words
The compound according to claim 1, which is 2,3-dimethoxy-5-methyl-6-[12-hydroxy-(Z,Z)-5,10-dodecadienyl]-1,4-benzoquinone.
Claim 7
Dependent Claim
9 words
The compound according to claim 1, which is 2,3,5-trimethyl-6-[12-hydroxy-(Z,Z)-5,10-dodecadienyl]-1,4-benzoquinone.
Claim 8
Dependent Claim
143 words
A compound of the formula: ##STR130## wherein R 1 is methyl or methoxy, or the two R 1 groups jointly represent --CH═CH--CH═CH--, X is --CH═CH-- or --C.tbd.C--, Y 1 is hydrogen, carboxyl, cyano, C 2-4 alkanoyloxy, benzoyloxy or --COZ in which Z is amino or mono- or di-C 1-4 alkylamino, m is zero or an integer of 1 to 3, n is zero or an integer of 1 to 10, n' is an integer of 1 to 5, k is an integer of 1 to 3, and when k is 2 or 3, n' is optionally variable within the range of 1 to 5 in each occurrence of the --X--(CH 2 ) n' group, with the proviso that there are 8-15 carbon atoms in series between the quinone ring and Y 1 , or its hydroquinone form, or a pharmaceutically acceptable salt thereof.
Claim 9
Dependent Claim
143 words
A compound of the formula: ##STR130## wherein R 1 is methyl or methoxy, or the two R 1 groups jointly represent --CH═CH--CH═CH--, X is --CH═CH-- or --C.tbd.C--, Y 1 is hydrogen, carboxyl, cyano, C 2-4 alkanoyloxy, benzoyloxy or --COZ in which Z is amino or mono- or di-C 1-4 alkylamino, m is zero or an integer of 1 to 3, n is zero or an integer of 1 to 10, n' is an integer of 1 to 5, k is an integer of 1 to 3, and when k is 2 or 3, n' is optionally variable within the range of 1 to 5 in each occurrence of the --X--(CH 2 ) n' group, with the proviso that there are 8-15 carbon atoms in series between the quinone ring and Y 1 , or its hydroquinone form, or a pharmaceutically acceptable salt thereof.
Claim 10
Dependent Claim
12 words
A compound according to claim 7, which is in the quinone form.
Claim 11
Dependent Claim
20 words
A compound according to claim 7, wherein R 1 is methyl or methoxy, X is --C.tbd.C--, and m is zero.
Claim 12
Dependent Claim
23 words
A compound according to claim 7, wherein Y 1 is carboxyl, cyano or --COZ in which Z is amino or C 1-4 alkylamino.
Claim 13
Dependent Claim
34 words
A compound according to claim 7, wherein m is zero or 1, n is an integer of 1 to 4, n' is an integer of 1 to 3 and k is 1 or 2.
Claim 14
Dependent Claim
136 words
A pharmaceutical composition suitable for suppressing the production of SRS-A in a mammal which comprises, as an active ingredient, an effective amount of a compound of the formula: ##STR131## wherein R 1 is methyl or methoxy, or the two R 1 groups jointly represent --CH═CH--CH═CH--, X is --CH═CH-- or --C.tbd.C--, Y 1 is hydroxyl, m is zero or an integer of 1 to 3, n is zero or an integer of 1 to 10, n' is an integer of 1 to 5, k is an integer of 1 to 3, and when k is 2 or 3, n' is optionally variable within the range of 1 to 5 in each occurrence of the --X--(CH 2 ) n' group, or its hydroquinone form, or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier or excipient therefor.
Claim 15
Dependent Claim
136 words
A pharmaceutical composition suitable for suppressing the production of SRS-A in a mammal which comprises, as an active ingredient, an effective amount of a compound of the formula: ##STR131## wherein R 1 is methyl or methoxy, or the two R 1 groups jointly represent --CH═CH--CH═CH--, X is --CH═CH-- or --C.tbd.C--, Y 1 is hydroxyl, m is zero or an integer of 1 to 3, n is zero or an integer of 1 to 10, n' is an integer of 1 to 5, k is an integer of 1 to 3, and when k is 2 or 3, n' is optionally variable within the range of 1 to 5 in each occurrence of the --X--(CH 2 ) n' group, or its hydroquinone form, or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier or excipient therefor.
Claim 16
Dependent Claim
174 words
A pharmaceutical composition suitable for suppressing the production of SRS-A in a mammal which comprises, as an active ingredient, an effective amount of a compound of the formula: ##STR132## wherein R 1 is methyl or methoxy, or the two R 1 groups jointly represent --CH═CH--CH═CH--, X is --CH═CH-- or --C.tbd.C--, Y 1 is hydrogen, carboxyl, cyano, C 2-4 alkanoyloxy, benzoyloxy or --COZ in which Z is amino or mono- or di-C 1-4 alkylamino, m is zero or an integer of 1 to 3, n is zero or an integer of 1 to 10, n' is an integer of 1 to 5, k is an integer of 1 to 3, and when k is 2 or 3, n' is optionally variable within the range of 1 to 5 in each occurrence of the --X--(CH 2 ) n' group, with the proviso that there are 8-15 carbon atoms in series between the quinone ring and Y 1 , or its hydroquinone form, or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier or excipient therefor.
Claim 17
Dependent Claim
174 words
A pharmaceutical composition suitable for suppressing the production of SRS-A in a mammal which comprises, as an active ingredient, an effective amount of a compound of the formula: ##STR132## wherein R 1 is methyl or methoxy, or the two R 1 groups jointly represent --CH═CH--CH═CH--, X is --CH═CH-- or --C.tbd.C--, Y 1 is hydrogen, carboxyl, cyano, C 2-4 alkanoyloxy, benzoyloxy or --COZ in which Z is amino or mono- or di-C 1-4 alkylamino, m is zero or an integer of 1 to 3, n is zero or an integer of 1 to 10, n' is an integer of 1 to 5, k is an integer of 1 to 3, and when k is 2 or 3, n' is optionally variable within the range of 1 to 5 in each occurrence of the --X--(CH 2 ) n' group, with the proviso that there are 8-15 carbon atoms in series between the quinone ring and Y 1 , or its hydroquinone form, or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier or excipient therefor.
Claim 18
Independent Claim
149 words
A method for suppressing the production of SRS-A in a mammal in need thereof, which comprises administering to said mammal an effective amount of a compound of the formula: ##STR133## wherein R 1 is methyl or methoxy, or the two R 1 groups jointly represent --CH═CH--CH═CH--, X is --CH═CH-- or --C.tbd.C--, Y 1 is hydrogen, hydroxyl, carboxyl, cyano, C 2-4 alkanoyloxy, benzoyloxy or --COZ in which Z is amino or mono- or di-C 1-4 alkylamino, m is zero or an integer of 1 to 3, n is zero or an integer of 1 to 10, n' is an integer of 1 to 5, k is an integer of 1 to 3, and when k is 2 or 3, n' is optionally variable within the range of 1 to 5 in each occurrence of the --X--(CH 2 ) n' group, or its hydroquinone form, or a pharmaceutically acceptable salt thereof.
Claim 19
Independent Claim
149 words
A method for suppressing the production of SRS-A in a mammal in need thereof, which comprises administering to said mammal an effective amount of a compound of the formula: ##STR133## wherein R 1 is methyl or methoxy, or the two R 1 groups jointly represent --CH═CH--CH═CH--, X is --CH═CH-- or --C.tbd.C--, Y 1 is hydrogen, hydroxyl, carboxyl, cyano, C 2-4 alkanoyloxy, benzoyloxy or --COZ in which Z is amino or mono- or di-C 1-4 alkylamino, m is zero or an integer of 1 to 3, n is zero or an integer of 1 to 10, n' is an integer of 1 to 5, k is an integer of 1 to 3, and when k is 2 or 3, n' is optionally variable within the range of 1 to 5 in each occurrence of the --X--(CH 2 ) n' group, or its hydroquinone form, or a pharmaceutically acceptable salt thereof.
References Cited (Backward Citations)
US3728362A
Cited
US4139545A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1986-07-11 | 1987-01-10 | 1987-07-12 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1990-07-11 | 1991-01-10 | 1991-07-12 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1994-07-11 | 1995-01-10 | 1995-07-12 | $7700.00 | Window Closed / Lapsed |