US4246409A
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Triazinones
Assignee: William H Rorer Inc
•
Filing: 1978-11-13
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Granted: 1981-01-20
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Expires: 1998-11-13
Abstract
Abstract Novel s-triazine compounds are prepared as derivatives of the corresponding amidinourea and amidinothiourea compounds by reacting with an activated form of an acid amide to give substituted s-triazinones and thiones respectively, of the formula ##STR1## The s-triazinones and thiones are useful derivatives in analyzing for the corresponding amidinourea or amidino thiourea precursors and also have useful pharmacological properties which make them suitable for a variety of medicinal purposes including use as antidiarrheal agents.
Inventors
- 👤 George H. Douglas
- 👤 William L. Studt
- 👤 Chong M. Won
- 👤 Stuart A. Dodson
- 👤 Jerome J. Zalipsky
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 13:19
CPC Classifications
C; C07; C07D; C07D251/00; C07D251/02; C07D251/12; C07D251/14; C07D251/16; A; A61; A61P; A61P1/00; A61P1/04; A61P1/10; A61P1/12
Claims Analysis
Total Claims: 41
Claim 1
Independent Claim
232 words
A compound of the formula ##STR283## wherein: X is oxygen or sulfur; R 1 is aryl, aryl lower alkyl, a 5 or 6 membered heterocycle or a lower alkyl substituted 5 or 6 membered heterocycle; R 2 is hydrogen or lower alkyl; and R 3 and R 4 are each independently selected from the group consisting of hydrogen, hydroxyl, lower alkanoyl, lower alkyl, cyclo-lower alkyl, lower alkenyl, lower alkynyl, halo-lower alkyl, lower alkoxy-lower alkyl, hydroxy-lower alkyl, phenoxy-lower alkyl, diloweralkyl amino, aryl or aryl-lower alkyl, lower alkoxy, phenoxy, a 5 or 6 membered heterocycle or a lower alkyl substituted 5 or 6 membered heterocycle or R 3 and R 4 together with the nitrogen to which they are attached form a 3 to 7 membered heterocyclic ring, selected from the group consisting of oxazolidinyl, thiazolidinyl, pyrazolidinyl, imidazolidinyl, piperidyl, piperazinyl, thiamorpholinyl, trimethylenetriaminyl, ethyleneiminyl, and morpholinyl; and, wherein: aryl means phenyl or phenyl in which one or more of the phenyl hydrogens has been replaced by the same or different substituents selected from the group consisting of halo, lower alkyl, halo-lower alkyl, nitro, amino, lower alkylacylamino, hydroxy, lower alkoxy, phenyl-lower alkoxy, lower alkyl acyloxy, cyano, halo-lower alkoxy or lower alkyl sulfonyl; and, 5 or 6 membered heterocycle means a heterocyclic substituent selected from the group consisting of pyridyl, pyrimidyl, pyrazolyl, imidazolyl, furyl, thienyl, oxazolyl, thiazolyl, piperidyl, and morpholinyl; and the non-toxic pharmaceutically acceptable salts thereof.
Claim 2
Dependent Claim
232 words
A compound of the formula ##STR283## wherein: X is oxygen or sulfur; R 1 is aryl, aryl lower alkyl, a 5 or 6 membered heterocycle or a lower alkyl substituted 5 or 6 membered heterocycle; R 2 is hydrogen or lower alkyl; and R 3 and R 4 are each independently selected from the group consisting of hydrogen, hydroxyl, lower alkanoyl, lower alkyl, cyclo-lower alkyl, lower alkenyl, lower alkynyl, halo-lower alkyl, lower alkoxy-lower alkyl, hydroxy-lower alkyl, phenoxy-lower alkyl, diloweralkyl amino, aryl or aryl-lower alkyl, lower alkoxy, phenoxy, a 5 or 6 membered heterocycle or a lower alkyl substituted 5 or 6 membered heterocycle or R 3 and R 4 together with the nitrogen to which they are attached form a 3 to 7 membered heterocyclic ring, selected from the group consisting of oxazolidinyl, thiazolidinyl, pyrazolidinyl, imidazolidinyl, piperidyl, piperazinyl, thiamorpholinyl, trimethylenetriaminyl, ethyleneiminyl, and morpholinyl; and, wherein: aryl means phenyl or phenyl in which one or more of the phenyl hydrogens has been replaced by the same or different substituents selected from the group consisting of halo, lower alkyl, halo-lower alkyl, nitro, amino, lower alkylacylamino, hydroxy, lower alkoxy, phenyl-lower alkoxy, lower alkyl acyloxy, cyano, halo-lower alkoxy or lower alkyl sulfonyl; and, 5 or 6 membered heterocycle means a heterocyclic substituent selected from the group consisting of pyridyl, pyrimidyl, pyrazolyl, imidazolyl, furyl, thienyl, oxazolyl, thiazolyl, piperidyl, and morpholinyl; and the non-toxic pharmaceutically acceptable salts thereof.
Claim 3
Dependent Claim
10 words
A compound according to claim 1 wherein X is oxygen.
Claim 4
Dependent Claim
185 words
A compound of the formula ##STR284## wherein X is oxygen or sulfur; R 1 is phenyl, benzyl or phenethyl; or phenyl, benzyl or phenethyl in which one or more of the phenyl hydrogens are substituted by lower alkyl, lower alkoxy, halo, halo-lower alkyl, amino, nitro, lower alkyl acyloxy, lower alkyl acylamino, hydroxy, cyano, carboxyl, or lower alkyl sulfonyl; pyridyl or pyridyl in which one or more of the hydrogens are substituted by lower alkyl, lower alkoxy, halo, halo-lower alkyl, amino, nitro, lower alkyl acyloxy, lower alkyl acylamino, hydroxy, cyano, carboxyl, or lower alkyl sulfonyl; R 2 is hydrogen or lower alkyl, and R 3 and R 4 are each independently selected from the group consisting of hydrogen, hydroxyl, lower alkanoyl, lower alkyl, lower alkenyl, lower alkynyl, lower alkoxy, halo-lower alkyl, hydroxy-lower alkyl, lower alkoxy-lower alkyl, phenoxy-lower alkyl, di-lower alkyl-amino-lower alkyl or R 3 and R 4 together with the nitrogen to which they are attached form a 5 or 6 membered nitrogen heterocycle selected from the group consisting of oxazolidinyl, thiazolidinyl, pyrazolidinyl, imidazolidinyl, piperidyl, piperazinyl, thiamorpholinyl, and morpholinyl; and the pharmaceutically acceptable non-toxic salts thereof.
Claim 5
Dependent Claim
185 words
A compound of the formula ##STR284## wherein X is oxygen or sulfur; R 1 is phenyl, benzyl or phenethyl; or phenyl, benzyl or phenethyl in which one or more of the phenyl hydrogens are substituted by lower alkyl, lower alkoxy, halo, halo-lower alkyl, amino, nitro, lower alkyl acyloxy, lower alkyl acylamino, hydroxy, cyano, carboxyl, or lower alkyl sulfonyl; pyridyl or pyridyl in which one or more of the hydrogens are substituted by lower alkyl, lower alkoxy, halo, halo-lower alkyl, amino, nitro, lower alkyl acyloxy, lower alkyl acylamino, hydroxy, cyano, carboxyl, or lower alkyl sulfonyl; R 2 is hydrogen or lower alkyl, and R 3 and R 4 are each independently selected from the group consisting of hydrogen, hydroxyl, lower alkanoyl, lower alkyl, lower alkenyl, lower alkynyl, lower alkoxy, halo-lower alkyl, hydroxy-lower alkyl, lower alkoxy-lower alkyl, phenoxy-lower alkyl, di-lower alkyl-amino-lower alkyl or R 3 and R 4 together with the nitrogen to which they are attached form a 5 or 6 membered nitrogen heterocycle selected from the group consisting of oxazolidinyl, thiazolidinyl, pyrazolidinyl, imidazolidinyl, piperidyl, piperazinyl, thiamorpholinyl, and morpholinyl; and the pharmaceutically acceptable non-toxic salts thereof.
Claim 6
Dependent Claim
10 words
A compound according to claim 3 wherein X is oxygen.
Claim 7
Dependent Claim
182 words
A compound of the formula ##STR285## wherein X is oxygen or sulfur; R 1 is phenyl, pyridyl, phenyl in which one or more of the phenyl hydrogens is replaced by lower alkyl, lower alkoxy, halo, halo-lower alkyl, amino, nitro, lower alkyl acyloxy, lower alkyl acylamino, hydroxy, cyano, carboxyl, or lower alkyl sulfonyl, or pyridyl in which one or more of the hydrogens is replaced by lower alkyl, lower alkoxy, halo, halo-lower alkyl, amino, nitro, lower alkyl acyloxy, lower alkyl acylamino, hydroxy, cyano, carboxyl, or lower alkyl sulfonyl; R 2 is hydrogen or lower alkyl, and R 3 and R 4 are each independently selected from the group consisting of hydrogen, hydroxyl, lower alkanoyl, lower alkyl, lower alkenyl, lower alkynyl, lower alkoxy, halo-lower alkyl, hydroxy lower alkyl, lower alkoxy lower alkyl, phenoxy lower alkyl, di-lower alkyl-amino lower alkyl or R 3 and R 4 together with the nitrogen to which they are attached form a 5 or 6 membered nitrogen heterocycle selected from the group consisting of oxazolidinyl, thiazolidinyl, pyrazolidinyl, imidazolidinyl, piperidyl, piperazinyl, thiamorpholinyl, and morpholinyl; and the pharmaceutically acceptable non-toxic salts thereof.
Claim 8
Dependent Claim
182 words
A compound of the formula ##STR285## wherein X is oxygen or sulfur; R 1 is phenyl, pyridyl, phenyl in which one or more of the phenyl hydrogens is replaced by lower alkyl, lower alkoxy, halo, halo-lower alkyl, amino, nitro, lower alkyl acyloxy, lower alkyl acylamino, hydroxy, cyano, carboxyl, or lower alkyl sulfonyl, or pyridyl in which one or more of the hydrogens is replaced by lower alkyl, lower alkoxy, halo, halo-lower alkyl, amino, nitro, lower alkyl acyloxy, lower alkyl acylamino, hydroxy, cyano, carboxyl, or lower alkyl sulfonyl; R 2 is hydrogen or lower alkyl, and R 3 and R 4 are each independently selected from the group consisting of hydrogen, hydroxyl, lower alkanoyl, lower alkyl, lower alkenyl, lower alkynyl, lower alkoxy, halo-lower alkyl, hydroxy lower alkyl, lower alkoxy lower alkyl, phenoxy lower alkyl, di-lower alkyl-amino lower alkyl or R 3 and R 4 together with the nitrogen to which they are attached form a 5 or 6 membered nitrogen heterocycle selected from the group consisting of oxazolidinyl, thiazolidinyl, pyrazolidinyl, imidazolidinyl, piperidyl, piperazinyl, thiamorpholinyl, and morpholinyl; and the pharmaceutically acceptable non-toxic salts thereof.
Claim 9
Dependent Claim
10 words
A compound according to claim 5 wherein X is oxygen.
Claim 10
Dependent Claim
232 words
A compound of the formula ##STR286## wherein: X is oxygen or sulfur; R 2 is hydrogen or lower alkyl; R 3 and R 4 are each independently selected from the group consisting of hydrogen, hydroxyl, lower alkanoyl, lower alkyl, cyclo-lower alkyl, lower alkenyl, lower alkynyl, halo-lower alkyl, lower alkoxy-lower alkyl, hydroxy-lower alkyl, phenoxy-lower alkyl, diloweralkylamino, aryl or aryl-lower alkyl, lower alkoxy, phenoxy and 5 or 6 membered heterocycles selected from the group consisting of pyridyl, pyrimidyl, pyrazolyl, imidazolyl, furyl, thienyl, oxazolyl, piperidyl and morpholinyl, or R 3 and R 4 together with the nitrogen to which they are attached form a 3 to 7 membered ring selected from the group consisting of oxazolidinyl, thiazolidinyl, pyrazolidinyl, imidazolidinyl, piperidyl, piperazinyl, thiamorpholinyl, trimethylenetriaminyl, ethyleneiminyl, and morpholinyl; and R 5 , R 6 , R 7 , R 8 and R 9 are each independently selected from the group consisting of hydrogen, lower alkyl, lower alkoxy, halo, halo-lower alkyl, amino, nitro, lower alkyl acyloxy, lower alkyl acylamino, hydroxy, cyano, carboxyl, or lower alkyl sulfonyl; and, wherein: aryl means phenyl or phenyl in which one or more of the phenyl hydrogens has been replaced by the same or different substituents selected from the group consisting of halo, lower alkyl, halo-lower alkyl, nitro, amino, lower alkylaclamino, hydroxy, lower alkoxy, phenyl-lower alkoxy, lower alkyl acyloxy, cyano, halo-lower alkoxy and lower alkyl sulfonyl; and the non-toxic pharmaceutically acceptable salts thereof.
Claim 11
Dependent Claim
232 words
A compound of the formula ##STR286## wherein: X is oxygen or sulfur; R 2 is hydrogen or lower alkyl; R 3 and R 4 are each independently selected from the group consisting of hydrogen, hydroxyl, lower alkanoyl, lower alkyl, cyclo-lower alkyl, lower alkenyl, lower alkynyl, halo-lower alkyl, lower alkoxy-lower alkyl, hydroxy-lower alkyl, phenoxy-lower alkyl, diloweralkylamino, aryl or aryl-lower alkyl, lower alkoxy, phenoxy and 5 or 6 membered heterocycles selected from the group consisting of pyridyl, pyrimidyl, pyrazolyl, imidazolyl, furyl, thienyl, oxazolyl, piperidyl and morpholinyl, or R 3 and R 4 together with the nitrogen to which they are attached form a 3 to 7 membered ring selected from the group consisting of oxazolidinyl, thiazolidinyl, pyrazolidinyl, imidazolidinyl, piperidyl, piperazinyl, thiamorpholinyl, trimethylenetriaminyl, ethyleneiminyl, and morpholinyl; and R 5 , R 6 , R 7 , R 8 and R 9 are each independently selected from the group consisting of hydrogen, lower alkyl, lower alkoxy, halo, halo-lower alkyl, amino, nitro, lower alkyl acyloxy, lower alkyl acylamino, hydroxy, cyano, carboxyl, or lower alkyl sulfonyl; and, wherein: aryl means phenyl or phenyl in which one or more of the phenyl hydrogens has been replaced by the same or different substituents selected from the group consisting of halo, lower alkyl, halo-lower alkyl, nitro, amino, lower alkylaclamino, hydroxy, lower alkoxy, phenyl-lower alkoxy, lower alkyl acyloxy, cyano, halo-lower alkoxy and lower alkyl sulfonyl; and the non-toxic pharmaceutically acceptable salts thereof.
Claim 12
Dependent Claim
10 words
A compound according to claim 7 wherein X is oxygen.
Claim 13
Dependent Claim
26 words
A compound according to claim 8 wherein each of R 6 , R 7 and R 8 is hydrogen; and the non-toxic pharmaceutically acceptable salts thereof.
Claim 14
Dependent Claim
18 words
A compound according to claim 9 wherein R 3 is hydrogen; and the non-toxic pharmaceutically acceptable salts thereof.
Claim 15
Dependent Claim
30 words
A compound according to claim 10 wherein each of R 5 and R 9 is halo, lower alkyl, lower alkoxy, or halo-lower alkyl; and the non-toxic pharmaceutically acceptable salts thereof.
Claim 16
Dependent Claim
24 words
A compound according to claim 11 wherein each of R 5 and R 9 is lower alkyl; and the non-toxic pharmaceutically acceptable salts thereof.
Claim 17
Dependent Claim
216 words
A compound of the formula ##STR287## wherein: X is oxygen or sulfur; R 2 is hydrogen or lower alkyl; R 3 and R 4 are each independently selected from the group consisting of hydrogen, hydroxyl, lower alkanoyl, lower alkyl, cycloloweralkyl, lower alkenyl, lower alkynyl, halo-lower alkyl, lower alkoxy-lower alkyl, hydroxy lower alkyl, phenoxy lower alkyl, diloweralkylamino, aryl, aryl lower alkyl, lower alkoxy, phenoxy, and 5 or 6 membered heterocycles selected from the group consisting of pyridyl, pyrimidyl, pyrazolyl, imidazolyl, furyl, thienyl, oxazolyl, thiazolyl, piperidyl, and morpholinyl, or R 3 and R 4 together with the nitrogen to which they are attached form a 3 to 7 membered ring selected from the group consisting of oxazolidinyl, thiazolidinyl, pyrazolidinyl, imidazolidinyl, piperidyl, piperazinyl, thiamorpholinyl, trimethylenetriaminyl, ethyleneiminyl, and morpholinyl; R 5 and R 9 are each independently hydrogen, lower alkyl, halo, halo lower alkyl, hydroxy, or lower alkoxy; R 6 , R 7 and R 8 are each hydrogen; and, wherein: aryl means phenyl or phenyl in which one or more of the phenyl hydrogens has been replaced by the same or different substituents selected from the group consisting of halo, lower alkyl, halo-lower alkyl, nitro, amino, lower alkylacylamino, hydroxy, lower alkoxy, phenyl-lower alkoxy, lower alkylacyloxy, cyano, halo-lower alkoxy, and lower alkyl sulfonyl; and the non-toxic pharmaceutically acceptable salts thereof.
Claim 18
Dependent Claim
216 words
A compound of the formula ##STR287## wherein: X is oxygen or sulfur; R 2 is hydrogen or lower alkyl; R 3 and R 4 are each independently selected from the group consisting of hydrogen, hydroxyl, lower alkanoyl, lower alkyl, cycloloweralkyl, lower alkenyl, lower alkynyl, halo-lower alkyl, lower alkoxy-lower alkyl, hydroxy lower alkyl, phenoxy lower alkyl, diloweralkylamino, aryl, aryl lower alkyl, lower alkoxy, phenoxy, and 5 or 6 membered heterocycles selected from the group consisting of pyridyl, pyrimidyl, pyrazolyl, imidazolyl, furyl, thienyl, oxazolyl, thiazolyl, piperidyl, and morpholinyl, or R 3 and R 4 together with the nitrogen to which they are attached form a 3 to 7 membered ring selected from the group consisting of oxazolidinyl, thiazolidinyl, pyrazolidinyl, imidazolidinyl, piperidyl, piperazinyl, thiamorpholinyl, trimethylenetriaminyl, ethyleneiminyl, and morpholinyl; R 5 and R 9 are each independently hydrogen, lower alkyl, halo, halo lower alkyl, hydroxy, or lower alkoxy; R 6 , R 7 and R 8 are each hydrogen; and, wherein: aryl means phenyl or phenyl in which one or more of the phenyl hydrogens has been replaced by the same or different substituents selected from the group consisting of halo, lower alkyl, halo-lower alkyl, nitro, amino, lower alkylacylamino, hydroxy, lower alkoxy, phenyl-lower alkoxy, lower alkylacyloxy, cyano, halo-lower alkoxy, and lower alkyl sulfonyl; and the non-toxic pharmaceutically acceptable salts thereof.
Claim 19
Dependent Claim
22 words
A compound according to claim 13 wherein R 5 and R 9 are each halo; and the non-toxic pharmaceutically acceptable salts thereof.
Claim 20
Dependent Claim
18 words
A compound according to claim 13 wherein R 3 is hydrogen; and the non-toxic pharmaceutically acceptable salts thereof.
Claim 21
Dependent Claim
29 words
A compound according to claim 15 wherein R 2 is hydrogen and R 4 is hydrogen lower alkyl, hydroxyl or lower alkoxy; and the non-toxic pharmaceutically acceptable salts thereof.
Claim 22
Dependent Claim
30 words
A compound according to claim 16 wherein R 5 and R 9 are each independently lower alkyl, lower alkoxy, halo or halo-lower alkyl; and the non-toxic pharmaceutically acceptable salts thereof.
Claim 23
Dependent Claim
219 words
A compound of the formula ##STR288## wherein: R 2 is hydrogen or lower alkyl; R 3 and R 4 are each independently selected from the group consisting of hydrogen, hydroxyl, lower alkanoyl, lower alkyl, cycloloweralkyl, lower alkenyl, lower alkynyl, halo-lower alkyl, lower alkoxy-lower alkyl, hydroxy lower alkyl, phenoxy lower alkyl, diloweralkylamino, aryl or aryl lower alkyl, lower alkoxy, and phenoxy, and 5 or 6 membered heterocycles selected from the group consisting of pyridyl, pyrimidyl, pyrazolyl, imidazolyl, furyl, thienyl, oxazolyl, thiazolyl, piperidyl and morpholinyl, or R 3 and R 4 together with the nitrogen to which they are attached form a 3 to 7 membered ring selected from the group consisting of oxazolidinyl, thiazolidinyl, pyrazolidinyl, imidazolidinyl, piperidyl, piperazinyl, thiamorpholinyl, trimethylenetriaminyl, ethyleneiminyl, and morpholinyl; R 6 , R 7 and R 8 are each independently hydrogen, lower alkyl, hydroxy or lower alkoxy; R 5 and R 9 are each hydrogen, lower alkyl, hydroxy, lower alkoxy, halo, or halo lower alkyl; and, wherein: aryl means phenyl or phenyl in which one or more of the phenyl hydrogens has been replaced by the same or different substituents selected from the group consisting of halo, lower alkyl, halo-lower alkyl, nitro, amino, lower alkylacylamino, hydroxy, lower alkoxy, phenyl-lower alkoxy, lower alkylacyloxy, cyano, halo-lower alkoxy, and lower alkyl sulfonyl; and the non-toxic pharmaceutically acceptable salts thereof.
Claim 24
Dependent Claim
219 words
A compound of the formula ##STR288## wherein: R 2 is hydrogen or lower alkyl; R 3 and R 4 are each independently selected from the group consisting of hydrogen, hydroxyl, lower alkanoyl, lower alkyl, cycloloweralkyl, lower alkenyl, lower alkynyl, halo-lower alkyl, lower alkoxy-lower alkyl, hydroxy lower alkyl, phenoxy lower alkyl, diloweralkylamino, aryl or aryl lower alkyl, lower alkoxy, and phenoxy, and 5 or 6 membered heterocycles selected from the group consisting of pyridyl, pyrimidyl, pyrazolyl, imidazolyl, furyl, thienyl, oxazolyl, thiazolyl, piperidyl and morpholinyl, or R 3 and R 4 together with the nitrogen to which they are attached form a 3 to 7 membered ring selected from the group consisting of oxazolidinyl, thiazolidinyl, pyrazolidinyl, imidazolidinyl, piperidyl, piperazinyl, thiamorpholinyl, trimethylenetriaminyl, ethyleneiminyl, and morpholinyl; R 6 , R 7 and R 8 are each independently hydrogen, lower alkyl, hydroxy or lower alkoxy; R 5 and R 9 are each hydrogen, lower alkyl, hydroxy, lower alkoxy, halo, or halo lower alkyl; and, wherein: aryl means phenyl or phenyl in which one or more of the phenyl hydrogens has been replaced by the same or different substituents selected from the group consisting of halo, lower alkyl, halo-lower alkyl, nitro, amino, lower alkylacylamino, hydroxy, lower alkoxy, phenyl-lower alkoxy, lower alkylacyloxy, cyano, halo-lower alkoxy, and lower alkyl sulfonyl; and the non-toxic pharmaceutically acceptable salts thereof.
Claim 25
Dependent Claim
23 words
A compound according to claim 18 wherein R 5 and R 9 are each independently halo; and the non-toxic pharmaceutically acceptable salts thereof.
Claim 26
Dependent Claim
18 words
A compound according to claim 18 wherein R 3 is hydrogen; and the non-toxic pharmaceutically acceptable salts thereof.
Claim 27
Dependent Claim
29 words
A compound according to claim 20 wherein R 2 is hydrogen and R 4 is hydrogen, lower alkyl, hydroxyl or lower alkoxy; and the non-toxic pharmaceutically acceptable salts thereof.
Claim 28
Dependent Claim
23 words
A compound according to claim 21 wherein R 5 and R 9 are each independently lower alkyl, lower alkoxy, halo, or halo-lower alkyl.
Claim 29
Dependent Claim
13 words
A compound of the formula ##STR289## and the non-toxic pharmaceutically acceptable salts thereof.
Claim 30
Dependent Claim
13 words
A compound of the formula ##STR289## and the non-toxic pharmaceutically acceptable salts thereof.
Claim 31
Dependent Claim
17 words
A compound according to claim 23 having the formula ##STR290## and the non-toxic pharmaceutically acceptable salts thereof.
Claim 32
Dependent Claim
13 words
A compound of the formula ##STR291## and the non-toxic pharmaceutically acceptable salts thereof.
Claim 33
Dependent Claim
13 words
A compound of the formula ##STR291## and the non-toxic pharmaceutically acceptable salts thereof.
Claim 34
Dependent Claim
8 words
1-(2',6'-dimethylphenyl)-4-methylamino-1,2-dihydro-1,3,5-triazin-2-one; and the non-toxic pharmaceutically acceptable salts thereof.
Claim 35
Dependent Claim
8 words
1-(2',6'-dimethylphenyl)-4-methylamino-1,2-dihydro-1,3,5-triazin-2-one; and the non-toxic pharmaceutically acceptable salts thereof.
Claim 36
Dependent Claim
2 words
1-(2',6'-dimethylphenyl)-4-methylamino-1,2-dihydro-1,3,5-triazin-2-one hydrochloride.
Claim 37
Dependent Claim
2 words
1-(2',6'-dimethylphenyl)-4-methylamino-1,2-dihydro-1,3,5-triazin-2-one hydrochloride.
Claim 38
Dependent Claim
8 words
1-(2',6'-diethylphenyl)-4-methylamino-1,2-dihydro-1,3,5-triazin-2-one; and the non-toxic pharmaceutically acceptable salts thereof.
Claim 39
Dependent Claim
8 words
1-(2',6'-diethylphenyl)-4-methylamino-1,2-dihydro-1,3,5-triazin-2-one; and the non-toxic pharmaceutically acceptable salts thereof.
Claim 40
Dependent Claim
2 words
1-(2',6'-diethylphenyl)-4-methylamino-1,2-dihydro-1,3,5-triazin-2-one hydrochloride.
Claim 41
Dependent Claim
2 words
1-(2',6'-diethylphenyl)-4-methylamino-1,2-dihydro-1,3,5-triazin-2-one hydrochloride.
References Cited (Backward Citations)
US4068081A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1984-01-20 | 1984-07-21 | 1985-01-20 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-01-20 | 1988-07-21 | 1989-01-20 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-01-20 | 1992-07-21 | 1993-01-20 | $7700.00 | Window Closed / Lapsed |