US4244950A
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Derivatives of 4-amino-3-sulfonamido-pyridine, their preparation and use
Assignee: FAMITALIA CARLO ERBA Srl MILAN (VIA CARLO IMBONATI NO 24)
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Filing: 1979-01-24
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Granted: 1981-01-13
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Expires: 1999-01-24
Abstract
Abstract This invention relates to new derivatives of 4-amino-3-sulfonamido-pyridine having diuretic properties. The new derivatives of pyridine may be represented by the following general formula: <IMAGE> (I), in which R1 represents hydrogen or an alkyl, cycloalkyl, carbamoyl or sulfonamido radical; R2 represents an alkyl, halogenoalkyl, cycloalkyl, alkenyl, alkynyl, hydroxyalkyl, alkoxyalkyl, phenyl (possibly substituted), phenylalkyl, diphenylmethyl, isobornyl, furfuryl, tetrahydrofurfuryl, dialkylaminoalkyl or heterocyclic radical; or R1 and R2 form together with the nitrogen atom a saturated heterocyclic radical; and X represents an alkoxy radical, an heterocyclic amino radical, or a secondary or tertiary amino radical having its first substituent selected from hydrogen and the alkyl and alkenyl groups, and its second substituent selected from the alkyl, alkenyl, alkynyl, hydroxyalkyl, diphenylmethyl, isorbornyl, furfuryl, tetrahydrofurfuryl, phenylalkyl and heterocyclic groups. The invention also relates to salts of addition of said compounds with pharmaceutically acceptable acids.
Inventors
- 👤 Rene R. De Ridder
- 👤 Andre H. Georges
- 👤 Arlette Ghys
- 👤 Charles L. Lapiere
- 👤 Jacques E. Delarge
- 👤 Leopold N. Thunus
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 19:10
CPC Classifications
C; C07; C07D; C07D213/00; C07D213/02; C07D213/04; C07D213/60; C07D213/72; C07D213/75; A; A61; A61P; A61P7/00; A61P7/10; C07D213/74
Claims Analysis
Total Claims: 17
Claim 1
Independent Claim
362 words
A compound of the following general formula ##STR154## in which R 1 represents a hydrogen atom, a straight or branched chain alkyl group, a cycloalkyl group, a carbamoyl group of the formula ##STR155## or a sulfonamide group of the formula ##STR156## in which R 5 and R 6 represent an alkyl group or together complete a hydrocarbon chain, forming with the nitrogen atom to which they are bound, a saturated nitrogen-containing heterocyclic ring; R 2 represents a straight or branched chain alkyl group, a haloalkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, a hydroxyalkyl group, an alkoxyalkyl group, a phenyl group, a phenylalkyl group, a diphenylmethyl group, an isobornyl group, a furfuryl group, a tetrahydrofurfuryl group, a lower dialkylaminoalkyl group or a saturated or unsaturated nitrogen-containing heterocyclic ring; or R 1 and R 2 complete together a hydrocarbon chain, forming, with the nitrogen atom to which they are bound, a saturated nitrogen-containing heterocyclic ring, which may be unsubstituted or substituted with one or more alkyl groups, and X represents an alkoxy group or a group of the formula ##STR157## in which R 3 represents a hydrogen atom, a straight or branched chain alkyl group, or an alkenyl group; and R 4 represents a straight or branched chain alkyl group, an alkenyl group, an alkynyl group, a hydroxyalkyl group, a diphenylmethyl group, an isobornyl group, a furfuryl group, a tetrahydrofurfuryl group, a phenylalkyl group, a pyridyl group or a saturated nitrogen-containing heterocyclic ring; or R 3 and R 4 complete together, with the nitrogen atom to which they are bound, a saturated nitrogen-containing heterocyclic ring, a saturated dinitrogen-containing diheterocyclic ring or a saturated nitrogen- and oxygen-containing diheterocyclic ring; with the provisos that R 1 is different from a hydrogen atom or a C 1 -C 4 alkyl group, when R 2 represents a phenyl group, a furfuryl group or a C 1 -C 4 alkyl group, and X represents a ##STR158## group, in which R 3 represents a hydrogen atom and R 4 represents a C 1 -C 4 alkyl group or a C 2 -C 3 alkenyl group, as well as the pharmaceutically acceptable acid and basic addition salts.
Claim 2
Dependent Claim
362 words
A compound of the following general formula ##STR154## in which R 1 represents a hydrogen atom, a straight or branched chain alkyl group, a cycloalkyl group, a carbamoyl group of the formula ##STR155## or a sulfonamide group of the formula ##STR156## in which R 5 and R 6 represent an alkyl group or together complete a hydrocarbon chain, forming with the nitrogen atom to which they are bound, a saturated nitrogen-containing heterocyclic ring; R 2 represents a straight or branched chain alkyl group, a haloalkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, a hydroxyalkyl group, an alkoxyalkyl group, a phenyl group, a phenylalkyl group, a diphenylmethyl group, an isobornyl group, a furfuryl group, a tetrahydrofurfuryl group, a lower dialkylaminoalkyl group or a saturated or unsaturated nitrogen-containing heterocyclic ring; or R 1 and R 2 complete together a hydrocarbon chain, forming, with the nitrogen atom to which they are bound, a saturated nitrogen-containing heterocyclic ring, which may be unsubstituted or substituted with one or more alkyl groups, and X represents an alkoxy group or a group of the formula ##STR157## in which R 3 represents a hydrogen atom, a straight or branched chain alkyl group, or an alkenyl group; and R 4 represents a straight or branched chain alkyl group, an alkenyl group, an alkynyl group, a hydroxyalkyl group, a diphenylmethyl group, an isobornyl group, a furfuryl group, a tetrahydrofurfuryl group, a phenylalkyl group, a pyridyl group or a saturated nitrogen-containing heterocyclic ring; or R 3 and R 4 complete together, with the nitrogen atom to which they are bound, a saturated nitrogen-containing heterocyclic ring, a saturated dinitrogen-containing diheterocyclic ring or a saturated nitrogen- and oxygen-containing diheterocyclic ring; with the provisos that R 1 is different from a hydrogen atom or a C 1 -C 4 alkyl group, when R 2 represents a phenyl group, a furfuryl group or a C 1 -C 4 alkyl group, and X represents a ##STR158## group, in which R 3 represents a hydrogen atom and R 4 represents a C 1 -C 4 alkyl group or a C 2 -C 3 alkenyl group, as well as the pharmaceutically acceptable acid and basic addition salts.
Claim 3
Dependent Claim
40 words
A compound according to claim 1, in which R 1 represents a hydrogen atom and R 2 represents a phenyl group, X being different from a C 1 -C 4 alkylamino group or a C 2 -C 3 alkenylamino group.
Claim 4
Dependent Claim
41 words
A compound according to claim 1, in which R 1 represents a hydrogen atom and R 2 represents an alkyl group, a cycloalkyl group, a haloalkyl group, a hydroxyalkyl group, an alkenyl group, an alkynyl group, or a lower dialkylamino group.
Claim 5
Dependent Claim
25 words
A compound according to claim 1, in which R 1 represents a dialkylcarbamoyl group of the formula (II) and R 2 represents a phenyl group.
Claim 6
Dependent Claim
22 words
A compound according to claim 1, 2, 3, or 4, in which X represents a dialkylamino group or a nitrogen-containing heterocyclic ring.
Claim 7
Dependent Claim
15 words
A compound according to claim 3, or 4, in which X represents an alkylamino group.
Claim 8
Dependent Claim
20 words
A compound according to claim 1, in which R 2 is an unsubstituted phenyl group or an unsubstituted phenylalkyl group.
Claim 9
Dependent Claim
17 words
A compound according to claim 1, in which R 4 is an unsubstituted saturated nitrogen-containing heterocyclic ring.
Claim 10
Dependent Claim
45 words
A compound according to claim 1, in which R 3 and R 4 complete, together with the nitrogen atom to which they are bound, an unsubstituted saturated nitrogen-containing heterocyclic ring, an unsubstituted saturated dinitrogen-containing diheterocyclic ring or an unsubstituted saturated nitrogen- and oxygen-containing diheterocyclic ring.
Claim 11
Dependent Claim
34 words
A compound according to claim 1, in which R 2 is a phenyl group or a phenylalkyl group in which the phenyl moiety thereof is halo substituted, methyl substituted, trifluoromethyl substituted or acetyl substituted.
Claim 12
Dependent Claim
21 words
A compound according to claim 1, in which R 4 is a saturated nitrogen-containing heterocyclic ring substituted with an alkyl group.
Claim 13
Dependent Claim
58 words
A compound according to claim 1, in which R 3 and R 4 complete, together with the nitrogen atom to which they are bound, a saturated nitrogen-containing heterocyclic ring, a saturated dinitrogen-containing diheterocyclic ring, or a saturated nitrogen- and oxygen-containing diheterocyclic ring, wherein said rings are substituted by an alkyl group, a phenyl group or a halophenyl group.
Claim 14
Dependent Claim
15 words
A compound according to claim 2, in which R 2 is an unsubstituted phenyl group.
Claim 15
Dependent Claim
15 words
A compound according to claim 4, in which R 2 is an unsubstituted phenyl group.
Claim 16
Dependent Claim
15 words
Compounds according to claim 1, wherein said compound of the general formula (I) is ##STR159##
Claim 17
Dependent Claim
39 words
A pharmaceutical composition containing as an active ingredient at least one compound of the formula (I), as defined in claim 1, or a pharmaceutically acceptable acid or basic addition salt thereof together with a pharmaceutically acceptable vehicle or carrier.
References Cited (Backward Citations)
US3956294A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1984-01-13 | 1984-07-14 | 1985-01-13 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-01-13 | 1988-07-14 | 1989-01-13 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-01-13 | 1992-07-14 | 1993-01-13 | $7700.00 | Window Closed / Lapsed |