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Heterocyclic spiro-linked amidines, compositions and use thereof

Assignee: Hoechst AG
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Filing: 1980-02-21
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Granted: 1981-07-07
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Expires: 2000-02-21
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Abstract

Abstract Heterocyclic, spiro-linked amidines of the formula I ##STR1## and their physiologically acceptable salts, in which (a) n is 1 or 2; (b) R 1 and R 2 are hydrogen or alkyl radicals which, together with the nitrogen atom, can form a 5-, 6- or 7-membered ring which can be substituted by C 1 -C 3 -alkyl, C 1 -C 2 -alkoxy, hydroxyl or C 1 -C 4 -alkoxy-carbonyl groups and in which one of the carbon atoms can also be replaced by an oxygen, sulfur or nitrogen atom, it being possible for the nitrogen atom to be substituted by hydrogen, by the formyl group or by a phenyl radical, which can in turn be monosubstituted or polysubstituted by a C 1 to C 4 -alkyl group or an alkoxy, methylenedioxy, hydroxyl, halogen, nitro or amino group, or it being possible for the nitrogen atom to be substituted by a C 1 -C 4 -alkyl group, or in which R 1 represents hydrogen and R 2 represents a C 5 -C 8 -cycloalkyl radical which can be substituted by C 1 -C 4 -dialkylamino groups; (c) R 3 is hydrogen or methyl and (d) R.sup. 4 denotes a phenyl radical which is optionally monosubstituted or polysubstituted by C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, methylenedioxy, hydroxyl, halogen, cyano, nitro, trifluoromethyl, amino, C 2 -C 5 -acylamino or mono- or di-C 1 -C 4 -alkylamino groups, or a thiophene radical, their stereoisomers and optical isomers, processes for their preparation and antidepressive medicaments containing these compounds.

Inventors

  • 👤 Manfred Forsch
  • 👤 Wolfgang Schaub
  • 👤 Hermann Gerhards

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-07 22:42
CPC Classifications
C; C07; C07D; C07D471/00; C07D471/02; C07D471/10; A; A61; A61P; A61P25/00; A61P25/24; A61P25/26; C07C; C07C205/00; C07C205/05; C07D209/00; C07D209/56; C07D209/96

Claims Analysis

Total Claims: 11
Claim 1
Independent Claim 247 words
Heterocyclic, spiro-linked amidines of the formula I ##STR81## in which (a) n is 1 or 2; (b) R 1 and R 2 are hydrogen or alkyl radicals which, together with the nitrogen atom, can form a 5-, 6- or 7-membered ring which can be substituted by C 1 -C 3 -alkyl, C 1 -C 2 -alkoxy, hydroxyl or C 1 -C 4 -alkoxycarbonyl groups and in which one of the carbon atoms can also be replaced by an oxygen, sulfur or nitrogen atom, it being possible for the nitrogen atom to be substituted by hydrogen, by the formyl group or by a phenyl radical, which can in turn be monosubstituted or polysubstituted by a C 1 to C 4 -alkyl group or an alkoxy, methylenedioxy, hydroxyl, halogen, nitro or amino group, or it being possible for the nitrogen atom to be substituted by a C 1 -C 4 -alkyl group, or in which R 1 represents hydrogen and R 2 represents a C 5 -C 8 -cycloalkyl radical which can be substituted by C 1 -C 4 -dialkylamino groups; (c) R 3 is hydrogen or methyl and (d) R 4 denotes a phenyl radical which is optionally monosubstituted or polysubstituted by C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, methylenedioxy, hydroxyl, halogen, cyano, nitro, trifluoromethyl, amino, C 2 -C 5 -acylamino or mono- or di-C 1 -C 4 -alkylamino groups, or a thiophene radical, and the physiologically acceptable salts of compounds of the formula I.
Claim 2
Dependent Claim 247 words
Heterocyclic, spiro-linked amidines of the formula I ##STR81## in which (a) n is 1 or 2; (b) R 1 and R 2 are hydrogen or alkyl radicals which, together with the nitrogen atom, can form a 5-, 6- or 7-membered ring which can be substituted by C 1 -C 3 -alkyl, C 1 -C 2 -alkoxy, hydroxyl or C 1 -C 4 -alkoxycarbonyl groups and in which one of the carbon atoms can also be replaced by an oxygen, sulfur or nitrogen atom, it being possible for the nitrogen atom to be substituted by hydrogen, by the formyl group or by a phenyl radical, which can in turn be monosubstituted or polysubstituted by a C 1 to C 4 -alkyl group or an alkoxy, methylenedioxy, hydroxyl, halogen, nitro or amino group, or it being possible for the nitrogen atom to be substituted by a C 1 -C 4 -alkyl group, or in which R 1 represents hydrogen and R 2 represents a C 5 -C 8 -cycloalkyl radical which can be substituted by C 1 -C 4 -dialkylamino groups; (c) R 3 is hydrogen or methyl and (d) R 4 denotes a phenyl radical which is optionally monosubstituted or polysubstituted by C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, methylenedioxy, hydroxyl, halogen, cyano, nitro, trifluoromethyl, amino, C 2 -C 5 -acylamino or mono- or di-C 1 -C 4 -alkylamino groups, or a thiophene radical, and the physiologically acceptable salts of compounds of the formula I.
Claim 3
Dependent Claim 41 words
Stereoisomeric exo-aryl-endo-pyrroline amidines as claimed in claim 1, of the general formula XII ##STR82## in which R 1 , R 2 , R 3 , R 4 and n have the meaning given for claim 1, and their physiologically acceptable salts.
Claim 4
Dependent Claim 41 words
Stereoisomeric endo-aryl-exo-pyrroline amidines as claimed in claim 1, of the general formula XVII ##STR83## in which R 1 , R 2 , R 3 , R 4 and n have the meaning given for claim 1, and their physiologically acceptable salts.
Claim 5
Dependent Claim 20 words
Optical isomers of the formula XII and XVII as claimed in claims 2 and 3, and their physiologically acceptable salts.
Claim 6
Dependent Claim 16 words
Laevo-rotatory enantiomers of the optical isomers as claimed in claim 4, and their physiologically acceptable salts.
Claim 7
Dependent Claim 12 words
The compound of claim 1 which is 3-(4-chlorophenyl)-5'-morpholino-spiro(bicyclo(2,2,1)-heptane-2,2'-5-pyrroline) or a salt thereof.
Claim 8
Dependent Claim 12 words
The compound of claim 1 which is 3-(4-fluorophenyl)-5'-morpholino-spiro(bicyclo(2,2,1)-heptane-2,2'-5-pyrroline) or a salt thereof.
Claim 9
Dependent Claim 12 words
The compound of claim 1 which is 3-(3,4-dichlorophenyl)-5-morpholino-spiro(bicyclo(2,2,1)-heptane-2,2'-5-pyrroline) or a salt thereof.
Claim 10
Dependent Claim 23 words
Antidepressant composition comprising an effective amount of a compound as defined in claim 1 and a physiologically acceptable auxiliary agent or carrier therefor.
Claim 11
Dependent Claim 35 words
A method of treating a human patient having depressions which comprises oral administration to said patient of an effective dosage of from about 20 to 120 mg/day of a compound as defined in claim 1.

References Cited (Backward Citations)

US2931805A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1984-07-06 1985-01-05 1985-07-07 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1988-07-06 1989-01-05 1989-07-07 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1992-07-06 1993-01-05 1993-07-07 $7700.00 Window Closed / Lapsed

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