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US4731374A Expired / Lapsed US ⏱️ 0.0 years remaining

Tetrahydro-benzthiazoles, the preparation thereof and their use as intermediate products or as pharmaceuticals

Assignee: Boehringer Ingelheim International GmbH
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Filing: 1985-12-19
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Granted: 1988-03-15
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Expires: 2005-12-19
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Abstract

Abstract This invention relates to new tetrahydrobenzthiazoles of general formula <IMAGE> (I) wherein R1 represents a hydrogen atom, an alkyl group, an alkenyl or alkynylk group, an alkanoyl group, a phenyl alkyl or phenyl alkanoyl group, while the above mentioned phenyl nuclei may each be substituted by 1 or 2 halogen atoms, R2 represents a hydrogen atom or an alkyl group, R3 represents a hydrogen atom, an alkyl group a cycloalkyl group, an alkenyl or alkynyl group, an alkanoyl group, a phenyl alkyl or phenyl alkanoyl group, while the phenyl nucleus may be substituted by flurorine, chlorine or bromine atoms, R4 represents a hydrogen atom, an alkyl group, an alkyl or alkenyl group, or R3 and R4 together with the nitrogen atom between them represent a pyrrolidino, piperidino, hexamethyleneimino or morpholino group, the enantiomers and the acid addition salts thereof. The compounds of general formula I above in which one of the groups R1 or R3 or both groups R1 and R3 represent an acyl group are valuable intermediate products for preparing the other compounds of general formula I which have valuable pharmacological properties. The new compounds may be prepared using methods known per se.

Inventors

  • 👤 Gerhart Griss, deceased
  • 👤 Rudolf Hurnaus
  • 👤 Walter Kobinger
  • 👤 Ludwig Pichler
  • 👤 Rudolf Bauer
  • 👤 Joachim Mierau
  • 👤 Dieter Hinzen
  • 👤 Gunter Schingnitz

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-06 22:09
CPC Classifications
C; C07; C07D; C07D277/00; C07D277/60; C07D277/62; C07D277/68; C07D277/82

Claims Analysis

Total Claims: 13
Claim 1
Independent Claim 116 words
A tetrahydro-benzthiazole of the formula: ##STR15## wherein R 1 is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkenyl or alkynyl group each having 3 to 6 carbon atoms, an alkanoyl group having 1 to 6 carbon atoms, a phenyl alkyl or phenyl alkanoyl group having 1 to 3 carbon atoms in the alkyl part, wherein the above mentioned phenyl nuclei may be substituted by 1 or 2 halogen atoms; R 2 is a hydrogen atom or an alkyl group with 1 to 4 carbon atoms; and R 3 and R 4 together with the nitrogen atom between them form a pyrrolidino group; or, a pharmaceutically acceptable acid addition salt thereof.
Claim 2
Dependent Claim 116 words
A tetrahydro-benzthiazole of the formula: ##STR15## wherein R 1 is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkenyl or alkynyl group each having 3 to 6 carbon atoms, an alkanoyl group having 1 to 6 carbon atoms, a phenyl alkyl or phenyl alkanoyl group having 1 to 3 carbon atoms in the alkyl part, wherein the above mentioned phenyl nuclei may be substituted by 1 or 2 halogen atoms; R 2 is a hydrogen atom or an alkyl group with 1 to 4 carbon atoms; and R 3 and R 4 together with the nitrogen atom between them form a pyrrolidino group; or, a pharmaceutically acceptable acid addition salt thereof.
Claim 3
Dependent Claim 20 words
A tetrahydro-benzthiazole of formula I, as claimed in claim 1, wherein the ##STR16## group is in the 5 or 6-position.
Claim 4
Dependent Claim 77 words
A tetrahydro-benzthiazole of the formula: ##STR17## wherein R 1 is a hydrogen atom, an alkyl group having 1 to 3 carbon atoms, an allyl, benzyl, 2-chloro-benzyl, 4-chloro-benzyl, 3,4-dichloro-benzyl or phenylethyl group; R 2 is a hydrogen atom, a methyl or ethyl group; and R 3 and R 4 together with the nitrogen atom between them form a pyrrolidino group, wherein said pyrrolidino group is in the 5- or 6-position; or, a pharmaceutically acceptable acid addition salt thereof.
Claim 5
Dependent Claim 77 words
A tetrahydro-benzthiazole of the formula: ##STR17## wherein R 1 is a hydrogen atom, an alkyl group having 1 to 3 carbon atoms, an allyl, benzyl, 2-chloro-benzyl, 4-chloro-benzyl, 3,4-dichloro-benzyl or phenylethyl group; R 2 is a hydrogen atom, a methyl or ethyl group; and R 3 and R 4 together with the nitrogen atom between them form a pyrrolidino group, wherein said pyrrolidino group is in the 5- or 6-position; or, a pharmaceutically acceptable acid addition salt thereof.
Claim 6
Dependent Claim 18 words
A tetrahydro-benzthiazole of formula Ia, as claimed in claim 3, wherein the ##STR18## group is in the 6-position.
Claim 7
Dependent Claim 42 words
A tetrahydro-benzthiazole of the formula: ##STR19## wherein R 1 and R 2 together with the nitrogen atom between them form an amino or allylamino group; and, R 3 and R 4 together with the nitrogen atom between them form a pyrrolidino group.
Claim 8
Dependent Claim 42 words
A tetrahydro-benzthiazole of the formula: ##STR19## wherein R 1 and R 2 together with the nitrogen atom between them form an amino or allylamino group; and, R 3 and R 4 together with the nitrogen atom between them form a pyrrolidino group.
Claim 9
Dependent Claim 9 words
2-amino-6-pyrrolidino-4,5,6,7-tetrahydro-benzthiazole, or a pharmaceutically acceptable acid addition salt thereof.
Claim 10
Dependent Claim 9 words
2-amino-6-pyrrolidino-4,5,6,7-tetrahydro-benzthiazole, or a pharmaceutically acceptable acid addition salt thereof.
Claim 11
Dependent Claim 29 words
A pharmaceutical composition for treating parkinsonism or Parkinson's Disease comprising a therapeutically effective amount of a compound of claims 3, 4, 5 or 6 and a pharmaceutically acceptable carrier.
Claim 12
Independent Claim 28 words
A method of treating parkinsonism which comprises administering to a host suffering from same a therapeutically effective amount of a compound of claims 3, 4, 5 or 6.
Claim 13
Independent Claim 29 words
A method of treating Parkinson's disease which comprises administering to a host suffering from same a therapeutically effective amount of a compound of claims 3, 4, 5 or 6.

References Cited (Backward Citations)

GB812512A Cited
EP0021940A1 Cited
US4337343A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1991-03-15 1991-09-14 1992-03-15 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1995-03-15 1995-09-14 1996-03-15 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1999-03-15 1999-09-14 2000-03-15 $7700.00 Window Closed / Lapsed

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