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US3627775A Expired / Lapsed US ⏱️ 0.0 years remaining

1-alkyl-1,2,5,6-tetrahydro-3-pyridylmethyl carboxylic

Assignee: C.H. Boehringer Sohn AG and Co KG
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Filing: 1969-06-25
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Granted: 1971-12-14
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Expires: 1989-06-25
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Abstract

Abstract 1-ALKYL-1,2,5,6-TETRAHYDRO-3-PYRIDYLMETHYL CARBOXYLIC ACID ESTERS OF THE FORMULA WHEREIN R is selected from the group consisting of alkyl of two to 10 carbon atoms optionally substituted with cyano or alkoxy of one to seven carbon atoms, branched alkyl of three to five carbon atoms, alkenyl of two to three carbon atoms optionally substituted with a halogen, alkynyl of two to three carbon atoms, cycloalkyl of three to six carbon atoms and phenyl alkyl of one to seven alkyl carbon atoms, R1 is selected from the group consisting of hydrogen, methyl, -OH and C1-, R2 is selected from the group consisting of hydrogen, phenyl, cycloalkyl of five to six carbon rings and R1 and R2 together with the carbon to which they are attached form a five to six member cycloaliphatic ring, R3 is phenyl and when R2 and R3 are each phenyl they may optionally be linked together in the orthopositions by a direct bond or through an oxygen atom and their nontoxic, pharmaceutically acceptable acid addition salts and quaternary ammonium salts which compounds possess spasmolytic and central sedative properties without undesirable side effects usually associated with spasmolytics.

Inventors

  • 👤 Hans-Hugo Hubner
  • 👤 Gerhard Walther
  • 👤 Karl Zeile
  • 👤 Helmut Wick
  • 👤 Klaus Stockhaus

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-09 00:36
CPC Classifications
C; C07; C07D; C07D213/00; C07D213/02; C07D213/04; C07D213/60; C07D213/78; C07D213/79; C07D211/00; C07D211/04; C07D211/68; C07D211/70

Claims Analysis

Total Claims: 7
Claim 1
Independent Claim 25 words
A compound according to claim 13, wherein R is alkyl of two to six carbon atoms or allyl, R1 is hydroxyl and R2 is phenyl.
Claim 2
Dependent Claim 22 words
A compound according to claim 13, which is 1-n-hexyl-1,2,5, 6-tetrahydro-3-pyridylmethyl benzilic acid ester or a nontoxic, pharmaceutically acceptable acid addition salt thereof.
Claim 3
Dependent Claim 21 words
A compound according to claim 13, which is 1-ethyl-1,2,5,6-tetrahydro-3-pyridylmethyl benzilic acid ester or a nontoxic, pharmaceutically acceptable acid addition salt thereof.
Claim 4
Dependent Claim 21 words
A compound according to claim 13, which is 1-n-amyl-1,2,5,6-tetrahydro-3-pyridylmethyl benzilic acid ester or a nontoxic, pharmaceutically acceptable acid addition salt thereof.
Claim 5
Dependent Claim 27 words
A compound according to claim 13, which is 1-phenylethyl-1,2, 5,6-tetrahydro-3-pyridylmethyl benzilic acid ester or a nontoxic, pharmaceutically acceptable acid addition salt thereof and its quaternary ammonium salts.
Claim 6
Dependent Claim 21 words
A compound according to claim 13, which is 1-allyl-1,2,5,6-tetrahydro-3-pyridylmethyl benzilic acid ester or a nontoxic, pharmaceutically acceptable acid addition salt thereof.
Claim 7
Dependent Claim 53 words
A compound according to claim 1, wherein R is alkyl of two to 10 carbon atoms, allyl, chloroallyl, propargyl or phenethyl, R1 is hydrogen or hydroxyl, R2 is phenyl, cyclopentyl or cyclohexyl, and R1 and R2, together with each other and the carbon atoms to which they are attached, are cyclopentyl or cyclohexyl.

References Cited (Backward Citations)

No citation records indexed.

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1974-12-13 1975-06-14 1975-12-14 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1978-12-13 1979-06-14 1979-12-14 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1982-12-13 1983-06-14 1983-12-14 $7700.00 Window Closed / Lapsed

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