Propanamine derivatives

• US 5,135,955 A
• Filed: 02/22/1989
• Issued: 08/04/1992
• Est. Priority Date: 04/25/1988
• Status: Expired due to Fees

• Current Assignee: Eli Lilly and Company
• Original Assignee: Eli Lilly and Company
• Inventors: Campbell, Jack B., Smith, Gerald F., Turner, William W.
• Primary Examiner(s): Waddell, Frederick E.
• Assistant Examiner(s): WEDDINGTON, KEVIN E
• Application Number:
  US07/313,571
• Time in Patent Office: 1,259 Days
• Field of Search: 514/649, 514/654, 514/822
• US Class Current: 514/654
• CPC Class Codes: C07C 211/27 having amino groups linked to the six-membered aromatic ring by saturated carbon chains
• CPC Class Codes: C07C 211/30 the six-membered aromatic ring being part of a condensed ring system formed by two rings
• CPC Class Codes: C07C 217/60 linked by carbon chains having two carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring
• CPC Class Codes: C07C 217/62 linked by carbon chains having at least three carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring
• CPC Class Codes: C07C 255/13 containing cyano groups and etherified hydroxy groups bound to the carbon skeleton
• CPC Class Codes: C07C 2601/02 with a three-membered ring
• CPC Class Codes: C07C 2601/08 the ring being saturated
• CPC Class Codes: C07C 2601/14 The ring being saturated
• CPC Class Codes: C07C 309/65 of a saturated carbon skeleton
• CPC Class Codes: C07C 309/73 to carbon atoms of non-condensed six-membered aromatic rings
• CPC Class Codes: C07C 323/12 the carbon skeleton being acyclic and saturated
• CPC Class Codes: C07D 213/38 having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
• CPC Class Codes: C07D 231/12 with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
• CPC Class Codes: C07D 233/56 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
• CPC Class Codes: C07D 249/08 1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
• CPC Class Codes: C07D 295/096 with the ring nitrogen atoms and the oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
• CPC Class Codes: C07D 317/58 Radicals substituted by nitrogen atoms nitro radicals C07D317/52

Abstract

Substituted propanamines having anticoagulant or antifungal activity are disclosed. Also disclosed are methods of use involving the substituted propanamines as well as pharmaceutical compositions containing them.

Claims

1. A method of inhibiting the coagulation of blood in a patient in need thereof comprising administering to said patient an effective anticoagulant amount of a compound of the formula ##STR10## wherein R¹ is ##STR11## wherein R⁷ is C₁ -C₁₄ alkyl or -(CH₂)_n Z, wherein n is an integer from 1-4, both inclusive and Z is phenyl;

R² is hydrogen, phenyl or naphthyl; and

R³, R⁴ and R⁵ are each independently hydrogen or C₁ -C₄ alkyl, and pharmaceutically acceptable salts thereof.

2. The method of claim 1 where, in the definition of R¹, the value R⁷ is C₃ -C₁₀ alkyl or, when R⁷ is --(CH₂)_n Z, n is 1 or 2;

R₂ is hydrogen or phenyl; and

R³, R⁴ and R⁵ are each independently hydrogen or C₁ -C₄ alkyl; and

pharmaceutically acceptable salts thereof.

3. The method of claim 1 where, in the definition of R¹, the value R⁷ is C₄ -C₇ alkyl and pharmaceutically acceptable salts thereof.

4. The method of claim 3 wherein the compound employed is α

-methyl-4-(pentyloxy)benzenepropanamine hydrochloride.

5. The method of claim 3 wherein the compound employed is 4-(heptyloxy)-α

-methylbenzenepropanamine hydrochloride.

6. The method of claim 3 wherein the compound employed is 4-(hexyloxy)-β

-phenylbenzenepropanamine hydrochloride.

7. The method of claim 3 wherein the compound employed is 4-butoxy-N,N,α

-trimethylbenzenepropanamine hydrochloride.