Use of 1-Phenyl-3-dimethylamino-propane Compounds for Treating Neuropathic Pain

US 20100311842A1
Filed: 08/04/2010
Published: 12/09/2010
Est. Priority Date: 03/12/2007
Status: Active Grant

First Claim

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1. A method of treating polyneuropathic pain in a subject suffering therefrom, said method comprising administering to said subject an effective polyneuropathic pain inhibiting amount of a 1-phenyl-3-dimethylamino-propane compound corresponding to Formula I:

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Abstract

Use of 1-phenyl-3-dimethylaminopropane compounds for the production of medicaments for treating neuropathic pain, preferably polyneuropathic pain, also preferably diabetic neuropathic pain, more preferably diabetic peripheral neuropathic pain, and furthermore preferably for treating diabetic peripheral neuropathy.

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21 Claims

1. A method of treating polyneuropathic pain in a subject suffering therefrom, said method comprising administering to said subject an effective polyneuropathic pain inhibiting amount of a 1-phenyl-3-dimethylamino-propane compound corresponding to Formula I:
- View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19)
- - 2. A method according to claim 1, wherein in said compound of Formula I:
    - X denotes OH, F, OC(O)CH₃or H;
      
      R¹denotes CH₃, C₂H₅, C₄H₉or t-butyl;
      
      R²and R³independently denote H, CH₃, C₂H₅, i-propyl or t-butyl;
      
      orR²and R³together with the carbon atom to which they are attached form a saturated and unsubstituted C_5-6-cycloalkyl group; and
      
      at least 3 of R⁹to R¹³denote H and the remainder are independently selected from the group consisting of H, Cl, F, OH, CF₂H, CF₃, OCH₃and SCH₃;
  - 3. A method according to claim 1, wherein in said compound of Formula I, R⁹, R¹¹and R¹³denote H, one of R¹⁰and R¹²also denotes H, and the other is selected from the group consisting of Cl, F, OH, CF₂H, CF₃, OR¹⁴and SR¹⁴.
  - 4. A method according to claim 3, wherein the other of R¹⁰and R¹²is selected from the group consisting of OH, CF₂H, OCH₃and SCH₃.
  - 5. A method according to claim 1, wherein in said compound of Formula I, R⁹and R¹³each denote H;
    - R¹¹denotes OH, OCH₃, Cl or F; and
      
      one of R¹⁰and R¹²denotes H, while the other denotes OH, OCH₃, Cl or F.
  - 6. A method according to claim 5, wherein R¹¹and the other of R¹⁰and R¹²each denote Cl.
  - 7. A method according to claim 1, wherein in said compound of Formula I, R⁹, R¹⁰, R¹²and R¹³each denote H;
    - andR¹¹denotes CF₃, CF₂H, Cl or F.
  - 8. A method according to claim 1, wherein in said compound of Formula I, R¹⁰, R¹¹and R¹²each denote H;
    - andone of R⁹and R¹³denotes H, while the other denotes OH, OC₂H₅or OC₃H₇.
  - 9. A method according to claim 1, wherein said compound of Formula I is in the form of an isolated stereoisomer.
  - 10. A method according to claim 1, wherein said compound of Formula I is in the form of a mixture of stereoisomers.
  - 11. A method according to claim 10, wherein said mixture is a racemic mixture.
  - 12. A method according to claim 1, wherein in said compound of Formula I, R³denotes H, and said compound is present in the form of an isolated diastereomer having the stereochemical configuration of Formula Ia
  - 13. A method according to claim 1, wherein said compound of Formula I is selected from the group consisting of:
    - (2RS, 3RS)-1-dimethylamino-3-(3-methoxyphenyl)-2-methyl-pentan-3-ol,(+)-(2R,3R)-1-dimethylamino-3-(3-methoxyphenyl)-2-methyl-pentan-3-ol,(2R,3R)-1-dimethylamino-3-(3-methoxyphenyl)-2-methylpentan-3-ol,(−
      
      )-(2S,3S)-1-dimethylamino-3-(3-methoxyphenyl)-2-methyl-pentan-3-ol,(2S,3S)-1-dimethylamino-3-(3-methoxyphenyl)-2-methylpentan-3-ol,(2RS,3RS)-3-(3,4-dichlorophenyl)-1-dimethylamino-2-methyl-pentan-3-ol,(2RS,3RS)-3-(3-difluoromethylphenyl)-1-dimethylamino-2-methyl-pentan-3-ol,(2RS, 3RS)-1-dimethylamino-2-methyl-3-(3-methylsulfanylphenyl)-pentan-3-ol,(3RS)-1-dimethylamino-3-(3-methoxyphenyl)-4,4-dimethylpentan-3-ol,(2RS,3RS)-3-(3-dimethylamino-1-ethyl-1-hydroxy-2-methylpropyl)-phenol,(1RS, 2RS)-3-(3-dimethylamino-1-hydroxy-1,2-dimethylpropyl)-phenol,(+)-(1R,2R)-3-(3-dimethylamino-1-hydroxy-1,2-dimethylpropyl)-phenol,(1R,2R)-3-(3-dimethylamino-1-hydroxy-1,2-dimethylpropyl)phenol,(−
      
      )-(1S,2S)-3-(3-dimethylamino-1-hydroxy-1,2-dimethylpropyl)-phenol,(1S,2S)-3-(3-dimethylamino-1-hydroxy-1,2-dimethylpropyl)phenol,(RS, RS)-3-(3-dimethylamino-1-ethyl-2-methylpropyl)phenol,(−
      
      )-(1R,2R)-3-(3-dimethylamino-1-ethyl-2-methylpropyl)phenol,(1R,2R)-3-(3-dimethylamino-1-ethyl-2-methylpropyl)phenol,(+)-(1S,2S)-3-(3-dimethylamino-1-ethyl-2-methylpropyl)phenol,(1S,2S)-3-(3-dimethylamino-1-ethyl-2-methylpropyl)phenol,(+)-(1R,2R)-acetic acid-3-dimethylamino-1-ethyl-1-(3-methoxy-phenyl)-2-methyl propyl ester,(2RS, 3RS)-3-(4-chlorophenyl)-1-dimethylamino-2-methylpentan-3-ol,(+)-(2R,3R)-3-(3-dimethylamino-1-ethyl-1-hydroxy-2-methylpropyl)-phenol,(2RS, 3RS)-4-dimethylamino-2-(3-methoxyphenyl)-3-methylbutan-2-ol,(+)-(2R,3R)-4-dimethylamino-2-(3-methoxyphenyl)-3-methylbutan-2-ol, and pharmaceutically acceptable salts of any of the foregoing.
  - 14. A method according to claim 13, wherein said compound of Formula I is selected from the group consisting of:
    - (RS, RS)-3-(3-dimethylamino-1-ethyl-2-methylpropyl)phenol,(−
      
      )-(1R,2R)-3-(3-dimethylamino-1-ethyl-2-methylpropyl)phenol,(1R,2R)-3-(3-dimethylamino-1-ethyl-2-methylpropyl)phenol,(−
      
      )-(1S,2S)-3-(3-dimethylamino-1-ethyl-2-methylpropyl)phenol,(1S,2S)-3-(3-dimethylamino-1-ethyl-2-methylpropyl)phenol, and pharmaceutically acceptable acid addition salts of any of the foregoing.
  - 15. A method according to claim 14, wherein said compound of Formula I is (1RS, 2RS)-3-(3-dimethylamino-1-ethyl-2-methylpropyl)-phenol or a hydrochloride salt thereof.
  - 16. A method according to claim 14, wherein said compound of Formula I is (−
    - )-(1R,2R)-3-(3-dimethylamino-1-ethyl-2-methyl-propyl)phenol or a hydrochloride salt thereof.
  - 17. A method according to claim 1, wherein said polyneuropathic pain is diabetic polyneuropathic pain.
  - 18. A method according to claim 1, wherein said polyneuropathic pain is peripheral polyneuropathic pain.
  - 19. A method according to claim 1, wherein said polyneuropathic pain is peripheral diabetic polyneuropathic pain.

20. A method of treating polyneuropathy in a subject suffering therefrom, said method comprising administering to said subject a pharmacologically effective amount of a compound corresponding to Formula I:
- View Dependent Claims (21)
- - 21. A method according to claim 20, wherein said polyneuropathy is diabetic polyneuropathy.

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Current Assignee
Grunenthal GMBH (Grünenthal Pharma GmbH & Co. KG)
Original Assignee
Grunenthal GMBH (Grünenthal Pharma GmbH & Co. KG)
Inventors
Meen, Murielle, CHRISTOPH, Thomas, Koegel, Babette-Yvonne, Friderichs, Elmar

Granted Patent

US 8,536,130 B2
Time in Patent Office

Days
Field of Search
US Class Current

514/653
CPC Class Codes

A61K 31/137   Arylalkylamines, e.g. amphe...

A61P 25/00   Drugs for disorders of the ...

A61P 25/02   for peripheral neuropathies

A61P 25/04   Centrally acting analgesics...

A61P 29/00   Non-central analgesic, anti...

A61P 3/10   for hyperglycaemia, e.g. an...

A61P 43/00   Drugs for specific purposes...

Use of 1-Phenyl-3-dimethylamino-propane Compounds for Treating Neuropathic Pain

First Claim

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Abstract

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Use of 1-Phenyl-3-dimethylamino-propane Compounds for Treating Neuropathic Pain

First Claim

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Abstract

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Specification

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