WO2000061234A1 - Combinaisons d'analogues d'acide glutamique et d'acide gamma-aminobutyrique (gaba) et de composes tricycliques permettant de traiter la depression - Google Patents

Combinaisons d'analogues d'acide glutamique et d'acide gamma-aminobutyrique (gaba) et de composes tricycliques permettant de traiter la depression Download PDF

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Publication number
WO2000061234A1
WO2000061234A1 PCT/US2000/003983 US0003983W WO0061234A1 WO 2000061234 A1 WO2000061234 A1 WO 2000061234A1 US 0003983 W US0003983 W US 0003983W WO 0061234 A1 WO0061234 A1 WO 0061234A1
Authority
WO
WIPO (PCT)
Prior art keywords
formula
gabapentin
hydrogen
composition
gaba analog
Prior art date
Application number
PCT/US2000/003983
Other languages
English (en)
Inventor
Leslie Magnus
Douglas A. Saltel
Original Assignee
Warner-Lambert Company
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Warner-Lambert Company filed Critical Warner-Lambert Company
Priority to AU34929/00A priority Critical patent/AU3492900A/en
Priority to KR1020017012788A priority patent/KR20010108466A/ko
Priority to NZ514401A priority patent/NZ514401A/en
Priority to JP2000610562A priority patent/JP2002541224A/ja
Priority to IL14573600A priority patent/IL145736A0/xx
Priority to CA002367494A priority patent/CA2367494A1/fr
Priority to EP00913490A priority patent/EP1180058A1/fr
Publication of WO2000061234A1 publication Critical patent/WO2000061234A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
    • A61K31/197—Carboxylic acids, e.g. valproic acid having an amino group the amino and the carboxyl groups being attached to the same acyclic carbon chain, e.g. gamma-aminobutyric acid [GABA], beta-alanine, epsilon-aminocaproic acid, pantothenic acid
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/415—1,2-Diazoles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/445—Non condensed piperidines, e.g. piperocaine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/24—Antidepressants

Definitions

  • the present invention relates to the use of analogs of glutamic acid and gamma-aminobutyric acid (GABA) in combination with tricyclic compounds for the treatment of depression.
  • GABA gamma-aminobutyric acid
  • the GABA analogs of the present invention are known agents useful in antiseizure therapy for central nervous system disorders such as epilepsy,
  • WO 97/33858 teaches that compounds related to gabapentin are useful or treating epilespy, faintness attacks, hypokinesia, cranial disorders, neurodegenerative disorders, depression, anxiety, panic, pain, and neuropathological disorders. WO 97/33858 does not specify what forms of pain are treated. Additionally, the compounds of the invention are known for treatment of neuropathic pain. For example, see Rosner H; Rubin L; Kestenbaum A., Gabapentin adjunctive therapy in neuropathic pain states. Clin J Pain, 1996 Mar, 12:1, 56-8; Segal AZ; Rordorf G., Gabapentin as a novel treatment for postherpetic neuralgia.
  • Tricyclic antidepressants are prescribed for endogenous depression, a condition thought to be caused by a defect in the uptake of amine neurotransmitters at the presynaptic junctions.
  • the tricyclic antidepressants benefit from a controlled delivery formulation for a number of reasons. Depressed patients are at a higher risk for suicide, and thus more likely to hoard the drug and then attempt to take an overdose. Furthermore, tricyclic antidepressants have a long induction period, sometimes taking several weeks before patients obtain
  • a controlled delivery form of the drug solves these problems by providing continuous release of the drug for the time period necessary to provide relief.
  • tricyclic antidepressants are much more likely to avoid a relapse if they are maintained on the drug.
  • patient compliance to long-term drug regimens is generally very poor. This problem is also eliminated with controlled release drug formulations. Representative examples of tricyclic antidepressants are shown below.
  • Tricyclic antidepressant drugs such as imipramine. 2 -chloroimipramine and amitriptyline; penfluridol; haloperidol; pimozide; clozapine; calmidazolin: and, mixtures and pharmaceutically acceptable salts of any of the foregoing are useful in the present invention
  • compositions comprising a gaba analog and a tricyclic antidepressant in a pharmaceutically-
  • compositions according to the invention comprise at least one gaba analog and at least one tricyclic antidepressant both in amounts effective to alleviate symptoms of depression.
  • This invention provides a method for treating depression comprising administering to a subject suffering from depression an effective amount of a GABA analog in combination with an effective amount of a tricyclic compounds.
  • a preferred embodiment utilizes a cyclic amino acid compound of Formula I
  • R ⁇ is hydrogen or lower alkyl and n is an integer of from 4 to 6, and the
  • An especially preferred embodiment utilizes a compound of Formula I where Ri is hydrogen and n is 4, which
  • gabapentin l-(aminomethyl)-cyclohexane acetic acid, known generically as gabapentin.
  • the invention includes treating depression with a compound of Formula II.
  • R ⁇ is a straight or branched alkyl of from 1 to 6 carbon atoms, phenyl, or
  • R 2 is hydrogen or methyl
  • R3 is hydrogen, methyl, or carboxyl; and tricyclic compounds.
  • Preferred compounds of the invention are those wherein R3 and R 2 are
  • R is -(CH 2 )o-2"i C4H9 as an (R), (S), or (R,S) isomer.
  • the more preferred compounds of Formula II invention are (S)-3-
  • the method of this invention utilizes any GABA analog.
  • a GABA analog is any compound derived from or based upon gamma-aminobutyric acid.
  • the compounds are readily available, either commercially, or by synthetic methodology well-known to those skilled in the art of organic chemistry.
  • the preferred GABA analogs to be utilized in the method of this invention are cyclic amino acids of Formula I. These are described in U.S. Patent 4,024,175, which is incorporated herein by reference.
  • Another preferred method utilizes the GABA analogs of Formula II, and these are described in U.S. Patent 5,563,175, which is incorporated herein by reference.
  • GABA analog in combination with tricyclic compounds All that is required to practice the method of this invention is to administer a GABA analog in combination with tricyclic compounds.
  • the amount of GABA analog in the composition will generally be from about 1 to about 300 mg per kg of subject body weight. Typical doses will be from about 10 to about 5000 mg per day for an adult subject of normal weight. It is expected that common doses that might be administered could be from 100 mg three times a day up to 600 mg four times a day.
  • Commercially available capsules of 100 mg, 300 mg, and 400 mg of gabapentin can be administered. Alternate forms include liquids and film-coated tablets.
  • the dosage level is one sixth that of gabapentin.
  • the dosage range for pregabalin is from about 0.15 mg to about 50 mg per kg per day of subject body weight Typical dosages for pregabalin will be from about 1.6 mg to about 840 mg per day with individual dosages ranging from abut 0.15 mg to about 65 mg per dose.
  • the dosage range for the tricyclic antidepressant can be determined by one skilled in the art.
  • Amitriptyline is available in 10, 25, 50, 75 and 150 mg tablets.
  • Daily dosages can range from between 75 to 350 mg.
  • a benefit of the claimed compositions is to lessen the chance of overdose. Overdoses of antidepressants are common reports to poison control centers. As a result, physicians and pharmacists are encouraged to provide small prescriptions
  • Antidepressant are therefore potential lethal as the dose is increased and patients have to be titrated up to an effective dose.
  • This invention would allow for a synergistic improvement in mood with lower doses (therefore) safer and potentially faster.
  • the different mechanism of action of the two drugs would offer greater benefit to patients.
  • the compounds of the present invention may form pharmaceutically
  • the acid addition salts of the basic compoxmds are prepared either by dissolving the free base in aqueous or aqueous alcohol solution or other suitable solvents containing the appropriate acid and isolating the salt by evaporating the solution.
  • Examples of pharmaceutically acceptable salts are hydrochlorides, hydrobromides, hydrosulfates, etc. as well as sodium, potassium, and magnesium, etc. salts.
  • the compounds of the Formula II can contain one or several asymmetric carbon atoms.
  • the invention includes the individual diastereomers or enantiomers, and the mixtures thereof.
  • the individual diastereomers or enantiomers may be prepared or isolated by methods already well-known in the art.
  • Formulating the active compound in dosage unit form with a pharmaceutical carrier produces pharmaceutical compositions of the compound of the present invention or its salts.
  • dosage unit forms are tablets, capsules, pills, powders, aqueous and nonaqueous oral solutions and suspensions, and parenteral solutions packaged in containers containing either one or some larger number of dosage units and capable of being subdivided into individual doses.
  • suitable pharmaceutical carriers are gelatin capsules; sugars such as lactose and sucrose; starches such as com starch and potato starch, cellulose derivatives such as sodium carboxymethyl cellulose, ethyl cellulose, methyl cellulose, and cellulose acetate phthalate; gelatin; talc; stearic acid; magnesium stearate; vegetable oils such as peanut oil, cottonseed oil, sesame oil, olive oil, com oil, and oil of theobroma; propylene glycol, glycerin; sorbitol; polyethylene glycol; water; agar; alginic acid; isotonic saline, and phosphate buffer solutions; as well as other compatible substances normally used in pharmaceutical formulations.
  • the compositions of the invention can also contain other components such as coloring agents, flavoring agents, and/or preservatives. These materials, if present, are usually used in relatively small amounts.
  • the compositions can, if desired, also contain other therapeutic agents, if present, are usually
  • the percentage of the active ingredients in the foregoing compositions can be varied within wide limits, but for practical purposes it is preferably present in a concentration of at least 10% in a solid composition and at least 2% in a primary liquid composition.
  • the most satisfactory compositions are those in which a much higher proportion of the active ingredient is present.
  • a useful intravenous dose is between 5 and 50 mg and a useful oral dosage is between 20 and 800 mg.
  • the dosage is within the dosing range used in treatment of pain or as would be with the needs of the patient as described by the physician.
  • the advantages of using the compounds of Formula I and II, especially gabapentin and pregabalin, in the instant invention include the relatively nontoxic nature of the compounds, the ease of preparation, the fact that the compounds are well-tolerated, and the ease of IN administration of the drugs.
  • Gabapentin has few interactions with major classes of drugs since it is not metabolized in the liver, but rather excreted unchanged from the body. Further, the drugs are not metabolized in the body.
  • the subjects treated with the method of the present invention are mammals, including humans.

Abstract

L'invention concerne une technique utilisant certains analogues d'acide glutamique et d'acide gamma-aminobutyrique associés à des composés tricycliques, afin de traiter la dépression.
PCT/US2000/003983 1999-04-09 2000-02-16 Combinaisons d'analogues d'acide glutamique et d'acide gamma-aminobutyrique (gaba) et de composes tricycliques permettant de traiter la depression WO2000061234A1 (fr)

Priority Applications (7)

Application Number Priority Date Filing Date Title
AU34929/00A AU3492900A (en) 1999-04-09 2000-02-16 Combinations of gaba analogs and tricyclic compounds to treat depression
KR1020017012788A KR20010108466A (ko) 1999-04-09 2000-02-16 우울증 치료용 ｇａｂａ 유사체와 삼환계 화합물의 복합제제
NZ514401A NZ514401A (en) 1999-04-09 2000-02-16 Combinations of GABA analogs and tricyclic compounds to treat depression
JP2000610562A JP2002541224A (ja) 1999-04-09 2000-02-16 うつ病の治療のためのｇａｂａ類縁体と三環系化合物の組合わせ
IL14573600A IL145736A0 (en) 1999-04-09 2000-02-16 Combinations of gaba analogs and tricyclic compounds to treat depression
CA002367494A CA2367494A1 (fr) 1999-04-09 2000-02-16 Combinaisons d'analogues d'acide glutamique et d'acide gamma-aminobutyrique (gaba) et de composes tricycliques permettant de traiter la depression
EP00913490A EP1180058A1 (fr) 1999-04-09 2000-02-16 Combinaisons d'analogues d'acide glutamique et d'acide gamma-aminobutyrique (gaba) et de composes tricycliques permettant de traiter la depression

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US12857199P 1999-04-09 1999-04-09
US60/128,571 1999-04-09

Publications (1)

Publication Number Publication Date
WO2000061234A1 true WO2000061234A1 (fr) 2000-10-19

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PCT/US2000/003983 WO2000061234A1 (fr) 1999-04-09 2000-02-16 Combinaisons d'analogues d'acide glutamique et d'acide gamma-aminobutyrique (gaba) et de composes tricycliques permettant de traiter la depression

Country Status (11)

Country Link
EP (1) EP1180058A1 (fr)
JP (1) JP2002541224A (fr)
KR (1) KR20010108466A (fr)
AU (1) AU3492900A (fr)
CA (1) CA2367494A1 (fr)
HU (1) HUP0200733A3 (fr)
IL (1) IL145736A0 (fr)
NZ (1) NZ514401A (fr)
TR (1) TR200102850T2 (fr)
WO (1) WO2000061234A1 (fr)
ZA (1) ZA200108259B (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005025675A1 (fr) * 2003-09-12 2005-03-24 Pfizer Limited Associations comprenant des ligands alpha-2-delta et des inhibiteurs du recaptage de la serotonine et de la noradrenaline
WO2005025563A1 (fr) * 2003-09-12 2005-03-24 Warner-Lambert Company Llc Combinaison comportant un ligand alpha-2-delta et un inhibiteur selectif du recaptage de la serotonine et/ou un inhibiteur selectif du recaptage de la noradrenaline et permettant le traitement de la depression et des troubles anxieux
JP2005518411A (ja) * 2002-01-16 2005-06-23 エンド ファーマシューティカルズ インコーポレーテッド 中枢神経系の障害を治療する製薬組成物及び方法
USRE41920E1 (en) 1996-07-24 2010-11-09 Warner-Lambert Company Llc Isobutylgaba and its derivatives for the treatment of pain

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2262997A1 (en) * 1974-03-07 1975-10-03 Hoechst Ag Psychotropic medicaments contg. (pyro)-Glue-His-Pro-amide - and thymoleptics, monoaminoxidase inhibitors or neuroleptics
FR2453643A2 (fr) * 1977-06-24 1980-11-07 Synthelabo Compositions pharmaceutiques actives sur le systeme nerveux central
US5025035A (en) * 1990-10-12 1991-06-18 Warner-Lambert Company Method of treating depression
WO1992009560A1 (fr) * 1990-11-27 1992-06-11 Northwestern University Analogues de l'acide gamma-aminobutyrique (gaba) et de l'acide l-glutamique utilises dans le traitement contre les attaques
EP0726073A2 (fr) * 1995-02-10 1996-08-14 Eduardo Samuel Bleiweiss Compositions pharmaceutique contenant au moins un composé choisi parmi le haloperidol, imipramine et le trifluoroperazine

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2262997A1 (en) * 1974-03-07 1975-10-03 Hoechst Ag Psychotropic medicaments contg. (pyro)-Glue-His-Pro-amide - and thymoleptics, monoaminoxidase inhibitors or neuroleptics
FR2453643A2 (fr) * 1977-06-24 1980-11-07 Synthelabo Compositions pharmaceutiques actives sur le systeme nerveux central
US5025035A (en) * 1990-10-12 1991-06-18 Warner-Lambert Company Method of treating depression
WO1992009560A1 (fr) * 1990-11-27 1992-06-11 Northwestern University Analogues de l'acide gamma-aminobutyrique (gaba) et de l'acide l-glutamique utilises dans le traitement contre les attaques
EP0726073A2 (fr) * 1995-02-10 1996-08-14 Eduardo Samuel Bleiweiss Compositions pharmaceutique contenant au moins un composé choisi parmi le haloperidol, imipramine et le trifluoroperazine

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
SABETKASAI, M. ET AL: "Baclofen and antidepressant -induced antinociception in formalin test: possible GABAB mechanism involvement", PSYCHOPHARMACOLOGY (BERLIN) (1999), 142(4), 426-431, XP000933550 *
WETZEL C H ET AL: "Use of gabapentin in pain management", ANNALS OF PHARMACOTHERAPY,XX,XX, vol. 31, no. 9, September 1997 (1997-09-01), pages 1082 - 1083, XP002101739, ISSN: 1060-0280 *

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
USRE41920E1 (en) 1996-07-24 2010-11-09 Warner-Lambert Company Llc Isobutylgaba and its derivatives for the treatment of pain
JP2005518411A (ja) * 2002-01-16 2005-06-23 エンド ファーマシューティカルズ インコーポレーテッド 中枢神経系の障害を治療する製薬組成物及び方法
WO2005025675A1 (fr) * 2003-09-12 2005-03-24 Pfizer Limited Associations comprenant des ligands alpha-2-delta et des inhibiteurs du recaptage de la serotonine et de la noradrenaline
WO2005025563A1 (fr) * 2003-09-12 2005-03-24 Warner-Lambert Company Llc Combinaison comportant un ligand alpha-2-delta et un inhibiteur selectif du recaptage de la serotonine et/ou un inhibiteur selectif du recaptage de la noradrenaline et permettant le traitement de la depression et des troubles anxieux
KR100828218B1 (ko) * 2003-09-12 2008-05-07 화이자 인코포레이티드 알파-2-델타 리간드 및 세로토닌/노르아드레날린 재흡수 억제제를 포함하는 조합물
EP2156863A3 (fr) * 2003-09-12 2011-01-12 Pfizer Limited Combinaisons d'inhibiteurs d'alpha-2-delta et d'inhibiteurs de récapture de sérotonine/noradrénaline

Also Published As

Publication number Publication date
NZ514401A (en) 2003-10-31
EP1180058A1 (fr) 2002-02-20
JP2002541224A (ja) 2002-12-03
AU3492900A (en) 2000-11-14
HUP0200733A3 (en) 2003-04-28
HUP0200733A2 (hu) 2002-07-29
IL145736A0 (en) 2002-07-25
KR20010108466A (ko) 2001-12-07
CA2367494A1 (fr) 2000-10-19
ZA200108259B (en) 2003-03-26
TR200102850T2 (tr) 2002-03-21

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