US20020004528A1 - Method for the treatment of insomnia - Google Patents
Method for the treatment of insomnia Download PDFInfo
- Publication number
- US20020004528A1 US20020004528A1 US09/921,682 US92168201A US2002004528A1 US 20020004528 A1 US20020004528 A1 US 20020004528A1 US 92168201 A US92168201 A US 92168201A US 2002004528 A1 US2002004528 A1 US 2002004528A1
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- Prior art keywords
- formula
- gabapentin
- insomnia
- hydrogen
- compounds
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- CBPLZJZJHASDCU-UHFFFAOYSA-N C.COC(=O)CCCN Chemical compound C.COC(=O)CCCN CBPLZJZJHASDCU-UHFFFAOYSA-N 0.000 description 2
- TVTQTVKMWDZEQA-UHFFFAOYSA-N CC(N)C(C)(C)CC(=O)O.II Chemical compound CC(N)C(C)(C)CC(=O)O.II TVTQTVKMWDZEQA-UHFFFAOYSA-N 0.000 description 2
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
- 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
- A61K31/185—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
-
- 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
- A61P25/08—Antiepileptics; Anticonvulsants
-
- 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
- A61P25/20—Hypnotics; Sedatives
Definitions
- the present invention relates to the use of analogs of glutamic acid and gamma-aminobutyric acid (GABA) for the treatment of insomnia.
- GABA gamma-aminobutyric acid
- GABA analogs are known agents useful in antiseizure therapy for central nervous system disorders such as epilepsy, Huntington's chorea, cerebral ischemia, Parkinson's disease, tardive dyskinesia, and spasticity. It has also been suggested that the compounds can be used as antidepressants, anxiolytics, and antipsychotics. See WO 92/09560 (U.S. Ser. No. 618,692 filed Nov. 27, 1990) and WP 93/23383 (U.S. Ser. No. 886,080 filed May 20, 1992).
- 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.
- the compounds of the invention are known for treatment of neuropathic pain.
- insomnia and sleeplessness are common problems. Often, the insomnia or sleeplessness is precipitated by stress, emotional and physical causes.
- U.S. Pat. No. 5,510,381 directed to the use of gabapentin to treat mania, mentions one study in which gabapentin has also been found to enhance delta-wave (deep) sleep. This effect is beneficial in acute mania and also leads to reducing the risk for onset of a new episode of mania.
- This invention provides a method for treating insomnia in a mammal comprising administering to a subject suffering from insomnia an effective amount of a GABA analog.
- a preferred embodiment utilizes a cyclic amino acid compound of Formula I
- R 1 is hydrogen or lower alkyl and n is an integer of from 4 to 6, and the pharmaceutically acceptable salts thereof.
- An especially preferred embodiment utilizes a compound of Formula I where R 1 is hydrogen and n is 4, which compound is 1-(aminomethyl)-cyclohexane acetic acid, known generically as gabapentin.
- the invention includes treating insomnia with a compound of Formula II.
- R 1 is a straight or branched alkyl of from 1 to 6 carbon atoms, phenyl, or cycloalkyl of from 3 to 6 carbon atoms;
- R 2 is hydrogen or methyl
- R 3 is hydrogen, methyl, or carboxyl.
- Preferred compounds of the invention are those wherein R 3 and R 2 are hydrogen, and R 1 is —(CH 2 ) 0-2 —i C 4 H 9 as an (R), (S), or (R,S) isomer.
- the more preferred compounds of Formula II invention are (S)-3-(aminomethyl)-5-methylhexanoic acid and 3-aminomethyl-5-methyl-hexanoic acid, now known generically as pregabalin.
- 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. Pat. No. 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. Pat. No. 5,563,175 which is incorporated herein by reference.
- All that is required to practice the method of this invention is to administer a GABA analog in an amount that is effective to treat insomnia.
- Such amounts 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 compounds used in the present invention may form pharmaceutically acceptable salts with both organic and inorganic acids or bases.
- the acid addition salts of the basic compounds 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.
- 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.
- compositions of the compound of the present invention or its salts are produced by formulating the active compound in dosage unit form with a pharmaceutical carrier.
- 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 corn 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, corn 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.
- 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.
- routes of administration of the subject compound or its salts are oral or parenteral.
- 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.
- GABA analogs to treat insomnia are not addictive. Additionally, GABA analogs have a half-life in the body that is suitable to work during the evening and subsequently clear the body by morning to allow for easy arousal. GAGA analog's, particularly gabapentin's, method of action is different from other sleep enchancing agents.
- the GABA analogs can be combined with other agents to enhance the sleep inducing effects. Such agents include melatonin, trytophan, valerian, passiflora, antihistamines, such as diphenydramine hydrochloride or doxylamine succinate, densokiazepene and non-benzodipend hypnotics.
- Additional advantages of using the compounds of Formula I and II, especially gabapentin and pregabalin, in the present 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 IV 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.
- the GABA analogs used in the method of the present invention are not addictive. This is a significant advantage over other sleep aids. Also, these compounds have a half life that is suitable to work during the evening and subsequently clear the body by morning to allow for easy arousal.
- the method of action of the GABA analogs is different than other hypnotics and thus can be combined with them to enhance the sleep inducing effects.
- These agents could include melatonin, trytophan, valerian, passiflora, classical antihistamines such as diphenhydramine hydrochloride or doxylamine succinate, as well as benzodiazepene and non-benzodiazepene hypnotics.
Abstract
The instant invention is a method of using certain analogs of glutamic acid and gamma-aminobutyric acid to treat insomnia.
Description
- 1. Field of the Invention
- The present invention relates to the use of analogs of glutamic acid and gamma-aminobutyric acid (GABA) for the treatment of insomnia.
- 2. Description of Related Art
- GABA analogs are known agents useful in antiseizure therapy for central nervous system disorders such as epilepsy, Huntington's chorea, cerebral ischemia, Parkinson's disease, tardive dyskinesia, and spasticity. It has also been suggested that the compounds can be used as antidepressants, anxiolytics, and antipsychotics. See WO 92/09560 (U.S. Ser. No. 618,692 filed Nov. 27, 1990) and WP 93/23383 (U.S. Ser. No. 886,080 filed May 20, 1992).
- 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 March, 12:1, 56-8; Segal A Z; Rordorf G., Gabapentin as a novel treatment for postherpetic neuralgia. Neurology, 1996 April, 46:4, 1175-6; Wetzel C H; Connelly J F., Use of gabapentin in pain management. Ann Pharmacother, 1997 September, 31:9, 1082-3; Zapp J J., Postpoliomyelitis pain treated with gabapentin [letter]. Am Fam Physician, 1996 June, 53:8, 2442, 2445; Cheville A, et al., Neuropathic pain in radiation myelopathy:a case report. Program book, American Pain Society (14th Annual Scientific Meeting). Abstract #95823, p. A-115; Sist T; Filadora V; Miner M; Lema M., Gabapentin for idiopathic trigeminal neuralgia: report of two cases. Neurology, 1997 May, 48:5, 1467; Waldman S D, Tutorial 28: Evaluation and Treatment of Trigeminal Neuralgia. Pain Digest (1997) 7:21-24; Mellick L B; Mellick G A., Successful treatment of reflex sympathetic dystrophy with gabapentin [letter]. Am J Emerg Med, 1995 January, 13:1, 96; Mellick G A; Seng M I., The use of gabapentin in the treatment of reflex sympathetic dystrophy and a phobic disorder. Am J Pain Manage 1995; 5:7-9; Mellick G A; Mellicy L B; Mellick L B., Gabapentin in the management of reflex sympathetic dystrophy [letter]. J Pain Symptom Manage, 1995 May, 10:4, 265-6; Mellick G A; Mellick L B., Reflex sympathetic dystrophy treated with gabapentin. Arch Phys Med Rehabil, 1997 January, 78:1, 98-105 and Mackin G A., Medical and pharmacologic management of upper extremity neuropathic pain syndromes. J Hand Ther, 1997 April-June, 10:2, 96-109.
- Insomnia and sleeplessness are common problems. Often, the insomnia or sleeplessness is precipitated by stress, emotional and physical causes.
- U.S. Pat. No. 5,510,381, directed to the use of gabapentin to treat mania, mentions one study in which gabapentin has also been found to enhance delta-wave (deep) sleep. This effect is beneficial in acute mania and also leads to reducing the risk for onset of a new episode of mania.
-
- wherein R1 is hydrogen or lower alkyl and n is an integer of from 4 to 6, and the pharmaceutically acceptable salts thereof. An especially preferred embodiment utilizes a compound of Formula I where R1 is hydrogen and n is 4, which compound is 1-(aminomethyl)-cyclohexane acetic acid, known generically as gabapentin.
-
- or a pharmaceutically acceptable salt thereof wherein
- R1 is a straight or branched alkyl of from 1 to 6 carbon atoms, phenyl, or cycloalkyl of from 3 to 6 carbon atoms;
- R2 is hydrogen or methyl; and
- R3 is hydrogen, methyl, or carboxyl.
- Preferred compounds of the invention are those wherein R3 and R2 are hydrogen, and R1 is —(CH2)0-2—i C4H9 as an (R), (S), or (R,S) isomer.
- The more preferred compounds of Formula II invention are (S)-3-(aminomethyl)-5-methylhexanoic acid and 3-aminomethyl-5-methyl-hexanoic acid, now known generically as pregabalin.
- 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. Pat. No. 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. Pat. No. 5,563,175 which is incorporated herein by reference.
- All that is required to practice the method of this invention is to administer a GABA analog in an amount that is effective to treat insomnia. Such amounts 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.
- If a compound of Formula II , such as pregabalin is used, 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 compounds used in the present invention may form pharmaceutically acceptable salts with both organic and inorganic acids or bases. For example, the acid addition salts of the basic compounds 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.
- Pharmaceutical compositions of the compound of the present invention or its salts are produced by formulating the active compound in dosage unit form with a pharmaceutical carrier. Some examples of 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. Some examples of suitable pharmaceutical carriers, including pharmaceutical diluents, are gelatin capsules; sugars such as lactose and sucrose; starches such as corn 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, corn 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.
- 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.
- Routes of administration of the subject compound or its salts are oral or parenteral. For example, 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 benefit of using GABA analogs to treat insomnia is that they are not addictive. Additionally, GABA analogs have a half-life in the body that is suitable to work during the evening and subsequently clear the body by morning to allow for easy arousal. GAGA analog's, particularly gabapentin's, method of action is different from other sleep enchancing agents. The GABA analogs can be combined with other agents to enhance the sleep inducing effects. Such agents include melatonin, trytophan, valerian, passiflora, antihistamines, such as diphenydramine hydrochloride or doxylamine succinate, densokiazepene and non-benzodipend hypnotics.
- Additional advantages of using the compounds of Formula I and II, especially gabapentin and pregabalin, in the present 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 IV 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.
- The GABA analogs used in the method of the present invention are not addictive. This is a significant advantage over other sleep aids. Also, these compounds have a half life that is suitable to work during the evening and subsequently clear the body by morning to allow for easy arousal. The method of action of the GABA analogs is different than other hypnotics and thus can be combined with them to enhance the sleep inducing effects. These agents could include melatonin, trytophan, valerian, passiflora, classical antihistamines such as diphenhydramine hydrochloride or doxylamine succinate, as well as benzodiazepene and non-benzodiazepene hypnotics.
Claims (9)
1. A method for treating a mammal suffering from insomnia comprising administering to said mammal a pharmaceutical composition comprising an effective amount of a GABA analog.
3. The method according to claim 2 , wherein Formula I comprises gabapentin.
4. The method according to claim 2 , comprising from about 10 mg to about 400 mg of Formula I.
5. The method according to claim 3 , comprising from about 10 mg to about 400 mg of gabapentin.
6. The method according to claim 1 , wherein the GABA analog is a compound according to Formula II:
or a pharmaceutically acceptable salt thereof wherein
R1 is a straight or branched alkyl of from 1 to 6 carbon atoms, phenyl, or cycloalkyl of from 3 to 6 carbon atoms;
R2 is hydrogen or methyl; and
R3 is hydrogen, methyl, or carboxyl;
7. The method according to claim 11, wherein Formula II comprises pregabalin.
8. The method according to claim 11, comprising from about 0.15 mg to about 65 mg of Formula II.
9. The method according to claim 12, comprising from about 0.15 mg to about 65 mg of pregabalin.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US09/921,682 US20020004528A1 (en) | 1998-07-09 | 2001-08-03 | Method for the treatment of insomnia |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US9216698P | 1998-07-09 | 1998-07-09 | |
US09/743,370 US6306910B1 (en) | 1998-07-09 | 1999-07-01 | Use of Gaba-analogues for treating insomnia |
US09/921,682 US20020004528A1 (en) | 1998-07-09 | 2001-08-03 | Method for the treatment of insomnia |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US09/743,370 Division US6306910B1 (en) | 1998-07-09 | 1999-07-01 | Use of Gaba-analogues for treating insomnia |
Publications (1)
Publication Number | Publication Date |
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US20020004528A1 true US20020004528A1 (en) | 2002-01-10 |
Family
ID=22231954
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US09/743,370 Expired - Fee Related US6306910B1 (en) | 1998-07-09 | 1999-07-01 | Use of Gaba-analogues for treating insomnia |
US09/921,682 Abandoned US20020004528A1 (en) | 1998-07-09 | 2001-08-03 | Method for the treatment of insomnia |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
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US09/743,370 Expired - Fee Related US6306910B1 (en) | 1998-07-09 | 1999-07-01 | Use of Gaba-analogues for treating insomnia |
Country Status (13)
Country | Link |
---|---|
US (2) | US6306910B1 (en) |
EP (1) | EP1094803A2 (en) |
JP (1) | JP2002520277A (en) |
KR (1) | KR20010071778A (en) |
AU (1) | AU765038B2 (en) |
BR (1) | BR9911887A (en) |
CA (1) | CA2333024C (en) |
ID (1) | ID27191A (en) |
NO (1) | NO20010117D0 (en) |
NZ (1) | NZ509231A (en) |
PL (1) | PL345338A1 (en) |
WO (1) | WO2000002546A2 (en) |
ZA (1) | ZA200007174B (en) |
Cited By (2)
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US20030212133A1 (en) * | 2000-06-26 | 2003-11-13 | Bryans Justin Stephen | Gabapentin analogues for sleep disorders |
US20070014260A1 (en) * | 2005-07-15 | 2007-01-18 | Samsung Electronics Co., Ltd. | Dual-mode mobile terminal and method for handover of packet service call between different communication networks |
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US6992109B1 (en) * | 1999-04-08 | 2006-01-31 | Segal Catherine A | Method for the treatment of incontinence |
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US8048917B2 (en) | 2005-04-06 | 2011-11-01 | Xenoport, Inc. | Prodrugs of GABA analogs, compositions and uses thereof |
US7186855B2 (en) | 2001-06-11 | 2007-03-06 | Xenoport, Inc. | Prodrugs of GABA analogs, compositions and uses thereof |
US20030225149A1 (en) * | 2002-04-30 | 2003-12-04 | Blazecka Peter G. | Process for preparing highly functionalized gamma-butyrolactams and gamma-amino acids |
US7071339B2 (en) * | 2002-08-29 | 2006-07-04 | Warner Lambert Company Llc | Process for preparing functionalized γ-butyrolactones from mucohalic acid |
US7025745B2 (en) * | 2002-10-07 | 2006-04-11 | Advanced Cardiovascular Systems, Inc. | Method of making a catheter balloon using a tapered mandrel |
MXPA05006209A (en) * | 2002-12-13 | 2005-08-19 | Warner Lambert Co | Pregabalin and derivates thereof for the treatment of fibromyalgia and other related disorders. |
NZ540336A (en) * | 2002-12-13 | 2008-03-28 | Warner Lambert Co | Gabapentin analogues for fibromyalgia and other related disorders |
CA2451267A1 (en) * | 2002-12-13 | 2004-06-13 | Warner-Lambert Company Llc | Pharmaceutical uses for alpha2delta ligands |
PL377520A1 (en) | 2002-12-13 | 2006-02-06 | Warner-Lambert Company Llc | Pregabalin derivatives for the treatment of fibromyalgia and other disorders |
EP1727620B1 (en) * | 2004-03-12 | 2007-08-29 | Warner-Lambert Company LLC | C1-symmetric bisphosphine ligands and their use in the asymmetric synthesis of pregabalin |
JP4504063B2 (en) * | 2004-03-30 | 2010-07-14 | エスエス製薬株式会社 | Sleep improvement medicine |
CA2561755A1 (en) * | 2004-04-01 | 2005-10-13 | Warner-Lambert Company Llc | Preparation of p-chirogenic phospholanes and their use in asymmetric synthesis |
JP4613031B2 (en) * | 2004-05-06 | 2011-01-12 | エスエス製薬株式会社 | Hypnotic composition |
CA2571040C (en) | 2004-06-21 | 2009-09-15 | Warner-Lambert Company Llc | Preparation of pregabalin and related compounds |
EP1806133A1 (en) * | 2004-10-14 | 2007-07-11 | Daikin Industries, Ltd. | Method for modifying the ambience, and spray liquid and sprayer used in the method |
US20080161393A1 (en) * | 2006-12-08 | 2008-07-03 | Barrett Ronald W | Use of prodrugs of GABA analogs for treating disease |
US20110015261A1 (en) * | 2007-08-03 | 2011-01-20 | Zleepax Europe ApS | Use of a composition comprising at least one beta-blocker for the treatment of sleep disorders |
JP2010043063A (en) | 2008-05-09 | 2010-02-25 | Agency For Science Technology & Research | Diagnosis and treatment of kawasaki disease |
WO2011141923A2 (en) | 2010-05-14 | 2011-11-17 | Lupin Limited | Improved synthesis of optically pure (s) - 3-cyano-5-methyl-hexanoic acid alkyl ester, an intermediate of (s)- pregabalin |
WO2012059797A1 (en) | 2010-11-04 | 2012-05-10 | Lupin Limited | Process for synthesis of (s) - pregabalin |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5510381A (en) | 1995-05-15 | 1996-04-23 | Warner-Lambert Company | Method of treatment of mania and bipolar disorder |
-
1999
- 1999-07-01 BR BR9911887-4A patent/BR9911887A/en not_active Application Discontinuation
- 1999-07-01 CA CA002333024A patent/CA2333024C/en not_active Expired - Fee Related
- 1999-07-01 WO PCT/US1999/015058 patent/WO2000002546A2/en not_active Application Discontinuation
- 1999-07-01 KR KR1020017000261A patent/KR20010071778A/en not_active Application Discontinuation
- 1999-07-01 NZ NZ509231A patent/NZ509231A/en unknown
- 1999-07-01 US US09/743,370 patent/US6306910B1/en not_active Expired - Fee Related
- 1999-07-01 EP EP99933667A patent/EP1094803A2/en not_active Withdrawn
- 1999-07-01 JP JP2000558806A patent/JP2002520277A/en active Pending
- 1999-07-01 AU AU49673/99A patent/AU765038B2/en not_active Ceased
- 1999-07-01 PL PL99345338A patent/PL345338A1/en unknown
- 1999-07-01 ID IDW20010056A patent/ID27191A/en unknown
-
2000
- 2000-12-04 ZA ZA200007174A patent/ZA200007174B/en unknown
-
2001
- 2001-01-08 NO NO20010117A patent/NO20010117D0/en not_active Application Discontinuation
- 2001-08-03 US US09/921,682 patent/US20020004528A1/en not_active Abandoned
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20030212133A1 (en) * | 2000-06-26 | 2003-11-13 | Bryans Justin Stephen | Gabapentin analogues for sleep disorders |
US7141606B2 (en) * | 2000-06-26 | 2006-11-28 | Warner-Lambert Company | Gabapentin analogues for sleep disorders |
US20070014260A1 (en) * | 2005-07-15 | 2007-01-18 | Samsung Electronics Co., Ltd. | Dual-mode mobile terminal and method for handover of packet service call between different communication networks |
US8107432B2 (en) | 2005-07-15 | 2012-01-31 | Samsung Electronics Co., Ltd | Dual-mode mobile terminal and method for handover of packet service call between different communication networks |
Also Published As
Publication number | Publication date |
---|---|
US6306910B1 (en) | 2001-10-23 |
ID27191A (en) | 2001-03-08 |
AU765038B2 (en) | 2003-09-04 |
PL345338A1 (en) | 2001-12-17 |
WO2000002546A3 (en) | 2000-06-15 |
NZ509231A (en) | 2003-08-29 |
KR20010071778A (en) | 2001-07-31 |
CA2333024A1 (en) | 2000-01-20 |
AU4967399A (en) | 2000-02-01 |
BR9911887A (en) | 2001-03-27 |
CA2333024C (en) | 2002-03-26 |
JP2002520277A (en) | 2002-07-09 |
ZA200007174B (en) | 2002-03-04 |
EP1094803A2 (en) | 2001-05-02 |
NO20010117L (en) | 2001-01-08 |
NO20010117D0 (en) | 2001-01-08 |
WO2000002546A2 (en) | 2000-01-20 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
STCB | Information on status: application discontinuation |
Free format text: ABANDONED -- FAILURE TO RESPOND TO AN OFFICE ACTION |