CA1263843A - Traitement des troubles du sommeil - Google Patents

Traitement des troubles du sommeil

Info

Publication number: CA1263843A
Authority: CA; Canada
Prior art keywords: composition; active ingredient; acetoxybutanoate; ethyl; lower alkyl
Prior art date: 1986-03-13
Legal status (The legal status 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 status listed.): Expired

Application number

CA000503996A

Other languages

English (en)

Inventor

Ronald H. Kluger

Mortimer Mamelak

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

University of Toronto Innovations Foundation

Original Assignee

University of Toronto Innovations Foundation

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.)

1986-03-13

Filing date

1986-03-13

Publication date

1989-12-12

1986-03-13 Application filed by University of Toronto Innovations Foundation filed Critical University of Toronto Innovations Foundation

1986-03-13 Priority to CA000503996A priority Critical patent/CA1263843A/fr

1989-12-12 Application granted granted Critical

1989-12-12 Publication of CA1263843A publication Critical patent/CA1263843A/fr

Status Expired legal-status Critical Current

Links

208000019116 sleep disease Diseases 0.000 title claims abstract description 7
150000001875 compounds Chemical class 0.000 claims abstract description 26
VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 claims abstract description 26
241001465754 Metazoa Species 0.000 claims abstract description 23
229960003638 dopamine Drugs 0.000 claims abstract description 13
KMPQIYXXLIFPKA-UHFFFAOYSA-N ethyl 4-acetyloxybutanoate Chemical compound CCOC(=O)CCCOC(C)=O KMPQIYXXLIFPKA-UHFFFAOYSA-N 0.000 claims abstract description 12
206010021118 Hypotonia Diseases 0.000 claims abstract description 6
230000036640 muscle relaxation Effects 0.000 claims abstract description 6
230000003444 anaesthetic effect Effects 0.000 claims abstract description 5
239000000203 mixture Substances 0.000 claims description 16
125000000217 alkyl group Chemical group 0.000 claims description 10
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 7
125000004432 carbon atom Chemical group C* 0.000 claims description 6
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 4
241000282414 Homo sapiens Species 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 3
125000003710 aryl alkyl group Chemical group 0.000 claims description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
239000002552 dosage form Substances 0.000 claims description 2
125000001153 fluoro group Chemical group F* 0.000 claims description 2
239000007903 gelatin capsule Substances 0.000 claims description 2
WLAKXJVBZHPARL-UHFFFAOYSA-N methyl 4-acetyloxybutanoate Chemical compound COC(=O)CCCOC(C)=O WLAKXJVBZHPARL-UHFFFAOYSA-N 0.000 claims description 2
MWWATHDPGQKSAR-UHFFFAOYSA-N propyne Chemical group CC#C MWWATHDPGQKSAR-UHFFFAOYSA-N 0.000 claims description 2
239000004480 active ingredient Substances 0.000 claims 9
239000003937 drug carrier Substances 0.000 claims 3
125000003118 aryl group Chemical group 0.000 claims 1
239000007788 liquid Substances 0.000 claims 1
239000008194 pharmaceutical composition Substances 0.000 claims 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
201000003631 narcolepsy Diseases 0.000 abstract description 6
241000124008 Mammalia Species 0.000 abstract description 5
208000018737 Parkinson disease Diseases 0.000 abstract description 5
208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 abstract description 4
206010022437 insomnia Diseases 0.000 abstract description 4
230000005856 abnormality Effects 0.000 abstract description 3
201000000980 schizophrenia Diseases 0.000 abstract description 3
229940124326 anaesthetic agent Drugs 0.000 abstract description 2
210000004556 brain Anatomy 0.000 abstract description 2
230000035945 sensitivity Effects 0.000 abstract description 2
SJZRECIVHVDYJC-UHFFFAOYSA-M 4-hydroxybutyrate Chemical compound OCCCC([O-])=O SJZRECIVHVDYJC-UHFFFAOYSA-M 0.000 description 16
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 13
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
230000000694 effects Effects 0.000 description 8
230000037396 body weight Effects 0.000 description 7
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
238000000034 method Methods 0.000 description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
241000700159 Rattus Species 0.000 description 6
239000003814 drug Substances 0.000 description 6
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 5
229940079593 drug Drugs 0.000 description 5
239000000047 product Substances 0.000 description 5
YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 4
AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 4
238000007792 addition Methods 0.000 description 4
-1 hydroxyL functions Chemical group 0.000 description 4
SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
230000002618 waking effect Effects 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
108010010803 Gelatin Proteins 0.000 description 3
239000002253 acid Substances 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
229920000159 gelatin Polymers 0.000 description 3
239000008273 gelatin Substances 0.000 description 3
235000019322 gelatine Nutrition 0.000 description 3
235000011852 gelatine desserts Nutrition 0.000 description 3
239000003158 myorelaxant agent Substances 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
238000002390 rotary evaporation Methods 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
231100000419 toxicity Toxicity 0.000 description 3
230000001988 toxicity Effects 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
241000282412 Homo Species 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
GOVNVPJYMDJYSR-UHFFFAOYSA-N aceburic acid Chemical compound CC(=O)OCCCC(O)=O GOVNVPJYMDJYSR-UHFFFAOYSA-N 0.000 description 2
229930188620 butyrolactone Natural products 0.000 description 2
239000002775 capsule Substances 0.000 description 2
208000035475 disorder Diseases 0.000 description 2
238000004821 distillation Methods 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 2
230000000147 hypnotic effect Effects 0.000 description 2
230000002045 lasting effect Effects 0.000 description 2
ZZUYIRISBMWFMV-UHFFFAOYSA-N methyl 4-chlorobutanoate Chemical compound COC(=O)CCCCl ZZUYIRISBMWFMV-UHFFFAOYSA-N 0.000 description 2
235000011056 potassium acetate Nutrition 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
238000010992 reflux Methods 0.000 description 2
XYGBKMMCQDZQOZ-UHFFFAOYSA-M sodium;4-hydroxybutanoate Chemical compound [Na+].OCCCC([O-])=O XYGBKMMCQDZQOZ-UHFFFAOYSA-M 0.000 description 2
239000000126 substance Substances 0.000 description 2
238000000967 suction filtration Methods 0.000 description 2
231100000331 toxic Toxicity 0.000 description 2
230000002588 toxic effect Effects 0.000 description 2
FEKPPKOQIFHYDH-UHFFFAOYSA-N (4-methoxy-4-oxobutyl) benzoate Chemical compound COC(=O)CCCOC(=O)C1=CC=CC=C1 FEKPPKOQIFHYDH-UHFFFAOYSA-N 0.000 description 1
241000661938 Capsus Species 0.000 description 1
AEMRFAOFKBGASW-UHFFFAOYSA-M Glycolate Chemical compound OCC([O-])=O AEMRFAOFKBGASW-UHFFFAOYSA-M 0.000 description 1
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
208000008238 Muscle Spasticity Diseases 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
241000700157 Rattus norvegicus Species 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
150000008065 acid anhydrides Chemical class 0.000 description 1
VWYANPOOORUCFJ-UHFFFAOYSA-N alpha-Fernenol Chemical compound CC1(C)C(O)CCC2(C)C3=CCC4(C)C5CCC(C(C)C)C5(C)CCC4(C)C3CCC21 VWYANPOOORUCFJ-UHFFFAOYSA-N 0.000 description 1
230000000202 analgesic effect Effects 0.000 description 1
238000010171 animal model Methods 0.000 description 1
230000003594 anti-tremorine Effects 0.000 description 1
239000002249 anxiolytic agent Substances 0.000 description 1
229940125717 barbiturate Drugs 0.000 description 1
229940049706 benzodiazepine Drugs 0.000 description 1
150000001557 benzodiazepines Chemical class 0.000 description 1
150000001734 carboxylic acid salts Chemical class 0.000 description 1
239000000969 carrier Substances 0.000 description 1
210000003169 central nervous system Anatomy 0.000 description 1
230000002490 cerebral effect Effects 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
230000000973 chemotherapeutic effect Effects 0.000 description 1
239000002026 chloroform extract Substances 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
239000000470 constituent Substances 0.000 description 1
230000007850 degeneration Effects 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
201000010099 disease Diseases 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
230000002708 enhancing effect Effects 0.000 description 1
OPXNFHAILOHHFO-UHFFFAOYSA-N ethyl 4-chlorobutanoate Chemical compound CCOC(=O)CCCCl OPXNFHAILOHHFO-UHFFFAOYSA-N 0.000 description 1
AYPJVXQBVHCUCJ-UHFFFAOYSA-N ethyl 4-hydroxybutanoate Chemical compound CCOC(=O)CCCO AYPJVXQBVHCUCJ-UHFFFAOYSA-N 0.000 description 1
239000000284 extract Substances 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000019634 flavors Nutrition 0.000 description 1
238000005187 foaming Methods 0.000 description 1
235000013305 food Nutrition 0.000 description 1
239000008241 heterogeneous mixture Substances 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
238000007912 intraperitoneal administration Methods 0.000 description 1
150000002596 lactones Chemical class 0.000 description 1
230000005923 long-lasting effect Effects 0.000 description 1
MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
229940126701 oral medication Drugs 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
235000020095 red wine Nutrition 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
230000001624 sedative effect Effects 0.000 description 1
230000004622 sleep time Effects 0.000 description 1
WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
229960003928 sodium oxybate Drugs 0.000 description 1
MOSCXNXKSOHVSQ-UHFFFAOYSA-M sodium;2-hydroxybutanoate Chemical compound [Na+].CCC(O)C([O-])=O MOSCXNXKSOHVSQ-UHFFFAOYSA-M 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008107 starch Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000001117 sulphuric acid Substances 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1

Landscapes

Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

CA000503996A 1986-03-13 1986-03-13 Traitement des troubles du sommeil Expired CA1263843A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000503996A CA1263843A (fr)	1986-03-13	1986-03-13	Traitement des troubles du sommeil

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA000503996A CA1263843A (fr)	1986-03-13	1986-03-13	Traitement des troubles du sommeil

Publications (1)

Publication Number	Publication Date
CA1263843A true CA1263843A (fr)	1989-12-12

Family

ID=4132674

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000503996A Expired CA1263843A (fr)	1986-03-13	1986-03-13	Traitement des troubles du sommeil

Country Status (1)

Country	Link
CA (1)	CA1263843A (fr)

1986
- 1986-03-13 CA CA000503996A patent/CA1263843A/fr not_active Expired

Legal Events

Date	Code	Title	Description
1999-12-13	MKLA	Lapsed

Publication	Publication Date	Title
US4738985A (en)	1988-04-19	Pharmaceutical composition and treatment
EP0235408B1 (fr)	1991-01-09	Composition pharmaceutique et traitement
EP0236684B1 (fr)	1992-05-20	Galanthamine ou ses analogues pour le traitement de la maladie d'Alzheimer
US5840331A (en)	1998-11-24	Use of γ-hydroxybutyrate for the stimulation of sleep-related secretion growth hormone and prolactin
US4444758A (en)	1984-04-24	Nonapeptide for treating addictive drug withdrawal conditions
JP3192141B2 (ja)	2001-07-23	抗うつ剤
EP2504311A1 (fr)	2012-10-03	Analogues de l'acide arachidonique et procédés pour un traitement analgésique l'utilisant
JPS61172828A (ja)	1986-08-04	外傷後の神経傷害を治療するための薬剤
US4599355A (en)	1986-07-08	Treatment of sleep disorders
US2817623A (en)	1957-12-24	Tabernanthine, ibogaine containing analgesic compositions
CA1263843A (fr)	1989-12-12	Traitement des troubles du sommeil
ES2255607T3 (es)	2006-07-01	Utilizacion de buprenorfina para el tratamiento de la incontinencia urinaria.
US5496823A (en)	1996-03-05	Pharmaceutical composition for increasing bladder capacity
EA006675B1 (ru)	2006-02-24	Фармацевтическая композиция, содержащая гамма-бутиробетаин
US3360434A (en)	1967-12-26	Method for reducing blood pressure with phenylalanine derivatives
US20040106671A1 (en)	2004-06-03	Remedies for vesical hyperesthesia
US4474801A (en)	1984-10-02	α-Amino-γ-butyrolactones for treating alcohol dependence
JP3535207B2 (ja)	2004-06-07	抗ガン剤及びｇｒｐレセプター拮抗剤
EP0429245B1 (fr)	1996-02-07	Agent thérapeutique pour les maladies du système central nerveux
DK164021B (da)	1992-05-04	Anvendelse af diltiazem til fremstilling af et farmaceutisk praeparat til behandling af hyperlipidemi
US2991225A (en)	1961-07-04	Omicron-methylbenzhydryl-beta-dimethylaminoethyl ether process and composition for symptomatic relief of the syndrome of parkinsonism and of spastic skeletal muscle disorders
EP0273253A2 (fr)	1988-07-06	L'emploi de 6-allyl-2-amino-5,6,7,8-tétrahydro-4H-thiazolo-[5,4d]azépine pour la libération de l'hormone somatotrope
KR920003580B1 (ko)	1992-05-04	동맥경화증 예방 및 치료제
US3976774A (en)	1976-08-24	Antiemetic method
JPH0374330A (ja)	1991-03-28	脱髄疾患治療剤