IL109982A - Pharmaceutical preparations containing isobramamide and methods for their preparation - Google Patents

Pharmaceutical preparations containing isobramamide and methods for their preparation

Info

Publication number: IL109982A
Authority: IL; Israel
Prior art keywords: isovaleramide; anxiolytic; sedative; activity; subject
Prior art date: 1993-06-11

Application number

IL10998294A

Other languages

English (en)

Hebrew (he)

Other versions

IL109982A0 (en

Original Assignee

Nps Pharma Inc

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.)

1993-06-11

Filing date

1994-06-10

Publication date

1998-09-24

1994-06-10 Application filed by Nps Pharma Inc filed Critical Nps Pharma Inc

1994-10-07 Publication of IL109982A0 publication Critical patent/IL109982A0/xx

1998-09-24 Publication of IL109982A publication Critical patent/IL109982A/en

Links

SANOUVWGPVYVAV-UHFFFAOYSA-N isovaleramide Chemical compound CC(C)CC(N)=O SANOUVWGPVYVAV-UHFFFAOYSA-N 0.000 title claims abstract description 105
239000008194 pharmaceutical composition Substances 0.000 title claims description 14
238000002360 preparation method Methods 0.000 title claims description 10
238000000034 method Methods 0.000 title claims description 7
230000000949 anxiolytic effect Effects 0.000 claims abstract description 42
241001465754 Metazoa Species 0.000 claims description 34
230000007958 sleep Effects 0.000 claims description 16
208000019901 Anxiety disease Diseases 0.000 claims description 11
230000036506 anxiety Effects 0.000 claims description 9
230000001939 inductive effect Effects 0.000 claims description 6
206010039897 Sedation Diseases 0.000 claims description 5
230000037396 body weight Effects 0.000 claims description 5
239000007924 injection Substances 0.000 claims description 5
238000002347 injection Methods 0.000 claims description 5
230000036280 sedation Effects 0.000 claims description 5
208000024891 symptom Diseases 0.000 claims description 3
206010001497 Agitation Diseases 0.000 claims description 2
208000007848 Alcoholism Diseases 0.000 claims description 2
206010056344 Menstrual discomfort Diseases 0.000 claims description 2
206010036618 Premenstrual syndrome Diseases 0.000 claims description 2
201000007930 alcohol dependence Diseases 0.000 claims description 2
230000005284 excitation Effects 0.000 claims description 2
230000005586 smoking cessation Effects 0.000 claims description 2
201000009032 substance abuse Diseases 0.000 claims description 2
231100000736 substance abuse Toxicity 0.000 claims description 2
208000011117 substance-related disease Diseases 0.000 claims description 2
239000002552 dosage form Substances 0.000 claims 1
230000001624 sedative effect Effects 0.000 abstract description 35
239000002249 anxiolytic agent Substances 0.000 abstract description 28
239000000932 sedative agent Substances 0.000 abstract description 26
210000003169 central nervous system Anatomy 0.000 abstract description 13
231100000065 noncytotoxic Toxicity 0.000 abstract description 2
230000002020 noncytotoxic effect Effects 0.000 abstract description 2
239000000463 material Substances 0.000 abstract 1
230000000694 effects Effects 0.000 description 33
238000012360 testing method Methods 0.000 description 30
150000001875 compounds Chemical class 0.000 description 29
QRCJOCOSPZMDJY-UHFFFAOYSA-N valnoctamide Chemical compound CCC(C)C(CC)C(N)=O QRCJOCOSPZMDJY-UHFFFAOYSA-N 0.000 description 24
229960001364 valnoctamide Drugs 0.000 description 24
230000000147 hypnotic effect Effects 0.000 description 22
239000000126 substance Substances 0.000 description 17
241000699670 Mus sp. Species 0.000 description 16
241000700159 Rattus Species 0.000 description 13
238000010171 animal model Methods 0.000 description 11
239000003795 chemical substances by application Substances 0.000 description 11
239000003814 drug Substances 0.000 description 11
229940125723 sedative agent Drugs 0.000 description 11
230000006742 locomotor activity Effects 0.000 description 10
WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 10
244000126014 Valeriana officinalis Species 0.000 description 9
235000013832 Valeriana officinalis Nutrition 0.000 description 9
238000003556 assay Methods 0.000 description 9
229940125717 barbiturate Drugs 0.000 description 9
229940079593 drug Drugs 0.000 description 9
235000016788 valerian Nutrition 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
BDIAUFOIMFAIPU-KVJIRVJXSA-N Valtratum Chemical compound C([C@]12[C@@H]3C(C(=CO[C@H]3OC(=O)CC(C)C)COC(C)=O)=C[C@@H]1OC(=O)CC(C)C)O2 BDIAUFOIMFAIPU-KVJIRVJXSA-N 0.000 description 7
239000000203 mixture Substances 0.000 description 7
230000035939 shock Effects 0.000 description 7
FWKBQAVMKVZEOT-STCFVSJZSA-N Acevaltrate Chemical compound C([C@]12[C@@H](OC(=O)CC(C)(C)OC(C)=O)C=C3C(COC(C)=O)=CO[C@H]([C@H]23)OC(=O)CC(C)C)O1 FWKBQAVMKVZEOT-STCFVSJZSA-N 0.000 description 6
HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 description 6
239000003179 convulsant agent Substances 0.000 description 6
239000000284 extract Substances 0.000 description 6
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239000004480 active ingredient Substances 0.000 description 5
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238000002474 experimental method Methods 0.000 description 5
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150000002773 monoterpene derivatives Chemical class 0.000 description 5
230000000144 pharmacologic effect Effects 0.000 description 5
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BDIAUFOIMFAIPU-UHFFFAOYSA-N valepotriate Natural products CC(C)CC(=O)OC1C=C(C(=COC2OC(=O)CC(C)C)COC(C)=O)C2C11CO1 BDIAUFOIMFAIPU-UHFFFAOYSA-N 0.000 description 5
241000196324 Embryophyta Species 0.000 description 4
AAOVKJBEBIDNHE-UHFFFAOYSA-N diazepam Chemical compound N=1CC(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 AAOVKJBEBIDNHE-UHFFFAOYSA-N 0.000 description 4
230000021824 exploration behavior Effects 0.000 description 4
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XYHKNCXZYYTLRG-UHFFFAOYSA-N 1h-imidazole-2-carbaldehyde Chemical compound O=CC1=NC=CN1 XYHKNCXZYYTLRG-UHFFFAOYSA-N 0.000 description 3
GWYFCOCPABKNJV-UHFFFAOYSA-M 3-Methylbutanoic acid Natural products CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 description 3
WQKBMPNNRRZQLG-UHFFFAOYSA-N Acevaltratum Natural products CC(C)CC(=O)OC1C=C(C(=COC2OC(=O)CC(C)(C)OC(C)=O)COC(C)=O)C2C11CO1 WQKBMPNNRRZQLG-UHFFFAOYSA-N 0.000 description 3
PHHROXLDZHUIGO-PNBTUHDLSA-N Didrovaltratum Chemical compound C([C@@]12[C@@H](OC(C)=O)C[C@H]3[C@@H]1[C@H](OC(=O)CC(C)C)OC=C3COC(=O)CC(C)C)O2 PHHROXLDZHUIGO-PNBTUHDLSA-N 0.000 description 3
KQEOKUJOWVGWDX-UHFFFAOYSA-N Isodihydrovaltrate Natural products CC(C)CC(=O)OC1CC(C(=COC2OC(=O)CC(C)C)COC(C)=O)C2C11CO1 KQEOKUJOWVGWDX-UHFFFAOYSA-N 0.000 description 3
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
FWKBQAVMKVZEOT-UHFFFAOYSA-N acevaltrat Natural products C12C(OC(=O)CC(C)C)OC=C(COC(C)=O)C2=CC(OC(=O)CC(C)(C)OC(C)=O)C21CO2 FWKBQAVMKVZEOT-UHFFFAOYSA-N 0.000 description 3
229950005206 acevaltrate Drugs 0.000 description 3
230000000338 anxiogenic effect Effects 0.000 description 3
GWYFCOCPABKNJV-UHFFFAOYSA-N beta-methyl-butyric acid Natural products CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 3
239000002775 capsule Substances 0.000 description 3
-1 diazepam ("VALIUM") Chemical class 0.000 description 3
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PVKOJQHHDYMUEI-UHFFFAOYSA-N didrovaltrate Natural products CC(C)CC(=O)COC1=COC(OC(=O)CC(C)C)C2C1CC(OC(=O)C)C23CO3 PVKOJQHHDYMUEI-UHFFFAOYSA-N 0.000 description 3
PHHROXLDZHUIGO-UHFFFAOYSA-N dihydrovaltrate Natural products CC(C)CC(=O)OCC1=COC(OC(=O)CC(C)C)C2C1CC(OC(C)=O)C21CO1 PHHROXLDZHUIGO-UHFFFAOYSA-N 0.000 description 3
235000013305 food Nutrition 0.000 description 3
239000005554 hypnotics and sedatives Substances 0.000 description 3
230000006698 induction Effects 0.000 description 3
239000007928 intraperitoneal injection Substances 0.000 description 3
239000006186 oral dosage form Substances 0.000 description 3
230000004043 responsiveness Effects 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
241000894007 species Species 0.000 description 3
238000013222 sprague-dawley male rat Methods 0.000 description 3
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HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
206010010904 Convulsion Diseases 0.000 description 2
206010013142 Disinhibition Diseases 0.000 description 2
VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 2
QGMRQYFBGABWDR-UHFFFAOYSA-M Pentobarbital sodium Chemical compound [Na+].CCCC(C)C1(CC)C(=O)NC(=O)[N-]C1=O QGMRQYFBGABWDR-UHFFFAOYSA-M 0.000 description 2
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239000013543 active substance Substances 0.000 description 2
201000010275 acute porphyria Diseases 0.000 description 2
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230000001773 anti-convulsant effect Effects 0.000 description 2
239000001961 anticonvulsive agent Substances 0.000 description 2
230000003542 behavioural effect Effects 0.000 description 2
235000013361 beverage Nutrition 0.000 description 2
DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 description 2
210000004027 cell Anatomy 0.000 description 2
230000000052 comparative effect Effects 0.000 description 2
230000034994 death Effects 0.000 description 2
231100000517 death Toxicity 0.000 description 2
229960003529 diazepam Drugs 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
230000012010 growth Effects 0.000 description 2
235000015220 hamburgers Nutrition 0.000 description 2
208000033552 hepatic porphyria Diseases 0.000 description 2
206010022437 insomnia Diseases 0.000 description 2
229950003188 isovaleryl diethylamide Drugs 0.000 description 2
238000005259 measurement Methods 0.000 description 2
230000001537 neural effect Effects 0.000 description 2
ADIMAYPTOBDMTL-UHFFFAOYSA-N oxazepam Chemical compound C12=CC(Cl)=CC=C2NC(=O)C(O)N=C1C1=CC=CC=C1 ADIMAYPTOBDMTL-UHFFFAOYSA-N 0.000 description 2
IPWFJLQDVFKJDU-UHFFFAOYSA-N pentanamide Chemical compound CCCCC(N)=O IPWFJLQDVFKJDU-UHFFFAOYSA-N 0.000 description 2
229960002275 pentobarbital sodium Drugs 0.000 description 2
108090000623 proteins and genes Proteins 0.000 description 2
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230000004799 sedative–hypnotic effect Effects 0.000 description 2
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239000000829 suppository Substances 0.000 description 2
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239000000341 volatile oil Substances 0.000 description 2
DIWRORZWFLOCLC-HNNXBMFYSA-N (3s)-7-chloro-5-(2-chlorophenyl)-3-hydroxy-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound N([C@H](C(NC1=CC=C(Cl)C=C11)=O)O)=C1C1=CC=CC=C1Cl DIWRORZWFLOCLC-HNNXBMFYSA-N 0.000 description 1
SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 description 1
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235000007319 Avena orientalis Nutrition 0.000 description 1
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PCLCDPVEEFVAAQ-UHFFFAOYSA-N BCA 1 Chemical compound CC(CO)CCCC(C)C1=CCC(C)(O)C1CC2=C(O)C(O)CCC2=O PCLCDPVEEFVAAQ-UHFFFAOYSA-N 0.000 description 1
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DIWRORZWFLOCLC-UHFFFAOYSA-N Lorazepam Chemical compound C12=CC(Cl)=CC=C2NC(=O)C(O)N=C1C1=CC=CC=C1Cl DIWRORZWFLOCLC-UHFFFAOYSA-N 0.000 description 1
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BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
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CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
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239000002269 analeptic agent Substances 0.000 description 1
230000003556 anti-epileptic effect Effects 0.000 description 1
230000002921 anti-spasmodic effect Effects 0.000 description 1
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231100000433 cytotoxic Toxicity 0.000 description 1
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230000003013 cytotoxicity Effects 0.000 description 1
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238000007405 data analysis Methods 0.000 description 1
238000013500 data storage Methods 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
238000001212 derivatisation Methods 0.000 description 1
NIJJYAXOARWZEE-UHFFFAOYSA-N di-n-propyl-acetic acid Natural products CCCC(C(O)=O)CCC NIJJYAXOARWZEE-UHFFFAOYSA-N 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
238000009510 drug design Methods 0.000 description 1
229940088679 drug related substance Drugs 0.000 description 1
239000002662 enteric coated tablet Substances 0.000 description 1
DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 1
238000009472 formulation Methods 0.000 description 1
239000007897 gelcap Substances 0.000 description 1
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238000000338 in vitro Methods 0.000 description 1
208000022119 inability to concentrate Diseases 0.000 description 1
QZMQDHNCNUGQSO-UHFFFAOYSA-N isovaleryl diethylamide Chemical compound CCN(CC)C(=O)CC(C)C QZMQDHNCNUGQSO-UHFFFAOYSA-N 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000008297 liquid dosage form Substances 0.000 description 1
239000012669 liquid formulation Substances 0.000 description 1
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230000004060 metabolic process Effects 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
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125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
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231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
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MSRILKIQRXUYCT-UHFFFAOYSA-M valproate semisodium Chemical compound [Na+].CCCC(C(O)=O)CCC.CCCC(C([O-])=O)CCC MSRILKIQRXUYCT-UHFFFAOYSA-M 0.000 description 1
229960000604 valproic acid Drugs 0.000 description 1
OMOMUFTZPTXCHP-UHFFFAOYSA-N valpromide Chemical compound CCCC(C(N)=O)CCC OMOMUFTZPTXCHP-UHFFFAOYSA-N 0.000 description 1
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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
- A61K31/16—Amides, e.g. hydroxamic acids
- 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
- 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
- A61P25/22—Anxiolytics

Landscapes

Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Biomedical Technology (AREA)
Organic Chemistry (AREA)
Bioinformatics & Cheminformatics (AREA)
Epidemiology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Engineering & Computer Science (AREA)
Anesthesiology (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Medicinal Preparation (AREA)
Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Medicines Containing Plant Substances (AREA)

IL10998294A 1993-06-11 1994-06-10 Pharmaceutical preparations containing isobramamide and methods for their preparation IL109982A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US08/075,126 US5506268A (en)	1993-06-11	1993-06-11	Use of isovaleramide as a mild anxiolytic and sedative agent

Publications (2)

Publication Number	Publication Date
IL109982A0 IL109982A0 (en)	1994-10-07
IL109982A true IL109982A (en)	1998-09-24

Family

ID=22123718

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL10998294A IL109982A (en)	1993-06-11	1994-06-10	Pharmaceutical preparations containing isobramamide and methods for their preparation

Country Status (15)

Country	Link
US (2)	US5506268A (de)
EP (1)	EP0706385B1 (de)
JP (2)	JP3790267B2 (de)
KR (1)	KR100341993B1 (de)
CN (1)	CN1108793C (de)
AT (1)	ATE213630T1 (de)
CA (1)	CA2164842C (de)
DE (1)	DE69429990T2 (de)
DK (1)	DK0706385T3 (de)
ES (1)	ES2170770T3 (de)
IL (1)	IL109982A (de)
PT (1)	PT706385E (de)
RU (1)	RU2136271C1 (de)
TW (1)	TW420606B (de)
WO (1)	WO1994028888A1 (de)

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* Cited by examiner, † Cited by third party
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DE4113984C2 (de) *	1991-04-29	2002-05-08	Koehler Chemie Dr Franz	Salze der 4-Hydroxy-Buttersäure
US5786382A (en) *	1995-11-03	1998-07-28	Childers-Zadah; Vsande	Use of valerian plant and/or root as a scent-attractant for stimulating canines and felines
DK0938304T3 (da) *	1996-08-30	2005-03-14	Nps Pharma Inc	Isovaleramid til behandlingen af kramper, epilepsi, hovedpine og spasticitet
US6589994B1 (en) *	1996-08-30	2003-07-08	Nps Pharmaceuticals, Inc.	Treating a variety of pathological conditions, including spasticity and convulsions, by effecting a modulation of CNS activity with isovaleramide, isovaleric acid, or a related compound
IL120006A (en) *	1997-01-14	2000-12-06	Yissum Res Dev Co	Valnoctamide stereoisomers and a method for their synthesis and separation
ATE309200T1 (de)	1997-12-10	2005-11-15	Nps Pharma Inc	Antikonvulsive und zns-aktive bis-fluoralkylamide
EP1576962A1 (de) *	1998-03-04	2005-09-21	Nps Pharmaceuticals, Inc.	Zusammensetzungen enthaltend Isovalerianamide zusammen mit ibuprofen
ATE295160T1 (de) *	1998-03-04	2005-05-15	Nps Pharma Inc	Zusammensetzungen enthaltend isovalerianamide zusammen mit ibuprofen
US6383527B1 (en) *	1999-03-04	2002-05-07	Nps Pharmaceuticals, Inc.	Compositions comprising valerian extracts, isovaleric acid or derivatives thereof with a NSAID
US6346283B1 (en)	1999-03-26	2002-02-12	Ancile Pharmaceuticals	Use of valeriana for the treatment of restless leg syndrome and related disorders
US7235258B1 (en)	1999-10-19	2007-06-26	Nps Pharmaceuticals, Inc.	Sustained-release formulations for treating CNS-mediated disorders
RU2199309C1 (ru) *	2001-12-29	2003-02-27	Закрытое акционерное общество "Брынцалов-А"	Лекарственное средство нобрассит седативного и анксиолитического действия
RU2209062C1 (ru) *	2002-03-19	2003-07-27	Институт физиологии им. И.П.Павлова РАН	Вещество, обладающее седативным действием
CA2487849A1 (en)	2002-07-18	2004-01-29	Cytos Biotechnology Ag	Hapten-carrier conjugates comprising virus like particles and uses thereof
WO2006012603A2 (en) *	2004-07-22	2006-02-02	Nps Pharmaceuticals, Inc.	Analogs of isovaleramide, a pharmaceutical composition including the same, and a method of treating central nervous system conditions or diseases
US20210130285A1 (en)	2008-03-19	2021-05-06	Aurimmed Pharma, Inc.	Novel compounds advantageous in the treatment of central nervous system diseases and disorders
US9212155B2 (en)	2008-03-19	2015-12-15	Aurimmed Pharma, Inc.	Compounds advantageous in the treatment of central nervous system diseases and disorders
US10793515B2 (en)	2008-03-19	2020-10-06	Aurimmed Pharma, Inc.	Compounds advantageous in the treatment of central nervous system diseases and disorders
KR102222910B1 (ko)	2019-04-30	2021-03-04	차은정	평상형 원목침대
KR102227555B1 (ko)	2019-12-24	2021-03-15	주식회사 리빙테크	황토볼이 구비된 편백나무 침대

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US4205083A (en) *	1968-03-30	1980-05-27	Kali-Chemie Aktiengesellschaft	Cyclopentapyrans
FR2306687A2 (fr) *	1975-04-08	1976-11-05	Buzas Andre	Derives d'acides phenoxy-acetiques, leur preparation et leur application en therapeutique
FR2209555B1 (de) *	1972-12-11	1975-11-28	Labaz
SU668261A1 (ru) *	1977-03-21	1985-03-15	Киевский научно-исследовательский институт фармакологии и токсикологии	@ -Алкил- @ -( @ -оксифенил)-амиды 3,4,5-триметоксибензойной кислоты,обладающие нейролептической активностью
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DE4008403A1 (de) *	1990-03-16	1991-09-19	Merck Patent Gmbh	Glykolsaeurederivate
FR2674524B1 (fr) *	1991-03-25	1993-05-21	Adir	Nouveaux amides alkyl heterocycliques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent.

1993
- 1993-06-11 US US08/075,126 patent/US5506268A/en not_active Expired - Lifetime
1994
- 1994-06-10 RU RU96102019A patent/RU2136271C1/ru not_active IP Right Cessation
- 1994-06-10 PT PT94920093T patent/PT706385E/pt unknown
- 1994-06-10 JP JP50202095A patent/JP3790267B2/ja not_active Expired - Fee Related
- 1994-06-10 EP EP94920093A patent/EP0706385B1/de not_active Expired - Lifetime
- 1994-06-10 DE DE69429990T patent/DE69429990T2/de not_active Expired - Fee Related
- 1994-06-10 KR KR1019950705615A patent/KR100341993B1/ko not_active Expired - Fee Related
- 1994-06-10 WO PCT/US1994/006356 patent/WO1994028888A1/en not_active Ceased
- 1994-06-10 AT AT94920093T patent/ATE213630T1/de not_active IP Right Cessation
- 1994-06-10 ES ES94920093T patent/ES2170770T3/es not_active Expired - Lifetime
- 1994-06-10 CA CA002164842A patent/CA2164842C/en not_active Expired - Fee Related
- 1994-06-10 IL IL10998294A patent/IL109982A/en not_active IP Right Cessation
- 1994-06-10 CN CN94192865A patent/CN1108793C/zh not_active Expired - Fee Related
- 1994-06-10 DK DK94920093T patent/DK0706385T3/da active
- 1994-06-11 TW TW083105347A patent/TW420606B/zh not_active IP Right Cessation
1996
- 1996-03-29 US US08/623,691 patent/US5763494A/en not_active Expired - Fee Related
2006
- 2006-02-03 JP JP2006026874A patent/JP2006169259A/ja active Pending

Also Published As

Publication number	Publication date
IL109982A0 (en)	1994-10-07
AU701360B2 (en)	1999-01-28
KR100341993B1 (ko)	2002-11-29
CN1127472A (zh)	1996-07-24
CA2164842C (en)	2006-08-29
EP0706385A1 (de)	1996-04-17
RU2136271C1 (ru)	1999-09-10
TW420606B (en)	2001-02-01
JP2006169259A (ja)	2006-06-29
US5763494A (en)	1998-06-09
JPH09501908A (ja)	1997-02-25
ES2170770T3 (es)	2002-08-16
DE69429990T2 (de)	2002-09-05
EP0706385B1 (de)	2002-02-27
DK0706385T3 (da)	2002-04-29
WO1994028888A1 (en)	1994-12-22
PT706385E (pt)	2002-07-31
JP3790267B2 (ja)	2006-06-28
US5506268A (en)	1996-04-09
ATE213630T1 (de)	2002-03-15
DE69429990D1 (de)	2002-04-04
AU7100694A (en)	1995-01-03
CN1108793C (zh)	2003-05-21
CA2164842A1 (en)	1994-12-22

Legal Events

Date	Code	Title
1999-01-26	FF	Patent granted
1999-10-28	KB	Patent renewed
2004-07-25	KB	Patent renewed
2008-08-10	KB	Patent renewed
2013-02-03	MM9K	Patent not in force due to non-payment of renewal fees

Publication	Publication Date	Title
EP0706385B1 (de)	2002-02-27	Verwendung vonSisovaleramid als mildes anxiolytisches und sedatives Mittel
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AU701360C (en)	2000-10-05	Use of isovaleramide as a mild anxiolytic and mild sedative agent
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