IL96372A - 3-(1,3-dioxoalkyl)-4,5-dihydro-4-oxoimidazo [1,5-c] quinoxaline compounds, their preparation and pharmaceutical compositions containing them - Google Patents

3-(1,3-dioxoalkyl)-4,5-dihydro-4-oxoimidazo [1,5-c] quinoxaline compounds, their preparation and pharmaceutical compositions containing them

Info

Publication number: IL96372A
Authority: IL; Israel
Prior art keywords: compound; dihydro; general formula; set forth; quinoxaline
Prior art date: 1989-11-22

Application number

IL9637290A

Other languages

English (en)

Other versions

IL96372A0 (en

Original Assignee

Novo Nordisk As

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.)

1989-11-22

Filing date

1990-11-16

Publication date

1994-10-21

1990-11-16 Application filed by Novo Nordisk As filed Critical Novo Nordisk As

1991-08-16 Publication of IL96372A0 publication Critical patent/IL96372A0/xx

1994-10-21 Publication of IL96372A publication Critical patent/IL96372A/en

Links

239000008194 pharmaceutical composition Substances 0.000 title claims description 9
238000002360 preparation method Methods 0.000 title abstract description 4
125000001567 quinoxalinyl group Chemical class N1=C(C=NC2=CC=CC=C12)* 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 44
150000002431 hydrogen Chemical class 0.000 claims abstract description 9
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
239000001257 hydrogen Substances 0.000 claims abstract description 9
229910052736 halogen Inorganic materials 0.000 claims abstract description 6
150000002367 halogens Chemical group 0.000 claims abstract description 6
YELMWJNXDALKFE-UHFFFAOYSA-N 3h-imidazo[4,5-f]quinoxaline Chemical class N1=CC=NC2=C(NC=N3)C3=CC=C21 YELMWJNXDALKFE-UHFFFAOYSA-N 0.000 claims abstract description 4
125000006196 aroyl alkyl group Chemical group 0.000 claims abstract description 3
125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 3
210000003169 central nervous system Anatomy 0.000 claims description 11
XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 10
238000000034 method Methods 0.000 claims description 8
-1 dioxopropyl Chemical group 0.000 claims description 6
239000003085 diluting agent Substances 0.000 claims description 4
239000003937 drug carrier Substances 0.000 claims description 4
UXNARFNFDKPMGZ-UHFFFAOYSA-N 1-(4-oxo-5-propan-2-ylimidazo[1,5-a]quinoxalin-3-yl)butane-1,3-dione Chemical compound O=C1N(C(C)C)C2=CC=CC=C2N2C1=C(C(=O)CC(C)=O)N=C2 UXNARFNFDKPMGZ-UHFFFAOYSA-N 0.000 claims description 2
150000001350 alkyl halides Chemical class 0.000 claims description 2
230000002152 alkylating effect Effects 0.000 claims description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 2
230000000949 anxiolytic effect Effects 0.000 abstract description 4
239000002249 anxiolytic agent Substances 0.000 abstract description 3
210000004556 brain Anatomy 0.000 abstract description 3
241000124008 Mammalia Species 0.000 abstract description 2
229940005530 anxiolytics Drugs 0.000 abstract description 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 3
125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 1
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 abstract 1
125000000882 C2-C6 alkenyl group Chemical group 0.000 abstract 1
230000003920 cognitive function Effects 0.000 abstract 1
239000003326 hypnotic agent Substances 0.000 abstract 1
230000000147 hypnotic effect Effects 0.000 abstract 1
239000000126 substance Substances 0.000 description 11
238000012360 testing method Methods 0.000 description 11
238000006243 chemical reaction Methods 0.000 description 10
230000027455 binding Effects 0.000 description 8
241000699670 Mus sp. Species 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
102000004300 GABA-A Receptors Human genes 0.000 description 6
108090000839 GABA-A Receptors Proteins 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
239000000243 solution Substances 0.000 description 6
230000009870 specific binding Effects 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical class CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
239000002552 dosage form Substances 0.000 description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
239000000203 mixture Substances 0.000 description 5
HVCFCNAITDHQFX-UHFFFAOYSA-N 1-cyclopropylethanone Chemical compound CC(=O)C1CC1 HVCFCNAITDHQFX-UHFFFAOYSA-N 0.000 description 4
229960002200 flunitrazepam Drugs 0.000 description 4
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
239000001961 anticonvulsive agent Substances 0.000 description 3
239000002775 capsule Substances 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
239000002904 solvent Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
PPTYJKAXVCCBDU-UHFFFAOYSA-N Rohypnol Chemical compound N=1CC(=O)N(C)C2=CC=C([N+]([O-])=O)C=C2C=1C1=CC=CC=C1F PPTYJKAXVCCBDU-UHFFFAOYSA-N 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
230000001773 anti-convulsant effect Effects 0.000 description 2
229960003965 antiepileptics Drugs 0.000 description 2
239000002585 base Substances 0.000 description 2
239000000872 buffer Substances 0.000 description 2
239000004359 castor oil Substances 0.000 description 2
235000019438 castor oil Nutrition 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
DGBIGWXXNGSACT-UHFFFAOYSA-N clonazepam Chemical compound C12=CC([N+](=O)[O-])=CC=C2NC(=O)CN=C1C1=CC=CC=C1Cl DGBIGWXXNGSACT-UHFFFAOYSA-N 0.000 description 2
229960003120 clonazepam Drugs 0.000 description 2
229940125782 compound 2 Drugs 0.000 description 2
235000014113 dietary fatty acids Nutrition 0.000 description 2
230000000694 effects Effects 0.000 description 2
230000008030 elimination Effects 0.000 description 2
238000003379 elimination reaction Methods 0.000 description 2
ORTSNSVIXDXASO-UHFFFAOYSA-N ethyl 4-oxo-5-propan-2-ylimidazo[1,5-a]quinoxaline-3-carboxylate Chemical compound C1=CC=C2N3C=NC(C(=O)OCC)=C3C(=O)N(C(C)C)C2=C1 ORTSNSVIXDXASO-UHFFFAOYSA-N 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
239000000194 fatty acid Substances 0.000 description 2
229930195729 fatty acid Natural products 0.000 description 2
ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 2
239000008101 lactose Substances 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
239000002480 mineral oil Substances 0.000 description 2
235000010446 mineral oil Nutrition 0.000 description 2
239000000825 pharmaceutical preparation Substances 0.000 description 2
102000005962 receptors Human genes 0.000 description 2
108020003175 receptors Proteins 0.000 description 2
229910000104 sodium hydride Inorganic materials 0.000 description 2
239000012312 sodium hydride Substances 0.000 description 2
238000007920 subcutaneous administration Methods 0.000 description 2
239000000454 talc Substances 0.000 description 2
229910052623 talc Inorganic materials 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
FRBFBGWFVHKCKG-UHFFFAOYSA-N 1-(5-tert-butyl-4-oxoimidazo[1,5-a]quinoxalin-3-yl)butane-1,3-dione Chemical compound C1=CC=C2N3C=NC(C(=O)CC(=O)C)=C3C(=O)N(C(C)(C)C)C2=C1 FRBFBGWFVHKCKG-UHFFFAOYSA-N 0.000 description 1
ZVAPWJGRRUHKGP-UHFFFAOYSA-N 1h-1,5-benzodiazepine Chemical class N1C=CC=NC2=CC=CC=C12 ZVAPWJGRRUHKGP-UHFFFAOYSA-N 0.000 description 1
229920000856 Amylose Polymers 0.000 description 1
208000019901 Anxiety disease Diseases 0.000 description 1
206010010904 Convulsion Diseases 0.000 description 1
229920002261 Corn starch Polymers 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
241000282412 Homo Species 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
235000004443 Ricinus communis Nutrition 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
241000251539 Vertebrata <Metazoa> Species 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
125000003342 alkenyl group Chemical group 0.000 description 1
150000004703 alkoxides Chemical class 0.000 description 1
229940125681 anticonvulsant agent Drugs 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
229940049706 benzodiazepine Drugs 0.000 description 1
150000001557 benzodiazepines Chemical class 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000037396 body weight Effects 0.000 description 1
235000014633 carbohydrates Nutrition 0.000 description 1
150000001720 carbohydrates Chemical class 0.000 description 1
239000000969 carrier Substances 0.000 description 1
229920001429 chelating resin Polymers 0.000 description 1
238000004040 coloring Methods 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
229940125904 compound 1 Drugs 0.000 description 1
229940126214 compound 3 Drugs 0.000 description 1
229940125898 compound 5 Drugs 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
230000036461 convulsion Effects 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
FDSGHYHRLSWSLQ-UHFFFAOYSA-N dichloromethane;propan-2-one Chemical compound ClCCl.CC(C)=O FDSGHYHRLSWSLQ-UHFFFAOYSA-N 0.000 description 1
238000006073 displacement reaction Methods 0.000 description 1
231100000673 dose–response relationship Toxicity 0.000 description 1
239000008298 dragée Substances 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
230000001804 emulsifying effect Effects 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
YJPKKTRLHRPYLL-UHFFFAOYSA-N ethyl 5-tert-butyl-4-oxoimidazo[1,5-a]quinoxaline-3-carboxylate Chemical compound C1=CC=C2N3C=NC(C(=O)OCC)=C3C(=O)N(C(C)(C)C)C2=C1 YJPKKTRLHRPYLL-UHFFFAOYSA-N 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
238000009472 formulation Methods 0.000 description 1
239000012458 free base Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
239000003365 glass fiber Substances 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
229920003063 hydroxymethyl cellulose Polymers 0.000 description 1
229940031574 hydroxymethyl cellulose Drugs 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
239000007788 liquid Substances 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
239000003921 oil Substances 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
239000002504 physiological saline solution Substances 0.000 description 1
PJGSXYOJTGTZAV-UHFFFAOYSA-N pinacolone Chemical compound CC(=O)C(C)(C)C PJGSXYOJTGTZAV-UHFFFAOYSA-N 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000002335 preservative effect Effects 0.000 description 1
239000000047 product Substances 0.000 description 1
210000004129 prosencephalon Anatomy 0.000 description 1
UPUZGXILYFKSGE-UHFFFAOYSA-N quinoxaline-2-carboxylic acid Chemical compound C1=CC=CC2=NC(C(=O)O)=CN=C21 UPUZGXILYFKSGE-UHFFFAOYSA-N 0.000 description 1
150000003252 quinoxalines Chemical class 0.000 description 1
230000002285 radioactive effect Effects 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000012266 salt solution Substances 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000003345 scintillation counting Methods 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000007787 solid Substances 0.000 description 1
230000003381 solubilizing effect Effects 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000829 suppository Substances 0.000 description 1
238000010189 synthetic method Methods 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000003826 tablet Substances 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
238000010998 test method Methods 0.000 description 1
MLGCXEBRWGEOQX-UHFFFAOYSA-N tetradifon Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C1=CC(Cl)=C(Cl)C=C1Cl MLGCXEBRWGEOQX-UHFFFAOYSA-N 0.000 description 1
231100001274 therapeutic index Toxicity 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
- 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
- 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

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Neurosurgery (AREA)
Life Sciences & Earth Sciences (AREA)
Neurology (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Biomedical Technology (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Pain & Pain Management (AREA)
Anesthesiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

IL9637290A 1989-11-22 1990-11-16 3-(1,3-dioxoalkyl)-4,5-dihydro-4-oxoimidazo [1,5-c] quinoxaline compounds, their preparation and pharmaceutical compositions containing them IL96372A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DK588389A DK588389D0 (da)	1989-11-22	1989-11-22	Heterocykliske forbindelser, deres fremstilling og anvendelse

Publications (2)

Publication Number	Publication Date
IL96372A0 IL96372A0 (en)	1991-08-16
IL96372A true IL96372A (en)	1994-10-21

Family

ID=8145913

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL9637290A IL96372A (en)	1989-11-22	1990-11-16	3-(1,3-dioxoalkyl)-4,5-dihydro-4-oxoimidazo [1,5-c] quinoxaline compounds, their preparation and pharmaceutical compositions containing them

Country Status (19)

Country	Link
US (1)	US5102885A (de)
EP (1)	EP0502885B1 (de)
JP (1)	JPH05503084A (de)
KR (1)	KR920703593A (de)
AT (1)	ATE106405T1 (de)
AU (1)	AU645508B2 (de)
CA (1)	CA2073046A1 (de)
DE (1)	DE69009493T2 (de)
DK (2)	DK588389D0 (de)
ES (1)	ES2055454T3 (de)
FI (1)	FI97228C (de)
HU (1)	HUT63420A (de)
IE (1)	IE69960B1 (de)
IL (1)	IL96372A (de)
NO (1)	NO300064B1 (de)
NZ (1)	NZ236156A (de)
PT (1)	PT95972B (de)
WO (1)	WO1991007408A1 (de)
ZA (1)	ZA909304B (de)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DK588489D0 (da) *	1989-11-22	1989-11-22	Ferrosan As	Heterocykliske forbindelser, deres fremstilling og anvendelse
FR2722789B1 (fr) *	1994-07-20	1996-08-23	Rhone Poulenc Rorer Sa	Derives d'acide imidazo (1,2-a)indeno(1,2-e) pyrazine-2-carboxylique, leur preparation et les medicaments les contenant

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DK476885D0 (da) *	1985-10-17	1985-10-17	Ferrosan As	Heterocycliske forbindelser og fremgangsmaader til fremstilling heraf
DK155524C (da) *	1987-03-18	1989-09-11	Ferrosan As	Kondenserede imidazolderivater og farmaceutiske praeparater indeholdende disse
DK160876C (da) *	1987-12-08	1991-10-14	Novo Nordisk As	Imidazoquinoxalinforbindelser, fremgangsmaade til deres fremstilling, anvendelse af forbindelserne og farmaceutiske praeparater, hvori forbindelserne indgaar
FR2659329B1 (fr) *	1990-03-09	1994-06-03	Adir	Nouveaux derives d'imidazo [1,2-c] quinazoline, leur procede de preparation et les compositions pharmaceutiques les renfermant.

1989
- 1989-11-22 DK DK588389A patent/DK588389D0/da not_active Application Discontinuation
1990
- 1990-11-16 IL IL9637290A patent/IL96372A/en not_active IP Right Cessation
- 1990-11-19 IE IE415790A patent/IE69960B1/en not_active IP Right Cessation
- 1990-11-20 US US07/616,136 patent/US5102885A/en not_active Expired - Fee Related
- 1990-11-20 NZ NZ236156A patent/NZ236156A/xx unknown
- 1990-11-20 ZA ZA909304A patent/ZA909304B/xx unknown
- 1990-11-22 DK DK90917143.1T patent/DK0502885T3/da active
- 1990-11-22 AU AU67429/90A patent/AU645508B2/en not_active Ceased
- 1990-11-22 ES ES90917143T patent/ES2055454T3/es not_active Expired - Lifetime
- 1990-11-22 DE DE69009493T patent/DE69009493T2/de not_active Expired - Fee Related
- 1990-11-22 WO PCT/DK1990/000303 patent/WO1991007408A1/en not_active Ceased
- 1990-11-22 PT PT95972A patent/PT95972B/pt not_active IP Right Cessation
- 1990-11-22 AT AT90917143T patent/ATE106405T1/de not_active IP Right Cessation
- 1990-11-22 EP EP90917143A patent/EP0502885B1/de not_active Expired - Lifetime
- 1990-11-22 HU HU9201709A patent/HUT63420A/hu unknown
- 1990-11-22 KR KR1019920701199A patent/KR920703593A/ko not_active Ceased
- 1990-11-22 JP JP3500074A patent/JPH05503084A/ja active Pending
- 1990-11-22 CA CA002073046A patent/CA2073046A1/en not_active Abandoned
1992
- 1992-05-13 NO NO921886A patent/NO300064B1/no unknown
- 1992-05-19 FI FI922269A patent/FI97228C/fi not_active IP Right Cessation

Also Published As

Publication number	Publication date
IL96372A0 (en)	1991-08-16
WO1991007408A1 (en)	1991-05-30
ES2055454T3 (es)	1994-08-16
EP0502885B1 (de)	1994-06-01
DE69009493D1 (de)	1994-07-07
IE904157A1 (en)	1991-05-22
NO921886D0 (no)	1992-05-13
US5102885A (en)	1992-04-07
EP0502885A1 (de)	1992-09-16
HU9201709D0 (en)	1992-09-28
DK0502885T3 (da)	1994-09-26
FI97228C (fi)	1996-11-11
FI922269A0 (fi)	1992-05-19
CA2073046A1 (en)	1991-05-23
ATE106405T1 (de)	1994-06-15
DE69009493T2 (de)	1994-12-08
AU645508B2 (en)	1994-01-20
PT95972A (pt)	1991-09-13
NO921886L (no)	1992-05-13
AU6742990A (en)	1991-06-13
PT95972B (pt)	1998-01-30
IE69960B1 (en)	1996-10-16
FI922269L (fi)	1992-05-19
NZ236156A (en)	1993-01-27
JPH05503084A (ja)	1993-05-27
DK588389D0 (da)	1989-11-22
HUT63420A (en)	1993-08-30
ZA909304B (en)	1991-09-25
NO300064B1 (no)	1997-04-01
KR920703593A (ko)	1992-12-18
FI97228B (fi)	1996-07-31

Legal Events

Date	Code	Title	Description
1997-02-18	KB	Patent renewed
2001-07-24	MM9K	Patent not in force due to non-payment of renewal fees

Publication	Publication Date	Title
US4774245A (en)	1988-09-27	Imidazoquinoxaline compounds
US5034530A (en)	1991-07-23	Imidazoquinoxaline compounds and their preparation and use
US4999354A (en)	1991-03-12	Imidazoquinoxaline compounds and their preparation and use
EP0226282B1 (de)	1989-07-05	Heterocyclische Verbindungen und ihre Herstellung und Verwendung
IL104099A (en)	1996-07-23	3-Substituted-5- amino-imidazo [1 5-a] quinazoline compounds their preparation and pharmaceutical compositions containing them
US5075304A (en)	1991-12-24	Imidazoquinoxaline compounds and their preparation and use
EP0201678B1 (de)	1988-06-22	3-(5-Cyclopropyl-1,2,4-oxadiazol-3-yl)-5,6-dihydro-5-methyl-6-oxo-4H-imidazo(1,5-a)(1,4)benzodiazepin, Verfahren zu seiner Herstellung und pharmazeutische Zubereitungen
IL96372A (en)	1994-10-21	3-(1,3-dioxoalkyl)-4,5-dihydro-4-oxoimidazo [1,5-c] quinoxaline compounds, their preparation and pharmaceutical compositions containing them
EP0502038B1 (de)	1997-02-05	Imidazoquinoxalinverbindungen, deren herstellung und verwendung
AU8063391A (en)	1992-01-23	Heterocyclic compounds and their preparation and use
EP0202441B1 (de)	1988-11-17	Oxadiazolylimidazobenzodiazepine, Verfahren zu ihrer Herstellung und pharmazeutische Zubereitungen
AU650733B2 (en)	1994-06-30	Tetracyclic imidazoquinazoline derivatives, process for their preparation and pharmaceutical compositions containing them
US4745112A (en)	1988-05-17	Oxadiazolylimidazobenzodiazepine, compositions, and method III
MXPA98007869A (en)	2000-05-01	Pyridines and pyrimidines fused with ariloxy yariltio, and derived from the mis