IL95490A - History of Diamidazo] A: (1, (2-C-5, 1 [Coinazoline and Imidazo] A-5, 1 [Pyrimido] C-2, 1 [Converted Coinazoline, Preparation and Pharmaceutical Preparations Containing or - Google Patents

History of Diamidazo] A: (1, (2-C-5, 1 [Coinazoline and Imidazo] A-5, 1 [Pyrimido] C-2, 1 [Converted Coinazoline, Preparation and Pharmaceutical Preparations Containing or

Info

Publication number: IL95490A
Authority: IL; Israel
Prior art keywords: compound; quinazoline; formula; cyclopropyl; defined above
Prior art date: 1989-09-08

Application number

IL9549090A

Other languages

English (en)

Hebrew (he)

Other versions

IL95490A0 (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.)

1989-09-08

Filing date

1990-08-27

Publication date

1994-04-12

1990-08-27 Application filed by Novo Nordisk As filed Critical Novo Nordisk As

1991-06-30 Publication of IL95490A0 publication Critical patent/IL95490A0/xx

1994-04-12 Publication of IL95490A publication Critical patent/IL95490A/en

Links

JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 title claims description 71
239000008194 pharmaceutical composition Substances 0.000 title claims description 9
238000002360 preparation method Methods 0.000 title abstract description 4
XQJNBSFKRIFIQW-UHFFFAOYSA-N 1,4,6,14-tetrazatetracyclo[11.4.0.02,6.07,12]heptadeca-2,4,7,9,11,13,15-heptaene Chemical compound N=1C=CCN2C=3N(C=4C=CC=CC4C21)C=NC3 XQJNBSFKRIFIQW-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 100
-1 aralkoxy Chemical group 0.000 claims abstract description 19
229910052736 halogen Inorganic materials 0.000 claims abstract description 12
150000002367 halogens Chemical class 0.000 claims abstract description 11
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 10
239000001257 hydrogen Substances 0.000 claims abstract description 10
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 9
229910052799 carbon Inorganic materials 0.000 claims abstract description 6
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 6
125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
150000001721 carbon Chemical group 0.000 claims abstract description 5
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 3
125000003277 amino group Chemical group 0.000 claims abstract description 3
125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 3
125000003118 aryl group Chemical group 0.000 claims abstract description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract 4
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims abstract 2
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract 2
238000000034 method Methods 0.000 claims description 15
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
210000003169 central nervous system Anatomy 0.000 claims description 11
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 6
239000002253 acid Substances 0.000 claims description 5
150000003839 salts Chemical class 0.000 claims description 5
239000003085 diluting agent Substances 0.000 claims description 4
239000003937 drug carrier Substances 0.000 claims description 4
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 3
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
150000001412 amines Chemical class 0.000 claims description 2
239000012024 dehydrating agents‎ Substances 0.000 claims description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 2
239000007800 oxidant agent Substances 0.000 claims description 2
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
WTEVQBCEXWBHNA-YFHOEESVSA-N neral Chemical compound CC(C)=CCC\C(C)=C/C=O WTEVQBCEXWBHNA-YFHOEESVSA-N 0.000 claims 2
WTEVQBCEXWBHNA-UHFFFAOYSA-N Citral Natural products CC(C)=CCCC(C)=CC=O WTEVQBCEXWBHNA-UHFFFAOYSA-N 0.000 claims 1
125000000217 alkyl group Chemical group 0.000 claims 1
WTEVQBCEXWBHNA-JXMROGBWSA-N citral A Natural products CC(C)=CCC\C(C)=C\C=O WTEVQBCEXWBHNA-JXMROGBWSA-N 0.000 claims 1
241000124008 Mammalia Species 0.000 abstract description 4
239000001961 anticonvulsive agent Substances 0.000 abstract description 4
230000000949 anxiolytic effect Effects 0.000 abstract description 4
KJMFQJFNQYWQAV-UHFFFAOYSA-N 3h-imidazo[4,5-h]quinazoline Chemical class C1=NC=NC2=C(NC=N3)C3=CC=C21 KJMFQJFNQYWQAV-UHFFFAOYSA-N 0.000 abstract description 3
239000002249 anxiolytic agent Substances 0.000 abstract description 3
210000004556 brain Anatomy 0.000 abstract description 3
230000000147 hypnotic effect Effects 0.000 abstract description 3
230000003474 anti-emetic effect Effects 0.000 abstract description 2
229940125681 anticonvulsant agent Drugs 0.000 abstract description 2
229940125683 antiemetic agent Drugs 0.000 abstract description 2
239000002111 antiemetic agent Substances 0.000 abstract description 2
239000000164 antipsychotic agent Substances 0.000 abstract description 2
229940005529 antipsychotics Drugs 0.000 abstract description 2
229940005530 anxiolytics Drugs 0.000 abstract description 2
230000003920 cognitive function Effects 0.000 abstract description 2
239000003326 hypnotic agent Substances 0.000 abstract description 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 3
150000002431 hydrogen Chemical class 0.000 abstract 3
125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 1
125000003601 C2-C6 alkynyl group Chemical group 0.000 abstract 1
125000004104 aryloxy group Chemical group 0.000 abstract 1
125000004122 cyclic group Chemical group 0.000 abstract 1
125000004984 dialkylaminoalkoxy group Chemical group 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
239000000203 mixture Substances 0.000 description 25
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 20
239000013078 crystal Substances 0.000 description 15
239000000243 solution Substances 0.000 description 13
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
239000002244 precipitate Substances 0.000 description 11
239000002904 solvent Substances 0.000 description 10
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
238000010992 reflux Methods 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 7
239000000706 filtrate Substances 0.000 description 7
239000000725 suspension Substances 0.000 description 7
VEUMBMHMMCOFAG-UHFFFAOYSA-N 2,3-dihydrooxadiazole Chemical compound N1NC=CO1 VEUMBMHMMCOFAG-UHFFFAOYSA-N 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-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
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 6
PIEAAARUUJGZGF-UHFFFAOYSA-N 2,4,5-trichloroquinazoline Chemical compound ClC1=CC=CC2=NC(Cl)=NC(Cl)=C21 PIEAAARUUJGZGF-UHFFFAOYSA-N 0.000 description 5
BGHGVAKKIBOJGS-UHFFFAOYSA-N 5-cyclopropyl-3-(isocyanomethyl)-1,2,4-oxadiazole Chemical compound [C-]#[N+]CC1=NOC(C2CC2)=N1 BGHGVAKKIBOJGS-UHFFFAOYSA-N 0.000 description 5
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
239000002552 dosage form Substances 0.000 description 5
238000001914 filtration Methods 0.000 description 5
238000003756 stirring Methods 0.000 description 5
KFVVSDPKGPUSEL-UHFFFAOYSA-N 3-cyclopropyl-5-(isocyanomethyl)-1,2,4-oxadiazole Chemical compound O1C(C[N+]#[C-])=NC(C2CC2)=N1 KFVVSDPKGPUSEL-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
239000007787 solid Substances 0.000 description 4
239000012258 stirred mixture Substances 0.000 description 4
239000000126 substance Substances 0.000 description 4
238000012360 testing method Methods 0.000 description 4
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
239000002775 capsule Substances 0.000 description 3
229940125782 compound 2 Drugs 0.000 description 3
239000002198 insoluble material Substances 0.000 description 3
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 3
229910052759 nickel Inorganic materials 0.000 description 3
239000012044 organic layer Substances 0.000 description 3
229910052700 potassium Inorganic materials 0.000 description 3
239000011591 potassium Substances 0.000 description 3
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
150000003246 quinazolines Chemical class 0.000 description 3
229910000104 sodium hydride Inorganic materials 0.000 description 3
UAOUIVVJBYDFKD-XKCDOFEDSA-N (1R,9R,10S,11R,12R,15S,18S,21R)-10,11,21-trihydroxy-8,8-dimethyl-14-methylidene-4-(prop-2-enylamino)-20-oxa-5-thia-3-azahexacyclo[9.7.2.112,15.01,9.02,6.012,18]henicosa-2(6),3-dien-13-one Chemical compound C([C@@H]1[C@@H](O)[C@@]23C(C1=C)=O)C[C@H]2[C@]12C(N=C(NCC=C)S4)=C4CC(C)(C)[C@H]1[C@H](O)[C@]3(O)OC2 UAOUIVVJBYDFKD-XKCDOFEDSA-N 0.000 description 2
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
IDPYPOATDTXYJZ-UHFFFAOYSA-N 2-[(5-bromo-2-chloroquinazolin-4-yl)amino]ethanol Chemical compound C1=CC(Br)=C2C(NCCO)=NC(Cl)=NC2=C1 IDPYPOATDTXYJZ-UHFFFAOYSA-N 0.000 description 2
RABIUUVAEMPACI-UHFFFAOYSA-N 2-[[2-chloro-5-(trifluoromethyl)quinazolin-4-yl]amino]ethanol Chemical compound C1=CC(C(F)(F)F)=C2C(NCCO)=NC(Cl)=NC2=C1 RABIUUVAEMPACI-UHFFFAOYSA-N 0.000 description 2
WQKHERPPDYPMNX-UHFFFAOYSA-N 6-chloro-3,4-dihydro-2h-naphthalen-1-one Chemical compound O=C1CCCC2=CC(Cl)=CC=C21 WQKHERPPDYPMNX-UHFFFAOYSA-N 0.000 description 2
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
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 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
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
LNUFLCYMSVYYNW-ZPJMAFJPSA-N [(2r,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[[(3s,5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-disulfo Chemical compound O([C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CCCC(C)C)[C@H]1O[C@H](COS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]1OS(O)(=O)=O LNUFLCYMSVYYNW-ZPJMAFJPSA-N 0.000 description 2
230000002378 acidificating effect Effects 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
239000000969 carrier Substances 0.000 description 2
239000004359 castor oil Substances 0.000 description 2
235000019438 castor oil Nutrition 0.000 description 2
229940126214 compound 3 Drugs 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
238000000354 decomposition reaction Methods 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
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 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
239000012065 filter cake Substances 0.000 description 2
229960002200 flunitrazepam Drugs 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
239000000825 pharmaceutical preparation Substances 0.000 description 2
ULSIYEODSMZIPX-UHFFFAOYSA-N phenylethanolamine Chemical compound NCC(O)C1=CC=CC=C1 ULSIYEODSMZIPX-UHFFFAOYSA-N 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
239000000377 silicon dioxide Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
239000012312 sodium hydride Substances 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
239000007858 starting material 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
ASGMFNBUXDJWJJ-JLCFBVMHSA-N (1R,3R)-3-[[3-bromo-1-[4-(5-methyl-1,3,4-thiadiazol-2-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]-N,1-dimethylcyclopentane-1-carboxamide Chemical compound BrC1=NN(C2=NC(=NC=C21)N[C@H]1C[C@@](CC1)(C(=O)NC)C)C1=CC=C(C=C1)C=1SC(=NN=1)C ASGMFNBUXDJWJJ-JLCFBVMHSA-N 0.000 description 1
AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 1
ABJSOROVZZKJGI-OCYUSGCXSA-N (1r,2r,4r)-2-(4-bromophenyl)-n-[(4-chlorophenyl)-(2-fluoropyridin-4-yl)methyl]-4-morpholin-4-ylcyclohexane-1-carboxamide Chemical compound C1=NC(F)=CC(C(NC(=O)[C@H]2[C@@H](C[C@@H](CC2)N2CCOCC2)C=2C=CC(Br)=CC=2)C=2C=CC(Cl)=CC=2)=C1 ABJSOROVZZKJGI-OCYUSGCXSA-N 0.000 description 1
GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 description 1
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239000008346 aqueous phase Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
125000004659 aryl alkyl thio group Chemical group 0.000 description 1
XRWSZZJLZRKHHD-WVWIJVSJSA-N asunaprevir Chemical compound O=C([C@@H]1C[C@H](CN1C(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)(C)C)OC1=NC=C(C2=CC=C(Cl)C=C21)OC)N[C@]1(C(=O)NS(=O)(=O)C2CC2)C[C@H]1C=C XRWSZZJLZRKHHD-WVWIJVSJSA-N 0.000 description 1
KGNDCEVUMONOKF-UGPLYTSKSA-N benzyl n-[(2r)-1-[(2s,4r)-2-[[(2s)-6-amino-1-(1,3-benzoxazol-2-yl)-1,1-dihydroxyhexan-2-yl]carbamoyl]-4-[(4-methylphenyl)methoxy]pyrrolidin-1-yl]-1-oxo-4-phenylbutan-2-yl]carbamate Chemical compound C1=CC(C)=CC=C1CO[C@H]1CN(C(=O)[C@@H](CCC=2C=CC=CC=2)NC(=O)OCC=2C=CC=CC=2)[C@H](C(=O)N[C@@H](CCCCN)C(O)(O)C=2OC3=CC=CC=C3N=2)C1 KGNDCEVUMONOKF-UGPLYTSKSA-N 0.000 description 1
230000027455 binding Effects 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000037396 body weight Effects 0.000 description 1
239000000872 buffer Substances 0.000 description 1
150000001720 carbohydrates Chemical class 0.000 description 1
235000014633 carbohydrates Nutrition 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
229920001429 chelating resin Polymers 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000004040 coloring Methods 0.000 description 1
229940125904 compound 1 Drugs 0.000 description 1
229940125773 compound 10 Drugs 0.000 description 1
229940125797 compound 12 Drugs 0.000 description 1
229940126543 compound 14 Drugs 0.000 description 1
229940125758 compound 15 Drugs 0.000 description 1
229940126142 compound 16 Drugs 0.000 description 1
229940125810 compound 20 Drugs 0.000 description 1
229940126086 compound 21 Drugs 0.000 description 1
229940126208 compound 22 Drugs 0.000 description 1
229940125833 compound 23 Drugs 0.000 description 1
229940125961 compound 24 Drugs 0.000 description 1
229940125846 compound 25 Drugs 0.000 description 1
229940125851 compound 27 Drugs 0.000 description 1
229940127204 compound 29 Drugs 0.000 description 1
229940125877 compound 31 Drugs 0.000 description 1
229940125878 compound 36 Drugs 0.000 description 1
229940125807 compound 37 Drugs 0.000 description 1
229940127573 compound 38 Drugs 0.000 description 1
229940126540 compound 41 Drugs 0.000 description 1
229940125936 compound 42 Drugs 0.000 description 1
229940125844 compound 46 Drugs 0.000 description 1
229940127271 compound 49 Drugs 0.000 description 1
229940125898 compound 5 Drugs 0.000 description 1
230000036461 convulsion Effects 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
239000012043 crude product Substances 0.000 description 1
RCJVRSBWZCNNQT-UHFFFAOYSA-N dichloridooxygen Chemical compound ClOCl RCJVRSBWZCNNQT-UHFFFAOYSA-N 0.000 description 1
FDSGHYHRLSWSLQ-UHFFFAOYSA-N dichloromethane;propan-2-one Chemical compound ClCCl.CC(C)=O FDSGHYHRLSWSLQ-UHFFFAOYSA-N 0.000 description 1
LGTLXDJOAJDFLR-UHFFFAOYSA-N diethyl chlorophosphate Chemical compound CCOP(Cl)(=O)OCC LGTLXDJOAJDFLR-UHFFFAOYSA-N 0.000 description 1
208000035475 disorder Diseases 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
238000006073 displacement reaction Methods 0.000 description 1
239000008298 dragée Substances 0.000 description 1
239000003480 eluent Substances 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
FPULFENIJDPZBX-UHFFFAOYSA-N ethyl 2-isocyanoacetate Chemical compound CCOC(=O)C[N+]#[C-] FPULFENIJDPZBX-UHFFFAOYSA-N 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
238000009472 formulation Methods 0.000 description 1
239000012458 free base Substances 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 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
239000012442 inert solvent Substances 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
206010022437 insomnia Diseases 0.000 description 1
ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
239000007788 liquid Substances 0.000 description 1
RENRQMCACQEWFC-UGKGYDQZSA-N lnp023 Chemical compound C1([C@H]2N(CC=3C=4C=CNC=4C(C)=CC=3OC)CC[C@@H](C2)OCC)=CC=C(C(O)=O)C=C1 RENRQMCACQEWFC-UGKGYDQZSA-N 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
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
239000000463 material Substances 0.000 description 1
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
239000002808 molecular sieve Substances 0.000 description 1
OMCUPXRCMTUDHI-UHFFFAOYSA-N n'-hydroxycyclopropanecarboximidamide Chemical compound ON=C(N)C1CC1 OMCUPXRCMTUDHI-UHFFFAOYSA-N 0.000 description 1
IOMMMLWIABWRKL-WUTDNEBXSA-N nazartinib Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCC[C@H]1N1C2=C(Cl)C=CC=C2N=C1NC(=O)C1=CC=NC(C)=C1 IOMMMLWIABWRKL-WUTDNEBXSA-N 0.000 description 1
230000001777 nootropic effect Effects 0.000 description 1
229940078552 o-xylene Drugs 0.000 description 1
239000004533 oil dispersion Substances 0.000 description 1
PIDFDZJZLOTZTM-KHVQSSSXSA-N ombitasvir Chemical compound COC(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C(=O)NC1=CC=C([C@H]2N([C@@H](CC2)C=2C=CC(NC(=O)[C@H]3N(CCC3)C(=O)[C@@H](NC(=O)OC)C(C)C)=CC=2)C=2C=CC(=CC=2)C(C)(C)C)C=C1 PIDFDZJZLOTZTM-KHVQSSSXSA-N 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
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
DDBREPKUVSBGFI-UHFFFAOYSA-N phenobarbital Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=O)NC1=O DDBREPKUVSBGFI-UHFFFAOYSA-N 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
DRYRBWIFRVMRPV-UHFFFAOYSA-N quinazolin-4-amine Chemical class C1=CC=C2C(N)=NC=NC2=C1 DRYRBWIFRVMRPV-UHFFFAOYSA-N 0.000 description 1
ATQUABCIJINPMX-UHFFFAOYSA-N quinazolin-5-ol Chemical compound C1=NC=C2C(O)=CC=CC2=N1 ATQUABCIJINPMX-UHFFFAOYSA-N 0.000 description 1
XZCGZJBJGLAZGG-UHFFFAOYSA-N quinazoline-5-carboxamide Chemical compound N1=CN=CC=2C(=CC=CC1=2)C(=O)N XZCGZJBJGLAZGG-UHFFFAOYSA-N 0.000 description 1
230000002285 radioactive effect Effects 0.000 description 1
239000000376 reactant Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
102000005962 receptors Human genes 0.000 description 1
108020003175 receptors Proteins 0.000 description 1
239000012266 salt solution Substances 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
239000002002 slurry Substances 0.000 description 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
230000009870 specific binding Effects 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
239000000829 suppository Substances 0.000 description 1
238000003786 synthesis reaction 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
IQSYKHVFMYGJER-UHFFFAOYSA-N tert-butyl 2-isocyanoacetate Chemical compound CC(C)(C)OC(=O)C[N+]#[C-] IQSYKHVFMYGJER-UHFFFAOYSA-N 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
231100001274 therapeutic index Toxicity 0.000 description 1
YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 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
- C07D487/12—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 three hetero rings
- C07D487/14—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
- 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

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Life Sciences & Earth Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (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)

IL9549090A 1989-09-08 1990-08-27 History of Diamidazo] A: (1, (2-C-5, 1 [Coinazoline and Imidazo] A-5, 1 [Pyrimido] C-2, 1 [Converted Coinazoline, Preparation and Pharmaceutical Preparations Containing or IL95490A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DK443589A DK443589D0 (da)	1989-09-08	1989-09-08	Heterocykliske forbindelser, deres fremstilling og anvendelse

Publications (2)

Publication Number	Publication Date
IL95490A0 IL95490A0 (en)	1991-06-30
IL95490A true IL95490A (en)	1994-04-12

Family

ID=8133490

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL9549090A IL95490A (en)	1989-09-08	1990-08-27	History of Diamidazo] A: (1, (2-C-5, 1 [Coinazoline and Imidazo] A-5, 1 [Pyrimido] C-2, 1 [Converted Coinazoline, Preparation and Pharmaceutical Preparations Containing or

Country Status (20)

Country	Link
US (1)	US5100895A (de)
EP (2)	EP0491814B1 (de)
JP (1)	JPH05504945A (de)
KR (1)	KR927003598A (de)
AT (1)	ATE131168T1 (de)
AU (1)	AU638758B2 (de)
CA (1)	CA2066695A1 (de)
DE (1)	DE69024058T2 (de)
DK (2)	DK443589D0 (de)
ES (1)	ES2080159T3 (de)
FI (1)	FI97137C (de)
GR (1)	GR3018774T3 (de)
HU (2)	HUT63423A (de)
IE (1)	IE76298B1 (de)
IL (1)	IL95490A (de)
NO (1)	NO180635C (de)
NZ (1)	NZ235116A (de)
PT (1)	PT95249B (de)
WO (1)	WO1991003478A1 (de)
ZA (1)	ZA907112B (de)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DK204291D0 (da) *	1991-12-20	1991-12-20	Novo Nordisk As	Heterocykliske forbindelser deres fremstilling og anvendelse
DK41191D0 (da) *	1991-03-07	1991-03-07	Novo Nordisk As	Heterocycliske forbindelser, deres fremstilling og anvendelse
NZ243065A (en) *	1991-06-13	1995-07-26	Lundbeck & Co As H	Piperidine derivatives and pharmaceutical compositions
TW201311B (de) *	1991-06-17	1993-03-01	Hoffmann La Roche
WO1993017025A1 (en) *	1992-02-19	1993-09-02	The Upjohn Company	3-substituted imidazo(1,5-a)quinoxalines and quinazolines with cns activity
CN101277939A (zh) *	2005-09-09	2008-10-01	布里斯托尔-迈尔斯斯奎布公司	无环ikur抑制剂

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3847918A (en) *	1973-05-17	1974-11-12	Sandoz Ag	S-triazolo(1,5-c)quinazolin-7(6h)-ones
DK476885D0 (da) *	1985-10-17	1985-10-17	Ferrosan As	Heterocycliske forbindelser og fremgangsmaader til fremstilling heraf
ATE44381T1 (de) *	1985-10-17	1989-07-15	Ferrosan As	Heterocyclische verbindungen und ihre herstellung und verwendung.
DE3730718A1 (de) *	1987-09-12	1989-03-23	Basf Ag	Tetracyclische chinazolinderivate, herstellung und verwendung

1989
- 1989-09-08 DK DK443589A patent/DK443589D0/da not_active Application Discontinuation
1990
- 1990-08-24 IE IE308390A patent/IE76298B1/en not_active IP Right Cessation
- 1990-08-27 IL IL9549090A patent/IL95490A/en not_active IP Right Cessation
- 1990-08-31 NZ NZ235116A patent/NZ235116A/en unknown
- 1990-09-05 US US07/578,054 patent/US5100895A/en not_active Expired - Fee Related
- 1990-09-06 DK DK90914139.2T patent/DK0491814T3/da active
- 1990-09-06 DE DE69024058T patent/DE69024058T2/de not_active Expired - Fee Related
- 1990-09-06 CA CA002066695A patent/CA2066695A1/en not_active Abandoned
- 1990-09-06 EP EP90914139A patent/EP0491814B1/de not_active Expired - Lifetime
- 1990-09-06 AU AU64297/90A patent/AU638758B2/en not_active Ceased
- 1990-09-06 JP JP2513237A patent/JPH05504945A/ja active Pending
- 1990-09-06 WO PCT/DK1990/000231 patent/WO1991003478A1/en not_active Ceased
- 1990-09-06 ZA ZA907112A patent/ZA907112B/xx unknown
- 1990-09-06 KR KR1019920700516A patent/KR927003598A/ko not_active Ceased
- 1990-09-06 ES ES90914139T patent/ES2080159T3/es not_active Expired - Lifetime
- 1990-09-06 AT AT90914139T patent/ATE131168T1/de not_active IP Right Cessation
- 1990-09-06 HU HU92774A patent/HUT63423A/hu unknown
- 1990-09-06 EP EP90610057A patent/EP0417027A1/de active Pending
- 1990-09-07 PT PT95249A patent/PT95249B/pt not_active IP Right Cessation
1992
- 1992-03-06 FI FI921004A patent/FI97137C/fi not_active IP Right Cessation
- 1992-03-06 HU HU9200774A patent/HU9200774D0/hu unknown
- 1992-03-06 NO NO920910A patent/NO180635C/no unknown
1996
- 1996-01-24 GR GR960400173T patent/GR3018774T3/el unknown

Also Published As

Publication number	Publication date
NO180635B (no)	1997-02-10
EP0491814B1 (de)	1995-12-06
ZA907112B (en)	1991-07-31
CA2066695A1 (en)	1991-03-09
FI97137C (fi)	1996-10-25
PT95249B (pt)	1997-06-30
HUT63423A (en)	1993-08-30
DE69024058D1 (de)	1996-01-18
NO180635C (no)	1997-05-21
HU9200774D0 (en)	1992-05-28
DK443589D0 (da)	1989-09-08
FI97137B (fi)	1996-07-15
NZ235116A (en)	1992-08-26
WO1991003478A1 (en)	1991-03-21
ATE131168T1 (de)	1995-12-15
GR3018774T3 (en)	1996-04-30
IL95490A0 (en)	1991-06-30
EP0491814A1 (de)	1992-07-01
NO920910D0 (no)	1992-03-06
ES2080159T3 (es)	1996-02-01
IE903083A1 (en)	1991-03-13
PT95249A (pt)	1991-05-22
NO920910L (no)	1992-03-06
DE69024058T2 (de)	1996-08-29
IE76298B1 (en)	1997-10-08
AU6429790A (en)	1991-04-08
AU638758B2 (en)	1993-07-08
EP0417027A1 (de)	1991-03-13
US5100895A (en)	1992-03-31
KR927003598A (ko)	1992-12-18
JPH05504945A (ja)	1993-07-29
DK0491814T3 (da)	1996-04-09
FI921004A0 (fi)	1992-03-06

Legal Events

Date	Code	Title	Description
1996-11-14	KB	Patent renewed
2001-06-14	RH	Patent void

Publication	Publication Date	Title
US4886797A (en)	1989-12-12	Heterocyclic compounds and their preparation and use
KR960010455B1 (ko)	1996-08-01	헤테로사이클릭 화합물, 이의 제법 및 용도
EP0241682B1 (de)	1990-11-28	Benzodiazepinderivate und ihre Herstellung und Verwendung
AU613392B2 (en)	1991-08-01	Imidazo (1,2-b) pyridazin-2-yl carbamate derivatives
EP0226282B1 (de)	1989-07-05	Heterocyclische Verbindungen und ihre Herstellung und Verwendung
AU627181B2 (en)	1992-08-20	Imidazoquinoxaline compounds and their preparation and use
EP0491814B1 (de)	1995-12-06	Tetrazyklische imidazochinazolinderivate, deren herstellung und pharmazeutische zusammensetzungen
RU2167877C2 (ru)	2001-05-27	Производные конденсированных полициклических гетероциклических соединений и способ их получения
US4723003A (en)	1988-02-02	Benzopyrrolobenzodiazepines and quinobenzodiazepines
EP0535104B1 (de)	1996-09-04	Heterocyclische verbindungen, herstellung und verwendung
EP0202441B1 (de)	1988-11-17	Oxadiazolylimidazobenzodiazepine, Verfahren zu ihrer Herstellung und pharmazeutische Zubereitungen
US4745112A (en)	1988-05-17	Oxadiazolylimidazobenzodiazepine, compositions, and method III
EP0575442B1 (de)	1995-12-27	Tetracyclische imidazochinazolin-derivate, verfahren zu ihrer herstellung und diese enthaltende arzneimittel
US3891643A (en)	1975-06-24	Pyrrolo{8 1,2,3-de{9 quinoxalin-2-(3H)-ones and related compounds
US3822259A (en)	1974-07-02	7-phenyl-1h(1,3)-oxazino(3,2-a)(1,4)benzodiazepine-1,3(2h)-diones
CA2217719A1 (en)	1996-10-17	Anellated .beta.-carbolines