NO853859L - Triazolikinazolin-forbindelser. - Google Patents
Triazolikinazolin-forbindelser.Info
- Publication number
- NO853859L NO853859L NO853859A NO853859A NO853859L NO 853859 L NO853859 L NO 853859L NO 853859 A NO853859 A NO 853859A NO 853859 A NO853859 A NO 853859A NO 853859 L NO853859 L NO 853859L
- Authority
- NO
- Norway
- Prior art keywords
- lower alkyl
- formula
- compound
- stands
- acid
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims description 72
- 125000000217 alkyl group Chemical group 0.000 claims description 68
- 229910052757 nitrogen Inorganic materials 0.000 claims description 60
- -1 hydroxy, amino Chemical group 0.000 claims description 44
- 150000003839 salts Chemical class 0.000 claims description 32
- 238000000034 method Methods 0.000 claims description 27
- 125000003118 aryl group Chemical group 0.000 claims description 21
- 238000006243 chemical reaction Methods 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 229910052760 oxygen Inorganic materials 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- 150000002367 halogens Chemical class 0.000 claims description 13
- 125000005842 heteroatom Chemical group 0.000 claims description 13
- 150000002431 hydrogen Chemical class 0.000 claims description 11
- 229910052717 sulfur Inorganic materials 0.000 claims description 11
- 125000003342 alkenyl group Chemical group 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 150000001721 carbon Chemical group 0.000 claims description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
- 239000001301 oxygen Substances 0.000 claims description 8
- 229920006395 saturated elastomer Polymers 0.000 claims description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- 239000007800 oxidant agent Substances 0.000 claims description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
- WOOIBJWFHSHPJN-UHFFFAOYSA-N 2h-triazolo[4,5-h]quinazoline Chemical group C1=CC2=NNN=C2C2=NC=NC=C21 WOOIBJWFHSHPJN-UHFFFAOYSA-N 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 150000002540 isothiocyanates Chemical class 0.000 claims description 3
- 125000003396 thiol group Chemical class [H]S* 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 238000006798 ring closing metathesis reaction Methods 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
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 98
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 90
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 80
- 238000002844 melting Methods 0.000 description 68
- 230000008018 melting Effects 0.000 description 68
- 239000000203 mixture Substances 0.000 description 68
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 53
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 44
- 239000007787 solid Substances 0.000 description 31
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
- 239000000243 solution Substances 0.000 description 26
- 238000010992 reflux Methods 0.000 description 25
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 23
- 239000000047 product Substances 0.000 description 22
- 239000011541 reaction mixture Substances 0.000 description 20
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 17
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- 238000001953 recrystallisation Methods 0.000 description 16
- 239000007858 starting material Substances 0.000 description 16
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 15
- 239000002253 acid Substances 0.000 description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- 239000002244 precipitate Substances 0.000 description 12
- 229910021529 ammonia Inorganic materials 0.000 description 11
- 239000002585 base Substances 0.000 description 11
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 11
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- 150000003852 triazoles Chemical class 0.000 description 10
- 238000001816 cooling Methods 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 8
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
- 239000004480 active ingredient Substances 0.000 description 8
- 150000001408 amides Chemical class 0.000 description 8
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 8
- 229940098779 methanesulfonic acid Drugs 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 7
- 125000005843 halogen group Chemical group 0.000 description 7
- 125000000623 heterocyclic group Chemical group 0.000 description 7
- 239000012312 sodium hydride Substances 0.000 description 7
- 229910000104 sodium hydride Inorganic materials 0.000 description 7
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 6
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 6
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 6
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 6
- 239000002775 capsule Substances 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 239000005457 ice water Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 150000002825 nitriles Chemical class 0.000 description 6
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 6
- 239000011343 solid material Substances 0.000 description 6
- 229910001220 stainless steel Inorganic materials 0.000 description 6
- 239000010935 stainless steel Substances 0.000 description 6
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000000908 ammonium hydroxide Substances 0.000 description 5
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 description 5
- SKTSVWWOAIAIKI-UHFFFAOYSA-N furan-2-carbohydrazide Chemical compound NNC(=O)C1=CC=CO1 SKTSVWWOAIAIKI-UHFFFAOYSA-N 0.000 description 5
- 239000012362 glacial acetic acid Substances 0.000 description 5
- 239000012442 inert solvent Substances 0.000 description 5
- 125000001810 isothiocyanato group Chemical group *N=C=S 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 229920001223 polyethylene glycol Polymers 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 5
- GDHYPPBFBJXNRE-UHFFFAOYSA-N 2-isothiocyanatobenzonitrile Chemical compound S=C=NC1=CC=CC=C1C#N GDHYPPBFBJXNRE-UHFFFAOYSA-N 0.000 description 4
- HGZKGYSDLSMMKA-UHFFFAOYSA-N 5-chloro-2-isocyanatobenzonitrile Chemical compound ClC1=CC=C(N=C=O)C(C#N)=C1 HGZKGYSDLSMMKA-UHFFFAOYSA-N 0.000 description 4
- MSJODEOZODDVGW-UHFFFAOYSA-N 9-chloro-2-(2-furanyl)-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound N=1N2C(N)=NC3=CC=C(Cl)C=C3C2=NC=1C1=CC=CO1 MSJODEOZODDVGW-UHFFFAOYSA-N 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 4
- LJWMIJROWBUNJV-UHFFFAOYSA-N N=1N2C(S)=NC3=CC=C(Cl)C=C3C2=NC=1C1=CC=CO1 Chemical compound N=1N2C(S)=NC3=CC=C(Cl)C=C3C2=NC=1C1=CC=CO1 LJWMIJROWBUNJV-UHFFFAOYSA-N 0.000 description 4
- 229920002472 Starch Polymers 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 4
- AXPGZURVLRWNBR-UHFFFAOYSA-N chembl330116 Chemical compound N=1N2C(O)=NC3=CC=CC=C3C2=NC=1C1=CC=CC=C1 AXPGZURVLRWNBR-UHFFFAOYSA-N 0.000 description 4
- XEVZWKHGVYHGAM-UHFFFAOYSA-N chembl414023 Chemical compound N1=C2C3=CC(Cl)=CC=C3NC(=O)N2N=C1C1=CC=CO1 XEVZWKHGVYHGAM-UHFFFAOYSA-N 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 239000012458 free base Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 4
- 125000001261 isocyanato group Chemical group *N=C=O 0.000 description 4
- 239000012452 mother liquor Substances 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- 239000004533 oil dispersion Substances 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 235000019698 starch Nutrition 0.000 description 4
- 239000000454 talc Substances 0.000 description 4
- 229910052623 talc Inorganic materials 0.000 description 4
- CYDGREISJRDSDE-UHFFFAOYSA-N 2-amino-5-chlorobenzohydrazide Chemical compound NNC(=O)C1=CC(Cl)=CC=C1N CYDGREISJRDSDE-UHFFFAOYSA-N 0.000 description 3
- YJCCKQQVXNNAAR-UHFFFAOYSA-N 2-fluorobenzohydrazide Chemical compound NNC(=O)C1=CC=CC=C1F YJCCKQQVXNNAAR-UHFFFAOYSA-N 0.000 description 3
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 3
- FQLNVWAFXQUXGW-UHFFFAOYSA-N 2-isocyanatobenzonitrile Chemical compound O=C=NC1=CC=CC=C1C#N FQLNVWAFXQUXGW-UHFFFAOYSA-N 0.000 description 3
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 3
- 108010010803 Gelatin Proteins 0.000 description 3
- 239000005909 Kieselgur Substances 0.000 description 3
- 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 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- 239000004202 carbamide Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- YKGMKSIHIVVYKY-UHFFFAOYSA-N dabrafenib mesylate Chemical compound CS(O)(=O)=O.S1C(C(C)(C)C)=NC(C=2C(=C(NS(=O)(=O)C=3C(=CC=CC=3F)F)C=CC=2)F)=C1C1=CC=NC(N)=N1 YKGMKSIHIVVYKY-UHFFFAOYSA-N 0.000 description 3
- AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000008273 gelatin Substances 0.000 description 3
- 229920000159 gelatin Polymers 0.000 description 3
- 235000019322 gelatine Nutrition 0.000 description 3
- 235000011852 gelatine desserts Nutrition 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 125000001475 halogen functional group Chemical group 0.000 description 3
- 239000008101 lactose Substances 0.000 description 3
- ACKFDYCQCBEDNU-UHFFFAOYSA-J lead(2+);tetraacetate Chemical compound [Pb+2].CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O ACKFDYCQCBEDNU-UHFFFAOYSA-J 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 239000000825 pharmaceutical preparation Substances 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 238000007363 ring formation reaction Methods 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- 239000008107 starch Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 2
- UUSJUENFEGZBBT-UHFFFAOYSA-N 2-(furan-2-yl)-5-methylsulfanyl-[1,2,4]triazolo[1,5-c]quinazoline Chemical compound N=1N2C(SC)=NC3=CC=CC=C3C2=NC=1C1=CC=CO1 UUSJUENFEGZBBT-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- QYRDWARBHMCOAG-UHFFFAOYSA-N 2-amino-5-chlorobenzonitrile Chemical compound NC1=CC=C(Cl)C=C1C#N QYRDWARBHMCOAG-UHFFFAOYSA-N 0.000 description 2
- HLCPWBZNUKCSBN-UHFFFAOYSA-N 2-aminobenzonitrile Chemical compound NC1=CC=CC=C1C#N HLCPWBZNUKCSBN-UHFFFAOYSA-N 0.000 description 2
- SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical compound OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 description 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 2
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 2
- ACGJIIRRFHEHAB-UHFFFAOYSA-N 4-chloro-2-[5-(furan-2-yl)-1h-1,2,4-triazol-3-yl]aniline Chemical compound NC1=CC=C(Cl)C=C1C1=NNC(C=2OC=CC=2)=N1 ACGJIIRRFHEHAB-UHFFFAOYSA-N 0.000 description 2
- XJVKXLHNCRNMAV-UHFFFAOYSA-N 5-chloro-2-isothiocyanatobenzonitrile Chemical compound ClC1=CC=C(N=C=S)C(C#N)=C1 XJVKXLHNCRNMAV-UHFFFAOYSA-N 0.000 description 2
- MYQFJMYJVJRSGP-UHFFFAOYSA-N 6-chloro-1h-3,1-benzoxazine-2,4-dione Chemical compound N1C(=O)OC(=O)C2=CC(Cl)=CC=C21 MYQFJMYJVJRSGP-UHFFFAOYSA-N 0.000 description 2
- QZUJVRFMFGQENA-UHFFFAOYSA-N 9-chloro-2-(furan-2-yl)-5-methylsulfanyl-[1,2,4]triazolo[1,5-c]quinazoline Chemical compound N=1N2C(SC)=NC3=CC=C(Cl)C=C3C2=NC=1C1=CC=CO1 QZUJVRFMFGQENA-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
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- 239000000594 mannitol Substances 0.000 description 1
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- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
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- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
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- 125000002757 morpholinyl group Chemical group 0.000 description 1
- FGDYAAXXBPMZDU-UHFFFAOYSA-N n,n-dimethylacetamide;ethanol Chemical compound CCO.CN(C)C(C)=O FGDYAAXXBPMZDU-UHFFFAOYSA-N 0.000 description 1
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- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- OPHDQDXGXHXWON-UHFFFAOYSA-N n-ethyl-2-(furan-2-yl)-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound N=1N2C(=NCC)NC3=CC=CC=C3C2=NC=1C1=CC=CO1 OPHDQDXGXHXWON-UHFFFAOYSA-N 0.000 description 1
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- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 229960003512 nicotinic acid Drugs 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- IUJBLZNOFNHTEQ-UHFFFAOYSA-N o-ethyl n-(2-cyanophenyl)carbamothioate Chemical compound CCOC(=S)NC1=CC=CC=C1C#N IUJBLZNOFNHTEQ-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
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- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 1
- LLGRORFWHFVNIK-UHFFFAOYSA-N oxolane-2-carbohydrazide Chemical compound NNC(=O)C1CCCO1 LLGRORFWHFVNIK-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
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- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical compound C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 description 1
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- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 239000000296 purinergic P1 receptor antagonist Substances 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 125000002755 pyrazolinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000001422 pyrrolinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000012713 reactive precursor Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- QCMHWZUFWLOOGI-UHFFFAOYSA-N s-ethyl chloromethanethioate Chemical compound CCSC(Cl)=O QCMHWZUFWLOOGI-UHFFFAOYSA-N 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- NYCVSSWORUBFET-UHFFFAOYSA-M sodium;bromite Chemical compound [Na+].[O-]Br=O NYCVSSWORUBFET-UHFFFAOYSA-M 0.000 description 1
- CRWJEUDFKNYSBX-UHFFFAOYSA-N sodium;hypobromite Chemical compound [Na+].Br[O-] CRWJEUDFKNYSBX-UHFFFAOYSA-N 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 229950000244 sulfanilic acid Drugs 0.000 description 1
- RYXNTTXRPACDJA-UHFFFAOYSA-N sulfanyl carbonochloridate Chemical compound SOC(Cl)=O RYXNTTXRPACDJA-UHFFFAOYSA-N 0.000 description 1
- GLBQVJGBPFPMMV-UHFFFAOYSA-N sulfilimine Chemical class S=N GLBQVJGBPFPMMV-UHFFFAOYSA-N 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 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
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000005958 tetrahydrothienyl group Chemical group 0.000 description 1
- 125000002769 thiazolinyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 150000003556 thioamides Chemical class 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 125000005881 triazolinyl group Chemical group 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000001993 wax 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US65583184A | 1984-10-01 | 1984-10-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO853859L true NO853859L (no) | 1986-04-02 |
Family
ID=24630556
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO853859A NO853859L (no) | 1984-10-01 | 1985-09-30 | Triazolikinazolin-forbindelser. |
Country Status (13)
| Country | Link |
|---|---|
| EP (1) | EP0181282A1 (da) |
| JP (1) | JPS61165386A (da) |
| AU (1) | AU4813285A (da) |
| DD (1) | DD236931A5 (da) |
| DK (1) | DK442385A (da) |
| ES (4) | ES8802387A1 (da) |
| FI (1) | FI853736L (da) |
| GR (1) | GR852343B (da) |
| HU (1) | HU194566B (da) |
| IL (1) | IL76528A0 (da) |
| NO (1) | NO853859L (da) |
| PT (1) | PT81225B (da) |
| ZA (1) | ZA857529B (da) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0217748B1 (en) * | 1985-09-30 | 1991-02-06 | Ciba-Geigy Ag | 2-Substituted-e-fused-[1,2,4,]triazolo-[1,5-c]pyrimidines pharmaceutical compositions and uses thereof |
| US4831013A (en) * | 1986-03-20 | 1989-05-16 | Ciba-Geigy Corporation | 2-substituted-e-fused-[1,2,4]triazolo[1,5-c]pyrimidines, pharmaceutical compositions, and uses thereof |
| WO1988002370A1 (en) * | 1986-09-30 | 1988-04-07 | Ciba-Geigy Ag | 2-substituted-e-fused-[1,2,4]triazolo[1,5-c]pyrimidines pharmaceutical compositions and uses thereof |
| HU198484B (en) * | 1986-11-05 | 1989-10-30 | Egyt Gyogyszervegyeszeti Gyar | Process for producing new condensed cyclic triazolo/1,5-a/pyrimidine derivatives |
| US4780464A (en) * | 1986-12-08 | 1988-10-25 | Warner-Lambert Company | (1,2,4)triazolo(4,3-a)quinoxaline-4-amines |
| IE64917B1 (en) * | 1988-02-05 | 1995-09-20 | Riker Laboratories Inc | Triazolo[1,5-c]pyrimido[1,4]azines as bronchodilators |
| US5338743A (en) * | 1988-06-06 | 1994-08-16 | Fujisawa Pharmaceutical Co., Ltd. | New use of the adenosine antagonist |
| US5095015A (en) * | 1990-07-24 | 1992-03-10 | Neurogen Corporation | Certain azacycloalkyl imidazopyrimidines; a new class of gaba brain receptor ligands |
| US5185446A (en) * | 1990-09-04 | 1993-02-09 | Neurogen Corporation | Certain cycloalkyl imidazopyrimidines; a new class of gaba brainreceptor ligands |
| US5744602A (en) * | 1990-10-31 | 1998-04-28 | Neurogen Corporation | Certain imidazoquinoxalines; a new class of GABA brain receptor ligands |
| US5130430A (en) * | 1990-10-31 | 1992-07-14 | Neurogen Corporation | 2-substituted imidazoquinoxaline diones, a new class of gaba brain receptor ligands |
| US5182290A (en) * | 1991-08-27 | 1993-01-26 | Neurogen Corporation | Certain oxazoloquinolinones; a new class of GABA brain receptor ligands |
| US5182386A (en) * | 1991-08-27 | 1993-01-26 | Neurogen Corporation | Certain imidazoquinoxalinones; a new class of gaba brain receptor ligands |
| US5243049A (en) * | 1992-01-22 | 1993-09-07 | Neurogen Corporation | Certain pyrroloquinolinones: a new class of GABA brain receptor ligands |
| US5266698A (en) * | 1992-04-30 | 1993-11-30 | Neurogen Corporation | Certain aryl and cycloalkyl fused imidazopyrazinediones; a new class of GABA brain receptor ligands |
| US5306819A (en) * | 1992-08-27 | 1994-04-26 | Neurogen Corporation | Certain aryl a cycloalkyl fused imidazopyrazinols; and new class of GABA brain receptor ligands |
| DE4241564A1 (de) * | 1992-12-10 | 1994-06-16 | Basf Ag | Triazolochinazoline zur Behandlung zentralnervöser Erkrankungen |
| WO1995003806A1 (fr) * | 1993-07-27 | 1995-02-09 | Kyowa Hakko Kogyo Co., Ltd. | Remede contre la maladie de parkinson |
| US5792766A (en) | 1996-03-13 | 1998-08-11 | Neurogen Corporation | Imidazo 1,5-c! quinazolines; a new class of GABA brain receptor ligands |
| US5955465A (en) * | 1996-03-22 | 1999-09-21 | Neurogen Corporation | 1,2,4-triazolo 4,3-c!quinazolin-3-ones and 1,2,4-triazolo 4,3-c!quinazolin-3-thiones |
| US5677309A (en) * | 1996-03-22 | 1997-10-14 | Neurogen Corporation | 1,2,4-triazolo 4,3-c! quinazolin-3-ones and 1,2,4-triazolo 4,3-c!quinazolin-3-thiones; a new class of GABA brain receptor ligands |
| WO2000024735A1 (en) * | 1998-10-23 | 2000-05-04 | Dow Agrosciences Llc | Insecticidal 1-(substituted pyridyl)-1,2,4-triazoles |
| JP6240180B2 (ja) | 2012-06-18 | 2017-11-29 | ダート・ニューロサイエンス・（ケイマン）・リミテッド | 置換チオフェン−およびフラン−縮合アゾロピリミジン−５−（６ｈ）−オン化合物 |
| WO2014101113A1 (en) * | 2012-12-28 | 2014-07-03 | Merck Sharp & Dohme Corp. | Piperazine-substituted 7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine compounds with a2a antagonist properties |
| WO2014101120A1 (en) | 2012-12-28 | 2014-07-03 | Merck Sharp & Dohme Corp. | Heterobicyclo-substituted-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine compounds with a2a antagonist properties |
| WO2017008205A1 (en) | 2015-07-10 | 2017-01-19 | Merck Sharp & Dohme Corp. | Substituted aminoquinazoline compounds as a2a antagonist |
| JP6420400B2 (ja) * | 2017-04-12 | 2018-11-07 | ダート・ニューロサイエンス・（ケイマン）・リミテッド | 置換ピリジンアゾロピリミジン−５−（６ｈ）−オン化合物 |
| GB2575490A (en) * | 2018-07-12 | 2020-01-15 | Recordati Ind Chimica E Farmaceutica Spa | P2X3 receptor antagonists |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4252945A (en) * | 1979-07-11 | 1981-02-24 | E. R. Squibb & Sons, Inc. | Process for preparing pyrazolo[1,5-c]-quinazoline derivatives and novel intermediates |
| DE3146599A1 (de) * | 1981-11-25 | 1983-07-07 | Basf Ag, 6700 Ludwigshafen | Neue triazolochinazoline, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische zubereitungen |
-
1985
- 1985-09-25 EP EP85810438A patent/EP0181282A1/de active Pending
- 1985-09-26 GR GR852343A patent/GR852343B/el unknown
- 1985-09-27 HU HU853741A patent/HU194566B/hu unknown
- 1985-09-27 IL IL76528A patent/IL76528A0/xx unknown
- 1985-09-27 FI FI853736A patent/FI853736L/fi not_active Application Discontinuation
- 1985-09-30 AU AU48132/85A patent/AU4813285A/en not_active Abandoned
- 1985-09-30 NO NO853859A patent/NO853859L/no unknown
- 1985-09-30 ZA ZA857529A patent/ZA857529B/xx unknown
- 1985-09-30 DD DD85281220A patent/DD236931A5/de unknown
- 1985-09-30 DK DK442385A patent/DK442385A/da not_active Application Discontinuation
- 1985-09-30 PT PT81225A patent/PT81225B/pt unknown
- 1985-10-01 JP JP60216280A patent/JPS61165386A/ja active Pending
-
1986
- 1986-10-01 ES ES557120A patent/ES8802387A1/es not_active Expired
- 1986-10-01 ES ES557119A patent/ES8802386A1/es not_active Expired
- 1986-10-01 ES ES557117A patent/ES8707732A1/es not_active Expired
- 1986-10-01 ES ES557118A patent/ES8801277A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FI853736A0 (fi) | 1985-09-27 |
| FI853736L (fi) | 1986-04-02 |
| DK442385D0 (da) | 1985-09-30 |
| IL76528A0 (en) | 1986-01-31 |
| AU4813285A (en) | 1986-04-10 |
| DK442385A (da) | 1986-04-02 |
| PT81225B (en) | 1987-07-15 |
| DD236931A5 (de) | 1986-06-25 |
| GR852343B (da) | 1986-01-28 |
| JPS61165386A (ja) | 1986-07-26 |
| ES8802386A1 (es) | 1988-05-16 |
| ES8802387A1 (es) | 1988-05-16 |
| ES8707732A1 (es) | 1987-08-16 |
| ES8801277A1 (es) | 1988-01-01 |
| EP0181282A1 (de) | 1986-05-14 |
| ES557117A0 (es) | 1987-08-16 |
| ES557118A0 (es) | 1988-01-01 |
| ZA857529B (en) | 1986-05-28 |
| ES557120A0 (es) | 1988-05-16 |
| HU194566B (en) | 1988-02-29 |
| PT81225A (en) | 1985-10-01 |
| ES557119A0 (es) | 1988-05-16 |
| HUT38941A (en) | 1986-07-28 |
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