NO811646L - Fremgangsmaate ved fremstilling av nye triazolkinoxalin-4-oner. - Google Patents

Fremgangsmaate ved fremstilling av nye triazolkinoxalin-4-oner.

Info

Publication number: NO811646L
Authority: NO; Norway
Prior art keywords: quinoxalin; methyl; product; mmol; ether
Prior art date: 1980-05-19

Application number

NO811646A

Other languages

English (en)

Norwegian (no)

Inventor

Bernard Loev

John T Suh

Bruce E Williams

Vasil St Georgiev

Original Assignee

Usv Pharma Corp

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.)

1980-05-19

Filing date

1981-05-14

Publication date

1981-11-20

1981-05-14 Application filed by Usv Pharma Corp filed Critical Usv Pharma Corp

1981-11-20 Publication of NO811646L publication Critical patent/NO811646L/no

Links

238000000034 method Methods 0.000 title claims description 10
238000002360 preparation method Methods 0.000 title claims description 5
150000001875 compounds Chemical class 0.000 claims description 24
150000003839 salts Chemical class 0.000 claims description 13
-1 cyano, hydroxy Chemical group 0.000 claims description 12
239000002253 acid Substances 0.000 claims description 10
229910052739 hydrogen Inorganic materials 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 6
125000001424 substituent group Chemical group 0.000 claims description 6
125000003118 aryl group Chemical group 0.000 claims description 5
125000003342 alkenyl group Chemical group 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 4
125000000304 alkynyl group Chemical group 0.000 claims description 4
125000003710 aryl alkyl group Chemical group 0.000 claims description 4
125000000753 cycloalkyl group Chemical group 0.000 claims description 4
LLBZPESJRQGYMB-UHFFFAOYSA-N 4-one Natural products O1C(C(=O)CC)CC(C)C11C2(C)CCC(C3(C)C(C(C)(CO)C(OC4C(C(O)C(O)C(COC5C(C(O)C(O)CO5)OC5C(C(OC6C(C(O)C(O)C(CO)O6)O)C(O)C(CO)O5)OC5C(C(O)C(O)C(C)O5)O)O4)O)CC3)CC3)=C3C2(C)CC1 LLBZPESJRQGYMB-UHFFFAOYSA-N 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 3
239000002220 antihypertensive agent Substances 0.000 claims description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
238000006460 hydrolysis reaction Methods 0.000 claims description 3
238000006467 substitution reaction Methods 0.000 claims description 3
125000002252 acyl group Chemical group 0.000 claims description 2
125000004423 acyloxy group Chemical group 0.000 claims description 2
125000005236 alkanoylamino group Chemical group 0.000 claims description 2
125000003302 alkenyloxy group Chemical group 0.000 claims description 2
125000003282 alkyl amino group Chemical group 0.000 claims description 2
125000005133 alkynyloxy group Chemical group 0.000 claims description 2
125000001589 carboacyl group Chemical group 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
150000002367 halogens Chemical class 0.000 claims description 2
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 2
FFRYUAVNPBUEIC-UHFFFAOYSA-N quinoxalin-2-ol Chemical compound C1=CC=CC2=NC(O)=CN=C21 FFRYUAVNPBUEIC-UHFFFAOYSA-N 0.000 claims description 2
125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims description 2
125000004953 trihalomethyl group Chemical group 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims 3
SEPPVOUBHWNCAW-FNORWQNLSA-N (E)-4-oxonon-2-enal Chemical compound CCCCCC(=O)\C=C\C=O SEPPVOUBHWNCAW-FNORWQNLSA-N 0.000 claims 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims 1
238000006722 reduction reaction Methods 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 50
239000000203 mixture Substances 0.000 description 23
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 18
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
238000001914 filtration Methods 0.000 description 16
239000000243 solution Substances 0.000 description 16
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
239000000047 product Substances 0.000 description 14
235000002639 sodium chloride Nutrition 0.000 description 14
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 12
239000000463 material Substances 0.000 description 11
239000007787 solid Substances 0.000 description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
239000012264 purified product Substances 0.000 description 7
239000013078 crystal Substances 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
230000003276 anti-hypertensive effect Effects 0.000 description 4
239000003814 drug Substances 0.000 description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
238000000746 purification Methods 0.000 description 4
229940124597 therapeutic agent Drugs 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
241000700159 Rattus Species 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
238000006243 chemical reaction Methods 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
230000000694 effects Effects 0.000 description 3
150000002391 heterocyclic compounds Chemical class 0.000 description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
238000002560 therapeutic procedure Methods 0.000 description 3
230000001988 toxicity Effects 0.000 description 3
231100000419 toxicity Toxicity 0.000 description 3
RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound 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
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
230000010933 acylation Effects 0.000 description 2
238000005917 acylation reaction Methods 0.000 description 2
229940030600 antihypertensive agent Drugs 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
239000012043 crude product Substances 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
125000004435 hydrogen atom Chemical class [H]* 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000002955 isolation Methods 0.000 description 2
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical class OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
238000010992 reflux Methods 0.000 description 2
239000002904 solvent Substances 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
239000008096 xylene Substances 0.000 description 2
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 description 1
DGMOBVGABMBZSB-UHFFFAOYSA-N 2-methylpropanoyl chloride Chemical compound CC(C)C(Cl)=O DGMOBVGABMBZSB-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
VUFIZWYBZJKRAM-UHFFFAOYSA-N 3-methyl-n'-[4-methyl-3-oxo-7-(trifluoromethyl)quinoxalin-2-yl]butanehydrazide Chemical compound FC(F)(F)C1=CC=C2N(C)C(=O)C(NNC(=O)CC(C)C)=NC2=C1 VUFIZWYBZJKRAM-UHFFFAOYSA-N 0.000 description 1
ISULZYQDGYXDFW-UHFFFAOYSA-N 3-methylbutanoyl chloride Chemical compound CC(C)CC(Cl)=O ISULZYQDGYXDFW-UHFFFAOYSA-N 0.000 description 1
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 1
YVNUWCYKMCHYJI-UHFFFAOYSA-N 7-methoxy-4-methyl-1h-quinoxaline-2,3-dione Chemical compound CN1C(=O)C(=O)NC2=CC(OC)=CC=C21 YVNUWCYKMCHYJI-UHFFFAOYSA-N 0.000 description 1
206010002198 Anaphylactic reaction Diseases 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical class F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
206010020772 Hypertension Diseases 0.000 description 1
UEZVMMHDMIWARA-UHFFFAOYSA-N Metaphosphoric acid Chemical compound OP(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-N 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
235000011054 acetic acid Nutrition 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
239000013543 active substance Substances 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
238000007098 aminolysis reaction Methods 0.000 description 1
230000036783 anaphylactic response Effects 0.000 description 1
208000003455 anaphylaxis Diseases 0.000 description 1
230000003266 anti-allergic effect Effects 0.000 description 1
239000000043 antiallergic agent Substances 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
239000002775 capsule Substances 0.000 description 1
150000003857 carboxamides Chemical class 0.000 description 1
235000015165 citric acid Nutrition 0.000 description 1
239000004927 clay Substances 0.000 description 1
239000003086 colorant Substances 0.000 description 1
125000004093 cyano group Chemical group *C#N 0.000 description 1
ZOOSILUVXHVRJE-UHFFFAOYSA-N cyclopropanecarbonyl chloride Chemical compound ClC(=O)C1CC1 ZOOSILUVXHVRJE-UHFFFAOYSA-N 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
238000009472 formulation Methods 0.000 description 1
239000000174 gluconic acid Substances 0.000 description 1
235000012208 gluconic acid Nutrition 0.000 description 1
239000008103 glucose Substances 0.000 description 1
230000000971 hippocampal effect Effects 0.000 description 1
229960001340 histamine Drugs 0.000 description 1
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
229940071870 hydroiodic acid Drugs 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
230000001631 hypertensive effect Effects 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
229950003188 isovaleryl diethylamide Drugs 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
RPJRYTIDXSYQNK-UHFFFAOYSA-N n'-(7-chloro-4-methyl-3-oxoquinoxalin-2-yl)butanehydrazide Chemical compound ClC1=CC=C2N(C)C(=O)C(NNC(=O)CCC)=NC2=C1 RPJRYTIDXSYQNK-UHFFFAOYSA-N 0.000 description 1
LGXYZJXMXYEBCY-UHFFFAOYSA-N n'-(7-methoxy-4-methyl-3-oxoquinoxalin-2-yl)benzohydrazide Chemical compound N=1C2=CC(OC)=CC=C2N(C)C(=O)C=1NNC(=O)C1=CC=CC=C1 LGXYZJXMXYEBCY-UHFFFAOYSA-N 0.000 description 1
CACRCJNJIZBERE-UHFFFAOYSA-N n'-(7-methoxy-4-methyl-3-oxoquinoxalin-2-yl)butanehydrazide Chemical compound COC1=CC=C2N(C)C(=O)C(NNC(=O)CCC)=NC2=C1 CACRCJNJIZBERE-UHFFFAOYSA-N 0.000 description 1
YLXRPZGRFWSVRZ-UHFFFAOYSA-N n'-(7-methoxy-4-methyl-3-oxoquinoxalin-2-yl)propanehydrazide Chemical compound COC1=CC=C2N(C)C(=O)C(NNC(=O)CC)=NC2=C1 YLXRPZGRFWSVRZ-UHFFFAOYSA-N 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
231100000956 nontoxicity Toxicity 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
125000005489 p-toluenesulfonic acid group Chemical class 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
XGISHOFUAFNYQF-UHFFFAOYSA-N pentanoyl chloride Chemical compound CCCCC(Cl)=O XGISHOFUAFNYQF-UHFFFAOYSA-N 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
238000006798 ring closing metathesis reaction Methods 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000012265 solid product Substances 0.000 description 1
230000002269 spontaneous effect Effects 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008107 starch Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000008174 sterile solution Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
238000011287 therapeutic dose Methods 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1
231100000820 toxicity test Toxicity 0.000 description 1
238000003828 vacuum filtration Methods 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
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
- C07D241/40—Benzopyrazines
- C07D241/44—Benzopyrazines with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Bioinformatics & Cheminformatics (AREA)
Life Sciences & Earth Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Engineering & Computer Science (AREA)
Public Health (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Immunology (AREA)
Pulmonology (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

NO811646A 1980-05-19 1981-05-14 Fremgangsmaate ved fremstilling av nye triazolkinoxalin-4-oner. NO811646L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US06/151,220 US4354027A (en)	1980-05-19	1980-05-19	Triazoloquinoxalin-4-ones

Publications (1)

Publication Number	Publication Date
NO811646L true NO811646L (no)	1981-11-20

Family

ID=22537818

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO811646A NO811646L (no)	1980-05-19	1981-05-14	Fremgangsmaate ved fremstilling av nye triazolkinoxalin-4-oner.

Country Status (12)

Country	Link
US (1)	US4354027A (es)
EP (1)	EP0040401B1 (es)
JP (1)	JPS5718681A (es)
AU (1)	AU538782B2 (es)
CA (1)	CA1176634A (es)
DE (1)	DE3162761D1 (es)
DK (1)	DK214981A (es)
ES (1)	ES502747A0 (es)
FI (1)	FI71148C (es)
NO (1)	NO811646L (es)
NZ (1)	NZ197101A (es)
ZA (1)	ZA813255B (es)

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US3141304A (en) *	1960-11-14	1964-07-21	Jefferson Chem Co Inc	Soil stabilization by atactic polypropylene coating
US4507300A (en) *	1980-05-09	1985-03-26	Usv Pharmaceutical Corporation	Pyridotriazolopyrazine-diones for treating allergy
US4400382A (en) *	1980-05-09	1983-08-23	Usv Pharmaceutical Corporation	Thiazoloquinoxalin-1,4-diones for treating allergy
US5153196A (en) *	1991-06-05	1992-10-06	Eli Lilly And Company	Excitatory amino acid receptor antagonists and methods for the use thereof
US5196421A (en) *	1991-06-05	1993-03-23	Eli Lilly And Company	Excitatory amino acid receptor antagonists in methods for the use thereof
DK162491D0 (da) *	1991-09-20	1991-09-20	Novo Nordisk As	Heterocycliske forbindelser, deres fremstilling og farmaceutiske praeparater indeholdende forbindelserne
FR2696466B1 (fr) *	1992-10-02	1994-11-25	Rhone Poulenc Rorer Sa	Dérivés de 5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazine-4-one, leur préparation et les médicaments les contenant.
DK31093D0 (es) *	1993-03-19	1993-03-19	Novo Nordisk As
FR2717814B1 (fr) *	1994-03-28	1996-04-26	Rhone Poulenc Rorer Sa	Dérivés de 1,2,4-triazolo(4,3-a)pyrazine-4-one, leur préparation et les médicaments les contenant.
FR2717813B1 (fr) *	1994-03-28	1996-05-10	Rhone Poulenc Rorer Sa	Dérivés d'imidazo[1,2-a]indeno[1,2-e]pyrazine-4-one, leur préparation et les médicaments les contenant .
FR2717812B1 (fr) *	1994-03-28	1996-05-10	Rhone Poulenc Rorer Sa	Indeno[1,2-e]pyrazine-4-ones, leur préparation et les médicaments les contenant.
FR2717805B1 (fr) *	1994-03-28	1996-05-10	Rhone Poulenc Rorer Sa	Dérivés de 5H-indeno[1,2-b]pyrazine-2,3-dione, leur préparation et les médicaments les contenant .
DK0781282T3 (da) *	1994-09-16	2000-02-28	Novo Nordisk As	[1,2]triazolo[4,3-a]quinoxalinonderivater, deres fremstilling og anvendelse
HUT76810A (en) *	1994-09-16	1997-11-28	Novo Nordisk As	[1,2,4]triazolo[4,3-a]quinoxalinone derivatives, process for their preparation and pharmaceutical compositions containing them
FR2726275B1 (fr) *	1994-11-02	1996-12-06	Rhone Poulenc Rorer Sa	Spiro heterocycle-imidazo(1,2-a)indeno(1,2-e)pyrazine)-4'- ones, leur preparation et les medicaments les contenants
US5679680A (en) *	1995-02-16	1997-10-21	Warner-Lambert Company	α-substituted hydrazides having calpain inhibitory activity
CN101553491B (zh) *	2006-12-13	2013-05-29	Aska制药株式会社	喹喔啉衍生物
AR107456A1 (es)	2016-02-12	2018-05-02	Lilly Co Eli	Inhibidor de pde1
JOP20170164A1 (ar)	2016-08-25	2019-01-30	Lilly Co Eli	مشتق ترايازولو بيرازينون مفيد كمثبط لـ pde1 بشري
AR112457A1 (es)	2017-08-02	2019-10-30	Lilly Co Eli	Derivados de [1,2,4]triazolo[4,3-a]pirazin-6(5h)-ona
AR112346A1 (es)	2017-08-10	2019-10-16	Lilly Co Eli	Derivados de [1,2,4]triazolo

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GB1301228A (es) *	1971-03-04	1972-12-29	Ici Ltd
JPS50116498A (es) *	1974-02-27	1975-09-11
US3979387A (en) *	1975-06-10	1976-09-07	Eli Lilly And Company	4,5-Dihydrotetrazolo(1,5-A)quinoxalines

1980
- 1980-05-19 US US06/151,220 patent/US4354027A/en not_active Expired - Lifetime
1981
- 1981-05-12 CA CA000377439A patent/CA1176634A/en not_active Expired
- 1981-05-13 AU AU70544/81A patent/AU538782B2/en not_active Ceased
- 1981-05-13 EP EP81103695A patent/EP0040401B1/en not_active Expired
- 1981-05-13 DE DE8181103695T patent/DE3162761D1/de not_active Expired
- 1981-05-14 NZ NZ197101A patent/NZ197101A/en unknown
- 1981-05-14 DK DK214981A patent/DK214981A/da not_active Application Discontinuation
- 1981-05-14 NO NO811646A patent/NO811646L/no unknown
- 1981-05-14 ES ES502747A patent/ES502747A0/es active Granted
- 1981-05-15 JP JP7239281A patent/JPS5718681A/ja active Pending
- 1981-05-15 ZA ZA00813255A patent/ZA813255B/xx unknown
- 1981-05-15 FI FI811504A patent/FI71148C/fi not_active IP Right Cessation

Also Published As

Publication number	Publication date
DE3162761D1 (en)	1984-04-26
NZ197101A (en)	1984-03-16
ES8203375A1 (es)	1982-04-01
EP0040401A1 (en)	1981-11-25
DK214981A (da)	1981-11-20
AU7054481A (en)	1981-11-19
US4354027A (en)	1982-10-12
AU538782B2 (en)	1984-08-30
CA1176634A (en)	1984-10-23
FI71148C (fi)	1986-11-24
FI811504L (fi)	1981-11-20
ZA813255B (en)	1982-06-30
EP0040401B1 (en)	1984-03-21
ES502747A0 (es)	1982-04-01
JPS5718681A (en)	1982-01-30
FI71148B (fi)	1986-08-14

Publication	Publication Date	Title
NO811646L (no)	1981-11-20	Fremgangsmaate ved fremstilling av nye triazolkinoxalin-4-oner.
SU820659A3 (ru)	1981-04-07	Способ получени производных 4-амино- 5-АлКилСульфОНилОАНизАМидОВ, иХ СОлЕй,ОКиСЕй, лЕВО- и пРАВОВРАщАющиХизОМЕРОВ /иХ ВАРиАНТы/
US5162318A (en)	1992-11-10	Benzimidazolinone derivatives
CA1290756C (en)	1991-10-15	Quinazolinone derivative and processes for preparing the same
US4017622A (en)	1977-04-12	Piperazine derivatives
KR870001167B1 (ko)	1987-06-15	치환된 2-(1h)-퀴놀론의 제조방법
EP0257850B1 (en)	1993-12-08	Pyrimidine derivatives
US4714762A (en)	1987-12-22	Antiarteriosclerotic substituted benzimidazol-2-yl-and 3H-imidazo[4,5-b]pyridin-2-yl-phenoxy-alkanoic acids and salts and esters thereof
AU582982B2 (en)	1989-04-13	Hydroxy and aminothiazolyl-benzodiazinone compounds, cardiotonic compositions including the same,and their uses
JP4323803B2 (ja)	2009-09-02	置換２−アニリノーベンゾイミダゾール及びｎｈｅ阻害剤としてのその使用
NO164476B (no)	1990-07-02	Analogifremgangsmaate ved fremstilling av terapeutisk virksomme 1,2,3,5-tetrahydroimidazo-(2,1-b)-kinazoliner.
CH653684A5 (fr)	1986-01-15	Derives de carbostyrile, procede pour leur preparation et compositions les contenant.
EP0198456B1 (en)	1992-06-10	1,7-naphthyridine derivatives and medicinal preparations containing same
JPH0597846A (ja)	1993-04-20	ベンゾイミダゾールから誘導される非鎮静性抗ヒスタミン作用を有する新規化合物
JP2544939B2 (ja)	1996-10-16	ベンゾヘテロ環誘導体
AU2007227811A1 (en)	2007-09-27	Crystalline forms of N- {2-tert -butyl -1- [ (4,4- dif luorocyclohexyl) methyl] -lH-benzimidazol-5- yl}ethanesulfonamide salts
JP2000506874A (ja)	2000-06-06	抗喘息性、抗アレルギー性、抗炎症性および免疫調節作用を有する１，３，５―トリ置換されたインダゾール誘導体
CA2141366A1 (en)	1995-08-02	Treatment of heart rhythm disorders by administration of 3-phenylsulfonyl-3,7-diazabicyclo[3.3.1]nonane compounds
EP0168003B1 (en)	1991-04-03	Oxindol compounds, compositions containing same and processes for preparing same
HU196408B (en)	1988-11-28	Process for producing tetrahydro-imidazo-quinazolines and stimulators of cardiac action containing them
US6083987A (en)	2000-07-04	Phenylenediamine derivative, radical scavenger, brain-infarction depressant, and brain-edema depressant
IE44184B1 (en)	1981-09-09	Imidazole derivatives,processes for their preparation and pharmaceutical compositions containing them
EP0308059B1 (en)	1992-09-09	1,2,3,4-tetrahydroisoquinoline antiarrhythmic agents
SU1433411A3 (ru)	1988-10-23	Способ получени производных 2-(1Н)-хинолона или их фармацевтически приемлемых солей
KR20190126525A (ko)	2019-11-12	신규 소듐채널 저해 화합물, 이의 제조방법, 및 이를 포함하는 소듐채널 관련 질환의 예방 또는 치료용 약학적 조성물