NO852981L - Tricykliske dihydropyridazinoner og fremstilling derav. - Google Patents
Tricykliske dihydropyridazinoner og fremstilling derav.Info
- Publication number
- NO852981L NO852981L NO852981A NO852981A NO852981L NO 852981 L NO852981 L NO 852981L NO 852981 A NO852981 A NO 852981A NO 852981 A NO852981 A NO 852981A NO 852981 L NO852981 L NO 852981L
- Authority
- NO
- Norway
- Prior art keywords
- formula
- acid
- compound
- hydrogen
- group
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 108
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 31
- 238000000034 method Methods 0.000 claims abstract description 30
- -1 hydroxy, amino Chemical group 0.000 claims abstract description 26
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 20
- 230000008569 process Effects 0.000 claims abstract description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 6
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims abstract description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 3
- 125000003118 aryl group Chemical group 0.000 claims abstract description 3
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 3
- 150000002367 halogens Chemical class 0.000 claims abstract description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 3
- 125000004404 heteroalkyl group Chemical group 0.000 claims abstract 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 55
- 239000000203 mixture Substances 0.000 claims description 31
- 239000001257 hydrogen Substances 0.000 claims description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 230000003287 optical effect Effects 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 150000002431 hydrogen Chemical class 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 8
- 239000007858 starting material Substances 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 6
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 150000001735 carboxylic acids Chemical class 0.000 claims description 4
- 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 4
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 3
- 235000019253 formic acid Nutrition 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 150000002170 ethers Chemical class 0.000 claims description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 2
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 1
- 101100294106 Caenorhabditis elegans nhr-3 gene Proteins 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 claims 1
- 150000002366 halogen compounds Chemical class 0.000 claims 1
- 230000001120 cytoprotective effect Effects 0.000 abstract description 4
- 230000002744 anti-aggregatory effect Effects 0.000 abstract description 3
- 239000003814 drug Substances 0.000 abstract description 2
- 101100079984 Caenorhabditis elegans nhr-9 gene Proteins 0.000 abstract 1
- 230000002785 anti-thrombosis Effects 0.000 abstract 1
- 239000003146 anticoagulant agent Substances 0.000 abstract 1
- 150000003573 thiols Chemical class 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 71
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 48
- 239000000243 solution Substances 0.000 description 41
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
- 239000002253 acid Substances 0.000 description 27
- 238000005160 1H NMR spectroscopy Methods 0.000 description 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- 235000011054 acetic acid Nutrition 0.000 description 15
- 239000002244 precipitate Substances 0.000 description 13
- 238000010992 reflux Methods 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 238000001914 filtration Methods 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000011282 treatment Methods 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 229960001138 acetylsalicylic acid Drugs 0.000 description 6
- 125000002252 acyl group Chemical group 0.000 description 6
- 239000008346 aqueous phase Substances 0.000 description 6
- 150000002576 ketones Chemical class 0.000 description 6
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 206010042434 Sudden death Diseases 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- 125000003277 amino group Chemical group 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- BGYKFEZDXJOZNT-UHFFFAOYSA-N n-(3-oxo-4,4a,5,6-tetrahydro-2h-benzo[h]cinnolin-8-yl)acetamide Chemical compound N1C(=O)CC2CCC3=CC(NC(=O)C)=CC=C3C2=N1 BGYKFEZDXJOZNT-UHFFFAOYSA-N 0.000 description 5
- 229920000137 polyphosphoric acid Polymers 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- NPYDCWYODHJJQB-UHFFFAOYSA-N 2-(6-acetamido-3-oxo-1,2-dihydroinden-2-yl)acetic acid Chemical compound CC(=O)NC1=CC=C2C(=O)C(CC(O)=O)CC2=C1 NPYDCWYODHJJQB-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 4
- 238000005804 alkylation reaction Methods 0.000 description 4
- 150000008064 anhydrides Chemical class 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Chemical group CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 230000001077 hypotensive effect Effects 0.000 description 4
- 238000011065 in-situ storage Methods 0.000 description 4
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 4
- 229960001367 tartaric acid Drugs 0.000 description 4
- 239000011975 tartaric acid Substances 0.000 description 4
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 4
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 4
- 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 3
- VEPUKHYQNXSSKV-UHFFFAOYSA-N 1-(5,6,7,8-tetrahydronaphthalen-2-yl)ethanone Chemical compound C1CCCC2=CC(C(=O)C)=CC=C21 VEPUKHYQNXSSKV-UHFFFAOYSA-N 0.000 description 3
- SHKWSBAVRQZYLE-UHFFFAOYSA-N 5-oxo-5-phenylpentanoic acid Chemical compound OC(=O)CCCC(=O)C1=CC=CC=C1 SHKWSBAVRQZYLE-UHFFFAOYSA-N 0.000 description 3
- FRTZAGJSMHUZSR-UHFFFAOYSA-N 9-amino-2,4,4a,5,6,7-hexahydrobenzo[1,2]cyclohepta[4,6-d]pyridazin-3-one Chemical compound C1CCC2=CC(N)=CC=C2C2=NNC(=O)CC21 FRTZAGJSMHUZSR-UHFFFAOYSA-N 0.000 description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 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 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- 238000005917 acylation reaction Methods 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 230000029936 alkylation Effects 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 3
- 238000000338 in vitro Methods 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- KTXZJVBDYSLVRN-UHFFFAOYSA-N n-(3-oxo-2,4,4a,5,6,7-hexahydrobenzo[1,2]cyclohepta[4,6-d]pyridazin-9-yl)acetamide Chemical compound C1CCC2=CC(NC(=O)C)=CC=C2C2=NNC(=O)CC21 KTXZJVBDYSLVRN-UHFFFAOYSA-N 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 150000007530 organic bases Chemical class 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 3
- 210000004623 platelet-rich plasma Anatomy 0.000 description 3
- 235000011056 potassium acetate Nutrition 0.000 description 3
- 230000002265 prevention Effects 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 238000006722 reduction reaction Methods 0.000 description 3
- 238000007363 ring formation reaction Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 3
- 235000002906 tartaric acid Nutrition 0.000 description 3
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- HCMWPTFPUCPKQM-UHFFFAOYSA-N 1-(2,3-dihydro-1h-inden-5-yl)ethanone Chemical compound CC(=O)C1=CC=C2CCCC2=C1 HCMWPTFPUCPKQM-UHFFFAOYSA-N 0.000 description 2
- KOPFEFZSAMLEHK-UHFFFAOYSA-N 1h-pyrazole-5-carboxylic acid Chemical compound OC(=O)C=1C=CNN=1 KOPFEFZSAMLEHK-UHFFFAOYSA-N 0.000 description 2
- LUQCSCGELARTSS-UHFFFAOYSA-N 2,2,2-trifluoro-n-(1-oxo-2,3-dihydroinden-5-yl)acetamide Chemical compound FC(F)(F)C(=O)NC1=CC=C2C(=O)CCC2=C1 LUQCSCGELARTSS-UHFFFAOYSA-N 0.000 description 2
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 2
- HEOQXHNKRXRCTO-UHFFFAOYSA-N 6,7,8,9-tetrahydro-5h-benzo[7]annulene Chemical compound C1CCCCC2=CC=CC=C21 HEOQXHNKRXRCTO-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical group CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- YVHAIVPPUIZFBA-UHFFFAOYSA-N Cyclopentylacetic acid Chemical compound OC(=O)CC1CCCC1 YVHAIVPPUIZFBA-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- 206010020772 Hypertension Diseases 0.000 description 2
- 208000001953 Hypotension Diseases 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- WEBCZGJWXXPNHB-UHFFFAOYSA-N N1-(5-oxo-5,6,7,8-tetrahydronaphthalen-2-yl)acetamide Chemical compound O=C1CCCC2=CC(NC(=O)C)=CC=C21 WEBCZGJWXXPNHB-UHFFFAOYSA-N 0.000 description 2
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
- 206010030113 Oedema Diseases 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 230000007059 acute toxicity Effects 0.000 description 2
- 231100000403 acute toxicity Toxicity 0.000 description 2
- 230000010933 acylation Effects 0.000 description 2
- 235000010443 alginic acid Nutrition 0.000 description 2
- 229920000615 alginic acid Polymers 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 2
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 2
- 238000010531 catalytic reduction reaction Methods 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000012050 conventional carrier Substances 0.000 description 2
- 239000002178 crystalline material Substances 0.000 description 2
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 2
- JBDSSBMEKXHSJF-UHFFFAOYSA-N cyclopentanecarboxylic acid Chemical compound OC(=O)C1CCCC1 JBDSSBMEKXHSJF-UHFFFAOYSA-N 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 2
- DSOJMGUVLXTQSE-UHFFFAOYSA-N ethyl 3-(3-nitrophenyl)-3-oxopropanoate Chemical compound CCOC(=O)CC(=O)C1=CC=CC([N+]([O-])=O)=C1 DSOJMGUVLXTQSE-UHFFFAOYSA-N 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- VANNPISTIUFMLH-UHFFFAOYSA-N glutaric anhydride Chemical compound O=C1CCCC(=O)O1 VANNPISTIUFMLH-UHFFFAOYSA-N 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
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- QERYCTSHXKAMIS-UHFFFAOYSA-N thiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/26—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings condensed with carbocyclic rings or ring systems
- C07D237/36—Benzo-cinnolines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- 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
- A61P9/08—Vasodilators for multiple indications
-
- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/56—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups bound to carbon atoms of six-membered aromatic rings and carboxyl groups bound to acyclic carbon atoms of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/46—Friedel-Crafts reactions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/782—Ketones containing a keto group bound to a six-membered aromatic ring polycyclic
- C07C49/792—Ketones containing a keto group bound to a six-membered aromatic ring polycyclic containing rings other than six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/76—Unsaturated compounds containing keto groups
- C07C59/84—Unsaturated compounds containing keto groups containing six membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/26—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings condensed with carbocyclic rings or ring systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB08419253A GB2164643B (en) | 1984-07-27 | 1984-07-27 | Tricyclic dihydropyridazinones and pharmaceutical compositions containing them |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO852981L true NO852981L (no) | 1986-01-28 |
Family
ID=10564580
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO852981A NO852981L (no) | 1984-07-27 | 1985-07-26 | Tricykliske dihydropyridazinoner og fremstilling derav. |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US4692447A (ko) |
| EP (1) | EP0169443A3 (ko) |
| JP (1) | JPS6147468A (ko) |
| KR (1) | KR880000728B1 (ko) |
| CN (1) | CN85107017A (ko) |
| AU (1) | AU576253B2 (ko) |
| DD (1) | DD238972A5 (ko) |
| DK (1) | DK327685A (ko) |
| ES (1) | ES8609274A1 (ko) |
| FI (1) | FI852699L (ko) |
| GB (1) | GB2164643B (ko) |
| GR (1) | GR851722B (ko) |
| HU (1) | HU195193B (ko) |
| IL (1) | IL75864A (ko) |
| NO (1) | NO852981L (ko) |
| NZ (1) | NZ212721A (ko) |
| PT (1) | PT80854B (ko) |
| ZA (1) | ZA855430B (ko) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2164643B (en) * | 1984-07-27 | 1988-11-02 | Boehringer Biochemia Srl | Tricyclic dihydropyridazinones and pharmaceutical compositions containing them |
| JPH06763B2 (ja) * | 1984-08-28 | 1994-01-05 | 吉富製薬株式会社 | ベンゾ〔ｈ〕シンノリン誘導体 |
| AU578496B2 (en) * | 1984-11-01 | 1988-10-27 | Smith Kline & French Laboratories Limited | Tricyclic heterocyclic compounds |
| US4861773A (en) * | 1986-04-28 | 1989-08-29 | Smith Kline & French Laboratories Limited | Heterocyclic compounds |
| EP0281045B1 (en) * | 1987-03-02 | 1991-12-27 | Yoshitomi Pharmaceutical Industries, Ltd. | Benzothiepino (5,4-c) pyridazine compounds and their pharmaceutical uses |
| WO1989004306A1 (en) * | 1987-11-02 | 1989-05-18 | Yoshitomi Pharmaceutical Industries, Ltd. | Fused pyridazine compounds and their medicinal uses |
| JP2717687B2 (ja) * | 1988-02-13 | 1998-02-18 | 日本曹達株式会社 | ピリダジノン誘導体及びその製造方法 |
| US5153194A (en) * | 1988-09-21 | 1992-10-06 | Yoshitomi Pharmaceutical Industries, Ltd. | Thienocycloheptapyridazine compounds and their pharmaceutical use |
| FR2692895A1 (fr) * | 1992-06-26 | 1993-12-31 | Adir | Nouveaux 1-oxo 2,4,5,6-tétrahydro 2,3,7-triazaphénalènes leurs procédés de préparation et les compositions pharmaceutiques qui les contiennent. |
| IL110172A (en) * | 1993-07-22 | 2001-10-31 | Lilly Co Eli | Bicycle compounds and pharmaceuticals containing them |
| US6137002A (en) * | 1993-07-22 | 2000-10-24 | Eli Lilly And Company | Glycoprotein IIb/IIIa antagonists |
| US5731324A (en) * | 1993-07-22 | 1998-03-24 | Eli Lilly And Company | Glycoprotein IIb/IIIa antagonists |
| US6448269B1 (en) | 1993-07-22 | 2002-09-10 | Eli Lilly And Company | Glycoprotein IIb/IIIa antagonists |
| US8304415B2 (en) | 2010-02-25 | 2012-11-06 | National Defense Medical Center | 1, 2-disubstituted amido-anthraquinone derivatives, preparation method and application thereof |
| CA2938615A1 (en) * | 2014-02-06 | 2015-08-13 | Basf Se | Insulating assembly for a storage vessel and process for its preparation |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1670043C3 (de) * | 1966-01-07 | 1975-05-22 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Herstellung von 3-(Aminophenyl)-pyridazon-(6)-derivaten |
| US3464988A (en) * | 1968-01-11 | 1969-09-02 | Bristol Myers Co | 3-hydrazinobenzo(h)cinnolines and 3 - hydrazinobenzocyclohepta-(5,6-c)pyridazines |
| US4602019A (en) * | 1983-04-22 | 1986-07-22 | Warner-Lambert Company | Indeno[1,2-c]pyridazin-3-one derivatives useful as cardiotonic and antihypertensive agents |
| GB2164643B (en) * | 1984-07-27 | 1988-11-02 | Boehringer Biochemia Srl | Tricyclic dihydropyridazinones and pharmaceutical compositions containing them |
-
1984
- 1984-07-27 GB GB08419253A patent/GB2164643B/en not_active Expired
-
1985
- 1985-07-08 FI FI852699A patent/FI852699L/fi not_active Application Discontinuation
- 1985-07-10 HU HU852670A patent/HU195193B/hu not_active IP Right Cessation
- 1985-07-10 EP EP85108605A patent/EP0169443A3/en not_active Withdrawn
- 1985-07-11 NZ NZ212721A patent/NZ212721A/xx unknown
- 1985-07-11 AU AU44814/85A patent/AU576253B2/en not_active Ceased
- 1985-07-11 GR GR851722A patent/GR851722B/el unknown
- 1985-07-18 ZA ZA855430A patent/ZA855430B/xx unknown
- 1985-07-18 DK DK327685A patent/DK327685A/da unknown
- 1985-07-22 US US06/757,429 patent/US4692447A/en not_active Expired - Fee Related
- 1985-07-22 IL IL75864A patent/IL75864A/xx not_active IP Right Cessation
- 1985-07-23 PT PT80854A patent/PT80854B/pt unknown
- 1985-07-26 KR KR1019850005362A patent/KR880000728B1/ko not_active IP Right Cessation
- 1985-07-26 NO NO852981A patent/NO852981L/no unknown
- 1985-07-26 JP JP60166618A patent/JPS6147468A/ja active Pending
- 1985-07-26 ES ES545574A patent/ES8609274A1/es not_active Expired
- 1985-07-26 DD DD85279023A patent/DD238972A5/de not_active IP Right Cessation
- 1985-09-19 CN CN198585107017A patent/CN85107017A/zh active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| FI852699A0 (fi) | 1985-07-08 |
| EP0169443A3 (en) | 1986-12-30 |
| NZ212721A (en) | 1989-01-06 |
| ZA855430B (en) | 1986-03-26 |
| PT80854A (en) | 1985-08-01 |
| PT80854B (en) | 1987-01-09 |
| GB2164643A (en) | 1986-03-26 |
| AU576253B2 (en) | 1988-08-18 |
| DK327685D0 (da) | 1985-07-18 |
| GR851722B (ko) | 1985-11-26 |
| IL75864A0 (en) | 1985-11-29 |
| EP0169443A2 (en) | 1986-01-29 |
| KR880000728B1 (ko) | 1988-04-29 |
| FI852699L (fi) | 1986-01-28 |
| US4692447A (en) | 1987-09-08 |
| HU195193B (en) | 1988-04-28 |
| CN85107017A (zh) | 1987-04-01 |
| GB8419253D0 (en) | 1984-08-30 |
| DD238972A5 (de) | 1986-09-10 |
| KR860001076A (ko) | 1986-02-22 |
| DK327685A (da) | 1986-01-28 |
| ES8609274A1 (es) | 1986-07-16 |
| ES545574A0 (es) | 1986-07-16 |
| JPS6147468A (ja) | 1986-03-07 |
| IL75864A (en) | 1990-07-26 |
| GB2164643B (en) | 1988-11-02 |
| AU4481485A (en) | 1986-01-30 |
| HUT38915A (en) | 1986-07-28 |
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