NO860319L - Fremgangsmaate for fremstillig av terapeutisk aktive 4h-1-benzopyran-4-on-derivater og deres svovelholdige analoger. - Google Patents
Fremgangsmaate for fremstillig av terapeutisk aktive 4h-1-benzopyran-4-on-derivater og deres svovelholdige analoger.Info
- Publication number
- NO860319L NO860319L NO860319A NO860319A NO860319L NO 860319 L NO860319 L NO 860319L NO 860319 A NO860319 A NO 860319A NO 860319 A NO860319 A NO 860319A NO 860319 L NO860319 L NO 860319L
- Authority
- NO
- Norway
- Prior art keywords
- formula
- compounds
- benzopyran
- prepared
- compound
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 19
- 238000002360 preparation method Methods 0.000 title claims description 7
- OTAFHZMPRISVEM-UHFFFAOYSA-N chromone Chemical class C1=CC=C2C(=O)C=COC2=C1 OTAFHZMPRISVEM-UHFFFAOYSA-N 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims description 58
- -1 4-pyridinyl Chemical group 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 9
- 125000004122 cyclic group Chemical group 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 3
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 3
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical class [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- TXKUJOMDRORGNV-UHFFFAOYSA-N 7-(3-chloropropoxy)chromen-4-one Chemical compound O1C=CC(=O)C=2C1=CC(OCCCCl)=CC=2 TXKUJOMDRORGNV-UHFFFAOYSA-N 0.000 description 4
- WVJCRTSTRGRJJT-UHFFFAOYSA-N 7-Hydroxy-4-chromone Chemical compound O1C=CC(=O)C=2C1=CC(O)=CC=2 WVJCRTSTRGRJJT-UHFFFAOYSA-N 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 4
- 208000028017 Psychotic disease Diseases 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- 150000001335 aliphatic alkanes Chemical class 0.000 description 4
- 230000000561 anti-psychotic effect Effects 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- 229910000027 potassium carbonate Chemical class 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 201000000980 schizophrenia Diseases 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- YPTJKHVBDCRKNF-UHFFFAOYSA-N 2',6'-Dihydroxyacetophenone Chemical compound CC(=O)C1=C(O)C=CC=C1O YPTJKHVBDCRKNF-UHFFFAOYSA-N 0.000 description 3
- 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 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- MFESCIUQSIBMSM-UHFFFAOYSA-N I-BCP Chemical compound ClCCCBr MFESCIUQSIBMSM-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- 239000000164 antipsychotic agent Substances 0.000 description 3
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 3
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 3
- 239000012458 free base Substances 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 238000011835 investigation Methods 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 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 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- NIDSRGCVYOEDFW-UHFFFAOYSA-N 1-bromo-4-chlorobutane Chemical compound ClCCCCBr NIDSRGCVYOEDFW-UHFFFAOYSA-N 0.000 description 2
- GZYJXGAYVLTOLE-UHFFFAOYSA-N 6-[4-(4-phenylpiperazin-1-yl)butoxy]chromen-4-one Chemical compound C1=C2C(=O)C=COC2=CC=C1OCCCCN(CC1)CCN1C1=CC=CC=C1 GZYJXGAYVLTOLE-UHFFFAOYSA-N 0.000 description 2
- JOTDHKBRHKMDKT-UHFFFAOYSA-N 6-hydroxychromen-4-one Chemical compound O1C=CC(=O)C2=CC(O)=CC=C21 JOTDHKBRHKMDKT-UHFFFAOYSA-N 0.000 description 2
- WCFXKYZEMCKBPV-UHFFFAOYSA-N 7-(4-chlorobutoxy)chromen-4-one Chemical compound O1C=CC(=O)C=2C1=CC(OCCCCCl)=CC=2 WCFXKYZEMCKBPV-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 102000015554 Dopamine receptor Human genes 0.000 description 2
- 108050004812 Dopamine receptor Proteins 0.000 description 2
- 206010020751 Hypersensitivity Diseases 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 2
- 150000008041 alkali metal carbonates Chemical class 0.000 description 2
- 230000007815 allergy Effects 0.000 description 2
- 229940077388 benzenesulfonate Drugs 0.000 description 2
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 210000004556 brain Anatomy 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical class C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 229960003638 dopamine Drugs 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 150000002391 heterocyclic compounds Chemical class 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 230000006742 locomotor activity Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000010534 mechanism of action Effects 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- YZTJYBJCZXZGCT-UHFFFAOYSA-N phenylpiperazine Chemical compound C1CNCCN1C1=CC=CC=C1 YZTJYBJCZXZGCT-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 208000024891 symptom Diseases 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 229940124549 vasodilator Drugs 0.000 description 2
- 239000003071 vasodilator agent Substances 0.000 description 2
- UBXIECYGXFARTC-UHFFFAOYSA-N 1-(2-chlorophenyl)piperazine;dihydrochloride Chemical compound Cl.Cl.ClC1=CC=CC=C1N1CCNCC1 UBXIECYGXFARTC-UHFFFAOYSA-N 0.000 description 1
- VKTFLEIEHOYNCQ-UHFFFAOYSA-N 2-(3-chloropropoxy)chromen-4-one Chemical compound C1=CC=C2OC(OCCCCl)=CC(=O)C2=C1 VKTFLEIEHOYNCQ-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 1
- ZLUVMCKRGUYVOY-UHFFFAOYSA-N 5-(3-chloropropoxy)chromen-4-one Chemical compound O1C=CC(=O)C2=C1C=CC=C2OCCCCl ZLUVMCKRGUYVOY-UHFFFAOYSA-N 0.000 description 1
- DSKKNPWNVCGPIN-UHFFFAOYSA-N 5-[3-(4-phenylpiperazin-1-yl)propoxy]chromen-4-one Chemical compound C=12C(=O)C=COC2=CC=CC=1OCCCN(CC1)CCN1C1=CC=CC=C1 DSKKNPWNVCGPIN-UHFFFAOYSA-N 0.000 description 1
- JHHJLRJRIYICHR-UHFFFAOYSA-N 6-(4-chlorobutoxy)chromen-4-one Chemical compound O1C=CC(=O)C2=CC(OCCCCCl)=CC=C21 JHHJLRJRIYICHR-UHFFFAOYSA-N 0.000 description 1
- GJRSIRXXLGTHBU-UHFFFAOYSA-N 7-(3-aminopropoxy)chromen-4-one Chemical compound O1C=CC(=O)C=2C1=CC(OCCCN)=CC=2 GJRSIRXXLGTHBU-UHFFFAOYSA-N 0.000 description 1
- DWINBSDTUZJIEX-UHFFFAOYSA-N 7-[3-(4-phenyl-3,6-dihydro-2h-pyridin-1-yl)propoxy]chromen-4-one Chemical compound C=1C=C2C(=O)C=COC2=CC=1OCCCN(CC=1)CCC=1C1=CC=CC=C1 DWINBSDTUZJIEX-UHFFFAOYSA-N 0.000 description 1
- CVMQOCJAUOWQRA-UHFFFAOYSA-N 7-[3-(4-phenylpiperazin-1-yl)propoxy]chromen-4-one Chemical compound C=1C=C2C(=O)C=COC2=CC=1OCCCN(CC1)CCN1C1=CC=CC=C1 CVMQOCJAUOWQRA-UHFFFAOYSA-N 0.000 description 1
- OZGHXNXNRIMNFP-UHFFFAOYSA-N 7-[3-(4-phenylpiperidin-1-yl)propoxy]chromen-4-one Chemical compound C=1C=C2C(=O)C=COC2=CC=1OCCCN(CC1)CCC1C1=CC=CC=C1 OZGHXNXNRIMNFP-UHFFFAOYSA-N 0.000 description 1
- BAEIVNMFMUBCGU-UHFFFAOYSA-N 7-[3-[4-(2-chlorophenyl)piperazin-1-yl]propoxy]chromen-4-one Chemical compound ClC1=CC=CC=C1N1CCN(CCCOC=2C=C3C(C(C=CO3)=O)=CC=2)CC1 BAEIVNMFMUBCGU-UHFFFAOYSA-N 0.000 description 1
- GBIOLIIBGHXJSC-UHFFFAOYSA-N 7-[4-(4-phenylpiperazin-1-yl)butoxy]chromen-4-one Chemical compound C=1C=C2C(=O)C=COC2=CC=1OCCCCN(CC1)CCN1C1=CC=CC=C1 GBIOLIIBGHXJSC-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 206010003591 Ataxia Diseases 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-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
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- NHTGHBARYWONDQ-JTQLQIEISA-N L-α-methyl-Tyrosine Chemical compound OC(=O)[C@](N)(C)CC1=CC=C(O)C=C1 NHTGHBARYWONDQ-JTQLQIEISA-N 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 102000003946 Prolactin Human genes 0.000 description 1
- 108010057464 Prolactin Proteins 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000002220 antihypertensive agent Substances 0.000 description 1
- 229940030600 antihypertensive agent Drugs 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 150000004777 chromones Chemical class 0.000 description 1
- HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 1
- 239000012738 dissolution medium Substances 0.000 description 1
- 230000003291 dopaminomimetic effect Effects 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000010304 firing Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haldol Decanoate Natural products C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 229950000188 halopropane Drugs 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 238000009533 lab test Methods 0.000 description 1
- 238000011005 laboratory method Methods 0.000 description 1
- 229940049920 malate Drugs 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
- BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- 230000000701 neuroleptic effect Effects 0.000 description 1
- 210000002569 neuron Anatomy 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 230000003518 presynaptic effect Effects 0.000 description 1
- 229940097325 prolactin Drugs 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229940086735 succinate Drugs 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-M sulfamate Chemical compound NS([O-])(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-M 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
- C07D335/04—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D335/06—Benzothiopyrans; Hydrogenated benzothiopyrans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US69636485A | 1985-01-30 | 1985-01-30 | |
| US06/799,580 US4678787A (en) | 1985-01-30 | 1985-11-22 | 4H-1-benzopyran-4-ones and their sulfur containing analogs |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO860319L true NO860319L (no) | 1986-07-31 |
Family
ID=27105777
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO860319A NO860319L (no) | 1985-01-30 | 1986-01-29 | Fremgangsmaate for fremstillig av terapeutisk aktive 4h-1-benzopyran-4-on-derivater og deres svovelholdige analoger. |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4678787A (fr) |
| EP (1) | EP0190015B1 (fr) |
| KR (1) | KR900001313B1 (fr) |
| CN (1) | CN1007352B (fr) |
| AU (1) | AU576466B2 (fr) |
| CA (1) | CA1241000A (fr) |
| DE (1) | DE3661914D1 (fr) |
| DK (1) | DK40986A (fr) |
| ES (1) | ES8706149A1 (fr) |
| FI (1) | FI860359A (fr) |
| GR (1) | GR860290B (fr) |
| NO (1) | NO860319L (fr) |
| NZ (1) | NZ214967A (fr) |
| PH (1) | PH21896A (fr) |
| PT (1) | PT81932B (fr) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4704390A (en) * | 1986-02-13 | 1987-11-03 | Warner-Lambert Company | Phenyl and heterocyclic tetrahydropyridyl alkoxy-benzheterocyclic compounds as antipsychotic agents |
| ZA873745B (en) * | 1986-06-04 | 1988-10-26 | Daiichi Seiyaku Co | Benzopyran derivatives |
| US5059609A (en) * | 1987-10-19 | 1991-10-22 | Pfizer Inc. | Substituted tetralins, chromans and related compounds in the treatment of asthma, arthritis and related diseases |
| US5149817A (en) * | 1990-03-05 | 1992-09-22 | Shionogi & Co., Ltd. | Teirahydropyridine derivatives |
| US5278174A (en) * | 1990-06-04 | 1994-01-11 | Scios Nova, Inc. | Sigma binding site agents |
| IT1254469B (it) * | 1992-02-25 | 1995-09-25 | Recordati Chem Pharm | Derivati benzopiranici e benzotiopiranici |
| US5605896A (en) * | 1992-02-25 | 1997-02-25 | Recordati S.A., Chemical And Pharmaceutical Company | Bicyclic heterocyclic derivatives having α1 adrenergic and 5HT1A activities |
| US5474994A (en) * | 1992-05-26 | 1995-12-12 | Recordati S.A., Chemical And Pharmaceutical Company | Bicyclic heterocyclic derivatives having α1 -adrenergic and 5HT1A |
| SG65570A1 (en) * | 1992-02-25 | 1999-06-22 | Recordati Chem Pharm | Heterobicyclic compounds |
| IT1258315B (it) * | 1992-04-10 | 1996-02-22 | Recordati Chem Pharm | Derivati del flavone |
| CN1040434C (zh) * | 1992-05-26 | 1998-10-28 | 瑞柯戴堤化学制药公司 | 杂二环化合物 |
| FR2693196B1 (fr) * | 1992-07-03 | 1994-12-23 | Lipha | Dérivés de benzopyranone ou de benzothiopyranone, procédé de préparation et composition pharmaceutique les contenant. |
| US5245051A (en) * | 1992-09-03 | 1993-09-14 | American Home Products Corporation | Antipsychotic chroman derivatives of benzodioxanmethylamine |
| ES2101620B1 (es) * | 1994-03-18 | 1998-04-01 | Ferrer Int | Nuevo compuesto derivado del cromeno. |
| IL112764A0 (en) * | 1994-03-18 | 1995-05-26 | Ferrer Int | New chromene derivatives |
| ES2101646B1 (es) * | 1995-04-12 | 1998-04-01 | Ferrer Int | Nuevo compuesto derivado del cromeno. |
| IL117646A (en) * | 1995-04-12 | 2000-06-01 | Ferrer Int | 7-¬3-¬4-(6-fluoro-1,2-benzisoxazole-3-YL)piperidin-1-YL¾propoxy¾3-alkyl-chromen-4-ones their preparation their uses and pharmaceutical compositions comprising them |
| ES2144355B1 (es) * | 1997-12-30 | 2001-01-01 | Ferrer Int | Compuestos derivados del cromeno. |
| CN102206214B (zh) * | 2011-04-07 | 2014-03-12 | 华中科技大学 | 苯并吡喃酮类衍生物及其应用 |
| CN102267966B (zh) * | 2011-08-01 | 2013-02-27 | 华中科技大学 | 取代的苯并吡喃酮类衍生物及其应用 |
| CN102267971B (zh) * | 2011-08-03 | 2013-03-27 | 华中科技大学 | 脂环并[c]苯并吡喃酮衍生物及其应用 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1134384B (de) * | 1960-10-18 | 1962-08-09 | Hans Voigt Chem Pharm Fabrik D | Verfahren zur Herstellung von Salzen aus Xanthinessigsaeure- und Flavonderivaten |
| DE2123923A1 (de) * | 1971-05-14 | 1972-11-23 | Boehringer Mannheim Gmbh, 6800 Mannheim | 4-eckige Klammer auf omega- (Flavon-7yl-oxy) -alkyl eckige Klammer zu -pigerazin-Derivate und Verfahren zu ihrer Herstellung |
| US4320128A (en) * | 1979-03-24 | 1982-03-16 | Beecham Group Limited | Chromanone derivatives and compositions containing them |
| EP0017352A3 (fr) * | 1979-03-24 | 1981-01-07 | Beecham Group Plc | Dérivés de chromanone, procédé pour leur préparation, compositions les contenant |
| HU184359B (en) * | 1980-12-16 | 1984-08-28 | Chinoin Gyogyszer Es Vegyeszet | Process for preparing substituted acyl-carbamides |
| DE3117389A1 (de) * | 1981-05-02 | 1982-11-18 | Boehringer Mannheim Gmbh, 6800 Mannheim | Benzopyranylether, verfahren zu deren herstellung sowie diese verbindungen enthaltende arzneimittel |
| EP0149223A3 (fr) * | 1981-07-16 | 1986-07-16 | Beecham Group Plc | Intermédiaires |
-
1985
- 1985-11-22 US US06/799,580 patent/US4678787A/en not_active Expired - Fee Related
-
1986
- 1986-01-20 CA CA000499919A patent/CA1241000A/fr not_active Expired
- 1986-01-22 AU AU52620/86A patent/AU576466B2/en not_active Ceased
- 1986-01-23 EP EP86300469A patent/EP0190015B1/fr not_active Expired
- 1986-01-23 DE DE8686300469T patent/DE3661914D1/de not_active Expired
- 1986-01-24 FI FI860359A patent/FI860359A/fi not_active IP Right Cessation
- 1986-01-28 DK DK40986A patent/DK40986A/da not_active Application Discontinuation
- 1986-01-29 PT PT81932A patent/PT81932B/pt not_active IP Right Cessation
- 1986-01-29 NZ NZ214967A patent/NZ214967A/xx unknown
- 1986-01-29 NO NO860319A patent/NO860319L/no unknown
- 1986-01-29 PH PH33348A patent/PH21896A/en unknown
- 1986-01-30 GR GR860290A patent/GR860290B/el unknown
- 1986-01-30 CN CN86100761A patent/CN1007352B/zh not_active Expired
- 1986-01-30 ES ES551439A patent/ES8706149A1/es not_active Expired
- 1986-01-30 KR KR1019860000607A patent/KR900001313B1/ko active IP Right Grant
Also Published As
| Publication number | Publication date |
|---|---|
| DE3661914D1 (en) | 1989-03-02 |
| DK40986D0 (da) | 1986-01-28 |
| FI860359A0 (fi) | 1986-01-24 |
| PT81932A (en) | 1986-02-01 |
| EP0190015A1 (fr) | 1986-08-06 |
| CN1007352B (zh) | 1990-03-28 |
| GR860290B (en) | 1986-06-02 |
| CA1241000A (fr) | 1988-08-23 |
| KR860005810A (ko) | 1986-08-13 |
| ES551439A0 (es) | 1987-06-01 |
| KR900001313B1 (ko) | 1990-03-08 |
| AU5262086A (en) | 1986-08-07 |
| PH21896A (en) | 1988-03-25 |
| CN86100761A (zh) | 1987-01-21 |
| NZ214967A (en) | 1988-08-30 |
| US4678787A (en) | 1987-07-07 |
| ES8706149A1 (es) | 1987-06-01 |
| EP0190015B1 (fr) | 1989-01-25 |
| AU576466B2 (en) | 1988-08-25 |
| DK40986A (da) | 1986-07-31 |
| FI860359A (fi) | 1986-07-31 |
| PT81932B (pt) | 1987-11-30 |
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