SK3332003A3 - Chromanone derivative, process for its preparation and its use - Google Patents

Chromanone derivative, process for its preparation and its use Download PDF

Info

Publication number: SK3332003A3
Authority: SK; Slovakia
Prior art keywords: formula; compound; chromanone; group; compounds
Prior art date: 2000-09-07

Application number

SK333-2003A

Other languages

English (en)

Slovak (sk)

Inventor

Heinz-Hermann Bokel

Christoph Murmann

Uschi Schmid

Original Assignee

Merck Patent Gmbh

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.)

2000-09-07

Filing date

2001-08-28

Publication date

2003-07-01

2001-08-28 Application filed by Merck Patent Gmbh filed Critical Merck Patent Gmbh

2003-07-01 Publication of SK3332003A3 publication Critical patent/SK3332003A3/sk

Links

238000002360 preparation method Methods 0.000 title claims description 17
238000000034 method Methods 0.000 title claims description 13
YLQDYYDPDQFLAU-UHFFFAOYSA-N 7-methoxy-2-(4-methoxyphenyl)-3-phenyl-2,3-dihydrochromen-4-one Chemical compound C1=CC(OC)=CC=C1C1C(C=2C=CC=CC=2)C(=O)C2=CC=C(OC)C=C2O1 YLQDYYDPDQFLAU-UHFFFAOYSA-N 0.000 title claims description 5
150000003839 salts Chemical class 0.000 claims abstract description 32
239000003814 drug Substances 0.000 claims abstract description 9
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 6
MSTDXOZUKAQDRL-UHFFFAOYSA-N 4-Chromanone Chemical class C1=CC=C2C(=O)CCOC2=C1 MSTDXOZUKAQDRL-UHFFFAOYSA-N 0.000 claims abstract description 5
229910052794 bromium Inorganic materials 0.000 claims abstract description 4
229910052801 chlorine Inorganic materials 0.000 claims abstract description 4
229910052731 fluorine Inorganic materials 0.000 claims abstract description 4
150000001875 compounds Chemical class 0.000 claims description 41
-1 (R) - (chroman-2-ylmethyl) amine Chemical class 0.000 claims description 23
239000003054 catalyst Substances 0.000 claims description 17
229910052739 hydrogen Inorganic materials 0.000 claims description 15
239000001257 hydrogen Substances 0.000 claims description 15
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 14
239000002253 acid Substances 0.000 claims description 13
125000002252 acyl group Chemical group 0.000 claims description 13
238000005984 hydrogenation reaction Methods 0.000 claims description 11
125000006239 protecting group Chemical group 0.000 claims description 9
HKFMQJUJWSFOLY-OAQYLSRUSA-N sarizotan Chemical compound C1=CC(F)=CC=C1C1=CN=CC(CNC[C@@H]2OC3=CC=CC=C3CC2)=C1 HKFMQJUJWSFOLY-OAQYLSRUSA-N 0.000 claims description 9
BSRHATGBRQMDRF-SECBINFHSA-N [(2r)-3,4-dihydro-2h-chromen-2-yl]methanamine Chemical compound C1=CC=C2O[C@@H](CN)CCC2=C1 BSRHATGBRQMDRF-SECBINFHSA-N 0.000 claims description 8
239000000203 mixture Substances 0.000 claims description 8
239000010948 rhodium Substances 0.000 claims description 7
229910052723 transition metal Inorganic materials 0.000 claims description 7
150000003624 transition metals Chemical class 0.000 claims description 7
239000000460 chlorine Substances 0.000 claims description 6
238000002425 crystallisation Methods 0.000 claims description 6
230000008025 crystallization Effects 0.000 claims description 6
210000003169 central nervous system Anatomy 0.000 claims description 5
VURFVHCLMJOLKN-UHFFFAOYSA-N diphosphane Chemical compound PP VURFVHCLMJOLKN-UHFFFAOYSA-N 0.000 claims description 5
239000003446 ligand Substances 0.000 claims description 5
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
229910052751 metal Inorganic materials 0.000 claims description 4
239000002184 metal Substances 0.000 claims description 4
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
239000011737 fluorine Substances 0.000 claims description 3
229910052703 rhodium Inorganic materials 0.000 claims description 3
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 3
UTIGGFSFSWUDIR-SSDOTTSWSA-N (2r)-2-(aminomethyl)-2,3-dihydrochromen-4-one Chemical compound C1=CC=C2O[C@@H](CN)CC(=O)C2=C1 UTIGGFSFSWUDIR-SSDOTTSWSA-N 0.000 claims description 2
UTIGGFSFSWUDIR-ZETCQYMHSA-N (2s)-2-(aminomethyl)-2,3-dihydrochromen-4-one Chemical compound C1=CC=C2O[C@H](CN)CC(=O)C2=C1 UTIGGFSFSWUDIR-ZETCQYMHSA-N 0.000 claims description 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
UTIGGFSFSWUDIR-UHFFFAOYSA-N 2-(aminomethyl)-2,3-dihydrochromen-4-one Chemical compound C1=CC=C2OC(CN)CC(=O)C2=C1 UTIGGFSFSWUDIR-UHFFFAOYSA-N 0.000 claims description 2
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
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 2
229940079593 drug Drugs 0.000 claims description 2
229910052741 iridium Inorganic materials 0.000 claims description 2
GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 2
229910052763 palladium Inorganic materials 0.000 claims description 2
229910052707 ruthenium Inorganic materials 0.000 claims description 2
238000003776 cleavage reaction Methods 0.000 claims 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 1
230000007017 scission Effects 0.000 claims 1
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 1
125000000217 alkyl group Chemical group 0.000 abstract description 2
230000015572 biosynthetic process Effects 0.000 abstract description 2
229910052740 iodine Inorganic materials 0.000 abstract description 2
238000003786 synthesis reaction Methods 0.000 abstract description 2
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 abstract description 2
239000013067 intermediate product Substances 0.000 abstract 1
238000006243 chemical reaction Methods 0.000 description 16
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 14
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 13
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
GOUBCYXYLMPDQA-UHFFFAOYSA-N n-[(4-oxo-2,3-dihydrochromen-2-yl)methyl]acetamide Chemical compound C1=CC=C2OC(CNC(=O)C)CC(=O)C2=C1 GOUBCYXYLMPDQA-UHFFFAOYSA-N 0.000 description 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 6
239000000543 intermediate Substances 0.000 description 6
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
GBGRGXDUABUUBE-BFHBGLAWSA-N n-[[(2r)-4-hydroxy-3,4-dihydro-2h-chromen-2-yl]methyl]acetamide Chemical compound C1=CC=C2O[C@@H](CNC(=O)C)CC(O)C2=C1 GBGRGXDUABUUBE-BFHBGLAWSA-N 0.000 description 5
229910000510 noble metal Inorganic materials 0.000 description 5
239000000047 product Substances 0.000 description 5
239000002585 base Substances 0.000 description 4
238000001035 drying Methods 0.000 description 4
GOUBCYXYLMPDQA-SECBINFHSA-N n-[[(2r)-4-oxo-2,3-dihydrochromen-2-yl]methyl]acetamide Chemical compound C1=CC=C2O[C@@H](CNC(=O)C)CC(=O)C2=C1 GOUBCYXYLMPDQA-SECBINFHSA-N 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
239000002904 solvent Substances 0.000 description 4
125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
125000003118 aryl group Chemical group 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
239000012442 inert solvent Substances 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
230000006340 racemization Effects 0.000 description 3
239000007858 starting material Substances 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
XVWSBJKJUXDTFK-YOXFSPIKSA-N (2r)-2-(aminomethyl)-3,4-dihydro-2h-chromen-4-ol Chemical compound C1=CC=C2O[C@@H](CN)CC(O)C2=C1 XVWSBJKJUXDTFK-YOXFSPIKSA-N 0.000 description 2
HQWIZLLTPUIFDL-DZQWQCQZSA-N (2r)-2-(aminomethyl)-3,4-dihydro-2h-chromen-4-ol;hydrochloride Chemical compound Cl.C1=CC=C2O[C@@H](CN)CC(O)C2=C1 HQWIZLLTPUIFDL-DZQWQCQZSA-N 0.000 description 2
XVWSBJKJUXDTFK-JAVCKPHESA-N (2s)-2-(aminomethyl)-3,4-dihydro-2h-chromen-4-ol Chemical compound C1=CC=C2O[C@H](CN)CC(O)C2=C1 XVWSBJKJUXDTFK-JAVCKPHESA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
XVWSBJKJUXDTFK-UHFFFAOYSA-N 2-(aminomethyl)-3,4-dihydro-2h-chromen-4-ol Chemical compound C1=CC=C2OC(CN)CC(O)C2=C1 XVWSBJKJUXDTFK-UHFFFAOYSA-N 0.000 description 2
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
238000005644 Wolff-Kishner reduction reaction Methods 0.000 description 2
125000002723 alicyclic group Chemical group 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
125000005092 alkenyloxycarbonyl group Chemical group 0.000 description 2
125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
FFGPTBGBLSHEPO-UHFFFAOYSA-N carbamazepine Chemical compound C1=CC2=CC=CC=C2N(C(=O)N)C2=CC=CC=C21 FFGPTBGBLSHEPO-UHFFFAOYSA-N 0.000 description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
VZWXIQHBIQLMPN-UHFFFAOYSA-N chromane Chemical class C1=CC=C2CCCOC2=C1 VZWXIQHBIQLMPN-UHFFFAOYSA-N 0.000 description 2
238000001816 cooling Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
238000001914 filtration Methods 0.000 description 2
150000002431 hydrogen Chemical class 0.000 description 2
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
GBGRGXDUABUUBE-UHFFFAOYSA-N n-[(4-hydroxy-3,4-dihydro-2h-chromen-2-yl)methyl]acetamide Chemical compound C1=CC=C2OC(CNC(=O)C)CC(O)C2=C1 GBGRGXDUABUUBE-UHFFFAOYSA-N 0.000 description 2
YPANBNNTDTUMLB-UHFFFAOYSA-N n-[(4-oxochromen-2-yl)methyl]acetamide Chemical compound C1=CC=C2OC(CNC(=O)C)=CC(=O)C2=C1 YPANBNNTDTUMLB-UHFFFAOYSA-N 0.000 description 2
GBGRGXDUABUUBE-FTNKSUMCSA-N n-[[(2s)-4-hydroxy-3,4-dihydro-2h-chromen-2-yl]methyl]acetamide Chemical compound C1=CC=C2O[C@H](CNC(=O)C)CC(O)C2=C1 GBGRGXDUABUUBE-FTNKSUMCSA-N 0.000 description 2
235000011007 phosphoric acid Nutrition 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 2
238000000746 purification Methods 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
238000006722 reduction reaction Methods 0.000 description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
238000009736 wetting Methods 0.000 description 2
DOUYEWTUNFBJEO-OGFXRTJISA-N (2r)-2-(aminomethyl)-2,3-dihydrochromen-4-one;hydrochloride Chemical compound Cl.C1=CC=C2O[C@@H](CN)CC(=O)C2=C1 DOUYEWTUNFBJEO-OGFXRTJISA-N 0.000 description 1
125000005919 1,2,2-trimethylpropyl group Chemical group 0.000 description 1
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
BHKKSKOHRFHHIN-MRVPVSSYSA-N 1-[[2-[(1R)-1-aminoethyl]-4-chlorophenyl]methyl]-2-sulfanylidene-5H-pyrrolo[3,2-d]pyrimidin-4-one Chemical compound N[C@H](C)C1=C(CN2C(NC(C3=C2C=CN3)=O)=S)C=CC(=C1)Cl BHKKSKOHRFHHIN-MRVPVSSYSA-N 0.000 description 1
LDMOEFOXLIZJOW-UHFFFAOYSA-N 1-dodecanesulfonic acid Chemical class CCCCCCCCCCCCS(O)(=O)=O LDMOEFOXLIZJOW-UHFFFAOYSA-N 0.000 description 1
125000006218 1-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
125000006219 1-ethylpentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
125000005916 2-methylpentyl group Chemical group 0.000 description 1
BSRHATGBRQMDRF-UHFFFAOYSA-N 3,4-dihydro-2h-chromen-2-ylmethanamine Chemical compound C1=CC=C2OC(CN)CCC2=C1 BSRHATGBRQMDRF-UHFFFAOYSA-N 0.000 description 1
125000005917 3-methylpentyl group Chemical group 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
241001310793 Podium Species 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
IOPQYDKQISFMJI-UHFFFAOYSA-N [1-[2-bis(4-methylphenyl)phosphanylnaphthalen-1-yl]naphthalen-2-yl]-bis(4-methylphenyl)phosphane Chemical compound C1=CC(C)=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 IOPQYDKQISFMJI-UHFFFAOYSA-N 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
238000006470 amide elimination reaction Methods 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
125000003435 aroyl group Chemical group 0.000 description 1
125000003710 aryl alkyl group Chemical group 0.000 description 1
125000005161 aryl oxy carbonyl group Chemical group 0.000 description 1
125000004391 aryl sulfonyl group Chemical group 0.000 description 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
230000000903 blocking effect Effects 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
238000006555 catalytic reaction Methods 0.000 description 1
FWXAUDSWDBGCMN-ZEQRLZLVSA-N chiraphos Chemical compound C=1C=CC=CC=1P([C@@H](C)[C@H](C)P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 FWXAUDSWDBGCMN-ZEQRLZLVSA-N 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
ZCDOYSPFYFSLEW-UHFFFAOYSA-N chromate(2-) Chemical class [O-][Cr]([O-])(=O)=O ZCDOYSPFYFSLEW-UHFFFAOYSA-N 0.000 description 1
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000012467 final product Substances 0.000 description 1
125000000623 heterocyclic group Chemical group 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
150000004677 hydrates Chemical class 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
238000002955 isolation Methods 0.000 description 1
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
150000007522 mineralic acids Chemical class 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
GOUBCYXYLMPDQA-VIFPVBQESA-N n-[[(2s)-4-oxo-2,3-dihydrochromen-2-yl]methyl]acetamide Chemical compound C1=CC=C2O[C@H](CNC(=O)C)CC(=O)C2=C1 GOUBCYXYLMPDQA-VIFPVBQESA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 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
150000002825 nitriles Chemical class 0.000 description 1
238000005580 one pot reaction Methods 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
125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
238000005191 phase separation Methods 0.000 description 1
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
150000003016 phosphoric acids Chemical class 0.000 description 1
OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical class OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000002243 precursor Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000012453 solvate Substances 0.000 description 1
241000894007 species Species 0.000 description 1
239000000758 substrate Substances 0.000 description 1
125000000542 sulfonic acid group Chemical group 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical class S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000010189 synthetic method Methods 0.000 description 1
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000005425 toluyl group Chemical group 0.000 description 1
ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- 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
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pyridine Compounds (AREA)
Pyrane Compounds (AREA)

SK333-2003A 2000-09-07 2001-08-28 Chromanone derivative, process for its preparation and its use SK3332003A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE10044091A DE10044091A1 (de)	2000-09-07	2000-09-07	Chromanonderivate
PCT/EP2001/009900 WO2002020507A1 (de)	2000-09-07	2001-08-28	Chromanonderivate

Publications (1)

Publication Number	Publication Date
SK3332003A3 true SK3332003A3 (en)	2003-07-01

Family

ID=7655302

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK333-2003A SK3332003A3 (en)	2000-09-07	2001-08-28	Chromanone derivative, process for its preparation and its use

Country Status (19)

Country	Link
US (1)	US6812353B2 (pl)
EP (1)	EP1317438A1 (pl)
JP (1)	JP2004508363A (pl)
KR (1)	KR20030040402A (pl)
CN (1)	CN1249044C (pl)
AR (1)	AR030625A1 (pl)
AU (1)	AU2001284039A1 (pl)
BR (1)	BR0113584A (pl)
CA (1)	CA2421287A1 (pl)
DE (1)	DE10044091A1 (pl)
HU (1)	HUP0302065A3 (pl)
MY (1)	MY133893A (pl)
NO (1)	NO20031034L (pl)
PL (1)	PL362761A1 (pl)
RU (1)	RU2273638C2 (pl)
SK (1)	SK3332003A3 (pl)
UA (1)	UA75892C2 (pl)
WO (1)	WO2002020507A1 (pl)
ZA (1)	ZA200302632B (pl)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE10044091A1 (de)	2000-09-07	2002-04-04	Merck Patent Gmbh	Chromanonderivate
EP1432694A1 (en)	2001-10-05	2004-06-30	Wyeth	Stereospecific process for the synthesis of 2-yl chroman derivatives
CN1564818A (zh)	2001-10-05	2005-01-12	惠氏公司	2－羟甲基－苯并二氢吡喃的立体选择性合成方法
US20050261347A1 (en) *	2003-10-24	2005-11-24	Wyeth	Dihydrobenzofuranyl alkanamine derivatives and methods for using same
US7435837B2 (en) *	2003-10-24	2008-10-14	Wyeth	Dihydrobenzofuranyl alkanamine derivatives and methods for using same
JP2008538576A (ja) *	2005-04-22	2008-10-30	ワイス	クロマンおよびクロメン誘導体およびその使用
US7528267B2 (en) *	2005-08-01	2009-05-05	Girindus America, Inc.	Method for enantioselective hydrogenation of chromenes
CN101300246A (zh) *	2005-11-03	2008-11-05	弗·哈夫曼-拉罗切有限公司	作为5－ht6抑制剂的芳基磺酰基色满类化合物作为蛋白激酶抑制剂的吲哚基马来酰亚胺衍生物
RU2468018C1 (ru) *	2011-10-06	2012-11-27	Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "Российский университет дружбы народов" (РУДН)	Способ получения производных 4-оксо-4h-хроменов, содержащих винильную и енаминную группировки
NO3078372T3 (pl) *	2013-07-18	2018-02-10
JP2017508728A (ja) *	2014-01-17	2017-03-30	メルクパテントゲーエムベーハー	有機エレクトロルミネッセント素子のための材料
WO2019212211A1 (en) *	2018-04-30	2019-11-07	Gachon University Of Industry-Academic Cooperation Foundation	Antiangiogenic chromane derivative and uses thereof

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2611910A1 (de)	1976-03-20	1977-09-22	Bayer Ag	Chromanone-(4)
CH619701A5 (pl) *	1975-08-07	1980-10-15	Bayer Ag
EP0459983A1 (en) *	1988-12-21	1991-12-11	PHARMACIA & UPJOHN COMPANY	Antiatherosclerotic and antithrombotic 1-benzopyran-4-ones and 2-amino-1,3-benzoxazine-4-ones
ES2169102T3 (es) *	1994-10-14	2002-07-01	Merck Patent Gmbh	(r)-(-)-2-(5-(4-fluorfenil)-3-piridilmetilaminometil)-cromano como agente activo sobre el sistema nervioso central.
DE19858341A1 (de) *	1998-12-17	2000-06-21	Merck Patent Gmbh	Chromanderivate
DE10044091A1 (de)	2000-09-07	2002-04-04	Merck Patent Gmbh	Chromanonderivate

2000
- 2000-09-07 DE DE10044091A patent/DE10044091A1/de not_active Withdrawn
2001
- 2001-08-28 RU RU2003108856/04A patent/RU2273638C2/ru not_active IP Right Cessation
- 2001-08-28 UA UA2003042933A patent/UA75892C2/uk unknown
- 2001-08-28 US US10/363,774 patent/US6812353B2/en not_active Expired - Fee Related
- 2001-08-28 CN CNB018150616A patent/CN1249044C/zh not_active Expired - Fee Related
- 2001-08-28 EP EP01962976A patent/EP1317438A1/de not_active Ceased
- 2001-08-28 WO PCT/EP2001/009900 patent/WO2002020507A1/de not_active Ceased
- 2001-08-28 HU HU0302065A patent/HUP0302065A3/hu unknown
- 2001-08-28 PL PL01362761A patent/PL362761A1/pl unknown
- 2001-08-28 CA CA002421287A patent/CA2421287A1/en not_active Abandoned
- 2001-08-28 AU AU2001284039A patent/AU2001284039A1/en not_active Abandoned
- 2001-08-28 BR BR0113584-8A patent/BR0113584A/pt not_active IP Right Cessation
- 2001-08-28 JP JP2002525128A patent/JP2004508363A/ja active Pending
- 2001-08-28 SK SK333-2003A patent/SK3332003A3/sk unknown
- 2001-08-28 KR KR10-2003-7002303A patent/KR20030040402A/ko not_active Withdrawn
- 2001-09-03 MY MYPI20014131 patent/MY133893A/en unknown
- 2001-09-07 AR ARP010104249A patent/AR030625A1/es not_active Application Discontinuation
2003
- 2003-03-06 NO NO20031034A patent/NO20031034L/no not_active Application Discontinuation
- 2003-04-03 ZA ZA200302632A patent/ZA200302632B/en unknown

Also Published As

Publication number	Publication date
KR20030040402A (ko)	2003-05-22
CN1249044C (zh)	2006-04-05
EP1317438A1 (de)	2003-06-11
DE10044091A1 (de)	2002-04-04
NO20031034D0 (no)	2003-03-06
ZA200302632B (en)	2004-09-02
HUP0302065A3 (en)	2005-07-28
WO2002020507A1 (de)	2002-03-14
PL362761A1 (pl)	2004-11-02
JP2004508363A (ja)	2004-03-18
MY133893A (en)	2007-11-30
US20040092579A1 (en)	2004-05-13
RU2273638C2 (ru)	2006-04-10
HUP0302065A2 (hu)	2003-09-29
NO20031034L (no)	2003-03-06
CA2421287A1 (en)	2003-03-05
UA75892C2 (en)	2006-06-15
BR0113584A (pt)	2003-07-15
US6812353B2 (en)	2004-11-02
AU2001284039A1 (en)	2002-03-22
AR030625A1 (es)	2003-08-27
CN1451001A (zh)	2003-10-22

Publication	Publication Date	Title
US6812353B2 (en)	2004-11-02	Chromanone derivatives
AU760501B2 (en)	2003-05-15	Chroman derivatives
US6762300B2 (en)	2004-07-13	Method for producing 5-(1-piperazinyl)-benzofuran-2-carboxamide by transition metal-catalyzed amination
EP1153023B1 (en)	2003-04-23	Process for the production of paroxetine
AU2014257594A1 (en)	2015-10-08	Synthesis of BACE inhibitors
HRP20000490A2 (en)	2002-02-28	Process for the preparation of amlodipine besilate
HK1058204A (en)	2004-05-07	Chromanone derivatives