HRP980086A2 - Sulfonamido substituted chromanes, processes for the preparation thereof, their use as medicines or diagnostic agents, as well as pharmaceutical preparations containing them - Google Patents

Sulfonamido substituted chromanes, processes for the preparation thereof, their use as medicines or diagnostic agents, as well as pharmaceutical preparations containing them

Info

Publication number: HRP980086A2
Authority: HR; Croatia
Prior art keywords: atoms; hydrogen; group; formula; phenyl
Prior art date: 1997-02-20

Application number

HR19706675.5A

Other languages

English (en)

Croatian (hr)

Inventor

Klaus Weidmann

Original Assignee

Klaus Weidmann

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.)

1997-02-20

Filing date

1998-02-19

Publication date

1998-10-31

1998-02-19 Application filed by Klaus Weidmann filed Critical Klaus Weidmann

1998-10-31 Publication of HRP980086A2 publication Critical patent/HRP980086A2/hr

Links

239000003814 drug Substances 0.000 title claims description 17
229940079593 drug Drugs 0.000 title claims description 12
238000000034 method Methods 0.000 title description 38
238000002360 preparation method Methods 0.000 title description 7
230000008569 process Effects 0.000 title description 3
150000001843 chromanes Chemical class 0.000 title description 2
229940039227 diagnostic agent Drugs 0.000 title 1
239000000032 diagnostic agent Substances 0.000 title 1
239000000825 pharmaceutical preparation Substances 0.000 title 1
125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 title 1
239000001257 hydrogen Substances 0.000 claims description 65
229910052739 hydrogen Inorganic materials 0.000 claims description 65
150000001875 compounds Chemical class 0.000 claims description 64
125000004432 carbon atom Chemical group C* 0.000 claims description 52
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 34
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 34
150000002431 hydrogen Chemical class 0.000 claims description 31
-1 methoxy, sulfamoyl Chemical group 0.000 claims description 31
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 30
125000001424 substituent group Chemical group 0.000 claims description 29
229910052801 chlorine Inorganic materials 0.000 claims description 27
125000000217 alkyl group Chemical group 0.000 claims description 25
229910052731 fluorine Inorganic materials 0.000 claims description 25
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 24
229910052794 bromium Inorganic materials 0.000 claims description 22
150000003839 salts Chemical class 0.000 claims description 16
125000000753 cycloalkyl group Chemical group 0.000 claims description 14
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 14
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
125000004076 pyridyl group Chemical group 0.000 claims description 10
206010003119 arrhythmia Diseases 0.000 claims description 9
125000002947 alkylene group Chemical group 0.000 claims description 8
125000005004 perfluoroethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 8
125000005009 perfluoropropyl group Chemical group FC(C(C(F)(F)F)(F)F)(F)* 0.000 claims description 8
230000006793 arrhythmia Effects 0.000 claims description 7
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
125000002883 imidazolyl group Chemical group 0.000 claims description 6
125000001544 thienyl group Chemical group 0.000 claims description 6
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims description 4
125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
230000000903 blocking effect Effects 0.000 claims description 4
125000005936 piperidyl group Chemical group 0.000 claims description 4
230000002265 prevention Effects 0.000 claims description 4
IVOMOUWHDPKRLL-KQYNXXCUSA-N Cyclic adenosine monophosphate Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-KQYNXXCUSA-N 0.000 claims description 3
206010049418 Sudden Cardiac Death Diseases 0.000 claims description 3
206010003130 Arrhythmia supraventricular Diseases 0.000 claims description 2
206010012735 Diarrhoea Diseases 0.000 claims description 2
206010042600 Supraventricular arrhythmias Diseases 0.000 claims description 2
208000025865 Ulcer Diseases 0.000 claims description 2
206010047281 Ventricular arrhythmia Diseases 0.000 claims description 2
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 2
125000004423 acyloxy group Chemical group 0.000 claims description 2
125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 2
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 2
125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 2
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
210000001198 duodenum Anatomy 0.000 claims description 2
208000021302 gastroesophageal reflux disease Diseases 0.000 claims description 2
230000002401 inhibitory effect Effects 0.000 claims description 2
230000000968 intestinal effect Effects 0.000 claims description 2
125000005956 isoquinolyl group Chemical group 0.000 claims description 2
208000000689 peptic esophagitis Diseases 0.000 claims description 2
125000005493 quinolyl group Chemical group 0.000 claims description 2
230000028327 secretion Effects 0.000 claims description 2
210000002784 stomach Anatomy 0.000 claims description 2
231100000397 ulcer Toxicity 0.000 claims description 2
230000002861 ventricular Effects 0.000 claims description 2
208000003663 ventricular fibrillation Diseases 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims 8
125000003016 chromanyl group Chemical class O1C(CCC2=CC=CC=C12)* 0.000 claims 1
230000002496 gastric effect Effects 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
238000006243 chemical reaction Methods 0.000 description 25
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 24
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
239000002904 solvent Substances 0.000 description 22
239000000126 substance Substances 0.000 description 21
238000002844 melting Methods 0.000 description 20
230000008018 melting Effects 0.000 description 20
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
239000000203 mixture Substances 0.000 description 18
239000000460 chlorine Substances 0.000 description 16
229940124530 sulfonamide Drugs 0.000 description 16
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
230000009471 action Effects 0.000 description 15
235000002639 sodium chloride Nutrition 0.000 description 15
150000003456 sulfonamides Chemical class 0.000 description 14
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 12
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 12
239000000243 solution Substances 0.000 description 12
ZKHQWZAMYRWXGA-UHFFFAOYSA-N Adenosine triphosphate Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(=O)OP(O)(=O)OP(O)(O)=O)C(O)C1O ZKHQWZAMYRWXGA-UHFFFAOYSA-N 0.000 description 11
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
235000019439 ethyl acetate Nutrition 0.000 description 9
239000000047 product Substances 0.000 description 9
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 8
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
239000002585 base Substances 0.000 description 8
239000000725 suspension Substances 0.000 description 8
108091006146 Channels Proteins 0.000 description 7
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 7
239000003921 oil Substances 0.000 description 7
235000019198 oils Nutrition 0.000 description 7
229910000104 sodium hydride Inorganic materials 0.000 description 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
238000005804 alkylation reaction Methods 0.000 description 5
150000001412 amines Chemical class 0.000 description 5
230000003288 anthiarrhythmic effect Effects 0.000 description 5
230000000144 pharmacologic effect Effects 0.000 description 5
239000011734 sodium Substances 0.000 description 5
VZAWCLCJGSBATP-UHFFFAOYSA-N 1-cycloundecyl-1,2-diazacycloundecane Chemical compound C1CCCCCCCCCC1N1NCCCCCCCCC1 VZAWCLCJGSBATP-UHFFFAOYSA-N 0.000 description 4
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
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 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
239000013543 active substance Substances 0.000 description 4
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
239000000969 carrier Substances 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
VZWXIQHBIQLMPN-UHFFFAOYSA-N chromane Chemical compound C1=CC=C2CCCOC2=C1 VZWXIQHBIQLMPN-UHFFFAOYSA-N 0.000 description 4
239000013078 crystal Substances 0.000 description 4
150000002118 epoxides Chemical class 0.000 description 4
238000010438 heat treatment Methods 0.000 description 4
230000007246 mechanism Effects 0.000 description 4
QSPPRYLTQFCUCH-UHFFFAOYSA-N n-methylethanesulfonamide Chemical compound CCS(=O)(=O)NC QSPPRYLTQFCUCH-UHFFFAOYSA-N 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
238000005727 Friedel-Crafts reaction Methods 0.000 description 3
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
230000004913 activation Effects 0.000 description 3
239000002168 alkylating agent Substances 0.000 description 3
229940100198 alkylating agent Drugs 0.000 description 3
230000029936 alkylation Effects 0.000 description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
238000002425 crystallisation Methods 0.000 description 3
230000008025 crystallization Effects 0.000 description 3
230000000694 effects Effects 0.000 description 3
239000003480 eluent Substances 0.000 description 3
239000003995 emulsifying agent Substances 0.000 description 3
229910052740 iodine Inorganic materials 0.000 description 3
BHEZVVIDLXXLPN-UHFFFAOYSA-N n-(6,8-dichloro-3-hydroxy-2,2-dimethyl-3,4-dihydrochromen-4-yl)-n-methylethanesulfonamide Chemical compound C1=C(Cl)C=C2C(N(C)S(=O)(=O)CC)C(O)C(C)(C)OC2=C1Cl BHEZVVIDLXXLPN-UHFFFAOYSA-N 0.000 description 3
RVKKLDBBHZGTAC-UHFFFAOYSA-N n-(6-cyano-7-fluoro-3-hydroxy-2,2-dimethyl-3,4-dihydrochromen-4-yl)-n-methylethanesulfonamide Chemical compound FC1=C(C#N)C=C2C(N(C)S(=O)(=O)CC)C(O)C(C)(C)OC2=C1 RVKKLDBBHZGTAC-UHFFFAOYSA-N 0.000 description 3
NIYGLRKUBPNXQS-FYYLOGMGSA-N n-[(4r)-1'-[(2r)-6-cyano-1,2,3,4-tetrahydronaphthalen-2-yl]-4-hydroxyspiro[3,4-dihydrochromene-2,4'-piperidine]-6-yl]methanesulfonamide Chemical compound C1CC2=CC(C#N)=CC=C2C[C@@H]1N(CC1)CCC11OC2=CC=C(NS(=O)(=O)C)C=C2[C@H](O)C1 NIYGLRKUBPNXQS-FYYLOGMGSA-N 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
229910052700 potassium Inorganic materials 0.000 description 3
239000011591 potassium Substances 0.000 description 3
230000009467 reduction Effects 0.000 description 3
210000002460 smooth muscle Anatomy 0.000 description 3
239000007787 solid Substances 0.000 description 3
WUXLIRTUXHXRNA-SCZZXKLOSA-N (3r,4r)-4-bromo-6,8-dichloro-2,2-dimethyl-3,4-dihydrochromen-3-ol Chemical compound C1=C(Cl)C=C2[C@@H](Br)[C@H](O)C(C)(C)OC2=C1Cl WUXLIRTUXHXRNA-SCZZXKLOSA-N 0.000 description 2
AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 2
MGSHXMOLUWTMGP-UHFFFAOYSA-N 3'-carboxy-alpha-chromanol Chemical compound C1=CC=C2C(O)CCOC2=C1 MGSHXMOLUWTMGP-UHFFFAOYSA-N 0.000 description 2
SEBPXHSZHLFWRL-UHFFFAOYSA-N 3,4-dihydro-2,2,5,7,8-pentamethyl-2h-1-benzopyran-6-ol Chemical compound O1C(C)(C)CCC2=C1C(C)=C(C)C(O)=C2C SEBPXHSZHLFWRL-UHFFFAOYSA-N 0.000 description 2
HBLDKCGIBIGVPC-UHFFFAOYSA-N 3,4-dihydro-2h-chromen-3-ol Chemical class C1=CC=C2CC(O)COC2=C1 HBLDKCGIBIGVPC-UHFFFAOYSA-N 0.000 description 2
MGQRLQVBMCPDMF-UHFFFAOYSA-N 4,6-dichloro-2,2-dimethyl-1a,7b-dihydrooxireno[2,3-c]chromene Chemical compound CC1(C)OC2=C(Cl)C=C(Cl)C=C2C2C1O2 MGQRLQVBMCPDMF-UHFFFAOYSA-N 0.000 description 2
MSTDXOZUKAQDRL-UHFFFAOYSA-N 4-Chromanone Chemical compound C1=CC=C2C(=O)CCOC2=C1 MSTDXOZUKAQDRL-UHFFFAOYSA-N 0.000 description 2
HUONCXXUTSXPJH-UHFFFAOYSA-N 5-chloro-6-fluoro-2,2-dimethyl-1a,7b-dihydrooxireno[2,3-c]chromene Chemical compound CC1(C)OC2=CC(Cl)=C(F)C=C2C2C1O2 HUONCXXUTSXPJH-UHFFFAOYSA-N 0.000 description 2
FTJGQWPWHNGFHU-UHFFFAOYSA-N 6,8-dichloro-2,2-dimethyl-3,4-dihydrochromen-4-ol Chemical compound ClC1=CC(Cl)=C2OC(C)(C)CC(O)C2=C1 FTJGQWPWHNGFHU-UHFFFAOYSA-N 0.000 description 2
IWKBJCINFJOFTK-UHFFFAOYSA-N 6,8-dichloro-2,2-dimethyl-3h-chromen-4-one Chemical compound ClC1=CC(Cl)=C2OC(C)(C)CC(=O)C2=C1 IWKBJCINFJOFTK-UHFFFAOYSA-N 0.000 description 2
OXKYGXYBKNTVBK-UHFFFAOYSA-N 7-chloro-4-hydroxy-2,2-dimethyl-3,4-dihydrochromene-6-carbonitrile Chemical compound N#CC1=C(Cl)C=C2OC(C)(C)CC(O)C2=C1 OXKYGXYBKNTVBK-UHFFFAOYSA-N 0.000 description 2
HBKNDJHRRKFWCO-UHFFFAOYSA-N 7-chloro-6-fluoro-2,2-dimethyl-3,4-dihydrochromen-4-ol Chemical compound FC1=C(Cl)C=C2OC(C)(C)CC(O)C2=C1 HBKNDJHRRKFWCO-UHFFFAOYSA-N 0.000 description 2
NKCIUOVMTURVQK-UHFFFAOYSA-N 7-chloro-6-fluoro-2,2-dimethyl-3h-chromen-4-one Chemical compound FC1=C(Cl)C=C2OC(C)(C)CC(=O)C2=C1 NKCIUOVMTURVQK-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 2
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-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
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
HBQAXYGYFMVWAU-UHFFFAOYSA-N [7-chloro-4-[ethylsulfonyl(methyl)amino]-6-fluoro-2,2-dimethyl-3,4-dihydrochromen-3-yl] acetate Chemical compound ClC1=C(F)C=C2C(N(C)S(=O)(=O)CC)C(OC(C)=O)C(C)(C)OC2=C1 HBQAXYGYFMVWAU-UHFFFAOYSA-N 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
230000003213 activating effect Effects 0.000 description 2
239000003416 antiarrhythmic agent Substances 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
229910052786 argon Inorganic materials 0.000 description 2
125000004429 atom Chemical group 0.000 description 2
229910021538 borax Inorganic materials 0.000 description 2
230000003197 catalytic effect Effects 0.000 description 2
230000001413 cellular effect Effects 0.000 description 2
QZHPTGXQGDFGEN-UHFFFAOYSA-N chromene Chemical compound C1=CC=C2C=C[CH]OC2=C1 QZHPTGXQGDFGEN-UHFFFAOYSA-N 0.000 description 2
238000001816 cooling Methods 0.000 description 2
230000003111 delayed effect Effects 0.000 description 2
201000010099 disease Diseases 0.000 description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
238000007336 electrophilic substitution reaction Methods 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
235000001727 glucose Nutrition 0.000 description 2
239000008103 glucose Substances 0.000 description 2
125000000623 heterocyclic group Chemical group 0.000 description 2
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 2
150000004679 hydroxides Chemical class 0.000 description 2
238000011065 in-situ storage Methods 0.000 description 2
239000003112 inhibitor Substances 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
229910052744 lithium Inorganic materials 0.000 description 2
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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
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
- C07D311/68—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with nitrogen atoms directly attached in position 4
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- 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
- 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
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
- C07D311/70—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with two hydrocarbon radicals attached in position 2 and elements other than carbon and hydrogen in position 6

Landscapes

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

HR19706675.5A 1997-02-20 1998-02-19 Sulfonamido substituted chromanes, processes for the preparation thereof, their use as medicines or diagnostic agents, as well as pharmaceutical preparations containing them HRP980086A2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19706675A DE19706675A1 (de)	1997-02-20	1997-02-20	Sulfonamid-substituierte Chromane, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament

Publications (1)

Publication Number	Publication Date
HRP980086A2 true HRP980086A2 (en)	1998-10-31

Family

ID=7820907

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
HR19706675.5A HRP980086A2 (en)	1997-02-20	1998-02-19	Sulfonamido substituted chromanes, processes for the preparation thereof, their use as medicines or diagnostic agents, as well as pharmaceutical preparations containing them

Country Status (21)

Country	Link
US (1)	US6071953A (fr)
EP (1)	EP0860440A1 (fr)
JP (1)	JPH10231293A (fr)
KR (1)	KR19980071530A (fr)
CN (1)	CN1194982A (fr)
AR (1)	AR011153A1 (fr)
AU (1)	AU5539798A (fr)
BR (1)	BR9800708A (fr)
CA (1)	CA2229947A1 (fr)
CZ (1)	CZ48598A3 (fr)
DE (1)	DE19706675A1 (fr)
HR (1)	HRP980086A2 (fr)
HU (1)	HUP9800374A3 (fr)
IL (1)	IL123360A0 (fr)
NO (1)	NO980694L (fr)
NZ (1)	NZ329788A (fr)
PL (1)	PL324942A1 (fr)
SK (1)	SK20998A3 (fr)
TR (1)	TR199800253A2 (fr)
TW (1)	TW474929B (fr)
ZA (1)	ZA981376B (fr)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0895994A3 (fr) *	1997-08-05	1999-12-15	Hoechst Marion Roussel Deutschland GmbH	Dérivés de pyranopyridine substitués par un sulfonamide, procédé pour leur préparation, leur utilisation comme médicaments ou diagnostics et médicament les contenant
DE19742509A1 (de) *	1997-09-26	1999-04-01	Hoechst Marion Roussel De Gmbh	Sulfonamid-substituierte Chromane, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltende pharmazeutische Zubereitungen
DE19742508A1 (de)	1997-09-26	1999-04-01	Hoechst Marion Roussel De Gmbh	Sulfonamid-substituierte Chromane, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltende pharmazeutische Zubereitungen
DE19748469A1 (de) *	1997-11-03	1999-05-06	Hoechst Marion Roussel De Gmbh	Sulfonamid-substituierte Benzopyranderivate, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament sowie sie enthaltende pharmazeutische Zubereitungen
JP2002524457A (ja) *	1998-09-04	2002-08-06	ザプロクターアンドギャンブルカンパニー	抗不整脈薬として有用な置換ジヒドロベンゾピラン
DE19858253A1 (de) *	1998-12-17	2000-06-21	Aventis Pharma Gmbh	Verwendung von Inhibitoren des KQt1-Kanals zur Herstellung eines Medikaments zur Behandlung von Krankheiten, die durch Helminthen und Ektoparasiten hervorgerufen werden
AU2830800A (en) *	1999-03-25	2000-10-16	Nissan Chemical Industries Ltd.	Chroman derivatives
TW200403058A (en)	2002-04-19	2004-03-01	Bristol Myers Squibb Co	Heterocyclo inhibitors of potassium channel function
US7368582B2 (en)	2003-10-17	2008-05-06	Solvay Pharmaceuticals Gmbh	Amidomethyl-substituted 2-(4-sulfonylamino)-3-hydroxy-3,4-dihydro-2H-chromen-6-yl compounds, a process and intermediates for their production, and pharmaceutical compositions containing them
EP2595623B1 (fr)	2010-07-19	2018-02-28	The U.S.A. as represented by the Secretary, Department of Health and Human Services	Utilisation de delta-tocophérol pour le traitement de maladies lysosomales
CN104870432B (zh)	2012-11-16	2017-05-03	美国健康及人类服务部	作为溶酶体贮积症的修复剂的生育酚和生育醌衍生物

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3864850D1 (de) *	1987-02-13	1991-10-24	Centre Rech Metallurgique	Anlage zur kontinuierlichen herstellung einer sehr duennen metallfolie durch elektrolytische abscheidung.
FR2639349B1 (fr) *	1988-11-23	1991-02-22	Sanofi Sa	Nouveaux derives du chromane actifs sur le systeme nerveux central, leur procede de preparation et les compositions pharmaceutiques en contenant
US5104890A (en) *	1989-03-28	1992-04-14	Fujisawa Pharmaceutical Company, Ltd.	Benzopyran derivatives and processes for preparation thereof
US5382587A (en) *	1993-06-30	1995-01-17	Merck & Co., Inc.	Spirocycles
HRP970255B1 (en) *	1996-05-15	2003-10-31	Hoechst Ag	Sulfonamido substituted chromane derivatives, method for their preparation, their use as medicaments or diagnostic agents as well as medicaments containing them

1997
- 1997-02-20 DE DE19706675A patent/DE19706675A1/de not_active Withdrawn
1998
- 1998-02-16 EP EP98102621A patent/EP0860440A1/fr not_active Withdrawn
- 1998-02-18 AR ARP980100729A patent/AR011153A1/es unknown
- 1998-02-18 NZ NZ329788A patent/NZ329788A/xx unknown
- 1998-02-18 SK SK209-98A patent/SK20998A3/sk unknown
- 1998-02-18 CZ CZ98485A patent/CZ48598A3/cs unknown
- 1998-02-18 TR TR1998/00253A patent/TR199800253A2/xx unknown
- 1998-02-19 CN CN98108030A patent/CN1194982A/zh active Pending
- 1998-02-19 ZA ZA981376A patent/ZA981376B/xx unknown
- 1998-02-19 NO NO980694A patent/NO980694L/no not_active Application Discontinuation
- 1998-02-19 BR BR9800708A patent/BR9800708A/pt not_active IP Right Cessation
- 1998-02-19 JP JP10037116A patent/JPH10231293A/ja active Pending
- 1998-02-19 IL IL12336098A patent/IL123360A0/xx unknown
- 1998-02-19 US US09/026,513 patent/US6071953A/en not_active Expired - Fee Related
- 1998-02-19 AU AU55397/98A patent/AU5539798A/en not_active Abandoned
- 1998-02-19 HR HR19706675.5A patent/HRP980086A2/hr not_active Application Discontinuation
- 1998-02-19 CA CA002229947A patent/CA2229947A1/fr not_active Abandoned
- 1998-02-20 KR KR1019980005252A patent/KR19980071530A/ko not_active Withdrawn
- 1998-02-20 PL PL98324942A patent/PL324942A1/xx unknown
- 1998-02-20 HU HU9800374A patent/HUP9800374A3/hu unknown
- 1998-03-23 TW TW087102218A patent/TW474929B/zh active

Also Published As

Publication number	Publication date
TR199800253A2 (xx)	1998-09-21
HU9800374D0 (en)	1998-04-28
PL324942A1 (en)	1998-08-31
AR011153A1 (es)	2000-08-02
HUP9800374A2 (en)	2000-07-28
KR19980071530A (ko)	1998-10-26
CN1194982A (zh)	1998-10-07
DE19706675A1 (de)	1998-08-27
IL123360A0 (en)	1998-09-24
SK20998A3 (en)	1998-10-07
ZA981376B (en)	1998-08-20
HUP9800374A3 (en)	2001-02-28
NO980694D0 (no)	1998-02-19
CA2229947A1 (fr)	1998-08-20
NO980694L (no)	1998-08-21
US6071953A (en)	2000-06-06
EP0860440A1 (fr)	1998-08-26
CZ48598A3 (cs)	1998-09-16
NZ329788A (en)	1999-06-29
AU5539798A (en)	1998-08-27
BR9800708A (pt)	1999-07-20
JPH10231293A (ja)	1998-09-02
TW474929B (en)	2002-02-01

Legal Events

Date	Code	Title
1998-10-31	A1OB	Publication of a patent application
1999-04-29	AIPI	Request for the grant of a patent on the basis of a substantive examination of a patent application
2006-04-13	ODBI	Application refused

Publication	Publication Date	Title
AU711986B2 (en)	1999-10-28	Sulfonamide-substituted chromans, processes for their preparation, their use as a medicament or diagnostic, and medicament comprising them
HRP980086A2 (en)	1998-10-31	Sulfonamido substituted chromanes, processes for the preparation thereof, their use as medicines or diagnostic agents, as well as pharmaceutical preparations containing them
ES2234044T3 (es)	2005-06-16	Compuestos anulares de siete miembros, condensados sustituidos con sulfonamido con actividad bloqueante del canal de potasio.
AU740814B2 (en)	2001-11-15	Sulfonamide-substituted benzopyran derivatives, processes for their preparation, their use as a medicament, and pharmaceutical preparations comprising them
HRP980528A2 (en)	1999-06-30	Sulfonamid-substituted chromanes, process for their preparation, their use as medicaments, and pharmaceutical preparations containing them
CN101265250A (zh)	2008-09-17	取代黄酮类化合物、其制备方法、其应用及其药物组合物
AU742918B2 (en)	2002-01-17	Sulfonamide-substituted compounds, processes for their preparation, their use as a medicament or diagnostic, and medicament comprising them
NO312546B1 (no)	2002-05-27	Sulfonamidsubstituerte kondenserte 5-ringforbindelser, deres anvendelse til fremstilling av medikament samt farmasöytiskepreparater inneholdende forbindelsene
US6191164B1 (en)	2001-02-20	Sulfonamide-substituted chromans, processes for their preparation, their use as a medicament or diagnostic, and medicament comprising them
AU727216B2 (en)	2000-12-07	Sulfonamide-substituted compounds, processes for their preparation, their use as a medicament or diagnostic, and medicament comprising them
AU725699B2 (en)	2000-10-19	Sulfonamide-substituted compounds, processes for their preparation, their use as a medicament or diagnostic, and pharmaceutical preparations comprising them
US6333349B1 (en)	2001-12-25	Sulfonamide-substituted fused 7-membered ring compounds, their use as a medicament, and pharmaceutical preparations comprising them
MXPA97010126A (en)	1998-11-09	Substituted compounds with sulfonamide, procedure for preparation, employment as a medicine or diagnostic agent, as well as pharmaceutical preparations that contain them
MXPA97003534A (en)	1998-07-03	Chromants replaced with sulfonamide, procedure for preparation, employment as a medicinal or diagnostic agent, and as a medication that conti
MXPA98001121A (en)	1998-11-12	Compositions replaced with sulfonamide, procedure for its preparation, its employment as a diagnostic medicine or agent as well as a medicine that conti
MXPA98006267A (en)	1999-04-27	Substituted compounds with sulfonamide, procedure for its preparation, its use as a diagnostic medicine or agent as well as a medicine that contains them