NO312159B1 - Nye trisykliske forbindelser og medikamentsammensetninger inneholdende slike - Google Patents

Nye trisykliske forbindelser og medikamentsammensetninger inneholdende slike Download PDF

Info

Publication number: NO312159B1
Authority: NO; Norway
Prior art keywords: yloxy; hydrogen atom; atom; ethylamino; carbazol
Prior art date: 1996-01-10

Application number

NO19983197A

Other languages

English (en)

Norwegian (no)

Other versions

NO983197L (no

Inventor

Shiro Miyoshi

Kohei Ogawa

Original Assignee

Asahi Chemical Ind

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.)

1996-01-10

Filing date

1998-07-10

Publication date

2002-04-02

1998-07-10 Application filed by Asahi Chemical Ind filed Critical Asahi Chemical Ind

1998-09-10 Publication of NO983197L publication Critical patent/NO983197L/no

2002-04-02 Publication of NO312159B1 publication Critical patent/NO312159B1/no

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 453
229940079593 drug Drugs 0.000 title claims abstract description 20
239000003814 drug Substances 0.000 title claims abstract description 20
239000000203 mixture Substances 0.000 title claims description 186
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 262
238000000034 method Methods 0.000 claims abstract description 138
-1 hydroxy, benzyloxy, amino Chemical group 0.000 claims abstract description 94
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 91
125000000217 alkyl group Chemical group 0.000 claims abstract description 65
150000003839 salts Chemical class 0.000 claims abstract description 50
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 47
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims abstract description 45
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 43
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 41
229910052717 sulfur Inorganic materials 0.000 claims abstract description 36
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims abstract description 33
238000011282 treatment Methods 0.000 claims abstract description 32
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 28
208000008589 Obesity Diseases 0.000 claims abstract description 9
235000020824 obesity Nutrition 0.000 claims abstract description 9
206010012601 diabetes mellitus Diseases 0.000 claims abstract description 7
201000005577 familial hyperlipidemia Diseases 0.000 claims abstract description 7
230000008569 process Effects 0.000 claims abstract description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 240
125000006239 protecting group Chemical group 0.000 claims description 88
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 81
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 51
125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 49
125000003277 amino group Chemical group 0.000 claims description 44
229910052799 carbon Inorganic materials 0.000 claims description 34
125000004432 carbon atom Chemical group C* 0.000 claims description 34
125000004433 nitrogen atom Chemical group N* 0.000 claims description 34
125000004430 oxygen atom Chemical group O* 0.000 claims description 33
125000004434 sulfur atom Chemical group 0.000 claims description 33
125000005843 halogen group Chemical group 0.000 claims description 28
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 26
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 24
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 23
230000009467 reduction Effects 0.000 claims description 18
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 17
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 16
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 15
229910052731 fluorine Inorganic materials 0.000 claims description 13
238000004519 manufacturing process Methods 0.000 claims description 12
HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims description 12
229910052801 chlorine Inorganic materials 0.000 claims description 11
125000001309 chloro group Chemical group Cl* 0.000 claims description 11
125000001153 fluoro group Chemical group F* 0.000 claims description 11
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 9
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 8
229910052740 iodine Chemical group 0.000 claims description 8
KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 7
230000003449 preventive effect Effects 0.000 claims description 6
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
230000001225 therapeutic effect Effects 0.000 claims description 5
101100294106 Caenorhabditis elegans nhr-3 gene Proteins 0.000 claims description 4
NVKHCBMVFOJXJB-UHFFFAOYSA-N n-[5-[2-[2-[(7-amino-9h-fluoren-2-yl)oxy]ethylamino]-1-hydroxyethyl]-2-hydroxyphenyl]methanesulfonamide Chemical compound C1=C(O)C(NS(=O)(=O)C)=CC(C(O)CNCCOC=2C=C3C(C4=CC=C(N)C=C4C3)=CC=2)=C1 NVKHCBMVFOJXJB-UHFFFAOYSA-N 0.000 claims description 4
OPYNTUQGVOERTC-UHFFFAOYSA-N 4-[2-[2-(9h-carbazol-2-yloxy)ethylamino]-1-hydroxyethyl]phenol Chemical compound C=1C=C(C2=CC=CC=C2N2)C2=CC=1OCCNCC(O)C1=CC=C(O)C=C1 OPYNTUQGVOERTC-UHFFFAOYSA-N 0.000 claims description 3
PYAPJIBHIHRYAJ-UHFFFAOYSA-N n-[2-amino-5-[2-[2-(9h-carbazol-2-yloxy)ethylamino]-1-methoxyethyl]phenyl]methanesulfonamide Chemical compound C=1C=C(C2=CC=CC=C2N2)C2=CC=1OCCNCC(OC)C1=CC=C(N)C(NS(C)(=O)=O)=C1 PYAPJIBHIHRYAJ-UHFFFAOYSA-N 0.000 claims description 3
GOEGMKAAILGFAS-UHFFFAOYSA-N n-[5-[2-(2-dibenzothiophen-3-yloxyethylamino)-1-methoxyethyl]-2-hydroxyphenyl]methanesulfonamide Chemical compound C=1C=C(C2=CC=CC=C2S2)C2=CC=1OCCNCC(OC)C1=CC=C(O)C(NS(C)(=O)=O)=C1 GOEGMKAAILGFAS-UHFFFAOYSA-N 0.000 claims description 3
MNQQHDGNJUBFGR-UHFFFAOYSA-N n-[5-[2-[2-(9h-carbazol-2-yloxy)ethylamino]-1-methoxyethyl]-2-hydroxyphenyl]methanesulfonamide Chemical compound C=1C=C(C2=CC=CC=C2N2)C2=CC=1OCCNCC(OC)C1=CC=C(O)C(NS(C)(=O)=O)=C1 MNQQHDGNJUBFGR-UHFFFAOYSA-N 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
230000001681 protective effect Effects 0.000 claims description 3
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
IXJKCHZJMPZZKF-UHFFFAOYSA-N 1-(3-aminophenyl)-2-[2-(9h-carbazol-2-yloxy)ethylamino]ethanol Chemical compound NC1=CC=CC(C(O)CNCCOC=2C=C3C(C4=CC=CC=C4N3)=CC=2)=C1 IXJKCHZJMPZZKF-UHFFFAOYSA-N 0.000 claims description 2
IJHWHKZMLDZXPN-UHFFFAOYSA-N 2-[2-(9h-carbazol-2-yloxy)ethylamino]-1-(2-fluorophenyl)ethanol Chemical compound C=1C=C(C2=CC=CC=C2N2)C2=CC=1OCCNCC(O)C1=CC=CC=C1F IJHWHKZMLDZXPN-UHFFFAOYSA-N 0.000 claims description 2
MLUIHKSMGSSIAZ-UHFFFAOYSA-N 2-[2-(9h-carbazol-2-yloxy)ethylamino]-1-(3-nitrophenyl)ethanol Chemical compound C=1C=C(C2=CC=CC=C2N2)C2=CC=1OCCNCC(O)C1=CC=CC([N+]([O-])=O)=C1 MLUIHKSMGSSIAZ-UHFFFAOYSA-N 0.000 claims description 2
ZIKXIHALQFRIQE-UHFFFAOYSA-N 2-[2-(9h-carbazol-2-yloxy)ethylamino]-1-[3-(methylamino)-4-phenylmethoxyphenyl]ethanol Chemical compound CNC1=CC(C(O)CNCCOC=2C=C3C(C4=CC=CC=C4N3)=CC=2)=CC=C1OCC1=CC=CC=C1 ZIKXIHALQFRIQE-UHFFFAOYSA-N 0.000 claims description 2
NTYZRYQWVHOSFC-UHFFFAOYSA-N 2-[2-[2-(9h-carbazol-2-yloxy)ethylamino]-1-hydroxyethyl]phenol Chemical compound C=1C=C(C2=CC=CC=C2N2)C2=CC=1OCCNCC(O)C1=CC=CC=C1O NTYZRYQWVHOSFC-UHFFFAOYSA-N 0.000 claims description 2
DUPOGPRETAXXJT-DEOSSOPVSA-N 2-[2-[[(2r)-2-[3-(dimethylsulfamoylamino)-4-hydroxyphenyl]-2-hydroxyethyl]amino]ethoxy]-9h-carbazole Chemical compound C1=C(O)C(NS(=O)(=O)N(C)C)=CC([C@@H](O)CNCCOC=2C=C3C(C4=CC=CC=C4N3)=CC=2)=C1 DUPOGPRETAXXJT-DEOSSOPVSA-N 0.000 claims description 2
DUPOGPRETAXXJT-XMMPIXPASA-N 2-[2-[[(2s)-2-[3-(dimethylsulfamoylamino)-4-hydroxyphenyl]-2-hydroxyethyl]amino]ethoxy]-9h-carbazole Chemical compound C1=C(O)C(NS(=O)(=O)N(C)C)=CC([C@H](O)CNCCOC=2C=C3C(C4=CC=CC=C4N3)=CC=2)=C1 DUPOGPRETAXXJT-XMMPIXPASA-N 0.000 claims description 2
OVUXYPOLJTVGNL-UHFFFAOYSA-N 2-[2-[[2-[3-(diethylsulfamoylamino)-4-hydroxyphenyl]-2-hydroxyethyl]amino]ethoxy]-9h-carbazole Chemical compound C1=C(O)C(NS(=O)(=O)N(CC)CC)=CC(C(O)CNCCOC=2C=C3C(C4=CC=CC=C4N3)=CC=2)=C1 OVUXYPOLJTVGNL-UHFFFAOYSA-N 0.000 claims description 2
OQSKLCAAJQXXNR-UHFFFAOYSA-N 2-[2-[[2-[3-(dimethylsulfamoylamino)-4-fluorophenyl]-2-hydroxyethyl]amino]ethoxy]-9h-carbazole Chemical compound C1=C(F)C(NS(=O)(=O)N(C)C)=CC(C(O)CNCCOC=2C=C3C(C4=CC=CC=C4N3)=CC=2)=C1 OQSKLCAAJQXXNR-UHFFFAOYSA-N 0.000 claims description 2
FIEWDKKCJXNSFS-UHFFFAOYSA-N 2-amino-4-[2-[2-(9h-carbazol-2-yloxy)ethylamino]-1-hydroxyethyl]phenol Chemical compound C1=C(O)C(N)=CC(C(O)CNCCOC=2C=C3C(C4=CC=CC=C4N3)=CC=2)=C1 FIEWDKKCJXNSFS-UHFFFAOYSA-N 0.000 claims description 2
NVMARZSMVAILSO-UHFFFAOYSA-N 3-[2-[2-(9h-carbazol-2-yloxy)ethylamino]-1-hydroxyethyl]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(C(O)CNCCOC=2C=C3C(C4=CC=CC=C4N3)=CC=2)=C1 NVMARZSMVAILSO-UHFFFAOYSA-N 0.000 claims description 2
JPXPXAOXDULILV-QFIPXVFZSA-N 3-[2-[[(2r)-2-[3-(dimethylsulfamoylamino)-4-hydroxyphenyl]-2-hydroxyethyl]amino]ethoxy]dibenzofuran Chemical compound C1=C(O)C(NS(=O)(=O)N(C)C)=CC([C@@H](O)CNCCOC=2C=C3C(C4=CC=CC=C4O3)=CC=2)=C1 JPXPXAOXDULILV-QFIPXVFZSA-N 0.000 claims description 2
NWRNHCJNFDISLJ-UHFFFAOYSA-N 4-[2-[2-(9h-carbazol-2-yloxy)ethylamino]-1-hydroxyethyl]-2-(hydroxymethyl)phenol Chemical compound C1=C(O)C(CO)=CC(C(O)CNCCOC=2C=C3C(C4=CC=CC=C4N3)=CC=2)=C1 NWRNHCJNFDISLJ-UHFFFAOYSA-N 0.000 claims description 2
IKCXSIRETPFEEO-UHFFFAOYSA-N 4-[2-[2-(9h-carbazol-2-yloxy)ethylamino]-1-hydroxyethyl]-2-(methylamino)phenol Chemical compound C1=C(O)C(NC)=CC(C(O)CNCCOC=2C=C3C(C4=CC=CC=C4N3)=CC=2)=C1 IKCXSIRETPFEEO-UHFFFAOYSA-N 0.000 claims description 2
KESXIKRVBNXWEA-UHFFFAOYSA-N 4-[2-[2-(9h-carbazol-2-yloxy)ethylamino]-1-hydroxyethyl]-2-nitrophenol Chemical compound C=1C=C(C2=CC=CC=C2N2)C2=CC=1OCCNCC(O)C1=CC=C(O)C([N+]([O-])=O)=C1 KESXIKRVBNXWEA-UHFFFAOYSA-N 0.000 claims description 2
HBRDJLQNJOKSQG-UHFFFAOYSA-N [5-[2-[2-(9h-carbazol-2-yloxy)ethylamino]-1-hydroxyethyl]-2-hydroxyphenyl]urea Chemical compound C1=C(O)C(NC(=O)N)=CC(C(O)CNCCOC=2C=C3C(C4=CC=CC=C4N3)=CC=2)=C1 HBRDJLQNJOKSQG-UHFFFAOYSA-N 0.000 claims description 2
PMQYHUDCVLRMBX-UHFFFAOYSA-N [5-[2-[2-(9h-carbazol-2-yloxy)ethylamino]-1-hydroxyethyl]-2-phenylmethoxyphenyl]urea Chemical compound NC(=O)NC1=CC(C(O)CNCCOC=2C=C3C(C4=CC=CC=C4N3)=CC=2)=CC=C1OCC1=CC=CC=C1 PMQYHUDCVLRMBX-UHFFFAOYSA-N 0.000 claims description 2
DWKVGEYYBUPTFU-UHFFFAOYSA-N n-[2-amino-5-[2-[2-(9h-carbazol-2-yloxy)ethylamino]-1-hydroxyethyl]phenyl]methanesulfonamide Chemical compound C1=C(N)C(NS(=O)(=O)C)=CC(C(O)CNCCOC=2C=C3C(C4=CC=CC=C4N3)=CC=2)=C1 DWKVGEYYBUPTFU-UHFFFAOYSA-N 0.000 claims description 2
HVSCONOCEJUEGP-UHFFFAOYSA-N n-[2-bromo-5-[2-[2-(9h-carbazol-2-yloxy)ethylamino]-1-hydroxyethyl]phenyl]methanesulfonamide Chemical compound C1=C(Br)C(NS(=O)(=O)C)=CC(C(O)CNCCOC=2C=C3C(C4=CC=CC=C4N3)=CC=2)=C1 HVSCONOCEJUEGP-UHFFFAOYSA-N 0.000 claims description 2
QQQJTXUWELTWSR-UHFFFAOYSA-N n-[2-chloro-5-[2-(2-dibenzofuran-3-yloxyethylamino)-1-hydroxyethyl]phenyl]methanesulfonamide Chemical compound C1=C(Cl)C(NS(=O)(=O)C)=CC(C(O)CNCCOC=2C=C3C(C4=CC=CC=C4O3)=CC=2)=C1 QQQJTXUWELTWSR-UHFFFAOYSA-N 0.000 claims description 2
UWXISSDMCHBBEA-UHFFFAOYSA-N n-[2-chloro-5-[2-(2-dibenzothiophen-3-yloxyethylamino)-1-hydroxyethyl]phenyl]methanesulfonamide Chemical compound C1=C(Cl)C(NS(=O)(=O)C)=CC(C(O)CNCCOC=2C=C3C(C4=CC=CC=C4S3)=CC=2)=C1 UWXISSDMCHBBEA-UHFFFAOYSA-N 0.000 claims description 2
VBXJNUVUFQZVBR-UHFFFAOYSA-N n-[2-hydroxy-5-[1-hydroxy-2-[2-[(3-hydroxy-9h-carbazol-2-yl)oxy]ethylamino]ethyl]phenyl]methanesulfonamide Chemical compound C1=C(O)C(NS(=O)(=O)C)=CC(C(O)CNCCOC=2C(=CC=3C4=CC=CC=C4NC=3C=2)O)=C1 VBXJNUVUFQZVBR-UHFFFAOYSA-N 0.000 claims description 2
MEJURHFWXLRFTN-UHFFFAOYSA-N n-[2-hydroxy-5-[1-hydroxy-2-[2-[(6-hydroxy-9h-carbazol-2-yl)oxy]ethylamino]ethyl]phenyl]methanesulfonamide Chemical compound C1=C(O)C(NS(=O)(=O)C)=CC(C(O)CNCCOC=2C=C3C(C4=CC(O)=CC=C4N3)=CC=2)=C1 MEJURHFWXLRFTN-UHFFFAOYSA-N 0.000 claims description 2
DTOHSKBTGDUVJL-QHCPKHFHSA-N n-[3-[(1r)-2-[2-(9h-carbazol-2-yloxy)ethylamino]-1-hydroxyethyl]phenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=CC([C@@H](O)CNCCOC=2C=C3C(C4=CC=CC=C4N3)=CC=2)=C1 DTOHSKBTGDUVJL-QHCPKHFHSA-N 0.000 claims description 2
DTOHSKBTGDUVJL-HSZRJFAPSA-N n-[3-[(1s)-2-[2-(9h-carbazol-2-yloxy)ethylamino]-1-hydroxyethyl]phenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=CC([C@H](O)CNCCOC=2C=C3C(C4=CC=CC=C4N3)=CC=2)=C1 DTOHSKBTGDUVJL-HSZRJFAPSA-N 0.000 claims description 2
JOZSWZXNFNAMQE-UHFFFAOYSA-N n-[3-[2-(2-dibenzofuran-3-yloxyethylamino)-1-hydroxyethyl]phenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=CC(C(O)CNCCOC=2C=C3C(C4=CC=CC=C4O3)=CC=2)=C1 JOZSWZXNFNAMQE-UHFFFAOYSA-N 0.000 claims description 2
GDAWGPRURXSDCE-UHFFFAOYSA-N n-[3-[2-(2-dibenzothiophen-3-yloxyethylamino)-1-hydroxyethyl]phenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=CC(C(O)CNCCOC=2C=C3C(C4=CC=CC=C4S3)=CC=2)=C1 GDAWGPRURXSDCE-UHFFFAOYSA-N 0.000 claims description 2
BRLFCGZMBLUHQH-UHFFFAOYSA-N n-[3-[2-[2-(9h-carbazol-2-yloxy)ethylamino]-1-hydroxyethyl]-2-hydroxyphenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=CC(C(O)CNCCOC=2C=C3C(C4=CC=CC=C4N3)=CC=2)=C1O BRLFCGZMBLUHQH-UHFFFAOYSA-N 0.000 claims description 2
OEJMSTWQZJOZET-UHFFFAOYSA-N n-[3-[2-[2-(9h-carbazol-2-yloxy)ethylamino]-1-hydroxyethyl]-4-hydroxyphenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=C(O)C(C(O)CNCCOC=2C=C3C(C4=CC=CC=C4N3)=CC=2)=C1 OEJMSTWQZJOZET-UHFFFAOYSA-N 0.000 claims description 2
QMHCLYPZXZLNIY-UHFFFAOYSA-N n-[3-[2-[2-(9h-carbazol-2-yloxy)ethylamino]-1-hydroxyethyl]-5-hydroxyphenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC(O)=CC(C(O)CNCCOC=2C=C3C(C4=CC=CC=C4N3)=CC=2)=C1 QMHCLYPZXZLNIY-UHFFFAOYSA-N 0.000 claims description 2
BZMKQOOKVCZRLZ-UHFFFAOYSA-N n-[3-[2-[2-(9h-carbazol-2-yloxy)ethylamino]-1-hydroxyethyl]phenyl]formamide Chemical compound C=1C=C(C2=CC=CC=C2N2)C2=CC=1OCCNCC(O)C1=CC=CC(NC=O)=C1 BZMKQOOKVCZRLZ-UHFFFAOYSA-N 0.000 claims description 2
COCLADHXYWRUIH-UHFFFAOYSA-N n-[3-[2-[2-[(7-amino-9h-fluoren-2-yl)oxy]ethylamino]-1-hydroxyethyl]phenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=CC(C(O)CNCCOC=2C=C3C(C4=CC=C(N)C=C4C3)=CC=2)=C1 COCLADHXYWRUIH-UHFFFAOYSA-N 0.000 claims description 2
RHRGYGCGWSZVCU-NRFANRHFSA-N n-[5-[(1r)-2-(2-dibenzofuran-3-yloxyethylamino)-1-hydroxyethyl]-2-hydroxyphenyl]methanesulfonamide Chemical compound C1=C(O)C(NS(=O)(=O)C)=CC([C@@H](O)CNCCOC=2C=C3C(C4=CC=CC=C4O3)=CC=2)=C1 RHRGYGCGWSZVCU-NRFANRHFSA-N 0.000 claims description 2
FXALXNZMNXWULQ-DEOSSOPVSA-N n-[5-[(1r)-2-[2-(9h-carbazol-2-yloxy)ethylamino]-1-hydroxyethyl]-2-(hydroxymethyl)phenyl]methanesulfonamide Chemical compound C1=C(CO)C(NS(=O)(=O)C)=CC([C@@H](O)CNCCOC=2C=C3C(C4=CC=CC=C4N3)=CC=2)=C1 FXALXNZMNXWULQ-DEOSSOPVSA-N 0.000 claims description 2
GJPWBSFNWKJIIC-QHCPKHFHSA-N n-[5-[(1r)-2-[2-(9h-carbazol-2-yloxy)ethylamino]-1-hydroxyethyl]-2-chlorophenyl]methanesulfonamide Chemical compound C1=C(Cl)C(NS(=O)(=O)C)=CC([C@@H](O)CNCCOC=2C=C3C(C4=CC=CC=C4N3)=CC=2)=C1 GJPWBSFNWKJIIC-QHCPKHFHSA-N 0.000 claims description 2
JANCFZMNYVRUDL-QHCPKHFHSA-N n-[5-[(1r)-2-[2-(9h-carbazol-2-yloxy)ethylamino]-1-hydroxyethyl]-2-fluorophenyl]methanesulfonamide Chemical compound C1=C(F)C(NS(=O)(=O)C)=CC([C@@H](O)CNCCOC=2C=C3C(C4=CC=CC=C4N3)=CC=2)=C1 JANCFZMNYVRUDL-QHCPKHFHSA-N 0.000 claims description 2
MWCDQOSTJHWLFI-QHCPKHFHSA-N n-[5-[(1r)-2-[2-(9h-carbazol-2-yloxy)ethylamino]-1-hydroxyethyl]-2-hydroxyphenyl]methanesulfonamide Chemical compound C1=C(O)C(NS(=O)(=O)C)=CC([C@@H](O)CNCCOC=2C=C3C(C4=CC=CC=C4N3)=CC=2)=C1 MWCDQOSTJHWLFI-QHCPKHFHSA-N 0.000 claims description 2
RHRGYGCGWSZVCU-OAQYLSRUSA-N n-[5-[(1s)-2-(2-dibenzofuran-3-yloxyethylamino)-1-hydroxyethyl]-2-hydroxyphenyl]methanesulfonamide Chemical compound C1=C(O)C(NS(=O)(=O)C)=CC([C@H](O)CNCCOC=2C=C3C(C4=CC=CC=C4O3)=CC=2)=C1 RHRGYGCGWSZVCU-OAQYLSRUSA-N 0.000 claims description 2
GJPWBSFNWKJIIC-HSZRJFAPSA-N n-[5-[(1s)-2-[2-(9h-carbazol-2-yloxy)ethylamino]-1-hydroxyethyl]-2-chlorophenyl]methanesulfonamide Chemical compound C1=C(Cl)C(NS(=O)(=O)C)=CC([C@H](O)CNCCOC=2C=C3C(C4=CC=CC=C4N3)=CC=2)=C1 GJPWBSFNWKJIIC-HSZRJFAPSA-N 0.000 claims description 2
MWCDQOSTJHWLFI-HSZRJFAPSA-N n-[5-[(1s)-2-[2-(9h-carbazol-2-yloxy)ethylamino]-1-hydroxyethyl]-2-hydroxyphenyl]methanesulfonamide Chemical compound C1=C(O)C(NS(=O)(=O)C)=CC([C@H](O)CNCCOC=2C=C3C(C4=CC=CC=C4N3)=CC=2)=C1 MWCDQOSTJHWLFI-HSZRJFAPSA-N 0.000 claims description 2
NJSOTNOENOAKJC-UHFFFAOYSA-N n-[5-[2-(2-dibenzofuran-3-yloxyethylamino)-1-hydroxyethyl]-2-fluorophenyl]methanesulfonamide Chemical compound C1=C(F)C(NS(=O)(=O)C)=CC(C(O)CNCCOC=2C=C3C(C4=CC=CC=C4O3)=CC=2)=C1 NJSOTNOENOAKJC-UHFFFAOYSA-N 0.000 claims description 2
RHRGYGCGWSZVCU-UHFFFAOYSA-N n-[5-[2-(2-dibenzofuran-3-yloxyethylamino)-1-hydroxyethyl]-2-hydroxyphenyl]methanesulfonamide Chemical compound C1=C(O)C(NS(=O)(=O)C)=CC(C(O)CNCCOC=2C=C3C(C4=CC=CC=C4O3)=CC=2)=C1 RHRGYGCGWSZVCU-UHFFFAOYSA-N 0.000 claims description 2
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NXFAZCYQQQPJAV-UHFFFAOYSA-N n-[5-[2-(2-dibenzofuran-3-yloxyethylamino)-1-hydroxyethyl]-2-hydroxyphenyl]methanesulfonamide;hydrochloride Chemical compound Cl.C1=C(O)C(NS(=O)(=O)C)=CC(C(O)CNCCOC=2C=C3C(C4=CC=CC=C4O3)=CC=2)=C1 NXFAZCYQQQPJAV-UHFFFAOYSA-N 0.000 description 1
ZWYBNTFWOBJJIB-UHFFFAOYSA-N n-[5-[2-(2-dibenzofuran-3-yloxyethylamino)-1-triethylsilyloxyethyl]-2-fluorophenyl]methanesulfonamide Chemical compound C=1C=C(C2=CC=CC=C2O2)C2=CC=1OCCNCC(O[Si](CC)(CC)CC)C1=CC=C(F)C(NS(C)(=O)=O)=C1 ZWYBNTFWOBJJIB-UHFFFAOYSA-N 0.000 description 1
CJSKPXLAZVGJRN-UHFFFAOYSA-N n-[5-[2-(2-dibenzothiophen-3-yloxyethylamino)-1-hydroxyethyl]-2-hydroxyphenyl]methanesulfonamide;hydrochloride Chemical compound Cl.C1=C(O)C(NS(=O)(=O)C)=CC(C(O)CNCCOC=2C=C3C(C4=CC=CC=C4S3)=CC=2)=C1 CJSKPXLAZVGJRN-UHFFFAOYSA-N 0.000 description 1
QRLLTSUNAYUSHM-UHFFFAOYSA-N n-[5-[2-[2-(9h-carbazol-2-yloxy)ethylamino]-1-hydroxyethyl]-2-hydroxyphenyl]formamide;hydrochloride Chemical compound Cl.C=1C=C(C2=CC=CC=C2N2)C2=CC=1OCCNCC(O)C1=CC=C(O)C(NC=O)=C1 QRLLTSUNAYUSHM-UHFFFAOYSA-N 0.000 description 1
VWCXVIIBSKSMLL-UHFFFAOYSA-N n-[5-[2-[2-(9h-carbazol-2-yloxy)ethylamino]-1-hydroxyethyl]-2-hydroxyphenyl]methanesulfonamide;hydrochloride Chemical compound Cl.C1=C(O)C(NS(=O)(=O)C)=CC(C(O)CNCCOC=2C=C3C(C4=CC=CC=C4N3)=CC=2)=C1 VWCXVIIBSKSMLL-UHFFFAOYSA-N 0.000 description 1
FJLFDWVKRSWJBZ-UHFFFAOYSA-N n-[5-[2-[2-(9h-carbazol-2-yloxy)ethylamino]-1-hydroxyethyl]-2-hydroxyphenyl]propane-2-sulfonamide;hydrochloride Chemical compound Cl.C1=C(O)C(NS(=O)(=O)C(C)C)=CC(C(O)CNCCOC=2C=C3C(C4=CC=CC=C4N3)=CC=2)=C1 FJLFDWVKRSWJBZ-UHFFFAOYSA-N 0.000 description 1
JKKJYROAFNBDBF-UHFFFAOYSA-N n-[5-[2-[2-(9h-carbazol-2-yloxy)ethylamino]-1-hydroxyethyl]-2-phenylmethoxyphenyl]formamide;hydrochloride Chemical compound Cl.C=1C=C(C2=CC=CC=C2N2)C2=CC=1OCCNCC(O)C(C=C1NC=O)=CC=C1OCC1=CC=CC=C1 JKKJYROAFNBDBF-UHFFFAOYSA-N 0.000 description 1
SSXOIJOXJHFFJA-UHFFFAOYSA-N n-[5-[2-[2-(9h-carbazol-2-yloxy)ethylamino]-1-hydroxyethyl]-2-phenylmethoxyphenyl]propane-2-sulfonamide;hydrochloride Chemical compound Cl.CC(C)S(=O)(=O)NC1=CC(C(O)CNCCOC=2C=C3C(C4=CC=CC=C4N3)=CC=2)=CC=C1OCC1=CC=CC=C1 SSXOIJOXJHFFJA-UHFFFAOYSA-N 0.000 description 1
UGCZOQLQIZIASR-UHFFFAOYSA-N n-[7-[2-[[2-[3-(dimethylsulfamoylamino)-4-hydroxyphenyl]-2-hydroxyethyl]amino]ethoxy]-9h-fluoren-2-yl]acetamide Chemical compound C1=C(O)C(NS(=O)(=O)N(C)C)=CC(C(O)CNCCOC=2C=C3C(C4=CC=C(NC(C)=O)C=C4C3)=CC=2)=C1 UGCZOQLQIZIASR-UHFFFAOYSA-N 0.000 description 1
VPJLBXYECOGMLI-UHFFFAOYSA-N n-benzyl-n-[3-(2-bromoacetyl)-4-methoxyphenyl]methanesulfonamide Chemical compound C1=C(C(=O)CBr)C(OC)=CC=C1N(S(C)(=O)=O)CC1=CC=CC=C1 VPJLBXYECOGMLI-UHFFFAOYSA-N 0.000 description 1
NKKWPDLMOVKRII-UHFFFAOYSA-N n-benzyl-n-[3-[2-[2-(9h-carbazol-2-yloxy)ethylamino]-1-hydroxyethyl]-4-hydroxyphenyl]methanesulfonamide;hydrochloride Chemical compound Cl.C=1C=C(O)C(C(O)CNCCOC=2C=C3C(C4=CC=CC=C4N3)=CC=2)=CC=1N(S(=O)(=O)C)CC1=CC=CC=C1 NKKWPDLMOVKRII-UHFFFAOYSA-N 0.000 description 1
NUXBUDNPQFMZEC-UHFFFAOYSA-N n-benzyl-n-[3-[2-[2-(9h-carbazol-2-yloxy)ethylamino]-1-hydroxyethyl]-4-methoxyphenyl]methanesulfonamide Chemical compound C1=C(C(O)CNCCOC=2C=C3C(C4=CC=CC=C4N3)=CC=2)C(OC)=CC=C1N(S(C)(=O)=O)CC1=CC=CC=C1 NUXBUDNPQFMZEC-UHFFFAOYSA-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
229910052759 nickel Inorganic materials 0.000 description 1
FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 description 1
230000000802 nitrating effect Effects 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
125000006501 nitrophenyl group Chemical group 0.000 description 1
238000010534 nucleophilic substitution reaction Methods 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
125000004043 oxo group Chemical group O=* 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
238000005191 phase separation Methods 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
OAHKWDDSKCRNFE-UHFFFAOYSA-N phenylmethanesulfonyl chloride Chemical compound ClS(=O)(=O)CC1=CC=CC=C1 OAHKWDDSKCRNFE-UHFFFAOYSA-N 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
239000000843 powder Substances 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
150000003138 primary alcohols Chemical class 0.000 description 1
DRINJBFRTLBHNF-UHFFFAOYSA-N propane-2-sulfonyl chloride Chemical compound CC(C)S(Cl)(=O)=O DRINJBFRTLBHNF-UHFFFAOYSA-N 0.000 description 1
239000003223 protective agent Substances 0.000 description 1
238000010791 quenching Methods 0.000 description 1
239000002516 radical scavenger Substances 0.000 description 1
238000011160 research Methods 0.000 description 1
230000004044 response Effects 0.000 description 1
229930195734 saturated hydrocarbon Natural products 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
238000000926 separation method Methods 0.000 description 1
DHNUAKOQUGJUGA-UHFFFAOYSA-N silicon;sulfane Chemical compound [Si].S DHNUAKOQUGJUGA-UHFFFAOYSA-N 0.000 description 1
210000002460 smooth muscle Anatomy 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
229940079827 sodium hydrogen sulfite Drugs 0.000 description 1
239000004289 sodium hydrogen sulphite Substances 0.000 description 1
UNHKSXOTUHOTAB-UHFFFAOYSA-N sodium;sulfane Chemical compound [Na].S UNHKSXOTUHOTAB-UHFFFAOYSA-N 0.000 description 1
239000001119 stannous chloride Substances 0.000 description 1
235000011150 stannous chloride Nutrition 0.000 description 1
239000007940 sugar coated tablet Substances 0.000 description 1
229940124530 sulfonamide Drugs 0.000 description 1
150000003456 sulfonamides Chemical class 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical group ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000003826 tablet Substances 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
KCKTYESZOMPSPM-UHFFFAOYSA-N tert-butyl n-[3-(9h-carbazol-2-yloxy)propyl]carbamate Chemical compound C1=CC=C2C3=CC=C(OCCCNC(=O)OC(C)(C)C)C=C3NC2=C1 KCKTYESZOMPSPM-UHFFFAOYSA-N 0.000 description 1
ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
238000012360 testing method Methods 0.000 description 1
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
238000005979 thermal decomposition reaction Methods 0.000 description 1
AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
238000007070 tosylation reaction Methods 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
UDZXJXBCEHWLIX-NRFANRHFSA-N triethyl-[(1r)-2-iodo-1-(3-nitro-4-phenylmethoxyphenyl)ethoxy]silane Chemical compound [O-][N+](=O)C1=CC([C@H](CI)O[Si](CC)(CC)CC)=CC=C1OCC1=CC=CC=C1 UDZXJXBCEHWLIX-NRFANRHFSA-N 0.000 description 1
JGPGTMGEXWTDDA-AWEZNQCLSA-N triethyl-[(1r)-2-iodo-1-(3-nitrophenyl)ethoxy]silane Chemical compound CC[Si](CC)(CC)O[C@@H](CI)C1=CC=CC([N+]([O-])=O)=C1 JGPGTMGEXWTDDA-AWEZNQCLSA-N 0.000 description 1
230000007306 turnover Effects 0.000 description 1
231100000397 ulcer Toxicity 0.000 description 1
238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
230000000304 vasodilatating effect Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C307/00—Amides of sulfuric acids, i.e. compounds having singly-bound oxygen atoms of sulfate groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C307/04—Diamides of sulfuric acids
- C07C307/10—Diamides of sulfuric acids having nitrogen atoms of the sulfamide groups bound to carbon atoms of six-membered aromatic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
- C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C311/08—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/30—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/37—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/88—Carbazoles; Hydrogenated carbazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/76—Dibenzothiophenes
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
- C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
- C07C2603/18—Fluorenes; Hydrogenated fluorenes

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Diabetes (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Bioinformatics & Cheminformatics (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Engineering & Computer Science (AREA)
Obesity (AREA)
Hematology (AREA)
Child & Adolescent Psychology (AREA)
Emergency Medicine (AREA)
Endocrinology (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Indole Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Saccharide Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Furan Compounds (AREA)

NO19983197A 1996-01-10 1998-07-10 Nye trisykliske forbindelser og medikamentsammensetninger inneholdende slike NO312159B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP257696		1996-01-10
PCT/JP1996/003689 WO1997025311A1 (fr)	1996-01-10	1996-12-18	Nouveaux composes tricycliques et compositions medicamenteuses contenant ces composes

Publications (2)

Publication Number	Publication Date
NO983197L NO983197L (no)	1998-09-10
NO312159B1 true NO312159B1 (no)	2002-04-02

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ID=11533209

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NO19983197A NO312159B1 (no)	1996-01-10	1998-07-10	Nye trisykliske forbindelser og medikamentsammensetninger inneholdende slike
NO20012876A NO20012876D0 (no)	1996-01-10	2001-06-11	Nye trisykliske forbindelser og medikamentsammensetninger inneholdende slike

Family Applications After (1)

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NO20012876A NO20012876D0 (no)	1996-01-10	2001-06-11	Nye trisykliske forbindelser og medikamentsammensetninger inneholdende slike

Country Status (14)

Country	Link
US (4)	US6037362A (de)
EP (1)	EP0882707B1 (de)
JP (1)	JP2000239255A (de)
KR (1)	KR100395280B1 (de)
CN (2)	CN1083831C (de)
AT (1)	ATE251608T1 (de)
AU (1)	AU715233B2 (de)
CA (1)	CA2242351C (de)
DE (1)	DE69630319T2 (de)
ES (1)	ES2208772T3 (de)
HK (1)	HK1017669A1 (de)
NO (2)	NO312159B1 (de)
PT (1)	PT882707E (de)
WO (1)	WO1997025311A1 (de)

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US6040344A (en) *	1996-11-11	2000-03-21	Sepracor Inc.	Formoterol process
JP2001503772A (ja) *	1996-11-11	2001-03-21	セプラクール，インコーポレイテッド	フォルモテロールの光学的に純粋な異性体の製造方法
US6172099B1 (en)	1997-07-03	2001-01-09	Asahi Kasei Kogyo Kabushiki Kaisha	Tricyclic compounds having saturated rings and medicinal compositions containing the same
ATE423555T1 (de) *	1998-04-06	2009-03-15	Astellas Pharma Inc	Verwendung von beta-3-adrenergen-rezeptoren agonisten in der behandlung von dysurie
US20030073644A1 (en) *	1998-11-11	2003-04-17	Smithkline Beecham P.L.C.	Combinations comprising a beta-agonist and a further antidiabetic agent
CN1332638A (zh) *	1998-11-11	2002-01-23	史密丝克莱恩比彻姆有限公司	包含β－激动剂和其它抗糖尿病药物的组合物
KR20010080761A (ko) *	1998-12-15	2001-08-22	야마모토 카즈모토	신규한 복소환 화합물 및 이를 함유하는 의약 조성물
TW519537B (en) *	1999-03-26	2003-02-01	Asahi Chemical Ind	Process for the preparation of tricylic amino-alcohol derivatives
EP1174426A1 (de) *	1999-04-01	2002-01-23	Asahi Kasei Kabushiki Kaisha	Methoden zur herstellung eines trizyklischen aminoalkoholes durch azide
WO2001004092A1 (fr) *	1999-07-09	2001-01-18	Asahi Kasei Kabushiki Kaisha	Procede de preparation de derives d'alcools amines tricycliques
MXPA02002283A (es) *	1999-09-03	2002-07-30	Asahi Chemical Ind	Proceso para preparar derivados triciclicos de amino alcoholes.
US20030220329A1 (en) *	1999-09-17	2003-11-27	Duke University	Method of improving beta-adrenergic receptor function
WO2001025198A1 (fr) *	1999-10-04	2001-04-12	Asahi Kasei Kabushiki Kaisha	Amelioration de la solubilite de derives d'alcools amines tricycliques
AU1888501A (en) *	1999-12-16	2001-06-25	Asahi Kasei Kabushiki Kaisha	Novel substituted tricyclic compounds
US20030018061A1 (en) *	2000-01-28	2003-01-23	Kohei Ogawa	Novel remedies with the use of beta 3 agonist
AU2001252575A1 (en) *	2000-04-28	2001-11-12	Asahi Kasei Kabushiki Kaisha	Novel tricyclic compounds
US6861444B2 (en) *	2000-04-28	2005-03-01	Asahi Kasei Pharma Corporation	Bicyclic compounds
WO2001083453A1 (fr) *	2000-04-28	2001-11-08	Asahi Kasei Kabushiki Kaisha	Nouveaux composes tricycliques substitues
GB0010757D0 (en) *	2000-05-05	2000-06-28	Astrazeneca Ab	Chemical compounds
WO2002051806A1 (en) *	2000-12-22	2002-07-04	Astrazeneca Ab	Carbazole derivatives and their use as neuropeptide y5 receptor ligands
WO2002074306A1 (fr) *	2001-03-19	2002-09-26	Asahi Kasei Kabushiki Kaisha	Remedes pour la steatose hepatique
GB0121941D0 (en) *	2001-09-11	2001-10-31	Astrazeneca Ab	Chemical compounds
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1996
- 1996-12-18 AT AT96942564T patent/ATE251608T1/de not_active IP Right Cessation
- 1996-12-18 WO PCT/JP1996/003689 patent/WO1997025311A1/ja active IP Right Grant
- 1996-12-18 EP EP96942564A patent/EP0882707B1/de not_active Expired - Lifetime
- 1996-12-18 US US09/101,232 patent/US6037362A/en not_active Expired - Fee Related
- 1996-12-18 AU AU11708/97A patent/AU715233B2/en not_active Ceased
- 1996-12-18 ES ES96942564T patent/ES2208772T3/es not_active Expired - Lifetime
- 1996-12-18 DE DE69630319T patent/DE69630319T2/de not_active Expired - Lifetime
- 1996-12-18 CA CA002242351A patent/CA2242351C/en not_active Expired - Fee Related
- 1996-12-18 CN CN96180079A patent/CN1083831C/zh not_active Expired - Fee Related
- 1996-12-18 KR KR10-1998-0705300A patent/KR100395280B1/ko not_active IP Right Cessation
- 1996-12-18 PT PT96942564T patent/PT882707E/pt unknown
1998
- 1998-07-10 NO NO19983197A patent/NO312159B1/no not_active IP Right Cessation
1999
- 1999-07-05 HK HK99102818A patent/HK1017669A1/xx not_active IP Right Cessation
- 1999-12-28 US US09/472,937 patent/US6187809B1/en not_active Expired - Fee Related
2000
- 2000-02-23 JP JP2000045460A patent/JP2000239255A/ja not_active Withdrawn
- 2000-11-02 CN CN00131988A patent/CN1295064A/zh active Pending
- 2000-11-16 US US09/713,202 patent/US6545053B1/en not_active Expired - Fee Related
2001
- 2001-06-11 NO NO20012876A patent/NO20012876D0/no not_active Application Discontinuation
2002
- 2002-09-30 US US10/259,462 patent/US20030139475A1/en not_active Abandoned

Also Published As

Publication number	Publication date
US6545053B1 (en)	2003-04-08
NO983197L (no)	1998-09-10
CN1209119A (zh)	1999-02-24
CA2242351A1 (en)	1997-07-17
EP0882707A1 (de)	1998-12-09
ES2208772T3 (es)	2004-06-16
DE69630319T2 (de)	2004-07-29
ATE251608T1 (de)	2003-10-15
JP2000239255A (ja)	2000-09-05
CA2242351C (en)	2003-03-11
US6187809B1 (en)	2001-02-13
KR19990077162A (ko)	1999-10-25
KR100395280B1 (ko)	2004-06-04
PT882707E (pt)	2004-02-27
EP0882707A4 (de)	2001-04-11
AU1170897A (en)	1997-08-01
CN1083831C (zh)	2002-05-01
WO1997025311A1 (fr)	1997-07-17
EP0882707B1 (de)	2003-10-08
NO20012876L (no)	1998-09-10
HK1017669A1 (en)	1999-11-26
US20030139475A1 (en)	2003-07-24
AU715233B2 (en)	2000-01-20
DE69630319D1 (de)	2003-11-13
US6037362A (en)	2000-03-14
NO20012876D0 (no)	2001-06-11
CN1295064A (zh)	2001-05-16

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EP0062503A1 (de)	1982-10-13	Benzothiophen-Verbindungen und Verfahren zu ihrer Herstellung
PT94158A (pt)	1991-01-08	Processo para a preparacao de derivados de benzo-ciclo-alcanos e de composicoes farmaceuticas que os contem
US20030040538A1 (en)	2003-02-27	Novel substituted tricyclic compounds
IL42640A (en)	1977-10-31	Substituted 2'-phenoxyalkane-sulfonanilides
FR2686339A1 (fr)	1993-07-23	Nouveaux amides et sulfonamides naphtaleniques, leurs procedes de preparation et les compositions pharmaceutiques qui les contiennent.
Barlow et al.	2010	Synthesis and evaluation of dimeric 1, 2, 3, 4-Tetrahydro-naphthalenylamine and Indan-1-ylamine derivatives with mast cell-stabilising and anti-allergic activity
JP3124242B2 (ja)	2001-01-15	新規な３環性化合物
JP4171097B2 (ja)	2008-10-22	スルホンアミド−置換された縮合７−員環化合物、医薬としてのそれらの使用およびそれらを含有する医薬製剤
AU9139898A (en)	1999-05-27	Sulfonamide-substituted fused 5-membered ring compounds, their use as a medicament, and pharmaceutical preparations comprising them
AU739696B2 (en)	2001-10-18	Novel tricyclic compounds and drug compositions containing same
FR2817257A1 (fr)	2002-05-31	Cyclohexyl(alkyl)-propanolamines, leur preparation et compositions pharmaceutiques en contenant
WO2001083453A1 (fr)	2001-11-08	Nouveaux composes tricycliques substitues
FR2682383A1 (fr)	1993-04-16	Derives du cyclopentane accole a un cycle benzenique, thiophenique ou furannique, leurs procedes de preparation et leur application en therapeutique.

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