RU2013154733A - Производные бензоциклогептенуксусной кислоты - Google Patents
Производные бензоциклогептенуксусной кислоты Download PDFInfo
- Publication number
- RU2013154733A RU2013154733A RU2013154733/04A RU2013154733A RU2013154733A RU 2013154733 A RU2013154733 A RU 2013154733A RU 2013154733/04 A RU2013154733/04 A RU 2013154733/04A RU 2013154733 A RU2013154733 A RU 2013154733A RU 2013154733 A RU2013154733 A RU 2013154733A
- Authority
- RU
- Russia
- Prior art keywords
- benzocyclohepten
- yloxy
- tetrahydro
- acetic acid
- methylamino
- Prior art date
Links
- 239000002253 acid Substances 0.000 title 2
- ZVCPCZRXWGOICC-UHFFFAOYSA-N 1h-benzo[7]annulene Chemical class C1=CC=CC=C2CC=CC=C21 ZVCPCZRXWGOICC-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 20
- 125000001424 substituent group Chemical group 0.000 claims abstract 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 11
- 125000000217 alkyl group Chemical group 0.000 claims abstract 10
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims abstract 7
- -1 3,5-Dichlorobenzenesulfonylamino Chemical group 0.000 claims abstract 4
- 239000004305 biphenyl Substances 0.000 claims abstract 4
- 235000010290 biphenyl Nutrition 0.000 claims abstract 4
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract 4
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 4
- 239000001257 hydrogen Substances 0.000 claims abstract 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims abstract 4
- FJYJWLQEZJEDPA-UHFFFAOYSA-N 2-[[5-[[3,5-bis(trifluoromethyl)phenyl]sulfonylamino]-6,7,8,9-tetrahydro-5h-benzo[7]annulen-1-yl]oxy]acetic acid Chemical compound C1CCCC=2C(OCC(=O)O)=CC=CC=2C1NS(=O)(=O)C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 FJYJWLQEZJEDPA-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 2
- 125000001246 bromo group Chemical group Br* 0.000 claims abstract 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract 2
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract 2
- 229910052736 halogen Inorganic materials 0.000 claims abstract 2
- 150000002367 halogens Chemical class 0.000 claims abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract 2
- 150000003222 pyridines Chemical class 0.000 claims abstract 2
- 150000003839 salts Chemical class 0.000 claims abstract 2
- 208000006673 asthma Diseases 0.000 claims 4
- 230000002265 prevention Effects 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- BBLGQWFFUJSQAF-UHFFFAOYSA-N 2-[[5-[(3,5-dichlorophenyl)sulfonylamino]-6,7,8,9-tetrahydro-5h-benzo[7]annulen-1-yl]oxy]acetic acid Chemical compound C1CCCC=2C(OCC(=O)O)=CC=CC=2C1NS(=O)(=O)C1=CC(Cl)=CC(Cl)=C1 BBLGQWFFUJSQAF-UHFFFAOYSA-N 0.000 claims 1
- XHNGTORTOTWQOK-UHFFFAOYSA-N 2-[[5-[(3-methylsulfonylphenyl)sulfonylamino]-6,7,8,9-tetrahydro-5h-benzo[7]annulen-1-yl]oxy]acetic acid Chemical compound CS(=O)(=O)C1=CC=CC(S(=O)(=O)NC2C3=CC=CC(OCC(O)=O)=C3CCCC2)=C1 XHNGTORTOTWQOK-UHFFFAOYSA-N 0.000 claims 1
- PMNILJISIOBWJG-UHFFFAOYSA-N 2-[[5-[(3-phenylphenyl)sulfonylamino]-6,7,8,9-tetrahydro-5h-benzo[7]annulen-1-yl]oxy]acetic acid Chemical compound C1CCCC=2C(OCC(=O)O)=CC=CC=2C1NS(=O)(=O)C(C=1)=CC=CC=1C1=CC=CC=C1 PMNILJISIOBWJG-UHFFFAOYSA-N 0.000 claims 1
- PXWGQBIVZYJKQJ-UHFFFAOYSA-N 2-[[5-[(4-phenylphenyl)sulfonylamino]-6,7,8,9-tetrahydro-5h-benzo[7]annulen-1-yl]oxy]acetic acid Chemical compound C1CCCC=2C(OCC(=O)O)=CC=CC=2C1NS(=O)(=O)C(C=C1)=CC=C1C1=CC=CC=C1 PXWGQBIVZYJKQJ-UHFFFAOYSA-N 0.000 claims 1
- SSTPXELTHMFXRK-UHFFFAOYSA-N 2-[[5-[[3,5-bis(methylsulfonyl)phenyl]sulfonyl-methylamino]-6,7,8,9-tetrahydro-5h-benzo[7]annulen-1-yl]oxy]acetic acid Chemical compound C1CCCC2=C(OCC(O)=O)C=CC=C2C1N(C)S(=O)(=O)C1=CC(S(C)(=O)=O)=CC(S(C)(=O)=O)=C1 SSTPXELTHMFXRK-UHFFFAOYSA-N 0.000 claims 1
- WREWKUDJSUNGFM-UHFFFAOYSA-N 2-[[5-[[3,5-bis(methylsulfonyl)phenyl]sulfonylamino]-6,7,8,9-tetrahydro-5h-benzo[7]annulen-1-yl]oxy]acetic acid Chemical compound CS(=O)(=O)C1=CC(S(C)(=O)=O)=CC(S(=O)(=O)NC2C3=CC=CC(OCC(O)=O)=C3CCCC2)=C1 WREWKUDJSUNGFM-UHFFFAOYSA-N 0.000 claims 1
- ZSDLPRGLAHWDGO-UHFFFAOYSA-N 2-[[5-[[3-(3-propan-2-ylphenyl)phenyl]sulfonylamino]-6,7,8,9-tetrahydro-5h-benzo[7]annulen-1-yl]oxy]acetic acid Chemical compound CC(C)C1=CC=CC(C=2C=C(C=CC=2)S(=O)(=O)NC2C3=CC=CC(OCC(O)=O)=C3CCCC2)=C1 ZSDLPRGLAHWDGO-UHFFFAOYSA-N 0.000 claims 1
- GESSFAUTHJTHJK-UHFFFAOYSA-N 2-[[5-[[3-(4-methylphenyl)phenyl]sulfonylamino]-6,7,8,9-tetrahydro-5h-benzo[7]annulen-1-yl]oxy]acetic acid Chemical compound C1=CC(C)=CC=C1C1=CC=CC(S(=O)(=O)NC2C3=CC=CC(OCC(O)=O)=C3CCCC2)=C1 GESSFAUTHJTHJK-UHFFFAOYSA-N 0.000 claims 1
- AIMFKZSXGLFPBP-UHFFFAOYSA-N 2-[[5-[[3-acetyl-5-(trifluoromethyl)phenyl]sulfonyl-methylamino]-6,7,8,9-tetrahydro-5h-benzo[7]annulen-1-yl]oxy]acetic acid Chemical compound C1CCCC2=C(OCC(O)=O)C=CC=C2C1N(C)S(=O)(=O)C1=CC(C(C)=O)=CC(C(F)(F)F)=C1 AIMFKZSXGLFPBP-UHFFFAOYSA-N 0.000 claims 1
- PRVISOMFOXLNPR-UHFFFAOYSA-N 2-[[5-[[3-acetyl-5-(trifluoromethyl)phenyl]sulfonylamino]-6,7,8,9-tetrahydro-5h-benzo[7]annulen-1-yl]oxy]acetic acid Chemical compound CC(=O)C1=CC(C(F)(F)F)=CC(S(=O)(=O)NC2C3=CC=CC(OCC(O)=O)=C3CCCC2)=C1 PRVISOMFOXLNPR-UHFFFAOYSA-N 0.000 claims 1
- IEYVIBXHSICDQS-UHFFFAOYSA-N 2-[[5-[[3-bromo-5-(trifluoromethyl)phenyl]sulfonyl-methylamino]-6,7,8,9-tetrahydro-5h-benzo[7]annulen-1-yl]oxy]acetic acid Chemical compound C1CCCC2=C(OCC(O)=O)C=CC=C2C1N(C)S(=O)(=O)C1=CC(Br)=CC(C(F)(F)F)=C1 IEYVIBXHSICDQS-UHFFFAOYSA-N 0.000 claims 1
- LFCJDXNFXNVOPP-UHFFFAOYSA-N 2-[[5-[[3-bromo-5-(trifluoromethyl)phenyl]sulfonylamino]-6,7,8,9-tetrahydro-5h-benzo[7]annulen-1-yl]oxy]acetic acid Chemical compound C1CCCC=2C(OCC(=O)O)=CC=CC=2C1NS(=O)(=O)C1=CC(Br)=CC(C(F)(F)F)=C1 LFCJDXNFXNVOPP-UHFFFAOYSA-N 0.000 claims 1
- UTILUAFNLZECFR-UHFFFAOYSA-N 2-[[5-[[3-fluoro-5-(trifluoromethyl)phenyl]sulfonyl-methylamino]-6,7,8,9-tetrahydro-5h-benzo[7]annulen-1-yl]oxy]acetic acid Chemical compound C1CCCC2=C(OCC(O)=O)C=CC=C2C1N(C)S(=O)(=O)C1=CC(F)=CC(C(F)(F)F)=C1 UTILUAFNLZECFR-UHFFFAOYSA-N 0.000 claims 1
- NUOZZBNHKFCLFK-UHFFFAOYSA-N 2-[[5-[[3-fluoro-5-(trifluoromethyl)phenyl]sulfonylamino]-6,7,8,9-tetrahydro-5h-benzo[7]annulen-1-yl]oxy]acetic acid Chemical compound C1CCCC=2C(OCC(=O)O)=CC=CC=2C1NS(=O)(=O)C1=CC(F)=CC(C(F)(F)F)=C1 NUOZZBNHKFCLFK-UHFFFAOYSA-N 0.000 claims 1
- JEDTXMYCLWBWNS-UHFFFAOYSA-N 2-[[5-[[3-methoxy-5-(trifluoromethyl)phenyl]sulfonyl-methylamino]-6,7,8,9-tetrahydro-5h-benzo[7]annulen-1-yl]oxy]acetic acid Chemical compound COC1=CC(C(F)(F)F)=CC(S(=O)(=O)N(C)C2C3=CC=CC(OCC(O)=O)=C3CCCC2)=C1 JEDTXMYCLWBWNS-UHFFFAOYSA-N 0.000 claims 1
- LLSUKDWLCBAWHJ-UHFFFAOYSA-N 2-[[5-[[3-methoxy-5-(trifluoromethyl)phenyl]sulfonylamino]-6,7,8,9-tetrahydro-5h-benzo[7]annulen-1-yl]oxy]acetic acid Chemical compound COC1=CC(C(F)(F)F)=CC(S(=O)(=O)NC2C3=CC=CC(OCC(O)=O)=C3CCCC2)=C1 LLSUKDWLCBAWHJ-UHFFFAOYSA-N 0.000 claims 1
- TVKADACOKQJEAB-UHFFFAOYSA-N 2-[[5-[[3-methylsulfonyl-5-(trifluoromethyl)phenyl]sulfonylamino]-6,7,8,9-tetrahydro-5h-benzo[7]annulen-1-yl]oxy]acetic acid Chemical compound CS(=O)(=O)C1=CC(C(F)(F)F)=CC(S(=O)(=O)NC2C3=CC=CC(OCC(O)=O)=C3CCCC2)=C1 TVKADACOKQJEAB-UHFFFAOYSA-N 0.000 claims 1
- SVVQOBPOSAHJDZ-UHFFFAOYSA-N 2-[[5-[[3-propan-2-yl-5-(trifluoromethyl)phenyl]sulfonylamino]-6,7,8,9-tetrahydro-5h-benzo[7]annulen-1-yl]oxy]acetic acid Chemical compound CC(C)C1=CC(C(F)(F)F)=CC(S(=O)(=O)NC2C3=CC=CC(OCC(O)=O)=C3CCCC2)=C1 SVVQOBPOSAHJDZ-UHFFFAOYSA-N 0.000 claims 1
- AFQDJUFUKOZVCV-UHFFFAOYSA-N 2-[[5-[[4-(3-methylsulfanylphenyl)phenyl]sulfonylamino]-6,7,8,9-tetrahydro-5h-benzo[7]annulen-1-yl]oxy]acetic acid Chemical compound CSC1=CC=CC(C=2C=CC(=CC=2)S(=O)(=O)NC2C3=CC=CC(OCC(O)=O)=C3CCCC2)=C1 AFQDJUFUKOZVCV-UHFFFAOYSA-N 0.000 claims 1
- SNPZFJZWDBTQNZ-UHFFFAOYSA-N 2-[[5-[[4-(3-methylsulfonylphenyl)phenyl]sulfonylamino]-6,7,8,9-tetrahydro-5h-benzo[7]annulen-1-yl]oxy]acetic acid Chemical compound CS(=O)(=O)C1=CC=CC(C=2C=CC(=CC=2)S(=O)(=O)NC2C3=CC=CC(OCC(O)=O)=C3CCCC2)=C1 SNPZFJZWDBTQNZ-UHFFFAOYSA-N 0.000 claims 1
- KBWGCNWVRCSUIG-UHFFFAOYSA-N 2-[[5-[[4-(3-propan-2-ylphenyl)phenyl]sulfonylamino]-6,7,8,9-tetrahydro-5h-benzo[7]annulen-1-yl]oxy]acetic acid Chemical compound CC(C)C1=CC=CC(C=2C=CC(=CC=2)S(=O)(=O)NC2C3=CC=CC(OCC(O)=O)=C3CCCC2)=C1 KBWGCNWVRCSUIG-UHFFFAOYSA-N 0.000 claims 1
- NJWMFNYGAVNRJO-UHFFFAOYSA-N 2-[[5-[[4-(3-tert-butyl-5-methylphenyl)phenyl]sulfonyl-methylamino]-6,7,8,9-tetrahydro-5h-benzo[7]annulen-1-yl]oxy]acetic acid Chemical compound C1CCCC2=C(OCC(O)=O)C=CC=C2C1N(C)S(=O)(=O)C(C=C1)=CC=C1C1=CC(C)=CC(C(C)(C)C)=C1 NJWMFNYGAVNRJO-UHFFFAOYSA-N 0.000 claims 1
- URWIFKCLYUNYCZ-UHFFFAOYSA-N 2-[[5-[[4-(3-tert-butyl-5-methylphenyl)phenyl]sulfonylamino]-6,7,8,9-tetrahydro-5h-benzo[7]annulen-1-yl]oxy]acetic acid Chemical compound CC(C)(C)C1=CC(C)=CC(C=2C=CC(=CC=2)S(=O)(=O)NC2C3=CC=CC(OCC(O)=O)=C3CCCC2)=C1 URWIFKCLYUNYCZ-UHFFFAOYSA-N 0.000 claims 1
- DFEKIHDTCXSXEU-UHFFFAOYSA-N 2-[[5-[[4-(4-hydroxyphenyl)phenyl]sulfonyl-methylamino]-6,7,8,9-tetrahydro-5h-benzo[7]annulen-1-yl]oxy]acetic acid Chemical compound C1CCCC2=C(OCC(O)=O)C=CC=C2C1N(C)S(=O)(=O)C(C=C1)=CC=C1C1=CC=C(O)C=C1 DFEKIHDTCXSXEU-UHFFFAOYSA-N 0.000 claims 1
- GNMIFQLLPXKRGX-UHFFFAOYSA-N 2-[[5-[[4-(4-hydroxyphenyl)phenyl]sulfonylamino]-6,7,8,9-tetrahydro-5h-benzo[7]annulen-1-yl]oxy]acetic acid Chemical compound C1CCCC=2C(OCC(=O)O)=CC=CC=2C1NS(=O)(=O)C(C=C1)=CC=C1C1=CC=C(O)C=C1 GNMIFQLLPXKRGX-UHFFFAOYSA-N 0.000 claims 1
- BEKZZBRXCMAGKD-UHFFFAOYSA-N 2-[[5-[[4-(5-methylpyridin-3-yl)phenyl]sulfonylamino]-6,7,8,9-tetrahydro-5h-benzo[7]annulen-1-yl]oxy]acetic acid Chemical compound CC1=CN=CC(C=2C=CC(=CC=2)S(=O)(=O)NC2C3=CC=CC(OCC(O)=O)=C3CCCC2)=C1 BEKZZBRXCMAGKD-UHFFFAOYSA-N 0.000 claims 1
- PNSAPMBLKZAZOQ-UHFFFAOYSA-N 2-[[5-[[5-(3-propan-2-ylphenyl)pyridin-2-yl]sulfonylamino]-6,7,8,9-tetrahydro-5h-benzo[7]annulen-1-yl]oxy]acetic acid Chemical compound CC(C)C1=CC=CC(C=2C=NC(=CC=2)S(=O)(=O)NC2C3=CC=CC(OCC(O)=O)=C3CCCC2)=C1 PNSAPMBLKZAZOQ-UHFFFAOYSA-N 0.000 claims 1
- UEAXSXZEVVPFRP-UHFFFAOYSA-N 2-[[5-[[5-(3-tert-butyl-5-methylphenyl)pyridin-2-yl]sulfonylamino]-6,7,8,9-tetrahydro-5h-benzo[7]annulen-1-yl]oxy]acetic acid Chemical compound CC(C)(C)C1=CC(C)=CC(C=2C=NC(=CC=2)S(=O)(=O)NC2C3=CC=CC(OCC(O)=O)=C3CCCC2)=C1 UEAXSXZEVVPFRP-UHFFFAOYSA-N 0.000 claims 1
- JIVQJBWQKDOKMY-UHFFFAOYSA-N 2-[[5-[[5-[3-(2-hydroxyethyl)phenyl]pyridin-2-yl]sulfonylamino]-6,7,8,9-tetrahydro-5h-benzo[7]annulen-1-yl]oxy]acetic acid Chemical compound OCCC1=CC=CC(C=2C=NC(=CC=2)S(=O)(=O)NC2C3=CC=CC(OCC(O)=O)=C3CCCC2)=C1 JIVQJBWQKDOKMY-UHFFFAOYSA-N 0.000 claims 1
- UNUFSMQESKFSPO-UHFFFAOYSA-N 2-[[5-[[5-[3-(trifluoromethyl)phenyl]pyridin-2-yl]sulfonylamino]-6,7,8,9-tetrahydro-5h-benzo[7]annulen-1-yl]oxy]acetic acid Chemical compound C1CCCC=2C(OCC(=O)O)=CC=CC=2C1NS(=O)(=O)C(N=C1)=CC=C1C1=CC=CC(C(F)(F)F)=C1 UNUFSMQESKFSPO-UHFFFAOYSA-N 0.000 claims 1
- DDHNSYXCOKMHJH-UHFFFAOYSA-N 2-[[5-[methyl-(4-phenylphenyl)sulfonylamino]-6,7,8,9-tetrahydro-5h-benzo[7]annulen-1-yl]oxy]acetic acid Chemical compound C1CCCC2=C(OCC(O)=O)C=CC=C2C1N(C)S(=O)(=O)C(C=C1)=CC=C1C1=CC=CC=C1 DDHNSYXCOKMHJH-UHFFFAOYSA-N 0.000 claims 1
- LRMPPVAOCWUSMW-UHFFFAOYSA-N 2-[[5-[methyl-[3-(3-propan-2-ylphenyl)phenyl]sulfonylamino]-6,7,8,9-tetrahydro-5h-benzo[7]annulen-1-yl]oxy]acetic acid Chemical compound CC(C)C1=CC=CC(C=2C=C(C=CC=2)S(=O)(=O)N(C)C2C3=CC=CC(OCC(O)=O)=C3CCCC2)=C1 LRMPPVAOCWUSMW-UHFFFAOYSA-N 0.000 claims 1
- RYNICGREANPPTP-UHFFFAOYSA-N 2-[[5-[methyl-[3-(4-methylphenyl)phenyl]sulfonylamino]-6,7,8,9-tetrahydro-5h-benzo[7]annulen-1-yl]oxy]acetic acid Chemical compound C1CCCC2=C(OCC(O)=O)C=CC=C2C1N(C)S(=O)(=O)C(C=1)=CC=CC=1C1=CC=C(C)C=C1 RYNICGREANPPTP-UHFFFAOYSA-N 0.000 claims 1
- UUETUWFAIZOTSQ-UHFFFAOYSA-N 2-[[5-[methyl-[3-methylsulfonyl-5-(trifluoromethyl)phenyl]sulfonylamino]-6,7,8,9-tetrahydro-5h-benzo[7]annulen-1-yl]oxy]acetic acid Chemical compound C1CCCC2=C(OCC(O)=O)C=CC=C2C1N(C)S(=O)(=O)C1=CC(C(F)(F)F)=CC(S(C)(=O)=O)=C1 UUETUWFAIZOTSQ-UHFFFAOYSA-N 0.000 claims 1
- FXCMJVJOKPGCIE-UHFFFAOYSA-N 2-[[5-[methyl-[3-propan-2-yl-5-(trifluoromethyl)phenyl]sulfonylamino]-6,7,8,9-tetrahydro-5h-benzo[7]annulen-1-yl]oxy]acetic acid Chemical compound CC(C)C1=CC(C(F)(F)F)=CC(S(=O)(=O)N(C)C2C3=CC=CC(OCC(O)=O)=C3CCCC2)=C1 FXCMJVJOKPGCIE-UHFFFAOYSA-N 0.000 claims 1
- IUXFNJVHGAFMON-UHFFFAOYSA-N 2-[[5-[methyl-[4-(3-methylsulfanylphenyl)phenyl]sulfonylamino]-6,7,8,9-tetrahydro-5h-benzo[7]annulen-1-yl]oxy]acetic acid Chemical compound CSC1=CC=CC(C=2C=CC(=CC=2)S(=O)(=O)N(C)C2C3=CC=CC(OCC(O)=O)=C3CCCC2)=C1 IUXFNJVHGAFMON-UHFFFAOYSA-N 0.000 claims 1
- KVBXCSUTEBYXPB-UHFFFAOYSA-N 2-[[5-[methyl-[4-(3-methylsulfonylphenyl)phenyl]sulfonylamino]-6,7,8,9-tetrahydro-5h-benzo[7]annulen-1-yl]oxy]acetic acid Chemical compound C1CCCC2=C(OCC(O)=O)C=CC=C2C1N(C)S(=O)(=O)C(C=C1)=CC=C1C1=CC=CC(S(C)(=O)=O)=C1 KVBXCSUTEBYXPB-UHFFFAOYSA-N 0.000 claims 1
- LLQRDZNLEGBYMN-UHFFFAOYSA-N 2-[[5-[methyl-[4-(3-propan-2-ylphenyl)phenyl]sulfonylamino]-6,7,8,9-tetrahydro-5h-benzo[7]annulen-1-yl]oxy]acetic acid Chemical compound CC(C)C1=CC=CC(C=2C=CC(=CC=2)S(=O)(=O)N(C)C2C3=CC=CC(OCC(O)=O)=C3CCCC2)=C1 LLQRDZNLEGBYMN-UHFFFAOYSA-N 0.000 claims 1
- SNRNRXDFBIBEOQ-UHFFFAOYSA-N 2-[[5-[methyl-[4-(5-methylpyridin-3-yl)phenyl]sulfonylamino]-6,7,8,9-tetrahydro-5h-benzo[7]annulen-1-yl]oxy]acetic acid Chemical compound C1CCCC2=C(OCC(O)=O)C=CC=C2C1N(C)S(=O)(=O)C(C=C1)=CC=C1C1=CN=CC(C)=C1 SNRNRXDFBIBEOQ-UHFFFAOYSA-N 0.000 claims 1
- BMIGAVILGPSYAT-UHFFFAOYSA-N 2-[[5-[methyl-[5-[3-(trifluoromethyl)phenyl]pyridin-2-yl]sulfonylamino]-6,7,8,9-tetrahydro-5h-benzo[7]annulen-1-yl]oxy]acetic acid Chemical compound C1CCCC2=C(OCC(O)=O)C=CC=C2C1N(C)S(=O)(=O)C(N=C1)=CC=C1C1=CC=CC(C(F)(F)F)=C1 BMIGAVILGPSYAT-UHFFFAOYSA-N 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/32—Sulfur atoms
- C07D213/34—Sulfur atoms to which a second hetero atom is attached
-
- 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
- C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
- C07C311/20—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring
-
- 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
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/18—Sulfonamides
-
- 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
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Abstract
1. Соединение формулы (I):,где Ar представляет собой:- фенил, незамещенный или содержащий один или два заместителя, независимо выбранных из следующих: галоген, низший алкил, -CF, -SOCH, алкоксигруппа, -С(O)СН, незамещенный гетероарил или гетероарил, замещенный низшим алкилом;- бифенил, незамещенный или содержащий один или два заместителя, независимо выбранных из следующих: -ОН, низший алкил, -SCHили -SOCH; или- пиридин, незамещенный или замещенным, независимо выбранных из следующих: незамещенный фенил или фенил, содержащий один или два заместителя, независимо выбранных из следующих: низший алкил, -CFили -CHCHOH; иRпредставляет собой водород или низший алкил,или их фармацевтически приемлемые соли.2. Соединение по п. 1, в котором Ar представляет собой фенил, незамещенный или содержащий один или два заместителя, независимо выбранных из следующих: фтор, хлор, бром, -СН(СН), -CF, -SOCH, -ОСН, -С(O)СНили -пиридинметил.3. Соединение по п. 1, в котором Ar представляет собой бифенил, незамещенный или содержащий один или два заместителя, независимо выбранных из следующих: -СН, -СН(СН), -С(СН), -ОН, -SCHили -SOCH.4. Соединение по п. 1, в котором Ar представляет собой замещенный пиридин, содержащий в качестве заместителя независимо незамещенный фенил или фенил, содержащий один или два заместителя, независимо выбранных из следующих: -СН, -СН(СН), -С(СН), -CFили -СНСНОН.5. Соединение по п. 1, в котором Rпредставляет собой водород.6. Соединение по п. 1, в котором Rпредставляет собой метил.7. Соединение по п. 1, которое представляет собой следующее:[5-(3,5-Бис-трифторметилбензолсульфониламино)-6,7,8,9-тетрагидро-5Н-бензоциклогептен-1-илокси]-уксусная кислота;[5-(3,5-Дихлорбензолсульфониламино)-6,7,8,9-те�
Claims (13)
1. Соединение формулы (I):
где Ar представляет собой:
- фенил, незамещенный или содержащий один или два заместителя, независимо выбранных из следующих: галоген, низший алкил, -CF3, -SO2CH3, алкоксигруппа, -С(O)СН3, незамещенный гетероарил или гетероарил, замещенный низшим алкилом;
- бифенил, незамещенный или содержащий один или два заместителя, независимо выбранных из следующих: -ОН, низший алкил, -SCH3 или -SO2CH3; или
- пиридин, незамещенный или замещенным, независимо выбранных из следующих: незамещенный фенил или фенил, содержащий один или два заместителя, независимо выбранных из следующих: низший алкил, -CF3 или -CH2CH2OH; и
R1 представляет собой водород или низший алкил,
или их фармацевтически приемлемые соли.
2. Соединение по п. 1, в котором Ar представляет собой фенил, незамещенный или содержащий один или два заместителя, независимо выбранных из следующих: фтор, хлор, бром, -СН(СН3)2, -CF3, -SO2CH3, -ОСН3, -С(O)СН3 или -пиридинметил.
3. Соединение по п. 1, в котором Ar представляет собой бифенил, незамещенный или содержащий один или два заместителя, независимо выбранных из следующих: -СН3, -СН(СН3)2, -С(СН3)3, -ОН, -SCH3 или -SO2CH3.
4. Соединение по п. 1, в котором Ar представляет собой замещенный пиридин, содержащий в качестве заместителя независимо незамещенный фенил или фенил, содержащий один или два заместителя, независимо выбранных из следующих: -СН3, -СН(СН3)2, -С(СН3)3, -CF3 или -СН2СН2ОН.
5. Соединение по п. 1, в котором R1 представляет собой водород.
6. Соединение по п. 1, в котором R1 представляет собой метил.
7. Соединение по п. 1, которое представляет собой следующее:
[5-(3,5-Бис-трифторметилбензолсульфониламино)-6,7,8,9-тетрагидро-5Н-бензоциклогептен-1-илокси]-уксусная кислота;
[5-(3,5-Дихлорбензолсульфониламино)-6,7,8,9-тетрагидро-5Н-бензоциклогептен-1-илокси]-уксусная кислота;
[5-(Бифенил-3-сульфониламино)-6,7,8,9-тетрагидро-5Н-бензоциклогептен-1-илокси]-уксусная кислота;
[5-(Бифенил-4-сульфониламино)-6,7,8,9-тетрагидро-5Н-бензоциклогептен-1-илокси]-уксусная кислота;
[5-(3-Метансульфонилбензолсульфониламино)-6,7,8,9-тетрагидро-5Н-бензоциклогептен-1-илокси]-уксусная кислота;
[5-(3-Фтор-5-трифторметилбензолсульфониламино)-6,7,8,9-тетрагидро-5Н-бензоциклогептен-1-илокси]-уксусная кислота;
{5-[(3-Фтор-5-трифторметилбензолсульфонил)-метиламино]-6,7,8,9-тетрагидро-5Н-бензоциклогептен-1-илокси}-уксусная кислота;
[5-(3-Бром-5-трифторметилбензолсульфониламино)-6,7,8,9-тетрагидро-5Н-бензоциклогептен-1-илокси]-уксусная кислота;
{5-[(3-Бром-5-трифторметилбензолсульфонил)-метиламино]-6,7,8,9-тетрагидро-5Н-бензоциклогептен-1-илокси}-уксусная кислота;
[5-(3,5-Бис-метансульфонилбензолсульфониламино)-6,7,8,9-тетрагидро-5Н-бензоциклогептен-1-илокси]-уксусная кислота;
{5-[(3,5-Бис-метансульфонилбензолсульфонил)-метиламино]-6,7,8,9-тетрагидро-5Н-бензоциклогептен-1-илокси}-уксусная кислота;
{5-[(Бифенил-4-сульфонил)-метиламино]-6,7,8,9-тетрагидро-5Н-бензоциклогептен-1-илокси}-уксусная кислота;
[5-(3-Метокси-5-трифторметилбензолсульфониламино)-6,7,8,9-тетрагидро-5Н-бензоциклогептен-1-илокси]-уксусная кислота;
{5-[(3-Метокси-5-трифторметилбензолсульфонил)-метиламино]-6,7,8,9-тетрагидро-5Н-бензоциклогептен-1-илокси}-уксусная кислота;
[5-(3-Ацетил-5-трифторметилбензолсульфониламино)-6,7,8,9-тетрагидро-5Н-бензоциклогептен-1-илокси]-уксусная кислота;
{5-[(3-Ацетил-5-трифторметилбензолсульфонил)-метиламино]-6,7,8,9-тетрагидро-5Н-бензоциклогептен-1-илокси}-уксусная кислота;
[5-(3-Метансульфонил-5-трифторметилбензолсульфониламино)-6,7,8,9-тетрагидро-5Н-бензоциклогептен-1-илокси]-уксусная кислота;
{5-[(3-Метансульфонил-5-трифторметилбензолсульфонил)-метиламино]-6,7,8,9-тетрагидро-5Н-бензоциклогептен-1-илокси}-уксусная кислота;
[5-(3′-Изопропилбифенил-4-сульфониламино)-6,7,8,9-тетрагидро-5Н-бензоциклогептен-1-илокси]-уксусная кислота;
{5-[(3′-Изопропилбифенил-4-сульфонил)-метиламино]-6,7,8,9-тетрагидро-5Н-бензоциклогептен-1-илокси}-уксусная кислота;
[5-(3′-трет-Бутил-5′-метилбифенил-4-сульфониламино)-6,7,8,9-тетрагидро-5Н-бензоциклогептен-1-илокси]-уксусная кислота;
{5-[(3′-трет-Бутил-5′-метилбифенил-4-сульфонил)-метиламино]-6,7,8,9-тетрагидро-5Н-бензоциклогептен-1-илокси}-уксусная кислота;
[5-(4′-Гидроксибифенил-4-сульфониламино)-6,7,8,9-тетрагидро-5Н-бензоциклогептен-1-илокси]-уксусная кислота;
{5-[(4′-Гидроксибифенил-4-сульфонил)-метиламино]-6,7,8,9-тетрагидро-5Н-бензоциклогептен-1-илокси}-уксусная кислота;
{5-[4-(5-Метилпиридин-3-ил)-бензолсульфониламино]-6,7,8,9-тетрагидро-5Н-бензоциклогептен-1-илокси}-уксусная кислота;
(5-{Метил-[4-(5-метилпиридин-3-ил)-бензолсульфонил]-амино}-6,7,8,9-тетрагидро-5Н-бензоциклогептен-1-илокси)-уксусная кислота;
[5-(3′-Метилсульфанилбифенил-4-сульфониламино)-6,7,8,9-тетрагидро-5Н-бензоциклогептен-1-илокси]-уксусная кислота;
{5-[Метил-(3′-метилсульфанилбифенил-4-сульфонил)-амино]-6,7,8,9-тетрагидро-5Н-бензоциклогептен-1-илокси}-уксусная кислота;
[5-(3′-Метансульфонилбифенил-4-сульфониламино)-6,7,8,9-тетрагидро-5Н-бензоциклогептен-1-илокси]-уксусная кислота;
{5-[(3′-Метансульфонилбифенил-4-сульфонил)-метиламино]-6,7,8,9-тетрагидро-5Н-бензоциклогептен-1-илокси}-уксусная кислота;
{5-[5-(3-Изопропилфенил)-пиридин-2-сульфониламино]-6,7,8,9-тетрагидро-5Н-бензоциклогептен-1-илокси}-уксусная кислота;
(5-{[5-(3-Изопропилфенил)-пиридин-2-сульфонил]-метиламино}-6,7,8,9-тетрагидро-5Н-бензоциклогептен-1-илокси)-уксусная кислота;
{5-[5-(3-Трифторметилфенил)-пиридин-2-сульфониламино]-6,7,8,9-тетрагидро-5Н-бензоциклогептен-1-илокси}-уксусная кислота;
(5-{Метил-[5-(3-трифторметилфенил)-пиридин-2-сульфонил]-амино}-6,7,8,9-тетрагидро-5Н-бензоциклогептен-1-илокси)-уксусная кислота;
{5-[5-(3-трет-Бутил-5-метилфенил)-пиридин-2-сульфониламино]-6,7,8,9-тетрагидро-5Н-бензоциклогептен-1-илокси}-уксусная кислота;
(5-{[5-(3-трет-Бутил-5-метилфенил)-пиридин-2-сульфонил]-метиламино}-6,7,8,9-тетрагидро-5Н-бензоциклогептен-1-илокси)-уксусная кислота;
(5-{5-[3-(2-Гидроксиэтил)-фенил]-пиридин-2-сульфониламино}-6,7,8,9-тетрагидро-5Н-бензоциклогептен-1-илокси)-уксусная кислота;
[5-({5-[3-(2-Гидроксиэтил)-фенил]-пиридин-2-сульфонил}-метиламино)-6,7,8,9-тетрагидро-5Н-бензоциклогептен-1-илокси]-уксусная кислота;
[5-(4′-Метилбифенил-3-сульфониламино)-6,7,8,9-тетрагидро-5Н-бензоциклогептен-1-илокси]-уксусная кислота;
{5-[Метил-(4′-метилбифенил-3-сульфонил)-амино]-6,7,8,9-тетрагидро-5Н-бензоциклогептен-1-илокси}-уксусная кислота;
[5-(3′-Изопропилбифенил-3-сульфониламино)-6,7,8,9-тетрагидро-5Н-бензоциклогептен-1-илокси]-уксусная кислота;
{5-[(3′-Изопропилбифенил-3-сульфонил)-метиламино]-6,7,8,9-тетрагидро-5Н-бензоциклогептен-1-илокси}-уксусная кислота;
[5-(3-Изопропил-5-трифторметилбензолсульфониламино)-6,7,8,9-тетрагидро-5Н-бензоциклогептен-1-илокси]-уксусная кислота; или
{5-[(3-Изопропил-5-трифторметилбензолсульфонил)-метиламино]-6,7,8,9-тетрагидро-5Н-бензоциклогептен-1-илокси}-уксусная кислота.
8. Соединение по любому из пп. 1-7 для применения в качестве терапевтически активного вещества.
9. Фармацевтическая композиция, включающая терапевтически эффективное количество соединения по любому из пп. 1-7 и терапевтически инертный носитель.
10. Применение соединения по любому из пп. 1-7 для лечения или профилактики астмы или COPD.
11. Применение соединения по любому из пп. 1-7 для изготовления лекарственного средства для лечения или профилактики астмы или COPD.
12. Соединение по любому из пп. 1-7 для лечения или профилактики астмы или COPD.
13. Способ лечения или профилактики астмы или COPD, включающий стадию введения эффективного количества соединения, раскрытого в любом из пп. 1-7, пациенту, который в этом нуждается.
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| PCT/EP2012/060455 WO2012168162A1 (en) | 2011-06-06 | 2012-06-04 | Benzocycloheptene acetic acids |
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-
2012
- 2012-05-11 US US13/469,177 patent/US20120309796A1/en not_active Abandoned
- 2012-06-04 EP EP12725741.8A patent/EP2718264B1/en not_active Not-in-force
- 2012-06-04 BR BR112013030264A patent/BR112013030264A2/pt not_active IP Right Cessation
- 2012-06-04 KR KR1020137034448A patent/KR20140041589A/ko not_active Withdrawn
- 2012-06-04 WO PCT/EP2012/060455 patent/WO2012168162A1/en not_active Ceased
- 2012-06-04 MX MX2013013849A patent/MX2013013849A/es not_active Application Discontinuation
- 2012-06-04 CN CN201280027840.6A patent/CN103596925A/zh active Pending
- 2012-06-04 CA CA2837146A patent/CA2837146A1/en not_active Abandoned
- 2012-06-04 JP JP2014514009A patent/JP2014522407A/ja active Pending
- 2012-06-04 RU RU2013154733/04A patent/RU2013154733A/ru not_active Application Discontinuation
Also Published As
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|---|---|
| MX2013013849A (es) | 2014-01-20 |
| EP2718264A1 (en) | 2014-04-16 |
| EP2718264B1 (en) | 2015-08-05 |
| CA2837146A1 (en) | 2012-12-13 |
| BR112013030264A2 (pt) | 2018-08-28 |
| US20120309796A1 (en) | 2012-12-06 |
| WO2012168162A1 (en) | 2012-12-13 |
| JP2014522407A (ja) | 2014-09-04 |
| KR20140041589A (ko) | 2014-04-04 |
| CN103596925A (zh) | 2014-02-19 |
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| FA92 | Acknowledgement of application withdrawn (lack of supplementary materials submitted) |
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