HRP20100402T1 - Formamidni derivati korisni kao ardrenoceptor - Google Patents
Formamidni derivati korisni kao ardrenoceptor Download PDFInfo
- Publication number
- HRP20100402T1 HRP20100402T1 HR20100402T HRP20100402T HRP20100402T1 HR P20100402 T1 HRP20100402 T1 HR P20100402T1 HR 20100402 T HR20100402 T HR 20100402T HR P20100402 T HRP20100402 T HR P20100402T HR P20100402 T1 HRP20100402 T1 HR P20100402T1
- Authority
- HR
- Croatia
- Prior art keywords
- hydroxyphenyl
- formylamino
- hydroxyethylamino
- methylpropyl
- phenyl
- Prior art date
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- 108060003345 Adrenergic Receptor Proteins 0.000 title 1
- 102000017910 Adrenergic receptor Human genes 0.000 title 1
- 150000003948 formamides Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 28
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 12
- 150000003839 salts Chemical class 0.000 claims abstract 10
- 229910052736 halogen Inorganic materials 0.000 claims abstract 7
- 150000002367 halogens Chemical class 0.000 claims abstract 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 7
- 239000012453 solvate Substances 0.000 claims abstract 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims abstract 4
- 229910052799 carbon Inorganic materials 0.000 claims abstract 3
- 125000002947 alkylene group Chemical group 0.000 claims abstract 2
- 150000001721 carbon Chemical group 0.000 claims abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract 2
- 230000000155 isotopic effect Effects 0.000 claims abstract 2
- 125000003386 piperidinyl group Chemical group 0.000 claims abstract 2
- 125000004076 pyridyl group Chemical group 0.000 claims abstract 2
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims abstract 2
- 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 claims abstract 2
- 208000006673 asthma Diseases 0.000 claims 19
- 206010006451 bronchitis Diseases 0.000 claims 13
- 201000009267 bronchiectasis Diseases 0.000 claims 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 6
- 239000005557 antagonist Substances 0.000 claims 5
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 4
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 4
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims 4
- 239000003814 drug Substances 0.000 claims 4
- 239000003112 inhibitor Substances 0.000 claims 4
- 201000010659 intrinsic asthma Diseases 0.000 claims 4
- 230000008506 pathogenesis Effects 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 229940079593 drug Drugs 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- FRUACYAYPLRWIE-HRFSGMKKSA-N 2-[3-[(2r)-2-[[(2r)-2-(3-formamido-4-hydroxyphenyl)-2-hydroxyethyl]amino]propyl]phenyl]-n-[(4-hydroxy-3,5-dimethylphenyl)methyl]acetamide Chemical compound C([C@@H](C)NC[C@H](O)C=1C=C(NC=O)C(O)=CC=1)C(C=1)=CC=CC=1CC(=O)NCC1=CC(C)=C(O)C(C)=C1 FRUACYAYPLRWIE-HRFSGMKKSA-N 0.000 claims 2
- QVRJEOFTQGXTQL-KEEVHDRGSA-N 2-[3-[(2r)-2-[[(2r)-2-(3-formamido-4-hydroxyphenyl)-2-hydroxyethyl]amino]propyl]phenyl]-n-[(6-hydroxynaphthalen-2-yl)methyl]acetamide Chemical compound C1([C@@H](O)CN[C@@H](CC=2C=C(CC(=O)NCC=3C=C4C=CC(O)=CC4=CC=3)C=CC=2)C)=CC=C(O)C(NC=O)=C1 QVRJEOFTQGXTQL-KEEVHDRGSA-N 0.000 claims 2
- PSXFDWMQVSFPAO-NZVRHLSZSA-N 3-[2-[[(2r)-2-(3-formamido-4-hydroxyphenyl)-2-hydroxyethyl]amino]propyl]-n-[2-(4-hydroxyphenyl)-2-methylpropyl]benzamide Chemical compound C([C@H](O)C=1C=C(NC=O)C(O)=CC=1)NC(C)CC(C=1)=CC=CC=1C(=O)NCC(C)(C)C1=CC=C(O)C=C1 PSXFDWMQVSFPAO-NZVRHLSZSA-N 0.000 claims 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 2
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims 2
- 102000001381 Arachidonate 5-Lipoxygenase Human genes 0.000 claims 2
- 108010093579 Arachidonate 5-lipoxygenase Proteins 0.000 claims 2
- 206010006458 Bronchitis chronic Diseases 0.000 claims 2
- 206010014561 Emphysema Diseases 0.000 claims 2
- 229940121948 Muscarinic receptor antagonist Drugs 0.000 claims 2
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims 2
- 230000001154 acute effect Effects 0.000 claims 2
- 208000011341 adult acute respiratory distress syndrome Diseases 0.000 claims 2
- 201000000028 adult respiratory distress syndrome Diseases 0.000 claims 2
- 239000000556 agonist Substances 0.000 claims 2
- 208000007451 chronic bronchitis Diseases 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 208000024711 extrinsic asthma Diseases 0.000 claims 2
- 208000015181 infectious disease Diseases 0.000 claims 2
- 230000002458 infectious effect Effects 0.000 claims 2
- 208000027866 inflammatory disease Diseases 0.000 claims 2
- 208000030603 inherited susceptibility to asthma Diseases 0.000 claims 2
- 239000003199 leukotriene receptor blocking agent Substances 0.000 claims 2
- UVRYKPVJJGRLPT-QUGAMOGWSA-N n-[(5-chloro-2-hydroxyphenyl)methyl]-2-[3-[(2r)-2-[[(2r)-2-(3-formamido-4-hydroxyphenyl)-2-hydroxyethyl]amino]propyl]phenyl]acetamide Chemical compound C([C@@H](C)NC[C@H](O)C=1C=C(NC=O)C(O)=CC=1)C(C=1)=CC=CC=1CC(=O)NCC1=CC(Cl)=CC=C1O UVRYKPVJJGRLPT-QUGAMOGWSA-N 0.000 claims 2
- PYEWFKVLEFEFMJ-SANMLTNESA-N n-[2-(4-chlorophenyl)ethyl]-3-[2-[[(2r)-2-(3-formamido-4-hydroxyphenyl)-2-hydroxyethyl]amino]-2-methylpropyl]benzamide Chemical compound C([C@H](O)C=1C=C(NC=O)C(O)=CC=1)NC(C)(C)CC(C=1)=CC=CC=1C(=O)NCCC1=CC=C(Cl)C=C1 PYEWFKVLEFEFMJ-SANMLTNESA-N 0.000 claims 2
- YTEUQVQZGGWAAL-SANMLTNESA-N n-[2-(5-chloro-2-hydroxyphenyl)ethyl]-3-[2-[[(2r)-2-(3-formamido-4-hydroxyphenyl)-2-hydroxyethyl]amino]-2-methylpropyl]benzamide Chemical compound C([C@H](O)C=1C=C(NC=O)C(O)=CC=1)NC(C)(C)CC(C=1)=CC=CC=1C(=O)NCCC1=CC(Cl)=CC=C1O YTEUQVQZGGWAAL-SANMLTNESA-N 0.000 claims 2
- 230000000414 obstructive effect Effects 0.000 claims 2
- 238000002360 preparation method Methods 0.000 claims 2
- 210000002345 respiratory system Anatomy 0.000 claims 2
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 claims 2
- LXPZNYMPUBXKTB-KEEVHDRGSA-N 2-[3-[(2r)-2-[[(2r)-2-(3-formamido-4-hydroxyphenyl)-2-hydroxyethyl]amino]propyl]phenyl]-n-[(2-hydroxynaphthalen-1-yl)methyl]acetamide Chemical compound C1([C@@H](O)CN[C@@H](CC=2C=C(CC(=O)NCC=3C4=CC=CC=C4C=CC=3O)C=CC=2)C)=CC=C(O)C(NC=O)=C1 LXPZNYMPUBXKTB-KEEVHDRGSA-N 0.000 claims 1
- SRSTWBAWKCDSAL-KCEHZKJRSA-N 2-[3-[(2r)-2-[[(2r)-2-(3-formamido-4-hydroxyphenyl)-2-hydroxyethyl]amino]propyl]phenyl]-n-[[4-(4-hydroxyphenyl)phenyl]methyl]acetamide Chemical compound C([C@@H](C)NC[C@H](O)C=1C=C(NC=O)C(O)=CC=1)C(C=1)=CC=CC=1CC(=O)NCC(C=C1)=CC=C1C1=CC=C(O)C=C1 SRSTWBAWKCDSAL-KCEHZKJRSA-N 0.000 claims 1
- JLRMZCOCIWONDX-DEOSSOPVSA-N 2-[3-[2-[[(2r)-2-(3-formamido-4-hydroxyphenyl)-2-hydroxyethyl]amino]-2-methylpropyl]phenyl]-n-(thian-4-yl)acetamide Chemical compound C([C@H](O)C=1C=C(NC=O)C(O)=CC=1)NC(C)(C)CC(C=1)=CC=CC=1CC(=O)NC1CCSCC1 JLRMZCOCIWONDX-DEOSSOPVSA-N 0.000 claims 1
- URIXFDZPGZEQQM-MHZLTWQESA-N 2-[3-[2-[[(2r)-2-(3-formamido-4-hydroxyphenyl)-2-hydroxyethyl]amino]-2-methylpropyl]phenyl]-n-[(4-methylsulfanylphenyl)methyl]acetamide Chemical compound C1=CC(SC)=CC=C1CNC(=O)CC1=CC=CC(CC(C)(C)NC[C@H](O)C=2C=C(NC=O)C(O)=CC=2)=C1 URIXFDZPGZEQQM-MHZLTWQESA-N 0.000 claims 1
- HDPKMDHLVIFJPM-MHZLTWQESA-N 2-[3-[2-[[(2r)-2-(3-formamido-4-hydroxyphenyl)-2-hydroxyethyl]amino]-2-methylpropyl]phenyl]-n-[(4-methylsulfonylphenyl)methyl]acetamide Chemical compound C([C@H](O)C=1C=C(NC=O)C(O)=CC=1)NC(C)(C)CC(C=1)=CC=CC=1CC(=O)NCC1=CC=C(S(C)(=O)=O)C=C1 HDPKMDHLVIFJPM-MHZLTWQESA-N 0.000 claims 1
- FBQYKARCTKVRLN-YTTGMZPUSA-N 2-[3-[2-[[(2r)-2-(3-formamido-4-hydroxyphenyl)-2-hydroxyethyl]amino]-2-methylpropyl]phenyl]-n-[[3-(4-hydroxyphenyl)phenyl]methyl]acetamide Chemical compound C([C@H](O)C=1C=C(NC=O)C(O)=CC=1)NC(C)(C)CC(C=1)=CC=CC=1CC(=O)NCC(C=1)=CC=CC=1C1=CC=C(O)C=C1 FBQYKARCTKVRLN-YTTGMZPUSA-N 0.000 claims 1
- AYMGMPUUXYDJTB-YTTGMZPUSA-N 2-[3-[2-[[(2r)-2-(3-formamido-4-hydroxyphenyl)-2-hydroxyethyl]amino]-2-methylpropyl]phenyl]-n-[[4-(4-hydroxyphenyl)phenyl]methyl]acetamide Chemical compound C([C@H](O)C=1C=C(NC=O)C(O)=CC=1)NC(C)(C)CC(C=1)=CC=CC=1CC(=O)NCC(C=C1)=CC=C1C1=CC=C(O)C=C1 AYMGMPUUXYDJTB-YTTGMZPUSA-N 0.000 claims 1
- BWGMYAAINUUTIH-SANMLTNESA-N 2-[3-[2-[[(2r)-2-(3-formamido-4-hydroxyphenyl)-2-hydroxyethyl]amino]-2-methylpropyl]phenyl]-n-[[4-(trifluoromethyl)phenyl]methyl]acetamide Chemical compound C([C@H](O)C=1C=C(NC=O)C(O)=CC=1)NC(C)(C)CC(C=1)=CC=CC=1CC(=O)NCC1=CC=C(C(F)(F)F)C=C1 BWGMYAAINUUTIH-SANMLTNESA-N 0.000 claims 1
- ZOKPPCSNPPHNAP-PMERELPUSA-N 3-[2-[[(2r)-2-(3-formamido-4-hydroxyphenyl)-2-hydroxyethyl]amino]-2-methylpropyl]-n-(2-naphthalen-1-ylethyl)benzamide Chemical compound C1([C@@H](O)CNC(C)(CC=2C=C(C=CC=2)C(=O)NCCC=2C3=CC=CC=C3C=CC=2)C)=CC=C(O)C(NC=O)=C1 ZOKPPCSNPPHNAP-PMERELPUSA-N 0.000 claims 1
- XLFGFAOMBIRBTK-SANMLTNESA-N 3-[2-[[(2r)-2-(3-formamido-4-hydroxyphenyl)-2-hydroxyethyl]amino]-2-methylpropyl]-n-(2-phenylethyl)benzamide Chemical compound C([C@H](O)C=1C=C(NC=O)C(O)=CC=1)NC(C)(C)CC(C=1)=CC=CC=1C(=O)NCCC1=CC=CC=C1 XLFGFAOMBIRBTK-SANMLTNESA-N 0.000 claims 1
- XEWGZNJFYYOCCE-VWLOTQADSA-N 3-[2-[[(2r)-2-(3-formamido-4-hydroxyphenyl)-2-hydroxyethyl]amino]-2-methylpropyl]-n-(2-pyridin-2-ylethyl)benzamide Chemical compound C([C@H](O)C=1C=C(NC=O)C(O)=CC=1)NC(C)(C)CC(C=1)=CC=CC=1C(=O)NCCC1=CC=CC=N1 XEWGZNJFYYOCCE-VWLOTQADSA-N 0.000 claims 1
- VNOMOUKHGDETNK-MHZLTWQESA-N 3-[2-[[(2r)-2-(3-formamido-4-hydroxyphenyl)-2-hydroxyethyl]amino]-2-methylpropyl]-n-(3-phenylpropyl)benzamide Chemical compound C([C@H](O)C=1C=C(NC=O)C(O)=CC=1)NC(C)(C)CC(C=1)=CC=CC=1C(=O)NCCCC1=CC=CC=C1 VNOMOUKHGDETNK-MHZLTWQESA-N 0.000 claims 1
- HCTPWAPLCLXRHW-LJAQVGFWSA-N 3-[2-[[(2r)-2-(3-formamido-4-hydroxyphenyl)-2-hydroxyethyl]amino]-2-methylpropyl]-n-[(2-hydroxynaphthalen-1-yl)methyl]benzamide Chemical compound C1([C@@H](O)CNC(C)(CC=2C=C(C=CC=2)C(=O)NCC=2C3=CC=CC=C3C=CC=2O)C)=CC=C(O)C(NC=O)=C1 HCTPWAPLCLXRHW-LJAQVGFWSA-N 0.000 claims 1
- SRWQEBBAYNXOIN-SANMLTNESA-N 3-[2-[[(2r)-2-(3-formamido-4-hydroxyphenyl)-2-hydroxyethyl]amino]-2-methylpropyl]-n-[(4-hydroxy-3,5-dimethylphenyl)methyl]benzamide Chemical compound CC1=C(O)C(C)=CC(CNC(=O)C=2C=C(CC(C)(C)NC[C@H](O)C=3C=C(NC=O)C(O)=CC=3)C=CC=2)=C1 SRWQEBBAYNXOIN-SANMLTNESA-N 0.000 claims 1
- KUDVAJNIMCJMRY-LJAQVGFWSA-N 3-[2-[[(2r)-2-(3-formamido-4-hydroxyphenyl)-2-hydroxyethyl]amino]-2-methylpropyl]-n-[(6-hydroxynaphthalen-2-yl)methyl]benzamide Chemical compound C1([C@@H](O)CNC(C)(CC=2C=C(C=CC=2)C(=O)NCC=2C=C3C=CC(O)=CC3=CC=2)C)=CC=C(O)C(NC=O)=C1 KUDVAJNIMCJMRY-LJAQVGFWSA-N 0.000 claims 1
- JZBROANLMHCYRC-MHZLTWQESA-N 3-[2-[[(2r)-2-(3-formamido-4-hydroxyphenyl)-2-hydroxyethyl]amino]-2-methylpropyl]-n-[2-(4-hydroxy-3-methylphenyl)ethyl]benzamide Chemical compound C1=C(O)C(C)=CC(CCNC(=O)C=2C=C(CC(C)(C)NC[C@H](O)C=3C=C(NC=O)C(O)=CC=3)C=CC=2)=C1 JZBROANLMHCYRC-MHZLTWQESA-N 0.000 claims 1
- CSHZSOPXCQGWHN-MHZLTWQESA-N 3-[2-[[(2r)-2-(3-formamido-4-hydroxyphenyl)-2-hydroxyethyl]amino]-2-methylpropyl]-n-[2-(4-hydroxyphenyl)-2-methylpropyl]benzamide Chemical compound C([C@H](O)C=1C=C(NC=O)C(O)=CC=1)NC(C)(C)CC(C=1)=CC=CC=1C(=O)NCC(C)(C)C1=CC=C(O)C=C1 CSHZSOPXCQGWHN-MHZLTWQESA-N 0.000 claims 1
- UAYLYESTPLEKPK-MHZLTWQESA-N 3-[2-[[(2r)-2-(3-formamido-4-hydroxyphenyl)-2-hydroxyethyl]amino]-2-methylpropyl]-n-[2-(4-methoxyphenyl)ethyl]benzamide Chemical compound C1=CC(OC)=CC=C1CCNC(=O)C1=CC=CC(CC(C)(C)NC[C@H](O)C=2C=C(NC=O)C(O)=CC=2)=C1 UAYLYESTPLEKPK-MHZLTWQESA-N 0.000 claims 1
- IGXHROJVYKVFSY-MHZLTWQESA-N 3-[2-[[(2r)-2-(3-formamido-4-hydroxyphenyl)-2-hydroxyethyl]amino]-2-methylpropyl]-n-[2-(4-methylphenyl)ethyl]benzamide Chemical compound C1=CC(C)=CC=C1CCNC(=O)C1=CC=CC(CC(C)(C)NC[C@H](O)C=2C=C(NC=O)C(O)=CC=2)=C1 IGXHROJVYKVFSY-MHZLTWQESA-N 0.000 claims 1
- PCOCIUHHAYBVLJ-SANMLTNESA-N 3-[2-[[(2r)-2-(3-formamido-4-hydroxyphenyl)-2-hydroxyethyl]amino]-2-methylpropyl]-n-[2-[3-(trifluoromethyl)phenyl]ethyl]benzamide Chemical compound C([C@H](O)C=1C=C(NC=O)C(O)=CC=1)NC(C)(C)CC(C=1)=CC=CC=1C(=O)NCCC1=CC=CC(C(F)(F)F)=C1 PCOCIUHHAYBVLJ-SANMLTNESA-N 0.000 claims 1
- QXKQAKGFRQCQDJ-HKBQPEDESA-N 3-[2-[[(2r)-2-(3-formamido-4-hydroxyphenyl)-2-hydroxyethyl]amino]-2-methylpropyl]-n-[[3-(4-hydroxyphenyl)phenyl]methyl]benzamide Chemical compound C([C@H](O)C=1C=C(NC=O)C(O)=CC=1)NC(C)(C)CC(C=1)=CC=CC=1C(=O)NCC(C=1)=CC=CC=1C1=CC=C(O)C=C1 QXKQAKGFRQCQDJ-HKBQPEDESA-N 0.000 claims 1
- VQGHXENVZOAJLP-HKBQPEDESA-N 3-[2-[[(2r)-2-(3-formamido-4-hydroxyphenyl)-2-hydroxyethyl]amino]-2-methylpropyl]-n-[[4-(4-hydroxyphenyl)phenyl]methyl]benzamide Chemical compound C([C@H](O)C=1C=C(NC=O)C(O)=CC=1)NC(C)(C)CC(C=1)=CC=CC=1C(=O)NCC(C=C1)=CC=C1C1=CC=C(O)C=C1 VQGHXENVZOAJLP-HKBQPEDESA-N 0.000 claims 1
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- VNYSSYRCGWBHLG-AMOLWHMGSA-N leukotriene B4 Chemical compound CCCCC\C=C/C[C@@H](O)\C=C\C=C\C=C/[C@@H](O)CCCC(O)=O VNYSSYRCGWBHLG-AMOLWHMGSA-N 0.000 claims 1
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- YEESKJGWJFYOOK-IJHYULJSSA-N leukotriene D4 Chemical compound CCCCC\C=C/C\C=C/C=C/C=C/[C@H]([C@@H](O)CCCC(O)=O)SC[C@H](N)C(=O)NCC(O)=O YEESKJGWJFYOOK-IJHYULJSSA-N 0.000 claims 1
- OTZRAYGBFWZKMX-JUDRUQEKSA-N leukotriene E4 Chemical compound CCCCCC=CCC=C\C=C\C=C\[C@@H](SC[C@H](N)C(O)=O)[C@@H](O)CCCC(O)=O OTZRAYGBFWZKMX-JUDRUQEKSA-N 0.000 claims 1
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- XIUZOEOMIBLBPX-MHZLTWQESA-N methyl 4-[[[2-[3-[2-[[(2r)-2-(3-formamido-4-hydroxyphenyl)-2-hydroxyethyl]amino]-2-methylpropyl]phenyl]acetyl]amino]methyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1CNC(=O)CC1=CC=CC(CC(C)(C)NC[C@H](O)C=2C=C(NC=O)C(O)=CC=2)=C1 XIUZOEOMIBLBPX-MHZLTWQESA-N 0.000 claims 1
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- FNUVWXCARQBDKB-RFZIMGSGSA-N n-(1-adamantyl)-3-[2-[[(2r)-2-(3-formamido-4-hydroxyphenyl)-2-hydroxyethyl]amino]-2-methylpropyl]benzamide Chemical compound C1([C@@H](O)CNC(C)(CC=2C=C(C=CC=2)C(=O)NC23CC4CC(CC(C4)C2)C3)C)=CC=C(O)C(NC=O)=C1 FNUVWXCARQBDKB-RFZIMGSGSA-N 0.000 claims 1
- YPFFPPCSHDPDQC-MHZLTWQESA-N n-(2,3-dihydro-1h-inden-2-yl)-3-[2-[[(2r)-2-(3-formamido-4-hydroxyphenyl)-2-hydroxyethyl]amino]-2-methylpropyl]benzamide Chemical compound C1([C@@H](O)CNC(C)(CC=2C=C(C=CC=2)C(=O)NC2CC3=CC=CC=C3C2)C)=CC=C(O)C(NC=O)=C1 YPFFPPCSHDPDQC-MHZLTWQESA-N 0.000 claims 1
- FOTGYUORDQTRKG-VWLOTQADSA-N n-(cyclohexylmethyl)-3-[2-[[(2r)-2-(3-formamido-4-hydroxyphenyl)-2-hydroxyethyl]amino]-2-methylpropyl]benzamide Chemical compound C([C@H](O)C=1C=C(NC=O)C(O)=CC=1)NC(C)(C)CC(C=1)=CC=CC=1C(=O)NCC1CCCCC1 FOTGYUORDQTRKG-VWLOTQADSA-N 0.000 claims 1
- UCBKWOXJEHJARP-NDEPHWFRSA-N n-[(3,4-dimethylphenyl)methyl]-2-[3-[2-[[(2r)-2-(3-formamido-4-hydroxyphenyl)-2-hydroxyethyl]amino]-2-methylpropyl]phenyl]acetamide Chemical compound C1=C(C)C(C)=CC=C1CNC(=O)CC1=CC=CC(CC(C)(C)NC[C@H](O)C=2C=C(NC=O)C(O)=CC=2)=C1 UCBKWOXJEHJARP-NDEPHWFRSA-N 0.000 claims 1
- CNRTXWUEYZSLMH-MHZLTWQESA-N n-[(3,4-dimethylphenyl)methyl]-2-[3-[2-[[(2r)-2-(3-formamido-4-hydroxyphenyl)-2-hydroxyethyl]amino]ethyl]phenyl]acetamide Chemical compound C1=C(C)C(C)=CC=C1CNC(=O)CC1=CC=CC(CCNC[C@H](O)C=2C=C(NC=O)C(O)=CC=2)=C1 CNRTXWUEYZSLMH-MHZLTWQESA-N 0.000 claims 1
- FEWIJKAMAJDQKA-CPJLOUKISA-N n-[(3,5-dichloro-2-hydroxyphenyl)methyl]-2-[3-[(2r)-2-[[(2r)-2-(3-formamido-4-hydroxyphenyl)-2-hydroxyethyl]amino]propyl]phenyl]acetamide Chemical compound C([C@@H](C)NC[C@H](O)C=1C=C(NC=O)C(O)=CC=1)C(C=1)=CC=CC=1CC(=O)NCC1=CC(Cl)=CC(Cl)=C1O FEWIJKAMAJDQKA-CPJLOUKISA-N 0.000 claims 1
- XAAMAYJCPIMJMJ-DEOSSOPVSA-N n-[(3,6-dichloro-2-hydroxyphenyl)methyl]-3-[2-[[(2r)-2-(3-formamido-4-hydroxyphenyl)-2-hydroxyethyl]amino]-2-methylpropyl]benzamide Chemical compound C([C@H](O)C=1C=C(NC=O)C(O)=CC=1)NC(C)(C)CC(C=1)=CC=CC=1C(=O)NCC1=C(Cl)C=CC(Cl)=C1O XAAMAYJCPIMJMJ-DEOSSOPVSA-N 0.000 claims 1
- YAGIMXCYPBCTSU-GDJIYFAZSA-N n-[(4-acetamidophenyl)methyl]-2-[3-[(2r)-2-[[(2r)-2-(3-formamido-4-hydroxyphenyl)-2-hydroxyethyl]amino]propyl]phenyl]acetamide Chemical compound C([C@@H](C)NC[C@H](O)C=1C=C(NC=O)C(O)=CC=1)C(C=1)=CC=CC=1CC(=O)NCC1=CC=C(NC(C)=O)C=C1 YAGIMXCYPBCTSU-GDJIYFAZSA-N 0.000 claims 1
- JFIVWTZJMBPVJM-MHZLTWQESA-N n-[(4-cyanophenyl)methyl]-2-[3-[2-[[(2r)-2-(3-formamido-4-hydroxyphenyl)-2-hydroxyethyl]amino]-2-methylpropyl]phenyl]acetamide Chemical compound C([C@H](O)C=1C=C(NC=O)C(O)=CC=1)NC(C)(C)CC(C=1)=CC=CC=1CC(=O)NCC1=CC=C(C#N)C=C1 JFIVWTZJMBPVJM-MHZLTWQESA-N 0.000 claims 1
- WFIVGBRCHBGQJQ-SANMLTNESA-N n-[(5-chloro-2-hydroxyphenyl)methyl]-2-[3-[2-[[(2r)-2-(3-formamido-4-hydroxyphenyl)-2-hydroxyethyl]amino]-2-methylpropyl]phenyl]acetamide Chemical compound C([C@H](O)C=1C=C(NC=O)C(O)=CC=1)NC(C)(C)CC(C=1)=CC=CC=1CC(=O)NCC1=CC(Cl)=CC=C1O WFIVGBRCHBGQJQ-SANMLTNESA-N 0.000 claims 1
- XIDUCKRMPLMUFF-NDEPHWFRSA-N n-[2-(2,6-dimethylphenyl)ethyl]-3-[2-[[(2r)-2-(3-formamido-4-hydroxyphenyl)-2-hydroxyethyl]amino]-2-methylpropyl]benzamide Chemical compound CC1=CC=CC(C)=C1CCNC(=O)C1=CC=CC(CC(C)(C)NC[C@H](O)C=2C=C(NC=O)C(O)=CC=2)=C1 XIDUCKRMPLMUFF-NDEPHWFRSA-N 0.000 claims 1
- CQCHRYVUNIEWNS-SANMLTNESA-N n-[2-(2-chlorophenyl)ethyl]-3-[2-[[(2r)-2-(3-formamido-4-hydroxyphenyl)-2-hydroxyethyl]amino]-2-methylpropyl]benzamide Chemical compound C([C@H](O)C=1C=C(NC=O)C(O)=CC=1)NC(C)(C)CC(C=1)=CC=CC=1C(=O)NCCC1=CC=CC=C1Cl CQCHRYVUNIEWNS-SANMLTNESA-N 0.000 claims 1
- JZSRHJFUBHGQGJ-QHCPKHFHSA-N n-[2-hydroxy-5-[(1r)-1-hydroxy-2-[[2-methyl-1-[3-(piperidine-1-carbonyl)phenyl]propan-2-yl]amino]ethyl]phenyl]formamide Chemical compound C([C@H](O)C=1C=C(NC=O)C(O)=CC=1)NC(C)(C)CC(C=1)=CC=CC=1C(=O)N1CCCCC1 JZSRHJFUBHGQGJ-QHCPKHFHSA-N 0.000 claims 1
- YCMMBHSOWRUSSO-PBBNMVCDSA-N n-[5-[(1r)-2-[[(2r)-1-[3-[3-(3,4-dihydro-1h-isoquinolin-2-yl)-3-oxopropyl]phenyl]propan-2-yl]amino]-1-hydroxyethyl]-2-hydroxyphenyl]formamide Chemical compound C1([C@@H](O)CN[C@@H](CC=2C=C(CCC(=O)N3CC4=CC=CC=C4CC3)C=CC=2)C)=CC=C(O)C(NC=O)=C1 YCMMBHSOWRUSSO-PBBNMVCDSA-N 0.000 claims 1
- XDTIKHMYYUVJET-NGOKVRLYSA-N n-[[4-(dimethylamino)phenyl]methyl]-2-[3-[(2r)-2-[[(2r)-2-(3-formamido-4-hydroxyphenyl)-2-hydroxyethyl]amino]propyl]phenyl]acetamide Chemical compound C([C@@H](C)NC[C@H](O)C=1C=C(NC=O)C(O)=CC=1)C(C=1)=CC=CC=1CC(=O)NCC1=CC=C(N(C)C)C=C1 XDTIKHMYYUVJET-NGOKVRLYSA-N 0.000 claims 1
- AGSMPNUCVWEPPP-SANMLTNESA-N n-benzyl-2-[3-[2-[[(2r)-2-(3-formamido-4-hydroxyphenyl)-2-hydroxyethyl]amino]-2-methylpropyl]phenyl]acetamide Chemical compound C([C@H](O)C=1C=C(NC=O)C(O)=CC=1)NC(C)(C)CC(C=1)=CC=CC=1CC(=O)NCC1=CC=CC=C1 AGSMPNUCVWEPPP-SANMLTNESA-N 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
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- 208000007892 occupational asthma Diseases 0.000 claims 1
- 102000002574 p38 Mitogen-Activated Protein Kinases Human genes 0.000 claims 1
- 108010068338 p38 Mitogen-Activated Protein Kinases Proteins 0.000 claims 1
- 230000001991 pathophysiological effect Effects 0.000 claims 1
- 230000037361 pathway Effects 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 239000002935 phosphatidylinositol 3 kinase inhibitor Substances 0.000 claims 1
- 239000002570 phosphodiesterase III inhibitor Substances 0.000 claims 1
- 239000002587 phosphodiesterase IV inhibitor Substances 0.000 claims 1
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
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- 125000000565 sulfonamide group Chemical group 0.000 claims 1
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- 239000002462 tachykinin receptor antagonist Substances 0.000 claims 1
- 229960000278 theophylline Drugs 0.000 claims 1
- 229940124597 therapeutic agent Drugs 0.000 claims 1
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
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- VMWNQDUVQKEIOC-CYBMUJFWSA-N apomorphine Chemical compound C([C@H]1N(C)CC2)C3=CC=C(O)C(O)=C3C3=C1C2=CC=C3 VMWNQDUVQKEIOC-CYBMUJFWSA-N 0.000 abstract 1
Classifications
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/54—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C217/56—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms
- C07C217/60—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms linked by carbon chains having two carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
- C07D335/02—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
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- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/34—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
- C07C233/42—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
- C07C233/43—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of a saturated carbon skeleton
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- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
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- C07C237/32—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton having the nitrogen atom of the carboxamide group bound to an acyclic carbon atom of a hydrocarbon radical substituted by oxygen atoms
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- 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
- C07C311/45—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups at least one of the singly-bound nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom, e.g. N-acylaminosulfonamides
- C07C311/46—Y being a hydrogen or a carbon atom
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- C07C317/00—Sulfones; Sulfoxides
- C07C317/26—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C317/32—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
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- C—CHEMISTRY; METALLURGY
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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- C07C323/39—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
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- C07C323/39—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
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- 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
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/40—Acylated substituent nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
- C07D217/06—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines with the ring nitrogen atom acylated by carboxylic or carbonic acids, or with sulfur or nitrogen analogues thereof, e.g. carbamates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
- C07D217/14—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals
- C07D217/16—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/22—Bridged ring systems
- C07D221/24—Camphidines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/192—Radicals derived from carboxylic acids from aromatic carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/56—Ring systems containing bridged rings
- C07C2603/58—Ring systems containing bridged rings containing three rings
- C07C2603/70—Ring systems containing bridged rings containing three rings containing only six-membered rings
- C07C2603/74—Adamantanes
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- Engineering & Computer Science (AREA)
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- Biomedical Technology (AREA)
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- Transplantation (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Hydrogenated Pyridines (AREA)
- Pyridine Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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EP04290767 | 2004-03-23 | ||
GB0425054A GB0425054D0 (en) | 2004-03-23 | 2004-11-12 | Formamide derivatives for the treatment of diseases |
PCT/IB2005/000619 WO2005092840A1 (en) | 2004-03-23 | 2005-03-10 | Formamide derivatives useful as adrenoceptor |
Publications (1)
Publication Number | Publication Date |
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HRP20100402T1 true HRP20100402T1 (hr) | 2010-09-30 |
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Application Number | Title | Priority Date | Filing Date |
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HR20100402T HRP20100402T1 (hr) | 2004-03-23 | 2010-07-20 | Formamidni derivati korisni kao ardrenoceptor |
Country Status (30)
Country | Link |
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JP (2) | JP4033892B2 (nl) |
KR (1) | KR100806478B1 (nl) |
AR (1) | AR050236A1 (nl) |
AT (1) | ATE469121T1 (nl) |
CA (1) | CA2560547C (nl) |
CY (1) | CY1112549T1 (nl) |
DE (1) | DE602005021472D1 (nl) |
DK (1) | DK1730103T3 (nl) |
DO (1) | DOP2005000045A (nl) |
EA (1) | EA010133B1 (nl) |
ES (1) | ES2343808T3 (nl) |
GB (1) | GB0425054D0 (nl) |
GE (1) | GEP20084455B (nl) |
HN (1) | HN2005000118A (nl) |
HR (1) | HRP20100402T1 (nl) |
IL (1) | IL178102A (nl) |
IS (1) | IS8552A (nl) |
MA (1) | MA28480B1 (nl) |
MX (1) | MXPA06011019A (nl) |
MY (1) | MY144103A (nl) |
NL (1) | NL1028597C2 (nl) |
NO (1) | NO20064806L (nl) |
NZ (1) | NZ549839A (nl) |
PE (1) | PE20060264A1 (nl) |
PT (1) | PT1730103E (nl) |
RS (1) | RS51438B (nl) |
SI (1) | SI1730103T1 (nl) |
SV (1) | SV2005002056A (nl) |
TW (1) | TWI335312B (nl) |
UY (1) | UY28819A1 (nl) |
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US8481569B2 (en) | 2008-04-23 | 2013-07-09 | Takeda Pharmaceutical Company Limited | Iminopyridine derivatives and use thereof |
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ES2005492A6 (es) * | 1987-12-23 | 1989-03-01 | Lasa Lab | Procedimiento de obtencion de n-(2-hidroxi-5-(1-hidroxi-2((2- (4-metoxifenil)-1metiletil)amino)etil)fenil)foramida (i). |
CH686869A5 (de) * | 1991-04-05 | 1996-07-31 | Sepracor Inc | Beta (2) -bronchienerweiternde Arzneistoffe in Form ihrer Bronchienerweiternden Enantiomeren zur Verwendung fuer die Herstellung eines Mittels zur verbesserten Therapie. |
UA73965C2 (en) * | 1999-12-08 | 2005-10-17 | Theravance Inc | b2 ADRENERGIC RECEPTOR ANTAGONISTS |
OA11558A (en) * | 1999-12-08 | 2004-06-03 | Advanced Medicine Inc | Beta 2-adrenergic receptor agonists. |
US6653323B2 (en) * | 2001-11-13 | 2003-11-25 | Theravance, Inc. | Aryl aniline β2 adrenergic receptor agonists |
TWI249515B (en) * | 2001-11-13 | 2006-02-21 | Theravance Inc | Aryl aniline beta2 adrenergic receptor agonists |
US6747043B2 (en) * | 2002-05-28 | 2004-06-08 | Theravance, Inc. | Alkoxy aryl β2 adrenergic receptor agonists |
US7317102B2 (en) * | 2003-04-01 | 2008-01-08 | Theravance, Inc. | Diarylmethyl and related compounds |
US7268147B2 (en) * | 2003-05-15 | 2007-09-11 | Pfizer Inc | Compounds useful for the treatment of diseases |
ES2293530T3 (es) * | 2004-01-22 | 2008-03-16 | Pfizer, Inc. | Derivados de sulfonamidas para el tratamiento de enfermedades. |
WO2005092861A1 (en) * | 2004-03-11 | 2005-10-06 | Pfizer Limited | Quinolinone derivatives pharmaceutical compositions containing them and their use |
BRPI0508927A (pt) * | 2004-03-17 | 2007-08-14 | Pfizer | compostos úteis para o tratamento de doenças |
WO2005092887A1 (en) * | 2004-03-23 | 2005-10-06 | Pfizer Limited | Compounds for the treatment of diseases |
WO2005092841A1 (en) * | 2004-03-23 | 2005-10-06 | Pfizer Limited | Compounds having beta-agonist activity |
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2004
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2005
- 2005-03-10 DK DK05708714.0T patent/DK1730103T3/da active
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- 2005-03-10 DE DE602005021472T patent/DE602005021472D1/de active Active
- 2005-03-10 CA CA2560547A patent/CA2560547C/en not_active Expired - Fee Related
- 2005-03-10 AT AT05708714T patent/ATE469121T1/de active
- 2005-03-10 NZ NZ549839A patent/NZ549839A/en not_active IP Right Cessation
- 2005-03-10 PT PT05708714T patent/PT1730103E/pt unknown
- 2005-03-10 JP JP2007504493A patent/JP4033892B2/ja not_active Expired - Fee Related
- 2005-03-10 EA EA200601544A patent/EA010133B1/ru not_active IP Right Cessation
- 2005-03-10 RS RSP-2010/0339A patent/RS51438B/en unknown
- 2005-03-10 SI SI200531057T patent/SI1730103T1/sl unknown
- 2005-03-10 ES ES05708714T patent/ES2343808T3/es active Active
- 2005-03-10 KR KR1020067019640A patent/KR100806478B1/ko not_active IP Right Cessation
- 2005-03-16 MY MYPI20051118A patent/MY144103A/en unknown
- 2005-03-18 SV SV2005002056A patent/SV2005002056A/es unknown
- 2005-03-18 HN HN2005000118A patent/HN2005000118A/es unknown
- 2005-03-21 PE PE2005000321A patent/PE20060264A1/es not_active Application Discontinuation
- 2005-03-22 TW TW094108791A patent/TWI335312B/zh not_active IP Right Cessation
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- 2005-03-22 AR ARP050101118A patent/AR050236A1/es not_active Application Discontinuation
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2006
- 2006-09-14 IL IL178102A patent/IL178102A/en not_active IP Right Cessation
- 2006-09-22 MA MA29335A patent/MA28480B1/fr unknown
- 2006-10-10 IS IS8552A patent/IS8552A/is unknown
- 2006-10-23 NO NO20064806A patent/NO20064806L/no not_active Application Discontinuation
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2007
- 2007-09-14 JP JP2007239523A patent/JP4819770B2/ja not_active Expired - Fee Related
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2010
- 2010-07-05 CY CY20101100620T patent/CY1112549T1/el unknown
- 2010-07-20 HR HR20100402T patent/HRP20100402T1/hr unknown
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