CA2472746A1 - Glucocorticoid mimetics, methods of making them, pharmaceutical formulations containing them and uses thereof - Google Patents
Glucocorticoid mimetics, methods of making them, pharmaceutical formulations containing them and uses thereof Download PDFInfo
- Publication number
- CA2472746A1 CA2472746A1 CA002472746A CA2472746A CA2472746A1 CA 2472746 A1 CA2472746 A1 CA 2472746A1 CA 002472746 A CA002472746 A CA 002472746A CA 2472746 A CA2472746 A CA 2472746A CA 2472746 A1 CA2472746 A1 CA 2472746A1
- Authority
- CA
- Canada
- Prior art keywords
- hydroxy
- amide
- oxo
- fluoro
- dihydroisobenzofuran
- Prior art date
- Legal status (The legal status 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 status listed.)
- Abandoned
Links
- 238000000034 method Methods 0.000 title claims abstract description 64
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 23
- 239000003862 glucocorticoid Substances 0.000 title description 23
- 150000001875 compounds Chemical class 0.000 claims abstract description 223
- 102000003676 Glucocorticoid Receptors Human genes 0.000 claims abstract description 66
- 108090000079 Glucocorticoid Receptors Proteins 0.000 claims abstract description 66
- 150000003839 salts Chemical class 0.000 claims abstract description 54
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 52
- 201000010099 disease Diseases 0.000 claims abstract description 44
- 239000000651 prodrug Substances 0.000 claims abstract description 41
- 229940002612 prodrug Drugs 0.000 claims abstract description 41
- 239000012453 solvate Substances 0.000 claims abstract description 36
- 230000002757 inflammatory effect Effects 0.000 claims abstract description 15
- 230000008569 process Effects 0.000 claims abstract description 12
- 208000010668 atopic eczema Diseases 0.000 claims abstract description 11
- 230000000172 allergic effect Effects 0.000 claims abstract description 10
- 230000001404 mediated effect Effects 0.000 claims abstract description 10
- 230000002062 proliferating effect Effects 0.000 claims abstract description 6
- -1 C1-C5 allcanoyloxy Chemical group 0.000 claims description 153
- 150000001408 amides Chemical class 0.000 claims description 87
- 125000001424 substituent group Chemical group 0.000 claims description 59
- 239000002904 solvent Substances 0.000 claims description 38
- 229910052799 carbon Inorganic materials 0.000 claims description 32
- 125000003118 aryl group Chemical group 0.000 claims description 25
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
- 229910052757 nitrogen Inorganic materials 0.000 claims description 20
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 19
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 18
- 238000011282 treatment Methods 0.000 claims description 18
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 17
- 239000003153 chemical reaction reagent Substances 0.000 claims description 17
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 17
- 229910052736 halogen Inorganic materials 0.000 claims description 17
- 150000002367 halogens Chemical class 0.000 claims description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
- ISMUWQMUWFPFBZ-UHFFFAOYSA-N 5-amino-3h-2-benzofuran-1-one Chemical compound NC1=CC=C2C(=O)OCC2=C1 ISMUWQMUWFPFBZ-UHFFFAOYSA-N 0.000 claims description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 13
- 125000003342 alkenyl group Chemical group 0.000 claims description 12
- 125000005195 alkyl amino carbonyloxy group Chemical group 0.000 claims description 12
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 11
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 11
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 11
- MOIPGXQKZSZOQX-UHFFFAOYSA-N carbonyl bromide Chemical compound BrC(Br)=O MOIPGXQKZSZOQX-UHFFFAOYSA-N 0.000 claims description 11
- 229910052717 sulfur Inorganic materials 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 125000004414 alkyl thio group Chemical group 0.000 claims description 10
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 125000001072 heteroaryl group Chemical group 0.000 claims description 10
- 125000000623 heterocyclic group Chemical group 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 150000003457 sulfones Chemical class 0.000 claims description 10
- 150000003462 sulfoxides Chemical class 0.000 claims description 10
- 125000004434 sulfur atom Chemical group 0.000 claims description 10
- OZBSREXZWADXQE-UHFFFAOYSA-N 2-benzyl-2-hydroxy-4-methyl-n-(1-oxo-3h-2-benzofuran-5-yl)-4-phenylpentanamide Chemical compound C=1C=CC=CC=1C(C)(C)CC(O)(C(=O)NC=1C=C2COC(=O)C2=CC=1)CC1=CC=CC=C1 OZBSREXZWADXQE-UHFFFAOYSA-N 0.000 claims description 9
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- 125000004423 acyloxy group Chemical group 0.000 claims description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- 229910052740 iodine Inorganic materials 0.000 claims description 9
- 125000002524 organometallic group Chemical group 0.000 claims description 9
- OMIMAFBBRNJDDU-UHFFFAOYSA-N 2-(cyclohexylmethyl)-2-hydroxy-4-methyl-n-(1-oxo-3h-2-benzofuran-5-yl)-4-phenylpentanamide Chemical compound C=1C=CC=CC=1C(C)(C)CC(O)(C(=O)NC=1C=C2COC(=O)C2=CC=1)CC1CCCCC1 OMIMAFBBRNJDDU-UHFFFAOYSA-N 0.000 claims description 8
- KDQXNWXYYPRMAG-UHFFFAOYSA-N 4-(5-fluoro-2-hydroxyphenyl)-2-hydroxy-4-methyl-n-(1-oxo-3h-2-benzofuran-5-yl)-2-(1-phenylethyl)pentanamide Chemical compound C=1C(F)=CC=C(O)C=1C(C)(C)CC(O)(C(=O)NC=1C=C2COC(=O)C2=CC=1)C(C)C1=CC=CC=C1 KDQXNWXYYPRMAG-UHFFFAOYSA-N 0.000 claims description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 8
- 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims description 8
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 8
- 125000000304 alkynyl group Chemical group 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- UCLMIPKAOVLOQS-UHFFFAOYSA-N 2-(cyclohexylmethyl)-2-hydroxy-4-methyl-n-(4-methyl-1-oxo-2,3-benzoxazin-6-yl)-4-phenylpentanamide Chemical compound C1=C2C(C)=NOC(=O)C2=CC=C1NC(=O)C(O)(CC(C)(C)C=1C=CC=CC=1)CC1CCCCC1 UCLMIPKAOVLOQS-UHFFFAOYSA-N 0.000 claims description 7
- ZZWNDPPQMABJJG-UHFFFAOYSA-N 2-(cyclohexylmethyl)-4-(5-fluoro-2-hydroxyphenyl)-2-hydroxy-4-methyl-n-(1-oxo-3h-2-benzofuran-5-yl)pentanamide Chemical compound C=1C(F)=CC=C(O)C=1C(C)(C)CC(O)(C(=O)NC=1C=C2COC(=O)C2=CC=1)CC1CCCCC1 ZZWNDPPQMABJJG-UHFFFAOYSA-N 0.000 claims description 7
- LVZOQUMLGOHFGL-UHFFFAOYSA-N 2-(cyclohexylmethyl)-4-(5-fluoro-2-hydroxyphenyl)-2-hydroxy-4-methyl-n-(4-methyl-1-oxo-2,3-benzoxazin-6-yl)pentanamide Chemical compound C1=C2C(C)=NOC(=O)C2=CC=C1NC(=O)C(O)(CC(C)(C)C=1C(=CC=C(F)C=1)O)CC1CCCCC1 LVZOQUMLGOHFGL-UHFFFAOYSA-N 0.000 claims description 7
- BENOKGPZUXADFC-UHFFFAOYSA-N 2-(cyclohexylmethyl)-4-(5-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-n-(1-oxo-3h-2-benzofuran-5-yl)pentanamide Chemical compound COC1=CC=C(F)C=C1C(C)(C)CC(O)(C(=O)NC=1C=C2COC(=O)C2=CC=1)CC1CCCCC1 BENOKGPZUXADFC-UHFFFAOYSA-N 0.000 claims description 7
- SDUVAUNHFNAIDY-UHFFFAOYSA-N 2-(cyclopentylmethyl)-4-(5-fluoro-2-hydroxyphenyl)-2-hydroxy-4-methyl-n-(1-oxo-3h-2-benzofuran-5-yl)pentanamide Chemical compound C=1C(F)=CC=C(O)C=1C(C)(C)CC(O)(C(=O)NC=1C=C2COC(=O)C2=CC=1)CC1CCCC1 SDUVAUNHFNAIDY-UHFFFAOYSA-N 0.000 claims description 7
- YLCLMJNYMQZSDD-UHFFFAOYSA-N 2-[(2-bromophenyl)methyl]-4-(5-fluoro-2-hydroxyphenyl)-2-hydroxy-4-methyl-n-(1-oxo-3h-2-benzofuran-5-yl)pentanamide Chemical compound C=1C(F)=CC=C(O)C=1C(C)(C)CC(O)(C(=O)NC=1C=C2COC(=O)C2=CC=1)CC1=CC=CC=C1Br YLCLMJNYMQZSDD-UHFFFAOYSA-N 0.000 claims description 7
- BYSKHLURWGQKRW-UHFFFAOYSA-N 2-[(2-chlorophenyl)methyl]-4-(5-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-n-(1-oxo-3h-2-benzofuran-5-yl)pentanamide Chemical compound COC1=CC=C(F)C=C1C(C)(C)CC(O)(C(=O)NC=1C=C2COC(=O)C2=CC=1)CC1=CC=CC=C1Cl BYSKHLURWGQKRW-UHFFFAOYSA-N 0.000 claims description 7
- NJNSLBJQTHFZEY-UHFFFAOYSA-N 2-[(3,4-difluorophenyl)methyl]-4-(5-fluoro-2-hydroxyphenyl)-2-hydroxy-4-methyl-n-(1-oxo-3h-2-benzofuran-5-yl)pentanamide Chemical compound C=1C(F)=CC=C(O)C=1C(C)(C)CC(O)(C(=O)NC=1C=C2COC(=O)C2=CC=1)CC1=CC=C(F)C(F)=C1 NJNSLBJQTHFZEY-UHFFFAOYSA-N 0.000 claims description 7
- DXVZGTRLQAZISS-UHFFFAOYSA-N 2-benzyl-2-hydroxy-4-methyl-n-(4-methyl-1-oxo-2,3-benzoxazin-6-yl)-4-phenylpentanamide Chemical compound C1=C2C(C)=NOC(=O)C2=CC=C1NC(=O)C(O)(CC(C)(C)C=1C=CC=CC=1)CC1=CC=CC=C1 DXVZGTRLQAZISS-UHFFFAOYSA-N 0.000 claims description 7
- MHWZNBBELRMCAO-UHFFFAOYSA-N 2-benzyl-4-(5-fluoro-2-hydroxyphenyl)-2-hydroxy-4-methyl-n-(4-methyl-1-oxo-2,3-benzoxazin-6-yl)pentanamide Chemical compound C1=C2C(C)=NOC(=O)C2=CC=C1NC(=O)C(O)(CC(C)(C)C=1C(=CC=C(F)C=1)O)CC1=CC=CC=C1 MHWZNBBELRMCAO-UHFFFAOYSA-N 0.000 claims description 7
- GGQRUDKBZGUEAN-UHFFFAOYSA-N 2-benzyl-4-(5-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-n-(1-oxo-3h-2-benzofuran-5-yl)pentanamide Chemical compound COC1=CC=C(F)C=C1C(C)(C)CC(O)(C(=O)NC=1C=C2COC(=O)C2=CC=1)CC1=CC=CC=C1 GGQRUDKBZGUEAN-UHFFFAOYSA-N 0.000 claims description 7
- WIPUSJIWHMQENS-UHFFFAOYSA-N 2-benzyl-4-(5-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-n-(4-methyl-1-oxo-2,3-benzoxazin-6-yl)pentanamide Chemical compound COC1=CC=C(F)C=C1C(C)(C)CC(O)(C(=O)NC=1C=C2C(C(ON=C2C)=O)=CC=1)CC1=CC=CC=C1 WIPUSJIWHMQENS-UHFFFAOYSA-N 0.000 claims description 7
- PQYRHFYCGKXFHA-UHFFFAOYSA-N 2-cyclopentyl-4-(5-fluoro-2-hydroxyphenyl)-2-hydroxy-4-methyl-n-(1-oxo-3h-2-benzofuran-5-yl)pentanamide Chemical compound C=1C(F)=CC=C(O)C=1C(C)(C)CC(O)(C(=O)NC=1C=C2COC(=O)C2=CC=1)C1CCCC1 PQYRHFYCGKXFHA-UHFFFAOYSA-N 0.000 claims description 7
- CPZRULIMUHTWKO-UHFFFAOYSA-N 2-hydroxy-4-methyl-2-(2-methyl-2-phenylpropyl)-n-(1-oxo-3h-2-benzofuran-5-yl)-4-phenylpentanamide Chemical compound C=1C=CC=CC=1C(C)(C)CC(O)(C(=O)NC=1C=C2COC(=O)C2=CC=1)CC(C)(C)C1=CC=CC=C1 CPZRULIMUHTWKO-UHFFFAOYSA-N 0.000 claims description 7
- DPOOFZQURZCWQM-UHFFFAOYSA-N 4-(5-fluoro-2-hydroxyphenyl)-2-[(2-fluorophenyl)methyl]-2-hydroxy-4-methyl-n-(1-oxo-3h-2-benzofuran-5-yl)pentanamide Chemical compound C=1C(F)=CC=C(O)C=1C(C)(C)CC(O)(C(=O)NC=1C=C2COC(=O)C2=CC=1)CC1=CC=CC=C1F DPOOFZQURZCWQM-UHFFFAOYSA-N 0.000 claims description 7
- LWEZJUNGMYMBEM-UHFFFAOYSA-N 4-(5-fluoro-2-hydroxyphenyl)-2-hydroxy-2-[(2-hydroxyphenyl)methyl]-4-methyl-n-(1-oxo-3h-2-benzofuran-5-yl)pentanamide Chemical compound C=1C(F)=CC=C(O)C=1C(C)(C)CC(O)(C(=O)NC=1C=C2COC(=O)C2=CC=1)CC1=CC=CC=C1O LWEZJUNGMYMBEM-UHFFFAOYSA-N 0.000 claims description 7
- JRIIXIXSRVUNTB-UHFFFAOYSA-N 4-(5-fluoro-2-hydroxyphenyl)-2-hydroxy-4-methyl-2-[(2-methylphenyl)methyl]-n-(1-oxo-3h-2-benzofuran-5-yl)pentanamide Chemical compound CC1=CC=CC=C1CC(O)(C(=O)NC=1C=C2COC(=O)C2=CC=1)CC(C)(C)C1=CC(F)=CC=C1O JRIIXIXSRVUNTB-UHFFFAOYSA-N 0.000 claims description 7
- VMQAICWFBKPLMD-UHFFFAOYSA-N 4-(5-fluoro-2-methoxyphenyl)-2-[(3-fluorophenyl)methyl]-2-hydroxy-4-methyl-n-(1-oxo-3h-2-benzofuran-5-yl)pentanamide Chemical compound COC1=CC=C(F)C=C1C(C)(C)CC(O)(C(=O)NC=1C=C2COC(=O)C2=CC=1)CC1=CC=CC(F)=C1 VMQAICWFBKPLMD-UHFFFAOYSA-N 0.000 claims description 7
- RHPMTVIFDOGGHG-UHFFFAOYSA-N 4-(5-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-[(2-methylphenyl)methyl]-n-(1-oxo-3h-2-benzofuran-5-yl)pentanamide Chemical compound COC1=CC=C(F)C=C1C(C)(C)CC(O)(C(=O)NC=1C=C2COC(=O)C2=CC=1)CC1=CC=CC=C1C RHPMTVIFDOGGHG-UHFFFAOYSA-N 0.000 claims description 7
- QQFIDVOPZHXZPF-UHFFFAOYSA-N 5-[[2-benzyl-4-(5-fluoro-2-methoxyphenyl)-2-hydroxy-4-methylpentyl]amino]-3h-2-benzofuran-1-one Chemical compound COC1=CC=C(F)C=C1C(C)(C)CC(O)(CC=1C=CC=CC=1)CNC1=CC=C(C(=O)OC2)C2=C1 QQFIDVOPZHXZPF-UHFFFAOYSA-N 0.000 claims description 7
- 206010028980 Neoplasm Diseases 0.000 claims description 7
- WZLNDBZQLWFOAV-UHFFFAOYSA-N O=C1OCC2=CC(=CC=C12)NC(C(CC(C)(C)C1=C(C=CC(=C1)F)O)CC(C1=CC=CC=C1)O)=O Chemical compound O=C1OCC2=CC(=CC=C12)NC(C(CC(C)(C)C1=C(C=CC(=C1)F)O)CC(C1=CC=CC=C1)O)=O WZLNDBZQLWFOAV-UHFFFAOYSA-N 0.000 claims description 7
- 208000025747 Rheumatic disease Diseases 0.000 claims description 7
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 7
- 150000001412 amines Chemical class 0.000 claims description 7
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 7
- 210000001519 tissue Anatomy 0.000 claims description 7
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 6
- BUANGJZKMBTAQD-UHFFFAOYSA-N 2-(cyclohexylmethyl)-4-(5-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-n-(4-methyl-1-oxo-2,3-benzoxazin-6-yl)pentanamide Chemical compound COC1=CC=C(F)C=C1C(C)(C)CC(O)(C(=O)NC=1C=C2C(C(ON=C2C)=O)=CC=1)CC1CCCCC1 BUANGJZKMBTAQD-UHFFFAOYSA-N 0.000 claims description 6
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- XNRQWDOYLDVCKY-UHFFFAOYSA-N 2-[(2-chlorophenyl)methyl]-4-(5-fluoro-2-hydroxyphenyl)-2-hydroxy-4-methyl-n-(1-oxo-3h-2-benzofuran-5-yl)pentanamide Chemical compound C=1C(F)=CC=C(O)C=1C(C)(C)CC(O)(C(=O)NC=1C=C2COC(=O)C2=CC=1)CC1=CC=CC=C1Cl XNRQWDOYLDVCKY-UHFFFAOYSA-N 0.000 claims description 6
- FIZLQKNWYSUVGF-UHFFFAOYSA-N 4-(5-fluoro-2-hydroxyphenyl)-2-[(4-fluorophenyl)methyl]-2-hydroxy-4-methyl-n-(1-oxo-3h-2-benzofuran-5-yl)pentanamide Chemical compound C=1C(F)=CC=C(O)C=1C(C)(C)CC(O)(C(=O)NC=1C=C2COC(=O)C2=CC=1)CC1=CC=C(F)C=C1 FIZLQKNWYSUVGF-UHFFFAOYSA-N 0.000 claims description 6
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- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 6
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- AMTYJDSDBBTHNB-UHFFFAOYSA-N 4-(5-fluoro-2-methoxyphenyl)-2-[(2-fluorophenyl)methyl]-2-hydroxy-4-methyl-n-(1-oxo-3h-2-benzofuran-5-yl)pentanamide Chemical compound COC1=CC=C(F)C=C1C(C)(C)CC(O)(C(=O)NC=1C=C2COC(=O)C2=CC=1)CC1=CC=CC=C1F AMTYJDSDBBTHNB-UHFFFAOYSA-N 0.000 claims description 5
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- WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 claims description 5
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- OOVRGYZCOKWMIO-UHFFFAOYSA-N 2-(cyclohexylmethyl)-n-(3,5-dichlorophenyl)-4-(5-fluoro-2-methoxyphenyl)-2-hydroxy-4-methylpentanamide Chemical compound COC1=CC=C(F)C=C1C(C)(C)CC(O)(C(=O)NC=1C=C(Cl)C=C(Cl)C=1)CC1CCCCC1 OOVRGYZCOKWMIO-UHFFFAOYSA-N 0.000 claims description 4
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Landscapes
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Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US34848602P | 2002-01-14 | 2002-01-14 | |
| US60/348,486 | 2002-01-14 | ||
| US37907802P | 2002-05-09 | 2002-05-09 | |
| US60/379,078 | 2002-05-09 | ||
| PCT/US2003/000300 WO2003059899A1 (en) | 2002-01-14 | 2003-01-03 | Glucocorticoid mimetics, methods of making them, pharmaceutical formulations containing them and uses thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2472746A1 true CA2472746A1 (en) | 2003-07-24 |
Family
ID=26995749
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002472746A Abandoned CA2472746A1 (en) | 2002-01-14 | 2003-01-03 | Glucocorticoid mimetics, methods of making them, pharmaceutical formulations containing them and uses thereof |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US6960581B2 (https=) |
| EP (1) | EP1467982B8 (https=) |
| JP (1) | JP2005519897A (https=) |
| AT (1) | ATE346058T1 (https=) |
| AU (1) | AU2003202216A1 (https=) |
| CA (1) | CA2472746A1 (https=) |
| DE (1) | DE60309829T2 (https=) |
| ES (1) | ES2276038T3 (https=) |
| WO (1) | WO2003059899A1 (https=) |
Families Citing this family (107)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2472746A1 (en) | 2002-01-14 | 2003-07-24 | Boehringer Ingelheim Pharmaceuticals, Inc. | Glucocorticoid mimetics, methods of making them, pharmaceutical formulations containing them and uses thereof |
| UA80120C2 (en) * | 2002-03-26 | 2007-08-27 | Boehringer Ingelheim Pharma | Glucocorticoid mimetics, pharmaceutical composition based thereon |
| CA2477764A1 (en) * | 2002-03-26 | 2003-10-09 | Boehringer Ingelheim Pharmaceuticals, Inc. | Glucocorticoid mimetics, methods of making them, pharmaceutical compositions, and uses thereof |
| US7186864B2 (en) * | 2002-05-29 | 2007-03-06 | Boehringer Ingelheim Pharmaceuticals, Inc. | Glucocorticoid mimetics, methods of making them, pharmaceutical compositions, and uses thereof |
| US7074806B2 (en) * | 2002-06-06 | 2006-07-11 | Boehringer Ingelheim Pharmaceuticals, Inc. | Glucocorticoid mimetics, methods of making them, pharmaceutical compositions, and uses thereof |
| CA2496175A1 (en) | 2002-08-21 | 2004-03-04 | Boehringer Ingelheim Pharmaceuticals, Inc. | Substituted hihydroquinolines as glucocorticoid mimetics, methods of making them, pharmaceutical compositions, and uses thereof |
| EA011095B1 (ru) * | 2002-08-29 | 2008-12-30 | Бёрингер Ингельхайм Фармасьютиклз, Инк. | Производные 3-(сульфонамидоэтил)индола, предназначенные для использования в качестве миметиков глюкокортикоидов при лечении воспалительных, аллергических и пролиферативных заболеваний |
| CA2512257A1 (en) * | 2003-01-03 | 2004-07-29 | Boehringer Ingelheim Pharmaceuticals, Inc. | 1-propanol and 1-propylamine derivatives and their use as glucocorticoid ligands |
| US20040224992A1 (en) * | 2003-02-27 | 2004-11-11 | Boehringer Ingelheim Pharmaceuticals, Inc. | Glucocorticoid mimetics, methods of making them, pharmaceutical compositions, and uses thereof |
| US20050090559A1 (en) * | 2003-07-01 | 2005-04-28 | Markus Berger | Heterocyclically-substituted pentanol derivatives, process for their production and their use as anti-inflammatory agents |
| EP1638945A1 (de) * | 2003-07-01 | 2006-03-29 | Schering Aktiengesellschaft | Heterozyklisch substituierte pentanol-derivate, verfahren zu ihrer herstellung und ihre verwendung als entz ndungshemmer |
| GB0316290D0 (en) | 2003-07-11 | 2003-08-13 | Glaxo Group Ltd | Novel compounds |
| UY28526A1 (es) | 2003-09-24 | 2005-04-29 | Boehringer Ingelheim Pharma | Miméticos de glucocorticoides, métodos de preparación composiciones farmacéuticas y usos de los mismos |
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| DE60309829T2 (de) | 2007-09-13 |
| US6960581B2 (en) | 2005-11-01 |
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| US20030232823A1 (en) | 2003-12-18 |
| WO2003059899A1 (en) | 2003-07-24 |
| EP1467982B1 (en) | 2006-11-22 |
| EP1467982B8 (en) | 2007-04-11 |
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