SK7212001A3 - Nonsteroidal antiinflammatories - Google Patents
Nonsteroidal antiinflammatories Download PDFInfo
- Publication number
- SK7212001A3 SK7212001A3 SK721-2001A SK7212001A SK7212001A3 SK 7212001 A3 SK7212001 A3 SK 7212001A3 SK 7212001 A SK7212001 A SK 7212001A SK 7212001 A3 SK7212001 A3 SK 7212001A3
- Authority
- SK
- Slovakia
- Prior art keywords
- methyl
- group
- hydroxy
- fluoro
- carbon atoms
- Prior art date
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- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 152
- 230000003110 anti-inflammatory effect Effects 0.000 claims abstract description 20
- 239000003814 drug Substances 0.000 claims abstract description 13
- -1 5,5,5,4,4-pentafluoropentyl Chemical group 0.000 claims description 81
- 125000004432 carbon atom Chemical group C* 0.000 claims description 63
- WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical compound C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 claims description 40
- 238000000034 method Methods 0.000 claims description 39
- 230000002757 inflammatory effect Effects 0.000 claims description 25
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 201000010099 disease Diseases 0.000 claims description 22
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 22
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 21
- 208000010668 atopic eczema Diseases 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 17
- 230000000172 allergic effect Effects 0.000 claims description 17
- 230000008569 process Effects 0.000 claims description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
- 230000002062 proliferating effect Effects 0.000 claims description 16
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 11
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- 229910052731 fluorine Inorganic materials 0.000 claims description 10
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 9
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 9
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- JFRDFBMXCNARFQ-UHFFFAOYSA-N 3,3,3-trifluoro-2-[[1-(5-fluoro-2-hydroxyphenyl)cyclopropyl]methyl]-2-hydroxy-n-(1-oxo-3h-2-benzofuran-5-yl)propanamide Chemical compound OC1=CC=C(F)C=C1C1(CC(O)(C(=O)NC=2C=C3COC(=O)C3=CC=2)C(F)(F)F)CC1 JFRDFBMXCNARFQ-UHFFFAOYSA-N 0.000 claims description 8
- 125000001153 fluoro group Chemical group F* 0.000 claims description 8
- 238000002560 therapeutic procedure Methods 0.000 claims description 8
- HRDWGLORAAHIRG-UHFFFAOYSA-N 3,3,3-trifluoro-2-[[1-(5-fluoro-2-methoxyphenyl)cyclopropyl]methyl]-2-hydroxy-n-(1-oxo-3h-2-benzofuran-5-yl)propanamide Chemical compound COC1=CC=C(F)C=C1C1(CC(O)(C(=O)NC=2C=C3COC(=O)C3=CC=2)C(F)(F)F)CC1 HRDWGLORAAHIRG-UHFFFAOYSA-N 0.000 claims description 7
- QNDBLFHVAMTSHZ-UHFFFAOYSA-N 5-[[4-(5-fluoro-2-hydroxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyl]amino]-3h-2-benzofuran-1-one Chemical compound C=1C=C2C(=O)OCC2=CC=1NCC(O)(C(F)(F)F)CC(C)(C)C1=CC(F)=CC=C1O QNDBLFHVAMTSHZ-UHFFFAOYSA-N 0.000 claims description 7
- 206010020751 Hypersensitivity Diseases 0.000 claims description 7
- 125000002252 acyl group Chemical group 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
- 230000004054 inflammatory process Effects 0.000 claims description 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 206010028980 Neoplasm Diseases 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 238000011282 treatment Methods 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 5
- VZRCPIGJGAFFMU-UHFFFAOYSA-N 4-(4-bromo-2-methoxyphenyl)-2-hydroxy-4-methyl-n-(4-methyl-1-oxo-2,3-benzoxazin-6-yl)-2-(trifluoromethyl)pentanamide Chemical compound COC1=CC(Br)=CC=C1C(C)(C)CC(O)(C(F)(F)F)C(=O)NC1=CC=C2C(=O)ON=C(C)C2=C1 VZRCPIGJGAFFMU-UHFFFAOYSA-N 0.000 claims description 5
- 206010061218 Inflammation Diseases 0.000 claims description 5
- 208000025747 Rheumatic disease Diseases 0.000 claims description 5
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 5
- 150000007513 acids Chemical class 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 4
- NLPNUYHHRWOSGM-UHFFFAOYSA-N 4-(5-fluoro-2-hydroxyphenyl)-2-hydroxy-4-methyl-n-(4-methyl-1-oxo-2,3-benzoxazin-6-yl)-2-(trifluoromethyl)pentanamide Chemical compound C1=C2C(C)=NOC(=O)C2=CC=C1NC(=O)C(O)(C(F)(F)F)CC(C)(C)C1=CC(F)=CC=C1O NLPNUYHHRWOSGM-UHFFFAOYSA-N 0.000 claims description 4
- GIBZLWRPPUSMTC-UHFFFAOYSA-N 4-(5-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-n-(4-methyl-1-oxo-2,3-benzoxazin-6-yl)-2-(trifluoromethyl)pentanamide Chemical compound COC1=CC=C(F)C=C1C(C)(C)CC(O)(C(F)(F)F)C(=O)NC1=CC=C2C(=O)ON=C(C)C2=C1 GIBZLWRPPUSMTC-UHFFFAOYSA-N 0.000 claims description 4
- PTRUFSHZSSJJNB-UHFFFAOYSA-N 4-bromo-5-[[4-(5-fluoro-2-hydroxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyl]amino]-3h-2-benzofuran-1-one Chemical compound C=1C=C2C(=O)OCC2=C(Br)C=1NCC(O)(C(F)(F)F)CC(C)(C)C1=CC(F)=CC=C1O PTRUFSHZSSJJNB-UHFFFAOYSA-N 0.000 claims description 4
- ZVCDNODZUJDLPU-UHFFFAOYSA-N 6-[[4-(5-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyl]amino]-4-methyl-2,3-benzoxazin-1-one Chemical compound COC1=CC=C(F)C=C1C(C)(C)CC(O)(C(F)(F)F)CNC1=CC=C2C(=O)ON=C(C)C2=C1 ZVCDNODZUJDLPU-UHFFFAOYSA-N 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- 206010047700 Vomiting Diseases 0.000 claims description 4
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 4
- 230000007815 allergy Effects 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 125000004122 cyclic group Chemical group 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 230000035939 shock Effects 0.000 claims description 4
- 230000008673 vomiting Effects 0.000 claims description 4
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 3
- URTADFDQTBTDPM-UHFFFAOYSA-N 4-bromo-5-[[4-(3-bromo-5-fluoro-2-hydroxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyl]amino]-3h-2-benzofuran-1-one Chemical compound C=1C=C2C(=O)OCC2=C(Br)C=1NCC(O)(C(F)(F)F)CC(C)(C)C1=CC(F)=CC(Br)=C1O URTADFDQTBTDPM-UHFFFAOYSA-N 0.000 claims description 3
- DUSKZEWQNAKIFC-UHFFFAOYSA-N 6-[[4-(4-bromo-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyl]amino]-4-methyl-2,3-benzoxazin-1-one Chemical compound COC1=CC(Br)=CC=C1C(C)(C)CC(O)(C(F)(F)F)CNC1=CC=C2C(=O)ON=C(C)C2=C1 DUSKZEWQNAKIFC-UHFFFAOYSA-N 0.000 claims description 3
- 208000023275 Autoimmune disease Diseases 0.000 claims description 3
- 208000008035 Back Pain Diseases 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 208000018522 Gastrointestinal disease Diseases 0.000 claims description 3
- 208000012659 Joint disease Diseases 0.000 claims description 3
- 208000008930 Low Back Pain Diseases 0.000 claims description 3
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- 208000030880 Nose disease Diseases 0.000 claims description 3
- 208000002193 Pain Diseases 0.000 claims description 3
- 206010047115 Vasculitis Diseases 0.000 claims description 3
- 125000004423 acyloxy group Chemical group 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- 201000011510 cancer Diseases 0.000 claims description 3
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 3
- 208000032625 disorder of ear Diseases 0.000 claims description 3
- 208000030172 endocrine system disease Diseases 0.000 claims description 3
- 208000030533 eye disease Diseases 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 208000017169 kidney disease Diseases 0.000 claims description 3
- 208000019423 liver disease Diseases 0.000 claims description 3
- ZGOYZJSOEDPWLZ-UHFFFAOYSA-N n-(4-ethyl-1-oxo-2,3-benzoxazin-6-yl)-2-hydroxy-4-(2-hydroxyphenyl)-4-methyl-2-(trifluoromethyl)pentanamide Chemical compound C1=C2C(CC)=NOC(=O)C2=CC=C1NC(=O)C(O)(C(F)(F)F)CC(C)(C)C1=CC=CC=C1O ZGOYZJSOEDPWLZ-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 3
- 238000006467 substitution reaction Methods 0.000 claims description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- HIZVCIIORGCREW-UHFFFAOYSA-N 1,4-dioxene Chemical group C1COC=CO1 HIZVCIIORGCREW-UHFFFAOYSA-N 0.000 claims description 2
- YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 claims description 2
- 125000001331 3-methylbutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])O* 0.000 claims description 2
- YDUNLELKYSGONE-UHFFFAOYSA-N 6-[[4-(5-fluoro-2-hydroxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyl]amino]-4-methyl-2,3-benzoxazin-1-one Chemical compound C1=C2C(C)=NOC(=O)C2=CC=C1NCC(O)(C(F)(F)F)CC(C)(C)C1=CC(F)=CC=C1O YDUNLELKYSGONE-UHFFFAOYSA-N 0.000 claims description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 2
- 229920001774 Perfluoroether Polymers 0.000 claims description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000006639 cyclohexyl carbonyl group Chemical group 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
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- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
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- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000005246 nonafluorobutyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 claims description 2
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- 229910052717 sulfur Chemical group 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 2
- BPBUAOIZTSGINR-UHFFFAOYSA-N 2-hydroxy-4-(2-methoxyphenyl)-4-methyl-n-(1-oxo-3h-2-benzofuran-5-yl)-2-(trifluoromethyl)pentanamide Chemical compound COC1=CC=CC=C1C(C)(C)CC(O)(C(F)(F)F)C(=O)NC1=CC=C(C(=O)OC2)C2=C1 BPBUAOIZTSGINR-UHFFFAOYSA-N 0.000 claims 1
- QLKLRODYRRCQIT-UHFFFAOYSA-N 4-(5-fluoro-2-phenylmethoxyphenyl)-2-hydroxy-4-methyl-n-(1-oxo-3h-2-benzofuran-5-yl)-2-(trifluoromethyl)pentanamide Chemical compound C=1C=C2C(=O)OCC2=CC=1NC(=O)C(O)(C(F)(F)F)CC(C)(C)C1=CC(F)=CC=C1OCC1=CC=CC=C1 QLKLRODYRRCQIT-UHFFFAOYSA-N 0.000 claims 1
- PULRWJHOJVCGNJ-UHFFFAOYSA-N 4-[2-(difluoromethoxy)-5-fluorophenyl]-2-hydroxy-4-methyl-n-(1-oxo-3h-2-benzofuran-5-yl)-2-(trifluoromethyl)pentanamide Chemical compound C=1C=C2C(=O)OCC2=CC=1NC(=O)C(O)(C(F)(F)F)CC(C)(C)C1=CC(F)=CC=C1OC(F)F PULRWJHOJVCGNJ-UHFFFAOYSA-N 0.000 claims 1
- HHFPOOWLGMMYSZ-UHFFFAOYSA-N 4-[5-fluoro-2-(methoxymethoxy)phenyl]-2-hydroxy-4-methyl-n-(1-oxo-3h-2-benzofuran-5-yl)-2-(trifluoromethyl)pentanamide Chemical compound COCOC1=CC=C(F)C=C1C(C)(C)CC(O)(C(F)(F)F)C(=O)NC1=CC=C(C(=O)OC2)C2=C1 HHFPOOWLGMMYSZ-UHFFFAOYSA-N 0.000 claims 1
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- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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Classifications
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- 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
- C07D307/87—Benzo [c] furans; Hydrogenated benzo [c] furans
- C07D307/88—Benzo [c] furans; Hydrogenated benzo [c] furans with one oxygen atom directly attached in position 1 or 3
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Immunology (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Otolaryngology (AREA)
- Diabetes (AREA)
- Heart & Thoracic Surgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
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- Anesthesiology (AREA)
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- Dermatology (AREA)
- Pulmonology (AREA)
- Cardiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Steroid Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19856475A DE19856475A1 (de) | 1998-11-27 | 1998-11-27 | Nichtsteroidale Entzündungshemmer |
| PCT/EP1999/009754 WO2000032584A2 (fr) | 1998-11-27 | 1999-11-29 | Inhibiteurs d'inflammation non steroidiques |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK7212001A3 true SK7212001A3 (en) | 2003-02-04 |
Family
ID=7890303
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK721-2001A SK7212001A3 (en) | 1998-11-27 | 1999-11-29 | Nonsteroidal antiinflammatories |
Country Status (31)
| Country | Link |
|---|---|
| US (1) | US6323199B1 (fr) |
| EP (1) | EP1133486B1 (fr) |
| JP (1) | JP2002531446A (fr) |
| KR (1) | KR100762058B1 (fr) |
| CN (1) | CN1171883C (fr) |
| AR (1) | AR021419A1 (fr) |
| AT (1) | ATE285405T1 (fr) |
| AU (1) | AU762735B2 (fr) |
| BG (1) | BG65030B1 (fr) |
| BR (1) | BR9915755A (fr) |
| CA (1) | CA2352367A1 (fr) |
| CO (1) | CO5140109A1 (fr) |
| CZ (1) | CZ20011866A3 (fr) |
| DE (2) | DE19856475A1 (fr) |
| EA (1) | EA003299B1 (fr) |
| EE (1) | EE200100283A (fr) |
| ES (1) | ES2235543T3 (fr) |
| HK (1) | HK1043592B (fr) |
| HR (1) | HRP20010483B1 (fr) |
| HU (1) | HUP0104578A3 (fr) |
| IL (2) | IL143393A0 (fr) |
| MY (1) | MY136016A (fr) |
| NO (1) | NO20012562L (fr) |
| NZ (1) | NZ511950A (fr) |
| PE (1) | PE20001245A1 (fr) |
| PL (1) | PL348329A1 (fr) |
| PT (1) | PT1133486E (fr) |
| SK (1) | SK7212001A3 (fr) |
| UA (1) | UA73102C2 (fr) |
| WO (1) | WO2000032584A2 (fr) |
| ZA (1) | ZA200105280B (fr) |
Families Citing this family (51)
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| DE10346940B3 (de) * | 2003-10-06 | 2005-06-16 | Schering Ag | Substituierte Pentanole, ihre Verwendung zur Herstellung von Arzneimitteln speziell Entzündungshemmer sowie diese enthaltende pharmazeutische Präparate |
| US7238707B2 (en) * | 2000-07-28 | 2007-07-03 | Schering Ag | Substituted pentanols, a process for their production and their use as anti-inflammatory agents |
| DE10038639A1 (de) * | 2000-07-28 | 2002-02-21 | Schering Ag | Nichtsteroidale Entzündungshemmer |
| EP1392639B1 (fr) * | 2001-05-03 | 2008-09-17 | Galileo Laboratories, Inc. | Derives de pyruvates |
| ATE346058T1 (de) * | 2002-01-14 | 2006-12-15 | Boehringer Ingelheim Pharma | Glucocorticoid mimetika, verfahren zu ihrer herstellung, pharmazeutische formulierungen sie enthaltend und verwendungen davon |
| HRP20040887A2 (en) * | 2002-03-26 | 2005-04-30 | Boehringer Ingelheim Pharmaceuticals Inc. | Glucocorticoid mimetics, methods of making them, pharmaceutical compositions, and uses thereof |
| EP1490317A1 (fr) * | 2002-03-26 | 2004-12-29 | Boehringer Ingelheim Pharmaceuticals Inc. | Mimetiques du glucocorticoide, procedes de fabrication de ces mimetiques, compositions pharmaceutiques et leurs utilisations |
| DE10215316C1 (de) * | 2002-04-02 | 2003-12-18 | Schering Ag | Chinolin- und Isochinolin-Derivate, ein pharmazeutisches Mittel und ihre Verwendung als Entzündungshemmer |
| US6897224B2 (en) * | 2002-04-02 | 2005-05-24 | Schering Ag | Quinoline and isoquinoline derivatives, a process for their production and their use as inflammation inhibitors |
| 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 |
| JP2006504678A (ja) * | 2002-08-21 | 2006-02-09 | ベーリンガー インゲルハイム ファーマシューティカルズ インコーポレイテッド | グルココルチコイドミメチックス、その製造方法、その医薬組成物、及び使用 |
| HRP20050185A2 (en) * | 2002-08-29 | 2006-05-31 | Boehringer Ingelheim Pharmaceuticals Inc. | -3 (sulfonamidoethyl)-indole derivatives for use as glucocorticoid mimetics in the treatment of inflammatory, allergic and proliferative diseases |
| US7112584B2 (en) * | 2002-12-20 | 2006-09-26 | Schering Ag | Nonsteroidal antiinflammatory agents |
| DE10261874A1 (de) * | 2002-12-20 | 2004-07-08 | Schering Ag | Nichtsteroidale Entzündungshemmer |
| KR20050109922A (ko) * | 2003-01-03 | 2005-11-22 | 베링거 인겔하임 파마슈티칼즈, 인코포레이티드 | 1-프로판올과 1-프로필아민 유도체 및 글루코코르티코이드리간드로서의 이들의 용도 |
| WO2004071389A2 (fr) * | 2003-02-15 | 2004-08-26 | Glaxo Group Limited | Composés |
| US20040224992A1 (en) * | 2003-02-27 | 2004-11-11 | Boehringer Ingelheim Pharmaceuticals, Inc. | Glucocorticoid mimetics, methods of making them, pharmaceutical compositions, and uses thereof |
| KR20060027376A (ko) * | 2003-07-01 | 2006-03-27 | 쉐링 악티엔게젤샤프트 | 헤테로시클릭 치환된 펜탄올 유도체, 그의 제조 방법 및그의 항염증제로서 용도 |
| 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 |
| UY28526A1 (es) | 2003-09-24 | 2005-04-29 | Boehringer Ingelheim Pharma | Miméticos de glucocorticoides, métodos de preparación composiciones farmacéuticas y usos de los mismos |
| DE10347385A1 (de) | 2003-10-08 | 2005-05-12 | Schering Ag | Umgelagerte Pentanole, ein Verfahren zu ihrer Herstellung und ihre Verwendung als Entzündungshemmer |
| EP1675839B1 (fr) * | 2003-10-16 | 2007-07-11 | Boehringer Ingelheim Pharmaceuticals Inc. | Synthese stereoselective de certains alcools a substitution trifluoromethyle |
| US7795272B2 (en) * | 2004-03-13 | 2010-09-14 | Boehringer Ingelheim Pharmaceutical, Inc. | Glucocorticoid mimetics, methods of making them, pharmaceutical compositions and uses thereof |
| GB0418045D0 (en) | 2004-08-12 | 2004-09-15 | Glaxo Group Ltd | Compounds |
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| DE102005030292A1 (de) * | 2005-06-24 | 2007-01-11 | Schering Ag | Nichtsteroidale Progesteronrezeptor-Modulatoren |
| GB0513297D0 (en) * | 2005-06-29 | 2005-08-03 | Glaxo Group Ltd | Novel compounds |
| CA2519010A1 (fr) | 2005-09-13 | 2007-03-13 | Cognos Incorporated | Systeme et methode pour cadre d'interrogation |
| TW200815361A (en) * | 2005-10-20 | 2008-04-01 | Astrazeneca Ab | Chemical compounds |
| GB0522880D0 (en) * | 2005-11-09 | 2005-12-21 | Glaxo Group Ltd | Novel compounds |
| BRPI0619519A2 (pt) * | 2005-12-09 | 2011-10-04 | Hoffmann La Roche | compostos de propionamida como agentes antiinflamatórios |
| WO2007065828A1 (fr) * | 2005-12-09 | 2007-06-14 | F. Hoffmann-La Roche Ag | Modulateurs du recepteur des glucocorticoides utiles en tant qu'agents anti-inflammatoires |
| WO2007120083A1 (fr) * | 2006-04-13 | 2007-10-25 | Astrazeneca Ab | Utilisation de derives de carboxamide dans la fabrication d'un medicament pour le traitement de conditions inflammatoires, allergiques et dermatologiques |
| CA2649509A1 (fr) | 2006-04-20 | 2007-11-01 | Glaxo Group Limited | Nouveaux composes |
| GB0611587D0 (en) * | 2006-06-12 | 2006-07-19 | Glaxo Group Ltd | Novel compounds |
| WO2008000777A2 (fr) * | 2006-06-29 | 2008-01-03 | Glaxo Group Limited | Nouveaux composés |
| TW200829578A (en) | 2006-11-23 | 2008-07-16 | Astrazeneca Ab | Chemical compounds 537 |
| KR20090097908A (ko) * | 2006-12-06 | 2009-09-16 | 베링거 인겔하임 인터내셔날 게엠베하 | 글루코코르티코이드 모사물, 이의 제조 방법, 이의 약제학적 조성물 및 용도 |
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| UY30805A1 (es) * | 2006-12-21 | 2008-07-31 | Bayer Schering Pharma Ag | Moduladores no esteroides de receptores de progesterona |
| JO2754B1 (en) * | 2006-12-21 | 2014-03-15 | استرازينكا ايه بي | Amylendazoleil derivatives for the treatment of glucocorticoid-mediated disorders |
| US20100056565A1 (en) * | 2007-02-15 | 2010-03-04 | Argenta Discovery Limited | Heterocyclic Derivatives as M3 Muscarinic Receptors |
| UY31831A (es) | 2008-05-20 | 2010-01-05 | Astrazeneca Ab | Derivados de indazoles sustituidos con fenilo o piridinilo |
| KR20110020902A (ko) * | 2008-06-06 | 2011-03-03 | 베링거 인겔하임 인터내셔날 게엠베하 | 글루코코르티코이드 유사체, 이의 제조방법, 약제학적 조성물 및 이의 용도 |
| GB0814729D0 (en) * | 2008-08-12 | 2008-09-17 | Argenta Discovery Ltd | New combination |
| US20120220590A1 (en) | 2009-07-31 | 2012-08-30 | Thombare Pravin S | Novel compounds as modulators of glucocorticoid receptors |
| WO2011061527A1 (fr) | 2009-11-17 | 2011-05-26 | Astrazeneca Ab | Combinaisons qui comprennent un modulateur du récepteur glucocorticoïde, destinées au traitement de maladies respiratoires |
| PL3700513T3 (pl) | 2017-10-27 | 2023-01-09 | Association Pour La Recherche À L'igbmc (Ari) | Niesteroidowe selektywne modulatory agonistyczne receptora glukokortykoidowego (segramy) i ich zastosowania |
| EP3569228A1 (fr) * | 2018-05-17 | 2019-11-20 | Association pour la recherche à l'IGBMC (ARI) | Modulateurs agonistes de récepteurs de glucocorticoïdes sélectifs (segrams) non stéroïdiens et leurs utilisations |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1261835A (fr) | 1984-08-20 | 1989-09-26 | Masaaki Toda | Benz(thio) amides fusionnes |
| GB8617652D0 (en) * | 1986-07-18 | 1986-08-28 | Ici Plc | Acylanilide derivatives |
| GB8617653D0 (en) | 1986-07-18 | 1986-08-28 | Ici Plc | Amide derivatives |
| DE19723722A1 (de) | 1997-05-30 | 1998-12-10 | Schering Ag | Nichtsteroidale Gestagene |
-
1998
- 1998-11-27 DE DE19856475A patent/DE19856475A1/de not_active Withdrawn
-
1999
- 1999-11-24 US US09/448,278 patent/US6323199B1/en not_active Expired - Fee Related
- 1999-11-26 AR ARP990106045A patent/AR021419A1/es unknown
- 1999-11-26 CO CO99074717A patent/CO5140109A1/es unknown
- 1999-11-26 MY MYPI99005172A patent/MY136016A/en unknown
- 1999-11-26 PE PE1999001188A patent/PE20001245A1/es not_active Application Discontinuation
- 1999-11-29 NZ NZ511950A patent/NZ511950A/en unknown
- 1999-11-29 WO PCT/EP1999/009754 patent/WO2000032584A2/fr not_active Ceased
- 1999-11-29 PL PL99348329A patent/PL348329A1/xx unknown
- 1999-11-29 AT AT99963476T patent/ATE285405T1/de not_active IP Right Cessation
- 1999-11-29 PT PT99963476T patent/PT1133486E/pt unknown
- 1999-11-29 EE EEP200100283A patent/EE200100283A/xx unknown
- 1999-11-29 ES ES99963476T patent/ES2235543T3/es not_active Expired - Lifetime
- 1999-11-29 EP EP99963476A patent/EP1133486B1/fr not_active Expired - Lifetime
- 1999-11-29 EA EA200100529A patent/EA003299B1/ru not_active IP Right Cessation
- 1999-11-29 CZ CZ20011866A patent/CZ20011866A3/cs unknown
- 1999-11-29 HU HU0104578A patent/HUP0104578A3/hu unknown
- 1999-11-29 JP JP2000585226A patent/JP2002531446A/ja not_active Withdrawn
- 1999-11-29 KR KR1020017006613A patent/KR100762058B1/ko not_active Expired - Fee Related
- 1999-11-29 DE DE59911340T patent/DE59911340D1/de not_active Expired - Fee Related
- 1999-11-29 CA CA002352367A patent/CA2352367A1/fr not_active Abandoned
- 1999-11-29 IL IL14339399A patent/IL143393A0/xx active IP Right Grant
- 1999-11-29 AU AU19760/00A patent/AU762735B2/en not_active Ceased
- 1999-11-29 CN CN99815852.6A patent/CN1171883C/zh not_active Expired - Fee Related
- 1999-11-29 BR BR9915755-1A patent/BR9915755A/pt not_active Application Discontinuation
- 1999-11-29 HK HK02105244.1A patent/HK1043592B/zh not_active IP Right Cessation
- 1999-11-29 HR HR20010483A patent/HRP20010483B1/xx not_active IP Right Cessation
- 1999-11-29 SK SK721-2001A patent/SK7212001A3/sk unknown
- 1999-11-29 UA UA2001064447A patent/UA73102C2/uk unknown
-
2001
- 2001-05-21 BG BG105527A patent/BG65030B1/bg unknown
- 2001-05-24 IL IL143393A patent/IL143393A/en not_active IP Right Cessation
- 2001-05-25 NO NO20012562A patent/NO20012562L/no not_active Application Discontinuation
- 2001-06-26 ZA ZA200105280A patent/ZA200105280B/en unknown
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