ZA200603602B - Rearranged pentanols, a method for the production thereof, and their use as antiphlogistics - Google Patents
Rearranged pentanols, a method for the production thereof, and their use as antiphlogistics Download PDFInfo
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- ZA200603602B ZA200603602B ZA200603602A ZA200603602A ZA200603602B ZA 200603602 B ZA200603602 B ZA 200603602B ZA 200603602 A ZA200603602 A ZA 200603602A ZA 200603602 A ZA200603602 A ZA 200603602A ZA 200603602 B ZA200603602 B ZA 200603602B
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- South Africa
- Prior art keywords
- alkyl
- atoms
- hydroxy
- group
- optionally
- Prior art date
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- 238000000034 method Methods 0.000 title claims abstract description 26
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 11
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical class CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 title description 2
- 230000001741 anti-phlogistic effect Effects 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 82
- 230000008569 process Effects 0.000 claims abstract description 23
- -1 thiophthalidyl Chemical group 0.000 claims description 60
- 229910052736 halogen Inorganic materials 0.000 claims description 21
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 21
- 150000002367 halogens Chemical class 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 20
- 150000003254 radicals Chemical class 0.000 claims description 19
- 125000004429 atom Chemical group 0.000 claims description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 11
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 11
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 10
- 150000002466 imines Chemical class 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- 239000000460 chlorine Chemical group 0.000 claims description 9
- 229910052731 fluorine Chemical group 0.000 claims description 9
- 239000011737 fluorine Chemical group 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 7
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 125000002950 monocyclic group Chemical group 0.000 claims description 6
- 125000006574 non-aromatic ring group Chemical group 0.000 claims description 6
- 239000008177 pharmaceutical agent Substances 0.000 claims description 6
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 5
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims description 5
- 125000001041 indolyl group Chemical group 0.000 claims description 5
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 5
- 125000005633 phthalidyl group Chemical group 0.000 claims description 5
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 5
- 125000004434 sulfur atom Chemical group 0.000 claims description 5
- 239000002841 Lewis acid Substances 0.000 claims description 4
- 125000002619 bicyclic group Chemical group 0.000 claims description 4
- 125000001070 dihydroindolyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 4
- 125000004611 dihydroisoindolyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 claims description 4
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 4
- 150000007517 lewis acids Chemical class 0.000 claims description 4
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 125000000332 coumarinyl group Chemical group O1C(=O)C(=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000003151 isocoumarinyl group Chemical group C1(=O)OC(=CC2=CC=CC=C12)* 0.000 claims description 3
- 238000000746 purification Methods 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 208000027866 inflammatory disease Diseases 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 125000005045 dihydroisoquinolinyl group Chemical group C1(NC=CC2=CC=CC=C12)* 0.000 claims 3
- IBPHXKCFBXEFQP-UHFFFAOYSA-N 1,1,1,2,2-pentafluoroethane Chemical compound F[C](F)C(F)(F)F IBPHXKCFBXEFQP-UHFFFAOYSA-N 0.000 claims 1
- 229940121363 anti-inflammatory agent Drugs 0.000 abstract description 4
- 239000002260 anti-inflammatory agent Substances 0.000 abstract description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 129
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 87
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 54
- 239000000243 solution Substances 0.000 description 43
- 238000005160 1H NMR spectroscopy Methods 0.000 description 41
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
- 239000002904 solvent Substances 0.000 description 39
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 38
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 36
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- 239000000741 silica gel Substances 0.000 description 29
- 229910002027 silica gel Inorganic materials 0.000 description 29
- 239000000203 mixture Substances 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 20
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 20
- 208000010668 atopic eczema Diseases 0.000 description 18
- 230000002757 inflammatory effect Effects 0.000 description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 17
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 17
- 238000004587 chromatography analysis Methods 0.000 description 17
- 229910052938 sodium sulfate Inorganic materials 0.000 description 17
- 235000011152 sodium sulphate Nutrition 0.000 description 17
- 230000000172 allergic effect Effects 0.000 description 16
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 15
- 230000002062 proliferating effect Effects 0.000 description 15
- 239000012074 organic phase Substances 0.000 description 14
- 239000011541 reaction mixture Substances 0.000 description 13
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
- 201000010099 disease Diseases 0.000 description 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 10
- 229910052740 iodine Inorganic materials 0.000 description 10
- 229960000583 acetic acid Drugs 0.000 description 9
- 238000001704 evaporation Methods 0.000 description 9
- 230000008020 evaporation Effects 0.000 description 9
- 239000012071 phase Substances 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 239000012267 brine Substances 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 8
- 102000003676 Glucocorticoid Receptors Human genes 0.000 description 7
- 108090000079 Glucocorticoid Receptors Proteins 0.000 description 7
- 239000012362 glacial acetic acid Substances 0.000 description 7
- 239000003862 glucocorticoid Substances 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- 229920006395 saturated elastomer Polymers 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical group [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 6
- 239000008346 aqueous phase Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- RFPMGSKVEAUNMZ-UHFFFAOYSA-N pentylidene Chemical group [CH2+]CCC[CH-] RFPMGSKVEAUNMZ-UHFFFAOYSA-N 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 229910052719 titanium Inorganic materials 0.000 description 6
- 239000010936 titanium Substances 0.000 description 6
- YGZZTGFUGGTXAN-UHFFFAOYSA-N 4-(4-chloro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentanal Chemical compound COC1=CC(Cl)=CC=C1C(C)(C)CC(O)(C=O)C(F)(F)F YGZZTGFUGGTXAN-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 230000003110 anti-inflammatory effect Effects 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- 229940037128 systemic glucocorticoids Drugs 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- DHLZALAGILMMKC-UHFFFAOYSA-N 2-methylquinazolin-5-amine Chemical compound NC1=CC=CC2=NC(C)=NC=C21 DHLZALAGILMMKC-UHFFFAOYSA-N 0.000 description 4
- VNYPAFNRKZFPTD-UHFFFAOYSA-N 4-amino-6-fluoro-2,3-dihydroisoindol-1-one Chemical compound NC1=CC(F)=CC2=C1CNC2=O VNYPAFNRKZFPTD-UHFFFAOYSA-N 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 4
- 102000004190 Enzymes Human genes 0.000 description 4
- 108090000790 Enzymes Proteins 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 239000005909 Kieselgur Substances 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 4
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
- 206010028980 Neoplasm Diseases 0.000 description 4
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
- 230000009471 action Effects 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 239000012298 atmosphere Substances 0.000 description 4
- 230000037396 body weight Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- 210000004185 liver Anatomy 0.000 description 4
- 239000002674 ointment Substances 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- 230000008707 rearrangement Effects 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 238000011282 treatment Methods 0.000 description 4
- PQHXXUIDHGVNKE-UHFFFAOYSA-N 2-methyl-5-nitrophthalazin-1-one Chemical compound C1=CC=C2C(=O)N(C)N=CC2=C1[N+]([O-])=O PQHXXUIDHGVNKE-UHFFFAOYSA-N 0.000 description 3
- GWYLLKSJTXXNKH-UHFFFAOYSA-N 4-(4-chloro-2-methoxyphenyl)-4-methyl-2-(trifluoromethyl)pentane-1,2-diol Chemical compound COC1=CC(Cl)=CC=C1C(C)(C)CC(O)(CO)C(F)(F)F GWYLLKSJTXXNKH-UHFFFAOYSA-N 0.000 description 3
- MSLZIEFTVIOSKM-UHFFFAOYSA-N 4-(4-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentanal Chemical compound COC1=CC(F)=CC=C1C(C)(C)CC(O)(C=O)C(F)(F)F MSLZIEFTVIOSKM-UHFFFAOYSA-N 0.000 description 3
- ZDRVCGZEWGFKSV-UHFFFAOYSA-N 5-nitro-2h-phthalazin-1-one Chemical compound C1=NNC(=O)C2=C1C([N+](=O)[O-])=CC=C2 ZDRVCGZEWGFKSV-UHFFFAOYSA-N 0.000 description 3
- 206010002199 Anaphylactic shock Diseases 0.000 description 3
- 206010020751 Hypersensitivity Diseases 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 230000001154 acute effect Effects 0.000 description 3
- 125000002252 acyl group Chemical group 0.000 description 3
- 208000003455 anaphylaxis Diseases 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 230000001684 chronic effect Effects 0.000 description 3
- 229940117173 croton oil Drugs 0.000 description 3
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- 239000003814 drug Substances 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
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- 208000006454 hepatitis Diseases 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 102000005969 steroid hormone receptors Human genes 0.000 description 3
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- 239000003981 vehicle Substances 0.000 description 3
- QISYDLGFNONVEU-UHFFFAOYSA-N 1,1,1-trifluoro-2-[(4-fluoro-2-methoxyphenyl)-[(2-methylquinazolin-5-yl)amino]methyl]-4-methylpent-3-en-2-ol Chemical compound COC1=CC(F)=CC=C1C(C(O)(C=C(C)C)C(F)(F)F)NC1=CC=CC2=NC(C)=NC=C12 QISYDLGFNONVEU-UHFFFAOYSA-N 0.000 description 2
- FLRLYULGFXLXIN-UHFFFAOYSA-N 1,1,1-trifluoro-2-[(4-fluoro-2-methoxyphenyl)-[(2-methylquinazolin-5-yl)amino]methyl]-4-methylpent-4-en-2-ol Chemical compound COC1=CC(F)=CC=C1C(C(O)(CC(C)=C)C(F)(F)F)NC1=CC=CC2=NC(C)=NC=C12 FLRLYULGFXLXIN-UHFFFAOYSA-N 0.000 description 2
- YUKILTJWFRTXGB-UHFFFAOYSA-N 1-chloro-3-methoxybenzene Chemical compound COC1=CC=CC(Cl)=C1 YUKILTJWFRTXGB-UHFFFAOYSA-N 0.000 description 2
- UJHJUCOIAPMNFY-UHFFFAOYSA-N 2-[(4-chloro-2-methoxyphenyl)-[(2-methylquinazolin-5-yl)amino]methyl]-1,1,1-trifluoro-4-methylpent-3-en-2-ol Chemical compound COC1=CC(Cl)=CC=C1C(C(O)(C=C(C)C)C(F)(F)F)NC1=CC=CC2=NC(C)=NC=C12 UJHJUCOIAPMNFY-UHFFFAOYSA-N 0.000 description 2
- PZUAWAZMZBGQFP-UHFFFAOYSA-N 2-[(4-chloro-2-methoxyphenyl)-[(8-fluoro-2-methylquinazolin-5-yl)amino]methyl]-1,1,1-trifluoro-4-methylpent-4-en-2-ol Chemical compound COC1=CC(Cl)=CC=C1C(C(O)(CC(C)=C)C(F)(F)F)NC1=CC=C(F)C2=NC(C)=NC=C12 PZUAWAZMZBGQFP-UHFFFAOYSA-N 0.000 description 2
- SQDLZADADYUWLA-UHFFFAOYSA-N 2-amino-3,6-difluorobenzoic acid Chemical compound NC1=C(F)C=CC(F)=C1C(O)=O SQDLZADADYUWLA-UHFFFAOYSA-N 0.000 description 2
- DJMRVQFVMPUTGM-UHFFFAOYSA-N 3-bromo-4-nitro-3h-2-benzofuran-1-one Chemical compound [O-][N+](=O)C1=CC=CC2=C1C(Br)OC2=O DJMRVQFVMPUTGM-UHFFFAOYSA-N 0.000 description 2
- KYASMAFCCAVHTQ-UHFFFAOYSA-N 4-(4-chloro-2-methoxyphenyl)-1,1,1-trifluoro-2-[(8-fluoro-2-methylquinazolin-5-yl)iminomethyl]-4-methylpentan-2-ol Chemical compound COC1=CC(Cl)=CC=C1C(C)(C)CC(O)(C(F)(F)F)C=NC1=CC=C(F)C2=NC(C)=NC=C12 KYASMAFCCAVHTQ-UHFFFAOYSA-N 0.000 description 2
- JQRMUDIBDCBLLF-UHFFFAOYSA-N 4-[[4-(5-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentylidene]amino]-2,3-dihydroisoindol-1-one Chemical compound COC1=CC=C(F)C=C1C(C)(C)CC(O)(C(F)(F)F)C=NC1=CC=CC2=C1CNC2=O JQRMUDIBDCBLLF-UHFFFAOYSA-N 0.000 description 2
- HQQTZCPKNZVLFF-UHFFFAOYSA-N 4h-1,2-benzoxazin-3-one Chemical class C1=CC=C2ONC(=O)CC2=C1 HQQTZCPKNZVLFF-UHFFFAOYSA-N 0.000 description 2
- VVSCNNHKPQSUFP-UHFFFAOYSA-N 5,8-difluoro-2-methylquinazoline Chemical compound FC1=CC=C(F)C2=NC(C)=NC=C21 VVSCNNHKPQSUFP-UHFFFAOYSA-N 0.000 description 2
- WZWQCRGQYMJCCM-UHFFFAOYSA-N 5-[[1-(4-fluoro-2-hydroxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pent-4-enyl]amino]-2-methylphthalazin-1-one Chemical compound C=1C=CC(C(N(C)N=C2)=O)=C2C=1NC(C(O)(CC(=C)C)C(F)(F)F)C1=CC=C(F)C=C1O WZWQCRGQYMJCCM-UHFFFAOYSA-N 0.000 description 2
- RHMXIEYNEBQMAC-UHFFFAOYSA-N 5-[[4-(5-bromo-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentylidene]amino]-2h-isoquinolin-1-one Chemical compound COC1=CC=C(Br)C=C1C(C)(C)CC(O)(C(F)(F)F)C=NC1=CC=CC2=C1C=CNC2=O RHMXIEYNEBQMAC-UHFFFAOYSA-N 0.000 description 2
- WJDIKSPSEFZBFL-UHFFFAOYSA-N 5-amino-2-methylphthalazin-1-one Chemical compound C1=CC=C2C(=O)N(C)N=CC2=C1N WJDIKSPSEFZBFL-UHFFFAOYSA-N 0.000 description 2
- SVASVGVAQIVSEZ-UHFFFAOYSA-N 5-amino-2H-isoquinolin-1-one Chemical compound C1=CNC(=O)C2=C1C(N)=CC=C2 SVASVGVAQIVSEZ-UHFFFAOYSA-N 0.000 description 2
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
- C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/26—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings condensed with carbocyclic rings or ring systems
- C07D237/30—Phthalazines
- C07D237/32—Phthalazines with oxygen atoms directly attached to carbon atoms of the nitrogen-containing ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/74—Quinazolines; Hydrogenated quinazolines with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to ring carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/76—Benzo[c]pyrans
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- Health & Medical Sciences (AREA)
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- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
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- Pharmacology & Pharmacy (AREA)
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- Transplantation (AREA)
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10347385A DE10347385A1 (de) | 2003-10-08 | 2003-10-08 | Umgelagerte Pentanole, ein Verfahren zu ihrer Herstellung und ihre Verwendung als Entzündungshemmer |
Publications (1)
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| ZA200603602B true ZA200603602B (en) | 2007-07-25 |
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| ZA200603602A ZA200603602B (en) | 2003-10-08 | 2006-05-05 | Rearranged pentanols, a method for the production thereof, and their use as antiphlogistics |
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| JP (1) | JP2007508269A (el) |
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| CN (1) | CN1867555A (el) |
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| PL (1) | PL1670778T3 (el) |
| PT (1) | PT1670778E (el) |
| RS (1) | RS20060297A (el) |
| WO (1) | WO2005035518A1 (el) |
| ZA (1) | ZA200603602B (el) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
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| DE10347385A1 (de) | 2003-10-08 | 2005-05-12 | Schering Ag | Umgelagerte Pentanole, ein Verfahren zu ihrer Herstellung und ihre Verwendung als Entzündungshemmer |
| US20060012020A1 (en) * | 2004-07-14 | 2006-01-19 | Gilleo Kenneth B | Wafer-level assembly method for semiconductor devices |
| TW200811111A (en) | 2006-04-20 | 2008-03-01 | Glaxo Group Ltd | Novel compounds |
| EP1878717A1 (en) * | 2006-07-14 | 2008-01-16 | Bayer Schering Pharma Aktiengesellschaft | Benzyl amines, a process for their production and their use as anti-inflammatory agents |
| EP2062880A1 (en) * | 2007-11-22 | 2009-05-27 | Bayer Schering Pharma Aktiengesellschaft | 5-[(3,3,3-Trifluoro-2-hydroxy-1-arylpropyl)amino]-1H-quinolin-2-ones, a process for their production and their use as anti-inflammatory agents |
| EP2149558A1 (en) | 2008-07-21 | 2010-02-03 | Bayer Schering Pharma Aktiengesellschaft | 5-[(3,3,3-Trifluoro-2-hydroxy-1-arylpropyl)amino-1-arylquinolin-2-ones, a process for their production and their use as anti-inflammatory agents |
| US20100016338A1 (en) * | 2008-07-21 | 2010-01-21 | Bayer Schering Pharma Aktiengesellschaft | 5-[(3,3,3-Trifluoro-2-hydroxy-1-arylpropyl)amino]-1-arylquinolin-2-ones, a Process for their Production and their Use as Anti-inflammatory Agents |
| US8236786B2 (en) | 2008-08-07 | 2012-08-07 | Pulmagen Therapeutics (Inflammation) Limited | Respiratory disease treatment |
| EA019441B1 (ru) | 2008-12-30 | 2014-03-31 | Палмаджен Терепьютикс (Инфлеммейшн) Лимитед | Сульфонамиды, предназначенные для лечения респираторных нарушений |
| WO2010150014A1 (en) | 2009-06-24 | 2010-12-29 | Pulmagen Therapeutics (Inflammation) Limited | 5r- 5 -deuterated glitazones for respiratory disease treatment |
| WO2011098746A1 (en) | 2010-02-09 | 2011-08-18 | Pulmagen Therapeutics (Inflammation) Limited | Crystalline acid addition salts of ( 5r) -enanti0mer of pioglitazone |
| GB201002224D0 (en) | 2010-02-10 | 2010-03-31 | Argenta Therapeutics Ltd | Respiratory disease treatment |
| GB201002243D0 (en) | 2010-02-10 | 2010-03-31 | Argenta Therapeutics Ltd | Respiratory disease treatment |
| CA2864085C (en) | 2012-02-08 | 2021-11-23 | Sunovion Pharmaceuticals Inc. | Heteroaryl compounds and methods of use thereof |
| WO2018023070A1 (en) | 2016-07-29 | 2018-02-01 | Sunovion Pharmaceuticals, Inc. | Compounds and compositions and uses thereof |
| US10196403B2 (en) | 2016-07-29 | 2019-02-05 | Sunovion Pharmaceuticals Inc. | Compounds and compositions and uses thereof |
| WO2018046678A1 (de) * | 2016-09-08 | 2018-03-15 | Bayer Aktiengesellschaft | Glukokorticoid-rezeptor-agonisten enthaltende formulierungen |
| WO2018046684A1 (en) * | 2016-09-08 | 2018-03-15 | Bayer Pharma Aktiengesellschaft | Process for the preparation of substituted 5-{[2-(alkoxymethyl)-3,3,3-trifluoro-2-hydroxy-1-phenylpropyl]amino}quinolin-2(1h)-ones |
| MX2020000523A (es) | 2017-08-02 | 2020-08-20 | Sunovion Pharmaceuticals Inc | Compuestos de isocromano y usos de los mismos. |
| WO2020186165A1 (en) | 2019-03-14 | 2020-09-17 | Sunovion Pharmaceuticals Inc. | Salts of a isochromanyl compound and crystalline forms, processes for preparing, therapeutic uses, and pharmaceutical compositions thereof |
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|---|---|---|---|---|
| DE19856475A1 (de) | 1998-11-27 | 2000-05-31 | Schering Ag | Nichtsteroidale Entzündungshemmer |
| DE10038639A1 (de) * | 2000-07-28 | 2002-02-21 | Schering Ag | Nichtsteroidale Entzündungshemmer |
| EP1375517A1 (en) * | 2002-06-21 | 2004-01-02 | Smithkline Beecham Corporation | Structure of a glucocorticoid receptor ligand binding domain comprising an expanded binding pocket and methods employing same |
| DE10347385A1 (de) | 2003-10-08 | 2005-05-12 | Schering Ag | Umgelagerte Pentanole, ein Verfahren zu ihrer Herstellung und ihre Verwendung als Entzündungshemmer |
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- 2004-10-06 PT PT04790276T patent/PT1670778E/pt unknown
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2007
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Also Published As
| Publication number | Publication date |
|---|---|
| JP2007508269A (ja) | 2007-04-05 |
| EA200600605A1 (ru) | 2006-10-27 |
| DE502004002037D1 (de) | 2006-12-28 |
| US20050131226A1 (en) | 2005-06-16 |
| BRPI0415203A (pt) | 2006-12-05 |
| EA009958B1 (ru) | 2008-04-28 |
| CA2539878A1 (en) | 2005-04-21 |
| ES2277296T3 (es) | 2007-07-01 |
| CN1867555A (zh) | 2006-11-22 |
| WO2005035518A1 (de) | 2005-04-21 |
| EP1670778B1 (de) | 2006-11-15 |
| IL174469A0 (en) | 2006-08-01 |
| DE10347385A1 (de) | 2005-05-12 |
| NO20062021L (no) | 2006-07-07 |
| AU2004279583A1 (en) | 2005-04-21 |
| KR20060120659A (ko) | 2006-11-27 |
| DK1670778T3 (da) | 2007-03-26 |
| RS20060297A (en) | 2008-08-07 |
| ECSP066540A (es) | 2006-10-17 |
| EP1670778A1 (de) | 2006-06-21 |
| PT1670778E (pt) | 2007-02-28 |
| CY1105994T1 (el) | 2011-04-06 |
| ATE345334T1 (de) | 2006-12-15 |
| CR8358A (es) | 2006-10-06 |
| US7442794B2 (en) | 2008-10-28 |
| MXPA06003999A (es) | 2006-07-05 |
| PL1670778T3 (pl) | 2007-04-30 |
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