CA2531060A1 - Derives de pentanol substitues par un heterocycle, procede de production de ces composes et leur utilisation comme agents anti-inflammatoires - Google Patents

Derives de pentanol substitues par un heterocycle, procede de production de ces composes et leur utilisation comme agents anti-inflammatoires Download PDF

Info

Publication number: CA2531060A1
Authority: CA; Canada
Prior art keywords: methyl; group; trifluoromethyl; alkyl; hydroxy
Prior art date: 2003-07-01
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

Application number

CA002531060A

Other languages

English (en)

Inventor

Markus Berger

Stefan Baeurle

Hartmut Rehwinkel

Norbert Schmees

Heike Schaecke

Manfred Lehmann

Konrad Krolikiewicz

Arndt J. B. Schottelius

Duy Nguyen

Anne Mengel

Stefan Jaroch

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Bayer Pharma AG

Original Assignee

Individual

Priority date (The priority date 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 date listed.)

2003-07-01

Filing date

2004-06-22

Publication date

2005-01-13

2003-07-01 Priority claimed from DE2003130358 external-priority patent/DE10330358A1/de

2003-10-06 Priority claimed from DE2003146939 external-priority patent/DE10346939A1/de

2004-06-22 Application filed by Individual filed Critical Individual

2005-01-13 Publication of CA2531060A1 publication Critical patent/CA2531060A1/fr

Status Abandoned legal-status Critical Current

Links

238000004519 manufacturing process Methods 0.000 title claims abstract description 37
238000000034 method Methods 0.000 title claims abstract description 36
AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical class CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 title abstract description 18
229940121363 anti-inflammatory agent Drugs 0.000 title abstract description 5
239000002260 anti-inflammatory agent Substances 0.000 title abstract description 5
230000008569 process Effects 0.000 title description 21
125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims abstract description 15
HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims abstract description 10
150000001875 compounds Chemical class 0.000 claims description 146
-1 benzothiazolinyl Chemical group 0.000 claims description 53
239000000203 mixture Substances 0.000 claims description 37
239000001257 hydrogen Substances 0.000 claims description 29
229910052739 hydrogen Inorganic materials 0.000 claims description 29
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 25
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
229910052736 halogen Inorganic materials 0.000 claims description 24
150000002367 halogens Chemical class 0.000 claims description 24
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 20
229910052799 carbon Inorganic materials 0.000 claims description 18
150000003254 radicals Chemical class 0.000 claims description 18
125000003118 aryl group Chemical group 0.000 claims description 16
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 12
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 12
125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 12
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 11
125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims description 11
125000004093 cyano group Chemical group *C#N 0.000 claims description 11
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 11
125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 10
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 10
125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 9
125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims description 9
150000003839 salts Chemical class 0.000 claims description 9
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 8
125000004432 carbon atom Chemical group C* 0.000 claims description 7
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 7
150000001721 carbon Chemical group 0.000 claims description 6
125000001072 heteroaryl group Chemical group 0.000 claims description 6
125000001041 indolyl group Chemical group 0.000 claims description 6
125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 6
125000004430 oxygen atom Chemical group O* 0.000 claims description 6
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 5
125000005843 halogen group Chemical group 0.000 claims description 4
239000008177 pharmaceutical agent 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
230000009467 reduction Effects 0.000 claims description 4
238000006722 reduction reaction Methods 0.000 claims description 4
LCGISIDBXHGCDW-VKHMYHEASA-N L-glutamine amide Chemical compound NC(=O)[C@@H](N)CCC(N)=O LCGISIDBXHGCDW-VKHMYHEASA-N 0.000 claims description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
239000000825 pharmaceutical preparation Substances 0.000 claims description 3
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 2
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
230000029936 alkylation Effects 0.000 claims description 2
238000005804 alkylation reaction Methods 0.000 claims description 2
125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 2
238000006268 reductive amination reaction Methods 0.000 claims description 2
125000006527 (C1-C5) alkyl group Chemical group 0.000 claims 9
125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 4
125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 1
208000027866 inflammatory disease Diseases 0.000 claims 1
XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical group N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 abstract description 13
IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 abstract description 12
BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical group C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 abstract description 11
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 abstract description 8
FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical group N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 abstract description 6
LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical group C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 abstract description 6
WCZVZNOTHYJIEI-UHFFFAOYSA-N cinnoline Chemical group N1=NC=CC2=CC=CC=C21 WCZVZNOTHYJIEI-UHFFFAOYSA-N 0.000 abstract description 4
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 abstract description 4
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 abstract description 4
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 375
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 195
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 159
239000000243 solution Substances 0.000 description 123
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 120
238000005160 1H NMR spectroscopy Methods 0.000 description 113
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 98
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 98
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 89
239000000741 silica gel Substances 0.000 description 84
229910002027 silica gel Inorganic materials 0.000 description 84
101150041968 CDC13 gene Proteins 0.000 description 74
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 69
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 67
239000000047 product Substances 0.000 description 64
238000001704 evaporation Methods 0.000 description 61
230000008020 evaporation Effects 0.000 description 61
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 59
238000004587 chromatography analysis Methods 0.000 description 58
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 48
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 46
239000002904 solvent Substances 0.000 description 45
239000012074 organic phase Substances 0.000 description 38
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 36
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 36
229960000583 acetic acid Drugs 0.000 description 34
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 29
229910052938 sodium sulfate Inorganic materials 0.000 description 29
235000011152 sodium sulphate Nutrition 0.000 description 29
229920006395 saturated elastomer Polymers 0.000 description 27
ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 26
238000006243 chemical reaction Methods 0.000 description 25
150000002466 imines Chemical class 0.000 description 25
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 24
239000011541 reaction mixture Substances 0.000 description 24
239000012071 phase Substances 0.000 description 23
239000012267 brine Substances 0.000 description 22
229910052740 iodine Inorganic materials 0.000 description 22
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 22
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 22
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 21
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
239000008346 aqueous phase Substances 0.000 description 20
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 20
230000002829 reductive effect Effects 0.000 description 19
238000005481 NMR spectroscopy Methods 0.000 description 18
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
208000010668 atopic eczema Diseases 0.000 description 18
230000002757 inflammatory effect Effects 0.000 description 18
MDELYEBAXHZXLZ-UHFFFAOYSA-N 1h-indazol-4-amine Chemical compound NC1=CC=CC2=C1C=NN2 MDELYEBAXHZXLZ-UHFFFAOYSA-N 0.000 description 17
230000000172 allergic effect Effects 0.000 description 16
238000003756 stirring Methods 0.000 description 16
FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 16
HOFRQNRWTVIMDE-UHFFFAOYSA-N 2-hydroxy-4-methyl-2-(trifluoromethyl)pentanal Chemical compound CC(C)CC(O)(C=O)C(F)(F)F HOFRQNRWTVIMDE-UHFFFAOYSA-N 0.000 description 15
239000003921 oil Substances 0.000 description 15
230000002062 proliferating effect Effects 0.000 description 15
229910000030 sodium bicarbonate Inorganic materials 0.000 description 15
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 14
239000003054 catalyst Substances 0.000 description 14
239000000284 extract Substances 0.000 description 14
238000001816 cooling Methods 0.000 description 13
239000000706 filtrate Substances 0.000 description 13
239000012298 atmosphere Substances 0.000 description 12
239000012230 colorless oil Substances 0.000 description 12
239000012043 crude product Substances 0.000 description 12
239000012280 lithium aluminium hydride Substances 0.000 description 12
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 12
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 12
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 12
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 11
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 11
238000003786 synthesis reaction Methods 0.000 description 11
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 10
230000015572 biosynthetic process Effects 0.000 description 10
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 10
150000002148 esters Chemical class 0.000 description 10
238000001914 filtration Methods 0.000 description 10
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
WRFLLCIDQDAHGU-UHFFFAOYSA-N 4-(5-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentanal Chemical compound COC1=CC=C(F)C=C1C(C)(C)CC(O)(C=O)C(F)(F)F WRFLLCIDQDAHGU-UHFFFAOYSA-N 0.000 description 9
BKAJNAXTPSGJCU-UHFFFAOYSA-N 4-methyl-2-oxopentanoic acid Chemical compound CC(C)CC(=O)C(O)=O BKAJNAXTPSGJCU-UHFFFAOYSA-N 0.000 description 9
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 9
102000003676 Glucocorticoid Receptors Human genes 0.000 description 9
108090000079 Glucocorticoid Receptors Proteins 0.000 description 9
239000002253 acid Substances 0.000 description 9
201000010099 disease Diseases 0.000 description 9
150000002431 hydrogen Chemical class 0.000 description 9
FHJBCUIFWOVOFO-UHFFFAOYSA-N 4-(1,3-benzodioxol-4-yl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentanal Chemical compound O=CC(O)(C(F)(F)F)CC(C)(C)C1=CC=CC2=C1OCO2 FHJBCUIFWOVOFO-UHFFFAOYSA-N 0.000 description 8
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 8
NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 8
239000002808 molecular sieve Substances 0.000 description 8
229910052763 palladium Inorganic materials 0.000 description 8
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
239000000126 substance Substances 0.000 description 8
125000001424 substituent group Chemical group 0.000 description 8
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 7
DHLZALAGILMMKC-UHFFFAOYSA-N 2-methylquinazolin-5-amine Chemical compound NC1=CC=CC2=NC(C)=NC=C21 DHLZALAGILMMKC-UHFFFAOYSA-N 0.000 description 7
VKDCEZNDLSXFLR-UHFFFAOYSA-N 8-fluoro-2-methylquinazolin-5-amine Chemical compound NC1=CC=C(F)C2=NC(C)=NC=C21 VKDCEZNDLSXFLR-UHFFFAOYSA-N 0.000 description 7
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 7
238000011097 chromatography purification Methods 0.000 description 7
239000003862 glucocorticoid Substances 0.000 description 7
239000013067 intermediate product Substances 0.000 description 7
HGBOYTHUEUWSSQ-UHFFFAOYSA-N pentanal Chemical compound CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 7
239000002244 precipitate Substances 0.000 description 7
JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 7
235000017557 sodium bicarbonate Nutrition 0.000 description 7
239000012279 sodium borohydride Substances 0.000 description 7
229910000033 sodium borohydride Inorganic materials 0.000 description 7
239000001142 4-methyl-2-oxopentanoic acid Substances 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 6
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 6
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 6
229910052796 boron Inorganic materials 0.000 description 6
238000005661 deetherification reaction Methods 0.000 description 6
239000012362 glacial acetic acid Substances 0.000 description 6
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 6
239000002243 precursor Substances 0.000 description 6
MWKJTNBSKNUMFN-UHFFFAOYSA-N trifluoromethyltrimethylsilane Chemical compound C[Si](C)(C)C(F)(F)F MWKJTNBSKNUMFN-UHFFFAOYSA-N 0.000 description 6
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
GOPYZMJAIPBUGX-UHFFFAOYSA-N [O-2].[O-2].[Mn+4] Chemical class [O-2].[O-2].[Mn+4] GOPYZMJAIPBUGX-UHFFFAOYSA-N 0.000 description 5
125000000217 alkyl group Chemical group 0.000 description 5
230000003110 anti-inflammatory effect Effects 0.000 description 5
244000309464 bull Species 0.000 description 5
239000002274 desiccant Substances 0.000 description 5
239000005457 ice water Substances 0.000 description 5
238000000926 separation method Methods 0.000 description 5
239000000725 suspension Substances 0.000 description 5
229940037128 systemic glucocorticoids Drugs 0.000 description 5
238000012360 testing method Methods 0.000 description 5
239000008096 xylene Substances 0.000 description 5
VUECAJACKRIDFC-UHFFFAOYSA-N 2-methyl-1,3-benzothiazol-7-amine Chemical compound C1=CC(N)=C2SC(C)=NC2=C1 VUECAJACKRIDFC-UHFFFAOYSA-N 0.000 description 4
JYVLIDXNZAXMDK-UHFFFAOYSA-N 2-pentanol Substances CCCC(C)O JYVLIDXNZAXMDK-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
102100032187 Androgen receptor Human genes 0.000 description 4
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
102000004190 Enzymes Human genes 0.000 description 4
108090000790 Enzymes Proteins 0.000 description 4
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 4
239000005909 Kieselgur Substances 0.000 description 4
241001465754 Metazoa Species 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
NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 4
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 4
230000009471 action Effects 0.000 description 4
150000001299 aldehydes Chemical class 0.000 description 4
108010080146 androgen receptors Proteins 0.000 description 4
SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 4
230000037396 body weight Effects 0.000 description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
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150000003624 transition metals Chemical class 0.000 description 1
230000000472 traumatic effect Effects 0.000 description 1
125000001425 triazolyl group Chemical group 0.000 description 1
IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
GHVOECJFQKLZHU-UHFFFAOYSA-N trifluoromethylcyclobutane Chemical compound FC(F)(F)C1CCC1 GHVOECJFQKLZHU-UHFFFAOYSA-N 0.000 description 1
241000701447 unidentified baculovirus Species 0.000 description 1
238000011144 upstream manufacturing Methods 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
230000003612 virological effect Effects 0.000 description 1
208000002003 vulvitis Diseases 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/46—Iso-indoles; Hydrogenated iso-indoles with an oxygen atom in position 1
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/16—Otologicals
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/32—Oxygen atoms
- C07D209/34—Oxygen atoms in position 2
- 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
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- 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
- C07D237/28—Cinnolines
- 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
- 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
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
- C07D241/40—Benzopyrazines
- C07D241/42—Benzopyrazines with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Public Health (AREA)
Pharmacology & Pharmacy (AREA)
General Health & Medical Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Immunology (AREA)
Pulmonology (AREA)
Rheumatology (AREA)
Diabetes (AREA)
Endocrinology (AREA)
Hematology (AREA)
Heart & Thoracic Surgery (AREA)
Pain & Pain Management (AREA)
Cardiology (AREA)
Ophthalmology & Optometry (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Orthopedic Medicine & Surgery (AREA)
Physical Education & Sports Medicine (AREA)
Gastroenterology & Hepatology (AREA)
Urology & Nephrology (AREA)
Dermatology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Indole Compounds (AREA)

CA002531060A 2003-07-01 2004-06-22 Derives de pentanol substitues par un heterocycle, procede de production de ces composes et leur utilisation comme agents anti-inflammatoires Abandoned CA2531060A1 (fr)

Applications Claiming Priority (5)

Application Number	Priority Date	Filing Date	Title
DE2003130358 DE10330358A1 (de)	2003-07-01	2003-07-01	Heterozyklisch substituierte Pentanol-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Entzündungshemmer
DE10330358.8		2003-07-01
DE2003146939 DE10346939A1 (de)	2003-10-06	2003-10-06	Heterocyclisch substituierte Pentanole, ein Verfahren zu ihrer Herstellung und ihre Verwendung als Entzündungshemmer
DE10346939.7		2003-10-06
PCT/EP2004/006765 WO2005003098A1 (fr)	2003-07-01	2004-06-22	Derives de pentanol substitues par un heterocycle, procede de production de ces composes et leur utilisation comme agents anti-inflammatoires

Publications (1)

Publication Number	Publication Date
CA2531060A1 true CA2531060A1 (fr)	2005-01-13

Family

ID=33566017

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002531060A Abandoned CA2531060A1 (fr)	2003-07-01	2004-06-22	Derives de pentanol substitues par un heterocycle, procede de production de ces composes et leur utilisation comme agents anti-inflammatoires

Country Status (13)

Country	Link
EP (1)	EP1638945A1 (fr)
JP (1)	JP2008529963A (fr)
KR (1)	KR20060027376A (fr)
AU (1)	AU2004254205A1 (fr)
BR (1)	BRPI0412231A (fr)
CA (1)	CA2531060A1 (fr)
EA (1)	EA200600148A1 (fr)
EC (1)	ECSP066329A (fr)
IL (1)	IL172899A0 (fr)
MX (1)	MXPA06000169A (fr)
NO (1)	NO20060534L (fr)
RS (1)	RS20050974A (fr)
WO (1)	WO2005003098A1 (fr)

Families Citing this family (31)

* Cited by examiner, † Cited by third party
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US7638515B2 (en)	2003-10-08	2009-12-29	Bayer Schering Pharma Aktiengesellschaft	Tetrahydronaphthalene derivatives, process for their production and their use as anti-inflammatory agents
US7662821B2 (en)	2003-10-08	2010-02-16	Bayer Schering Pharma Ag	Tetrahydronaphthalene derivatives, process for their production and their use as anti-inflammatory agents
PT1670458E (pt)	2003-10-08	2007-03-30	Schering Ag	Derivados de tetra-hidronaftaleno, processo para a sua preparação e utilização como inibidor de inflamação
US20080153859A1 (en)	2004-04-05	2008-06-26	Hartmut Rehwinkel	Multiply-substituted tetrahydronaphthalene derivatives, process for their production and their use as anti-inflammatory agents
GB0418045D0 (en)	2004-08-12	2004-09-15	Glaxo Group Ltd	Compounds
US8093281B2 (en)	2005-04-14	2012-01-10	Glaxo Group Limited	Indazoles as glucocorticoid receptor ligands
DE102005030293A1 (de) *	2005-06-24	2007-01-04	Schering Ag	Verwendung von nichtsteroidale Progesteronrezeptor-Modulatoren
DE102005030292A1 (de) *	2005-06-24	2007-01-11	Schering Ag	Nichtsteroidale Progesteronrezeptor-Modulatoren
GB0522880D0 (en) *	2005-11-09	2005-12-21	Glaxo Group Ltd	Novel compounds
EP1834948A1 (fr)	2006-03-15	2007-09-19	Bayer Schering Pharma Aktiengesellschaft	Derives de tetrahydronaphtalene , procedes pour leur production et leur utilisation en tant qu'anti-inflammatoires
KR20090003349A (ko)	2006-04-20	2009-01-09	글락소 그룹 리미티드	화합물
EP1878717A1 (fr) *	2006-07-14	2008-01-16	Bayer Schering Pharma Aktiengesellschaft	Benzylamines, leur procédé de préparation, leur utilisation comme agents anti-inflammatoires
GB0620385D0 (en)	2006-10-13	2006-11-22	Glaxo Group Ltd	Novel compounds
GB0620406D0 (en) *	2006-10-13	2006-11-22	Glaxo Group Ltd	Novel compounds
EP2089355A2 (fr)	2006-11-01	2009-08-19	Brystol-Myers Squibb Company	Modulateurs de recepteur de glucocorticoide, d'activite ap-1 et/ou nf- kappa b, et leur utilisation
EP1921068A1 (fr) *	2006-11-08	2008-05-14	Bayer Schering Pharma Aktiengesellschaft	Dérivés d'indazole et d'indole comme agents anti-inflammatoires
WO2008055709A1 (fr) *	2006-11-08	2008-05-15	Bayer Schering Pharma Aktiengesellschaft	Dérivés indoles et indazoles en tant qu'agents anti-inflammatoires
EP1921067A1 (fr) *	2006-11-08	2008-05-14	Bayer Schering Pharma Aktiengesellschaft	Dérivés d'indole et d'indazole comme agents anti-inflammatoires
CA2666685A1 (fr) *	2006-11-09	2008-05-22	Bausch & Lomb, Incorporated	Synthese de stereoisomeres selectionnes de certains alcools substitues
UY30805A1 (es) *	2006-12-21	2008-07-31	Bayer Schering Pharma Ag	Moduladores no esteroides de receptores de progesterona
GB0720549D0 (en) *	2007-10-19	2007-11-28	Glaxo Group Ltd	Novel compounds
GB0720544D0 (en) *	2007-10-19	2007-11-28	Glaxo Group Ltd	Novel compounds
GB0720556D0 (en) *	2007-10-19	2007-11-28	Glaxo Group Ltd	Novel compounds
EP2062880A1 (fr)	2007-11-22	2009-05-27	Bayer Schering Pharma Aktiengesellschaft	5-[(3,3,3-Trifluoro-2-hydroxy-1-arylpropyl)amino]-1H-quinolin-2-ones, procédé pour leur production et leur utilisation comme agents anti-inflammatoires
WO2009069736A1 (fr) *	2007-11-28	2009-06-04	Kyowa Hakko Kirin Co., Ltd.	Composé azoté
US8236786B2 (en)	2008-08-07	2012-08-07	Pulmagen Therapeutics (Inflammation) Limited	Respiratory disease treatment
SI2379507T1 (sl)	2008-12-30	2014-02-28	Pulmagen Therapeutics (Inflammation) Limited	Spojine sulfonamida za zdravljenje respiratornih motenj
WO2010150014A1 (fr)	2009-06-24	2010-12-29	Pulmagen Therapeutics (Inflammation) Limited	Glitazones 5r-5–deutérés pour le traitement de maladies respiratoires
WO2011098746A1 (fr)	2010-02-09	2011-08-18	Pulmagen Therapeutics (Inflammation) Limited	Sels d'addition acide cristallins de l'énantiomère (5r) de la 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

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Publication number	Priority date	Publication date	Assignee	Title
DE19723722A1 (de) *	1997-05-30	1998-12-10	Schering Ag	Nichtsteroidale Gestagene
DE19856475A1 (de) *	1998-11-27	2000-05-31	Schering Ag	Nichtsteroidale Entzündungshemmer
DE10038639A1 (de) *	2000-07-28	2002-02-21	Schering Ag	Nichtsteroidale Entzündungshemmer
WO2003059899A1 (fr) *	2002-01-14	2003-07-24	Boehringer Ingelheim Pharmaceuticals, Inc.	Mimetiques de glucocorticoides, procedes de fabrication, preparations pharmaceutiques renfermant ces mimetiques et utilisations
DE10215316C1 (de) *	2002-04-02	2003-12-18	Schering Ag	Chinolin- und Isochinolin-Derivate, ein pharmazeutisches Mittel und ihre Verwendung als Entzündungshemmer

2004
- 2004-06-22 EP EP04740190A patent/EP1638945A1/fr not_active Withdrawn
- 2004-06-22 JP JP2006516031A patent/JP2008529963A/ja not_active Withdrawn
- 2004-06-22 MX MXPA06000169A patent/MXPA06000169A/es unknown
- 2004-06-22 WO PCT/EP2004/006765 patent/WO2005003098A1/fr not_active Ceased
- 2004-06-22 RS YUP-2005/0974A patent/RS20050974A/sr unknown
- 2004-06-22 CA CA002531060A patent/CA2531060A1/fr not_active Abandoned
- 2004-06-22 KR KR1020057025375A patent/KR20060027376A/ko not_active Withdrawn
- 2004-06-22 EA EA200600148A patent/EA200600148A1/ru unknown
- 2004-06-22 BR BRPI0412231-3A patent/BRPI0412231A/pt not_active IP Right Cessation
- 2004-06-22 AU AU2004254205A patent/AU2004254205A1/en not_active Abandoned
2005
- 2005-12-29 IL IL172899A patent/IL172899A0/en unknown
2006
- 2006-01-30 EC EC2006006329A patent/ECSP066329A/es unknown
- 2006-02-01 NO NO20060534A patent/NO20060534L/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
BRPI0412231A (pt)	2006-08-22
WO2005003098A1 (fr)	2005-01-13
NO20060534L (no)	2006-04-03
ECSP066329A (es)	2006-07-28
RS20050974A (sr)	2007-09-21
KR20060027376A (ko)	2006-03-27
MXPA06000169A (es)	2006-04-27
IL172899A0 (en)	2006-06-11
WO2005003098B1 (fr)	2005-03-03
JP2008529963A (ja)	2008-08-07
AU2004254205A1 (en)	2005-01-13
EP1638945A1 (fr)	2006-03-29
EA200600148A1 (ru)	2006-08-25

Legal Events

Date	Code	Title	Description
2009-03-23	EEER	Examination request
2011-06-22	FZDE	Discontinued

Publication	Publication Date	Title
CA2481012C (fr)	2010-01-26	Derives de quinoleine et d'isoquinoleine, procede de production de ces derives et leur utilisation comme agents anti-inflammatoires
AU2004254205A1 (en)	2005-01-13	Heterocyclically substituted pentanol derivatives, method for the production thereof, and use thereof as anti-inflammatory agents
US7109212B2 (en)	2006-09-19	Quinoline and isoquinoline derivatives, a process for their production and their use as inflammation inhibitors
US20050090559A1 (en)	2005-04-28	Heterocyclically-substituted pentanol derivatives, process for their production and their use as anti-inflammatory agents
US7442794B2 (en)	2008-10-28	Rearranged pentanols, a process for their production and their use as anti-inflammatory agents
NZ546473A (en)	2009-09-25	1-amino-2-oxy-substituted tetrahydronaphthalene derivatives, methods for the production thereof, and their use as antiphlogistics
US8097627B2 (en)	2012-01-17	Multiply-substituted tetrahydronaphthalene derivatives, process for their production and their use as anti-inflammatory agents
JP2009529496A (ja)	2009-08-20	誘導型一酸化窒素シンターゼ抑制剤として有用なキノロン類
US7662821B2 (en)	2010-02-16	Tetrahydronaphthalene derivatives, process for their production and their use as anti-inflammatory agents
US7638515B2 (en)	2009-12-29	Tetrahydronaphthalene derivatives, process for their production and their use as anti-inflammatory agents
US20050222154A1 (en)	2005-10-06	Multiply-substituted tetrahydronaphthalene derivatives, process for their production and their use as anti-inflammatory agents
CA2577861A1 (fr)	2006-03-16	Derives d'alkylidene-tetrahydronaphtalene, procedes pour leur production et leur utilisation comme anti-inflammatoires
US20060084652A1 (en)	2006-04-20	Alkylidene-tetrahydronaphthalene derivatives, process for their production and their use as anti-inflammatory agents
DE10346939A1 (de)	2005-05-19	Heterocyclisch substituierte Pentanole, ein Verfahren zu ihrer Herstellung und ihre Verwendung als Entzündungshemmer
US20050267202A1 (en)	2005-12-01	Chromanol derivatives, a process for their production and their use as anti-inflammatory agents
DE10347386B4 (de)	2006-05-24	Tetrahydronaphthalinderivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Entzündungshemmer
DE102004017662B3 (de)	2005-12-08	Mehrfach substituierte Tetrahydronaphthalinderivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Entzündungshemmer
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