NO310356B1 - Trisubstituerte fenylderivater, farmasöytisk preparat inneholdende slike derivater, anvendelse derav og fremgangsmåtefor deres fremstilling - Google Patents

Trisubstituerte fenylderivater, farmasöytisk preparat inneholdende slike derivater, anvendelse derav og fremgangsmåtefor deres fremstilling Download PDF

Info

Publication number: NO310356B1
Authority: NO; Norway
Prior art keywords: formula; compound; compounds; hydroxy; dimethoxyphenyl
Prior art date: 1995-03-14

Application number

NO19974118A

Other languages

English (en)

Norwegian (no)

Other versions

NO974118D0 (no

NO974118L (no

Inventor

Peter Nussbaumer

Original Assignee

Novartis Ag

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.)

1995-03-14

Filing date

1997-09-08

Publication date

2001-06-25

1995-03-14 Priority claimed from GBGB9505080.3A external-priority patent/GB9505080D0/en

1995-03-23 Priority claimed from GBGB9505858.2A external-priority patent/GB9505858D0/en

1995-12-28 Priority claimed from GBGB9526593.0A external-priority patent/GB9526593D0/en

1997-09-08 Application filed by Novartis Ag filed Critical Novartis Ag

1997-09-08 Publication of NO974118D0 publication Critical patent/NO974118D0/no

1997-09-08 Publication of NO974118L publication Critical patent/NO974118L/no

2001-06-25 Publication of NO310356B1 publication Critical patent/NO310356B1/no

Links

238000000034 method Methods 0.000 title claims description 31
230000008569 process Effects 0.000 title claims description 24
238000002360 preparation method Methods 0.000 title claims description 17
239000000825 pharmaceutical preparation Substances 0.000 title claims description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 title description 6
150000001875 compounds Chemical class 0.000 claims abstract description 119
230000002062 proliferating effect Effects 0.000 claims abstract description 9
230000002757 inflammatory effect Effects 0.000 claims abstract description 8
208000000453 Skin Neoplasms Diseases 0.000 claims abstract description 7
201000000849 skin cancer Diseases 0.000 claims abstract description 7
208000017520 skin disease Diseases 0.000 claims abstract description 7
230000002265 prevention Effects 0.000 claims abstract description 6
125000001424 substituent group Chemical group 0.000 claims description 21
125000004356 hydroxy functional group Chemical group O* 0.000 claims description 18
125000004432 carbon atom Chemical group C* 0.000 claims description 17
-1 amino, diacetylamino Chemical group 0.000 claims description 16
239000001257 hydrogen Substances 0.000 claims description 14
229910052739 hydrogen Inorganic materials 0.000 claims description 14
125000000217 alkyl group Chemical group 0.000 claims description 13
238000006243 chemical reaction Methods 0.000 claims description 12
125000003545 alkoxy group Chemical group 0.000 claims description 10
150000003839 salts Chemical group 0.000 claims description 8
239000003085 diluting agent Substances 0.000 claims description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
125000002252 acyl group Chemical group 0.000 claims description 5
125000004122 cyclic group Chemical group 0.000 claims description 5
239000003937 drug carrier Substances 0.000 claims description 5
125000000623 heterocyclic group Chemical group 0.000 claims description 5
230000009467 reduction Effects 0.000 claims description 5
PLSOFLNMARXGBD-UHFFFAOYSA-N 6-[2-(2,5-dimethoxyphenyl)ethyl]-4-ethylquinazoline Chemical group C1=C2C(CC)=NC=NC2=CC=C1CCC1=CC(OC)=CC=C1OC PLSOFLNMARXGBD-UHFFFAOYSA-N 0.000 claims description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
125000003282 alkyl amino group Chemical group 0.000 claims description 4
230000008878 coupling Effects 0.000 claims description 4
238000010168 coupling process Methods 0.000 claims description 4
238000005859 coupling reaction Methods 0.000 claims description 4
125000000524 functional group Chemical group 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
229910052760 oxygen Inorganic materials 0.000 claims description 4
PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 4
229910052717 sulfur Inorganic materials 0.000 claims description 4
125000002950 monocyclic group Chemical group 0.000 claims description 3
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
230000010933 acylation Effects 0.000 claims description 2
238000005917 acylation reaction Methods 0.000 claims description 2
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
125000004414 alkyl thio group Chemical group 0.000 claims description 2
230000029936 alkylation Effects 0.000 claims description 2
238000005804 alkylation reaction Methods 0.000 claims description 2
229940111121 antirheumatic drug quinolines Drugs 0.000 claims description 2
125000004104 aryloxy group Chemical group 0.000 claims description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
ZDQWVKDDJDIVAL-UHFFFAOYSA-N catecholborane Chemical compound C1=CC=C2O[B]OC2=C1 ZDQWVKDDJDIVAL-UHFFFAOYSA-N 0.000 claims description 2
125000004093 cyano group Chemical group *C#N 0.000 claims description 2
125000000753 cycloalkyl group Chemical group 0.000 claims description 2
238000006114 decarboxylation reaction Methods 0.000 claims description 2
238000005661 deetherification reaction Methods 0.000 claims description 2
229910052757 nitrogen Inorganic materials 0.000 claims description 2
239000001301 oxygen Substances 0.000 claims description 2
125000004430 oxygen atom Chemical group O* 0.000 claims description 2
239000002243 precursor Substances 0.000 claims description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
125000006239 protecting group Chemical group 0.000 claims description 2
150000003246 quinazolines Chemical class 0.000 claims description 2
150000003248 quinolines Chemical class 0.000 claims description 2
238000006798 ring closing metathesis reaction Methods 0.000 claims description 2
239000000126 substance Substances 0.000 claims description 2
239000011593 sulfur Substances 0.000 claims description 2
230000001225 therapeutic effect Effects 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 4
PANNVTILWOIJNS-UHFFFAOYSA-N 6-[2-(2,5-dimethoxyphenyl)ethyl]-4-ethoxyquinazoline Chemical compound C1=C2C(OCC)=NC=NC2=CC=C1CCC1=CC(OC)=CC=C1OC PANNVTILWOIJNS-UHFFFAOYSA-N 0.000 claims 1
CTOVSSHKAQWXDM-UHFFFAOYSA-N 6-[2-(2,5-dimethoxyphenyl)ethyl]-4-methylquinazoline Chemical compound COC1=CC=C(OC)C(CCC=2C=C3C(C)=NC=NC3=CC=2)=C1 CTOVSSHKAQWXDM-UHFFFAOYSA-N 0.000 claims 1
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims 1
238000006470 amide elimination reaction Methods 0.000 claims 1
238000007257 deesterification reaction Methods 0.000 claims 1
238000011084 recovery Methods 0.000 claims 1
229910052720 vanadium Inorganic materials 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 120
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 38
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
239000000203 mixture Substances 0.000 description 28
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
239000013078 crystal Substances 0.000 description 20
229910052943 magnesium sulfate Inorganic materials 0.000 description 19
235000019341 magnesium sulphate Nutrition 0.000 description 19
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
210000004027 cell Anatomy 0.000 description 15
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
239000000243 solution Substances 0.000 description 15
239000000741 silica gel Substances 0.000 description 14
229910002027 silica gel Inorganic materials 0.000 description 14
238000005160 1H NMR spectroscopy Methods 0.000 description 13
239000002904 solvent Substances 0.000 description 12
238000003756 stirring Methods 0.000 description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
238000010992 reflux Methods 0.000 description 9
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 8
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
239000000284 extract Substances 0.000 description 8
239000012044 organic layer Substances 0.000 description 8
KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
108091003079 Bovine Serum Albumin Proteins 0.000 description 7
239000007853 buffer solution Substances 0.000 description 7
238000010898 silica gel chromatography Methods 0.000 description 7
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
238000004587 chromatography analysis Methods 0.000 description 6
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
239000003513 alkali Substances 0.000 description 5
239000012043 crude product Substances 0.000 description 5
239000012894 fetal calf serum Substances 0.000 description 5
150000002431 hydrogen Chemical group 0.000 description 5
239000007858 starting material Substances 0.000 description 5
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
230000003110 anti-inflammatory effect Effects 0.000 description 4
230000001028 anti-proliverative effect Effects 0.000 description 4
230000004663 cell proliferation Effects 0.000 description 4
USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 4
238000001704 evaporation Methods 0.000 description 4
230000008020 evaporation Effects 0.000 description 4
239000002480 mineral oil Substances 0.000 description 4
235000010446 mineral oil Nutrition 0.000 description 4
229910052763 palladium Inorganic materials 0.000 description 4
NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 4
239000012312 sodium hydride Substances 0.000 description 4
229910000104 sodium hydride Inorganic materials 0.000 description 4
238000010561 standard procedure Methods 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
IRWASZXFFDVXAA-UHFFFAOYSA-N 6-[2-(2,5-dimethoxyphenyl)ethyl]-1h-quinazolin-4-one Chemical compound COC1=CC=C(OC)C(CCC=2C=C3C(=O)NC=NC3=CC=2)=C1 IRWASZXFFDVXAA-UHFFFAOYSA-N 0.000 description 3
YUEFBUYEPRXDBB-UHFFFAOYSA-N 6-iodoquinazolin-4-amine Chemical compound C1=C(I)C=C2C(N)=NC=NC2=C1 YUEFBUYEPRXDBB-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
239000006144 Dulbecco’s modiﬁed Eagle's medium Substances 0.000 description 3
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 3
206010028980 Neoplasm Diseases 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
201000011510 cancer Diseases 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
238000001816 cooling Methods 0.000 description 3
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
238000000605 extraction Methods 0.000 description 3
210000002510 keratinocyte Anatomy 0.000 description 3
239000002609 medium Substances 0.000 description 3
XBWYZWUREJXJAA-UHFFFAOYSA-N methyl 2-amino-5-[2-(2,5-dimethoxyphenyl)ethyl]benzoate Chemical compound C1=C(N)C(C(=O)OC)=CC(CCC=2C(=CC=C(OC)C=2)OC)=C1 XBWYZWUREJXJAA-UHFFFAOYSA-N 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
239000000047 product Substances 0.000 description 3
238000000746 purification Methods 0.000 description 3
239000011734 sodium Substances 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000000725 suspension Substances 0.000 description 3
210000004881 tumor cell Anatomy 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
CZDKYDOSKNCXSM-UHFFFAOYSA-N 2-(bromomethyl)-1,4-dimethoxybenzene Chemical compound COC1=CC=C(OC)C(CBr)=C1 CZDKYDOSKNCXSM-UHFFFAOYSA-N 0.000 description 2
IOOMXAQUNPWDLL-UHFFFAOYSA-N 2-[6-(diethylamino)-3-(diethyliminiumyl)-3h-xanthen-9-yl]-5-sulfobenzene-1-sulfonate Chemical compound C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=C(S(O)(=O)=O)C=C1S([O-])(=O)=O IOOMXAQUNPWDLL-UHFFFAOYSA-N 0.000 description 2
XYJAHKATEAXAOA-UHFFFAOYSA-N 2-ethynyl-1,4-dimethoxybenzene Chemical group COC1=CC=C(OC)C(C#C)=C1 XYJAHKATEAXAOA-UHFFFAOYSA-N 0.000 description 2
LFRNYDQHQSEOOO-UHFFFAOYSA-N 3-[(2,6-dimethoxyphenyl)methyl]-6-hydroxyquinazolin-4-one Chemical compound COC1=CC=CC(OC)=C1CN1C(=O)C2=CC(O)=CC=C2N=C1 LFRNYDQHQSEOOO-UHFFFAOYSA-N 0.000 description 2
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
BDAIUOPDSRAOKI-UHFFFAOYSA-N 4-chloro-6-iodoquinazoline Chemical compound C1=C(I)C=C2C(Cl)=NC=NC2=C1 BDAIUOPDSRAOKI-UHFFFAOYSA-N 0.000 description 2
DYVGZBUGKQQBDL-UHFFFAOYSA-N 5-[(2,5-dimethoxyphenyl)methoxy]-2-formamidobenzamide Chemical compound COC1=CC=C(OC)C(COC=2C=C(C(NC=O)=CC=2)C(N)=O)=C1 DYVGZBUGKQQBDL-UHFFFAOYSA-N 0.000 description 2
KIRKUSKXZCMJJK-UHFFFAOYSA-N 6-[2-(2,5-dimethoxyphenyl)ethynyl]-n-methylquinazolin-4-amine Chemical compound C1=C2C(NC)=NC=NC2=CC=C1C#CC1=CC(OC)=CC=C1OC KIRKUSKXZCMJJK-UHFFFAOYSA-N 0.000 description 2
QJRNXXLTDWMENM-UHFFFAOYSA-N 6-hydroxy-1h-quinazolin-4-one Chemical compound N1C=NC(=O)C2=CC(O)=CC=C21 QJRNXXLTDWMENM-UHFFFAOYSA-N 0.000 description 2
LHMRXHSULRDCLE-UHFFFAOYSA-N 6-iodo-4-methoxyquinazoline Chemical compound C1=C(I)C=C2C(OC)=NC=NC2=C1 LHMRXHSULRDCLE-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
206010006187 Breast cancer Diseases 0.000 description 2
208000026310 Breast neoplasm Diseases 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
206010009944 Colon cancer Diseases 0.000 description 2
201000004624 Dermatitis Diseases 0.000 description 2
102000001301 EGF receptor Human genes 0.000 description 2
108060006698 EGF receptor Proteins 0.000 description 2
102000009024 Epidermal Growth Factor Human genes 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
239000000908 ammonium hydroxide Substances 0.000 description 2
239000002260 anti-inflammatory agent Substances 0.000 description 2
239000002246 antineoplastic agent Substances 0.000 description 2
239000012298 atmosphere Substances 0.000 description 2
239000002585 base Substances 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
229940098773 bovine serum albumin Drugs 0.000 description 2
201000008275 breast carcinoma Diseases 0.000 description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
238000011097 chromatography purification Methods 0.000 description 2
238000007398 colorimetric assay Methods 0.000 description 2
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
125000002534 ethynyl group Chemical class [H]C#C* 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
239000012737 fresh medium Substances 0.000 description 2
150000004678 hydrides Chemical class 0.000 description 2
238000005984 hydrogenation reaction Methods 0.000 description 2
230000005764 inhibitory process Effects 0.000 description 2
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
239000010410 layer Substances 0.000 description 2
AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 2
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
SQQDDKUFOBMLKY-UHFFFAOYSA-N methyl 2-acetamido-5-[2-(2,5-dimethoxyphenyl)ethenyl]benzoate Chemical compound C1=C(NC(C)=O)C(C(=O)OC)=CC(C=CC=2C(=CC=C(OC)C=2)OC)=C1 SQQDDKUFOBMLKY-UHFFFAOYSA-N 0.000 description 2
YGASXVZXXXSXMH-UHFFFAOYSA-N methyl 2-acetamido-5-[2-(2,5-dimethoxyphenyl)ethyl]benzoate Chemical compound C1=C(NC(C)=O)C(C(=O)OC)=CC(CCC=2C(=CC=C(OC)C=2)OC)=C1 YGASXVZXXXSXMH-UHFFFAOYSA-N 0.000 description 2
BCZUGNNYCCZPAA-UHFFFAOYSA-N n-acetyl-n-[6-[2-(2,5-dimethoxyphenyl)ethynyl]quinazolin-4-yl]acetamide Chemical compound COC1=CC=C(OC)C(C#CC=2C=C3C(N(C(C)=O)C(C)=O)=NC=NC3=CC=2)=C1 BCZUGNNYCCZPAA-UHFFFAOYSA-N 0.000 description 2
BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
230000035755 proliferation Effects 0.000 description 2
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 2
DAEPDZWVDSPTHF-UHFFFAOYSA-M sodium pyruvate Chemical compound [Na+].CC(=O)C([O-])=O DAEPDZWVDSPTHF-UHFFFAOYSA-M 0.000 description 2
239000007787 solid Substances 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
FVUDWHPJVYTKDT-UHFFFAOYSA-M (2,5-dimethoxyphenyl)methyl-triphenylphosphanium;bromide Chemical compound [Br-].COC1=CC=C(OC)C(C[P+](C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 FVUDWHPJVYTKDT-UHFFFAOYSA-M 0.000 description 1
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VBEQCZHXXJYVRD-GACYYNSASA-N uroanthelone Chemical compound C([C@@H](C(=O)N[C@H](C(=O)N[C@@H](CS)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CS)C(=O)N[C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)NCC(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CS)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O)C(C)C)[C@@H](C)O)NC(=O)[C@H](CO)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H](CCSC)NC(=O)[C@H](CS)NC(=O)[C@@H](NC(=O)CNC(=O)CNC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CS)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)CNC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CS)NC(=O)CNC(=O)[C@H]1N(CCC1)C(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@@H](N)CC(N)=O)C(C)C)[C@@H](C)CC)C1=CC=C(O)C=C1 VBEQCZHXXJYVRD-GACYYNSASA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/45—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
- C07C233/53—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
- C07C233/54—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of a saturated carbon skeleton
- 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
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/52—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C07C229/54—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton with amino and carboxyl groups bound to carbon atoms of the same non-condensed six-membered aromatic ring
- C07C229/56—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton with amino and carboxyl groups bound to carbon atoms of the same non-condensed six-membered aromatic ring with amino and carboxyl groups bound in ortho-position
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/52—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C07C229/54—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton with amino and carboxyl groups bound to carbon atoms of the same non-condensed six-membered aromatic ring
- C07C229/64—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton with amino and carboxyl groups bound to carbon atoms of the same non-condensed six-membered aromatic ring the carbon skeleton being further substituted by singly-bound oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/26—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring
- C07C271/28—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring to a carbon atom of a non-condensed six-membered aromatic 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
- 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
- C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
- C07D239/88—Oxygen atoms
- 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
- C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
- C07D239/94—Nitrogen atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
Rheumatology (AREA)
Pain & Pain Management (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Dermatology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Quinoline Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Photoreceptors In Electrophotography (AREA)

NO19974118A 1995-03-14 1997-09-08 Trisubstituerte fenylderivater, farmasöytisk preparat inneholdende slike derivater, anvendelse derav og fremgangsmåtefor deres fremstilling NO310356B1 (no)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
GBGB9505080.3A GB9505080D0 (en)	1995-03-14	1995-03-14	Organic compounds
GBGB9505858.2A GB9505858D0 (en)	1995-03-23	1995-03-23	Organic Compounds
GBGB9526593.0A GB9526593D0 (en)	1995-12-28	1995-12-28	Organic compounds
PCT/EP1996/001116 WO1996028430A1 (en)	1995-03-14	1996-03-14	Trisubstituted phenyl derivatives

Publications (3)

Publication Number	Publication Date
NO974118D0 NO974118D0 (no)	1997-09-08
NO974118L NO974118L (no)	1997-09-08
NO310356B1 true NO310356B1 (no)	2001-06-25

Family

ID=27267624

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO19974118A NO310356B1 (no)	1995-03-14	1997-09-08	Trisubstituerte fenylderivater, farmasöytisk preparat inneholdende slike derivater, anvendelse derav og fremgangsmåtefor deres fremstilling

Country Status (23)

Country	Link
US (1)	US5990116A (de)
EP (1)	EP0815087B1 (de)
JP (1)	JP3194963B2 (de)
KR (1)	KR100437580B1 (de)
CN (1)	CN1101386C (de)
AT (1)	ATE208763T1 (de)
AU (1)	AU704544B2 (de)
BR (1)	BR9607240A (de)
CA (1)	CA2214131C (de)
CZ (1)	CZ289944B6 (de)
DE (1)	DE69616993T2 (de)
DK (1)	DK0815087T3 (de)
ES (1)	ES2168463T3 (de)
FI (1)	FI120537B (de)
HU (1)	HUP9801828A3 (de)
MX (1)	MX9707022A (de)
NO (1)	NO310356B1 (de)
NZ (1)	NZ304291A (de)
PL (1)	PL185875B1 (de)
PT (1)	PT815087E (de)
RU (1)	RU2164224C2 (de)
SK (1)	SK282155B6 (de)
WO (1)	WO1996028430A1 (de)

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UA74803C2 (uk)	1999-11-11	2006-02-15	Осі Фармасьютікалз, Інк.	Стійкий поліморф гідрохлориду n-(3-етинілфеніл)-6,7-біс(2-метоксіетокси)-4-хіназолінаміну, спосіб його одержання (варіанти) та фармацевтичне застосування
JP4665331B2 (ja) *	2000-04-07	2011-04-06	チッソ株式会社	新規なジアミノ化合物、該ジアミノ化合物を用いて合成された重合体、並びに該重合体を用いたワニス、配向膜及び液晶表示素子
BR0213233A (pt) *	2001-10-12	2005-01-04	Warner Lambert Co	Alcinos inibidores de metaloproteinase de matriz
AU2002366103A1 (en) *	2001-11-19	2003-06-10	Iconix Pharmaceuticals, Inc.	Modulators of rho c activity
US7214800B2 (en)	2002-05-09	2007-05-08	Cytokinetics, Inc.	Compounds, compositions, and methods
EP1513820A4 (de)	2002-05-23	2006-09-13	Cytokinetics Inc	Verbindungen, zusammensetzungen und verfahren
AU2003281168A1 (en) *	2002-07-17	2004-02-02	Warner-Lambert Company Llc	Combination of an allosteric alkyne inhibitor of matrix metalloproteinase-13 with a selective inhibitor of cyclooxygenase-2 that is not celecoxib or valdecoxib
WO2004006914A1 (en) *	2002-07-17	2004-01-22	Warner-Lambert Company Llc	Combination of an allosteric alkyne inhibitor of matrix metalloproteinase-13 with celecoxib or valdecoxib
AU2003256805A1 (en)	2002-07-23	2004-02-09	Cytokinetics, Inc.	Compounds compositions and methods
AU2003249539A1 (en) *	2002-08-13	2004-02-25	Warner-Lambert Company Llc	Cyclic compounds containing zinc binding groups as matrix metalloproteinase inhibitors
WO2004034972A2 (en)	2002-09-30	2004-04-29	Cytokinetics, Inc.	Compounds, compositions, and methods
ES2270154T3 (es) *	2002-12-13	2007-04-01	F. Hoffmann-La Roche Ag	Derivados de 3h-quinazolin-4-ona.
GB0319497D0 (en) *	2003-08-19	2003-09-17	Novartis Ag	Organic compounds
SE0400234D0 (sv) *	2004-02-06	2004-02-06	Active Biotech Ab	New compounds, methods for their preparation and use thereof
WO2005091891A2 (en) *	2004-03-11	2005-10-06	Kythera Biopharmaceuticals, Inc.	Compositions and methods for preventing and treating skin and hair conditions
US20080031898A1 (en) *	2004-03-26	2008-02-07	David Nathaniel E	Compositions and methods to increase the effect of a neurotoxin treatment
GB0412769D0 (en) *	2004-06-08	2004-07-07	Novartis Ag	Organic compounds
AU2005268166B2 (en) *	2004-08-04	2011-10-20	Meiji Seika Pharma Co., Ltd.	Quinoline derivative and insecticide containing same as active constituent
WO2008044688A1 (en) *	2006-10-11	2008-04-17	Daiichi Sankyo Company, Limited	Urea derivative
JP5349332B2 (ja) *	2007-02-06	2013-11-20	チェルシー・セラピューティクス，インコーポレイテッド	新規化合物、その調製方法、およびその使用
JP2021515767A (ja)	2018-03-07	2021-06-24	バイエル・アクチエンゲゼルシヤフト	Ｅｒｋ５阻害剤の同定及び使用
WO2021026672A1 (en) *	2019-08-09	2021-02-18	Novartis Ag	Heterocyclic wdr5 inhibitors as anti-cancer compounds

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1996
- 1996-03-14 DE DE69616993T patent/DE69616993T2/de not_active Expired - Fee Related
- 1996-03-14 US US08/913,597 patent/US5990116A/en not_active Expired - Fee Related
- 1996-03-14 HU HU9801828A patent/HUP9801828A3/hu unknown
- 1996-03-14 CA CA002214131A patent/CA2214131C/en not_active Expired - Fee Related
- 1996-03-14 WO PCT/EP1996/001116 patent/WO1996028430A1/en not_active Ceased
- 1996-03-14 JP JP52729096A patent/JP3194963B2/ja not_active Expired - Fee Related
- 1996-03-14 ES ES96908043T patent/ES2168463T3/es not_active Expired - Lifetime
- 1996-03-14 PT PT96908043T patent/PT815087E/pt unknown
- 1996-03-14 NZ NZ304291A patent/NZ304291A/xx not_active IP Right Cessation
- 1996-03-14 EP EP96908043A patent/EP0815087B1/de not_active Expired - Lifetime
- 1996-03-14 BR BR9607240A patent/BR9607240A/pt not_active IP Right Cessation
- 1996-03-14 KR KR1019970706458A patent/KR100437580B1/ko not_active Expired - Fee Related
- 1996-03-14 RU RU97117169/04A patent/RU2164224C2/ru not_active IP Right Cessation
- 1996-03-14 SK SK1245-97A patent/SK282155B6/sk not_active IP Right Cessation
- 1996-03-14 PL PL96322134A patent/PL185875B1/pl not_active IP Right Cessation
- 1996-03-14 AU AU51443/96A patent/AU704544B2/en not_active Ceased
- 1996-03-14 CZ CZ19972869A patent/CZ289944B6/cs not_active IP Right Cessation
- 1996-03-14 DK DK96908043T patent/DK0815087T3/da active
- 1996-03-14 AT AT96908043T patent/ATE208763T1/de not_active IP Right Cessation
- 1996-03-14 CN CN96193716A patent/CN1101386C/zh not_active Expired - Fee Related
1997
- 1997-08-21 FI FI973440A patent/FI120537B/fi not_active IP Right Cessation
- 1997-09-08 NO NO19974118A patent/NO310356B1/no not_active IP Right Cessation
- 1997-09-12 MX MX9707022A patent/MX9707022A/es not_active IP Right Cessation

Also Published As

Publication number	Publication date
CN1101386C (zh)	2003-02-12
ES2168463T3 (es)	2002-06-16
HK1014440A1 (en)	1999-09-30
MX9707022A (es)	1998-06-30
JP3194963B2 (ja)	2001-08-06
WO1996028430A1 (en)	1996-09-19
EP0815087A1 (de)	1998-01-07
CZ289944B6 (cs)	2002-04-17
CZ286997A3 (en)	1997-12-17
AU5144396A (en)	1996-10-02
KR100437580B1 (ko)	2004-07-16
PL185875B1 (pl)	2003-08-29
US5990116A (en)	1999-11-23
FI120537B (fi)	2009-11-30
CA2214131A1 (en)	1996-09-19
DE69616993T2 (de)	2002-07-04
HUP9801828A2 (hu)	1999-03-29
AU704544B2 (en)	1999-04-29
NZ304291A (en)	1999-01-28
KR19980703049A (ko)	1998-09-05
ATE208763T1 (de)	2001-11-15
SK282155B6 (sk)	2001-11-06
NO974118D0 (no)	1997-09-08
DK0815087T3 (da)	2002-03-11
FI973440L (fi)	1997-10-24
DE69616993D1 (de)	2001-12-20
EP0815087B1 (de)	2001-11-14
SK124597A3 (en)	1998-01-14
CA2214131C (en)	2009-06-23
PL322134A1 (en)	1998-01-05
NO974118L (no)	1997-09-08
PT815087E (pt)	2002-04-29
BR9607240A (pt)	1997-11-11
HUP9801828A3 (en)	2001-02-28
JPH11503412A (ja)	1999-03-26
RU2164224C2 (ru)	2001-03-20
CN1183774A (zh)	1998-06-03
FI973440A0 (fi)	1997-08-21

Legal Events

Date	Code	Title	Description
2011-10-24	MM1K	Lapsed by not paying the annual fees

Publication	Publication Date	Title
NO310356B1 (no)	2001-06-25	Trisubstituerte fenylderivater, farmasöytisk preparat inneholdende slike derivater, anvendelse derav og fremgangsmåtefor deres fremstilling
JP6715357B2 (ja)	2020-07-01	イミダゾピリジンアミンフェニル誘導体およびその使用
AU635593B2 (en)	1993-03-25	Azaoxindole derivatives
WO2008008059A1 (en)	2008-01-17	Anti-cancer agents ans uses thereof
AU2017237362A1 (en)	2018-08-09	Naphthyridines as integrin antagonists
KR20140144696A (ko)	2014-12-19	２환성 화합물
CA2929562A1 (en)	2015-06-25	Dimethylbenzoic acid compounds
EP1992622B1 (de)	2011-07-27	4-(3-benzoylaminophenyl)-6,7-dimethoxy-2-methylaminochinazolinderivat
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