NO318800B1 - Benzamidderivater, fremgangsmate for fremstillimg og anvendelse derav samt farmasoytisk sammensetning - Google Patents
Benzamidderivater, fremgangsmate for fremstillimg og anvendelse derav samt farmasoytisk sammensetning Download PDFInfo
- Publication number
- NO318800B1 NO318800B1 NO20011492A NO20011492A NO318800B1 NO 318800 B1 NO318800 B1 NO 318800B1 NO 20011492 A NO20011492 A NO 20011492A NO 20011492 A NO20011492 A NO 20011492A NO 318800 B1 NO318800 B1 NO 318800B1
- Authority
- NO
- Norway
- Prior art keywords
- alkyl
- carboxamide
- methylphenyl
- alkylamino
- formula
- Prior art date
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- 238000000034 method Methods 0.000 title claims abstract description 79
- 238000002360 preparation method Methods 0.000 title claims abstract description 24
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 6
- 230000008569 process Effects 0.000 title claims abstract description 5
- 150000003936 benzamides Chemical class 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 40
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 30
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 30
- 150000003839 salts Chemical class 0.000 claims abstract description 27
- 150000002148 esters Chemical class 0.000 claims abstract description 25
- 102000004127 Cytokines Human genes 0.000 claims abstract description 22
- 108090000695 Cytokines Proteins 0.000 claims abstract description 22
- 150000001408 amides Chemical class 0.000 claims abstract description 21
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 17
- 238000011282 treatment Methods 0.000 claims abstract description 9
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 6
- 230000001404 mediated effect Effects 0.000 claims abstract description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 115
- -1 piperidinyloxy Chemical group 0.000 claims description 66
- 238000006243 chemical reaction Methods 0.000 claims description 38
- 125000001424 substituent group Chemical group 0.000 claims description 32
- 150000001412 amines Chemical class 0.000 claims description 25
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 24
- 239000002253 acid Substances 0.000 claims description 24
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 21
- 238000001727 in vivo Methods 0.000 claims description 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
- 125000006239 protecting group Chemical group 0.000 claims description 19
- 238000004519 manufacturing process Methods 0.000 claims description 15
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 12
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- 125000000524 functional group Chemical group 0.000 claims description 9
- 125000004076 pyridyl group Chemical group 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical group 0.000 claims description 8
- 230000029936 alkylation Effects 0.000 claims description 6
- 238000005804 alkylation reaction Methods 0.000 claims description 6
- 238000003776 cleavage reaction Methods 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 6
- 125000002757 morpholinyl group Chemical group 0.000 claims description 6
- 230000010933 acylation Effects 0.000 claims description 5
- 238000005917 acylation reaction Methods 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 230000007017 scission Effects 0.000 claims description 5
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- QWYCXSDHMJCTLX-UHFFFAOYSA-N n-[3-[[4-(diethylaminomethyl)benzoyl]amino]-4-methylphenyl]-2-morpholin-4-ylpyridine-4-carboxamide Chemical compound C1=CC(CN(CC)CC)=CC=C1C(=O)NC1=CC(NC(=O)C=2C=C(N=CC=2)N2CCOCC2)=CC=C1C QWYCXSDHMJCTLX-UHFFFAOYSA-N 0.000 claims description 4
- SUDGKXVNLSNRAZ-UHFFFAOYSA-N n-[4-methyl-3-[[3-[(4-methylpiperazin-1-yl)methyl]benzoyl]amino]phenyl]-2-morpholin-4-ylpyridine-4-carboxamide Chemical compound C1CN(C)CCN1CC1=CC=CC(C(=O)NC=2C(=CC=C(NC(=O)C=3C=C(N=CC=3)N3CCOCC3)C=2)C)=C1 SUDGKXVNLSNRAZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000001425 triazolyl group Chemical group 0.000 claims description 4
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 3
- 238000003556 assay Methods 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- OXFISQVMPFVVTP-UHFFFAOYSA-N n-[4-methyl-3-[[3-[(4-methyl-1,4-diazepan-1-yl)methyl]benzoyl]amino]phenyl]-2-morpholin-4-ylpyridine-4-carboxamide Chemical compound C1CN(C)CCCN1CC1=CC=CC(C(=O)NC=2C(=CC=C(NC(=O)C=3C=C(N=CC=3)N3CCOCC3)C=2)C)=C1 OXFISQVMPFVVTP-UHFFFAOYSA-N 0.000 claims description 3
- UDSRUJPSZUHVOI-UHFFFAOYSA-N n-[4-methyl-3-[[3-[(4-methylpiperazin-1-yl)methyl]benzoyl]amino]phenyl]furan-2-carboxamide Chemical compound C1CN(C)CCN1CC1=CC=CC(C(=O)NC=2C(=CC=C(NC(=O)C=3OC=CC=3)C=2)C)=C1 UDSRUJPSZUHVOI-UHFFFAOYSA-N 0.000 claims description 3
- 125000003386 piperidinyl group Chemical group 0.000 claims description 3
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 3
- 125000000335 thiazolyl group Chemical group 0.000 claims description 3
- JKGPQSYGOYJTNI-UHFFFAOYSA-N 2-(azepan-1-yl)-n-[4-methyl-3-[[3-[(4-methylpiperazin-1-yl)methyl]benzoyl]amino]phenyl]pyridine-4-carboxamide Chemical compound C1CN(C)CCN1CC1=CC=CC(C(=O)NC=2C(=CC=C(NC(=O)C=3C=C(N=CC=3)N3CCCCCC3)C=2)C)=C1 JKGPQSYGOYJTNI-UHFFFAOYSA-N 0.000 claims description 2
- 125000004601 benzofurazanyl group Chemical group N1=C2C(=NO1)C(=CC=C2)* 0.000 claims description 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
- 125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 claims description 2
- 125000000723 dihydrobenzofuranyl group Chemical group O1C(CC2=C1C=CC=C2)* 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- RDJBEKWNXOCCKC-UHFFFAOYSA-N n-[3-[[3-(diethylaminomethyl)benzoyl]amino]-4-methylphenyl]-2-morpholin-4-ylpyridine-4-carboxamide Chemical compound CCN(CC)CC1=CC=CC(C(=O)NC=2C(=CC=C(NC(=O)C=3C=C(N=CC=3)N3CCOCC3)C=2)C)=C1 RDJBEKWNXOCCKC-UHFFFAOYSA-N 0.000 claims description 2
- ZCMCJFZYZYUTRF-UHFFFAOYSA-N n-[4-methyl-3-[(3-piperidin-4-yloxybenzoyl)amino]phenyl]-2-morpholin-4-ylpyridine-4-carboxamide Chemical compound C1=C(NC(=O)C=2C=C(OC3CCNCC3)C=CC=2)C(C)=CC=C1NC(=O)C(C=1)=CC=NC=1N1CCOCC1 ZCMCJFZYZYUTRF-UHFFFAOYSA-N 0.000 claims description 2
- XVWKPEDUAVMRRU-UHFFFAOYSA-N n-[4-methyl-3-[[3-(1-methylazepan-4-yl)oxybenzoyl]amino]phenyl]-2-morpholin-4-ylpyridine-4-carboxamide Chemical compound C1CN(C)CCCC1OC1=CC=CC(C(=O)NC=2C(=CC=C(NC(=O)C=3C=C(N=CC=3)N3CCOCC3)C=2)C)=C1 XVWKPEDUAVMRRU-UHFFFAOYSA-N 0.000 claims description 2
- LMGRQKNWVZHCFE-UHFFFAOYSA-N n-[4-methyl-3-[[3-[(4-methylpiperazin-1-yl)methyl]benzoyl]amino]phenyl]-2-(3-methylpiperidin-1-yl)pyridine-4-carboxamide Chemical compound C1C(C)CCCN1C1=CC(C(=O)NC=2C=C(NC(=O)C=3C=C(CN4CCN(C)CC4)C=CC=3)C(C)=CC=2)=CC=N1 LMGRQKNWVZHCFE-UHFFFAOYSA-N 0.000 claims description 2
- BSYDZPCFCUVMPO-UHFFFAOYSA-N n-[4-methyl-3-[[4-[(2-methyl-1,3-thiazol-4-yl)methoxy]benzoyl]amino]phenyl]-2-morpholin-4-ylpyridine-4-carboxamide Chemical compound S1C(C)=NC(COC=2C=CC(=CC=2)C(=O)NC=2C(=CC=C(NC(=O)C=3C=C(N=CC=3)N3CCOCC3)C=2)C)=C1 BSYDZPCFCUVMPO-UHFFFAOYSA-N 0.000 claims description 2
- 125000004193 piperazinyl group Chemical group 0.000 claims description 2
- 125000005493 quinolyl group Chemical group 0.000 claims description 2
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 150000003857 carboxamides Chemical class 0.000 claims 2
- RXZIRKRDXDRFAA-UHFFFAOYSA-N n-[3-[[4-[(3-hydroxypyrrolidin-1-yl)methyl]benzoyl]amino]-4-methylphenyl]-2-morpholin-4-ylpyridine-4-carboxamide Chemical compound C1=C(NC(=O)C=2C=CC(CN3CC(O)CC3)=CC=2)C(C)=CC=C1NC(=O)C(C=1)=CC=NC=1N1CCOCC1 RXZIRKRDXDRFAA-UHFFFAOYSA-N 0.000 claims 1
- QSNZIHAHDWFKEB-UHFFFAOYSA-N n-[3-[[4-[[3-(dimethylamino)propyl-methylamino]methyl]benzoyl]amino]-4-methylphenyl]-2-morpholin-4-ylpyridine-4-carboxamide Chemical compound C1=CC(CN(C)CCCN(C)C)=CC=C1C(=O)NC1=CC(NC(=O)C=2C=C(N=CC=2)N2CCOCC2)=CC=C1C QSNZIHAHDWFKEB-UHFFFAOYSA-N 0.000 claims 1
- FUYPFZDBJVTCNE-UHFFFAOYSA-N n-[4-methyl-3-[[3-(piperazin-1-ylmethyl)benzoyl]amino]phenyl]-2-morpholin-4-ylpyridine-4-carboxamide Chemical compound C1=C(NC(=O)C=2C=C(CN3CCNCC3)C=CC=2)C(C)=CC=C1NC(=O)C(C=1)=CC=NC=1N1CCOCC1 FUYPFZDBJVTCNE-UHFFFAOYSA-N 0.000 claims 1
- YVGHLOWUEYFJIJ-UHFFFAOYSA-N n-[4-methyl-3-[[3-[(3-pyrrolidin-1-ylpropylamino)methyl]benzoyl]amino]phenyl]-2-morpholin-4-ylpyridine-4-carboxamide Chemical compound C1=C(NC(=O)C=2C=C(CNCCCN3CCCC3)C=CC=2)C(C)=CC=C1NC(=O)C(C=1)=CC=NC=1N1CCOCC1 YVGHLOWUEYFJIJ-UHFFFAOYSA-N 0.000 claims 1
- DJGVVEBKFSLTAC-UHFFFAOYSA-N n-[4-methyl-3-[[3-[(4-methylpiperazin-1-yl)methyl]benzoyl]amino]phenyl]-1,2-oxazole-5-carboxamide Chemical compound C1CN(C)CCN1CC1=CC=CC(C(=O)NC=2C(=CC=C(NC(=O)C=3ON=CC=3)C=2)C)=C1 DJGVVEBKFSLTAC-UHFFFAOYSA-N 0.000 claims 1
- XLWOLGYQFOJFCG-UHFFFAOYSA-N n-[4-methyl-3-[[3-[2-(1-methylpyrrolidin-2-yl)ethoxy]benzoyl]amino]phenyl]-2-morpholin-4-ylpyridine-4-carboxamide Chemical compound CN1CCCC1CCOC1=CC=CC(C(=O)NC=2C(=CC=C(NC(=O)C=3C=C(N=CC=3)N3CCOCC3)C=2)C)=C1 XLWOLGYQFOJFCG-UHFFFAOYSA-N 0.000 claims 1
- WQFORXTUXFQTPL-UHFFFAOYSA-N n-[4-methyl-3-[[4-[(4-methyl-1,4-diazepan-1-yl)methyl]benzoyl]amino]phenyl]-2-morpholin-4-ylpyridine-4-carboxamide Chemical compound C1CN(C)CCCN1CC1=CC=C(C(=O)NC=2C(=CC=C(NC(=O)C=3C=C(N=CC=3)N3CCOCC3)C=2)C)C=C1 WQFORXTUXFQTPL-UHFFFAOYSA-N 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 16
- 201000010099 disease Diseases 0.000 abstract description 14
- 125000005843 halogen group Chemical group 0.000 abstract description 4
- 125000001072 heteroaryl group Chemical group 0.000 abstract description 3
- 125000005553 heteroaryloxy group Chemical group 0.000 abstract 2
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 125000005844 heterocyclyloxy group Chemical group 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 267
- 239000000203 mixture Substances 0.000 description 183
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 135
- 239000000047 product Substances 0.000 description 117
- 238000005481 NMR spectroscopy Methods 0.000 description 101
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 93
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- 239000007858 starting material Substances 0.000 description 81
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 72
- 238000001819 mass spectrum Methods 0.000 description 67
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- 238000004440 column chromatography Methods 0.000 description 35
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- APCBTRDHCDOPNY-UHFFFAOYSA-N tert-butyl 3-hydroxypyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(O)C1 APCBTRDHCDOPNY-UHFFFAOYSA-N 0.000 description 1
- GBRBENQCAHILTC-UHFFFAOYSA-N tert-butyl 4-(3-ethoxycarbonylphenoxy)piperidine-1-carboxylate Chemical compound CCOC(=O)C1=CC=CC(OC2CCN(CC2)C(=O)OC(C)(C)C)=C1 GBRBENQCAHILTC-UHFFFAOYSA-N 0.000 description 1
- TVRROPABYXECLG-UHFFFAOYSA-N tert-butyl 4-[2-methoxy-5-[[2-methyl-5-[(2-morpholin-4-ylpyridine-4-carbonyl)amino]phenyl]carbamoyl]phenoxy]piperidine-1-carboxylate Chemical compound COC1=CC=C(C(=O)NC=2C(=CC=C(NC(=O)C=3C=C(N=CC=3)N3CCOCC3)C=2)C)C=C1OC1CCN(C(=O)OC(C)(C)C)CC1 TVRROPABYXECLG-UHFFFAOYSA-N 0.000 description 1
- MBIXWTNOPXZXOA-UHFFFAOYSA-N tert-butyl 4-[3-[[2-methyl-5-[(2-morpholin-4-ylpyridine-4-carbonyl)amino]phenyl]carbamoyl]phenoxy]piperidine-1-carboxylate Chemical compound C1=C(NC(=O)C=2C=C(OC3CCN(CC3)C(=O)OC(C)(C)C)C=CC=2)C(C)=CC=C1NC(=O)C(C=1)=CC=NC=1N1CCOCC1 MBIXWTNOPXZXOA-UHFFFAOYSA-N 0.000 description 1
- NLIUZCIBZXUWPL-UHFFFAOYSA-N tert-butyl 4-[4-[[2-methyl-5-[(2-morpholin-4-ylpyridine-4-carbonyl)amino]phenyl]carbamoyl]phenoxy]piperidine-1-carboxylate Chemical compound C1=C(NC(=O)C=2C=CC(OC3CCN(CC3)C(=O)OC(C)(C)C)=CC=2)C(C)=CC=C1NC(=O)C(C=1)=CC=NC=1N1CCOCC1 NLIUZCIBZXUWPL-UHFFFAOYSA-N 0.000 description 1
- SNPNVOVZKDPPLZ-UHFFFAOYSA-N tert-butyl 5-morpholin-4-ylpyridine-3-carboxylate Chemical compound CC(C)(C)OC(=O)C1=CN=CC(N2CCOCC2)=C1 SNPNVOVZKDPPLZ-UHFFFAOYSA-N 0.000 description 1
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- UPSPUYADGBWSHF-UHFFFAOYSA-N tolmetin Chemical compound C1=CC(C)=CC=C1C(=O)C1=CC=C(CC(O)=O)N1C UPSPUYADGBWSHF-UHFFFAOYSA-N 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 231100000765 toxin Toxicity 0.000 description 1
- 108700012359 toxins Proteins 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- IHIXIJGXTJIKRB-UHFFFAOYSA-N trisodium vanadate Chemical compound [Na+].[Na+].[Na+].[O-][V]([O-])([O-])=O IHIXIJGXTJIKRB-UHFFFAOYSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
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- 230000009385 viral infection Effects 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
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Classifications
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen 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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- 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
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
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- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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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- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
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Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GBGB9820770.7A GB9820770D0 (en) | 1998-09-25 | 1998-09-25 | Amide derivatives |
GBGB9826938.4A GB9826938D0 (en) | 1998-12-09 | 1998-12-09 | Amide derivatives |
GBGB9905969.3A GB9905969D0 (en) | 1999-03-17 | 1999-03-17 | Amide derivatives |
PCT/GB1999/003144 WO2000018738A1 (en) | 1998-09-25 | 1999-09-21 | Benzamide derivatives and their use as cytokine inhibitors |
Publications (3)
Publication Number | Publication Date |
---|---|
NO20011492D0 NO20011492D0 (no) | 2001-03-23 |
NO20011492L NO20011492L (no) | 2001-05-23 |
NO318800B1 true NO318800B1 (no) | 2005-05-09 |
Family
ID=27269489
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO20011492A NO318800B1 (no) | 1998-09-25 | 2001-03-23 | Benzamidderivater, fremgangsmate for fremstillimg og anvendelse derav samt farmasoytisk sammensetning |
Country Status (24)
Country | Link |
---|---|
US (1) | US6455520B1 (hu) |
EP (1) | EP1115707B1 (hu) |
JP (1) | JP2002525358A (hu) |
KR (1) | KR100618074B1 (hu) |
CN (1) | CN1146542C (hu) |
AT (1) | ATE254105T1 (hu) |
AU (1) | AU761361B2 (hu) |
BR (1) | BR9913947A (hu) |
CA (1) | CA2340454A1 (hu) |
DE (1) | DE69912823T2 (hu) |
DK (1) | DK1115707T3 (hu) |
ES (1) | ES2211172T3 (hu) |
HK (1) | HK1038556A1 (hu) |
HU (1) | HUP0104060A3 (hu) |
ID (1) | ID28267A (hu) |
IL (2) | IL141979A0 (hu) |
NO (1) | NO318800B1 (hu) |
NZ (1) | NZ509836A (hu) |
PL (1) | PL346854A1 (hu) |
PT (1) | PT1115707E (hu) |
RU (1) | RU2219171C2 (hu) |
SK (1) | SK285520B6 (hu) |
TR (1) | TR200100840T2 (hu) |
WO (1) | WO2000018738A1 (hu) |
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BRPI0916576A2 (pt) * | 2008-08-04 | 2017-06-27 | Chdi Inc | pelo menos uma entidade química, composição farmacêutica, e, método para tratar uma condição ou distúrbio. |
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NZ502702A (en) * | 1997-09-23 | 2002-10-25 | Astrazeneca Ab | Amide derivatives for the treatment of diseases mediated by TNF, IL-1, IL-6 or IL-8 |
CA2328699A1 (en) | 1998-05-15 | 1999-11-25 | Dearg Sutherland Brown | Benzamide derivatives for the treatment of diseases mediated by cytokines |
BR9910474A (pt) | 1998-05-15 | 2001-01-02 | Astrazeneca Ab | Composto derivado de amida, processo para preparação do mesmo, composição farmacêutica, e, uso de um composto derivado de amida |
EP1102750A1 (en) | 1998-08-04 | 2001-05-30 | AstraZeneca AB | Amide derivatives useful as inhibitors of the production of cytokines |
ES2211172T3 (es) | 1998-09-25 | 2004-07-01 | Astrazeneca Ab | Derivados de benzamida y su utilizacion como inhibidores de citoquinas. |
WO2000020402A1 (en) | 1998-10-01 | 2000-04-13 | Astrazeneca Ab | Chemical compounds |
PT1163237E (pt) | 1999-03-17 | 2004-08-31 | Astrazeneca Ab | Derivados de amida |
NZ513726A (en) | 1999-03-17 | 2001-09-28 | Astrazeneca Ab | Amide derivatives |
GB9906566D0 (en) | 1999-03-23 | 1999-05-19 | Zeneca Ltd | Chemical compounds |
GB9924092D0 (en) | 1999-10-13 | 1999-12-15 | Zeneca Ltd | Pyrimidine derivatives |
-
1999
- 1999-09-21 ES ES99947653T patent/ES2211172T3/es not_active Expired - Lifetime
- 1999-09-21 CN CNB998112968A patent/CN1146542C/zh not_active Expired - Fee Related
- 1999-09-21 SK SK421-2001A patent/SK285520B6/sk unknown
- 1999-09-21 HU HU0104060A patent/HUP0104060A3/hu unknown
- 1999-09-21 AU AU61034/99A patent/AU761361B2/en not_active Ceased
- 1999-09-21 IL IL14197999A patent/IL141979A0/xx active IP Right Grant
- 1999-09-21 RU RU2001111320/04A patent/RU2219171C2/ru not_active IP Right Cessation
- 1999-09-21 WO PCT/GB1999/003144 patent/WO2000018738A1/en active IP Right Grant
- 1999-09-21 TR TR2001/00840T patent/TR200100840T2/xx unknown
- 1999-09-21 PL PL99346854A patent/PL346854A1/xx not_active Application Discontinuation
- 1999-09-21 PT PT99947653T patent/PT1115707E/pt unknown
- 1999-09-21 DE DE69912823T patent/DE69912823T2/de not_active Expired - Fee Related
- 1999-09-21 DK DK99947653T patent/DK1115707T3/da active
- 1999-09-21 JP JP2000572198A patent/JP2002525358A/ja active Pending
- 1999-09-21 EP EP99947653A patent/EP1115707B1/en not_active Expired - Lifetime
- 1999-09-21 KR KR1020017003551A patent/KR100618074B1/ko not_active IP Right Cessation
- 1999-09-21 US US09/787,882 patent/US6455520B1/en not_active Expired - Fee Related
- 1999-09-21 CA CA002340454A patent/CA2340454A1/en not_active Abandoned
- 1999-09-21 NZ NZ509836A patent/NZ509836A/xx unknown
- 1999-09-21 ID IDW20010593A patent/ID28267A/id unknown
- 1999-09-21 BR BR9913947-2A patent/BR9913947A/pt not_active Application Discontinuation
- 1999-09-21 AT AT99947653T patent/ATE254105T1/de not_active IP Right Cessation
-
2001
- 2001-03-13 IL IL141979A patent/IL141979A/en not_active IP Right Cessation
- 2001-03-23 NO NO20011492A patent/NO318800B1/no unknown
- 2001-11-13 HK HK01107980A patent/HK1038556A1/xx not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
RU2219171C2 (ru) | 2003-12-20 |
IL141979A0 (en) | 2002-03-10 |
AU6103499A (en) | 2000-04-17 |
CN1319092A (zh) | 2001-10-24 |
CA2340454A1 (en) | 2000-04-06 |
KR20010085828A (ko) | 2001-09-07 |
HUP0104060A2 (hu) | 2002-03-28 |
US6455520B1 (en) | 2002-09-24 |
ATE254105T1 (de) | 2003-11-15 |
BR9913947A (pt) | 2001-06-12 |
WO2000018738A1 (en) | 2000-04-06 |
EP1115707B1 (en) | 2003-11-12 |
DE69912823D1 (de) | 2003-12-18 |
NO20011492L (no) | 2001-05-23 |
HK1038556A1 (en) | 2002-03-22 |
TR200100840T2 (tr) | 2001-10-22 |
SK4212001A3 (en) | 2001-08-06 |
NZ509836A (en) | 2003-06-30 |
NO20011492D0 (no) | 2001-03-23 |
IL141979A (en) | 2006-08-20 |
DE69912823T2 (de) | 2004-09-23 |
PL346854A1 (en) | 2002-03-11 |
PT1115707E (pt) | 2004-04-30 |
SK285520B6 (sk) | 2007-03-01 |
KR100618074B1 (ko) | 2006-08-30 |
HUP0104060A3 (en) | 2002-04-29 |
EP1115707A1 (en) | 2001-07-18 |
DK1115707T3 (da) | 2004-03-01 |
ID28267A (id) | 2001-05-10 |
JP2002525358A (ja) | 2002-08-13 |
CN1146542C (zh) | 2004-04-21 |
AU761361B2 (en) | 2003-06-05 |
ES2211172T3 (es) | 2004-07-01 |
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