NO321017B1 - Amid-derivater som er egnet som cytokininhibitorer, fremgangsmate for fremstilling derav, anvendelse derav og farmasoytisk preparat som omfatter amid-derivater. - Google Patents
Amid-derivater som er egnet som cytokininhibitorer, fremgangsmate for fremstilling derav, anvendelse derav og farmasoytisk preparat som omfatter amid-derivater. Download PDFInfo
- Publication number
- NO321017B1 NO321017B1 NO20010533A NO20010533A NO321017B1 NO 321017 B1 NO321017 B1 NO 321017B1 NO 20010533 A NO20010533 A NO 20010533A NO 20010533 A NO20010533 A NO 20010533A NO 321017 B1 NO321017 B1 NO 321017B1
- Authority
- NO
- Norway
- Prior art keywords
- alkyl
- alkylamino
- formula
- amino
- substituent
- Prior art date
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- 238000000034 method Methods 0.000 title claims abstract description 54
- 150000001408 amides Chemical class 0.000 title claims abstract description 44
- 238000002360 preparation method Methods 0.000 title claims abstract description 28
- 102000004127 Cytokines Human genes 0.000 title claims abstract description 25
- 108090000695 Cytokines Proteins 0.000 title claims abstract description 25
- 230000008569 process Effects 0.000 title claims abstract description 5
- 239000008194 pharmaceutical composition Substances 0.000 title abstract 2
- 239000003112 inhibitor Substances 0.000 title description 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 171
- 125000001424 substituent group Chemical group 0.000 claims abstract description 152
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 119
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 91
- 150000003839 salts Chemical class 0.000 claims abstract description 49
- 150000002148 esters Chemical class 0.000 claims abstract description 36
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 28
- 238000011282 treatment Methods 0.000 claims abstract description 15
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 14
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 13
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims abstract description 9
- 230000001404 mediated effect Effects 0.000 claims abstract description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 6
- -1 cyano, nitro, amino, carboxy Chemical group 0.000 claims description 469
- 150000001875 compounds Chemical class 0.000 claims description 159
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 38
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 35
- 239000000460 chlorine Chemical group 0.000 claims description 35
- 229910052801 chlorine Inorganic materials 0.000 claims description 35
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 35
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 35
- 238000006243 chemical reaction Methods 0.000 claims description 34
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 29
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 28
- 239000002253 acid Substances 0.000 claims description 23
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 23
- 238000001727 in vivo Methods 0.000 claims description 20
- 229910052736 halogen Inorganic materials 0.000 claims description 19
- 150000002367 halogens Chemical class 0.000 claims description 19
- 150000001412 amines Chemical class 0.000 claims description 18
- 238000004519 manufacturing process Methods 0.000 claims description 18
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 17
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 16
- 125000006239 protecting group Chemical group 0.000 claims description 16
- 125000004076 pyridyl group Chemical group 0.000 claims description 14
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 13
- 125000005493 quinolyl group Chemical group 0.000 claims description 13
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 12
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 12
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 12
- 229910052731 fluorine Inorganic materials 0.000 claims description 12
- 239000011737 fluorine Substances 0.000 claims description 12
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 10
- 230000029936 alkylation Effects 0.000 claims description 10
- 238000005804 alkylation reaction Methods 0.000 claims description 10
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 10
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 10
- 125000006264 diethylaminomethyl group Chemical group [H]C([H])([H])C([H])([H])N(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 claims description 9
- 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 claims description 9
- 125000000524 functional group Chemical group 0.000 claims description 9
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 9
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 9
- 125000001064 morpholinomethyl group Chemical group [H]C([H])(*)N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 claims description 9
- 125000004193 piperazinyl group Chemical group 0.000 claims description 9
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
- 229910052794 bromium Chemical group 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 7
- 125000006534 ethyl amino methyl group Chemical group [H]N(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 claims description 7
- 125000006533 methyl amino methyl group Chemical group [H]N(C([H])([H])[H])C([H])([H])* 0.000 claims description 7
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 6
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 6
- 239000005711 Benzoic acid Substances 0.000 claims description 6
- 235000010233 benzoic acid Nutrition 0.000 claims description 6
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 6
- 125000003386 piperidinyl group Chemical group 0.000 claims description 6
- 230000009467 reduction Effects 0.000 claims description 6
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- 125000000335 thiazolyl group Chemical group 0.000 claims description 6
- FWEAULFQIPJOSB-UHFFFAOYSA-N 3-hydroxy-n-[2-methyl-5-(phenylcarbamoyl)phenyl]naphthalene-2-carboxamide Chemical compound C1=C(NC(=O)C=2C(=CC3=CC=CC=C3C=2)O)C(C)=CC=C1C(=O)NC1=CC=CC=C1 FWEAULFQIPJOSB-UHFFFAOYSA-N 0.000 claims description 5
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 5
- 125000004414 alkyl thio group Chemical group 0.000 claims description 5
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 5
- 125000001589 carboacyl group Chemical group 0.000 claims description 5
- 238000003776 cleavage reaction Methods 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 5
- QKYUESQZCADLCZ-UHFFFAOYSA-N n-(2-cyclohexylethyl)-3-[(3,4-dimethoxybenzoyl)amino]-4-methylbenzamide Chemical compound C1=C(OC)C(OC)=CC=C1C(=O)NC1=CC(C(=O)NCCC2CCCCC2)=CC=C1C QKYUESQZCADLCZ-UHFFFAOYSA-N 0.000 claims description 5
- VKKSPOMAAWSDMV-UHFFFAOYSA-N n-(2-cyclohexylethyl)-3-[(4-hydroxybenzoyl)amino]-4-methylbenzamide Chemical compound CC1=CC=C(C(=O)NCCC2CCCCC2)C=C1NC(=O)C1=CC=C(O)C=C1 VKKSPOMAAWSDMV-UHFFFAOYSA-N 0.000 claims description 5
- QIWLMFODGNOEDN-UHFFFAOYSA-N n-[2-chloro-5-[(2-fluoroanilino)carbamoyl]phenyl]benzamide Chemical compound FC1=CC=CC=C1NNC(=O)C1=CC=C(Cl)C(NC(=O)C=2C=CC=CC=2)=C1 QIWLMFODGNOEDN-UHFFFAOYSA-N 0.000 claims description 5
- YPPPNDSCSKRYRI-UHFFFAOYSA-N n-[6-chloro-2-methyl-3-(phenylcarbamoyl)phenyl]-3-hydroxynaphthalene-2-carboxamide Chemical compound C1=CC(Cl)=C(NC(=O)C=2C(=CC3=CC=CC=C3C=2)O)C(C)=C1C(=O)NC1=CC=CC=C1 YPPPNDSCSKRYRI-UHFFFAOYSA-N 0.000 claims description 5
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 5
- IHXHNRYWUULXPN-UHFFFAOYSA-N 4-[[5-[[3-(dimethylamino)phenyl]carbamoyl]-2-methylphenyl]carbamoyl]benzoic acid Chemical compound CN(C)C1=CC=CC(NC(=O)C=2C=C(NC(=O)C=3C=CC(=CC=3)C(O)=O)C(C)=CC=2)=C1 IHXHNRYWUULXPN-UHFFFAOYSA-N 0.000 claims description 4
- NRXZAADHVZVJDX-UHFFFAOYSA-N 4-chloro-n-[3-(dimethylamino)phenyl]-3-[(4-propylbenzoyl)amino]benzamide Chemical compound C1=CC(CCC)=CC=C1C(=O)NC1=CC(C(=O)NC=2C=C(C=CC=2)N(C)C)=CC=C1Cl NRXZAADHVZVJDX-UHFFFAOYSA-N 0.000 claims description 4
- 125000004423 acyloxy group Chemical group 0.000 claims description 4
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims description 4
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 4
- KYQFAJYEKPDLRY-UHFFFAOYSA-N n-[2-chloro-5-[[3-(dimethylamino)phenyl]carbamoyl]phenyl]quinoline-6-carboxamide Chemical compound CN(C)C1=CC=CC(NC(=O)C=2C=C(NC(=O)C=3C=C4C=CC=NC4=CC=3)C(Cl)=CC=2)=C1 KYQFAJYEKPDLRY-UHFFFAOYSA-N 0.000 claims description 4
- NITTYOFBJISXMK-UHFFFAOYSA-N n-[5-[[3-(dimethylamino)phenyl]carbamoyl]-2-methylphenyl]quinoline-6-carboxamide Chemical compound CN(C)C1=CC=CC(NC(=O)C=2C=C(NC(=O)C=3C=C4C=CC=NC4=CC=3)C(C)=CC=2)=C1 NITTYOFBJISXMK-UHFFFAOYSA-N 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 230000007017 scission Effects 0.000 claims description 4
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
- KMDXOAQBSWRVBX-UHFFFAOYSA-N 6-[(2-amino-2-methylpropyl)amino]-n-[2-chloro-5-[(3-fluoro-5-morpholin-4-ylphenyl)carbamoyl]phenyl]pyridine-3-carboxamide Chemical compound C1=NC(NCC(C)(N)C)=CC=C1C(=O)NC1=CC(C(=O)NC=2C=C(C=C(F)C=2)N2CCOCC2)=CC=C1Cl KMDXOAQBSWRVBX-UHFFFAOYSA-N 0.000 claims description 3
- 230000010933 acylation Effects 0.000 claims description 3
- 238000005917 acylation reaction Methods 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- KQIWOLCWODSUMC-UHFFFAOYSA-N n-[5-[(3,4-dichlorophenyl)methylcarbamoyl]-2-methylphenyl]-3,4,5-trimethoxybenzamide Chemical compound COC1=C(OC)C(OC)=CC(C(=O)NC=2C(=CC=C(C=2)C(=O)NCC=2C=C(Cl)C(Cl)=CC=2)C)=C1 KQIWOLCWODSUMC-UHFFFAOYSA-N 0.000 claims description 3
- FVLVBVSILSHUAF-UHFFFAOYSA-N n-benzyl-3,5-dimethyl-n-propan-2-ylbenzamide Chemical compound C=1C(C)=CC(C)=CC=1C(=O)N(C(C)C)CC1=CC=CC=C1 FVLVBVSILSHUAF-UHFFFAOYSA-N 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- YOJREAPIHAAZRC-UHFFFAOYSA-N 3-[(3,4-dimethoxybenzoyl)amino]-n-[3-(dimethylamino)phenyl]-4-methylbenzamide Chemical compound C1=C(OC)C(OC)=CC=C1C(=O)NC1=CC(C(=O)NC=2C=C(C=CC=2)N(C)C)=CC=C1C YOJREAPIHAAZRC-UHFFFAOYSA-N 0.000 claims description 2
- RWRMMONJQFLJBY-UHFFFAOYSA-N 3-[(4-butoxybenzoyl)amino]-n-[3-(dimethylamino)phenyl]-4-methylbenzamide Chemical compound C1=CC(OCCCC)=CC=C1C(=O)NC1=CC(C(=O)NC=2C=C(C=CC=2)N(C)C)=CC=C1C RWRMMONJQFLJBY-UHFFFAOYSA-N 0.000 claims description 2
- XVZJLSUIOGRPOW-UHFFFAOYSA-N 4-methyl-3-[[3-[(4-methylpiperazin-1-yl)methyl]benzoyl]amino]-n-(3-morpholin-4-ylphenyl)benzamide Chemical compound C1CN(C)CCN1CC1=CC=CC(C(=O)NC=2C(=CC=C(C=2)C(=O)NC=2C=C(C=CC=2)N2CCOCC2)C)=C1 XVZJLSUIOGRPOW-UHFFFAOYSA-N 0.000 claims description 2
- NGIRRLKLECTBCU-UHFFFAOYSA-N 4-methyl-n-(3-morpholin-4-ylphenyl)-3-[(3-piperidin-4-yloxybenzoyl)amino]benzamide Chemical compound CC1=CC=C(C(=O)NC=2C=C(C=CC=2)N2CCOCC2)C=C1NC(=O)C(C=1)=CC=CC=1OC1CCNCC1 NGIRRLKLECTBCU-UHFFFAOYSA-N 0.000 claims description 2
- AQYSYJUIMQTRMV-UHFFFAOYSA-N hypofluorous acid Chemical compound FO AQYSYJUIMQTRMV-UHFFFAOYSA-N 0.000 claims description 2
- LRYKFSYYLJMOSX-UHFFFAOYSA-N n-[3-(dimethylamino)phenyl]-4-methyl-3-[(4-propylbenzoyl)amino]benzamide Chemical compound C1=CC(CCC)=CC=C1C(=O)NC1=CC(C(=O)NC=2C=C(C=CC=2)N(C)C)=CC=C1C LRYKFSYYLJMOSX-UHFFFAOYSA-N 0.000 claims description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 20
- 201000010099 disease Diseases 0.000 abstract description 18
- 125000003118 aryl group Chemical group 0.000 abstract description 11
- 125000005843 halogen group Chemical group 0.000 abstract description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 125000003107 substituted aryl group Chemical group 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 171
- 238000001819 mass spectrum Methods 0.000 description 153
- 239000000203 mixture Substances 0.000 description 147
- 239000000047 product Substances 0.000 description 116
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 88
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 78
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 69
- 239000000243 solution Substances 0.000 description 66
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 49
- 239000007787 solid Substances 0.000 description 44
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 43
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 39
- 239000007858 starting material Substances 0.000 description 39
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 38
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 36
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 33
- 229920006395 saturated elastomer Polymers 0.000 description 29
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 28
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
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- 235000019341 magnesium sulphate Nutrition 0.000 description 19
- 238000012360 testing method Methods 0.000 description 19
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- 235000017557 sodium bicarbonate Nutrition 0.000 description 18
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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 230000002401 inhibitory effect Effects 0.000 description 9
- 229920006008 lipopolysaccharide Polymers 0.000 description 9
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 8
- 241000700159 Rattus Species 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 108060008682 Tumor Necrosis Factor Proteins 0.000 description 8
- 102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 description 8
- 239000003701 inert diluent Substances 0.000 description 8
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- 108091000080 Phosphotransferase Proteins 0.000 description 7
- VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
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- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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- C07C237/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton having nitrogen atoms of amino groups bound to the carbon skeleton of the acid part, further acylated
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- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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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Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GBGB9816837.0A GB9816837D0 (en) | 1998-08-04 | 1998-08-04 | Amide derivatives |
PCT/GB1999/002494 WO2000007980A1 (en) | 1998-08-04 | 1999-07-29 | Amide derivatives which are useful as cytokine inhibitors |
Publications (3)
Publication Number | Publication Date |
---|---|
NO20010533D0 NO20010533D0 (no) | 2001-01-31 |
NO20010533L NO20010533L (no) | 2001-03-30 |
NO321017B1 true NO321017B1 (no) | 2006-02-27 |
Family
ID=10836592
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO20010533A NO321017B1 (no) | 1998-08-04 | 2001-01-31 | Amid-derivater som er egnet som cytokininhibitorer, fremgangsmate for fremstilling derav, anvendelse derav og farmasoytisk preparat som omfatter amid-derivater. |
Country Status (25)
Country | Link |
---|---|
US (1) | US6821965B1 (hu) |
EP (1) | EP1102743B1 (hu) |
JP (1) | JP4502509B2 (hu) |
KR (1) | KR100628285B1 (hu) |
CN (1) | CN1243724C (hu) |
AT (1) | ATE221047T1 (hu) |
AU (1) | AU756292B2 (hu) |
BR (1) | BRPI9912726B8 (hu) |
CA (1) | CA2337770C (hu) |
CZ (1) | CZ301971B6 (hu) |
DE (1) | DE69902277T2 (hu) |
DK (1) | DK1102743T3 (hu) |
ES (1) | ES2178895T3 (hu) |
GB (1) | GB9816837D0 (hu) |
HK (1) | HK1037608A1 (hu) |
HU (1) | HU230343B1 (hu) |
IL (2) | IL141184A0 (hu) |
NO (1) | NO321017B1 (hu) |
NZ (1) | NZ509162A (hu) |
PL (1) | PL195722B1 (hu) |
PT (1) | PT1102743E (hu) |
RU (1) | RU2220951C2 (hu) |
SK (1) | SK286446B6 (hu) |
WO (1) | WO2000007980A1 (hu) |
ZA (1) | ZA200100617B (hu) |
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1998
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