NO314182B1 - Nikotinamid-derivater, anvendelse derav, samt farmasöytisk blanding - Google Patents
Nikotinamid-derivater, anvendelse derav, samt farmasöytisk blanding Download PDFInfo
- Publication number
- NO314182B1 NO314182B1 NO19994791A NO994791A NO314182B1 NO 314182 B1 NO314182 B1 NO 314182B1 NO 19994791 A NO19994791 A NO 19994791A NO 994791 A NO994791 A NO 994791A NO 314182 B1 NO314182 B1 NO 314182B1
- Authority
- NO
- Norway
- Prior art keywords
- nicotinamide
- hydroxy
- fluorophenoxy
- mmol
- methylethyl
- Prior art date
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- 150000005480 nicotinamides Chemical class 0.000 title description 3
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 224
- 208000027866 inflammatory disease Diseases 0.000 claims abstract description 21
- 238000011282 treatment Methods 0.000 claims abstract description 13
- 208000006673 asthma Diseases 0.000 claims abstract description 12
- 230000002757 inflammatory effect Effects 0.000 claims abstract description 12
- 230000002685 pulmonary effect Effects 0.000 claims abstract description 11
- 208000030507 AIDS Diseases 0.000 claims abstract description 10
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims abstract description 10
- 206010012438 Dermatitis atopic Diseases 0.000 claims abstract description 10
- 206010016654 Fibrosis Diseases 0.000 claims abstract description 10
- 206010020751 Hypersensitivity Diseases 0.000 claims abstract description 10
- 208000005314 Multi-Infarct Dementia Diseases 0.000 claims abstract description 10
- 201000004681 Psoriasis Diseases 0.000 claims abstract description 10
- 208000025747 Rheumatic disease Diseases 0.000 claims abstract description 10
- 206010039085 Rhinitis allergic Diseases 0.000 claims abstract description 10
- 201000004810 Vascular dementia Diseases 0.000 claims abstract description 10
- 208000026935 allergic disease Diseases 0.000 claims abstract description 10
- 230000000172 allergic effect Effects 0.000 claims abstract description 10
- 201000010105 allergic rhinitis Diseases 0.000 claims abstract description 10
- 230000002917 arthritic effect Effects 0.000 claims abstract description 10
- 201000008937 atopic dermatitis Diseases 0.000 claims abstract description 10
- 208000010668 atopic eczema Diseases 0.000 claims abstract description 10
- 208000015114 central nervous system disease Diseases 0.000 claims abstract description 10
- 230000004761 fibrosis Effects 0.000 claims abstract description 10
- 230000009610 hypersensitivity Effects 0.000 claims abstract description 10
- 230000000241 respiratory effect Effects 0.000 claims abstract description 10
- 208000023504 respiratory system disease Diseases 0.000 claims abstract description 10
- 230000000552 rheumatic effect Effects 0.000 claims abstract description 10
- 230000035939 shock Effects 0.000 claims abstract description 10
- 208000011580 syndromic disease Diseases 0.000 claims abstract description 10
- 238000004260 weight control Methods 0.000 claims abstract description 10
- 206010039073 rheumatoid arthritis Diseases 0.000 claims abstract description 9
- 239000000203 mixture Substances 0.000 claims description 267
- 239000011570 nicotinamide Substances 0.000 claims description 139
- 229960003966 nicotinamide Drugs 0.000 claims description 139
- 238000002360 preparation method Methods 0.000 claims description 93
- -1 oxaspirononenyl Chemical group 0.000 claims description 55
- 239000000460 chlorine Substances 0.000 claims description 47
- 229910052739 hydrogen Inorganic materials 0.000 claims description 42
- 239000001257 hydrogen Substances 0.000 claims description 42
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 28
- 150000003839 salts Chemical class 0.000 claims description 25
- 108010044467 Isoenzymes Proteins 0.000 claims description 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
- 229910052736 halogen Inorganic materials 0.000 claims description 20
- 150000002367 halogens Chemical class 0.000 claims description 20
- 210000003979 eosinophil Anatomy 0.000 claims description 15
- 230000005764 inhibitory process Effects 0.000 claims description 15
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 14
- 150000002431 hydrogen Chemical group 0.000 claims description 14
- 239000001301 oxygen Substances 0.000 claims description 14
- 229910052760 oxygen Inorganic materials 0.000 claims description 14
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 13
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 12
- 201000010099 disease Diseases 0.000 claims description 12
- 239000011737 fluorine Chemical group 0.000 claims description 12
- 229910052731 fluorine Chemical group 0.000 claims description 12
- 230000004913 activation Effects 0.000 claims description 11
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
- 206010006895 Cachexia Diseases 0.000 claims description 9
- 206010009900 Colitis ulcerative Diseases 0.000 claims description 9
- 241000124008 Mammalia Species 0.000 claims description 9
- 201000006704 Ulcerative Colitis Diseases 0.000 claims description 9
- 230000037396 body weight Effects 0.000 claims description 9
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 9
- 230000001225 therapeutic effect Effects 0.000 claims description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
- 208000011231 Crohn disease Diseases 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
- 230000001105 regulatory effect Effects 0.000 claims description 7
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 6
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 5
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims description 5
- NFIPEXBVZIKXDB-UHFFFAOYSA-N n-[1-(5-chlorothiophen-2-yl)ethyl]-2-(4-fluorophenoxy)pyridine-3-carboxamide Chemical compound C=1C=C(Cl)SC=1C(C)NC(=O)C1=CC=CN=C1OC1=CC=C(F)C=C1 NFIPEXBVZIKXDB-UHFFFAOYSA-N 0.000 claims description 5
- 229910052700 potassium Inorganic materials 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 230000002401 inhibitory effect Effects 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- MRPUOLUWSANGMT-UHFFFAOYSA-N 2-(2,3-dihydro-1,4-benzodioxin-6-yloxy)-n-[[4-(1-hydroxyethyl)cyclohexyl]methyl]pyridine-3-carboxamide Chemical compound C1CC(C(O)C)CCC1CNC(=O)C1=CC=CN=C1OC1=CC=C(OCCO2)C2=C1 MRPUOLUWSANGMT-UHFFFAOYSA-N 0.000 claims description 3
- JHJWSJAXJVNGRT-UHFFFAOYSA-N 2-(3-aminophenoxy)-n-[(2-chlorophenyl)methyl]pyridine-3-carboxamide Chemical compound NC1=CC=CC(OC=2C(=CC=CN=2)C(=O)NCC=2C(=CC=CC=2)Cl)=C1 JHJWSJAXJVNGRT-UHFFFAOYSA-N 0.000 claims description 3
- WCQDTRSGAOJSFH-UHFFFAOYSA-N 2-(3-cyano-4-fluorophenoxy)-n-[[4-(1-hydroxyethyl)cyclohexyl]methyl]pyridine-3-carboxamide Chemical compound C1CC(C(O)C)CCC1CNC(=O)C1=CC=CN=C1OC1=CC=C(F)C(C#N)=C1 WCQDTRSGAOJSFH-UHFFFAOYSA-N 0.000 claims description 3
- WUXRYUPJZOCPAW-UHFFFAOYSA-N 2-(3-nitrophenoxy)-n-[(2-oxo-1,3-dihydroindol-5-yl)methyl]pyridine-3-carboxamide Chemical compound [O-][N+](=O)C1=CC=CC(OC=2C(=CC=CN=2)C(=O)NCC=2C=C3CC(=O)NC3=CC=2)=C1 WUXRYUPJZOCPAW-UHFFFAOYSA-N 0.000 claims description 3
- HNHPGXXUHGQYRI-UHFFFAOYSA-N 2-(4-fluorophenoxy)-n-(furan-2-ylmethyl)pyridine-3-carboxamide Chemical compound C1=CC(F)=CC=C1OC1=NC=CC=C1C(=O)NCC1=CC=CO1 HNHPGXXUHGQYRI-UHFFFAOYSA-N 0.000 claims description 3
- VODZXDFLWAYBNO-CQSZACIVSA-N 2-(4-fluorophenoxy)-n-[(1r)-1-(4-methoxyphenyl)ethyl]pyridine-3-carboxamide Chemical compound C1=CC(OC)=CC=C1[C@@H](C)NC(=O)C1=CC=CN=C1OC1=CC=C(F)C=C1 VODZXDFLWAYBNO-CQSZACIVSA-N 0.000 claims description 3
- VODZXDFLWAYBNO-AWEZNQCLSA-N 2-(4-fluorophenoxy)-n-[(1s)-1-(4-methoxyphenyl)ethyl]pyridine-3-carboxamide Chemical compound C1=CC(OC)=CC=C1[C@H](C)NC(=O)C1=CC=CN=C1OC1=CC=C(F)C=C1 VODZXDFLWAYBNO-AWEZNQCLSA-N 0.000 claims description 3
- BFPWMXDGAFJBBS-UHFFFAOYSA-N 2-(4-fluorophenoxy)-n-[(2-oxo-1,3-dihydroindol-5-yl)methyl]pyridine-3-carboxamide Chemical compound C1=CC(F)=CC=C1OC1=NC=CC=C1C(=O)NCC1=CC=C(NC(=O)C2)C2=C1 BFPWMXDGAFJBBS-UHFFFAOYSA-N 0.000 claims description 3
- DVRRRSRXSUVSIJ-UHFFFAOYSA-N n-[(2-chloro-6-fluorophenyl)methyl]-2-(4-fluorophenoxy)pyridine-3-carboxamide Chemical compound C1=CC(F)=CC=C1OC1=NC=CC=C1C(=O)NCC1=C(F)C=CC=C1Cl DVRRRSRXSUVSIJ-UHFFFAOYSA-N 0.000 claims description 3
- BAWMHOHBQLRKDC-UHFFFAOYSA-N n-[(2-chlorophenyl)methyl]-2-[3-(trifluoromethyl)phenoxy]pyridine-3-carboxamide Chemical compound FC(F)(F)C1=CC=CC(OC=2C(=CC=CN=2)C(=O)NCC=2C(=CC=CC=2)Cl)=C1 BAWMHOHBQLRKDC-UHFFFAOYSA-N 0.000 claims description 3
- KKXAURDDIVXLEC-UHFFFAOYSA-N n-[(4,5-dichlorothiophen-2-yl)methyl]-2-(4-fluorophenoxy)pyridine-3-carboxamide Chemical compound C1=CC(F)=CC=C1OC1=NC=CC=C1C(=O)NCC1=CC(Cl)=C(Cl)S1 KKXAURDDIVXLEC-UHFFFAOYSA-N 0.000 claims description 3
- KFCYXOKCAAEYNT-UHFFFAOYSA-N n-[(4-aminophenyl)methyl]-2-(4-fluorophenoxy)pyridine-3-carboxamide Chemical compound C1=CC(N)=CC=C1CNC(=O)C1=CC=CN=C1OC1=CC=C(F)C=C1 KFCYXOKCAAEYNT-UHFFFAOYSA-N 0.000 claims description 3
- ZCBQXKPIBUSXKP-UHFFFAOYSA-N n-[(5-chlorothiophen-2-yl)methyl]-2-(3-cyanophenoxy)pyridine-3-carboxamide Chemical compound S1C(Cl)=CC=C1CNC(=O)C1=CC=CN=C1OC1=CC=CC(C#N)=C1 ZCBQXKPIBUSXKP-UHFFFAOYSA-N 0.000 claims description 3
- OMLHMSPAFRDWBP-UHFFFAOYSA-N n-[(5-chlorothiophen-2-yl)methyl]-2-(4-fluorophenoxy)pyridine-3-carboxamide Chemical compound C1=CC(F)=CC=C1OC1=NC=CC=C1C(=O)NCC1=CC=C(Cl)S1 OMLHMSPAFRDWBP-UHFFFAOYSA-N 0.000 claims description 3
- 201000003068 rheumatic fever Diseases 0.000 claims description 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 2
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 2
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 2
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 2
- JJISIDKWPAQXEO-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-yloxy)-n-[[4-(1-hydroxyethyl)cyclohexyl]methyl]pyridine-3-carboxamide Chemical compound C1CC(C(O)C)CCC1CNC(=O)C1=CC=CN=C1OC1=CC=C(OCO2)C2=C1 JJISIDKWPAQXEO-UHFFFAOYSA-N 0.000 claims description 2
- USQXTVCIHJYYNN-UHFFFAOYSA-N 2-(2,3-dihydro-1,4-benzodioxin-6-yloxy)-n-[[4-(2-hydroxypropan-2-yl)cyclohexyl]methyl]pyridine-3-carboxamide Chemical compound C1CC(C(C)(O)C)CCC1CNC(=O)C1=CC=CN=C1OC1=CC=C(OCCO2)C2=C1 USQXTVCIHJYYNN-UHFFFAOYSA-N 0.000 claims description 2
- MEWIXEPIWPRGDZ-UHFFFAOYSA-N 2-(2,3-dihydro-1,4-benzodioxin-6-yloxy)-n-[[4-(2-hydroxypropan-2-yl)phenyl]methyl]pyridine-3-carboxamide Chemical compound C1=CC(C(C)(O)C)=CC=C1CNC(=O)C1=CC=CN=C1OC1=CC=C(OCCO2)C2=C1 MEWIXEPIWPRGDZ-UHFFFAOYSA-N 0.000 claims description 2
- JBDAGDAECDLBCE-UHFFFAOYSA-N 2-(3-cyano-4-fluorophenoxy)-n-[[2-fluoro-4-(2-hydroxypropan-2-yl)phenyl]methyl]pyridine-3-carboxamide Chemical compound FC1=CC(C(C)(O)C)=CC=C1CNC(=O)C1=CC=CN=C1OC1=CC=C(F)C(C#N)=C1 JBDAGDAECDLBCE-UHFFFAOYSA-N 0.000 claims description 2
- WCZOYOXIFFNNFV-UHFFFAOYSA-N 2-(3-cyano-4-fluorophenoxy)-n-[[4-(2-hydroxypropan-2-yl)cyclohexyl]methyl]pyridine-3-carboxamide Chemical compound C1CC(C(C)(O)C)CCC1CNC(=O)C1=CC=CN=C1OC1=CC=C(F)C(C#N)=C1 WCZOYOXIFFNNFV-UHFFFAOYSA-N 0.000 claims description 2
- BDJDEYDGCVDOBL-UHFFFAOYSA-N 2-(3-cyanophenoxy)-n-[(2-oxo-1,3-dihydroindol-5-yl)methyl]pyridine-3-carboxamide Chemical compound C=1C=C2NC(=O)CC2=CC=1CNC(=O)C1=CC=CN=C1OC1=CC=CC(C#N)=C1 BDJDEYDGCVDOBL-UHFFFAOYSA-N 0.000 claims description 2
- NSOZETMBBZHUEU-UHFFFAOYSA-N 2-(3-fluorophenoxy)-n-[[4-(2-hydroxypropan-2-yl)phenyl]methyl]pyridine-3-carboxamide Chemical compound C1=CC(C(C)(O)C)=CC=C1CNC(=O)C1=CC=CN=C1OC1=CC=CC(F)=C1 NSOZETMBBZHUEU-UHFFFAOYSA-N 0.000 claims description 2
- WQRKCXQECWRJBG-UHFFFAOYSA-N 2-(4-fluorophenoxy)-n-(2-oxo-3h-1,3-benzoxazol-6-yl)pyridine-3-carboxamide Chemical compound C1=CC(F)=CC=C1OC1=NC=CC=C1C(=O)NC1=CC=C(NC(=O)O2)C2=C1 WQRKCXQECWRJBG-UHFFFAOYSA-N 0.000 claims description 2
- BJSRBYOJJULYSJ-UHFFFAOYSA-N 2-(4-fluorophenoxy)-n-(thiophen-2-ylmethyl)pyridine-3-carboxamide Chemical compound C1=CC(F)=CC=C1OC1=NC=CC=C1C(=O)NCC1=CC=CS1 BJSRBYOJJULYSJ-UHFFFAOYSA-N 0.000 claims description 2
- MAYFDYDEHBBQBH-UHFFFAOYSA-N 2-(4-fluorophenoxy)-n-[(4-nitrophenyl)methyl]pyridine-3-carboxamide Chemical compound C1=CC([N+](=O)[O-])=CC=C1CNC(=O)C1=CC=CN=C1OC1=CC=C(F)C=C1 MAYFDYDEHBBQBH-UHFFFAOYSA-N 0.000 claims description 2
- IIBOOXXMSWFBEG-UHFFFAOYSA-N 2-(4-fluorophenoxy)-n-[(5-oxomorpholin-2-yl)methyl]pyridine-3-carboxamide Chemical compound C1=CC(F)=CC=C1OC1=NC=CC=C1C(=O)NCC1OCC(=O)NC1 IIBOOXXMSWFBEG-UHFFFAOYSA-N 0.000 claims description 2
- BUDUHQWLNCFSKU-UHFFFAOYSA-N 2-[3-(2-hydroxypropan-2-yl)phenoxy]-n-(pyridin-4-ylmethyl)pyridine-3-carboxamide Chemical compound CC(C)(O)C1=CC=CC(OC=2C(=CC=CN=2)C(=O)NCC=2C=CN=CC=2)=C1 BUDUHQWLNCFSKU-UHFFFAOYSA-N 0.000 claims description 2
- 150000001204 N-oxides Chemical class 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 239000005864 Sulphur Substances 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000002393 azetidinyl group Chemical group 0.000 claims description 2
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000005050 dihydrooxazolyl group Chemical group O1C(NC=C1)* 0.000 claims description 2
- 125000005043 dihydropyranyl group Chemical group O1C(CCC=C1)* 0.000 claims description 2
- 229940079593 drug Drugs 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 2
- 125000001041 indolyl group Chemical group 0.000 claims description 2
- UCFFGYASXIPWPD-UHFFFAOYSA-N methyl hypochlorite Chemical group COCl UCFFGYASXIPWPD-UHFFFAOYSA-N 0.000 claims description 2
- 125000002757 morpholinyl group Chemical group 0.000 claims description 2
- VQANAUZRMOJPOI-UHFFFAOYSA-N n-(1-benzothiophen-2-ylmethyl)-2-(4-fluorophenoxy)pyridine-3-carboxamide Chemical compound C1=CC(F)=CC=C1OC1=NC=CC=C1C(=O)NCC1=CC2=CC=CC=C2S1 VQANAUZRMOJPOI-UHFFFAOYSA-N 0.000 claims description 2
- SAVBBXIRPLSMIB-UHFFFAOYSA-N n-[(2,3-difluorophenyl)methyl]-2-(4-fluorophenoxy)pyridine-3-carboxamide Chemical compound C1=CC(F)=CC=C1OC1=NC=CC=C1C(=O)NCC1=CC=CC(F)=C1F SAVBBXIRPLSMIB-UHFFFAOYSA-N 0.000 claims description 2
- XLQVQGNOQGHSBN-UHFFFAOYSA-N n-[(2-chlorophenyl)methyl]-2-(1h-indol-4-yloxy)pyridine-3-carboxamide Chemical compound ClC1=CC=CC=C1CNC(=O)C1=CC=CN=C1OC1=CC=CC2=C1C=CN2 XLQVQGNOQGHSBN-UHFFFAOYSA-N 0.000 claims description 2
- TUIZQXRLCNRPKD-UHFFFAOYSA-N n-[(2-chlorophenyl)methyl]-2-(3-cyanophenoxy)pyridine-3-carboxamide Chemical compound ClC1=CC=CC=C1CNC(=O)C1=CC=CN=C1OC1=CC=CC(C#N)=C1 TUIZQXRLCNRPKD-UHFFFAOYSA-N 0.000 claims description 2
- KWBBXYWTCCLXIT-UHFFFAOYSA-N n-[(2-chlorophenyl)methyl]-2-(4-cyanophenoxy)pyridine-3-carboxamide Chemical compound ClC1=CC=CC=C1CNC(=O)C1=CC=CN=C1OC1=CC=C(C#N)C=C1 KWBBXYWTCCLXIT-UHFFFAOYSA-N 0.000 claims description 2
- UGJDYDVYPRCCIC-UHFFFAOYSA-N n-[(2-chlorophenyl)methyl]-2-[3-(2-hydroxypropan-2-yl)phenoxy]pyridine-3-carboxamide Chemical compound CC(C)(O)C1=CC=CC(OC=2C(=CC=CN=2)C(=O)NCC=2C(=CC=CC=2)Cl)=C1 UGJDYDVYPRCCIC-UHFFFAOYSA-N 0.000 claims description 2
- XHZHDCRLOAYJGR-UHFFFAOYSA-N n-[(3,5-dichlorothiophen-2-yl)methyl]-2-(4-fluorophenoxy)pyridine-3-carboxamide Chemical compound C1=CC(F)=CC=C1OC1=NC=CC=C1C(=O)NCC1=C(Cl)C=C(Cl)S1 XHZHDCRLOAYJGR-UHFFFAOYSA-N 0.000 claims description 2
- PWPLHLKHBANAND-UHFFFAOYSA-N n-[(3,5-difluorophenyl)methyl]-2-(4-fluorophenoxy)pyridine-3-carboxamide Chemical compound C1=CC(F)=CC=C1OC1=NC=CC=C1C(=O)NCC1=CC(F)=CC(F)=C1 PWPLHLKHBANAND-UHFFFAOYSA-N 0.000 claims description 2
- XURNMKPJSBVRDH-UHFFFAOYSA-N n-[(4-chlorothiophen-2-yl)methyl]-2-(4-fluorophenoxy)pyridine-3-carboxamide Chemical compound C1=CC(F)=CC=C1OC1=NC=CC=C1C(=O)NCC1=CC(Cl)=CS1 XURNMKPJSBVRDH-UHFFFAOYSA-N 0.000 claims description 2
- ZLTNSRVWDRZSHD-UHFFFAOYSA-N n-[(5-chlorothiophen-2-yl)methyl]-2-(3-nitrophenoxy)pyridine-3-carboxamide Chemical compound [O-][N+](=O)C1=CC=CC(OC=2C(=CC=CN=2)C(=O)NCC=2SC(Cl)=CC=2)=C1 ZLTNSRVWDRZSHD-UHFFFAOYSA-N 0.000 claims description 2
- MXZNRVIMQNDNMW-UHFFFAOYSA-N n-[1-(4-bromophenyl)ethyl]-2-(4-fluorophenoxy)pyridine-3-carboxamide Chemical compound C=1C=C(Br)C=CC=1C(C)NC(=O)C1=CC=CN=C1OC1=CC=C(F)C=C1 MXZNRVIMQNDNMW-UHFFFAOYSA-N 0.000 claims description 2
- AQIVOZRZMGARTM-UHFFFAOYSA-N n-[[2-chloro-4-(2-hydroxypropan-2-yl)phenyl]methyl]-2-(3-cyano-4-fluorophenoxy)pyridine-3-carboxamide Chemical compound ClC1=CC(C(C)(O)C)=CC=C1CNC(=O)C1=CC=CN=C1OC1=CC=C(F)C(C#N)=C1 AQIVOZRZMGARTM-UHFFFAOYSA-N 0.000 claims description 2
- GZFPXIOEQOFNFD-UHFFFAOYSA-N n-[[2-chloro-4-(2-hydroxypropan-2-yl)phenyl]methyl]-2-(3-cyanophenoxy)pyridine-3-carboxamide Chemical compound ClC1=CC(C(C)(O)C)=CC=C1CNC(=O)C1=CC=CN=C1OC1=CC=CC(C#N)=C1 GZFPXIOEQOFNFD-UHFFFAOYSA-N 0.000 claims description 2
- LBAYRXVNEJQRJP-UHFFFAOYSA-N n-[[3-chloro-5-(2-hydroxypropan-2-yl)thiophen-2-yl]methyl]-2-(3-cyanophenoxy)pyridine-3-carboxamide Chemical compound S1C(C(C)(O)C)=CC(Cl)=C1CNC(=O)C1=CC=CN=C1OC1=CC=CC(C#N)=C1 LBAYRXVNEJQRJP-UHFFFAOYSA-N 0.000 claims description 2
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- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- FQFILJKFZCVHNH-UHFFFAOYSA-N tert-butyl n-[3-[(5-bromo-2-chloropyrimidin-4-yl)amino]propyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCNC1=NC(Cl)=NC=C1Br FQFILJKFZCVHNH-UHFFFAOYSA-N 0.000 description 1
- OSBSFAARYOCBHB-UHFFFAOYSA-N tetrapropylammonium Chemical compound CCC[N+](CCC)(CCC)CCC OSBSFAARYOCBHB-UHFFFAOYSA-N 0.000 description 1
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- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- MWKJTNBSKNUMFN-UHFFFAOYSA-N trifluoromethyltrimethylsilane Chemical compound C[Si](C)(C)C(F)(F)F MWKJTNBSKNUMFN-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
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- 230000006433 tumor necrosis factor production Effects 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
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Classifications
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- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pulmonology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Virology (AREA)
- Rheumatology (AREA)
- Dermatology (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Immunology (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Physical Education & Sports Medicine (AREA)
- Oncology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Molecular Biology (AREA)
- Communicable Diseases (AREA)
- Hospice & Palliative Care (AREA)
- Otolaryngology (AREA)
- Child & Adolescent Psychology (AREA)
- Orthopedic Medicine & Surgery (AREA)
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Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US4340397P | 1997-04-04 | 1997-04-04 | |
PCT/IB1998/000315 WO1998045268A1 (en) | 1997-04-04 | 1998-03-10 | Nicotinamide derivatives |
Publications (3)
Publication Number | Publication Date |
---|---|
NO994791D0 NO994791D0 (no) | 1999-10-01 |
NO994791L NO994791L (no) | 1999-12-01 |
NO314182B1 true NO314182B1 (no) | 2003-02-10 |
Family
ID=21927000
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO19994791A NO314182B1 (no) | 1997-04-04 | 1999-10-01 | Nikotinamid-derivater, anvendelse derav, samt farmasöytisk blanding |
Country Status (37)
Country | Link |
---|---|
US (1) | US6380218B1 (sh) |
EP (1) | EP0971894A1 (sh) |
JP (2) | JP2000510481A (sh) |
KR (1) | KR20010005954A (sh) |
CN (1) | CN1254335A (sh) |
AP (1) | AP1388A (sh) |
AR (1) | AR012574A1 (sh) |
AU (1) | AU738037B2 (sh) |
BG (1) | BG64356B1 (sh) |
BR (1) | BR9810733A (sh) |
CA (1) | CA2285548C (sh) |
CO (1) | CO4950625A1 (sh) |
DZ (1) | DZ2457A1 (sh) |
EA (1) | EA003528B1 (sh) |
GT (1) | GT199800058A (sh) |
HN (1) | HN1998000057A (sh) |
HR (1) | HRP980181B1 (sh) |
HU (1) | HUP0001243A3 (sh) |
ID (1) | ID22781A (sh) |
IL (1) | IL132033A0 (sh) |
IS (1) | IS5197A (sh) |
MA (1) | MA26479A1 (sh) |
MY (1) | MY141513A (sh) |
NO (1) | NO314182B1 (sh) |
NZ (1) | NZ337698A (sh) |
OA (1) | OA11163A (sh) |
PA (1) | PA8449601A1 (sh) |
PE (1) | PE73299A1 (sh) |
PL (1) | PL336148A1 (sh) |
SK (1) | SK132899A3 (sh) |
TN (1) | TNSN98045A1 (sh) |
TR (2) | TR200001847T2 (sh) |
TW (1) | TW519539B (sh) |
UA (1) | UA67737C2 (sh) |
WO (1) | WO1998045268A1 (sh) |
YU (1) | YU49899A (sh) |
ZA (1) | ZA982853B (sh) |
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- 1998-03-10 PL PL98336148A patent/PL336148A1/xx unknown
- 1998-03-10 AU AU62273/98A patent/AU738037B2/en not_active Ceased
- 1998-03-10 US US09/308,956 patent/US6380218B1/en not_active Expired - Fee Related
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- 1998-03-10 TR TR1999/02432T patent/TR199902432T2/xx unknown
- 1998-03-10 SK SK1328-99A patent/SK132899A3/sk unknown
- 1998-03-10 HU HU0001243A patent/HUP0001243A3/hu unknown
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- 1998-03-10 IL IL13203398A patent/IL132033A0/xx unknown
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- 1998-03-10 KR KR1019997009031A patent/KR20010005954A/ko active IP Right Grant
- 1998-03-10 YU YU49899A patent/YU49899A/sh unknown
- 1998-03-10 CA CA002285548A patent/CA2285548C/en not_active Expired - Fee Related
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- 1998-04-01 TN TNTNSN98045A patent/TNSN98045A1/fr unknown
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1999
- 1999-09-09 BG BG103725A patent/BG64356B1/bg unknown
- 1999-09-24 IS IS5197A patent/IS5197A/is unknown
- 1999-10-01 OA OA9900220A patent/OA11163A/en unknown
- 1999-10-01 NO NO19994791A patent/NO314182B1/no unknown
-
2003
- 2003-07-24 JP JP2003201291A patent/JP2004083583A/ja active Pending
Also Published As
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