CA2700559A1 - Derives de nicotinamide, leur preparation et leur application en therapeutique - Google Patents
Derives de nicotinamide, leur preparation et leur application en therapeutique Download PDFInfo
- Publication number
- CA2700559A1 CA2700559A1 CA2700559A CA2700559A CA2700559A1 CA 2700559 A1 CA2700559 A1 CA 2700559A1 CA 2700559 A CA2700559 A CA 2700559A CA 2700559 A CA2700559 A CA 2700559A CA 2700559 A1 CA2700559 A1 CA 2700559A1
- Authority
- CA
- Canada
- Prior art keywords
- pyridin
- phenyl
- ylmethyl
- cndot
- ureido
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 238000002360 preparation method Methods 0.000 title claims description 15
- 230000001225 therapeutic effect Effects 0.000 title description 3
- 150000005480 nicotinamides Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 161
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 72
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 63
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 47
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims abstract description 33
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 29
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract description 19
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 19
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 18
- 125000003118 aryl group Chemical group 0.000 claims abstract description 15
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 12
- 125000001424 substituent group Chemical group 0.000 claims abstract description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 10
- 125000005843 halogen group Chemical group 0.000 claims abstract description 10
- -1 -OH Chemical group 0.000 claims description 109
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 26
- 239000002253 acid Substances 0.000 claims description 25
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 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 22
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 125000003386 piperidinyl group Chemical group 0.000 claims description 16
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 16
- 125000004429 atom Chemical group 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 15
- 125000004193 piperazinyl group Chemical group 0.000 claims description 12
- 239000012190 activator Substances 0.000 claims description 9
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 8
- 229910052731 fluorine Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 125000002757 morpholinyl group Chemical group 0.000 claims description 7
- 229910052700 potassium Inorganic materials 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 230000008878 coupling Effects 0.000 claims description 6
- 238000010168 coupling process Methods 0.000 claims description 6
- 238000005859 coupling reaction Methods 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 125000005988 1,1-dioxo-thiomorpholinyl group Chemical group 0.000 claims description 5
- 125000005987 1-oxo-thiomorpholinyl group Chemical group 0.000 claims description 5
- 206010028980 Neoplasm Diseases 0.000 claims description 5
- 125000003725 azepanyl group Chemical group 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 5
- UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 claims description 5
- YNSJXHGTZJTEMM-UHFFFAOYSA-N 2-amino-n-methyl-6-[4-(pyridin-3-ylmethylcarbamoylamino)phenyl]pyridine-3-carboxamide Chemical compound N1=C(N)C(C(=O)NC)=CC=C1C(C=C1)=CC=C1NC(=O)NCC1=CC=CN=C1 YNSJXHGTZJTEMM-UHFFFAOYSA-N 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- ZZLBMYCVJGKGOF-UHFFFAOYSA-N pyridin-3-ylmethyl n-[4-[6-(ethylamino)-5-(methylcarbamoyl)pyridin-2-yl]phenyl]carbamate Chemical compound C1=C(C(=O)NC)C(NCC)=NC(C=2C=CC(NC(=O)OCC=3C=NC=CC=3)=CC=2)=C1 ZZLBMYCVJGKGOF-UHFFFAOYSA-N 0.000 claims description 4
- 239000012453 solvate Substances 0.000 claims description 4
- FTLVEXPJIRCUQK-UHFFFAOYSA-N 2-(ethylamino)-n-(2-piperidin-1-ylethyl)-6-[4-[[6-(propan-2-ylamino)pyridin-3-yl]methylcarbamoylamino]phenyl]pyridine-3-carboxamide Chemical compound CCNC1=NC(C=2C=CC(NC(=O)NCC=3C=NC(NC(C)C)=CC=3)=CC=2)=CC=C1C(=O)NCCN1CCCCC1 FTLVEXPJIRCUQK-UHFFFAOYSA-N 0.000 claims description 3
- NDLQRWHJWRVRND-UHFFFAOYSA-N 2-(ethylamino)-n-methyl-6-[4-(pyridin-3-ylmethylcarbamoylamino)phenyl]pyridine-3-carboxamide Chemical compound C1=C(C(=O)NC)C(NCC)=NC(C=2C=CC(NC(=O)NCC=3C=NC=CC=3)=CC=2)=C1 NDLQRWHJWRVRND-UHFFFAOYSA-N 0.000 claims description 3
- AYYCFAAFMVSETP-UHFFFAOYSA-N 2-[2-(dimethylamino)ethylamino]-n-methyl-6-[4-(pyridin-3-ylmethylcarbamoylamino)phenyl]pyridine-3-carboxamide Chemical compound N1=C(NCCN(C)C)C(C(=O)NC)=CC=C1C(C=C1)=CC=C1NC(=O)NCC1=CC=CN=C1 AYYCFAAFMVSETP-UHFFFAOYSA-N 0.000 claims description 3
- PUCQJJNWHNZEGN-UHFFFAOYSA-N 2-ethoxy-n-methyl-6-[4-(pyridin-3-ylmethylcarbamoylamino)phenyl]pyridine-3-carboxamide Chemical compound C1=C(C(=O)NC)C(OCC)=NC(C=2C=CC(NC(=O)NCC=3C=NC=CC=3)=CC=2)=C1 PUCQJJNWHNZEGN-UHFFFAOYSA-N 0.000 claims description 3
- QYBUNXBARMAXNY-UHFFFAOYSA-N 4-(ethylamino)-n-(2-piperidin-1-ylethyl)-2-[4-(pyridin-3-ylmethylcarbamoylamino)phenyl]pyrimidine-5-carboxamide Chemical compound CCNC1=NC(C=2C=CC(NC(=O)NCC=3C=NC=CC=3)=CC=2)=NC=C1C(=O)NCCN1CCCCC1 QYBUNXBARMAXNY-UHFFFAOYSA-N 0.000 claims description 3
- QZAVKQCNHAJXED-UHFFFAOYSA-N 6-[4-[(6-aminopyridin-3-yl)methylcarbamoylamino]phenyl]-2-(ethylamino)-n-(2-piperidin-1-ylethyl)pyridine-3-carboxamide Chemical compound CCNC1=NC(C=2C=CC(NC(=O)NCC=3C=NC(N)=CC=3)=CC=2)=CC=C1C(=O)NCCN1CCCCC1 QZAVKQCNHAJXED-UHFFFAOYSA-N 0.000 claims description 3
- GEFMTLXUJXKRCQ-UHFFFAOYSA-N 6-[4-[(6-aminopyridin-3-yl)methylcarbamoylamino]phenyl]-2-(ethylamino)-n-methylpyridine-3-carboxamide Chemical compound C1=C(C(=O)NC)C(NCC)=NC(C=2C=CC(NC(=O)NCC=3C=NC(N)=CC=3)=CC=2)=C1 GEFMTLXUJXKRCQ-UHFFFAOYSA-N 0.000 claims description 3
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 3
- 125000002393 azetidinyl group Chemical group 0.000 claims description 3
- 229910052796 boron Inorganic materials 0.000 claims description 3
- 238000010511 deprotection reaction Methods 0.000 claims description 3
- LIQUIDFGSAJZBQ-UHFFFAOYSA-N n-methyl-2-(oxolan-2-ylmethylamino)-6-[4-(pyridin-3-ylmethylcarbamoylamino)phenyl]pyridine-3-carboxamide Chemical compound CNC(=O)C1=CC=C(C=2C=CC(NC(=O)NCC=3C=NC=CC=3)=CC=2)N=C1NCC1CCCO1 LIQUIDFGSAJZBQ-UHFFFAOYSA-N 0.000 claims description 3
- CLHWNALKFOUJQE-UHFFFAOYSA-N 2-(benzylamino)-n-methyl-6-[4-(pyridin-3-ylmethylcarbamoylamino)phenyl]pyridine-3-carboxamide Chemical compound CNC(=O)C1=CC=C(C=2C=CC(NC(=O)NCC=3C=NC=CC=3)=CC=2)N=C1NCC1=CC=CC=C1 CLHWNALKFOUJQE-UHFFFAOYSA-N 0.000 claims description 2
- APBCRLMAOKRNTP-UHFFFAOYSA-N 2-(cyclobutylamino)-n-methyl-6-[4-(pyridin-3-ylmethylcarbamoylamino)phenyl]pyridine-3-carboxamide Chemical compound CNC(=O)C1=CC=C(C=2C=CC(NC(=O)NCC=3C=NC=CC=3)=CC=2)N=C1NC1CCC1 APBCRLMAOKRNTP-UHFFFAOYSA-N 0.000 claims description 2
- UZTGLCQPKADOPO-UHFFFAOYSA-N 2-(cyclohexylamino)-n-methyl-6-[4-(pyridin-3-ylmethylcarbamoylamino)phenyl]pyridine-3-carboxamide Chemical compound CNC(=O)C1=CC=C(C=2C=CC(NC(=O)NCC=3C=NC=CC=3)=CC=2)N=C1NC1CCCCC1 UZTGLCQPKADOPO-UHFFFAOYSA-N 0.000 claims description 2
- YWWCGZYXNKQEQU-UHFFFAOYSA-N 2-(cyclopentylamino)-n-methyl-6-[4-(pyridin-3-ylmethylcarbamoylamino)phenyl]pyridine-3-carboxamide Chemical compound CNC(=O)C1=CC=C(C=2C=CC(NC(=O)NCC=3C=NC=CC=3)=CC=2)N=C1NC1CCCC1 YWWCGZYXNKQEQU-UHFFFAOYSA-N 0.000 claims description 2
- OCUJOZZBTLSMRH-UHFFFAOYSA-N 2-(cyclopropylamino)-n-ethyl-6-[4-(pyridin-3-ylmethylcarbamoylamino)phenyl]pyridine-3-carboxamide Chemical compound CCNC(=O)C1=CC=C(C=2C=CC(NC(=O)NCC=3C=NC=CC=3)=CC=2)N=C1NC1CC1 OCUJOZZBTLSMRH-UHFFFAOYSA-N 0.000 claims description 2
- BMBDRNXJFVGCSZ-UHFFFAOYSA-N 2-(cyclopropylamino)-n-methyl-6-[4-(pyridin-3-ylmethylcarbamoylamino)phenyl]pyridine-3-carboxamide Chemical compound CNC(=O)C1=CC=C(C=2C=CC(NC(=O)NCC=3C=NC=CC=3)=CC=2)N=C1NC1CC1 BMBDRNXJFVGCSZ-UHFFFAOYSA-N 0.000 claims description 2
- YHKDINZRFWSAAO-UHFFFAOYSA-N 2-(diethylamino)-n-methyl-6-[4-(pyridin-3-ylmethylcarbamoylamino)phenyl]pyridine-3-carboxamide Chemical compound C1=C(C(=O)NC)C(N(CC)CC)=NC(C=2C=CC(NC(=O)NCC=3C=NC=CC=3)=CC=2)=C1 YHKDINZRFWSAAO-UHFFFAOYSA-N 0.000 claims description 2
- OCGODQPPCJDETO-UHFFFAOYSA-N 2-(ethylamino)-6-[4-(pyridin-3-ylmethylcarbamoylamino)phenyl]pyridine-3-carboxamide Chemical compound C1=C(C(N)=O)C(NCC)=NC(C=2C=CC(NC(=O)NCC=3C=NC=CC=3)=CC=2)=C1 OCGODQPPCJDETO-UHFFFAOYSA-N 0.000 claims description 2
- VTUZXJBGVHETGO-UHFFFAOYSA-N 2-(ethylamino)-6-[4-[(2-methoxypyridin-3-yl)methylcarbamoylamino]phenyl]-n-(2-piperidin-1-ylethyl)pyridine-3-carboxamide Chemical compound CCNC1=NC(C=2C=CC(NC(=O)NCC=3C(=NC=CC=3)OC)=CC=2)=CC=C1C(=O)NCCN1CCCCC1 VTUZXJBGVHETGO-UHFFFAOYSA-N 0.000 claims description 2
- KSNHGGVOQWKDQT-UHFFFAOYSA-N 2-(ethylamino)-6-[4-[(5-fluoropyridin-3-yl)methylcarbamoylamino]phenyl]-n-(2-piperidin-1-ylethyl)pyridine-3-carboxamide Chemical compound CCNC1=NC(C=2C=CC(NC(=O)NCC=3C=C(F)C=NC=3)=CC=2)=CC=C1C(=O)NCCN1CCCCC1 KSNHGGVOQWKDQT-UHFFFAOYSA-N 0.000 claims description 2
- YBCHSNFJSQZHER-UHFFFAOYSA-N 2-(ethylamino)-6-[4-[(5-methylpyridin-3-yl)methylcarbamoylamino]phenyl]-n-(2-piperidin-1-ylethyl)pyridine-3-carboxamide Chemical compound CCNC1=NC(C=2C=CC(NC(=O)NCC=3C=C(C)C=NC=3)=CC=2)=CC=C1C(=O)NCCN1CCCCC1 YBCHSNFJSQZHER-UHFFFAOYSA-N 0.000 claims description 2
- PAFLWKSQOATTPW-UHFFFAOYSA-N 2-(ethylamino)-6-[4-[(6-fluoropyridin-3-yl)methylcarbamoylamino]phenyl]-n-(2-piperidin-1-ylethyl)pyridine-3-carboxamide Chemical compound CCNC1=NC(C=2C=CC(NC(=O)NCC=3C=NC(F)=CC=3)=CC=2)=CC=C1C(=O)NCCN1CCCCC1 PAFLWKSQOATTPW-UHFFFAOYSA-N 0.000 claims description 2
- JZEDQOVFDBGKJN-UHFFFAOYSA-N 2-(ethylamino)-6-[4-[(6-methylpyridin-3-yl)methylcarbamoylamino]phenyl]-n-(2-piperidin-1-ylethyl)pyridine-3-carboxamide Chemical compound CCNC1=NC(C=2C=CC(NC(=O)NCC=3C=NC(C)=CC=3)=CC=2)=CC=C1C(=O)NCCN1CCCCC1 JZEDQOVFDBGKJN-UHFFFAOYSA-N 0.000 claims description 2
- YKEYHLMPWPHUTH-UHFFFAOYSA-N 2-(ethylamino)-6-[4-[[6-(methylamino)pyridin-3-yl]methylcarbamoylamino]phenyl]-n-(2-piperidin-1-ylethyl)pyridine-3-carboxamide Chemical compound CCNC1=NC(C=2C=CC(NC(=O)NCC=3C=NC(NC)=CC=3)=CC=2)=CC=C1C(=O)NCCN1CCCCC1 YKEYHLMPWPHUTH-UHFFFAOYSA-N 0.000 claims description 2
- YOHWAXXIFGEZNX-UHFFFAOYSA-N 2-(ethylamino)-n-(1-pyridin-3-ylethyl)-6-[4-(pyridin-3-ylmethylcarbamoylamino)phenyl]pyridine-3-carboxamide Chemical compound CCNC1=NC(C=2C=CC(NC(=O)NCC=3C=NC=CC=3)=CC=2)=CC=C1C(=O)NC(C)C1=CC=CN=C1 YOHWAXXIFGEZNX-UHFFFAOYSA-N 0.000 claims description 2
- HVRJRYKKWQFHEJ-UHFFFAOYSA-N 2-(ethylamino)-n-(2-piperazin-1-ylethyl)-6-[4-(pyridin-3-ylmethylcarbamoylamino)phenyl]pyridine-3-carboxamide Chemical compound CCNC1=NC(C=2C=CC(NC(=O)NCC=3C=NC=CC=3)=CC=2)=CC=C1C(=O)NCCN1CCNCC1 HVRJRYKKWQFHEJ-UHFFFAOYSA-N 0.000 claims description 2
- IZNVRNVHWYIXEF-UHFFFAOYSA-N 2-(ethylamino)-n-(2-piperidin-1-ylethyl)-6-[4-(pyridin-3-ylmethylcarbamoylamino)phenyl]pyridine-3-carboxamide Chemical compound CCNC1=NC(C=2C=CC(NC(=O)NCC=3C=NC=CC=3)=CC=2)=CC=C1C(=O)NCCN1CCCCC1 IZNVRNVHWYIXEF-UHFFFAOYSA-N 0.000 claims description 2
- SCJVGQDSOPAGSV-UHFFFAOYSA-N 2-(ethylamino)-n-(2-piperidin-1-ylethyl)-6-[4-[(2,5,6-trifluoropyridin-3-yl)methylcarbamoylamino]phenyl]pyridine-3-carboxamide Chemical compound CCNC1=NC(C=2C=CC(NC(=O)NCC=3C(=NC(F)=C(F)C=3)F)=CC=2)=CC=C1C(=O)NCCN1CCCCC1 SCJVGQDSOPAGSV-UHFFFAOYSA-N 0.000 claims description 2
- UNWBJFNUWOKHSQ-UHFFFAOYSA-N 2-(ethylamino)-n-(2-pyridin-2-ylethyl)-6-[4-(pyridin-3-ylmethylcarbamoylamino)phenyl]pyridine-3-carboxamide Chemical compound CCNC1=NC(C=2C=CC(NC(=O)NCC=3C=NC=CC=3)=CC=2)=CC=C1C(=O)NCCC1=CC=CC=N1 UNWBJFNUWOKHSQ-UHFFFAOYSA-N 0.000 claims description 2
- CODQEUJLCKXYLL-UHFFFAOYSA-N 2-(ethylamino)-n-(3-piperidin-1-ylpropyl)-6-[4-(pyridin-3-ylmethylcarbamoylamino)phenyl]pyridine-3-carboxamide Chemical compound CCNC1=NC(C=2C=CC(NC(=O)NCC=3C=NC=CC=3)=CC=2)=CC=C1C(=O)NCCCN1CCCCC1 CODQEUJLCKXYLL-UHFFFAOYSA-N 0.000 claims description 2
- MRGUYMUYZUILCN-UHFFFAOYSA-N 2-(ethylamino)-n-(4-piperidin-1-ylbutyl)-6-[4-(pyridin-3-ylmethylcarbamoylamino)phenyl]pyridine-3-carboxamide Chemical compound CCNC1=NC(C=2C=CC(NC(=O)NCC=3C=NC=CC=3)=CC=2)=CC=C1C(=O)NCCCCN1CCCCC1 MRGUYMUYZUILCN-UHFFFAOYSA-N 0.000 claims description 2
- BIECWHKYRVJYSI-UHFFFAOYSA-N 2-(ethylamino)-n-[2-(3-hydroxypiperidin-1-yl)ethyl]-6-[4-(pyridin-3-ylmethylcarbamoylamino)phenyl]pyridine-3-carboxamide Chemical compound CCNC1=NC(C=2C=CC(NC(=O)NCC=3C=NC=CC=3)=CC=2)=CC=C1C(=O)NCCN1CCCC(O)C1 BIECWHKYRVJYSI-UHFFFAOYSA-N 0.000 claims description 2
- CTKAJPYTUYQFCT-UHFFFAOYSA-N 2-(ethylamino)-n-[2-(4-hydroxypiperidin-1-yl)ethyl]-6-[4-(pyridin-3-ylmethylcarbamoylamino)phenyl]pyridine-3-carboxamide Chemical compound CCNC1=NC(C=2C=CC(NC(=O)NCC=3C=NC=CC=3)=CC=2)=CC=C1C(=O)NCCN1CCC(O)CC1 CTKAJPYTUYQFCT-UHFFFAOYSA-N 0.000 claims description 2
- BBADFUVNOFFPOQ-UHFFFAOYSA-N 2-(ethylamino)-n-[2-(4-methoxypiperidin-1-yl)ethyl]-6-[4-(pyridin-3-ylmethylcarbamoylamino)phenyl]pyridine-3-carboxamide Chemical compound CCNC1=NC(C=2C=CC(NC(=O)NCC=3C=NC=CC=3)=CC=2)=CC=C1C(=O)NCCN1CCC(OC)CC1 BBADFUVNOFFPOQ-UHFFFAOYSA-N 0.000 claims description 2
- DHVOOBNVMONLDZ-UHFFFAOYSA-N 2-(ethylamino)-n-methyl-4-[4-(pyridin-3-ylmethylcarbamoylamino)phenyl]benzamide Chemical compound C1=C(C(=O)NC)C(NCC)=CC(C=2C=CC(NC(=O)NCC=3C=NC=CC=3)=CC=2)=C1 DHVOOBNVMONLDZ-UHFFFAOYSA-N 0.000 claims description 2
- LQRBQWQSQXKXHH-UHFFFAOYSA-N 2-(ethylamino)-n-methyl-6-[4-(3-pyridin-3-ylpropanoylamino)phenyl]pyridine-3-carboxamide Chemical compound C1=C(C(=O)NC)C(NCC)=NC(C=2C=CC(NC(=O)CCC=3C=NC=CC=3)=CC=2)=C1 LQRBQWQSQXKXHH-UHFFFAOYSA-N 0.000 claims description 2
- MNGYRCGVNRNLPK-UHFFFAOYSA-N 2-(ethylamino)-n-pyridin-2-yl-6-[4-(pyridin-3-ylmethylcarbamoylamino)phenyl]pyridine-3-carboxamide Chemical compound CCNC1=NC(C=2C=CC(NC(=O)NCC=3C=NC=CC=3)=CC=2)=CC=C1C(=O)NC1=CC=CC=N1 MNGYRCGVNRNLPK-UHFFFAOYSA-N 0.000 claims description 2
- ZRNFSAZGWPMRJC-UHFFFAOYSA-N 2-(ethylamino)-n-pyridin-3-yl-6-[4-(pyridin-3-ylmethylcarbamoylamino)phenyl]pyridine-3-carboxamide Chemical compound CCNC1=NC(C=2C=CC(NC(=O)NCC=3C=NC=CC=3)=CC=2)=CC=C1C(=O)NC1=CC=CN=C1 ZRNFSAZGWPMRJC-UHFFFAOYSA-N 0.000 claims description 2
- AYOAIRRSXHQLOQ-UHFFFAOYSA-N 2-[4-[(6-aminopyridin-3-yl)methylcarbamoylamino]phenyl]-4-(ethylamino)-n-(2-piperidin-1-ylethyl)pyrimidine-5-carboxamide Chemical compound CCNC1=NC(C=2C=CC(NC(=O)NCC=3C=NC(N)=CC=3)=CC=2)=NC=C1C(=O)NCCN1CCCCC1 AYOAIRRSXHQLOQ-UHFFFAOYSA-N 0.000 claims description 2
- BQOMAILCSRXVQV-UHFFFAOYSA-N 2-amino-6-[4-(pyridin-3-ylmethylcarbamoylamino)phenyl]pyridine-3-carboxamide Chemical compound N1=C(N)C(C(=O)N)=CC=C1C(C=C1)=CC=C1NC(=O)NCC1=CC=CN=C1 BQOMAILCSRXVQV-UHFFFAOYSA-N 0.000 claims description 2
- MGUBQCJZFVNVLQ-UHFFFAOYSA-N 2-anilino-n-methyl-6-[4-(pyridin-3-ylmethylcarbamoylamino)phenyl]pyridine-3-carboxamide Chemical compound CNC(=O)C1=CC=C(C=2C=CC(NC(=O)NCC=3C=NC=CC=3)=CC=2)N=C1NC1=CC=CC=C1 MGUBQCJZFVNVLQ-UHFFFAOYSA-N 0.000 claims description 2
- MRTCUPYTTVBHEK-UHFFFAOYSA-N 2-piperidin-1-ylethyl 6-[4-[(6-aminopyridin-3-yl)methylcarbamoylamino]phenyl]-2-(ethylamino)pyridine-3-carboxylate Chemical compound CCNC1=NC(C=2C=CC(NC(=O)NCC=3C=NC(N)=CC=3)=CC=2)=CC=C1C(=O)OCCN1CCCCC1 MRTCUPYTTVBHEK-UHFFFAOYSA-N 0.000 claims description 2
- NXCPGFZOYNHHAU-UHFFFAOYSA-N 4-(ethylamino)-n-methyl-2-[4-(pyridin-3-ylmethylcarbamoylamino)phenyl]pyrimidine-5-carboxamide Chemical compound C1=C(C(=O)NC)C(NCC)=NC(C=2C=CC(NC(=O)NCC=3C=NC=CC=3)=CC=2)=N1 NXCPGFZOYNHHAU-UHFFFAOYSA-N 0.000 claims description 2
- IHNDQALKRYRGNP-UHFFFAOYSA-N 4-(ethylamino)-n-methyl-6-[4-(pyridin-3-ylmethylcarbamoylamino)phenyl]pyridine-3-carboxamide Chemical compound C1=C(C(=O)NC)C(NCC)=CC(C=2C=CC(NC(=O)NCC=3C=NC=CC=3)=CC=2)=N1 IHNDQALKRYRGNP-UHFFFAOYSA-N 0.000 claims description 2
- PADXLJCSJODLEM-UHFFFAOYSA-N 4-[4-[(6-amino-5-methylpyridin-3-yl)methylcarbamoylamino]phenyl]-2-(ethylamino)-n-(2-piperidin-1-ylethyl)benzamide Chemical compound CCNC1=CC(C=2C=CC(NC(=O)NCC=3C=C(C)C(N)=NC=3)=CC=2)=CC=C1C(=O)NCCN1CCCCC1 PADXLJCSJODLEM-UHFFFAOYSA-N 0.000 claims description 2
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 230000004663 cell proliferation Effects 0.000 description 1
- XJHCXCQVJFPJIK-UHFFFAOYSA-M cesium fluoride Substances [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 1
- 239000007806 chemical reaction intermediate Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 229940126086 compound 21 Drugs 0.000 description 1
- 229940127204 compound 29 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
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- 229910052802 copper Inorganic materials 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 238000006880 cross-coupling reaction Methods 0.000 description 1
- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- NXQGGXCHGDYOHB-UHFFFAOYSA-L cyclopenta-1,4-dien-1-yl(diphenyl)phosphane;dichloropalladium;iron(2+) Chemical compound [Fe+2].Cl[Pd]Cl.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 NXQGGXCHGDYOHB-UHFFFAOYSA-L 0.000 description 1
- UHDGCWIWMRVCDJ-ZAKLUEHWSA-N cytidine Chemical class O=C1N=C(N)C=CN1[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O1 UHDGCWIWMRVCDJ-ZAKLUEHWSA-N 0.000 description 1
- 229940127089 cytotoxic agent Drugs 0.000 description 1
- AZLYZRGJCVQKKK-UHFFFAOYSA-N dioxohydrazine Chemical compound O=NN=O AZLYZRGJCVQKKK-UHFFFAOYSA-N 0.000 description 1
- 230000006806 disease prevention Effects 0.000 description 1
- 239000003534 dna topoisomerase inhibitor Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000001076 estrogenic effect Effects 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- SRJBDGLSCPDXBL-UHFFFAOYSA-N ethyl 2,4-dichloropyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=CN=C(Cl)N=C1Cl SRJBDGLSCPDXBL-UHFFFAOYSA-N 0.000 description 1
- 238000000105 evaporative light scattering detection Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 150000005699 fluoropyrimidines Chemical class 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000006445 hexyl cyclopropyl group Chemical group 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 1
- GLXDVVHUTZTUQK-UHFFFAOYSA-M lithium;hydroxide;hydrate Chemical compound [Li+].O.[OH-] GLXDVVHUTZTUQK-UHFFFAOYSA-M 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 125000006431 methyl cyclopropyl group Chemical group 0.000 description 1
- 230000002438 mitochondrial effect Effects 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- CURJNMSGPBXOGK-UHFFFAOYSA-N n',n'-di(propan-2-yl)ethane-1,2-diamine Chemical compound CC(C)N(C(C)C)CCN CURJNMSGPBXOGK-UHFFFAOYSA-N 0.000 description 1
- FUIWYQORJIDUEN-UHFFFAOYSA-N n-(5-cyanopyridin-2-yl)-2-methylpropanamide Chemical compound CC(C)C(=O)NC1=CC=C(C#N)C=N1 FUIWYQORJIDUEN-UHFFFAOYSA-N 0.000 description 1
- QPIWSYSAKLNUMB-UHFFFAOYSA-N n-cyclopentyl-2-(cyclopropylamino)-6-[4-(pyridin-3-ylmethylcarbamoylamino)phenyl]pyridine-3-carboxamide Chemical compound C=1C=C(C=2N=C(NC3CC3)C(C(=O)NC3CCCC3)=CC=2)C=CC=1NC(=O)NCC1=CC=CN=C1 QPIWSYSAKLNUMB-UHFFFAOYSA-N 0.000 description 1
- HGSJXFRQJQMELD-UHFFFAOYSA-N n-cyclopropyl-2-(cyclopropylamino)-6-[4-(pyridin-3-ylmethylcarbamoylamino)phenyl]pyridine-3-carboxamide Chemical compound C=1C=C(C=2N=C(NC3CC3)C(C(=O)NC3CC3)=CC=2)C=CC=1NC(=O)NCC1=CC=CN=C1 HGSJXFRQJQMELD-UHFFFAOYSA-N 0.000 description 1
- WQZXJTWTIYVJLT-UHFFFAOYSA-N n-ethylpiperidin-1-amine Chemical compound CCNN1CCCCC1 WQZXJTWTIYVJLT-UHFFFAOYSA-N 0.000 description 1
- DBGFNLVRAFYZBI-UHFFFAOYSA-N n-methylpyridin-3-amine Chemical compound CNC1=CC=CN=C1 DBGFNLVRAFYZBI-UHFFFAOYSA-N 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229960002715 nicotine Drugs 0.000 description 1
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 1
- 229960004738 nicotinyl alcohol Drugs 0.000 description 1
- 235000020824 obesity Nutrition 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 150000002940 palladium Chemical class 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 230000007170 pathology Effects 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 1
- 150000003057 platinum Chemical class 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 239000011698 potassium fluoride Substances 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000001012 protector Effects 0.000 description 1
- 230000005588 protonation Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical group OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 1
- TXQWFIVRZNOPCK-UHFFFAOYSA-N pyridin-4-ylmethanamine Chemical compound NCC1=CC=NC=C1 TXQWFIVRZNOPCK-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- LFKDJXLFVYVEFG-UHFFFAOYSA-N tert-butyl carbamate Chemical compound CC(C)(C)OC(N)=O LFKDJXLFVYVEFG-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- RBDZEJHRPTUXLF-UHFFFAOYSA-N tert-butyl n-[5-[[[4-[6-(ethylamino)-5-(2-piperidin-1-ylethylcarbamoyl)pyridin-2-yl]phenyl]carbamoylamino]methyl]pyridin-2-yl]carbamate Chemical compound CCNC1=NC(C=2C=CC(NC(=O)NCC=3C=NC(NC(=O)OC(C)(C)C)=CC=3)=CC=2)=CC=C1C(=O)NCCN1CCCCC1 RBDZEJHRPTUXLF-UHFFFAOYSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- CMQCNTNASCDNGR-UHFFFAOYSA-N toluene;hydrate Chemical compound O.CC1=CC=CC=C1 CMQCNTNASCDNGR-UHFFFAOYSA-N 0.000 description 1
- 229940044693 topoisomerase inhibitor Drugs 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
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 1
- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 1
- 235000019798 tripotassium phosphate Nutrition 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- ZXYAAVBXHKCJJB-UHFFFAOYSA-N uracil-5-carboxylic acid Chemical compound OC(=O)C1=CNC(=O)NC1=O ZXYAAVBXHKCJJB-UHFFFAOYSA-N 0.000 description 1
- 239000004066 vascular targeting agent Substances 0.000 description 1
- 230000035899 viability Effects 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—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
- 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides in position 3
-
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0706799 | 2007-09-28 | ||
| FR0706799A FR2921657A1 (fr) | 2007-09-28 | 2007-09-28 | Derives de nicotinamide, leur preparation et leur application en therapeutique |
| PCT/FR2008/001338 WO2009074749A2 (fr) | 2007-09-28 | 2008-09-26 | Dérives de nicotinamide. leur préparation et leur application en thérapeutique |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2700559A1 true CA2700559A1 (fr) | 2009-06-18 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2700559A Abandoned CA2700559A1 (fr) | 2007-09-28 | 2008-09-26 | Derives de nicotinamide, leur preparation et leur application en therapeutique |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US20100222319A1 (https=) |
| EP (1) | EP2205566A2 (https=) |
| JP (1) | JP2010540504A (https=) |
| KR (1) | KR20100065165A (https=) |
| CN (1) | CN101808996A (https=) |
| AR (1) | AR066171A1 (https=) |
| AU (1) | AU2008334457A1 (https=) |
| BR (1) | BRPI0817973A2 (https=) |
| CA (1) | CA2700559A1 (https=) |
| CL (1) | CL2008002893A1 (https=) |
| FR (1) | FR2921657A1 (https=) |
| IL (1) | IL204663A0 (https=) |
| MX (1) | MX2010003445A (https=) |
| PA (1) | PA8797301A1 (https=) |
| PE (1) | PE20091033A1 (https=) |
| RU (1) | RU2010116765A (https=) |
| TW (1) | TW200918056A (https=) |
| UY (1) | UY31367A1 (https=) |
| WO (1) | WO2009074749A2 (https=) |
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| CN102775396B (zh) | 2005-11-08 | 2014-10-08 | 沃泰克斯药物股份有限公司 | Atp-结合弹夹转运蛋白的杂环调控剂 |
| CN104447716A (zh) | 2007-05-09 | 2015-03-25 | 沃泰克斯药物股份有限公司 | Cftr调节剂 |
| MX365732B (es) | 2007-12-07 | 2019-06-12 | Vertex Pharma | Procesos para producir acidos cicloalquilcarboxamido-piridin benzoicos. |
| EP3683218B1 (en) | 2007-12-07 | 2024-09-18 | Vertex Pharmaceuticals Incorporated | Solid forms of 3-(6-(1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl) cyclopropanecarboxamido)-3-methylpyridin-2-yl) benzoic acid |
| NZ720282A (en) | 2008-02-28 | 2017-12-22 | Vertex Pharma | Heteroaryl derivatives as cftr modulators |
| FR2943675A1 (fr) * | 2009-03-24 | 2010-10-01 | Sanofi Aventis | Composes anticancereux, leur preparation et leur application en therapeutique |
| FR2943670B1 (fr) * | 2009-03-24 | 2011-05-06 | Sanofi Aventis | Derives anticancereux,leur preparation et leur application en therapeutique |
| FR2943669B1 (fr) * | 2009-03-24 | 2011-05-06 | Sanofi Aventis | Derives de nicotinamide,leur preparation et leur application en therapeutique |
| EP2440204B1 (en) * | 2009-06-12 | 2013-12-18 | Bristol-Myers Squibb Company | Nicotinamide compounds useful as kinase modulators |
| AU2011223790A1 (en) * | 2010-03-01 | 2012-08-30 | Myrexis, Inc. | Compounds and therapeutic uses thereof |
| US8912184B1 (en) | 2010-03-01 | 2014-12-16 | Alzheimer's Institute Of America, Inc. | Therapeutic and diagnostic methods |
| JP2013523833A (ja) | 2010-04-07 | 2013-06-17 | バーテックス ファーマシューティカルズ インコーポレイテッド | ３−（６−（１−（２，２−ジフルオロベンゾ［ｄ］［１，３］ジオキソール−５−イル）シクロプロパンカルボキサミド）−３−メチルピリジン−２−イル）安息香酸の医薬組成物およびその投与 |
| US8827372B2 (en) | 2010-07-07 | 2014-09-09 | Frontis Corp. | Blowing system |
| FR2965263A1 (fr) * | 2010-09-24 | 2012-03-30 | Sanofi Aventis | Derives de thienopyridine nicotinamide, leur preparation et leur application en therapeutique |
| US9169246B2 (en) | 2011-09-26 | 2015-10-27 | Sanofi | Pyrazoloquinolinone derivatives, preparation thereof and therapeutic use thereof |
| CN103012397B (zh) * | 2011-09-26 | 2017-03-01 | 赛诺菲 | 吡唑并喹啉酮衍生物、其制备方法及其治疗用途 |
| PT2573073E (pt) * | 2011-09-26 | 2015-02-05 | Sanofi Sa | Derivados de pirazoloquinolinona, sua preparação e sua utilização terapêutica |
| NZ727015A (en) | 2012-01-25 | 2017-12-22 | Vertex Pharma | Formulations of 3-(6-(1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl) cyclopropanecarboxamido)-3-methylpyridin-2-yl)benzoic acid |
| AU2014349010C1 (en) | 2013-11-12 | 2020-08-06 | Vertex Pharmaceuticals Incorporated | Process of preparing pharmaceutical compositions for the treatment of CFTR mediated diseases |
| CN103804270B (zh) * | 2014-01-23 | 2016-06-22 | 中国药科大学 | 5-(4-甲脒基苄氧基)色氨酸衍生物、其制法及应用 |
| RU2691136C2 (ru) | 2014-11-18 | 2019-06-11 | Вертекс Фармасьютикалз Инкорпорейтед | Способ проведения высокопроизводительной тестовой высокоэффективной жидкостной хроматографии |
| JP7092356B2 (ja) * | 2016-06-22 | 2022-06-28 | フーダン ユニヴァーシティ | ビアリール尿素誘導体またはそれらの塩、およびそれらの調製方法および使用 |
| CN107522641B (zh) * | 2016-06-22 | 2020-05-05 | 复旦大学 | 联芳基脲类衍生物或其盐及其制备方法和用途 |
| KR102831570B1 (ko) | 2018-05-04 | 2025-07-10 | 레미디 플랜, 인크. | 암 줄기 세포를 표적화하는 암 치료 |
| CN110396065A (zh) * | 2019-06-25 | 2019-11-01 | 南京普锐达医药科技有限公司 | 一种2,4-二氯-5-嘧啶甲酰氯的合成方法 |
| AU2020378067A1 (en) * | 2019-11-06 | 2022-05-26 | Remedy Plan, Inc. | Cancer treatments targeting cancer stem cells |
| WO2021219513A1 (en) | 2020-04-28 | 2021-11-04 | Basf Se | Pesticidal compounds |
| JP2024518089A (ja) * | 2021-05-13 | 2024-04-24 | リメディー プラン，インコーポレーテッド | Ｎａｍｐｔ阻害剤とその使用 |
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| DE4301110A1 (de) * | 1993-01-18 | 1994-07-21 | Bayer Ag | Verfahren zur Herstellung von 2-Amino-5-aminomethyl-pyridin |
| CZ20012185A3 (cs) * | 1998-12-16 | 2001-10-17 | Bayer Aktiengesellschaft | Nové bifenylové sloučeniny a sloučeniny analogické bifenylovým sloučeninám, způsob jejich přípravy, farmaceutické prostředky a pouľití těchto sloučenin a prostředků jako antagonistů integrinu |
| DE10063008A1 (de) * | 2000-12-16 | 2002-06-20 | Merck Patent Gmbh | Carbonsäureamidderivate |
| US20040067985A1 (en) * | 2002-10-04 | 2004-04-08 | Fortuna Haviv | Method of inhibiting angiogenesis |
| JP2007515400A (ja) * | 2003-11-28 | 2007-06-14 | ノバルティス アクチエンゲゼルシャフト | タンパク質キナーゼ依存性疾患の処置におけるジアリール尿素誘導体 |
| US20060216288A1 (en) * | 2005-03-22 | 2006-09-28 | Amgen Inc | Combinations for the treatment of cancer |
-
2007
- 2007-09-28 FR FR0706799A patent/FR2921657A1/fr not_active Withdrawn
-
2008
- 2008-09-24 TW TW097136703A patent/TW200918056A/zh unknown
- 2008-09-26 JP JP2010526335A patent/JP2010540504A/ja not_active Withdrawn
- 2008-09-26 KR KR1020107006595A patent/KR20100065165A/ko not_active Withdrawn
- 2008-09-26 EP EP08859496A patent/EP2205566A2/fr not_active Withdrawn
- 2008-09-26 BR BRPI0817973-5A patent/BRPI0817973A2/pt not_active IP Right Cessation
- 2008-09-26 CA CA2700559A patent/CA2700559A1/fr not_active Abandoned
- 2008-09-26 PE PE2008001687A patent/PE20091033A1/es not_active Application Discontinuation
- 2008-09-26 MX MX2010003445A patent/MX2010003445A/es not_active Application Discontinuation
- 2008-09-26 CN CN200880109332A patent/CN101808996A/zh active Pending
- 2008-09-26 CL CL2008002893A patent/CL2008002893A1/es unknown
- 2008-09-26 AU AU2008334457A patent/AU2008334457A1/en not_active Abandoned
- 2008-09-26 UY UY31367A patent/UY31367A1/es not_active Application Discontinuation
- 2008-09-26 RU RU2010116765/04A patent/RU2010116765A/ru not_active Application Discontinuation
- 2008-09-26 PA PA20088797301A patent/PA8797301A1/es unknown
- 2008-09-26 AR ARP080104193A patent/AR066171A1/es unknown
- 2008-09-26 WO PCT/FR2008/001338 patent/WO2009074749A2/fr not_active Ceased
-
2010
- 2010-03-22 IL IL204663A patent/IL204663A0/en unknown
- 2010-03-26 US US12/732,749 patent/US20100222319A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| AU2008334457A1 (en) | 2009-06-18 |
| WO2009074749A2 (fr) | 2009-06-18 |
| WO2009074749A3 (fr) | 2009-08-20 |
| CN101808996A (zh) | 2010-08-18 |
| RU2010116765A (ru) | 2011-11-27 |
| PA8797301A1 (es) | 2009-05-15 |
| FR2921657A1 (fr) | 2009-04-03 |
| MX2010003445A (es) | 2010-04-27 |
| EP2205566A2 (fr) | 2010-07-14 |
| PE20091033A1 (es) | 2009-08-17 |
| US20100222319A1 (en) | 2010-09-02 |
| UY31367A1 (es) | 2009-04-30 |
| CL2008002893A1 (es) | 2009-10-16 |
| KR20100065165A (ko) | 2010-06-15 |
| IL204663A0 (en) | 2010-11-30 |
| AR066171A1 (es) | 2009-07-29 |
| JP2010540504A (ja) | 2010-12-24 |
| BRPI0817973A2 (pt) | 2019-04-09 |
| TW200918056A (en) | 2009-05-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |
Effective date: 20130926 |