FR2926297A1 - Molecules chimiques inhibitrices du mecanisme d'epissage pour traiter des maladies resultant d'anomalies d'epissage. - Google Patents
Molecules chimiques inhibitrices du mecanisme d'epissage pour traiter des maladies resultant d'anomalies d'epissage. Download PDFInfo
- Publication number
- FR2926297A1 FR2926297A1 FR0850144A FR0850144A FR2926297A1 FR 2926297 A1 FR2926297 A1 FR 2926297A1 FR 0850144 A FR0850144 A FR 0850144A FR 0850144 A FR0850144 A FR 0850144A FR 2926297 A1 FR2926297 A1 FR 2926297A1
- Authority
- FR
- France
- Prior art keywords
- benzamide
- phenylamino
- methyl
- group
- diethylamino
- 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.)
- Granted
Links
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims abstract description 20
- 201000010099 disease Diseases 0.000 title claims abstract description 18
- 230000007246 mechanism Effects 0.000 title description 5
- 230000002401 inhibitory effect Effects 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 111
- 238000002360 preparation method Methods 0.000 claims abstract description 9
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 4
- 239000003814 drug Substances 0.000 claims abstract description 3
- -1 3-Imidazol-1-yl-propyl Chemical group 0.000 claims description 57
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 47
- 210000004027 cell Anatomy 0.000 claims description 35
- 238000000034 method Methods 0.000 claims description 23
- 108090000623 proteins and genes Proteins 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 229910052757 nitrogen Inorganic materials 0.000 claims description 17
- 230000008569 process Effects 0.000 claims description 16
- 230000035772 mutation Effects 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 11
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 11
- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 10
- 108020004999 messenger RNA Proteins 0.000 claims description 9
- 230000032683 aging Effects 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 7
- 230000003612 virological effect Effects 0.000 claims description 7
- 208000030507 AIDS Diseases 0.000 claims description 6
- 125000004429 atom Chemical group 0.000 claims description 6
- NOCSCLVSJBOTTB-UHFFFAOYSA-N n-[3-(diethylamino)propyl]-3-[3-[(3-methoxybenzoyl)amino]anilino]benzamide Chemical compound CCN(CC)CCCNC(=O)C1=CC=CC(NC=2C=C(NC(=O)C=3C=C(OC)C=CC=3)C=CC=2)=C1 NOCSCLVSJBOTTB-UHFFFAOYSA-N 0.000 claims description 6
- XXMMMCMUEOONLX-UHFFFAOYSA-N n-[3-(diethylamino)propyl]-4-[3-[(3-methoxybenzoyl)amino]anilino]-3-methylbenzamide Chemical compound CC1=CC(C(=O)NCCCN(CC)CC)=CC=C1NC1=CC=CC(NC(=O)C=2C=C(OC)C=CC=2)=C1 XXMMMCMUEOONLX-UHFFFAOYSA-N 0.000 claims description 6
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 6
- ZEJFPRRKAYPBRR-UHFFFAOYSA-N 3-methoxy-n-[3-[4-(3-methylbutylcarbamoyl)anilino]phenyl]benzamide Chemical compound COC1=CC=CC(C(=O)NC=2C=C(NC=3C=CC(=CC=3)C(=O)NCCC(C)C)C=CC=2)=C1 ZEJFPRRKAYPBRR-UHFFFAOYSA-N 0.000 claims description 5
- FARHIFIXEBMFLL-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-4-[4-(trifluoromethoxy)anilino]benzamide Chemical compound C1=CC(C(=O)NCCN(C)C)=CC=C1NC1=CC=C(OC(F)(F)F)C=C1 FARHIFIXEBMFLL-UHFFFAOYSA-N 0.000 claims description 5
- ZCRNEOWAENGMKO-UHFFFAOYSA-N 4-[3-[(4-methoxybenzoyl)amino]anilino]-3-methyl-n-(3-methylbutyl)benzamide Chemical compound C1=CC(OC)=CC=C1C(=O)NC1=CC=CC(NC=2C(=CC(=CC=2)C(=O)NCCC(C)C)C)=C1 ZCRNEOWAENGMKO-UHFFFAOYSA-N 0.000 claims description 4
- PJBPBHKZDXGKJG-CMDGGOBGSA-N 4-methyl-n-(3-methylbutyl)-3-[3-[(e)-2-pyridin-4-ylethenyl]anilino]benzamide Chemical compound CC(C)CCNC(=O)C1=CC=C(C)C(NC=2C=C(\C=C\C=3C=CN=CC=3)C=CC=2)=C1 PJBPBHKZDXGKJG-CMDGGOBGSA-N 0.000 claims description 4
- DTMOKOVLSJWVHF-VOTSOKGWSA-N n-(3-methylbutyl)-4-[3-[(e)-2-pyridin-4-ylethenyl]anilino]benzamide Chemical compound C1=CC(C(=O)NCCC(C)C)=CC=C1NC1=CC=CC(\C=C\C=2C=CN=CC=2)=C1 DTMOKOVLSJWVHF-VOTSOKGWSA-N 0.000 claims description 4
- HQIVOIXZAPUWLY-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-4-(pyridin-3-ylamino)benzamide Chemical compound C1=CC(C(=O)NCCN(C)C)=CC=C1NC1=CC=CN=C1 HQIVOIXZAPUWLY-UHFFFAOYSA-N 0.000 claims description 4
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- GNISBZMJFHJXNU-MDZDMXLPSA-N 3-[1-[3-[3-[(e)-2-pyridin-4-ylethenyl]anilino]phenyl]triazol-4-yl]propan-1-ol Chemical compound N1=NC(CCCO)=CN1C1=CC=CC(NC=2C=C(\C=C\C=3C=CN=CC=3)C=CC=2)=C1 GNISBZMJFHJXNU-MDZDMXLPSA-N 0.000 claims description 3
- UEUHRHHHIWCCFK-UHFFFAOYSA-N 3-[4-[diethylamino(methyl)amino]triazol-1-yl]-n-(4-methoxyphenyl)aniline Chemical compound N1=NC(N(C)N(CC)CC)=CN1C1=CC=CC(NC=2C=CC(OC)=CC=2)=C1 UEUHRHHHIWCCFK-UHFFFAOYSA-N 0.000 claims description 3
- 201000001320 Atherosclerosis Diseases 0.000 claims description 3
- 208000002177 Cataract Diseases 0.000 claims description 3
- 206010022489 Insulin Resistance Diseases 0.000 claims description 3
- 208000001132 Osteoporosis Diseases 0.000 claims description 3
- 210000000481 breast Anatomy 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 208000037819 metastatic cancer Diseases 0.000 claims description 3
- 208000011575 metastatic malignant neoplasm Diseases 0.000 claims description 3
- RPIINHOYBAFYGL-UHFFFAOYSA-N n-(3-imidazol-1-ylpropyl)-2-[4-(trifluoromethoxy)anilino]benzamide Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC1=CC=CC=C1C(=O)NCCCN1C=NC=C1 RPIINHOYBAFYGL-UHFFFAOYSA-N 0.000 claims description 3
- YQCSORIIPSUFJA-MDZDMXLPSA-N n-(3-methylbutyl)-3-[3-[(e)-2-pyridin-4-ylethenyl]anilino]benzamide Chemical compound CC(C)CCNC(=O)C1=CC=CC(NC=2C=C(\C=C\C=3C=CN=CC=3)C=CC=2)=C1 YQCSORIIPSUFJA-MDZDMXLPSA-N 0.000 claims description 3
- CMLCVHOQRIGFRS-UHFFFAOYSA-N n-(3-methylbutyl)-4-(pyridin-3-ylamino)benzamide Chemical compound C1=CC(C(=O)NCCC(C)C)=CC=C1NC1=CC=CN=C1 CMLCVHOQRIGFRS-UHFFFAOYSA-N 0.000 claims description 3
- GFJGXGKCRUYVJH-UHFFFAOYSA-N n-[2-(diethylamino)propyl]-2-[4-(trifluoromethoxy)anilino]benzamide Chemical compound CCN(CC)C(C)CNC(=O)C1=CC=CC=C1NC1=CC=C(OC(F)(F)F)C=C1 GFJGXGKCRUYVJH-UHFFFAOYSA-N 0.000 claims description 3
- XOKDWZOUYOXSBJ-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-2-[4-(trifluoromethoxy)anilino]benzamide Chemical compound CN(C)CCNC(=O)C1=CC=CC=C1NC1=CC=C(OC(F)(F)F)C=C1 XOKDWZOUYOXSBJ-UHFFFAOYSA-N 0.000 claims description 3
- YIZJTUSBTZHCIV-OUKQBFOZSA-N n-[3-(diethylamino)propyl]-3-[3-[(e)-2-pyridin-4-ylethenyl]anilino]benzamide Chemical compound CCN(CC)CCCNC(=O)C1=CC=CC(NC=2C=C(\C=C\C=3C=CN=CC=3)C=CC=2)=C1 YIZJTUSBTZHCIV-OUKQBFOZSA-N 0.000 claims description 3
- TZDYLWZAPZHIHR-ZHACJKMWSA-N n-[3-(diethylamino)propyl]-3-methyl-4-[3-[(e)-2-pyridin-4-ylethenyl]anilino]benzamide Chemical compound CC1=CC(C(=O)NCCCN(CC)CC)=CC=C1NC1=CC=CC(\C=C\C=2C=CN=CC=2)=C1 TZDYLWZAPZHIHR-ZHACJKMWSA-N 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 230000009759 skin aging Effects 0.000 claims description 3
- WJGLFEUAYGIPRN-UHFFFAOYSA-N 2-[4-(dimethylamino)anilino]-n-(3-imidazol-1-ylpropyl)benzamide Chemical compound C1=CC(N(C)C)=CC=C1NC1=CC=CC=C1C(=O)NCCCN1C=NC=C1 WJGLFEUAYGIPRN-UHFFFAOYSA-N 0.000 claims description 2
- RYZMHJCWSQMDPT-UHFFFAOYSA-N 3-[1-[4-(4-methoxyanilino)phenyl]triazol-4-yl]propan-1-ol Chemical compound C1=CC(OC)=CC=C1NC1=CC=C(N2N=NC(CCCO)=C2)C=C1 RYZMHJCWSQMDPT-UHFFFAOYSA-N 0.000 claims description 2
- DTZUWPMJAHFPFG-UHFFFAOYSA-N 3-methyl-n-(3-methylbutyl)-4-(pyridin-3-ylamino)benzamide Chemical compound CC1=CC(C(=O)NCCC(C)C)=CC=C1NC1=CC=CN=C1 DTZUWPMJAHFPFG-UHFFFAOYSA-N 0.000 claims description 2
- RRNFHBAWFDBTBS-UHFFFAOYSA-N 3-methyl-n-(3-methylbutyl)-4-[4-(trifluoromethoxy)anilino]benzamide Chemical compound CC1=CC(C(=O)NCCC(C)C)=CC=C1NC1=CC=C(OC(F)(F)F)C=C1 RRNFHBAWFDBTBS-UHFFFAOYSA-N 0.000 claims description 2
- MJNPBAIZWHGFQN-UHFFFAOYSA-N 4-(4-methoxyanilino)-3-methyl-n-(3-methylbutyl)benzamide Chemical compound C1=CC(OC)=CC=C1NC1=CC=C(C(=O)NCCC(C)C)C=C1C MJNPBAIZWHGFQN-UHFFFAOYSA-N 0.000 claims description 2
- OLQDONPZUXJKHK-UHFFFAOYSA-N 4-[4-[diethylamino(methyl)amino]triazol-1-yl]-n-(4-methoxyphenyl)aniline Chemical compound N1=NC(N(C)N(CC)CC)=CN1C(C=C1)=CC=C1NC1=CC=C(OC)C=C1 OLQDONPZUXJKHK-UHFFFAOYSA-N 0.000 claims description 2
- IKXUYEHWXOXZSD-UHFFFAOYSA-N 4-[4-[diethylamino(methyl)amino]triazol-1-yl]-n-[4-(trifluoromethoxy)phenyl]aniline Chemical compound N1=NC(N(C)N(CC)CC)=CN1C(C=C1)=CC=C1NC1=CC=C(OC(F)(F)F)C=C1 IKXUYEHWXOXZSD-UHFFFAOYSA-N 0.000 claims description 2
- 206010002027 Amyotrophy Diseases 0.000 claims description 2
- 208000014644 Brain disease Diseases 0.000 claims description 2
- 201000003883 Cystic fibrosis Diseases 0.000 claims description 2
- 101000869592 Daucus carota Major allergen Dau c 1 Proteins 0.000 claims description 2
- 208000032274 Encephalopathy Diseases 0.000 claims description 2
- 208000007982 Frasier Syndrome Diseases 0.000 claims description 2
- 201000011240 Frontotemporal dementia Diseases 0.000 claims description 2
- 101000650136 Homo sapiens WAS/WASL-interacting protein family member 3 Proteins 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 208000006136 Leigh Disease Diseases 0.000 claims description 2
- 208000017507 Leigh syndrome Diseases 0.000 claims description 2
- 206010025323 Lymphomas Diseases 0.000 claims description 2
- 206010058799 Mitochondrial encephalomyopathy Diseases 0.000 claims description 2
- 208000018737 Parkinson disease Diseases 0.000 claims description 2
- 102100027539 WAS/WASL-interacting protein family member 3 Human genes 0.000 claims description 2
- 125000003368 amide group Chemical group 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 210000000349 chromosome Anatomy 0.000 claims description 2
- 210000001072 colon Anatomy 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 210000002161 motor neuron Anatomy 0.000 claims description 2
- BASNBMRFRNZZRC-UHFFFAOYSA-N n-(3-imidazol-1-ylpropyl)-2-(4-methoxyanilino)benzamide Chemical compound C1=CC(OC)=CC=C1NC1=CC=CC=C1C(=O)NCCCN1C=NC=C1 BASNBMRFRNZZRC-UHFFFAOYSA-N 0.000 claims description 2
- QOWOCAIBBUSUOK-UHFFFAOYSA-N n-[2-(diethylamino)ethyl]-2-[4-(trifluoromethoxy)anilino]benzamide Chemical compound CCN(CC)CCNC(=O)C1=CC=CC=C1NC1=CC=C(OC(F)(F)F)C=C1 QOWOCAIBBUSUOK-UHFFFAOYSA-N 0.000 claims description 2
- NYNWBLCWWOFPFI-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-3-methyl-4-[4-(trifluoromethoxy)anilino]benzamide Chemical compound CC1=CC(C(=O)NCCN(C)C)=CC=C1NC1=CC=C(OC(F)(F)F)C=C1 NYNWBLCWWOFPFI-UHFFFAOYSA-N 0.000 claims description 2
- PNZMAMKNMDRBAM-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-4-(4-methoxyanilino)-3-methylbenzamide Chemical compound C1=CC(OC)=CC=C1NC1=CC=C(C(=O)NCCN(C)C)C=C1C PNZMAMKNMDRBAM-UHFFFAOYSA-N 0.000 claims description 2
- KZYKDQMDKSZBJR-UHFFFAOYSA-N n-[3-(diethylamino)propyl]-3-methyl-4-(pyridin-3-ylamino)benzamide Chemical compound CC1=CC(C(=O)NCCCN(CC)CC)=CC=C1NC1=CC=CN=C1 KZYKDQMDKSZBJR-UHFFFAOYSA-N 0.000 claims description 2
- CUUVIRNLGNFTPV-UHFFFAOYSA-N n-[3-(diethylamino)propyl]-3-methyl-4-[4-(trifluoromethoxy)anilino]benzamide Chemical compound CC1=CC(C(=O)NCCCN(CC)CC)=CC=C1NC1=CC=C(OC(F)(F)F)C=C1 CUUVIRNLGNFTPV-UHFFFAOYSA-N 0.000 claims description 2
- BQFHBXFWSZEKJI-UHFFFAOYSA-N n-[3-(diethylamino)propyl]-4-(4-methoxyanilino)-3-methylbenzamide Chemical compound CC1=CC(C(=O)NCCCN(CC)CC)=CC=C1NC1=CC=C(OC)C=C1 BQFHBXFWSZEKJI-UHFFFAOYSA-N 0.000 claims description 2
- NEHAWPULKZRPDY-UHFFFAOYSA-N n-[3-(diethylamino)propyl]-4-(4-methoxyanilino)benzamide Chemical compound C1=CC(C(=O)NCCCN(CC)CC)=CC=C1NC1=CC=C(OC)C=C1 NEHAWPULKZRPDY-UHFFFAOYSA-N 0.000 claims description 2
- PMZQLPHQXCEYLK-UHFFFAOYSA-N n-[3-(dimethylamino)propyl]-3-(pyridin-3-ylamino)benzamide Chemical compound CN(C)CCCNC(=O)C1=CC=CC(NC=2C=NC=CC=2)=C1 PMZQLPHQXCEYLK-UHFFFAOYSA-N 0.000 claims description 2
- FFSAKCDOKQPAEU-UHFFFAOYSA-N n-[3-(dimethylamino)propyl]-3-[4-(trifluoromethoxy)anilino]benzamide Chemical compound CN(C)CCCNC(=O)C1=CC=CC(NC=2C=CC(OC(F)(F)F)=CC=2)=C1 FFSAKCDOKQPAEU-UHFFFAOYSA-N 0.000 claims description 2
- PDWGNSJLBDFKRZ-UHFFFAOYSA-N n-[4-[4-[diethylamino(methyl)amino]triazol-1-yl]phenyl]pyridin-3-amine Chemical compound N1=NC(N(C)N(CC)CC)=CN1C(C=C1)=CC=C1NC1=CC=CN=C1 PDWGNSJLBDFKRZ-UHFFFAOYSA-N 0.000 claims description 2
- 230000007171 neuropathology Effects 0.000 claims description 2
- 229940076279 serotonin Drugs 0.000 claims description 2
- 230000004083 survival effect Effects 0.000 claims description 2
- 102000013498 tau Proteins Human genes 0.000 claims description 2
- 108010026424 tau Proteins Proteins 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 230000005856 abnormality Effects 0.000 abstract description 5
- 208000026350 Inborn Genetic disease Diseases 0.000 abstract description 4
- 208000016361 genetic disease Diseases 0.000 abstract description 4
- 102000001708 Protein Isoforms Human genes 0.000 description 14
- 108010029485 Protein Isoforms Proteins 0.000 description 14
- 238000011282 treatment Methods 0.000 description 13
- 230000014509 gene expression Effects 0.000 description 12
- 102000004169 proteins and genes Human genes 0.000 description 12
- 239000000460 chlorine Substances 0.000 description 11
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 210000003819 peripheral blood mononuclear cell Anatomy 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 241000713772 Human immunodeficiency virus 1 Species 0.000 description 7
- 108020004414 DNA Proteins 0.000 description 6
- 108010069091 Dystrophin Proteins 0.000 description 6
- 241000725303 Human immunodeficiency virus Species 0.000 description 6
- 206010028980 Neoplasm Diseases 0.000 description 6
- 230000002159 abnormal effect Effects 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 208000025500 Hutchinson-Gilford progeria syndrome Diseases 0.000 description 5
- 208000007932 Progeria Diseases 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000003623 enhancer Substances 0.000 description 5
- 125000005843 halogen group Chemical group 0.000 description 5
- 230000005764 inhibitory process Effects 0.000 description 5
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 5
- 201000006938 muscular dystrophy Diseases 0.000 description 5
- 229960003966 nicotinamide Drugs 0.000 description 5
- 239000011570 nicotinamide Substances 0.000 description 5
- 210000001519 tissue Anatomy 0.000 description 5
- 108091032973 (ribonucleotides)n+m Proteins 0.000 description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- 101150077556 LMNA gene Proteins 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 4
- 241000700605 Viruses Species 0.000 description 4
- 230000001594 aberrant effect Effects 0.000 description 4
- 230000004075 alteration Effects 0.000 description 4
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 4
- 229940054051 antipsychotic indole derivative Drugs 0.000 description 4
- 201000011510 cancer Diseases 0.000 description 4
- 238000011161 development Methods 0.000 description 4
- 230000018109 developmental process Effects 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 150000002475 indoles Chemical class 0.000 description 4
- 208000026585 laminopathy Diseases 0.000 description 4
- 210000002540 macrophage Anatomy 0.000 description 4
- 230000007170 pathology Effects 0.000 description 4
- 239000013612 plasmid Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 description 3
- IMRGVWZLCZERSQ-UHFFFAOYSA-N 4-chloropyridine-3-carboxylic acid Chemical compound OC(=O)C1=CN=CC=C1Cl IMRGVWZLCZERSQ-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 102000001039 Dystrophin Human genes 0.000 description 3
- 206010027476 Metastases Diseases 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 101100386054 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) CYS3 gene Proteins 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000033228 biological regulation Effects 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 230000003833 cell viability Effects 0.000 description 3
- 230000001413 cellular effect Effects 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
- 125000004430 oxygen atom Chemical group O* 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 230000001105 regulatory effect Effects 0.000 description 3
- 230000010076 replication Effects 0.000 description 3
- 101150035983 str1 gene Proteins 0.000 description 3
- 208000011580 syndromic disease Diseases 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 2
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 2
- 125000001359 1,2,3-triazol-4-yl group Chemical group [H]N1N=NC([*])=C1[H] 0.000 description 2
- IQFYYKKMVGJFEH-OFKYTIFKSA-N 1-[(2r,4s,5r)-4-hydroxy-5-(tritiooxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione Chemical compound C1[C@H](O)[C@@H](CO[3H])O[C@H]1N1C(=O)NC(=O)C(C)=C1 IQFYYKKMVGJFEH-OFKYTIFKSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- YPMFAVFEHKDWJD-UHFFFAOYSA-N 2-(3-imidazol-1-ylpropylamino)-n-pyridin-3-ylbenzamide Chemical compound C=1C=CC=C(NCCCN2C=NC=C2)C=1C(=O)NC1=CC=CN=C1 YPMFAVFEHKDWJD-UHFFFAOYSA-N 0.000 description 2
- QNRFETAIXFVWEM-UHFFFAOYSA-N 2-[2-(dimethylamino)ethylamino]-n-[4-(trifluoromethoxy)phenyl]pyridine-3-carboxamide Chemical compound CN(C)CCNC1=NC=CC=C1C(=O)NC1=CC=C(OC(F)(F)F)C=C1 QNRFETAIXFVWEM-UHFFFAOYSA-N 0.000 description 2
- RRFODRCTTKIXJQ-UHFFFAOYSA-N 2-[3-(dimethylamino)propylamino]-n-[4-(trifluoromethoxy)phenyl]pyridine-3-carboxamide Chemical compound CN(C)CCCNC1=NC=CC=C1C(=O)NC1=CC=C(OC(F)(F)F)C=C1 RRFODRCTTKIXJQ-UHFFFAOYSA-N 0.000 description 2
- VOQKSODWFALURE-ONEGZZNKSA-N 3-[1-[4-[4-[(e)-2-pyridin-4-ylethenyl]anilino]phenyl]triazol-4-yl]propan-1-ol Chemical compound N1=NC(CCCO)=CN1C(C=C1)=CC=C1NC(C=C1)=CC=C1\C=C\C1=CC=NC=C1 VOQKSODWFALURE-ONEGZZNKSA-N 0.000 description 2
- QSAZGUXUFYSUFB-UHFFFAOYSA-N 3-[4-[(3-methoxybenzoyl)amino]anilino]-n-(3-methylbutyl)benzamide Chemical compound COC1=CC=CC(C(=O)NC=2C=CC(NC=3C=C(C=CC=3)C(=O)NCCC(C)C)=CC=2)=C1 QSAZGUXUFYSUFB-UHFFFAOYSA-N 0.000 description 2
- VXOLWJRLEHQZSP-SNAWJCMRSA-N 3-methyl-n-(3-methylbutyl)-4-[4-[(e)-2-pyridin-4-ylethenyl]anilino]benzamide Chemical compound CC1=CC(C(=O)NCCC(C)C)=CC=C1NC(C=C1)=CC=C1\C=C\C1=CC=NC=C1 VXOLWJRLEHQZSP-SNAWJCMRSA-N 0.000 description 2
- ODJWKTMPQRXFOP-UHFFFAOYSA-N 4-[4-[(3-methoxybenzoyl)amino]anilino]-3-methyl-n-(3-methylbutyl)benzamide Chemical compound COC1=CC=CC(C(=O)NC=2C=CC(NC=3C(=CC(=CC=3)C(=O)NCCC(C)C)C)=CC=2)=C1 ODJWKTMPQRXFOP-UHFFFAOYSA-N 0.000 description 2
- PVMNPAUTCMBOMO-UHFFFAOYSA-N 4-chloropyridine Chemical compound ClC1=CC=NC=C1 PVMNPAUTCMBOMO-UHFFFAOYSA-N 0.000 description 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 2
- 108020000948 Antisense Oligonucleotides Proteins 0.000 description 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 2
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 2
- 206010055113 Breast cancer metastatic Diseases 0.000 description 2
- 102100031277 Calcineurin B homologous protein 1 Human genes 0.000 description 2
- 101710205625 Capsid protein p24 Proteins 0.000 description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
- 238000002965 ELISA Methods 0.000 description 2
- 108700024394 Exon Proteins 0.000 description 2
- 108091060211 Expressed sequence tag Proteins 0.000 description 2
- 102100031181 Glyceraldehyde-3-phosphate dehydrogenase Human genes 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- 102100034343 Integrase Human genes 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 101710177166 Phosphoprotein Proteins 0.000 description 2
- 101710149951 Protein Tat Proteins 0.000 description 2
- 102000052575 Proto-Oncogene Human genes 0.000 description 2
- 108700020978 Proto-Oncogene Proteins 0.000 description 2
- 108020005067 RNA Splice Sites Proteins 0.000 description 2
- 108010092799 RNA-directed DNA polymerase Proteins 0.000 description 2
- 101710149279 Small delta antigen Proteins 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 230000000692 anti-sense effect Effects 0.000 description 2
- 239000000074 antisense oligonucleotide Substances 0.000 description 2
- 238000012230 antisense oligonucleotides Methods 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 230000007541 cellular toxicity Effects 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 229940125797 compound 12 Drugs 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 208000035475 disorder Diseases 0.000 description 2
- 231100000673 dose–response relationship Toxicity 0.000 description 2
- CTSPAMFJBXKSOY-UHFFFAOYSA-N ellipticine Chemical compound N1=CC=C2C(C)=C(NC=3C4=CC=CC=3)C4=C(C)C2=C1 CTSPAMFJBXKSOY-UHFFFAOYSA-N 0.000 description 2
- 230000002255 enzymatic effect Effects 0.000 description 2
- 239000012894 fetal calf serum Substances 0.000 description 2
- 108020004445 glyceraldehyde-3-phosphate dehydrogenase Proteins 0.000 description 2
- 239000001963 growth medium Substances 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 239000000138 intercalating agent Substances 0.000 description 2
- 238000009830 intercalation Methods 0.000 description 2
- 230000009545 invasion Effects 0.000 description 2
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 2
- LYFSTPNZBYZVEJ-VOTSOKGWSA-N n-(3-methylbutyl)-3-[4-[(e)-2-pyridin-4-ylethenyl]anilino]benzamide Chemical compound CC(C)CCNC(=O)C1=CC=CC(NC=2C=CC(\C=C\C=3C=CN=CC=3)=CC=2)=C1 LYFSTPNZBYZVEJ-VOTSOKGWSA-N 0.000 description 2
- GOLYRLCIPDPOKM-UHFFFAOYSA-N n-(3-methylbutyl)-4-(pyridin-4-ylamino)benzamide Chemical compound C1=CC(C(=O)NCCC(C)C)=CC=C1NC1=CC=NC=C1 GOLYRLCIPDPOKM-UHFFFAOYSA-N 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- WMTYKHZKVALIPB-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-2-(pyridin-4-ylamino)benzamide Chemical compound CN(C)CCNC(=O)C1=CC=CC=C1NC1=CC=NC=C1 WMTYKHZKVALIPB-UHFFFAOYSA-N 0.000 description 2
- RDRLQCQCSWDJGY-UHFFFAOYSA-N n-[3-(diethylamino)propyl]-3-[4-[(3-methoxybenzoyl)amino]anilino]benzamide Chemical compound CCN(CC)CCCNC(=O)C1=CC=CC(NC=2C=CC(NC(=O)C=3C=C(OC)C=CC=3)=CC=2)=C1 RDRLQCQCSWDJGY-UHFFFAOYSA-N 0.000 description 2
- ZESWQWOYEBKTBQ-MDZDMXLPSA-N n-[3-(diethylamino)propyl]-3-[4-[(e)-2-pyridin-4-ylethenyl]anilino]benzamide Chemical compound CCN(CC)CCCNC(=O)C1=CC=CC(NC=2C=CC(\C=C\C=3C=CN=CC=3)=CC=2)=C1 ZESWQWOYEBKTBQ-MDZDMXLPSA-N 0.000 description 2
- ZAPRZCVJOPXSGS-BQYQJAHWSA-N n-[3-(diethylamino)propyl]-3-methyl-4-[4-[(e)-2-pyridin-4-ylethenyl]anilino]benzamide Chemical compound CC1=CC(C(=O)NCCCN(CC)CC)=CC=C1NC(C=C1)=CC=C1\C=C\C1=CC=NC=C1 ZAPRZCVJOPXSGS-BQYQJAHWSA-N 0.000 description 2
- MUOXAOUNCOFGPW-UHFFFAOYSA-N n-[3-(diethylamino)propyl]-4-(3-methoxyanilino)-3-methylbenzamide Chemical compound CC1=CC(C(=O)NCCCN(CC)CC)=CC=C1NC1=CC=CC(OC)=C1 MUOXAOUNCOFGPW-UHFFFAOYSA-N 0.000 description 2
- IWYIYEYQYJYWQV-UHFFFAOYSA-N n-[3-(diethylamino)propyl]-4-[4-[(3-methoxybenzoyl)amino]anilino]-3-methylbenzamide Chemical compound CC1=CC(C(=O)NCCCN(CC)CC)=CC=C1NC(C=C1)=CC=C1NC(=O)C1=CC=CC(OC)=C1 IWYIYEYQYJYWQV-UHFFFAOYSA-N 0.000 description 2
- PGYVMLPHOHSYQD-UHFFFAOYSA-N n-[4-[4-[3-(diethylamino)propylcarbamoyl]anilino]phenyl]-3-methoxybenzamide Chemical compound C1=CC(C(=O)NCCCN(CC)CC)=CC=C1NC(C=C1)=CC=C1NC(=O)C1=CC=CC(OC)=C1 PGYVMLPHOHSYQD-UHFFFAOYSA-N 0.000 description 2
- 239000002777 nucleoside Substances 0.000 description 2
- 150000003833 nucleoside derivatives Chemical class 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 239000013641 positive control Substances 0.000 description 2
- LBKJNHPKYFYCLL-UHFFFAOYSA-N potassium;trimethyl(oxido)silane Chemical compound [K+].C[Si](C)(C)[O-] LBKJNHPKYFYCLL-UHFFFAOYSA-N 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 230000003584 silencer Effects 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- NHFVAONVLCETEV-UHFFFAOYSA-N tert-butyl 4-isoquinolin-5-ylpiperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1C1=CC=CC2=CN=CC=C12 NHFVAONVLCETEV-UHFFFAOYSA-N 0.000 description 2
- 230000014616 translation Effects 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 1
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- HXQDUTIKJZTSAE-UHFFFAOYSA-N 2-(3-imidazol-1-ylpropylamino)-n-pyridin-3-ylpyridine-3-carboxamide Chemical compound C=1C=CN=C(NCCCN2C=NC=C2)C=1C(=O)NC1=CC=CN=C1 HXQDUTIKJZTSAE-UHFFFAOYSA-N 0.000 description 1
- KMWYKVYOUACXOJ-UHFFFAOYSA-N 2-(3-imidazol-1-ylpropylamino)-n-pyridin-4-ylpyridine-3-carboxamide Chemical compound C=1C=CN=C(NCCCN2C=NC=C2)C=1C(=O)NC1=CC=NC=C1 KMWYKVYOUACXOJ-UHFFFAOYSA-N 0.000 description 1
- DYPFRGBASAWOEN-UHFFFAOYSA-N 2-(4-hydroxybutylamino)-n-[4-(trifluoromethoxy)phenyl]pyridine-3-carboxamide Chemical compound OCCCCNC1=NC=CC=C1C(=O)NC1=CC=C(OC(F)(F)F)C=C1 DYPFRGBASAWOEN-UHFFFAOYSA-N 0.000 description 1
- HLGDEHUSXIGGMP-UHFFFAOYSA-N 2-(pyridin-3-ylamino)benzamide Chemical compound N1=CC(=CC=C1)NC1=C(C(=O)N)C=CC=C1 HLGDEHUSXIGGMP-UHFFFAOYSA-N 0.000 description 1
- GWFRXASQNMRZDR-UHFFFAOYSA-N 2-(pyridin-4-ylamino)benzamide Chemical compound NC(=O)C1=CC=CC=C1NC1=CC=NC=C1 GWFRXASQNMRZDR-UHFFFAOYSA-N 0.000 description 1
- KJAUCERQDLHEIH-SNAWJCMRSA-N 2-[1-[4-[(e)-2-(4-methoxyphenyl)ethenyl]phenyl]triazol-4-yl]propan-2-ol Chemical compound C1=CC(OC)=CC=C1\C=C\C1=CC=C(N2N=NC(=C2)C(C)(C)O)C=C1 KJAUCERQDLHEIH-SNAWJCMRSA-N 0.000 description 1
- FTGWDWCOBTYNDN-UHFFFAOYSA-N 2-[2-(diethylamino)ethylamino]-n-pyridin-3-ylpyridine-3-carboxamide Chemical compound CCN(CC)CCNC1=NC=CC=C1C(=O)NC1=CC=CN=C1 FTGWDWCOBTYNDN-UHFFFAOYSA-N 0.000 description 1
- AFXHCAUBEVRWHV-UHFFFAOYSA-N 2-[2-(dimethylamino)ethylamino]-n-pyridin-3-ylpyridine-3-carboxamide Chemical compound CN(C)CCNC1=NC=CC=C1C(=O)NC1=CC=CN=C1 AFXHCAUBEVRWHV-UHFFFAOYSA-N 0.000 description 1
- BRZATTRACHIJHI-UHFFFAOYSA-N 2-[3-(diethylamino)propylamino]-n-[4-(trifluoromethoxy)phenyl]pyridine-3-carboxamide Chemical compound CCN(CC)CCCNC1=NC=CC=C1C(=O)NC1=CC=C(OC(F)(F)F)C=C1 BRZATTRACHIJHI-UHFFFAOYSA-N 0.000 description 1
- QMQBVFKJYRLFNJ-UHFFFAOYSA-N 2-[3-(diethylamino)propylamino]-n-pyridin-3-ylpyridine-3-carboxamide Chemical compound CCN(CC)CCCNC1=NC=CC=C1C(=O)NC1=CC=CN=C1 QMQBVFKJYRLFNJ-UHFFFAOYSA-N 0.000 description 1
- ZREMPGYRQSWPTH-UHFFFAOYSA-N 2-[3-(diethylamino)propylamino]-n-pyridin-4-ylpyridine-3-carboxamide Chemical compound CCN(CC)CCCNC1=NC=CC=C1C(=O)NC1=CC=NC=C1 ZREMPGYRQSWPTH-UHFFFAOYSA-N 0.000 description 1
- LJEXIDUXQYKEBN-UHFFFAOYSA-N 2-[3-(dimethylamino)propylamino]-n-pyridin-3-ylbenzamide Chemical compound CN(C)CCCNC1=CC=CC=C1C(=O)NC1=CC=CN=C1 LJEXIDUXQYKEBN-UHFFFAOYSA-N 0.000 description 1
- KLPHUGOVFZOMJH-UHFFFAOYSA-N 2-[3-(dimethylamino)propylamino]-n-pyridin-3-ylpyridine-3-carboxamide Chemical compound CN(C)CCCNC1=NC=CC=C1C(=O)NC1=CC=CN=C1 KLPHUGOVFZOMJH-UHFFFAOYSA-N 0.000 description 1
- OBUCEUMCUBBUQJ-UHFFFAOYSA-N 2-butyl-3-methyl-1-(4-pyridin-2-ylpiperazin-1-yl)pyrido[1,2-a]benzimidazole-4-carbonitrile Chemical compound CCCCC=1C(C)=C(C#N)C2=NC3=CC=CC=C3N2C=1N(CC1)CCN1C1=CC=CC=N1 OBUCEUMCUBBUQJ-UHFFFAOYSA-N 0.000 description 1
- CSDSSGBPEUDDEE-UHFFFAOYSA-N 2-formylpyridine Chemical compound O=CC1=CC=CC=N1 CSDSSGBPEUDDEE-UHFFFAOYSA-N 0.000 description 1
- NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 description 1
- RRHXAWKJWSHFDZ-UHFFFAOYSA-N 2-pyridin-2-ylpyridine-3-carboxamide Chemical compound NC(=O)C1=CC=CN=C1C1=CC=CC=N1 RRHXAWKJWSHFDZ-UHFFFAOYSA-N 0.000 description 1
- QDVCMXVFTFQFBN-VOTSOKGWSA-N 3-[1-[3-[4-[(e)-2-pyridin-4-ylethenyl]anilino]phenyl]triazol-4-yl]propan-1-ol Chemical compound N1=NC(CCCO)=CN1C1=CC=CC(NC=2C=CC(\C=C\C=3C=CN=CC=3)=CC=2)=C1 QDVCMXVFTFQFBN-VOTSOKGWSA-N 0.000 description 1
- CLTXIYBNCQSLOW-UHFFFAOYSA-N 3-methyl-n-(3-methylbutyl)-4-(pyridin-4-ylamino)benzamide Chemical compound CC1=CC(C(=O)NCCC(C)C)=CC=C1NC1=CC=NC=C1 CLTXIYBNCQSLOW-UHFFFAOYSA-N 0.000 description 1
- MPOYBFYHRQBZPM-UHFFFAOYSA-N 3h-pyridin-4-one Chemical group O=C1CC=NC=C1 MPOYBFYHRQBZPM-UHFFFAOYSA-N 0.000 description 1
- WDKHNFWZQCZFNF-UHFFFAOYSA-N 4-(3-methoxyanilino)-3-methyl-n-(3-methylbutyl)benzamide Chemical compound COC1=CC=CC(NC=2C(=CC(=CC=2)C(=O)NCCC(C)C)C)=C1 WDKHNFWZQCZFNF-UHFFFAOYSA-N 0.000 description 1
- FWMNVWWHGCHHJJ-SKKKGAJSSA-N 4-amino-1-[(2r)-6-amino-2-[[(2r)-2-[[(2r)-2-[[(2r)-2-amino-3-phenylpropanoyl]amino]-3-phenylpropanoyl]amino]-4-methylpentanoyl]amino]hexanoyl]piperidine-4-carboxylic acid Chemical compound C([C@H](C(=O)N[C@H](CC(C)C)C(=O)N[C@H](CCCCN)C(=O)N1CCC(N)(CC1)C(O)=O)NC(=O)[C@H](N)CC=1C=CC=CC=1)C1=CC=CC=C1 FWMNVWWHGCHHJJ-SKKKGAJSSA-N 0.000 description 1
- NUKYPUAOHBNCPY-UHFFFAOYSA-N 4-aminopyridine Chemical compound NC1=CC=NC=C1 NUKYPUAOHBNCPY-UHFFFAOYSA-N 0.000 description 1
- XGAFCCUNHIMIRV-UHFFFAOYSA-N 4-chloropyridine;hydron;chloride Chemical compound Cl.ClC1=CC=NC=C1 XGAFCCUNHIMIRV-UHFFFAOYSA-N 0.000 description 1
- CYHGSUODHZDQER-UHFFFAOYSA-N 4-hydroxy-1-methyl-6-oxopyridine-3-carboxylic acid Chemical compound CN1C=C(C(O)=O)C(O)=CC1=O CYHGSUODHZDQER-UHFFFAOYSA-N 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- IYPSYYLXHFGFPC-UHFFFAOYSA-N 4-oxo-1h-pyridine-3-carbaldehyde Chemical compound OC1=CC=NC=C1C=O IYPSYYLXHFGFPC-UHFFFAOYSA-N 0.000 description 1
- CHCUBGPSZDGABM-UHFFFAOYSA-N 4-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC(=O)C1=CNC=CC1=O CHCUBGPSZDGABM-UHFFFAOYSA-N 0.000 description 1
- 125000004863 4-trifluoromethoxyphenyl group Chemical group [H]C1=C([H])C(OC(F)(F)F)=C([H])C([H])=C1* 0.000 description 1
- 239000004475 Arginine Substances 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 102100031650 C-X-C chemokine receptor type 4 Human genes 0.000 description 1
- 241000282465 Canis Species 0.000 description 1
- 230000004543 DNA replication Effects 0.000 description 1
- 208000012239 Developmental disease Diseases 0.000 description 1
- 102000010834 Extracellular Matrix Proteins Human genes 0.000 description 1
- 108010037362 Extracellular Matrix Proteins Proteins 0.000 description 1
- 241000282324 Felis Species 0.000 description 1
- 229920001917 Ficoll Polymers 0.000 description 1
- 108090000288 Glycoproteins Proteins 0.000 description 1
- 102000003886 Glycoproteins Human genes 0.000 description 1
- 108010002459 HIV Integrase Proteins 0.000 description 1
- 101000922348 Homo sapiens C-X-C chemokine receptor type 4 Proteins 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- 108010002350 Interleukin-2 Proteins 0.000 description 1
- 108091092195 Intron Proteins 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
- 108010021099 Lamin Type A Proteins 0.000 description 1
- 102000008201 Lamin Type A Human genes 0.000 description 1
- 108010047294 Lamins Proteins 0.000 description 1
- 102000006835 Lamins Human genes 0.000 description 1
- 206010064912 Malignant transformation Diseases 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 108091027974 Mature messenger RNA Proteins 0.000 description 1
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 1
- FTPDYCGMYXWGPY-UHFFFAOYSA-N N'-[3-[4-(aminomethyl)triazol-1-yl]phenyl]-4-methoxy-N'-phenylbenzohydrazide Chemical compound COC1=CC=C(C(=O)NN(C=2C=C(C=CC=2)N2N=NC(=C2)CN)C2=CC=CC=C2)C=C1 FTPDYCGMYXWGPY-UHFFFAOYSA-N 0.000 description 1
- 101150041095 NEFM gene Proteins 0.000 description 1
- 206010061309 Neoplasm progression Diseases 0.000 description 1
- 108091005804 Peptidases Proteins 0.000 description 1
- 108010047620 Phytohemagglutinins Proteins 0.000 description 1
- 206010063493 Premature ageing Diseases 0.000 description 1
- 208000032038 Premature aging Diseases 0.000 description 1
- 241000288906 Primates Species 0.000 description 1
- 239000004365 Protease Substances 0.000 description 1
- 239000013614 RNA sample Substances 0.000 description 1
- 230000004570 RNA-binding Effects 0.000 description 1
- 239000012979 RPMI medium Substances 0.000 description 1
- 239000012980 RPMI-1640 medium Substances 0.000 description 1
- 102000004278 Receptor Protein-Tyrosine Kinases Human genes 0.000 description 1
- 108090000873 Receptor Protein-Tyrosine Kinases Proteins 0.000 description 1
- 102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 description 1
- 241000283984 Rodentia Species 0.000 description 1
- 239000006146 Roswell Park Memorial Institute medium Substances 0.000 description 1
- 101150081509 SLC16A10 gene Proteins 0.000 description 1
- GLNADSQYFUSGOU-GPTZEZBUSA-J Trypan blue Chemical compound [Na+].[Na+].[Na+].[Na+].C1=C(S([O-])(=O)=O)C=C2C=C(S([O-])(=O)=O)C(/N=N/C3=CC=C(C=C3C)C=3C=C(C(=CC=3)\N=N\C=3C(=CC4=CC(=CC(N)=C4C=3O)S([O-])(=O)=O)S([O-])(=O)=O)C)=C(O)C2=C1N GLNADSQYFUSGOU-GPTZEZBUSA-J 0.000 description 1
- 108010067390 Viral Proteins Proteins 0.000 description 1
- 238000007239 Wittig reaction Methods 0.000 description 1
- LNUFLCYMSVYYNW-ZPJMAFJPSA-N [(2r,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[[(3s,5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-disulfo Chemical compound O([C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CCCC(C)C)[C@H]1O[C@H](COS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]1OS(O)(=O)=O LNUFLCYMSVYYNW-ZPJMAFJPSA-N 0.000 description 1
- IGUGLOQBLCMITB-UHFFFAOYSA-N [N].C1=CC=C2NCCC2=C1 Chemical compound [N].C1=CC=C2NCCC2=C1 IGUGLOQBLCMITB-UHFFFAOYSA-N 0.000 description 1
- 239000000370 acceptor Substances 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000003321 amplification Effects 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 1
- 230000036436 anti-hiv Effects 0.000 description 1
- 230000000798 anti-retroviral effect Effects 0.000 description 1
- 239000000427 antigen Substances 0.000 description 1
- 102000036639 antigens Human genes 0.000 description 1
- 108091007433 antigens Proteins 0.000 description 1
- 230000001640 apoptogenic effect Effects 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000027455 binding Effects 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 238000006664 bond formation reaction Methods 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 210000004970 cd4 cell Anatomy 0.000 description 1
- 230000006369 cell cycle progression Effects 0.000 description 1
- 239000013592 cell lysate Substances 0.000 description 1
- 210000003855 cell nucleus Anatomy 0.000 description 1
- 230000004663 cell proliferation Effects 0.000 description 1
- 108091092356 cellular DNA Proteins 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000002299 complementary DNA Substances 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 239000012228 culture supernatant Substances 0.000 description 1
- 230000007850 degeneration Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 230000004064 dysfunction Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 210000002919 epithelial cell Anatomy 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000013604 expression vector Substances 0.000 description 1
- 210000002744 extracellular matrix Anatomy 0.000 description 1
- 229960004979 fampridine Drugs 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 238000012268 genome sequencing Methods 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 210000000987 immune system Anatomy 0.000 description 1
- 230000000415 inactivating effect Effects 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000002458 infectious effect Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000002850 integrase inhibitor Substances 0.000 description 1
- 229940124524 integrase inhibitor Drugs 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 210000005053 lamin Anatomy 0.000 description 1
- 231100000518 lethal Toxicity 0.000 description 1
- 230000001665 lethal effect Effects 0.000 description 1
- 208000032839 leukemia Diseases 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000036212 malign transformation Effects 0.000 description 1
- 230000003211 malignant effect Effects 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 230000035800 maturation Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 230000001394 metastastic effect Effects 0.000 description 1
- 206010061289 metastatic neoplasm Diseases 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- 125000006178 methyl benzyl group Chemical group 0.000 description 1
- 239000004530 micro-emulsion Substances 0.000 description 1
- 230000002438 mitochondrial effect Effects 0.000 description 1
- 230000004899 motility Effects 0.000 description 1
- 210000003098 myoblast Anatomy 0.000 description 1
- 210000004165 myocardium Anatomy 0.000 description 1
- VJMRKWPMFQGIPI-UHFFFAOYSA-N n-(2-hydroxyethyl)-5-(hydroxymethyl)-3-methyl-1-[2-[[3-(trifluoromethyl)phenyl]methyl]-1-benzothiophen-7-yl]pyrazole-4-carboxamide Chemical compound OCC1=C(C(=O)NCCO)C(C)=NN1C1=CC=CC2=C1SC(CC=1C=C(C=CC=1)C(F)(F)F)=C2 VJMRKWPMFQGIPI-UHFFFAOYSA-N 0.000 description 1
- BAVYWRAVQKVHPJ-UHFFFAOYSA-N n-(3-imidazol-1-ylpropyl)-2-(3-methoxyanilino)benzamide Chemical compound COC1=CC=CC(NC=2C(=CC=CC=2)C(=O)NCCCN2C=NC=C2)=C1 BAVYWRAVQKVHPJ-UHFFFAOYSA-N 0.000 description 1
- GNBHZXFMOKYEBD-UHFFFAOYSA-N n-(3-imidazol-1-ylpropyl)-2-(pyridin-3-ylamino)benzamide Chemical compound C=1C=CC=C(NC=2C=NC=CC=2)C=1C(=O)NCCCN1C=CN=C1 GNBHZXFMOKYEBD-UHFFFAOYSA-N 0.000 description 1
- CLSOMGHKWAMGJV-MDZDMXLPSA-N n-(4-hydroxybutyl)-3-[(e)-2-pyridin-2-ylethenyl]benzamide Chemical compound OCCCCNC(=O)C1=CC=CC(\C=C\C=2N=CC=CC=2)=C1 CLSOMGHKWAMGJV-MDZDMXLPSA-N 0.000 description 1
- MMHATUXDXYEJCU-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-3-(3-methoxyanilino)benzamide Chemical compound COC1=CC=CC(NC=2C=C(C=CC=2)C(=O)NCCN(C)C)=C1 MMHATUXDXYEJCU-UHFFFAOYSA-N 0.000 description 1
- CWQBXMIEWVXIKQ-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-4-(3-methoxyanilino)benzamide Chemical compound COC1=CC=CC(NC=2C=CC(=CC=2)C(=O)NCCN(C)C)=C1 CWQBXMIEWVXIKQ-UHFFFAOYSA-N 0.000 description 1
- CVHIJLXXLCRDAQ-UHFFFAOYSA-N n-[3-(diethylamino)propyl]-4-[4-(dimethylamino)anilino]-3-methylbenzamide Chemical compound CC1=CC(C(=O)NCCCN(CC)CC)=CC=C1NC1=CC=C(N(C)C)C=C1 CVHIJLXXLCRDAQ-UHFFFAOYSA-N 0.000 description 1
- BXPBVTZCEFLYBY-UHFFFAOYSA-N n-[3-(dimethylamino)propyl]-3-(3-methoxyanilino)benzamide Chemical compound COC1=CC=CC(NC=2C=C(C=CC=2)C(=O)NCCCN(C)C)=C1 BXPBVTZCEFLYBY-UHFFFAOYSA-N 0.000 description 1
- MHCZPAMQENSUGP-UHFFFAOYSA-N n-[3-(dimethylamino)propyl]-3-(4-methoxyanilino)benzamide Chemical compound C1=CC(OC)=CC=C1NC1=CC=CC(C(=O)NCCCN(C)C)=C1 MHCZPAMQENSUGP-UHFFFAOYSA-N 0.000 description 1
- JWFUNROPKOHIKJ-UHFFFAOYSA-N n-butan-2-yl-2-methylbenzamide Chemical compound CCC(C)NC(=O)C1=CC=CC=C1C JWFUNROPKOHIKJ-UHFFFAOYSA-N 0.000 description 1
- RIVIDPPYRINTTH-UHFFFAOYSA-N n-ethylpropan-2-amine Chemical compound CCNC(C)C RIVIDPPYRINTTH-UHFFFAOYSA-N 0.000 description 1
- 239000013642 negative control Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 235000005152 nicotinamide Nutrition 0.000 description 1
- DFPAKSUCGFBDDF-UHFFFAOYSA-N nicotinic acid amide Natural products NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 238000010606 normalization Methods 0.000 description 1
- 238000003199 nucleic acid amplification method Methods 0.000 description 1
- 239000002773 nucleotide Substances 0.000 description 1
- 125000003729 nucleotide group Chemical group 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 230000002018 overexpression Effects 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 238000005897 peptide coupling reaction Methods 0.000 description 1
- 239000000137 peptide hydrolase inhibitor Substances 0.000 description 1
- 210000005259 peripheral blood Anatomy 0.000 description 1
- 239000011886 peripheral blood Substances 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical class [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
- 230000001885 phytohemagglutinin Effects 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 238000002264 polyacrylamide gel electrophoresis Methods 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 230000000306 recurrent effect Effects 0.000 description 1
- 230000001177 retroviral effect Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 239000003419 rna directed dna polymerase inhibitor Substances 0.000 description 1
- 125000003607 serino group Chemical group [H]N([H])[C@]([H])(C(=O)[*])C(O[H])([H])[H] 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 210000002027 skeletal muscle Anatomy 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 210000003699 striated muscle Anatomy 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 230000008685 targeting Effects 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000013519 translation Methods 0.000 description 1
- 230000005751 tumor progression Effects 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 230000029812 viral genome replication Effects 0.000 description 1
- 230000006514 viral protein processing Effects 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
- A61K31/166—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide having the carbon of a carboxamide group directly attached to the aromatic ring, e.g. procainamide, procarbazine, metoclopramide, labetalol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
- A61K31/417—Imidazole-alkylamines, e.g. histamine, phentolamine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4192—1,2,3-Triazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4406—Non condensed pyridines; Hydrogenated derivatives thereof only substituted in position 3, e.g. zimeldine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4409—Non condensed pyridines; Hydrogenated derivatives thereof only substituted in position 4, e.g. isoniazid, iproniazid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/472—Non-condensed isoquinolines, e.g. papaverine
- A61K31/4725—Non-condensed isoquinolines, e.g. papaverine containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/18—Drugs for disorders of the alimentary tract or the digestive system for pancreatic disorders, e.g. pancreatic enzymes
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/06—Anabolic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/12—Antidiuretics, e.g. drugs for diabetes insipidus
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
- C07C233/67—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
- C07C233/75—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
- C07C233/77—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
- C07C233/80—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/28—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
- C07C237/30—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 the nitrogen atom of the carboxamide group bound to hydrogen atoms or to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/28—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
- C07C237/34—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 the nitrogen atom of the carboxamide group bound to an acyclic carbon atom of a hydrocarbon radical substituted by nitrogen atoms not being part of nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/28—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
- C07C237/40—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 the nitrogen atom of the carboxamide group bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/28—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
- 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
-
- 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
- C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
-
- 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
- C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/56—Amides
-
- 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
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- 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
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C07D233/61—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms not forming part of a nitro radical, attached to ring nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
- C07D249/06—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles with aryl radicals directly attached to ring atoms
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Neurology (AREA)
- Epidemiology (AREA)
- Physical Education & Sports Medicine (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Virology (AREA)
- Diabetes (AREA)
- Oncology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Communicable Diseases (AREA)
- Endocrinology (AREA)
- Hematology (AREA)
- Psychiatry (AREA)
- Molecular Biology (AREA)
- Rheumatology (AREA)
- Urology & Nephrology (AREA)
- Obesity (AREA)
- Hospice & Palliative Care (AREA)
- Tropical Medicine & Parasitology (AREA)
- AIDS & HIV (AREA)
- Ophthalmology & Optometry (AREA)
- Psychology (AREA)
- Pain & Pain Management (AREA)
- Emergency Medicine (AREA)
- Dermatology (AREA)
Abstract
Description
Claims (9)
Priority Applications (26)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR0850144A FR2926297B1 (fr) | 2008-01-10 | 2008-01-10 | Molecules chimiques inhibitrices du mecanisme d'epissage pour traiter des maladies resultant d'anomalies d'epissage. |
PT97004998T PT2235000T (pt) | 2008-01-10 | 2009-01-12 | Moléculas químicas que inibem o mecanismo de corte para o tratamento de doenças resultantes de anomalias de splicing |
DK09700499.8T DK2235000T3 (da) | 2008-01-10 | 2009-01-12 | Kemiske molekyler, der hæmmer splejsningsmekanismen, til behandling af sygdomme, der skyldes splejsningsanomalier |
PCT/EP2009/050280 WO2009087238A2 (fr) | 2008-01-10 | 2009-01-12 | Molécules chimiques inhibant le mécanisme d'épissage pour traiter des maladies résultant d'anomalies d'épissage |
CA2711652A CA2711652C (fr) | 2008-01-10 | 2009-01-12 | Molecules chimiques inhibant le mecanisme d'epissage pour traiter des maladies resultant d'anomalies d'epissage |
CA2946329A CA2946329C (fr) | 2008-01-10 | 2009-01-12 | Molecules chimiques inhibant le mecanisme d'epissage pour traiter des maladies resultant d'anomalies d'epissage |
PL09700499T PL2235000T3 (pl) | 2008-01-10 | 2009-01-12 | Cząsteczki chemiczne hamujące mechanizm splicingu do leczenia chorób wynikających z nieprawidłowości splicingu |
CN201410299552.7A CN104086482B (zh) | 2008-01-10 | 2009-01-12 | 用于治疗由剪接异常引起的疾病的抑制剪接机理的化学分子 |
CA3072245A CA3072245C (fr) | 2008-01-10 | 2009-01-12 | Molecules chimiques inhibant le mecanisme d'epissage pour traiter des maladies resultant d'anomalies d'epissage |
EP09700499.8A EP2235000B1 (fr) | 2008-01-10 | 2009-01-12 | Molécules chimiques inhibant le mécanisme d'épissage pour traiter des maladies résultant d'anomalies d'épissage |
CA2946336A CA2946336C (fr) | 2008-01-10 | 2009-01-12 | Molecules chimiques inhibant le mecanisme d'epissage pour traiter des maladies resultant d'anomalies d'epissage |
US12/811,931 US8604063B2 (en) | 2008-01-10 | 2009-01-12 | Chemical molecules that inhibit the slicing mechanism for treating diseases resulting from splicing anomalies |
ES19164367T ES2934810T3 (es) | 2008-01-10 | 2009-01-12 | Moléculas químicas que inhiben el mecanismo de empalme para tratar enfermedades causadas por anomalías de empalme |
ES09700499T ES2816178T3 (es) | 2008-01-10 | 2009-01-12 | Moléculas químicas que inhiben el mecanismo de corte para tratar enfermedades causadas por anomalías de empalme |
CN201410301260.2A CN104130242B (zh) | 2008-01-10 | 2009-01-12 | 用于治疗由剪接异常引起的疾病的抑制剪接机理的化学分子 |
EP19164367.5A EP3536691B1 (fr) | 2008-01-10 | 2009-01-12 | Molécules chimiques inhibant le mécanisme d'épissage pour traiter des maladies résultant d'anomalies d'épissage |
CN200980106361.1A CN101965341B (zh) | 2008-01-10 | 2009-01-12 | 用于治疗由剪接异常引起的疾病的抑制剪接机理的化学分子 |
JP2010541800A JP5784909B2 (ja) | 2008-01-10 | 2009-01-12 | スプライシング異常からもたらされる疾患を処置する為のスライスする機構を阻害する化学分子 |
CA2946326A CA2946326C (fr) | 2008-01-10 | 2009-01-12 | Molecules chimiques inhibant le mecanisme d'epissage pour traiter des maladies resultant d'anomalies d'epissage |
FR1350601A FR2983200B1 (fr) | 2008-01-10 | 2013-01-24 | Molecules chimiques inhibitrices du mecanisme d'epissage pour traiter des maladies resultant d'anomalies d'epissage. |
FR1350599A FR2983199B1 (fr) | 2008-01-10 | 2013-01-24 | Molecules chimiques inhibitrices du mecanisme d'epissage pour traiter des maladies resultant d'anomalies d'epissage. |
FR1350600A FR2983196B1 (fr) | 2008-01-10 | 2013-01-24 | Molecules chimiques inhibitrices du mecanisme d'epissage pour traiter des maladies resultant d'anomalies d'epissage. |
US14/070,799 US9233931B2 (en) | 2008-01-10 | 2013-11-04 | Chemical molecules that inhibit the slicing mechanism for treating diseases resulting from splicing anomalies |
US14/958,602 US10130595B2 (en) | 2008-01-10 | 2015-12-03 | Chemical molecules that inhibit the slicing mechanism for treating diseases resulting from splicing anomalies |
US16/153,249 US10654813B2 (en) | 2008-01-10 | 2018-10-05 | Chemical molecules that inhibit the slicing mechanism for treating diseases resulting from splicing anomalies |
HRP20201369TT HRP20201369T1 (hr) | 2008-01-10 | 2020-08-28 | Kemijske molekule koje inhibiraju mehanizam prekrajanja za lječenje bolesti koje proizlaze iz anomalija prekrajanja |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR0850144A FR2926297B1 (fr) | 2008-01-10 | 2008-01-10 | Molecules chimiques inhibitrices du mecanisme d'epissage pour traiter des maladies resultant d'anomalies d'epissage. |
Publications (2)
Publication Number | Publication Date |
---|---|
FR2926297A1 true FR2926297A1 (fr) | 2009-07-17 |
FR2926297B1 FR2926297B1 (fr) | 2013-03-08 |
Family
ID=39720243
Family Applications (4)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
FR0850144A Active FR2926297B1 (fr) | 2008-01-10 | 2008-01-10 | Molecules chimiques inhibitrices du mecanisme d'epissage pour traiter des maladies resultant d'anomalies d'epissage. |
FR1350599A Active FR2983199B1 (fr) | 2008-01-10 | 2013-01-24 | Molecules chimiques inhibitrices du mecanisme d'epissage pour traiter des maladies resultant d'anomalies d'epissage. |
FR1350600A Active FR2983196B1 (fr) | 2008-01-10 | 2013-01-24 | Molecules chimiques inhibitrices du mecanisme d'epissage pour traiter des maladies resultant d'anomalies d'epissage. |
FR1350601A Active FR2983200B1 (fr) | 2008-01-10 | 2013-01-24 | Molecules chimiques inhibitrices du mecanisme d'epissage pour traiter des maladies resultant d'anomalies d'epissage. |
Family Applications After (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
FR1350599A Active FR2983199B1 (fr) | 2008-01-10 | 2013-01-24 | Molecules chimiques inhibitrices du mecanisme d'epissage pour traiter des maladies resultant d'anomalies d'epissage. |
FR1350600A Active FR2983196B1 (fr) | 2008-01-10 | 2013-01-24 | Molecules chimiques inhibitrices du mecanisme d'epissage pour traiter des maladies resultant d'anomalies d'epissage. |
FR1350601A Active FR2983200B1 (fr) | 2008-01-10 | 2013-01-24 | Molecules chimiques inhibitrices du mecanisme d'epissage pour traiter des maladies resultant d'anomalies d'epissage. |
Country Status (12)
Country | Link |
---|---|
US (4) | US8604063B2 (fr) |
EP (2) | EP3536691B1 (fr) |
JP (1) | JP5784909B2 (fr) |
CN (3) | CN104130242B (fr) |
CA (5) | CA2946326C (fr) |
DK (1) | DK2235000T3 (fr) |
ES (2) | ES2816178T3 (fr) |
FR (4) | FR2926297B1 (fr) |
HR (1) | HRP20201369T1 (fr) |
PL (1) | PL2235000T3 (fr) |
PT (1) | PT2235000T (fr) |
WO (1) | WO2009087238A2 (fr) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ITMI20130444A1 (it) * | 2013-03-22 | 2014-09-23 | S B M Science Of Biology In Medici Ne Srl | Composto di inclusione comprendente adjudin [1-(2,4-diclorobenzil) - 1h-indazolo-3-carboidrazide] e ciclodestrina, sua preparazione e utilizzo. |
Families Citing this family (51)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8367669B2 (en) | 2005-06-15 | 2013-02-05 | Vanderbilt University | Inhibitors of hemeprotein-catalyzed lipid peroxidation |
US9133212B1 (en) | 2005-06-15 | 2015-09-15 | Vanderbilt University | Inhibitors of hemeprotein-catalyzed lipid peroxidation |
FR2926297B1 (fr) | 2008-01-10 | 2013-03-08 | Centre Nat Rech Scient | Molecules chimiques inhibitrices du mecanisme d'epissage pour traiter des maladies resultant d'anomalies d'epissage. |
AR077033A1 (es) | 2009-06-11 | 2011-07-27 | Hoffmann La Roche | Compuestos inhibidores de las quinasas de janus y su uso en el tratamiento de enfermedades inmunologicas |
EP2266972A1 (fr) * | 2009-06-12 | 2010-12-29 | Splicos | Nouvelles molécules chimiques qui inhibent le mécanisme d'épissage pour le traitement de maladies résultant d'anomalies d'épissage |
FI2440546T3 (fi) | 2009-06-12 | 2023-03-30 | Abivax | Ennenaikaisen vanhenemisen ja erityisesti progerian hoitamiseen hyödyllisiä yhdisteitä |
US10253020B2 (en) | 2009-06-12 | 2019-04-09 | Abivax | Compounds for preventing, inhibiting, or treating cancer, AIDS and/or premature aging |
DK2488486T3 (da) * | 2009-10-13 | 2019-11-18 | Ligand Pharm Inc | Småmolekylære forbindelser der efterligner hæmapoetisk vækstfaktor og anvendelse deraf |
CN106994124A (zh) * | 2010-06-28 | 2017-08-01 | 萩原正敏 | 遗传性疾病的预防/改善剂 |
EP2465502A1 (fr) | 2010-12-15 | 2012-06-20 | Société Splicos | Composés utiles pour traiter le SIDA |
WO2012088266A2 (fr) | 2010-12-22 | 2012-06-28 | Incyte Corporation | Imidazopyridazines et benzimidazoles substitués en tant qu'inhibiteurs de fgfr3 |
EP2505198A1 (fr) | 2011-04-01 | 2012-10-03 | Société Splicos | Composés pour leur utilisation en tant qu'agents thérapeutiques affectant l'expression et/ou l'activité de p53 |
FR2987627B1 (fr) | 2012-03-05 | 2016-03-18 | Splicos | Utilisation de rbm39 comme biomarqueur |
CN107383009B (zh) | 2012-06-13 | 2020-06-09 | 因塞特控股公司 | 作为fgfr抑制剂的取代的三环化合物 |
WO2014026125A1 (fr) | 2012-08-10 | 2014-02-13 | Incyte Corporation | Dérivés de pyrazine en tant qu'inhibiteurs de fgfr |
EP2712862A1 (fr) | 2012-09-28 | 2014-04-02 | Splicos | Nouveaux composés anti-invasifs |
US9266892B2 (en) | 2012-12-19 | 2016-02-23 | Incyte Holdings Corporation | Fused pyrazoles as FGFR inhibitors |
EP2757161A1 (fr) | 2013-01-17 | 2014-07-23 | Splicos | miRNA-124 comme biomarqueur de l'infection virale |
SG11201508328PA (en) | 2013-04-19 | 2015-11-27 | Incyte Corp | Bicyclic heterocycles as fgfr inhibitors |
ES2898385T3 (es) | 2013-07-05 | 2022-03-07 | Abivax | Compuestos bicíclicos útiles para el tratamiento de enfermedades causadas por retrovirus |
KR102412220B1 (ko) * | 2013-12-24 | 2022-06-23 | 온코타르티스, 아이엔씨. | 벤즈아미드 및 니코틴아미드 화합물 및 이를 사용하는 방법 |
EP2974729A1 (fr) | 2014-07-17 | 2016-01-20 | Abivax | Dérivés de quinoléine utilisés dans le traitement de maladies inflammatoires |
WO2016022465A1 (fr) | 2014-08-04 | 2016-02-11 | Drexel University | Nouveaux composés et procédés pour traiter ou atténuer un trouble ou une maladie à médiation par il-1r au moyen de ces composés |
CA2959130A1 (fr) * | 2014-08-11 | 2016-02-18 | The Board Of Regents Of The University Of Texas System | Prevention de la dystrophie musculaire par edition de gene mediee par crispr/cas9 |
US10851105B2 (en) | 2014-10-22 | 2020-12-01 | Incyte Corporation | Bicyclic heterocycles as FGFR4 inhibitors |
CN107438607B (zh) | 2015-02-20 | 2021-02-05 | 因赛特公司 | 作为fgfr抑制剂的双环杂环 |
MA41551A (fr) | 2015-02-20 | 2017-12-26 | Incyte Corp | Hétérocycles bicycliques utilisés en tant qu'inhibiteurs de fgfr4 |
WO2016134294A1 (fr) | 2015-02-20 | 2016-08-25 | Incyte Corporation | Hétérocycles bicycliques utilisés en tant qu'inhibiteurs de fgfr4 |
AU2017407272B2 (en) * | 2017-03-30 | 2024-06-13 | Kyoto University | Method for inducing exon skipping by genome editing |
AR111960A1 (es) | 2017-05-26 | 2019-09-04 | Incyte Corp | Formas cristalinas de un inhibidor de fgfr y procesos para su preparación |
KR20200142039A (ko) * | 2018-04-10 | 2020-12-21 | 스카이호크 테라퓨틱스, 인코포레이티드 | 암 치료용 화합물 |
CA3099116A1 (fr) | 2018-05-04 | 2019-11-07 | Incyte Corporation | Sels d'un inhibiteur de fgfr |
AU2019262195B2 (en) | 2018-05-04 | 2024-09-12 | Incyte Corporation | Solid forms of an FGFR inhibitor and processes for preparing the same |
EP3594206A1 (fr) | 2018-07-09 | 2020-01-15 | Abivax | Dérivés de phenyl-n-quinoline pour traiter une infection par un virus à arn |
EP3594205A1 (fr) * | 2018-07-09 | 2020-01-15 | Abivax | Dérivés phényl-n-aryl pour traiter une infection par le virus d'arn |
EP3669873A1 (fr) | 2018-12-20 | 2020-06-24 | Abivax | Dérivés de quinoline destinés à être utilisés dans le traitement de maladies inflammatoires |
US11628162B2 (en) | 2019-03-08 | 2023-04-18 | Incyte Corporation | Methods of treating cancer with an FGFR inhibitor |
CN110172037A (zh) * | 2019-07-01 | 2019-08-27 | 华北理工大学 | 一种含吡啶结构的苯乙烯基吡啶化合物、制备方法及其制备抗肿瘤药物的应用 |
WO2021007269A1 (fr) | 2019-07-09 | 2021-01-14 | Incyte Corporation | Hétérocycles bicycliques en tant qu'inhibiteurs de fgfr |
CA3145776A1 (fr) * | 2019-07-19 | 2021-01-28 | Abivax | Derives de groupe aryle et aryle pour traiter une infection de virus a arn |
EP3848356A1 (fr) * | 2020-01-07 | 2021-07-14 | Abivax | Dérivés aryl-n-aryl pour traiter une infection par le virus d'arn |
JP2022552324A (ja) | 2019-10-14 | 2022-12-15 | インサイト・コーポレイション | Fgfr阻害剤としての二環式複素環 |
US11566028B2 (en) | 2019-10-16 | 2023-01-31 | Incyte Corporation | Bicyclic heterocycles as FGFR inhibitors |
CA3163875A1 (fr) | 2019-12-04 | 2021-06-10 | Incyte Corporation | Heterocycles tricycliques en tant qu'inhibiteurs de fgfr |
KR20220131900A (ko) | 2019-12-04 | 2022-09-29 | 인사이트 코포레이션 | Fgfr 억제제의 유도체 |
WO2021146424A1 (fr) | 2020-01-15 | 2021-07-22 | Incyte Corporation | Hétérocycles bicycliques en tant qu'inhibiteurs de fgfr |
US12065494B2 (en) | 2021-04-12 | 2024-08-20 | Incyte Corporation | Combination therapy comprising an FGFR inhibitor and a Nectin-4 targeting agent |
JP2024522189A (ja) | 2021-06-09 | 2024-06-11 | インサイト・コーポレイション | Fgfr阻害剤としての三環式ヘテロ環 |
AU2022388884A1 (en) | 2021-11-15 | 2024-05-30 | Pi Industries Ltd. | Bicyclic heteroaromatic compounds and their use as pest control agents |
WO2023173081A2 (fr) * | 2022-03-11 | 2023-09-14 | The Johns Hopkins University | Ciblage d'une alpha kinase du facteur d'initiation eucaryote 2 pour réguler la traduction sous contrainte |
WO2023218245A1 (fr) * | 2022-05-13 | 2023-11-16 | Voronoi Inc. | Composés dérivés d'hétéroaryle et composition pharmaceutique les comprenant |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4855308A (en) * | 1987-12-04 | 1989-08-08 | Warner-Lambert Company | Method of treating senile cognitive decline with N'-substituted aminopyridine adrenergic agents |
US20040171833A1 (en) * | 1998-07-10 | 2004-09-02 | Buchwald Stephen L. | Ligands for metals and improved metal-catalyzed processes based thereon |
FR2859475A1 (fr) * | 2003-09-04 | 2005-03-11 | Centre Nat Rech Scient | Utilisation de composes derives d'ellipticine et d'aza-ellipticine pour la preparation d'un medicament utile pour le traitement de maladies genetiques resultant de l'alteration des processus d'epissage |
FR2859474A1 (fr) * | 2003-09-04 | 2005-03-11 | Centre Nat Rech Scient | Utilisation de composes derives d'indole pour la preparation d'un medicament utile pour le traitement de maladies genetiques resultant de l'alteration des processus d'epissage |
Family Cites Families (40)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR400973A (fr) | 1909-03-19 | 1909-08-13 | Jean Victor Massillon | Nouveau sertisseur à main pour la fabrication des cartouches |
DE374291C (de) * | 1914-03-24 | 1923-04-21 | Alexei Ewgenjewitsch Tschitsch | Verfahren zur Darstellung von Aminosubstitutionsprodukten der Pyridin- und Chinolinreihe |
US2274620A (en) * | 1940-01-02 | 1942-02-24 | S M A Corp | Substituted aryl amides of pyridine carboxylic acid |
US2671805A (en) | 1952-07-02 | 1954-03-09 | Searle & Co | Basically substituted o-arylamino-benzamides |
DE1168435B (de) * | 1961-12-09 | 1964-04-23 | Kali Chemie Ag | Verfahren zur Herstellung von 4-Oxo-3, 4-dihydrochinazolinen |
NL132603C (fr) * | 1964-08-29 | |||
US3409668A (en) | 1964-11-07 | 1968-11-05 | Palazzo Giuseppe | Substituted anthranilamides and process for the preparation thereof |
GB1318291A (en) * | 1970-04-15 | 1973-05-23 | Shell Int Research | Carboxamide derivatives and fungicidal compositions containing them |
JPS5095285A (fr) | 1973-12-26 | 1975-07-29 | ||
DE2417216A1 (de) * | 1974-04-09 | 1975-11-06 | Basf Ag | Fungizide |
JPS52133939A (en) * | 1976-04-30 | 1977-11-09 | Ihara Chem Ind Co Ltd | Preparation of 2-substituted benzanilides |
FR2436786A1 (fr) | 1978-09-21 | 1980-04-18 | Anvar | Nouveaux derives des pyrido (4,3-b) carbazoles (ellipticines), substitues en position 1 par une chaine polyaminee, leur obtention et leur application a titre de medicaments |
US4510139A (en) * | 1984-01-06 | 1985-04-09 | Sterling Drug Inc. | Substituted aminobenzamides and their use as agents which inhibit lipoxygenase activity |
JPS62158252A (ja) * | 1985-12-28 | 1987-07-14 | Kirin Brewery Co Ltd | 4−アミノピリジンベンズアミド誘導体 |
DE3819025A1 (de) * | 1987-09-01 | 1989-05-24 | Fuji Photo Film Co Ltd | Verfahren zur herstellung von alkoxybenzolverbindungen |
FR2627493B1 (fr) * | 1988-02-23 | 1991-10-31 | Sanofi Sa | Procede de preparation de derives d'isoquinoleine |
FR2645861A1 (fr) | 1989-04-17 | 1990-10-19 | Inst Nat Sante Rech Med | Utilisation de dipyrido (4,3-b) (3,4-f) indoles pour la preparation de medicaments utiles pour le traitement du sida |
US5579033A (en) * | 1992-05-20 | 1996-11-26 | International Business Machines Corporation | Pointing device for retrofitting onto the keyboard of an existing computer system |
GB9715584D0 (en) * | 1997-07-23 | 1997-10-01 | Eisai Co Ltd | Compounds |
AU1529799A (en) * | 1997-12-23 | 1999-07-12 | Warner-Lambert Company | Thiourea and benzamide compounds, compositions and methods of treating or preventing inflammatory diseases and atherosclerosis |
DE69929609T2 (de) * | 1998-07-10 | 2006-09-28 | Massachusetts Institute Of Technology, Cambridge | Liganden für metalle und metall-katalysiertes verfahren |
FR2787444B1 (fr) | 1998-12-22 | 2001-02-09 | Rhodia Chimie Sa | Composition et procede d'inhibition de la polymerisation radicalaire de monomeres aliphatiques a insaturation ethylenique |
ATE326453T1 (de) * | 1998-12-23 | 2006-06-15 | Lilly Co Eli | Antithrombotische amide |
FR2789576B1 (fr) | 1999-02-16 | 2002-04-26 | Oreal | Composition de teinture d'oxydation des fibres keratiniques et procede de teinture mettant en oeuvre cette composition |
US6878714B2 (en) * | 2001-01-12 | 2005-04-12 | Amgen Inc. | Substituted alkylamine derivatives and methods of use |
US7101948B2 (en) | 2001-12-21 | 2006-09-05 | Air Products And Chemicals, Inc. | Stabilizers to inhibit the polymerization of substituted cyclotetrasiloxane |
FR2836917B1 (fr) * | 2002-03-11 | 2006-02-24 | Lipha | Derives nitroso de la diphenylamine, compositions pharmaceutiques les contenant en tant que medicaments utilisables dans le traitement des pathologies caracterisees par une situation de stress oxydatif |
JPWO2004052871A1 (ja) * | 2002-12-06 | 2006-04-13 | 東レ株式会社 | ベンゾモルホリン誘導体 |
EP2583958B1 (fr) * | 2002-12-09 | 2016-08-10 | Massachusetts Institute of Technology (MIT) | Ligands pour métaux et processus à catalyse par métaux améliorés basés sur ces ligands |
US7125997B2 (en) | 2002-12-20 | 2006-10-24 | Irm Llc | Differential tumor cytotoxicity compounds and compositions |
WO2005025498A2 (fr) * | 2003-09-08 | 2005-03-24 | Corus Pharma | Acetanilides et benzamides substitues utilises dans le traitement de l'asthme et des inflammations pulmonaires |
FR2862965B1 (fr) * | 2003-11-27 | 2007-09-07 | Merck Sante Sas | Nouveaux derives de phenoxyacetamides et leur utilisation pour la preparation de diphenylamides. |
FR2862964B1 (fr) | 2003-11-27 | 2006-12-29 | Merck Sante Sas | Derives de la diphenylamine. |
TWI380975B (zh) | 2004-03-25 | 2013-01-01 | Otsuka Pharma Co Ltd | 製造胺基酚類化合物的方法 |
WO2006084116A2 (fr) | 2005-02-02 | 2006-08-10 | Nexuspharma Inc. | Compositions contenant des derives amine et procedes permettant de traiter des infections virales associees a l'etiologie du cancer |
WO2006133848A1 (fr) | 2005-06-13 | 2006-12-21 | Dsm Ip Assets. B.V. | Composition d'additif comprenant un polymère amidé ou imidé |
WO2007096647A2 (fr) * | 2006-02-27 | 2007-08-30 | Sterix Limited | Composé |
WO2008154207A1 (fr) | 2007-06-08 | 2008-12-18 | The Burnham Institute For Medical Research | Méthodes et composés de régulation de l'apoptose |
FR2926297B1 (fr) | 2008-01-10 | 2013-03-08 | Centre Nat Rech Scient | Molecules chimiques inhibitrices du mecanisme d'epissage pour traiter des maladies resultant d'anomalies d'epissage. |
EP2712862A1 (fr) | 2012-09-28 | 2014-04-02 | Splicos | Nouveaux composés anti-invasifs |
-
2008
- 2008-01-10 FR FR0850144A patent/FR2926297B1/fr active Active
-
2009
- 2009-01-12 PL PL09700499T patent/PL2235000T3/pl unknown
- 2009-01-12 EP EP19164367.5A patent/EP3536691B1/fr active Active
- 2009-01-12 CA CA2946326A patent/CA2946326C/fr active Active
- 2009-01-12 US US12/811,931 patent/US8604063B2/en active Active
- 2009-01-12 CA CA3072245A patent/CA3072245C/fr active Active
- 2009-01-12 DK DK09700499.8T patent/DK2235000T3/da active
- 2009-01-12 CA CA2946336A patent/CA2946336C/fr active Active
- 2009-01-12 CA CA2946329A patent/CA2946329C/fr active Active
- 2009-01-12 PT PT97004998T patent/PT2235000T/pt unknown
- 2009-01-12 CN CN201410301260.2A patent/CN104130242B/zh active Active
- 2009-01-12 CN CN200980106361.1A patent/CN101965341B/zh active Active
- 2009-01-12 CA CA2711652A patent/CA2711652C/fr active Active
- 2009-01-12 CN CN201410299552.7A patent/CN104086482B/zh active Active
- 2009-01-12 EP EP09700499.8A patent/EP2235000B1/fr active Active
- 2009-01-12 JP JP2010541800A patent/JP5784909B2/ja active Active
- 2009-01-12 WO PCT/EP2009/050280 patent/WO2009087238A2/fr active Application Filing
- 2009-01-12 ES ES09700499T patent/ES2816178T3/es active Active
- 2009-01-12 ES ES19164367T patent/ES2934810T3/es active Active
-
2013
- 2013-01-24 FR FR1350599A patent/FR2983199B1/fr active Active
- 2013-01-24 FR FR1350600A patent/FR2983196B1/fr active Active
- 2013-01-24 FR FR1350601A patent/FR2983200B1/fr active Active
- 2013-11-04 US US14/070,799 patent/US9233931B2/en active Active
-
2015
- 2015-12-03 US US14/958,602 patent/US10130595B2/en active Active
-
2018
- 2018-10-05 US US16/153,249 patent/US10654813B2/en active Active
-
2020
- 2020-08-28 HR HRP20201369TT patent/HRP20201369T1/hr unknown
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4855308A (en) * | 1987-12-04 | 1989-08-08 | Warner-Lambert Company | Method of treating senile cognitive decline with N'-substituted aminopyridine adrenergic agents |
US20040171833A1 (en) * | 1998-07-10 | 2004-09-02 | Buchwald Stephen L. | Ligands for metals and improved metal-catalyzed processes based thereon |
FR2859475A1 (fr) * | 2003-09-04 | 2005-03-11 | Centre Nat Rech Scient | Utilisation de composes derives d'ellipticine et d'aza-ellipticine pour la preparation d'un medicament utile pour le traitement de maladies genetiques resultant de l'alteration des processus d'epissage |
FR2859474A1 (fr) * | 2003-09-04 | 2005-03-11 | Centre Nat Rech Scient | Utilisation de composes derives d'indole pour la preparation d'un medicament utile pour le traitement de maladies genetiques resultant de l'alteration des processus d'epissage |
Non-Patent Citations (9)
Title |
---|
ALFONSO R. GENNARO: "Pyrido[3,2-b][1,4]benzothiazine(1-azaphenothiazine)", JOURNAL OF THE ORGANIC CHEMISTRY, vol. 24, 1959, pages 1156 - 1157, XP002499121 * |
COYNE W E ET AL: "3,4-DIHYDRO-2(1H)-QUINAZOLINONES", JOURNAL OF MEDICINAL CHEMISTRY, US AMERICAN CHEMICAL SOCIETY. WASHINGTON, vol. 11, no. 6, 1 January 1968 (1968-01-01), pages 1208 - 1213, XP000909664, ISSN: 0022-2623 * |
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; 1966, "Aminopyridines", XP002499122, retrieved from STN Database accession no. 1966:412224 * |
HUANG X ET AL: "Expanding Pd-Catalyzed C-N Bond-Forming Processes: The First Amidation of Aryl Sulfonates, Aqueous Amination, and Complementarity with Cu-Catalyzed Reactions", CAPLUS,, 1 January 1900 (1900-01-01), XP002366815 * |
K. EITER AND CO: "über das 9-methyl-3-carbolin und das 6-methyl-3-carbolin", MONATSHEFTE FUER CHEMIE, vol. 81, 1950, pages 404 - 413, XP002499120 * |
K. SHANKARAN AND CO: "Silicon in benzamide directed ortho methalation formation and reactions of benzamide benzynes", TETRAHEDRON LETTERS, vol. 25, no. 27, 1984, pages 2827 - 2830, XP002499118 * |
NORTON P. PEET AND CO: "A novel oxanide rearrangement", JOURNAL OF HETEROCYCLIC CHEMISTRY, vol. 17, 1980, pages 1513 - 1518, XP002499119 * |
SORENSON R J: "Selective N-arylation of aminobenzanilides under mild conditions using triarylbismuthanes", JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY, EASTON.; US, vol. 65, 21 October 2000 (2000-10-21), pages 7747 - 7749, XP002398734, ISSN: 0022-3263 * |
WARD Y D ET AL: "Solid Phase Synthesis of Aryl Amines Via Palladium Catalyzed Amination of Resin-Bound Aromatic Bromides", TETRAHEDRON LETTERS, ELSEVIER, AMSTERDAM, vol. 37, no. 39, 23 September 1996 (1996-09-23), pages 6993 - 6996, XP004030807, ISSN: 0040-4039 * |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ITMI20130444A1 (it) * | 2013-03-22 | 2014-09-23 | S B M Science Of Biology In Medici Ne Srl | Composto di inclusione comprendente adjudin [1-(2,4-diclorobenzil) - 1h-indazolo-3-carboidrazide] e ciclodestrina, sua preparazione e utilizzo. |
Also Published As
Similar Documents
Publication | Publication Date | Title |
---|---|---|
FR2926297A1 (fr) | Molecules chimiques inhibitrices du mecanisme d'epissage pour traiter des maladies resultant d'anomalies d'epissage. | |
US10195186B2 (en) | N-substituted-5-substituted phthalamic acids as sortilin inhibitors | |
CA2916623C (fr) | Composes bicycliques utiles pour le traitement de maladies causees par des retrovirus | |
KR20120054585A (ko) | 에이즈 치료에 유용한 화합물 | |
CA2656716A1 (fr) | Derives de n-(amino-heteroaryl)-1h-indole-2-carboxamides, leur preparation et leur application en therapeutique | |
CA2576727A1 (fr) | Derives de n-(1h-indolyl)-1h-indole-2-carboxamides, leur preparation et leur application en therapeutique | |
EP0526342A1 (fr) | Isoquinolein-5-yl sulfonamides, leur procédé de préparation et les compositions pharmaceutiques qui les contiennent | |
JP7428833B2 (ja) | ヒストン脱アセチル化酵素6阻害剤としての1,3,4-オキサジアゾール誘導体化合物、およびそれを含む医薬組成物 | |
TW200422293A (en) | Novel aminoindazole derivatives as medicaments and pharmaceutical compositions including them |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
TQ | Partial transmission of property |
Owner name: UNIVERSITE DE MONTPELLIER 2 SCIENCES ET TECHNI, FR Effective date: 20110901 Owner name: CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE C, FR Effective date: 20110901 Owner name: INSTITUT CURIE, FR Effective date: 20110901 |
|
PLFP | Fee payment |
Year of fee payment: 9 |
|
PLFP | Fee payment |
Year of fee payment: 10 |
|
TQ | Partial transmission of property |
Owner name: INSTITUT CURIE, FR Effective date: 20170124 Owner name: CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE, FR Effective date: 20170124 Owner name: UNIVERSITE DE MONTPELLIER, FR Effective date: 20170124 |
|
PLFP | Fee payment |
Year of fee payment: 11 |
|
PLFP | Fee payment |
Year of fee payment: 13 |
|
PLFP | Fee payment |
Year of fee payment: 14 |
|
PLFP | Fee payment |
Year of fee payment: 15 |
|
PLFP | Fee payment |
Year of fee payment: 16 |
|
PLFP | Fee payment |
Year of fee payment: 17 |