JP2013539777A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2013539777A5 JP2013539777A5 JP2013533225A JP2013533225A JP2013539777A5 JP 2013539777 A5 JP2013539777 A5 JP 2013539777A5 JP 2013533225 A JP2013533225 A JP 2013533225A JP 2013533225 A JP2013533225 A JP 2013533225A JP 2013539777 A5 JP2013539777 A5 JP 2013539777A5
- Authority
- JP
- Japan
- Prior art keywords
- piperidin
- diazepan
- carboxamide
- pyridine
- pyridin
- 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
- -1 isopropylmethyl Chemical group 0.000 claims description 97
- 150000001875 compounds Chemical class 0.000 claims description 44
- 150000003839 salts Chemical class 0.000 claims description 40
- 239000000203 mixture Substances 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims 73
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 65
- 125000001424 substituent group Chemical group 0.000 claims 26
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 25
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 20
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 16
- 125000001072 heteroaryl group Chemical group 0.000 claims 16
- 125000000623 heterocyclic group Chemical group 0.000 claims 16
- 125000000217 alkyl group Chemical group 0.000 claims 15
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 14
- 229910052731 fluorine Inorganic materials 0.000 claims 14
- 239000011737 fluorine Substances 0.000 claims 14
- 229910052736 halogen Inorganic materials 0.000 claims 13
- 150000002367 halogens Chemical class 0.000 claims 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 12
- 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims 10
- 125000001153 fluoro group Chemical group F* 0.000 claims 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims 8
- 229910052739 hydrogen Inorganic materials 0.000 claims 8
- 239000001257 hydrogen Substances 0.000 claims 8
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 7
- FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical compound C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 claims 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 6
- IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical compound NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 claims 6
- 125000003545 alkoxy group Chemical group 0.000 claims 5
- 150000002431 hydrogen Chemical class 0.000 claims 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 5
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 4
- 238000002512 chemotherapy Methods 0.000 claims 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 4
- 150000003254 radicals Chemical group 0.000 claims 4
- 238000001959 radiotherapy Methods 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 206010028980 Neoplasm Diseases 0.000 claims 3
- 238000002617 apheresis Methods 0.000 claims 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 3
- 125000002733 (C1-C6) fluoroalkyl group Chemical group 0.000 claims 2
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 2
- 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 claims 2
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
- 125000002877 alkyl aryl group Chemical group 0.000 claims 2
- 230000033115 angiogenesis Effects 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000001041 indolyl group Chemical group 0.000 claims 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 2
- 230000007823 neuropathy Effects 0.000 claims 2
- 201000001119 neuropathy Diseases 0.000 claims 2
- 208000033808 peripheral neuropathy Diseases 0.000 claims 2
- 210000000130 stem cell Anatomy 0.000 claims 2
- XJFQACJBMOHUPD-HXUWFJFHSA-N (3r)-1-[6-(5-cyclopropyl-1h-imidazol-2-yl)pyridin-2-yl]-n-[(1-propan-2-ylpiperidin-4-yl)methyl]pyrrolidin-3-amine Chemical compound C1CN(C(C)C)CCC1CN[C@H]1CN(C=2N=C(C=CC=2)C=2NC=C(N=2)C2CC2)CC1 XJFQACJBMOHUPD-HXUWFJFHSA-N 0.000 claims 1
- UUCZFULDFFWPQL-TZIWHRDSSA-N (3r)-n-[[(3r)-1-cyclopentylpyrrolidin-3-yl]methyl]-1-[6-(4-cyclopropyl-5-methyl-1h-imidazol-2-yl)pyridin-2-yl]pyrrolidin-3-amine Chemical compound CC=1NC(C=2N=C(C=CC=2)N2C[C@@H](CC2)NC[C@@H]2CN(CC2)C2CCCC2)=NC=1C1CC1 UUCZFULDFFWPQL-TZIWHRDSSA-N 0.000 claims 1
- UUCZFULDFFWPQL-PZJWPPBQSA-N (3r)-n-[[(3s)-1-cyclopentylpyrrolidin-3-yl]methyl]-1-[6-(4-cyclopropyl-5-methyl-1h-imidazol-2-yl)pyridin-2-yl]pyrrolidin-3-amine Chemical compound CC=1NC(C=2N=C(C=CC=2)N2C[C@@H](CC2)NC[C@H]2CN(CC2)C2CCCC2)=NC=1C1CC1 UUCZFULDFFWPQL-PZJWPPBQSA-N 0.000 claims 1
- PTRSCUBZJLQOPV-UHFFFAOYSA-N 1-(1-cyclopentyl-3-fluoropiperidin-4-yl)-4-[6-(4-cyclopropyl-5-methyl-1h-imidazol-2-yl)pyridin-2-yl]-1,4-diazepane Chemical compound CC=1NC(C=2N=C(C=CC=2)N2CCN(CCC2)C2C(CN(CC2)C2CCCC2)F)=NC=1C1CC1 PTRSCUBZJLQOPV-UHFFFAOYSA-N 0.000 claims 1
- SUDYACQBHZCBSU-ZETCQYMHSA-N 1-[(2s)-1,1,1-trifluoropropan-2-yl]piperidine Chemical compound FC(F)(F)[C@H](C)N1CCCCC1 SUDYACQBHZCBSU-ZETCQYMHSA-N 0.000 claims 1
- HTJRDHBQVNHSNW-UHFFFAOYSA-N 1-[1-(3-imidazol-1-ylpropyl)-2H-pyridin-6-yl]-4-(1-propan-2-ylpiperidin-4-yl)-1,4-diazepane Chemical compound N1(C=NC=C1)CCCN1CC=CC=C1N1CCN(CCC1)C1CCN(CC1)C(C)C HTJRDHBQVNHSNW-UHFFFAOYSA-N 0.000 claims 1
- DRUQFFOVQXWCSK-UHFFFAOYSA-N 1-[1-[(2-chlorophenyl)methyl]piperidin-4-yl]-4-(4-methylpyridin-2-yl)-1,4-diazepane Chemical compound CC1=CC=NC(N2CCN(CCC2)C2CCN(CC=3C(=CC=CC=3)Cl)CC2)=C1 DRUQFFOVQXWCSK-UHFFFAOYSA-N 0.000 claims 1
- GUYOPNMJNVCHIO-UHFFFAOYSA-N 1-[1-[(2-chlorophenyl)methyl]piperidin-4-yl]-4-(5-methylpyridin-2-yl)-1,4-diazepane Chemical compound N1=CC(C)=CC=C1N1CCN(C2CCN(CC=3C(=CC=CC=3)Cl)CC2)CCC1 GUYOPNMJNVCHIO-UHFFFAOYSA-N 0.000 claims 1
- QUCPAIHGUSBGJA-UHFFFAOYSA-N 1-[1-[(2-chlorophenyl)methyl]piperidin-4-yl]-4-(6-methylpyridin-2-yl)-1,4-diazepane Chemical compound CC1=CC=CC(N2CCN(CCC2)C2CCN(CC=3C(=CC=CC=3)Cl)CC2)=N1 QUCPAIHGUSBGJA-UHFFFAOYSA-N 0.000 claims 1
- MCTUAPVULTZQGY-UHFFFAOYSA-N 1-[1-[(2-chlorophenyl)methyl]piperidin-4-yl]-4-pyridin-2-yl-1,4-diazepane Chemical compound ClC1=CC=CC=C1CN1CCC(N2CCN(CCC2)C=2N=CC=CC=2)CC1 MCTUAPVULTZQGY-UHFFFAOYSA-N 0.000 claims 1
- FXGWDSZHKMXCMI-LJQANCHMSA-N 1-[1-[(2r)-butan-2-yl]piperidin-4-yl]-4-[6-(5-ethyl-1h-imidazol-2-yl)pyridin-2-yl]-1,4-diazepane Chemical compound C1CN([C@H](C)CC)CCC1N1CCN(C=2N=C(C=CC=2)C=2NC=C(CC)N=2)CCC1 FXGWDSZHKMXCMI-LJQANCHMSA-N 0.000 claims 1
- KJFJVIGDEMVWSA-UHFFFAOYSA-N 1-[6-(4,5-diethyl-1h-imidazol-2-yl)pyridin-2-yl]-4-(1-propan-2-ylpiperidin-4-yl)-1,4-diazepane Chemical compound N1C(CC)=C(CC)N=C1C1=CC=CC(N2CCN(CCC2)C2CCN(CC2)C(C)C)=N1 KJFJVIGDEMVWSA-UHFFFAOYSA-N 0.000 claims 1
- BDHKWHHBRXCYDL-UHFFFAOYSA-N 1-[6-(4,5-dimethyl-1h-imidazol-2-yl)pyridin-2-yl]-4-(1-propan-2-ylpiperidin-4-yl)-1,4-diazepane Chemical compound C1CN(C(C)C)CCC1N1CCN(C=2N=C(C=CC=2)C=2NC(C)=C(C)N=2)CCC1 BDHKWHHBRXCYDL-UHFFFAOYSA-N 0.000 claims 1
- QGOKYFIRHYLROG-UHFFFAOYSA-N 1-[6-(4-cyclopropyl-5-ethyl-1h-imidazol-2-yl)pyridin-2-yl]-4-(1-propan-2-ylpiperidin-4-yl)-1,4-diazepane Chemical compound CCC=1NC(C=2N=C(C=CC=2)N2CCN(CCC2)C2CCN(CC2)C(C)C)=NC=1C1CC1 QGOKYFIRHYLROG-UHFFFAOYSA-N 0.000 claims 1
- JNHUPAUQWMOZID-UHFFFAOYSA-N 1-[6-(4-ethyl-1-methylimidazol-2-yl)pyridin-2-yl]-4-(1-propan-2-ylpiperidin-4-yl)-1,4-diazepane Chemical compound CCC1=CN(C)C(C=2N=C(C=CC=2)N2CCN(CCC2)C2CCN(CC2)C(C)C)=N1 JNHUPAUQWMOZID-UHFFFAOYSA-N 0.000 claims 1
- RLKBQQMIPWRSTN-UHFFFAOYSA-N 1-[6-(4-ethyl-5-methyl-1h-imidazol-2-yl)pyridin-2-yl]-4-(1-propan-2-ylpiperidin-4-yl)-1,4-diazepane Chemical compound CC1=C(CC)NC(C=2N=C(C=CC=2)N2CCN(CCC2)C2CCN(CC2)C(C)C)=N1 RLKBQQMIPWRSTN-UHFFFAOYSA-N 0.000 claims 1
- CPGDFUKRCVKNNC-UHFFFAOYSA-N 1-[6-(4-methyl-1h-pyrazol-5-yl)pyridin-2-yl]-4-(1-propan-2-ylpiperidin-4-yl)-1,4-diazepane Chemical compound C1CN(C(C)C)CCC1N1CCN(C=2N=C(C=CC=2)C2=C(C=NN2)C)CCC1 CPGDFUKRCVKNNC-UHFFFAOYSA-N 0.000 claims 1
- UHZQXDZDBIOACM-UHFFFAOYSA-N 1-[6-(5-cyclopropyl-1h-imidazol-2-yl)pyridin-2-yl]-4-(3-fluoro-1-propan-2-ylpiperidin-4-yl)-1,4-diazepane Chemical compound FC1CN(C(C)C)CCC1N1CCN(C=2N=C(C=CC=2)C=2NC=C(N=2)C2CC2)CCC1 UHZQXDZDBIOACM-UHFFFAOYSA-N 0.000 claims 1
- ZNRYIRCBOYHEEC-UHFFFAOYSA-N 1-[6-(5-cyclopropyl-1h-imidazol-2-yl)pyridin-2-yl]-4-(4-pyrrolidin-1-ylcyclohexyl)-1,4-diazepane Chemical compound C1CC1C1=CNC(C=2N=C(C=CC=2)N2CCN(CCC2)C2CCC(CC2)N2CCCC2)=N1 ZNRYIRCBOYHEEC-UHFFFAOYSA-N 0.000 claims 1
- BERIDYVWZNOICH-UHFFFAOYSA-N 1-[6-(5-methyl-4-propyl-1h-imidazol-2-yl)pyridin-2-yl]-4-(1-propan-2-ylpiperidin-4-yl)-1,4-diazepane Chemical compound N1C(C)=C(CCC)N=C1C1=CC=CC(N2CCN(CCC2)C2CCN(CC2)C(C)C)=N1 BERIDYVWZNOICH-UHFFFAOYSA-N 0.000 claims 1
- CQRPLMGSGBYRHU-UHFFFAOYSA-N 1-[6-(5-tert-butyl-1h-imidazol-2-yl)pyridin-2-yl]-4-(1-tert-butylpiperidin-4-yl)-1,4-diazepane Chemical compound C1CN(C(C)(C)C)CCC1N1CCN(C=2N=C(C=CC=2)C=2NC=C(N=2)C(C)(C)C)CCC1 CQRPLMGSGBYRHU-UHFFFAOYSA-N 0.000 claims 1
- KIMKFSFLHPINST-UHFFFAOYSA-N 1-[6-[4-(1-propan-2-ylpiperidin-4-yl)-1,4-diazepan-1-yl]pyridin-2-yl]butan-1-one Chemical compound CCCC(=O)C1=CC=CC(N2CCN(CCC2)C2CCN(CC2)C(C)C)=N1 KIMKFSFLHPINST-UHFFFAOYSA-N 0.000 claims 1
- VEXIBQGHRYNKAQ-UHFFFAOYSA-N 1-cyclopentyl-4-[4-[6-(4-cyclopropyl-5-methyl-1h-imidazol-2-yl)pyridin-2-yl]piperazin-1-yl]azepane Chemical compound CC=1N=C(C=2N=C(C=CC=2)N2CCN(CC2)C2CCN(CCC2)C2CCCC2)NC=1C1CC1 VEXIBQGHRYNKAQ-UHFFFAOYSA-N 0.000 claims 1
- PPMSCHPFBVKUCV-UHFFFAOYSA-N 1-methyl-2-[6-[4-(1-propan-2-ylpiperidin-4-yl)-1,4-diazepan-1-yl]pyridin-2-yl]benzimidazole Chemical compound C1CN(C(C)C)CCC1N1CCN(C=2N=C(C=CC=2)C=2N(C3=CC=CC=C3N=2)C)CCC1 PPMSCHPFBVKUCV-UHFFFAOYSA-N 0.000 claims 1
- KXIXHISTUVHOCY-UHFFFAOYSA-N 1-propan-2-ylpiperidine Chemical compound CC(C)N1CCCCC1 KXIXHISTUVHOCY-UHFFFAOYSA-N 0.000 claims 1
- BJKHSTDISPLINH-UHFFFAOYSA-N 2-[4-[1-(2,3-dihydro-1h-inden-1-yl)piperidin-4-yl]-1,4-diazepan-1-yl]-1,3-thiazole Chemical compound C1CC2=CC=CC=C2C1N(CC1)CCC1N(CC1)CCCN1C1=NC=CS1 BJKHSTDISPLINH-UHFFFAOYSA-N 0.000 claims 1
- CRMVACNKGGRPCC-UHFFFAOYSA-N 2-[4-[1-[(2-chlorophenyl)methyl]piperidin-4-yl]-1,4-diazepan-1-yl]-1,3-thiazole Chemical compound ClC1=CC=CC=C1CN1CCC(N2CCN(CCC2)C=2SC=CN=2)CC1 CRMVACNKGGRPCC-UHFFFAOYSA-N 0.000 claims 1
- WOXFBRXGAYESEW-UHFFFAOYSA-N 2-[4-[1-[(2-chlorophenyl)methyl]piperidin-4-yl]-1,4-diazepan-1-yl]-n-(3-imidazol-1-ylpropyl)-6-methylpyrimidine-4-carboxamide Chemical compound N=1C(C)=CC(C(=O)NCCCN2C=NC=C2)=NC=1N(CC1)CCCN1C(CC1)CCN1CC1=CC=CC=C1Cl WOXFBRXGAYESEW-UHFFFAOYSA-N 0.000 claims 1
- YVSAQUNJJPRNTP-UHFFFAOYSA-N 2-[4-[1-[(2-chlorophenyl)methyl]piperidin-4-yl]-1,4-diazepan-1-yl]-n-(cyclopropylmethyl)-1,3-thiazole-4-carboxamide Chemical compound ClC1=CC=CC=C1CN1CCC(N2CCN(CCC2)C=2SC=C(N=2)C(=O)NCC2CC2)CC1 YVSAQUNJJPRNTP-UHFFFAOYSA-N 0.000 claims 1
- RMRZJNFFWPLVOQ-UHFFFAOYSA-N 2-[4-[1-[(2-chlorophenyl)methyl]piperidin-4-yl]-1,4-diazepan-1-yl]-n-(cyclopropylmethyl)pyridine-4-carboxamide Chemical compound ClC1=CC=CC=C1CN1CCC(N2CCN(CCC2)C=2N=CC=C(C=2)C(=O)NCC2CC2)CC1 RMRZJNFFWPLVOQ-UHFFFAOYSA-N 0.000 claims 1
- CXWMSSAQYYNIGK-UHFFFAOYSA-N 2-[6-[4-(1-propan-2-ylpiperidin-4-yl)-1,4-diazepan-1-yl]pyridin-2-yl]-1,3-benzothiazole Chemical compound C1CN(C(C)C)CCC1N1CCN(C=2N=C(C=CC=2)C=2SC3=CC=CC=C3N=2)CCC1 CXWMSSAQYYNIGK-UHFFFAOYSA-N 0.000 claims 1
- HGVGOXXITQWWIS-UHFFFAOYSA-N 2-[6-[4-(1-propan-2-ylpiperidin-4-yl)-1,4-diazepan-1-yl]pyridin-2-yl]-1h-benzimidazole Chemical compound C1CN(C(C)C)CCC1N1CCN(C=2N=C(C=CC=2)C=2NC3=CC=CC=C3N=2)CCC1 HGVGOXXITQWWIS-UHFFFAOYSA-N 0.000 claims 1
- KCYUERPUDTYDIB-UHFFFAOYSA-N 2-[6-[4-(1-propan-2-ylpiperidin-4-yl)-1,4-diazepan-1-yl]pyridin-2-yl]-3h-benzimidazole-5-carbonitrile Chemical compound C1CN(C(C)C)CCC1N1CCN(C=2N=C(C=CC=2)C=2NC3=CC(=CC=C3N=2)C#N)CCC1 KCYUERPUDTYDIB-UHFFFAOYSA-N 0.000 claims 1
- YGHOCXZFRXXQPL-UHFFFAOYSA-N 2-[6-[4-(1-propan-2-ylpiperidin-4-yl)-1,4-diazepan-1-yl]pyridin-2-yl]-6-(trifluoromethyl)-1h-benzimidazole Chemical compound C1CN(C(C)C)CCC1N1CCN(C=2N=C(C=CC=2)C=2NC3=CC(=CC=C3N=2)C(F)(F)F)CCC1 YGHOCXZFRXXQPL-UHFFFAOYSA-N 0.000 claims 1
- JQWJRZINMMEFND-UHFFFAOYSA-N 2-cyclopropyl-5-[6-[4-(1-propan-2-ylpiperidin-4-yl)-1,4-diazepan-1-yl]pyridin-2-yl]-1,3,4-oxadiazole Chemical compound C1CN(C(C)C)CCC1N1CCN(C=2N=C(C=CC=2)C=2OC(=NN=2)C2CC2)CCC1 JQWJRZINMMEFND-UHFFFAOYSA-N 0.000 claims 1
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 1
- KCJWZUWUQKEYFM-UHFFFAOYSA-N 2-phenyl-1-[6-[4-(1-propan-2-ylpiperidin-4-yl)-1,4-diazepan-1-yl]pyridin-2-yl]ethanone Chemical compound C1CN(C(C)C)CCC1N1CCN(C=2N=C(C=CC=2)C(=O)CC=2C=CC=CC=2)CCC1 KCJWZUWUQKEYFM-UHFFFAOYSA-N 0.000 claims 1
- WSKPUJRCGIQAIL-UHFFFAOYSA-N 3,4-dihydro-1h-isoquinolin-2-yl-[6-[4-(1-propan-2-ylpiperidin-4-yl)-1,4-diazepan-1-yl]pyridin-2-yl]methanone Chemical compound C1CN(C(C)C)CCC1N1CCN(C=2N=C(C=CC=2)C(=O)N2CC3=CC=CC=C3CC2)CCC1 WSKPUJRCGIQAIL-UHFFFAOYSA-N 0.000 claims 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- ZLKUEXXAPJUZEX-UHFFFAOYSA-N 4-[4-[6-(4-cyclopropyl-5-methyl-1h-imidazol-2-yl)pyridin-2-yl]piperazin-1-yl]-1-propan-2-ylazepane Chemical compound C1CN(C(C)C)CCCC1N1CCN(C=2N=C(C=CC=2)C=2NC(=C(C)N=2)C2CC2)CC1 ZLKUEXXAPJUZEX-UHFFFAOYSA-N 0.000 claims 1
- GKWVJBPZZHVZND-UHFFFAOYSA-N 4-fluoro-2-[6-[4-(1-propan-2-ylpiperidin-4-yl)-1,4-diazepan-1-yl]pyridin-2-yl]-1h-benzimidazole Chemical compound C1CN(C(C)C)CCC1N1CCN(C=2N=C(C=CC=2)C=2NC3=C(F)C=CC=C3N=2)CCC1 GKWVJBPZZHVZND-UHFFFAOYSA-N 0.000 claims 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 1
- XTEOXRCHHWCHJB-UHFFFAOYSA-N 4-methyl-2-[6-[4-(1-propan-2-ylpiperidin-4-yl)-1,4-diazepan-1-yl]pyridin-2-yl]-1h-benzimidazole Chemical compound C1CN(C(C)C)CCC1N1CCN(C=2N=C(C=CC=2)C=2NC3=C(C)C=CC=C3N=2)CCC1 XTEOXRCHHWCHJB-UHFFFAOYSA-N 0.000 claims 1
- DMPLJICYJKFHSR-UHFFFAOYSA-N 5,6-difluoro-2-[6-[4-(1-propan-2-ylpiperidin-4-yl)-1,4-diazepan-1-yl]pyridin-2-yl]-1h-benzimidazole Chemical compound C1CN(C(C)C)CCC1N1CCN(C=2N=C(C=CC=2)C=2NC3=CC(F)=C(F)C=C3N=2)CCC1 DMPLJICYJKFHSR-UHFFFAOYSA-N 0.000 claims 1
- KCJPRKHAJSSXBI-UHFFFAOYSA-N 5,6-dimethyl-2-[6-[4-(1-propan-2-ylpiperidin-4-yl)-1,4-diazepan-1-yl]pyridin-2-yl]-1h-benzimidazole Chemical compound C1CN(C(C)C)CCC1N1CCN(C=2N=C(C=CC=2)C=2NC3=CC(C)=C(C)C=C3N=2)CCC1 KCJPRKHAJSSXBI-UHFFFAOYSA-N 0.000 claims 1
- ZIBQDBWBEQVWKN-UHFFFAOYSA-N 5-butyl-2-[6-[4-(1-propan-2-ylpiperidin-4-yl)-1,4-diazepan-1-yl]pyridin-2-yl]-1,3-oxazole Chemical compound O1C(CCCC)=CN=C1C1=CC=CC(N2CCN(CCC2)C2CCN(CC2)C(C)C)=N1 ZIBQDBWBEQVWKN-UHFFFAOYSA-N 0.000 claims 1
- FUFZNHHSSMCXCZ-UHFFFAOYSA-N 5-piperidin-4-yl-3-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazole Chemical compound FC(F)(F)C1=CC=CC(C=2N=C(ON=2)C2CCNCC2)=C1 FUFZNHHSSMCXCZ-UHFFFAOYSA-N 0.000 claims 1
- IFQJUQSMHMAQDY-UHFFFAOYSA-N 6-[4-(1-benzylpiperidin-4-yl)-1,4-diazepan-1-yl]-n-(cyclopropylmethyl)pyridine-2-carboxamide Chemical compound C=1C=CC(N2CCN(CCC2)C2CCN(CC=3C=CC=CC=3)CC2)=NC=1C(=O)NCC1CC1 IFQJUQSMHMAQDY-UHFFFAOYSA-N 0.000 claims 1
- SDSNIFIRRPBMDV-UHFFFAOYSA-N 6-[4-(1-cyclopentylpiperidin-4-yl)-1,4-diazepan-1-yl]-n-(cyclopropylmethyl)pyridine-2-carboxamide Chemical compound C=1C=CC(N2CCN(CCC2)C2CCN(CC2)C2CCCC2)=NC=1C(=O)NCC1CC1 SDSNIFIRRPBMDV-UHFFFAOYSA-N 0.000 claims 1
- OMGPXNAIRVGIBF-UHFFFAOYSA-N 6-[4-(1-propan-2-ylpiperidin-4-yl)-1,4-diazepan-1-yl]-n-propylpyridine-2-carboxamide Chemical compound CCCNC(=O)C1=CC=CC(N2CCN(CCC2)C2CCN(CC2)C(C)C)=N1 OMGPXNAIRVGIBF-UHFFFAOYSA-N 0.000 claims 1
- AUIFTFPZVWGYMI-UHFFFAOYSA-N 6-[4-(1-tert-butylpiperidin-4-yl)-1,4-diazepan-1-yl]-n-(cyclopropylmethyl)pyridine-2-carboxamide Chemical compound C1CN(C(C)(C)C)CCC1N1CCN(C=2N=C(C=CC=2)C(=O)NCC2CC2)CCC1 AUIFTFPZVWGYMI-UHFFFAOYSA-N 0.000 claims 1
- WIAOVWFZTPGGEI-UHFFFAOYSA-N 6-[4-(4-tert-butylcyclohexyl)-1,4-diazepan-1-yl]-n-(pyridin-3-ylmethyl)pyridine-2-carboxamide Chemical compound C1CC(C(C)(C)C)CCC1N1CCN(C=2N=C(C=CC=2)C(=O)NCC=2C=NC=CC=2)CCC1 WIAOVWFZTPGGEI-UHFFFAOYSA-N 0.000 claims 1
- UQHVZVDGWGKQGC-XMMPIXPASA-N 6-[4-[1-[(1r)-1-phenylethyl]piperidin-4-yl]-1,4-diazepan-1-yl]-n-(pyridin-3-ylmethyl)pyridine-2-carboxamide Chemical compound C1CN([C@H](C)C=2C=CC=CC=2)CCC1N(CC1)CCCN1C(N=1)=CC=CC=1C(=O)NCC1=CC=CN=C1 UQHVZVDGWGKQGC-XMMPIXPASA-N 0.000 claims 1
- WNKNQSCEUFVRIT-UHFFFAOYSA-N 6-[4-[1-[(2-chloro-4-fluorophenyl)methyl]piperidin-4-yl]-1,4-diazepan-1-yl]-n-(cyclopropylmethyl)pyridine-2-carboxamide Chemical compound ClC1=CC(F)=CC=C1CN1CCC(N2CCN(CCC2)C=2N=C(C=CC=2)C(=O)NCC2CC2)CC1 WNKNQSCEUFVRIT-UHFFFAOYSA-N 0.000 claims 1
- COGMOTHICHMETH-UHFFFAOYSA-N 6-[4-[1-[(2-chlorophenyl)methyl]piperidin-4-yl]-1,4-diazepan-1-yl]-n-(1,3-oxazol-4-ylmethyl)pyridine-2-carboxamide Chemical compound ClC1=CC=CC=C1CN1CCC(N2CCN(CCC2)C=2N=C(C=CC=2)C(=O)NCC=2N=COC=2)CC1 COGMOTHICHMETH-UHFFFAOYSA-N 0.000 claims 1
- XUVVELOOVSMFDE-UHFFFAOYSA-N 6-[4-[1-[(2-chlorophenyl)methyl]piperidin-4-yl]-1,4-diazepan-1-yl]-n-(2,2,2-trifluoroethyl)pyridine-2-carboxamide Chemical compound FC(F)(F)CNC(=O)C1=CC=CC(N2CCN(CCC2)C2CCN(CC=3C(=CC=CC=3)Cl)CC2)=N1 XUVVELOOVSMFDE-UHFFFAOYSA-N 0.000 claims 1
- QIJMAEYJLKGTNS-UHFFFAOYSA-N 6-[4-[1-[(2-chlorophenyl)methyl]piperidin-4-yl]-1,4-diazepan-1-yl]-n-(2,6-dimethylpyridin-4-yl)pyridine-2-carboxamide Chemical compound CC1=NC(C)=CC(NC(=O)C=2N=C(C=CC=2)N2CCN(CCC2)C2CCN(CC=3C(=CC=CC=3)Cl)CC2)=C1 QIJMAEYJLKGTNS-UHFFFAOYSA-N 0.000 claims 1
- MHEPYCPJHMSOSL-UHFFFAOYSA-N 6-[4-[1-[(2-chlorophenyl)methyl]piperidin-4-yl]-1,4-diazepan-1-yl]-n-(2-methoxyethyl)pyridine-2-carboxamide Chemical compound COCCNC(=O)C1=CC=CC(N2CCN(CCC2)C2CCN(CC=3C(=CC=CC=3)Cl)CC2)=N1 MHEPYCPJHMSOSL-UHFFFAOYSA-N 0.000 claims 1
- QDFDWYGXMAMJPM-UHFFFAOYSA-N 6-[4-[1-[(2-chlorophenyl)methyl]piperidin-4-yl]-1,4-diazepan-1-yl]-n-(2-methylpyridin-4-yl)pyridine-2-carboxamide Chemical compound C1=NC(C)=CC(NC(=O)C=2N=C(C=CC=2)N2CCN(CCC2)C2CCN(CC=3C(=CC=CC=3)Cl)CC2)=C1 QDFDWYGXMAMJPM-UHFFFAOYSA-N 0.000 claims 1
- FHUJQPJAGZJSQH-UHFFFAOYSA-N 6-[4-[1-[(2-chlorophenyl)methyl]piperidin-4-yl]-1,4-diazepan-1-yl]-n-(3-methylbutyl)pyridine-2-carboxamide Chemical compound CC(C)CCNC(=O)C1=CC=CC(N2CCN(CCC2)C2CCN(CC=3C(=CC=CC=3)Cl)CC2)=N1 FHUJQPJAGZJSQH-UHFFFAOYSA-N 0.000 claims 1
- OHZHMJSVHZQQAF-UHFFFAOYSA-N 6-[4-[1-[(2-chlorophenyl)methyl]piperidin-4-yl]-1,4-diazepan-1-yl]-n-(cyclopropylmethyl)-4-methylpyridine-2-carboxamide Chemical compound C=1C(C)=CC(N2CCN(CCC2)C2CCN(CC=3C(=CC=CC=3)Cl)CC2)=NC=1C(=O)NCC1CC1 OHZHMJSVHZQQAF-UHFFFAOYSA-N 0.000 claims 1
- QJVGPWYHAMAJLN-UHFFFAOYSA-N 6-[4-[1-[(2-chlorophenyl)methyl]piperidin-4-yl]-1,4-diazepan-1-yl]-n-(cyclopropylmethyl)-5-methoxypyridine-2-carboxamide Chemical compound COC1=CC=C(C(=O)NCC2CC2)N=C1N(CC1)CCCN1C(CC1)CCN1CC1=CC=CC=C1Cl QJVGPWYHAMAJLN-UHFFFAOYSA-N 0.000 claims 1
- CVPQHEOLCSYAIH-UHFFFAOYSA-N 6-[4-[1-[(2-chlorophenyl)methyl]piperidin-4-yl]-1,4-diazepan-1-yl]-n-(cyclopropylmethyl)pyridine-2-carboxamide Chemical compound ClC1=CC=CC=C1CN1CCC(N2CCN(CCC2)C=2N=C(C=CC=2)C(=O)NCC2CC2)CC1 CVPQHEOLCSYAIH-UHFFFAOYSA-N 0.000 claims 1
- FOFBIZCIAKBAFU-UHFFFAOYSA-N 6-[4-[1-[(2-chlorophenyl)methyl]piperidin-4-yl]-1,4-diazepan-1-yl]-n-(oxan-4-yl)pyridine-2-carboxamide Chemical compound ClC1=CC=CC=C1CN1CCC(N2CCN(CCC2)C=2N=C(C=CC=2)C(=O)NC2CCOCC2)CC1 FOFBIZCIAKBAFU-UHFFFAOYSA-N 0.000 claims 1
- QANGZSQBJRVOCB-UHFFFAOYSA-N 6-[4-[1-[(2-chlorophenyl)methyl]piperidin-4-yl]-1,4-diazepan-1-yl]-n-(oxan-4-ylmethyl)pyridine-2-carboxamide Chemical compound ClC1=CC=CC=C1CN1CCC(N2CCN(CCC2)C=2N=C(C=CC=2)C(=O)NCC2CCOCC2)CC1 QANGZSQBJRVOCB-UHFFFAOYSA-N 0.000 claims 1
- LCBFYYNDRCMLNZ-UHFFFAOYSA-N 6-[4-[1-[(2-chlorophenyl)methyl]piperidin-4-yl]-1,4-diazepan-1-yl]-n-(pyridin-3-ylmethyl)pyridine-2-carboxamide Chemical compound ClC1=CC=CC=C1CN1CCC(N2CCN(CCC2)C=2N=C(C=CC=2)C(=O)NCC=2C=NC=CC=2)CC1 LCBFYYNDRCMLNZ-UHFFFAOYSA-N 0.000 claims 1
- GRRKCCLKCKFWKN-UHFFFAOYSA-N 6-[4-[1-[(2-chlorophenyl)methyl]piperidin-4-yl]-1,4-diazepan-1-yl]-n-(pyridin-4-ylmethyl)pyridine-2-carboxamide Chemical compound ClC1=CC=CC=C1CN1CCC(N2CCN(CCC2)C=2N=C(C=CC=2)C(=O)NCC=2C=CN=CC=2)CC1 GRRKCCLKCKFWKN-UHFFFAOYSA-N 0.000 claims 1
- SIYVAAXUIZBWGZ-UHFFFAOYSA-N 6-[4-[1-[(2-chlorophenyl)methyl]piperidin-4-yl]-1,4-diazepan-1-yl]-n-ethylpyridine-2-carboxamide Chemical compound CCNC(=O)C1=CC=CC(N2CCN(CCC2)C2CCN(CC=3C(=CC=CC=3)Cl)CC2)=N1 SIYVAAXUIZBWGZ-UHFFFAOYSA-N 0.000 claims 1
- SMEXXYBDDXFPKI-UHFFFAOYSA-N 6-[4-[1-[(2-chlorophenyl)methyl]piperidin-4-yl]-1,4-diazepan-1-yl]pyridine-2-carbonitrile Chemical compound ClC1=CC=CC=C1CN1CCC(N2CCN(CCC2)C=2N=C(C=CC=2)C#N)CC1 SMEXXYBDDXFPKI-UHFFFAOYSA-N 0.000 claims 1
- JHRKIDPSDKPQOD-UHFFFAOYSA-N 6-[4-[1-[(2-chlorophenyl)methyl]piperidin-4-yl]-1,4-diazepan-1-yl]pyridine-2-carboxamide Chemical compound NC(=O)C1=CC=CC(N2CCN(CCC2)C2CCN(CC=3C(=CC=CC=3)Cl)CC2)=N1 JHRKIDPSDKPQOD-UHFFFAOYSA-N 0.000 claims 1
- ARYKYCQMTWQKQU-UHFFFAOYSA-N 6-[4-[1-[(3-chlorophenyl)methyl]piperidin-4-yl]-1,4-diazepan-1-yl]-n-(cyclopropylmethyl)pyridine-2-carboxamide Chemical compound ClC1=CC=CC(CN2CCC(CC2)N2CCN(CCC2)C=2N=C(C=CC=2)C(=O)NCC2CC2)=C1 ARYKYCQMTWQKQU-UHFFFAOYSA-N 0.000 claims 1
- GSKLVKOTVICTQP-UHFFFAOYSA-N 6-[4-[2-hydroxy-3-(propan-2-ylamino)propyl]-1,4-diazepan-1-yl]-n-(pyridin-3-ylmethyl)pyridine-2-carboxamide Chemical compound C1CN(CC(O)CNC(C)C)CCCN1C1=CC=CC(C(=O)NCC=2C=NC=CC=2)=N1 GSKLVKOTVICTQP-UHFFFAOYSA-N 0.000 claims 1
- WNGXKXSOYJGNMC-UHFFFAOYSA-N 6-fluoro-2-[6-[4-(1-propan-2-ylpiperidin-4-yl)-1,4-diazepan-1-yl]pyridin-2-yl]-1h-benzimidazole Chemical compound C1CN(C(C)C)CCC1N1CCN(C=2N=C(C=CC=2)C=2NC3=CC(F)=CC=C3N=2)CCC1 WNGXKXSOYJGNMC-UHFFFAOYSA-N 0.000 claims 1
- KXDRXNZOOOKAEI-UHFFFAOYSA-N 6-methoxy-2-[6-[4-(1-propan-2-ylpiperidin-4-yl)-1,4-diazepan-1-yl]pyridin-2-yl]-1h-benzimidazole Chemical compound N1C2=CC(OC)=CC=C2N=C1C(N=1)=CC=CC=1N(CC1)CCCN1C1CCN(C(C)C)CC1 KXDRXNZOOOKAEI-UHFFFAOYSA-N 0.000 claims 1
- JMVNLDIFYOVCPI-UHFFFAOYSA-N 6-methyl-2-[6-[4-(1-propan-2-ylpiperidin-4-yl)-1,4-diazepan-1-yl]pyridin-2-yl]-1h-benzimidazole Chemical compound C1CN(C(C)C)CCC1N1CCN(C=2N=C(C=CC=2)C=2NC3=CC(C)=CC=C3N=2)CCC1 JMVNLDIFYOVCPI-UHFFFAOYSA-N 0.000 claims 1
- 208000030507 AIDS Diseases 0.000 claims 1
- 206010006187 Breast cancer Diseases 0.000 claims 1
- 208000026310 Breast neoplasm Diseases 0.000 claims 1
- 102100031650 C-X-C chemokine receptor type 4 Human genes 0.000 claims 1
- CNMGCUPLLZKQOY-JOCHJYFZSA-N CC(C)N1C[C@@H](CN(CCC2)CCN2C2=CC=CCN2C2=CC=NC=C2)OCC1 Chemical compound CC(C)N1C[C@@H](CN(CCC2)CCN2C2=CC=CCN2C2=CC=NC=C2)OCC1 CNMGCUPLLZKQOY-JOCHJYFZSA-N 0.000 claims 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims 1
- 206010012689 Diabetic retinopathy Diseases 0.000 claims 1
- 102100039619 Granulocyte colony-stimulating factor Human genes 0.000 claims 1
- 101000922348 Homo sapiens C-X-C chemokine receptor type 4 Proteins 0.000 claims 1
- 101000746367 Homo sapiens Granulocyte colony-stimulating factor Proteins 0.000 claims 1
- 206010061218 Inflammation Diseases 0.000 claims 1
- 206010027476 Metastases Diseases 0.000 claims 1
- 208000034578 Multiple myelomas Diseases 0.000 claims 1
- 206010029260 Neuroblastoma Diseases 0.000 claims 1
- 208000015914 Non-Hodgkin lymphomas Diseases 0.000 claims 1
- 208000002193 Pain Diseases 0.000 claims 1
- 206010035226 Plasma cell myeloma Diseases 0.000 claims 1
- 208000007135 Retinal Neovascularization Diseases 0.000 claims 1
- 208000036142 Viral infection Diseases 0.000 claims 1
- DOTSVTLLCPXTPA-UHFFFAOYSA-N [6-[4-[1-[(2-chlorophenyl)methyl]piperidin-4-yl]-1,4-diazepan-1-yl]pyridin-2-yl]methanol Chemical compound OCC1=CC=CC(N2CCN(CCC2)C2CCN(CC=3C(=CC=CC=3)Cl)CC2)=N1 DOTSVTLLCPXTPA-UHFFFAOYSA-N 0.000 claims 1
- 206010064930 age-related macular degeneration Diseases 0.000 claims 1
- 125000005334 azaindolyl group Chemical group N1N=C(C2=CC=CC=C12)* 0.000 claims 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims 1
- 208000025698 brain inflammatory disease Diseases 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 150000003857 carboxamides Chemical class 0.000 claims 1
- 125000000068 chlorophenyl group Chemical group 0.000 claims 1
- 230000001149 cognitive effect Effects 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 230000007850 degeneration Effects 0.000 claims 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
- WJJMNDUMQPNECX-UHFFFAOYSA-N dipicolinic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=N1 WJJMNDUMQPNECX-UHFFFAOYSA-N 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 206010014599 encephalitis Diseases 0.000 claims 1
- 230000003394 haemopoietic effect Effects 0.000 claims 1
- 238000003306 harvesting Methods 0.000 claims 1
- 201000005787 hematologic cancer Diseases 0.000 claims 1
- 208000024200 hematopoietic and lymphoid system neoplasm Diseases 0.000 claims 1
- 210000003958 hematopoietic stem cell Anatomy 0.000 claims 1
- 125000004464 hydroxyphenyl group Chemical group 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 230000004054 inflammatory process Effects 0.000 claims 1
- 201000002364 leukopenia Diseases 0.000 claims 1
- 231100001022 leukopenia Toxicity 0.000 claims 1
- 208000002780 macular degeneration Diseases 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- 230000009401 metastasis Effects 0.000 claims 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 1
- LRJFDHBVNNNIKA-KRWDZBQOSA-N n-(1,3-thiazol-2-ylmethyl)-6-[4-[1-[(2s)-1,1,1-trifluoropropan-2-yl]piperidin-4-yl]-1,4-diazepan-1-yl]pyridine-2-carboxamide Chemical compound C1CN([C@@H](C)C(F)(F)F)CCC1N1CCN(C=2N=C(C=CC=2)C(=O)NCC=2SC=CN=2)CCC1 LRJFDHBVNNNIKA-KRWDZBQOSA-N 0.000 claims 1
- PSRYOOFOGQKUPJ-UHFFFAOYSA-N n-(cyclopropylmethyl)-6-[4-(1-ethylpiperidin-4-yl)-1,4-diazepan-1-yl]pyridine-2-carboxamide Chemical compound C1CN(CC)CCC1N1CCN(C=2N=C(C=CC=2)C(=O)NCC2CC2)CCC1 PSRYOOFOGQKUPJ-UHFFFAOYSA-N 0.000 claims 1
- FINMDSFGSIJYLU-UHFFFAOYSA-N n-(cyclopropylmethyl)-6-[4-(1-propylpiperidin-4-yl)-1,4-diazepan-1-yl]pyridine-2-carboxamide Chemical compound C1CN(CCC)CCC1N1CCN(C=2N=C(C=CC=2)C(=O)NCC2CC2)CCC1 FINMDSFGSIJYLU-UHFFFAOYSA-N 0.000 claims 1
- RRUTYWLNFYFUPN-UHFFFAOYSA-N n-(cyclopropylmethyl)-6-[4-[1-(1,1-difluoropropan-2-yl)piperidin-4-yl]-1,4-diazepan-1-yl]pyridine-2-carboxamide Chemical compound C1CN(C(C(F)F)C)CCC1N1CCN(C=2N=C(C=CC=2)C(=O)NCC2CC2)CCC1 RRUTYWLNFYFUPN-UHFFFAOYSA-N 0.000 claims 1
- DNDXGBICVPDZIL-UHFFFAOYSA-N n-(cyclopropylmethyl)-6-[4-[1-(1,3-difluoropropan-2-yl)piperidin-4-yl]-1,4-diazepan-1-yl]pyridine-2-carboxamide Chemical compound C1CN(C(CF)CF)CCC1N1CCN(C=2N=C(C=CC=2)C(=O)NCC2CC2)CCC1 DNDXGBICVPDZIL-UHFFFAOYSA-N 0.000 claims 1
- CXDFICOPUWBTQQ-UHFFFAOYSA-N n-(cyclopropylmethyl)-6-[4-[1-(1-fluoropropan-2-yl)piperidin-4-yl]-1,4-diazepan-1-yl]pyridine-2-carboxamide Chemical compound C1CN(C(CF)C)CCC1N1CCN(C=2N=C(C=CC=2)C(=O)NCC2CC2)CCC1 CXDFICOPUWBTQQ-UHFFFAOYSA-N 0.000 claims 1
- CGDQDVQOJMKCAO-UHFFFAOYSA-N n-(cyclopropylmethyl)-6-[4-[1-(1-methoxypropan-2-yl)piperidin-4-yl]-1,4-diazepan-1-yl]pyridine-2-carboxamide Chemical compound C1CN(C(C)COC)CCC1N1CCN(C=2N=C(C=CC=2)C(=O)NCC2CC2)CCC1 CGDQDVQOJMKCAO-UHFFFAOYSA-N 0.000 claims 1
- UUEAVSHIIHXNTB-UHFFFAOYSA-N n-(cyclopropylmethyl)-6-[4-[1-(2-fluorocyclopentyl)piperidin-4-yl]-1,4-diazepan-1-yl]pyridine-2-carboxamide Chemical compound FC1CCCC1N1CCC(N2CCN(CCC2)C=2N=C(C=CC=2)C(=O)NCC2CC2)CC1 UUEAVSHIIHXNTB-UHFFFAOYSA-N 0.000 claims 1
- DGLUSUYKMAXEBU-UHFFFAOYSA-N n-(cyclopropylmethyl)-6-[4-[1-(2-methoxyethyl)piperidin-4-yl]-1,4-diazepan-1-yl]pyridine-2-carboxamide Chemical compound C1CN(CCOC)CCC1N1CCN(C=2N=C(C=CC=2)C(=O)NCC2CC2)CCC1 DGLUSUYKMAXEBU-UHFFFAOYSA-N 0.000 claims 1
- HXGDMWAJBXHPMF-UHFFFAOYSA-N n-(cyclopropylmethyl)-6-[4-[1-(4,4,4-trifluorobutan-2-yl)piperidin-4-yl]-1,4-diazepan-1-yl]pyridine-2-carboxamide Chemical compound C1CN(C(CC(F)(F)F)C)CCC1N1CCN(C=2N=C(C=CC=2)C(=O)NCC2CC2)CCC1 HXGDMWAJBXHPMF-UHFFFAOYSA-N 0.000 claims 1
- LOOYIPQJFNSIEJ-UHFFFAOYSA-N n-(cyclopropylmethyl)-6-[4-[1-(oxolan-3-yl)piperidin-4-yl]-1,4-diazepan-1-yl]pyridine-2-carboxamide Chemical compound C=1C=CC(N2CCN(CCC2)C2CCN(CC2)C2COCC2)=NC=1C(=O)NCC1CC1 LOOYIPQJFNSIEJ-UHFFFAOYSA-N 0.000 claims 1
- SAKTYHHWBVGBGB-OAQYLSRUSA-N n-(cyclopropylmethyl)-6-[4-[1-[(1r)-1-(4-fluorophenyl)ethyl]piperidin-4-yl]-1,4-diazepan-1-yl]pyridine-2-carboxamide Chemical compound C1CN([C@H](C)C=2C=CC(F)=CC=2)CCC1N(CC1)CCCN1C(N=1)=CC=CC=1C(=O)NCC1CC1 SAKTYHHWBVGBGB-OAQYLSRUSA-N 0.000 claims 1
- GTMJGQSXFUKBIY-JOCHJYFZSA-N n-(cyclopropylmethyl)-6-[4-[1-[(1r)-1-phenylethyl]piperidin-4-yl]-1,4-diazepan-1-yl]pyridine-2-carboxamide Chemical compound C1CN([C@H](C)C=2C=CC=CC=2)CCC1N(CC1)CCCN1C(N=1)=CC=CC=1C(=O)NCC1CC1 GTMJGQSXFUKBIY-JOCHJYFZSA-N 0.000 claims 1
- DEODWOMJVYYSEW-HHHXNRCGSA-N n-(cyclopropylmethyl)-6-[4-[1-[(1r)-2,3-dihydro-1h-inden-1-yl]piperidin-4-yl]-1,4-diazepan-1-yl]pyridine-2-carboxamide Chemical compound C=1C=CC(N2CCN(CCC2)C2CCN(CC2)[C@H]2C3=CC=CC=C3CC2)=NC=1C(=O)NCC1CC1 DEODWOMJVYYSEW-HHHXNRCGSA-N 0.000 claims 1
- DEODWOMJVYYSEW-MHZLTWQESA-N n-(cyclopropylmethyl)-6-[4-[1-[(1s)-2,3-dihydro-1h-inden-1-yl]piperidin-4-yl]-1,4-diazepan-1-yl]pyridine-2-carboxamide Chemical compound C=1C=CC(N2CCN(CCC2)C2CCN(CC2)[C@@H]2C3=CC=CC=C3CC2)=NC=1C(=O)NCC1CC1 DEODWOMJVYYSEW-MHZLTWQESA-N 0.000 claims 1
- NSGQTIGMSQJNPN-UHFFFAOYSA-N n-(cyclopropylmethyl)-6-[4-[1-[(2-methoxyphenyl)methyl]piperidin-4-yl]-1,4-diazepan-1-yl]pyridine-2-carboxamide Chemical compound COC1=CC=CC=C1CN1CCC(N2CCN(CCC2)C=2N=C(C=CC=2)C(=O)NCC2CC2)CC1 NSGQTIGMSQJNPN-UHFFFAOYSA-N 0.000 claims 1
- VDVIKFHHJNWFIU-UHFFFAOYSA-N n-(cyclopropylmethyl)-6-[4-[1-[(2-methylphenyl)methyl]piperidin-4-yl]-1,4-diazepan-1-yl]pyridine-2-carboxamide Chemical compound CC1=CC=CC=C1CN1CCC(N2CCN(CCC2)C=2N=C(C=CC=2)C(=O)NCC2CC2)CC1 VDVIKFHHJNWFIU-UHFFFAOYSA-N 0.000 claims 1
- LWZPJRZBOQTALO-KRWDZBQOSA-N n-(cyclopropylmethyl)-6-[4-[1-[(2s)-1,1,1-trifluoropropan-2-yl]piperidin-4-yl]-1,4-diazepan-1-yl]pyridine-2-carboxamide Chemical compound C1CN([C@@H](C)C(F)(F)F)CCC1N1CCN(C=2N=C(C=CC=2)C(=O)NCC2CC2)CCC1 LWZPJRZBOQTALO-KRWDZBQOSA-N 0.000 claims 1
- DQKXHIIZISWEJA-UHFFFAOYSA-N n-(cyclopropylmethyl)-6-[4-[1-[(4-fluorophenyl)methyl]piperidin-4-yl]-1,4-diazepan-1-yl]pyridine-2-carboxamide Chemical compound C1=CC(F)=CC=C1CN1CCC(N2CCN(CCC2)C=2N=C(C=CC=2)C(=O)NCC2CC2)CC1 DQKXHIIZISWEJA-UHFFFAOYSA-N 0.000 claims 1
- ZIIKXOULEZWBIK-UHFFFAOYSA-N n-(cyclopropylmethyl)-6-[4-[3-(3,3-difluoropyrrolidin-1-yl)propyl]-1,4-diazepan-1-yl]pyridine-2-carboxamide Chemical compound C1C(F)(F)CCN1CCCN1CCN(C=2N=C(C=CC=2)C(=O)NCC2CC2)CCC1 ZIIKXOULEZWBIK-UHFFFAOYSA-N 0.000 claims 1
- VYNPVMVJEXJNBL-UHFFFAOYSA-N n-(pyridin-3-ylmethyl)-6-[4-[1-(4,4,4-trifluorobutan-2-yl)piperidin-4-yl]-1,4-diazepan-1-yl]pyridine-2-carboxamide Chemical compound C1CN(C(CC(F)(F)F)C)CCC1N1CCN(C=2N=C(C=CC=2)C(=O)NCC=2C=NC=CC=2)CCC1 VYNPVMVJEXJNBL-UHFFFAOYSA-N 0.000 claims 1
- FHGDHXBNJHAMCI-UHFFFAOYSA-N n-butyl-6-[4-[1-[(2-chlorophenyl)methyl]piperidin-4-yl]-1,4-diazepan-1-yl]pyridine-2-carboxamide Chemical compound CCCCNC(=O)C1=CC=CC(N2CCN(CCC2)C2CCN(CC=3C(=CC=CC=3)Cl)CC2)=N1 FHGDHXBNJHAMCI-UHFFFAOYSA-N 0.000 claims 1
- FEJVGEHNFCKXLG-SFHVURJKSA-N n-butyl-6-[4-[1-[(2s)-1,1,1-trifluoropropan-2-yl]piperidin-4-yl]-1,4-diazepan-1-yl]pyridine-2-carboxamide Chemical compound CCCCNC(=O)C1=CC=CC(N2CCN(CCC2)C2CCN(CC2)[C@@H](C)C(F)(F)F)=N1 FEJVGEHNFCKXLG-SFHVURJKSA-N 0.000 claims 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 230000014399 negative regulation of angiogenesis Effects 0.000 claims 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 230000004770 neurodegeneration Effects 0.000 claims 1
- 210000004967 non-hematopoietic stem cell Anatomy 0.000 claims 1
- 208000002154 non-small cell lung carcinoma Diseases 0.000 claims 1
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000004193 piperazinyl group Chemical group 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 1
- 125000006223 tetrahydrofuranylmethyl group Chemical group 0.000 claims 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 1
- 125000006173 tetrahydropyranylmethyl group Chemical group 0.000 claims 1
- 125000003831 tetrazolyl group Chemical group 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- 125000005302 thiazolylmethyl group Chemical group [H]C1=C([H])N=C(S1)C([H])([H])* 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
- 238000011282 treatment Methods 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims 1
- 230000009385 viral infection Effects 0.000 claims 1
- 239000002253 acid Substances 0.000 description 7
- 239000012453 solvate Substances 0.000 description 5
- 239000002585 base Substances 0.000 description 4
- 150000004677 hydrates Chemical class 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 229930006000 Sucrose Natural products 0.000 description 3
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 235000013681 dietary sucrose Nutrition 0.000 description 3
- 229960004793 sucrose Drugs 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- 150000001204 N-oxides Chemical class 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 235000010443 alginic acid Nutrition 0.000 description 2
- 229920000615 alginic acid Polymers 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 229920000609 methyl cellulose Polymers 0.000 description 2
- 239000001923 methylcellulose Substances 0.000 description 2
- 235000010981 methylcellulose Nutrition 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 229940032147 starch Drugs 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical class O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- BWLUMTFWVZZZND-UHFFFAOYSA-N Dibenzylamine Chemical compound C=1C=CC=CC=1CNCC1=CC=CC=C1 BWLUMTFWVZZZND-UHFFFAOYSA-N 0.000 description 1
- LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical compound OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 description 1
- 229930064664 L-arginine Natural products 0.000 description 1
- 235000014852 L-arginine Nutrition 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-UHFFFAOYSA-N 0.000 description 1
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 235000010419 agar Nutrition 0.000 description 1
- 229940072056 alginate Drugs 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
- 229960001126 alginic acid Drugs 0.000 description 1
- 150000004781 alginic acids Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 229960004365 benzoic acid Drugs 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
- 239000008116 calcium stearate Substances 0.000 description 1
- 235000013539 calcium stearate Nutrition 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 235000010980 cellulose Nutrition 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
- 229960001231 choline Drugs 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
- 229940043264 dodecyl sulfate Drugs 0.000 description 1
- LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
- 229940093471 ethyl oleate Drugs 0.000 description 1
- 239000007888 film coating Substances 0.000 description 1
- 238000009501 film coating Methods 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 229960002989 glutamic acid Drugs 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 229960000448 lactic acid Drugs 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 229960004393 lidocaine hydrochloride Drugs 0.000 description 1
- YECIFGHRMFEPJK-UHFFFAOYSA-N lidocaine hydrochloride monohydrate Chemical compound O.[Cl-].CC[NH+](CC)CC(=O)NC1=C(C)C=CC=C1C YECIFGHRMFEPJK-UHFFFAOYSA-N 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- YZMHQCWXYHARLS-UHFFFAOYSA-N naphthalene-1,2-disulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(S(=O)(=O)O)=CC=C21 YZMHQCWXYHARLS-UHFFFAOYSA-N 0.000 description 1
- 229920001206 natural gum Polymers 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229950008882 polysorbate Drugs 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 229920003109 sodium starch glycolate Polymers 0.000 description 1
- 229940079832 sodium starch glycolate Drugs 0.000 description 1
- 239000008109 sodium starch glycolate Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- WPLOVIFNBMNBPD-ATHMIXSHSA-N subtilin Chemical compound CC1SCC(NC2=O)C(=O)NC(CC(N)=O)C(=O)NC(C(=O)NC(CCCCN)C(=O)NC(C(C)CC)C(=O)NC(=C)C(=O)NC(CCCCN)C(O)=O)CSC(C)C2NC(=O)C(CC(C)C)NC(=O)C1NC(=O)C(CCC(N)=O)NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C1NC(=O)C(=C/C)/NC(=O)C(CCC(N)=O)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)CNC(=O)C(NC(=O)C(NC(=O)C2NC(=O)CNC(=O)C3CCCN3C(=O)C(NC(=O)C3NC(=O)C(CC(C)C)NC(=O)C(=C)NC(=O)C(CCC(O)=O)NC(=O)C(NC(=O)C(CCCCN)NC(=O)C(N)CC=4C5=CC=CC=C5NC=4)CSC3)C(C)SC2)C(C)C)C(C)SC1)CC1=CC=CC=C1 WPLOVIFNBMNBPD-ATHMIXSHSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 238000009495 sugar coating Methods 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 229950000339 xinafoate Drugs 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1017345.8 | 2010-10-14 | ||
| GB201017345A GB201017345D0 (en) | 2010-10-14 | 2010-10-14 | Receptor antagonists |
| PCT/EP2011/067946 WO2012049277A1 (en) | 2010-10-14 | 2011-10-13 | Cxcr4 receptor antagonists |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015189271A Division JP6348891B2 (ja) | 2010-10-14 | 2015-09-28 | Ｃｘｃｒ４受容体アンタゴニスト |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013539777A JP2013539777A (ja) | 2013-10-28 |
| JP2013539777A5 true JP2013539777A5 (https=) | 2015-01-22 |
| JP5881718B2 JP5881718B2 (ja) | 2016-03-09 |
Family
ID=43304554
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013533225A Expired - Fee Related JP5881718B2 (ja) | 2010-10-14 | 2011-10-13 | Ｃｘｃｒ４受容体アンタゴニスト |
| JP2015189271A Expired - Fee Related JP6348891B2 (ja) | 2010-10-14 | 2015-09-28 | Ｃｘｃｒ４受容体アンタゴニスト |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015189271A Expired - Fee Related JP6348891B2 (ja) | 2010-10-14 | 2015-09-28 | Ｃｘｃｒ４受容体アンタゴニスト |
Country Status (15)
| Country | Link |
|---|---|
| US (5) | US9353086B2 (https=) |
| EP (2) | EP2927224B8 (https=) |
| JP (2) | JP5881718B2 (https=) |
| CN (1) | CN103282360B (https=) |
| AU (1) | AU2011315498C1 (https=) |
| BR (1) | BR112013009036B1 (https=) |
| CA (1) | CA2814419C (https=) |
| DK (2) | DK2627649T3 (https=) |
| ES (2) | ES2536281T3 (https=) |
| GB (1) | GB201017345D0 (https=) |
| IL (1) | IL225550A (https=) |
| PL (2) | PL2627649T3 (https=) |
| PT (2) | PT2627649E (https=) |
| SG (1) | SG189387A1 (https=) |
| WO (1) | WO2012049277A1 (https=) |
Families Citing this family (60)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB201017345D0 (en) | 2010-10-14 | 2010-11-24 | Proximagen Ltd | Receptor antagonists |
| BR112014015197A8 (pt) | 2011-12-21 | 2017-06-13 | Novira Therapeutics Inc | agentes antivirais de hepatite b |
| KR102271574B1 (ko) | 2012-08-28 | 2021-07-01 | 얀센 사이언시즈 아일랜드 언리미티드 컴퍼니 | 설파모일-아릴아미드 및 b형 간염 치료제로서의 그 용도 |
| MX359651B (es) | 2012-11-29 | 2018-10-05 | Chemocentryx Inc | Antagonistas de cxcr7. |
| CN105164107B (zh) * | 2012-12-20 | 2017-12-05 | 卢庆彬 | 用于与放射结合使用的放射增敏剂化合物 |
| EP2746259A1 (en) | 2012-12-21 | 2014-06-25 | Basf Se | Substituted [1,2,4]triazole and imidazole compounds |
| EP2746260A1 (en) | 2012-12-21 | 2014-06-25 | Basf Se | Substituted [1,2,4]triazole and imidazole compounds |
| WO2014131847A1 (en) | 2013-02-28 | 2014-09-04 | Janssen R&D Ireland | Sulfamoyl-arylamides and the use thereof as medicaments for the treatment of hepatitis b |
| MX353412B (es) | 2013-04-03 | 2018-01-10 | Janssen Sciences Ireland Uc | Derivados de n-fenil-carboxamida y su uso como medicamentos para el tratamiento de la hepatitis b. |
| TWI733288B (zh) | 2013-05-17 | 2021-07-11 | 愛爾蘭商健生科學愛爾蘭無限公司 | 胺磺醯基吡咯醯胺衍生物及其作為用於治療ｂ型肝炎藥物的用途 |
| HRP20180791T1 (hr) | 2013-07-25 | 2018-09-07 | Janssen Sciences Ireland Uc | Glioksamid supstituirani derivati pirolamida i njihova uporaba kao lijekova za liječenje hepatitisa b |
| CA2923712C (en) | 2013-10-23 | 2021-11-02 | Janssen Sciences Ireland Uc | Carboxamide derivatives and the use thereof as medicaments for the treatment of hepatitis b |
| US10392349B2 (en) | 2014-01-16 | 2019-08-27 | Novira Therapeutics, Inc. | Azepane derivatives and methods of treating hepatitis B infections |
| US9169212B2 (en) | 2014-01-16 | 2015-10-27 | Novira Therapeutics, Inc. | Azepane derivatives and methods of treating hepatitis B infections |
| CA2936947A1 (en) | 2014-02-05 | 2015-08-13 | Novira Therapeutics, Inc. | Combination therapy for treatment of hbv infections |
| TW201620893A (zh) | 2014-02-06 | 2016-06-16 | 健生科學愛爾蘭無限公司 | 磺醯胺基吡咯醯胺衍生物及其用作治療ｂ型肝炎之醫藥品的用途 |
| JP2018510159A (ja) | 2015-03-19 | 2018-04-12 | ノヴィラ・セラピューティクス・インコーポレイテッド | アゾカン及びアゾナン誘導体及びｂ型肝炎感染症の治療法 |
| AU2016242118B2 (en) * | 2015-04-02 | 2021-07-08 | Proximagen, Llc | Novel therapies for cancer |
| US10875876B2 (en) | 2015-07-02 | 2020-12-29 | Janssen Sciences Ireland Uc | Cyclized sulfamoylarylamide derivatives and the use thereof as medicaments for the treatment of hepatitis B |
| US10709697B2 (en) | 2015-07-16 | 2020-07-14 | Emory University | Bis-amines, compositions, and uses related to CXCR4 inhibition |
| TW201718496A (zh) | 2015-09-29 | 2017-06-01 | 諾維拉治療公司 | B型肝炎抗病毒劑之晶型 |
| CN109069426B (zh) | 2015-12-14 | 2021-10-29 | X4 制药有限公司 | 治疗癌症的方法 |
| CA3008279A1 (en) | 2015-12-14 | 2017-06-22 | X4 Pharmaceuticals, Inc. | Methods for treating cancer |
| WO2017112894A1 (en) | 2015-12-22 | 2017-06-29 | X4 Pharmaceuticals, Inc. | Methods for treating immunodeficiency disease |
| GB201604213D0 (en) * | 2016-03-11 | 2016-04-27 | Proximagen Ltd | Drug combination and its use in therapy |
| CA3019394A1 (en) | 2016-04-08 | 2017-10-12 | X4 Pharmaceuticals, Inc. | Methods for treating cancer |
| AU2017248828A1 (en) | 2016-04-15 | 2018-11-01 | Janssen Sciences Ireland Uc | Combinations and methods comprising a capsid assembly inhibitor |
| EP3246330A1 (en) | 2016-05-18 | 2017-11-22 | Istituto Europeo di Oncologia S.r.l. | Imidazoles as histone demethylase inhibitors |
| EP3472129A4 (en) | 2016-06-21 | 2019-12-04 | X4 Pharmaceuticals, Inc. | CXCR4 INHIBITORS AND USES THEREOF |
| ES2870920T3 (es) | 2016-06-21 | 2021-10-28 | X4 Pharmaceuticals Inc | Inhibidores de CXCR4 y usos de los mismos |
| CN109640988A (zh) | 2016-06-21 | 2019-04-16 | X4 制药有限公司 | Cxcr4抑制剂及其用途 |
| WO2018049214A1 (en) | 2016-09-09 | 2018-03-15 | Incyte Corporation | Pyrazolopyridine derivatives as hpk1 modulators and uses thereof for the treatment of cancer |
| CN115819417A (zh) | 2016-09-09 | 2023-03-21 | 因赛特公司 | 作为hpk1调节剂的吡唑并吡啶衍生物及其用于治疗癌症的用途 |
| US20180072741A1 (en) | 2016-09-09 | 2018-03-15 | Incyte Corporation | Pyrazolopyrimidine compounds and uses thereof |
| US10280164B2 (en) | 2016-09-09 | 2019-05-07 | Incyte Corporation | Pyrazolopyridone compounds and uses thereof |
| WO2018152220A1 (en) | 2017-02-15 | 2018-08-23 | Incyte Corporation | Pyrazolopyridine compounds and uses thereof |
| GB201703907D0 (en) * | 2017-03-10 | 2017-04-26 | Proximagen Ltd | Novel therapies for cancer |
| US10722495B2 (en) | 2017-09-08 | 2020-07-28 | Incyte Corporation | Cyanoindazole compounds and uses thereof |
| CN109553604B (zh) * | 2017-09-25 | 2021-08-27 | 盛世泰科生物医药技术(苏州)有限公司 | 4-氨基嘧啶衍生物作cxcr4抑制剂及其应用 |
| US10745388B2 (en) | 2018-02-20 | 2020-08-18 | Incyte Corporation | Indazole compounds and uses thereof |
| US10752635B2 (en) | 2018-02-20 | 2020-08-25 | Incyte Corporation | Indazole compounds and uses thereof |
| EP3755703B1 (en) | 2018-02-20 | 2022-05-04 | Incyte Corporation | N-(phenyl)-2-(phenyl)pyrimidine-4-carboxamide derivatives and related compounds as hpk1 inhibitors for treating cancer |
| MX2020009531A (es) | 2018-03-14 | 2020-10-05 | Janssen Sciences Ireland Unlimited Co | Regimen posologico del modulador del ensamblaje de la capside. |
| US11299473B2 (en) | 2018-04-13 | 2022-04-12 | Incyte Corporation | Benzimidazole and indole compounds and uses thereof |
| CN112839648B (zh) | 2018-06-07 | 2025-04-04 | 达萨玛治疗公司 | Sarm1抑制剂 |
| US10899755B2 (en) | 2018-08-08 | 2021-01-26 | Incyte Corporation | Benzothiazole compounds and uses thereof |
| US10548889B1 (en) | 2018-08-31 | 2020-02-04 | X4 Pharmaceuticals, Inc. | Compositions of CXCR4 inhibitors and methods of preparation and use |
| WO2020068729A1 (en) | 2018-09-25 | 2020-04-02 | Incyte Corporation | Pyrazolo[4,3-d]pyrimidine compounds as alk2 abd/or fgfr modulators |
| MX2021006915A (es) | 2018-12-12 | 2021-08-24 | Chemocentryx Inc | Inhibidores de cxcr7 para el tratamiento de cancer. |
| EP3897670A4 (en) | 2018-12-19 | 2022-09-07 | Disarm Therapeutics, Inc. | MRSA1 INHIBITORS IN COMBINATION WITH NEUROPROTECTIVE AGENTS |
| WO2020169784A1 (en) | 2019-02-22 | 2020-08-27 | Janssen Sciences Ireland Unlimited Company | Amide derivatives useful in the treatment of hbv infection or hbv-induced diseases |
| WO2020222190A1 (en) | 2019-05-02 | 2020-11-05 | Proximagen, Llc | Crystalline form of 6-[4-[1 -(propan-2-yl)piperidin-4-yl]-1,4-diazepan-1 -yl]-n-(pyrdin-4-yl)pyridine-2-carboxamide |
| WO2020222189A1 (en) | 2019-05-02 | 2020-11-05 | Proximagen, Llc | Crystalline form of 6-[4-[1-(propan-2-yl)piperidin-4-yl]-1,4-diazepan-1-yl]-n-(pyrdin-4-yl)pyridine-2-carboxamide |
| AR119732A1 (es) | 2019-05-06 | 2022-01-05 | Janssen Sciences Ireland Unlimited Co | Derivados de amida útiles en el tratamiento de la infección por vhb o de enfermedades inducidas por vhb |
| AR119009A1 (es) | 2019-05-29 | 2021-11-17 | Syngenta Crop Protection Ag | Derivados de alcoxipiridina y alcoxipirimidina microbicidas |
| US11969522B2 (en) * | 2019-07-08 | 2024-04-30 | The Board Of Regents Of The University Of Texas System | Use of immune modulators to improve nerve regeneration |
| BR112022002059A2 (pt) | 2019-08-06 | 2022-06-07 | Incyte Corp | Formas sólidas de um inibidor de hpk1 |
| CA3171250A1 (en) | 2020-03-10 | 2021-09-16 | E. Lynne KELLEY | Methods for treating neutropenia |
| WO2021261601A1 (ja) | 2020-06-26 | 2021-12-30 | ラクオリア創薬株式会社 | レチノイドとがん治療薬との併用療法が有効ながん患者の選択方法およびレチノイドとがん治療薬との併用医薬 |
| CN113845439B (zh) * | 2021-10-11 | 2024-02-09 | 杭州师范大学 | 双苄酰胺类cxcr4拮抗剂及其制备和应用 |
Family Cites Families (43)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5047406A (en) | 1989-12-06 | 1991-09-10 | Warner-Lambert Co. | Substituted cyclohexanols as central nervous system agents |
| GB9300194D0 (en) * | 1993-01-06 | 1993-03-03 | Wyeth John & Brother Ltd | Piperazine derivatives |
| US6506770B1 (en) | 1996-06-06 | 2003-01-14 | Anormed, Inc. | Antiviral compounds |
| AU5522498A (en) | 1996-12-13 | 1998-07-03 | Merck & Co., Inc. | Substituted aryl piperazines as modulators of chemokine receptor activity |
| FR2769913B1 (fr) | 1997-10-16 | 2000-03-10 | Pf Medicament | Nouveaux derives cyclohexaniques difonctionnalises en 1, 4, leur preparation et leur application therapeutique humaine |
| SE9902987D0 (sv) * | 1999-08-24 | 1999-08-24 | Astra Pharma Prod | Novel compounds |
| EP1294704A1 (en) | 2000-06-29 | 2003-03-26 | Abbott Laboratories | Aryl phenylheterocyclyl sulfide derivatives and their use as cell adhesion-inhibiting anti-inflammatory and immune-suppressive agents |
| AR036366A1 (es) | 2001-08-29 | 2004-09-01 | Schering Corp | Derivados de piperidina utiles como antagonistas de ccr5, composiciones farmaceuticas, el uso de dichos derivados para la fabricación de un medicamento y un kit |
| WO2003082855A1 (en) * | 2002-03-28 | 2003-10-09 | Kyowa Hakko Kogyo Co., Ltd. | Anti-inflammatory agent |
| EP1571146A4 (en) | 2002-12-10 | 2010-09-01 | Ono Pharmaceutical Co | NITROGENIC HETEROCYCLIC COMPOUNDS AND THEIR MEDICAL USE |
| GB0308466D0 (en) * | 2003-04-11 | 2003-05-21 | Novartis Ag | Organic compounds |
| FR2854633B1 (fr) | 2003-05-07 | 2005-06-24 | Sanofi Synthelabo | Derives de piperidinyl-et piperazinyl-alkylcarbamates, leur preparation et leur application en therapeutique |
| US7498346B2 (en) | 2003-12-11 | 2009-03-03 | Genzyme Corporation | Chemokine receptor binding compounds |
| EP1708703A4 (en) | 2003-12-11 | 2008-04-09 | Anormed Inc | CHEMOKIN RECEPTOR BINDING COMPOUNDS |
| WO2006071875A1 (en) * | 2004-12-29 | 2006-07-06 | Millennium Pharmaceuticals, Inc. | Compounds useful as chemokine receptor antagonists |
| WO2006071958A1 (en) | 2004-12-29 | 2006-07-06 | Millennium Pharmaceuticals, Inc. | Compounds useful as chemokine receptor antagonists |
| MX2007010067A (es) | 2005-02-16 | 2007-12-07 | Schering Corp | Compuestos heterociclicos novedosos sustituidos con piridina o fenilo con actividad antagonista de cxcr3. |
| JP2008530218A (ja) | 2005-02-16 | 2008-08-07 | シェーリング コーポレイション | Ｃｘｃｒ３アンタゴニスト活性を有する、ピリジルおよびフェニルで置換されたピペラジン−ピペリジン |
| MX2007010068A (es) | 2005-02-16 | 2007-10-10 | Schering Corp | Piperazino-piperidinas con actividad antagonista de cxcr3. |
| PE20061164A1 (es) * | 2005-02-16 | 2006-10-27 | Schering Corp | Piperazin-piperidinas sustituidas con pirazinilo con actividad antagonista de cxcr3 |
| EP1853583B1 (en) | 2005-02-16 | 2011-09-07 | Schering Corporation | Amine-linked pyridyl and phenyl substituted piperazine-piperidines with cxcr3 antagonist activity |
| US20060235028A1 (en) | 2005-04-14 | 2006-10-19 | Li James J | Inhibitors of 11-beta hydroxysteroid dehydrogenase type I |
| WO2006130426A2 (en) | 2005-05-27 | 2006-12-07 | Kemia, Inc. | Modulators of ccr-5 activity |
| GB0525957D0 (en) | 2005-12-21 | 2006-02-01 | Astrazeneca Ab | Methods |
| CN101460482B (zh) | 2006-03-21 | 2013-03-27 | 默沙东公司 | 具有cxcr3拮抗剂活性的杂环取代的吡啶化合物 |
| EP1849781A1 (en) | 2006-04-28 | 2007-10-31 | Laboratorios del Dr. Esteve S.A. | Substituted 3-Amino-4-hydroxy pyrrolidines compounds, their preparation and use as medicaments |
| MX2009000577A (es) * | 2006-07-14 | 2009-03-09 | Schering Corp | Compuestos de piperazina sustituida heterociclica con actividad antagonista de cxcr3. |
| JP2008050220A (ja) * | 2006-08-25 | 2008-03-06 | Hitachi Metals Ltd | 六方晶ｚ型フェライト焼結体およびその製造方法 |
| JP5606736B2 (ja) | 2006-09-02 | 2014-10-15 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング | 反応性メソゲンを配向するための粒子ビーム法 |
| PL2066662T3 (pl) | 2006-09-21 | 2013-05-31 | Kyorin Seiyaku Kk | Inhibitory hydrolaz serynowych |
| CN101534824A (zh) | 2006-11-17 | 2009-09-16 | 艾博特公司 | 作为化学活素受体拮抗剂的氨基吡咯烷 |
| AR064609A1 (es) * | 2006-12-22 | 2009-04-15 | Schering Corp | Piperazinas sustituidas, composiciones farmaceuticas que las comprenden y su uso en el tratamiento de enfermedades mediadas por el receptor de quimiocinas cxcr3. |
| AU2008210455A1 (en) | 2007-01-31 | 2008-08-07 | Vertex Pharmaceuticals Incorporated | 2-aminopyridine derivatives useful as kinase inhibitors |
| WO2008121065A1 (en) | 2007-03-30 | 2008-10-09 | Astrazeneca Ab | Novel pyrrolidine derivatives as antagonists of the chemokine receptor |
| CA2707989A1 (en) * | 2007-12-07 | 2009-06-11 | Novartis Ag | Pyrazole derivatives and use thereof as inhibitors of cyclin dependent kinases |
| CA2742515C (en) * | 2008-11-04 | 2017-07-11 | Chemocentryx, Inc. | 1,4-diazepane modulators of cxcr7 |
| CN102471339A (zh) * | 2009-07-15 | 2012-05-23 | 雅培制药有限公司 | 激酶的吡咯并吡啶抑制剂 |
| KR20110123657A (ko) * | 2010-05-07 | 2011-11-15 | 에스케이케미칼주식회사 | 피콜린아마이드 및 피리미딘-4-카복사미드 화합물, 이의 제조방법 및 이를 함유하는 약제학적 조성물 |
| WO2012047339A2 (en) | 2010-06-28 | 2012-04-12 | The General Hospital Corporation | Anti-cxcr4 as a sensitizer to cancer therapeutics |
| GB201017345D0 (en) * | 2010-10-14 | 2010-11-24 | Proximagen Ltd | Receptor antagonists |
| AU2016242118B2 (en) | 2015-04-02 | 2021-07-08 | Proximagen, Llc | Novel therapies for cancer |
| GB201604213D0 (en) | 2016-03-11 | 2016-04-27 | Proximagen Ltd | Drug combination and its use in therapy |
| GB201703907D0 (en) | 2017-03-10 | 2017-04-26 | Proximagen Ltd | Novel therapies for cancer |
-
2010
- 2010-10-14 GB GB201017345A patent/GB201017345D0/en not_active Ceased
-
2011
- 2011-10-13 PL PL11773227T patent/PL2627649T3/pl unknown
- 2011-10-13 CN CN201180049854.3A patent/CN103282360B/zh not_active Expired - Fee Related
- 2011-10-13 PL PL15158267T patent/PL2927224T3/pl unknown
- 2011-10-13 JP JP2013533225A patent/JP5881718B2/ja not_active Expired - Fee Related
- 2011-10-13 US US13/878,968 patent/US9353086B2/en not_active Expired - Fee Related
- 2011-10-13 ES ES11773227.1T patent/ES2536281T3/es active Active
- 2011-10-13 DK DK11773227.1T patent/DK2627649T3/en active
- 2011-10-13 WO PCT/EP2011/067946 patent/WO2012049277A1/en not_active Ceased
- 2011-10-13 DK DK15158267.3T patent/DK2927224T3/en active
- 2011-10-13 EP EP15158267.3A patent/EP2927224B8/en active Active
- 2011-10-13 AU AU2011315498A patent/AU2011315498C1/en not_active Ceased
- 2011-10-13 ES ES15158267T patent/ES2699470T3/es active Active
- 2011-10-13 EP EP11773227.1A patent/EP2627649B1/en active Active
- 2011-10-13 PT PT117732271T patent/PT2627649E/pt unknown
- 2011-10-13 BR BR112013009036-7A patent/BR112013009036B1/pt not_active IP Right Cessation
- 2011-10-13 SG SG2013027800A patent/SG189387A1/en unknown
- 2011-10-13 CA CA2814419A patent/CA2814419C/en active Active
- 2011-10-13 PT PT15158267T patent/PT2927224T/pt unknown
-
2013
- 2013-04-04 IL IL225550A patent/IL225550A/en active IP Right Grant
-
2015
- 2015-09-14 US US14/852,835 patent/US20160046606A1/en not_active Abandoned
- 2015-09-28 JP JP2015189271A patent/JP6348891B2/ja not_active Expired - Fee Related
-
2017
- 2017-04-26 US US15/497,324 patent/US10155761B2/en active Active
-
2018
- 2018-10-22 US US16/167,084 patent/US10995091B2/en not_active Expired - Fee Related
-
2021
- 2021-03-02 US US17/190,266 patent/US20220348577A1/en not_active Abandoned
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2013539777A5 (https=) | ||
| JP6348891B2 (ja) | Ｃｘｃｒ４受容体アンタゴニスト | |
| JP6517976B2 (ja) | 炎症性障害の治療のための化合物及びその医薬組成物 | |
| KR102722493B1 (ko) | Mdm2-p53 억제제로서의 스피로[3h-인돌-3,2'-피롤리딘]-2(1h)-온 화합물 및 유도체 | |
| EP3010922B1 (en) | Novel compounds and pharmaceutical compositions thereof for the treatment of inflammatory disorders | |
| BR112019018991A2 (pt) | compostos e composições para tratar distúrbios hematológicos | |
| JP2016519096A5 (https=) | ||
| JP2016507548A (ja) | ムスカリンｍ４受容体アゴニストとしてのピペリジン−１−イル及びアゼピン−１−イルカルボキシレート | |
| ES2260316T3 (es) | Derivados de quinazolina y quinolina 4-sustituidos que inhiben la farnesil transferasa. | |
| KR20170020522A (ko) | 인돌린-2-온 또는 피롤로-피리딘-2-온 유도체 | |
| JP2018507235A (ja) | ステロール調節エレメント結合タンパク質（ｓｒｅｂｐ）阻害剤 | |
| AU2023261964A1 (en) | Compounds for inhibiting kif18a | |
| JP2018532788A5 (https=) | ||
| TW202313048A (zh) | 組合療法 | |
| JP7716777B2 (ja) | 窒素含有多環式縮合環系化合物、その医薬組成物、製造方法及び用途 | |
| RU2015120217A (ru) | Замещенные 1,6-нафтиридины | |
| EP3585365A1 (en) | Combination of atr kinase inhibitors with parp inhibitors | |
| TW202400589A (zh) | 四氫異喹啉異雙功能ｂｃｌ—ｘｌ降解劑 | |
| ES2328225T3 (es) | Derivados benzoheterociclicos inhibidores de la farnesil-transferasa. | |
| WO2018195471A1 (en) | Syk inhibitors in combination with hypomethylating agents | |
| RU2833004C2 (ru) | Производные гетероциклического пиразола как ингибиторы рецепторной тирозикиназы типа III | |
| AU2018447240A1 (en) | Indazole kinase inhibitor and use thereof | |
| JP2018111688A (ja) | 医薬組成物 | |
| RU2022107496A (ru) | Производные гетероциклического пиразола как ингибиторы рецепторной тирозикиназы типа III | |
| WO2025181828A1 (en) | Triamino pyrimidine compounds as cdk7 inhibitors and methods thereof |