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 |
|---|---|---|---|
| GB201017345A GB201017345D0 (en) | 2010-10-14 | 2010-10-14 | Receptor antagonists |
| GB1017345.8 | 2010-10-14 | ||
| 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) | EP2627649B1 (https=) |
| JP (2) | JP5881718B2 (https=) |
| CN (1) | CN103282360B (https=) |
| AU (1) | AU2011315498C1 (https=) |
| BR (1) | BR112013009036B1 (https=) |
| CA (1) | CA2814419C (https=) |
| DK (2) | DK2927224T3 (https=) |
| ES (2) | ES2699470T3 (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 |
| WO2013096744A1 (en) | 2011-12-21 | 2013-06-27 | Novira Therapeutics, Inc. | Hepatitis b antiviral agents |
| EA038942B1 (ru) | 2012-08-28 | 2021-11-12 | Янссен Сайенсиз Айрлэнд Юси | Сульфамоил-ариламиды и их применение в качестве лекарственных препаратов для лечения гепатита b |
| JP6272897B2 (ja) | 2012-11-29 | 2018-01-31 | ケモセントリックス，インコーポレイティド | Ｃｘｃｒ７アンタゴニスト |
| JP6321673B2 (ja) * | 2012-12-20 | 2018-05-09 | ルゥ チーン−ビン | 放射線と組み合わせて使用するための放射線増感剤化合物 |
| EP2746260A1 (en) | 2012-12-21 | 2014-06-25 | Basf Se | Substituted [1,2,4]triazole and imidazole compounds |
| EP2746259A1 (en) | 2012-12-21 | 2014-06-25 | Basf Se | Substituted [1,2,4]triazole and imidazole compounds |
| HUE034820T2 (en) | 2013-02-28 | 2018-02-28 | Janssen Sciences Ireland Uc | Sulphamoyl arylamides and their use as medicaments for the treatment of hepatitis B |
| EA027068B1 (ru) | 2013-04-03 | 2017-06-30 | Янссен Сайенсиз Айрлэнд Юси | Производные n-фенилкарбоксамида и их применение в качестве лекарственных препаратов для лечения гепатита b |
| TWI651300B (zh) | 2013-05-17 | 2019-02-21 | 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 |
| DK3024819T3 (en) | 2013-07-25 | 2018-06-06 | Janssen Sciences Ireland Uc | GLYOXAMIDE-SUBSTITUTED PYRROLAMIDE DERIVATIVES AND THE USE THEREOF AS MEDICINES FOR TREATING HEPATITIS B |
| KR102290189B1 (ko) | 2013-10-23 | 2021-08-17 | 얀센 사이언시즈 아일랜드 언리미티드 컴퍼니 | 카르복스아미드 유도체 및 ｂ형 간염 치료용 의약으로서의 이의 용도 |
| 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 |
| JP6553059B2 (ja) | 2014-02-05 | 2019-07-31 | ノヴィラ・セラピューティクス・インコーポレイテッド | Ｈｂｖ感染の治療のための併用療法 |
| WO2015118057A1 (en) | 2014-02-06 | 2015-08-13 | Janssen Sciences Ireland Uc | Sulphamoylpyrrolamide derivatives and the use thereof as medicaments for the treatment of hepatitis b |
| EP3271019A1 (en) | 2015-03-19 | 2018-01-24 | Novira Therapeutics Inc. | Azocane and azonane derivatives and methods of treating hepatitis b infections |
| US11311552B2 (en) | 2015-04-02 | 2022-04-26 | Proximagen, Llc | 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 |
| WO2017011517A1 (en) | 2015-07-16 | 2017-01-19 | Emory University | Bis-amines, compositions, and uses related to cxcr4 inhibition |
| HK1259410A1 (zh) | 2015-09-29 | 2019-11-29 | 诺维拉治疗公司 | 乙型肝炎抗病毒剂的晶体形式 |
| CN109069426B (zh) | 2015-12-14 | 2021-10-29 | X4 制药有限公司 | 治疗癌症的方法 |
| WO2017106332A1 (en) | 2015-12-14 | 2017-06-22 | X4 Pharmaceuticals, Inc. | Methods for treating cancer |
| PL3393468T3 (pl) | 2015-12-22 | 2023-01-23 | X4 Pharmaceuticals, Inc. | Metody leczenia niedoboru odporności |
| GB201604213D0 (en) | 2016-03-11 | 2016-04-27 | Proximagen Ltd | Drug combination and its use in therapy |
| US11337969B2 (en) | 2016-04-08 | 2022-05-24 | X4 Pharmaceuticals, Inc. | Methods for treating cancer |
| SG10202011827YA (en) | 2016-04-15 | 2021-01-28 | Novira Therapeutics Inc | 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 |
| WO2017223243A1 (en) | 2016-06-21 | 2017-12-28 | 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 |
| US10280164B2 (en) | 2016-09-09 | 2019-05-07 | Incyte Corporation | Pyrazolopyridone compounds and uses thereof |
| UA125650C2 (uk) | 2016-09-09 | 2022-05-11 | Інсайт Корпорейшн | Регулятори нрk1 на основі похідних піразолопіридину та їх застосування для лікування раку |
| TW201811799A (zh) | 2016-09-09 | 2018-04-01 | 美商英塞特公司 | 吡唑并嘧啶化合物及其用途 |
| US20180228786A1 (en) | 2017-02-15 | 2018-08-16 | 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 |
| US10800761B2 (en) | 2018-02-20 | 2020-10-13 | Incyte Corporation | Carboxamide compounds and uses thereof |
| WO2019164847A1 (en) | 2018-02-20 | 2019-08-29 | Incyte Corporation | Indazole compounds and uses thereof |
| CA3090125A1 (en) | 2018-03-14 | 2019-09-19 | Janssen Sciences Ireland Unlimited Company | Capsid assembly modulator dosing regimen |
| US11299473B2 (en) | 2018-04-13 | 2022-04-12 | Incyte Corporation | Benzimidazole and indole compounds and uses thereof |
| US12448374B2 (en) | 2018-06-07 | 2025-10-21 | Disarm Therapeutics, Inc. | Inhibitors of SARM1 |
| 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 |
| ES2973117T3 (es) | 2018-09-25 | 2024-06-18 | Incyte Corp | Compuestos de pirazolo[4,3-d]pirimidina como moduladores de ALK2 y/o FGFR |
| MX2021006915A (es) | 2018-12-12 | 2021-08-24 | Chemocentryx Inc | Inhibidores de cxcr7 para el tratamiento de cancer. |
| WO2020132045A1 (en) | 2018-12-19 | 2020-06-25 | Disarm Therapeutics, Inc. | Inhibitors of sarm1 in combination with neuroprotective agents |
| MX2021010145A (es) | 2019-02-22 | 2021-09-14 | Janssen Sciences Ireland Unlimited Co | Derivados de amida utiles en el tratamiento de una infeccion por vhb o de enfermedades inducidas por vhb. |
| 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 |
| MA55879A (fr) | 2019-05-06 | 2022-03-16 | Janssen Sciences Ireland Unlimited Co | Dérivés d'amide utiles dans le traitement d'une infection par le virus de l'hépatite b ou de maladies induites par le virus de l'hépatite b |
| AR119009A1 (es) * | 2019-05-29 | 2021-11-17 | Syngenta Crop Protection Ag | Derivados de alcoxipiridina y alcoxipirimidina microbicidas |
| BR112022000254A2 (pt) * | 2019-07-08 | 2022-03-15 | Edward Keefer | Uso de moduladores imunológicos para melhorar a regeneração nervosa |
| MX2022001562A (es) | 2019-08-06 | 2022-04-26 | Incyte Corp | Formas solidas de un inhibidor de la cinasa 1 del progenitor hematopoyetico (hpk1). |
| CA3171250A1 (en) | 2020-03-10 | 2021-09-16 | E. Lynne KELLEY | Methods for treating neutropenia |
| EP4173639A4 (en) | 2020-06-26 | 2024-03-13 | RaQualia Pharma Inc. | METHOD FOR SELECTING A CANCER PATIENT FOR WHICH COMBINATION THERAPY OF A RETINOID AND A CANCER TREATMENT AGENT WILL BE EFFECTIVE, AND COMBINATION DRUG OF A RETINOID AND A CANCER TREATMENT AGENT |
| 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 |
| NZ523445A (en) | 2000-06-29 | 2004-10-29 | Abbott Lab | 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 |
| JPWO2003082855A1 (ja) * | 2002-03-28 | 2005-08-04 | 協和醗酵工業株式会社 | 抗炎症剤 |
| WO2004052862A1 (ja) * | 2002-12-10 | 2004-06-24 | Ono Pharmaceutical Co., Ltd. | 含窒素複素環化合物およびその医薬用途 |
| 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 |
| US7635698B2 (en) | 2004-12-29 | 2009-12-22 | Millennium Pharmaceuticals, Inc. | Compounds useful as chemokine receptor antagonists |
| US7880002B2 (en) * | 2004-12-29 | 2011-02-01 | Millennium Pharmaceuticals, Inc. | Substituted piperazinyl-pyrrolidine compounds useful as chemokine receptor antagonists |
| BRPI0607946A2 (pt) | 2005-02-16 | 2009-10-20 | Schering Corp | piperazina-piperidinas substituìdas por pirazinila com atividade de antagonista cxcr3 |
| AU2006214378A1 (en) | 2005-02-16 | 2006-08-24 | Pharmacopeia, Inc. | Pyridyl and phenyl substituted piperazine-piperidines with CXCR3 antagonist activity |
| CN101146793A (zh) | 2005-02-16 | 2008-03-19 | 先灵公司 | 具有cxcr3拮抗剂活性的新的杂环取代了的吡啶或苯基化合物 |
| EP1853583B1 (en) | 2005-02-16 | 2011-09-07 | Schering Corporation | Amine-linked pyridyl and phenyl substituted piperazine-piperidines with cxcr3 antagonist activity |
| CA2598489A1 (en) | 2005-02-16 | 2006-08-24 | Schering Corporation | Piperazine-piperidines with cxcr3 antagonist activity |
| EP2527337A1 (en) | 2005-04-14 | 2012-11-28 | Bristol-Myers Squibb Company | 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 |
| WO2008028553A1 (en) | 2006-09-02 | 2008-03-13 | Merck Patent Gmbh | Particle beam process for the alignment of reactive mesogens |
| PL2066662T3 (pl) | 2006-09-21 | 2013-05-31 | Kyorin Seiyaku Kk | Inhibitory hydrolaz serynowych |
| CA2669917A1 (en) | 2006-11-17 | 2008-05-22 | Dawn M. George | Aminopyrrolidines as chemokine receptor antagonists |
| 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 |
| MX2011004490A (es) * | 2008-11-04 | 2011-07-20 | Chemocentryx Inc | Moduladores de cxcr7. |
| CA2767089A1 (en) * | 2009-07-15 | 2011-01-20 | Abbott Laboratories | Pyrrolopyridine inhibitors of kinases |
| KR20110123657A (ko) * | 2010-05-07 | 2011-11-15 | 에스케이케미칼주식회사 | 피콜린아마이드 및 피리미딘-4-카복사미드 화합물, 이의 제조방법 및 이를 함유하는 약제학적 조성물 |
| US9155723B2 (en) | 2010-06-28 | 2015-10-13 | The General Hospital Corporation | Anti-CXCR4 as a sensitizer to cancer therapeutics |
| GB201017345D0 (en) | 2010-10-14 | 2010-11-24 | Proximagen Ltd | Receptor antagonists |
| US11311552B2 (en) | 2015-04-02 | 2022-04-26 | Proximagen, Llc | 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 EP EP11773227.1A patent/EP2627649B1/en active Active
- 2011-10-13 EP EP15158267.3A patent/EP2927224B8/en active Active
- 2011-10-13 ES ES15158267T patent/ES2699470T3/es active Active
- 2011-10-13 CA CA2814419A patent/CA2814419C/en active Active
- 2011-10-13 PL PL11773227T patent/PL2627649T3/pl unknown
- 2011-10-13 DK DK15158267.3T patent/DK2927224T3/en active
- 2011-10-13 AU AU2011315498A patent/AU2011315498C1/en not_active Ceased
- 2011-10-13 JP JP2013533225A patent/JP5881718B2/ja not_active Expired - Fee Related
- 2011-10-13 WO PCT/EP2011/067946 patent/WO2012049277A1/en not_active Ceased
- 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 PL PL15158267T patent/PL2927224T3/pl unknown
- 2011-10-13 SG SG2013027800A patent/SG189387A1/en unknown
- 2011-10-13 PT PT117732271T patent/PT2627649E/pt unknown
- 2011-10-13 DK DK11773227.1T patent/DK2627649T3/en active
- 2011-10-13 PT PT15158267T patent/PT2927224T/pt unknown
- 2011-10-13 BR BR112013009036-7A patent/BR112013009036B1/pt not_active IP Right Cessation
- 2011-10-13 CN CN201180049854.3A patent/CN103282360B/zh not_active Expired - Fee Related
-
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 | |
| 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 | |
| JPWO2021041276A5 (https=) |