RU2352567C2 - Производные тетрагидрохинолина, демонстрирующие защитное от вич-инфекции действие - Google Patents
Производные тетрагидрохинолина, демонстрирующие защитное от вич-инфекции действие Download PDFInfo
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- RU2352567C2 RU2352567C2 RU2007106780/04A RU2007106780A RU2352567C2 RU 2352567 C2 RU2352567 C2 RU 2352567C2 RU 2007106780/04 A RU2007106780/04 A RU 2007106780/04A RU 2007106780 A RU2007106780 A RU 2007106780A RU 2352567 C2 RU2352567 C2 RU 2352567C2
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- Prior art keywords
- methyl
- alkyl
- cycloalkyl
- amino
- het
- Prior art date
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- 230000000694 effects Effects 0.000 title claims abstract 4
- 150000001875 compounds Chemical class 0.000 claims abstract 82
- 125000000217 alkyl group Chemical group 0.000 claims abstract 64
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract 50
- 125000003342 alkenyl group Chemical group 0.000 claims abstract 31
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 20
- 125000005842 heteroatom Chemical group 0.000 claims abstract 18
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract 13
- 125000002947 alkylene group Chemical group 0.000 claims abstract 11
- 229910052736 halogen Inorganic materials 0.000 claims abstract 11
- 150000002367 halogens Chemical class 0.000 claims abstract 11
- 238000000034 method Methods 0.000 claims abstract 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 10
- 125000000392 cycloalkenyl group Chemical group 0.000 claims abstract 9
- 125000002993 cycloalkylene group Chemical group 0.000 claims abstract 9
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract 9
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract 9
- 125000002950 monocyclic group Chemical group 0.000 claims abstract 9
- 125000001624 naphthyl group Chemical group 0.000 claims abstract 9
- 125000003367 polycyclic group Chemical group 0.000 claims abstract 9
- 150000003839 salts Chemical class 0.000 claims abstract 5
- 208000031886 HIV Infections Diseases 0.000 claims abstract 4
- 208000037357 HIV infectious disease Diseases 0.000 claims abstract 4
- 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 claims abstract 4
- 102100031650 C-X-C chemokine receptor type 4 Human genes 0.000 claims abstract 3
- 102000009410 Chemokine receptor Human genes 0.000 claims abstract 3
- 108050000299 Chemokine receptor Proteins 0.000 claims abstract 3
- 101000922348 Homo sapiens C-X-C chemokine receptor type 4 Proteins 0.000 claims abstract 3
- 150000003973 alkyl amines Chemical group 0.000 claims abstract 2
- 150000001412 amines Chemical group 0.000 claims abstract 2
- 125000000304 alkynyl group Chemical group 0.000 claims 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 8
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims 6
- -1 methyl-1-piperazinyl Chemical group 0.000 claims 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 5
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 4
- 150000002148 esters Chemical class 0.000 claims 4
- 238000011282 treatment Methods 0.000 claims 4
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 3
- 230000015572 biosynthetic process Effects 0.000 claims 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 3
- 230000002265 prevention Effects 0.000 claims 3
- 238000006722 reduction reaction Methods 0.000 claims 3
- ARAOGFXYEZOODJ-HMTLIYDFSA-N 1-[5-(4-methylpiperazin-1-yl)-2-[[methyl-[(8s)-5,6,7,8-tetrahydroquinolin-8-yl]amino]methyl]imidazo[1,2-a]pyridin-3-yl]propan-1-ol Chemical compound N12C(C(O)CC)=C(CN(C)[C@@H]3C4=NC=CC=C4CCC3)N=C2C=CC=C1N1CCN(C)CC1 ARAOGFXYEZOODJ-HMTLIYDFSA-N 0.000 claims 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- OMQGJJGRSZIQQJ-QHCPKHFHSA-N [2-[[cyclopropylmethyl-[(8s)-5,6,7,8-tetrahydroquinolin-8-yl]amino]methyl]-5-(4-methylpiperazin-1-yl)imidazo[1,2-a]pyridin-3-yl]methanol Chemical compound C1CN(C)CCN1C1=CC=CC2=NC(CN(CC3CC3)[C@@H]3C4=NC=CC=C4CCC3)=C(CO)N12 OMQGJJGRSZIQQJ-QHCPKHFHSA-N 0.000 claims 2
- UAWUQXPDPOEYPP-VWNXMTODSA-N [2-[[cyclopropylmethyl-[(8s)-5,6,7,8-tetrahydroquinolin-8-yl]amino]methyl]-5-[(3r)-3-(dimethylamino)pyrrolidin-1-yl]imidazo[1,2-a]pyridin-3-yl]methanol Chemical compound C1[C@H](N(C)C)CCN1C1=CC=CC2=NC(CN(CC3CC3)[C@@H]3C4=NC=CC=C4CCC3)=C(CO)N12 UAWUQXPDPOEYPP-VWNXMTODSA-N 0.000 claims 2
- VCFMOLJXJJHRDI-NRFANRHFSA-N [2-[[ethyl-[(8s)-5,6,7,8-tetrahydroquinolin-8-yl]amino]methyl]-5-(4-methylpiperazin-1-yl)imidazo[1,2-a]pyridin-3-yl]methanol Chemical compound CCN([C@@H]1C2=NC=CC=C2CCC1)CC(=C(N12)CO)N=C1C=CC=C2N1CCN(C)CC1 VCFMOLJXJJHRDI-NRFANRHFSA-N 0.000 claims 2
- OSKWWXWMHXCEBW-QFIPXVFZSA-N [2-[[methyl-[(8s)-5,6,7,8-tetrahydroquinolin-8-yl]amino]methyl]-5-(4-propan-2-ylpiperazin-1-yl)imidazo[1,2-a]pyridin-3-yl]methanol Chemical compound C1CN(C(C)C)CCN1C1=CC=CC2=NC(CN(C)[C@@H]3C4=NC=CC=C4CCC3)=C(CO)N12 OSKWWXWMHXCEBW-QFIPXVFZSA-N 0.000 claims 2
- ITOXKJBXAWDJBA-NRFANRHFSA-N [5-(4-ethylpiperazin-1-yl)-2-[[methyl-[(8s)-5,6,7,8-tetrahydroquinolin-8-yl]amino]methyl]imidazo[1,2-a]pyridin-3-yl]methanol Chemical compound C1CN(CC)CCN1C1=CC=CC2=NC(CN(C)[C@@H]3C4=NC=CC=C4CCC3)=C(CO)N12 ITOXKJBXAWDJBA-NRFANRHFSA-N 0.000 claims 2
- QUDMHFVRKBVGBY-UHFFFAOYSA-N [5-(4-methylpiperazin-1-yl)-2-[[methyl(5,6,7,8-tetrahydroquinolin-8-yl)amino]methyl]imidazo[1,2-a]pyridin-3-yl]methanol Chemical compound C1CCC2=CC=CN=C2C1N(C)CC(=C(N12)CO)N=C1C=CC=C2N1CCN(C)CC1 QUDMHFVRKBVGBY-UHFFFAOYSA-N 0.000 claims 2
- NJBRZHKNUUOYBN-QFIPXVFZSA-N [5-(4-methylpiperazin-1-yl)-2-[[propan-2-yl-[(8s)-5,6,7,8-tetrahydroquinolin-8-yl]amino]methyl]imidazo[1,2-a]pyridin-3-yl]methanol Chemical compound CC(C)N([C@@H]1C2=NC=CC=C2CCC1)CC(=C(N12)CO)N=C1C=CC=C2N1CCN(C)CC1 NJBRZHKNUUOYBN-QFIPXVFZSA-N 0.000 claims 2
- HGWYUSJZJFIGOG-QFIPXVFZSA-N [5-(4-methylpiperazin-1-yl)-2-[[propyl-[(8s)-5,6,7,8-tetrahydroquinolin-8-yl]amino]methyl]imidazo[1,2-a]pyridin-3-yl]methanol Chemical compound CCCN([C@@H]1C2=NC=CC=C2CCC1)CC(=C(N12)CO)N=C1C=CC=C2N1CCN(C)CC1 HGWYUSJZJFIGOG-QFIPXVFZSA-N 0.000 claims 2
- CZWUXDXQKLXFBS-CTNGQTDRSA-N [5-[(3r)-3-(dimethylamino)pyrrolidin-1-yl]-2-[[methyl-[(8s)-5,6,7,8-tetrahydroquinolin-8-yl]amino]methyl]imidazo[1,2-a]pyridin-3-yl]methanol Chemical compound C1[C@H](N(C)C)CCN1C1=CC=CC2=NC(CN(C)[C@@H]3C4=NC=CC=C4CCC3)=C(CO)N12 CZWUXDXQKLXFBS-CTNGQTDRSA-N 0.000 claims 2
- FMKQGTBQHSFAOK-GGAORHGYSA-N [5-[(3r)-3-(dimethylamino)pyrrolidin-1-yl]-2-[[propyl-[(8s)-5,6,7,8-tetrahydroquinolin-8-yl]amino]methyl]imidazo[1,2-a]pyridin-3-yl]methanol Chemical compound CCCN([C@@H]1C2=NC=CC=C2CCC1)CC(=C(N12)CO)N=C1C=CC=C2N1CC[C@@H](N(C)C)C1 FMKQGTBQHSFAOK-GGAORHGYSA-N 0.000 claims 2
- LJZYHHSTUCZUCV-QUCCMNQESA-N [5-[(3r)-3-(methylamino)pyrrolidin-1-yl]-2-[[methyl-[(8s)-5,6,7,8-tetrahydroquinolin-8-yl]amino]methyl]imidazo[1,2-a]pyridin-3-yl]methanol Chemical compound C1[C@H](NC)CCN1C1=CC=CC2=NC(CN(C)[C@@H]3C4=NC=CC=C4CCC3)=C(CO)N12 LJZYHHSTUCZUCV-QUCCMNQESA-N 0.000 claims 2
- BIABECXOMDEQRN-MJGOQNOKSA-N [5-[(3r)-3-aminopyrrolidin-1-yl]-2-[[methyl-[(8s)-5,6,7,8-tetrahydroquinolin-8-yl]amino]methyl]imidazo[1,2-a]pyridin-3-yl]methanol Chemical compound CN([C@@H]1C2=NC=CC=C2CCC1)CC(=C(N12)CO)N=C1C=CC=C2N1CC[C@@H](N)C1 BIABECXOMDEQRN-MJGOQNOKSA-N 0.000 claims 2
- CZWUXDXQKLXFBS-FPOVZHCZSA-N [5-[(3s)-3-(dimethylamino)pyrrolidin-1-yl]-2-[[methyl-[(8s)-5,6,7,8-tetrahydroquinolin-8-yl]amino]methyl]imidazo[1,2-a]pyridin-3-yl]methanol Chemical compound C1[C@@H](N(C)C)CCN1C1=CC=CC2=NC(CN(C)[C@@H]3C4=NC=CC=C4CCC3)=C(CO)N12 CZWUXDXQKLXFBS-FPOVZHCZSA-N 0.000 claims 2
- DBLIBYXKCXRXKI-QWAKEFERSA-N [5-[methyl-(1-methylpyrrolidin-3-yl)amino]-2-[[methyl-[(8s)-5,6,7,8-tetrahydroquinolin-8-yl]amino]methyl]imidazo[1,2-a]pyridin-3-yl]methanol Chemical compound CN([C@@H]1C2=NC=CC=C2CCC1)CC(=C(N12)CO)N=C1C=CC=C2N(C)C1CCN(C)C1 DBLIBYXKCXRXKI-QWAKEFERSA-N 0.000 claims 2
- 230000002378 acidificating effect Effects 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000003282 alkyl amino group Chemical group 0.000 claims 2
- 239000003054 catalyst Substances 0.000 claims 2
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 2
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims 2
- 238000006268 reductive amination reaction Methods 0.000 claims 2
- XZLMELLMHWWEMK-ZYZRXSCRSA-N 1-[5-(4-methylpiperazin-1-yl)-2-[[methyl-[(8s)-5,6,7,8-tetrahydroquinolin-8-yl]amino]methyl]imidazo[1,2-a]pyridin-3-yl]ethanol Chemical compound N12C(C(O)C)=C(CN(C)[C@@H]3C4=NC=CC=C4CCC3)N=C2C=CC=C1N1CCN(C)CC1 XZLMELLMHWWEMK-ZYZRXSCRSA-N 0.000 claims 1
- CXISALFKUJXLHF-UHFFFAOYSA-N 2,2,2-trifluoro-1-[5-(4-methylpiperazin-1-yl)-2-[[methyl(5,6,7,8-tetrahydroquinolin-8-yl)amino]methyl]imidazo[1,2-a]pyridin-3-yl]ethanol Chemical compound C1CCC2=CC=CN=C2C1N(C)CC(=C(N12)C(O)C(F)(F)F)N=C1C=CC=C2N1CCN(C)CC1 CXISALFKUJXLHF-UHFFFAOYSA-N 0.000 claims 1
- FWHLIPKBOBBOAB-SANMLTNESA-N [2-[[benzyl-[(8s)-5,6,7,8-tetrahydroquinolin-8-yl]amino]methyl]-5-(4-methylpiperazin-1-yl)imidazo[1,2-a]pyridin-3-yl]methanol Chemical compound C1CN(C)CCN1C1=CC=CC2=NC(CN(CC=3C=CC=CC=3)[C@@H]3C4=NC=CC=C4CCC3)=C(CO)N12 FWHLIPKBOBBOAB-SANMLTNESA-N 0.000 claims 1
- IGWJIEYXVYINTM-FQEVSTJZSA-N [5-(1,4-diazepan-1-yl)-2-[[methyl-[(8s)-5,6,7,8-tetrahydroquinolin-8-yl]amino]methyl]imidazo[1,2-a]pyridin-3-yl]methanol Chemical compound CN([C@@H]1C2=NC=CC=C2CCC1)CC(=C(N12)CO)N=C1C=CC=C2N1CCCNCC1 IGWJIEYXVYINTM-FQEVSTJZSA-N 0.000 claims 1
- OJERPJRKPFSYOK-IAXKEJLGSA-N [5-(3,4,6,7,8,8a-hexahydro-1h-pyrrolo[1,2-a]pyrazin-2-yl)-2-[[methyl-[(8s)-5,6,7,8-tetrahydroquinolin-8-yl]amino]methyl]imidazo[1,2-a]pyridin-3-yl]methanol Chemical compound C1CCC2=CC=CN=C2[C@H]1N(C)CC1=C(CO)N2C(N3CC4CCCN4CC3)=CC=CC2=N1 OJERPJRKPFSYOK-IAXKEJLGSA-N 0.000 claims 1
- HEFHSVQEDGDAGF-FQEVSTJZSA-N [5-(4-aminopiperidin-1-yl)-2-[[methyl-[(8s)-5,6,7,8-tetrahydroquinolin-8-yl]amino]methyl]imidazo[1,2-a]pyridin-3-yl]methanol Chemical compound CN([C@@H]1C2=NC=CC=C2CCC1)CC(=C(N12)CO)N=C1C=CC=C2N1CCC(N)CC1 HEFHSVQEDGDAGF-FQEVSTJZSA-N 0.000 claims 1
- CYISDEQXPXFRCV-NRFANRHFSA-N [5-(4-methyl-1,4-diazepan-1-yl)-2-[[methyl-[(8s)-5,6,7,8-tetrahydroquinolin-8-yl]amino]methyl]imidazo[1,2-a]pyridin-3-yl]methanol Chemical compound CN([C@@H]1C2=NC=CC=C2CCC1)CC(=C(N12)CO)N=C1C=CC=C2N1CCCN(C)CC1 CYISDEQXPXFRCV-NRFANRHFSA-N 0.000 claims 1
- IUTANJSSQZHMSG-IJHRGXPZSA-N [5-(4-methylpiperazin-1-yl)-2-[1-[methyl-[(8s)-5,6,7,8-tetrahydroquinolin-8-yl]amino]ethyl]imidazo[1,2-a]pyridin-3-yl]methanol Chemical compound CN([C@@H]1C2=NC=CC=C2CCC1)C(C)C(=C(N12)CO)N=C1C=CC=C2N1CCN(C)CC1 IUTANJSSQZHMSG-IJHRGXPZSA-N 0.000 claims 1
- XHGQCPHNQYYJRF-SANMLTNESA-N [5-(4-methylpiperazin-1-yl)-2-[[[(8s)-5,6,7,8-tetrahydroquinolin-8-yl]-[[4-(trifluoromethyl)phenyl]methyl]amino]methyl]imidazo[1,2-a]pyridin-3-yl]methanol Chemical compound C1CN(C)CCN1C1=CC=CC2=NC(CN(CC=3C=CC(=CC=3)C(F)(F)F)[C@@H]3C4=NC=CC=C4CCC3)=C(CO)N12 XHGQCPHNQYYJRF-SANMLTNESA-N 0.000 claims 1
- QWHDVDASMCRJJZ-UHFFFAOYSA-N [5-(4-methylpiperazin-1-yl)-2-[[methyl(6,7,8,9-tetrahydro-5h-cyclohepta[b]pyridin-9-yl)amino]methyl]imidazo[1,2-a]pyridin-3-yl]methanol Chemical compound C1CCCC2=CC=CN=C2C1N(C)CC(=C(N12)CO)N=C1C=CC=C2N1CCN(C)CC1 QWHDVDASMCRJJZ-UHFFFAOYSA-N 0.000 claims 1
- QUDMHFVRKBVGBY-FQEVSTJZSA-N [5-(4-methylpiperazin-1-yl)-2-[[methyl-[(8s)-5,6,7,8-tetrahydroquinolin-8-yl]amino]methyl]imidazo[1,2-a]pyridin-3-yl]methanol Chemical compound CN([C@@H]1C2=NC=CC=C2CCC1)CC(=C(N12)CO)N=C1C=CC=C2N1CCN(C)CC1 QUDMHFVRKBVGBY-FQEVSTJZSA-N 0.000 claims 1
- CYYJZCMKOQFVEU-IRLDBZIGSA-N [5-[(3r)-3-(dimethylamino)pyrrolidin-1-yl]-2-[[ethyl-[(8s)-5,6,7,8-tetrahydroquinolin-8-yl]amino]methyl]imidazo[1,2-a]pyridin-3-yl]methanol Chemical compound CCN([C@@H]1C2=NC=CC=C2CCC1)CC(=C(N12)CO)N=C1C=CC=C2N1CC[C@@H](N(C)C)C1 CYYJZCMKOQFVEU-IRLDBZIGSA-N 0.000 claims 1
- TZXUJAFBNRHKQL-FQEVSTJZSA-N [5-[2-(dimethylamino)ethyl-methylamino]-2-[[methyl-[(8s)-5,6,7,8-tetrahydroquinolin-8-yl]amino]methyl]imidazo[1,2-a]pyridin-3-yl]methanol Chemical compound C1CCC2=CC=CN=C2[C@H]1N(C)CC1=C(CO)N2C(N(C)CCN(C)C)=CC=CC2=N1 TZXUJAFBNRHKQL-FQEVSTJZSA-N 0.000 claims 1
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000004857 imidazopyridinyl group Chemical group N1C(=NC2=C1C=CC=N2)* 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 238000011321 prophylaxis Methods 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 1
- 125000006193 alkinyl group Chemical group 0.000 abstract 3
- 102100035875 C-C chemokine receptor type 5 Human genes 0.000 abstract 1
- 101710149870 C-C chemokine receptor type 5 Proteins 0.000 abstract 1
- 102000019034 Chemokines Human genes 0.000 abstract 1
- 108010012236 Chemokines Proteins 0.000 abstract 1
- 230000027455 binding Effects 0.000 abstract 1
- 150000002170 ethers Chemical class 0.000 abstract 1
- 239000003446 ligand Substances 0.000 abstract 1
- 230000001681 protective effect Effects 0.000 abstract 1
- 102000005962 receptors Human genes 0.000 abstract 1
- 108020003175 receptors Proteins 0.000 abstract 1
- 230000009870 specific binding Effects 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 125000000147 tetrahydroquinolinyl group Chemical class N1(CCCC2=CC=CC=C12)* 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
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| JP5257068B2 (ja) | 2006-05-16 | 2013-08-07 | 小野薬品工業株式会社 | 保護されていてもよい酸性基を含有する化合物およびその用途 |
| US20090325992A1 (en) | 2006-07-31 | 2009-12-31 | Ono Pharmaceutical Co., Ltd. | Compound having cyclic group bound thereto through spiro binding and use thereof |
| US7767826B2 (en) * | 2007-10-05 | 2010-08-03 | Pharmatech International, Inc. | Process for the synthesis of L-(+)-ergothioneine |
| WO2009061856A1 (en) * | 2007-11-09 | 2009-05-14 | The Salk Instituite For Biological Studies | Non-nucleoside reverse transcriptase inhibitors |
| CN102675305B (zh) * | 2011-03-08 | 2014-11-12 | 中国科学院上海药物研究所 | 一类咪唑并吡啶类化合物及其制备方法和用途 |
| CN103570683B (zh) * | 2012-07-30 | 2018-04-17 | 中国科学院上海药物研究所 | 多取代胺类化合物及其制备方法和用途 |
| KR102421235B1 (ko) | 2014-02-13 | 2022-07-15 | 인사이트 코포레이션 | Lsd1 저해제로서 사이클로프로필아민 |
| TWI720451B (zh) | 2014-02-13 | 2021-03-01 | 美商英塞特控股公司 | 作為lsd1抑制劑之環丙胺 |
| WO2016007722A1 (en) | 2014-07-10 | 2016-01-14 | Incyte Corporation | Triazolopyridines and triazolopyrazines as lsd1 inhibitors |
| SG11201708047UA (en) * | 2015-04-03 | 2017-10-30 | Incyte Corp | Heterocyclic compounds as lsd1 inhibitors |
| CN110402244B (zh) | 2015-08-12 | 2023-02-03 | 因赛特公司 | Lsd1抑制剂的盐 |
| CN109069486A (zh) | 2015-12-14 | 2018-12-21 | X4 制药有限公司 | 治疗癌症的方法 |
| JP6864296B2 (ja) | 2015-12-14 | 2021-04-28 | エックス４ ファーマシューティカルズ， インコーポレイテッド | がんを処置する方法 |
| EP3390406A1 (en) * | 2015-12-15 | 2018-10-24 | Bristol-Myers Squibb Company | Cxcr4 receptor antagonists |
| WO2017112894A1 (en) | 2015-12-22 | 2017-06-29 | X4 Pharmaceuticals, Inc. | Methods for treating immunodeficiency disease |
| EP3440112A4 (en) | 2016-04-08 | 2019-10-09 | X4 Pharmaceuticals, Inc. | METHOD FOR THE TREATMENT OF CANCER |
| JP7054529B2 (ja) | 2016-06-21 | 2022-04-14 | エックス４ ファーマシューティカルズ， インコーポレイテッド | Ｃｘｃｒ４阻害剤およびその使用 |
| WO2017223243A1 (en) | 2016-06-21 | 2017-12-28 | X4 Pharmaceuticals, Inc. | Cxcr4 inhibitors and uses thereof |
| CN109640988A (zh) | 2016-06-21 | 2019-04-16 | X4 制药有限公司 | Cxcr4抑制剂及其用途 |
| IL309069A (en) | 2017-02-21 | 2024-02-01 | Univ Emory | CXCR4 cytokine receptor modulators and related uses |
| WO2019060860A1 (en) * | 2017-09-25 | 2019-03-28 | Suzhou Yunxuan Yiyao Keji Youxian Gongsi | HETEROARYL COMPOUNDS AS INHIBITORS OF CXCR4, COMPOSITION AND METHOD OF USE THEREOF |
| JP7282786B2 (ja) * | 2017-09-25 | 2023-05-29 | シージーンテック （スーチョウ， チャイナ） カンパニー リミテッド | Ｃｘｃｒ４阻害剤としてのヘテロアリール化合物、それを用いた組成物及び方法 |
| EP3768256A4 (en) | 2018-03-19 | 2021-11-24 | Emory University | PANTROPIC ENTRY INHIBITORS |
| WO2020047198A1 (en) | 2018-08-31 | 2020-03-05 | Incyte Corporation | Salts of an lsd1 inhibitor and processes for preparing the same |
| US10548889B1 (en) | 2018-08-31 | 2020-02-04 | X4 Pharmaceuticals, Inc. | Compositions of CXCR4 inhibitors and methods of preparation and use |
| CA3171250A1 (en) | 2020-03-10 | 2021-09-16 | E. Lynne KELLEY | Methods for treating neutropenia |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU1738088A3 (ru) * | 1987-07-17 | 1992-05-30 | Жансен Фармасетика Н.В. (Фирма) | Способ получени цис-производных N-(3-окси-4-пиперидинил)бензамида |
| US6734191B2 (en) * | 2000-09-15 | 2004-05-11 | Anormed, Inc. | Chemokine receptor binding heterocyclic compounds |
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| JP2004512336A (ja) * | 2000-09-15 | 2004-04-22 | アノーメッド インコーポレイティド | ケモカインレセプター結合複素環式化合物 |
| IL154227A0 (en) * | 2000-09-15 | 2003-07-31 | Anormed Inc | Chemokine receptor binding heterocyclic compounds |
| NZ524421A (en) * | 2000-09-15 | 2005-02-25 | Anormed Inc | Chemokine receptor binding heterocyclic compounds |
| CN1596255A (zh) * | 2001-12-21 | 2005-03-16 | 阿诺麦德股份有限公司 | 具有强效的与趋化因子受体结合的杂环化合物 |
| US7291631B2 (en) * | 2003-04-11 | 2007-11-06 | Genzyme Corporation | CXCR4 chemokine receptor binding compounds |
| MX2007002679A (es) * | 2004-09-02 | 2007-05-16 | Smithkline Beecham Corp | Compuestos quimicos. |
| JP2008514622A (ja) * | 2004-09-24 | 2008-05-08 | スミスクライン ビーチャム コーポレーション | 化合物 |
| JP2009507795A (ja) * | 2005-08-31 | 2009-02-26 | スミスクライン ビーチャム コーポレーション | 化合物 |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU1738088A3 (ru) * | 1987-07-17 | 1992-05-30 | Жансен Фармасетика Н.В. (Фирма) | Способ получени цис-производных N-(3-окси-4-пиперидинил)бензамида |
| US6734191B2 (en) * | 2000-09-15 | 2004-05-11 | Anormed, Inc. | Chemokine receptor binding heterocyclic compounds |
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