ZA200206073B - Antiviral azaindole derivatives. - Google Patents
Antiviral azaindole derivatives. Download PDFInfo
- Publication number
- ZA200206073B ZA200206073B ZA200206073A ZA200206073A ZA200206073B ZA 200206073 B ZA200206073 B ZA 200206073B ZA 200206073 A ZA200206073 A ZA 200206073A ZA 200206073 A ZA200206073 A ZA 200206073A ZA 200206073 B ZA200206073 B ZA 200206073B
- Authority
- ZA
- South Africa
- Prior art keywords
- group
- compound
- alkynyl
- carbon
- alkyl
- Prior art date
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- 230000000840 anti-viral effect Effects 0.000 title claims description 12
- 125000005334 azaindolyl group Chemical class N1N=C(C2=CC=CC=C12)* 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 40
- -1 C.-C Chemical group 0.000 claims description 13
- 239000003814 drug Substances 0.000 claims description 12
- 208000030507 AIDS Diseases 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 7
- 241000700605 Viruses Species 0.000 claims description 5
- 239000003112 inhibitor Substances 0.000 claims description 5
- 208000015181 infectious disease Diseases 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims 105
- 229910052739 hydrogen Inorganic materials 0.000 claims 35
- 125000000217 alkyl group Chemical group 0.000 claims 29
- 125000000304 alkynyl group Chemical group 0.000 claims 29
- 125000003342 alkenyl group Chemical group 0.000 claims 27
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 25
- 125000000753 cycloalkyl group Chemical group 0.000 claims 24
- 150000003839 salts Chemical class 0.000 claims 22
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 14
- 125000004432 carbon atom Chemical group C* 0.000 claims 12
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 11
- 229910052736 halogen Inorganic materials 0.000 claims 9
- 239000000203 mixture Substances 0.000 claims 9
- 239000001257 hydrogen Substances 0.000 claims 8
- 229910052757 nitrogen Inorganic materials 0.000 claims 8
- 150000002367 halogens Chemical class 0.000 claims 7
- 239000000126 substance Substances 0.000 claims 7
- 229910052792 caesium Inorganic materials 0.000 claims 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
- 241000124008 Mammalia Species 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 4
- 229920002554 vinyl polymer Polymers 0.000 claims 4
- 229960005475 antiinfective agent Drugs 0.000 claims 3
- 239000004599 antimicrobial Substances 0.000 claims 3
- 239000003443 antiviral agent Substances 0.000 claims 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 3
- 239000003795 chemical substances by application Substances 0.000 claims 3
- 150000002431 hydrogen Chemical class 0.000 claims 3
- 239000002955 immunomodulating agent Substances 0.000 claims 3
- 229940121354 immunomodulator Drugs 0.000 claims 3
- 230000002584 immunomodulator Effects 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 239000001301 oxygen Substances 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 229910052794 bromium Inorganic materials 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 125000006329 ethyl amino carbonyl group Chemical group [H]N(C(*)=O)C([H])([H])C([H])([H])[H] 0.000 claims 2
- 229910052731 fluorine Inorganic materials 0.000 claims 2
- 239000002835 hiv fusion inhibitor Substances 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
- 229910019567 Re Re Inorganic materials 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 102100028651 Tenascin-N Human genes 0.000 claims 1
- 101710087911 Tenascin-N Proteins 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- 229940079593 drug Drugs 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
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- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical class C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 4
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- WHBIGIKBNXZKFE-UHFFFAOYSA-N delavirdine Chemical compound CC(C)NC1=CC=CN=C1N1CCN(C(=O)C=2NC3=CC=C(NS(C)(=O)=O)C=C3C=2)CC1 WHBIGIKBNXZKFE-UHFFFAOYSA-N 0.000 description 4
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- DMPXDLRQZYXVHL-UHFFFAOYSA-N 2,5-dihydroxy-3,6-bis[6-(3-methylbut-2-enyl)-1h-indol-3-yl]cyclohexa-2,5-diene-1,4-dione Chemical compound CC(C)=CCC1=CC=C2C(C=3C(=O)C(O)=C(C(C=3O)=O)C=3C4=CC=C(C=C4NC=3)CC=C(C)C)=CNC2=C1 DMPXDLRQZYXVHL-UHFFFAOYSA-N 0.000 description 2
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 2
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- CBVCZFGXHXORBI-PXQQMZJSSA-N indinavir Chemical compound C([C@H](N(CC1)C[C@@H](O)C[C@@H](CC=2C=CC=CC=2)C(=O)N[C@H]2C3=CC=CC=C3C[C@H]2O)C(=O)NC(C)(C)C)N1CC1=CC=CN=C1 CBVCZFGXHXORBI-PXQQMZJSSA-N 0.000 description 2
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- 150000002475 indoles Chemical class 0.000 description 2
- 239000002777 nucleoside Substances 0.000 description 2
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- 238000002360 preparation method Methods 0.000 description 2
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- XNQAJERZSLDENY-UHFFFAOYSA-N semicochliodinol A Chemical compound C1=CC=C2C(C=3C(=O)C(O)=C(C(C=3O)=O)C3=CNC4=CC=C(C=C43)CC=C(C)C)=CNC2=C1 XNQAJERZSLDENY-UHFFFAOYSA-N 0.000 description 2
- RXCOGDYOZQGGMK-UHFFFAOYSA-N (3,4-diaminophenyl)-phenylmethanone Chemical compound C1=C(N)C(N)=CC=C1C(=O)C1=CC=CC=C1 RXCOGDYOZQGGMK-UHFFFAOYSA-N 0.000 description 1
- OQJVXNHMUWQQEW-UHFFFAOYSA-N 1,2,3,4-tetrahydropyrazine Chemical class C1CNC=CN1 OQJVXNHMUWQQEW-UHFFFAOYSA-N 0.000 description 1
- GUJAGMICFDYKNR-UHFFFAOYSA-N 1,4-benzodiazepine Chemical class N1C=CN=CC2=CC=CC=C12 GUJAGMICFDYKNR-UHFFFAOYSA-N 0.000 description 1
- HIYWOHBEPVGIQN-UHFFFAOYSA-N 1h-benzo[g]indole Chemical class C1=CC=CC2=C(NC=C3)C3=CC=C21 HIYWOHBEPVGIQN-UHFFFAOYSA-N 0.000 description 1
- YGBYVNQFNMXDJM-UHFFFAOYSA-N 1h-indazole-5-carbonitrile Chemical compound N#CC1=CC=C2NN=CC2=C1 YGBYVNQFNMXDJM-UHFFFAOYSA-N 0.000 description 1
- VFHUJFBEFDVZPJ-UHFFFAOYSA-N 1h-indole-2-carboxamide Chemical class C1=CC=C2NC(C(=O)N)=CC2=C1 VFHUJFBEFDVZPJ-UHFFFAOYSA-N 0.000 description 1
- PMBKVWCLVTYNAG-UHFFFAOYSA-N 1h-pyrrolo[3,2-b]pyridine-3-carboxamide Chemical class C1=CN=C2C(C(=O)N)=CNC2=C1 PMBKVWCLVTYNAG-UHFFFAOYSA-N 0.000 description 1
- HNGJGZFTQRJUIF-UHFFFAOYSA-N 2,5-dihydroxy-3,6-bis(1h-indol-3-yl)cyclohexa-2,5-diene-1,4-dione Chemical compound C1=CC=C2C(C3=C(O)C(=O)C(C=4C5=CC=CC=C5NC=4)=C(C3=O)O)=CNC2=C1 HNGJGZFTQRJUIF-UHFFFAOYSA-N 0.000 description 1
- FBCZWQNVHNIQOD-UHFFFAOYSA-N 2-piperazin-1-yl-1h-indole Chemical class C1CNCCN1C1=CC2=CC=CC=C2N1 FBCZWQNVHNIQOD-UHFFFAOYSA-N 0.000 description 1
- HQQTZCPKNZVLFF-UHFFFAOYSA-N 4h-1,2-benzoxazin-3-one Chemical compound C1=CC=C2ONC(=O)CC2=C1 HQQTZCPKNZVLFF-UHFFFAOYSA-N 0.000 description 1
- RWHZLSHOGJONCU-UHFFFAOYSA-N 5h-indolo[3,2-b][1,5]benzothiazepine Chemical class C1=NC2=CC=CC=C2SC2=C1NC1=CC=CC=C21 RWHZLSHOGJONCU-UHFFFAOYSA-N 0.000 description 1
- LLGMYKPLPYSPKQ-UHFFFAOYSA-N 6-chloro-1h-pyrrolo[2,3-b]pyridine-5-carbonitrile Chemical class C1=C(C#N)C(Cl)=NC2=C1C=CN2 LLGMYKPLPYSPKQ-UHFFFAOYSA-N 0.000 description 1
- CHVRKRDEYKTBKI-UHFFFAOYSA-N 6-oxo-1,2,3,7-tetrahydropyrrolo[2,3-b]pyridine-5-carbonitrile Chemical class C1=C(C#N)C(O)=NC2=C1CCN2 CHVRKRDEYKTBKI-UHFFFAOYSA-N 0.000 description 1
- QKEBGAUJUHZNNU-UHFFFAOYSA-N 9h-pyrrolo[2,3-f]quinoxaline Chemical class N1=CC=NC2=C(NC=C3)C3=CC=C21 QKEBGAUJUHZNNU-UHFFFAOYSA-N 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical class N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
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- QAGYKUNXZHXKMR-UHFFFAOYSA-N CPD000469186 Natural products CC1=C(O)C=CC=C1C(=O)NC(C(O)CN1C(CC2CCCCC2C1)C(=O)NC(C)(C)C)CSC1=CC=CC=C1 QAGYKUNXZHXKMR-UHFFFAOYSA-N 0.000 description 1
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- 206010061818 Disease progression Diseases 0.000 description 1
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- 108010016183 Human immunodeficiency virus 1 p16 protease Proteins 0.000 description 1
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- GIIWGCBLYNDKBO-UHFFFAOYSA-N Quinoline 1-oxide Chemical compound C1=CC=C2[N+]([O-])=CC=CC2=C1 GIIWGCBLYNDKBO-UHFFFAOYSA-N 0.000 description 1
- NCDNCNXCDXHOMX-UHFFFAOYSA-N Ritonavir Natural products C=1C=CC=CC=1CC(NC(=O)OCC=1SC=NC=1)C(O)CC(CC=1C=CC=CC=1)NC(=O)C(C(C)C)NC(=O)N(C)CC1=CSC(C(C)C)=N1 NCDNCNXCDXHOMX-UHFFFAOYSA-N 0.000 description 1
- XNKLLVCARDGLGL-JGVFFNPUSA-N Stavudine Chemical compound O=C1NC(=O)C(C)=CN1[C@H]1C=C[C@@H](CO)O1 XNKLLVCARDGLGL-JGVFFNPUSA-N 0.000 description 1
- 206010066901 Treatment failure Diseases 0.000 description 1
- 206010058874 Viraemia Diseases 0.000 description 1
- WREGKURFCTUGRC-POYBYMJQSA-N Zalcitabine Chemical compound O=C1N=C(N)C=CN1[C@@H]1O[C@H](CO)CC1 WREGKURFCTUGRC-POYBYMJQSA-N 0.000 description 1
- XDNADZYPWVQFRI-UHFFFAOYSA-N [1]benzofuro[2,3-h]quinoline Chemical class C1=CC=NC2=C3C4=CC=CC=C4OC3=CC=C21 XDNADZYPWVQFRI-UHFFFAOYSA-N 0.000 description 1
- 229960004748 abacavir Drugs 0.000 description 1
- MCGSCOLBFJQGHM-SCZZXKLOSA-N abacavir Chemical compound C=12N=CN([C@H]3C=C[C@@H](CO)C3)C2=NC(N)=NC=1NC1CC1 MCGSCOLBFJQGHM-SCZZXKLOSA-N 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
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- YMARZQAQMVYCKC-OEMFJLHTSA-N amprenavir Chemical compound C([C@@H]([C@H](O)CN(CC(C)C)S(=O)(=O)C=1C=CC(N)=CC=1)NC(=O)O[C@@H]1COCC1)C1=CC=CC=C1 YMARZQAQMVYCKC-OEMFJLHTSA-N 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
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- 125000003118 aryl group Chemical group 0.000 description 1
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- 230000001747 exhibiting effect Effects 0.000 description 1
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- 238000005984 hydrogenation reaction Methods 0.000 description 1
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- OPXLLQIJSORQAM-UHFFFAOYSA-N mebendazole Chemical compound C=1C=C2NC(NC(=O)OC)=NC2=CC=1C(=O)C1=CC=CC=C1 OPXLLQIJSORQAM-UHFFFAOYSA-N 0.000 description 1
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- GYGNNRWBBHJVNM-UHFFFAOYSA-N n-(1h-1,2-benzodiazepin-7-yl)hydroxylamine Chemical class N1N=CC=CC2=CC(NO)=CC=C21 GYGNNRWBBHJVNM-UHFFFAOYSA-N 0.000 description 1
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- NCDNCNXCDXHOMX-XGKFQTDJSA-N ritonavir Chemical compound N([C@@H](C(C)C)C(=O)N[C@H](C[C@H](O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1SC=NC=1)CC=1C=CC=CC=1)C(=O)N(C)CC1=CSC(C(C)C)=N1 NCDNCNXCDXHOMX-XGKFQTDJSA-N 0.000 description 1
- QWAXKHKRTORLEM-UGJKXSETSA-N saquinavir Chemical compound C([C@@H]([C@H](O)CN1C[C@H]2CCCC[C@H]2C[C@H]1C(=O)NC(C)(C)C)NC(=O)[C@H](CC(N)=O)NC(=O)C=1N=C2C=CC=CC2=CC=1)C1=CC=CC=C1 QWAXKHKRTORLEM-UGJKXSETSA-N 0.000 description 1
- 229960001852 saquinavir Drugs 0.000 description 1
- JWHQWQQROAZMII-UHFFFAOYSA-N semicochliodinol B Chemical compound C1=CC=C2C(C=3C(=O)C(O)=C(C(C=3O)=O)C=3C4=CC=C(C=C4NC=3)CC=C(C)C)=CNC2=C1 JWHQWQQROAZMII-UHFFFAOYSA-N 0.000 description 1
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- HBOMLICNUCNMMY-XLPZGREQSA-N zidovudine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](N=[N+]=[N-])C1 HBOMLICNUCNMMY-XLPZGREQSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
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- 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
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- 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
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- A61K31/33—Heterocyclic compounds
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- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
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- Chemical Kinetics & Catalysis (AREA)
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- Virology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- AIDS & HIV (AREA)
- Tropical Medicine & Parasitology (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
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| US18400400P | 2000-02-22 | 2000-02-22 |
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Families Citing this family (44)
| Publication number | Priority date | Publication date | Assignee | Title |
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| EP1363705B9 (en) * | 2001-02-02 | 2012-11-07 | Bristol-Myers Squibb Company | Composition and antiviral activity of substituted azaindoleoxoacetic piperazine derivatives |
| US20030207910A1 (en) * | 2001-02-02 | 2003-11-06 | Tao Wang | Composition and antiviral activity of substituted azaindoleoxoacetic piperazine derivatives |
| US20040110785A1 (en) * | 2001-02-02 | 2004-06-10 | Tao Wang | Composition and antiviral activity of substituted azaindoleoxoacetic piperazine derivatives |
| US6825201B2 (en) * | 2001-04-25 | 2004-11-30 | Bristol-Myers Squibb Company | Indole, azaindole and related heterocyclic amidopiperazine derivatives |
| US20030236277A1 (en) | 2002-02-14 | 2003-12-25 | Kadow John F. | Indole, azaindole and related heterocyclic pyrrolidine derivatives |
| WO2003072028A2 (en) * | 2002-02-23 | 2003-09-04 | Bristol-Myers Squibb Company | Method of treating hiv infection by preventing interaction of cd4 and gp120 |
| US20040063744A1 (en) * | 2002-05-28 | 2004-04-01 | Tao Wang | Indole, azaindole and related heterocyclic 4-alkenyl piperidine amides |
| US20050075364A1 (en) * | 2003-07-01 | 2005-04-07 | Kap-Sun Yeung | Indole, azaindole and related heterocyclic N-substituted piperazine derivatives |
| UA88297C2 (ru) * | 2004-03-15 | 2009-10-12 | Бристол-Майэрс Сквибб Компани | Пиперазиновые пролекарства и замещенные пиперидиновые антивирусные средства |
| US7745625B2 (en) | 2004-03-15 | 2010-06-29 | Bristol-Myers Squibb Company | Prodrugs of piperazine and substituted piperidine antiviral agents |
| US20050252408A1 (en) * | 2004-05-17 | 2005-11-17 | Richardson H W | Particulate wood preservative and method for producing same |
| PT1753764E (pt) | 2004-06-09 | 2009-01-28 | Glaxo Group Ltd | Derivados de pirrolopiridina |
| US7498342B2 (en) | 2004-06-17 | 2009-03-03 | Plexxikon, Inc. | Compounds modulating c-kit activity |
| US20060100432A1 (en) * | 2004-11-09 | 2006-05-11 | Matiskella John D | Crystalline materials of 1-(4-benzoyl-piperazin-1-yl)-2-[4-methoxy-7-(3-methyl-[1,2,4]triazol-1-yl)-1H-pyrrolo[2,3-c]pyridin-3-yl]-ethane-1,2-dione |
| US20060100209A1 (en) * | 2004-11-09 | 2006-05-11 | Chong-Hui Gu | Formulations of 1-(4-benzoyl-piperazin-1-yl)-2-[4-methoxy-7-(3-methyl-[1,2,4]triazol-1-yl)-1H-pyrrolo[2,3-c]pyridin-3-yl]-ethane-1,2-dione |
| US7183284B2 (en) * | 2004-12-29 | 2007-02-27 | Bristol-Myers Squibb Company | Aminium salts of 1,2,3-triazoles as prodrugs of drugs including antiviral agents |
| US7601715B2 (en) | 2005-06-22 | 2009-10-13 | Bristol-Myers Squibb Company | Process for preparing triazole substituted azaindoleoxoacetic piperazine derivatives and novel salt forms produced therein |
| AU2006272750B2 (en) | 2005-07-22 | 2011-09-29 | Cytodyn, Inc. | Methods for reducing viral load in HIV-1-infected patients |
| US7598380B2 (en) * | 2005-08-03 | 2009-10-06 | Bristol-Myers Squibb Company | Method of preparation of azaindole derivatives |
| US7396830B2 (en) * | 2005-10-04 | 2008-07-08 | Bristol-Myers Squibb Company | Piperazine amidines as antiviral agents |
| US7851476B2 (en) * | 2005-12-14 | 2010-12-14 | Bristol-Myers Squibb Company | Crystalline forms of 1-benzoyl-4-[2-[4-methoxy-7-(3-methyl-1H-1,2,4-triazol-1-YL)-1-[(phosphonooxy)methyl]-1H-pyrrolo[2,3-C]pyridin-3-YL]-1,2-dioxoethyl]-piperazine |
| US7807671B2 (en) * | 2006-04-25 | 2010-10-05 | Bristol-Myers Squibb Company | Diketo-piperazine and piperidine derivatives as antiviral agents |
| WO2008063888A2 (en) | 2006-11-22 | 2008-05-29 | Plexxikon, Inc. | Compounds modulating c-fms and/or c-kit activity and uses therefor |
| BRPI0812912A2 (pt) * | 2007-06-18 | 2014-12-09 | Sanofi Aventis | Derivados de pirrol como antagonistas de p2y12 |
| WO2009012283A1 (en) | 2007-07-17 | 2009-01-22 | Plexxikon Inc. | Compounds and methods for kinase modulation, and indications therefor |
| WO2009011912A1 (en) * | 2007-07-18 | 2009-01-22 | Bristol-Myers Squibb Company | A composition for treating hiv comprising virus-like particles |
| PT2240482E (pt) | 2008-01-31 | 2013-09-06 | Sanofi Sa | Azaindole-3-carboxamidas cíclicas, sua preparação e sua utilização como fármacos |
| JP5638527B2 (ja) * | 2008-09-04 | 2014-12-10 | ブリストル−マイヤーズ スクイブ カンパニーＢｒｉｓｔｏｌ−Ｍｙｅｒｓ Ｓｑｕｉｂｂ Ｃｏｍｐａｎｙ | Ｈｉｖ結合阻害剤の最適な送達のための安定な医薬組成物 |
| ES2552386T3 (es) | 2009-04-03 | 2015-11-27 | F. Hoffmann-La Roche Ag | Composiciones de {3-[5-(4-cloro-fenil)-1H-pirrol[2,3-b]piridin-3-carbonil]-2,4-difluoro-fenil}-amida del ácido propano-1-sulfónico y usos de las mismas |
| JP2013510166A (ja) | 2009-11-06 | 2013-03-21 | プレキシコン インコーポレーテッド | キナーゼ調節のための化合物、方法およびその適用 |
| EP2646439B1 (en) | 2010-12-02 | 2016-05-25 | Bristol-Myers Squibb Company | Alkyl amides as hiv attachment inhibitors |
| AU2012214762B2 (en) | 2011-02-07 | 2015-08-13 | Plexxikon Inc. | Compounds and methods for kinase modulation, and indications therefor |
| TWI558702B (zh) | 2011-02-21 | 2016-11-21 | 普雷辛肯公司 | 醫藥活性物質的固態形式 |
| ES2636312T3 (es) | 2011-04-12 | 2017-10-05 | VIIV Healthcare UK (No.5) Limited | Derivados de tioamida, amidoxima y amidrazona como inhibidores de la fijación del VIH |
| EP2751119B1 (en) | 2011-08-29 | 2016-11-23 | VIIV Healthcare UK (No.5) Limited | Fused bicyclic diamine derivatives as hiv attachment inhibitors |
| US8664213B2 (en) | 2011-08-29 | 2014-03-04 | Bristol-Myers Squibb Company | Spiro bicyclic diamine derivatives as HIV attachment inhibitors |
| US9193725B2 (en) | 2012-03-14 | 2015-11-24 | Bristol-Meyers Squibb Company | Cyclic hydrazine derivatives as HIV attachment inhibitors |
| US9150570B2 (en) | 2012-05-31 | 2015-10-06 | Plexxikon Inc. | Synthesis of heterocyclic compounds |
| CN102746295B (zh) * | 2012-06-20 | 2014-10-15 | 上海阿达玛斯试剂有限公司 | 4位取代-7-氮杂吲哚的制备方法 |
| US9655888B2 (en) | 2012-08-09 | 2017-05-23 | VIIV Healthcare UK (No.5) Limited | Tricyclic alkene derivatives as HIV attachment inhibitors |
| ES2616492T3 (es) | 2012-08-09 | 2017-06-13 | VIIV Healthcare UK (No.5) Limited | Derivados de piperidina amida como inhibidores de la fijación del VIH |
| CN109528749B (zh) * | 2017-09-22 | 2023-04-28 | 上海交通大学医学院附属瑞金医院 | 长链非编码rna-h19在制备治疗垂体瘤药物中的用途 |
| US11767321B2 (en) | 2020-10-05 | 2023-09-26 | Enliven Inc. | 5- and 6-azaindole compounds for inhibition of BCR-ABL tyrosine kinases |
| CN112430223B (zh) * | 2020-11-24 | 2022-11-25 | 中国人民解放军海军军医大学 | 一类取代苯甲酰哌嗪类化合物及其应用 |
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2001
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- 2001-01-19 PL PL01357434A patent/PL357434A1/xx not_active Application Discontinuation
- 2001-01-19 JP JP2001561320A patent/JP3868814B2/ja not_active Expired - Fee Related
- 2001-01-19 EP EP01904970A patent/EP1257276B1/en not_active Expired - Lifetime
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- 2001-01-19 DK DK01904970T patent/DK1257276T3/da active
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- 2001-01-19 ES ES01904970T patent/ES2254367T3/es not_active Expired - Lifetime
- 2001-01-19 MX MXPA02008113A patent/MXPA02008113A/es active IP Right Grant
- 2001-01-19 AT AT01904970T patent/ATE314072T1/de active
- 2001-01-19 RU RU2002125494/04A patent/RU2259372C2/ru not_active IP Right Cessation
- 2001-01-19 TR TR2002/01961T patent/TR200201961T2/xx unknown
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- 2001-01-19 WO PCT/US2001/002009 patent/WO2001062255A1/en active IP Right Grant
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- 2001-02-21 UY UY26593A patent/UY26593A1/es not_active IP Right Cessation
- 2001-02-22 PE PE2001000190A patent/PE20020786A1/es not_active Application Discontinuation
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2002
- 2002-07-30 ZA ZA200206073A patent/ZA200206073B/en unknown
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2003
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2006
- 2006-03-27 CY CY20061100420T patent/CY1107460T1/el unknown
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