CA2534866A1 - Piperazine derivatives for the treatment of hiv infections - Google Patents
Piperazine derivatives for the treatment of hiv infections Download PDFInfo
- Publication number
- CA2534866A1 CA2534866A1 CA002534866A CA2534866A CA2534866A1 CA 2534866 A1 CA2534866 A1 CA 2534866A1 CA 002534866 A CA002534866 A CA 002534866A CA 2534866 A CA2534866 A CA 2534866A CA 2534866 A1 CA2534866 A1 CA 2534866A1
- Authority
- CA
- Canada
- Prior art keywords
- compound
- methyl
- preparation
- piperazin
- benzoyl
- 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.)
- Abandoned
Links
- 238000011282 treatment Methods 0.000 title claims abstract description 25
- 229940066771 systemic antihistamines piperazine derivative Drugs 0.000 title description 4
- 150000004885 piperazines Chemical class 0.000 title description 3
- 208000031886 HIV Infections Diseases 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 371
- 150000003839 salts Chemical class 0.000 claims abstract description 55
- 238000000034 method Methods 0.000 claims abstract description 53
- 239000012453 solvate Substances 0.000 claims abstract description 43
- 208000030507 AIDS Diseases 0.000 claims abstract description 13
- 206010038997 Retroviral infections Diseases 0.000 claims abstract description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 90
- -1 benzopiperidinyl Chemical group 0.000 claims description 39
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 30
- 239000003814 drug Substances 0.000 claims description 29
- 125000002947 alkylene group Chemical group 0.000 claims description 24
- 229910052757 nitrogen Inorganic materials 0.000 claims description 21
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 18
- 125000004076 pyridyl group Chemical group 0.000 claims description 16
- 125000004429 atom Chemical group 0.000 claims description 14
- 125000005843 halogen group Chemical group 0.000 claims description 14
- 229940124597 therapeutic agent Drugs 0.000 claims description 13
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 10
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 7
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical class C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
- 229920006395 saturated elastomer Polymers 0.000 claims description 6
- 239000003085 diluting agent Substances 0.000 claims description 5
- 241000124008 Mammalia Species 0.000 claims description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical class C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical class C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 4
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 4
- 239000000969 carrier Substances 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000002883 imidazolyl group Chemical group 0.000 claims description 4
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 4
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 4
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 4
- 125000001425 triazolyl group Chemical group 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 3
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 3
- KXLKYTFVIKKVMW-MOPGFXCFSA-N (2s)-1-[(2r)-4-benzoyl-2-methylpiperazin-1-yl]-2-[2-(1h-pyrazol-5-ylamino)quinolin-5-yl]oxypropan-1-one Chemical compound O([C@@H](C)C(=O)N1[C@@H](CN(CC1)C(=O)C=1C=CC=CC=1)C)C(C1=CC=2)=CC=CC1=NC=2NC1=CC=NN1 KXLKYTFVIKKVMW-MOPGFXCFSA-N 0.000 claims description 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 2
- 125000002733 (C1-C6) fluoroalkyl group Chemical group 0.000 claims description 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
- OQRSXFNMNAQFEB-SJORKVTESA-N 4-[(2s)-1-[(2r)-4-benzoyl-2-methylpiperazin-1-yl]-1-oxopropan-2-yl]oxy-3-methoxy-n-methylbenzamide Chemical compound COC1=CC(C(=O)NC)=CC=C1O[C@@H](C)C(=O)N1[C@H](C)CN(C(=O)C=2C=CC=CC=2)CC1 OQRSXFNMNAQFEB-SJORKVTESA-N 0.000 claims description 2
- KVDRFBPETGPOMO-CVEARBPZSA-N 5-[(2s)-1-[(2r)-4-benzoyl-2-methylpiperazin-1-yl]-1-oxopropan-2-yl]oxy-4-methoxy-n-methylpyridine-2-carboxamide Chemical compound C1=NC(C(=O)NC)=CC(OC)=C1O[C@@H](C)C(=O)N1[C@H](C)CN(C(=O)C=2C=CC=CC=2)CC1 KVDRFBPETGPOMO-CVEARBPZSA-N 0.000 claims description 2
- AHSGKFLIDGDUAT-CABCVRRESA-N 5-[(2s)-1-[(2r)-4-benzoyl-2-methylpiperazin-1-yl]-1-oxopropan-2-yl]oxy-4-methoxypyridine-2-carboxamide Chemical compound COC1=CC(C(N)=O)=NC=C1O[C@@H](C)C(=O)N1[C@H](C)CN(C(=O)C=2C=CC=CC=2)CC1 AHSGKFLIDGDUAT-CABCVRRESA-N 0.000 claims description 2
- VMJUDEOSVIYEMQ-SJORKVTESA-N 5-[(2s)-1-[(2r)-4-benzoyl-2-methylpiperazin-1-yl]-1-oxopropan-2-yl]oxy-n-cyclopropyl-4-methoxypyridine-2-carboxamide Chemical compound O=C([C@H](C)OC1=CN=C(C=C1OC)C(=O)NC1CC1)N([C@@H](C1)C)CCN1C(=O)C1=CC=CC=C1 VMJUDEOSVIYEMQ-SJORKVTESA-N 0.000 claims description 2
- ZZEULHDTBKKLTM-MSOLQXFVSA-N 5-[(2s)-1-[(2r)-4-benzoyl-2-methylpiperazin-1-yl]-1-oxopropan-2-yl]oxy-n-methylisoquinoline-1-carboxamide Chemical compound O=C([C@H](C)OC1=C2C=CN=C(C2=CC=C1)C(=O)NC)N([C@@H](C1)C)CCN1C(=O)C1=CC=CC=C1 ZZEULHDTBKKLTM-MSOLQXFVSA-N 0.000 claims description 2
- 150000001539 azetidines Chemical class 0.000 claims description 2
- 125000002619 bicyclic group Chemical group 0.000 claims description 2
- 125000001207 fluorophenyl group Chemical group 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000002950 monocyclic group Chemical group 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 125000002971 oxazolyl group Chemical group 0.000 claims description 2
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 2
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 2
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 2
- 125000000335 thiazolyl group Chemical group 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical class C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- LHWZXDKKFSHAAG-MOPGFXCFSA-N (2s)-1-[(2r)-4-benzoyl-2-methylpiperazin-1-yl]-2-[1-(1h-pyrazol-5-ylamino)isoquinolin-5-yl]oxypropan-1-one Chemical compound O([C@@H](C)C(=O)N1[C@@H](CN(CC1)C(=O)C=1C=CC=CC=1)C)C(C1=CC=N2)=CC=CC1=C2NC1=CC=NN1 LHWZXDKKFSHAAG-MOPGFXCFSA-N 0.000 claims 1
- QXBJKOAVZCBULE-SJORKVTESA-N (2s)-1-[(2r)-4-benzoyl-2-methylpiperazin-1-yl]-2-[8-chloro-2-(methylamino)quinolin-5-yl]oxypropan-1-one Chemical compound O=C([C@H](C)OC=1C2=CC=C(N=C2C(Cl)=CC=1)NC)N([C@@H](C1)C)CCN1C(=O)C1=CC=CC=C1 QXBJKOAVZCBULE-SJORKVTESA-N 0.000 claims 1
- MASAQSXMNRMCGV-SJORKVTESA-N 5-[(2s)-1-[(2r)-4-benzoyl-2-methylpiperazin-1-yl]-1-oxopropan-2-yl]oxy-n-ethyl-4-methoxypyridine-2-carboxamide Chemical compound C1=NC(C(=O)NCC)=CC(OC)=C1O[C@@H](C)C(=O)N1[C@H](C)CN(C(=O)C=2C=CC=CC=2)CC1 MASAQSXMNRMCGV-SJORKVTESA-N 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 176
- 239000000203 mixture Substances 0.000 abstract description 126
- 230000008569 process Effects 0.000 abstract description 10
- 239000000543 intermediate Substances 0.000 abstract description 8
- 230000003993 interaction Effects 0.000 abstract description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 375
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 183
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 159
- 239000000243 solution Substances 0.000 description 107
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 102
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 87
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 84
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 79
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 76
- 239000011541 reaction mixture Substances 0.000 description 73
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 64
- 239000007787 solid Substances 0.000 description 61
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 51
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 51
- 235000019341 magnesium sulphate Nutrition 0.000 description 51
- 230000002829 reductive effect Effects 0.000 description 51
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 49
- 239000000741 silica gel Substances 0.000 description 49
- 229910002027 silica gel Inorganic materials 0.000 description 49
- 238000004440 column chromatography Methods 0.000 description 48
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 42
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 42
- 239000002904 solvent Substances 0.000 description 38
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 34
- 239000003921 oil Substances 0.000 description 32
- 235000019198 oils Nutrition 0.000 description 32
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 31
- 239000012074 organic phase Substances 0.000 description 31
- 239000006260 foam Substances 0.000 description 29
- 238000009472 formulation Methods 0.000 description 29
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 24
- 239000002253 acid Substances 0.000 description 23
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 22
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical class OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 21
- 210000004027 cell Anatomy 0.000 description 21
- 239000000284 extract Substances 0.000 description 21
- 241000725303 Human immunodeficiency virus Species 0.000 description 20
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical class C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 19
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 18
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- 238000000746 purification Methods 0.000 description 17
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- 239000003795 chemical substances by application Substances 0.000 description 16
- 238000004128 high performance liquid chromatography Methods 0.000 description 16
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- 239000008346 aqueous phase Substances 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 15
- 239000000706 filtrate Substances 0.000 description 15
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 14
- 229910052739 hydrogen Inorganic materials 0.000 description 14
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 13
- 229940079593 drug Drugs 0.000 description 13
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 12
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 12
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 12
- 102100036011 T-cell surface glycoprotein CD4 Human genes 0.000 description 12
- 239000012267 brine Substances 0.000 description 12
- 238000010992 reflux Methods 0.000 description 12
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 12
- 238000005406 washing Methods 0.000 description 12
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 11
- 239000000725 suspension Substances 0.000 description 11
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
- 238000005481 NMR spectroscopy Methods 0.000 description 10
- 239000002585 base Substances 0.000 description 10
- 239000002552 dosage form Substances 0.000 description 10
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 9
- BCXBBYDLRSJZTE-SNVBAGLBSA-N [(3r)-3-methylpiperazin-1-yl]-phenylmethanone Chemical compound C1CN[C@H](C)CN1C(=O)C1=CC=CC=C1 BCXBBYDLRSJZTE-SNVBAGLBSA-N 0.000 description 9
- 229960000583 acetic acid Drugs 0.000 description 9
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- 239000000843 powder Substances 0.000 description 9
- 239000002244 precipitate Substances 0.000 description 9
- 239000000651 prodrug Substances 0.000 description 9
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- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 8
- 241000713772 Human immunodeficiency virus 1 Species 0.000 description 8
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- 229960001760 dimethyl sulfoxide Drugs 0.000 description 8
- LPEKGGXMPWTOCB-GSVOUGTGSA-N methyl (R)-lactate Chemical compound COC(=O)[C@@H](C)O LPEKGGXMPWTOCB-GSVOUGTGSA-N 0.000 description 8
- DDBKATBZHGPNRV-CVEARBPZSA-N methyl 5-[(2s)-1-[(2r)-4-benzoyl-2-methylpiperazin-1-yl]-1-oxopropan-2-yl]oxy-4-methoxypyridine-2-carboxylate Chemical compound C1=NC(C(=O)OC)=CC(OC)=C1O[C@@H](C)C(=O)N1[C@H](C)CN(C(=O)C=2C=CC=CC=2)CC1 DDBKATBZHGPNRV-CVEARBPZSA-N 0.000 description 8
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- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 8
- 108010050904 Interferons Proteins 0.000 description 7
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium on carbon Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
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- VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 description 7
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- 230000008878 coupling Effects 0.000 description 6
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- 239000003112 inhibitor Substances 0.000 description 6
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 6
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- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 5
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- 101710149870 C-C chemokine receptor type 5 Proteins 0.000 description 5
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- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
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- 125000000217 alkyl group Chemical group 0.000 description 5
- 150000001350 alkyl halides Chemical class 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 5
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Classifications
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
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- C04B35/00—Shaped ceramic products characterised by their composition; Ceramics compositions; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products
- C04B35/622—Forming processes; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products
- C04B35/626—Preparing or treating the powders individually or as batches ; preparing or treating macroscopic reinforcing agents for ceramic products, e.g. fibres; mechanical aspects section B
- C04B35/63—Preparing or treating the powders individually or as batches ; preparing or treating macroscopic reinforcing agents for ceramic products, e.g. fibres; mechanical aspects section B using additives specially adapted for forming the products, e.g.. binder binders
- C04B35/632—Organic additives
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
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- C07D215/22—Oxygen atoms attached in position 2 or 4
- C07D215/227—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 2
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- C07D215/24—Oxygen atoms attached in position 8
- C07D215/26—Alcohols; Ethers thereof
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- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/38—Nitrogen atoms
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- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Virology (AREA)
- Manufacturing & Machinery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Ceramic Engineering (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Molecular Biology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Inorganic Chemistry (AREA)
- Tropical Medicine & Parasitology (AREA)
- AIDS & HIV (AREA)
- Materials Engineering (AREA)
- Structural Engineering (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB0319149.1 | 2003-08-14 | ||
GB0319149A GB0319149D0 (en) | 2003-08-14 | 2003-08-14 | Chemical compounds |
GB0322153.8 | 2003-09-22 | ||
GB0322153A GB0322153D0 (en) | 2003-09-22 | 2003-09-22 | Chemical compounds |
GB0406656A GB0406656D0 (en) | 2004-03-24 | 2004-03-24 | Chemical compounds |
GB0406656.9 | 2004-03-24 | ||
PCT/IB2004/002562 WO2005016344A1 (en) | 2003-08-14 | 2004-08-04 | Piperazine derivatives for the treatment of hiv infections |
Publications (1)
Publication Number | Publication Date |
---|---|
CA2534866A1 true CA2534866A1 (en) | 2005-02-24 |
Family
ID=34198586
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA002534866A Abandoned CA2534866A1 (en) | 2003-08-14 | 2004-08-04 | Piperazine derivatives for the treatment of hiv infections |
Country Status (23)
Country | Link |
---|---|
EP (1) | EP1663234A1 (no) |
JP (1) | JP2007502266A (no) |
KR (1) | KR20060037442A (no) |
AP (1) | AP2006003514A0 (no) |
AR (1) | AR045931A1 (no) |
AU (1) | AU2004264724A1 (no) |
BR (1) | BRPI0413469A (no) |
CA (1) | CA2534866A1 (no) |
EA (1) | EA200600225A1 (no) |
EC (1) | ECSP066361A (no) |
IL (1) | IL173365A0 (no) |
IS (1) | IS8275A (no) |
MA (1) | MA27990A1 (no) |
MX (1) | MXPA06001762A (no) |
NL (1) | NL1026827C2 (no) |
NO (1) | NO20061170L (no) |
OA (1) | OA13235A (no) |
PA (1) | PA8608901A1 (no) |
PE (1) | PE20050867A1 (no) |
TN (1) | TNSN06051A1 (no) |
TW (1) | TW200512208A (no) |
UY (1) | UY28466A1 (no) |
WO (1) | WO2005016344A1 (no) |
Families Citing this family (36)
Publication number | Priority date | Publication date | Assignee | Title |
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TWI329105B (en) | 2002-02-01 | 2010-08-21 | Rigel Pharmaceuticals Inc | 2,4-pyrimidinediamine compounds and their uses |
RS53109B (en) | 2003-07-30 | 2014-06-30 | Rigel Pharmaceuticals Inc. | 2,4 PIRIMIDINDIAMINE COMPOUNDS FOR USE IN TREATMENT OR PREVENTION OF AUTOIMMUNE DISEASES |
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 |
FR2880887B1 (fr) * | 2005-01-14 | 2009-01-30 | Merck Sante Soc Par Actions Si | Derives d'hydroxyphenols, procedes pour leur preparation, compositions pharmaceutiques les contenant et applications en therapeutique |
WO2006085199A1 (en) * | 2005-02-14 | 2006-08-17 | Pfizer Limited | Piperazine derivatives |
NZ563454A (en) | 2005-06-08 | 2011-03-31 | Rigel Pharmaceuticals Inc | 2,4-diaminopyrimidine derivatives for inhibition of the JAK pathway |
US20070203161A1 (en) | 2006-02-24 | 2007-08-30 | Rigel Pharmaceuticals, Inc. | Compositions and methods for inhibition of the jak pathway |
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 |
EP1991532B1 (en) | 2006-02-24 | 2017-01-11 | Rigel Pharmaceuticals, Inc. | Compositions and methods for inhibition of the jak pathway |
US7807671B2 (en) | 2006-04-25 | 2010-10-05 | Bristol-Myers Squibb Company | Diketo-piperazine and piperidine derivatives as antiviral agents |
US7501419B2 (en) | 2006-04-25 | 2009-03-10 | Bristol-Myers Squibb Company | 4-Squarylpiperazine derivatives as antiviral agents |
US7572810B2 (en) | 2006-06-08 | 2009-08-11 | Bristol-Myers Squibb Company | Alkene piperidine derivatives as antiviral agents |
US7504399B2 (en) | 2006-06-08 | 2009-03-17 | Bristol-Meyers Squibb Company | Piperazine enamines as antiviral agents |
MX2010008926A (es) | 2008-02-15 | 2011-02-23 | Rigel Pharmaceuticals Inc | Compuestos de pirimidin-2-amina y su uso como inhibidores de jak cinasas. |
US8138339B2 (en) | 2008-04-16 | 2012-03-20 | Portola Pharmaceuticals, Inc. | Inhibitors of protein kinases |
ES2546502T3 (es) | 2008-04-16 | 2015-09-24 | Portola Pharmaceuticals, Inc. | 2,6-Diamino-pirimidin-5-il-carboxamidas como inhibidores de syk o JAK quinasas |
JP2011518219A (ja) | 2008-04-22 | 2011-06-23 | ポートラ ファーマシューティカルズ, インコーポレイテッド | タンパク質キナーゼの阻害剤 |
CN102131810B (zh) | 2008-06-25 | 2014-02-26 | 百时美施贵宝公司 | 作为抗hiv剂的二酮稠合的吡咯并哌啶类和吡咯并哌嗪类 |
CN102076686B (zh) | 2008-06-25 | 2013-03-06 | 百时美施贵宝公司 | 作为hiv附着抑制剂的二酮哌啶衍生物 |
US8450361B2 (en) | 2010-08-06 | 2013-05-28 | Bristol-Myers Squibb Company | Substituted indole and azaindole oxoacetyl piperazinamide derivatives |
EP2975027A1 (en) | 2010-11-01 | 2016-01-20 | Portola Pharmaceuticals, Inc. | Nicotinamides as jak kinase modulators |
US8912195B2 (en) | 2010-12-02 | 2014-12-16 | Bristol-Myers Squibb Company | Alkyl amides as HIV attachment inhibitors |
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 |
US8664213B2 (en) | 2011-08-29 | 2014-03-04 | Bristol-Myers Squibb Company | Spiro bicyclic diamine derivatives as HIV attachment inhibitors |
US8835454B2 (en) | 2011-08-29 | 2014-09-16 | Bristol-Myers Squibb Company | Fused bicyclic diamine derivatives as HIV attachment inhibitors |
US9359308B2 (en) | 2011-11-23 | 2016-06-07 | Portola Pharmaceuticals, Inc. | Pyrazine kinase inhibitors |
WO2013138436A1 (en) | 2012-03-14 | 2013-09-19 | Bristol-Myers Squibb Company | Cyclolic hydrazine 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 |
WO2014025852A1 (en) | 2012-08-09 | 2014-02-13 | Bristol-Myers Squibb Company | Tricyclic alkene derivatives as hiv attachment inhibitors |
WO2014058921A2 (en) | 2012-10-08 | 2014-04-17 | Portola Pharmaceuticals, Inc. | Substituted pyrimidinyl kinase inhibitors |
DK2968316T3 (da) | 2013-03-13 | 2019-10-07 | Forma Therapeutics Inc | 2-hydroxy-1-{4-[(4-phenylphenyl)carbonyl]piperazin-1-yl}ethan-1-on-derivater og relaterede forbindelser som fedtsyresyntase (fasn)-inhibitorer til behandlingen af cancer |
EP3250209B1 (en) | 2015-01-30 | 2023-09-13 | Lieber Institute For Brain Development | Comt inhibiting methods and compositions |
EP3380471B8 (en) | 2015-11-25 | 2022-01-19 | Lieber Institute Inc. DBA Lieber Institute For Brain Development | Tetrahydro-8h-pyrido[1,2-a]pyrazine-8-ones as comt inhibitors for the treatment of neurodegenerative disorders |
TWI767148B (zh) | 2018-10-10 | 2022-06-11 | 美商弗瑪治療公司 | 抑制脂肪酸合成酶(fasn) |
US10793554B2 (en) | 2018-10-29 | 2020-10-06 | Forma Therapeutics, Inc. | Solid forms of 4-(2-fluoro-4-(1-methyl-1H-benzo[d]imidazol-5-yl)benzoyl)piperazin-1-yl)(1-hydroxycyclopropyl)methanone |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR1397193A (fr) * | 1963-12-06 | 1965-04-30 | Lepetit Spa | Procédé de préparation de nouveaux dérivés de la pipérazine |
US3865828A (en) * | 1972-03-22 | 1975-02-11 | Egyt Gyogyszervegyeszeti Gyar | Pyridine derivatives having antidepressant activity |
JPS5139039A (ja) * | 1974-09-28 | 1976-04-01 | Mitsubishi Paper Mills Ltd | Karaayokankozairyo |
UA73553C2 (en) * | 2000-03-31 | 2005-08-15 | Pfizer Prod Inc | Piperazine derivatives |
US6573262B2 (en) * | 2000-07-10 | 2003-06-03 | Bristol-Myers Sqibb Company | Composition and antiviral activity of substituted indoleoxoacetic piperazine derivatives |
US6825201B2 (en) * | 2001-04-25 | 2004-11-30 | Bristol-Myers Squibb Company | Indole, azaindole and related heterocyclic amidopiperazine derivatives |
-
2004
- 2004-08-04 MX MXPA06001762A patent/MXPA06001762A/es not_active Application Discontinuation
- 2004-08-04 CA CA002534866A patent/CA2534866A1/en not_active Abandoned
- 2004-08-04 AP AP2006003514A patent/AP2006003514A0/xx unknown
- 2004-08-04 EA EA200600225A patent/EA200600225A1/ru unknown
- 2004-08-04 OA OA1200600049A patent/OA13235A/en unknown
- 2004-08-04 EP EP04744202A patent/EP1663234A1/en not_active Withdrawn
- 2004-08-04 AU AU2004264724A patent/AU2004264724A1/en not_active Abandoned
- 2004-08-04 KR KR1020067003015A patent/KR20060037442A/ko not_active Application Discontinuation
- 2004-08-04 BR BRPI0413469-9A patent/BRPI0413469A/pt not_active IP Right Cessation
- 2004-08-04 JP JP2006523071A patent/JP2007502266A/ja active Pending
- 2004-08-04 WO PCT/IB2004/002562 patent/WO2005016344A1/en not_active Application Discontinuation
- 2004-08-10 PE PE2004000779A patent/PE20050867A1/es not_active Application Discontinuation
- 2004-08-11 TW TW093124083A patent/TW200512208A/zh unknown
- 2004-08-12 NL NL1026827A patent/NL1026827C2/nl not_active IP Right Cessation
- 2004-08-12 PA PA20048608901A patent/PA8608901A1/es unknown
- 2004-08-12 AR ARP040102888A patent/AR045931A1/es unknown
- 2004-08-12 UY UY28466A patent/UY28466A1/es not_active Application Discontinuation
-
2006
- 2006-01-25 IL IL173365A patent/IL173365A0/en unknown
- 2006-01-31 IS IS8275A patent/IS8275A/is unknown
- 2006-02-13 EC EC2006006361A patent/ECSP066361A/es unknown
- 2006-02-14 TN TNP2006000051A patent/TNSN06051A1/fr unknown
- 2006-02-14 MA MA28803A patent/MA27990A1/fr unknown
- 2006-03-13 NO NO20061170A patent/NO20061170L/no not_active Application Discontinuation
Also Published As
Publication number | Publication date |
---|---|
AP2006003514A0 (en) | 2006-02-28 |
JP2007502266A (ja) | 2007-02-08 |
AU2004264724A1 (en) | 2005-02-24 |
MXPA06001762A (es) | 2006-05-12 |
UY28466A1 (es) | 2005-03-31 |
EA200600225A1 (ru) | 2006-08-25 |
PE20050867A1 (es) | 2005-11-10 |
OA13235A (en) | 2006-12-13 |
TNSN06051A1 (fr) | 2007-10-03 |
ECSP066361A (es) | 2006-08-30 |
PA8608901A1 (es) | 2005-03-03 |
NL1026827A1 (nl) | 2005-03-09 |
MA27990A1 (fr) | 2006-07-03 |
TW200512208A (en) | 2005-04-01 |
IL173365A0 (en) | 2006-06-11 |
WO2005016344A1 (en) | 2005-02-24 |
EP1663234A1 (en) | 2006-06-07 |
KR20060037442A (ko) | 2006-05-03 |
BRPI0413469A (pt) | 2006-10-17 |
NO20061170L (no) | 2006-05-15 |
AR045931A1 (es) | 2005-11-16 |
IS8275A (is) | 2006-01-31 |
NL1026827C2 (nl) | 2005-11-23 |
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Legal Events
Date | Code | Title | Description |
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EEER | Examination request | ||
FZDE | Discontinued |