NZ527193A - Composition and antiviral activity of substituted azaindoleoxoacetic piperazine derivatives - Google Patents

Info

Publication number

NZ527193A

NZ527193A NZ527193A NZ52719302A NZ527193A NZ 527193 A NZ527193 A NZ 527193A NZ 527193 A NZ527193 A NZ 527193A NZ 52719302 A NZ52719302 A NZ 52719302A NZ 527193 A NZ527193 A NZ 527193A

Authority

NZ

New Zealand

Prior art keywords

group

alkyl

heteroaryl

same

optionally substituted

Prior art date

2001-02-02

Links

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• 239000000203 mixture Substances 0.000 title claims description 38
• 230000000840 anti-viral effect Effects 0.000 title claims description 15
• 150000004885 piperazines Chemical class 0.000 title abstract description 21
• 229940066771 systemic antihistamines piperazine derivative Drugs 0.000 title description 6
• 238000011282 treatment Methods 0.000 claims abstract description 21
• 125000001072 heteroaryl group Chemical group 0.000 claims description 252
• 125000000217 alkyl group Chemical group 0.000 claims description 232
• 150000001875 compounds Chemical class 0.000 claims description 210
• 239000000543 intermediate Substances 0.000 claims description 208
• -1 alkynyl ketone Chemical class 0.000 claims description 206
• 229910052736 halogen Inorganic materials 0.000 claims description 200
• 150000002367 halogens Chemical class 0.000 claims description 190
• 238000000034 method Methods 0.000 claims description 186
• 229910052739 hydrogen Inorganic materials 0.000 claims description 150
• 239000001257 hydrogen Substances 0.000 claims description 135
• 125000003118 aryl group Chemical group 0.000 claims description 125
• 125000001424 substituent group Chemical group 0.000 claims description 123
• 238000006243 chemical reaction Methods 0.000 claims description 116
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 110
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 108
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 92
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 84
• 208000030507 AIDS Diseases 0.000 claims description 79
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 64
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 64
• BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 claims description 62
• 125000003545 alkoxy group Chemical group 0.000 claims description 60
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 59
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 58
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 58
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 52
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 48
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 45
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Chemical group C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 45
• KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical group C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 44
• 239000002904 solvent Substances 0.000 claims description 43
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 42
• 150000003839 salts Chemical class 0.000 claims description 40
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 39
• 125000000304 alkynyl group Chemical group 0.000 claims description 39
• 238000002360 preparation method Methods 0.000 claims description 39
• 125000001544 thienyl group Chemical group 0.000 claims description 39
• 125000003342 alkenyl group Chemical group 0.000 claims description 38
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 38
• 229910052757 nitrogen Inorganic materials 0.000 claims description 37
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 35
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 34
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical group C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 33
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 32
• 125000002541 furyl group Chemical group 0.000 claims description 32
• 125000004076 pyridyl group Chemical group 0.000 claims description 31
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical group C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 30
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 30
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 26
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 26
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 25
• 125000005309 thioalkoxy group Chemical group 0.000 claims description 25
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 24
• 125000005842 heteroatom Chemical group 0.000 claims description 24
• 125000004122 cyclic group Chemical group 0.000 claims description 23
• 125000002950 monocyclic group Chemical group 0.000 claims description 23
• WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 23
• PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Chemical group C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 22
• QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 22
• 229910052760 oxygen Inorganic materials 0.000 claims description 21
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical group C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 20
• 229910052799 carbon Inorganic materials 0.000 claims description 20
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 20
• 229910052717 sulfur Inorganic materials 0.000 claims description 20
• 208000015181 infectious disease Diseases 0.000 claims description 19
• 125000001153 fluoro group Chemical group F* 0.000 claims description 18
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 18
• 150000003852 triazoles Chemical group 0.000 claims description 18
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 17
• 125000004104 aryloxy group Chemical group 0.000 claims description 17
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 17
• 150000003536 tetrazoles Chemical group 0.000 claims description 17
• NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 claims description 16
• ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical group C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 16
• XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 claims description 16
• FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 15
• HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims description 15
• 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 15
• PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Chemical group CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 15
• RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Chemical group C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 15
• JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 14
• VIESAWGOYVNHLV-UHFFFAOYSA-N 1,3-dihydropyrrol-2-one Chemical compound O=C1CC=CN1 VIESAWGOYVNHLV-UHFFFAOYSA-N 0.000 claims description 14
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 14
• CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical group C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 14
• PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 14
• 125000006413 ring segment Chemical group 0.000 claims description 14
• 229910052796 boron Inorganic materials 0.000 claims description 13
• 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 13
• ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical group C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims description 13
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 13
• VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical group C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims description 13
• DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims description 12
• 125000004432 carbon atom Chemical group C* 0.000 claims description 12
• 125000005843 halogen group Chemical group 0.000 claims description 12
• 125000005553 heteroaryloxy group Chemical group 0.000 claims description 12
• 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 12
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 12
• 125000005296 thioaryloxy group Chemical group 0.000 claims description 12
• 125000002971 oxazolyl group Chemical group 0.000 claims description 11
• 125000005190 thiohydroxy group Chemical group 0.000 claims description 10
• HUTNOYOBQPAKIA-UHFFFAOYSA-N 1h-pyrazin-2-one Chemical compound OC1=CN=CC=N1 HUTNOYOBQPAKIA-UHFFFAOYSA-N 0.000 claims description 9
• 125000004429 atom Chemical group 0.000 claims description 9
• 239000003795 chemical substances by application Substances 0.000 claims description 9
• 125000002883 imidazolyl group Chemical group 0.000 claims description 9
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 9
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 9
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 9
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 9
• 125000000335 thiazolyl group Chemical group 0.000 claims description 9
• 125000005404 thioheteroaryloxy group Chemical group 0.000 claims description 9
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 8
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 8
• 239000003443 antiviral agent Substances 0.000 claims description 8
• QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 claims description 8
• 125000002619 bicyclic group Chemical group 0.000 claims description 8
• 239000008194 pharmaceutical composition Substances 0.000 claims description 8
• 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 8
• 125000004306 triazinyl group Chemical group 0.000 claims description 8
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 7
• 241000700605 Viruses Species 0.000 claims description 7
• 125000005499 phosphonyl group Chemical group 0.000 claims description 7
• 238000002560 therapeutic procedure Methods 0.000 claims description 7
• IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 claims description 6
• 229960005475 antiinfective agent Drugs 0.000 claims description 6
• 230000000694 effects Effects 0.000 claims description 6
• 239000002955 immunomodulating agent Substances 0.000 claims description 6
• 229940121354 immunomodulator Drugs 0.000 claims description 6
• 125000004193 piperazinyl group Chemical group 0.000 claims description 6
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
• 241000124008 Mammalia Species 0.000 claims description 5
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
• 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 5
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 5
• 150000001721 carbon Chemical group 0.000 claims description 5
• 239000002835 hiv fusion inhibitor Substances 0.000 claims description 5
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 5
• 125000001786 isothiazolyl group Chemical group 0.000 claims description 5
• 150000002545 isoxazoles Chemical class 0.000 claims description 5
• 239000001301 oxygen Substances 0.000 claims description 5
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 5
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 5
• 239000000725 suspension Substances 0.000 claims description 5
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
• 125000003107 substituted aryl group Chemical group 0.000 claims description 4
• 229940124530 sulfonamide Drugs 0.000 claims description 4
• 150000003456 sulfonamides Chemical class 0.000 claims description 4
• 239000011593 sulfur Substances 0.000 claims description 4
• 239000004599 antimicrobial Substances 0.000 claims description 3
• 239000000460 chlorine Substances 0.000 claims description 3
• 229910052801 chlorine Inorganic materials 0.000 claims description 3
• 229910052731 fluorine Inorganic materials 0.000 claims description 3
• 230000002584 immunomodulator Effects 0.000 claims description 3
• 229910052705 radium Inorganic materials 0.000 claims description 3
• 229910052701 rubidium Inorganic materials 0.000 claims description 3
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
• 150000002429 hydrazines Chemical class 0.000 claims description 2
• 230000002503 metabolic effect Effects 0.000 claims description 2
• RUZLIIJDZBWWSA-INIZCTEOSA-N methyl 2-[[(1s)-1-(7-methyl-2-morpholin-4-yl-4-oxopyrido[1,2-a]pyrimidin-9-yl)ethyl]amino]benzoate Chemical group COC(=O)C1=CC=CC=C1N[C@@H](C)C1=CC(C)=CN2C(=O)C=C(N3CCOCC3)N=C12 RUZLIIJDZBWWSA-INIZCTEOSA-N 0.000 claims description 2
• 231100000252 nontoxic Toxicity 0.000 claims description 2
• 230000003000 nontoxic effect Effects 0.000 claims description 2
• 150000003217 pyrazoles Chemical class 0.000 claims description 2
• 150000002431 hydrogen Chemical class 0.000 claims 13
• 230000037396 body weight Effects 0.000 claims 4
• PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 claims 2
• 229920000168 Microcrystalline cellulose Polymers 0.000 claims 2
• 229910003827 NRaRb Inorganic materials 0.000 claims 2
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims 2
• 239000003085 diluting agent Substances 0.000 claims 2
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 claims 2
• 229940016286 microcrystalline cellulose Drugs 0.000 claims 2
• 235000019813 microcrystalline cellulose Nutrition 0.000 claims 2
• 239000008108 microcrystalline cellulose Substances 0.000 claims 2
• 239000000825 pharmaceutical preparation Substances 0.000 claims 2
• 229940127557 pharmaceutical product Drugs 0.000 claims 2
• 239000000375 suspending agent Substances 0.000 claims 2
• WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims 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 claims 1
• LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims 1
• QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims 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 claims 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 claims 1
• 235000019739 Dicalciumphosphate Nutrition 0.000 claims 1
• MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 1
• 241000790917 Dioxys <bee> Species 0.000 claims 1
• 239000004606 Fillers/Extenders Substances 0.000 claims 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 claims 1
• 229930195725 Mannitol Natural products 0.000 claims 1
• 239000005642 Oleic acid Substances 0.000 claims 1
• ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims 1
• 241001415395 Spea Species 0.000 claims 1
• 229920002472 Starch Polymers 0.000 claims 1
• 235000010443 alginic acid Nutrition 0.000 claims 1
• 239000000783 alginic acid Substances 0.000 claims 1
• 229920000615 alginic acid Polymers 0.000 claims 1
• 229960001126 alginic acid Drugs 0.000 claims 1
• 150000004781 alginic acids Chemical class 0.000 claims 1
• 239000011230 binding agent Substances 0.000 claims 1
• 239000001506 calcium phosphate Substances 0.000 claims 1
• NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 claims 1
• 229940038472 dicalcium phosphate Drugs 0.000 claims 1
• 229910000390 dicalcium phosphate Inorganic materials 0.000 claims 1
• 235000005911 diet Nutrition 0.000 claims 1
• 230000037213 diet Effects 0.000 claims 1
• 235000014113 dietary fatty acids Nutrition 0.000 claims 1
• 239000007884 disintegrant Substances 0.000 claims 1
• 239000003937 drug carrier Substances 0.000 claims 1
• 239000000890 drug combination Substances 0.000 claims 1
• 239000003623 enhancer Substances 0.000 claims 1
• 230000029142 excretion Effects 0.000 claims 1
• 239000000194 fatty acid Substances 0.000 claims 1
• 229930195729 fatty acid Natural products 0.000 claims 1
• 150000004665 fatty acids Chemical class 0.000 claims 1
• 239000000796 flavoring agent Substances 0.000 claims 1
• 235000013355 food flavoring agent Nutrition 0.000 claims 1
• 150000002443 hydroxylamines Chemical class 0.000 claims 1
• 239000012729 immediate-release (IR) formulation Substances 0.000 claims 1
• QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims 1
• 239000008101 lactose Substances 0.000 claims 1
• 239000000314 lubricant Substances 0.000 claims 1
• 235000019359 magnesium stearate Nutrition 0.000 claims 1
• 239000000594 mannitol Substances 0.000 claims 1
• 235000010355 mannitol Nutrition 0.000 claims 1
• 229920000609 methyl cellulose Polymers 0.000 claims 1
• 239000001923 methylcellulose Substances 0.000 claims 1
• 239000007922 nasal spray Substances 0.000 claims 1
• 239000000346 nonvolatile oil Substances 0.000 claims 1
• ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims 1
• 239000000546 pharmaceutical excipient Substances 0.000 claims 1
• 239000000661 sodium alginate Substances 0.000 claims 1
• 235000010413 sodium alginate Nutrition 0.000 claims 1
• 229940005550 sodium alginate Drugs 0.000 claims 1
• 239000011780 sodium chloride Substances 0.000 claims 1
• 239000008107 starch Substances 0.000 claims 1
• 235000019698 starch Nutrition 0.000 claims 1
• 229940032147 starch Drugs 0.000 claims 1
• 239000000829 suppository Substances 0.000 claims 1
• 238000009736 wetting Methods 0.000 claims 1
• 239000000080 wetting agent Substances 0.000 claims 1
• 208000031886 HIV Infections Diseases 0.000 abstract description 33
• 208000037357 HIV infectious disease Diseases 0.000 abstract description 31
• 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 abstract description 31
• 239000003814 drug Substances 0.000 abstract description 20
• 208000036142 Viral infection Diseases 0.000 abstract description 2
• 230000009385 viral infection Effects 0.000 abstract description 2
• 238000004519 manufacturing process Methods 0.000 abstract 1
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 108
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 107
• 230000015572 biosynthetic process Effects 0.000 description 54
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 47
• 238000003786 synthesis reaction Methods 0.000 description 47
• 239000002253 acid Substances 0.000 description 46
• 125000000623 heterocyclic group Chemical group 0.000 description 45
• 238000004128 high performance liquid chromatography Methods 0.000 description 35
• 125000005334 azaindolyl group Chemical group N1N=C(C2=CC=CC=C12)* 0.000 description 33
• 238000005859 coupling reaction Methods 0.000 description 32
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 31
• 150000001299 aldehydes Chemical group 0.000 description 30
• 238000004949 mass spectrometry Methods 0.000 description 30
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 29
• 230000008878 coupling Effects 0.000 description 29
• 238000010168 coupling process Methods 0.000 description 29
• 230000014759 maintenance of location Effects 0.000 description 29
• 239000003153 chemical reaction reagent Substances 0.000 description 26
• 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 26
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