NO334095B1 - Ikke-Nukleoside Revers Transkriptase-Inhibitorer I for behandling av HIV-medierte sydommer - Google Patents

Info

Publication number

NO334095B1

NO334095B1 NO20054264A NO20054264A NO334095B1 NO 334095 B1 NO334095 B1 NO 334095B1 NO 20054264 A NO20054264 A NO 20054264A NO 20054264 A NO20054264 A NO 20054264A NO 334095 B1 NO334095 B1 NO 334095B1

Authority

NO

Norway

Prior art keywords

mmol

filtered

solution

added

give

Prior art date

2003-03-24

Links

• Espacenet
• Global Dossier
• Discuss

• 238000011282 treatment Methods 0.000 title claims description 27
• 201000010099 disease Diseases 0.000 title claims description 12
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims description 12
• 230000001404 mediated effect Effects 0.000 title claims description 10
• 229940042402 non-nucleoside reverse transcriptase inhibitor Drugs 0.000 title description 6
• 239000002726 nonnucleoside reverse transcriptase inhibitor Substances 0.000 title description 6
• 150000001875 compounds Chemical class 0.000 claims description 73
• 239000003814 drug Substances 0.000 claims description 18
• 241000725303 Human immunodeficiency virus Species 0.000 claims description 13
• 208000031886 HIV Infections Diseases 0.000 claims description 12
• 239000000825 pharmaceutical preparation Substances 0.000 claims description 11
• 208000037357 HIV infectious disease Diseases 0.000 claims description 10
• 229940079593 drug Drugs 0.000 claims description 10
• 229910052736 halogen Inorganic materials 0.000 claims description 10
• 150000002367 halogens Chemical class 0.000 claims description 10
• 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 claims description 10
• 150000003839 salts Chemical class 0.000 claims description 10
• 239000001257 hydrogen Substances 0.000 claims description 9
• 229910052739 hydrogen Inorganic materials 0.000 claims description 9
• 208000030507 AIDS Diseases 0.000 claims description 8
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
• 238000004519 manufacturing process Methods 0.000 claims description 6
• 230000002265 prevention Effects 0.000 claims description 6
• 239000003085 diluting agent Substances 0.000 claims description 5
• 229910052760 oxygen Inorganic materials 0.000 claims description 4
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
• 229910052717 sulfur Inorganic materials 0.000 claims description 4
• 239000003937 drug carrier Substances 0.000 claims description 3
• 125000005843 halogen group Chemical group 0.000 claims description 3
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 120
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 108
• 239000000243 solution Substances 0.000 description 87
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 85
• 235000019439 ethyl acetate Nutrition 0.000 description 59
• 239000000460 chlorine Substances 0.000 description 58
• 239000011541 reaction mixture Substances 0.000 description 58
• 239000000203 mixture Substances 0.000 description 51
• -1 benzoyl-substituted benzylpyridazinone compounds Chemical class 0.000 description 50
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 41
• 239000012267 brine Substances 0.000 description 39
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 39
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 38
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 32
• 239000007787 solid Substances 0.000 description 32
• 238000002360 preparation method Methods 0.000 description 31
• 239000012043 crude product Substances 0.000 description 27
• 239000011734 sodium Substances 0.000 description 27
• 238000000034 method Methods 0.000 description 22
• 239000000741 silica gel Substances 0.000 description 22
• 229910002027 silica gel Inorganic materials 0.000 description 22
• 238000006243 chemical reaction Methods 0.000 description 21
• 239000000284 extract Substances 0.000 description 21
• 125000000217 alkyl group Chemical group 0.000 description 19
• 238000009472 formulation Methods 0.000 description 19
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
• 239000002904 solvent Substances 0.000 description 18
• 239000000725 suspension Substances 0.000 description 18
• 230000015572 biosynthetic process Effects 0.000 description 17
• OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 17
• 238000010992 reflux Methods 0.000 description 17
• 238000003786 synthesis reaction Methods 0.000 description 16
• 239000000706 filtrate Substances 0.000 description 15
• 238000010898 silica gel chromatography Methods 0.000 description 15
• 229940122313 Nucleoside reverse transcriptase inhibitor Drugs 0.000 description 14
• 125000003118 aryl group Chemical group 0.000 description 14
• 239000002808 molecular sieve Substances 0.000 description 14
• 239000003419 rna directed dna polymerase inhibitor Substances 0.000 description 14
• URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 14
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
• 239000010410 layer Substances 0.000 description 13
• 239000012074 organic phase Substances 0.000 description 13
• 239000000843 powder Substances 0.000 description 13
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
• 239000004480 active ingredient Substances 0.000 description 12
• 125000001072 heteroaryl group Chemical group 0.000 description 12
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
• 125000000623 heterocyclic group Chemical group 0.000 description 11
• 239000003921 oil Substances 0.000 description 11
• 235000019198 oils Nutrition 0.000 description 11
• HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 11
• 125000001424 substituent group Chemical group 0.000 description 11
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
• 229910004373 HOAc Inorganic materials 0.000 description 10
• 102100034343 Integrase Human genes 0.000 description 10
• PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 10
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
• ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 10
• 239000002775 capsule Substances 0.000 description 10
• 150000001987 diarylethers Chemical class 0.000 description 10
• 229920006395 saturated elastomer Polymers 0.000 description 10
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
• 108010092799 RNA-directed DNA polymerase Proteins 0.000 description 9
• 239000002253 acid Substances 0.000 description 9
• 125000002252 acyl group Chemical group 0.000 description 9
• 238000004587 chromatography analysis Methods 0.000 description 9
• KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 9
• 239000000047 product Substances 0.000 description 9
• 239000007858 starting material Substances 0.000 description 9
• 239000003826 tablet Substances 0.000 description 9
• 239000007864 aqueous solution Substances 0.000 description 8
• 238000005859 coupling reaction Methods 0.000 description 8
• 239000002552 dosage form Substances 0.000 description 8
• 229910052757 nitrogen Inorganic materials 0.000 description 8
• 238000004809 thin layer chromatography Methods 0.000 description 8
• DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
• ZMANZCXQSJIPKH-UHFFFAOYSA-N N,N-Diethylethanamine Substances CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 7
• 125000004453 alkoxycarbonyl group Chemical group 0.000 description 7
• 125000004432 carbon atom Chemical group C* 0.000 description 7
• 230000008878 coupling Effects 0.000 description 7
• 238000010168 coupling process Methods 0.000 description 7
• 239000004615 ingredient Substances 0.000 description 7
• 239000003112 inhibitor Substances 0.000 description 7
• 239000000463 material Substances 0.000 description 7
• WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 7
• 239000003039 volatile agent Substances 0.000 description 7
• YRAJNWYBUCUFBD-UHFFFAOYSA-N 2,2,6,6-tetramethylheptane-3,5-dione Chemical compound CC(C)(C)C(=O)CC(=O)C(C)(C)C YRAJNWYBUCUFBD-UHFFFAOYSA-N 0.000 description 6
• WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
• 125000004104 aryloxy group Chemical group 0.000 description 6
• 239000012230 colorless oil Substances 0.000 description 6
• 239000000839 emulsion Substances 0.000 description 6
• 125000001188 haloalkyl group Chemical group 0.000 description 6
• 150000002825 nitriles Chemical class 0.000 description 6
• 239000012299 nitrogen atmosphere Substances 0.000 description 6
• 239000012044 organic layer Substances 0.000 description 6
• 239000000546 pharmaceutical excipient Substances 0.000 description 6
• 230000009467 reduction Effects 0.000 description 6
• 229910052938 sodium sulfate Inorganic materials 0.000 description 6
• 235000011152 sodium sulphate Nutrition 0.000 description 6
• 238000006467 substitution reaction Methods 0.000 description 6
• 238000002560 therapeutic procedure Methods 0.000 description 6
• WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 6
• 230000003612 virological effect Effects 0.000 description 6
• 206010001513 AIDS related complex Diseases 0.000 description 5
• 108010078851 HIV Reverse Transcriptase Proteins 0.000 description 5
• 125000005118 N-alkylcarbamoyl group Chemical group 0.000 description 5
• 239000007832 Na2SO4 Substances 0.000 description 5
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
• 125000003282 alkyl amino group Chemical group 0.000 description 5
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 5
• 125000004663 dialkyl amino group Chemical group 0.000 description 5
• 230000000694 effects Effects 0.000 description 5
• RSZHYFRZHOICLC-UHFFFAOYSA-N ethyl 2-(3-hydroxy-4,5-dimethylphenyl)acetate Chemical compound CCOC(=O)CC1=CC(C)=C(C)C(O)=C1 RSZHYFRZHOICLC-UHFFFAOYSA-N 0.000 description 5
• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
• 239000000543 intermediate Substances 0.000 description 5
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 5
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 5
• 238000000746 purification Methods 0.000 description 5
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
• 150000003254 radicals Chemical class 0.000 description 5
• 230000002829 reductive effect Effects 0.000 description 5
• 239000007921 spray Substances 0.000 description 5
• 238000003756 stirring Methods 0.000 description 5
• 239000000829 suppository Substances 0.000 description 5
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 description 4
• KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 4
• HBEDSQVIWPRPAY-UHFFFAOYSA-N 2,3-dihydrobenzofuran Chemical compound C1=CC=C2OCCC2=C1 HBEDSQVIWPRPAY-UHFFFAOYSA-N 0.000 description 4
• RIERSGULWXEJKL-UHFFFAOYSA-N 3-hydroxy-2-methylbenzoic acid Chemical compound CC1=C(O)C=CC=C1C(O)=O RIERSGULWXEJKL-UHFFFAOYSA-N 0.000 description 4
• HCZRPIVKIPIGDM-UHFFFAOYSA-N 6-chloro-2-fluoro-3-methylphenol Chemical compound CC1=CC=C(Cl)C(O)=C1F HCZRPIVKIPIGDM-UHFFFAOYSA-N 0.000 description 4
• DYHSDKLCOJIUFX-UHFFFAOYSA-N Di-tert-butyl dicarbonate Substances CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 4
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
• 150000007513 acids Chemical class 0.000 description 4
• 125000003545 alkoxy group Chemical group 0.000 description 4
• 125000000266 alpha-aminoacyl group Chemical group 0.000 description 4
• 239000008346 aqueous phase Substances 0.000 description 4
• 230000037396 body weight Effects 0.000 description 4
• 230000031709 bromination Effects 0.000 description 4
• 238000005893 bromination reaction Methods 0.000 description 4
• 239000000969 carrier Substances 0.000 description 4
• HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 4
• 238000002648 combination therapy Methods 0.000 description 4
• 125000004093 cyano group Chemical group *C#N 0.000 description 4
• 230000017858 demethylation Effects 0.000 description 4
• 238000010520 demethylation reaction Methods 0.000 description 4
• CSJLBAMHHLJAAS-UHFFFAOYSA-N diethylaminosulfur trifluoride Chemical compound CCN(CC)S(F)(F)F CSJLBAMHHLJAAS-UHFFFAOYSA-N 0.000 description 4
• AYFUSKRBXHFKCU-UHFFFAOYSA-N ethyl 2-(4-chloro-3-hydroxyphenyl)acetate Chemical compound CCOC(=O)CC1=CC=C(Cl)C(O)=C1 AYFUSKRBXHFKCU-UHFFFAOYSA-N 0.000 description 4
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
• 230000001965 increasing effect Effects 0.000 description 4
• 239000007788 liquid Substances 0.000 description 4
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
• 230000004048 modification Effects 0.000 description 4
• 238000012986 modification Methods 0.000 description 4
• 239000007922 nasal spray Substances 0.000 description 4
• 229940097496 nasal spray Drugs 0.000 description 4
• 230000008569 process Effects 0.000 description 4
• MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 4
• 239000003381 stabilizer Substances 0.000 description 4
• 239000000126 substance Substances 0.000 description 4
• KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 4
• 239000000375 suspending agent Substances 0.000 description 4
• 239000002562 thickening agent Substances 0.000 description 4
• SDEAGACSNFSZCU-UHFFFAOYSA-N (3-chlorophenyl)boronic acid Chemical compound OB(O)C1=CC=CC(Cl)=C1 SDEAGACSNFSZCU-UHFFFAOYSA-N 0.000 description 3
• WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
• OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 3
• NTEZWIQFQYKLJI-UHFFFAOYSA-N 2-[3-(3-bromo-5-fluorophenoxy)-4-chlorophenyl]acetonitrile Chemical compound FC1=CC(Br)=CC(OC=2C(=CC=C(CC#N)C=2)Cl)=C1 NTEZWIQFQYKLJI-UHFFFAOYSA-N 0.000 description 3
• DBWPADILUQENLH-UHFFFAOYSA-N 2-bromo-1,3-dichloro-4-methylbenzene Chemical compound CC1=CC=C(Cl)C(Br)=C1Cl DBWPADILUQENLH-UHFFFAOYSA-N 0.000 description 3
• FEVGECIVWRLFRP-UHFFFAOYSA-N 3-[[4-chloro-3-(2-chlorophenoxy)phenyl]methyl]-4-methyl-1h-1,2,4-triazol-5-one Chemical compound N1C(=O)N(C)C(CC=2C=C(OC=3C(=CC=CC=3)Cl)C(Cl)=CC=2)=N1 FEVGECIVWRLFRP-UHFFFAOYSA-N 0.000 description 3
• JGHSLPPKDMNNPS-UHFFFAOYSA-N 5-[[4-chloro-3-(2-chlorophenoxy)phenyl]methyl]-3h-1,3,4-thiadiazol-2-one Chemical compound ClC1=CC=CC=C1OC1=CC(CC=2SC(=O)NN=2)=CC=C1Cl JGHSLPPKDMNNPS-UHFFFAOYSA-N 0.000 description 3
• OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 3
• 239000004342 Benzoyl peroxide Substances 0.000 description 3
• OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 3
• CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical group O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 3
• VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical class [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 description 3
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
• 102000004190 Enzymes Human genes 0.000 description 3
• 108090000790 Enzymes Proteins 0.000 description 3
• 108010010803 Gelatin Proteins 0.000 description 3
• 229920000084 Gum arabic Polymers 0.000 description 3
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
• BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 3
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
• 108091005804 Peptidases Proteins 0.000 description 3
• 239000004365 Protease Substances 0.000 description 3
• 102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 description 3
• 241000700605 Viruses Species 0.000 description 3
• 235000010489 acacia gum Nutrition 0.000 description 3
• DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 3
• WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 3
• 125000004390 alkyl sulfonyl group Chemical group 0.000 description 3
• 125000004414 alkyl thio group Chemical group 0.000 description 3
• 230000000840 anti-viral effect Effects 0.000 description 3
• 239000007900 aqueous suspension Substances 0.000 description 3
• 125000003710 aryl alkyl group Chemical group 0.000 description 3
• 150000008378 aryl ethers Chemical class 0.000 description 3
• 239000012298 atmosphere Substances 0.000 description 3
• 235000019400 benzoyl peroxide Nutrition 0.000 description 3
• 239000001768 carboxy methyl cellulose Substances 0.000 description 3
• 239000003795 chemical substances by application Substances 0.000 description 3
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
• 238000007796 conventional method Methods 0.000 description 3
• 239000006071 cream Substances 0.000 description 3
• DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 3
• 239000002270 dispersing agent Substances 0.000 description 3
• 239000003995 emulsifying agent Substances 0.000 description 3
• JAPDFCINMIJCKL-UHFFFAOYSA-N ethyl 2-(3-hydroxy-4-methylphenyl)acetate Chemical compound CCOC(=O)CC1=CC=C(C)C(O)=C1 JAPDFCINMIJCKL-UHFFFAOYSA-N 0.000 description 3
• VKVKRXYUIUTHAT-UHFFFAOYSA-N ethyl 2-(3-hydroxy-4-propan-2-ylphenyl)acetate Chemical compound CCOC(=O)CC1=CC=C(C(C)C)C(O)=C1 VKVKRXYUIUTHAT-UHFFFAOYSA-N 0.000 description 3
• 239000008273 gelatin Substances 0.000 description 3
• 229920000159 gelatin Polymers 0.000 description 3
• 235000019322 gelatine Nutrition 0.000 description 3
• 235000011852 gelatine desserts Nutrition 0.000 description 3
• 125000005842 heteroatom Chemical group 0.000 description 3
• 238000002347 injection Methods 0.000 description 3
• 239000007924 injection Substances 0.000 description 3
• 239000012669 liquid formulation Substances 0.000 description 3
• 239000007937 lozenge Substances 0.000 description 3
• 125000002950 monocyclic group Chemical group 0.000 description 3
• 125000004433 nitrogen atom Chemical group N* 0.000 description 3
• 150000002989 phenols Chemical class 0.000 description 3
• 239000002243 precursor Substances 0.000 description 3
• 239000003755 preservative agent Substances 0.000 description 3
• 230000035945 sensitivity Effects 0.000 description 3
• 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 3
• 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 3
• 239000000758 substrate Substances 0.000 description 3
• 208000024891 symptom Diseases 0.000 description 3
• 239000006188 syrup Substances 0.000 description 3
• 235000020357 syrup Nutrition 0.000 description 3
• 230000001225 therapeutic effect Effects 0.000 description 3
• AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 3
• 239000003981 vehicle Substances 0.000 description 3
• NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 2
• AFSSVCNPDKKSRR-UHFFFAOYSA-N (3-bromophenyl)boronic acid Chemical compound OB(O)C1=CC=CC(Br)=C1 AFSSVCNPDKKSRR-UHFFFAOYSA-N 0.000 description 2
• 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 description 2
• 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 description 2
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 description 2
• IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
• KBRLTYHUJDMMLI-UHFFFAOYSA-N 1-chloro-2-methoxy-4-methylbenzene Chemical compound COC1=CC(C)=CC=C1Cl KBRLTYHUJDMMLI-UHFFFAOYSA-N 0.000 description 2
• OJTCZLWBSWYHJU-UHFFFAOYSA-N 1-chloro-3-fluoro-4-methyl-2-phenoxybenzene Chemical compound CC1=CC=C(Cl)C(OC=2C=CC=CC=2)=C1F OJTCZLWBSWYHJU-UHFFFAOYSA-N 0.000 description 2
• IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 2
• AQJFATAFTQCRGC-UHFFFAOYSA-N 2-Chloro-4-methylphenol Chemical compound CC1=CC=C(O)C(Cl)=C1 AQJFATAFTQCRGC-UHFFFAOYSA-N 0.000 description 2
• SMFHPCZZAAMJJO-UHFFFAOYSA-N 2-chloro-5-methylphenol Chemical compound CC1=CC=C(Cl)C(O)=C1 SMFHPCZZAAMJJO-UHFFFAOYSA-N 0.000 description 2
• CQXZSEXZQVKCHW-UHFFFAOYSA-N 3,5-difluorobenzonitrile Chemical compound FC1=CC(F)=CC(C#N)=C1 CQXZSEXZQVKCHW-UHFFFAOYSA-N 0.000 description 2
• FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 2
• OVZHELCFKSFINS-UHFFFAOYSA-N 3h-1,3,4-thiadiazol-2-one Chemical class O=C1NN=CS1 OVZHELCFKSFINS-UHFFFAOYSA-N 0.000 description 2
• WNEJYQLUYFVDMN-UHFFFAOYSA-N 5-[(4-chloro-3-phenoxyphenyl)methyl]-3h-1,3,4-oxadiazol-2-one Chemical compound C1=C(OC=2C=CC=CC=2)C(Cl)=CC=C1CC1=NNC(=O)O1 WNEJYQLUYFVDMN-UHFFFAOYSA-N 0.000 description 2
• AMKGKYQBASDDJB-UHFFFAOYSA-N 9$l^{2}-borabicyclo[3.3.1]nonane Chemical compound C1CCC2CCCC1[B]2 AMKGKYQBASDDJB-UHFFFAOYSA-N 0.000 description 2
• 244000215068 Acacia senegal Species 0.000 description 2
• 235000006491 Acacia senegal Nutrition 0.000 description 2
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 2
• 241000416162 Astragalus gummifer Species 0.000 description 2
• 229910021591 Copper(I) chloride Inorganic materials 0.000 description 2
• XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 2
• VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
• 241000282412 Homo Species 0.000 description 2
• 241000713772 Human immunodeficiency virus 1 Species 0.000 description 2
• GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
• TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
• 241001465754 Metazoa Species 0.000 description 2
• 239000012359 Methanesulfonyl chloride Substances 0.000 description 2
• 229910019093 NaOCl Inorganic materials 0.000 description 2
• 229910002666 PdCl2 Inorganic materials 0.000 description 2
• YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
• 239000002202 Polyethylene glycol Substances 0.000 description 2
• 229920002472 Starch Polymers 0.000 description 2
• 229930006000 Sucrose Natural products 0.000 description 2
• CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
• 229920001615 Tragacanth Polymers 0.000 description 2
• 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 2
• 239000012346 acetyl chloride Substances 0.000 description 2
• 239000013543 active substance Substances 0.000 description 2
• 239000000443 aerosol Substances 0.000 description 2
• 125000004471 alkyl aminosulfonyl group Chemical group 0.000 description 2
• 125000002947 alkylene group Chemical group 0.000 description 2
• 239000003443 antiviral agent Substances 0.000 description 2
• 150000001543 aryl boronic acids Chemical class 0.000 description 2
• 150000001502 aryl halides Chemical class 0.000 description 2
• 125000005135 aryl sulfinyl group Chemical group 0.000 description 2
• 238000006254 arylation reaction Methods 0.000 description 2
• 238000003556 assay Methods 0.000 description 2
• 125000004429 atom Chemical group 0.000 description 2
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
• 235000019445 benzyl alcohol Nutrition 0.000 description 2
• 229960004217 benzyl alcohol Drugs 0.000 description 2
• KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 2
• 229940073608 benzyl chloride Drugs 0.000 description 2
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
• 125000001743 benzylic group Chemical group 0.000 description 2
• 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 2
• ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 2
• 125000002837 carbocyclic group Chemical group 0.000 description 2
• 229910052799 carbon Inorganic materials 0.000 description 2
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
• 239000003054 catalyst Substances 0.000 description 2
• 239000003153 chemical reaction reagent Substances 0.000 description 2
• 229940110456 cocoa butter Drugs 0.000 description 2
• 235000019868 cocoa butter Nutrition 0.000 description 2
• 238000009833 condensation Methods 0.000 description 2
• 230000005494 condensation Effects 0.000 description 2
• 239000010949 copper Substances 0.000 description 2
• OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 2
• ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 2
• NHVNXKFIZYSCEB-XLPZGREQSA-N dTTP Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](O)C1 NHVNXKFIZYSCEB-XLPZGREQSA-N 0.000 description 2
• 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 2
• 239000012973 diazabicyclooctane Substances 0.000 description 2
• FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 2
• CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 2
• 230000032050 esterification Effects 0.000 description 2
• 238000005886 esterification reaction Methods 0.000 description 2
• 150000002148 esters Chemical class 0.000 description 2
• LDSSZAKPTWIXGJ-UHFFFAOYSA-N ethyl 2-(4-ethyl-3-hydroxyphenyl)acetate Chemical compound CCOC(=O)CC1=CC=C(CC)C(O)=C1 LDSSZAKPTWIXGJ-UHFFFAOYSA-N 0.000 description 2
• AWPMWZHWVKXADV-UHFFFAOYSA-N ethyl 2-(4-hydroxy-3-methoxyphenyl)acetate Chemical compound CCOC(=O)CC1=CC=C(O)C(OC)=C1 AWPMWZHWVKXADV-UHFFFAOYSA-N 0.000 description 2
• WUDNUHPRLBTKOJ-UHFFFAOYSA-N ethyl isocyanate Chemical compound CCN=C=O WUDNUHPRLBTKOJ-UHFFFAOYSA-N 0.000 description 2
• 238000013265 extended release Methods 0.000 description 2
• 239000012065 filter cake Substances 0.000 description 2
• 238000001914 filtration Methods 0.000 description 2
• 238000003818 flash chromatography Methods 0.000 description 2
• 239000000796 flavoring agent Substances 0.000 description 2
• 125000002541 furyl group Chemical group 0.000 description 2
• 239000000499 gel Substances 0.000 description 2
• 125000004438 haloalkoxy group Chemical group 0.000 description 2
• 125000004995 haloalkylthio group Chemical group 0.000 description 2
• 125000005553 heteroaryloxy group Chemical group 0.000 description 2
• 150000002391 heterocyclic compounds Chemical class 0.000 description 2
• VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 2
• QRMZSPFSDQBLIX-UHFFFAOYSA-N homovanillic acid Chemical compound COC1=CC(CC(O)=O)=CC=C1O QRMZSPFSDQBLIX-UHFFFAOYSA-N 0.000 description 2
• IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
• 125000004356 hydroxy functional group Chemical group O* 0.000 description 2
• 208000015181 infectious disease Diseases 0.000 description 2
• 238000001802 infusion Methods 0.000 description 2
• 230000005764 inhibitory process Effects 0.000 description 2
• 238000001990 intravenous administration Methods 0.000 description 2
• 229910052740 iodine Inorganic materials 0.000 description 2
• 125000000842 isoxazolyl group Chemical group 0.000 description 2
• 125000000468 ketone group Chemical group 0.000 description 2
• 150000002576 ketones Chemical class 0.000 description 2
• 239000008101 lactose Substances 0.000 description 2
• JTEGQNOMFQHVDC-NKWVEPMBSA-N lamivudine Chemical compound O=C1N=C(N)C=CN1[C@H]1O[C@@H](CO)SC1 JTEGQNOMFQHVDC-NKWVEPMBSA-N 0.000 description 2
• 235000010445 lecithin Nutrition 0.000 description 2
• 239000000787 lecithin Substances 0.000 description 2
• 229940067606 lecithin Drugs 0.000 description 2
• KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
• 239000006210 lotion Substances 0.000 description 2
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
• 238000002844 melting Methods 0.000 description 2
• 239000012528 membrane Substances 0.000 description 2
• 238000003328 mesylation reaction Methods 0.000 description 2
• QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
• 229920000609 methyl cellulose Polymers 0.000 description 2
• 239000001923 methylcellulose Substances 0.000 description 2
• 235000010981 methylcellulose Nutrition 0.000 description 2
• 210000003928 nasal cavity Anatomy 0.000 description 2
• NQDJXKOVJZTUJA-UHFFFAOYSA-N nevirapine Chemical compound C12=NC=CC=C2C(=O)NC=2C(C)=CC=NC=2N1C1CC1 NQDJXKOVJZTUJA-UHFFFAOYSA-N 0.000 description 2
• 231100000252 nontoxic Toxicity 0.000 description 2
• 230000003000 nontoxic effect Effects 0.000 description 2
• 150000003833 nucleoside derivatives Chemical class 0.000 description 2
• 239000002674 ointment Substances 0.000 description 2
• ZVTQYRVARPYRRE-UHFFFAOYSA-N oxadiazol-4-one Chemical compound O=C1CON=N1 ZVTQYRVARPYRRE-UHFFFAOYSA-N 0.000 description 2
• 125000004043 oxo group Chemical group O=* 0.000 description 2
• PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 2
• 239000002245 particle Substances 0.000 description 2
• 229920001223 polyethylene glycol Polymers 0.000 description 2
• 229920006316 polyvinylpyrrolidine Polymers 0.000 description 2
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
• 239000002244 precipitate Substances 0.000 description 2
• LEHBURLTIWGHEM-UHFFFAOYSA-N pyridinium chlorochromate Chemical compound [O-][Cr](Cl)(=O)=O.C1=CC=[NH+]C=C1 LEHBURLTIWGHEM-UHFFFAOYSA-N 0.000 description 2
• 125000000714 pyrimidinyl group Chemical group 0.000 description 2
• 238000002976 reverse transcriptase assay Methods 0.000 description 2
• 238000007363 ring formation reaction Methods 0.000 description 2
• YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
• 238000009097 single-agent therapy Methods 0.000 description 2
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
• 235000017557 sodium bicarbonate Nutrition 0.000 description 2
• 239000011780 sodium chloride Substances 0.000 description 2
• SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 2
• 239000008107 starch Substances 0.000 description 2
• 235000019698 starch Nutrition 0.000 description 2
• 238000007920 subcutaneous administration Methods 0.000 description 2
• 125000003107 substituted aryl group Chemical group 0.000 description 2
• 229960002317 succinimide Drugs 0.000 description 2
• 239000005720 sucrose Substances 0.000 description 2
• 238000013268 sustained release Methods 0.000 description 2
• 239000012730 sustained-release form Substances 0.000 description 2
• VCMJCVGFSROFHV-WZGZYPNHSA-N tenofovir disoproxil fumarate Chemical compound OC(=O)\C=C\C(O)=O.N1=CN=C2N(C[C@@H](C)OCP(=O)(OCOC(=O)OC(C)C)OCOC(=O)OC(C)C)C=NC2=C1N VCMJCVGFSROFHV-WZGZYPNHSA-N 0.000 description 2
• VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
• 125000001544 thienyl group Chemical group 0.000 description 2
• 230000000929 thyromimetic effect Effects 0.000 description 2
• FWPIDFUJEMBDLS-UHFFFAOYSA-L tin(II) chloride dihydrate Chemical compound O.O.Cl[Sn]Cl FWPIDFUJEMBDLS-UHFFFAOYSA-L 0.000 description 2
• 230000000699 topical effect Effects 0.000 description 2
• 235000010487 tragacanth Nutrition 0.000 description 2
• 239000000196 tragacanth Substances 0.000 description 2
• 229940116362 tragacanth Drugs 0.000 description 2
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
• 230000009466 transformation Effects 0.000 description 2
• FFSJPOPLSWBGQY-UHFFFAOYSA-N triazol-4-one Chemical class O=C1C=NN=N1 FFSJPOPLSWBGQY-UHFFFAOYSA-N 0.000 description 2
• 239000008215 water for injection Substances 0.000 description 2
• 229960002555 zidovudine Drugs 0.000 description 2
• 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 2
• JRPGMCRJPQJYPE-UHFFFAOYSA-N zinc;carbanide Chemical group [CH3-].[CH3-].[Zn+2] JRPGMCRJPQJYPE-UHFFFAOYSA-N 0.000 description 2
• RRCMGJCFMJBHQC-UHFFFAOYSA-N (2-chlorophenyl)boronic acid Chemical compound OB(O)C1=CC=CC=C1Cl RRCMGJCFMJBHQC-UHFFFAOYSA-N 0.000 description 1
• UERNRFHISLXQFU-DFWYDOINSA-N (2S)-5-oxopyrrolidine-2-carboxylic acid pyridine Chemical compound c1ccncc1.OC(=O)[C@@H]1CCC(=O)N1 UERNRFHISLXQFU-DFWYDOINSA-N 0.000 description 1
• QBLFZIBJXUQVRF-UHFFFAOYSA-N (4-bromophenyl)boronic acid Chemical compound OB(O)C1=CC=C(Br)C=C1 QBLFZIBJXUQVRF-UHFFFAOYSA-N 0.000 description 1
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 1
• BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
• ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 1
• DDMOUSALMHHKOS-UHFFFAOYSA-N 1,2-dichloro-1,1,2,2-tetrafluoroethane Chemical compound FC(F)(Cl)C(F)(F)Cl DDMOUSALMHHKOS-UHFFFAOYSA-N 0.000 description 1
• 150000005072 1,3,4-oxadiazoles Chemical class 0.000 description 1
• GPPYYGWYUFOWSR-UHFFFAOYSA-N 1,3-dibromo-2-fluorobenzene Chemical compound FC1=C(Br)C=CC=C1Br GPPYYGWYUFOWSR-UHFFFAOYSA-N 0.000 description 1
• OINVKXKWZXMAEO-UHFFFAOYSA-N 1,3-dichloro-4-methyl-2-phenoxybenzene Chemical compound CC1=CC=C(Cl)C(OC=2C=CC=CC=2)=C1Cl OINVKXKWZXMAEO-UHFFFAOYSA-N 0.000 description 1
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
• LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 1
• MICMHFIQSAMEJG-UHFFFAOYSA-N 1-bromopyrrolidine-2,5-dione Chemical compound BrN1C(=O)CCC1=O.BrN1C(=O)CCC1=O MICMHFIQSAMEJG-UHFFFAOYSA-N 0.000 description 1
• MPEOPBCQHNWNFB-UHFFFAOYSA-N 1-chloro-2-iodobenzene Chemical compound ClC1=CC=CC=C1I MPEOPBCQHNWNFB-UHFFFAOYSA-N 0.000 description 1
• GURVMPKVXURGHI-UHFFFAOYSA-N 1-chloro-4-methyl-2-phenoxybenzene Chemical compound CC1=CC=C(Cl)C(OC=2C=CC=CC=2)=C1 GURVMPKVXURGHI-UHFFFAOYSA-N 0.000 description 1
• 125000001478 1-chloroethyl group Chemical group [H]C([H])([H])C([H])(Cl)* 0.000 description 1
• NFDXQGNDWIPXQL-UHFFFAOYSA-N 1-cyclooctyldiazocane Chemical compound C1CCCCCCC1N1NCCCCCC1 NFDXQGNDWIPXQL-UHFFFAOYSA-N 0.000 description 1
• AXTGDCSMTYGJND-UHFFFAOYSA-N 1-dodecylazepan-2-one Chemical compound CCCCCCCCCCCCN1CCCCCC1=O AXTGDCSMTYGJND-UHFFFAOYSA-N 0.000 description 1
• WFQDTOYDVUWQMS-UHFFFAOYSA-N 1-fluoro-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(F)C=C1 WFQDTOYDVUWQMS-UHFFFAOYSA-N 0.000 description 1
• 125000004776 1-fluoroethyl group Chemical group [H]C([H])([H])C([H])(F)* 0.000 description 1
• 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
• YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
• RYRLLAOLJVDVNN-UHFFFAOYSA-N 2,2,2-trifluoroethanethiol Chemical compound FC(F)(F)CS RYRLLAOLJVDVNN-UHFFFAOYSA-N 0.000 description 1
• 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
• JVSDZAGCHKCSGR-UHFFFAOYSA-N 2,5-dichloropyrazine Chemical compound ClC1=CN=C(Cl)C=N1 JVSDZAGCHKCSGR-UHFFFAOYSA-N 0.000 description 1
• PQEGHSRDYPYKKO-UHFFFAOYSA-N 2-(3-hydroxy-1-benzofuran-2-yl)acetic acid Chemical compound C1=CC=C2C(O)=C(CC(=O)O)OC2=C1 PQEGHSRDYPYKKO-UHFFFAOYSA-N 0.000 description 1
• QAOJXZSPCDKVBM-UHFFFAOYSA-N 2-(3-hydroxy-4-methylphenyl)acetonitrile Chemical compound CC1=CC=C(CC#N)C=C1O QAOJXZSPCDKVBM-UHFFFAOYSA-N 0.000 description 1
• QJNHQRNWKZVZKA-UHFFFAOYSA-N 2-(4-bromophenoxy)-1-chloro-4-methylbenzene Chemical compound CC1=CC=C(Cl)C(OC=2C=CC(Br)=CC=2)=C1 QJNHQRNWKZVZKA-UHFFFAOYSA-N 0.000 description 1
• BDXNRURKMWYDDW-UHFFFAOYSA-N 2-(4-chloro-2-methyl-3-phenoxyphenyl)acetonitrile Chemical compound CC1=C(CC#N)C=CC(Cl)=C1OC1=CC=CC=C1 BDXNRURKMWYDDW-UHFFFAOYSA-N 0.000 description 1
• XLOXWMJPYBQHMY-UHFFFAOYSA-N 2-[3-(3-bromophenoxy)-4-chlorophenyl]acetonitrile Chemical compound ClC1=CC=C(CC#N)C=C1OC1=CC=CC(Br)=C1 XLOXWMJPYBQHMY-UHFFFAOYSA-N 0.000 description 1
• BVGUZVVZYNIUCS-UHFFFAOYSA-N 2-[3-(3-bromophenoxy)-4-fluorophenyl]acetonitrile Chemical compound FC1=CC=C(CC#N)C=C1OC1=CC=CC(Br)=C1 BVGUZVVZYNIUCS-UHFFFAOYSA-N 0.000 description 1
• OVXVQBCRONSPDC-UHFFFAOYSA-N 2-bromo-1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Br)=C1 OVXVQBCRONSPDC-UHFFFAOYSA-N 0.000 description 1
• 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
• WJKISRFVKIOBCQ-UHFFFAOYSA-N 2-fluoro-4-methylphenol Chemical compound CC1=CC=C(O)C(F)=C1 WJKISRFVKIOBCQ-UHFFFAOYSA-N 0.000 description 1
• 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 1
• 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
• NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
• IBWYHNOFSKJKKY-UHFFFAOYSA-N 3-chloropyridazine Chemical compound ClC1=CC=CN=N1 IBWYHNOFSKJKKY-UHFFFAOYSA-N 0.000 description 1
• 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• WTSXVIMLKCKWIW-UHFFFAOYSA-N 3h-1,3,4-oxadiazol-2-one Chemical class O=C1NN=CO1 WTSXVIMLKCKWIW-UHFFFAOYSA-N 0.000 description 1
• JVVRCYWZTJLJSG-UHFFFAOYSA-N 4-dimethylaminophenol Chemical compound CN(C)C1=CC=C(O)C=C1 JVVRCYWZTJLJSG-UHFFFAOYSA-N 0.000 description 1
• 229960000549 4-dimethylaminophenol Drugs 0.000 description 1
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-dimethylaminopyridine Substances CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 1
• ZVWPYTWNTGAGTM-UHFFFAOYSA-N 4-methoxythiadiazole Chemical compound COC1=CSN=N1 ZVWPYTWNTGAGTM-UHFFFAOYSA-N 0.000 description 1
• BJTFDWHEUALZNA-UHFFFAOYSA-N 4h-1,2-thiazol-5-one Chemical compound O=C1CC=NS1 BJTFDWHEUALZNA-UHFFFAOYSA-N 0.000 description 1
• GZVJKNAPQDHVHH-UHFFFAOYSA-N 5-benzyl-1h-pyridazin-6-one Chemical class O=C1NN=CC=C1CC1=CC=CC=C1 GZVJKNAPQDHVHH-UHFFFAOYSA-N 0.000 description 1
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
• FEJUGLKDZJDVFY-UHFFFAOYSA-N 9-borabicyclo[3.3.1]nonane Substances C1CCC2CCCC1B2 FEJUGLKDZJDVFY-UHFFFAOYSA-N 0.000 description 1
• 229910015845 BBr3 Inorganic materials 0.000 description 1
• 238000006220 Baeyer-Villiger oxidation reaction Methods 0.000 description 1
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
• JGLMVXWAHNTPRF-CMDGGOBGSA-N CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O Chemical compound CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O JGLMVXWAHNTPRF-CMDGGOBGSA-N 0.000 description 1
• CNDZFIPGGBJNKM-UHFFFAOYSA-N COC=S.NN Chemical compound COC=S.NN CNDZFIPGGBJNKM-UHFFFAOYSA-N 0.000 description 1
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
• 239000004215 Carbon black (E152) Substances 0.000 description 1
• KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
• RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
• 229910021592 Copper(II) chloride Inorganic materials 0.000 description 1
• XUIIKFGFIJCVMT-GFCCVEGCSA-N D-thyroxine Chemical class IC1=CC(C[C@@H](N)C(O)=O)=CC(I)=C1OC1=CC(I)=C(O)C(I)=C1 XUIIKFGFIJCVMT-GFCCVEGCSA-N 0.000 description 1
• 239000004375 Dextrin Substances 0.000 description 1
• 229920001353 Dextrin Polymers 0.000 description 1
• 239000004338 Dichlorodifluoromethane Substances 0.000 description 1
• BXZVVICBKDXVGW-NKWVEPMBSA-N Didanosine Chemical compound O1[C@H](CO)CC[C@@H]1N1C(NC=NC2=O)=C2N=C1 BXZVVICBKDXVGW-NKWVEPMBSA-N 0.000 description 1
• 206010061818 Disease progression Diseases 0.000 description 1
• 206010059866 Drug resistance Diseases 0.000 description 1
• KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
• XPOQHMRABVBWPR-UHFFFAOYSA-N Efavirenz Natural products O1C(=O)NC2=CC=C(Cl)C=C2C1(C(F)(F)F)C#CC1CC1 XPOQHMRABVBWPR-UHFFFAOYSA-N 0.000 description 1
• LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
• 102100031780 Endonuclease Human genes 0.000 description 1
• 108010042407 Endonucleases Proteins 0.000 description 1
• PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
• 238000005863 Friedel-Crafts acylation reaction Methods 0.000 description 1
• WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
• 108010010369 HIV Protease Proteins 0.000 description 1
• 229940122440 HIV protease inhibitor Drugs 0.000 description 1
• CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
• 108010061833 Integrases Proteins 0.000 description 1
• 229930194542 Keto Natural products 0.000 description 1
• 241001572350 Lycaena mariposa Species 0.000 description 1
• 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
• 229920000881 Modified starch Polymers 0.000 description 1
• HSHXDCVZWHOWCS-UHFFFAOYSA-N N'-hexadecylthiophene-2-carbohydrazide Chemical compound CCCCCCCCCCCCCCCCNNC(=O)c1cccs1 HSHXDCVZWHOWCS-UHFFFAOYSA-N 0.000 description 1
• ZKGNPQKYVKXMGJ-UHFFFAOYSA-N N,N-dimethylacetamide Chemical compound CN(C)C(C)=O.CN(C)C(C)=O ZKGNPQKYVKXMGJ-UHFFFAOYSA-N 0.000 description 1
• DIKPQFXYECAYPC-UHFFFAOYSA-N N-butyl-N-(4-hydroxybutyl)nitrosamine Chemical compound CCCCN(N=O)CCCCO DIKPQFXYECAYPC-UHFFFAOYSA-N 0.000 description 1
• 150000001204 N-oxides Chemical class 0.000 description 1
• 241001274216 Naso Species 0.000 description 1
• 208000001388 Opportunistic Infections Diseases 0.000 description 1
• 206010049025 Persistent generalised lymphadenopathy Diseases 0.000 description 1
• 102000004160 Phosphoric Monoester Hydrolases Human genes 0.000 description 1
• 108090000608 Phosphoric Monoester Hydrolases Proteins 0.000 description 1
• OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
• 102000014961 Protein Precursors Human genes 0.000 description 1
• 108010078762 Protein Precursors Proteins 0.000 description 1
• 206010037660 Pyrexia Diseases 0.000 description 1
• 206010057190 Respiratory tract infections Diseases 0.000 description 1
• 206010039085 Rhinitis allergic Diseases 0.000 description 1
• 102000014400 SH2 domains Human genes 0.000 description 1
• 108050003452 SH2 domains Proteins 0.000 description 1
• 238000000297 Sandmeyer reaction Methods 0.000 description 1
• VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 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
• 101710172711 Structural protein Proteins 0.000 description 1
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
• 210000001744 T-lymphocyte Anatomy 0.000 description 1
• AUYYCJSJGJYCDS-LBPRGKRZSA-N Thyrolar Chemical class IC1=CC(C[C@H](N)C(O)=O)=CC(I)=C1OC1=CC=C(O)C(I)=C1 AUYYCJSJGJYCDS-LBPRGKRZSA-N 0.000 description 1
• ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
• 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
• 239000007983 Tris buffer Substances 0.000 description 1
• 238000010752 Ullmann ether synthesis reaction Methods 0.000 description 1
• 238000006959 Williamson synthesis reaction Methods 0.000 description 1
• 238000007295 Wittig olefination reaction Methods 0.000 description 1
• QQIRAVWVGBTHMJ-UHFFFAOYSA-N [dimethyl-(trimethylsilylamino)silyl]methane;lithium Chemical compound [Li].C[Si](C)(C)N[Si](C)(C)C QQIRAVWVGBTHMJ-UHFFFAOYSA-N 0.000 description 1
• 239000000205 acacia gum Substances 0.000 description 1
• 230000001133 acceleration Effects 0.000 description 1
• IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
• 230000002378 acidificating effect Effects 0.000 description 1
• 125000004442 acylamino group Chemical group 0.000 description 1
• 230000010933 acylation Effects 0.000 description 1
• 238000005917 acylation reaction Methods 0.000 description 1
• 239000000853 adhesive Substances 0.000 description 1
• 150000001299 aldehydes Chemical class 0.000 description 1
• 125000000278 alkyl amino alkyl group Chemical group 0.000 description 1
• 150000001346 alkyl aryl ethers Chemical class 0.000 description 1
• 125000004448 alkyl carbonyl group Chemical group 0.000 description 1
• 125000004644 alkyl sulfinyl group Chemical group 0.000 description 1
• 201000010105 allergic rhinitis Diseases 0.000 description 1
• 230000003281 allosteric effect Effects 0.000 description 1
• BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
• 150000001408 amides Chemical class 0.000 description 1
• 150000001409 amidines Chemical class 0.000 description 1
• 150000001412 amines Chemical class 0.000 description 1
• 125000003277 amino group Chemical group 0.000 description 1
• 125000004103 aminoalkyl group Chemical group 0.000 description 1
• 230000000202 analgesic effect Effects 0.000 description 1
• 208000007502 anemia Diseases 0.000 description 1
• 239000005557 antagonist Substances 0.000 description 1
• 230000001760 anti-analgesic effect Effects 0.000 description 1
• 230000036436 anti-hiv Effects 0.000 description 1
• 230000003110 anti-inflammatory effect Effects 0.000 description 1
• 238000011225 antiretroviral therapy Methods 0.000 description 1
• 239000008365 aqueous carrier Substances 0.000 description 1
• 239000008135 aqueous vehicle Substances 0.000 description 1
• 150000004982 aromatic amines Chemical class 0.000 description 1
• 235000021311 artificial sweeteners Nutrition 0.000 description 1
• 150000005840 aryl radicals Chemical group 0.000 description 1
• 208000006673 asthma Diseases 0.000 description 1
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
• 230000004888 barrier function Effects 0.000 description 1
• 230000009286 beneficial effect Effects 0.000 description 1
• 150000007962 benzene acetonitriles Chemical class 0.000 description 1
• WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
• 230000001588 bifunctional effect Effects 0.000 description 1
• 239000011230 binding agent Substances 0.000 description 1
• 229920002988 biodegradable polymer Polymers 0.000 description 1
• 239000004621 biodegradable polymer Substances 0.000 description 1
• 230000000903 blocking effect Effects 0.000 description 1
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
• 229910052794 bromium Inorganic materials 0.000 description 1
• 125000001246 bromo group Chemical group Br* 0.000 description 1
• 239000000872 buffer Substances 0.000 description 1
• 244000309464 bull Species 0.000 description 1
• FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
• 229910000024 caesium carbonate Inorganic materials 0.000 description 1
• 230000021235 carbamoylation Effects 0.000 description 1
• 239000001569 carbon dioxide Substances 0.000 description 1
• 229910002092 carbon dioxide Inorganic materials 0.000 description 1
• 229960004424 carbon dioxide Drugs 0.000 description 1
• PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 1
• 150000001733 carboxylic acid esters Chemical class 0.000 description 1
• 230000000747 cardiac effect Effects 0.000 description 1
• 230000005792 cardiovascular activity Effects 0.000 description 1
• 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
• 238000006555 catalytic reaction Methods 0.000 description 1
• 230000008859 change Effects 0.000 description 1
• 239000013522 chelant Substances 0.000 description 1
• 238000002512 chemotherapy Methods 0.000 description 1
• 150000001804 chlorine Chemical class 0.000 description 1
• 229910052801 chlorine Inorganic materials 0.000 description 1
• 150000001805 chlorine compounds Chemical group 0.000 description 1
• KYKAJFCTULSVSH-UHFFFAOYSA-N chloro(fluoro)methane Chemical compound F[C]Cl KYKAJFCTULSVSH-UHFFFAOYSA-N 0.000 description 1
• 239000003086 colorant Substances 0.000 description 1
• 230000002860 competitive effect Effects 0.000 description 1
• 230000001010 compromised effect Effects 0.000 description 1
• 238000010276 construction Methods 0.000 description 1
• 238000013270 controlled release Methods 0.000 description 1
• 229910052802 copper Inorganic materials 0.000 description 1
• 150000001907 coumarones Chemical class 0.000 description 1
• 238000006880 cross-coupling reaction Methods 0.000 description 1
• 239000013078 crystal Substances 0.000 description 1
• 238000002425 crystallisation Methods 0.000 description 1
• 230000008025 crystallization Effects 0.000 description 1
• 125000000753 cycloalkyl group Chemical group 0.000 description 1
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
• 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
• 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
• 230000006378 damage Effects 0.000 description 1
• DEZRYPDIMOWBDS-UHFFFAOYSA-N dcm dichloromethane Chemical compound ClCCl.ClCCl DEZRYPDIMOWBDS-UHFFFAOYSA-N 0.000 description 1
• 230000007423 decrease Effects 0.000 description 1
• 238000006704 dehydrohalogenation reaction Methods 0.000 description 1
• 229960005319 delavirdine Drugs 0.000 description 1
• 238000011161 development Methods 0.000 description 1
• 230000018109 developmental process Effects 0.000 description 1
• 235000019425 dextrin Nutrition 0.000 description 1
• 239000008121 dextrose Substances 0.000 description 1
• 125000004985 dialkyl amino alkyl group Chemical group 0.000 description 1
• 238000006193 diazotization reaction Methods 0.000 description 1
• PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
• 235000019404 dichlorodifluoromethane Nutrition 0.000 description 1
• 229940042935 dichlorodifluoromethane Drugs 0.000 description 1
• 229940087091 dichlorotetrafluoroethane Drugs 0.000 description 1
• 229960002656 didanosine Drugs 0.000 description 1
• 235000014113 dietary fatty acids Nutrition 0.000 description 1
• 125000004852 dihydrofuranyl group Chemical class O1C(CC=C1)* 0.000 description 1
• UXGNZZKBCMGWAZ-UHFFFAOYSA-N dimethylformamide dmf Chemical compound CN(C)C=O.CN(C)C=O UXGNZZKBCMGWAZ-UHFFFAOYSA-N 0.000 description 1
• AXAZMDOAUQTMOW-UHFFFAOYSA-N dimethylzinc Chemical compound C[Zn]C AXAZMDOAUQTMOW-UHFFFAOYSA-N 0.000 description 1
• 231100000676 disease causative agent Toxicity 0.000 description 1
• 230000005750 disease progression Effects 0.000 description 1
• 238000004821 distillation Methods 0.000 description 1
• 239000008298 dragée Substances 0.000 description 1
• 238000012377 drug delivery Methods 0.000 description 1
• XPOQHMRABVBWPR-ZDUSSCGKSA-N efavirenz Chemical compound C([C@]1(C2=CC(Cl)=CC=C2NC(=O)O1)C(F)(F)F)#CC1CC1 XPOQHMRABVBWPR-ZDUSSCGKSA-N 0.000 description 1
• 229960003804 efavirenz Drugs 0.000 description 1
• 239000003480 eluent Substances 0.000 description 1
• 238000010828 elution Methods 0.000 description 1
• 125000002587 enol group Chemical group 0.000 description 1
• 239000002702 enteric coating Substances 0.000 description 1
• 238000009505 enteric coating Methods 0.000 description 1
• 210000002615 epidermis Anatomy 0.000 description 1
• 230000010437 erythropoiesis Effects 0.000 description 1
• LHWWETDBWVTKJO-UHFFFAOYSA-N et3n triethylamine Chemical compound CCN(CC)CC.CCN(CC)CC LHWWETDBWVTKJO-UHFFFAOYSA-N 0.000 description 1
• OCLXJTCGWSSVOE-UHFFFAOYSA-N ethanol etoh Chemical compound CCO.CCO OCLXJTCGWSSVOE-UHFFFAOYSA-N 0.000 description 1
• FVVOTZZCIZCSLY-UHFFFAOYSA-N ethyl 2-(3-formyl-4-hydroxy-5-methoxyphenyl)acetate Chemical compound CCOC(=O)CC1=CC(OC)=C(O)C(C=O)=C1 FVVOTZZCIZCSLY-UHFFFAOYSA-N 0.000 description 1
• YMDVKNRXTWQWQL-UHFFFAOYSA-N ethyl 2-(3-methoxy-4-methylphenyl)acetate Chemical compound CCOC(=O)CC1=CC=C(C)C(OC)=C1 YMDVKNRXTWQWQL-UHFFFAOYSA-N 0.000 description 1
• WFHINRVBSYHWDE-UHFFFAOYSA-N ethyl 2-(3-methoxy-4-propan-2-ylphenyl)acetate Chemical compound CCOC(=O)CC1=CC=C(C(C)C)C(OC)=C1 WFHINRVBSYHWDE-UHFFFAOYSA-N 0.000 description 1
• XXVVNHCWPHMLEZ-UHFFFAOYSA-N ethyl 2-(3-methoxyphenyl)acetate Chemical compound CCOC(=O)CC1=CC=CC(OC)=C1 XXVVNHCWPHMLEZ-UHFFFAOYSA-N 0.000 description 1
• BOGSCTFXCVMCFW-UHFFFAOYSA-N ethyl 2-(4-acetyl-3-methoxyphenyl)acetate Chemical compound CCOC(=O)CC1=CC=C(C(C)=O)C(OC)=C1 BOGSCTFXCVMCFW-UHFFFAOYSA-N 0.000 description 1
• FYHRIDNUCHIWQD-UHFFFAOYSA-N ethyl 2-(4-chloro-3-methoxyphenyl)acetate Chemical compound CCOC(=O)CC1=CC=C(Cl)C(OC)=C1 FYHRIDNUCHIWQD-UHFFFAOYSA-N 0.000 description 1
• XHEZSVGUFAWBOF-UHFFFAOYSA-N ethyl 2-(4-ethyl-3-methoxyphenyl)acetate Chemical compound CCOC(=O)CC1=CC=C(CC)C(OC)=C1 XHEZSVGUFAWBOF-UHFFFAOYSA-N 0.000 description 1
• KZQRMISMLFJFNH-UHFFFAOYSA-N ethyl 2-[3-(2-chlorophenoxy)-4-methylphenyl]acetate Chemical compound CCOC(=O)CC1=CC=C(C)C(OC=2C(=CC=CC=2)Cl)=C1 KZQRMISMLFJFNH-UHFFFAOYSA-N 0.000 description 1
• AVUMLISFGKBUAH-UHFFFAOYSA-N ethyl 2-[3-(3-chlorophenoxy)-4-ethylphenyl]acetate Chemical compound CCOC(=O)CC1=CC=C(CC)C(OC=2C=C(Cl)C=CC=2)=C1 AVUMLISFGKBUAH-UHFFFAOYSA-N 0.000 description 1
• WKQVPNMPWPVBLF-UHFFFAOYSA-N ethyl 2-[3-(3-chlorophenoxy)-4-propan-2-ylphenyl]acetate Chemical compound CCOC(=O)CC1=CC=C(C(C)C)C(OC=2C=C(Cl)C=CC=2)=C1 WKQVPNMPWPVBLF-UHFFFAOYSA-N 0.000 description 1
• UKPAEGLBKRSBKR-UHFFFAOYSA-N ethyl 2-[3-(3-fluorophenoxy)-4-methylphenyl]acetate Chemical compound CCOC(=O)CC1=CC=C(C)C(OC=2C=C(F)C=CC=2)=C1 UKPAEGLBKRSBKR-UHFFFAOYSA-N 0.000 description 1
• YYUXGXIHUWHESH-UHFFFAOYSA-N ethyl 2-[4-chloro-3-(2,5-dichlorophenoxy)phenyl]acetate Chemical compound CCOC(=O)CC1=CC=C(Cl)C(OC=2C(=CC=C(Cl)C=2)Cl)=C1 YYUXGXIHUWHESH-UHFFFAOYSA-N 0.000 description 1
• QVJPGOFXNXPTRQ-UHFFFAOYSA-N ethyl 2-[4-chloro-3-(3-cyano-5-fluorophenoxy)phenyl]acetate Chemical compound CCOC(=O)CC1=CC=C(Cl)C(OC=2C=C(C=C(F)C=2)C#N)=C1 QVJPGOFXNXPTRQ-UHFFFAOYSA-N 0.000 description 1
• OWZFULPEVHKEKS-UHFFFAOYSA-N ethyl 2-chloro-2-oxoacetate Chemical compound CCOC(=O)C(Cl)=O OWZFULPEVHKEKS-UHFFFAOYSA-N 0.000 description 1
• VKNVDLNENTXLIS-UHFFFAOYSA-N ethyl 3-(3-chlorophenoxy)-4,5-dimethylbenzoate Chemical compound CCOC(=O)C1=CC(C)=C(C)C(OC=2C=C(Cl)C=CC=2)=C1 VKNVDLNENTXLIS-UHFFFAOYSA-N 0.000 description 1
• CEIPQQODRKXDSB-UHFFFAOYSA-N ethyl 3-(6-hydroxynaphthalen-2-yl)-1H-indazole-5-carboximidate dihydrochloride Chemical compound Cl.Cl.C1=C(O)C=CC2=CC(C3=NNC4=CC=C(C=C43)C(=N)OCC)=CC=C21 CEIPQQODRKXDSB-UHFFFAOYSA-N 0.000 description 1
• 125000004494 ethyl ester group Chemical group 0.000 description 1
• FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 1
• LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
• 229940093471 ethyl oleate Drugs 0.000 description 1
• OJCSPXHYDFONPU-UHFFFAOYSA-N etoac etoac Chemical compound CCOC(C)=O.CCOC(C)=O OJCSPXHYDFONPU-UHFFFAOYSA-N 0.000 description 1
• 238000001704 evaporation Methods 0.000 description 1
• 230000008020 evaporation Effects 0.000 description 1
• 239000000194 fatty acid Substances 0.000 description 1
• 229930195729 fatty acid Natural products 0.000 description 1
• 239000011737 fluorine Substances 0.000 description 1
• 229910052731 fluorine Inorganic materials 0.000 description 1
• 239000006260 foam Substances 0.000 description 1
• 235000013355 food flavoring agent Nutrition 0.000 description 1
• 230000022244 formylation Effects 0.000 description 1
• 238000006170 formylation reaction Methods 0.000 description 1
• 238000004108 freeze drying Methods 0.000 description 1
• 239000001530 fumaric acid Substances 0.000 description 1
• 108010027225 gag-pol Fusion Proteins Proteins 0.000 description 1
• 239000007789 gas Substances 0.000 description 1
• 239000007903 gelatin capsule Substances 0.000 description 1
• 239000003349 gelling agent Substances 0.000 description 1
• 239000011521 glass Substances 0.000 description 1
• 239000003365 glass fiber Substances 0.000 description 1
• 235000011187 glycerol Nutrition 0.000 description 1
• 239000008187 granular material Substances 0.000 description 1
• 238000009499 grossing Methods 0.000 description 1
• 230000003394 haemopoietic effect Effects 0.000 description 1
• 230000036541 health Effects 0.000 description 1
• 238000010438 heat treatment Methods 0.000 description 1
• 230000011132 hemopoiesis Effects 0.000 description 1
• 239000004312 hexamethylene tetramine Substances 0.000 description 1
• 235000010299 hexamethylene tetramine Nutrition 0.000 description 1
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• 239000004030 hiv protease inhibitor Substances 0.000 description 1
• 239000008240 homogeneous mixture Substances 0.000 description 1
• 239000012456 homogeneous solution Substances 0.000 description 1
• 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 1
• 229930195733 hydrocarbon Natural products 0.000 description 1
• 238000005984 hydrogenation reaction Methods 0.000 description 1
• 238000007327 hydrogenolysis reaction Methods 0.000 description 1
• 230000007062 hydrolysis Effects 0.000 description 1
• 238000006460 hydrolysis reaction Methods 0.000 description 1
• RCBVKBFIWMOMHF-UHFFFAOYSA-L hydroxy-(hydroxy(dioxo)chromio)oxy-dioxochromium;pyridine Chemical compound C1=CC=NC=C1.C1=CC=NC=C1.O[Cr](=O)(=O)O[Cr](O)(=O)=O RCBVKBFIWMOMHF-UHFFFAOYSA-L 0.000 description 1
• 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
• 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
• 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
• 125000002883 imidazolyl group Chemical group 0.000 description 1
• 210000000987 immune system Anatomy 0.000 description 1
• 239000007943 implant Substances 0.000 description 1
• 238000000338 in vitro Methods 0.000 description 1
• 239000005414 inactive ingredient Substances 0.000 description 1
• 238000010348 incorporation Methods 0.000 description 1
• 238000011534 incubation Methods 0.000 description 1
• 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
• 125000001041 indolyl group Chemical group 0.000 description 1
• 230000002458 infectious effect Effects 0.000 description 1
• 230000002401 inhibitory effect Effects 0.000 description 1
• 239000013067 intermediate product Substances 0.000 description 1
• 238000007918 intramuscular administration Methods 0.000 description 1
• 239000011630 iodine Substances 0.000 description 1
• 238000002955 isolation Methods 0.000 description 1
• 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
• 229960001627 lamivudine Drugs 0.000 description 1
• CFHGBZLNZZVTAY-UHFFFAOYSA-N lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 description 1
• 239000012280 lithium aluminium hydride Substances 0.000 description 1
• YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 1
• ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
• 239000001095 magnesium carbonate Substances 0.000 description 1
• 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
• 229910001629 magnesium chloride Inorganic materials 0.000 description 1
• 235000019359 magnesium stearate Nutrition 0.000 description 1
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
• 235000019341 magnesium sulphate Nutrition 0.000 description 1
• VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
• 239000011976 maleic acid Substances 0.000 description 1
• 239000001630 malic acid Substances 0.000 description 1
• 235000011090 malic acid Nutrition 0.000 description 1
• WRIRWRKPLXCTFD-UHFFFAOYSA-N malonamide Chemical class NC(=O)CC(N)=O WRIRWRKPLXCTFD-UHFFFAOYSA-N 0.000 description 1
• 230000007246 mechanism Effects 0.000 description 1
• BCVXHSPFUWZLGQ-UHFFFAOYSA-N mecn acetonitrile Chemical compound CC#N.CC#N BCVXHSPFUWZLGQ-UHFFFAOYSA-N 0.000 description 1
• 230000008018 melting Effects 0.000 description 1
• COTNUBDHGSIOTA-UHFFFAOYSA-N meoh methanol Chemical compound OC.OC COTNUBDHGSIOTA-UHFFFAOYSA-N 0.000 description 1
• VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
• CSJDCSCTVDEHRN-UHFFFAOYSA-N methane;molecular oxygen Chemical compound C.O=O CSJDCSCTVDEHRN-UHFFFAOYSA-N 0.000 description 1
• 229940098779 methanesulfonic acid Drugs 0.000 description 1
• IXUBSYNPXRKYCL-UHFFFAOYSA-N methyl 4-chloro-2-methyl-3-phenoxybenzoate Chemical compound COC(=O)C1=CC=C(Cl)C(OC=2C=CC=CC=2)=C1C IXUBSYNPXRKYCL-UHFFFAOYSA-N 0.000 description 1
• ZGNRUDNXCMVACI-UHFFFAOYSA-N methyl 4-chloro-3-hydroxy-2-methylbenzoate Chemical compound COC(=O)C1=CC=C(Cl)C(O)=C1C ZGNRUDNXCMVACI-UHFFFAOYSA-N 0.000 description 1
• 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 description 1
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
• 239000008108 microcrystalline cellulose Substances 0.000 description 1
• 229940016286 microcrystalline cellulose Drugs 0.000 description 1
• 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
• 230000005012 migration Effects 0.000 description 1
• 238000013508 migration Methods 0.000 description 1
• 150000007522 mineralic acids Chemical class 0.000 description 1
• 235000019426 modified starch Nutrition 0.000 description 1
• 239000002324 mouth wash Substances 0.000 description 1
• 229940051866 mouthwash Drugs 0.000 description 1
• 230000035772 mutation Effects 0.000 description 1
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• 235000021096 natural sweeteners Nutrition 0.000 description 1
• 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• 229960000689 nevirapine Drugs 0.000 description 1
• VWBWQOUWDOULQN-UHFFFAOYSA-N nmp n-methylpyrrolidone Chemical compound CN1CCCC1=O.CN1CCCC1=O VWBWQOUWDOULQN-UHFFFAOYSA-N 0.000 description 1
• 150000007523 nucleic acids Chemical class 0.000 description 1
• 102000039446 nucleic acids Human genes 0.000 description 1
• 108020004707 nucleic acids Proteins 0.000 description 1
• 239000012038 nucleophile Substances 0.000 description 1
• 238000007339 nucleophilic aromatic substitution reaction Methods 0.000 description 1
• 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
• 239000002777 nucleoside Substances 0.000 description 1
• 229940127073 nucleoside analogue Drugs 0.000 description 1
• 235000008390 olive oil Nutrition 0.000 description 1
• 239000004006 olive oil Substances 0.000 description 1
• 210000000056 organ Anatomy 0.000 description 1
• 150000007524 organic acids Chemical class 0.000 description 1
• 235000005985 organic acids Nutrition 0.000 description 1
• 150000002895 organic esters Chemical class 0.000 description 1
• 238000006053 organic reaction Methods 0.000 description 1
• WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
• 125000002971 oxazolyl group Chemical group 0.000 description 1
• 239000001301 oxygen Substances 0.000 description 1
• FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
• 238000007911 parenteral administration Methods 0.000 description 1
• 239000006072 paste Substances 0.000 description 1
• 239000001814 pectin Substances 0.000 description 1
• 235000010987 pectin Nutrition 0.000 description 1
• 229920001277 pectin Polymers 0.000 description 1
• 230000035515 penetration Effects 0.000 description 1
• 239000003961 penetration enhancing agent Substances 0.000 description 1
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
• 201000003450 persistent generalized lymphadenopathy Diseases 0.000 description 1
• 239000008024 pharmaceutical diluent Substances 0.000 description 1
• 239000012071 phase Substances 0.000 description 1
• WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
• 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
• UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
• 235000011007 phosphoric acid Nutrition 0.000 description 1
• 150000003016 phosphoric acids Chemical class 0.000 description 1
• 230000000704 physical effect Effects 0.000 description 1
• 239000006187 pill Substances 0.000 description 1
• 229920000747 poly(lactic acid) Polymers 0.000 description 1
• 125000003367 polycyclic group Chemical group 0.000 description 1
• 239000004626 polylactic acid Substances 0.000 description 1
• 229910000027 potassium carbonate Inorganic materials 0.000 description 1
• 230000002335 preservative effect Effects 0.000 description 1
• 238000012545 processing Methods 0.000 description 1
• 230000001737 promoting effect Effects 0.000 description 1
• VVWRJUBEIPHGQF-MDZDMXLPSA-N propan-2-yl (ne)-n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)\N=N\C(=O)OC(C)C VVWRJUBEIPHGQF-MDZDMXLPSA-N 0.000 description 1
• 239000003380 propellant Substances 0.000 description 1
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 239000002599 prostaglandin synthase inhibitor Substances 0.000 description 1
• 125000003373 pyrazinyl group Chemical group 0.000 description 1
• 125000003226 pyrazolyl group Chemical group 0.000 description 1
• 125000005412 pyrazyl group Chemical group 0.000 description 1
• 125000002098 pyridazinyl group Chemical group 0.000 description 1
• 125000004076 pyridyl group Chemical group 0.000 description 1
• 125000000168 pyrrolyl group Chemical group 0.000 description 1
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
• 238000006894 reductive elimination reaction Methods 0.000 description 1
• 230000003362 replicative effect Effects 0.000 description 1
• 239000011347 resin Substances 0.000 description 1
• 229920005989 resin Polymers 0.000 description 1
• 210000002345 respiratory system Anatomy 0.000 description 1
• 230000004044 response Effects 0.000 description 1
• 230000001177 retroviral effect Effects 0.000 description 1
• 238000006798 ring closing metathesis reaction Methods 0.000 description 1
• 229960004889 salicylic acid Drugs 0.000 description 1
• 229930195734 saturated hydrocarbon Natural products 0.000 description 1
• 229920002379 silicone rubber Polymers 0.000 description 1
• 239000004945 silicone rubber Substances 0.000 description 1
• 239000002002 slurry Substances 0.000 description 1
• 229910052708 sodium Inorganic materials 0.000 description 1
• WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
• 229910000342 sodium bisulfate Inorganic materials 0.000 description 1
• GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 1
• 235000010265 sodium sulphite Nutrition 0.000 description 1
• 239000011343 solid material Substances 0.000 description 1
• 239000012453 solvate Substances 0.000 description 1
• 235000011069 sorbitan monooleate Nutrition 0.000 description 1
• 239000001593 sorbitan monooleate Substances 0.000 description 1
• 229940035049 sorbitan monooleate Drugs 0.000 description 1
• 230000003595 spectral effect Effects 0.000 description 1
• 230000004936 stimulating effect Effects 0.000 description 1
• 235000011044 succinic acid Nutrition 0.000 description 1
• 150000003444 succinic acids Chemical class 0.000 description 1
• 239000011593 sulfur Substances 0.000 description 1
• 239000004094 surface-active agent Substances 0.000 description 1
• 238000001356 surgical procedure Methods 0.000 description 1
• 208000011580 syndromic disease Diseases 0.000 description 1
• 230000009897 systematic effect Effects 0.000 description 1
• 239000007885 tablet disintegrant Substances 0.000 description 1
• 239000000454 talc Substances 0.000 description 1
• 229910052623 talc Inorganic materials 0.000 description 1
• 238000003419 tautomerization reaction Methods 0.000 description 1
• 229960004556 tenofovir Drugs 0.000 description 1
• 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
• 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
• 125000003507 tetrahydrothiofenyl group Chemical group 0.000 description 1
• 125000003831 tetrazolyl group Chemical group 0.000 description 1
• WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
• VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
• XWMXMWHHTIEXRE-UHFFFAOYSA-N thiadiazole 1-oxide Chemical compound O=S1C=CN=N1 XWMXMWHHTIEXRE-UHFFFAOYSA-N 0.000 description 1
• 125000000335 thiazolyl group Chemical group 0.000 description 1
• HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
• 210000001519 tissue Anatomy 0.000 description 1
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
• 125000003944 tolyl group Chemical group 0.000 description 1
• 238000011200 topical administration Methods 0.000 description 1
• 239000012049 topical pharmaceutical composition Substances 0.000 description 1
• 231100000419 toxicity Toxicity 0.000 description 1
• 230000001988 toxicity Effects 0.000 description 1
• 230000037317 transdermal delivery Effects 0.000 description 1
• 238000000844 transformation Methods 0.000 description 1
• 229910052723 transition metal Inorganic materials 0.000 description 1
• 150000003624 transition metals Chemical class 0.000 description 1
• 238000011269 treatment regimen Methods 0.000 description 1
• 125000004306 triazinyl group Chemical group 0.000 description 1
• CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
• 229940029284 trichlorofluoromethane Drugs 0.000 description 1
• 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
• IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
• ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
• 150000008648 triflates Chemical class 0.000 description 1
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
• 235000011178 triphosphate Nutrition 0.000 description 1
• 239000001226 triphosphate Substances 0.000 description 1
• UNXRWKVEANCORM-UHFFFAOYSA-N triphosphoric acid Chemical compound OP(O)(=O)OP(O)(=O)OP(O)(O)=O UNXRWKVEANCORM-UHFFFAOYSA-N 0.000 description 1
• LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
• 235000002374 tyrosine Nutrition 0.000 description 1
• 150000003668 tyrosines Chemical class 0.000 description 1
• 241001430294 unidentified retrovirus Species 0.000 description 1
• 235000015112 vegetable and seed oil Nutrition 0.000 description 1
• 239000008158 vegetable oil Substances 0.000 description 1
• 239000011345 viscous material Substances 0.000 description 1
• 208000016261 weight loss Diseases 0.000 description 1
• 230000004580 weight loss Effects 0.000 description 1
• 239000000080 wetting agent Substances 0.000 description 1
• 229960000523 zalcitabine Drugs 0.000 description 1