BG107839A - Нови съединения за използване като hiv протеазни инхибитори - Google Patents

Нови съединения за използване като hiv протеазни инхибитори Download PDF

Info

Publication number: BG107839A
Authority: BG; Bulgaria
Prior art keywords: alkyl; aryl; heterocyclyl; carbonyl; amino
Prior art date: 2000-11-22

Application number

BG107839A

Other languages

Bulgarian (bg)

English (en)

Inventor

Armstrong J. Martin

Sally Redshaw

Steven Swallow

John G. Thomas

Original Assignee

F. Hoffmann- La Roche Ag

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2000-11-22

Filing date

2003-05-22

Publication date

2004-06-30

2003-05-22 Application filed by F. Hoffmann- La Roche Ag filed Critical F. Hoffmann- La Roche Ag

2004-06-30 Publication of BG107839A publication Critical patent/BG107839A/bg

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 113
239000004030 hiv protease inhibitor Substances 0.000 title description 3
-1 wherein R2 is H Chemical group 0.000 claims abstract description 215
125000000217 alkyl group Chemical group 0.000 claims abstract description 59
125000004415 heterocyclylalkyl group Chemical group 0.000 claims abstract description 43
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 42
125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 39
125000003118 aryl group Chemical group 0.000 claims abstract description 35
229910052717 sulfur Inorganic materials 0.000 claims abstract description 16
125000003342 alkenyl group Chemical group 0.000 claims abstract description 13
125000005129 aryl carbonyl group Chemical group 0.000 claims abstract description 13
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 13
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 13
150000003839 salts Chemical class 0.000 claims abstract description 13
229910052799 carbon Inorganic materials 0.000 claims abstract description 12
125000004448 alkyl carbonyl group Chemical group 0.000 claims abstract description 10
125000005842 heteroatom Chemical group 0.000 claims abstract description 10
229910052760 oxygen Inorganic materials 0.000 claims abstract description 10
125000000304 alkynyl group Chemical group 0.000 claims abstract description 9
125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims abstract description 9
125000006517 heterocyclyl carbonyl group Chemical group 0.000 claims abstract description 9
150000001721 carbon Chemical group 0.000 claims abstract description 8
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 8
229920006395 saturated elastomer Polymers 0.000 claims abstract description 8
125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 7
125000004391 aryl sulfonyl group Chemical group 0.000 claims abstract description 7
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims abstract description 7
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims abstract description 7
125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 6
125000005099 aryl alkyl carbonyl group Chemical group 0.000 claims abstract description 6
125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract description 5
125000004103 aminoalkyl group Chemical group 0.000 claims abstract description 5
125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 5
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 4
125000003709 fluoroalkyl group Chemical group 0.000 claims abstract description 4
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 4
125000004434 sulfur atom Chemical group 0.000 claims abstract description 4
125000004356 hydroxy functional group Chemical group O* 0.000 claims abstract 3
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 77
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 23
PIGFYZPCRLYGLF-UHFFFAOYSA-N Aluminum nitride Chemical compound [Al]#N PIGFYZPCRLYGLF-UHFFFAOYSA-N 0.000 claims description 18
239000002253 acid Substances 0.000 claims description 18
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 13
150000007522 mineralic acids Chemical class 0.000 claims description 4
125000005098 aryl alkoxy carbonyl group Chemical group 0.000 claims description 3
125000004452 carbocyclyl group Chemical group 0.000 claims description 3
108010017640 Aspartic Acid Proteases Proteins 0.000 abstract description 4
102000004580 Aspartic Acid Proteases Human genes 0.000 abstract description 4
201000010099 disease Diseases 0.000 abstract description 4
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 4
101100294102 Caenorhabditis elegans nhr-2 gene Proteins 0.000 abstract 1
229940121649 protein inhibitor Drugs 0.000 abstract 1
239000012268 protein inhibitor Substances 0.000 abstract 1
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 355
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 350
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 186
LLVBUQHDQQCEAO-UHFFFAOYSA-N isoquinoline-8-carboxamide Chemical compound C1=NC=C2C(C(=O)N)=CC=CC2=C1 LLVBUQHDQQCEAO-UHFFFAOYSA-N 0.000 description 168
229950003188 isovaleryl diethylamide Drugs 0.000 description 132
LEINOXRFIYQSFV-ZPGRZCPFSA-N (3s)-n-[(2s)-6-amino-1-(2,2-diphenylethylamino)-1-oxohexan-2-yl]-2-(4-oxo-4-phenylbutanoyl)-3,4-dihydro-1h-isoquinoline-3-carboxamide Chemical compound C([C@H]1C(=O)N[C@@H](CCCCN)C(=O)NCC(C=2C=CC=CC=2)C=2C=CC=CC=2)C2=CC=CC=C2CN1C(=O)CCC(=O)C1=CC=CC=C1 LEINOXRFIYQSFV-ZPGRZCPFSA-N 0.000 description 95
239000000243 solution Substances 0.000 description 90
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 84
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 75
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 63
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 63
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 60
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 57
238000000034 method Methods 0.000 description 55
238000006243 chemical reaction Methods 0.000 description 45
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 42
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 42
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 42
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 41
239000007787 solid Substances 0.000 description 38
239000003039 volatile agent Substances 0.000 description 38
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 30
229910052943 magnesium sulfate Inorganic materials 0.000 description 30
235000019341 magnesium sulphate Nutrition 0.000 description 30
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 29
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 29
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 28
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 27
230000002829 reductive effect Effects 0.000 description 27
239000012267 brine Substances 0.000 description 26
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 26
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 24
239000007858 starting material Substances 0.000 description 24
239000011347 resin Substances 0.000 description 22
229920005989 resin Polymers 0.000 description 22
239000000741 silica gel Substances 0.000 description 22
229910002027 silica gel Inorganic materials 0.000 description 22
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
239000012074 organic phase Substances 0.000 description 20
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 18
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
239000000203 mixture Substances 0.000 description 18
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 16
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 16
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
239000003153 chemical reaction reagent Substances 0.000 description 16
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 15
LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 14
239000003921 oil Substances 0.000 description 14
235000019198 oils Nutrition 0.000 description 14
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
238000002360 preparation method Methods 0.000 description 14
241000725303 Human immunodeficiency virus Species 0.000 description 13
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 13
239000006260 foam Substances 0.000 description 13
ZRALMJNLWLKCOK-SMOXQLQSSA-N (3S,4aS)-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline-3-carboxamide Chemical compound C1N[C@@H](C[C@@H]2CCCCC12)C(=O)N ZRALMJNLWLKCOK-SMOXQLQSSA-N 0.000 description 12
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
241000700605 Viruses Species 0.000 description 12
229960000583 acetic acid Drugs 0.000 description 12
HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 description 11
125000003580 L-valyl group Chemical group [H]N([H])[C@]([H])(C(=O)[*])C(C([H])([H])[H])(C([H])([H])[H])[H] 0.000 description 11
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 11
235000011054 acetic acid Nutrition 0.000 description 10
230000015572 biosynthetic process Effects 0.000 description 10
125000004432 carbon atom Chemical group C* 0.000 description 10
229940024606 amino acid Drugs 0.000 description 9
235000001014 amino acid Nutrition 0.000 description 9
150000001413 amino acids Chemical class 0.000 description 9
239000008346 aqueous phase Substances 0.000 description 9
229910000030 sodium bicarbonate Inorganic materials 0.000 description 9
235000017557 sodium bicarbonate Nutrition 0.000 description 9
238000003786 synthesis reaction Methods 0.000 description 9
GRFNBEZIAWKNCO-UHFFFAOYSA-N 3-pyridinol Chemical compound OC1=CC=CN=C1 GRFNBEZIAWKNCO-UHFFFAOYSA-N 0.000 description 8
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
239000003054 catalyst Substances 0.000 description 8
239000012044 organic layer Substances 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 8
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
108091005804 Peptidases Proteins 0.000 description 7
239000004365 Protease Substances 0.000 description 7
102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 description 7
150000001732 carboxylic acid derivatives Chemical class 0.000 description 7
239000001257 hydrogen Substances 0.000 description 7
229910052739 hydrogen Inorganic materials 0.000 description 7
239000003112 inhibitor Substances 0.000 description 7
230000002401 inhibitory effect Effects 0.000 description 7
239000003208 petroleum Substances 0.000 description 7
229910000027 potassium carbonate Inorganic materials 0.000 description 7
235000011181 potassium carbonates Nutrition 0.000 description 7
108090000765 processed proteins & peptides Proteins 0.000 description 7
229960004295 valine Drugs 0.000 description 7
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
102000004190 Enzymes Human genes 0.000 description 6
108090000790 Enzymes Proteins 0.000 description 6
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
LSQZJLSUYDQPKJ-NJBDSQKTSA-N amoxicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=C(O)C=C1 LSQZJLSUYDQPKJ-NJBDSQKTSA-N 0.000 description 6
229960003022 amoxicillin Drugs 0.000 description 6
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 6
239000003814 drug Substances 0.000 description 6
LSQZJLSUYDQPKJ-UHFFFAOYSA-N p-Hydroxyampicillin Natural products O=C1N2C(C(O)=O)C(C)(C)SC2C1NC(=O)C(N)C1=CC=C(O)C=C1 LSQZJLSUYDQPKJ-UHFFFAOYSA-N 0.000 description 6
239000012312 sodium hydride Substances 0.000 description 6
229910000104 sodium hydride Inorganic materials 0.000 description 6
239000002904 solvent Substances 0.000 description 6
239000000725 suspension Substances 0.000 description 6
125000002114 valyl group Chemical group 0.000 description 6
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
150000001299 aldehydes Chemical class 0.000 description 5
125000005093 alkyl carbonyl alkyl group Chemical group 0.000 description 5
150000001412 amines Chemical class 0.000 description 5
239000012298 atmosphere Substances 0.000 description 5
239000000460 chlorine Substances 0.000 description 5
238000010511 deprotection reaction Methods 0.000 description 5
150000002148 esters Chemical class 0.000 description 5
238000001914 filtration Methods 0.000 description 5
229910052736 halogen Inorganic materials 0.000 description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
239000012442 inert solvent Substances 0.000 description 5
229910052740 iodine Inorganic materials 0.000 description 5
150000002576 ketones Chemical class 0.000 description 5
125000006239 protecting group Chemical group 0.000 description 5
238000010992 reflux Methods 0.000 description 5
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 4
244000166102 Eucalyptus leucoxylon Species 0.000 description 4
235000004694 Eucalyptus leucoxylon Nutrition 0.000 description 4
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 4
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
102100034343 Integrase Human genes 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 4
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
239000013543 active substance Substances 0.000 description 4
125000002619 bicyclic group Chemical group 0.000 description 4
239000006071 cream Substances 0.000 description 4
239000006185 dispersion Substances 0.000 description 4
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 4
239000007903 gelatin capsule Substances 0.000 description 4
150000002367 halogens Chemical class 0.000 description 4
208000015181 infectious disease Diseases 0.000 description 4
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 4
239000007788 liquid Substances 0.000 description 4
239000000463 material Substances 0.000 description 4
230000007246 mechanism Effects 0.000 description 4
239000000546 pharmaceutical excipient Substances 0.000 description 4
229920005862 polyol Polymers 0.000 description 4
150000003077 polyols Chemical class 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
125000004076 pyridyl group Chemical group 0.000 description 4
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
238000003756 stirring Methods 0.000 description 4
239000000126 substance Substances 0.000 description 4
239000000758 substrate Substances 0.000 description 4
BNWCETAHAJSBFG-UHFFFAOYSA-N tert-butyl 2-bromoacetate Chemical compound CC(C)(C)OC(=O)CBr BNWCETAHAJSBFG-UHFFFAOYSA-N 0.000 description 4
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 4
NXLNNXIXOYSCMB-UHFFFAOYSA-N (4-nitrophenyl) carbonochloridate Chemical compound [O-][N+](=O)C1=CC=C(OC(Cl)=O)C=C1 NXLNNXIXOYSCMB-UHFFFAOYSA-N 0.000 description 3
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 3
KQFNGUIYAAXYKN-UHFFFAOYSA-N 2-(6-methylpyridin-3-yl)oxyacetic acid;hydrobromide Chemical compound Br.CC1=CC=C(OCC(O)=O)C=N1 KQFNGUIYAAXYKN-UHFFFAOYSA-N 0.000 description 3
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 3
LXVSANCQXSSLPA-UHFFFAOYSA-N 2-Ethyl-2-hydroxy-butyric acid Chemical compound CCC(O)(CC)C(O)=O LXVSANCQXSSLPA-UHFFFAOYSA-N 0.000 description 3
YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 description 3
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LBHDXZPKFNCPNS-UHFFFAOYSA-N 2-pyridin-1-ium-3-yloxyacetic acid;2,2,2-trifluoroacetate Chemical compound OC(=O)C(F)(F)F.OC(=O)COC1=CC=CN=C1 LBHDXZPKFNCPNS-UHFFFAOYSA-N 0.000 description 3
ZMNXEJAYOVOXJH-UHFFFAOYSA-N 2-pyrimidin-2-yloxyacetic acid;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)COC1=NC=CC=N1 ZMNXEJAYOVOXJH-UHFFFAOYSA-N 0.000 description 3
MQTZUKPHZMUGHH-UHFFFAOYSA-N 3-methyl-3-methylsulfonylbutanoic acid Chemical compound CS(=O)(=O)C(C)(C)CC(O)=O MQTZUKPHZMUGHH-UHFFFAOYSA-N 0.000 description 3
BNVXYXRSJIWWDX-UHFFFAOYSA-N 4,5-dimethylfuran-2-carboxylic acid Chemical compound CC=1C=C(C(O)=O)OC=1C BNVXYXRSJIWWDX-UHFFFAOYSA-N 0.000 description 3
208000030507 AIDS Diseases 0.000 description 3
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208000031886 HIV Infections Diseases 0.000 description 3
108010010369 HIV Protease Proteins 0.000 description 3
VVNCNSJFMMFHPL-GSVOUGTGSA-N L-penicillamine Chemical compound CC(C)(S)[C@H](N)C(O)=O VVNCNSJFMMFHPL-GSVOUGTGSA-N 0.000 description 3
239000002841 Lewis acid Substances 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
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150000007513 acids Chemical class 0.000 description 3
125000003277 amino group Chemical group 0.000 description 3
150000008064 anhydrides Chemical class 0.000 description 3
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the nitrogen-containing ring
- C07D217/26—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
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Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
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Molecular Biology (AREA)
Oncology (AREA)
Communicable Diseases (AREA)
AIDS & HIV (AREA)
Engineering & Computer Science (AREA)
Tropical Medicine & Parasitology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Other In-Based Heterocyclic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

BG107839A 2000-11-22 2003-05-22 Нови съединения за използване като hiv протеазни инхибитори BG107839A (bg)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GBGB0028483.6A GB0028483D0 (en)	2000-11-22	2000-11-22	Hydroxyethylamine HIV protease inhibitors
PCT/EP2001/013068 WO2002042277A1 (en)	2000-11-22	2001-11-12	Novel compounds for use as hiv protease inhibitors

Publications (1)

Publication Number	Publication Date
BG107839A true BG107839A (bg)	2004-06-30

Family

ID=9903670

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BG107839A BG107839A (bg)	2000-11-22	2003-05-22	Нови съединения за използване като hiv протеазни инхибитори

Country Status (27)

Country	Link
US (1)	US6472404B1 (es)
EP (1)	EP1339692A1 (es)
JP (1)	JP2004520283A (es)
KR (1)	KR20030060953A (es)
CN (1)	CN1476436A (es)
AR (1)	AR031763A1 (es)
AU (2)	AU2002229546B2 (es)
BG (1)	BG107839A (es)
BR (1)	BR0115566A (es)
CA (1)	CA2428459A1 (es)
CZ (1)	CZ20031667A3 (es)
EC (1)	ECSP034618A (es)
GB (1)	GB0028483D0 (es)
GT (1)	GT200100233A (es)
HU (1)	HUP0303007A2 (es)
IL (1)	IL155573A0 (es)
MA (1)	MA26966A1 (es)
MX (1)	MXPA03004534A (es)
NO (1)	NO20032290L (es)
NZ (1)	NZ525550A (es)
PA (1)	PA8533401A1 (es)
PE (1)	PE20020610A1 (es)
PL (1)	PL366704A1 (es)
RU (1)	RU2265016C2 (es)
SK (1)	SK7602003A3 (es)
UY (1)	UY27033A1 (es)
WO (1)	WO2002042277A1 (es)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN101014572B (zh) *	2004-09-15	2011-07-06	盐野义制药株式会社	具有hiv整合酶抑制活性的氨基甲酰基吡啶酮衍生物
UA87884C2 (uk) *	2004-12-03	2009-08-25	Мерк Энд Ко., Инк.	Безводна кристалічна калієва сіль інгібітора віл-інтегрази
MY161992A (en) *	2008-03-26	2017-05-31	Daiichi Sankyo Co Ltd	Novel tetrahydroisoquinoline derivative
US12083099B2 (en)	2020-10-28	2024-09-10	Accencio LLC	Methods of treating symptoms of coronavirus infection with viral protease inhibitors

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB8927913D0 (en)	1989-12-11	1990-02-14	Hoffmann La Roche	Amino acid derivatives
MX9308016A (es) *	1992-12-22	1994-08-31	Lilly Co Eli	Compuestos inhibidores de la proteasa del virus de la inmunodeficiencia humana, procedimiento para su preparacion y formulacion farmaceutica que los contiene.

2000
- 2000-11-22 GB GBGB0028483.6A patent/GB0028483D0/en not_active Ceased
2001
- 2001-11-12 AU AU2002229546A patent/AU2002229546B2/en not_active Ceased
- 2001-11-12 MX MXPA03004534A patent/MXPA03004534A/es active IP Right Grant
- 2001-11-12 CZ CZ20031667A patent/CZ20031667A3/cs unknown
- 2001-11-12 RU RU2003117468/04A patent/RU2265016C2/ru not_active IP Right Cessation
- 2001-11-12 PL PL01366704A patent/PL366704A1/xx not_active Application Discontinuation
- 2001-11-12 HU HU0303007A patent/HUP0303007A2/hu unknown
- 2001-11-12 SK SK760-2003A patent/SK7602003A3/sk unknown
- 2001-11-12 WO PCT/EP2001/013068 patent/WO2002042277A1/en active IP Right Grant
- 2001-11-12 NZ NZ525550A patent/NZ525550A/en unknown
- 2001-11-12 CA CA002428459A patent/CA2428459A1/en not_active Abandoned
- 2001-11-12 AU AU2954602A patent/AU2954602A/xx active Pending
- 2001-11-12 EP EP01990405A patent/EP1339692A1/en not_active Withdrawn
- 2001-11-12 IL IL15557301A patent/IL155573A0/xx unknown
- 2001-11-12 CN CNA018192890A patent/CN1476436A/zh active Pending
- 2001-11-12 JP JP2002544412A patent/JP2004520283A/ja active Pending
- 2001-11-12 BR BR0115566-0A patent/BR0115566A/pt not_active IP Right Cessation
- 2001-11-12 KR KR10-2003-7006907A patent/KR20030060953A/ko not_active Application Discontinuation
- 2001-11-20 US US09/999,082 patent/US6472404B1/en not_active Expired - Fee Related
- 2001-11-21 AR ARP010105431A patent/AR031763A1/es unknown
- 2001-11-21 GT GT200100233A patent/GT200100233A/es unknown
- 2001-11-21 PA PA20018533401A patent/PA8533401A1/es unknown
- 2001-11-21 UY UY27033A patent/UY27033A1/es not_active Application Discontinuation
- 2001-11-22 PE PE2001001170A patent/PE20020610A1/es not_active Application Discontinuation
2003
- 2003-05-21 EC EC2003004618A patent/ECSP034618A/es unknown
- 2003-05-21 NO NO20032290A patent/NO20032290L/no unknown
- 2003-05-22 MA MA27172A patent/MA26966A1/fr unknown
- 2003-05-22 BG BG107839A patent/BG107839A/bg unknown

Also Published As

Publication number	Publication date
EP1339692A1 (en)	2003-09-03
RU2265016C2 (ru)	2005-11-27
GB0028483D0 (en)	2001-01-10
CN1476436A (zh)	2004-02-18
NO20032290D0 (no)	2003-05-21
ECSP034618A (es)	2003-06-25
RU2003117468A (ru)	2005-01-27
PA8533401A1 (es)	2002-10-31
AU2954602A (en)	2002-06-03
SK7602003A3 (en)	2004-01-08
US6472404B1 (en)	2002-10-29
PE20020610A1 (es)	2002-07-13
CA2428459A1 (en)	2002-05-30
MA26966A1 (fr)	2004-12-20
KR20030060953A (ko)	2003-07-16
IL155573A0 (en)	2003-11-23
CZ20031667A3 (cs)	2004-01-14
NZ525550A (en)	2004-11-26
UY27033A1 (es)	2002-06-20
BR0115566A (pt)	2003-09-30
NO20032290L (no)	2003-05-21
MXPA03004534A (es)	2003-09-10
WO2002042277A1 (en)	2002-05-30
HUP0303007A2 (hu)	2003-12-29
AR031763A1 (es)	2003-10-01
GT200100233A (es)	2002-07-04
AU2002229546B2 (en)	2006-05-04
JP2004520283A (ja)	2004-07-08
PL366704A1 (en)	2005-02-07

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