NO326174B1 - Bredspektrede 2-(substituert-amino)-benzotiazolsulfonamid-hiv-proteaseinhibitorer - Google Patents

Bredspektrede 2-(substituert-amino)-benzotiazolsulfonamid-hiv-proteaseinhibitorer Download PDF

Info

Publication number: NO326174B1
Authority: NO; Norway
Prior art keywords: het; 4alkyl; alkyl; compound according; hydrogen
Prior art date: 2001-02-14

Application number

NO20033584A

Other languages

English (en)

Norwegian (no)

Other versions

NO20033584L (no

NO20033584D0 (no

Inventor

Wim Gaston Verschueren

Piet Tom Bert Paul Wigerinck

Sandrine Marie Hele Vendeville

Marie-Pierre T M M G D Bethune

Jan Octaaf Antoon De Kerpel

Samuel Leo Christiaan Moors

Herman Augustinus De Kock

Marieke Christiane Johan Voets

Daniel P Getman

Dominique Louis Nest Surleraux

Original Assignee

Tibotec Pharm Ltd

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.)

2001-02-14

Filing date

2003-08-13

Publication date

2008-10-13

2003-08-13 Application filed by Tibotec Pharm Ltd filed Critical Tibotec Pharm Ltd

2003-08-13 Publication of NO20033584D0 publication Critical patent/NO20033584D0/no

2003-10-14 Publication of NO20033584L publication Critical patent/NO20033584L/no

2008-10-13 Publication of NO326174B1 publication Critical patent/NO326174B1/no

Links

-1 2- (substituted-amino) benzothiazole sulfonamide Chemical class 0.000 title claims description 72
239000004030 hiv protease inhibitor Substances 0.000 title description 3
238000001228 spectrum Methods 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims description 199
239000000543 intermediate Substances 0.000 claims description 147
239000000203 mixture Substances 0.000 claims description 61
229910052739 hydrogen Inorganic materials 0.000 claims description 59
125000000217 alkyl group Chemical group 0.000 claims description 55
239000001257 hydrogen Substances 0.000 claims description 55
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 53
241000725303 Human immunodeficiency virus Species 0.000 claims description 38
238000002360 preparation method Methods 0.000 claims description 35
238000000034 method Methods 0.000 claims description 33
150000002431 hydrogen Chemical class 0.000 claims description 29
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 26
239000003814 drug Substances 0.000 claims description 24
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 22
150000003839 salts Chemical class 0.000 claims description 21
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
125000003118 aryl group Chemical group 0.000 claims description 18
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 15
125000003277 amino group Chemical group 0.000 claims description 13
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
229940079593 drug Drugs 0.000 claims description 11
125000004043 oxo group Chemical group O=* 0.000 claims description 11
239000000546 pharmaceutical excipient Substances 0.000 claims description 11
241001430294 unidentified retrovirus Species 0.000 claims description 11
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 9
229910052757 nitrogen Inorganic materials 0.000 claims description 9
125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
150000001204 N-oxides Chemical class 0.000 claims description 8
108091005804 Peptidases Proteins 0.000 claims description 8
239000008194 pharmaceutical composition Substances 0.000 claims description 8
125000001424 substituent group Chemical group 0.000 claims description 8
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 claims description 7
239000004365 Protease Substances 0.000 claims description 7
102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 claims description 7
125000006239 protecting group Chemical group 0.000 claims description 7
125000006284 3-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(F)=C1[H])C([H])([H])* 0.000 claims description 6
238000004519 manufacturing process Methods 0.000 claims description 6
230000001177 retroviral effect Effects 0.000 claims description 6
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 6
241000124008 Mammalia Species 0.000 claims description 5
125000003545 alkoxy group Chemical group 0.000 claims description 5
229910052736 halogen Inorganic materials 0.000 claims description 5
150000002367 halogens Chemical group 0.000 claims description 5
230000002401 inhibitory effect Effects 0.000 claims description 5
125000004104 aryloxy group Chemical group 0.000 claims description 4
239000003153 chemical reaction reagent Substances 0.000 claims description 4
201000010099 disease Diseases 0.000 claims description 4
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 4
208000015181 infectious disease Diseases 0.000 claims description 4
FODOUIXGKGNSMR-UHFFFAOYSA-L magnesium;2-oxidooxycarbonylbenzoate;hexahydrate Chemical compound O.O.O.O.O.O.[Mg+2].[O-]OC(=O)C1=CC=CC=C1C([O-])=O FODOUIXGKGNSMR-UHFFFAOYSA-L 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
KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 claims description 3
IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 3
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical group O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 2
208000005074 Retroviridae Infections Diseases 0.000 claims description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
125000002541 furyl group Chemical group 0.000 claims description 2
125000002632 imidazolidinyl group Chemical group 0.000 claims description 2
125000000842 isoxazolyl group Chemical group 0.000 claims description 2
125000002757 morpholinyl group Chemical group 0.000 claims description 2
125000004193 piperazinyl group Chemical group 0.000 claims description 2
125000003386 piperidinyl group Chemical group 0.000 claims description 2
125000004076 pyridyl group Chemical group 0.000 claims description 2
230000010076 replication Effects 0.000 claims description 2
125000000335 thiazolyl group Chemical group 0.000 claims description 2
125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 10
125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 2
125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 2
IHKOXYNAMXNNDK-UHFFFAOYSA-N 2,3,3a,4,5,6a-hexahydrofuro[2,3-b]furan Chemical compound C1COC2OCCC21 IHKOXYNAMXNNDK-UHFFFAOYSA-N 0.000 claims 1
BIPRNLSSLKASRT-UHFFFAOYSA-N 2,3,3a,4,5,6a-hexahydrofuro[2,3-b]furan-4-yl n-[4-[[2-[2-(dimethylamino)ethylamino]-1,3-benzothiazol-6-yl]sulfonyl-(2-methylpropyl)amino]-3-hydroxy-1-phenylbutan-2-yl]carbamate Chemical compound C=1C=C2N=C(NCCN(C)C)SC2=CC=1S(=O)(=O)N(CC(C)C)CC(O)C(NC(=O)OC1C2CCOC2OC1)CC1=CC=CC=C1 BIPRNLSSLKASRT-UHFFFAOYSA-N 0.000 claims 1
HBJMMMAJSBLTMB-UHFFFAOYSA-N 2,3,3a,4,5,6a-hexahydrofuro[2,3-b]furan-4-yl n-[4-[[2-[3-(dimethylamino)propyl-methylamino]-1,3-benzothiazol-6-yl]sulfonyl-(2-methylpropyl)amino]-3-hydroxy-1-phenylbutan-2-yl]carbamate Chemical compound C=1C=C2N=C(N(C)CCCN(C)C)SC2=CC=1S(=O)(=O)N(CC(C)C)CC(O)C(NC(=O)OC1C2CCOC2OC1)CC1=CC=CC=C1 HBJMMMAJSBLTMB-UHFFFAOYSA-N 0.000 claims 1
QAGMBTAACMQRSS-MTULOOOASA-N [(2r,3s)-3,5-diacetyloxyoxolan-2-yl]methyl acetate Chemical compound CC(=O)OC[C@H]1OC(OC(C)=O)C[C@@H]1OC(C)=O QAGMBTAACMQRSS-MTULOOOASA-N 0.000 claims 1
125000001589 carboacyl group Chemical group 0.000 claims 1
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 1
KRLZUGUOORSXFA-UHFFFAOYSA-N oxolan-3-yl n-[4-[[2-[2-(dimethylamino)ethylamino]-1,3-benzothiazol-6-yl]sulfonyl-(2-methylpropyl)amino]-3-hydroxy-1-phenylbutan-2-yl]carbamate Chemical compound C=1C=C2N=C(NCCN(C)C)SC2=CC=1S(=O)(=O)N(CC(C)C)CC(O)C(NC(=O)OC1COCC1)CC1=CC=CC=C1 KRLZUGUOORSXFA-UHFFFAOYSA-N 0.000 claims 1
125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 222
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 75
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 60
239000000243 solution Substances 0.000 description 51
239000002904 solvent Substances 0.000 description 41
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 33
239000011541 reaction mixture Substances 0.000 description 33
230000003595 spectral effect Effects 0.000 description 30
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 28
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 20
230000000694 effects Effects 0.000 description 20
239000012044 organic layer Substances 0.000 description 19
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 18
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
239000000741 silica gel Substances 0.000 description 17
229910002027 silica gel Inorganic materials 0.000 description 17
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 15
230000002829 reductive effect Effects 0.000 description 15
241000700605 Viruses Species 0.000 description 14
239000002253 acid Substances 0.000 description 14
239000002585 base Substances 0.000 description 14
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
238000011282 treatment Methods 0.000 description 13
239000012503 blood component Substances 0.000 description 12
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 12
238000006243 chemical reaction Methods 0.000 description 12
239000012043 crude product Substances 0.000 description 12
229940042399 direct acting antivirals protease inhibitors Drugs 0.000 description 12
238000001704 evaporation Methods 0.000 description 12
230000008020 evaporation Effects 0.000 description 12
239000000137 peptide hydrolase inhibitor Substances 0.000 description 12
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 12
239000003795 chemical substances by application Substances 0.000 description 11
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
229920000858 Cyclodextrin Polymers 0.000 description 10
229910052943 magnesium sulfate Inorganic materials 0.000 description 10
235000019341 magnesium sulphate Nutrition 0.000 description 10
150000003254 radicals Chemical class 0.000 description 10
238000003756 stirring Methods 0.000 description 10
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 10
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 9
125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 9
241000713772 Human immunodeficiency virus 1 Species 0.000 description 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
210000004027 cell Anatomy 0.000 description 9
238000004587 chromatography analysis Methods 0.000 description 9
239000012074 organic phase Substances 0.000 description 9
229910000029 sodium carbonate Inorganic materials 0.000 description 9
239000000126 substance Substances 0.000 description 9
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 8
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
230000036436 anti-hiv Effects 0.000 description 8
238000003556 assay Methods 0.000 description 8
239000012267 brine Substances 0.000 description 8
239000000306 component Substances 0.000 description 8
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 8
239000007787 solid Substances 0.000 description 8
150000001412 amines Chemical class 0.000 description 7
230000001965 increasing effect Effects 0.000 description 7
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
208000030507 AIDS Diseases 0.000 description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
150000007513 acids Chemical class 0.000 description 6
125000004432 carbon atom Chemical group C* 0.000 description 6
238000004895 liquid chromatography mass spectrometry Methods 0.000 description 6
239000007962 solid dispersion Substances 0.000 description 6
241001465754 Metazoa Species 0.000 description 5
230000000840 anti-viral effect Effects 0.000 description 5
125000004429 atom Chemical group 0.000 description 5
238000009472 formulation Methods 0.000 description 5
230000014509 gene expression Effects 0.000 description 5
239000003112 inhibitor Substances 0.000 description 5
210000004379 membrane Anatomy 0.000 description 5
238000002953 preparative HPLC Methods 0.000 description 5
229910052705 radium Inorganic materials 0.000 description 5
239000007858 starting material Substances 0.000 description 5
238000006467 substitution reaction Methods 0.000 description 5
238000005406 washing Methods 0.000 description 5
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 4
JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 description 4
DCXYFEDJOCDNAF-UHFFFAOYSA-N Asparagine Natural products OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 description 4
VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 4
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
108010010369 HIV Protease Proteins 0.000 description 4
DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
229910021529 ammonia Inorganic materials 0.000 description 4
229960001230 asparagine Drugs 0.000 description 4
235000009582 asparagine Nutrition 0.000 description 4
229940125810 compound 20 Drugs 0.000 description 4
239000006185 dispersion Substances 0.000 description 4
JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 description 4
125000004356 hydroxy functional group Chemical group O* 0.000 description 4
NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 4
239000000463 material Substances 0.000 description 4
239000012528 membrane Substances 0.000 description 4
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HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 4
210000002966 serum Anatomy 0.000 description 4
239000011734 sodium Substances 0.000 description 4
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
238000002560 therapeutic procedure Methods 0.000 description 4
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ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 description 3
WRXNJTBODVGDRY-UHFFFAOYSA-N 2-pyrrolidin-1-ylethanamine Chemical compound NCCN1CCCC1 WRXNJTBODVGDRY-UHFFFAOYSA-N 0.000 description 3
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JQUNFHFWXCXPRK-AMMMHQJVSA-N [(3as,4r,6ar)-2,3,3a,4,5,6a-hexahydrofuro[2,3-b]furan-4-yl] n-[(2s,3r)-4-[[2-[(1-cyclopentylpiperidin-4-yl)amino]-1,3-benzothiazol-6-yl]sulfonyl-(2-methylpropyl)amino]-3-hydroxy-1-phenylbutan-2-yl]carbamate Chemical group C([C@@H]([C@H](O)CN(CC(C)C)S(=O)(=O)C=1C=C2SC(NC3CCN(CC3)C3CCCC3)=NC2=CC=1)NC(=O)O[C@@H]1[C@@H]2CCO[C@@H]2OC1)C1=CC=CC=C1 JQUNFHFWXCXPRK-AMMMHQJVSA-N 0.000 description 3
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
- 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
- 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
- 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
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles 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 in position 2
- C07D277/82—Nitrogen atoms

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Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Virology (AREA)
Veterinary Medicine (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Molecular Biology (AREA)
Communicable Diseases (AREA)
Oncology (AREA)
Tropical Medicine & Parasitology (AREA)
AIDS & HIV (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Thiazole And Isothizaole Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

NO20033584A 2001-02-14 2003-08-13 Bredspektrede 2-(substituert-amino)-benzotiazolsulfonamid-hiv-proteaseinhibitorer NO326174B1 (no)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
EP01200529		2001-02-14
US28775801P	2001-05-02	2001-05-02
PCT/EP2002/001788 WO2002083657A2 (en)	2001-02-14	2002-02-14	Broadspectrum 2-(substituted-amino)-benzothiazole sulfonamide hiv protease inhibitors

Publications (3)

Publication Number	Publication Date
NO20033584D0 NO20033584D0 (no)	2003-08-13
NO20033584L NO20033584L (no)	2003-10-14
NO326174B1 true NO326174B1 (no)	2008-10-13

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NO20033584A NO326174B1 (no)	2001-02-14	2003-08-13	Bredspektrede 2-(substituert-amino)-benzotiazolsulfonamid-hiv-proteaseinhibitorer

Country Status (30)

Country	Link
US (1)	US7659404B2 (pt)
EP (1)	EP1370543B1 (pt)
JP (1)	JP4530612B2 (pt)
KR (1)	KR100870184B1 (pt)
CN (2)	CN101230067B (pt)
AP (1)	AP1504A (pt)
AT (1)	ATE343567T1 (pt)
AU (1)	AU2002302363B2 (pt)
BG (1)	BG66301B1 (pt)
BR (1)	BR0207862A (pt)
CA (1)	CA2438304C (pt)
CY (1)	CY1108073T1 (pt)
CZ (1)	CZ304273B6 (pt)
DE (1)	DE60215623T2 (pt)
DK (1)	DK1370543T3 (pt)
EA (1)	EA006096B1 (pt)
EE (1)	EE05385B1 (pt)
ES (1)	ES2275866T3 (pt)
HR (1)	HRP20030735B1 (pt)
HU (1)	HU229224B1 (pt)
IL (2)	IL157171A0 (pt)
MX (1)	MXPA03007236A (pt)
NO (1)	NO326174B1 (pt)
NZ (1)	NZ527391A (pt)
PL (1)	PL213327B1 (pt)
PT (1)	PT1370543E (pt)
SI (1)	SI1370543T1 (pt)
SK (1)	SK287582B6 (pt)
WO (1)	WO2002083657A2 (pt)
ZA (1)	ZA200306086B (pt)

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2002
- 2002-02-14 PT PT02729930T patent/PT1370543E/pt unknown
- 2002-02-14 AT AT02729930T patent/ATE343567T1/de active
- 2002-02-14 HU HU0303257A patent/HU229224B1/hu not_active IP Right Cessation
- 2002-02-14 US US10/467,609 patent/US7659404B2/en not_active Expired - Fee Related
- 2002-02-14 CA CA2438304A patent/CA2438304C/en not_active Expired - Fee Related
- 2002-02-14 DK DK02729930T patent/DK1370543T3/da active
- 2002-02-14 EA EA200300891A patent/EA006096B1/ru not_active IP Right Cessation
- 2002-02-14 JP JP2002581413A patent/JP4530612B2/ja not_active Expired - Fee Related
- 2002-02-14 WO PCT/EP2002/001788 patent/WO2002083657A2/en not_active Ceased
- 2002-02-14 CN CN2007101997173A patent/CN101230067B/zh not_active Expired - Fee Related
- 2002-02-14 BR BR0207862-7A patent/BR0207862A/pt not_active IP Right Cessation
- 2002-02-14 SK SK1102-2003A patent/SK287582B6/sk not_active IP Right Cessation
- 2002-02-14 NZ NZ527391A patent/NZ527391A/xx not_active IP Right Cessation
- 2002-02-14 IL IL15717102A patent/IL157171A0/xx unknown
- 2002-02-14 AP APAP/P/2003/002856A patent/AP1504A/en active
- 2002-02-14 AU AU2002302363A patent/AU2002302363B2/en not_active Ceased
- 2002-02-14 EP EP02729930A patent/EP1370543B1/en not_active Expired - Lifetime
- 2002-02-14 PL PL363778A patent/PL213327B1/pl unknown
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- 2002-02-14 KR KR1020037010506A patent/KR100870184B1/ko not_active Expired - Fee Related
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- 2002-02-14 EE EEP200300381A patent/EE05385B1/xx not_active IP Right Cessation
- 2002-02-14 SI SI200230467T patent/SI1370543T1/sl unknown
- 2002-02-14 CZ CZ2003-2415A patent/CZ304273B6/cs not_active IP Right Cessation
- 2002-02-14 DE DE60215623T patent/DE60215623T2/de not_active Expired - Lifetime
- 2002-02-14 ES ES02729930T patent/ES2275866T3/es not_active Expired - Lifetime
- 2002-02-14 CN CNB028049829A patent/CN100369904C/zh not_active Expired - Fee Related
2003
- 2003-07-30 IL IL157171A patent/IL157171A/en not_active IP Right Cessation
- 2003-08-06 ZA ZA2003/06086A patent/ZA200306086B/en unknown
- 2003-08-13 NO NO20033584A patent/NO326174B1/no not_active IP Right Cessation
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Also Published As

Publication number	Publication date
JP2004518767A (ja)	2004-06-24
EA006096B1 (ru)	2005-08-25
AU2002302363B2 (en)	2008-05-01
NZ527391A (en)	2005-04-29
BG108143A (en)	2004-07-30
ES2275866T3 (es)	2007-06-16
CN101230067A (zh)	2008-07-30
SI1370543T1 (sl)	2007-04-30
DE60215623T2 (de)	2007-08-30
CY1108073T1 (el)	2014-02-12
KR100870184B1 (ko)	2008-11-24
EE05385B1 (et)	2011-02-15
NO20033584L (no)	2003-10-14
HRP20030735B1 (en)	2012-02-29
EE200300381A (et)	2003-12-15
AP1504A (en)	2005-12-10
CN1525962A (zh)	2004-09-01
AP2003002856A0 (en)	2003-09-30
NO20033584D0 (no)	2003-08-13
HUP0303257A2 (hu)	2004-01-28
US7659404B2 (en)	2010-02-09
SK287582B6 (sk)	2011-03-04
CA2438304C (en)	2011-04-12
PL363778A1 (en)	2004-11-29
EP1370543A2 (en)	2003-12-17
IL157171A (en)	2012-10-31
EP1370543B1 (en)	2006-10-25
WO2002083657A3 (en)	2003-02-13
CZ20032415A3 (cs)	2004-04-14
BR0207862A (pt)	2004-06-22
PL213327B1 (pl)	2013-02-28
EA200300891A1 (ru)	2004-02-26
US20040116485A1 (en)	2004-06-17
PT1370543E (pt)	2007-02-28
HK1061233A1 (en)	2004-09-10
WO2002083657A2 (en)	2002-10-24
IL157171A0 (en)	2004-02-08
MXPA03007236A (es)	2003-12-04
CA2438304A1 (en)	2002-10-24
HU229224B1 (en)	2013-09-30
JP4530612B2 (ja)	2010-08-25
CN101230067B (zh)	2011-06-15
ATE343567T1 (de)	2006-11-15
KR20030077017A (ko)	2003-09-29
BG66301B1 (bg)	2013-03-29
SK11022003A3 (sk)	2004-07-07
HRP20030735A2 (en)	2005-08-31
ZA200306086B (en)	2005-01-26
CZ304273B6 (cs)	2014-02-12
DK1370543T3 (da)	2007-02-19
CN100369904C (zh)	2008-02-20
DE60215623D1 (de)	2006-12-07

Publication	Publication Date	Title
NO326174B1 (no)	2008-10-13	Bredspektrede 2-(substituert-amino)-benzotiazolsulfonamid-hiv-proteaseinhibitorer
AU2002302363A1 (en)	2003-04-10	Broadspectrum 2-(substituted-amino)-benzothiazole sulfonamide HIV protease inhibitors
PL209029B1 (pl)	2011-07-29	Pochodne 2-aminobenzoksazolo-sulfonamidów jako inhibitory proteazy HIV, oraz kompozycje zawierające te związki
KR100942743B1 (ko)	2010-02-16	광범위 스펙트럼 헤테로사이클릭 치환된 페닐 포함설폰아미드 ｈｉｖ 프로테아제 저해제
KR20050025647A (ko)	2005-03-14	광범위 2-아미노-벤조티아졸 설폰아미드 ｈｉｖ프로테아제 저해제
NO328896B1 (no)	2010-06-07	2-(substituert-amino)-benzoxasolsulfonamid med HIV proteasehemmende virkning
EA010908B1 (ru)	2008-12-30	Ингибиторы вич-протеазы на основе замещённых бензизоксазолсульфонамидов широкого спектра действия
KR101302421B1 (ko)	2013-09-02	광범위 치환된 벤즈이미다졸 설폰아미드 ｈｉｖ 프로테아제 저해제
KR101327772B1 (ko)	2013-11-11	광범위 2-아미노-벤조티아졸 설폰아미드 ｈｉｖ 프로테아제 저해제
TWI325783B (en)	2010-06-11	Broadspectrum 2-(substituted-amino)-benzothiazole sulfonamide hiv protease inhibitors
HK1061233B (en)	2007-04-27	Broadspectrum 2-(substituted-amino)-benzothiazole sulfonamide hiv protease inhibitors

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