SK7602003A3 - Novel compounds for use as HIV protease inhibitors - Google Patents

Novel compounds for use as HIV protease inhibitors Download PDF

Info

Publication number: SK7602003A3
Authority: SK; Slovakia
Prior art keywords: tert; butyl; decahydro; isoquinolinecarboxamide; amino
Prior art date: 2000-11-22

Application number

SK760-2003A

Other languages

English (en)

Slovak (sk)

Inventor

Joseph Armstrong Martin

Sally Redshaw

Steven Swallow

Gareth John Thomas

Original Assignee

Hoffmann La Roche

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

2001-11-12

Publication date

2004-01-08

2001-11-12 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

2004-01-08 Publication of SK7602003A3 publication Critical patent/SK7602003A3/sk

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 131
239000004030 hiv protease inhibitor Substances 0.000 title description 4
-1 heterocyclyalkyl Chemical group 0.000 claims abstract description 328
125000000217 alkyl group Chemical group 0.000 claims abstract description 60
125000003118 aryl group Chemical group 0.000 claims abstract description 41
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 36
125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 32
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 24
229910052717 sulfur Inorganic materials 0.000 claims abstract description 20
229910052760 oxygen Inorganic materials 0.000 claims abstract description 18
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 17
229910052799 carbon Inorganic materials 0.000 claims abstract description 14
150000003839 salts Chemical class 0.000 claims abstract description 14
125000003342 alkenyl group Chemical group 0.000 claims abstract description 13
125000005129 aryl carbonyl group Chemical group 0.000 claims abstract description 13
125000004448 alkyl carbonyl group Chemical group 0.000 claims abstract description 11
125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims abstract description 10
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 10
229920006395 saturated elastomer Polymers 0.000 claims abstract description 10
125000005842 heteroatom Chemical group 0.000 claims abstract description 9
125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 8
125000000304 alkynyl group Chemical group 0.000 claims abstract description 8
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims abstract description 8
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims abstract description 8
125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 7
201000010099 disease Diseases 0.000 claims abstract description 7
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 7
125000005098 aryl alkoxy carbonyl group Chemical group 0.000 claims abstract description 6
125000005099 aryl alkyl carbonyl group Chemical group 0.000 claims abstract description 6
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 5
125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract description 5
125000004103 aminoalkyl group Chemical group 0.000 claims abstract description 5
125000004391 aryl sulfonyl group Chemical group 0.000 claims abstract description 5
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims abstract description 5
125000003709 fluoroalkyl group Chemical group 0.000 claims abstract description 5
125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 5
150000002485 inorganic esters Chemical class 0.000 claims abstract description 5
125000004434 sulfur atom Chemical group 0.000 claims abstract description 4
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 551
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 548
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 241
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 claims description 165
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 126
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 claims description 125
229950003188 isovaleryl diethylamide Drugs 0.000 claims description 85
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 63
SJFXVNZZLJUPCS-UHFFFAOYSA-N isoquinoline-5-carboxamide Chemical compound N1=CC=C2C(C(=O)N)=CC=CC2=C1 SJFXVNZZLJUPCS-UHFFFAOYSA-N 0.000 claims description 48
229910052739 hydrogen Inorganic materials 0.000 claims description 40
239000001257 hydrogen Substances 0.000 claims description 40
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 35
239000000203 mixture Substances 0.000 claims description 28
125000000592 heterocycloalkyl group Chemical group 0.000 claims description 26
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 24
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 24
PIGFYZPCRLYGLF-UHFFFAOYSA-N Aluminum nitride Chemical compound [Al]#N PIGFYZPCRLYGLF-UHFFFAOYSA-N 0.000 claims description 22
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 22
150000002431 hydrogen Chemical class 0.000 claims description 17
238000002360 preparation method Methods 0.000 claims description 17
PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 13
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 13
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 claims description 12
CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 12
125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims description 11
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 10
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 9
239000003814 drug Substances 0.000 claims description 9
125000002114 valyl group Chemical group 0.000 claims description 8
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
229910052757 nitrogen Inorganic materials 0.000 claims description 7
125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 6
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 6
150000001721 carbon Chemical group 0.000 claims description 6
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 6
230000001404 mediated effect Effects 0.000 claims description 6
150000002148 esters Chemical class 0.000 claims description 5
150000002895 organic esters Chemical group 0.000 claims description 5
239000013543 active substance Substances 0.000 claims description 4
125000000539 amino acid group Chemical group 0.000 claims description 4
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 4
125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
125000004512 1,2,3-thiadiazol-4-yl group Chemical group S1N=NC(=C1)* 0.000 claims description 3
QDKWLJJOYIFEBS-UHFFFAOYSA-N 1-fluoro-4-$l^{1}-oxidanylbenzene Chemical group [O]C1=CC=C(F)C=C1 QDKWLJJOYIFEBS-UHFFFAOYSA-N 0.000 claims description 3
125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
125000006508 2,6-difluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C(F)=C1[H])C([H])([H])* 0.000 claims description 3
125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
125000004847 2-fluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
125000006290 2-hydroxybenzyl group Chemical group [H]OC1=C(C([H])=C([H])C([H])=C1[H])C([H])([H])* 0.000 claims description 3
125000002927 2-methoxybenzyl group Chemical group [H]C1=C([H])C([H])=C(C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 claims description 3
125000006179 2-methyl benzyl group Chemical group [H]C1=C([H])C(=C(C([H])=C1[H])C([H])([H])*)C([H])([H])[H] 0.000 claims description 3
125000005979 2-naphthyloxy group Chemical group 0.000 claims description 3
125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 claims description 3
125000006284 3-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(F)=C1[H])C([H])([H])* 0.000 claims description 3
125000006291 3-hydroxybenzyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(=C1[H])C([H])([H])* 0.000 claims description 3
125000003143 4-hydroxybenzyl group Chemical group [H]C([*])([H])C1=C([H])C([H])=C(O[H])C([H])=C1[H] 0.000 claims description 3
125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 0.000 claims description 3
CWDWFSXUQODZGW-UHFFFAOYSA-N 5-thiazolyl Chemical group [C]1=CN=CS1 CWDWFSXUQODZGW-UHFFFAOYSA-N 0.000 claims description 3
125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
125000006637 cyclobutyl carbonyl group Chemical group 0.000 claims description 3
125000006639 cyclohexyl carbonyl group Chemical group 0.000 claims description 3
125000006638 cyclopentyl carbonyl group Chemical group 0.000 claims description 3
125000006255 cyclopropyl carbonyl group Chemical group [H]C1([H])C([H])([H])C1([H])C(*)=O 0.000 claims description 3
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 3
125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 3
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 3
125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 claims description 3
125000006518 morpholino carbonyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])N(C(*)=O)C1([H])[H] 0.000 claims description 3
125000001064 morpholinomethyl group Chemical group [H]C([H])(*)N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 claims description 3
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
125000004742 propyloxycarbonyl group Chemical group 0.000 claims description 3
125000004076 pyridyl group Chemical group 0.000 claims description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
229910052727 yttrium Inorganic materials 0.000 claims description 3
125000005978 1-naphthyloxy group Chemical group 0.000 claims description 2
125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 claims description 2
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 2
125000001424 substituent group Chemical group 0.000 claims 2
101000961172 Homo sapiens Intraflagellar transport protein 27 homolog Proteins 0.000 claims 1
241001135382 Hypostomus agna Species 0.000 claims 1
102100039343 Intraflagellar transport protein 27 homolog Human genes 0.000 claims 1
230000006806 disease prevention Effects 0.000 claims 1
ACGUYXCXAPNIKK-UHFFFAOYSA-N hexachlorophene Chemical compound OC1=C(Cl)C=C(Cl)C(Cl)=C1CC1=C(O)C(Cl)=CC(Cl)=C1Cl ACGUYXCXAPNIKK-UHFFFAOYSA-N 0.000 claims 1
IVXQBCUBSIPQGU-UHFFFAOYSA-N piperazine-1-carboxamide Chemical compound NC(=O)N1CCNCC1 IVXQBCUBSIPQGU-UHFFFAOYSA-N 0.000 claims 1
125000004432 carbon atom Chemical group C* 0.000 abstract description 12
239000003112 inhibitor Substances 0.000 abstract description 8
108010017640 Aspartic Acid Proteases Proteins 0.000 abstract description 4
102000004580 Aspartic Acid Proteases Human genes 0.000 abstract description 4
230000003389 potentiating effect Effects 0.000 abstract description 3
125000004429 atom Chemical group 0.000 abstract description 2
125000004415 heterocyclylalkyl group Chemical group 0.000 abstract 6
125000006517 heterocyclyl carbonyl group Chemical group 0.000 abstract 1
125000004356 hydroxy functional group Chemical group O* 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 186
239000000243 solution Substances 0.000 description 93
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 84
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 66
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 58
238000000034 method Methods 0.000 description 58
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 43
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 43
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 42
230000002829 reductive effect Effects 0.000 description 41
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 40
239000007787 solid Substances 0.000 description 37
239000003039 volatile agent Substances 0.000 description 36
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229910052943 magnesium sulfate Inorganic materials 0.000 description 29
235000019341 magnesium sulphate Nutrition 0.000 description 29
239000011347 resin Substances 0.000 description 28
229920005989 resin Polymers 0.000 description 28
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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
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
239000012074 organic phase Substances 0.000 description 22
229910004298 SiO 2 Inorganic materials 0.000 description 21
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 21
239000007858 starting material Substances 0.000 description 21
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 19
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 18
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
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239000002253 acid Substances 0.000 description 15
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
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239000003921 oil Substances 0.000 description 13
235000019198 oils Nutrition 0.000 description 13
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
241000725303 Human immunodeficiency virus Species 0.000 description 12
210000004027 cell Anatomy 0.000 description 12
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HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 description 11
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CQXDYHPBXDZWBA-UHFFFAOYSA-N tert-butyl 2,2,2-trichloroethanimidate Chemical compound CC(C)(C)OC(=N)C(Cl)(Cl)Cl CQXDYHPBXDZWBA-UHFFFAOYSA-N 0.000 description 1
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235000019157 thiamine Nutrition 0.000 description 1
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JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
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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)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Virology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Bioinformatics & Cheminformatics (AREA)
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)

SK760-2003A 2000-11-22 2001-11-12 Novel compounds for use as HIV protease inhibitors SK7602003A3 (en)

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
SK7602003A3 true SK7602003A3 (en)	2004-01-08

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ID=9903670

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK760-2003A SK7602003A3 (en)	2000-11-22	2001-11-12	Novel compounds for use as HIV protease inhibitors

Country Status (27)

Country	Link
US (1)	US6472404B1 (cs)
EP (1)	EP1339692A1 (cs)
JP (1)	JP2004520283A (cs)
KR (1)	KR20030060953A (cs)
CN (1)	CN1476436A (cs)
AR (1)	AR031763A1 (cs)
AU (2)	AU2954602A (cs)
BG (1)	BG107839A (cs)
BR (1)	BR0115566A (cs)
CA (1)	CA2428459A1 (cs)
CZ (1)	CZ20031667A3 (cs)
EC (1)	ECSP034618A (cs)
GB (1)	GB0028483D0 (cs)
GT (1)	GT200100233A (cs)
HU (1)	HUP0303007A2 (cs)
IL (1)	IL155573A0 (cs)
MA (1)	MA26966A1 (cs)
MX (1)	MXPA03004534A (cs)
NO (1)	NO20032290D0 (cs)
NZ (1)	NZ525550A (cs)
PA (1)	PA8533401A1 (cs)
PE (1)	PE20020610A1 (cs)
PL (1)	PL366704A1 (cs)
RU (1)	RU2265016C2 (cs)
SK (1)	SK7602003A3 (cs)
UY (1)	UY27033A1 (cs)
WO (1)	WO2002042277A1 (cs)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP4953297B2 (ja) *	2004-09-15	2012-06-13	塩野義製薬株式会社	Ｈｉｖインテグラーゼ阻害活性を有するカルバモイルピリドン誘導体
UA87884C2 (uk) *	2004-12-03	2009-08-25	Мерк Энд Ко., Инк.	Безводна кристалічна калієва сіль інгібітора віл-інтегрази
MX2010010471A (es) *	2008-03-26	2010-10-20	Daiichi Sankyo Co Ltd	Derivado de tetrahidroisoquinolina novedoso.
US12083099B2 (en)	2020-10-28	2024-09-10	Accencio LLC	Methods of treating symptoms of coronavirus infection with viral protease inhibitors

Family Cites Families (3)

* 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.
US5484926A (en) *	1993-10-07	1996-01-16	Agouron Pharmaceuticals, Inc.	HIV protease inhibitors

2000
- 2000-11-22 GB GBGB0028483.6A patent/GB0028483D0/en not_active Ceased
2001
- 2001-11-12 HU HU0303007A patent/HUP0303007A2/hu unknown
- 2001-11-12 NZ NZ525550A patent/NZ525550A/en unknown
- 2001-11-12 BR BR0115566-0A patent/BR0115566A/pt not_active IP Right Cessation
- 2001-11-12 AU AU2954602A patent/AU2954602A/xx active Pending
- 2001-11-12 KR KR10-2003-7006907A patent/KR20030060953A/ko not_active Ceased
- 2001-11-12 CZ CZ20031667A patent/CZ20031667A3/cs unknown
- 2001-11-12 EP EP01990405A patent/EP1339692A1/en not_active Withdrawn
- 2001-11-12 MX MXPA03004534A patent/MXPA03004534A/es active IP Right Grant
- 2001-11-12 IL IL15557301A patent/IL155573A0/xx unknown
- 2001-11-12 WO PCT/EP2001/013068 patent/WO2002042277A1/en not_active Ceased
- 2001-11-12 AU AU2002229546A patent/AU2002229546B2/en not_active Ceased
- 2001-11-12 PL PL01366704A patent/PL366704A1/xx not_active Application Discontinuation
- 2001-11-12 CN CNA018192890A patent/CN1476436A/zh active Pending
- 2001-11-12 CA CA002428459A patent/CA2428459A1/en not_active Abandoned
- 2001-11-12 RU RU2003117468/04A patent/RU2265016C2/ru not_active IP Right Cessation
- 2001-11-12 SK SK760-2003A patent/SK7602003A3/sk unknown
- 2001-11-12 JP JP2002544412A patent/JP2004520283A/ja active Pending
- 2001-11-20 US US09/999,082 patent/US6472404B1/en not_active Expired - Fee Related
- 2001-11-21 UY UY27033A patent/UY27033A1/es not_active Application Discontinuation
- 2001-11-21 PA PA20018533401A patent/PA8533401A1/es unknown
- 2001-11-21 AR ARP010105431A patent/AR031763A1/es unknown
- 2001-11-21 GT GT200100233A patent/GT200100233A/es unknown
- 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/NO20032290D0/no unknown
- 2003-05-22 BG BG107839A patent/BG107839A/bg unknown
- 2003-05-22 MA MA27172A patent/MA26966A1/fr unknown

Also Published As

Publication number	Publication date
RU2265016C2 (ru)	2005-11-27
PE20020610A1 (es)	2002-07-13
RU2003117468A (ru)	2005-01-27
MA26966A1 (fr)	2004-12-20
BR0115566A (pt)	2003-09-30
AU2002229546B2 (en)	2006-05-04
ECSP034618A (es)	2003-06-25
CN1476436A (zh)	2004-02-18
JP2004520283A (ja)	2004-07-08
NO20032290L (no)	2003-05-21
CZ20031667A3 (cs)	2004-01-14
KR20030060953A (ko)	2003-07-16
UY27033A1 (es)	2002-06-20
CA2428459A1 (en)	2002-05-30
PA8533401A1 (es)	2002-10-31
US6472404B1 (en)	2002-10-29
IL155573A0 (en)	2003-11-23
AU2954602A (en)	2002-06-03
GT200100233A (es)	2002-07-04
HUP0303007A2 (hu)	2003-12-29
EP1339692A1 (en)	2003-09-03
AR031763A1 (es)	2003-10-01
GB0028483D0 (en)	2001-01-10
MXPA03004534A (es)	2003-09-10
NO20032290D0 (no)	2003-05-21
NZ525550A (en)	2004-11-26
BG107839A (bg)	2004-06-30
WO2002042277A1 (en)	2002-05-30
PL366704A1 (en)	2005-02-07

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