CA2711424A1 - Nouveaux derives de lupane - Google Patents

Nouveaux derives de lupane Download PDF

Info

Publication number: CA2711424A1
Authority: CA; Canada
Prior art keywords: beta; alkyl; ene; oxolup; dimethylsuccinyl
Prior art date: 2008-01-03
Legal status (The legal status 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 status listed.): Abandoned

Application number

CA2711424A

Other languages

English (en)

Inventor

Christophe Moinet

Laval Chan Chun Kong

Liliane Halab

Nathalie Turcotte

Monica Bubenik

Marc Courchesne

Carl Poisson

Oswy Z. Pereira

Paul Nguyen-Ba

Nathalie Chauret

Caroline Cadilhac

Bingcan Liu

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Virochem Pharma Inc

Original Assignee

Individual

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.)

2008-01-03

Filing date

2008-12-23

Publication date

2009-07-09

2008-12-23 Application filed by Individual filed Critical Individual

2009-07-09 Publication of CA2711424A1 publication Critical patent/CA2711424A1/fr

Status Abandoned legal-status Critical Current

Links

150000002654 lupanes Chemical class 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 227
238000000034 method Methods 0.000 claims abstract description 49
150000003839 salts Chemical class 0.000 claims abstract description 32
208000031886 HIV Infections Diseases 0.000 claims abstract description 5
230000002265 prevention Effects 0.000 claims abstract description 4
125000000217 alkyl group Chemical group 0.000 claims description 615
-1 glutaryl Chemical group 0.000 claims description 118
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 101
229910052736 halogen Inorganic materials 0.000 claims description 93
150000002367 halogens Chemical group 0.000 claims description 78
239000000203 mixture Substances 0.000 claims description 72
125000003545 alkoxy group Chemical group 0.000 claims description 62
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 57
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 56
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 53
125000003342 alkenyl group Chemical group 0.000 claims description 50
125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 49
125000000304 alkynyl group Chemical group 0.000 claims description 46
125000004093 cyano group Chemical group *C#N 0.000 claims description 43
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 41
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 39
125000000623 heterocyclic group Chemical group 0.000 claims description 38
125000001072 heteroaryl group Chemical group 0.000 claims description 36
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 34
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 31
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 28
239000003443 antiviral agent Substances 0.000 claims description 25
125000004475 heteroaralkyl group Chemical group 0.000 claims description 25
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 20
125000003710 aryl alkyl group Chemical group 0.000 claims description 20
125000003118 aryl group Chemical group 0.000 claims description 19
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
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 claims description 18
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 17
239000003112 inhibitor Substances 0.000 claims description 17
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 16
239000003814 drug Substances 0.000 claims description 16
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
229910006074 SO2NH2 Inorganic materials 0.000 claims description 15
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 15
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 15
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 15
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 14
125000000018 nitroso group Chemical group N(=O)* 0.000 claims description 14
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 13
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 13
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 13
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 12
NQDJXKOVJZTUJA-UHFFFAOYSA-N nevirapine Chemical compound C12=NC=CC=C2C(=O)NC=2C(C)=CC=NC=2N1C1CC1 NQDJXKOVJZTUJA-UHFFFAOYSA-N 0.000 claims description 12
239000008194 pharmaceutical composition Substances 0.000 claims description 12
108010019625 Atazanavir Sulfate Proteins 0.000 claims description 11
XQSPYNMVSIKCOC-NTSWFWBYSA-N Emtricitabine Chemical compound C1=C(F)C(N)=NC(=O)N1[C@H]1O[C@@H](CO)SC1 XQSPYNMVSIKCOC-NTSWFWBYSA-N 0.000 claims description 11
AXRYRYVKAWYZBR-GASGPIRDSA-N atazanavir Chemical compound C([C@H](NC(=O)[C@@H](NC(=O)OC)C(C)(C)C)[C@@H](O)CN(CC=1C=CC(=CC=1)C=1N=CC=CC=1)NC(=O)[C@@H](NC(=O)OC)C(C)(C)C)C1=CC=CC=C1 AXRYRYVKAWYZBR-GASGPIRDSA-N 0.000 claims description 11
QWAXKHKRTORLEM-UGJKXSETSA-N saquinavir Chemical compound C([C@@H]([C@H](O)CN1C[C@H]2CCCC[C@H]2C[C@H]1C(=O)NC(C)(C)C)NC(=O)[C@H](CC(N)=O)NC(=O)C=1N=C2C=CC=CC2=CC=1)C1=CC=CC=C1 QWAXKHKRTORLEM-UGJKXSETSA-N 0.000 claims description 11
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 claims description 11
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 10
NCDNCNXCDXHOMX-XGKFQTDJSA-N ritonavir Chemical compound N([C@@H](C(C)C)C(=O)N[C@H](C[C@H](O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1SC=NC=1)CC=1C=CC=CC=1)C(=O)N(C)CC1=CSC(C(C)C)=N1 NCDNCNXCDXHOMX-XGKFQTDJSA-N 0.000 claims description 10
AXRYRYVKAWYZBR-UHFFFAOYSA-N Atazanavir Natural products C=1C=C(C=2N=CC=CC=2)C=CC=1CN(NC(=O)C(NC(=O)OC)C(C)(C)C)CC(O)C(NC(=O)C(NC(=O)OC)C(C)(C)C)CC1=CC=CC=C1 AXRYRYVKAWYZBR-UHFFFAOYSA-N 0.000 claims description 9
MCGSCOLBFJQGHM-SCZZXKLOSA-N abacavir Chemical compound C=12N=CN([C@H]3C=C[C@@H](CO)C3)C2=NC(N)=NC=1NC1CC1 MCGSCOLBFJQGHM-SCZZXKLOSA-N 0.000 claims description 9
229960004748 abacavir Drugs 0.000 claims description 9
YMARZQAQMVYCKC-OEMFJLHTSA-N amprenavir Chemical compound C([C@@H]([C@H](O)CN(CC(C)C)S(=O)(=O)C=1C=CC(N)=CC=1)NC(=O)O[C@@H]1COCC1)C1=CC=CC=C1 YMARZQAQMVYCKC-OEMFJLHTSA-N 0.000 claims description 9
229960003277 atazanavir Drugs 0.000 claims description 9
CBVCZFGXHXORBI-PXQQMZJSSA-N indinavir Chemical compound C([C@H](N(CC1)C[C@@H](O)C[C@@H](CC=2C=CC=CC=2)C(=O)N[C@H]2C3=CC=CC=C3C[C@H]2O)C(=O)NC(C)(C)C)N1CC1=CC=CN=C1 CBVCZFGXHXORBI-PXQQMZJSSA-N 0.000 claims description 9
125000000714 pyrimidinyl group Chemical group 0.000 claims description 9
229960002555 zidovudine Drugs 0.000 claims description 9
KDISMIMTGUMORD-UHFFFAOYSA-N 1-acetylpiperidine Chemical group CC(=O)N1CCCCC1 KDISMIMTGUMORD-UHFFFAOYSA-N 0.000 claims description 8
NCDNCNXCDXHOMX-UHFFFAOYSA-N Ritonavir Natural products C=1C=CC=CC=1CC(NC(=O)OCC=1SC=NC=1)C(O)CC(CC=1C=CC=CC=1)NC(=O)C(C(C)C)NC(=O)N(C)CC1=CSC(C(C)C)=N1 NCDNCNXCDXHOMX-UHFFFAOYSA-N 0.000 claims description 8
WREGKURFCTUGRC-POYBYMJQSA-N Zalcitabine Chemical compound O=C1N=C(N)C=CN1[C@@H]1O[C@H](CO)CC1 WREGKURFCTUGRC-POYBYMJQSA-N 0.000 claims description 8
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 8
QAGYKUNXZHXKMR-HKWSIXNMSA-N nelfinavir Chemical compound CC1=C(O)C=CC=C1C(=O)N[C@H]([C@H](O)CN1[C@@H](C[C@@H]2CCCC[C@@H]2C1)C(=O)NC(C)(C)C)CSC1=CC=CC=C1 QAGYKUNXZHXKMR-HKWSIXNMSA-N 0.000 claims description 8
WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 8
125000003386 piperidinyl group Chemical group 0.000 claims description 8
125000003226 pyrazolyl group Chemical group 0.000 claims description 8
BXZVVICBKDXVGW-NKWVEPMBSA-N Didanosine Chemical compound O1[C@H](CO)CC[C@@H]1N1C(NC=NC2=O)=C2N=C1 BXZVVICBKDXVGW-NKWVEPMBSA-N 0.000 claims description 7
KJHKTHWMRKYKJE-SUGCFTRWSA-N Kaletra Chemical compound N1([C@@H](C(C)C)C(=O)N[C@H](C[C@H](O)[C@H](CC=2C=CC=CC=2)NC(=O)COC=2C(=CC=CC=2C)C)CC=2C=CC=CC=2)CCCNC1=O KJHKTHWMRKYKJE-SUGCFTRWSA-N 0.000 claims description 7
229960001830 amprenavir Drugs 0.000 claims description 7
125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 7
CJBJHOAVZSMMDJ-HEXNFIEUSA-N darunavir Chemical compound C([C@@H]([C@H](O)CN(CC(C)C)S(=O)(=O)C=1C=CC(N)=CC=1)NC(=O)O[C@@H]1[C@@H]2CCO[C@@H]2OC1)C1=CC=CC=C1 CJBJHOAVZSMMDJ-HEXNFIEUSA-N 0.000 claims description 7
239000003937 drug carrier Substances 0.000 claims description 7
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 claims description 7
229960003586 elvitegravir Drugs 0.000 claims description 7
JUZYLCPPVHEVSV-LJQANCHMSA-N elvitegravir Chemical compound COC1=CC=2N([C@H](CO)C(C)C)C=C(C(O)=O)C(=O)C=2C=C1CC1=CC=CC(Cl)=C1F JUZYLCPPVHEVSV-LJQANCHMSA-N 0.000 claims description 7
229960000366 emtricitabine Drugs 0.000 claims description 7
PEASPLKKXBYDKL-FXEVSJAOSA-N enfuvirtide Chemical compound C([C@@H](C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](C)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(N)=O)NC(=O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(C)=O)[C@@H](C)O)[C@@H](C)CC)C1=CN=CN1 PEASPLKKXBYDKL-FXEVSJAOSA-N 0.000 claims description 7
PYGWGZALEOIKDF-UHFFFAOYSA-N etravirine Chemical compound CC1=CC(C#N)=CC(C)=C1OC1=NC(NC=2C=CC(=CC=2)C#N)=NC(N)=C1Br PYGWGZALEOIKDF-UHFFFAOYSA-N 0.000 claims description 7
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229910052760 oxygen Inorganic materials 0.000 claims description 7
229960001852 saquinavir Drugs 0.000 claims description 7
GWNOTCOIYUNTQP-FQLXRVMXSA-N 4-[4-[[(3r)-1-butyl-3-[(r)-cyclohexyl(hydroxy)methyl]-2,5-dioxo-1,4,9-triazaspiro[5.5]undecan-9-yl]methyl]phenoxy]benzoic acid Chemical compound N([C@@H](C(=O)N1CCCC)[C@H](O)C2CCCCC2)C(=O)C1(CC1)CCN1CC(C=C1)=CC=C1OC1=CC=C(C(O)=O)C=C1 GWNOTCOIYUNTQP-FQLXRVMXSA-N 0.000 claims description 6
HSBKFSPNDWWPSL-VDTYLAMSSA-N 4-amino-5-fluoro-1-[(2s,5r)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]pyrimidin-2-one Chemical compound C1=C(F)C(N)=NC(=O)N1[C@@H]1C=C[C@H](CO)O1 HSBKFSPNDWWPSL-VDTYLAMSSA-N 0.000 claims description 6
102000002004 Cytochrome P-450 Enzyme System Human genes 0.000 claims description 6
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108010002350 Interleukin-2 Proteins 0.000 claims description 6
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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 claims description 6
JORVRJNILJXMMG-OLNQLETPSA-N brecanavir Chemical compound C([C@@H]([C@H](O)CN(CC(C)C)S(=O)(=O)C=1C=C2OCOC2=CC=1)NC(=O)O[C@@H]1[C@@H]2CCO[C@@H]2OC1)C(C=C1)=CC=C1OCC1=CSC(C)=N1 JORVRJNILJXMMG-OLNQLETPSA-N 0.000 claims description 6
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 6
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CNPVJJQCETWNEU-CYFREDJKSA-N (4,6-dimethyl-5-pyrimidinyl)-[4-[(3S)-4-[(1R)-2-methoxy-1-[4-(trifluoromethyl)phenyl]ethyl]-3-methyl-1-piperazinyl]-4-methyl-1-piperidinyl]methanone Chemical compound N([C@@H](COC)C=1C=CC(=CC=1)C(F)(F)F)([C@H](C1)C)CCN1C(CC1)(C)CCN1C(=O)C1=C(C)N=CN=C1C CNPVJJQCETWNEU-CYFREDJKSA-N 0.000 claims description 5
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238000013207 serial dilution Methods 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229940054269 sodium pyruvate Drugs 0.000 description 1
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
235000019345 sodium thiosulphate Nutrition 0.000 description 1
239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
241000894007 species Species 0.000 description 1
125000003003 spiro group Chemical group 0.000 description 1
230000000087 stabilizing effect Effects 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
238000013268 sustained release Methods 0.000 description 1
239000012730 sustained-release form Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
SGOIRFVFHAKUTI-ZCFIWIBFSA-N tenofovir (anhydrous) Chemical compound N1=CN=C2N(C[C@@H](C)OCP(O)(O)=O)C=NC2=C1N SGOIRFVFHAKUTI-ZCFIWIBFSA-N 0.000 description 1
LZRDHSFPLUWYAX-UHFFFAOYSA-N tert-butyl 4-aminopiperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(N)CC1 LZRDHSFPLUWYAX-UHFFFAOYSA-N 0.000 description 1
125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
125000001412 tetrahydropyranyl 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
230000001225 therapeutic effect Effects 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
125000004525 thiadiazinyl group Chemical group S1NN=C(C=C1)* 0.000 description 1
125000005996 thiadiazolopyrimidinyl group Chemical group 0.000 description 1
125000001113 thiadiazolyl group Chemical group 0.000 description 1
125000002769 thiazolinyl group Chemical group 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
230000008719 thickening Effects 0.000 description 1
125000004588 thienopyridyl group Chemical group S1C(=CC2=C1C=CC=N2)* 0.000 description 1
125000004587 thienothienyl group Chemical group S1C(=CC2=C1C=CS2)* 0.000 description 1
229960000790 thymol Drugs 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
RUVINXPYWBROJD-ONEGZZNKSA-N trans-anethole Chemical compound COC1=CC=C(\C=C\C)C=C1 RUVINXPYWBROJD-ONEGZZNKSA-N 0.000 description 1
125000006000 trichloroethyl 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
125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
229960000281 trometamol Drugs 0.000 description 1
229960005486 vaccine Drugs 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
229940023080 viracept Drugs 0.000 description 1
230000007502 viral entry Effects 0.000 description 1
230000017613 viral reproduction Effects 0.000 description 1
239000003643 water by type Substances 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/575—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of three or more carbon atoms, e.g. cholane, cholestane, ergosterol, sitosterol
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/58—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids containing heterocyclic rings, e.g. danazol, stanozolol, pancuronium or digitogenin
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
- A61K38/05—Dipeptides
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/16—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- A61K38/55—Protease inhibitors
- 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
- 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

Landscapes

Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Medicinal Chemistry (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Virology (AREA)
Oncology (AREA)
Gastroenterology & Hepatology (AREA)
Organic Chemistry (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Communicable Diseases (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Immunology (AREA)
Bioinformatics & Cheminformatics (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Engineering & Computer Science (AREA)
AIDS & HIV (AREA)
Tropical Medicine & Parasitology (AREA)
Molecular Biology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Steroid Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

CA2711424A 2008-01-03 2008-12-23 Nouveaux derives de lupane Abandoned CA2711424A1 (fr)

Applications Claiming Priority (5)

Application Number	Priority Date	Filing Date	Title
US1875908P	2008-01-03	2008-01-03
US61/018,759		2008-01-31
US3966008P	2008-03-26	2008-03-26
US61/039,660		2008-03-26
PCT/CA2008/002291 WO2009082819A1 (fr)	2008-01-03	2008-12-23	Nouveaux dérivés de lupane

Publications (1)

Publication Number	Publication Date
CA2711424A1 true CA2711424A1 (fr)	2009-07-09

Family

ID=40823729

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA2711424A Abandoned CA2711424A1 (fr)	2008-01-03	2008-12-23	Nouveaux derives de lupane

Country Status (7)

Country	Link
EP (1)	EP2250185A4 (fr)
JP (1)	JP2011508748A (fr)
CN (1)	CN101981047A (fr)
AU (1)	AU2008342537A1 (fr)
CA (1)	CA2711424A1 (fr)
MX (1)	MX2010007375A (fr)
WO (1)	WO2009082819A1 (fr)

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CN101977610B (zh)	2008-01-25	2012-05-16	奇默里克斯公司	治疗病毒感染的方法
US8624023B2 (en) *	2008-12-11	2014-01-07	Shionogi & Co., Ltd.	Synthesis of carbamoylpyridone HIV integrase inhibitors and intermediates
US9067966B2 (en) *	2009-07-14	2015-06-30	Hetero Research Foundation, Hetero Drugs Ltd.	Lupeol-type triterpene derivatives as antivirals
US8802727B2 (en)	2009-07-14	2014-08-12	Hetero Research Foundation, Hetero Drugs Limited	Pharmaceutically acceptable salts of betulinic acid derivatives
EA032868B1 (ru)	2010-01-27	2019-07-31	Вайв Хелткер Компани	Комбинация для лечения вич-инфекции
WO2011100308A1 (fr) *	2010-02-11	2011-08-18	Glaxosmithkline Llc	Dérivés de bétuline
DK2534150T3 (en)	2010-02-12	2017-06-12	Chimerix Inc	METHODS OF TREATING VIRUS INFECTION
WO2011139709A2 (fr)	2010-04-26	2011-11-10	Chimerix, Inc.	Méthodes de traitement d'infections rétrovirales et régimes posologiques associés
ES2584684T3 (es) *	2011-12-14	2016-09-28	Glaxosmithkline Llc	Derivados de propenoato de betulina
JO3387B1 (ar)	2011-12-16	2019-03-13	Glaxosmithkline Llc	مشتقات بيتولين
CN103242413B (zh) *	2012-02-08	2015-08-26	江西青峰药业有限公司	Lupane三萜系衍生物及其药学用途
US8906889B2 (en) *	2012-02-15	2014-12-09	Bristol-Myers Squibb Company	C-3 cycloalkenyl triterpenoids with HIV maturation inhibitory activity
KR20150093819A (ko)	2012-12-14	2015-08-18	글락소스미스클라인 엘엘씨	약제 조성물
WO2014105926A1 (fr)	2012-12-31	2014-07-03	Hetero Research Foundation	Nouveaux dérivés proline de l'acide bétulinique utilisés comme inhibiteurs du vih
US20170129916A1 (en)	2014-06-26	2017-05-11	Hetero Research Foundation	Novel betulinic proline imidazole derivatives as hiv inhibitors
KR20170056702A (ko)	2014-09-26	2017-05-23	글락소스미스클라인 인털렉츄얼 프로퍼티 (넘버 2) 리미티드	지효성 약제학적 조성물
RU2017118489A (ru) *	2014-11-14	2018-12-14	ВАЙВ ХЕЛТКЕР ЮКей (N5) ЛИМИТЕД	Оксолупеновые производные
MA40886B1 (fr) *	2015-02-09	2020-03-31	Hetero Research Foundation	Nouveau triterpénone en c-3 avec des dérivés d'amide inverse en c-28 en tant qu'inhibiteurs du vih
WO2016147099A2 (fr) *	2015-03-16	2016-09-22	Hetero Research Foundation	Nouveaux triterpénone c-3 avec des dérivés amide c-28 servant d'inhibiteurs de vih
US10669305B2 (en) *	2015-10-13	2020-06-02	Hetero Labs Limited	C-3 novel triterpenone with C-28 urea derivatives as HIV inhibitors
EP3405474A1 (fr) *	2016-01-20	2018-11-28	Glaxosmithkline Intellectual Property (No. 2) Limited	Dérivés amine de lupanes ayant une activité inhibitrice de la maturation du vih
WO2018025247A1 (fr) *	2016-08-05	2018-02-08	Hetero Labs Limited	Nouvelle triterpénone en c-3 avec des dérivés de diamide en c-28 en tant qu'inhibiteurs du vih
WO2018029604A1 (fr) *	2016-08-08	2018-02-15	Hetero Labs Limited	Nouveau triterpénone en c-3 avec des dérivés d'amide inverse en c-17 en tant qu'inhibiteurs du vih
WO2018029610A1 (fr) *	2016-08-09	2018-02-15	Hetero Labs Limited	Nouvelle triterpénone en c-3 avec des dérivés de n-amide en c-17 en tant qu'inhibiteurs du vih
WO2018065930A1 (fr) *	2016-10-05	2018-04-12	Hetero Labs Limited	Triterpénone en c-3 avec des dérivés amides inversés en c-17 en tant qu'inhibiteurs du vih
WO2018069857A1 (fr) *	2016-10-12	2018-04-19	Hetero Labs Limited	Nouvelle triterpénone en c-3 à dérivés hétérocycliques d'amide inverse en c-17 utilisés comme inhibiteurs du vih
US11116737B1 (en)	2020-04-10	2021-09-14	University Of Georgia Research Foundation, Inc.	Methods of using probenecid for treatment of coronavirus infections

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EP1292562A1 (fr) *	2000-05-23	2003-03-19	Univerzita palackeho V Olomouci	Derives triterpenoides
GB0012528D0 (en) *	2000-05-23	2000-07-12	Univ Palackeho	Triterpenoid derivatives
WO2005112929A2 (fr) *	2004-05-20	2005-12-01	Cornell Research Foundation, Inc.	Activite anti vih-1 de derives de betulinol
TW200628161A (en) *	2004-11-12	2006-08-16	Panacos Pharmaceuticals Inc	Novel betulin derivatives, preparation thereof and use thereof

2008
- 2008-12-23 MX MX2010007375A patent/MX2010007375A/es not_active Application Discontinuation
- 2008-12-23 JP JP2010540997A patent/JP2011508748A/ja not_active Withdrawn
- 2008-12-23 CN CN2008801275273A patent/CN101981047A/zh active Pending
- 2008-12-23 AU AU2008342537A patent/AU2008342537A1/en not_active Abandoned
- 2008-12-23 CA CA2711424A patent/CA2711424A1/fr not_active Abandoned
- 2008-12-23 EP EP08869088A patent/EP2250185A4/fr not_active Withdrawn
- 2008-12-23 WO PCT/CA2008/002291 patent/WO2009082819A1/fr not_active Ceased

Also Published As

Publication number	Publication date
CN101981047A (zh)	2011-02-23
WO2009082819A1 (fr)	2009-07-09
WO2009082819A8 (fr)	2009-10-22
MX2010007375A (es)	2010-09-30
AU2008342537A1 (en)	2009-07-09
EP2250185A1 (fr)	2010-11-17
JP2011508748A (ja)	2011-03-17
EP2250185A4 (fr)	2011-11-16

Publication	Publication Date	Title
CA2711424A1 (fr)	2009-07-09	Nouveaux derives de lupane
US20110077251A1 (en)	2011-03-31	Novel 17 beta lupane derivatives
WO2009082818A1 (fr)	2009-07-09	Préparation de nouveaux dérivés de c-21-céto lupane et leur utilisation
US20060205697A1 (en)	2006-09-14	Novel betulin derivatives, preparation thereof and use thereof
US8748415B2 (en)	2014-06-10	C-28 amines of C-3 modified betulinic acid derivatives as HIV maturation inhibitors
JP6001560B2 (ja)	2016-10-05	Ｈｉｖ成熟阻害活性を有するｃ−１７およびｃ−３修飾トリテルペノイド
US8802661B2 (en)	2014-08-12	C-28 amides of modified C-3 betulinic acid derivatives as HIV maturation inhibitors
US8269026B2 (en)	2012-09-18	Lupane derivatives useful for treating HIV
CA2634499A1 (fr)	2006-06-29	Hydroxydihydropyridopy razine-1,8-diones et procedes d'inhibition de l'integrase du vih
US10245275B2 (en)	2019-04-02	Triterpenoids with HIV maturation inhibitory activity
ES2957767T3 (es)	2024-01-25	Triterpenoides modificados en C-3 y C-17 como inhibidores del VIH-1
US20050176767A1 (en)	2005-08-11	Pyridine carboxamide and methods for inhibiting HIV integrase
HK1149019A (en)	2011-09-23	Novel lupane derivatives
HK1151030A (en)	2012-01-20	Novel c-21-keto lupane derivatives preparation and use thereof
JP6851489B2 (ja)	2021-03-31	新規エルゴステノールグリコシド誘導体
Classen-Houben et al.	2013	Kosma et a
MXPA06003252A (en)	2007-04-20	Novel triterpene derivatives, preparation thereof and use thereof

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Date	Code	Title	Description
2013-02-18	FZDE	Dead	Effective date: 20121224