CA2540160A1

CA2540160A1 - Novel triterpene derivatives, preparation thereof and use thereof

Novel triterpene derivatives, preparation thereof and use thereof Download PDF

Info

Publication number: CA2540160A1
Authority: CA; Canada
Prior art keywords: compound; methyl; dimethylsuccinyl; hydrogen; acid
Prior art date: 2003-09-26
Legal status : Abandoned

Application number

CA002540160A

Other languages

English (en)

French (fr)

Inventor

Carl T. Wild

Gary N. Robinson

Mark Ashton

Russell Thomas

Current Assignee

Individual

Original Assignee

Individual

Priority date

2003-09-26

Filing date

2004-09-27

Publication date

2005-04-07

2004-09-27 Application filed by Individual filed Critical Individual

2005-04-07 Publication of CA2540160A1 publication Critical patent/CA2540160A1/en

Status Abandoned legal-status Critical Current

Links

150000003648 triterpenes Chemical class 0.000 title abstract description 30
238000002360 preparation method Methods 0.000 title description 9
239000003814 drug Substances 0.000 claims abstract description 31
230000002401 inhibitory effect Effects 0.000 claims abstract description 17
206010038997 Retroviral infections Diseases 0.000 claims abstract description 7
150000001875 compounds Chemical class 0.000 claims description 116
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 59
229910052739 hydrogen Inorganic materials 0.000 claims description 46
239000001257 hydrogen Substances 0.000 claims description 44
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 34
239000000203 mixture Substances 0.000 claims description 30
-1 carboxyalkoxymethyl Chemical group 0.000 claims description 27
238000000034 method Methods 0.000 claims description 27
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 26
150000002431 hydrogen Chemical class 0.000 claims description 21
230000001177 retroviral effect Effects 0.000 claims description 19
125000004080 3-carboxypropanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C(O[H])=O 0.000 claims description 18
229940079593 drug Drugs 0.000 claims description 18
239000008194 pharmaceutical composition Substances 0.000 claims description 18
125000000217 alkyl group Chemical group 0.000 claims description 15
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
150000002148 esters Chemical class 0.000 claims description 14
125000005843 halogen group Chemical group 0.000 claims description 14
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 12
229910052736 halogen Inorganic materials 0.000 claims description 11
NQDJXKOVJZTUJA-UHFFFAOYSA-N nevirapine Chemical compound C12=NC=CC=C2C(=O)NC=2C(C)=CC=NC=2N1C1CC1 NQDJXKOVJZTUJA-UHFFFAOYSA-N 0.000 claims description 11
150000003839 salts Chemical class 0.000 claims description 11
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
239000003443 antiviral agent Substances 0.000 claims description 10
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 10
150000002367 halogens Chemical class 0.000 claims description 10
125000004849 alkoxymethyl group Chemical group 0.000 claims description 9
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 9
229960002555 zidovudine Drugs 0.000 claims description 9
108010032976 Enfuvirtide Proteins 0.000 claims description 8
208000031886 HIV Infections Diseases 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
125000005042 acyloxymethyl group Chemical group 0.000 claims description 8
230000037396 body weight Effects 0.000 claims description 8
230000001568 sexual effect Effects 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
208000037357 HIV infectious disease Diseases 0.000 claims description 7
241001465754 Metazoa Species 0.000 claims description 7
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 7
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 7
230000005540 biological transmission Effects 0.000 claims description 7
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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 7
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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 6
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ZJAOAACCNHFJAH-UHFFFAOYSA-N phosphonoformic acid Chemical compound OC(=O)P(O)(O)=O ZJAOAACCNHFJAH-UHFFFAOYSA-N 0.000 claims description 6
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229960001852 saquinavir Drugs 0.000 claims description 6
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QAGYKUNXZHXKMR-UHFFFAOYSA-N CPD000469186 Natural products CC1=C(O)C=CC=C1C(=O)NC(C(O)CN1C(CC2CCCCC2C1)C(=O)NC(C)(C)C)CSC1=CC=CC=C1 QAGYKUNXZHXKMR-UHFFFAOYSA-N 0.000 claims description 5
XPOQHMRABVBWPR-UHFFFAOYSA-N Efavirenz Natural products O1C(=O)NC2=CC=C(Cl)C=C2C1(C(F)(F)F)C#CC1CC1 XPOQHMRABVBWPR-UHFFFAOYSA-N 0.000 claims description 5
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 5
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
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 5
229960004748 abacavir Drugs 0.000 claims description 5
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
229960001830 amprenavir Drugs 0.000 claims description 5
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 5
229960003277 atazanavir Drugs 0.000 claims description 5
229960005319 delavirdine Drugs 0.000 claims description 5
239000003937 drug carrier Substances 0.000 claims description 5
229960003804 efavirenz Drugs 0.000 claims description 5
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 5
210000003754 fetus Anatomy 0.000 claims description 5
229960003142 fosamprenavir Drugs 0.000 claims description 5
MLBVMOWEQCZNCC-OEMFJLHTSA-N fosamprenavir Chemical compound C([C@@H]([C@H](OP(O)(O)=O)CN(CC(C)C)S(=O)(=O)C=1C=CC(N)=CC=1)NC(=O)O[C@@H]1COCC1)C1=CC=CC=C1 MLBVMOWEQCZNCC-OEMFJLHTSA-N 0.000 claims description 5
229960001936 indinavir Drugs 0.000 claims description 5
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 5
229960000884 nelfinavir Drugs 0.000 claims description 5
229960000689 nevirapine Drugs 0.000 claims description 5
229910052757 nitrogen Inorganic materials 0.000 claims description 5
125000004430 oxygen atom Chemical group O* 0.000 claims description 5
229960000311 ritonavir Drugs 0.000 claims description 5
229910052717 sulfur Inorganic materials 0.000 claims description 5
239000011593 sulfur Substances 0.000 claims description 5
229960004556 tenofovir Drugs 0.000 claims description 5
XUARCIYIVXVTAE-ZAPOICBTSA-N uvaol Chemical compound C1C[C@H](O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(CO)CC[C@@H](C)[C@H](C)[C@H]5C4=CC[C@@H]3[C@]21C XUARCIYIVXVTAE-ZAPOICBTSA-N 0.000 claims description 5
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 4
102000000588 Interleukin-2 Human genes 0.000 claims description 4
108010002350 Interleukin-2 Proteins 0.000 claims description 4
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 4
IWUCXVSUMQZMFG-AFCXAGJDSA-N Ribavirin Chemical compound N1=C(C(=O)N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 IWUCXVSUMQZMFG-AFCXAGJDSA-N 0.000 claims description 4
MKUXAQIIEYXACX-UHFFFAOYSA-N aciclovir Chemical compound N1C(N)=NC(=O)C2=C1N(COCCO)C=N2 MKUXAQIIEYXACX-UHFFFAOYSA-N 0.000 claims description 4
229960002656 didanosine Drugs 0.000 claims description 4
229960000366 emtricitabine Drugs 0.000 claims description 4
IRSCQMHQWWYFCW-UHFFFAOYSA-N ganciclovir Chemical compound O=C1NC(N)=NC2=C1N=CN2COC(CO)CO IRSCQMHQWWYFCW-UHFFFAOYSA-N 0.000 claims description 4
239000003022 immunostimulating agent Substances 0.000 claims description 4
JTEGQNOMFQHVDC-NKWVEPMBSA-N lamivudine Chemical compound O=C1N=C(N)C=CN1[C@H]1O[C@@H](CO)SC1 JTEGQNOMFQHVDC-NKWVEPMBSA-N 0.000 claims description 4
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210000004877 mucosa Anatomy 0.000 claims description 4
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UBLNLUPLUKPSPP-UHFFFAOYSA-N 3-beta-form-3-Lupanol Natural products C1CC(O)C(C)(C)C2CCC3(C)C4(C)CCC5(C)CCC(C(C)C)C5C4CCC3C21C UBLNLUPLUKPSPP-UHFFFAOYSA-N 0.000 claims description 3
CBMYJHIOYJEBSB-YSZCXEEOSA-N 5alpha-androstane-3beta,17beta-diol Chemical compound C1[C@@H](O)CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CC[C@H]21 CBMYJHIOYJEBSB-YSZCXEEOSA-N 0.000 claims description 3
YKOPWPOFWMYZJZ-FMMUPTMQSA-N Echinocystic acid Natural products C1C[C@H](O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)C[C@H](O)[C@@]5(C(O)=O)CCC(C)(C)C[C@H]5C4=CC[C@@H]3[C@]21C YKOPWPOFWMYZJZ-FMMUPTMQSA-N 0.000 claims description 3
YKOPWPOFWMYZJZ-UHFFFAOYSA-N Echinocystsaeure Natural products C1CC(O)C(C)(C)C2CCC3(C)C4(C)CC(O)C5(C(O)=O)CCC(C)(C)CC5C4=CCC3C21C YKOPWPOFWMYZJZ-UHFFFAOYSA-N 0.000 claims description 3
PSZDOEIIIJFCFE-UHFFFAOYSA-N Oleanolic alcohol Natural products C1CC(O)C(C)(C)C2CCC3(C)C4(C)CCC5(CO)CCC(C)(C)CC5C4=CCC3C21C PSZDOEIIIJFCFE-UHFFFAOYSA-N 0.000 claims description 3
KLHSKTMVSOWVLD-WPDRYGPBSA-N Sumaresinol Chemical compound C1C[C@H](O)C(C)(C)[C@@H]2[C@H](O)C[C@@]3(C)[C@]4(C)CC[C@@]5(C(O)=O)CCC(C)(C)C[C@H]5C4=CC[C@@H]3[C@]21C KLHSKTMVSOWVLD-WPDRYGPBSA-N 0.000 claims description 3
229960004150 aciclovir Drugs 0.000 claims description 3
125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 3
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125000005125 aryl alkyl amino carbonyl group Chemical group 0.000 claims description 3
125000005100 aryl amino carbonyl group Chemical group 0.000 claims description 3
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
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MQYXUWHLBZFQQO-QGTGJCAVSA-N lupeol Chemical compound C1C[C@H](O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C)CC[C@@H](C(=C)C)[C@@H]5[C@H]4CC[C@@H]3[C@]21C MQYXUWHLBZFQQO-QGTGJCAVSA-N 0.000 claims description 3
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