RU2012132218A - Соединения и фармацевтические композиции для лечения вирусных инфекций - Google Patents
Соединения и фармацевтические композиции для лечения вирусных инфекций Download PDFInfo
- Publication number
- RU2012132218A RU2012132218A RU2012132218/04A RU2012132218A RU2012132218A RU 2012132218 A RU2012132218 A RU 2012132218A RU 2012132218/04 A RU2012132218/04 A RU 2012132218/04A RU 2012132218 A RU2012132218 A RU 2012132218A RU 2012132218 A RU2012132218 A RU 2012132218A
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- Prior art keywords
- compound according
- interferon
- pharmaceutically acceptable
- acceptable salt
- formula
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- 150000001875 compounds Chemical class 0.000 title claims abstract 22
- 239000008194 pharmaceutical composition Substances 0.000 title claims 4
- 208000036142 Viral infection Diseases 0.000 title 1
- 150000003839 salts Chemical class 0.000 claims abstract 11
- 125000000547 substituted alkyl group Chemical group 0.000 claims abstract 9
- 239000001257 hydrogen Substances 0.000 claims abstract 7
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 7
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract 6
- 125000003118 aryl group Chemical group 0.000 claims abstract 5
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract 5
- 150000002431 hydrogen Chemical group 0.000 claims abstract 5
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract 5
- -1 hydroxyarylalkyl Chemical group 0.000 claims abstract 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 abstract 4
- IWUCXVSUMQZMFG-AFCXAGJDSA-N Ribavirin Chemical group 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 abstract 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract 4
- 229960000329 ribavirin Drugs 0.000 claims abstract 4
- HZCAHMRRMINHDJ-DBRKOABJSA-N ribavirin Natural products O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1N=CN=C1 HZCAHMRRMINHDJ-DBRKOABJSA-N 0.000 claims abstract 4
- IRZRJANZDIOOIF-GAJNKVMBSA-N (2r,3r,4r,5r)-2-(4-aminopyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)-3-methyloxolane-3,4-diol Chemical compound C[C@@]1(O)[C@H](O)[C@@H](CO)O[C@H]1N1C2=NC=NC(N)=C2C=C1 IRZRJANZDIOOIF-GAJNKVMBSA-N 0.000 claims abstract 2
- NYPIRLYMDJMKGW-VPCXQMTMSA-N 4-amino-1-[(2r,3r,4r,5r)-3-fluoro-4-hydroxy-5-(hydroxymethyl)-3-methyloxolan-2-yl]pyrimidin-2-one Chemical compound C[C@@]1(F)[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)N=C(N)C=C1 NYPIRLYMDJMKGW-VPCXQMTMSA-N 0.000 claims abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 2
- HTJGLYIJVSDQAE-VWNXEWBOSA-N [(1s,6s,7s,8r,8ar)-1,7,8-trihydroxy-1,2,3,5,6,7,8,8a-octahydroindolizin-6-yl] butanoate Chemical compound O[C@H]1[C@H](O)[C@@H](OC(=O)CCC)CN2CC[C@H](O)[C@@H]21 HTJGLYIJVSDQAE-VWNXEWBOSA-N 0.000 claims abstract 2
- RLAHNGKRJJEIJL-RFZPGFLSSA-N [(2r,4r)-4-(2,6-diaminopurin-9-yl)-1,3-dioxolan-2-yl]methanol Chemical compound C12=NC(N)=NC(N)=C2N=CN1[C@H]1CO[C@@H](CO)O1 RLAHNGKRJJEIJL-RFZPGFLSSA-N 0.000 claims abstract 2
- 125000002252 acyl group Chemical group 0.000 claims abstract 2
- 125000005041 acyloxyalkyl group Chemical group 0.000 claims abstract 2
- 125000003342 alkenyl group Chemical group 0.000 claims abstract 2
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims abstract 2
- 125000000304 alkynyl group Chemical group 0.000 claims abstract 2
- 229950005846 amdoxovir Drugs 0.000 claims abstract 2
- 125000000539 amino acid group Chemical group 0.000 claims abstract 2
- 150000001413 amino acids Chemical class 0.000 claims abstract 2
- 125000005097 aminocarbonylalkyl group Chemical group 0.000 claims abstract 2
- IQFYYKKMVGJFEH-UHFFFAOYSA-N beta-L-thymidine Natural products O=C1NC(=O)C(C)=CN1C1OC(CO)C(O)C1 IQFYYKKMVGJFEH-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract 2
- 125000004181 carboxyalkyl group Chemical group 0.000 claims abstract 2
- 229950003414 celgosivir Drugs 0.000 claims abstract 2
- 229960005338 clevudine Drugs 0.000 claims abstract 2
- GBBJCSTXCAQSSJ-XQXXSGGOSA-N clevudine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1[C@H](F)[C@@H](O)[C@H](CO)O1 GBBJCSTXCAQSSJ-XQXXSGGOSA-N 0.000 claims abstract 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims abstract 2
- 229960000366 emtricitabine Drugs 0.000 claims abstract 2
- 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 abstract 2
- 229960001627 lamivudine Drugs 0.000 claims abstract 2
- 150000002632 lipids Chemical class 0.000 claims abstract 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract 2
- BXNMTOQRYBFHNZ-UHFFFAOYSA-N resiquimod Chemical compound C1=CC=CC2=C(N(C(COCC)=N3)CC(C)(C)O)C3=C(N)N=C21 BXNMTOQRYBFHNZ-UHFFFAOYSA-N 0.000 claims abstract 2
- 229950010550 resiquimod Drugs 0.000 claims abstract 2
- NHKZSTHOYNWEEZ-AFCXAGJDSA-N taribavirin Chemical group N1=C(C(=N)N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 NHKZSTHOYNWEEZ-AFCXAGJDSA-N 0.000 claims abstract 2
- 229950006081 taribavirin Drugs 0.000 claims abstract 2
- IQFYYKKMVGJFEH-CSMHCCOUSA-N telbivudine Chemical compound O=C1NC(=O)C(C)=CN1[C@H]1O[C@@H](CO)[C@H](O)C1 IQFYYKKMVGJFEH-CSMHCCOUSA-N 0.000 claims abstract 2
- 229960005311 telbivudine Drugs 0.000 claims abstract 2
- 229960004556 tenofovir Drugs 0.000 claims abstract 2
- VCMJCVGFSROFHV-WZGZYPNHSA-N tenofovir disoproxil fumarate Chemical compound OC(=O)\C=C\C(O)=O.N1=CN=C2N(C[C@@H](C)OCP(=O)(OCOC(=O)OC(C)C)OCOC(=O)OC(C)C)C=NC2=C1N VCMJCVGFSROFHV-WZGZYPNHSA-N 0.000 claims abstract 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 5
- 108010050904 Interferons Proteins 0.000 claims 4
- 102000014150 Interferons Human genes 0.000 claims 4
- 229940079322 interferon Drugs 0.000 claims 4
- OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- GVEZIHKRYBHEFX-MNOVXSKESA-N 13C-Cerulenin Natural products CC=CCC=CCCC(=O)[C@H]1O[C@@H]1C(N)=O GVEZIHKRYBHEFX-MNOVXSKESA-N 0.000 claims 2
- 102000053642 Catalytic RNA Human genes 0.000 claims 2
- 108090000994 Catalytic RNA Proteins 0.000 claims 2
- 101000749287 Clitocybe nebularis Clitocypin Proteins 0.000 claims 2
- 101000767029 Clitocybe nebularis Clitocypin-1 Proteins 0.000 claims 2
- 229940094664 Cysteine protease inhibitor Drugs 0.000 claims 2
- 229940121759 Helicase inhibitor Drugs 0.000 claims 2
- 108010047761 Interferon-alpha Proteins 0.000 claims 2
- 102000006992 Interferon-alpha Human genes 0.000 claims 2
- 102000015696 Interleukins Human genes 0.000 claims 2
- 108010063738 Interleukins Proteins 0.000 claims 2
- 229940123066 Polymerase inhibitor Drugs 0.000 claims 2
- 229940124158 Protease/peptidase inhibitor Drugs 0.000 claims 2
- 101800001838 Serine protease/helicase NS3 Proteins 0.000 claims 2
- 230000000692 anti-sense effect Effects 0.000 claims 2
- 239000003443 antiviral agent Substances 0.000 claims 2
- FIVPIPIDMRVLAY-UHFFFAOYSA-N aspergillin Natural products C1C2=CC=CC(O)C2N2C1(SS1)C(=O)N(C)C1(CO)C2=O FIVPIPIDMRVLAY-UHFFFAOYSA-N 0.000 claims 2
- ZVSKZLHKADLHSD-UHFFFAOYSA-N benzanilide Chemical compound C=1C=CC=CC=1C(=O)NC1=CC=CC=C1 ZVSKZLHKADLHSD-UHFFFAOYSA-N 0.000 claims 2
- GVEZIHKRYBHEFX-UHFFFAOYSA-N caerulein A Natural products CC=CCC=CCCC(=O)C1OC1C(N)=O GVEZIHKRYBHEFX-UHFFFAOYSA-N 0.000 claims 2
- GVEZIHKRYBHEFX-NQQPLRFYSA-N cerulenin Chemical compound C\C=C\C\C=C\CCC(=O)[C@H]1O[C@H]1C(N)=O GVEZIHKRYBHEFX-NQQPLRFYSA-N 0.000 claims 2
- 229950005984 cerulenin Drugs 0.000 claims 2
- 230000001419 dependent effect Effects 0.000 claims 2
- FIVPIPIDMRVLAY-RBJBARPLSA-N gliotoxin Chemical compound C1C2=CC=C[C@H](O)[C@H]2N2[C@]1(SS1)C(=O)N(C)[C@@]1(CO)C2=O FIVPIPIDMRVLAY-RBJBARPLSA-N 0.000 claims 2
- 229940103893 gliotoxin Drugs 0.000 claims 2
- 229930190252 gliotoxin Natural products 0.000 claims 2
- 208000002672 hepatitis B Diseases 0.000 claims 2
- 239000003112 inhibitor Substances 0.000 claims 2
- 125000003729 nucleotide group Chemical group 0.000 claims 2
- 229940046166 oligodeoxynucleotide Drugs 0.000 claims 2
- 239000000137 peptide hydrolase inhibitor Substances 0.000 claims 2
- 108091092562 ribozyme Proteins 0.000 claims 2
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 claims 2
- 241000710831 Flavivirus Species 0.000 claims 1
- 208000005176 Hepatitis C Diseases 0.000 claims 1
- 108010005716 Interferon beta-1a Proteins 0.000 claims 1
- 108010074328 Interferon-gamma Proteins 0.000 claims 1
- 102000008070 Interferon-gamma Human genes 0.000 claims 1
- TVRCRTJYMVTEFS-ICGCPXGVSA-N [(2r,3r,4r,5r)-5-(4-amino-2-oxopyrimidin-1-yl)-4-hydroxy-2-(hydroxymethyl)-4-methyloxolan-3-yl] (2s)-2-amino-3-methylbutanoate Chemical compound C[C@@]1(O)[C@H](OC(=O)[C@@H](N)C(C)C)[C@@H](CO)O[C@H]1N1C(=O)N=C(N)C=C1 TVRCRTJYMVTEFS-ICGCPXGVSA-N 0.000 claims 1
- 108010080374 albuferon Proteins 0.000 claims 1
- 235000001014 amino acid Nutrition 0.000 claims 1
- 125000004103 aminoalkyl group Chemical group 0.000 claims 1
- 150000001720 carbohydrates Chemical class 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 238000009472 formulation Methods 0.000 claims 1
- 108010010648 interferon alfacon-1 Proteins 0.000 claims 1
- 229960003358 interferon alfacon-1 Drugs 0.000 claims 1
- 229960004461 interferon beta-1a Drugs 0.000 claims 1
- 229960003130 interferon gamma Drugs 0.000 claims 1
- 108010042414 interferon gamma-1b Proteins 0.000 claims 1
- 229940028862 interferon gamma-1b Drugs 0.000 claims 1
- 108010045648 interferon omega 1 Proteins 0.000 claims 1
- 108700027921 interferon tau Proteins 0.000 claims 1
- 210000004185 liver Anatomy 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
- 150000003548 thiazolidines Chemical class 0.000 claims 1
- 229950002810 valopicitabine Drugs 0.000 claims 1
- 229960000980 entecavir Drugs 0.000 abstract 1
- YXPVEXCTPGULBZ-WQYNNSOESA-N entecavir hydrate Chemical compound O.C1=NC=2C(=O)NC(N)=NC=2N1[C@H]1C[C@H](O)[C@@H](CO)C1=C YXPVEXCTPGULBZ-WQYNNSOESA-N 0.000 abstract 1
- KJMAQQYJHXGQLO-HXKVNORTSA-N CC(C)(CO)C(SCCOP(NCc1ccccc1)(OCC(CC1)O[C@@H]1[n]1c2ncnc(N)c2nc1)=O)=O Chemical compound CC(C)(CO)C(SCCOP(NCc1ccccc1)(OCC(CC1)O[C@@H]1[n]1c2ncnc(N)c2nc1)=O)=O KJMAQQYJHXGQLO-HXKVNORTSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/02—Heterocyclic radicals containing only nitrogen as ring hetero atoms
-
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- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/22—Amides of acids of phosphorus
- C07F9/24—Esteramides
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Abstract
1. Соединение формулыили его фармацевтически приемлемая соль, стереоизомерная, таутомерная или полиморфная форма, в котором;Rпредставляет собой необязательно замещенный алкил, алкенил, алкинил, арил, арилалкил, циклоалкил, циклоалкенил, гидроксиалкил, амино, гетероциклил или гетероарил;Rи Rвыбирают следующим образом:i) Rи Rкаждый независимо представляют собой водород или необязательно замещенный алкил, карбоксиалкил, гидроксиалкил, гидроксиарилалкил, ацилоксиалкил, аминокарбонилалкил, алкоксикарбонилалкил, арил, арилалкил, циклоалкил, гетероарил или гетероциклил; илиii) Rи Rвместе с атомом азота, на который они замещены, образуют гетероциклическое или гетероарильное кольцо, имеющее от 3 до 7 членов; иRвыбран из группы состоящей из рибавирина, вирамидина, валопицитабина, PSI-6130, МК-0608, резиквимода, целгосивира, ламивудина, энтекавира, телбивудина, рацивира, эмтрицитабина, клевудина, амдоксовира, тенофовира и адефовира.2. Соединение по п.1, имеющее формулу:или его фармацевтически приемлемая соль, стереоизомерная, таутомерная или полиморфная форма.3. Соединение по п.1, имеющее формулу:или его фармацевтически приемлемая соль, стереоизомерная, таутомерная или полиморфная форма.4. Соединение по п.1, имеющее формулу:или его фармацевтически приемлемая соль, стереоизомерная, таутомерная или полиморфная форма.5. Соединение по п.1, имеющее формулу:илиRпредставляет собой водород, метил или метокси;Rнезависимо представляет собой H, карбамил, линейный, разветвленный или циклический алкил; ацил; СО-алкил, СО-арил, СО-алкоксиалкил, CO-арилоксиалкил, СО-замещенный арил, сложный эфир сульфоната, липид, аминокислота; аминокислотный остаток
Claims (19)
1. Соединение формулы
или его фармацевтически приемлемая соль, стереоизомерная, таутомерная или полиморфная форма, в котором;
Ry представляет собой необязательно замещенный алкил, алкенил, алкинил, арил, арилалкил, циклоалкил, циклоалкенил, гидроксиалкил, амино, гетероциклил или гетероарил;
Ra и Rb выбирают следующим образом:
i) Ra и Rb каждый независимо представляют собой водород или необязательно замещенный алкил, карбоксиалкил, гидроксиалкил, гидроксиарилалкил, ацилоксиалкил, аминокарбонилалкил, алкоксикарбонилалкил, арил, арилалкил, циклоалкил, гетероарил или гетероциклил; или
ii) Ra и Rb вместе с атомом азота, на который они замещены, образуют гетероциклическое или гетероарильное кольцо, имеющее от 3 до 7 членов; и
R1 выбран из группы состоящей из рибавирина, вирамидина, валопицитабина, PSI-6130, МК-0608, резиквимода, целгосивира, ламивудина, энтекавира, телбивудина, рацивира, эмтрицитабина, клевудина, амдоксовира, тенофовира и адефовира.
5. Соединение по п.1, имеющее формулу:
Rd представляет собой водород, метил или метокси;
RL независимо представляет собой H, карбамил, линейный, разветвленный или циклический алкил; ацил; СО-алкил, СО-арил, СО-алкоксиалкил, CO-арилоксиалкил, СО-замещенный арил, сложный эфир сульфоната, липид, аминокислота; аминокислотный остаток, или углевод;
или его фармацевтически приемлемая соль, стереоизомерная, таутомерная или полиморфная форма.
7. Соединение по любому из пп.1-5, в котором Ry является замещенным алкилом и Ra и Rb независимо представляют собой водород, алкил, замещенный алкил, бензил или замещенный бензил.
8. Соединение по п.7, в котором Ry является гидроксиалкилом или аминоалкилом.
9. Соединение по п.1, в котором Ry представляет собой -ORC, -C(RC)3 или -NHRC, где каждый из RC независимо представляет собой алкил, замещенный алкил, арил или замещеннвй арил; и Ra и Rb независимо представляют собой водород, алкил, замещенный алкил, бензил или замещенный бензил.
10. Соединение по п.1, в котором Ra и Rb независимо представляют собой водород, бензил или замещенный алкил.
12. Фармацевтическая композиция, содержащая соединение по любому из пп.1-11 и фармацевтически приемлемый наполнитель, носитель или разбавитель.
13. Композиция по п.12, в котором композиция представляет собой рецептуру для перорального приема.
14. Применение соединения согласно любому из пп.1-11, для лечения организма-хозяина, инфицированного флавивирусом или вирусом гепатита B.
15. Применение по п.14 для лечения организма-хозяина, инфицированного вирусом гепатита B.
16. Применение по п.14 для лечения организма-хозяина, инфицированного вирусом гепатита C.
17. Применение по п.14, в котором указанное соединение или фармацевтическую композицию вводят в комбинации или чередовании со вторым противовирусным средством, необязательно выбираемым из группы, состоящей из интерферона, рибавирина, интерлейкина, ингибитора протеазы NS3, ингибитора цистеин-протеазы, фенантренхинона, производного тиазолидина, тиазолидина, бензанилида, ингибитора геликазы, ингибитора полимеразы, нуклеотидного аналога, глиотоксина, церуленина, антисмыслового олигодезоксинуклеотида фосфоротиоата, ингибитора IRES-зависимой трансляции и рибозима; или в котором соединение или его фармацевтически приемлемую соль или стереоизомер вводят в комбинации или чередовании со вторым противовирусным средством, необязательно выбираемым из группы, состоящей из интерферона, рибавирина, интерлейкина, ингибитора протеазы NS3, ингибитора цистеин-протеазы, фенантренхинона, производного тиазолидина, тиазолидина, бензанилида, ингибитора геликазы, ингибитора полимеразы, нуклеотидного аналога, глиотоксина, церуленина, антисмыслового олигодезоксинуклеотида фосфоротиоата, ингибитора IRES-зависимой трансляции и рибозима, причем необязательно второе средство выбирают из группы, состоящей из пегилированного интерферона-альфа 2a, интерферона альфакон-1, интерферона природного происхождения, альбуферона, интерферона-бета 1a, интерферона омега, интерферона альфа, интерферона гамма, интерферона тау, интерферона дельта и интерферона γ-1b.
18. Применение по п.14, в котором организмом-хозяином является человек.
19. Применение по п.14, в котором при указанном введении существенное количество указанного соединения или фармацевтической композиции направленно поступает в печень указанного организма-хозяина.
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