RU2007135053A - Замещенные производные пиридо(2, 3-d)пиримидина, пригодные в качестве лекарственных средств для лечения аутоиммунных нарушений - Google Patents
Замещенные производные пиридо(2, 3-d)пиримидина, пригодные в качестве лекарственных средств для лечения аутоиммунных нарушений Download PDFInfo
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- RU2007135053A RU2007135053A RU2007135053/04A RU2007135053A RU2007135053A RU 2007135053 A RU2007135053 A RU 2007135053A RU 2007135053/04 A RU2007135053/04 A RU 2007135053/04A RU 2007135053 A RU2007135053 A RU 2007135053A RU 2007135053 A RU2007135053 A RU 2007135053A
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- Prior art keywords
- pyrimidine
- pyrido
- amino
- dimethoxyphenyl
- pivaloylamino
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- 159000000018 pyrido[2,3-d]pyrimidines Chemical class 0.000 title claims abstract 9
- 208000023275 Autoimmune disease Diseases 0.000 title claims 3
- 239000003814 drug Substances 0.000 title 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract 7
- 208000035475 disorder Diseases 0.000 claims abstract 6
- MZOFCQQQCNRIBI-VMXHOPILSA-N (3s)-4-[[(2s)-1-[[(2s)-1-[[(1s)-1-carboxy-2-hydroxyethyl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-3-[[2-[[(2s)-2,6-diaminohexanoyl]amino]acetyl]amino]-4-oxobutanoic acid Chemical compound OC[C@@H](C(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@@H](N)CCCCN MZOFCQQQCNRIBI-VMXHOPILSA-N 0.000 claims abstract 3
- 208000024172 Cardiovascular disease Diseases 0.000 claims abstract 3
- 108060008682 Tumor Necrosis Factor Proteins 0.000 claims abstract 3
- 102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 claims abstract 3
- 230000002062 proliferating effect Effects 0.000 claims abstract 3
- 150000001204 N-oxides Chemical class 0.000 claims abstract 2
- 150000003839 salts Chemical class 0.000 claims abstract 2
- 239000012453 solvate Substances 0.000 claims abstract 2
- -1 N-piperidinyl Chemical group 0.000 claims 5
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 4
- UDJFFSGCRRMVFH-UHFFFAOYSA-N pyrido[2,3-d]pyrimidine Chemical compound N1=CN=CC2=CC=CN=C21 UDJFFSGCRRMVFH-UHFFFAOYSA-N 0.000 claims 4
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 125000003282 alkyl amino group Chemical group 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 125000003118 aryl group Chemical group 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- GSYSFVSGPABNNL-UHFFFAOYSA-N methyl 2-dimethoxyphosphoryl-2-(phenylmethoxycarbonylamino)acetate Chemical group COC(=O)C(P(=O)(OC)OC)NC(=O)OCC1=CC=CC=C1 GSYSFVSGPABNNL-UHFFFAOYSA-N 0.000 claims 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims 2
- 208000015114 central nervous system disease Diseases 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- 208000026278 immune system disease Diseases 0.000 claims 2
- 125000004193 piperazinyl group Chemical group 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- XKEBMWRWBWRQAO-UHFFFAOYSA-N 1h-pyrido[2,3-d]pyrimidin-4-one Chemical compound C1=CC=C2C(=O)N=CNC2=N1 XKEBMWRWBWRQAO-UHFFFAOYSA-N 0.000 claims 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 1
- 125000002252 acyl group Chemical class 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 125000001769 aryl amino group Chemical group 0.000 claims 1
- 150000001543 aryl boronic acids Chemical class 0.000 claims 1
- 125000004104 aryloxy group Chemical group 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 125000002757 morpholinyl group Chemical group 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000003395 phenylethylamino group Chemical group [H]N(*)C([H])([H])C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 125000001425 triazolyl group Chemical group 0.000 claims 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 abstract 1
- 206010052779 Transplant rejections Diseases 0.000 abstract 1
- 210000003169 central nervous system Anatomy 0.000 abstract 1
- 229940125721 immunosuppressive agent Drugs 0.000 abstract 1
- 239000003018 immunosuppressive agent Substances 0.000 abstract 1
- 208000027866 inflammatory disease Diseases 0.000 abstract 1
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
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Claims (9)
1. Производное пиридо(2,3-d)пиримидина, имеющее общую формулу:
где
R1 представляет собой аминогруппу;
R2 выбран из группы, состоящей из гидрокси, галогена, моноC1-7алкиламино; моноариламино; моноарилC1-7алкиламино; морфолинила; N-пиперидинила; триазолила; замещенного гетероциклом амино; C1-7алкокси; оксигетероциклической группы; пиперазинила или гомопиперазинила, где указанный пиперазинил необязательно является N-замещенным ацилом, C1-7алкилом или арилалкилом;
R3 выбран из группы, состоящей из арильной и гетероарильной групп, необязательно замещенных одним или более заместителями, выбранными из группы, состоящей из галогена, галогенC1-7алкила, C1-7алкокси и алкиламино; и
R4 представляет собой водород,
или его фармацевтически приемлемая аддитивная соль, или его дигидропроизводное, или тетрагидропроизводное, или его стереохимическая изомерная форма, или его N-оксид, или его сольват.
2. Производное пиридо(2,3-d)пиримидина по п.1, где R3 представляет собой монозамещенную или полизамещенную фенильную группу или R3 представляет собой тиенил.
3. Производное пиридо(2,3-d)пиримидина по п.1 или 2, где R2 выбран из группы, состоящей из C1-4алкокси, тетрагидропиранилокси, метилпиперидинокси, монопропиламино, анилино, броманилино, бензиламино и фенилэтиламино.
4. Производное пиридо(2,3-d)пиримидина по п.1 или 2, где R2 представляет собой группу пиперазин-1-ила, где указанная группа необязательно замещена в 4 положении заместителем R5, где R5 выбран из группы, состоящей из COR8, где R8 выбран из водорода, C1-7алкила, арила, необязательно замещенного одним или более заместителями, арилокси, и ариламино; и R11, где R11 представляет собой арилалкил.
5. Производное пиридо(2,3-d)пиримидина, выбранное из группы, состоящей из
- 2-амино-4-изопропокси-6-бромпиридо[2,3-d]пиримидина,
- 2-амино-4-изопропокси-6-(3,4-диметоксифенил)пиридо[2,3-d]пиримидина,
- 2-пивалоиламино-4-морфолино-6-бромпиридо[2,3-d]пиримидина,
- 2-амино-4-морфолино-6-(3,4-диметоксифенил)пиридо[2,3-d]пиримидина,
- 2-пивалоиламино-4-N-пиперазино-6-бромпиридо[2,3-d]пиримидина,
- 2-пивалоиламино-4-[N-4-метилфенилкарбамоилпиперазин-1-ил]-6-бромпиридо[2,3-d]пиримидина,
- 2-амино-4-[N-4-метилфенилкарбамоилпиперазин-1-ил]-6-бромпиридо[2,3-d]пиримидина,
- 2-пивалоиламино-4-N-пиперазинил-6-(3,4-диметоксифенил)пиридо[2,3-d]пиримидина,
- 2-пивалоиламино-4-[(N-феноксиацетил)-N-пиперазин-1-ил]-6-(3,4-диметоксифенил)пиридо[2,3-d]пиримидина,
- 2-амино-4-(N-феноксиацетил-N-пиперазин-1-ил)-6-(3,4-диметоксифенил)пиридо[2,3-d]пиримидина,
- 2-пивалоиламино-4-[N-4-метилфенилкарбамоилпиперазин-1-ил]-6-(3,4-диметоксифенил)пиридо[2,3-d]пиримидина,
- 2-амино-4-(N-4-метилфенилкарбамоилпиперазин-1-ил)-6-(3,4-диметоксифенил)пиридо[2,3-d]пиримидина,
- 2-пивалоиламино-4-[(N-бензилоксикарбонил)пиперазин-1-ил]-6-бромпиридо[2,3-d]пиримидина,
- 2-пивалоиламино-4-[(N-бензилоксикарбонил)пиперазин-1-ил]-6-(3,4-диметоксифенил)пиридо[2,3-d]пиримидина,
- 2-амино-6-(3,4-диметоксифенил)-4-[(N-бензилоксикарбонил)пиперазин-1-ил]пиридо[2,3-d]пиримидина,
- 2-пивалоиламино-4-изопропокси-6-(4-диметиламинофенил)пиридо[2,3-d]пиримидина,
- 2-пивалоиламино-4-изопропокси-6-(4-трифторметилфенил)пиридо[2,3-d]пиримидина;
- 2-пивалоиламино-4-изопропокси-6-(2-тиенил)пиридо[2,3-d]пиримидина,
- 2-амино-4-изопропокси-6-(4-диметиламинофенил)пиридо[2,3-d]пиримидина;
- 2-амино-4-изопропокси-6-(4-трифторметилфенил)пиридо[2,3-d]пиримидина,
- 2-амино-4-изопропокси-6-(2-тиенил)пиридо[2,3-d]пиримидина,
- 2-амино-4-(пиперазин-1-ил)-6-(3,4-диметоксифенил)пиридо[2,3-d]пиримидина,
- 2-амино-4-(4-бензилпиперазин-1-ил)-6-(3,4-диметоксифенил)пиридо[2,3-d]пиримидина,
- 2-пивалоиламино-4-(1,2,4-триазолил)-6-(3,4-диметоксифенил)пиридо[2,3-d]пиримидина,
- 2-пивалоиламино-4-н-пропиламино-6-(3,4-диметоксифенил)пиридо[2,3-d]пиримидина;
- 2-пивалоиламино-4-изопропиламино-6-(3,4-диметоксифенил)пиридо[2,3-d]пиримидина;
- 2-пивалоиламино-4-(1-пиперидино)-6-(3,4-диметоксифенил)пиридо[2,3-d]пиримидина;
- 2-пивалоиламино-4-(тетрагидро-2H-пиран-4-илокси)-6-(3,4-диметоксифенил)пиридо[2,3-d]пиримидина,
- 2-пивалоиламино-6-(3,4-диметоксифенил)-4-(4-N-метилпиперидинокси)пиридо[2,3-d]пиримидина;
- 2-амино-4-н-пропиламино-6-(3,4-диметоксифенил)пиридо[2,3-d]пиримидина;
- 2-амино-4-изопропиламино-6-(3,4-диметоксифенил)пиридо[2,3-d]пиримидина;
- 2-амино-4-(1-пиперидино)-6-(3,4-диметоксифенил)пиридо[2,3-d]пиримидина;
- 2-амино-4-(тетрагидро-2H-пиран-4-илокси)-6-(3,4-диметоксифенил)пиридо[2,3-d]пиримидина;
- 2-амино-6-(3,4-диметоксифенил)-4-(4-N-метилпиперидинокси)пиридо[2,3-d]пиримидина;
- 2-амино-4-метокси-6-(3,4-диметоксифенил)пиридо[2,3-d]пиримидина;
- 2-пивалоиламино-4-N-гомопиперазино-6-бромпиридо[2,3-d]пиримидина;
- 2-пивалоиламино-4-N-гомопиперазино-6-(3,4-диметоксифенил)пиридо[2,3-d]пиримидина;
- 2-амино-4-N-гомопиперазино-6-бромпиридо[2,3-d]пиримидина;
- 2-амино-4-N-гомопиперазино-6-(3,4-диметоксифенил)пиридо[2,3-d]пиримидина;
- 2-амино-4-(втор-бутокси)-6-(3,4-диметоксифенил)пиридо[2,3-d]пиримидина;
- 2-амино-4-(втор-бутокси)-6-(3,4-диметоксифенил)пиридо[2,3-d]пиримидина, соль гидрохлорида;
- 2-амино-4-изопропокси-6-(3,4-диметилфенил)пиридо[2,3-d]пиримидина;
- 2-пивалоиламино-4-(3-броманилино)-6-(3,4-диметоксифенил)пиридо[2,3-d]пиримидина;
- 2-пивалоиламино-4-(бензиламино)-6-(3,4-диметоксифенил)пиридо[2,3-d]пиримидина;
- 2-пивалоиламино-4-(фенилэтиламино)-6-(3,4-диметоксифенил)пиридо[2,3-d]пиримидина;
- 2-амино-4-(3-броманилино)-6-(3,4-диметоксифенил)пиридо[2,3-d]пиримидина;
- 2-амино-4-(бензиламино)-6-(3,4-диметоксифенил)пиридо[2,3-d]пиримидина;
- 2-амино-4-(фенилэтиламино)-6-(3,4-диметоксифенил)пиридо[2,3-d]пиримидина;
- 2-пивалоиламино-4-N-гомопиперазино-6-бромпиридо[2,3-d]пиримидина;
- 2-амино-4-N-гомопиперазино-6-бромпиридо[2,3-d]пиримидина;
- 2-пивалоиламино-4-N-гомопиперазино-6-(3,4-диметоксифенил)пиридо[2,3-d]пиримидина;
- 2-амино-4-N-гомопиперазино-6-(3,4-диметоксифенил)пиридо[2,3-d]пиримидина;
- 2-пивалоиламино-6-(4-фторфенил)пиридо[2,3-d]пиримидин-4-(3H)-она;
- 2-пивалоиламино-4-(1,2,4-триазолил)-6-бромпиридо[2,3-d]пиримидина;
- 2-пивалоиламино-4-(3-метиланилино)-6-бромпиридо[2,3-d]пиримидина;
- 2-амино-4-(3-метиланилино)-6-бромпиридо[2,3-d]пиримидина;
- 2-пивалоиламино-4-(N-пиперидино)-6-(4-фторфенил)пиридо[2,3-d]пиримидина;
- 2-пивалоиламино-4-(N-морфолино)-6-(4-фторфенил)пиридо[2,3-d]пиримидина;
- 2-пивалоиламино-4-(N-ацетил-N-пиперазин-1-ил)-6-(4-фторфенил)пиридо[2,3-d]пиримидина;
- 2-пивалоиламино-4-(N-метил-N-пиперазин-1-ил)-6-(4-фторфенил)пиридо[2,3-d]пиримидина;
- 2-амино-4-(N-пиперидино)-6-(4-фторфенил)пиридо[2,3-d]пиримидина;
- 2-амино-4-(N-морфолино)-6-(4-фторфенил)пиридо[2,3-d]пиримидина;
- 2-амино-4-(N-ацетил-N-пиперазин-1-ил)-6-(4-фторфенил)пиридо[2,3-d]пиримидина;
- 2-амино-4-(N-метил-N-пиперазин-1-ил)-6-(4-фторфенил)пиридо[2,3-d]пиримидина;
- 2-пивалоиламино-4-этокси-6-(4-фторфенил)пиридо[2,3-d]пиримидина;
- 2-пивалоиламино-4-изопропокси-6-(4-фторфенил)пиридо[2,3-d]пиримидина;
- 2-амино-4-этокси-6-(4-фторфенил)пиридо[2,3-d]пиримидина; и
- 2-амино-4-изопропокси-6-(4-фторфенил)пиридо[2,3-d]пиримидина.
6. Фармацевтическая композиция, содержащая один или более фармацевтически приемлемых носителей и производное пиридо[2,3-d]пиримидина по пп.1-5.
7. Способ получения производного пиридо(2,3-d)пиримидина по п.1, включающий стадию проведения реакции 2-R1-замещенного 6-бромпиридо[2,3-d]пиримидина или 2-R1-замещенного 6-хлорпиридо[2,3-d]пиримидина, где R1 является таким, как определено в структурной формуле (I), с арилбороновой кислотой, включающей радикал R3, где R3 представляет собой группу арила или гетероарила, как определено в структурной формуле (I).
8. Способ лечения или профилактики заболевания, выбранного из группы, состоящей из иммунных нарушений, аутоиммунных нарушений, сердечно-сосудистых нарушений, нарушений центральной нервной системы, связанных с TNF-α нарушений и клеточно-пролиферативных нарушений, включающий стадию введения индивидууму, нуждающемуся в этом, терапевтически эффективного количества производного пиридо(2,3-d)пиримидина по любому из пп.1-5.
9. Производное (2,3-d)пиримидина по п.1 или 5 для применения для предотвращения или лечения иммунных нарушений, аутоиммунных нарушений, сердечно-сосудистых нарушений, нарушений центральной нервной системы, нарушений, опосредованных TNF-α, и клеточно-пролиферативных нарушений.
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GBGB0503506.8A GB0503506D0 (en) | 2005-02-21 | 2005-02-21 | Substituted pyrido(2,3-d) pyrimidine derivatives and pharmaceutical compositions useful as medicines for the treatment of autoimmune disorders |
GB0503506.8 | 2005-02-21 |
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US11945814B2 (en) | 2018-06-08 | 2024-04-02 | Crt Pioneer Fund Lp | Salt form |
US11964972B2 (en) | 2018-06-08 | 2024-04-23 | Crt Pioneer Fund Lp | Salt form |
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US8338435B2 (en) * | 2006-07-20 | 2012-12-25 | Gilead Sciences, Inc. | Substituted pyrido(3,2-D) pyrimidines and pharmaceutical compositions for treating viral infections |
WO2008009078A2 (en) | 2006-07-20 | 2008-01-24 | Gilead Sciences, Inc. | 4,6-dl- and 2,4,6-trisubstituted quinazoline derivatives useful for treating viral infections |
US10144736B2 (en) * | 2006-07-20 | 2018-12-04 | Gilead Sciences, Inc. | Substituted pteridines useful for the treatment and prevention of viral infections |
WO2008077650A1 (en) * | 2006-12-26 | 2008-07-03 | Gilead Sciences, Inc. | Pyrido(3,2-d)pyrimidines useful for treating viral infections |
TW200840584A (en) * | 2006-12-26 | 2008-10-16 | Gilead Sciences Inc | Pyrido(3,2-d)pyrimidines useful for treating viral infections |
MX2011008505A (es) | 2009-02-12 | 2012-10-15 | Merck Serono Sa | 2-morfolino-pirido[3,2-d]pirimidinas. |
AU2014250836C1 (en) | 2013-04-12 | 2019-01-17 | Asana Biosciences, Llc | Quinazolines and azaquinazolines as dual inhibitors of RAS/RAF/MEK/ERK and PI3K/AKT/PTEN/mTOR pathways |
CN103694255A (zh) * | 2014-01-09 | 2014-04-02 | 华中师范大学 | 吡啶并噁嗪酮和吡啶并嘧啶酮类化合物及其制备方法与应用 |
GB201416186D0 (en) | 2014-09-12 | 2014-10-29 | Redx Pharma Ltd | Compounds |
CA2978188C (en) | 2015-03-04 | 2020-05-12 | Gilead Sciences, Inc. | Toll-like receptor modulating 4,6-diamino-pyrido[3,2-d]pyrimidine compounds |
US10640499B2 (en) | 2016-09-02 | 2020-05-05 | Gilead Sciences, Inc. | Toll like receptor modulator compounds |
WO2018045144A1 (en) | 2016-09-02 | 2018-03-08 | Gilead Sciences, Inc. | Toll like receptor modulator compounds |
TW202210480A (zh) | 2019-04-17 | 2022-03-16 | 美商基利科學股份有限公司 | 類鐸受體調節劑之固體形式 |
TW202212339A (zh) | 2019-04-17 | 2022-04-01 | 美商基利科學股份有限公司 | 類鐸受體調節劑之固體形式 |
TW202115056A (zh) | 2019-06-28 | 2021-04-16 | 美商基利科學股份有限公司 | 類鐸受體調節劑化合物的製備方法 |
CN113801114B (zh) * | 2020-06-11 | 2022-11-18 | 江苏恒瑞医药股份有限公司 | 稠合二环杂芳基类衍生物、其制备方法及其在医药上的应用 |
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US11945814B2 (en) | 2018-06-08 | 2024-04-02 | Crt Pioneer Fund Lp | Salt form |
US11964972B2 (en) | 2018-06-08 | 2024-04-23 | Crt Pioneer Fund Lp | Salt form |
RU2800877C2 (ru) * | 2018-09-19 | 2023-07-31 | Чиа Тай Тяньцин Фармасьютикал Груп Ко., Лтд. | Агонист tlr8 |
US12054482B2 (en) | 2018-09-19 | 2024-08-06 | Chia Tai Tianqing Pharmaceutical Group Co., Ltd. | TLR8 agonist |
Also Published As
Publication number | Publication date |
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IL185289A0 (en) | 2008-02-09 |
DK1851217T3 (da) | 2009-03-23 |
EP1851217B1 (en) | 2009-02-11 |
KR20070112174A (ko) | 2007-11-22 |
US20080312227A1 (en) | 2008-12-18 |
MX2007010156A (es) | 2008-02-19 |
HRP20090208T1 (en) | 2009-05-31 |
DE602006005136D1 (de) | 2009-03-26 |
WO2006087229A1 (en) | 2006-08-24 |
ATE422496T1 (de) | 2009-02-15 |
PT1851217E (pt) | 2009-05-14 |
CN101203514A (zh) | 2008-06-18 |
SI1851217T1 (sl) | 2009-06-30 |
ES2318723T3 (es) | 2009-05-01 |
BRPI0606844A2 (pt) | 2009-07-21 |
EP1851217A1 (en) | 2007-11-07 |
PL1851217T3 (pl) | 2009-07-31 |
GB0503506D0 (en) | 2005-03-30 |
AU2006215700A1 (en) | 2006-08-24 |
JP2008530167A (ja) | 2008-08-07 |
CA2598465A1 (en) | 2006-08-24 |
NO20074207L (no) | 2007-10-26 |
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