UA124100C2 - Спосіб одержання сполуки піроло[3,2-d]піримідину і проміжних сполук - Google Patents
Спосіб одержання сполуки піроло[3,2-d]піримідину і проміжних сполук Download PDFInfo
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- UA124100C2 UA124100C2 UAA201809087A UAA201809087A UA124100C2 UA 124100 C2 UA124100 C2 UA 124100C2 UA A201809087 A UAA201809087 A UA A201809087A UA A201809087 A UAA201809087 A UA A201809087A UA 124100 C2 UA124100 C2 UA 124100C2
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- Ukraine
- Prior art keywords
- compound
- formula
- acid
- sodium
- hydroxide
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 108
- 238000000034 method Methods 0.000 title claims abstract description 24
- -1 PYRIMIDINE COMPOUND Chemical class 0.000 title claims abstract description 4
- 238000002360 preparation method Methods 0.000 title description 10
- GSSXLFACIJSBOM-UHFFFAOYSA-N 2h-pyran-2-ol Chemical compound OC1OC=CC=C1 GSSXLFACIJSBOM-UHFFFAOYSA-N 0.000 title 1
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 28
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 27
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 24
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 24
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 24
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 14
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 14
- AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 claims description 14
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 13
- 235000011181 potassium carbonates Nutrition 0.000 claims description 13
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 12
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 238000005906 dihydroxylation reaction Methods 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical group 0.000 claims description 9
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 9
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 8
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 230000003993 interaction Effects 0.000 claims description 8
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 claims description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 6
- 239000003638 chemical reducing agent Substances 0.000 claims description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- SFWWGMKXCYLZEG-UHFFFAOYSA-N 3-methylmorpholine Chemical compound CC1COCCN1 SFWWGMKXCYLZEG-UHFFFAOYSA-N 0.000 claims description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 235000011054 acetic acid Nutrition 0.000 claims description 4
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 claims description 4
- 229910001863 barium hydroxide Inorganic materials 0.000 claims description 4
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 claims description 4
- 229910000024 caesium carbonate Inorganic materials 0.000 claims description 4
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 claims description 4
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 claims description 4
- 239000000347 magnesium hydroxide Substances 0.000 claims description 4
- 229910001862 magnesium hydroxide Inorganic materials 0.000 claims description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 4
- 239000011736 potassium bicarbonate Substances 0.000 claims description 4
- 229910000028 potassium bicarbonate Inorganic materials 0.000 claims description 4
- 235000015497 potassium bicarbonate Nutrition 0.000 claims description 4
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 claims description 4
- 229910000160 potassium phosphate Inorganic materials 0.000 claims description 4
- 235000011009 potassium phosphates Nutrition 0.000 claims description 4
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims description 4
- 235000017550 sodium carbonate Nutrition 0.000 claims description 4
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 4
- JEGMWWXJUXDNJN-UHFFFAOYSA-N 3-methylpiperidine Chemical compound CC1CCCNC1 JEGMWWXJUXDNJN-UHFFFAOYSA-N 0.000 claims description 3
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 claims description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 2
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 claims description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims description 2
- 235000015165 citric acid Nutrition 0.000 claims description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 2
- 235000019253 formic acid Nutrition 0.000 claims description 2
- 239000001530 fumaric acid Substances 0.000 claims description 2
- 235000011087 fumaric acid Nutrition 0.000 claims description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 2
- 239000011976 maleic acid Substances 0.000 claims description 2
- 239000001630 malic acid Substances 0.000 claims description 2
- 235000011090 malic acid Nutrition 0.000 claims description 2
- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 claims description 2
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- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 125000002632 imidazolidinyl group Chemical group 0.000 description 1
- 229960002751 imiquimod Drugs 0.000 description 1
- DOUYETYNHWVLEO-UHFFFAOYSA-N imiquimod Chemical compound C1=CC=CC2=C3N(CC(C)C)C=NC3=C(N)N=C21 DOUYETYNHWVLEO-UHFFFAOYSA-N 0.000 description 1
- 230000028993 immune response Effects 0.000 description 1
- 210000000987 immune system Anatomy 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 229940047124 interferons Drugs 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000004628 isothiazolidinyl group Chemical group S1N(CCC1)* 0.000 description 1
- 125000003965 isoxazolidinyl group Chemical group 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- OKKJLVBELUTLKV-VMNATFBRSA-N methanol-d1 Chemical compound [2H]OC OKKJLVBELUTLKV-VMNATFBRSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 244000000010 microbial pathogen Species 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000013642 negative control Substances 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000000160 oxazolidinyl group Chemical group 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 210000005134 plasmacytoid dendritic cell Anatomy 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 239000013641 positive control Substances 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 150000004944 pyrrolopyrimidines Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229950010550 resiquimod Drugs 0.000 description 1
- 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 description 1
- 238000005316 response function Methods 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 230000019491 signal transduction Effects 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
- SYXYWTXQFUUWLP-UHFFFAOYSA-N sodium;butan-1-olate Chemical compound [Na+].CCCC[O-] SYXYWTXQFUUWLP-UHFFFAOYSA-N 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- KUCOHFSKRZZVRO-UHFFFAOYSA-N terephthalaldehyde Chemical compound O=CC1=CC=C(C=O)C=C1 KUCOHFSKRZZVRO-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001984 thiazolidinyl group Chemical group 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 102000003390 tumor necrosis factor Human genes 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610082028.3A CN107043378A (zh) | 2016-02-05 | 2016-02-05 | 一种吡咯并[3,2-d]嘧啶类化合物的制备方法及其中间体 |
| PCT/CN2017/072893 WO2017133686A1 (zh) | 2016-02-05 | 2017-02-04 | 一种吡咯并[3,2-d]嘧啶类化合物的制备方法及其中间体 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA124100C2 true UA124100C2 (uk) | 2021-07-21 |
Family
ID=59500148
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UAA201809087A UA124100C2 (uk) | 2016-02-05 | 2017-02-04 | Спосіб одержання сполуки піроло[3,2-d]піримідину і проміжних сполук |
Country Status (28)
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|---|---|
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| EP (1) | EP3412673B1 (https=) |
| JP (1) | JP6877449B2 (https=) |
| KR (1) | KR102371500B1 (https=) |
| CN (2) | CN107043378A (https=) |
| AR (1) | AR107549A1 (https=) |
| AU (1) | AU2017214134B2 (https=) |
| BR (1) | BR112018015879B1 (https=) |
| CA (1) | CA3013520C (https=) |
| CL (1) | CL2018002094A1 (https=) |
| DK (1) | DK3412673T3 (https=) |
| EA (1) | EA034581B1 (https=) |
| ES (1) | ES2852323T3 (https=) |
| HR (1) | HRP20210103T1 (https=) |
| HU (1) | HUE053455T2 (https=) |
| IL (1) | IL260999B (https=) |
| LT (1) | LT3412673T (https=) |
| MX (1) | MX374298B (https=) |
| MY (1) | MY190551A (https=) |
| NZ (1) | NZ744885A (https=) |
| PH (1) | PH12018501642B1 (https=) |
| PL (1) | PL3412673T3 (https=) |
| PT (1) | PT3412673T (https=) |
| SG (1) | SG11201806685VA (https=) |
| SI (1) | SI3412673T1 (https=) |
| TW (1) | TW201728590A (https=) |
| UA (1) | UA124100C2 (https=) |
| WO (1) | WO2017133686A1 (https=) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN107043380A (zh) | 2016-02-05 | 2017-08-15 | 正大天晴药业集团股份有限公司 | 一种tlr7激动剂的马来酸盐、其晶型c、晶型d、晶型e、制备方法和用途 |
| MA44007A (fr) | 2016-02-05 | 2018-12-19 | Denali Therapeutics Inc | Inhibiteurs du récepteur interagissant avec protéine kinase 1 |
| JP7287708B2 (ja) | 2019-02-08 | 2023-06-06 | プロジェニア インコーポレイテッド | Ｔｏｌｌ－ｌｉｋｅ受容体７または８アゴニストとコレステロールの結合体およびその用途 |
| JP7811014B2 (ja) | 2020-03-02 | 2026-02-04 | プロジェニア インコーポレイテッド | 病原菌外壁成分基盤の生病原体模倣ナノ粒子及びその製造方法 |
| CN116322751A (zh) | 2020-08-04 | 2023-06-23 | 蛋白科技先锋 | 包含能够动力学控制的佐剂的mRNA疫苗 |
| JP2023536954A (ja) | 2020-08-04 | 2023-08-30 | プロジェニア インコーポレイテッド | 活性化部位が一時的に不活性化したトール様受容体７または８作用薬と機能性薬物の結合体およびその用途 |
| US20230355750A1 (en) | 2020-08-04 | 2023-11-09 | Progeneer Inc. | Kinetically acting adjuvant ensemble |
| IL314082A (en) | 2022-01-12 | 2024-09-01 | Denali Therapeutics Inc | Crystal forms of (S)-5-benzyl-N-(5-methyl-4-oxo-2,3,4,5-tetrahydropyrido[3,2-b][1,4]oxazapin-3-yl)- H4- 1,2,4-triazole-3-carboxamide |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009082247A1 (en) * | 2007-12-21 | 2009-07-02 | Industrial Research Limited | Process for preparing immucillins having a methylene link |
| ES2467108T3 (es) | 2008-12-09 | 2014-06-11 | Gilead Sciences, Inc. | Moduladores de receptores tipo toll |
| LT2906563T (lt) * | 2012-10-10 | 2018-06-11 | Janssen Sciences Ireland Uc | Pirolo[3,2-d]pirimidino dariniai virusinių infekcijų ir kitų ligų gydymui |
| MX358025B (es) * | 2012-11-20 | 2018-08-02 | Glaxosmithkline Llc Star | Compuestos novedosos. |
| US9550785B2 (en) * | 2012-11-20 | 2017-01-24 | Glaxosmithkline Llc | Pyrrolopyrimidines as therapeutic agents for the treatment of diseases |
| JP6484253B2 (ja) * | 2014-05-01 | 2019-03-13 | ノバルティス アーゲー | Ｔｏｌｌ様受容体７アゴニストとしての化合物および組成物 |
| CN105367576A (zh) | 2014-08-15 | 2016-03-02 | 正大天晴药业集团股份有限公司 | 作为tlr7激动剂的吡咯并嘧啶化合物 |
| HUE054672T2 (hu) | 2014-08-15 | 2021-09-28 | Chia Tai Tianqing Pharmaceutical Group Co Ltd | TLR7 agonistaként alkalmazott pirrolopirimidin vegyületek |
| CA3004173C (en) | 2015-11-05 | 2020-07-14 | Chia Tai Tianqing Pharmaceutical Group Co., Ltd. | 7-(thiazol-5-yl)pyrrolopyrimidine compound as tlr7 agonist |
| CN107043379A (zh) * | 2016-02-05 | 2017-08-15 | 正大天晴药业集团股份有限公司 | 一种tlr7激动剂的晶型a、其制备方法和医药用途 |
| CN107043380A (zh) * | 2016-02-05 | 2017-08-15 | 正大天晴药业集团股份有限公司 | 一种tlr7激动剂的马来酸盐、其晶型c、晶型d、晶型e、制备方法和用途 |
| CN107043377A (zh) * | 2016-02-05 | 2017-08-15 | 正大天晴药业集团股份有限公司 | 一种tlr7激动剂的三氟乙酸盐、晶型b及其制备方法、药物组合物和用途 |
-
2016
- 2016-02-05 CN CN201610082028.3A patent/CN107043378A/zh active Pending
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2017
- 2017-02-03 TW TW106103696A patent/TW201728590A/zh unknown
- 2017-02-04 CA CA3013520A patent/CA3013520C/en active Active
- 2017-02-04 AU AU2017214134A patent/AU2017214134B2/en active Active
- 2017-02-04 UA UAA201809087A patent/UA124100C2/uk unknown
- 2017-02-04 JP JP2018540720A patent/JP6877449B2/ja active Active
- 2017-02-04 SG SG11201806685VA patent/SG11201806685VA/en unknown
- 2017-02-04 LT LTEP17747006.9T patent/LT3412673T/lt unknown
- 2017-02-04 PT PT177470069T patent/PT3412673T/pt unknown
- 2017-02-04 US US16/075,300 patent/US10654856B2/en active Active
- 2017-02-04 WO PCT/CN2017/072893 patent/WO2017133686A1/zh not_active Ceased
- 2017-02-04 SI SI201730605T patent/SI3412673T1/sl unknown
- 2017-02-04 MY MYPI2018702701A patent/MY190551A/en unknown
- 2017-02-04 BR BR112018015879-8A patent/BR112018015879B1/pt active IP Right Grant
- 2017-02-04 PL PL17747006T patent/PL3412673T3/pl unknown
- 2017-02-04 NZ NZ744885A patent/NZ744885A/en unknown
- 2017-02-04 EA EA201891769A patent/EA034581B1/ru not_active IP Right Cessation
- 2017-02-04 CN CN201780009748.XA patent/CN108602832B/zh active Active
- 2017-02-04 HU HUE17747006A patent/HUE053455T2/hu unknown
- 2017-02-04 KR KR1020187024628A patent/KR102371500B1/ko active Active
- 2017-02-04 MX MX2018009502A patent/MX374298B/es active IP Right Grant
- 2017-02-04 ES ES17747006T patent/ES2852323T3/es active Active
- 2017-02-04 DK DK17747006.9T patent/DK3412673T3/da active
- 2017-02-04 EP EP17747006.9A patent/EP3412673B1/en active Active
- 2017-02-04 HR HRP20210103TT patent/HRP20210103T1/hr unknown
- 2017-02-06 AR ARP170100298A patent/AR107549A1/es active IP Right Grant
-
2018
- 2018-08-02 PH PH12018501642A patent/PH12018501642B1/en unknown
- 2018-08-03 CL CL2018002094A patent/CL2018002094A1/es unknown
- 2018-08-05 IL IL260999A patent/IL260999B/en active IP Right Grant
-
2020
- 2020-04-13 US US16/847,394 patent/US20200239484A1/en not_active Abandoned
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