HRP20210103T1 - Postupak za proizvodnju spoja pirol0[3,2-d]pirimidina, kao i odgovarajućih intermedijera - Google Patents
Postupak za proizvodnju spoja pirol0[3,2-d]pirimidina, kao i odgovarajućih intermedijera Download PDFInfo
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- HRP20210103T1 HRP20210103T1 HRP20210103TT HRP20210103T HRP20210103T1 HR P20210103 T1 HRP20210103 T1 HR P20210103T1 HR P20210103T T HRP20210103T T HR P20210103TT HR P20210103 T HRP20210103 T HR P20210103T HR P20210103 T1 HRP20210103 T1 HR P20210103T1
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- 238000000034 method Methods 0.000 title claims 13
- 239000000543 intermediate Substances 0.000 title 1
- -1 pyrrolo[3,2-d]pyrimidine compound Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 20
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims 12
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 6
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims 6
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 claims 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims 6
- 229910000027 potassium carbonate Inorganic materials 0.000 claims 6
- 235000011181 potassium carbonates Nutrition 0.000 claims 6
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 claims 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims 4
- 238000005906 dihydroxylation reaction Methods 0.000 claims 4
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 4
- 229910000029 sodium carbonate Inorganic materials 0.000 claims 4
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 claims 4
- AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 claims 4
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 claims 4
- 238000006243 chemical reaction Methods 0.000 claims 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 2
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 claims 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 2
- 235000011054 acetic acid Nutrition 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 claims 2
- 229910001863 barium hydroxide Inorganic materials 0.000 claims 2
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 claims 2
- 229910000024 caesium carbonate Inorganic materials 0.000 claims 2
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 claims 2
- 239000000920 calcium hydroxide Substances 0.000 claims 2
- 229910001861 calcium hydroxide Inorganic materials 0.000 claims 2
- 239000003638 chemical reducing agent Substances 0.000 claims 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical group 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 claims 2
- 239000000347 magnesium hydroxide Substances 0.000 claims 2
- 229910001862 magnesium hydroxide Inorganic materials 0.000 claims 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims 2
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 239000011736 potassium bicarbonate Substances 0.000 claims 2
- 229910000028 potassium bicarbonate Inorganic materials 0.000 claims 2
- 235000015497 potassium bicarbonate Nutrition 0.000 claims 2
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 claims 2
- 229910000160 potassium phosphate Inorganic materials 0.000 claims 2
- 235000011009 potassium phosphates Nutrition 0.000 claims 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims 2
- 235000017550 sodium carbonate Nutrition 0.000 claims 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 claims 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 claims 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims 1
- 235000015165 citric acid Nutrition 0.000 claims 1
- 235000019253 formic acid Nutrition 0.000 claims 1
- 239000001530 fumaric acid Substances 0.000 claims 1
- 235000011087 fumaric acid Nutrition 0.000 claims 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims 1
- 239000011976 maleic acid Substances 0.000 claims 1
- 239000001630 malic acid Substances 0.000 claims 1
- 235000011090 malic acid Nutrition 0.000 claims 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims 1
- 235000019260 propionic acid Nutrition 0.000 claims 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims 1
- 229960004889 salicylic acid Drugs 0.000 claims 1
- 239000012279 sodium borohydride Substances 0.000 claims 1
- 229910000033 sodium borohydride Inorganic materials 0.000 claims 1
Classifications
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- 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)
Claims (13)
1. Postupak za proizvodnju spoja formule I, naznačen time, da obuhvaća dehidroksiliranje spoja formule VI, u svrhu dobivanja spoja formule I:
[image]
gdje
R1 i R2 su neovisno odabrani iz skupine koju čini C1-4 alkil, ili
R1 i R2 zajedno s N atomom na koji se vežu, tvore 4-8-člani heterocikloaIkiI, pri čemu je heterocikloalkil opcionalno supstituiran s jednim ili više supstituenata neovisno odabranih iz skupine koju čine hidroksil, halogen, C1-4 alkil i C1-4 alkoksi.
2. Postupak prema patentnom zahtjevu 1, naznačen time, da obuhvaća sljedeće korake:
(a) reakciju spoja formule II sa spojem formule III u prisutnosti baze, u svrhu dobivanja spoja formule IV:
[image]
reakciju spoja formule IV sa spojem formule V u prisutnosti redukcijskog sredstva, u svrhu dobivanja spoja formule VI:
[image]
(b) dehidroksiliranje spoja formule VI, u svrhu dobivanja spoja formule I:
[image]
3. Postupak prema patentnom zahtjevu 2, naznačen time, da je baza u koraku (a) odabrana iz skupine koju čine natrijev karbonat, natrijev bikarbonat, kalijev karbonat, kalijev fosfat, kalijev bikarbonat, cezijev karbonat, litijev hidroksid, natrijev hidroksid, kalijev hidroksid, kalcijev hidroksid, magnezijev hidroksid, barijev hidroksid, natrijev metoksid, natrijev etoksid, natrijev t-butoksid, kalijev t-butoksid, trietilamin, diizopropiletilamin, piridin, N,N-dimetilaminopiridin, piperidin, N-metilpiperidin, morfolin, N-metilmorfolin i bilo koja njihova kombinacija, poželjno natrijev karbonat, kalijev karbonat, natrijev hidroksid, kalijev hidroksid i bilo koja njihova kombinacija, najpoželjnije kalijev karbonat.
4. Postupak prema patentnom zahtjevu 2 ili 3, naznačen time, da se korak (b) provodi u prisutnosti kiseline, primjerice kiselina se odabire iz skupine koju čine klorovodična kiselina, bromovodična kiselina, fosforna kiselina, sumporna kiselina, mravlja kiselina, octena kiselina, propionska kiselina, limunska kiselina, fumarna kiselina, jabučna kiselina, jantarna kiselina, salicilna kiselina, maleinska kiselina, trifluoroctena kiselina i bilo koja njihova kombinacija, poželjno octena kiselina.
5. Postupak prema bilo kojem od patentnih zahtjeva 2 do 4, naznačen time, da se redukcijsko sredstvo u koraku (b) odabire iz skupine koju čine BH3, NaBH4, NaBH3CN, NaBH(AcO)3 i bilo koja njihova kombinacija, poželjno NaBH(AcO)3.
6. Postupak prema bilo kojem od patentnih zahtjeva 2 do 5, naznačen time, da je spoj formule V odabran od:
[image]
[image]
7. Postupak prema patentnom zahtjevu 1, naznačen time, da postupak obuhvaća sljedeće korake:
(a') reakciju spoja formule II sa spojem formule III' u prisutnosti baze, u svrhu dobivanja spoja formule VI:
[image]
(b') dehidroksiliranje spoja formule VI, u svrhu dobivanja spoja formule I:
[image]
8. Postupak prema patentnom zahtjevu 7, naznačen time, da je baza u koraku (a') odabrana iz skupine koju čine natrijev karbonat, natrijev bikarbonat, kalijev karbonat, kalijev fosfat, kalijev bikarbonat, cezijev karbonat, litijev hidroksid, natrijev hidroksid, kalijev hidroksid, kalcijev hidroksid, magnezijev hidroksid, barijev hidroksid, natrijev metoksid, natrijev etoksid, natrijev t-butoksid, kalijev t-butoksid, trietilamin, diizopropiletilamin, piridin, N,N-dimetilaminopiridin, piperidin, N-metilpiperidin, morfolin, N-metilmorfolin i bilo koja njihova kombinacija, poželjno natrijev karbonat, kalijev karbonat, natrijev hidroksid, kalijev hidroksid i bilo koja njihova kombinacija, najpoželjnije kalijev karbonat.
9. Postupak prema bilo kojem od patentnih zahtjeva 1 do 8, naznačen time, da se dehidroksiliranje provodi u prisutnosti trietilsilana i trifluoroctene kiseline.
10. Postupak prema patentnom zahtjevu 9, naznačen time, da molarni omjer spoja formule VI prema trietilsilanu iznosi 1:1 ~ 10, poželjno 1:2 ~ 8, još poželjnije 1:5; a molarni omjer spoja formule VI prema trifluoroctenoj kiselini iznosi 1:2 ~ 20, poželjno 1:5 ~ 15, još poželjnije 1:10 ~ 12.
11. Postupak prema bilo kojem od patentnih zahtjeva 1 do 10, naznačen time, da se spoj formule I odabire od:
[image]
[image]
[image]
[image]
[image]
[image]
[image]
[image]
12. Spoj, naznačen time, da je predstavljen formulom VI:
[image]
u kojoj
R1 i R2 su neovisno odabrani iz skupine koju čini C1-4 alkil, ili
R1 i R2 zajedno s N atomom na koji se vežu, tvore 4-8-člani heterocikloaIkil, pri čemu je heterocikloalkil opcionalno supstituiran s jednim ili više supstituenata neovisno odabranih od hidroksila, halogena, C1-4 alkila i C1-4 alkoksi.
13. Spoj formule VI prema patentnom zahtjevu 12, naznačen time, da je odabran od:
[image]
[image]
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Applications Claiming Priority (3)
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 |
EP17747006.9A EP3412673B1 (en) | 2016-02-05 | 2017-02-04 | Method for preparing pyrrolo[3,2-d]pyrimidine compound, and intermediates thereof |
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 |
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HRP20210103T1 true HRP20210103T1 (hr) | 2021-03-05 |
Family
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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HRP20210103TT HRP20210103T1 (hr) | 2016-02-05 | 2021-01-21 | Postupak za proizvodnju spoja pirol0[3,2-d]pirimidina, kao i odgovarajućih intermedijera |
Country Status (29)
Country | Link |
---|---|
US (2) | US10654856B2 (hr) |
EP (1) | EP3412673B1 (hr) |
JP (1) | JP6877449B2 (hr) |
KR (1) | KR102371500B1 (hr) |
CN (2) | CN107043378A (hr) |
AR (1) | AR107549A1 (hr) |
AU (1) | AU2017214134B2 (hr) |
BR (1) | BR112018015879B1 (hr) |
CA (1) | CA3013520C (hr) |
CL (1) | CL2018002094A1 (hr) |
DK (1) | DK3412673T3 (hr) |
EA (1) | EA034581B1 (hr) |
ES (1) | ES2852323T3 (hr) |
HK (1) | HK1259183A1 (hr) |
HR (1) | HRP20210103T1 (hr) |
HU (1) | HUE053455T2 (hr) |
IL (1) | IL260999B (hr) |
LT (1) | LT3412673T (hr) |
MX (1) | MX2018009502A (hr) |
MY (1) | MY190551A (hr) |
NZ (1) | NZ744885A (hr) |
PH (1) | PH12018501642B1 (hr) |
PL (1) | PL3412673T3 (hr) |
PT (1) | PT3412673T (hr) |
SG (1) | SG11201806685VA (hr) |
SI (1) | SI3412673T1 (hr) |
TW (1) | TW201728590A (hr) |
UA (1) | UA124100C2 (hr) |
WO (1) | WO2017133686A1 (hr) |
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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 |
WO2020162705A1 (ko) | 2019-02-08 | 2020-08-13 | 성균관대학교산학협력단 | 톨-유사 수용체 7 또는 8 작용자와 콜레스테롤의 결합체 및 그 용도 |
WO2021177679A1 (ko) | 2020-03-02 | 2021-09-10 | 성균관대학교산학협력단 | 병원균 외벽 성분 기반 생병원체 모방 나노 입자 및 그 제조 방법 |
EP4194006A1 (en) | 2020-08-04 | 2023-06-14 | Progeneer Inc. | Mrna vaccine comprising adjuvant capable of kinetic control |
US20230277525A1 (en) | 2020-08-04 | 2023-09-07 | Progeneer Inc | Conjugate of functional drug and toll-like receptor 7 or 8 agonist of which active site is temporarily inactivated and use thereof |
WO2022031011A1 (ko) | 2020-08-04 | 2022-02-10 | 성균관대학교산학협력단 | 동력학적으로 작용하는 아주번트 앙상블 |
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WO2009082247A1 (en) | 2007-12-21 | 2009-07-02 | Industrial Research Limited | Process for preparing immucillins having a methylene link |
CN102272134B (zh) | 2008-12-09 | 2013-10-16 | 吉里德科学公司 | Toll样受体调节剂 |
ES2670513T3 (es) * | 2012-10-10 | 2018-05-30 | Janssen Sciences Ireland Uc | Derivados pirrolo[3,2-d]pirimidínicos para el tratamiento de infecciones víricas y otras enfermedades |
US9550785B2 (en) * | 2012-11-20 | 2017-01-24 | Glaxosmithkline Llc | Pyrrolopyrimidines as therapeutic agents for the treatment of diseases |
RS56233B1 (sr) * | 2012-11-20 | 2017-11-30 | Glaxosmithkline Llc | Nova jedinjenja |
PE20170325A1 (es) * | 2014-05-01 | 2017-04-21 | Novartis Ag | Compuestos y composiciones como agonistas del receptor tipo toll |
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 |
LT3190113T (lt) * | 2014-08-15 | 2021-08-25 | Chia Tai Tianqing Pharmaceutical Group Co., Ltd. | Pirolopirimidino junginiai, naudotini kaip tlr7 agonistai |
JP6524355B2 (ja) | 2015-11-05 | 2019-06-05 | チア タイ ティエンチン ファーマシューティカル グループ カンパニー リミテッドChia Tai Tianqing Pharmaceutical Group Co., Ltd. | Tlr7アゴニストとしての7−(チアゾール−5−イル)ピロロピリミジン化合物 |
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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 |
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