JP2015520729A5 - - Google Patents
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- Publication number
- JP2015520729A5 JP2015520729A5 JP2014555888A JP2014555888A JP2015520729A5 JP 2015520729 A5 JP2015520729 A5 JP 2015520729A5 JP 2014555888 A JP2014555888 A JP 2014555888A JP 2014555888 A JP2014555888 A JP 2014555888A JP 2015520729 A5 JP2015520729 A5 JP 2015520729A5
- Authority
- JP
- Japan
- Prior art keywords
- amino
- alkyl
- pharmaceutically acceptable
- acceptable salt
- methylpyrimidin
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 150000003839 salts Chemical class 0.000 claims description 33
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 229910052760 oxygen Inorganic materials 0.000 claims description 17
- 125000005842 heteroatom Chemical group 0.000 claims description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
- 239000001301 oxygen Substances 0.000 claims description 10
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 125000000623 heterocyclic group Chemical group 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 229920006395 saturated elastomer Polymers 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 5
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 4
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims 31
- 239000003814 drug Substances 0.000 claims 5
- 206010028980 Neoplasm Diseases 0.000 claims 4
- 239000004480 active ingredient Substances 0.000 claims 4
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 3
- 101000669402 Homo sapiens Toll-like receptor 7 Proteins 0.000 claims 3
- 102100039390 Toll-like receptor 7 Human genes 0.000 claims 3
- 201000011510 cancer Diseases 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 230000001404 mediated effect Effects 0.000 claims 3
- 125000006239 protecting group Chemical group 0.000 claims 3
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 2
- 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 claims 2
- NZMIALRJUDGDME-UHFFFAOYSA-N CCCC(CCO)Nc1nc(N)nc(C)c1Cc1ccc(CN(CC(F)F)CC(O)=O)cc1OC Chemical compound CCCC(CCO)Nc1nc(N)nc(C)c1Cc1ccc(CN(CC(F)F)CC(O)=O)cc1OC NZMIALRJUDGDME-UHFFFAOYSA-N 0.000 claims 2
- XWGKZKKNJOQUSG-UHFFFAOYSA-N CCCC(CCO)Nc1nc(N)nc(C)c1Cc1ccc(CN(CC(O)=O)CC(F)(F)F)cc1OC Chemical compound CCCC(CCO)Nc1nc(N)nc(C)c1Cc1ccc(CN(CC(O)=O)CC(F)(F)F)cc1OC XWGKZKKNJOQUSG-UHFFFAOYSA-N 0.000 claims 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 2
- OZVFUUXGCDMGIG-UHFFFAOYSA-N 2-[3-[4-[[2-amino-4-(1-hydroxyhexan-3-ylamino)-6-methylpyrimidin-5-yl]methyl]-3-methoxyphenoxy]propyl-(2,2-difluoroethyl)amino]acetic acid Chemical compound CCCC(CCO)NC1=NC(N)=NC(C)=C1CC1=CC=C(OCCCN(CC(F)F)CC(O)=O)C=C1OC OZVFUUXGCDMGIG-UHFFFAOYSA-N 0.000 claims 1
- ANCBWBFMSIQTEX-UHFFFAOYSA-N 2-[[4-[[2-amino-4-(1-hydroxyhexan-3-ylamino)-6-methylpyrimidin-5-yl]methyl]-3-methoxyphenyl]methyl-ethylamino]acetic acid Chemical compound CCCC(CCO)NC1=NC(N)=NC(C)=C1CC1=CC=C(CN(CC)CC(O)=O)C=C1OC ANCBWBFMSIQTEX-UHFFFAOYSA-N 0.000 claims 1
- ZXPNPUZYBKVZFN-UHFFFAOYSA-N 2-[[4-[[2-amino-4-(butylamino)-6-methylpyrimidin-5-yl]methyl]-3-methoxyphenyl]methyl-ethylamino]acetic acid Chemical compound CCCCNC1=NC(N)=NC(C)=C1CC1=CC=C(CN(CC)CC(O)=O)C=C1OC ZXPNPUZYBKVZFN-UHFFFAOYSA-N 0.000 claims 1
- XWGKZKKNJOQUSG-SFHVURJKSA-N 2-[[4-[[2-amino-4-[[(3s)-1-hydroxyhexan-3-yl]amino]-6-methylpyrimidin-5-yl]methyl]-3-methoxyphenyl]methyl-(2,2,2-trifluoroethyl)amino]acetic acid Chemical compound CCC[C@@H](CCO)NC1=NC(N)=NC(C)=C1CC1=CC=C(CN(CC(O)=O)CC(F)(F)F)C=C1OC XWGKZKKNJOQUSG-SFHVURJKSA-N 0.000 claims 1
- NZMIALRJUDGDME-SFHVURJKSA-N 2-[[4-[[2-amino-4-[[(3s)-1-hydroxyhexan-3-yl]amino]-6-methylpyrimidin-5-yl]methyl]-3-methoxyphenyl]methyl-(2,2-difluoroethyl)amino]acetic acid Chemical compound CCC[C@@H](CCO)NC1=NC(N)=NC(C)=C1CC1=CC=C(CN(CC(F)F)CC(O)=O)C=C1OC NZMIALRJUDGDME-SFHVURJKSA-N 0.000 claims 1
- FIMNMHMOKYVGGK-UHFFFAOYSA-N 2-[acetyl-[[4-[[2-amino-4-(1-hydroxyhexan-3-ylamino)-6-methylpyrimidin-5-yl]methyl]-3-methoxyphenyl]methyl]amino]acetic acid Chemical compound CCCC(CCO)NC1=NC(N)=NC(C)=C1CC1=CC=C(CN(CC(O)=O)C(C)=O)C=C1OC FIMNMHMOKYVGGK-UHFFFAOYSA-N 0.000 claims 1
- -1 2-monofluoroethyl Chemical group 0.000 claims 1
- VLBOFYFPALJWKB-UHFFFAOYSA-N 3-[3-[4-[[2-amino-4-(1-hydroxyhexan-3-ylamino)-6-methylpyrimidin-5-yl]methyl]-3-methoxyphenoxy]propyl-ethylamino]propanoic acid Chemical compound CCCC(CCO)NC1=NC(N)=NC(C)=C1CC1=CC=C(OCCCN(CC)CCC(O)=O)C=C1OC VLBOFYFPALJWKB-UHFFFAOYSA-N 0.000 claims 1
- WKSQSVJHSIYNRQ-UHFFFAOYSA-N 3-[[4-[[2-amino-4-(1-hydroxyhexan-3-ylamino)-6-methylpyrimidin-5-yl]methyl]-3-methoxyphenyl]methyl-ethylamino]propanoic acid Chemical compound CCCC(CCO)NC1=NC(N)=NC(C)=C1CC1=CC=C(CN(CC)CCC(O)=O)C=C1OC WKSQSVJHSIYNRQ-UHFFFAOYSA-N 0.000 claims 1
- CTZXFKZRJMILBC-UHFFFAOYSA-N 3-[[4-[[2-amino-4-(1-hydroxyhexan-3-ylamino)-6-methylpyrimidin-5-yl]methyl]-3-methoxyphenyl]methyl]imidazole-4-carboxylic acid Chemical compound CCCC(CCO)NC1=NC(N)=NC(C)=C1CC(C(=C1)OC)=CC=C1CN1C(C(O)=O)=CN=C1 CTZXFKZRJMILBC-UHFFFAOYSA-N 0.000 claims 1
- 208000015898 Bacterial Skin disease Diseases 0.000 claims 1
- 208000035143 Bacterial infection Diseases 0.000 claims 1
- 206010005003 Bladder cancer Diseases 0.000 claims 1
- 208000003174 Brain Neoplasms Diseases 0.000 claims 1
- 206010006187 Breast cancer Diseases 0.000 claims 1
- 208000026310 Breast neoplasm Diseases 0.000 claims 1
- ZSLUPNMTHNULTB-UHFFFAOYSA-N CCCC(CCO)Nc1nc(N)nc(C)c1Cc1ccc(CN(CCC(O)=O)CC(F)F)cc1OC Chemical compound CCCC(CCO)Nc1nc(N)nc(C)c1Cc1ccc(CN(CCC(O)=O)CC(F)F)cc1OC ZSLUPNMTHNULTB-UHFFFAOYSA-N 0.000 claims 1
- SPPCRMFPGSSTAD-UHFFFAOYSA-N CCCC(CCO)Nc1nc(N)nc(C)c1Cc1ccc(CN2CCCC2C(O)=O)cc1OC Chemical compound CCCC(CCO)Nc1nc(N)nc(C)c1Cc1ccc(CN2CCCC2C(O)=O)cc1OC SPPCRMFPGSSTAD-UHFFFAOYSA-N 0.000 claims 1
- QZFXSCDMRRGGHK-UHFFFAOYSA-N CCCC(CCO)Nc1nc(N)nc(C)c1Cc1ccc(OCCCN(CC)CC(O)=O)cc1OC Chemical compound CCCC(CCO)Nc1nc(N)nc(C)c1Cc1ccc(OCCCN(CC)CC(O)=O)cc1OC QZFXSCDMRRGGHK-UHFFFAOYSA-N 0.000 claims 1
- RAOIMTPEPSLKEC-UHFFFAOYSA-N CCCC(CCO)Nc1nc(N)nc(C)c1Cc1ccc(OCCCN2CCCC2C(O)=O)cc1OC Chemical compound CCCC(CCO)Nc1nc(N)nc(C)c1Cc1ccc(OCCCN2CCCC2C(O)=O)cc1OC RAOIMTPEPSLKEC-UHFFFAOYSA-N 0.000 claims 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 1
- 206010009944 Colon cancer Diseases 0.000 claims 1
- 206010010744 Conjunctivitis allergic Diseases 0.000 claims 1
- 206010012438 Dermatitis atopic Diseases 0.000 claims 1
- 208000005176 Hepatitis C Diseases 0.000 claims 1
- 208000022361 Human papillomavirus infectious disease Diseases 0.000 claims 1
- 208000008839 Kidney Neoplasms Diseases 0.000 claims 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 1
- 206010033128 Ovarian cancer Diseases 0.000 claims 1
- 206010061535 Ovarian neoplasm Diseases 0.000 claims 1
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims 1
- 206010035226 Plasma cell myeloma Diseases 0.000 claims 1
- 206010060862 Prostate cancer Diseases 0.000 claims 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 1
- 206010038389 Renal cancer Diseases 0.000 claims 1
- 206010039085 Rhinitis allergic Diseases 0.000 claims 1
- 208000000453 Skin Neoplasms Diseases 0.000 claims 1
- 208000005718 Stomach Neoplasms Diseases 0.000 claims 1
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims 1
- 208000002495 Uterine Neoplasms Diseases 0.000 claims 1
- 208000002205 allergic conjunctivitis Diseases 0.000 claims 1
- 201000010105 allergic rhinitis Diseases 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 208000024998 atopic conjunctivitis Diseases 0.000 claims 1
- 201000008937 atopic dermatitis Diseases 0.000 claims 1
- 208000022362 bacterial infectious disease Diseases 0.000 claims 1
- 239000012830 cancer therapeutic Substances 0.000 claims 1
- 208000029742 colonic neoplasm Diseases 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 206010017758 gastric cancer Diseases 0.000 claims 1
- 201000010536 head and neck cancer Diseases 0.000 claims 1
- 208000014829 head and neck neoplasm Diseases 0.000 claims 1
- 208000002672 hepatitis B Diseases 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 201000010982 kidney cancer Diseases 0.000 claims 1
- 201000007270 liver cancer Diseases 0.000 claims 1
- 208000014018 liver neoplasm Diseases 0.000 claims 1
- 201000005202 lung cancer Diseases 0.000 claims 1
- 208000020816 lung neoplasm Diseases 0.000 claims 1
- 230000001589 lymphoproliferative effect Effects 0.000 claims 1
- 230000003211 malignant effect Effects 0.000 claims 1
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims 1
- 201000000050 myeloid neoplasm Diseases 0.000 claims 1
- 201000002528 pancreatic cancer Diseases 0.000 claims 1
- 208000008443 pancreatic carcinoma Diseases 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
- 201000000849 skin cancer Diseases 0.000 claims 1
- 201000011549 stomach cancer Diseases 0.000 claims 1
- 229940124597 therapeutic agent Drugs 0.000 claims 1
- 201000005112 urinary bladder cancer Diseases 0.000 claims 1
- 206010046766 uterine cancer Diseases 0.000 claims 1
- 0 CCC(C)(C)CC(C)(C)C(*)N Chemical compound CCC(C)(C)CC(C)(C)C(*)N 0.000 description 2
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261648816P | 2012-05-18 | 2012-05-18 | |
| US61/648,816 | 2012-05-18 | ||
| US201361806158P | 2013-03-28 | 2013-03-28 | |
| US61/806,158 | 2013-03-28 | ||
| PCT/JP2013/064420 WO2013172479A1 (en) | 2012-05-18 | 2013-05-17 | Carboxylic acid compounds |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2015520729A JP2015520729A (ja) | 2015-07-23 |
| JP2015520729A5 true JP2015520729A5 (enExample) | 2016-06-30 |
| JP6184423B2 JP6184423B2 (ja) | 2017-08-23 |
Family
ID=49583875
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014555888A Active JP6184423B2 (ja) | 2012-05-18 | 2013-05-17 | カルボン酸化合物 |
Country Status (17)
| Country | Link |
|---|---|
| US (5) | US9376398B2 (enExample) |
| EP (1) | EP2850067B1 (enExample) |
| JP (1) | JP6184423B2 (enExample) |
| KR (1) | KR102194585B1 (enExample) |
| CN (1) | CN104302628B (enExample) |
| AU (1) | AU2013261267B2 (enExample) |
| BR (1) | BR112014029261A2 (enExample) |
| CA (1) | CA2871589C (enExample) |
| DK (1) | DK2850067T3 (enExample) |
| ES (1) | ES2644702T3 (enExample) |
| MX (1) | MX2014014031A (enExample) |
| MY (1) | MY178053A (enExample) |
| PH (1) | PH12014502524B1 (enExample) |
| RU (1) | RU2636146C2 (enExample) |
| SG (1) | SG11201407115XA (enExample) |
| TW (1) | TWI619704B (enExample) |
| WO (1) | WO2013172479A1 (enExample) |
Families Citing this family (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MY178053A (en) | 2012-05-18 | 2020-09-30 | Sumitomo Dainippon Pharma Co Ltd | Carboxylic acid compounds |
| US10822357B2 (en) | 2015-08-28 | 2020-11-03 | Sekisui Medical Co., Ltd. | Benzyl compound |
| CA3001283C (en) * | 2015-10-07 | 2023-10-10 | Sumitomo Dainippon Pharma Co., Ltd. | Pyrimidine compound |
| EP4071174A1 (en) * | 2016-02-15 | 2022-10-12 | AstraZeneca AB | Methods comprising fixed intermittent dosing of cediranib |
| US10071079B2 (en) | 2016-06-29 | 2018-09-11 | Bristol-Myers Squibb Company | [1,2,4]triazolo[1,5-a]pyridinyl substituted indole compounds |
| CA3031675A1 (en) | 2016-07-30 | 2018-02-08 | Bristol-Myers Squibb Company | Dimethoxyphenyl substituted indole compounds as tlr7, tlr8 or tlr9 inhibitors |
| WO2018049089A1 (en) | 2016-09-09 | 2018-03-15 | Bristol-Myers Squibb Company | Pyridyl substituted indole compounds |
| WO2018106606A1 (en) * | 2016-12-05 | 2018-06-14 | Apros Therapeutics, Inc. | Pyrimidine compounds containing acidic groups |
| US10786502B2 (en) | 2016-12-05 | 2020-09-29 | Apros Therapeutics, Inc. | Substituted pyrimidines containing acidic groups as TLR7 modulators |
| US11253476B2 (en) | 2017-03-29 | 2022-02-22 | Sumitomo Dainippon Pharma Co., Ltd. | Vaccine adjuvant formulation |
| JP7266576B2 (ja) | 2017-08-04 | 2023-04-28 | ブリストル－マイヤーズ スクイブ カンパニー | ［１，２，４］トリアゾロ［４，３－ａ］ピリジニル置換のインドール化合物 |
| JP7104775B2 (ja) | 2017-08-04 | 2022-07-21 | ブリストル－マイヤーズ スクイブ カンパニー | Ｔｌｒ７／８／９の阻害剤として有用な置換インドール化合物 |
| WO2019099336A1 (en) | 2017-11-14 | 2019-05-23 | Bristol-Myers Squibb Company | Substituted indole compounds |
| KR102781141B1 (ko) | 2017-12-15 | 2025-03-13 | 브리스톨-마이어스 스큅 컴퍼니 | 치환된 인돌 에테르 화합물 |
| LT3728252T (lt) | 2017-12-18 | 2023-10-25 | Bristol-Myers Squibb Company | 4-azaindolo junginiai |
| SG11202005704RA (en) | 2017-12-19 | 2020-07-29 | Bristol Myers Squibb Co | 6-azaindole compounds |
| SG11202005700SA (en) | 2017-12-19 | 2020-07-29 | Bristol Myers Squibb Co | Amide substituted indole compounds useful as tlr inhibitors |
| AU2018390820A1 (en) | 2017-12-19 | 2020-08-06 | Bristol-Myers Squibb Company | Substituted indole compounds useful as TLR inhibitors |
| BR112020011984A2 (pt) | 2017-12-20 | 2020-11-17 | Bristol-Myers Squibb Company | compostos de amino indol úteis como inibidores de tlr |
| KR102730859B1 (ko) | 2017-12-20 | 2024-11-15 | 브리스톨-마이어스 스큅 컴퍼니 | 아릴 및 헤테로아릴 치환된 인돌 화합물 |
| ES2904773T3 (es) | 2017-12-20 | 2022-04-06 | Bristol Myers Squibb Co | Compuestos de diazaindol |
| SG11202005535UA (en) * | 2017-12-21 | 2020-07-29 | Sumitomo Dainippon Pharma Co Ltd | Combination drug including tlr7 agonist |
| WO2019236496A1 (en) * | 2018-06-04 | 2019-12-12 | Apros Therapeutics, Inc. | Pyrimidine compounds containing acidic groups useful to treat diseases connected to the modulation of tlr7 |
| US12059462B2 (en) | 2018-07-23 | 2024-08-13 | Japan As Represented By Director General Of National Institute Of Infectious Diseases | Composition containing influenza vaccine |
| CN112955450A (zh) | 2018-10-24 | 2021-06-11 | 百时美施贵宝公司 | 经取代的吲哚和吲唑化合物 |
| KR20210080462A (ko) | 2018-10-24 | 2021-06-30 | 브리스톨-마이어스 스큅 컴퍼니 | 치환된 인돌 이량체 화합물 |
| 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 |
| WO2020227484A1 (en) | 2019-05-09 | 2020-11-12 | Bristol-Myers Squibb Company | Substituted benzimidazolone compounds |
| WO2021067326A1 (en) | 2019-10-01 | 2021-04-08 | Bristol-Myers Squibb Company | Substituted bicyclic heteroaryl compounds |
| EP4038059B1 (en) | 2019-10-04 | 2023-09-20 | Bristol-Myers Squibb Company | Substituted carbazole compounds |
| JP2023516372A (ja) | 2020-03-02 | 2023-04-19 | 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 |
| WO2022031057A1 (ko) | 2020-08-04 | 2022-02-10 | 성균관대학교산학협력단 | 활성화 부위가 일시적으로 비활성화된 톨-유사 수용체 7 또는 8 작용자와 기능성 약물의 결합체 및 그 용도 |
| EP4194006A4 (en) | 2020-08-04 | 2024-12-04 | Progeneer Inc. | mRNA VACCINE WITH AN ADJUVANT CAPABLE OF KINETIC CONTROL |
| US20230355750A1 (en) | 2020-08-04 | 2023-11-09 | Progeneer Inc. | Kinetically acting adjuvant ensemble |
| JPWO2022202814A1 (enExample) * | 2021-03-23 | 2022-09-29 |
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-
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- 2013-05-17 MY MYPI2014703361A patent/MY178053A/en unknown
- 2013-05-17 KR KR1020147035540A patent/KR102194585B1/ko active Active
- 2013-05-17 WO PCT/JP2013/064420 patent/WO2013172479A1/en not_active Ceased
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- 2013-05-17 BR BR112014029261A patent/BR112014029261A2/pt not_active IP Right Cessation
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