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
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- 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 (cg-RX-API-DMAC10.html) | 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)
Families Citing this family (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2871589C (en) | 2012-05-18 | 2020-12-22 | Seiji Hori | Pyrimidine carboxylic acid derivatives and their use as tlr7 agonists |
| JP6116782B1 (ja) | 2015-08-28 | 2017-04-19 | 積水メディカル株式会社 | ベンジル化合物 |
| HUE055079T2 (hu) * | 2015-10-07 | 2021-10-28 | Sumitomo Dainippon Pharma Co Ltd | Pirimidin vegyületek |
| WO2017142871A1 (en) * | 2016-02-15 | 2017-08-24 | 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 |
| CN109715617B (zh) | 2016-07-30 | 2022-04-19 | 百时美施贵宝公司 | 作为tlr7、tlr8或tlr9抑制剂的二甲氧基苯基取代的吲哚化合物 |
| ES2902504T3 (es) | 2016-09-09 | 2022-03-28 | Bristol Myers Squibb Co | Compuestos de indol sustituidos con piridilo |
| 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 |
| PL3603619T3 (pl) | 2017-03-29 | 2025-11-17 | Sumitomo Pharma Co., Ltd. | Preparat adjuwantu szczepionkowego |
| CN110997670B (zh) | 2017-08-04 | 2022-11-01 | 百时美施贵宝公司 | [1,2,4]三唑并[4,3-a]吡啶基取代的吲哚化合物 |
| EP3661926B1 (en) | 2017-08-04 | 2022-02-23 | Bristol-Myers Squibb Company | Substituted indole compounds useful as inhibitors of tlr7/8/9 |
| CN111448190B (zh) | 2017-11-14 | 2023-09-26 | 百时美施贵宝公司 | 取代的吲哚化合物 |
| US12030878B2 (en) | 2017-12-15 | 2024-07-09 | Bristol-Myers Squibb Company | Substituted indole ether compounds |
| MX2020006168A (es) | 2017-12-18 | 2020-08-13 | Bristol Myers Squibb Co | Compuestos de 4-azaindol. |
| WO2019126081A1 (en) | 2017-12-19 | 2019-06-27 | Bristol-Myers Squibb Company | Amide substituted indole compounds useful as tlr inhibitors |
| EP3728253B1 (en) | 2017-12-19 | 2024-03-27 | Bristol-Myers Squibb Company | 6-azaindole compounds |
| EA202091474A1 (ru) | 2017-12-19 | 2020-11-18 | Бристол-Маерс Сквибб Компани | Замещенные индольные соединения, применимые в качестве ингибиторов tlr |
| EA202091530A1 (ru) | 2017-12-20 | 2020-09-14 | Бристол-Маерс Сквибб Компани | Диазаиндольные соединения |
| JP7287967B2 (ja) | 2017-12-20 | 2023-06-06 | ブリストル－マイヤーズ スクイブ カンパニー | Ｔｌｒ阻害剤として有効なアミノインドール化合物 |
| KR102730859B1 (ko) | 2017-12-20 | 2024-11-15 | 브리스톨-마이어스 스큅 컴퍼니 | 아릴 및 헤테로아릴 치환된 인돌 화합물 |
| RU2020124007A (ru) * | 2017-12-21 | 2022-01-21 | Сумитомо Дайниппон Фарма Ко., Лтд. | Комбинированный препарат, включающий агонист tlr7 |
| JP7351859B2 (ja) * | 2018-06-04 | 2023-09-27 | アプロス セラピューティクス， インコーポレイテッド | Ｔｌｒ７の調節に関係する疾患を処置するのに有用な酸性基を含むピリミジン化合物 |
| AU2019311965B2 (en) | 2018-07-23 | 2026-02-19 | Japan Institute For Health Security | Composition containing influenza vaccine |
| ES2963696T3 (es) | 2018-10-24 | 2024-04-01 | Bristol Myers Squibb Co | Compuestos diméricos de indol sustituidos |
| US12172995B2 (en) | 2018-10-24 | 2024-12-24 | Bristol-Myers Squibb Company | Substituted indole and indazole compounds |
| BR112021015577A2 (pt) | 2019-02-08 | 2021-10-05 | Research & Business Foundation Sungkyunkwan University | Complexo-colesterol agonista do receptor toll-like 7 ou 8 e uso do mesmo |
| KR102904576B1 (ko) | 2019-05-09 | 2025-12-24 | 브리스톨-마이어스 스큅 컴퍼니 | 치환된 벤즈이미다졸론 화합물 |
| WO2021067326A1 (en) | 2019-10-01 | 2021-04-08 | Bristol-Myers Squibb Company | Substituted bicyclic heteroaryl compounds |
| CN114829350B (zh) | 2019-10-04 | 2024-05-28 | 百时美施贵宝公司 | 经取代的咔唑化合物 |
| CN115666637A (zh) | 2020-03-02 | 2023-01-31 | 蛋白科技先锋 | 基于病原体细胞壁骨架的模拟活病原体的纳米粒子及其制备方法 |
| 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 |
| WO2022031021A1 (ko) | 2020-08-04 | 2022-02-10 | 성균관대학교산학협력단 | 동력학적 제어가 가능한 아주번트를 포함하는 mrna 백신 |
| EP4194008A4 (en) | 2020-08-04 | 2025-01-08 | Progeneer Inc. | Kinetically acting adjuvant ensemble |
| WO2022202814A1 (ja) * | 2021-03-23 | 2022-09-29 | 住友ファーマ株式会社 | ピリミジン化合物の製造方法 |
| WO2025110816A1 (ko) | 2023-11-23 | 2025-05-30 | 프로지니어 주식회사 | 암의 치료를 위한 활성화 부위가 일시적으로 비활성화된 톨-유사 수용체 7 또는 8 작용자와 항암 치료의 병용요법 |
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