JP2013527142A5 - - Google Patents
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- JP2013527142A5 JP2013527142A5 JP2013501437A JP2013501437A JP2013527142A5 JP 2013527142 A5 JP2013527142 A5 JP 2013527142A5 JP 2013501437 A JP2013501437 A JP 2013501437A JP 2013501437 A JP2013501437 A JP 2013501437A JP 2013527142 A5 JP2013527142 A5 JP 2013527142A5
- Authority
- JP
- Japan
- Prior art keywords
- amino
- acid
- thia
- alkyl
- thio
- 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.)
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- 150000001875 compounds Chemical class 0.000 claims description 22
- 206010028980 Neoplasm Diseases 0.000 claims description 5
- 201000011510 cancer Diseases 0.000 claims description 5
- -1 wherein Chemical group 0.000 claims 96
- 239000002253 acid Substances 0.000 claims 46
- 125000000217 alkyl group Chemical group 0.000 claims 30
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims 29
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 29
- 125000003118 aryl group Chemical group 0.000 claims 11
- 150000003839 salts Chemical class 0.000 claims 9
- 229910052799 carbon Inorganic materials 0.000 claims 8
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 8
- 125000006832 (C1-C10) alkylene group Chemical group 0.000 claims 7
- 125000005842 heteroatom Chemical group 0.000 claims 7
- 229910052757 nitrogen Inorganic materials 0.000 claims 7
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 6
- 125000004432 carbon atom Chemical group C* 0.000 claims 6
- 201000010099 disease Diseases 0.000 claims 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 4
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims 4
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims 4
- 208000011341 adult acute respiratory distress syndrome Diseases 0.000 claims 4
- 201000000028 adult respiratory distress syndrome Diseases 0.000 claims 4
- 125000005843 halogen group Chemical group 0.000 claims 4
- 125000001072 heteroaryl group Chemical group 0.000 claims 4
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 4
- 229910052760 oxygen Inorganic materials 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 229910052717 sulfur Inorganic materials 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 2
- 206010004146 Basal cell carcinoma Diseases 0.000 claims 2
- 206010006187 Breast cancer Diseases 0.000 claims 2
- 208000026310 Breast neoplasm Diseases 0.000 claims 2
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 2
- 206010009900 Colitis ulcerative Diseases 0.000 claims 2
- 208000035473 Communicable disease Diseases 0.000 claims 2
- 208000011231 Crohn disease Diseases 0.000 claims 2
- 201000004624 Dermatitis Diseases 0.000 claims 2
- 201000004681 Psoriasis Diseases 0.000 claims 2
- 206010039085 Rhinitis allergic Diseases 0.000 claims 2
- 206010039710 Scleroderma Diseases 0.000 claims 2
- 208000012658 Skin autoimmune disease Diseases 0.000 claims 2
- 102000008228 Toll-like receptor 2 Human genes 0.000 claims 2
- 108010060888 Toll-like receptor 2 Proteins 0.000 claims 2
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 2
- 208000024780 Urticaria Diseases 0.000 claims 2
- 208000009621 actinic keratosis Diseases 0.000 claims 2
- 201000010105 allergic rhinitis Diseases 0.000 claims 2
- 208000006673 asthma Diseases 0.000 claims 2
- 206010006451 bronchitis Diseases 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 208000015181 infectious disease Diseases 0.000 claims 2
- 208000027866 inflammatory disease Diseases 0.000 claims 2
- 206010025135 lupus erythematosus Diseases 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 201000006417 multiple sclerosis Diseases 0.000 claims 2
- 208000023504 respiratory system disease Diseases 0.000 claims 2
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 2
- 208000017520 skin disease Diseases 0.000 claims 2
- 125000006708 (C5-C14) heteroaryl group Chemical group 0.000 claims 1
- RNROZPSWLBMWPE-XDSPJLLDSA-N 10-[[(2r)-2-amino-3-[(2r)-2,3-di(dodecanoyloxy)propyl]sulfanylpropanoyl]amino]decanoic acid Chemical compound CCCCCCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCCCCCC)CSC[C@H](N)C(=O)NCCCCCCCCCC(O)=O RNROZPSWLBMWPE-XDSPJLLDSA-N 0.000 claims 1
- AVJXIKLAXVAVJL-XDSPJLLDSA-N 2-[2-[2-[2-[[(2r)-2-amino-3-[(2r)-2-(dodecanoylamino)-3-dodecoxypropyl]sulfanylpropanoyl]amino]ethoxy]ethoxy]ethoxy]ethylphosphonic acid Chemical compound CCCCCCCCCCCCOC[C@@H](NC(=O)CCCCCCCCCCC)CSC[C@H](N)C(=O)NCCOCCOCCOCCP(O)(O)=O AVJXIKLAXVAVJL-XDSPJLLDSA-N 0.000 claims 1
- CXTMUHYINLGHIJ-PDHQKIGBSA-N 2-[2-[2-[[(2s)-2-[[(2r)-2-amino-3-[(2r)-2-(dodecanoylamino)-3-dodecoxypropyl]sulfanylpropanoyl]amino]propanoyl]amino]ethoxy]ethoxy]ethylphosphonic acid Chemical compound CCCCCCCCCCCCOC[C@@H](NC(=O)CCCCCCCCCCC)CSC[C@H](N)C(=O)N[C@@H](C)C(=O)NCCOCCOCCP(O)(O)=O CXTMUHYINLGHIJ-PDHQKIGBSA-N 0.000 claims 1
- OWYSSBCQPFLCKM-SAIUNTKASA-N 3-[2-[2-[2-[[(2r)-2-amino-3-[(2r)-2,3-bis(decylcarbamoyloxy)propyl]sulfanylpropanoyl]amino]ethoxy]ethoxy]ethoxy]propanoic acid Chemical compound CCCCCCCCCCNC(=O)OC[C@@H](OC(=O)NCCCCCCCCCC)CSC[C@H](N)C(=O)NCCOCCOCCOCCC(O)=O OWYSSBCQPFLCKM-SAIUNTKASA-N 0.000 claims 1
- PBBVIJOYGHFWPR-GPOMZPHUSA-N 3-[2-[2-[2-[[(2r)-2-amino-3-[(2r)-2,3-di(dodecanoyloxy)propyl]sulfanylpropanoyl]amino]ethoxy]ethoxy]ethoxy]propanoic acid Chemical compound CCCCCCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCCCCCC)CSC[C@H](N)C(=O)NCCOCCOCCOCCC(O)=O PBBVIJOYGHFWPR-GPOMZPHUSA-N 0.000 claims 1
- KNSLGSFUKSVBCY-AARKOHAPSA-N 3-[2-[2-[2-[[(2r)-2-amino-3-[(2r)-2,3-didodecoxypropyl]sulfanylpropanoyl]amino]ethoxy]ethoxy]ethoxy]propanoic acid Chemical compound CCCCCCCCCCCCOC[C@@H](OCCCCCCCCCCCC)CSC[C@H](N)C(=O)NCCOCCOCCOCCC(O)=O KNSLGSFUKSVBCY-AARKOHAPSA-N 0.000 claims 1
- AKDQYJWOQJRVEJ-XDSPJLLDSA-N 3-[2-[2-[2-[[(2r)-2-amino-3-[(2r)-2-(dodecanoylamino)-3-dodecoxypropyl]sulfanylpropanoyl]amino]ethoxy]ethoxy]ethoxy]propanoic acid Chemical compound CCCCCCCCCCCCOC[C@@H](NC(=O)CCCCCCCCCCC)CSC[C@H](N)C(=O)NCCOCCOCCOCCC(O)=O AKDQYJWOQJRVEJ-XDSPJLLDSA-N 0.000 claims 1
- IPNXWVGUWKZJCP-IHLOFXLRSA-N 3-[[(2r)-2-amino-3-[(2r)-2,3-di(dodecanoyloxy)propyl]sulfanylpropanoyl]amino]propane-1-sulfonic acid Chemical compound CCCCCCCCCCCC(=O)OC[C@H](CSC[C@H](N)C(=O)NCCCS(O)(=O)=O)OC(=O)CCCCCCCCCCC IPNXWVGUWKZJCP-IHLOFXLRSA-N 0.000 claims 1
- OFHIDHOBIKLOEQ-IHLOFXLRSA-N 3-[[(2r)-2-amino-3-[(2r)-2,3-di(dodecanoyloxy)propyl]sulfanylpropanoyl]amino]propylphosphonic acid Chemical compound CCCCCCCCCCCC(=O)OC[C@H](CSC[C@H](N)C(=O)NCCCP(O)(O)=O)OC(=O)CCCCCCCCCCC OFHIDHOBIKLOEQ-IHLOFXLRSA-N 0.000 claims 1
- MOJCWSMGIRIAQB-SAIUNTKASA-N 3-[[1-[[(2r)-2-amino-3-[(2r)-2,3-di(dodecanoyloxy)propyl]sulfanylpropanoyl]amino]cyclopropyl]methoxy]propylphosphonic acid Chemical compound CCCCCCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCCCCCC)CSC[C@H](N)C(=O)NC1(COCCCP(O)(O)=O)CC1 MOJCWSMGIRIAQB-SAIUNTKASA-N 0.000 claims 1
- QVMCOJRWJKRLHH-ZWXJPIIXSA-N 6-[[(2r)-2-amino-3-[(2r)-2,3-di(dodecanoyloxy)propyl]sulfanylpropanoyl]amino]hexanoic acid Chemical compound CCCCCCCCCCCC(=O)OC[C@H](CSC[C@H](N)C(=O)NCCCCCC(O)=O)OC(=O)CCCCCCCCCCC QVMCOJRWJKRLHH-ZWXJPIIXSA-N 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000002757 morpholinyl group Chemical group 0.000 claims 1
- BMTLPKHNLUIEIX-GPOMZPHUSA-N n-[(2r)-1-[(2r)-2-amino-3-[[1-(hydroxymethyl)cyclopropyl]amino]-3-oxopropyl]sulfanyl-3-hexadecoxypropan-2-yl]dodecanamide Chemical compound CCCCCCCCCCCCCCCCOC[C@@H](NC(=O)CCCCCCCCCCC)CSC[C@H](N)C(=O)NC1(CO)CC1 BMTLPKHNLUIEIX-GPOMZPHUSA-N 0.000 claims 1
- XYLZTOZVEYGERP-IHLOFXLRSA-N n-[(2r)-3-[(2r)-2-amino-3-[[1-(hydroxymethyl)cyclopropyl]amino]-3-oxopropyl]sulfanyl-2-(dodecanoylamino)propyl]dodecanamide Chemical compound CCCCCCCCCCCC(=O)NC[C@@H](NC(=O)CCCCCCCCCCC)CSC[C@H](N)C(=O)NC1(CO)CC1 XYLZTOZVEYGERP-IHLOFXLRSA-N 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- VHOCUJPBKOZGJD-UHFFFAOYSA-N triacontanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O VHOCUJPBKOZGJD-UHFFFAOYSA-N 0.000 claims 1
- 102000036639 antigens Human genes 0.000 description 12
- 108091007433 antigens Proteins 0.000 description 12
- 239000000427 antigen Substances 0.000 description 11
- 230000002163 immunogen Effects 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 230000001580 bacterial effect Effects 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 102000040430 polynucleotide Human genes 0.000 description 3
- 108091033319 polynucleotide Proteins 0.000 description 3
- 239000002157 polynucleotide Substances 0.000 description 3
- 241000894006 Bacteria Species 0.000 description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
- 241000293869 Salmonella enterica subsp. enterica serovar Typhimurium Species 0.000 description 2
- VHJLVAABSRFDPM-ZXZARUISSA-N dithioerythritol Chemical compound SC[C@H](O)[C@H](O)CS VHJLVAABSRFDPM-ZXZARUISSA-N 0.000 description 2
- UNLYAPBBIOKKDC-UHFFFAOYSA-N 2-(phenylmethoxycarbonylamino)-3-sulfanylpropanoic acid Chemical compound OC(=O)C(CS)NC(=O)OCC1=CC=CC=C1 UNLYAPBBIOKKDC-UHFFFAOYSA-N 0.000 description 1
- 108010071134 CRM197 (non-toxic variant of diphtheria toxin) Proteins 0.000 description 1
- 102000014914 Carrier Proteins Human genes 0.000 description 1
- 108010078791 Carrier Proteins Proteins 0.000 description 1
- 241000192125 Firmicutes Species 0.000 description 1
- 241000588677 Neisseria meningitidis serogroup B Species 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 241001148470 aerobic bacillus Species 0.000 description 1
- 238000002648 combination therapy Methods 0.000 description 1
- 230000037430 deletion Effects 0.000 description 1
- 238000012217 deletion Methods 0.000 description 1
- 235000019439 ethyl acetate Nutrition 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 230000035772 mutation Effects 0.000 description 1
- 102000039446 nucleic acids Human genes 0.000 description 1
- 108020004707 nucleic acids Proteins 0.000 description 1
- 150000007523 nucleic acids Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000002741 site-directed mutagenesis Methods 0.000 description 1
- XZPVPNZTYPUODG-UHFFFAOYSA-M sodium;chloride;dihydrate Chemical compound O.O.[Na+].[Cl-] XZPVPNZTYPUODG-UHFFFAOYSA-M 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000004083 survival effect Effects 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
- 229960000814 tetanus toxoid Drugs 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 241001148471 unidentified anaerobic bacterium Species 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US31655110P | 2010-03-23 | 2010-03-23 | |
| US61/316,551 | 2010-03-23 | ||
| PCT/US2011/029661 WO2011119759A1 (en) | 2010-03-23 | 2011-03-23 | Compounds (cystein based lipopeptides) and compositions as tlr2 agonists used for treating infections, inflammations, respiratory diseases etc. |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013527142A JP2013527142A (ja) | 2013-06-27 |
| JP2013527142A5 true JP2013527142A5 (https=) | 2014-05-01 |
| JP5848748B2 JP5848748B2 (ja) | 2016-01-27 |
Family
ID=43982260
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013501437A Expired - Fee Related JP5848748B2 (ja) | 2010-03-23 | 2011-03-23 | 感染症、炎症、呼吸器疾患などの処置に使用するｔｌｒ２アゴニストとしての化合物（システインベースのリポペプチド）および組成物 |
Country Status (10)
| Country | Link |
|---|---|
| US (2) | US8808703B2 (https=) |
| EP (1) | EP2549990A1 (https=) |
| JP (1) | JP5848748B2 (https=) |
| KR (1) | KR101853513B1 (https=) |
| CN (1) | CN102905703B (https=) |
| AU (1) | AU2011232421B2 (https=) |
| CA (1) | CA2792938C (https=) |
| EA (2) | EA031379B1 (https=) |
| MX (1) | MX341395B (https=) |
| WO (1) | WO2011119759A1 (https=) |
Families Citing this family (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011027222A2 (en) | 2009-09-02 | 2011-03-10 | Novartis Ag | Immunogenic compositions including tlr activity modulators |
| AU2011295853A1 (en) * | 2010-09-01 | 2013-04-04 | Irm Llc | Adsorption of immunopotentiators to insoluble metal salts |
| EP2618842B1 (en) | 2010-09-22 | 2019-04-24 | Ena Therapeutics Pty Ltd | Novel immunostimulatory method |
| WO2012117377A1 (en) | 2011-03-02 | 2012-09-07 | Novartis Ag | Combination vaccines with lower doses of antigen and/or adjuvant |
| EP2502631A1 (en) * | 2011-03-22 | 2012-09-26 | Medizinische Hochschule Hannover | Immune suppressor and its use |
| RU2014112343A (ru) | 2011-09-01 | 2015-10-10 | Новартис Аг | Оставы антигенов staphylococcus aureus, содержащие адъюванты |
| NL2007536C2 (en) * | 2011-10-05 | 2013-04-08 | Academisch Ziekenhuis Leiden Lumc | Adjuvant compound. |
| AU2013229465A1 (en) | 2012-03-07 | 2014-09-04 | Novartis Ag | Adjuvanted formulations of rabies virus immunogens |
| JP2015510872A (ja) | 2012-03-07 | 2015-04-13 | ノバルティス アーゲー | Ｓｔｒｅｐｔｏｃｏｃｃｕｓｐｎｅｕｍｏｎｉａｅ抗原の増強された製剤 |
| MX372965B (es) | 2012-03-08 | 2020-04-01 | Glaxosmithkline Biologicals Sa | Formulaciones adyuvadas de vacunas de difteria, tetanos y tos ferina (dtp) de refuerzo. |
| US8782263B1 (en) * | 2012-04-20 | 2014-07-15 | Disney Enterprises, Inc. | Authenticated session controller |
| CN103570809B (zh) * | 2012-07-20 | 2015-06-24 | 华东师范大学 | 一种抗炎症的脂肽及其制备方法和应用 |
| JP6324961B2 (ja) | 2012-09-06 | 2018-05-16 | ノバルティス アーゲー | 血清群ｂ髄膜炎菌とｄ／ｔ／ｐとの組み合わせワクチン |
| WO2014113634A1 (en) * | 2013-01-17 | 2014-07-24 | University Of Kansas | Toll-like receptor 2-agonistic lipopeptides, and method of making the same |
| BR112015018014A2 (pt) | 2013-02-01 | 2017-07-11 | Glaxosmithkline Biologicals Sa | liberação intradérmica de composições imunológicas compreendendo agonistas do receptor do tipo toll |
| SG11201509265SA (en) | 2013-05-10 | 2015-12-30 | Novartis Ag | Avoiding narcolepsy risk in influenza vaccines |
| CN104338129B (zh) * | 2013-07-26 | 2017-05-24 | 中国科学院上海巴斯德研究所 | 雷帕霉素作为疫苗佐剂的用途及制备方法 |
| WO2015065168A1 (en) * | 2013-10-28 | 2015-05-07 | Universiti Malaya | Oligo-ethylene glycol based phosphonate surface modification reagents and use thereof |
| KR20160102210A (ko) | 2013-12-27 | 2016-08-29 | 노버스 인터내쇼날 인코포레이티드 | 에톡시화 계면활성제 |
| CA3026178C (en) * | 2016-06-29 | 2024-05-21 | The Scripps Research Institute | Diprovocims: a new and potent class of tlr agonists |
| CN110461351B (zh) * | 2017-03-31 | 2024-03-26 | 艾娜呼吸私人有限公司 | 用tlr2激动剂治疗呼吸道感染 |
| US10584306B2 (en) | 2017-08-11 | 2020-03-10 | Board Of Regents Of The University Of Oklahoma | Surfactant microemulsions |
| EP3678693A1 (en) | 2017-09-08 | 2020-07-15 | Evelo Biosciences, Inc. | Bacterial extracellular vesicles |
| AU2018391325B2 (en) * | 2017-12-21 | 2024-07-11 | Axelia Oncology Pty Ltd | Optimised compounds |
| RU2703264C1 (ru) * | 2018-05-30 | 2019-10-16 | Татьяна Борисовна Корженевская | Способ лечения катаральных осложнений верхних дыхательных путей при острых респираторных вирусных инфекциях у детей |
| US12594286B2 (en) | 2018-07-02 | 2026-04-07 | Ayuvis Research, Inc. | Immunodulating small molecules |
| WO2020023872A1 (en) * | 2018-07-27 | 2020-01-30 | Children's Medical Center Corporation | Use of toll-like receptor 2 (tlr-2) agonist for modulating human immune response |
| US20210393621A1 (en) | 2018-10-26 | 2021-12-23 | The Research Foundation For The State University Of New York | Combination serotonin specific reuptake inhibitor and serotonin 1a receptor partial agonist for reducing l-dopa-induced dyskinesia |
| CN109758467B (zh) * | 2019-03-08 | 2020-12-25 | 中国农业科学院兰州兽医研究所 | 一种吉西他滨在制备预防口蹄疫病毒感染的药物中的应用 |
| MX2021015961A (es) * | 2019-06-26 | 2022-03-22 | Ena Respiratory Pty Ltd | Moleculas novedosas. |
| CN110742880A (zh) * | 2019-10-24 | 2020-02-04 | 上海长海医院 | Cl419在制备治疗炎性肠病药物中的用途 |
| JP7829485B2 (ja) | 2019-12-20 | 2026-03-13 | ナミ セラピューティクス， インコーポレイテッド | がんの処置において有用なＴｏｌｌ様受容体（「ＴＬＲ」）アゴニストプロドラッグを含有する製剤化および／または共製剤化リポソーム組成物ならびにその方法 |
| EP4132547A4 (en) * | 2020-04-06 | 2024-05-01 | The Trustees of Indiana University | ALKALINE RESPIRATORY EPITHELIUM THERAPY TO TREAT VIRAL RESPIRATORY INFECTION |
| JP7744936B2 (ja) * | 2020-06-26 | 2025-09-26 | イーナ レスパラトリー ピーティーワイ リミテッド | 分岐脂質化合物 |
| US20250152611A1 (en) * | 2022-01-19 | 2025-05-15 | President And Fellows Of Harvard College | Immunomodulatory lipids and uses thereof |
| EP4531867A1 (en) * | 2022-05-25 | 2025-04-09 | Ayuvis Research, Inc. | Novel immunodulating small molecules |
| WO2025101524A1 (en) * | 2023-11-06 | 2025-05-15 | Hbc Immunology Inc. | Lipopeptide compounds, and use in modulating eosinophilia |
| CN118161478B (zh) * | 2024-03-07 | 2024-08-27 | 中国农业大学 | 肥大细胞抑制剂在制备防治猪繁殖与呼吸综合征早期感染药物中的应用 |
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|---|---|---|---|---|
| DE2848965A1 (de) | 1978-11-11 | 1980-05-22 | Behringwerke Ag | Verfahren zur herstellung von membranproteinen aus neisseria meningitidis und diese enthaltende vaccine |
| EP0114787B1 (de) | 1983-01-25 | 1991-09-25 | Ciba-Geigy Ag | Neue Peptidderivate |
| DE3813821A1 (de) | 1988-04-22 | 1989-11-02 | Hoechst Ag | Synthetische vakzine gegen die maul- und klauenseuche und verfahren zu deren herstellung |
| DE3546150A1 (de) * | 1985-06-24 | 1987-01-22 | Hoechst Ag | Membrananker-wirkstoffkonjugat, seine herstellung sowie seine verwendung |
| DE3937412A1 (de) * | 1989-11-10 | 1991-05-16 | Hoechst Ag | Synthetische vakzine zur spezifischen induktion zytotoxischer t-lymphozyten |
| DE4116256C2 (de) * | 1991-05-17 | 1996-08-29 | Max Planck Gesellschaft | Bestimmung von Peptidmotiven auf MHC-Molekülen |
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-
2011
- 2011-03-23 EA EA201501033A patent/EA031379B1/ru not_active IP Right Cessation
- 2011-03-23 CA CA2792938A patent/CA2792938C/en not_active Expired - Fee Related
- 2011-03-23 EA EA201201321A patent/EA023725B1/ru not_active IP Right Cessation
- 2011-03-23 MX MX2012010968A patent/MX341395B/es active IP Right Grant
- 2011-03-23 JP JP2013501437A patent/JP5848748B2/ja not_active Expired - Fee Related
- 2011-03-23 CN CN201180025589.5A patent/CN102905703B/zh not_active Expired - Fee Related
- 2011-03-23 KR KR1020127027449A patent/KR101853513B1/ko not_active Expired - Fee Related
- 2011-03-23 US US13/636,328 patent/US8808703B2/en active Active
- 2011-03-23 AU AU2011232421A patent/AU2011232421B2/en not_active Ceased
- 2011-03-23 EP EP11715325A patent/EP2549990A1/en not_active Withdrawn
- 2011-03-23 WO PCT/US2011/029661 patent/WO2011119759A1/en not_active Ceased
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2014
- 2014-07-09 US US14/326,957 patent/US9365506B2/en active Active
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