JP2012506908A5 - - Google Patents
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- JP2012506908A5 JP2012506908A5 JP2011534666A JP2011534666A JP2012506908A5 JP 2012506908 A5 JP2012506908 A5 JP 2012506908A5 JP 2011534666 A JP2011534666 A JP 2011534666A JP 2011534666 A JP2011534666 A JP 2011534666A JP 2012506908 A5 JP2012506908 A5 JP 2012506908A5
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- JP
- Japan
- Prior art keywords
- compound
- formula
- tert
- producing
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- 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 52
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims 27
- 239000001257 hydrogen Substances 0.000 claims 15
- 229910052739 hydrogen Inorganic materials 0.000 claims 15
- 150000003839 salts Chemical class 0.000 claims 15
- 125000001475 halogen functional group Chemical group 0.000 claims 13
- 239000008213 purified water Substances 0.000 claims 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 12
- 239000000203 mixture Substances 0.000 claims 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 10
- 125000000217 alkyl group Chemical group 0.000 claims 10
- 150000002431 hydrogen Chemical class 0.000 claims 9
- -1 3- (dimethylamino) -propyl Chemical group 0.000 claims 8
- 241000894006 Bacteria Species 0.000 claims 8
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims 8
- XIEOKRXVAACBHI-UHFFFAOYSA-N pyrimidine-4,6-dicarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=NC=N1 XIEOKRXVAACBHI-UHFFFAOYSA-N 0.000 claims 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 6
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 claims 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 6
- 239000003054 catalyst Substances 0.000 claims 5
- 208000015181 infectious disease Diseases 0.000 claims 5
- 238000000034 method Methods 0.000 claims 5
- 230000000813 microbial effect Effects 0.000 claims 5
- 239000008194 pharmaceutical composition Substances 0.000 claims 5
- 229910052723 transition metal Inorganic materials 0.000 claims 5
- 150000003624 transition metals Chemical class 0.000 claims 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 4
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 235000011187 glycerol Nutrition 0.000 claims 4
- 244000005700 microbiome Species 0.000 claims 4
- 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 4
- SEFMSAJRZMNUSP-FGZHOGPDSA-N tert-butyl (3r)-3-[2-amino-6-[[6-[[3-amino-2-[(3r)-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidin-3-yl]oxy-5-(trifluoromethyl)phenyl]carbamoyl]pyrimidine-4-carbonyl]amino]-4-(trifluoromethyl)phenoxy]pyrrolidine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CC[C@H]1OC1=C(N)C=C(C(F)(F)F)C=C1NC(=O)C1=CC(C(=O)NC=2C(=C(N)C=C(C=2)C(F)(F)F)O[C@H]2CN(CC2)C(=O)OC(C)(C)C)=NC=N1 SEFMSAJRZMNUSP-FGZHOGPDSA-N 0.000 claims 4
- APCBTRDHCDOPNY-SSDOTTSWSA-N tert-butyl (3r)-3-hydroxypyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CC[C@@H](O)C1 APCBTRDHCDOPNY-SSDOTTSWSA-N 0.000 claims 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims 4
- 241000124008 Mammalia Species 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 3
- 238000009472 formulation Methods 0.000 claims 3
- 125000004970 halomethyl group Chemical group 0.000 claims 3
- 239000002504 physiological saline solution Substances 0.000 claims 3
- DBLXCJSPHCRQFO-SNVBAGLBSA-N tert-butyl (3r)-3-[2,6-dinitro-4-(trifluoromethyl)phenoxy]pyrrolidine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CC[C@H]1OC1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O DBLXCJSPHCRQFO-SNVBAGLBSA-N 0.000 claims 3
- WDCYWAQPCXBPJA-UHFFFAOYSA-N 1,3-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC([N+]([O-])=O)=C1 WDCYWAQPCXBPJA-UHFFFAOYSA-N 0.000 claims 2
- HFHAVERNVFNSHL-UHFFFAOYSA-N 2-chloro-1,3-dinitro-5-(trifluoromethyl)benzene Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=CC([N+]([O-])=O)=C1Cl HFHAVERNVFNSHL-UHFFFAOYSA-N 0.000 claims 2
- GPIQOFWTZXXOOV-UHFFFAOYSA-N 2-chloro-4,6-dimethoxy-1,3,5-triazine Chemical compound COC1=NC(Cl)=NC(OC)=N1 GPIQOFWTZXXOOV-UHFFFAOYSA-N 0.000 claims 2
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 claims 2
- 240000004808 Saccharomyces cerevisiae Species 0.000 claims 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims 2
- WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 claims 2
- 229960004853 betadex Drugs 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- 229940069078 citric acid / sodium citrate Drugs 0.000 claims 2
- 238000010168 coupling process Methods 0.000 claims 2
- 238000005859 coupling reaction Methods 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- BXGTVNLGPMZLAZ-UHFFFAOYSA-N n'-ethylmethanediimine;hydrochloride Chemical compound Cl.CCN=C=N BXGTVNLGPMZLAZ-UHFFFAOYSA-N 0.000 claims 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 claims 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims 2
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 claims 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 2
- 239000011780 sodium chloride Substances 0.000 claims 2
- VILONDWFCAFQMY-SNVBAGLBSA-N tert-butyl (3r)-3-[2,6-diamino-4-(trifluoromethyl)phenoxy]pyrrolidine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CC[C@H]1OC1=C(N)C=C(C(F)(F)F)C=C1N VILONDWFCAFQMY-SNVBAGLBSA-N 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims 1
- 229920002565 Polyethylene Glycol 400 Polymers 0.000 claims 1
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N acetaldehyde dimethyl acetal Natural products COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 claims 1
- 230000000845 anti-microbial effect Effects 0.000 claims 1
- 239000004599 antimicrobial Substances 0.000 claims 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims 1
- 230000005595 deprotonation Effects 0.000 claims 1
- 238000010537 deprotonation reaction Methods 0.000 claims 1
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 238000007327 hydrogenolysis reaction Methods 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- JLFNLZLINWHATN-UHFFFAOYSA-N pentaethylene glycol Chemical compound OCCOCCOCCOCCOCCO JLFNLZLINWHATN-UHFFFAOYSA-N 0.000 claims 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 claims 1
- 238000004366 reverse phase liquid chromatography Methods 0.000 claims 1
- 239000000243 solution Substances 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 claims 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10859508P | 2008-10-27 | 2008-10-27 | |
| US61/108,595 | 2008-10-27 | ||
| US12/605,584 | 2009-10-26 | ||
| US12/605,584 US8278309B2 (en) | 2008-10-27 | 2009-10-26 | Synthetic mimetics of host defense and uses thereof |
| PCT/US2009/062147 WO2010062573A1 (en) | 2008-10-27 | 2009-10-27 | Synthetic mimetics of host defense and uses thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2012506908A JP2012506908A (ja) | 2012-03-22 |
| JP2012506908A5 true JP2012506908A5 (https=) | 2012-10-11 |
Family
ID=42118100
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011534666A Pending JP2012506908A (ja) | 2008-10-27 | 2009-10-27 | 宿主防御の合成模倣体とその使用 |
Country Status (14)
| Country | Link |
|---|---|
| US (2) | US8278309B2 (https=) |
| EP (1) | EP2358380A4 (https=) |
| JP (1) | JP2012506908A (https=) |
| KR (1) | KR20110074995A (https=) |
| CN (1) | CN102256614B (https=) |
| AU (1) | AU2009320139B2 (https=) |
| BR (1) | BRPI0920251A2 (https=) |
| CA (1) | CA2741764A1 (https=) |
| IL (1) | IL212275A0 (https=) |
| MX (1) | MX2011004360A (https=) |
| RU (1) | RU2540077C2 (https=) |
| TW (1) | TWI478915B (https=) |
| UA (1) | UA104875C2 (https=) |
| WO (1) | WO2010062573A1 (https=) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20090092574A1 (en) * | 2006-12-29 | 2009-04-09 | Scott Richard W | Ophthalmic And Otic Compositions Of Facially Amphiphilic Polymers And Oligomers And Uses Thereof |
| TWI478915B (zh) * | 2008-10-27 | 2015-04-01 | Cellceutix Corp | 宿主防禦之合成模擬物及其用途 |
| EP2709619B1 (en) * | 2011-05-16 | 2017-10-11 | Cellceutix Corporation | Compounds for use in treatment of mucositis |
| US9758607B2 (en) | 2013-10-10 | 2017-09-12 | Research Foundation Of The City University Of New York | Polymer with antibacterial activity |
| JP6047203B2 (ja) * | 2015-02-20 | 2016-12-21 | セルセウティックス コーポレイション | 消化管の炎症性疾患の予防および／または治療のための宿主防御タンパク質（ｈｄｐ）模倣薬 |
| CN107574581B (zh) * | 2017-08-03 | 2019-09-10 | 天津大学 | 一种抗菌性聚(ε-己内酯)/模拟抗菌肽电纺纤维膜及其制备方法 |
| US20230218644A1 (en) | 2020-04-16 | 2023-07-13 | Som Innovation Biotech, S.A. | Compounds for use in the treatment of viral infections by respiratory syndrome-related coronavirus |
| WO2021248008A1 (en) * | 2020-06-05 | 2021-12-09 | Innovation Pharmaceuticals Inc. | Arylamide compounds for treatment and prevention of viral infections |
Family Cites Families (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3496179A (en) | 1967-10-11 | 1970-02-17 | Pfizer & Co C | 2-amino-3,4-dihydroquinazolines |
| DK0629347T3 (da) | 1992-01-23 | 1998-02-16 | Morinaga Milk Industry Co Ltd | Antibakterielt middel og behandling af genstande dermed |
| DE69907476T2 (de) | 1998-08-20 | 2004-04-15 | The University Of North Carolina At Chapel Hill Office Of Technology Development | Dibenzothiophene derivate und ihre verwendung |
| US6482799B1 (en) | 1999-05-25 | 2002-11-19 | The Regents Of The University Of California | Self-preserving multipurpose ophthalmic solutions incorporating a polypeptide antimicrobial |
| JP2001261674A (ja) | 2000-03-22 | 2001-09-26 | Mitsui Chemicals Inc | ベンゾチオフェン誘導体およびそれを有効成分として含有する核内レセプター作動薬 |
| FR2813080B1 (fr) | 2000-08-17 | 2002-11-29 | Stago Diagnostica | Peptides anti-heparine |
| EP3045168A1 (en) | 2000-11-08 | 2016-07-20 | FXS Ventures, LLC | Improved ophthalmic and contact lens solution |
| EP2289524A1 (en) | 2001-03-08 | 2011-03-02 | The Trustees Of The University Of Pennsylvania | Facially amphiphillic polymers as anti-infective agents |
| WO2003045307A2 (en) | 2001-11-21 | 2003-06-05 | Sugen, Inc. | Pharmaceutical formulations comprising indolinone derivatives |
| CA2487454A1 (en) | 2002-05-28 | 2003-12-04 | The Trustees Of The University Of Pennsylvania | Methods, systems, and computer program products for computational analysis and design of amphiphilic polymers |
| EP1513622A4 (en) | 2002-06-13 | 2005-09-14 | Univ Pennsylvania | METHODS, SYSTEMS AND COMPUTER PROGRAM PRODUCTS FOR STIMULATING BIOMEMBRANES USING ROUGH GRAIN MODELS |
| EP2471526A3 (en) | 2003-03-17 | 2012-12-12 | The Trustees Of The University Of Pennsylvania | Facially amphiphillic polymers and oligomers and uses thereof |
| AU2003249114A1 (en) | 2003-03-20 | 2004-10-11 | Shiseido International France | Cosmetic composition |
| US20050065091A1 (en) | 2003-09-18 | 2005-03-24 | Gholam Peyman | Stabilized ocular solutions |
| CN1922133A (zh) | 2004-01-23 | 2007-02-28 | 宾夕法尼亚州大学理事会 | 表面两亲性聚芳基和聚芳基炔基聚合物和低聚物及其用途 |
| PL2708225T3 (pl) | 2004-04-23 | 2019-07-31 | Cydex Pharmaceuticals, Inc. | Formulacja DPI zawierająca eter sulfoalkilowy cyklodekstryny |
| AU2005254574B2 (en) | 2004-06-15 | 2012-02-02 | Polymedix, Inc. | Polycationic compounds and uses thereof |
| JP5027659B2 (ja) | 2004-07-23 | 2012-09-19 | ザ トラスティーズ オブ ザ ユニバーシティ オブ ペンシルバニア | 抗菌コポリマーおよびその使用 |
| DK2377557T3 (en) | 2004-11-24 | 2017-02-06 | Meda Pharmaceuticals Inc | Compositions comprising azelastine and methods for its use |
| US20100048498A1 (en) | 2004-12-21 | 2010-02-25 | Johnson Barbara A | Stable non-dihydrate azithromycin oral suspensions |
| US20060241052A1 (en) | 2005-02-25 | 2006-10-26 | Degrado William F | Facially amphiphilic polymers and oligomers, compositions thereof, and use thereof in methods of treating cancer |
| RU2325151C2 (ru) * | 2006-06-29 | 2008-05-27 | ООО "Научно-производственный центр "Амфион" | Способ получения системы доставки водонерастворимых и плохорастворимых биологически активных веществ и лекарственная форма на ее основе |
| JP2008137978A (ja) | 2006-12-05 | 2008-06-19 | Canon Inc | カルバゾール誘導体及びこれを用いた有機発光素子 |
| US20090092574A1 (en) * | 2006-12-29 | 2009-04-09 | Scott Richard W | Ophthalmic And Otic Compositions Of Facially Amphiphilic Polymers And Oligomers And Uses Thereof |
| WO2009061697A1 (en) | 2007-11-09 | 2009-05-14 | The Board Of Trustees Of The University Of Illinois | Anticoagulant antagonist and hemophilia procoagulant |
| RU2530899C2 (ru) | 2008-07-28 | 2014-10-20 | Селлсьютикс Корпорейшн | Противомалярийные соединения |
| TWI478915B (zh) * | 2008-10-27 | 2015-04-01 | Cellceutix Corp | 宿主防禦之合成模擬物及其用途 |
-
2009
- 2009-10-26 TW TW098136112A patent/TWI478915B/zh active
- 2009-10-26 US US12/605,584 patent/US8278309B2/en not_active Expired - Fee Related
- 2009-10-27 WO PCT/US2009/062147 patent/WO2010062573A1/en not_active Ceased
- 2009-10-27 MX MX2011004360A patent/MX2011004360A/es active IP Right Grant
- 2009-10-27 UA UAA201106679A patent/UA104875C2/uk unknown
- 2009-10-27 BR BRPI0920251A patent/BRPI0920251A2/pt not_active IP Right Cessation
- 2009-10-27 AU AU2009320139A patent/AU2009320139B2/en not_active Ceased
- 2009-10-27 RU RU2011121354/04A patent/RU2540077C2/ru not_active IP Right Cessation
- 2009-10-27 JP JP2011534666A patent/JP2012506908A/ja active Pending
- 2009-10-27 CA CA2741764A patent/CA2741764A1/en not_active Abandoned
- 2009-10-27 CN CN200980151723.9A patent/CN102256614B/zh not_active Expired - Fee Related
- 2009-10-27 KR KR1020117009356A patent/KR20110074995A/ko not_active Ceased
- 2009-10-27 EP EP09829578A patent/EP2358380A4/en not_active Withdrawn
-
2011
- 2011-04-12 IL IL212275A patent/IL212275A0/en unknown
-
2012
- 2012-08-01 US US13/563,928 patent/US8975262B2/en not_active Expired - Fee Related
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