JP2002505292A5 - - Google Patents
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- Publication number
- JP2002505292A5 JP2002505292A5 JP2000534218A JP2000534218A JP2002505292A5 JP 2002505292 A5 JP2002505292 A5 JP 2002505292A5 JP 2000534218 A JP2000534218 A JP 2000534218A JP 2000534218 A JP2000534218 A JP 2000534218A JP 2002505292 A5 JP2002505292 A5 JP 2002505292A5
- Authority
- JP
- Japan
- Prior art keywords
- substituted
- unsubstituted
- compound
- group
- alkyl
- 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.)
- Withdrawn
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- 150000001875 compounds Chemical class 0.000 description 82
- 238000000034 method Methods 0.000 description 42
- 239000000126 substance Substances 0.000 description 30
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 21
- 125000002431 aminoalkoxy group Chemical group 0.000 description 18
- 230000000845 anti-microbial effect Effects 0.000 description 17
- 150000001413 amino acids Chemical class 0.000 description 16
- 125000004103 aminoalkyl group Chemical group 0.000 description 16
- 150000003431 steroids Chemical class 0.000 description 16
- 241000894006 Bacteria Species 0.000 description 15
- 125000005416 guanidinoalkyloxy group Chemical group 0.000 description 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 15
- 239000000203 mixture Substances 0.000 description 15
- 125000005096 aminoalkylaminocarbonyl group Chemical group 0.000 description 14
- 125000005123 aminoalkylcarboxy group Chemical group 0.000 description 13
- 229910052739 hydrogen Inorganic materials 0.000 description 13
- 239000001257 hydrogen Substances 0.000 description 13
- 244000005700 microbiome Species 0.000 description 13
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 12
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 11
- 125000003118 aryl group Chemical group 0.000 description 11
- 125000001188 haloalkyl group Chemical group 0.000 description 11
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 11
- 125000004043 oxo group Chemical group O=* 0.000 description 11
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 10
- -1 alkyl ether compound Chemical class 0.000 description 9
- 230000000813 microbial effect Effects 0.000 description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 9
- 239000004599 antimicrobial Substances 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 7
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 7
- 230000003115 biocidal effect Effects 0.000 description 6
- 125000004122 cyclic group Chemical group 0.000 description 6
- 208000015181 infectious disease Diseases 0.000 description 6
- 230000035699 permeability Effects 0.000 description 6
- 239000008194 pharmaceutical composition Substances 0.000 description 6
- 229920006395 saturated elastomer Polymers 0.000 description 6
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 125000004429 atom Chemical group 0.000 description 5
- 150000001721 carbon Chemical group 0.000 description 5
- 239000012039 electrophile Substances 0.000 description 5
- 239000002243 precursor Substances 0.000 description 4
- 239000003242 anti bacterial agent Substances 0.000 description 3
- 230000002708 enhancing effect Effects 0.000 description 3
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 description 3
- GZQKNULLWNGMCW-PWQABINMSA-N lipid A (E. coli) Chemical compound O1[C@H](CO)[C@@H](OP(O)(O)=O)[C@H](OC(=O)C[C@@H](CCCCCCCCCCC)OC(=O)CCCCCCCCCCCCC)[C@@H](NC(=O)C[C@@H](CCCCCCCCCCC)OC(=O)CCCCCCCCCCC)[C@@H]1OC[C@@H]1[C@@H](O)[C@H](OC(=O)C[C@H](O)CCCCCCCCCCC)[C@@H](NC(=O)C[C@H](O)CCCCCCCCCCC)[C@@H](OP(O)(O)=O)O1 GZQKNULLWNGMCW-PWQABINMSA-N 0.000 description 3
- 125000006239 protecting group Chemical group 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 231100000331 toxic Toxicity 0.000 description 3
- 230000002588 toxic effect Effects 0.000 description 3
- 208000035143 Bacterial infection Diseases 0.000 description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
- 208000022362 bacterial infectious disease Diseases 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 210000002808 connective tissue Anatomy 0.000 description 2
- 239000000645 desinfectant Substances 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 230000026267 regulation of growth Effects 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical group BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
- IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical group [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 description 1
- 125000005335 azido alkyl group Chemical group 0.000 description 1
- 230000003385 bacteriostatic effect Effects 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 208000027096 gram-negative bacterial infections Diseases 0.000 description 1
- 125000001165 hydrophobic group Chemical group 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/US1998/004489 WO1999044616A1 (en) | 1998-03-06 | 1998-03-06 | Steroid derived antibiotics |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009258873A Division JP5147814B2 (ja) | 2009-11-12 | 2009-11-12 | ステロイド由来抗生物質 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2002505292A JP2002505292A (ja) | 2002-02-19 |
| JP2002505292A5 true JP2002505292A5 (enExample) | 2005-12-22 |
Family
ID=22266538
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000534218A Withdrawn JP2002505292A (ja) | 1998-03-06 | 1998-03-06 | ステロイド由来抗生物質 |
Country Status (9)
| Country | Link |
|---|---|
| EP (1) | EP1058552B1 (enExample) |
| JP (1) | JP2002505292A (enExample) |
| CN (1) | CN100398109C (enExample) |
| AT (1) | ATE269086T1 (enExample) |
| AU (1) | AU759333B2 (enExample) |
| BR (1) | BR9815711B1 (enExample) |
| CA (1) | CA2322847C (enExample) |
| DE (1) | DE69824638T2 (enExample) |
| WO (1) | WO1999044616A1 (enExample) |
Families Citing this family (41)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6350738B1 (en) * | 1998-03-06 | 2002-02-26 | Brigham Young University | Steroid derived antibiotics |
| EP1223941B1 (en) * | 1999-10-25 | 2008-11-05 | Hollis-Eden Pharmaceuticals Inc. | Therapeutic treatments for blood cell deficiencies using sreroids |
| SK15692002A3 (sk) | 2000-04-28 | 2003-11-04 | Inflazyme Pharmaceuticals Limited | 3-Amino-6,7-dioxygénované steroidy a s nimi súvisiace použitie |
| CA2419801C (en) * | 2000-08-15 | 2010-08-10 | Brigham Young University | Steroid derived antibiotics |
| US7141559B2 (en) | 2002-06-19 | 2006-11-28 | Karo Bio Ab | Glucocorticoid receptor ligands for the treatment of metabolic disorders |
| KR100552567B1 (ko) * | 2003-08-23 | 2006-02-15 | 한국유나이티드제약 주식회사 | 수분 흡수에 안정하고 빠르게 붕해되는 세푸록심 악세틸을포함하는 정제의 조성물 및 제조 방법 |
| WO2010036427A1 (en) | 2008-06-17 | 2010-04-01 | Brigham Young University | Cationic steroid antimicrobial diagnostic, detection, screening and imaging methods |
| KR20140063616A (ko) | 2011-07-20 | 2014-05-27 | 브라이엄 영 유니버시티 | 소수성 세라게닌 화합물 및 이를 포함하는 기구 |
| US8932614B2 (en) | 2011-08-25 | 2015-01-13 | Paul B. Savage | Incorporation of particulate ceragenins in polymers |
| US9694019B2 (en) | 2011-09-13 | 2017-07-04 | Brigham Young University | Compositions and methods for treating bone diseases and broken bones |
| US9603859B2 (en) | 2011-09-13 | 2017-03-28 | Brigham Young University | Methods and products for increasing the rate of healing of tissue wounds |
| BR112014005914B1 (pt) | 2011-09-13 | 2021-11-09 | Brigham Young University | Produtos para cicatrização de feridas tecidulares |
| EP2755661B1 (en) | 2011-09-13 | 2026-08-05 | Brigham Young University | Compositions for treating bone diseases and broken bones |
| EP3449900A1 (en) * | 2011-12-21 | 2019-03-06 | Brigham Young University | Oral care compositions |
| US9533063B1 (en) | 2012-03-01 | 2017-01-03 | Brigham Young University | Aerosols incorporating ceragenin compounds and methods of use thereof |
| US20130280391A1 (en) * | 2012-04-24 | 2013-10-24 | Brigham Young University | Anti-microbial wash compositions including ceragenin compounds and methods of use for treating non-meat food products |
| CA2872399C (en) | 2012-05-02 | 2021-01-12 | Brigham Young University | Ceragenin particulate materials and methods for making same |
| CA2888259C (en) | 2012-10-17 | 2019-05-28 | Brigham Young University | Treatment and prevention of mastitis |
| AU2014203882B2 (en) | 2013-01-07 | 2016-06-23 | Brigham Young University | Methods for reducing cellular proliferation and treating certain diseases |
| US11524015B2 (en) | 2013-03-15 | 2022-12-13 | Brigham Young University | Methods for treating inflammation, autoimmune disorders and pain |
| BR112015023747B1 (pt) * | 2013-03-15 | 2023-04-18 | Brigham Young University | Uso de um composto antimicrobiano catiônico esteroide (csa) para a preparação de uma composição para tratar, reduzir, ou prevenir inflamação aguda ou crônica e/ou dor aguda ou crônica associada com uma doença ou um sintoma de doença |
| US10568893B2 (en) | 2013-03-15 | 2020-02-25 | Brigham Young University | Methods for treating inflammation, autoimmune disorders and pain |
| US9387215B2 (en) | 2013-04-22 | 2016-07-12 | Brigham Young University | Animal feed including cationic cholesterol additive and related methods |
| US11690855B2 (en) | 2013-10-17 | 2023-07-04 | Brigham Young University | Methods for treating lung infections and inflammation |
| US20150203527A1 (en) | 2014-01-23 | 2015-07-23 | Brigham Young University | Cationic steroidal antimicrobials |
| CA2844321C (en) | 2014-02-27 | 2021-03-16 | Brigham Young University | Cationic steroidal antimicrobial compounds |
| US9867836B2 (en) | 2014-03-13 | 2018-01-16 | Brigham Young University | Lavage and/or infusion using CSA compounds for increasing fertility in a mammal |
| US10220045B2 (en) | 2014-03-13 | 2019-03-05 | Brigham Young University | Compositions and methods for forming stabilized compositions with reduced CSA agglomeration |
| US9931350B2 (en) | 2014-03-14 | 2018-04-03 | Brigham Young University | Anti-infective and osteogenic compositions and methods of use |
| US9686966B2 (en) | 2014-04-30 | 2017-06-27 | Brigham Young University | Methods and apparatus for cleaning or disinfecting a water delivery system |
| US10238665B2 (en) | 2014-06-26 | 2019-03-26 | Brigham Young University | Methods for treating fungal infections |
| US10441595B2 (en) | 2014-06-26 | 2019-10-15 | Brigham Young University | Methods for treating fungal infections |
| US10227376B2 (en) | 2014-08-22 | 2019-03-12 | Brigham Young University | Radiolabeled cationic steroid antimicrobials and diagnostic methods |
| US10155788B2 (en) | 2014-10-07 | 2018-12-18 | Brigham Young University | Cationic steroidal antimicrobial prodrug compositions and uses thereof |
| US9527883B2 (en) | 2015-04-22 | 2016-12-27 | Brigham Young University | Methods for the synthesis of ceragenins |
| US10370403B2 (en) | 2015-04-22 | 2019-08-06 | Brigham Young University | Methods for the synthesis of ceragenins |
| US9434759B1 (en) | 2015-05-18 | 2016-09-06 | Brigham Young University | Cationic steroidal antimicrobial compounds and methods of manufacturing such compounds |
| US10226550B2 (en) | 2016-03-11 | 2019-03-12 | Brigham Young University | Cationic steroidal antimicrobial compositions for the treatment of dermal tissue |
| JP2017031201A (ja) * | 2016-09-30 | 2017-02-09 | ブリガム ヤング ユニバーシティ | 口腔ケア組成物 |
| US10959433B2 (en) | 2017-03-21 | 2021-03-30 | Brigham Young University | Use of cationic steroidal antimicrobials for sporicidal activity |
| US12186328B2 (en) | 2019-05-23 | 2025-01-07 | Brigham Young University | Use of CSA compounds to stimulate stem cells and hair growth |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3519714A (en) * | 1966-03-15 | 1970-07-07 | Herchel Smith | Synthesis of gona-1,3,5(10)-trienes |
| US4192871A (en) * | 1976-01-06 | 1980-03-11 | Glaxo Laboratories Limited | Chemical compounds |
| CA2157594A1 (en) * | 1993-03-10 | 1994-09-15 | Leah L. Frye | Steroid derivatives, pharmaceutical compositions containing them, and their use as antibiotics or disinfectants |
| JPH09511486A (ja) * | 1994-01-13 | 1997-11-18 | ザ・トラスティーズ・オブ・コランビア・ユニバーシティー・イン・ザ・シティー・オブ・ニューヨーク | 合成レセプター、ライブラリー及びこれらの使用 |
| DK0749437T3 (da) * | 1994-03-10 | 2002-03-04 | Magainin Pharma | Farmaceutisk anvendelse af steroidderivater |
| US5834453A (en) * | 1995-05-30 | 1998-11-10 | Lehigh University | Methods for the manufacture and use of antimicrobial sterol conjugates |
-
1998
- 1998-03-06 AT AT98909028T patent/ATE269086T1/de not_active IP Right Cessation
- 1998-03-06 CA CA002322847A patent/CA2322847C/en not_active Expired - Lifetime
- 1998-03-06 JP JP2000534218A patent/JP2002505292A/ja not_active Withdrawn
- 1998-03-06 WO PCT/US1998/004489 patent/WO1999044616A1/en not_active Ceased
- 1998-03-06 CN CNB988138611A patent/CN100398109C/zh not_active Expired - Lifetime
- 1998-03-06 AU AU66911/98A patent/AU759333B2/en not_active Expired
- 1998-03-06 BR BRPI9815711-6A patent/BR9815711B1/pt not_active IP Right Cessation
- 1998-03-06 DE DE69824638T patent/DE69824638T2/de not_active Expired - Lifetime
- 1998-03-06 EP EP98909028A patent/EP1058552B1/en not_active Expired - Lifetime
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