JP2017519036A5 - - Google Patents
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- JP2017519036A5 JP2017519036A5 JP2016575387A JP2016575387A JP2017519036A5 JP 2017519036 A5 JP2017519036 A5 JP 2017519036A5 JP 2016575387 A JP2016575387 A JP 2016575387A JP 2016575387 A JP2016575387 A JP 2016575387A JP 2017519036 A5 JP2017519036 A5 JP 2017519036A5
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- JP
- Japan
- Prior art keywords
- unsubstituted
- substituted
- alkyl
- alkylamino
- group
- 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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- 125000000217 alkyl group Chemical group 0.000 claims description 119
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 46
- 125000003282 alkyl amino group Chemical group 0.000 claims description 28
- 125000002431 aminoalkoxy group Chemical group 0.000 claims description 28
- 125000005123 aminoalkylcarboxy group Chemical group 0.000 claims description 26
- 150000003839 salts Chemical class 0.000 claims description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims description 25
- 239000001257 hydrogen Substances 0.000 claims description 25
- 125000005096 aminoalkylaminocarbonyl group Chemical group 0.000 claims description 23
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 22
- 125000005416 guanidinoalkyloxy group Chemical group 0.000 claims description 21
- 206010017533 Fungal infection Diseases 0.000 claims description 20
- 241000233866 Fungi Species 0.000 claims description 20
- 208000031888 Mycoses Diseases 0.000 claims description 20
- 150000001875 compounds Chemical class 0.000 claims description 20
- 150000002431 hydrogen Chemical class 0.000 claims description 20
- 125000003118 aryl group Chemical group 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 18
- 241000223238 Trichophyton Species 0.000 claims description 17
- 125000003342 alkenyl group Chemical group 0.000 claims description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
- -1 isconazole Chemical compound 0.000 claims description 14
- 125000000304 alkynyl group Chemical group 0.000 claims description 13
- 241000222120 Candida <Saccharomycetales> Species 0.000 claims description 11
- 208000010195 Onychomycosis Diseases 0.000 claims description 10
- 201000005882 tinea unguium Diseases 0.000 claims description 10
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 9
- 208000015181 infectious disease Diseases 0.000 claims description 9
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 8
- 150000001413 amino acids Chemical class 0.000 claims description 8
- 125000001188 haloalkyl group Chemical group 0.000 claims description 8
- 125000005647 linker group Chemical group 0.000 claims description 8
- 125000004043 oxo group Chemical group O=* 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- 125000006239 protecting group Chemical group 0.000 claims description 8
- 150000003431 steroids Chemical class 0.000 claims description 8
- 208000002474 Tinea Diseases 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 7
- 210000002615 epidermis Anatomy 0.000 claims description 7
- 206010040872 skin infection Diseases 0.000 claims description 7
- 241000228212 Aspergillus Species 0.000 claims description 6
- 241000222122 Candida albicans Species 0.000 claims description 6
- 241000893966 Trichophyton verrucosum Species 0.000 claims description 6
- 229940095731 candida albicans Drugs 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 230000002685 pulmonary effect Effects 0.000 claims description 6
- 241001480043 Arthrodermataceae Species 0.000 claims description 5
- 241001225321 Aspergillus fumigatus Species 0.000 claims description 5
- 201000007336 Cryptococcosis Diseases 0.000 claims description 5
- 241000221204 Cryptococcus neoformans Species 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 241000223259 Trichoderma Species 0.000 claims description 5
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 5
- 229940091771 aspergillus fumigatus Drugs 0.000 claims description 5
- 230000037304 dermatophytes Effects 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 5
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 4
- 239000004471 Glycine Substances 0.000 claims description 4
- 241000228402 Histoplasma Species 0.000 claims description 4
- 208000019693 Lung disease Diseases 0.000 claims description 4
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 4
- 229940121375 antifungal agent Drugs 0.000 claims description 4
- 125000005128 aryl amino alkyl group Chemical group 0.000 claims description 4
- 125000004452 carbocyclyl group Chemical group 0.000 claims description 4
- 230000001684 chronic effect Effects 0.000 claims description 4
- 229940124597 therapeutic agent Drugs 0.000 claims description 4
- 241000124008 Mammalia Species 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 239000003429 antifungal agent Substances 0.000 claims description 3
- 229940079593 drug Drugs 0.000 claims description 3
- YKSVGLFNJPQDJE-YDMQLZBCSA-N (19E,21E,23E,25E,27E,29E,31E)-33-[(2R,3S,4R,5S,6R)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy-17-[7-(4-aminophenyl)-5-hydroxy-4-methyl-7-oxoheptan-2-yl]-1,3,5,7,37-pentahydroxy-18-methyl-9,13,15-trioxo-16,39-dioxabicyclo[33.3.1]nonatriaconta-19,21,23,25,27,29,31-heptaene-36-carboxylic acid Chemical compound CC(CC(C)C1OC(=O)CC(=O)CCCC(=O)CC(O)CC(O)CC(O)CC2(O)CC(O)C(C(CC(O[C@@H]3O[C@H](C)[C@@H](O)[C@@H](N)[C@@H]3O)\C=C\C=C\C=C\C=C\C=C\C=C\C=C\C1C)O2)C(O)=O)C(O)CC(=O)C1=CC=C(N)C=C1 YKSVGLFNJPQDJE-YDMQLZBCSA-N 0.000 claims description 2
- XMAYWYJOQHXEEK-OZXSUGGESA-N (2R,4S)-ketoconazole Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1OC[C@@H]1O[C@@](CN2C=NC=C2)(C=2C(=CC(Cl)=CC=2)Cl)OC1 XMAYWYJOQHXEEK-OZXSUGGESA-N 0.000 claims description 2
- BLSQLHNBWJLIBQ-OZXSUGGESA-N (2R,4S)-terconazole Chemical compound C1CN(C(C)C)CCN1C(C=C1)=CC=C1OC[C@@H]1O[C@@](CN2N=CN=C2)(C=2C(=CC(Cl)=CC=2)Cl)OC1 BLSQLHNBWJLIBQ-OZXSUGGESA-N 0.000 claims description 2
- MQHLMHIZUIDKOO-OKZBNKHCSA-N (2R,6S)-2,6-dimethyl-4-[(2S)-2-methyl-3-[4-(2-methylbutan-2-yl)phenyl]propyl]morpholine Chemical compound C1=CC(C(C)(C)CC)=CC=C1C[C@H](C)CN1C[C@@H](C)O[C@@H](C)C1 MQHLMHIZUIDKOO-OKZBNKHCSA-N 0.000 claims description 2
- AFNXATANNDIXLG-SFHVURJKSA-N 1-[(2r)-2-[(4-chlorophenyl)methylsulfanyl]-2-(2,4-dichlorophenyl)ethyl]imidazole Chemical compound C1=CC(Cl)=CC=C1CS[C@H](C=1C(=CC(Cl)=CC=1)Cl)CN1C=NC=C1 AFNXATANNDIXLG-SFHVURJKSA-N 0.000 claims description 2
- ZCJYUTQZBAIHBS-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenyl)-2-{[4-(phenylsulfanyl)benzyl]oxy}ethyl]imidazole Chemical compound ClC1=CC(Cl)=CC=C1C(OCC=1C=CC(SC=2C=CC=CC=2)=CC=1)CN1C=NC=C1 ZCJYUTQZBAIHBS-UHFFFAOYSA-N 0.000 claims description 2
- OCAPBUJLXMYKEJ-UHFFFAOYSA-N 1-[biphenyl-4-yl(phenyl)methyl]imidazole Chemical compound C1=NC=CN1C(C=1C=CC(=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 OCAPBUJLXMYKEJ-UHFFFAOYSA-N 0.000 claims description 2
- LEZWWPYKPKIXLL-UHFFFAOYSA-N 1-{2-(4-chlorobenzyloxy)-2-(2,4-dichlorophenyl)ethyl}imidazole Chemical compound C1=CC(Cl)=CC=C1COC(C=1C(=CC(Cl)=CC=1)Cl)CN1C=NC=C1 LEZWWPYKPKIXLL-UHFFFAOYSA-N 0.000 claims description 2
- VHVPQPYKVGDNFY-DFMJLFEVSA-N 2-[(2r)-butan-2-yl]-4-[4-[4-[4-[[(2r,4s)-2-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]phenyl]-1,2,4-triazol-3-one Chemical compound O=C1N([C@H](C)CC)N=CN1C1=CC=C(N2CCN(CC2)C=2C=CC(OC[C@@H]3O[C@](CN4N=CN=C4)(OC3)C=3C(=CC(Cl)=CC=3)Cl)=CC=2)C=C1 VHVPQPYKVGDNFY-DFMJLFEVSA-N 0.000 claims description 2
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical group N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims description 2
- APKFDSVGJQXUKY-KKGHZKTASA-N Amphotericin-B Natural products O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1C=CC=CC=CC=CC=CC=CC=C[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 APKFDSVGJQXUKY-KKGHZKTASA-N 0.000 claims description 2
- 241000222173 Candida parapsilosis Species 0.000 claims description 2
- 241000222290 Cladosporium Species 0.000 claims description 2
- 201000003883 Cystic fibrosis Diseases 0.000 claims description 2
- 208000001860 Eye Infections Diseases 0.000 claims description 2
- 229930195098 Hamycin Natural products 0.000 claims description 2
- 241000725303 Human immunodeficiency virus Species 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 2
- YTAOBBFIOAEMLL-REQDGWNSSA-N Luliconazole Chemical compound ClC1=CC(Cl)=CC=C1[C@H](CS\1)SC/1=C(\C#N)N1C=NC=C1 YTAOBBFIOAEMLL-REQDGWNSSA-N 0.000 claims description 2
- 206010027236 Meningitis fungal Diseases 0.000 claims description 2
- BYBLEWFAAKGYCD-UHFFFAOYSA-N Miconazole Chemical compound ClC1=CC(Cl)=CC=C1COC(C=1C(=CC(Cl)=CC=1)Cl)CN1C=NC=C1 BYBLEWFAAKGYCD-UHFFFAOYSA-N 0.000 claims description 2
- 241001480037 Microsporum Species 0.000 claims description 2
- 102000003840 Opioid Receptors Human genes 0.000 claims description 2
- 108090000137 Opioid Receptors Proteins 0.000 claims description 2
- 241000233870 Pneumocystis Species 0.000 claims description 2
- 206010035664 Pneumonia Diseases 0.000 claims description 2
- AWGBZRVEGDNLDZ-UHFFFAOYSA-N Rimocidin Natural products C1C(C(C(O)C2)C(O)=O)OC2(O)CC(O)CCCC(=O)CC(O)C(CC)C(=O)OC(CCC)CC=CC=CC=CC=CC1OC1OC(C)C(O)C(N)C1O AWGBZRVEGDNLDZ-UHFFFAOYSA-N 0.000 claims description 2
- AWGBZRVEGDNLDZ-JCUCCFEFSA-N Rimocidine Chemical compound O([C@H]1/C=C/C=C/C=C/C=C/C[C@H](OC(=O)[C@@H](CC)[C@H](O)CC(=O)CCC[C@H](O)C[C@@]2(O)O[C@H]([C@@H]([C@@H](O)C2)C(O)=O)C1)CCC)[C@@H]1O[C@H](C)[C@@H](O)[C@H](N)[C@@H]1O AWGBZRVEGDNLDZ-JCUCCFEFSA-N 0.000 claims description 2
- 240000004808 Saccharomyces cerevisiae Species 0.000 claims description 2
- 235000014680 Saccharomyces cerevisiae Nutrition 0.000 claims description 2
- 241000191963 Staphylococcus epidermidis Species 0.000 claims description 2
- 241000222126 [Candida] glabrata Species 0.000 claims description 2
- 239000000048 adrenergic agonist Substances 0.000 claims description 2
- 229940126157 adrenergic receptor agonist Drugs 0.000 claims description 2
- 229950006816 albaconazole Drugs 0.000 claims description 2
- UHIXWHUVLCAJQL-MPBGBICISA-N albaconazole Chemical compound C([C@@](O)([C@H](N1C(C2=CC=C(Cl)C=C2N=C1)=O)C)C=1C(=CC(F)=CC=1)F)N1C=NC=N1 UHIXWHUVLCAJQL-MPBGBICISA-N 0.000 claims description 2
- 125000005093 alkyl carbonyl alkyl group Chemical group 0.000 claims description 2
- 125000005197 alkyl carbonyloxy alkyl group Chemical group 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 125000006242 amine protecting group Chemical group 0.000 claims description 2
- 229960003204 amorolfine Drugs 0.000 claims description 2
- APKFDSVGJQXUKY-INPOYWNPSA-N amphotericin B Chemical compound O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 APKFDSVGJQXUKY-INPOYWNPSA-N 0.000 claims description 2
- 229960003942 amphotericin b Drugs 0.000 claims description 2
- 239000003242 anti bacterial agent Substances 0.000 claims description 2
- 230000000845 anti-microbial effect Effects 0.000 claims description 2
- 230000000798 anti-retroviral effect Effects 0.000 claims description 2
- 229940065524 anticholinergics inhalants for obstructive airway diseases Drugs 0.000 claims description 2
- 239000002111 antiemetic agent Substances 0.000 claims description 2
- 229940125715 antihistaminic agent Drugs 0.000 claims description 2
- 239000000739 antihistaminic agent Substances 0.000 claims description 2
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- 239000002221 antipyretic Substances 0.000 claims description 2
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- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000001769 aryl amino group Chemical group 0.000 claims description 2
- 229960002206 bifonazole Drugs 0.000 claims description 2
- 229960002962 butenafine Drugs 0.000 claims description 2
- ABJKWBDEJIDSJZ-UHFFFAOYSA-N butenafine Chemical compound C=1C=CC2=CC=CC=C2C=1CN(C)CC1=CC=C(C(C)(C)C)C=C1 ABJKWBDEJIDSJZ-UHFFFAOYSA-N 0.000 claims description 2
- 229960004348 candicidin Drugs 0.000 claims description 2
- 208000032343 candida glabrata infection Diseases 0.000 claims description 2
- 229940055022 candida parapsilosis Drugs 0.000 claims description 2
- JYIKNQVWKBUSNH-WVDDFWQHSA-N caspofungin Chemical compound C1([C@H](O)[C@@H](O)[C@H]2C(=O)N[C@H](C(=O)N3CC[C@H](O)[C@H]3C(=O)N[C@H](NCCN)[C@H](O)C[C@@H](C(N[C@H](C(=O)N3C[C@H](O)C[C@H]3C(=O)N2)[C@@H](C)O)=O)NC(=O)CCCCCCCC[C@@H](C)C[C@@H](C)CC)[C@H](O)CCN)=CC=C(O)C=C1 JYIKNQVWKBUSNH-WVDDFWQHSA-N 0.000 claims description 2
- 229940044683 chemotherapy drug Drugs 0.000 claims description 2
- 239000000812 cholinergic antagonist Substances 0.000 claims description 2
- 229960004022 clotrimazole Drugs 0.000 claims description 2
- VNFPBHJOKIVQEB-UHFFFAOYSA-N clotrimazole Chemical compound ClC1=CC=CC=C1C(N1C=NC=C1)(C=1C=CC=CC=1)C1=CC=CC=C1 VNFPBHJOKIVQEB-UHFFFAOYSA-N 0.000 claims description 2
- 239000003221 ear drop Substances 0.000 claims description 2
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- 208000011323 eye infectious disease Diseases 0.000 claims description 2
- 229960001274 fenticonazole Drugs 0.000 claims description 2
- 210000004905 finger nail Anatomy 0.000 claims description 2
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- RFHAOTPXVQNOHP-UHFFFAOYSA-N fluconazole Chemical compound C1=NC=NN1CC(C=1C(=CC(F)=CC=1)F)(O)CN1C=NC=N1 RFHAOTPXVQNOHP-UHFFFAOYSA-N 0.000 claims description 2
- 201000010056 fungal meningitis Diseases 0.000 claims description 2
- 229910052602 gypsum Inorganic materials 0.000 claims description 2
- 239000010440 gypsum Substances 0.000 claims description 2
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- 239000002955 immunomodulating agent Substances 0.000 claims description 2
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- 239000007924 injection Substances 0.000 claims description 2
- 238000002347 injection Methods 0.000 claims description 2
- 230000003601 intercostal effect Effects 0.000 claims description 2
- 238000010255 intramuscular injection Methods 0.000 claims description 2
- 239000007927 intramuscular injection Substances 0.000 claims description 2
- 239000007928 intraperitoneal injection Substances 0.000 claims description 2
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- 229960004130 itraconazole Drugs 0.000 claims description 2
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- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 claims description 2
- 229960000988 nystatin Drugs 0.000 claims description 2
- VQOXZBDYSJBXMA-NQTDYLQESA-N nystatin A1 Chemical compound O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/CC/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 VQOXZBDYSJBXMA-NQTDYLQESA-N 0.000 claims description 2
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- JMFOSJNGKJCTMJ-ZHZULCJRSA-N omoconazole Chemical compound C1=CN=CN1C(/C)=C(C=1C(=CC(Cl)=CC=1)Cl)\OCCOC1=CC=C(Cl)C=C1 JMFOSJNGKJCTMJ-ZHZULCJRSA-N 0.000 claims description 2
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- DOMXUEMWDBAQBQ-WEVVVXLNSA-N terbinafine Chemical compound C1=CC=C2C(CN(C\C=C\C#CC(C)(C)C)C)=CC=CC2=C1 DOMXUEMWDBAQBQ-WEVVVXLNSA-N 0.000 claims description 2
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- FUSNMLFNXJSCDI-UHFFFAOYSA-N tolnaftate Chemical compound C=1C=C2C=CC=CC2=CC=1OC(=S)N(C)C1=CC=CC(C)=C1 FUSNMLFNXJSCDI-UHFFFAOYSA-N 0.000 claims 1
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- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
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| US20130004586A1 (en) | 2011-06-24 | 2013-01-03 | Vachon David J | Biologically Efficacious Compositions, Articles of Manufacture and Processes for Producing and/or Using Same |
| CA2842462C (en) | 2011-07-20 | 2020-01-28 | Brigham Young University | Hydrogel materials incorporating eluting ceragenin compound |
| WO2013029055A1 (en) | 2011-08-25 | 2013-02-28 | Brigham Young University | Incorporation of particulate ceragenins in polymers |
| US8932614B2 (en) | 2011-08-25 | 2015-01-13 | Paul B. Savage | Incorporation of particulate ceragenins in polymers |
| WO2013029059A1 (en) | 2011-08-25 | 2013-02-28 | Brigham Young University | Medical devices incorporating ceragenin-containing composites |
| EP2755661A1 (en) | 2011-09-13 | 2014-07-23 | Brigham Young University | Compositions for treating bone diseases and broken bones |
| MX369385B (es) * | 2011-09-13 | 2019-11-07 | Univ Brigham Young | Productos para cicatrizar heridas tisulares. |
| AU2011383326B2 (en) | 2011-12-15 | 2016-01-28 | Colgate-Palmolive Company | Aqueous oral care compositions |
| JP6051230B2 (ja) | 2011-12-21 | 2016-12-27 | ブリガム ヤング ユニバーシティ | 口腔ケア組成物 |
| US20140363780A1 (en) | 2011-12-21 | 2014-12-11 | Brigham Young University | Oral care compositions |
| BR112014021505A2 (pt) | 2012-03-01 | 2017-07-18 | Univ Brigham Young | composições de processamento de alimentos antimicrobianas incluindo compostos de ceragenina e métodos de uso |
| 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 |
| EP3225113B1 (en) | 2012-05-02 | 2020-09-02 | Brigham Young University | Methods for making ceragenin particulate materials |
| EP2846788A1 (en) | 2012-05-11 | 2015-03-18 | Akron Molecules AG | Use of compounds for the treatment of pain |
| KR20140029864A (ko) | 2012-08-30 | 2014-03-11 | 삼성디스플레이 주식회사 | 표시 장치 및 이를 이용한 에어 터치 인식 방법 및 이를 이용한 입체 영상 표시 방법 |
| US9314472B2 (en) | 2012-10-17 | 2016-04-19 | Brigham Young University | Treatment and prevention of mastitis |
| PL2900277T3 (pl) | 2012-12-13 | 2022-05-16 | Immunomedics, Inc. | Dawkowanie immunokoniugatów przeciwciał i sn-38 dla poprawy skuteczności i zmniejszenia toksyczności |
| 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 |
| RU2669800C2 (ru) | 2013-03-15 | 2018-10-16 | Брихэм Янг Юниверсити | Способы лечения воспаления, аутоиммунных расстройств и боли |
| 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 |
| US10441595B2 (en) * | 2014-06-26 | 2019-10-15 | Brigham Young University | Methods for treating fungal infections |
| US10238665B2 (en) | 2014-06-26 | 2019-03-26 | Brigham Young University | Methods for treating fungal infections |
| AU2016250816B2 (en) | 2015-04-22 | 2020-10-22 | Brigham Young University | Cationic steroidal antimicrobial salts |
| WO2016172543A1 (en) | 2015-04-22 | 2016-10-27 | Savage Paul B | Methods for the synthesis of ceragenins |
| US9527883B2 (en) | 2015-04-22 | 2016-12-27 | 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 |
| US20170080128A1 (en) | 2015-09-21 | 2017-03-23 | Brigham Young University | Novel endotracheal tube for the reduction of intubation-related complication in neonates and babies |
| US10226550B2 (en) | 2016-03-11 | 2019-03-12 | Brigham Young University | Cationic steroidal antimicrobial compositions for the treatment of dermal tissue |
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- 2015-06-26 BR BR112016030541-8A patent/BR112016030541B1/pt active IP Right Grant
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- 2015-06-26 CN CN202210362688.2A patent/CN114588166A/zh active Pending
- 2015-06-26 WO PCT/US2015/038029 patent/WO2015200815A1/en not_active Ceased
- 2015-06-26 CA CA2953136A patent/CA2953136C/en active Active
- 2015-06-26 KR KR1020177002469A patent/KR102601412B1/ko active Active
- 2015-06-26 CN CN201580045470.2A patent/CN106900172A/zh active Pending
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2020
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