KR20170028979A - 주쇄 폴리아민 - Google Patents
주쇄 폴리아민 Download PDFInfo
- Publication number
- KR20170028979A KR20170028979A KR1020177003470A KR20177003470A KR20170028979A KR 20170028979 A KR20170028979 A KR 20170028979A KR 1020177003470 A KR1020177003470 A KR 1020177003470A KR 20177003470 A KR20177003470 A KR 20177003470A KR 20170028979 A KR20170028979 A KR 20170028979A
- Authority
- KR
- South Korea
- Prior art keywords
- alkyl
- compound
- cycloalkyl
- cooh
- integer
- 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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- 229920000768 polyamine Polymers 0.000 title abstract description 100
- 229920000642 polymer Polymers 0.000 claims abstract description 103
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 57
- 206010028116 Mucosal inflammation Diseases 0.000 claims abstract description 56
- 201000010927 Mucositis Diseases 0.000 claims abstract description 56
- 208000035473 Communicable disease Diseases 0.000 claims abstract description 46
- 208000003265 stomatitis Diseases 0.000 claims abstract description 42
- 230000002265 prevention Effects 0.000 claims abstract description 22
- 208000031650 Surgical Wound Infection Diseases 0.000 claims abstract description 17
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 509
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 243
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 232
- 150000001875 compounds Chemical class 0.000 claims description 207
- 125000001072 heteroaryl group Chemical group 0.000 claims description 133
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 129
- 125000005915 C6-C14 aryl group Chemical group 0.000 claims description 125
- 238000000034 method Methods 0.000 claims description 123
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 119
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 106
- 208000015181 infectious disease Diseases 0.000 claims description 100
- -1 dihydroxypropyl Chemical group 0.000 claims description 98
- 150000001408 amides Chemical class 0.000 claims description 73
- 206010057190 Respiratory tract infections Diseases 0.000 claims description 72
- 239000000126 substance Substances 0.000 claims description 52
- 125000003368 amide group Chemical group 0.000 claims description 48
- 229910052799 carbon Inorganic materials 0.000 claims description 45
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 43
- 201000010099 disease Diseases 0.000 claims description 39
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 39
- 241000589517 Pseudomonas aeruginosa Species 0.000 claims description 33
- 229910052739 hydrogen Inorganic materials 0.000 claims description 31
- 208000032376 Lung infection Diseases 0.000 claims description 30
- 150000003839 salts Chemical class 0.000 claims description 30
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 27
- 125000000217 alkyl group Chemical group 0.000 claims description 27
- 150000001450 anions Chemical class 0.000 claims description 27
- 125000005349 heteroarylcycloalkyl group Chemical group 0.000 claims description 25
- 201000003883 Cystic fibrosis Diseases 0.000 claims description 23
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims description 16
- QRJZGVVKGFIGLI-UHFFFAOYSA-N 2-phenylguanidine Chemical group NC(=N)NC1=CC=CC=C1 QRJZGVVKGFIGLI-UHFFFAOYSA-N 0.000 claims description 15
- 230000002685 pulmonary effect Effects 0.000 claims description 14
- 150000003973 alkyl amines Chemical class 0.000 claims description 12
- 125000004429 atom Chemical group 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- PJJJBBJSCAKJQF-UHFFFAOYSA-N guanidinium chloride Chemical group [Cl-].NC(N)=[NH2+] PJJJBBJSCAKJQF-UHFFFAOYSA-N 0.000 claims description 6
- 229910052698 phosphorus Inorganic materials 0.000 claims description 5
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 10
- 125000001475 halogen functional group Chemical group 0.000 claims 8
- 206010048685 Oral infection Diseases 0.000 claims 1
- 239000004952 Polyamide Substances 0.000 claims 1
- 229920002647 polyamide Polymers 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 abstract description 12
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 abstract description 4
- 239000000825 pharmaceutical preparation Substances 0.000 abstract description 2
- 239000000243 solution Substances 0.000 description 111
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 105
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 102
- 238000005119 centrifugation Methods 0.000 description 94
- 239000011541 reaction mixture Substances 0.000 description 94
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 93
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 84
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 78
- 239000007787 solid Substances 0.000 description 72
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 66
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 66
- 238000006243 chemical reaction Methods 0.000 description 58
- 239000002904 solvent Substances 0.000 description 46
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 45
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 41
- 230000015572 biosynthetic process Effects 0.000 description 39
- 238000003786 synthesis reaction Methods 0.000 description 37
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 36
- 238000001914 filtration Methods 0.000 description 34
- 238000001990 intravenous administration Methods 0.000 description 33
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 33
- 239000000706 filtrate Substances 0.000 description 31
- 239000002244 precipitate Substances 0.000 description 31
- 238000004108 freeze drying Methods 0.000 description 30
- 239000012528 membrane Substances 0.000 description 29
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 27
- 239000007864 aqueous solution Substances 0.000 description 23
- 229920001577 copolymer Polymers 0.000 description 23
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 22
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 22
- 125000003118 aryl group Chemical group 0.000 description 22
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 22
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 17
- 125000005843 halogen group Chemical group 0.000 description 17
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 15
- OXEZLYIDQPBCBB-UHFFFAOYSA-N 4-(3-piperidin-4-ylpropyl)piperidine Chemical compound C1CNCCC1CCCC1CCNCC1 OXEZLYIDQPBCBB-UHFFFAOYSA-N 0.000 description 14
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 11
- 235000019341 magnesium sulphate Nutrition 0.000 description 11
- SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical compound O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 description 10
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 10
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000008346 aqueous phase Substances 0.000 description 9
- 239000012267 brine Substances 0.000 description 9
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- 239000000377 silicon dioxide Substances 0.000 description 9
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 9
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical compound CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 8
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 8
- 125000001931 aliphatic group Chemical group 0.000 description 8
- 238000003556 assay Methods 0.000 description 8
- 210000004027 cell Anatomy 0.000 description 8
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 239000003814 drug Substances 0.000 description 8
- 229940079593 drug Drugs 0.000 description 8
- 239000001257 hydrogen Substances 0.000 description 7
- 210000004072 lung Anatomy 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
- 230000008901 benefit Effects 0.000 description 6
- 125000000524 functional group Chemical group 0.000 description 6
- 239000001301 oxygen Substances 0.000 description 6
- 229920001223 polyethylene glycol Chemical group 0.000 description 6
- 230000000069 prophylactic effect Effects 0.000 description 6
- 230000001225 therapeutic effect Effects 0.000 description 6
- JVVKVEQZDLEVTI-UHFFFAOYSA-N 1-pentyl-4-[3-(1-pentylpiperidin-4-yl)propyl]piperidine Chemical compound CCCCCN1CCC(CCCC2CCN(CCCCC)CC2)CC1 JVVKVEQZDLEVTI-UHFFFAOYSA-N 0.000 description 5
- KKPHCGQBSWMCNS-UHFFFAOYSA-N 3-[4-[3-[1-(3-aminopropyl)piperidin-4-yl]propyl]piperidin-1-yl]propan-1-amine Chemical compound NCCCN1CCC(CC1)CCCC1CCN(CC1)CCCN KKPHCGQBSWMCNS-UHFFFAOYSA-N 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 238000000502 dialysis Methods 0.000 description 5
- 150000004985 diamines Chemical class 0.000 description 5
- 150000005690 diesters Chemical class 0.000 description 5
- 229940015043 glyoxal Drugs 0.000 description 5
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 5
- 231100000682 maximum tolerated dose Toxicity 0.000 description 5
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 5
- 239000001294 propane Substances 0.000 description 5
- 125000006413 ring segment Chemical group 0.000 description 5
- 229910052717 sulfur Inorganic materials 0.000 description 5
- 239000011593 sulfur Substances 0.000 description 5
- 238000001356 surgical procedure Methods 0.000 description 5
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 4
- 125000004042 4-aminobutyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])N([H])[H] 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical group N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 4
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 4
- PCSMJKASWLYICJ-UHFFFAOYSA-N Succinic aldehyde Chemical compound O=CCCC=O PCSMJKASWLYICJ-UHFFFAOYSA-N 0.000 description 4
- 239000004599 antimicrobial Substances 0.000 description 4
- 230000001684 chronic effect Effects 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- 238000002784 cytotoxicity assay Methods 0.000 description 4
- 231100000263 cytotoxicity test Toxicity 0.000 description 4
- WRZXKWFJEFFURH-UHFFFAOYSA-N dodecaethylene glycol Chemical compound OCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCO WRZXKWFJEFFURH-UHFFFAOYSA-N 0.000 description 4
- 210000003097 mucus Anatomy 0.000 description 4
- FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 4
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 4
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 3
- BDNKZNFMNDZQMI-UHFFFAOYSA-N 1,3-diisopropylcarbodiimide Chemical compound CC(C)N=C=NC(C)C BDNKZNFMNDZQMI-UHFFFAOYSA-N 0.000 description 3
- AMBFNDRKYCJLNH-UHFFFAOYSA-N 1-(3-piperidin-1-ylpropyl)piperidine Chemical compound C1CCCCN1CCCN1CCCCC1 AMBFNDRKYCJLNH-UHFFFAOYSA-N 0.000 description 3
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- 239000002202 Polyethylene glycol Chemical group 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 208000025865 Ulcer Diseases 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
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- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 3
- 230000005587 bubbling Effects 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- BGRWYRAHAFMIBJ-UHFFFAOYSA-N diisopropylcarbodiimide Natural products CC(C)NC(=O)NC(C)C BGRWYRAHAFMIBJ-UHFFFAOYSA-N 0.000 description 3
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- 238000000338 in vitro Methods 0.000 description 3
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 description 3
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- RIYFDCXURUKYPE-UHFFFAOYSA-N n5-hexanoylspermidine Chemical compound CCCCCC(=O)N(CCCN)CCCCN RIYFDCXURUKYPE-UHFFFAOYSA-N 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
- 239000000546 pharmaceutical excipient Substances 0.000 description 3
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- 239000000843 powder Substances 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
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- 239000012279 sodium borohydride Substances 0.000 description 3
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- 125000001424 substituent group Chemical group 0.000 description 3
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- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 3
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- PVMIWQRYEVGYJK-ZVAWYAOSSA-N (2S)-6-amino-2-[[4-[[6-amino-1-(3-aminopropylamino)-1-oxohexan-2-yl]amino]-6-(3-methylbutylsulfanyl)-1,3,5-triazin-2-yl]amino]hexanoic acid Chemical compound NCCCCC(C(=O)NCCCN)NC1=NC(=NC(=N1)SCCC(C)C)N[C@@H](CCCCN)C(=O)O PVMIWQRYEVGYJK-ZVAWYAOSSA-N 0.000 description 2
- IIXYSYIDGODCPA-UHFFFAOYSA-N 1-(4-butoxybutyl)-4-[3-[1-(4-butoxybutyl)piperidin-4-yl]propyl]piperidine Chemical compound C(CCC1CCN(CC1)CCCCOCCCC)C1CCN(CC1)CCCCOCCCC IIXYSYIDGODCPA-UHFFFAOYSA-N 0.000 description 2
- QZDNQECFESEXPA-UHFFFAOYSA-N 2-[[4-(2-aminoethylsulfanyl)-1,3,5-triazin-2-yl]amino]-N-(3-aminopropyl)-4-methylpentanamide Chemical compound NCCSC1=NC=NC(=N1)NC(C(=O)NCCCN)CC(C)C QZDNQECFESEXPA-UHFFFAOYSA-N 0.000 description 2
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- 108010088751 Albumins Proteins 0.000 description 2
- 240000000662 Anethum graveolens Species 0.000 description 2
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- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- BCPFWSWROVXGQA-UHFFFAOYSA-N CC(C)(C)CC(C)(C)NC(N)=N Chemical compound CC(C)(C)CC(C)(C)NC(N)=N BCPFWSWROVXGQA-UHFFFAOYSA-N 0.000 description 2
- ZIWIAZVGSHKNQE-UHFFFAOYSA-N CC(C)(C)CC(C)(C)NC(N)NC Chemical compound CC(C)(C)CC(C)(C)NC(N)NC ZIWIAZVGSHKNQE-UHFFFAOYSA-N 0.000 description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 2
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- 241000606768 Haemophilus influenzae Species 0.000 description 2
- GIJGXNFNUUFEGH-UHFFFAOYSA-N Isopentyl mercaptan Chemical compound CC(C)CCS GIJGXNFNUUFEGH-UHFFFAOYSA-N 0.000 description 2
- YKNIGEZABHBMFY-UHFFFAOYSA-N N-(4-aminobutyl)-N-[3-(ethylamino)propyl]propanamide Chemical compound NCCCCN(C(CC)=O)CCCNCC YKNIGEZABHBMFY-UHFFFAOYSA-N 0.000 description 2
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical compound CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 208000002847 Surgical Wound Diseases 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 239000003242 anti bacterial agent Substances 0.000 description 2
- 229940088710 antibiotic agent Drugs 0.000 description 2
- 238000009635 antibiotic susceptibility testing Methods 0.000 description 2
- 229940121375 antifungal agent Drugs 0.000 description 2
- 239000003429 antifungal agent Substances 0.000 description 2
- 239000003443 antiviral agent Substances 0.000 description 2
- 208000022362 bacterial infectious disease Diseases 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 2
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- C08G73/028—Polyamidoamines
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G73/0644—Poly(1,3,5)triazines
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- C—CHEMISTRY; METALLURGY
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- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Saccharide Compounds (AREA)
- Phenolic Resins Or Amino Resins (AREA)
- Hydrogenated Pyridines (AREA)
- Polyamides (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
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| US201462023330P | 2014-07-11 | 2014-07-11 | |
| US62/023,330 | 2014-07-11 | ||
| PCT/US2015/039881 WO2016007821A2 (en) | 2014-07-11 | 2015-07-10 | Main chain polyamines |
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| KR20170028979A true KR20170028979A (ko) | 2017-03-14 |
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| US10301254B2 (en) | 2015-04-23 | 2019-05-28 | Temple University—Of the Commonwealth System of Higher Education | Substituted polycationic multi-quaternary ammonium salts as antimicrobial agents |
| US11111216B2 (en) | 2016-10-26 | 2021-09-07 | Temple University-Of The Commonwealth System Of Higher Education | Polycationic amphiphiles as antimicrobial agents and methods using same |
| GB201700404D0 (en) * | 2017-01-10 | 2017-02-22 | Saraswati Res And Dev Inst | Compounds and composistions |
| GB2584074B (en) | 2019-04-16 | 2021-08-11 | Alectrona Pte Ltd | Monoterpene phenol derivatives |
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| BE793157A (fr) * | 1971-12-21 | 1973-06-21 | Beecham Group Ltd | Substance antivirale |
| IT981412B (it) * | 1973-03-15 | 1974-10-10 | Montedison Spa | Poliammidi da acidi eterociclici aromatici ortocarbossilici e pro cedimento per prepararle |
| US4013507A (en) * | 1973-09-18 | 1977-03-22 | California Institute Of Technology | Ionene polymers for selectively inhibiting the vitro growth of malignant cells |
| USRE38417E1 (en) * | 1986-12-02 | 2004-02-03 | University Of Florida Research Foundation, Inc. | Anti-neoplastic, anti-viral or anti-retroviral spermine derivatives |
| CA1305425C (en) * | 1986-12-02 | 1992-07-21 | Raymond J. Bergeron | Anti-neoplastic spermine derivative |
| JPH02116843A (ja) * | 1988-10-27 | 1990-05-01 | Konica Corp | 帯電防止されたハロゲン化銀写真感光材料 |
| JP2847164B2 (ja) * | 1989-05-19 | 1999-01-13 | ダウコーニングアジア株式会社 | 繊維体用抗菌剤 |
| DE10065710A1 (de) * | 2000-12-29 | 2002-07-04 | Bayer Ag | Arzneimittel enthaltend ein Polyamin als Wirksubstanz |
| US6955806B2 (en) * | 2001-01-18 | 2005-10-18 | Genzyme Corporation | Ionene polymers and their use as antimicrobial agents |
| WO2004046223A2 (en) * | 2002-11-19 | 2004-06-03 | Genzyme Corporation | Polyionene polymers with hydrolyzable linkages |
| WO2004046109A2 (en) * | 2002-11-19 | 2004-06-03 | Genzyme Corporation | Ionene oligomers and polymers |
| WO2004045629A1 (en) * | 2002-11-19 | 2004-06-03 | Genzyme Corporation | Polyionenes for treating infections associated with cystic fibrosis |
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| US8853457B2 (en) * | 2010-01-04 | 2014-10-07 | Rhodia Operations | Polyamine and method for producing thereof |
| KR101291642B1 (ko) * | 2010-03-03 | 2013-08-01 | 성균관대학교산학협력단 | 폴리(아미도 아민) 올리고머 하이드로젤 조성물 및 이를 이용한 약물전달체 |
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| MX373164B (es) * | 2013-03-15 | 2020-05-07 | Genzyme Corp | Composiciones antimicrobianas de poliamida y tratamiento de mastitis. |
-
2015
- 2015-07-10 CN CN201580048444.5A patent/CN106687504A/zh active Pending
- 2015-07-10 AR ARP150102211A patent/AR101184A1/es unknown
- 2015-07-10 US US15/325,290 patent/US20170182087A1/en not_active Abandoned
- 2015-07-10 JP JP2017501288A patent/JP6765363B2/ja not_active Expired - Fee Related
- 2015-07-10 KR KR1020177003470A patent/KR20170028979A/ko not_active Withdrawn
- 2015-07-10 SG SG11201610886VA patent/SG11201610886VA/en unknown
- 2015-07-10 AU AU2015287661A patent/AU2015287661B2/en not_active Ceased
- 2015-07-10 WO PCT/US2015/039881 patent/WO2016007821A2/en not_active Ceased
- 2015-07-10 EP EP15739481.8A patent/EP3189091A2/en not_active Withdrawn
- 2015-07-10 MX MX2017000447A patent/MX2017000447A/es unknown
- 2015-07-10 BR BR112017000258A patent/BR112017000258A2/pt not_active Application Discontinuation
- 2015-07-10 RU RU2017104223A patent/RU2017104223A/ru not_active Application Discontinuation
- 2015-07-10 CA CA2954768A patent/CA2954768A1/en not_active Abandoned
- 2015-07-13 TW TW104122474A patent/TW201615694A/zh unknown
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2017
- 2017-01-08 IL IL249963A patent/IL249963A0/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU2015287661B2 (en) | 2019-07-11 |
| SG11201610886VA (en) | 2017-01-27 |
| JP6765363B2 (ja) | 2020-10-07 |
| EP3189091A2 (en) | 2017-07-12 |
| US20170182087A1 (en) | 2017-06-29 |
| AU2015287661A1 (en) | 2017-02-02 |
| MX2017000447A (es) | 2017-04-27 |
| CA2954768A1 (en) | 2016-01-14 |
| WO2016007821A2 (en) | 2016-01-14 |
| TW201615694A (zh) | 2016-05-01 |
| WO2016007821A3 (en) | 2016-05-19 |
| RU2017104223A (ru) | 2018-08-14 |
| JP2017526767A (ja) | 2017-09-14 |
| IL249963A0 (en) | 2017-03-30 |
| BR112017000258A2 (pt) | 2017-10-31 |
| AR101184A1 (es) | 2016-11-30 |
| CN106687504A (zh) | 2017-05-17 |
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