CA1088569A - Diphenyl-alkyl polyamine compounds - Google Patents
Diphenyl-alkyl polyamine compoundsInfo
- Publication number
- CA1088569A CA1088569A CA259,706A CA259706A CA1088569A CA 1088569 A CA1088569 A CA 1088569A CA 259706 A CA259706 A CA 259706A CA 1088569 A CA1088569 A CA 1088569A
- Authority
- CA
- Canada
- Prior art keywords
- butylphenyl
- triazanonane
- hydrogen
- heptyl
- prepared
- 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.)
- Expired
Links
- 150000001875 compounds Chemical class 0.000 title claims description 26
- 229920000768 polyamine Polymers 0.000 title abstract description 19
- 238000002360 preparation method Methods 0.000 claims abstract description 9
- 238000000034 method Methods 0.000 claims description 29
- -1 aminopropyl Chemical group 0.000 claims description 21
- 150000002576 ketones Chemical class 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 239000000047 product Substances 0.000 claims description 16
- 150000001412 amines Chemical class 0.000 claims description 14
- 239000000126 substance Substances 0.000 claims description 14
- 125000004990 dihydroxyalkyl group Chemical group 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 9
- OTBHHUPVCYLGQO-UHFFFAOYSA-N bis(3-aminopropyl)amine Chemical compound NCCCNCCCN OTBHHUPVCYLGQO-UHFFFAOYSA-N 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 claims description 5
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 5
- ISWDNSXWJAABIV-UHFFFAOYSA-N 1,5-bis(4-propan-2-ylphenyl)pentan-3-one Chemical compound C1=CC(C(C)C)=CC=C1CCC(=O)CCC1=CC=C(C(C)C)C=C1 ISWDNSXWJAABIV-UHFFFAOYSA-N 0.000 claims description 4
- OGPAWPFGIJXWOI-UHFFFAOYSA-N 1,7-bis(4-tert-butylphenyl)heptan-4-one Chemical compound C1=CC(C(C)(C)C)=CC=C1CCCC(=O)CCCC1=CC=C(C(C)(C)C)C=C1 OGPAWPFGIJXWOI-UHFFFAOYSA-N 0.000 claims description 4
- ZAXCZCOUDLENMH-UHFFFAOYSA-N 3,3,3-tetramine Chemical compound NCCCNCCCNCCCN ZAXCZCOUDLENMH-UHFFFAOYSA-N 0.000 claims description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
- CONJOKWUCFGRHI-UHFFFAOYSA-N 1,7-bis(5-tert-butyl-2-methylphenyl)heptan-4-one Chemical compound CC1=CC=C(C(C)(C)C)C=C1CCCC(=O)CCCC1=CC(C(C)(C)C)=CC=C1C CONJOKWUCFGRHI-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- OSGPGEAQELLQCB-UHFFFAOYSA-N 1,5-bis(2,4,6-trimethylphenyl)pentan-3-one Chemical compound CC1=CC(C)=CC(C)=C1CCC(=O)CCC1=C(C)C=C(C)C=C1C OSGPGEAQELLQCB-UHFFFAOYSA-N 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims 8
- 125000004103 aminoalkyl group Chemical group 0.000 claims 2
- MHWGYSANIMPWPV-UHFFFAOYSA-N n'-[2-[2-[1,7-bis(4-tert-butylphenyl)heptan-4-ylamino]ethylamino]ethyl]ethane-1,2-diamine Chemical compound C1=CC(C(C)(C)C)=CC=C1CCCC(NCCNCCNCCN)CCCC1=CC=C(C(C)(C)C)C=C1 MHWGYSANIMPWPV-UHFFFAOYSA-N 0.000 claims 2
- HEXIYJAQAXKPFE-UHFFFAOYSA-N n'-[2-[2-[1,7-bis(5-tert-butyl-2-methylphenyl)heptan-4-ylamino]ethylamino]ethyl]ethane-1,2-diamine Chemical compound CC1=CC=C(C(C)(C)C)C=C1CCCC(NCCNCCNCCN)CCCC1=CC(C(C)(C)C)=CC=C1C HEXIYJAQAXKPFE-UHFFFAOYSA-N 0.000 claims 2
- LFXOLMRCILNIIZ-UHFFFAOYSA-N n'-[3-[1,5-bis(2,4,6-trimethylphenyl)pentan-3-ylamino]propyl]propane-1,3-diamine Chemical compound CC1=CC(C)=CC(C)=C1CCC(NCCCNCCCN)CCC1=C(C)C=C(C)C=C1C LFXOLMRCILNIIZ-UHFFFAOYSA-N 0.000 claims 2
- XFCNUFOJGXUIRS-UHFFFAOYSA-N n'-[3-[1,5-bis(4-propan-2-ylphenyl)pentan-3-ylamino]propyl]propane-1,3-diamine Chemical compound C1=CC(C(C)C)=CC=C1CCC(NCCCNCCCN)CCC1=CC=C(C(C)C)C=C1 XFCNUFOJGXUIRS-UHFFFAOYSA-N 0.000 claims 2
- ZISQOKUWSDPPKN-UHFFFAOYSA-N n'-[3-[1,7-bis(5-tert-butyl-2-methylphenyl)heptan-4-ylamino]propyl]propane-1,3-diamine Chemical compound CC1=CC=C(C(C)(C)C)C=C1CCCC(NCCCNCCCN)CCCC1=CC(C(C)(C)C)=CC=C1C ZISQOKUWSDPPKN-UHFFFAOYSA-N 0.000 claims 2
- GGNFPQZRUXPRPN-UHFFFAOYSA-N n'-[3-[3-[1,7-bis(4-tert-butylphenyl)heptan-4-ylamino]propylamino]propyl]propane-1,3-diamine Chemical compound C1=CC(C(C)(C)C)=CC=C1CCCC(NCCCNCCCNCCCN)CCCC1=CC=C(C(C)(C)C)C=C1 GGNFPQZRUXPRPN-UHFFFAOYSA-N 0.000 claims 2
- 229960001124 trientine Drugs 0.000 claims 2
- 239000004599 antimicrobial Substances 0.000 abstract description 6
- 241000195493 Cryptophyta Species 0.000 abstract description 4
- 235000010290 biphenyl Nutrition 0.000 abstract description 4
- 239000004305 biphenyl Substances 0.000 abstract description 4
- 125000006267 biphenyl group Chemical group 0.000 abstract description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 abstract description 4
- 208000002874 Acne Vulgaris Diseases 0.000 abstract description 3
- 206010000496 acne Diseases 0.000 abstract description 3
- 230000001580 bacterial effect Effects 0.000 abstract description 3
- 231100000053 low toxicity Toxicity 0.000 abstract description 3
- 239000002537 cosmetic Substances 0.000 abstract description 2
- 239000003112 inhibitor Substances 0.000 abstract description 2
- 239000000344 soap Substances 0.000 abstract description 2
- 230000000699 topical effect Effects 0.000 abstract description 2
- 239000013543 active substance Substances 0.000 abstract 1
- 230000000844 anti-bacterial effect Effects 0.000 abstract 1
- 239000003755 preservative agent Substances 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 41
- 238000006243 chemical reaction Methods 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- 230000002829 reductive effect Effects 0.000 description 17
- 239000000203 mixture Substances 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- 239000002262 Schiff base Substances 0.000 description 13
- 150000004753 Schiff bases Chemical class 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 11
- 239000003921 oil Substances 0.000 description 11
- 238000010992 reflux Methods 0.000 description 11
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 239000003054 catalyst Substances 0.000 description 9
- 150000004820 halides Chemical class 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 241000894006 Bacteria Species 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- 150000002825 nitriles Chemical class 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 239000007818 Grignard reagent Substances 0.000 description 5
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 5
- 150000004795 grignard reagents Chemical class 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- 150000001450 anions Chemical class 0.000 description 4
- 239000003638 chemical reducing agent Substances 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 229910052742 iron Inorganic materials 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- 241000186427 Cutibacterium acnes Species 0.000 description 3
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 3
- 241000233866 Fungi Species 0.000 description 3
- 229910019020 PtO2 Inorganic materials 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical compound O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 239000012259 ether extract Substances 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 150000002431 hydrogen Chemical group 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 244000005700 microbiome Species 0.000 description 3
- 235000010755 mineral Nutrition 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 229910052697 platinum Inorganic materials 0.000 description 3
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 238000006722 reduction reaction Methods 0.000 description 3
- ATHGHQPFGPMSJY-UHFFFAOYSA-N spermidine Chemical class NCCCCNCCCN ATHGHQPFGPMSJY-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
- 238000010531 catalytic reduction reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 238000006114 decarboxylation reaction Methods 0.000 description 2
- 239000000645 desinfectant Substances 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 238000004508 fractional distillation Methods 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- GKQPCPXONLDCMU-CCEZHUSRSA-N lacidipine Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCC)C1C1=CC=CC=C1\C=C\C(=O)OC(C)(C)C GKQPCPXONLDCMU-CCEZHUSRSA-N 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 230000000813 microbial effect Effects 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 229940051866 mouthwash Drugs 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 2
- SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 150000003141 primary amines Chemical group 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 230000003134 recirculating effect Effects 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- PFNFFQXMRSDOHW-UHFFFAOYSA-N spermine Chemical compound NCCCNCCCCNCCCN PFNFFQXMRSDOHW-UHFFFAOYSA-N 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- 150000003624 transition metals Chemical class 0.000 description 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- 239000003643 water by type Substances 0.000 description 2
- ULPMRIXXHGUZFA-UHFFFAOYSA-N (R)-4-Methyl-3-hexanone Natural products CCC(C)C(=O)CC ULPMRIXXHGUZFA-UHFFFAOYSA-N 0.000 description 1
- YFKBXYGUSOXJGS-UHFFFAOYSA-N 1,3-Diphenyl-2-propanone Chemical compound C=1C=CC=CC=1CC(=O)CC1=CC=CC=C1 YFKBXYGUSOXJGS-UHFFFAOYSA-N 0.000 description 1
- PUYZOZADEJTOAS-UHFFFAOYSA-N 1,3-bis(4-propan-2-ylphenyl)propan-2-one Chemical compound C1=CC(C(C)C)=CC=C1CC(=O)CC1=CC=C(C(C)C)C=C1 PUYZOZADEJTOAS-UHFFFAOYSA-N 0.000 description 1
- BJZBPRYVJCHAKB-UHFFFAOYSA-N 1,3-bis(4-tert-butylphenyl)propan-2-one Chemical compound C1=CC(C(C)(C)C)=CC=C1CC(=O)CC1=CC=C(C(C)(C)C)C=C1 BJZBPRYVJCHAKB-UHFFFAOYSA-N 0.000 description 1
- AFKAOMNABPMCOT-UHFFFAOYSA-N 1,4-bis(4-propan-2-ylphenyl)butan-2-one Chemical compound C1=CC(C(C)C)=CC=C1CCC(=O)CC1=CC=C(C(C)C)C=C1 AFKAOMNABPMCOT-UHFFFAOYSA-N 0.000 description 1
- QACXFKJXAJAVHP-UHFFFAOYSA-N 1,5-bis(2-propan-2-ylphenyl)pentan-3-one Chemical compound CC(C)C1=CC=CC=C1CCC(=O)CCC1=CC=CC=C1C(C)C QACXFKJXAJAVHP-UHFFFAOYSA-N 0.000 description 1
- YABFQBKJLHRNAF-UHFFFAOYSA-N 1,5-bis(4-methylphenyl)pentan-3-one Chemical compound C1=CC(C)=CC=C1CCC(=O)CCC1=CC=C(C)C=C1 YABFQBKJLHRNAF-UHFFFAOYSA-N 0.000 description 1
- QQXIMQSGUZEVAM-UHFFFAOYSA-N 1,5-bis(4-tert-butylphenyl)pentan-3-one Chemical compound C1=CC(C(C)(C)C)=CC=C1CCC(=O)CCC1=CC=C(C(C)(C)C)C=C1 QQXIMQSGUZEVAM-UHFFFAOYSA-N 0.000 description 1
- JENANTGGBLOTIB-UHFFFAOYSA-N 1,5-diphenylpentan-3-one Chemical compound C=1C=CC=CC=1CCC(=O)CCC1=CC=CC=C1 JENANTGGBLOTIB-UHFFFAOYSA-N 0.000 description 1
- RIQUHYIAWLPHOG-UHFFFAOYSA-N 1,7-bis(4-ethylphenyl)heptan-4-one Chemical compound C1=CC(CC)=CC=C1CCCC(=O)CCCC1=CC=C(CC)C=C1 RIQUHYIAWLPHOG-UHFFFAOYSA-N 0.000 description 1
- HNGNWOHSWLPDBF-UHFFFAOYSA-N 1,7-bis(4-methylphenyl)heptan-4-one Chemical compound C1=CC(C)=CC=C1CCCC(=O)CCCC1=CC=C(C)C=C1 HNGNWOHSWLPDBF-UHFFFAOYSA-N 0.000 description 1
- YOEBWNWEBDXJOR-UHFFFAOYSA-N 1,7-bis(4-propan-2-ylphenyl)heptan-4-one Chemical compound C1=CC(C(C)C)=CC=C1CCCC(=O)CCCC1=CC=C(C(C)C)C=C1 YOEBWNWEBDXJOR-UHFFFAOYSA-N 0.000 description 1
- ZNLYIEICWRDFDA-UHFFFAOYSA-N 1,7-diphenylheptan-4-one Chemical compound C=1C=CC=CC=1CCCC(=O)CCCC1=CC=CC=C1 ZNLYIEICWRDFDA-UHFFFAOYSA-N 0.000 description 1
- RJDOLOQANHYDFG-UHFFFAOYSA-N 1,9-bis(2-ethylphenyl)nonan-5-one Chemical compound CCC1=CC=CC=C1CCCCC(=O)CCCCC1=CC=CC=C1CC RJDOLOQANHYDFG-UHFFFAOYSA-N 0.000 description 1
- JIAMHGYWJYSVIM-UHFFFAOYSA-N 1,9-diphenylnonan-5-one Chemical compound C=1C=CC=CC=1CCCCC(=O)CCCCC1=CC=CC=C1 JIAMHGYWJYSVIM-UHFFFAOYSA-N 0.000 description 1
- QUMNRLZRDVNICW-UHFFFAOYSA-N 1-(3,4-dimethylphenyl)-5-(4-propan-2-ylphenyl)pentan-3-one Chemical compound C1=CC(C(C)C)=CC=C1CCC(=O)CCC1=CC=C(C)C(C)=C1 QUMNRLZRDVNICW-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- QGBATQSWEUHONK-UHFFFAOYSA-N 2,6-diphenylheptan-4-one Chemical compound C=1C=CC=CC=1C(C)CC(=O)CC(C)C1=CC=CC=C1 QGBATQSWEUHONK-UHFFFAOYSA-N 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- YTSNVWMTVVGZTI-UHFFFAOYSA-N 2-[2-[2-(2-aminoethylamino)ethylamino]ethylamino]ethanol Chemical compound NCCNCCNCCNCCO YTSNVWMTVVGZTI-UHFFFAOYSA-N 0.000 description 1
- POGBEGTVYWWXSF-UHFFFAOYSA-N 2-[bis(3-aminopropyl)amino]ethanol Chemical compound NCCCN(CCO)CCCN POGBEGTVYWWXSF-UHFFFAOYSA-N 0.000 description 1
- SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical compound OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
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- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/41—Amines
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/48—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation involving decarboxylation
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/213—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing six-membered aromatic rings
- C07C49/215—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing six-membered aromatic rings polycyclic
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
- C10M2201/02—Water
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2215/042—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Alkoxylated derivatives thereof
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/24—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions having hydrocarbon substituents containing thirty or more carbon atoms, e.g. nitrogen derivatives of substituted succinic acid
- C10M2215/26—Amines
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2217/04—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2217/046—Polyamines, i.e. macromoleculars obtained by condensation of more than eleven amine monomers
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2217/06—Macromolecular compounds obtained by functionalisation op polymers with a nitrogen containing compound
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/20—Metal working
- C10N2040/22—Metal working with essential removal of material, e.g. cutting, grinding or drilling
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Dermatology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cosmetics (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Lubricants (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US609,773 | 1975-09-02 | ||
| US05/609,773 US4061775A (en) | 1975-09-02 | 1975-09-02 | Polyamine compounds as antibacterial agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1088569A true CA1088569A (en) | 1980-10-28 |
Family
ID=24442266
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA259,706A Expired CA1088569A (en) | 1975-09-02 | 1976-08-24 | Diphenyl-alkyl polyamine compounds |
Country Status (25)
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IE49936B1 (en) * | 1979-07-11 | 1986-01-08 | Int Minerals & Chem Corp | Zinc-containing antibiotic agents |
| US4311709A (en) * | 1979-12-26 | 1982-01-19 | Merck & Co., Inc. | Loweralkyl substituted diphenyl polyamine as an antimicrobial agent |
| US4340756A (en) * | 1981-02-04 | 1982-07-20 | Merck & Co., Inc. | Polyamine compounds as antibacterial agents |
| US4582822A (en) * | 1984-10-09 | 1986-04-15 | Eli Lilly And Company | Antibiotic A80190, pharmaceutical compositions containing same and method of use |
| US4824863A (en) * | 1985-05-28 | 1989-04-25 | Eli Lilly And Company | Antibiotic A80438 |
| US5785959A (en) * | 1996-08-16 | 1998-07-28 | Revlon Consumer Products Corporation | Nail strengthening compositions and a method for strengthening nails |
| US6096152A (en) * | 1997-04-30 | 2000-08-01 | Kimberly-Clark Worldwide, Inc. | Creped tissue product having a low friction surface and improved wet strength |
| MXPA00009705A (es) * | 1998-04-03 | 2003-07-14 | Univ Manitoba | Uso de poliaminas en el tratamiento de sintomas dermatologicos. |
| US6464830B1 (en) | 2000-11-07 | 2002-10-15 | Kimberly-Clark Worldwide, Inc. | Method for forming a multi-layered paper web |
| US20060270648A1 (en) * | 2005-05-27 | 2006-11-30 | Chung-Dar Lu | Use of polyamines with antibiotics |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2483434A (en) * | 1946-04-08 | 1949-10-04 | Parke Davis & Co | Disubstituted amino-alkyl benzhydryl amines |
| US2781398A (en) * | 1954-11-18 | 1957-02-12 | Union Chimique Belge Sa | Phenyl cyclohexyl bis diethylaminoethanes |
| US3064052A (en) * | 1958-04-17 | 1962-11-13 | Hoffmann La Roche | Symmetrical alicyclic amine derivatives |
| US3197510A (en) * | 1962-03-01 | 1965-07-27 | Universal Oil Prod Co | N1-secondary-alkyl-aminoalkyl alkanolamines |
| GB1109502A (en) * | 1964-04-18 | 1968-04-10 | Fisons Pharmaceuticals Ltd | Substituted n-benzyl-ethylenediamines |
| CH481569A (de) * | 1966-02-25 | 1969-11-30 | R Maag Ag Chem Fab Dielsdorf D | Mittel zur Bekämpfung von Algen |
| US3876702A (en) * | 1968-04-26 | 1975-04-08 | Rudolf Theodor Petersen | N,n-bis-(diphenylalkyl)-alkylendiamine and their salts |
| US3862330A (en) * | 1971-03-18 | 1975-01-21 | Robert P Johnson | N-(c{hd 8{b -c{hd 12 {b alkyl) diaralkylamines used to combat plant fungi |
| US3900565A (en) * | 1971-09-13 | 1975-08-19 | Richardson Merrell Inc | Hypoglycemic compositions containing benzhydryllactamimide derivatives |
| US3823155A (en) * | 1971-12-20 | 1974-07-09 | Gist Brocades Nv | Imidazoline derivatives with diuretic properties |
| NL7304578A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1972-04-24 | 1973-10-26 | ||
| DE2304153A1 (de) | 1973-01-29 | 1974-08-01 | Ichthyol Ges Cordes Hermanni & | Substituierte piperazin- und homopiperazinderivate |
-
1975
- 1975-09-02 US US05/609,773 patent/US4061775A/en not_active Expired - Lifetime
-
1976
- 1976-08-16 NL NL7609085A patent/NL7609085A/xx not_active Application Discontinuation
- 1976-08-17 FI FI762346A patent/FI64572C/fi not_active IP Right Cessation
- 1976-08-18 DK DK372576A patent/DK372576A/da not_active Application Discontinuation
- 1976-08-18 SE SE7609181A patent/SE7609181L/xx not_active Application Discontinuation
- 1976-08-19 NO NO762857A patent/NO142782C/no unknown
- 1976-08-23 IL IL50335A patent/IL50335A/xx unknown
- 1976-08-23 NZ NZ181833A patent/NZ181833A/xx unknown
- 1976-08-24 CH CH1071976A patent/CH621224B/xx not_active IP Right Cessation
- 1976-08-24 AR AR264430A patent/AR223303A1/es active
- 1976-08-24 AU AU17110/76A patent/AU505339B2/en not_active Expired
- 1976-08-24 CA CA259,706A patent/CA1088569A/en not_active Expired
- 1976-08-25 BR BR7605595A patent/BR7605595A/pt unknown
- 1976-08-25 IT IT51026/76A patent/IT1066395B/it active
- 1976-08-27 LU LU75669A patent/LU75669A1/xx unknown
- 1976-08-27 PT PT65522A patent/PT65522A/pt unknown
- 1976-08-31 IE IE1933/76A patent/IE44070B1/en unknown
- 1976-08-31 GB GB36000/76A patent/GB1520598A/en not_active Expired
- 1976-08-31 FR FR7626241A patent/FR2322590A1/fr active Granted
- 1976-09-01 BE BE170269A patent/BE845747A/xx not_active IP Right Cessation
- 1976-09-01 AT AT649376A patent/AT350196B/de not_active IP Right Cessation
- 1976-09-01 DE DE19762639357 patent/DE2639357A1/de not_active Ceased
- 1976-09-01 ZA ZA00765252A patent/ZA765252B/xx unknown
- 1976-09-02 ES ES451188A patent/ES451188A1/es not_active Expired
- 1976-09-02 JP JP51104374A patent/JPS5233655A/ja active Pending
Also Published As
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| Date | Code | Title | Description |
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| MKEX | Expiry |