PL55444B1 - - Google Patents

Info

Publication number

PL55444B1

PL55444B1 PL111474A PL11147465A PL55444B1 PL 55444 B1 PL55444 B1 PL 55444B1 PL 111474 A PL111474 A PL 111474A PL 11147465 A PL11147465 A PL 11147465A PL 55444 B1 PL55444 B1 PL 55444B1

Authority

PL

Poland

Prior art keywords

amine

formula

alcohol

alkyl

calculated

Prior art date

1965-11-05

Links

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• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 12
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 11
• -1 alkyl radical Chemical group 0.000 claims description 11
• 239000000460 chlorine Substances 0.000 claims description 10
• 150000001412 amines Chemical class 0.000 claims description 9
• 150000001875 compounds Chemical class 0.000 claims description 6
• 238000000034 method Methods 0.000 claims description 5
• 239000003960 organic solvent Substances 0.000 claims description 5
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
• 239000000203 mixture Substances 0.000 claims description 4
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
• 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 3
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 3
• YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 claims description 3
• HLHNOIAOWQFNGW-UHFFFAOYSA-N 3-bromo-4-hydroxybenzonitrile Chemical compound OC1=CC=C(C#N)C=C1Br HLHNOIAOWQFNGW-UHFFFAOYSA-N 0.000 claims description 2
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
• OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical group [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 claims description 2
• 125000003342 alkenyl group Chemical group 0.000 claims description 2
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
• 229910052794 bromium Chemical group 0.000 claims description 2
• 125000004432 carbon atom Chemical group C* 0.000 claims description 2
• 229910052801 chlorine Inorganic materials 0.000 claims description 2
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
• 238000002360 preparation method Methods 0.000 claims description 2
• 238000002844 melting Methods 0.000 claims 3
• 230000008018 melting Effects 0.000 claims 3
• 125000000217 alkyl group Chemical group 0.000 claims 2
• 238000000921 elemental analysis Methods 0.000 claims 2
• WPWHSFAFEBZWBB-UHFFFAOYSA-N 1-butyl radical Chemical compound [CH2]CCC WPWHSFAFEBZWBB-UHFFFAOYSA-N 0.000 claims 1
• 125000002723 alicyclic group Chemical group 0.000 claims 1
• SJSWRKNSCWKNIR-UHFFFAOYSA-N azane;dihydrochloride Chemical compound N.Cl.Cl SJSWRKNSCWKNIR-UHFFFAOYSA-N 0.000 claims 1
• 238000001816 cooling Methods 0.000 claims 1
• 239000012043 crude product Substances 0.000 claims 1
• 238000002425 crystallisation Methods 0.000 claims 1
• 230000008025 crystallization Effects 0.000 claims 1
• 230000009089 cytolysis Effects 0.000 claims 1
• 238000000354 decomposition reaction Methods 0.000 claims 1
• 238000010586 diagram Methods 0.000 claims 1
• 239000007789 gas Substances 0.000 claims 1
• 239000002798 polar solvent Substances 0.000 claims 1
• 229920006395 saturated elastomer Polymers 0.000 claims 1
• 239000002904 solvent Substances 0.000 claims 1
• LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 16
• 238000006243 chemical reaction Methods 0.000 description 5
• 239000002253 acid Substances 0.000 description 4
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
• 241000699670 Mus sp. Species 0.000 description 2
• 230000000259 anti-tumor effect Effects 0.000 description 2
• 239000007795 chemical reaction product Substances 0.000 description 2
• 150000003141 primary amines Chemical class 0.000 description 2
• 239000011541 reaction mixture Substances 0.000 description 2
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
• 235000014785 Bergenia crassifolia Nutrition 0.000 description 1
• 240000004972 Bergenia crassifolia Species 0.000 description 1
• 101100037762 Caenorhabditis elegans rnh-2 gene Proteins 0.000 description 1
• 241000238631 Hexapoda Species 0.000 description 1
• 206010028980 Neoplasm Diseases 0.000 description 1
• 241000700605 Viruses Species 0.000 description 1
• 230000002378 acidificating effect Effects 0.000 description 1
• 230000004071 biological effect Effects 0.000 description 1
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
• 230000000694 effects Effects 0.000 description 1
• 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
• 238000010438 heat treatment Methods 0.000 description 1
• 125000000623 heterocyclic group Chemical group 0.000 description 1
• 150000002466 imines Chemical class 0.000 description 1
• 238000000338 in vitro Methods 0.000 description 1
• 230000002779 inactivation Effects 0.000 description 1
• 239000000543 intermediate Substances 0.000 description 1
• 238000002955 isolation Methods 0.000 description 1
• 150000003254 radicals Chemical class 0.000 description 1
• 230000001954 sterilising effect Effects 0.000 description 1
• 238000003786 synthesis reaction Methods 0.000 description 1
• 231100000331 toxic Toxicity 0.000 description 1
• 230000002588 toxic effect Effects 0.000 description 1