BE555290A - - Google Patents

Info

Publication number

BE555290A

BE555290A BE555290DA BE555290A BE 555290 A BE555290 A BE 555290A BE 555290D A BE555290D A BE 555290DA BE 555290 A BE555290 A BE 555290A

Authority

BE

Belgium

Prior art keywords

emi

formula

compound

group

halogen

Prior art date

1956-02-25

Links

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• -1 pyrrolidyl Chemical group 0.000 claims description 11
• 229910052736 halogen Inorganic materials 0.000 claims description 7
• 150000002367 halogens Chemical class 0.000 claims description 6
• 238000007327 hydrogenolysis reaction Methods 0.000 claims description 6
• 239000002253 acid Substances 0.000 claims description 4
• 229910052739 hydrogen Inorganic materials 0.000 claims description 4
• 239000001257 hydrogen Substances 0.000 claims description 4
• 125000000217 alkyl group Chemical group 0.000 claims description 3
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 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
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
• 125000005936 piperidyl group Chemical group 0.000 claims description 2
• 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 4
• 125000000490 cinnamyl group Chemical group C(C=CC1=CC=CC=C1)* 0.000 claims 1
• 125000005843 halogen group Chemical group 0.000 claims 1
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
• 150000003856 quaternary ammonium compounds Chemical class 0.000 claims 1
• 150000001875 compounds Chemical class 0.000 description 12
• 239000000047 product Substances 0.000 description 7
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
• 239000003054 catalyst Substances 0.000 description 4
• 238000000034 method Methods 0.000 description 4
• 229950000688 phenothiazine Drugs 0.000 description 4
• 150000002990 phenothiazines Chemical class 0.000 description 4
• 150000003839 salts Chemical class 0.000 description 4
• WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 3
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
• 238000002844 melting Methods 0.000 description 3
• 230000008018 melting Effects 0.000 description 3
• 229910052763 palladium Inorganic materials 0.000 description 3
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
• WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
• 239000003610 charcoal Substances 0.000 description 2
• 238000006243 chemical reaction Methods 0.000 description 2
• 150000002148 esters Chemical class 0.000 description 2
• 238000005984 hydrogenation reaction Methods 0.000 description 2
• 239000000155 melt Substances 0.000 description 2
• 150000003254 radicals Chemical class 0.000 description 2
• 238000001953 recrystallisation Methods 0.000 description 2
• 239000000126 substance Substances 0.000 description 2
• 229940066767 systemic antihistamines phenothiazine derivative Drugs 0.000 description 2
• DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical class C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
• LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
• SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 1
• FLOIPEIJCYCQCB-UHFFFAOYSA-N 3-(3-chlorophenothiazin-10-yl)-n,n-dimethylpropan-1-amine;hydrochloride Chemical compound [Cl-].ClC1=CC=C2N(CCC[NH+](C)C)C3=CC=CC=C3SC2=C1 FLOIPEIJCYCQCB-UHFFFAOYSA-N 0.000 description 1
• NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
• 241001331845 Equus asinus x caballus Species 0.000 description 1
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
• 238000010521 absorption reaction Methods 0.000 description 1
• 230000015572 biosynthetic process Effects 0.000 description 1
• 229910052799 carbon Inorganic materials 0.000 description 1
• 239000003518 caustics Substances 0.000 description 1
• MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
• 238000001914 filtration Methods 0.000 description 1
• 150000002431 hydrogen Chemical group 0.000 description 1
• LLCOIQRNSJBFSN-UHFFFAOYSA-N methane;sulfurochloridic acid Chemical compound C.OS(Cl)(=O)=O LLCOIQRNSJBFSN-UHFFFAOYSA-N 0.000 description 1
• 239000000203 mixture Substances 0.000 description 1
• 150000002825 nitriles Chemical class 0.000 description 1
• 229910052757 nitrogen Inorganic materials 0.000 description 1
• 239000003208 petroleum Substances 0.000 description 1
• 239000002244 precipitate Substances 0.000 description 1
• 150000003138 primary alcohols Chemical class 0.000 description 1
• 125000001424 substituent group Chemical group 0.000 description 1
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
• 239000006188 syrup Substances 0.000 description 1
• 235000020357 syrup Nutrition 0.000 description 1
• 150000003512 tertiary amines Chemical class 0.000 description 1
• 238000005406 washing Methods 0.000 description 1