CN1082534A - 烷酰氨基铵化合物 - Google Patents
烷酰氨基铵化合物 Download PDFInfo
- Publication number
- CN1082534A CN1082534A CN93101376A CN93101376A CN1082534A CN 1082534 A CN1082534 A CN 1082534A CN 93101376 A CN93101376 A CN 93101376A CN 93101376 A CN93101376 A CN 93101376A CN 1082534 A CN1082534 A CN 1082534A
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- CN
- China
- Prior art keywords
- acid
- propyl group
- compound
- sulfenyl
- formula
- 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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- -1 amido ammonium compound Chemical class 0.000 title claims abstract description 63
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 5
- 239000001257 hydrogen Substances 0.000 claims abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000000129 anionic group Chemical group 0.000 claims abstract description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000001301 oxygen Substances 0.000 claims abstract description 3
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 98
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 45
- 229910052799 carbon Inorganic materials 0.000 claims description 21
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 claims description 5
- 125000002837 carbocyclic group Chemical group 0.000 claims description 3
- 125000001118 alkylidene group Chemical group 0.000 abstract description 3
- 230000000694 effects Effects 0.000 abstract description 3
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 125000002769 thiazolinyl group Chemical group 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 77
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 58
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 40
- 238000004519 manufacturing process Methods 0.000 description 40
- 239000002904 solvent Substances 0.000 description 39
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
- 235000019441 ethanol Nutrition 0.000 description 26
- 229950001902 dimevamide Drugs 0.000 description 25
- IPWFJLQDVFKJDU-UHFFFAOYSA-N pentanamide Chemical compound CCCCC(N)=O IPWFJLQDVFKJDU-UHFFFAOYSA-N 0.000 description 25
- 239000002585 base Substances 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 19
- 238000000034 method Methods 0.000 description 19
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 239000003795 chemical substances by application Substances 0.000 description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 14
- 239000002253 acid Substances 0.000 description 14
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 229910052794 bromium Inorganic materials 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
- 125000005843 halogen group Chemical group 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 10
- 238000005160 1H NMR spectroscopy Methods 0.000 description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 239000003513 alkali Substances 0.000 description 9
- 238000009835 boiling Methods 0.000 description 9
- FKVMWDZRDMCIAJ-UHFFFAOYSA-N undecanamide Chemical compound CCCCCCCCCCC(N)=O FKVMWDZRDMCIAJ-UHFFFAOYSA-N 0.000 description 9
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical class [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 8
- 229910052801 chlorine Inorganic materials 0.000 description 8
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 8
- 239000000284 extract Substances 0.000 description 8
- 229910052740 iodine Chemical class 0.000 description 8
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 7
- 235000014113 dietary fatty acids Nutrition 0.000 description 7
- 238000001035 drying Methods 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- 239000000194 fatty acid Substances 0.000 description 7
- 229930195729 fatty acid Natural products 0.000 description 7
- RZJRJXONCZWCBN-UHFFFAOYSA-N octadecane Chemical compound CCCCCCCCCCCCCCCCCC RZJRJXONCZWCBN-UHFFFAOYSA-N 0.000 description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 6
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 6
- 229940038384 octadecane Drugs 0.000 description 6
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 6
- 235000002639 sodium chloride Nutrition 0.000 description 6
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 5
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 235000019198 oils Nutrition 0.000 description 5
- BGHCVCJVXZWKCC-UHFFFAOYSA-N tetradecane Chemical compound CCCCCCCCCCCCCC BGHCVCJVXZWKCC-UHFFFAOYSA-N 0.000 description 5
- 229940005605 valeric acid Drugs 0.000 description 5
- LSEDQAPMYXQDRC-UHFFFAOYSA-N 11-dodecylsulfanylundecanoic acid Chemical compound CCCCCCCCCCCCSCCCCCCCCCCC(O)=O LSEDQAPMYXQDRC-UHFFFAOYSA-N 0.000 description 4
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 4
- AFPHTEQTJZKQAQ-UHFFFAOYSA-N 3-nitrobenzoic acid Chemical compound OC(=O)C1=CC=CC([N+]([O-])=O)=C1 AFPHTEQTJZKQAQ-UHFFFAOYSA-N 0.000 description 4
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- RFFFKMOABOFIDF-UHFFFAOYSA-N Pentanenitrile Chemical compound CCCCC#N RFFFKMOABOFIDF-UHFFFAOYSA-N 0.000 description 4
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- CUBCNYWQJHBXIY-UHFFFAOYSA-N benzoic acid;2-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=CC=C1.OC(=O)C1=CC=CC=C1O CUBCNYWQJHBXIY-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 235000019253 formic acid Nutrition 0.000 description 4
- 239000011630 iodine Substances 0.000 description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 235000015320 potassium carbonate Nutrition 0.000 description 4
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 4
- 235000019260 propionic acid Nutrition 0.000 description 4
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 235000017550 sodium carbonate Nutrition 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- IIYFAKIEWZDVMP-UHFFFAOYSA-N tridecane Chemical compound CCCCCCCCCCCCC IIYFAKIEWZDVMP-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 3
- DNXHEGUUPJUMQT-CBZIJGRNSA-N Estrone Chemical compound OC1=CC=C2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 DNXHEGUUPJUMQT-CBZIJGRNSA-N 0.000 description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 3
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 3
- RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical class C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- SXDBWCPKPHAZSM-UHFFFAOYSA-N bromic acid Chemical compound OBr(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical class CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 238000005755 formation reaction Methods 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- YCOZIPAWZNQLMR-UHFFFAOYSA-N heptane - octane Natural products CCCCCCCCCCCCCCC YCOZIPAWZNQLMR-UHFFFAOYSA-N 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 239000004310 lactic acid Substances 0.000 description 3
- 235000014655 lactic acid Nutrition 0.000 description 3
- 238000002386 leaching Methods 0.000 description 3
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229910017604 nitric acid Inorganic materials 0.000 description 3
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 3
- QJAOYSPHSNGHNC-UHFFFAOYSA-N octadecane-1-thiol Chemical compound CCCCCCCCCCCCCCCCCCS QJAOYSPHSNGHNC-UHFFFAOYSA-N 0.000 description 3
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 229910001961 silver nitrate Inorganic materials 0.000 description 3
- 229910000108 silver(I,III) oxide Inorganic materials 0.000 description 3
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 238000010025 steaming Methods 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- MPDGHEJMBKOTSU-YKLVYJNSSA-N 18beta-glycyrrhetic acid Chemical compound C([C@H]1C2=CC(=O)[C@H]34)[C@@](C)(C(O)=O)CC[C@]1(C)CC[C@@]2(C)[C@]4(C)CC[C@@H]1[C@]3(C)CC[C@H](O)C1(C)C MPDGHEJMBKOTSU-YKLVYJNSSA-N 0.000 description 2
- XYPISWUKQGWYGX-UHFFFAOYSA-N 2,2,2-trifluoroethaneperoxoic acid Chemical compound OOC(=O)C(F)(F)F XYPISWUKQGWYGX-UHFFFAOYSA-N 0.000 description 2
- YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 description 2
- CDBQZFAWRRUUIC-UHFFFAOYSA-N 3-octadecylsulfanylpropanoic acid Chemical compound CCCCCCCCCCCCCCCCCCSCCC(O)=O CDBQZFAWRRUUIC-UHFFFAOYSA-N 0.000 description 2
- OWXXRDGGTZWLQY-UHFFFAOYSA-N 3-tetradecylsulfanylpropanoic acid Chemical compound CCCCCCCCCCCCCCSCCC(O)=O OWXXRDGGTZWLQY-UHFFFAOYSA-N 0.000 description 2
- SQDAZGGFXASXDW-UHFFFAOYSA-N 5-bromo-2-(trifluoromethoxy)pyridine Chemical compound FC(F)(F)OC1=CC=C(Br)C=N1 SQDAZGGFXASXDW-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 229920001287 Chondroitin sulfate Polymers 0.000 description 2
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- MKYBYDHXWVHEJW-UHFFFAOYSA-N N-[1-oxo-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propan-2-yl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(C(C)NC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 MKYBYDHXWVHEJW-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
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- DCAYPVUWAIABOU-UHFFFAOYSA-N alpha-n-hexadecene Natural products CCCCCCCCCCCCCCCC DCAYPVUWAIABOU-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 2
- 229940073608 benzyl chloride Drugs 0.000 description 2
- KVYGGMBOZFWZBQ-UHFFFAOYSA-N benzyl nicotinate Chemical compound C=1C=CN=CC=1C(=O)OCC1=CC=CC=C1 KVYGGMBOZFWZBQ-UHFFFAOYSA-N 0.000 description 2
- VHRGRCVQAFMJIZ-UHFFFAOYSA-N cadaverine Chemical compound NCCCCCN VHRGRCVQAFMJIZ-UHFFFAOYSA-N 0.000 description 2
- 239000004359 castor oil Substances 0.000 description 2
- 235000019438 castor oil Nutrition 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- 229940059329 chondroitin sulfate Drugs 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 230000003750 conditioning effect Effects 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- LVTYICIALWPMFW-UHFFFAOYSA-N diisopropanolamine Chemical compound CC(O)CNCC(C)O LVTYICIALWPMFW-UHFFFAOYSA-N 0.000 description 2
- HOWGUJZVBDQJKV-UHFFFAOYSA-N docosane Chemical compound CCCCCCCCCCCCCCCCCCCCCC HOWGUJZVBDQJKV-UHFFFAOYSA-N 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 2
- 229930182470 glycoside Natural products 0.000 description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C235/10—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atom of at least one of the carboxamide groups bound to an acyclic carbon atom of a hydrocarbon radical substituted by nitrogen atoms not being part of nitro or nitroso groups
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- 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
- A61K8/42—Amides
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q7/00—Preparations for affecting hair growth
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- C—CHEMISTRY; METALLURGY
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Abstract
上式的烷酰氨基铵化合物具有优异的生毛发作
用[式中R1为烷基或环烷基,R2为亚烷基,R3为氢或
烷基,R4为亚烷基,R5和R6相同或不同,为烷基,R7
为烷基,烯基或“苯基取代的烷基”,A为氧或
(式中n为0—2的整数),Xm-为阴离子,m为与X中
阴离子电荷数相应的整数]。
Description
本发明涉及有生发作用的烷酰氨基铵化合物。
目前还不知道与本发明化合物结构类似并具有同样作用的化合物。
本发明目的是提出具有生发作用的新型化合物。
本发明为下式烷酰氨基铵化合物
〔式中R1为1-22碳烷基或3-8碳环烷基,R2为1-15碳亚烷基,R3为氢或1-5碳烷基,R4为2-10碳亚烷基,R5和R6相同或不同,为1-5碳烷基,R7为1-22碳烷基,2-10碳烯基或苯基取代的1-5碳烷基,A为氧或
(式中n为0-2的整数)所示基,Xm-为阴离子,m为相当于X中阴离子电荷数的整数〕。
本发明中1-22碳烷基为甲基,乙基,正丙基,异丙基,正丁基,异丁基,仲丁基,叔丁基,正戊基,异戊基,新戊基,叔戊基,正己基,异己基,正庚基,正辛基,正壬基,正癸基,正十一烷基,正十二烷基,正十三烷基,正十四烷基,正十五烷基,正十六烷基,正十七烷基,正十八烷基,正十九烷基,正二十烷基,正二十一烷基,正二十二烷基等直链或支链烷基。
3-8碳环烷基为环丙基,环丁基,环戊基,环己基,环庚基,环辛基等。
1-15碳亚烷基为亚甲基,亚乙基,三亚甲基,四亚甲基,五亚甲基,六亚甲基,八亚烷基,九亚甲基,十亚甲基,十二亚甲基,十二亚甲基,十三亚甲基,十五亚甲基,亚丙基,1-甲基三亚甲基,2,2-二甲基三亚甲基,1-甲基六亚甲基,乙叉,丙叉,丁叉基直链或支链亚烷基。
1-5碳烷基为甲基,乙基,正丙基,异丙基,正丁基,异丁基,正戊基等直链或支链烷基。
2-10碳亚烷基为上述1-15碳亚烷基中2-10碳亚烷基。
2-10碳烯基为乙烯基,烯丙基,1-丁烯基,戊二烯基,牛儿基等。
苯基取代基的1-5碳烷基为苄基,苯乙基,苯丙基等苯基取代的直链或支链烷基。
Xm-可为氟,氯,溴,碘,硫酸。硝酸,亚硝酸,硫酸甲酯,硫酸乙酯,磷酸二甲酯,甲磺酸,苯磺酸,对甲苯磺酸,甲酸,乙酸,丙酸,乙醇酸,乳酸,溴酸,安息香酸,水杨酸等的阴离子。
本发明化合物可用例如以下方法制成(以下的R1,R2,R3,R4,R5,R6,R7,A和n未作具体限定,其定义同上述),其中将式(Ⅲ)化合物与式(Ⅳ)胺酰胺生成反应而得式(Ⅴ)化合物。
酰胺生成反应在通常的酰胺生成反应条件下进行,如(a)加热脱水法,(b)酰卤法,(c)混合酸酐法,(d)活性酯法,(e)碳化二亚胺法等,优选(a)和(b)法。
(a)法可在无溶剂或有溶剂存在下除去1mol水而进行,无溶剂时反应温度常为130-200℃左右,优选150-170℃,有溶剂时在溶剂沸点下进行。只要溶剂不对反应造成坏影响,则可使用与水的共沸物,如二甲苯等。
(b)法是将式(Ⅲ)化合物与卤化剂反应所得酰卤再与式(Ⅳ)化合物反应,其中式(Ⅲ)化物与等mol量至大过剩量卤化剂(如亚硫酰二氯,五氯化磷,氧氯化磷,草酰氯,亚硫酰二溴,三溴化磷等)在无溶剂或非活性溶剂(如苯,甲苯,四氢呋喃,二氯甲烷,氯仿等)中室温~溶剂沸点下搅拌0.5-10小时而得式(Ⅲ)化合物酰卤,再将其与式(Ⅳ)化合物在无溶剂或溶剂(如二氯甲烷,氯仿,四氯化碳等卤代烃类,乙醚,四氢呋喃,二噁烷等的醚类,苯,甲苯,二甲苯等芳族烃类,乙酸乙酯,乙酸甲酯等酯类,N,N-二甲基甲酰胺,二甲亚砜等非质子极性溶剂等)存在下-30~100℃(优选0-50℃)反应,其中前半反应不必要加催化剂,但可加催化量~等mol量的吡啶,三乙胺,N,N-二甲基甲酰胺等促进反应。
然后再将式(Ⅴ)化合物与式
(式中Y为卤原子)化合物或有R7的酸酯在无溶剂时或溶剂中进行四元化反应而得本发明化合物。
卤原子可为氯原子,溴原子或碘原子,酸酯可为无机酸酯(如硫酸二乙酯,硫酸二甲酯,磷酸三甲酯等)或有机酸酯(如甲磺酸甲酯,苯磺酸甲酯,对甲苯磺酸甲酯,对甲苯磺酸戊酯等),溶剂可为水,丙酮,醇类(如甲醇,乙醇等),二乙醚,苯,乙腈等,反应温度0-150℃沸点。
式(Ⅰ)中Xm-为羧酸(如甲酸,乙酸,丙酸,乙醇酸,乳酸,溴酸,安息香酸,水杨酸等)的化合物可按以下方法制得,其中将前述制造的化合物溶于溶剂并将其与各种形态(如甲酸形,乙酸形,丙酸形,乙醇酸形,乳酸形,溴酸形,安息香酸形,水杨酸形等)阴离子交换树脂进行离子交换而得。
溶剂可用水,醇类(如甲醇,乙醇等)及其混合物。
式(Ⅰ)中A为式(Ⅱ)基且n为1或2的化合物制造方法是将前述方法得到的式(Ⅴ)化合物(A为式(Ⅳ)基且n为0)在溶剂中与1-3倍mol量酸化剂反应后用于前述方法反应而得。
酸化剂可用过氧化氢,有机过氧酸(如过乙酸,三氟过乙酸,过安息香酸,过苯二酸,间氯过安息香酸等),溶剂可用水,二氯甲烷,氯仿,二氯乙烷,苯,甲苯。乙酸乙酯,乙酸等,反应温度-30-150℃。
式(Ⅰ)中Xm-为氟,氯,溴,硫酸,硝酸,亚硝酸阴离子的化合物可用以下方法制得。
将前述方法制成的本发明化合物之一,即下式化合物,碘离子和离子交换银盐(氟化银,氯化银,溴化银,硫酸银,硝酸银或亚硝酸银)在溶剂中室温-溶剂沸点反应而得式(Ⅰ)中Xm-为氟,氯,溴,硫酸,硝酸,亚硝酸阴离子等的化合物。
溶剂可用水,醇类(如甲醇,乙醇等)及其混合物。
初始物质式(Ⅲ)化合物可按以下方法用公知化合物制成。
(1)式(Ⅲ)中A为式(Ⅱ)基且n为0的化合物可将下式化合物
与下式化合物
(式中Z1为卤原子)在碱存在下于溶剂中0℃-溶剂沸点搅拌0.5-10小时而得A为式(Ⅱ)基且n为0的式(Ⅲ)化合物。
卤原子可为氯,溴或碘,而碱可为氢氧化钠,氢氧化钾,碳酸钠,碳酸钾,三乙胺等,溶剂可用水,醇类(如甲醇,乙醇等),丙酮,N,N-二甲基甲酰胺,乙腈,二噁烷,四氢呋喃等,并可加碘化钾等反应促进剂。
(2)式(Ⅲ)中A为式(Ⅱ)基且n为1或2的化合物
可将前述(1)的方法所得A为式(Ⅱ)基且n为0的式(Ⅲ)化合物在溶剂中与1-3倍mol量酸化剂反应而得A为式(Ⅱ)基且n为1或2的式(Ⅲ)化合物。
酸化剂可用过氧化氢,有机过氧酸(如过乙酸,三氟过乙酸,过安息香酸,过苯二酸,间氯过安息香酸等),溶剂可用水,二氯甲烷,氯仿,二氯乙烷,苯,甲苯,乙酸乙酯,乙酸等,反应温度-30-150℃。
(3)式(Ⅲ)中A为氧原子的化合物
可将下式醇
与下式化合物
(式中Z2为卤原子)在碱存在下溶剂中0℃-溶剂沸点搅拌1-48小时而得A为氧原子的式(Ⅲ)化合物。
卤原子可为氯,溴或碘原子,碱可为氢氧化钠,氢氧化钾,碳酸钠,碳酸钾,氢化钠,氨基钠,三乙胺,氧化钡,氧化银等,溶剂可用水,丙酮,醚,四氢呋喃,N,N-二甲基甲酰胺(DMF),二甲亚砜,1,2-二甲氧基乙烷,乙腈,二噁烷等,还可加碘化钾等反应促进剂。
式(Ⅹ)化合物与下式化合物
(式中Z3和Z4相同或不同,为卤原子)在碱存在下于溶剂(如水,丙酮,醚,四氢呋喃,N,N-二甲基甲酰胺,二甲亚砜,1,2-二甲氧基乙烷等)中0℃-溶剂沸点搅拌1-48小时得卤化醚后在溶剂(乙醚,四氢呋喃等)中将其与镁反应而得到格利雅试剂,之后与二氧化碳反应而得A为氧原子的式(Ⅲ)化合物。
卤原子可为氯,溴或碘原子,碱可为氢氧化钠,氢氧化钾,碳酸钠,碳酸钾,氢化钠,氨基钠,三乙胺,氧化钡,氧化银等。
式(Ⅹ)化合物与下式化合物
(式中Z5为卤原子)在碱(如氢氧化钠,氢氧化钾,碳酸钠,碳酸钾,氢化钠,氨基钠,三乙胺,氧化钡,氧化银等)存在下溶剂(如水,丙酮,乙醚,四氢呋喃,N,N-二甲基甲酰胺,二甲亚砜,1,2-二甲氧基乙烷等)中0℃-溶剂沸点搅拌1-48小时而得醚腈化合物并将其加水分解而得A为氧原子的式(Ⅲ)化合物。
卤原子可为氯、溴或碘原子,前述加水分解在酸或碱存在溶剂中室温-溶剂沸点搅拌1-12小时进行反应,酸可用盐酸,硫酸,乙酸,甲酸等,碱可用氢氧化钠,氢氧化钾,氢氧化钡等,溶剂可用水,含水醇(如甲醇水溶液,乙醇水溶液等)。
至于式(Ⅰ)化合物的用量和用法,可用例如常用基剂将其1种或2种以上配制成洗剂,乳液,雪花膏,凝胶,气雾剂等外用剂,1日用数次涂抹头皮,其中还可加入其它药效物质。
上述常用基剂及其它药效物质可举出例如溶剂(乙醇,异丙醇,1,3-丁二醇,1,4-丁二醇,丙二醇,二丙二醇,甘油,二甘油,聚乙二醇,精馏水等),粘多糖类(透明质酸,软骨素4-硫酸,软骨素-6-硫酸,硫酸软骨素,硫酸
ラタン,硫酸类肝素,软骨素硫酸酯等多硫酸酯等),保存剂(熊去氧胆酸,安息香酸等),维生素类〔维生素A,B1,B2,B6,C,D,E及其衍生物(如维生素E乙酸酯等)〕,油分(流动石蜡,白色凡士林,固体石蜡,白地蜡,微晶蜡,胆固醇,鲨烯,橄榄油,ロ-ズヒツプ油,貂油,ホホバ油,硬化蓖麻油,硬化棕榈油,内豆蔻酸异丙酯,癸酸乙酯,辛酸乙酯,棕榈油酸,棕榈油酸乙酯,亚油酸乙酯,亚麻酸乙酯,油酸,硬脂酸,亚油酸,亚麻酸,棕榈酸,山萮酸,月桂酸,硬脂醇,鲸蜡醇,月桂醇,油醇,异辛酸鲸蜡酯等),杀菌剂〔硫黄,葡萄糖酸洗必泰,盐酸洗必泰,氯代鲸蜡基吡啶,氯代萘烷,异丙基乙基酚,季铵盐(如杀藻铵等),桧醇等〕,非离子表面活性剂(聚氧乙烯脂肪酸酯,聚氧乙烯脱水山梨糖酯脂肪酸酯,脱水山梨糖醇脂肪酸酯,脂肪酸甘油酯,聚氧乙烯甘油脂肪酸酯,聚甘油脂肪酸酯,脂肪酸丙二醇酯,聚甘油烷基苯基醚,聚氧乙烯硬化蓖麻油,聚氧乙烯和聚丙二醇的共聚物等),阴离子表面活性剂(N-酰基氨基酸盐,N-酰基水杨酸盐,烷基磷酸酯盐,酰基甲基牛磺酸盐等),阳离子表面活性剂(烷基三甲基铵,烷基-N,N-二烷基氨基乙酸酯等),两性表面活性剂(咪唑啉,胺氧化物等),高分子表面活性剂(酪蛋白等),硅衍生物(硅油,多元醇改性硅,硅树脂等),增粘剂(甲基纤维素,聚乙烯基吡咯烷酮,羧甲基纤维素,羧乙基纤维素,羟丙基纤维素,羧乙烯聚合物等),粘土矿(蒙脱石,皂石,锂蒙脱石等),PH调节剂(二异丙醇胺,柠檬酸等),酸化防止剂(二丁基羧基甲苯,亚硫酸氢钠,儿茶素,ダルクノデルタラクトン等),美白剂(能果苷,曲酸等),清凉化剂(1-
醇,樟脑等),抗炎症剂(甘草次酸,甘草酸二钾盐,氯化小檗碱,莽草宁,愈创薁,尿囊素,δ-氨基己酸等),末梢血管扩张剂(烟酸甲酯,烟酸苄酯,シユエルチアマリン,长压定,重氮氧化物,辣椒提取物,辣椒素,氯代三甲胺丁酸乙酯等),副肾皮质激素(乙酸氢化可的松,缬草酸倍他米松等),抗组胺剂(盐酸苯海拉明,盐酸氨杂异丙嗪等),局部麻醉剂(盐酸沙夫卡因,盐酸利多卡因等),角质溶解剂(尿素,水杨酸等),角化调节剂〔维生素A酸及其衍生物(如13-顺式视黄酸,エトレチホ-ト等)〕,卵胞激素(17β-雌二醇,乙炔基雌二醇,雌酮等),黄体激素(孕酮,17α-羟基孕酮乙酸盐等),抗雄激素剂(环孕酮乙酸盐,4-雄烯-3-酮-17β-羧酸等),香料,金属离子封锁剂,紫外线吸收剂,保湿剂(丝瓜提取物,胡罗卜提取物,二异丙基乙酸盐,吡咯烷酮羧酸,聚谷氨酰胺酸,聚环氧烷烷基糖苷醚,骨胺原,卵磷脂,神经酰胺,2-氨基乙磺酸等),生药提取物(腰果提取物,竹节人参提取物,ランヅツク提取物,藏红花提取物等)等等。
以下制造例,实施例及试验例详述本发明。
制造例1
11-(十二烷硫基)十一烷酸
十二烷基硫醇101.2g,11-溴十一烷酸132.6g及乙醇300ml的混合物中60℃搅拌条件下滴加氢氧化钠40.0g水溶液120ml并回流3小时。冷却后加3N盐酸使其成酸性,用氯仿抽出后,用水,饱和食盐水依顺洗净后用无水硫酸钠干燥。蒸除溶剂后生成物用氯仿再结晶而得标题化合物174.5g。
m.p.69-71℃
用相应的硫醇和11-溴十一烷酸基本上同于制造例得以下化合物,
11-(异戊硫基)十一烷酸
m.p.47-49℃
11-(环己硫基)十一烷酸
m.p.46-48℃
11-(癸硫基)十一烷酸
m.p.63-65℃
用相应硫醇和3-溴丙酸基本上同于制造例1得以下化合物。
3-(十四烷硫基)丙酸
m.p.66-68℃
3-(十八烷硫基)丙酸
m.p.78-80℃
用相应硫醇和5-溴缬草酸(戊酸)基本上用于制造例1得以下化合物。
5-(十四烷硫基)缬草酸
m.p.59-61℃
5-(十六烷硫基)缬草酸
m.p.65-67℃
5-(十八烷硫基)缬草酸
m.p.72-74℃
用十八烷硫醇和溴乙酸基本上同于制造例1得以下化合物。
(十八烷硫基)乙酸
m.p.73-75℃
用十八烷硫醇和2-溴丁酸基本上同于制造例1得以下化合物。
2-(十八烷硫基)丁酸
m.p.55-57℃
用十八烷硫醇和2-溴丙酸基本上同于制造例1得以下化合物。
2-(十八烷硫基)丙酸
m.p.65-67℃
制造例2
3-(十四烷磺酰)丙酸
制造例1得3-(十四烷硫基)丙酸5.2g溶于二氯甲烷70ml中室温搅拌条件下滴加溶于二氯甲烷70ml中的间氯过安息香酸8.9g,室温搅拌66小时。滤取析出结晶,硅胶柱色谱精制并乙酸乙酯再结晶而得标题化合物2.5g。
m.p.136-138℃
用制造例1所得3-(十八烷硫基)丙酸基本上同于制造例2得以下化合物。
3-(十八烷磺酰)丙酸
m.p.135-137℃
制造例3
5-(十三烷氧)缬草酸
(1)1-十三烷醇28.0g,1,4-二溴丁烷60.5g和硫酸氢四正丁铵0.4g中加40%氢氧化钠水溶液56ml,室温搅拌过夜,乙醚萃取后用无水硫酸镁干燥,蒸除溶剂后减压蒸馏而得1-(4-溴丁氧基)十三烷11.7g。
b.p.148-149℃/0.80mmHg
(2)镁2.4g中加四氢呋喃20ml和少量碘,氩气流下回流至碘色消失为止,该反应液中回流下滴加(1)所得化合物26.8g的四氢呋喃液30ml,再回流30分钟,-5℃下冷却,加干冰150g使反应液不致于从0℃上升,室温下搅拌1小时,加25硫酸100ml加水分解后用乙醚萃取,用20%氢氧化钠水溶液使其呈碱性后分出水相,再使其呈酸性后用氯仿萃取,无水硫酸镁干燥并减压蒸除溶剂而得标题化合物11.8g。
m.p.43-44℃
制造例4
5-(十四烷氧)缬草酸
(1)1-十四烷醇15.0g溶于四氢呋喃70ml中,冰冷下加入5-溴戊腈12.2ml和96%氢氧化钾粉4.9g,室温搅拌24小时后加乙酸乙酯,反应液用饱和食盐水洗净后用无水硫酸镁干燥。减压蒸除溶剂,剩余物用硅胶柱色谱精制(展开溶剂为乙醚∶正己烷=1∶4)而得5-(十四烷氧)戊腈7.4g。
m.p.30-31℃
用1-十六烷醇代替1-十四烷醇基本上同于制造例4(1)得以下化合物。
5-(十六烷氧)戊腈
m.p.40-41℃
用1-十八烷醇代替1-十四烷醇基本上同于制造例4(1)得以下化合物。
5-(十八烷氧)戊腈
m.p。46-47℃
(2)将(1)所得化合物8。6g溶于乙醇50ml中,加25%氢氧化钠水溶液50ml,回流8小时,冷却后加浓盐酸呈酸性并用乙酸乙酯萃取,用饱和食盐水洗涤后用无水硫酸镁干燥并减压蒸除溶剂而得标题化合物8.6g。
m.p.56-57℃
基本上同于制造例4(2)得以下化合物。
5-(十六烷氧)缬草酸
m.p.64-65℃
5-(十八烷氧)缬草酸
m.p.68-69℃
制造例5
N-〔3-(二甲基氨基)丙基〕-11-(十二烷硫基)十一烷酰胺
制造例1所得11-(十二烷硫基)十一烷酸150.0g和N,N-二甲基-1,3-二氨基丙烷47.6g在二甲苯200ml中回流5小时并除去生成的水,冷却后滤取生成物,用甲乙酮再结晶得标题化合物153.3g。
m.p.68-70℃
用N,N-二乙基-1,3-二氨基丙烷代替N,N-二甲基-1,3-二氨基丙烷基本上同于制造例5得以下化合物。
N-〔3-(二乙基氨基)丙基〕-11-(十二烷硫基)十一烷酰胺
m.p.59-61℃
用N,N-二乙基-1,2-乙二胺代替N,N-二甲基-1,3-二氨基丙烷基本上同于制造例5得以下化合物。
N-〔2-(二乙基氨基)乙基〕-11-(十二烷硫基)十一烷酰胺
m.p。63-65℃
N,N-二甲基-1,3-二氨基丙烷用N,N-二甲基-1,2-乙二胺代替并基本上同于制造例5得以下化合物。
N-〔2-(二乙基氨基)乙基〕-11-(十二烷硫基)十一烷酰胺
m.p.71-73℃
N,N-二甲基-1,3-二氨基丙烷用N,N-二甲基新戊二胺代替并基本上同于制造例5得以下化合物。
N-〔2,2-二甲基-3-(二甲基氨基)丙基〕-11-(十二烷硫基)十一烷酰胺
m.p.59-61℃
11-(十二烷硫基)十一烷酸用同于制造例1-4制造的化合物代替并基本上同于制造例5得以下化合物。
N-〔3-(二甲基氨基)丙基〕-11-(异戊硫基)十一烷酰胺
m.p.47-49℃
N-〔3-(二甲基氨基)丙基〕-11-(环己硫基)十一烷酰胺
m.p.61-63℃
N-〔3-(二甲基氨基)丙基〕-11-(癸硫基)十一烷酰胺
m.p.62-64℃
N-〔3-(二甲基氨基)丙基〕-3-(十四烷硫基)丙酰胺
m.p.46-48℃
N-〔3-(二甲基氨基)丙基〕-3-(十四烷磺酰)丙酰胺
m.p.89-91℃
N-〔3-(二甲基氨基)丙基〕-5-(十四烷硫基)戊酰胺
m.p.58-60℃
N-〔3-(二甲基氨基)丙基〕-5-(十六烷硫基)戊酰胺
m.p.68-70℃
N-〔3-(二甲基氨基)丙基〕-2-(十八烷硫基)乙酰胺
m.p.53-55℃
N-〔3-(二甲基氨基)丙基〕-3-(十八烷硫基)丙酰胺
m.p.58-60℃
N-〔3-(二甲基氨基)丙基〕-3-(十八烷硫酰)丙酰胺
m.p.98-100℃
N-〔3-(二甲基氨基)丙基〕-5-(十八烷硫基)戊酰胺
m.p.68-70℃
N-〔3-(二甲基氨基)丙基〕-5-(十四烷氧)戊酰胺
m.p.53-54℃
N-〔3-(二甲基氨基)丙基〕-5-(十三烷氧)戊酰胺
m.p.46-47℃
N-〔3-(二甲基氨基)丙基〕-5-(十六烷氧)戊酰胺
m.p.58-59℃
N-〔3-(二甲基氨基)丙基〕-5-(十八烷氧)戊酰胺
m.p.66-67℃
11-(十二烷硫基)十一烷酸用同于制造例1-4制得的化合物代替且N,N-二甲基-1,3-二氨基丙烷用N,N-二甲基-1,2-乙二胺代替并基本上同于例5制成以下化合物。
N-〔2-(二甲基氨基)乙基〕-5-(十四烷氧)戊酰胺
m.p。58-59℃
N-〔2-(二甲基氨基)乙基〕-5-(十八烷硫基)戊酰胺
m.p.72-74℃
N-〔2-(二甲基氨基)乙基〕-5-(十三烷氧)戊酰胺
m.p.52-53℃
制造例6
N-〔3-(二甲基氨基)丙基〕-3-(甲硫基)丙酰胺
3-(甲硫基)丙酸4.3g溶于甲苯40ml中,加亚硫酰二氯8.5g,80℃搅拌3小时,减压蒸除甲苯和过剩的亚硫酰二氯,得粗氯化物,将其溶于氯仿10ml中,冰冷搅拌下滴加N,N-二甲基-1,3-二氨基丙烷3.7g的氯仿液20ml,室温搅拌16小时,该反应液用重曹水,水,饱和食盐水依顺洗净,无水硫酸钠干燥并减压蒸除溶剂,得油液状标题化合物6.0g。
1H-NMR(CDCl3)δ(ppm);1.75(2H,quint.,J=6.3Hz),2.14(3H,s),2.35(6H,s),2.43~2.61(4H,m),2.80(2H,t,J=6.9Hz),3.37(2H,quart.,J=6.0Hz),7.22(1H,br.s)
制造例7
N-〔3-(二甲基氨基)丙基〕-11-十二烷亚硫酰基)十一烷酰胺
制造例5所得N-〔3-(二甲基氨基)丙基〕-11-(十二烷硫基)十一烷酰胺1.0g溶于氯仿50ml,冰冷搅拌下滴加溶于氯仿15ml中的间氯过安息香酸0.5g,再于冰冷条件下搅拌4小时,该反应液用重曹水,水,饱和食盐水依序洗净,无水硫酸钠干燥,蒸除溶剂后生成物用氯仿-乙醚再结晶得标题化合物0.91g。
m.p.110-112℃
实施例1
N-{3-〔11-(十二烷硫基)十一烷酰胺〕丙基}-N,N,N-三甲基铵碘化物。
将制造例5制得的N-〔3-(二甲基氨基)丙基〕-11-(十二烷硫基)十一烷酰胺120.0g溶于乙醇1L中,加甲基碘52.4g后室温搅拌3天,滤取生成物,乙醇再结晶得标题化合物141.5g。
m.p.103~105℃
1H-NMR(CDCl3)δ(ppm);0.88(3H,t,J=6.5Hz),1.19~1.71(36H,m),2.06~2.24(2H,m),2.32(2H,t,J=7.5Hz),2.50(4H,t,J=7.4Hz),3.32~3.49(11H,m),3.80~3.93(2H,m),7.30~7.41(1H,m)
N-〔3-(二甲基氨基)丙基〕-11-(十二烷硫基)十一烷酰胺用同于制造例5的方法制造的相应酰胺代替并以基本上同于实施例1的方法得以下化合物。
N-{3-〔3-(甲硫基)丙酰胺〕丙基}-N,N,N-三甲基铵碘化物
m.p.118-120℃
N-{2-(N′-甲基-3-(甲硫基)丙酰胺〕丙基}-N,N,N-三甲基铵碘化物
m.p.132-134℃
N-{3-(11-异戊硫基)十一烷酰胺〕丙基}-N,N,N-三甲基铵碘化物
m.p。98-100℃
N-{3-〔11-(环己硫基)十一烷酰胺〕丙基}-N,N,N-三甲基铵碘化物
m.p.101-103℃
N-{3-〔11-(癸硫基)十一烷酰胺〕丙基}-N,N,N-三甲基铵碘化物
m.p.99-101℃
N-{2-〔11-(十二烷硫基)十一烷酰胺〕乙基}-N,N,N-三甲基铵碘化物
m.p.115-117℃
N-{2-〔11-(十二烷硫基)十一烷酰胺〕乙基}-N,N,N-二乙基-N-甲基铵碘化物
m.p.75-77℃
N-{3-〔11-(十二烷基亚硫酰基)十一烷酰胺〕丙基}-N,N,N-三甲基铵碘化物
m.p.123-125℃
N-{3-〔11-(十二烷硫基)十一烷酰胺〕丙基}-N,N-二乙基-N-甲基铵碘化物
m.p.88-90℃
N-{2,2-二甲基-3-〔11-(十二烷硫基)十一烷酰胺〕丙基}-N,N,N-三甲基铵碘化物
m.p.127-129℃
N-{3-〔3-(十四烷硫基)丙酰胺〕丙基}-N,N,N-三甲基铵碘化物
m.p。116-118℃
N-{3-〔3-(十四烷基磺酰基)丙酰胺〕丙基}-N,N,N-三甲基铵碘化物
m。p。76-78℃
N-{3-〔5-(十四烷硫基)戊酰胺〕丙基}-N,N,N-三甲基铵碘化物
m。p.91-93℃
N-{3-〔5-(十六烷硫基)戊酰胺〕丙基}-N,N,N-三甲基铵碘化物
m.p。95-97℃
N-{3-〔3-(十八烷硫基)丙酰胺〕丙基}-N,N,N-三甲基铵碘化物
m.p。116-118℃
N-{3-〔3-(十八烷基磺酰)丙酰胺〕丙基}-N,N,N-三甲基铵碘化物
m.p。96-98℃
N-{3-〔2-(十八烷硫基)丙酰胺〕丙基}-N,N,N-三甲基铵碘化物
m.p。131-133℃
N-{2-〔5-(十八烷硫基)戊酰胺〕乙基}-N,N,N-三甲基铵碘化物
m.p。88-90℃
N-{3-〔5-(十八烷硫基)戊酰胺〕丙基}-N,N,N-三甲基铵碘化物
m.p.96-98℃
实施例2
N-{3-〔5-(十四烷氧)戊酰胺〕丙基}-N,N,N-三甲基铵碘化物
将同于制造例5得到的N-〔3-(二甲基氨基)丙基〕-5-(十四烷氧)戊酰胺2.5g溶于乙醇10ml中,加甲基碘0.6ml,室温搅拌24小时,减压蒸除溶剂后生成物用乙醇-乙醚再结晶得标记化合物2.9g。
m.p.94-96℃
1H-NMR(CDCl3)δ(ppm);0.88(3H,t,J=6.5Hz),1.26(22H,s),1.46~1.78(6H,m),2.03~2.22(2H,m),2.34(2H,t,J=7.0Hz),3.32~3.48(15H,m),3.78~3.91(2H,m),7.17~7.27(1H,m)
N-〔3-(二甲基氨基)丙基〕-5-(十四烷氧)戊酰胺用相应酰胺代替并基本上同于实施例2得以下化合物。
N-{2-〔5-(十三烷氧)戊酰胺〕乙基}-N,N,N-三甲基铵碘化物
m.p。91-92℃
N-{3-〔5-(十三烷氧)戊酰胺〕丙基}-N,N,N-三甲基铵碘化物
m.p。96-98℃
N-{2-〔5-(十四烷氧)戊酰胺〕乙基}-N,N,N-三甲基铵碘化物
m.p.93-94℃
N-{3-〔5-(十六烷氧)戊酰胺〕丙基}-N,N,N-三甲基铵碘化物
m。p。98-100℃
N-{3-〔5-(十八烷氧)戊酰胺〕丙基}-N,N,N-三甲基铵碘化物
m.p.101-103℃
实施例3
N-{3-〔11-(十四烷硫基)十一烷酰胺〕丙基}-N,N,N-三甲基铵溴化物
将制造例5得的N-〔3-(二甲基氨基)丙基〕-11-(十二烷硫基)十一烷酰胺1.5g溶于乙醇100ml,加甲基溴并于室温下搅拌4小时,蒸除溶剂后乙醇再结晶得标记化合物1.2g。
m.p.92-94℃
1H-NMR(CDCl3)δ(ppm);0.88(3H,t,J=6.5Hz),1.20~1.74(36H,m),2.11~2.29(2H,m),2.40~2.56(6H,m),3.31~3.53(11H,m),3.89~4.04(2H,m),8.62(1H,br.s)
实施例4
N-苄基-N-{3-〔11-(十二烷硫基)十一烷酰胺〕丙基}-N,N-二甲基铵氯化物
将同于制造例5得到的N-〔3-(二甲基氨基)丙基〕-11-(癸硫基)十一烷酰胺1.5g和苄基氯0.5g溶于乙醇20ml,回流11小时并蒸除溶剂后生成物用乙醇再结晶而得标记化合物1.8g。
m.p.75~77℃
1H-NMR(CDCl3)δ(ppm);0.88(3H,t,J=6.5Hz),1.16~1.70(32H,m),2.13~2.32(2H,m),2.37(2H,t,J=7.8Hz),2.49(4H,t,J=7.3Hz),3.19(6H,s),3.35~3.47(2H,m),3.85~3.98(2H,m),4.79(2H,s),7.41~7.63(5H,m),8.60(1H,br.s)
苄基氯用丙基氯或烯丙氯代替以基本上同于实施例4反应得以下化合物。
N-{3-〔11-(癸硫基)十一烷酰胺〕丙基}-N,N-二甲基-N-丙基铵氯化物
m。p.70-72℃
N-烯丙基-N-{3-〔11-(十二烷硫基)十一烷酰胺〕丙基}-N,N-二甲基铵氯化物
m.p.80-82℃
实施例5
N-{3-〔11-(十二烷硫基)十一烷酰胺〕丙基}-N,N,N-三甲基铵甲基硫酸盐
将制造例5得的N-〔3-(二甲基氨基)丙基〕-11-(十二烷硫基)十一烷酰胺2.0g和硫酸二甲基酯0.6g溶于甲醇30ml中,回流2小时。溶剂蒸除后生成物用甲醇再结晶得标记化合物2.4g。
m.p.90~92℃
1H-NMR(CDCl3)δ(ppm);0.88(3H,t,J=6.5Hz),1.20~1.69(36H,m),2.02~2.19(2H,m),2.34(2H,t,J=7.7Hz),2.50(4H,t,J=7.3Hz),3.24(9H,s),3.33~3.47(2H,m),3.58~3.71(2H,m),3.72(3H,s),8.07(1H,br.s)
硫酸二甲酯用磷酸三甲酯并基本上同于实施例5反应得以下化合物。
N-{3-〔11-(十二烷硫基)十一烷酰胺〕丙基}-N,N,N-三甲基铵二甲基磷酸盐
m.p.65-67℃
实施例6
N-{3-〔11-(十二烷硫基)十一烷酰胺〕丙基}-N,N,N-三甲基铵对甲苯磺酸盐
将制造例5所得N-〔3-(二甲基氨基)丙基〕-11-(十二烷硫基)十一烷酰胺1.5g和对甲苯磺酸甲酯0.7g溶于乙醇中,回流2小时并蒸除溶剂后生成物用乙醇-乙酯再结晶得标记化合物1.6g。
m.p.90~92℃
1H-NMR(CDCl3)δ(ppm);0.88(3H,t,J=6.5Hz),1.11~1.66(36H,m),1.98~2.26(4H,m),2.36(3H,s),2.50(4H,t,J=7.3Hz),3.23(9H,s),3.29~3.43(2H,m),3.67~3.81(2H,m),7.18(2H,d,J=7.9Hz),7.72(2H,d,J=8.1Hz),8.30(1H,br.s)
用各种磺酸酯及硫酸酯基本上同于实施例6反应而得以下化合物。
N-{3-〔11-(十二烷硫基)十一烷酰胺〕丙基}-N,N,N-三甲基铵甲基磺酸盐
m.p。88-90℃
N-{3-〔11-(十二烷硫基)十一烷酰胺〕丙基}-N,N,N-三甲基铵苯磺酸盐
m.p.86-88℃
N-{3-〔11-(十二烷硫基)十一烷酰胺〕丙基}-N,N,N-三甲基铵乙基硫酸盐
m.p.98-100℃
N-{3-〔11-(十二烷硫基)十一烷酰胺〕丙基}-N-乙基-N,N-二甲基铵乙基硫酸盐
m.p.52-54℃
实施例7
N-{3-〔11-(十二烷硫基)十一烷酰胺〕丙基}-N,N,N-三甲基铵硝酸盐
将实施例1得的N-{3-〔11-(十二烷硫基)十一烷酰胺〕丙基}-N,N,N-三甲基铵碘化物1.5g溶于乙醇150ml,加溶于水15ml的硝酸银0.4g,室温下搅拌15小时,除去析出的碘化银,蒸除溶剂后生成物用乙醇重结晶得标记化合物0.5g。
m.p.93~95℃
1H-NMR(CDCl3)δ(ppm);0.88(3H,t,J=6.5Hz),1.19~1.69(36H,m),2.00~2.17(2H,m),2.27(2H,t,J=7.5Hz),2.50(4H,t,J=7.4Hz),3.27(9H,s),3.30~3.43(2H,m),3.64~3.78(2H,m),7.78(1H,br.s)
硝酸银用各种银盐代替并基本上同于实施例7反应得以下化合物。
N-{3-〔11-(十二烷硫基)十一烷酰胺〕丙基}-N,N,N-三甲基铵氟化物
m。p。
63-65℃
N-{3-〔11-(十二烷硫基)十一烷酰胺〕丙基}-N,N,N-三甲基铵氯化物
m.p。93-95℃
N-{3-〔11-(十二烷硫基)十一烷酰胺〕丙基}-N,N,N-三甲基铵亚硝酸盐
m.p.94-96℃
实施例8
N-{3-〔11-(十二烷硫基)十一烷酰胺〕丙基}-N,N,N-三甲基铵乙酸盐
将实施例6所得N-{3-〔11-(十二烷硫基)十一烷酰胺〕丙基}-N,N,N-三甲基铵对甲苯磺酸盐3.0g溶于乙醇50ml中,然后通入乙酸形阴离子交换强碱性阴离子交换树脂100ml充填的柱中,溶剂蒸出后生成物乙醇-乙醚再结晶而得标记化合物0.5g。
m.p.79~81℃
1H-NMR(CDCl3)δ(ppm);0.88(3H,t,J=6.5Hz),1.15~1.69(36H,m),1.95~2.11(5H,m),2.26(2H,t,J=7.7Hz),2.49(4H,t,J=7.2Hz),3.25(9H,s),3.31~3.42(2H,m),4.03~4.15(2H,m),9.28~9.39(1H,m)
生发效果试验
烷酰氨基铵化合物生毛发效果试验用CH鼠(雄性,7周龄)5只进行,其背部毛用推子脱毛,然后在此部位1日1次涂抹表1所示试料0.2ml,共涂10日,最后肉眼评价生毛发程度,其标准如下。
可认为未生毛发 0
生一点软毛 1
生一点硬毛 2
除毛部位生25%硬毛 3
除毛部位生50%硬毛 4
除毛部位生75%硬毛 5
除毛部位生100%硬毛 6
试料涂抹开始后42天的结果以评价点平均值列于表2。
表1
试料号 化合物名
A N-{3-〔11-(十二烷硫基)十一烷酰胺〕丙基}-N,N,N-三甲基铵碘化物的2%乙醇溶液
B N-{3-〔5-(十四烷硫基)戊酰胺〕丙基}-N,N,N-三甲基铵碘化物的2%乙醇溶液
C N-苄基-N-{3-〔11-(十二烷硫基)十一烷酰胺〕丙基}-N,N-二甲基铵碘化物的2%乙醇溶液
D N-{3-〔5-(十四烷氧)戊酰胺〕丙基}-N,N,N-三甲基铵碘化物的2%乙醇溶液
E N-{3-〔5-(十六烷氧)戊酰胺〕丙基}-N,N,N-三甲基铵碘化物的2%乙醇溶液
F 乙醇
G 比较(未涂抹)
表2
试料No. 评价点评价值
A 2.4
B 4.6
C 5.8
D 4.2
E 1.6
F 0
G 0
本发明化合物具有优异的生毛发作用,所以可用作生毛发剂。
Claims (2)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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JP3287374A JPH0543529A (ja) | 1991-08-10 | 1991-08-10 | アルカンアミドアンモニウム化合物 |
JPPCT/JP92/01014 | 1992-08-07 | ||
PCT/JP1992/001014 WO1993003005A1 (en) | 1991-08-10 | 1992-08-07 | Alkanamidoammonium compound |
Publications (1)
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CN1082534A true CN1082534A (zh) | 1994-02-23 |
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CN93101376A Pending CN1082534A (zh) | 1991-08-10 | 1993-02-10 | 烷酰氨基铵化合物 |
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JP (1) | JPH0543529A (zh) |
CN (1) | CN1082534A (zh) |
AU (1) | AU656625B2 (zh) |
CA (1) | CA2115345A1 (zh) |
WO (1) | WO1993003005A1 (zh) |
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US5610198A (en) * | 1994-03-18 | 1997-03-11 | The United States Of America As Represented By The Department Of Health And Human Services | Anti-mycobacterial compositions and their use for the treatment of tuberculosis and related diseases |
FR2778405B1 (fr) * | 1998-05-07 | 2000-09-08 | Ceca Sa | N-(dialkylamino) alkyl alpha carboxamides, compositions les contenant, procedes de preparation et utilisations |
EP0965584A3 (en) * | 1998-06-15 | 2003-12-17 | Transgene S.A. | Polyamine compounds and compositions containing them useful for the transfer of active substances into a cell |
EP0965583A1 (en) * | 1998-06-15 | 1999-12-22 | Transgene S.A. | Polyamine compounds and compositions containing them useful for the transfer of active substances into a cell |
ES2733353T3 (es) | 2007-11-09 | 2019-11-28 | Basf As | Compuestos lípidos para uso en productos cosméticos, como suplemento alimenticio o como un medicamento |
EP2147910A1 (en) * | 2008-07-15 | 2010-01-27 | Pronova BioPharma Norge AS | Novel lipid compounds |
US8735436B2 (en) | 2009-05-08 | 2014-05-27 | Pronova Biopharma Norge As | Polyunsaturated fatty acids for the treatment of diseases related to cardiovascular, metabolic and inflammatory disease areas |
SG10201509127YA (en) | 2010-11-05 | 2015-12-30 | Pronova Biopharma Norge As | Methods of treatment using lipid compounds |
CN105120842B (zh) | 2013-02-28 | 2020-12-01 | 普罗诺瓦生物医药挪威公司 | 包含脂质化合物、甘油三酯和表面活性剂的组合物以及使用它们的方法 |
EP3288550B1 (en) | 2015-04-28 | 2024-06-05 | Basf As | Structurally enhanced fatty acids containing sulphur for their use in treating non-alcoholic steatohepatitis |
IL308604A (en) | 2017-12-06 | 2024-01-01 | Basf As | Fatty acid antecedents for the treatment of nonalcoholic fatty liver disease |
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CA1002534A (en) * | 1973-06-27 | 1976-12-28 | Donald E. Conner | Quaternary halides of gluconamides |
JPS54130509A (en) * | 1977-06-29 | 1979-10-09 | Procter & Gamble | Organism decomposing cationic surfactant |
-
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CA2115345A1 (en) | 1993-02-18 |
WO1993003005A1 (en) | 1993-02-18 |
AU2402792A (en) | 1993-03-02 |
AU656625B2 (en) | 1995-02-09 |
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