JP3993908B2 - アミノアルコール誘導体及び該誘導体の製造方法 - Google Patents
アミノアルコール誘導体及び該誘導体の製造方法 Download PDFInfo
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- JP3993908B2 JP3993908B2 JP34238596A JP34238596A JP3993908B2 JP 3993908 B2 JP3993908 B2 JP 3993908B2 JP 34238596 A JP34238596 A JP 34238596A JP 34238596 A JP34238596 A JP 34238596A JP 3993908 B2 JP3993908 B2 JP 3993908B2
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- Prior art keywords
- group
- phenyl
- lower alkyl
- amino
- mmol
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- 150000001414 amino alcohols Chemical class 0.000 title claims description 20
- 238000004519 manufacturing process Methods 0.000 title claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 62
- -1 phenylazo group Chemical group 0.000 claims description 62
- 125000003118 aryl group Chemical group 0.000 claims description 44
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 36
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- 125000003277 amino group Chemical group 0.000 claims description 12
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 239000000126 substance Substances 0.000 claims description 12
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 10
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 9
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 9
- 125000003282 alkyl amino group Chemical group 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 4
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- MXZROAOUCUVNHX-UHFFFAOYSA-N 2-Aminopropanol Chemical class CCC(N)O MXZROAOUCUVNHX-UHFFFAOYSA-N 0.000 claims description 3
- 125000002252 acyl group Chemical group 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000005350 hydroxycycloalkyl group Chemical group 0.000 claims description 3
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 3
- 125000004423 acyloxy group Chemical group 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 2
- 125000006312 cyclopentyl amino group Chemical group [H]N(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 366
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 215
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 104
- 230000015572 biosynthetic process Effects 0.000 description 77
- 238000003786 synthesis reaction Methods 0.000 description 74
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 62
- 239000000203 mixture Substances 0.000 description 58
- 238000005160 1H NMR spectroscopy Methods 0.000 description 48
- 239000002904 solvent Substances 0.000 description 47
- 239000012230 colorless oil Substances 0.000 description 46
- 238000006243 chemical reaction Methods 0.000 description 44
- 239000000463 material Substances 0.000 description 43
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 41
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 33
- 238000000034 method Methods 0.000 description 33
- 238000010898 silica gel chromatography Methods 0.000 description 33
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 30
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 28
- 239000000243 solution Substances 0.000 description 28
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 26
- 239000012044 organic layer Substances 0.000 description 26
- 229910052938 sodium sulfate Inorganic materials 0.000 description 26
- 235000011152 sodium sulphate Nutrition 0.000 description 26
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 21
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 14
- 150000001875 compounds Chemical class 0.000 description 14
- 235000019441 ethanol Nutrition 0.000 description 14
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 14
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 13
- UYNCFCUHRNOSCN-FYYLOGMGSA-N N-[(1R,2R)-1-hydroxy-3-(4-morpholinyl)-1-phenylpropan-2-yl]decanamide Chemical compound C([C@@H](NC(=O)CCCCCCCCC)[C@H](O)C=1C=CC=CC=1)N1CCOCC1 UYNCFCUHRNOSCN-FYYLOGMGSA-N 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- IPIVAXLHTVNRBS-UHFFFAOYSA-N decanoyl chloride Chemical compound CCCCCCCCCC(Cl)=O IPIVAXLHTVNRBS-UHFFFAOYSA-N 0.000 description 11
- 239000003921 oil Substances 0.000 description 11
- 239000012043 crude product Substances 0.000 description 10
- 239000013078 crystal Substances 0.000 description 10
- 238000001914 filtration Methods 0.000 description 10
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 9
- 125000006355 carbonyl methylene group Chemical group [H]C([H])([*:2])C([*:1])=O 0.000 description 9
- 238000001816 cooling Methods 0.000 description 9
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 9
- 239000007858 starting material Substances 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- HDOWRFHMPULYOA-UHFFFAOYSA-N piperidin-4-ol Chemical compound OC1CCNCC1 HDOWRFHMPULYOA-UHFFFAOYSA-N 0.000 description 6
- 125000006239 protecting group Chemical group 0.000 description 6
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
- GHPVDCPCKSNJDR-UHFFFAOYSA-N 2-hydroxydecanoic acid Chemical compound CCCCCCCCC(O)C(O)=O GHPVDCPCKSNJDR-UHFFFAOYSA-N 0.000 description 5
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 4
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 4
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 230000002194 synthesizing effect Effects 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000012156 elution solvent Substances 0.000 description 3
- 238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 3
- VFXVAXFIFHSGNR-UHFFFAOYSA-N octyl carbonochloridate Chemical compound CCCCCCCCOC(Cl)=O VFXVAXFIFHSGNR-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 230000000707 stereoselective effect Effects 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- KXYGLCHZMVIZML-STQMWFEESA-N (1s,2s)-2-amino-3-morpholin-4-yl-1-phenylpropan-1-ol Chemical compound C([C@H](N)[C@@H](O)C=1C=CC=CC=1)N1CCOCC1 KXYGLCHZMVIZML-STQMWFEESA-N 0.000 description 2
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- JYZJYKOZGGEXSX-UHFFFAOYSA-N 2-hydroxymyristic acid Chemical compound CCCCCCCCCCCCC(O)C(O)=O JYZJYKOZGGEXSX-UHFFFAOYSA-N 0.000 description 2
- IMLXLGZJLAOKJN-UHFFFAOYSA-N 4-aminocyclohexan-1-ol Chemical compound NC1CCC(O)CC1 IMLXLGZJLAOKJN-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 229930186217 Glycolipid Natural products 0.000 description 2
- 206010027476 Metastases Diseases 0.000 description 2
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 2
- 235000021314 Palmitic acid Nutrition 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 238000005575 aldol reaction Methods 0.000 description 2
- 230000000259 anti-tumor effect Effects 0.000 description 2
- 230000000840 anti-viral effect Effects 0.000 description 2
- ICKMPMAGRYUKNA-HOTGVXAUSA-N benzyl n-[(1s,2s)-1,3-dihydroxy-1-phenylpropan-2-yl]carbamate Chemical compound N([C@@H](CO)[C@@H](O)C=1C=CC=CC=1)C(=O)OCC1=CC=CC=C1 ICKMPMAGRYUKNA-HOTGVXAUSA-N 0.000 description 2
- 201000011510 cancer Diseases 0.000 description 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 2
- 125000006364 carbonyl oxy methylene group Chemical group [H]C([H])([*:2])OC([*:1])=O 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- NISGSNTVMOOSJQ-UHFFFAOYSA-N cyclopentanamine Chemical compound NC1CCCC1 NISGSNTVMOOSJQ-UHFFFAOYSA-N 0.000 description 2
- HTWWKYKIBSHDPC-UHFFFAOYSA-N decanoyl decanoate Chemical compound CCCCCCCCCC(=O)OC(=O)CCCCCCCCC HTWWKYKIBSHDPC-UHFFFAOYSA-N 0.000 description 2
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N hydrochloric acid Substances Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 150000002632 lipids Chemical class 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 230000009401 metastasis Effects 0.000 description 2
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 2
- 230000005709 nerve cell growth Effects 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 230000037361 pathway Effects 0.000 description 2
- 230000001737 promoting effect Effects 0.000 description 2
- JHHZLHWJQPUNKB-UHFFFAOYSA-N pyrrolidin-3-ol Chemical compound OC1CCNC1 JHHZLHWJQPUNKB-UHFFFAOYSA-N 0.000 description 2
- 235000009518 sodium iodide Nutrition 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- GHPVDCPCKSNJDR-SECBINFHSA-N (2r)-2-hydroxydecanoic acid Chemical compound CCCCCCCC[C@@H](O)C(O)=O GHPVDCPCKSNJDR-SECBINFHSA-N 0.000 description 1
- MUCMKTPAZLSKTL-UHFFFAOYSA-N (3RS)-3-hydroxydodecanoic acid Natural products CCCCCCCCCC(O)CC(O)=O MUCMKTPAZLSKTL-UHFFFAOYSA-N 0.000 description 1
- GYSCBCSGKXNZRH-UHFFFAOYSA-N 1-benzothiophene-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=CC2=C1 GYSCBCSGKXNZRH-UHFFFAOYSA-N 0.000 description 1
- UYNCFCUHRNOSCN-UHFFFAOYSA-N 1-phenyl-2-(decanoylamino)-3-morpholino-1-propanol Chemical compound C=1C=CC=CC=1C(O)C(NC(=O)CCCCCCCCC)CN1CCOCC1 UYNCFCUHRNOSCN-UHFFFAOYSA-N 0.000 description 1
- BWZVCCNYKMEVEX-UHFFFAOYSA-N 2,4,6-Trimethylpyridine Chemical compound CC1=CC(C)=NC(C)=C1 BWZVCCNYKMEVEX-UHFFFAOYSA-N 0.000 description 1
- QEKPBYCXURULNE-UHFFFAOYSA-N 2-aminopropane-1,1-diol Chemical class CC(N)C(O)O QEKPBYCXURULNE-UHFFFAOYSA-N 0.000 description 1
- ZEFNPEQYWMAJDA-WMEOFMBSSA-N 2-hydroxy-n-[(1s,2s)-1-hydroxy-3-morpholin-4-yl-1-phenylpropan-2-yl]octanamide Chemical compound C([C@H](NC(=O)C(O)CCCCCC)[C@@H](O)C=1C=CC=CC=1)N1CCOCC1 ZEFNPEQYWMAJDA-WMEOFMBSSA-N 0.000 description 1
- JKRDADVRIYVCCY-UHFFFAOYSA-N 2-hydroxyoctanoic acid Chemical compound CCCCCCC(O)C(O)=O JKRDADVRIYVCCY-UHFFFAOYSA-N 0.000 description 1
- HVCOBJNICQPDBP-UHFFFAOYSA-N 3-[3-[3,5-dihydroxy-6-methyl-4-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-2-yl]oxydecanoyloxy]decanoic acid;hydrate Chemical compound O.OC1C(OC(CC(=O)OC(CCCCCCC)CC(O)=O)CCCCCCC)OC(C)C(O)C1OC1C(O)C(O)C(O)C(C)O1 HVCOBJNICQPDBP-UHFFFAOYSA-N 0.000 description 1
- NAKFRQULMGLXBT-UHFFFAOYSA-N 6-methoxyquinolin-8-ol Chemical compound N1=CC=CC2=CC(OC)=CC(O)=C21 NAKFRQULMGLXBT-UHFFFAOYSA-N 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Natural products CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 238000006683 Mannich reaction Methods 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical class NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- HVVNJUAVDAZWCB-YFKPBYRVSA-N [(2s)-pyrrolidin-2-yl]methanol Chemical compound OC[C@@H]1CCCN1 HVVNJUAVDAZWCB-YFKPBYRVSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 238000010306 acid treatment Methods 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
- YDZIJQXINJLRLL-UHFFFAOYSA-N alpha-hydroxydodecanoic acid Natural products CCCCCCCCCCC(O)C(O)=O YDZIJQXINJLRLL-UHFFFAOYSA-N 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- LEYBQDIMQJQSSF-NHCUHLMSSA-N benzyl n-[(1r,2r)-1-hydroxy-1-phenyl-3-piperidin-1-ylpropan-2-yl]carbamate Chemical compound C([C@H]([C@H](O)C=1C=CC=CC=1)NC(=O)OCC=1C=CC=CC=1)N1CCCCC1 LEYBQDIMQJQSSF-NHCUHLMSSA-N 0.000 description 1
- XXEDULMPNMTUGC-WOJBJXKFSA-N benzyl n-[(1r,2r)-1-hydroxy-1-phenyl-3-pyrrolidin-1-ylpropan-2-yl]carbamate Chemical compound C([C@H]([C@H](O)C=1C=CC=CC=1)NC(=O)OCC=1C=CC=CC=1)N1CCCC1 XXEDULMPNMTUGC-WOJBJXKFSA-N 0.000 description 1
- DUFIMTILBGNQCR-NHCUHLMSSA-N benzyl n-[(1r,2r)-1-hydroxy-3-(4-hydroxypiperidin-1-yl)-1-phenylpropan-2-yl]carbamate Chemical compound C([C@H]([C@H](O)C=1C=CC=CC=1)NC(=O)OCC=1C=CC=CC=1)N1CCC(O)CC1 DUFIMTILBGNQCR-NHCUHLMSSA-N 0.000 description 1
- ZVJLXNLODMBZHS-WOJBJXKFSA-N benzyl n-[(1r,2r)-1-hydroxy-3-morpholin-4-yl-1-phenylpropan-2-yl]carbamate Chemical compound C([C@H]([C@H](O)C=1C=CC=CC=1)NC(=O)OCC=1C=CC=CC=1)N1CCOCC1 ZVJLXNLODMBZHS-WOJBJXKFSA-N 0.000 description 1
- DSDVKZNEYVPHGG-FGZHOGPDSA-N benzyl n-[(1r,2r)-3-(cyclohexylamino)-1-hydroxy-1-phenylpropan-2-yl]carbamate Chemical compound C([C@H]([C@H](O)C=1C=CC=CC=1)NC(=O)OCC=1C=CC=CC=1)NC1CCCCC1 DSDVKZNEYVPHGG-FGZHOGPDSA-N 0.000 description 1
- CSYLUTLCYUSJOQ-NHCUHLMSSA-N benzyl n-[(1r,2r)-3-(cyclopentylamino)-1-hydroxy-1-phenylpropan-2-yl]carbamate Chemical compound C([C@H]([C@H](O)C=1C=CC=CC=1)NC(=O)OCC=1C=CC=CC=1)NC1CCCC1 CSYLUTLCYUSJOQ-NHCUHLMSSA-N 0.000 description 1
- DUFIMTILBGNQCR-LEWJYISDSA-N benzyl n-[(1r,2s)-1-hydroxy-3-(4-hydroxypiperidin-1-yl)-1-phenylpropan-2-yl]carbamate Chemical compound C([C@@H]([C@H](O)C=1C=CC=CC=1)NC(=O)OCC=1C=CC=CC=1)N1CCC(O)CC1 DUFIMTILBGNQCR-LEWJYISDSA-N 0.000 description 1
- DUFIMTILBGNQCR-RTWAWAEBSA-N benzyl n-[(1s,2r)-1-hydroxy-3-(4-hydroxypiperidin-1-yl)-1-phenylpropan-2-yl]carbamate Chemical compound C([C@H]([C@@H](O)C=1C=CC=CC=1)NC(=O)OCC=1C=CC=CC=1)N1CCC(O)CC1 DUFIMTILBGNQCR-RTWAWAEBSA-N 0.000 description 1
- LDTMMBJNEWWLFN-PMACEKPBSA-N benzyl n-[(1s,2s)-1-cyclohexyl-1-hydroxy-3-morpholin-4-ylpropan-2-yl]carbamate Chemical compound C([C@@H]([C@@H](O)C1CCCCC1)NC(=O)OCC=1C=CC=CC=1)N1CCOCC1 LDTMMBJNEWWLFN-PMACEKPBSA-N 0.000 description 1
- XXEDULMPNMTUGC-PMACEKPBSA-N benzyl n-[(1s,2s)-1-hydroxy-1-phenyl-3-pyrrolidin-1-ylpropan-2-yl]carbamate Chemical compound C([C@@H]([C@@H](O)C=1C=CC=CC=1)NC(=O)OCC=1C=CC=CC=1)N1CCCC1 XXEDULMPNMTUGC-PMACEKPBSA-N 0.000 description 1
- XYZQPEYHDMIJAI-YPJRHXLCSA-N benzyl n-[(1s,2s)-1-hydroxy-3-(3-hydroxypyrrolidin-1-yl)-1-phenylpropan-2-yl]carbamate Chemical compound C([C@@H]([C@@H](O)C=1C=CC=CC=1)NC(=O)OCC=1C=CC=CC=1)N1CCC(O)C1 XYZQPEYHDMIJAI-YPJRHXLCSA-N 0.000 description 1
- DUFIMTILBGNQCR-SFTDATJTSA-N benzyl n-[(1s,2s)-1-hydroxy-3-(4-hydroxypiperidin-1-yl)-1-phenylpropan-2-yl]carbamate Chemical compound C([C@@H]([C@@H](O)C=1C=CC=CC=1)NC(=O)OCC=1C=CC=CC=1)N1CCC(O)CC1 DUFIMTILBGNQCR-SFTDATJTSA-N 0.000 description 1
- XSPZBOCIYIKRSN-SFTDATJTSA-N benzyl n-[(1s,2s)-1-hydroxy-3-(4-methylpiperazin-1-yl)-1-phenylpropan-2-yl]carbamate Chemical compound C1CN(C)CCN1C[C@@H]([C@@H](O)C=1C=CC=CC=1)NC(=O)OCC1=CC=CC=C1 XSPZBOCIYIKRSN-SFTDATJTSA-N 0.000 description 1
- VWFQTUPAKKMDEU-UJKMTWAASA-N benzyl n-[(1s,2s)-1-hydroxy-3-[(4-hydroxycyclohexyl)amino]-1-phenylpropan-2-yl]carbamate Chemical compound C([C@@H]([C@@H](O)C=1C=CC=CC=1)NC(=O)OCC=1C=CC=CC=1)NC1CCC(O)CC1 VWFQTUPAKKMDEU-UJKMTWAASA-N 0.000 description 1
- MPWDIXRMOBZADX-GFUWAVFVSA-N benzyl n-[(1s,2s)-1-hydroxy-3-[3-(hydroxymethyl)piperidin-1-yl]-1-phenylpropan-2-yl]carbamate Chemical compound C1C(CO)CCCN1C[C@@H]([C@@H](O)C=1C=CC=CC=1)NC(=O)OCC1=CC=CC=C1 MPWDIXRMOBZADX-GFUWAVFVSA-N 0.000 description 1
- ZVJLXNLODMBZHS-PMACEKPBSA-N benzyl n-[(1s,2s)-1-hydroxy-3-morpholin-4-yl-1-phenylpropan-2-yl]carbamate Chemical compound C([C@@H]([C@@H](O)C=1C=CC=CC=1)NC(=O)OCC=1C=CC=CC=1)N1CCOCC1 ZVJLXNLODMBZHS-PMACEKPBSA-N 0.000 description 1
- KXKIGQOQPNFXDL-PMACEKPBSA-N benzyl n-[(2s,3s)-3-hydroxy-1-morpholin-4-ylnonan-2-yl]carbamate Chemical compound C([C@@H]([C@@H](O)CCCCCC)NC(=O)OCC=1C=CC=CC=1)N1CCOCC1 KXKIGQOQPNFXDL-PMACEKPBSA-N 0.000 description 1
- APJQUZRPQBFXHS-VMPREFPWSA-N benzyl n-[(2s,3s)-3-hydroxy-1-morpholin-4-yloctadecan-2-yl]carbamate Chemical compound C([C@@H]([C@@H](O)CCCCCCCCCCCCCCC)NC(=O)OCC=1C=CC=CC=1)N1CCOCC1 APJQUZRPQBFXHS-VMPREFPWSA-N 0.000 description 1
- KCFWJDXJJMIWCN-ZEQRLZLVSA-N benzyl n-[(2s,3s)-3-hydroxy-1-morpholin-4-yltridecan-2-yl]carbamate Chemical compound C([C@@H]([C@@H](O)CCCCCCCCCC)NC(=O)OCC=1C=CC=CC=1)N1CCOCC1 KCFWJDXJJMIWCN-ZEQRLZLVSA-N 0.000 description 1
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 125000005805 dimethoxy phenyl group Chemical group 0.000 description 1
- NQGIJDNPUZEBRU-UHFFFAOYSA-N dodecanoyl chloride Chemical compound CCCCCCCCCCCC(Cl)=O NQGIJDNPUZEBRU-UHFFFAOYSA-N 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- YWGHUJQYGPDNKT-UHFFFAOYSA-N hexanoyl chloride Chemical compound CCCCCC(Cl)=O YWGHUJQYGPDNKT-UHFFFAOYSA-N 0.000 description 1
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 238000003328 mesylation reaction Methods 0.000 description 1
- 238000003541 multi-stage reaction Methods 0.000 description 1
- CSUIAIOTSFXBKQ-ISKFKSNPSA-N n-[(1r,2r)-1-hydroxy-3-(4-hydroxypiperidin-1-yl)-1-phenylpropan-2-yl]decanamide Chemical compound C([C@@H](NC(=O)CCCCCCCCC)[C@H](O)C=1C=CC=CC=1)N1CCC(O)CC1 CSUIAIOTSFXBKQ-ISKFKSNPSA-N 0.000 description 1
- CSUIAIOTSFXBKQ-LADGPHEKSA-N n-[(1r,2s)-1-hydroxy-3-(4-hydroxypiperidin-1-yl)-1-phenylpropan-2-yl]decanamide Chemical compound C([C@H](NC(=O)CCCCCCCCC)[C@H](O)C=1C=CC=CC=1)N1CCC(O)CC1 CSUIAIOTSFXBKQ-LADGPHEKSA-N 0.000 description 1
- ZZFKJMVGIRWCLD-AZGAKELHSA-N n-[(1r,2s)-1-hydroxy-3-(4-hydroxypiperidin-1-yl)-1-phenylpropan-2-yl]dodecanamide Chemical compound C([C@H](NC(=O)CCCCCCCCCCC)[C@H](O)C=1C=CC=CC=1)N1CCC(O)CC1 ZZFKJMVGIRWCLD-AZGAKELHSA-N 0.000 description 1
- GUCOOGJUAWKOTH-AZUAARDMSA-N n-[(1r,2s)-1-hydroxy-3-(4-hydroxypiperidin-1-yl)-1-phenylpropan-2-yl]hexanamide Chemical compound C([C@H](NC(=O)CCCCC)[C@H](O)C=1C=CC=CC=1)N1CCC(O)CC1 GUCOOGJUAWKOTH-AZUAARDMSA-N 0.000 description 1
- ZZMJIZHRLDPBIG-RBBKRZOGSA-N n-[(1r,2s)-1-hydroxy-3-(4-hydroxypiperidin-1-yl)-1-phenylpropan-2-yl]octanamide Chemical compound C([C@H](NC(=O)CCCCCCC)[C@H](O)C=1C=CC=CC=1)N1CCC(O)CC1 ZZMJIZHRLDPBIG-RBBKRZOGSA-N 0.000 description 1
- DNDCAKNVQVRGPA-JTHBVZDNSA-N n-[(1r,2s)-3-(diethylamino)-1-hydroxy-1-phenylpropan-2-yl]decanamide Chemical compound CCCCCCCCCC(=O)N[C@@H](CN(CC)CC)[C@H](O)C1=CC=CC=C1 DNDCAKNVQVRGPA-JTHBVZDNSA-N 0.000 description 1
- CSUIAIOTSFXBKQ-VWNXMTODSA-N n-[(1s,2r)-1-hydroxy-3-(4-hydroxypiperidin-1-yl)-1-phenylpropan-2-yl]decanamide Chemical compound C([C@@H](NC(=O)CCCCCCCCC)[C@@H](O)C=1C=CC=CC=1)N1CCC(O)CC1 CSUIAIOTSFXBKQ-VWNXMTODSA-N 0.000 description 1
- ZZFKJMVGIRWCLD-RSXGOPAZSA-N n-[(1s,2r)-1-hydroxy-3-(4-hydroxypiperidin-1-yl)-1-phenylpropan-2-yl]dodecanamide Chemical compound C([C@@H](NC(=O)CCCCCCCCCCC)[C@@H](O)C=1C=CC=CC=1)N1CCC(O)CC1 ZZFKJMVGIRWCLD-RSXGOPAZSA-N 0.000 description 1
- GUCOOGJUAWKOTH-QUCCMNQESA-N n-[(1s,2r)-1-hydroxy-3-(4-hydroxypiperidin-1-yl)-1-phenylpropan-2-yl]hexanamide Chemical compound C([C@@H](NC(=O)CCCCC)[C@@H](O)C=1C=CC=CC=1)N1CCC(O)CC1 GUCOOGJUAWKOTH-QUCCMNQESA-N 0.000 description 1
- ZZMJIZHRLDPBIG-IRLDBZIGSA-N n-[(1s,2r)-1-hydroxy-3-(4-hydroxypiperidin-1-yl)-1-phenylpropan-2-yl]octanamide Chemical compound C([C@@H](NC(=O)CCCCCCC)[C@@H](O)C=1C=CC=CC=1)N1CCC(O)CC1 ZZMJIZHRLDPBIG-IRLDBZIGSA-N 0.000 description 1
- DNDCAKNVQVRGPA-GGAORHGYSA-N n-[(1s,2r)-3-(diethylamino)-1-hydroxy-1-phenylpropan-2-yl]decanamide Chemical compound CCCCCCCCCC(=O)N[C@H](CN(CC)CC)[C@@H](O)C1=CC=CC=C1 DNDCAKNVQVRGPA-GGAORHGYSA-N 0.000 description 1
- BLWOBQRSCFXNIN-GMAHTHKFSA-N n-[(1s,2s)-1-hydroxy-1-phenyl-3-pyrrolidin-1-ylpropan-2-yl]decanamide Chemical compound C([C@H](NC(=O)CCCCCCCCC)[C@@H](O)C=1C=CC=CC=1)N1CCCC1 BLWOBQRSCFXNIN-GMAHTHKFSA-N 0.000 description 1
- GOCIDFXPEKDUQR-ZXNYFWILSA-N n-[(1s,2s)-1-hydroxy-3-(3-hydroxypyrrolidin-1-yl)-1-phenylpropan-2-yl]decanamide Chemical compound C([C@H](NC(=O)CCCCCCCCC)[C@@H](O)C=1C=CC=CC=1)N1CCC(O)C1 GOCIDFXPEKDUQR-ZXNYFWILSA-N 0.000 description 1
- IRRBSQVQIDBQJN-UPVQGACJSA-N n-[(1s,2s)-1-hydroxy-3-(4-methylpiperazin-1-yl)-1-phenylpropan-2-yl]decanamide Chemical compound C([C@H](NC(=O)CCCCCCCCC)[C@@H](O)C=1C=CC=CC=1)N1CCN(C)CC1 IRRBSQVQIDBQJN-UPVQGACJSA-N 0.000 description 1
- ZBMXXQGITYSKRI-FIXSFTCYSA-N n-[(1s,2s)-1-hydroxy-3-[(2s)-2-(hydroxymethyl)pyrrolidin-1-yl]-1-phenylpropan-2-yl]decanamide Chemical compound C([C@H](NC(=O)CCCCCCCCC)[C@@H](O)C=1C=CC=CC=1)N1CCC[C@H]1CO ZBMXXQGITYSKRI-FIXSFTCYSA-N 0.000 description 1
- UEADBUVTVLGQAH-BKKSKEKOSA-N n-[(1s,2s)-1-hydroxy-3-[(4-hydroxycyclohexyl)amino]-1-phenylpropan-2-yl]decanamide Chemical compound C([C@H](NC(=O)CCCCCCCCC)[C@@H](O)C=1C=CC=CC=1)NC1CCC(O)CC1 UEADBUVTVLGQAH-BKKSKEKOSA-N 0.000 description 1
- SHVHLBYEFZMGKD-XIAJTGEISA-N n-[(1s,2s)-1-hydroxy-3-[3-(hydroxymethyl)piperidin-1-yl]-1-phenylpropan-2-yl]decanamide Chemical compound C([C@H](NC(=O)CCCCCCCCC)[C@@H](O)C=1C=CC=CC=1)N1CCCC(CO)C1 SHVHLBYEFZMGKD-XIAJTGEISA-N 0.000 description 1
- UYNCFCUHRNOSCN-GMAHTHKFSA-N n-[(1s,2s)-1-hydroxy-3-morpholin-4-yl-1-phenylpropan-2-yl]decanamide Chemical compound C([C@H](NC(=O)CCCCCCCCC)[C@@H](O)C=1C=CC=CC=1)N1CCOCC1 UYNCFCUHRNOSCN-GMAHTHKFSA-N 0.000 description 1
- NIWVKIFVGPQIHH-ZCYQVOJMSA-N n-[(1s,2s)-3-(cyclohexylamino)-1-hydroxy-1-phenylpropan-2-yl]decanamide Chemical compound C([C@H](NC(=O)CCCCCCCCC)[C@@H](O)C=1C=CC=CC=1)NC1CCCCC1 NIWVKIFVGPQIHH-ZCYQVOJMSA-N 0.000 description 1
- ROBOUDAPTUQXKC-UHFFFAOYSA-N n-phenacyldecanamide Chemical compound CCCCCCCCCC(=O)NCC(=O)C1=CC=CC=C1 ROBOUDAPTUQXKC-UHFFFAOYSA-N 0.000 description 1
- REEZZSHJLXOIHL-UHFFFAOYSA-N octanoyl chloride Chemical compound CCCCCCCC(Cl)=O REEZZSHJLXOIHL-UHFFFAOYSA-N 0.000 description 1
- 125000005447 octyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000001148 pentyloxycarbonyl group Chemical group 0.000 description 1
- 238000010647 peptide synthesis reaction Methods 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- VUNPWIPIOOMCPT-UHFFFAOYSA-N piperidin-3-ylmethanol Chemical compound OCC1CCCNC1 VUNPWIPIOOMCPT-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- CYDAIPOXGDPDLN-HOTGVXAUSA-N tert-butyl n-[(1s,2s)-1-hydroxy-3-morpholin-4-yl-1-phenylpropan-2-yl]carbamate Chemical compound C([C@H](NC(=O)OC(C)(C)C)[C@@H](O)C=1C=CC=CC=1)N1CCOCC1 CYDAIPOXGDPDLN-HOTGVXAUSA-N 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
Images
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP34238596A JP3993908B2 (ja) | 1995-12-08 | 1996-12-09 | アミノアルコール誘導体及び該誘導体の製造方法 |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP34508095 | 1995-12-08 | ||
| JP7-345080 | 1995-12-08 | ||
| JP34238596A JP3993908B2 (ja) | 1995-12-08 | 1996-12-09 | アミノアルコール誘導体及び該誘導体の製造方法 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007118032A Division JP4484897B2 (ja) | 1995-12-08 | 2007-04-27 | アミノアルコール誘導体の製造方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JPH09216856A JPH09216856A (ja) | 1997-08-19 |
| JPH09216856A5 JPH09216856A5 (2) | 2004-11-18 |
| JP3993908B2 true JP3993908B2 (ja) | 2007-10-17 |
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| JP34238596A Expired - Fee Related JP3993908B2 (ja) | 1995-12-08 | 1996-12-09 | アミノアルコール誘導体及び該誘導体の製造方法 |
Country Status (1)
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|---|---|
| JP (1) | JP3993908B2 (2) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5009459B2 (ja) * | 1999-12-06 | 2012-08-22 | 生化学工業株式会社 | アミノアルコール誘導体及びそれを含有する医薬 |
| CA2453978C (en) | 2001-07-16 | 2011-10-11 | Genzyme Corporation | Synthesis of udp-glucose: n-acylsphingosine glucosyltransferase inhibitors |
| JP2005104895A (ja) * | 2003-09-30 | 2005-04-21 | Nippon Kayaku Co Ltd | 光学活性なアミノアルコール化合物の製造法 |
| US8003617B2 (en) | 2004-11-10 | 2011-08-23 | Genzyme Corporation | Methods of treating diabetes mellitus |
| ES2380904T3 (es) * | 2005-01-26 | 2012-05-21 | Allergan, Inc. | Composiciones farmacéuticas que tienen un efecto analgésico y contienen 1-bencil-1-hidroxi-2,3-diamino-propil aminas, amidas del ácido 3-bencil-3-hidroxi-2-amino propiónico o compuestos relacionados |
| PL2032134T3 (pl) | 2006-05-09 | 2015-11-30 | Genzyme Corp | Sposoby leczenia stłuszczeniowej choroby wątroby obejmujące hamowanie syntezy glikosfingolipidów |
| EP2594562B1 (en) | 2007-05-31 | 2016-07-20 | Genzyme Corporation | 2-acylaminopropanol-type glucosylceramide synthase inhibitors |
| ES2660690T3 (es) | 2007-10-05 | 2018-03-23 | Genzyme Corporation | Método para tratar poliquistosis renales con derivados de ceramida |
| CA2731685A1 (en) | 2008-07-28 | 2010-02-04 | Genzyme Corporation | Glucosylceramide synthase inhibition for the treatment of collapsing glomerulopathy and other glomerular disease |
| EP3078373A1 (en) | 2008-10-03 | 2016-10-12 | Genzyme Corporation | 2-acylaminopropanol-type glucosylceramide synthase inhibitor |
| WO2011066352A1 (en) | 2009-11-27 | 2011-06-03 | Genzyme Corporation | An amorphous and a crystalline form of genz 112638 hemitartrat as inhibitor of glucosylceramide synthase |
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1996
- 1996-12-09 JP JP34238596A patent/JP3993908B2/ja not_active Expired - Fee Related
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| Publication number | Publication date |
|---|---|
| JPH09216856A (ja) | 1997-08-19 |
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