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 (enrdf_load_html_response) | 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 (enrdf_load_html_response) |
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| 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 |
| BRPI0211379B8 (pt) | 2001-07-16 | 2021-05-25 | Genzyme Corp | síntese de inibidores de udp-glicose: n-acil-esfingosina glicosiltransferase |
| 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 |
| WO2006053043A2 (en) | 2004-11-10 | 2006-05-18 | Genzyme Corporation | Methods of treating diabetes mellitus |
| JP5042039B2 (ja) * | 2005-01-26 | 2012-10-03 | アラーガン、インコーポレイテッド | 鎮痛活性および／または免疫賦活活性を有する３−アリール−３−ヒドロキシ−２−アミノ−プロピオン酸アミド、３−ヘテロアリール−３−ヒドロキシ−２−アミノ−プロピオン酸アミドおよび関連化合物 |
| SI2032134T1 (sl) | 2006-05-09 | 2015-10-30 | Genzyme Corporation | Postopki zdravljenja bolezni zamaščenih jeter, ki obsegajo inhibicijo sintezo glukosfingolipida |
| EP2167485B1 (en) | 2007-05-31 | 2015-09-30 | Genzyme Corporation | 2-acylaminopropoanol-type glucosylceramide synthase inhibitors |
| AU2008307516B2 (en) | 2007-10-05 | 2011-11-17 | Genzyme Corporation | Method of treating polycystic kidney diseases with ceramide derivatives |
| JP2011529500A (ja) | 2008-07-28 | 2011-12-08 | ジェンザイム コーポレーション | 虚脱性糸球体症および他の糸球体疾患の処置のためのグルコシルセラミドシンターゼ阻害 |
| CN107935983A (zh) * | 2008-10-03 | 2018-04-20 | 简詹姆公司 | 2‑酰胺基丙醇型葡糖神经酰胺合酶抑制剂 |
| CN105753846B (zh) | 2009-11-27 | 2019-11-15 | 基酶有限公司 | 作为葡糖神经酰胺合酶的抑制剂的无定型和结晶形式的Genz 112638半酒石酸盐 |
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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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