JP3819955B2 - α，α’−ジアミノアルコールの製造法 - Google Patents
α，α’−ジアミノアルコールの製造法 Download PDFInfo
- Publication number
- JP3819955B2 JP3819955B2 JP26204995A JP26204995A JP3819955B2 JP 3819955 B2 JP3819955 B2 JP 3819955B2 JP 26204995 A JP26204995 A JP 26204995A JP 26204995 A JP26204995 A JP 26204995A JP 3819955 B2 JP3819955 B2 JP 3819955B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- alkyl
- phenyl
- reacting
- butyl
- 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.)
- Expired - Lifetime
Links
- 238000004519 manufacturing process Methods 0.000 title 1
- -1 halomethyl lithium Chemical compound 0.000 claims abstract description 22
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 13
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 claims abstract description 12
- 229910052744 lithium Inorganic materials 0.000 claims abstract description 9
- 150000005690 diesters Chemical class 0.000 claims abstract description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 7
- 229960005190 phenylalanine Drugs 0.000 claims abstract description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 5
- 125000005907 alkyl ester group Chemical group 0.000 claims abstract description 4
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 4
- 125000005843 halogen group Chemical group 0.000 claims abstract 2
- 150000001367 organochlorosilanes Chemical class 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 7
- KZKUQOJWPNFIQV-XYIZDEMUSA-N (3s,4as,8as)-1-butyl-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline-3-carboxamide Chemical compound C1CCC[C@@H]2C(CCCC)N[C@H](C(N)=O)C[C@@H]21 KZKUQOJWPNFIQV-XYIZDEMUSA-N 0.000 claims description 6
- JFBZPFYRPYOZCQ-UHFFFAOYSA-N [Li].[Al] Chemical compound [Li].[Al] JFBZPFYRPYOZCQ-UHFFFAOYSA-N 0.000 claims description 5
- 229910052782 aluminium Inorganic materials 0.000 claims description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical class C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 claims description 3
- VUKDWNGELRZGOE-MFKCLSPESA-N methyl n-[(2s,3r)-4-[(3s,4as,8as)-3-[(2-methylpropan-2-yl)oxycarbamoyl]-3,4,4a,5,6,7,8,8a-octahydro-1h-isoquinolin-2-yl]-3-hydroxy-1-phenylbutan-2-yl]carbamate Chemical compound C([C@H](NC(=O)OC)[C@H](O)CN1[C@@H](C[C@@H]2CCCC[C@@H]2C1)C(=O)NOC(C)(C)C)C1=CC=CC=C1 VUKDWNGELRZGOE-MFKCLSPESA-N 0.000 claims description 3
- YKKKRYQDJBXHPO-VHSXEESVSA-N [(1s)-1-[(2s)-oxiran-2-yl]-2-phenylethyl]carbamic acid Chemical compound C([C@H](NC(=O)O)[C@@H]1OC1)C1=CC=CC=C1 YKKKRYQDJBXHPO-VHSXEESVSA-N 0.000 claims description 2
- 239000003638 chemical reducing agent Substances 0.000 claims 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 34
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- JPOXNPPZZKNXOV-UHFFFAOYSA-N bromochloromethane Chemical compound ClCBr JPOXNPPZZKNXOV-UHFFFAOYSA-N 0.000 description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 150000001408 amides Chemical class 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- CETVQRFGPOGIQJ-UHFFFAOYSA-N lithium;hexane Chemical compound [Li+].CCCCC[CH2-] CETVQRFGPOGIQJ-UHFFFAOYSA-N 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- VFHUZXQGMFOLRF-JTQLQIEISA-N methyl n-[(2s)-4-chloro-3-oxo-1-phenylbutan-2-yl]carbamate Chemical compound COC(=O)N[C@H](C(=O)CCl)CC1=CC=CC=C1 VFHUZXQGMFOLRF-JTQLQIEISA-N 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 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 3
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- JIHFRPSFLTXYEP-JTQLQIEISA-N methyl (2s)-2-(methoxycarbonylamino)-3-phenylpropanoate Chemical compound COC(=O)N[C@H](C(=O)OC)CC1=CC=CC=C1 JIHFRPSFLTXYEP-JTQLQIEISA-N 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- 239000005046 Chlorosilane Substances 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- ZSALEBOIWNAMBX-VHSXEESVSA-N [(2s,3s)-4-chloro-3-hydroxy-1-phenylbutan-2-yl]carbamic acid Chemical compound ClC[C@@H](O)[C@@H](NC(O)=O)CC1=CC=CC=C1 ZSALEBOIWNAMBX-VHSXEESVSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 2
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 2
- 150000004703 alkoxides Chemical class 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical compound Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- 150000003944 halohydrins Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 150000002924 oxiranes Chemical class 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 229960005235 piperonyl butoxide Drugs 0.000 description 2
- 229930195734 saturated hydrocarbon Natural products 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- 0 *CC(C(Cc1ccccc1)NC(O)=O)=O Chemical compound *CC(C(Cc1ccccc1)NC(O)=O)=O 0.000 description 1
- NKJOXAZJBOMXID-UHFFFAOYSA-N 1,1'-Oxybisoctane Chemical compound CCCCCCCCOCCCCCCCC NKJOXAZJBOMXID-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- CXBDYQVECUFKRK-UHFFFAOYSA-N 1-methoxybutane Chemical compound CCCCOC CXBDYQVECUFKRK-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 208000036142 Viral infection Diseases 0.000 description 1
- JEDZLBFUGJTJGQ-UHFFFAOYSA-N [Na].COCCO[AlH]OCCOC Chemical compound [Na].COCCO[AlH]OCCOC JEDZLBFUGJTJGQ-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- FLLNLJJKHKZKMB-UHFFFAOYSA-N boron;tetramethylazanium Chemical compound [B].C[N+](C)(C)C FLLNLJJKHKZKMB-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Chemical group 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Chemical group 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 229910052740 iodine Chemical group 0.000 description 1
- 239000011630 iodine Chemical group 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- JSHKLIOFGHTOIV-WDEREUQCSA-N methyl N-[(1S)-1-[(2S)-oxiran-2-yl]-2-phenylethyl]carbamate Chemical compound C([C@H](NC(=O)OC)[C@@H]1OC1)C1=CC=CC=C1 JSHKLIOFGHTOIV-WDEREUQCSA-N 0.000 description 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
- ZAZXPIZQYVPWAW-UHFFFAOYSA-N methyl n-(4-chloro-3-hydroxy-1-phenylbutan-2-yl)carbamate Chemical compound COC(=O)NC(C(O)CCl)CC1=CC=CC=C1 ZAZXPIZQYVPWAW-UHFFFAOYSA-N 0.000 description 1
- ZAZXPIZQYVPWAW-WDEREUQCSA-N methyl n-[(2s,3s)-4-chloro-3-hydroxy-1-phenylbutan-2-yl]carbamate Chemical compound COC(=O)N[C@H]([C@H](O)CCl)CC1=CC=CC=C1 ZAZXPIZQYVPWAW-WDEREUQCSA-N 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000012419 sodium bis(2-methoxyethoxy)aluminum hydride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 241001430294 unidentified retrovirus Species 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/36—Compounds containing oxirane rings with hydrocarbon radicals, substituted by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/16—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by singly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/18—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by doubly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the nitrogen-containing ring
- C07D217/26—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH290494 | 1994-09-23 | ||
| CH02904/94-1 | 1994-12-09 | ||
| CH373694 | 1994-12-09 | ||
| CH03736/94-0 | 1994-12-09 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JPH0899959A JPH0899959A (ja) | 1996-04-16 |
| JPH0899959A5 JPH0899959A5 (enExample) | 2005-06-02 |
| JP3819955B2 true JP3819955B2 (ja) | 2006-09-13 |
Family
ID=25691689
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP26204995A Expired - Lifetime JP3819955B2 (ja) | 1994-09-23 | 1995-09-18 | α，α’−ジアミノアルコールの製造法 |
Country Status (9)
| Country | Link |
|---|---|
| US (5) | US5591885A (enExample) |
| EP (1) | EP0710651B1 (enExample) |
| JP (1) | JP3819955B2 (enExample) |
| KR (1) | KR100418237B1 (enExample) |
| CN (3) | CN1116284C (enExample) |
| AT (1) | ATE198740T1 (enExample) |
| DE (1) | DE59508973D1 (enExample) |
| DK (1) | DK0710651T3 (enExample) |
| ES (1) | ES2154310T3 (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5523463A (en) * | 1994-09-23 | 1996-06-04 | Hoffmann-La Roche Inc. | Method of producing halogenated and alpha-aminoalchohols |
| JP3665343B2 (ja) * | 1995-02-03 | 2005-06-29 | 株式会社カネカ | α−ハロケトン、α−ハロヒドリン及びエポキシドの製造法 |
| WO1997028105A1 (fr) * | 1996-01-29 | 1997-08-07 | Kaneka Corporation | Procede de reduction de composes de carbonyle |
| EP0847994B1 (de) | 1996-12-11 | 2003-04-09 | F. Hoffmann-La Roche Ag | Verfahren zur Herstellung gemischter Anhydride |
| AU2321900A (en) * | 1999-01-28 | 2000-08-18 | Ajinomoto Co., Inc. | Process for the preparation of alpha-aminoketones |
| US6605732B1 (en) | 1999-05-03 | 2003-08-12 | Aerojet Fine Chemicals Llc | Clean, high-yield preparation of S,S and R,S amino acid isosteres |
| JP4143787B2 (ja) * | 1999-07-28 | 2008-09-03 | 味の素株式会社 | α−アミノハロメチルケトン誘導体の製造方法 |
| DE10143742A1 (de) | 2001-09-06 | 2003-03-27 | Consortium Elektrochem Ind | Verfahren zur Herstellung von alpha-Halogenketonen |
| US7038553B2 (en) * | 2002-10-03 | 2006-05-02 | International Business Machines Corporation | Scalable computer system having surface-mounted capacitive couplers for intercommunication |
| EP1604662A1 (en) * | 2004-06-08 | 2005-12-14 | Santhera Pharmaceuticals (Deutschland) Aktiengesellschaft | 1-[(3R)-Amino-4-(2-fluoro-phenyl)-butyl]-pyrrolidine-(2R)-carboxylic acid benzyl amine derivatives and related compounds as dipeptidyl peptidase IV (DPP-IV) inhibitors for the treatment of type 2 diabetes mellitus |
| PL2328883T3 (pl) * | 2008-09-24 | 2015-01-30 | Zach System | Sposób wytwarzania nebivololu |
| CN102127061B (zh) * | 2010-01-15 | 2016-02-17 | 浙江华海药业股份有限公司 | 一种制备6-氟-3，4-二氢-2h-1-苯并吡喃-2-环氧乙烷的改进方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1340588C (en) * | 1988-06-13 | 1999-06-08 | Balraj Krishan Handa | Amino acid derivatives |
| GB8927913D0 (en) * | 1989-12-11 | 1990-02-14 | Hoffmann La Roche | Amino acid derivatives |
| GB8927915D0 (en) * | 1989-12-11 | 1990-02-14 | Hoffmann La Roche | Novel alcohols |
| US5430041A (en) * | 1991-05-10 | 1995-07-04 | Hoffmann-La Roche Inc. | Amino acid derivatives having antiviral activity |
| JP2551901B2 (ja) * | 1991-07-26 | 1996-11-06 | エフ エム シー コーポレーション | 接触アルキル化方法 |
| JPH06184069A (ja) * | 1991-11-19 | 1994-07-05 | Lonza Ag | α−ヒドロキシ−β−アミノカルボン酸の製造方法 |
| US5380849A (en) * | 1992-11-09 | 1995-01-10 | Merck & Co., Inc. | Process for optically pure decahydroisoqiunolines |
| US5455353A (en) * | 1993-03-24 | 1995-10-03 | Hoffmann-La Roche Inc. | 4-(benzyl-2-oxo-oxazolidin-5 ylmethyl)N tertbutyl-decahydroisoquinoline-3-carboxamides |
| ATE172970T1 (de) * | 1993-07-15 | 1998-11-15 | Hoffmann La Roche | Verfahren zur herstellung eines n-tert.butylamids |
| US5523463A (en) * | 1994-09-23 | 1996-06-04 | Hoffmann-La Roche Inc. | Method of producing halogenated and alpha-aminoalchohols |
-
1995
- 1995-08-11 US US08/514,329 patent/US5591885A/en not_active Expired - Lifetime
- 1995-09-11 EP EP95114205A patent/EP0710651B1/de not_active Expired - Lifetime
- 1995-09-11 DK DK95114205T patent/DK0710651T3/da active
- 1995-09-11 AT AT95114205T patent/ATE198740T1/de active
- 1995-09-11 DE DE59508973T patent/DE59508973D1/de not_active Expired - Lifetime
- 1995-09-11 ES ES95114205T patent/ES2154310T3/es not_active Expired - Lifetime
- 1995-09-18 JP JP26204995A patent/JP3819955B2/ja not_active Expired - Lifetime
- 1995-09-21 CN CN95116887A patent/CN1116284C/zh not_active Expired - Lifetime
- 1995-09-22 KR KR1019950031290A patent/KR100418237B1/ko not_active Expired - Lifetime
-
1996
- 1996-09-18 US US08/718,109 patent/US5684176A/en not_active Expired - Lifetime
-
1997
- 1997-07-25 US US08/900,413 patent/US5847144A/en not_active Expired - Lifetime
-
1998
- 1998-07-09 US US09/112,651 patent/US5977388A/en not_active Expired - Lifetime
- 1998-11-16 US US09/192,656 patent/US5965733A/en not_active Expired - Lifetime
-
1999
- 1999-12-30 CN CNB991274121A patent/CN1133620C/zh not_active Expired - Lifetime
- 1999-12-30 CN CN99127411A patent/CN1111156C/zh not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| US5965733A (en) | 1999-10-12 |
| CN1116284C (zh) | 2003-07-30 |
| JPH0899959A (ja) | 1996-04-16 |
| US5847144A (en) | 1998-12-08 |
| CN1127251A (zh) | 1996-07-24 |
| KR100418237B1 (ko) | 2004-07-23 |
| US5977388A (en) | 1999-11-02 |
| US5684176A (en) | 1997-11-04 |
| ES2154310T3 (es) | 2001-04-01 |
| CN1275563A (zh) | 2000-12-06 |
| CN1111156C (zh) | 2003-06-11 |
| US5591885A (en) | 1997-01-07 |
| CN1275562A (zh) | 2000-12-06 |
| EP0710651B1 (de) | 2001-01-17 |
| DK0710651T3 (da) | 2001-05-14 |
| ATE198740T1 (de) | 2001-02-15 |
| CN1133620C (zh) | 2004-01-07 |
| KR960010629A (ko) | 1996-04-20 |
| DE59508973D1 (de) | 2001-02-22 |
| EP0710651A1 (de) | 1996-05-08 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP1840125B1 (fr) | Intermédiaires pour la production de dioxane-2-alkylcarbamates | |
| JP3819955B2 (ja) | α，α’−ジアミノアルコールの製造法 | |
| CA2075869C (en) | Production of fluoxetine and new intermediates | |
| US7309803B2 (en) | Clean, High-yield preparation of S,S and R,S amino acid isosteres | |
| JP3599855B2 (ja) | ハロゲン化α−アミノケトン及びα−アミノアルコールの製造法 | |
| JP2002533430A (ja) | アリールエーテルの調製方法 | |
| JP3467043B2 (ja) | ブチルチオ−イソキノリン及びそれの中間体を製造するための方法 | |
| US6437134B2 (en) | Process for a phenylthiobutyl-isoquinoline and intermediates therefor | |
| US6573388B1 (en) | Ethylaziridine derivatives and their preparation methods | |
| KR20030055304A (ko) | 보호된 1-(1-아미노알킬)-옥시란의 제조 방법 | |
| JPH0220625B2 (enExample) | ||
| JP2000256236A (ja) | 光学活性アルコール化合物の製造方法 | |
| JPH0867663A (ja) | １，４−ジアミノブタン−２−オール誘導体の製造法 | |
| JPWO2000010986A1 (ja) | （２ｒ，３ｓ）−３−アミノ−１，２−オキシランの製造法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20040812 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20051122 |
|
| A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20051122 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20060221 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20060228 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20060517 |
|
| TRDD | Decision of grant or rejection written | ||
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20060613 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20060616 |
|
| R150 | Certificate of patent or registration of utility model |
Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20100623 Year of fee payment: 4 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20110623 Year of fee payment: 5 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20110623 Year of fee payment: 5 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20120623 Year of fee payment: 6 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20120623 Year of fee payment: 6 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20130623 Year of fee payment: 7 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| EXPY | Cancellation because of completion of term |