JPS5927337B2 - Ｎ−メチルモラノリンの製造法 - Google Patents

Ｎ−メチルモラノリンの製造法

Info

Publication number: JPS5927337B2
Authority: JP; Japan
Prior art keywords: nojirimycin; methylmoranoline; substance; producing; added
Prior art date: 1977-11-10
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

Application number

JP13550677A

Other languages

English (en)

Japanese (ja)

Other versions

JPS5470282A (en

Inventor

進午松村

宏榎本

良明青柳

洋治江連

義明吉国

政広八木

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Nippon Shinyaku Co Ltd

Original Assignee

Nippon Shinyaku Co Ltd

Priority date (The priority date 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 date listed.)

1977-11-10

Filing date

1977-11-10

Publication date

1984-07-05

1977-11-10 Application filed by Nippon Shinyaku Co Ltd filed Critical Nippon Shinyaku Co Ltd

1977-11-10 Priority to JP13550677A priority Critical patent/JPS5927337B2/ja

1978-10-16 Priority to GB7840674A priority patent/GB2009152B/en

1978-10-23 Priority to DE19782857509 priority patent/DE2857509C2/de

1978-10-23 Priority to DE2846118A priority patent/DE2846118C3/de

1978-11-06 Priority to AT0792378A priority patent/AT366032B/de

1978-11-08 Priority to NLAANVRAGE7811106,A priority patent/NL175819C/xx

1978-11-08 Priority to DK496478A priority patent/DK149806C/da

1978-11-09 Priority to US05/959,163 priority patent/US4339585A/en

1978-11-09 Priority to FR7831724A priority patent/FR2409986A1/fr

1978-11-09 Priority to IT51847/78A priority patent/IT1111075B/it

1978-11-09 Priority to SE7811582A priority patent/SE439630B/sv

1978-11-10 Priority to CH1161078A priority patent/CH637936A5/de

1979-04-03 Priority to FR7908397A priority patent/FR2414042A1/fr

1979-06-05 Publication of JPS5470282A publication Critical patent/JPS5470282A/ja

1983-12-22 Priority to NL8304395A priority patent/NL8304395A/nl

1984-07-05 Publication of JPS5927337B2 publication Critical patent/JPS5927337B2/ja

Status Expired legal-status Critical Current

Links

AAKDPDFZMNYDLR-XZBKPIIZSA-N N-methyl-1-deoxynojirimycin Chemical compound CN1C[C@H](O)[C@@H](O)[C@H](O)[C@H]1CO AAKDPDFZMNYDLR-XZBKPIIZSA-N 0.000 title claims description 16
AAKDPDFZMNYDLR-UHFFFAOYSA-N N-methyl deoxynojirimycin Natural products CN1CC(O)C(O)C(O)C1CO AAKDPDFZMNYDLR-UHFFFAOYSA-N 0.000 title claims description 9
238000004519 manufacturing process Methods 0.000 title claims description 6
BGMYHTUCJVZIRP-GASJEMHNSA-N nojirimycin Chemical compound OC[C@H]1NC(O)[C@H](O)[C@@H](O)[C@@H]1O BGMYHTUCJVZIRP-GASJEMHNSA-N 0.000 claims description 27
BGMYHTUCJVZIRP-UHFFFAOYSA-N Nojirimycin Natural products OCC1NC(O)C(O)C(O)C1O BGMYHTUCJVZIRP-UHFFFAOYSA-N 0.000 claims description 20
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 19
239000000126 substance Substances 0.000 claims description 14
238000000034 method Methods 0.000 description 15
239000000243 solution Substances 0.000 description 9
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
229920001467 poly(styrenesulfonates) Polymers 0.000 description 5
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
238000010531 catalytic reduction reaction Methods 0.000 description 4
239000013078 crystal Substances 0.000 description 4
238000000605 extraction Methods 0.000 description 4
239000002994 raw material Substances 0.000 description 4
229910000564 Raney nickel Inorganic materials 0.000 description 3
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 3
LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical class OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 3
239000013076 target substance Substances 0.000 description 3
241000186361 Actinobacteria <class> Species 0.000 description 2
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
239000007788 liquid Substances 0.000 description 2
238000007069 methylation reaction Methods 0.000 description 2
239000000203 mixture Substances 0.000 description 2
238000006722 reduction reaction Methods 0.000 description 2
238000005406 washing Methods 0.000 description 2
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
229930040373 Paraformaldehyde Natural products 0.000 description 1
239000004952 Polyamide Substances 0.000 description 1
239000004280 Sodium formate Substances 0.000 description 1
239000002253 acid Substances 0.000 description 1
238000005377 adsorption chromatography Methods 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000008280 blood Substances 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
-1 but if necessary Substances 0.000 description 1
239000007810 chemical reaction solvent Substances 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
LXBIFEVIBLOUGU-JGWLITMVSA-N duvoglustat Chemical compound OC[C@H]1NC[C@H](O)[C@@H](O)[C@@H]1O LXBIFEVIBLOUGU-JGWLITMVSA-N 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
238000000855 fermentation Methods 0.000 description 1
230000004151 fermentation Effects 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000003456 ion exchange resin Substances 0.000 description 1
229920003303 ion-exchange polymer Polymers 0.000 description 1
238000002955 isolation Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
229920002866 paraformaldehyde Polymers 0.000 description 1
238000004810 partition chromatography Methods 0.000 description 1
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
229920002647 polyamide Polymers 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
238000011403 purification operation Methods 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000001179 sorption measurement Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000001308 synthesis method Methods 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
241001446247 uncultured actinomycete Species 0.000 description 1

Landscapes

Hydrogenated Pyridines (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)

JP13550677A 1977-11-10 1977-11-10 Ｎ−メチルモラノリンの製造法 Expired JPS5927337B2 (ja)

Priority Applications (14)

Application Number	Priority Date	Filing Date	Title
JP13550677A JPS5927337B2 (ja)	1977-11-10	1977-11-10	Ｎ−メチルモラノリンの製造法
GB7840674A GB2009152B (en)	1977-11-10	1978-10-16	Method for producing moranoline and n-methylmoranoline
DE19782857509 DE2857509C2 (de)	1977-11-10	1978-10-23	Verfahren zur Herstellung von N-Methylmoranolin
DE2846118A DE2846118C3 (de)	1977-11-10	1978-10-23	Verfahren zur Herstellung von Moranolin
AT0792378A AT366032B (de)	1977-11-10	1978-11-06	Verfahren zur herstellung von moranolin und n-methylmoranolin
NLAANVRAGE7811106,A NL175819C (nl)	1977-11-10	1978-11-08	Werkwijze voor de bereiding van moranoline.
DK496478A DK149806C (da)	1977-11-10	1978-11-08	Fremgangsmaade til fremstilling af n-metylmoranolin
US05/959,163 US4339585A (en)	1977-11-10	1978-11-09	Method for the production of 2-hydroxymethyl-3,4,5-trihydroxy piperidine and the corresponding N-methyl derivative
FR7831724A FR2409986A1 (fr)	1977-11-10	1978-11-09	Procede de production de moranoline et nouveau produit ainsi obtenu
IT51847/78A IT1111075B (it)	1977-11-10	1978-11-09	Procedimento per produrre moranolina e n-metilmoranolina
SE7811582A SE439630B (sv)	1977-11-10	1978-11-09	Sett att framstella moranolin och n-metylmoranolin
CH1161078A CH637936A5 (de)	1977-11-10	1978-11-10	Verfahren zur herstellung von moranolin und n-methylmoranolin.
FR7908397A FR2414042A1 (fr)	1977-11-10	1979-04-03	Procede de production de n-methylmoranoline et nouveau produit ainsi obtenu
NL8304395A NL8304395A (nl)	1977-11-10	1983-12-22	Werkwijze voor de bereiding van n-methylmoranoline.

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP13550677A JPS5927337B2 (ja)	1977-11-10	1977-11-10	Ｎ−メチルモラノリンの製造法

Publications (2)

Publication Number	Publication Date
JPS5470282A JPS5470282A (en)	1979-06-05
JPS5927337B2 true JPS5927337B2 (ja)	1984-07-05

Family

ID=15153341

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP13550677A Expired JPS5927337B2 (ja)	1977-11-10	1977-11-10	Ｎ−メチルモラノリンの製造法

Country Status (2)

Country	Link
JP (1)	JPS5927337B2 (da)
DK (1)	DK149806C (da)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN110655487A (zh) *	2018-06-29	2020-01-07	江苏紫奇化工科技有限公司	一种1,2,2,6,6-五甲基哌啶醇的合成方法

1977
- 1977-11-10 JP JP13550677A patent/JPS5927337B2/ja not_active Expired
1978
- 1978-11-08 DK DK496478A patent/DK149806C/da not_active IP Right Cessation

Also Published As

Publication number	Publication date
DK149806C (da)	1987-04-06
DK149806B (da)	1986-10-06
DK496478A (da)	1979-05-11
JPS5470282A (en)	1979-06-05

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