JPS5943946B2 - Ｎ−アルケニルモラノリン誘導体 - Google Patents

Ｎ−アルケニルモラノリン誘導体

Info

Publication number: JPS5943946B2
Authority: JP; Japan
Prior art keywords: substances; moranoline; alkenylmoranoline; derivative; formula
Prior art date: 1978-04-28
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

JP53051023A

Other languages

English (en)

Japanese (ja)

Other versions

JPS54144380A (en

Inventor

進午松村

宏榎本

良明青柳

義明吉国

紘平倉

政広八木

一朗白波瀬

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.)

1978-04-28

Filing date

1978-04-28

Publication date

1984-10-25

1978-04-28 Application filed by Nippon Shinyaku Co Ltd filed Critical Nippon Shinyaku Co Ltd

1978-04-28 Priority to JP53051023A priority Critical patent/JPS5943946B2/ja

1979-03-07 Priority to GB7908030A priority patent/GB2019843B/en

1979-03-12 Priority to DE2909646A priority patent/DE2909646C3/de

1979-04-17 Priority to SE7903336A priority patent/SE420311B/sv

1979-04-18 Priority to FR7909795A priority patent/FR2424258A1/fr

1979-04-18 Priority to NLAANVRAGE7903017,A priority patent/NL179053C/xx

1979-04-20 Priority to IT48802/79A priority patent/IT1116869B/it

1979-04-23 Priority to BE0/194793A priority patent/BE875799A/xx

1979-04-25 Priority to AT0310779A priority patent/AT371438B/de

1979-04-26 Priority to DK172479A priority patent/DK149750C/da

1979-04-26 Priority to CH395579A priority patent/CH639373A5/de

1979-11-10 Publication of JPS54144380A publication Critical patent/JPS54144380A/ja

1984-10-25 Publication of JPS5943946B2 publication Critical patent/JPS5943946B2/ja

Status Expired legal-status Critical Current

Links

239000000126 substance Substances 0.000 claims description 22
239000002253 acid Substances 0.000 claims description 4
125000001189 phytyl group Chemical group [H]C([*])([H])/C([H])=C(C([H])([H])[H])/C([H])([H])C([H])([H])C([H])([H])[C@@](C([H])([H])[H])([H])C([H])([H])C([H])([H])C([H])([H])[C@@](C([H])([H])[H])([H])C([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])C([H])([H])[H] 0.000 claims description 3
150000003839 salts Chemical class 0.000 claims description 2
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
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 15
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
LXBIFEVIBLOUGU-UHFFFAOYSA-N Deoxymannojirimycin Natural products OCC1NCC(O)C(O)C1O LXBIFEVIBLOUGU-UHFFFAOYSA-N 0.000 description 11
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
230000015572 biosynthetic process Effects 0.000 description 5
150000001875 compounds Chemical class 0.000 description 5
238000000034 method Methods 0.000 description 5
230000002829 reductive effect Effects 0.000 description 5
238000003786 synthesis reaction Methods 0.000 description 5
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
-1 alkenyl halide Chemical class 0.000 description 4
239000000203 mixture Substances 0.000 description 4
229910000027 potassium carbonate Inorganic materials 0.000 description 4
239000000741 silica gel Substances 0.000 description 4
229910002027 silica gel Inorganic materials 0.000 description 4
238000003756 stirring Methods 0.000 description 4
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 3
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
239000003513 alkali Substances 0.000 description 3
239000008280 blood Substances 0.000 description 3
210000004369 blood Anatomy 0.000 description 3
239000007795 chemical reaction product Substances 0.000 description 3
238000004440 column chromatography Methods 0.000 description 3
239000003814 drug Substances 0.000 description 3
239000003456 ion exchange resin Substances 0.000 description 3
229920003303 ion-exchange polymer Polymers 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
229920001467 poly(styrenesulfonates) Polymers 0.000 description 3
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
JVDWKJQBWSKJOJ-UHFFFAOYSA-N 1-bromo-3-methylbuta-1,3-diene Chemical compound CC(=C)C=CBr JVDWKJQBWSKJOJ-UHFFFAOYSA-N 0.000 description 2
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
125000003342 alkenyl group Chemical group 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
239000002798 polar solvent Substances 0.000 description 2
125000006239 protecting group Chemical group 0.000 description 2
230000002194 synthesizing effect Effects 0.000 description 2
238000005406 washing Methods 0.000 description 2
WLAUCMCTKPXDIY-JXMROGBWSA-N (2e)-1-chloro-3,7-dimethylocta-2,6-diene Chemical compound CC(C)=CCC\C(C)=C\CCl WLAUCMCTKPXDIY-JXMROGBWSA-N 0.000 description 1
FOFMBFMTJFSEEY-YFVJMOTDSA-N (2e,6e)-1-bromo-3,7,11-trimethyldodeca-2,6,10-triene Chemical compound CC(C)=CCC\C(C)=C\CC\C(C)=C\CBr FOFMBFMTJFSEEY-YFVJMOTDSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
235000008708 Morus alba Nutrition 0.000 description 1
240000000249 Morus alba Species 0.000 description 1
241000700159 Rattus Species 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
229910001854 alkali hydroxide Inorganic materials 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
RTEXIPZMMDUXMR-UHFFFAOYSA-N benzene;ethyl acetate Chemical compound CCOC(C)=O.C1=CC=CC=C1 RTEXIPZMMDUXMR-UHFFFAOYSA-N 0.000 description 1
239000003093 cationic surfactant Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
229940079593 drug Drugs 0.000 description 1
230000000694 effects Effects 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
230000003345 hyperglycaemic effect Effects 0.000 description 1
201000001421 hyperglycemia Diseases 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
239000000463 material Substances 0.000 description 1
239000012046 mixed solvent Substances 0.000 description 1
229930014626 natural product Natural products 0.000 description 1
239000012454 non-polar solvent Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000003444 phase transfer catalyst Substances 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
230000001766 physiological effect Effects 0.000 description 1
239000000843 powder Substances 0.000 description 1
230000003449 preventive effect Effects 0.000 description 1
238000005932 reductive alkylation reaction Methods 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
229940126585 therapeutic drug Drugs 0.000 description 1
CRDAMVZIKSXKFV-UHFFFAOYSA-N trans-Farnesol Natural products CC(C)=CCCC(C)=CCCC(C)=CCO CRDAMVZIKSXKFV-UHFFFAOYSA-N 0.000 description 1
235000001459 whitebark Nutrition 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members 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 ring carbon atoms
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Diabetes (AREA)
Chemical Kinetics & Catalysis (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Hematology (AREA)
Obesity (AREA)
Emergency Medicine (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Endocrinology (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Hydrogenated Pyridines (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Steroid Compounds (AREA)

JP53051023A 1978-04-28 1978-04-28 Ｎ−アルケニルモラノリン誘導体 Expired JPS5943946B2 (ja)

Priority Applications (11)

Application Number	Priority Date	Filing Date	Title
JP53051023A JPS5943946B2 (ja)	1978-04-28	1978-04-28	Ｎ−アルケニルモラノリン誘導体
GB7908030A GB2019843B (en)	1978-04-28	1979-03-07	N-alkenylmoranoline derivatives
DE2909646A DE2909646C3 (de)	1978-04-28	1979-03-12	N-Alkenylmoranolinderivate
SE7903336A SE420311B (sv)	1978-04-28	1979-04-17	N-alkenyl-2-hydroximetyl-3,4,5-trihydroxipiperidin
FR7909795A FR2424258A1 (fr)	1978-04-28	1979-04-18	Derives de n-alkenylmoranoline et leur utilisation comme produits inhibant l'augmentation de sucre dans le sang
NLAANVRAGE7903017,A NL179053C (nl)	1978-04-28	1979-04-18	N-gesubstitueerde moranolinederivaten, werkwijze voor de bereiding ervan, alsmede werkwijze voor de bereiding van een geneesmiddel met een dergelijk derivaat erin.
IT48802/79A IT1116869B (it)	1978-04-28	1979-04-20	Derivati di n-alcheni-moranolina aventi attivita'farmacologica
BE0/194793A BE875799A (fr)	1978-04-28	1979-04-23	N-alkenylmoranolines
AT0310779A AT371438B (de)	1978-04-28	1979-04-25	Verfahren zur herstellung von neuen n-alkenylmoranolinderivaten und ihrer saeureadditionssalze
DK172479A DK149750C (da)	1978-04-28	1979-04-26	Analogifremgangsmaade til fremstilling af n-alkenylmoranolin-derivater eller farmaceutiske acceptable syreadditionssalte deraf
CH395579A CH639373A5 (de)	1978-04-28	1979-04-26	N-alkenylmoranolin derivate.

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP53051023A JPS5943946B2 (ja)	1978-04-28	1978-04-28	Ｎ−アルケニルモラノリン誘導体

Publications (2)

Publication Number	Publication Date
JPS54144380A JPS54144380A (en)	1979-11-10
JPS5943946B2 true JPS5943946B2 (ja)	1984-10-25

Family

ID=12875196

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP53051023A Expired JPS5943946B2 (ja)	1978-04-28	1978-04-28	Ｎ−アルケニルモラノリン誘導体

Country Status (11)

Country	Link
JP (1)	JPS5943946B2 (da)
AT (1)	AT371438B (da)
BE (1)	BE875799A (da)
CH (1)	CH639373A5 (da)
DE (1)	DE2909646C3 (da)
DK (1)	DK149750C (da)
FR (1)	FR2424258A1 (da)
GB (1)	GB2019843B (da)
IT (1)	IT1116869B (da)
NL (1)	NL179053C (da)
SE (1)	SE420311B (da)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2925943A1 (de) *	1979-06-27	1981-01-29	Bayer Ag	1-alkadien-2,4-yl-2-hydroxymethyl3,4,5-trihydroxypiperidine, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel
JPS56108767A (en) *	1980-01-28	1981-08-28	Nippon Shinyaku Co Ltd	Bismoranoline derivative
GB8827701D0 (en) *	1987-12-09	1988-12-29	Nippon Shinyaku Co Ltd	Thrombolytic &c compositions
US5536732A (en) *	1990-04-27	1996-07-16	Merrell Pharmaceuticals Inc.	N-derivatives of 1-deoxy nojirimycin
US5252587A (en) *	1990-04-27	1993-10-12	Merrell Dow Pharmaceuticals, Inc.	N-derivatives of 1-deoxy nojirimycin
JP2016510306A (ja) *	2012-05-08	2016-04-07	セリックスビオプライヴェートリミテッド	高血糖の治療のための組成物及び方法

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NO154918C (no) *	1977-08-27	1987-01-14	Bayer Ag	Analogifremgangsmaate til fremstilling av terapeutisk aktive derivater av 3,4,5-trihydroksypiperidin.

1978
- 1978-04-28 JP JP53051023A patent/JPS5943946B2/ja not_active Expired
1979
- 1979-03-07 GB GB7908030A patent/GB2019843B/en not_active Expired
- 1979-03-12 DE DE2909646A patent/DE2909646C3/de not_active Expired
- 1979-04-17 SE SE7903336A patent/SE420311B/sv not_active IP Right Cessation
- 1979-04-18 FR FR7909795A patent/FR2424258A1/fr active Granted
- 1979-04-18 NL NLAANVRAGE7903017,A patent/NL179053C/xx not_active IP Right Cessation
- 1979-04-20 IT IT48802/79A patent/IT1116869B/it active
- 1979-04-23 BE BE0/194793A patent/BE875799A/xx not_active IP Right Cessation
- 1979-04-25 AT AT0310779A patent/AT371438B/de not_active IP Right Cessation
- 1979-04-26 DK DK172479A patent/DK149750C/da not_active IP Right Cessation
- 1979-04-26 CH CH395579A patent/CH639373A5/de not_active IP Right Cessation

Also Published As

Publication number	Publication date
SE7903336L (sv)	1979-10-29
GB2019843A (en)	1979-11-07
NL179053C (nl)	1986-07-01
DK172479A (da)	1979-10-29
CH639373A5 (de)	1983-11-15
DE2909646A1 (de)	1979-10-31
JPS54144380A (en)	1979-11-10
IT7948802A0 (it)	1979-04-20
DK149750B (da)	1986-09-22
NL7903017A (nl)	1979-10-30
FR2424258B1 (da)	1981-12-11
SE420311B (sv)	1981-09-28
IT1116869B (it)	1986-02-10
ATA310779A (de)	1982-11-15
FR2424258A1 (fr)	1979-11-23
AT371438B (de)	1983-06-27
BE875799A (fr)	1979-08-16
DE2909646C3 (de)	1980-09-11
GB2019843B (en)	1982-08-04
DK149750C (da)	1987-12-14
DE2909646B1 (de)	1980-01-10

Publication	Publication Date	Title
US4423044A (en)	1983-12-27	3,4-Dihydro-5H-2,3-benzodiazepine derivatives and pharmaceutical use thereof
JPS5943459B2 (ja)	1984-10-22	Ｎ−アルキルピペリジン誘導体
SU1356960A3 (ru)	1987-11-30	Способ получени производных пиридазина
US3953456A (en)	1976-04-27	Carbostyril derivatives and process for preparing the same
FR2479821A1 (fr)	1981-10-09	Derives de n4-carbamoylpiperazinopropanol utiles pour leur activite de b-blocage d'adrenaline
JPS5943946B2 (ja)	1984-10-25	Ｎ−アルケニルモラノリン誘導体
JPS6312063B2 (da)	1988-03-17
JPS5943949B2 (ja)	1984-10-25	モラノリンのｎ−置換誘導体
EP0011747B1 (de)	1982-05-19	Aminopropanolderivate des 6-Hydroxy-2,3,4,5-tetrahydro-1H-1-benzazepin-2-ons, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Zubereitungen
JPS5857373A (ja)	1983-04-05	Ｌ−アスコルビン酸誘導体の製法
US4511566A (en)	1985-04-16	2-N-Cycloalkylmethyl 3-oxo 5,6-diaryl-as-triazines
FR2478094A1 (fr)	1981-09-18	Derives de cinnamylmoranoline a substitution ammonio, a activite d'inhibition de l'augmentation de niveau de sucre dans le sang
KR820001122B1 (ko)	1982-06-26	N-알케닐 몰라노린 유도체의 제조방법
JPS6026387B2 (ja)	1985-06-24	シンナミルモラノリン誘導体
JPS6042795B2 (ja)	1985-09-25	カルバモイルピペラジン誘導体
JPS5943947B2 (ja)	1984-10-25	Ｎ−置換モラノリン誘導体
KR820001124B1 (ko)	1982-06-26	N-알케닐 몰라노린 유도체의 제법
US3093652A (en)	1963-06-11	Alkyl 1-(2-aryl-2-oxoalkyl)-4-phenylpiperidine-4-carboxylates and their preparation
EP0240338B1 (en)	1990-07-04	Butenoic acid derivatives
US2970159A (en)	1961-01-31	Hydrazine derivatives
US4643996A (en)	1987-02-17	5-phenyl-2-furoic acid hydrazides
KR820001123B1 (ko)	1982-06-26	N-치환 몰라노린 유도체의 제조방법
CA1242200A (en)	1988-09-20	N-nitroso compounds, and their preparation and use
FI63016B (fi)	1982-12-31	Foerfarande foer framstaellning av en terapeutiskt aktiv propanolamin
KR820001081B1 (ko)	1982-06-21	모라노린 유도체의 제법