FI59985C - Foerfarande foer framstaellning av terapeutiskt aktiv 1-isopropylamino-3-(4-(2-metoxietyl)fenoxi)-2-propanol samt dess syra-additionssalter - Google Patents

Foerfarande foer framstaellning av terapeutiskt aktiv 1-isopropylamino-3-(4-(2-metoxietyl)fenoxi)-2-propanol samt dess syra-additionssalter Download PDF

Info

Publication number: FI59985C
Authority: FI; Finland
Prior art keywords: methoxyethyl; phenoxy; isopropylamino; propanol; phenol
Prior art date: 1980-05-26

Application number

FI801680A

Other languages

English (en)

Finnish (fi)

Other versions

FI59985B (fi

Inventor

Lasse Antero Koskenniska

Arto Johannes Karjalainen

Reijo Juhani Toivola

Original Assignee

Farmos Oy

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.)

1980-05-26

Filing date

1980-05-26

Publication date

1982-01-08

1980-05-26 Application filed by Farmos Oy filed Critical Farmos Oy

1980-05-26 Priority to FI801680A priority Critical patent/FI59985C/fi

1981-05-14 Priority to FI811495A priority patent/FI61473C/fi

1981-05-22 Priority to AT81200558T priority patent/ATE5772T1/de

1981-05-22 Priority to EP81200558A priority patent/EP0041295B1/en

1981-05-25 Priority to JP7994381A priority patent/JPS5711947A/ja

1981-05-25 Priority to DK227981A priority patent/DK153143C/da

1981-07-31 Publication of FI59985B publication Critical patent/FI59985B/fi

1982-01-08 Application granted granted Critical

1982-01-08 Publication of FI59985C publication Critical patent/FI59985C/fi

Links

KFZMGEQAYNKOFK-UHFFFAOYSA-N 2-propanol Substances CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 title claims abstract description 8
150000003839 salts Chemical class 0.000 title claims description 5
101100148710 Clarkia breweri SAMT gene Proteins 0.000 title 1
230000004913 activation Effects 0.000 title 1
KHUXNRRPPZOJPT-UHFFFAOYSA-N phenoxy radical Chemical class O=C1C=C[CH]C=C1 KHUXNRRPPZOJPT-UHFFFAOYSA-N 0.000 title 1
JMSVCTWVEWCHDZ-UHFFFAOYSA-N syringic acid Chemical compound COC1=CC(C(O)=O)=CC(OC)=C1O JMSVCTWVEWCHDZ-UHFFFAOYSA-N 0.000 title 1
230000001225 therapeutic effect Effects 0.000 title 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 30
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 19
IUBSYMUCCVWXPE-UHFFFAOYSA-N metoprolol Chemical compound COCCC1=CC=C(OCC(O)CNC(C)C)C=C1 IUBSYMUCCVWXPE-UHFFFAOYSA-N 0.000 claims abstract description 14
238000000034 method Methods 0.000 claims abstract description 12
HUXGFSJRCMJOAK-UHFFFAOYSA-N 1-(4-hydroxyphenyl)-2-methoxyethanone Chemical compound COCC(=O)C1=CC=C(O)C=C1 HUXGFSJRCMJOAK-UHFFFAOYSA-N 0.000 claims abstract description 8
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims abstract description 7
PETGYPBYTINWKW-UHFFFAOYSA-N 4-(1-hydroxy-2-methoxyethyl)phenol Chemical compound COCC(O)C1=CC=C(O)C=C1 PETGYPBYTINWKW-UHFFFAOYSA-N 0.000 claims abstract description 6
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 claims abstract description 6
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims abstract description 6
238000002360 preparation method Methods 0.000 claims abstract description 6
239000002253 acid Substances 0.000 claims abstract description 5
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims abstract 6
239000001294 propane Substances 0.000 claims abstract 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 12
239000002904 solvent Substances 0.000 claims description 11
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 10
-1 ethyl ethyl Chemical group 0.000 claims description 7
239000003054 catalyst Substances 0.000 claims description 5
239000003377 acid catalyst Substances 0.000 claims description 4
UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 claims description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
159000000000 sodium salts Chemical class 0.000 claims description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 2
230000002378 acidificating effect Effects 0.000 claims 1
239000003638 chemical reducing agent Substances 0.000 claims 1
238000007796 conventional method Methods 0.000 claims 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
239000003960 organic solvent Substances 0.000 claims 1
238000006243 chemical reaction Methods 0.000 abstract description 17
150000001875 compounds Chemical class 0.000 abstract description 3
239000000203 mixture Substances 0.000 description 23
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
239000000243 solution Substances 0.000 description 12
239000000543 intermediate Substances 0.000 description 11
LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 description 8
238000003756 stirring Methods 0.000 description 8
HJBDONUFSITAEF-UHFFFAOYSA-N 1-[4-(1,2-dimethoxyethyl)phenoxy]-3-(propan-2-ylamino)propan-2-ol Chemical compound COCC(OC)C1=CC=C(OCC(O)CNC(C)C)C=C1 HJBDONUFSITAEF-UHFFFAOYSA-N 0.000 description 7
238000001704 evaporation Methods 0.000 description 7
230000008020 evaporation Effects 0.000 description 7
229960002237 metoprolol Drugs 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 5
KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
229910000033 sodium borohydride Inorganic materials 0.000 description 5
239000012279 sodium borohydride Substances 0.000 description 5
FLVRAMDWTASCBO-UHFFFAOYSA-N 2-[[4-(1,2-dimethoxyethyl)phenoxy]methyl]oxirane Chemical compound C1=CC(C(OC)COC)=CC=C1OCC1OC1 FLVRAMDWTASCBO-UHFFFAOYSA-N 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
239000007787 solid Substances 0.000 description 4
OGZSYTRHUJFHEX-UHFFFAOYSA-N 1-[4-(1-ethoxy-2-methoxyethyl)phenoxy]-3-(propan-2-ylamino)propan-2-ol Chemical compound CCOC(COC)C1=CC=C(OCC(O)CNC(C)C)C=C1 OGZSYTRHUJFHEX-UHFFFAOYSA-N 0.000 description 3
MOEFFSWKSMRFRQ-UHFFFAOYSA-N 2-ethoxyphenol Chemical compound CCOC1=CC=CC=C1O MOEFFSWKSMRFRQ-UHFFFAOYSA-N 0.000 description 3
125000003545 alkoxy group Chemical group 0.000 description 3
238000009903 catalytic hydrogenation reaction Methods 0.000 description 3
238000005984 hydrogenation reaction Methods 0.000 description 3
229910000027 potassium carbonate Inorganic materials 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
PNNZEIHPTJGIAN-UHFFFAOYSA-N 2-[[4-(1-ethoxy-2-methoxyethyl)phenoxy]methyl]oxirane Chemical compound C1=CC(C(COC)OCC)=CC=C1OCC1OC1 PNNZEIHPTJGIAN-UHFFFAOYSA-N 0.000 description 2
SMWUXCFAVCWDJZ-UHFFFAOYSA-N 4-(1,2-dimethoxyethyl)phenol Chemical compound COCC(OC)C1=CC=C(O)C=C1 SMWUXCFAVCWDJZ-UHFFFAOYSA-N 0.000 description 2
ZAUPKBDSRHOTCE-UHFFFAOYSA-N 4-(1-ethoxy-2-methoxyethyl)phenol Chemical compound CCOC(COC)C1=CC=C(O)C=C1 ZAUPKBDSRHOTCE-UHFFFAOYSA-N 0.000 description 2
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
102000012740 beta Adrenergic Receptors Human genes 0.000 description 2
108010079452 beta Adrenergic Receptors Proteins 0.000 description 2
238000009835 boiling Methods 0.000 description 2
238000001816 cooling Methods 0.000 description 2
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
238000001914 filtration Methods 0.000 description 2
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
238000010992 reflux Methods 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 2
229940095064 tartrate Drugs 0.000 description 2
150000003892 tartrate salts Chemical class 0.000 description 2
238000005303 weighing Methods 0.000 description 2
XADVLVSLKPEHAS-UHFFFAOYSA-N 1-[1-(2-methoxyethyl)cyclohexa-2,4-dien-1-yl]oxy-3-(propan-2-ylamino)propan-2-ol Chemical compound COCCC1(OCC(CNC(C)C)O)CC=CC=C1 XADVLVSLKPEHAS-UHFFFAOYSA-N 0.000 description 1
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
FAYGEALAEQKPDI-UHFFFAOYSA-N 4-(2-methoxyethyl)phenol Chemical compound COCCC1=CC=C(O)C=C1 FAYGEALAEQKPDI-UHFFFAOYSA-N 0.000 description 1
239000007868 Raney catalyst Substances 0.000 description 1
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
229910000564 Raney nickel Inorganic materials 0.000 description 1
125000006177 alkyl benzyl group Chemical group 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
125000004104 aryloxy group Chemical group 0.000 description 1
UKXSKSHDVLQNKG-UHFFFAOYSA-N benzilic acid Chemical group C=1C=CC=CC=1C(O)(C(=O)O)C1=CC=CC=C1 UKXSKSHDVLQNKG-UHFFFAOYSA-N 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
239000002876 beta blocker Substances 0.000 description 1
244000309464 bull Species 0.000 description 1
230000000747 cardiac effect Effects 0.000 description 1
150000004292 cyclic ethers Chemical class 0.000 description 1
MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical class C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 1
230000029087 digestion Effects 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
ROAYSRAUMPWBQX-UHFFFAOYSA-N ethanol;sulfuric acid Chemical compound CCO.OS(O)(=O)=O ROAYSRAUMPWBQX-UHFFFAOYSA-N 0.000 description 1
125000001033 ether group Chemical group 0.000 description 1
238000000605 extraction Methods 0.000 description 1
208000019622 heart disease Diseases 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
238000007327 hydrogenolysis reaction Methods 0.000 description 1
238000009413 insulation Methods 0.000 description 1
238000002955 isolation Methods 0.000 description 1
235000015250 liver sausages Nutrition 0.000 description 1
210000004072 lung Anatomy 0.000 description 1
WCYAALZQFZMMOM-UHFFFAOYSA-N methanol;sulfuric acid Chemical compound OC.OS(O)(=O)=O WCYAALZQFZMMOM-UHFFFAOYSA-N 0.000 description 1
238000006053 organic reaction Methods 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
102000005962 receptors Human genes 0.000 description 1
108020003175 receptors Proteins 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
230000002792 vascular Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/14—Unsaturated ethers
- C07C43/178—Unsaturated ethers containing hydroxy or O-metal groups
- C07C43/1782—Unsaturated ethers containing hydroxy or O-metal groups containing six-membered aromatic rings
- 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
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
- C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
- C07D303/24—Ethers with hydroxy compounds containing no oxirane rings with polyhydroxy compounds
- C07D303/26—Ethers with hydroxy compounds containing no oxirane rings with polyhydroxy compounds having one or more free hydroxyl radicals

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Catalysts (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

FI801680A 1980-05-26 1980-05-26 Foerfarande foer framstaellning av terapeutiskt aktiv 1-isopropylamino-3-(4-(2-metoxietyl)fenoxi)-2-propanol samt dess syra-additionssalter FI59985C (fi)

Priority Applications (6)

Application Number	Priority Date	Filing Date	Title
FI801680A FI59985C (fi)	1980-05-26	1980-05-26	Foerfarande foer framstaellning av terapeutiskt aktiv 1-isopropylamino-3-(4-(2-metoxietyl)fenoxi)-2-propanol samt dess syra-additionssalter
FI811495A FI61473C (fi)	1980-05-26	1981-05-14	Mellanprodukt vid framstaellning av terapeutiskt aktiv 1-isopropylamino-3-(4-(2-metoxietyl)-fenoxi)-2-propanol
AT81200558T ATE5772T1 (de)	1980-05-26	1981-05-22	Verfahren zur herstellung von 1-isopropylamino-3(4-(2-methoxy-ethyl)-phenoxy)-2-propanol.
EP81200558A EP0041295B1 (en)	1980-05-26	1981-05-22	Process for the preparation of 1-isopropylamino-3-(4-(2-methoxy-ethyl)-phenoxy)-2-propanol
JP7994381A JPS5711947A (en)	1980-05-26	1981-05-25	Manufacture of 1-isopropylamino-3-(4-(2- methoxyethyl)-phenoxy)-2-propanol
DK227981A DK153143C (da)	1980-05-26	1981-05-25	Fremgangsmaade til fremstilling af 1-isopropylamino-3-(4-(2-methoxyethyl)-phenoxy)-2-propanol eller syreadditionssalte deraf

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FI801680		1980-05-26
FI801680A FI59985C (fi)	1980-05-26	1980-05-26	Foerfarande foer framstaellning av terapeutiskt aktiv 1-isopropylamino-3-(4-(2-metoxietyl)fenoxi)-2-propanol samt dess syra-additionssalter

Publications (2)

Publication Number	Publication Date
FI59985B FI59985B (fi)	1981-07-31
FI59985C true FI59985C (fi)	1982-01-08

Family

ID=8513506

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
FI801680A FI59985C (fi)	1980-05-26	1980-05-26	Foerfarande foer framstaellning av terapeutiskt aktiv 1-isopropylamino-3-(4-(2-metoxietyl)fenoxi)-2-propanol samt dess syra-additionssalter

Country Status (5)

Country	Link
EP (1)	EP0041295B1 (da)
JP (1)	JPS5711947A (da)
AT (1)	ATE5772T1 (da)
DK (1)	DK153143C (da)
FI (1)	FI59985C (da)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4665094A (en) *	1985-08-29	1987-05-12	Merck & Co., Inc.	Oculoselective beta-blockers for treatment of elevated intraocular pressure
US4945182A (en) *	1985-12-24	1990-07-31	Merck & Co., Inc.	Oculoselective beta-blockers
CN102964258B (zh) *	2012-12-11	2014-01-29	上海奥博生物医药技术有限公司	一种美托洛尔有关物质j的制备方法

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
SE354851B (da) *	1970-02-18	1973-03-26	Haessle Ab
FI59392C (fi) *	1978-04-01	1982-02-02	Farmos Oy	Foerfarande foer framstaellning av terapeutiskt aktiv 1-isopropylamino-3-(4-(2-metoxietyl)fenoxi)-2-propanol samt dess syraadditionssalter
NL7907207A (nl) *	1979-09-27	1981-03-31	Farmos Oy	Werkwijze voor het bereiden van therapeutisch actief propanolamine.

1980
- 1980-05-26 FI FI801680A patent/FI59985C/fi not_active IP Right Cessation
1981
- 1981-05-22 EP EP81200558A patent/EP0041295B1/en not_active Expired
- 1981-05-22 AT AT81200558T patent/ATE5772T1/de active
- 1981-05-25 JP JP7994381A patent/JPS5711947A/ja active Granted
- 1981-05-25 DK DK227981A patent/DK153143C/da not_active IP Right Cessation

Also Published As

Publication number	Publication date
DK153143C (da)	1988-10-31
JPH027937B2 (da)	1990-02-21
ATE5772T1 (de)	1984-01-15
EP0041295B1 (en)	1984-01-04
FI59985B (fi)	1981-07-31
EP0041295A1 (en)	1981-12-09
DK153143B (da)	1988-06-20
JPS5711947A (en)	1982-01-21
DK227981A (da)	1981-11-27

Legal Events

Date	Code	Title	Description
2004-08-31	MM	Patent lapsed	Owner name: AB HAESSLE

Publication	Publication Date	Title
EP0188248B1 (en)	1990-07-11	Naphthalene derivatives, process for the preparation thereof and pharmaceutical composition containing same
FI61027B (fi)	1982-01-29	Foerfarande foer framstaellning av terapeutiskt anvaendbara alkanolaminderivat
US5589514A (en)	1996-12-31	Arylcycloalkyl derivatives, their production and their use
US20080300271A1 (en)	2008-12-04	Novel compounds and a novel process for their preparation
HU187611B (en)	1986-02-28	Process for production of substituaded amino-acetofenon derivates
US6159988A (en)	2000-12-12	Arylcycloalkyl derivatives, their production and their use
US4059622A (en)	1977-11-22	Alkanolamine derivatives
JPS6110528A (ja)	1986-01-18	フエノ−ル誘導体、その製造法、および該化合物を含有する抗エストロゲン作用を有する医薬組成物
FI69835C (fi)	1986-05-26	Foerfarande foer framstaellning av terapeutiskt anvaendbara 3-ndolyl-tertiaerbutylaminopropanolderivat
FI59985C (fi)	1982-01-08	Foerfarande foer framstaellning av terapeutiskt aktiv 1-isopropylamino-3-(4-(2-metoxietyl)fenoxi)-2-propanol samt dess syra-additionssalter
IE40267B1 (en)	1979-04-25	Alkanolamine derivatives
FI59999C (fi)	1981-11-10	Foerfarande foer framstaellning av farmakologiskt vaerdefulla cyklopropylmetylamino- 2-oxazoliner
EP0094102A2 (fr)	1983-11-16	Nouveaux dérivés de 1-(1-cyclohexénylméthyl) pyrrolidine et leur procédé de préparation
EP0936212B1 (en)	2004-04-21	Fluorine-containing aniline compounds
KR20010029733A (ko)	2001-04-16	시스-1-[2-[4-(6-메톡시-2-페닐-1,2,3,4-테트라히드로나프탈렌-1-일)페녹시]에틸]피롤리딘의 제조 방법
US4515814A (en)	1985-05-07	3-Phenoxypropan-2-ol derivatives for treating glaucoma
US3934032A (en)	1976-01-20	Alkanolamine derivatives for treating hypertension
FI61473B (fi)	1982-04-30	Mellanprodukt vid framstaellning av terapeutiskt aktiv 1-isopropylamino-3-(4-(2-metoxietyl)-fenoxi)-2-propanol
Borude et al.	2013	Synthesis of β-amino alcohol derivatives from phenols in presence of phase transfer catalyst and lipase biocatalyst
FI63016B (fi)	1982-12-31	Foerfarande foer framstaellning av en terapeutiskt aktiv propanolamin
US3959486A (en)	1976-05-25	Method for producing β-adrenergic blockage with alkanolamine derivatives
US4321398A (en)	1982-03-23	Thienyl and benzothienyl-tertiary butylaminophenoxypropanols
FI58909C (fi)	1981-05-11	Foerfarande foer framstaellning av den terapeutiskt aktiva foereningen 1-isopropylamino-3-(4-(2-metoxietyl)-fenoxi)-2-propanol och dess syraadditionssalter
FI58491B (fi)	1980-10-31	Foerfarande foer framstaellning av 1-isopropylamino-3-(4-(2-metoxietyl)fenoxi)-2-propanol med terapeutisk aktivitet samt syra-additionssalter daerav
KR840001077B1 (ko)	1984-07-31	N⁴-카르바모일 피페라지노 프로판올 유도체의 제조방법