DD268158A5 - Verfahren zur herstellung von tert.-butylamino-3-(phenyl-2'-phenoxy)-1-propanol-2 und seine salze mit saeuren enthaltenden arzneimittelpraeparaten - Google Patents

Verfahren zur herstellung von tert.-butylamino-3-(phenyl-2'-phenoxy)-1-propanol-2 und seine salze mit saeuren enthaltenden arzneimittelpraeparaten Download PDF

Info

Publication number: DD268158A5
Authority: DD; German Democratic Republic
Prior art keywords: salts; propanol; butylamino; phenoxy; phenyl
Prior art date: 1987-03-25

Application number

DD88313963A

Other languages

German (de)

English (en)

Inventor

Gerd Petrik

Original Assignee

��@�K@��@��@�K@��K@��k��

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.)

1987-03-25

Filing date

1988-03-24

Publication date

1989-05-24

1988-03-24 Application filed by ��@�K@��@��@�K@��K@��k�� filed Critical ��@�K@��@��@�K@��K@��k��

1989-05-24 Publication of DD268158A5 publication Critical patent/DD268158A5/de

Links

238000002360 preparation method Methods 0.000 title claims abstract description 10
239000003814 drug Substances 0.000 title description 8
238000004519 manufacturing process Methods 0.000 title description 3
150000003839 salts Chemical class 0.000 claims abstract description 10
238000000034 method Methods 0.000 claims abstract description 5
DBHPVKNFKBKJCE-UHFFFAOYSA-N 1-(tert-butylamino)-3-(2-phenylphenoxy)propan-2-ol Chemical compound CC(C)(C)NCC(O)COC1=CC=CC=C1C1=CC=CC=C1 DBHPVKNFKBKJCE-UHFFFAOYSA-N 0.000 claims description 21
239000012050 conventional carrier Substances 0.000 claims 1
229940079920 digestives acid preparations Drugs 0.000 claims 1
239000002253 acid Substances 0.000 abstract description 8
150000007513 acids Chemical class 0.000 abstract description 6
239000003416 antiarrhythmic agent Substances 0.000 abstract description 4
239000000825 pharmaceutical preparation Substances 0.000 abstract description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
230000000694 effects Effects 0.000 description 10
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
230000003288 anthiarrhythmic effect Effects 0.000 description 7
JWHAUXFOSRPERK-UHFFFAOYSA-N propafenone Chemical compound CCCNCC(O)COC1=CC=CC=C1C(=O)CCC1=CC=CC=C1 JWHAUXFOSRPERK-UHFFFAOYSA-N 0.000 description 7
229960000203 propafenone Drugs 0.000 description 7
241000282472 Canis lupus familiaris Species 0.000 description 6
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
239000000243 solution Substances 0.000 description 6
150000001875 compounds Chemical class 0.000 description 5
229910000041 hydrogen chloride Inorganic materials 0.000 description 5
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
230000000297 inotrophic effect Effects 0.000 description 5
206010003119 arrhythmia Diseases 0.000 description 4
VDKMYSMWQCFYBQ-UHFFFAOYSA-N diprafenone Chemical compound CCC(C)(C)NCC(O)COC1=CC=CC=C1C(=O)CCC1=CC=CC=C1 VDKMYSMWQCFYBQ-UHFFFAOYSA-N 0.000 description 4
229950002948 diprafenone Drugs 0.000 description 4
229940079593 drug Drugs 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
241000700159 Rattus Species 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
239000004480 active ingredient Substances 0.000 description 3
230000000004 hemodynamic effect Effects 0.000 description 3
238000001727 in vivo Methods 0.000 description 3
235000019359 magnesium stearate Nutrition 0.000 description 3
239000000203 mixture Substances 0.000 description 3
239000003826 tablet Substances 0.000 description 3
230000001225 therapeutic effect Effects 0.000 description 3
231100000331 toxic Toxicity 0.000 description 3
230000002588 toxic effect Effects 0.000 description 3
241000700199 Cavia porcellus Species 0.000 description 2
206010019280 Heart failures Diseases 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
239000003929 acidic solution Substances 0.000 description 2
230000036982 action potential Effects 0.000 description 2
UCTWMZQNUQWSLP-UHFFFAOYSA-N adrenaline Chemical compound CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 description 2
239000002876 beta blocker Substances 0.000 description 2
239000004305 biphenyl Substances 0.000 description 2
230000037396 body weight Effects 0.000 description 2
230000000747 cardiac effect Effects 0.000 description 2
230000008602 contraction Effects 0.000 description 2
239000013078 crystal Substances 0.000 description 2
239000012458 free base Substances 0.000 description 2
239000008187 granular material Substances 0.000 description 2
238000002156 mixing Methods 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
230000009090 positive inotropic effect Effects 0.000 description 2
239000000843 powder Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
108010014172 Factor V Proteins 0.000 description 1
DJBNUMBKLMJRSA-UHFFFAOYSA-N Flecainide Chemical compound FC(F)(F)COC1=CC=C(OCC(F)(F)F)C(C(=O)NCC2NCCCC2)=C1 DJBNUMBKLMJRSA-UHFFFAOYSA-N 0.000 description 1
208000001953 Hypotension Diseases 0.000 description 1
238000012404 In vitro experiment Methods 0.000 description 1
206010022998 Irritability Diseases 0.000 description 1
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
229920000168 Microcrystalline cellulose Polymers 0.000 description 1
WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
239000000219 Sympatholytic Substances 0.000 description 1
206010047281 Ventricular arrhythmia Diseases 0.000 description 1
235000011037 adipic acid Nutrition 0.000 description 1
150000001279 adipic acids Chemical class 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
239000011260 aqueous acid Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
210000001367 artery Anatomy 0.000 description 1
230000001746 atrial effect Effects 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
150000001559 benzoic acids Chemical class 0.000 description 1
229940097320 beta blocking agent Drugs 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical group OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 1
238000009835 boiling Methods 0.000 description 1
230000005587 bubbling Effects 0.000 description 1
239000002775 capsule Substances 0.000 description 1
230000001778 cardiodepressive effect Effects 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
YDVNLQGCLLPHAH-UHFFFAOYSA-N dichloromethane;hydrate Chemical compound O.ClCCl YDVNLQGCLLPHAH-UHFFFAOYSA-N 0.000 description 1
BLEBFDYUDVZRFG-UHFFFAOYSA-N dichloromethane;propan-2-ol Chemical compound ClCCl.CC(C)O BLEBFDYUDVZRFG-UHFFFAOYSA-N 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
239000008298 dragée Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000000835 fiber Substances 0.000 description 1
239000000945 filler Substances 0.000 description 1
239000007941 film coated tablet Substances 0.000 description 1
229960000449 flecainide Drugs 0.000 description 1
-1 flow regulators Substances 0.000 description 1
239000012530 fluid Substances 0.000 description 1
238000009472 formulation Methods 0.000 description 1
239000007789 gas Substances 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
229940031705 hydroxypropyl methylcellulose 2910 Drugs 0.000 description 1
208000021822 hypotensive Diseases 0.000 description 1
230000001077 hypotensive effect Effects 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000007788 liquid Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
235000019813 microcrystalline cellulose Nutrition 0.000 description 1
239000008108 microcrystalline cellulose Substances 0.000 description 1
229940016286 microcrystalline cellulose Drugs 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
210000003205 muscle Anatomy 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
210000003540 papillary muscle Anatomy 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
239000003340 retarding agent Substances 0.000 description 1
150000003870 salicylic acids Chemical class 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000007885 tablet disintegrant Substances 0.000 description 1
125000006318 tert-butyl amino group Chemical group [H]N(*)C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
238000011287 therapeutic dose Methods 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000048 toxicity data Toxicity 0.000 description 1
230000002861 ventricular Effects 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
General Chemical & Material Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Heart & Thoracic Surgery (AREA)
Chemical Kinetics & Catalysis (AREA)
Cardiology (AREA)
Epidemiology (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

DD88313963A 1987-03-25 1988-03-24 Verfahren zur herstellung von tert.-butylamino-3-(phenyl-2'-phenoxy)-1-propanol-2 und seine salze mit saeuren enthaltenden arzneimittelpraeparaten DD268158A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19873709689 DE3709689A1 (de)	1987-03-25	1987-03-25	Tert.-butylamino-3-(phenyl-2'-phenoxy)- 1-propanol-2 und seine salze mit saeuren als antiarrhythmika

Publications (1)

Publication Number	Publication Date
DD268158A5 true DD268158A5 (de)	1989-05-24

Family

ID=6323880

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD88313963A DD268158A5 (de)	1987-03-25	1988-03-24	Verfahren zur herstellung von tert.-butylamino-3-(phenyl-2'-phenoxy)-1-propanol-2 und seine salze mit saeuren enthaltenden arzneimittelpraeparaten

Country Status (11)

Country	Link
EP (1)	EP0291663A3 (fr)
JP (1)	JPS63255218A (fr)
KR (1)	KR880011077A (fr)
AU (1)	AU1370188A (fr)
DD (1)	DD268158A5 (fr)
DE (1)	DE3709689A1 (fr)
DK (1)	DK160388A (fr)
HU (1)	HUT50282A (fr)
IL (1)	IL85856A0 (fr)
PT (1)	PT87077B (fr)
ZA (1)	ZA882096B (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
ATE67480T1 (de) *	1987-03-26	1991-10-15	Helopharm Petrik Co Kg	Verfahren zur herstellung von 5-hydroxydiprafenon und seiner salze mit saeuren.

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1183847A (en) *	1966-04-18	1970-03-11	Lipha	Diphenyl Derivatives
FR1494749A (fr) *	1966-04-18	1967-09-15	Lipha	Nouveaux amino alcools dérivés du diphényle
DE2320646A1 (de) *	1973-04-24	1974-11-14	Klinge Co Chem Pharm Fab	Mittel zur behandlung von herzrhythmusstoerungen

1987
- 1987-03-25 DE DE19873709689 patent/DE3709689A1/de not_active Withdrawn
1988
- 1988-03-24 HU HU881509A patent/HUT50282A/hu unknown
- 1988-03-24 KR KR1019880003169A patent/KR880011077A/ko not_active Abandoned
- 1988-03-24 DK DK160388A patent/DK160388A/da not_active IP Right Cessation
- 1988-03-24 EP EP88104747A patent/EP0291663A3/fr not_active Withdrawn
- 1988-03-24 DD DD88313963A patent/DD268158A5/de not_active IP Right Cessation
- 1988-03-24 AU AU13701/88A patent/AU1370188A/en not_active Abandoned
- 1988-03-24 JP JP63071738A patent/JPS63255218A/ja active Pending
- 1988-03-24 PT PT87077A patent/PT87077B/pt not_active IP Right Cessation
- 1988-03-24 IL IL85856A patent/IL85856A0/xx unknown
- 1988-03-24 ZA ZA882096A patent/ZA882096B/xx unknown

Also Published As

Publication number	Publication date
HUT50282A (en)	1990-01-29
DK160388D0 (da)	1988-03-24
EP0291663A2 (fr)	1988-11-23
JPS63255218A (ja)	1988-10-21
AU1370188A (en)	1988-09-29
ZA882096B (en)	1989-12-27
IL85856A0 (en)	1988-09-30
EP0291663A3 (fr)	1990-07-04
DK160388A (da)	1988-09-26
KR880011077A (ko)	1988-10-26
PT87077B (pt)	1992-07-31
PT87077A (pt)	1988-04-01
DE3709689A1 (de)	1988-10-06

Legal Events

Date	Code	Title	Description
1996-04-25	ENJ	Ceased due to non-payment of renewal fee

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DE2635209C2 (de)	1983-01-27	4-(2-Benzoyloxy-3-tert.butylamino-propoxy)-2-methylindol, dessen (S)-Enantiomeres, deren Säureadditionssalze, Verfahren zu deren Herstellung und diese Verbindungen enthaltende Heilmittel
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DD268158A5 (de)	1989-05-24	Verfahren zur herstellung von tert.-butylamino-3-(phenyl-2'-phenoxy)-1-propanol-2 und seine salze mit saeuren enthaltenden arzneimittelpraeparaten
DE2451933C2 (fr)	1988-06-09
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DE1470074B2 (de)	1973-06-14	1,2,3,4,6,7-hexahydro-11bh-benzo eckige klammer auf a eckige klammer zu chinolizine sowie deren acetate und/oder physiologisch vertraegliche saeureadditionssalze sowie verfahren zu ihrer herstellung
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DE3410218A1 (de)	1985-09-19	Tergurid als antihypertensivum
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