SE443779B - Forfarande for framstellning av den terapeutiskt aktiva foreningen 1-isopropylamino-3-/4-(2-metoxietyl) fenoxi/-2-propanol och dess syraadditionssalter - Google Patents

Forfarande for framstellning av den terapeutiskt aktiva foreningen 1-isopropylamino-3-/4-(2-metoxietyl) fenoxi/-2-propanol och dess syraadditionssalter

Info

Publication number: SE443779B
Authority: SE; Sweden
Prior art keywords: compound; formula; acid addition; isopropylamino; propanol
Prior art date: 1978-11-29

Application number

SE7909816A

Other languages

English (en)

Swedish (sv)

Other versions

SE7909816L (sv

Inventor

S K Huhta

A J Karjalainen

Original Assignee

Haessle Ab

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.)

1978-11-29

Filing date

1979-11-28

Publication date

1986-03-10

1979-11-28 Application filed by Haessle Ab filed Critical Haessle Ab

1980-05-30 Publication of SE7909816L publication Critical patent/SE7909816L/xx

1986-03-10 Publication of SE443779B publication Critical patent/SE443779B/sv

Links

150000001875 compounds Chemical class 0.000 title claims description 22
239000002253 acid Substances 0.000 title claims description 14
238000000034 method Methods 0.000 title claims description 14
150000003839 salts Chemical class 0.000 title claims description 8
KFZMGEQAYNKOFK-UHFFFAOYSA-N 2-propanol Substances CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 title claims description 5
KHUXNRRPPZOJPT-UHFFFAOYSA-N phenoxy radical Chemical class O=C1C=C[CH]C=C1 KHUXNRRPPZOJPT-UHFFFAOYSA-N 0.000 title 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 36
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 12
239000003377 acid catalyst Substances 0.000 claims description 7
-1 alkali metal methoxide Chemical class 0.000 claims description 7
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
230000007935 neutral effect Effects 0.000 claims description 3
OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 claims description 2
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 2
229910052783 alkali metal Inorganic materials 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims description 2
239000003513 alkali Substances 0.000 claims 1
NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 claims 1
238000006243 chemical reaction Methods 0.000 description 11
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
239000002904 solvent Substances 0.000 description 7
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
239000000203 mixture Substances 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 4
239000000047 product Substances 0.000 description 4
238000003786 synthesis reaction Methods 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
FEWJPZIEWOKRBE-JCYAYHJZSA-L L-tartrate(2-) Chemical compound [O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O FEWJPZIEWOKRBE-JCYAYHJZSA-L 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
150000002148 esters Chemical group 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
229940095064 tartrate Drugs 0.000 description 3
NVSVLJBHRDKPOS-UHFFFAOYSA-N 2-[4-(oxiran-2-ylmethoxy)phenyl]ethyl 4-methylbenzenesulfonate Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)OCCC1=CC=C(OCC2CO2)C=C1 NVSVLJBHRDKPOS-UHFFFAOYSA-N 0.000 description 2
125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 2
FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
239000002585 base Substances 0.000 description 2
238000009835 boiling Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
239000007789 gas Substances 0.000 description 2
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
229910000041 hydrogen chloride Inorganic materials 0.000 description 2
150000002894 organic compounds Chemical class 0.000 description 2
ISYORFGKSZLPNW-UHFFFAOYSA-N propan-2-ylazanium;chloride Chemical compound [Cl-].CC(C)[NH3+] ISYORFGKSZLPNW-UHFFFAOYSA-N 0.000 description 2
239000007858 starting material Substances 0.000 description 2
CGQNVKGUSGZQJA-UHFFFAOYSA-N 4-methylbenzenesulfonic acid;propan-2-amine Chemical compound CC(C)N.CC1=CC=C(S(O)(=O)=O)C=C1 CGQNVKGUSGZQJA-UHFFFAOYSA-N 0.000 description 1
IQXASIUYQZYQPH-UHFFFAOYSA-N CC1=CC=C(C=C1)S(=O)(=O)OC(C)C2=CC=C(C=C2)O Chemical compound CC1=CC=C(C=C1)S(=O)(=O)OC(C)C2=CC=C(C=C2)O IQXASIUYQZYQPH-UHFFFAOYSA-N 0.000 description 1
239000004593 Epoxy Substances 0.000 description 1
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 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
229910000272 alkali metal oxide Inorganic materials 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
239000002026 chloroform extract Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
150000002118 epoxides Chemical group 0.000 description 1
238000009472 formulation Methods 0.000 description 1
229960002237 metoprolol Drugs 0.000 description 1
IUBSYMUCCVWXPE-UHFFFAOYSA-N metoprolol Chemical group COCCC1=CC=C(OCC(O)CNC(C)C)C=C1 IUBSYMUCCVWXPE-UHFFFAOYSA-N 0.000 description 1
229960001300 metoprolol tartrate Drugs 0.000 description 1
239000008267 milk Substances 0.000 description 1
210000004080 milk Anatomy 0.000 description 1
235000013336 milk Nutrition 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
238000002156 mixing Methods 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 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
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
239000002994 raw material Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
NESLWCLHZZISNB-UHFFFAOYSA-M sodium phenolate Chemical class [Na+].[O-]C1=CC=CC=C1 NESLWCLHZZISNB-UHFFFAOYSA-M 0.000 description 1
239000000243 solution Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
WUBVEMGCQRSBBT-UHFFFAOYSA-N tert-butyl 4-(trifluoromethylsulfonyloxy)-3,6-dihydro-2h-pyridine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(OS(=O)(=O)C(F)(F)F)=CC1 WUBVEMGCQRSBBT-UHFFFAOYSA-N 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
- C07D303/12—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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

SE7909816A 1978-11-29 1979-11-28 Forfarande for framstellning av den terapeutiskt aktiva foreningen 1-isopropylamino-3-/4-(2-metoxietyl) fenoxi/-2-propanol och dess syraadditionssalter SE443779B (sv)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FI783646A FI58909C (fi)	1978-11-29	1978-11-29	Foerfarande foer framstaellning av den terapeutiskt aktiva foereningen 1-isopropylamino-3-(4-(2-metoxietyl)-fenoxi)-2-propanol och dess syraadditionssalter

Publications (2)

Publication Number	Publication Date
SE7909816L SE7909816L (sv)	1980-05-30
SE443779B true SE443779B (sv)	1986-03-10

Family

ID=8512188

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SE7909816A SE443779B (sv)	1978-11-29	1979-11-28	Forfarande for framstellning av den terapeutiskt aktiva foreningen 1-isopropylamino-3-/4-(2-metoxietyl) fenoxi/-2-propanol och dess syraadditionssalter

Country Status (5)

Country	Link
DK (1)	DK154072C (da)
FI (1)	FI58909C (da)
NL (1)	NL7908669A (da)
NO (1)	NO793871L (da)
SE (1)	SE443779B (da)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN101665441B (zh) *	2009-09-18	2013-04-10	安徽省庆云医药化工有限公司	左旋盐酸倍他洛尔的制备方法
CN102381995B (zh) *	2010-08-31	2015-04-15	扬子江药业集团北京海燕药业有限公司	美托洛尔的制备方法

1978
- 1978-11-29 FI FI783646A patent/FI58909C/fi not_active IP Right Cessation
1979
- 1979-11-28 SE SE7909816A patent/SE443779B/sv not_active IP Right Cessation
- 1979-11-28 NO NO793871A patent/NO793871L/no unknown
- 1979-11-28 DK DK504879A patent/DK154072C/da not_active IP Right Cessation
- 1979-11-29 NL NL7908669A patent/NL7908669A/nl not_active Application Discontinuation

Also Published As

Publication number	Publication date
FI58909B (fi)	1981-01-30
DK154072B (da)	1988-10-10
DK504879A (da)	1980-05-30
FI58909C (fi)	1981-05-11
FI783646A7 (fi)	1980-05-30
NO793871L (no)	1980-05-30
SE7909816L (sv)	1980-05-30
NL7908669A (nl)	1980-06-02
DK154072C (da)	1989-03-06

Legal Events

Date

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Title

Description

1995-01-31

NUG

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Effective date: 19910611

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