NO793871L - Fremgangsmaate for fremstilling av metoprol. - Google Patents

Fremgangsmaate for fremstilling av metoprol.

Info

Publication number: NO793871L
Authority: NO; Norway
Prior art keywords: formula; compound; propanol; stated; isopropylamino
Prior art date: 1978-11-29

Application number

NO793871A

Other languages

English (en)

Norwegian (no)

Inventor

Soini Kanerva Huhta

Arto Johannes Karjalainen

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.)

1978-11-29

Filing date

1979-11-28

Publication date

1980-05-30

1979-11-28 Application filed by Farmos Oy filed Critical Farmos Oy

1980-05-30 Publication of NO793871L publication Critical patent/NO793871L/no

Links

238000000034 method Methods 0.000 title claims description 22
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 36
150000001875 compounds Chemical class 0.000 claims description 24
IUBSYMUCCVWXPE-UHFFFAOYSA-N metoprolol Chemical compound COCCC1=CC=C(OCC(O)CNC(C)C)C=C1 IUBSYMUCCVWXPE-UHFFFAOYSA-N 0.000 claims description 15
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 12
239000002253 acid Substances 0.000 claims description 11
150000003839 salts Chemical class 0.000 claims description 11
229960002237 metoprolol Drugs 0.000 claims description 10
-1 alkali metal methoxide Chemical class 0.000 claims description 9
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 claims description 9
239000003377 acid catalyst Substances 0.000 claims description 6
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 compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 5
KFZMGEQAYNKOFK-UHFFFAOYSA-N 2-propanol Substances CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
150000002148 esters Chemical group 0.000 claims description 4
229910052783 alkali metal Inorganic materials 0.000 claims description 3
230000007935 neutral effect Effects 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims description 2
125000005228 aryl sulfonate group Chemical group 0.000 claims description 2
125000005843 halogen group Chemical group 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 8
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
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
239000000203 mixture 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
NVSVLJBHRDKPOS-UHFFFAOYSA-N 2-[4-(oxiran-2-ylmethoxy)phenyl]ethyl 4-methylbenzenesulfonate Chemical compound S(=O)(=O)(C1=CC=C(C)C=C1)OCCC1=CC=C(OCC2CO2)C=C1 NVSVLJBHRDKPOS-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 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
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
239000000047 product Substances 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
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
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 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
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 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
238000002360 preparation method Methods 0.000 description 2
ISYORFGKSZLPNW-UHFFFAOYSA-N propan-2-ylazanium;chloride Chemical compound [Cl-].CC(C)[NH3+] ISYORFGKSZLPNW-UHFFFAOYSA-N 0.000 description 2
239000003087 receptor blocking agent Substances 0.000 description 2
RRVCVIKEEIVNJV-UHFFFAOYSA-N 2-(4-hydroxyphenyl)ethyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCCC1=CC=C(O)C=C1 RRVCVIKEEIVNJV-UHFFFAOYSA-N 0.000 description 1
GSJKJPRTYNBOKU-UHFFFAOYSA-N 4-(2-chloroethyl)phenol Chemical compound OC1=CC=C(CCCl)C=C1 GSJKJPRTYNBOKU-UHFFFAOYSA-N 0.000 description 1
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
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
238000007171 acid catalysis Methods 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
210000004204 blood vessel Anatomy 0.000 description 1
229940030602 cardiac therapy drug Drugs 0.000 description 1
239000003054 catalyst 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
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
150000002118 epoxides Chemical class 0.000 description 1
125000003700 epoxy group Chemical group 0.000 description 1
239000012467 final product Substances 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
210000004072 lung Anatomy 0.000 description 1
XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical group COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 1
229960001300 metoprolol tartrate Drugs 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
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
238000001953 recrystallisation Methods 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
239000007858 starting material Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
150000003892 tartrate salts Chemical class 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
125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 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)

NO793871A 1978-11-29 1979-11-28 Fremgangsmaate for fremstilling av metoprol. NO793871L (no)

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 (1)

Publication Number	Publication Date
NO793871L true NO793871L (no)	1980-05-30

Family

ID=8512188

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO793871A NO793871L (no)	1978-11-29	1979-11-28	Fremgangsmaate for fremstilling av metoprol.

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
NL7908669A (nl)	1980-06-02
SE7909816L (sv)	1980-05-30
FI58909B (fi)	1981-01-30
DK154072B (da)	1988-10-10
DK154072C (da)	1989-03-06
SE443779B (sv)	1986-03-10
DK504879A (da)	1980-05-30
FI783646A7 (fi)	1980-05-30
FI58909C (fi)	1981-05-11

Publication	Publication Date	Title
HU193161B (en)	1987-08-28	Process for preparing new n-alkyl-norscopines
US2826588A (en)	1958-03-11	J-di-substituted pyrrolidine compounds
SU577971A3 (ru)	1977-10-25	Способ получени производных пропаноламина или их солей
CH506536A (de)	1971-04-30	Verfahren zur Herstellung von aromatischen Äthern
FI69835C (fi)	1986-05-26	Foerfarande foer framstaellning av terapeutiskt anvaendbara 3-ndolyl-tertiaerbutylaminopropanolderivat
JPH0662519B2 (ja)	1994-08-17	環状中間体を用いたフエノ−ルエ−テルの製法
SU843733A3 (ru)	1981-06-30	Способ получени производных амино-пРОпАНОлА или иХ СОлЕй (ЕгО ВАРиАНТы)
EP0406386A1 (en)	1991-01-09	Improved process for the preparation of amidoxime derivatives.
TW407142B (en)	2000-10-01	Process to chloroketoamines using carbamates
US3965112A (en)	1976-06-22	Imidazoline derivatives
DK154072B (da)	1988-10-10	Fremgangsmaade til fremstilling af 1-isopropylamino-3-(4-(2-methoxyethyl)-phenoxy)-2-propanol eller syreadditionssalte deraf
SU617007A3 (ru)	1978-07-25	Способ получени аминов или их солей
Edwards et al.	1974	1-Alkylamino-3-(2-thiazolyloxy)-2-propanols. Novel class of mixed myocardial. beta.-stimulants/. beta.-blockers
SU841582A3 (ru)	1981-06-23	Способ получени аминопроиз-ВОдНыХ АзидОфЕНОлА или иХ СОлЕй
NO162461B (no)	1989-09-25	Fremgangsm te for fremstilling av aminderivater.
EP0041760B1 (en)	1984-03-07	Process for the preparation of 1-isopropylamino-3-(4-(2-methoxy-ethyl)-phenoxy)-2-propanol
CA1265523A (en)	1990-02-06	Preparation of phenol ethers using cyclic intermediates
CA1042463A (en)	1978-11-14	Tertiary-alkylamino-lower acyl-xylidides
US3184473A (en)	1965-05-18	Imidazoline derivatives
SU622395A3 (ru)	1978-08-30	Способ получени аминов или их солей
JPS60184067A (ja)	1985-09-19	新規ピリミジン誘導体およびその製造法
Vidal	1959	Reaction of ethylene dibromide with triethylamine and the restoring action of some alkanebis (triethylammonium) ions upon sodium-deficient nerve fibers
SU486670A1 (ru)	1990-01-23	Способ получени производных 5-окси-6-аминометилбензофурана
DE2950479A1 (de)	1981-06-19	N-(3-alkylamino-2-hydroxypropoxy-phenyl)-lactame, deren herstellungsverfahren und arzneimitttel auf deren basis
NO157417B (no)	1987-12-07	Fremgangsmaate for fremstlling av 3,4-diisobutyryloksy-n-metyl-fenetylamin.