DD212957A5 - Verfahren zur herstellung von 1-isopropylamino-3-aryloxy-2-propanols und mittel zu ihrer herstellung - Google Patents

Verfahren zur herstellung von 1-isopropylamino-3-aryloxy-2-propanols und mittel zu ihrer herstellung Download PDF

Info

Publication number: DD212957A5
Authority: DD; German Democratic Republic
Prior art keywords: compound; preparation; general formula; isopropylamino; formula
Prior art date: 1982-12-22

Application number

DD83258478A

Other languages

German (de)

English (en)

Inventor

Erkki J Honkanen

Pekka J Kairisalo

Aino K Pippuri

Original Assignee

Orion Yhtymae 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.)

1982-12-22

Filing date

1983-12-22

Publication date

1984-08-29

1983-12-22 Application filed by Orion Yhtymae Oy filed Critical Orion Yhtymae Oy

1984-08-29 Publication of DD212957A5 publication Critical patent/DD212957A5/de

Links

238000000034 method Methods 0.000 title claims abstract description 16
238000002360 preparation method Methods 0.000 title claims abstract description 11
150000001875 compounds Chemical class 0.000 claims abstract description 16
-1 benzhydryl group Chemical group 0.000 claims abstract description 6
238000006243 chemical reaction Methods 0.000 claims description 5
239000003054 catalyst Substances 0.000 claims description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N 2-propanol Substances CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 3
239000012299 nitrogen atmosphere Substances 0.000 claims description 2
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims 2
MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 claims 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
229910052700 potassium Inorganic materials 0.000 claims 1
239000011591 potassium Substances 0.000 claims 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
101100109871 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) aro-8 gene Proteins 0.000 abstract description 2
239000002876 beta blocker Substances 0.000 abstract description 2
229940097320 beta blocking agent Drugs 0.000 abstract description 2
239000003814 drug Substances 0.000 abstract 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 abstract 1
238000004519 manufacturing process Methods 0.000 abstract 1
239000000047 product Substances 0.000 description 13
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
239000002904 solvent Substances 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
239000007795 chemical reaction product Substances 0.000 description 3
239000000243 solution Substances 0.000 description 3
GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 2
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
101150065749 Churc1 gene Proteins 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
102100038239 Protein Churchill Human genes 0.000 description 2
239000012298 atmosphere Substances 0.000 description 2
238000009835 boiling Methods 0.000 description 2
239000012043 crude product Substances 0.000 description 2
QILSFLSDHQAZET-UHFFFAOYSA-N diphenylmethanol Chemical compound C=1C=CC=CC=1C(O)C1=CC=CC=C1 QILSFLSDHQAZET-UHFFFAOYSA-N 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
239000000203 mixture Substances 0.000 description 2
WSMBTEDNTPDCJM-UHFFFAOYSA-N n-benzhydryl-n-(oxiran-2-ylmethyl)propan-2-amine Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)N(C(C)C)CC1CO1 WSMBTEDNTPDCJM-UHFFFAOYSA-N 0.000 description 2
239000007858 starting material Substances 0.000 description 2
METKIMKYRPQLGS-GFCCVEGCSA-N (R)-atenolol Chemical compound CC(C)NC[C@@H](O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-GFCCVEGCSA-N 0.000 description 1
HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
QNFVQJPWLUTYNN-UHFFFAOYSA-N 1-[benzhydryl(propan-2-yl)amino]-3-chloropropan-2-ol Chemical compound C=1C=CC=CC=1C(N(CC(O)CCl)C(C)C)C1=CC=CC=C1 QNFVQJPWLUTYNN-UHFFFAOYSA-N 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
101000588924 Anthopleura elegantissima Delta-actitoxin-Ael1a Proteins 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
RDRZAYABFBGPDQ-UHFFFAOYSA-N C(C)(C)N(C(C1=CC=CC=C1)C1=CC=CC=C1)CC(COC1=C(C=C(C=C1)NC(CCC)=O)C(C)=O)O Chemical compound C(C)(C)N(C(C1=CC=CC=C1)C1=CC=CC=C1)CC(COC1=C(C=C(C=C1)NC(CCC)=O)C(C)=O)O RDRZAYABFBGPDQ-UHFFFAOYSA-N 0.000 description 1
OOQNFLSZMQVWEP-UHFFFAOYSA-N C(C)(C)N(C(C1=CC=CC=C1)C1=CC=CC=C1)CC(COC1=CC=C(C=C1)CC(N)=O)O Chemical compound C(C)(C)N(C(C1=CC=CC=C1)C1=CC=CC=C1)CC(COC1=CC=C(C=C1)CC(N)=O)O OOQNFLSZMQVWEP-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
241000257303 Hymenoptera Species 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
ZDVDCDLBOLSVGM-UHFFFAOYSA-N [chloro(phenyl)methyl]benzene Chemical compound C=1C=CC=CC=1C(Cl)C1=CC=CC=C1 ZDVDCDLBOLSVGM-UHFFFAOYSA-N 0.000 description 1
229960002122 acebutolol Drugs 0.000 description 1
GOEMGAFJFRBGGG-UHFFFAOYSA-N acebutolol Chemical compound CCCC(=O)NC1=CC=C(OCC(O)CNC(C)C)C(C(C)=O)=C1 GOEMGAFJFRBGGG-UHFFFAOYSA-N 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 description 1
229960002274 atenolol Drugs 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
FGWZEOPEZISTTR-UHFFFAOYSA-N n-(3-acetyl-4-hydroxyphenyl)butanamide Chemical compound CCCC(=O)NC1=CC=C(O)C(C(C)=O)=C1 FGWZEOPEZISTTR-UHFFFAOYSA-N 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000001103 potassium chloride Substances 0.000 description 1
235000011164 potassium chloride Nutrition 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-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
- C07D303/36—Compounds containing oxirane rings with hydrocarbon radicals, substituted by nitrogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C217/28—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines
- C07C217/30—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines having the oxygen atom of at least one of the etherified hydroxy groups further bound to a carbon atom of a six-membered aromatic ring

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

DD83258478A 1982-12-22 1983-12-22 Verfahren zur herstellung von 1-isopropylamino-3-aryloxy-2-propanols und mittel zu ihrer herstellung DD212957A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FI824411A FI66839C (fi)	1982-12-22	1982-12-22	Foerfarande foer framstaellning av terapeutiskt anvaendbara deivat av 1-isopropylamino-3-fenoxi-2-propanoler samt mella npodukt foer anvaendning vid foerfarandet

Publications (1)

Publication Number	Publication Date
DD212957A5 true DD212957A5 (de)	1984-08-29

Family

ID=8516499

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD83258478A DD212957A5 (de)	1982-12-22	1983-12-22	Verfahren zur herstellung von 1-isopropylamino-3-aryloxy-2-propanols und mittel zu ihrer herstellung

Country Status (6)

Country	Link
DD (1)	DD212957A5 (da)
DK (1)	DK586083A (da)
FI (1)	FI66839C (da)
NL (1)	NL8304392A (da)
SE (1)	SE8307129L (da)
SU (1)	SU1321371A3 (da)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
RU2423346C2 (ru) *	2006-11-03	2011-07-10	Эмкьюар Фармасьютикалз Лимитед	Улучшенный способ получения бета-блокатора
RU2396248C1 (ru) *	2008-12-03	2010-08-10	Новосибирский институт органической химии им. Н.Н. Ворожцова Сибирского отделения Российской академии наук (НИОХ СО РАН) (статус государственного учреждения)	Сукцинат ди-3-(3,5-ди-трет-бутил-4-гидроксифенил)-2-гидрокси-1-(n-изопропиламино)пропана, обладающий антиаритмической активностью

1982
- 1982-12-22 FI FI824411A patent/FI66839C/fi not_active IP Right Cessation
1983
- 1983-12-20 DK DK586083A patent/DK586083A/da not_active Application Discontinuation
- 1983-12-21 SU SU833703901A patent/SU1321371A3/ru active
- 1983-12-21 NL NL8304392A patent/NL8304392A/nl not_active Application Discontinuation
- 1983-12-22 DD DD83258478A patent/DD212957A5/de unknown
- 1983-12-22 SE SE8307129A patent/SE8307129L/xx not_active Application Discontinuation

Also Published As

Publication number	Publication date
DK586083A (da)	1984-06-23
NL8304392A (nl)	1984-07-16
SE8307129D0 (sv)	1983-12-22
FI824411A0 (fi)	1982-12-22
FI66839C (fi)	1984-12-10
SE8307129L (sv)	1984-06-23
DK586083D0 (da)	1983-12-20
FI824411L (fi)	1984-06-23
SU1321371A3 (ru)	1987-06-30
FI66839B (fi)	1984-08-31

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