FI64581C - Nytt foerfarande foer framstaellning av terapeutiskt aktiva 1-4-bromfenyl)-1-(3-pyridyl)-3-aminopropenderivat - Google Patents

Nytt foerfarande foer framstaellning av terapeutiskt aktiva 1-4-bromfenyl)-1-(3-pyridyl)-3-aminopropenderivat Download PDF

Info

Publication number: FI64581C
Authority: FI; Finland
Prior art keywords: formula; bromophenyl; pyridyl; ph3p; eller
Prior art date: 1977-07-04

Application number

FI782115A

Other languages

English (en)

Finnish (fi)

Other versions

FI64581B (fi

FI782115A7 (fi

Inventor

Peter Bamberg

Original Assignee

Astra Laekemedel 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.)

1977-07-04

Filing date

1978-06-30

Publication date

1983-12-12

1978-06-30 Application filed by Astra Laekemedel Ab filed Critical Astra Laekemedel Ab

1979-01-05 Publication of FI782115A7 publication Critical patent/FI782115A7/fi

1983-08-31 Publication of FI64581B publication Critical patent/FI64581B/fi

1983-12-12 Application granted granted Critical

1983-12-12 Publication of FI64581C publication Critical patent/FI64581C/fi

Links

-1 3-PYRIDYL Chemical class 0.000 title description 2
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 27
238000006243 chemical reaction Methods 0.000 claims description 19
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 17
238000000034 method Methods 0.000 claims description 16
238000002360 preparation method Methods 0.000 claims description 14
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 12
239000003153 chemical reaction reagent Substances 0.000 claims description 12
150000001875 compounds Chemical class 0.000 claims description 12
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 claims description 6
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
IDGVUIHZWDVXOQ-UHFFFAOYSA-N (4-bromophenyl)-pyridin-3-ylmethanone Chemical compound C1=CC(Br)=CC=C1C(=O)C1=CC=CN=C1 IDGVUIHZWDVXOQ-UHFFFAOYSA-N 0.000 claims description 3
AEQRYRORWFYTDQ-UHFFFAOYSA-N 3-(4-bromophenyl)-3-pyridin-3-ylprop-2-en-1-amine Chemical class C=1C=CN=CC=1C(=CCN)C1=CC=C(Br)C=C1 AEQRYRORWFYTDQ-UHFFFAOYSA-N 0.000 claims description 3
125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 3
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 claims description 3
229910052739 hydrogen Chemical group 0.000 claims description 2
239000001257 hydrogen Chemical group 0.000 claims description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 1
230000036571 hydration Effects 0.000 claims 1
238000006703 hydration reaction Methods 0.000 claims 1
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims 1
230000004048 modification Effects 0.000 claims 1
238000012986 modification Methods 0.000 claims 1
239000003960 organic solvent Substances 0.000 claims 1
239000012429 reaction media Substances 0.000 claims 1
150000003839 salts Chemical class 0.000 claims 1
239000007858 starting material Substances 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 12
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
239000000047 product Substances 0.000 description 12
239000000203 mixture Substances 0.000 description 9
239000000126 substance Substances 0.000 description 8
239000013078 crystal Substances 0.000 description 5
238000004519 manufacturing process Methods 0.000 description 5
PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
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 4
229910052708 sodium Inorganic materials 0.000 description 4
239000011734 sodium Substances 0.000 description 4
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
238000001816 cooling Methods 0.000 description 3
239000012467 final product Substances 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
239000008096 xylene Substances 0.000 description 3
YIIHEMGEQQWSMA-UHFFFAOYSA-M 2-(dimethylamino)ethyl-triphenylphosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCN(C)C)C1=CC=CC=C1 YIIHEMGEQQWSMA-UHFFFAOYSA-M 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
239000000935 antidepressant agent Substances 0.000 description 2
WLNKGGRXEOAKBY-UHFFFAOYSA-N bis(4-bromo-2-pyridin-3-ylphenyl)methanone Chemical compound C=1C=CN=CC=1C1=CC(Br)=CC=C1C(=O)C1=CC=C(Br)C=C1C1=CC=CN=C1 WLNKGGRXEOAKBY-UHFFFAOYSA-N 0.000 description 2
238000001914 filtration Methods 0.000 description 2
239000003607 modifier Substances 0.000 description 2
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
230000009257 reactivity Effects 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 2
OYPPVKRFBIWMSX-UHFFFAOYSA-N Cis-zimelidine Chemical compound C=1C=CN=CC=1C(=CCN(C)C)C1=CC=C(Br)C=C1 OYPPVKRFBIWMSX-UHFFFAOYSA-N 0.000 description 1
QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
239000013543 active substance Substances 0.000 description 1
230000001430 anti-depressive effect Effects 0.000 description 1
229940005513 antidepressants Drugs 0.000 description 1
238000004061 bleaching Methods 0.000 description 1
235000014121 butter Nutrition 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
239000005457 ice water Substances 0.000 description 1
238000002955 isolation Methods 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
238000002156 mixing Methods 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
230000001225 therapeutic effect Effects 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
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pyridine Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

FI782115A 1977-07-04 1978-06-30 Nytt foerfarande foer framstaellning av terapeutiskt aktiva 1-4-bromfenyl)-1-(3-pyridyl)-3-aminopropenderivat FI64581C (fi)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
SE7707707		1977-07-04
SE7707707A SE409861B (sv)	1977-07-04	1977-07-04	Ett nytt forfarande for framstellning av en terapeutisk aktiv pyridinforening

Publications (3)

Publication Number	Publication Date
FI782115A7 FI782115A7 (fi)	1979-01-05
FI64581B FI64581B (fi)	1983-08-31
FI64581C true FI64581C (fi)	1983-12-12

Family

ID=20331764

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
FI782115A FI64581C (fi)	1977-07-04	1978-06-30	Nytt foerfarande foer framstaellning av terapeutiskt aktiva 1-4-bromfenyl)-1-(3-pyridyl)-3-aminopropenderivat

Country Status (13)

Country	Link
JP (1)	JPS5414976A (da)
AT (1)	AT365171B (da)
CA (1)	CA1082198A (da)
CH (1)	CH641163A5 (da)
DK (1)	DK295378A (da)
ES (1)	ES471302A1 (da)
FI (1)	FI64581C (da)
IT (1)	IT1105226B (da)
NL (1)	NL7807246A (da)
NO (1)	NO782304L (da)
SE (1)	SE409861B (da)
SU (1)	SU923366A3 (da)
WO (1)	WO1979000023A1 (da)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
SE7909514L (sv) *	1979-11-16	1981-05-17	Astra Laekemedel Ab	Nya halofenyl-pyridyl-allylaminderivat
FI20090389L (fi) *	2009-10-23	2011-04-24	Kone Corp	Menetelmä hissin valmistamisessa
FI122066B (fi) *	2009-12-31	2011-08-15	Kone Corp	Menetelmä hissin valmistamisessa
FI20100223A0 (fi) *	2010-05-28	2010-05-28	Kone Corp	Menetelmä ja hissijärjestely
FI20106273A7 (fi) *	2010-12-01	2012-06-02	Kone Corp	Hissijärjestely ja menetelmä
EP2636629B1 (en) *	2012-03-06	2015-05-06	KONE Corporation	A method and an elevator arrangement
US9388020B2 (en) *	2012-03-06	2016-07-12	Kone Corporation	Method and an elevator arrangement

1977
- 1977-07-04 SE SE7707707A patent/SE409861B/sv unknown
1978
- 1978-06-26 WO PCT/SE1978/000009 patent/WO1979000023A1/en not_active Ceased
- 1978-06-26 CH CH329979A patent/CH641163A5/de not_active IP Right Cessation
- 1978-06-27 CA CA306,260A patent/CA1082198A/en not_active Expired
- 1978-06-29 DK DK782953A patent/DK295378A/da not_active Application Discontinuation
- 1978-06-30 IT IT50123/78A patent/IT1105226B/it active
- 1978-06-30 ES ES471302A patent/ES471302A1/es not_active Expired
- 1978-06-30 FI FI782115A patent/FI64581C/fi not_active IP Right Cessation
- 1978-07-03 NO NO782304A patent/NO782304L/no unknown
- 1978-07-04 JP JP8182078A patent/JPS5414976A/ja active Pending
- 1978-07-04 NL NL7807246A patent/NL7807246A/xx not_active Application Discontinuation
- 1978-07-04 AT AT0483778A patent/AT365171B/de not_active IP Right Cessation
1979
- 1979-08-03 SU SU792798502A patent/SU923366A3/ru active

Also Published As

Publication number	Publication date
IT1105226B (it)	1985-10-28
NO782304L (no)	1979-01-05
SU923366A3 (ru)	1982-04-23
CH641163A5 (de)	1984-02-15
ES471302A1 (es)	1979-09-01
IT7850123A0 (it)	1978-06-30
CA1082198A (en)	1980-07-22
DK295378A (da)	1979-01-05
SE409861B (sv)	1979-09-10
AT365171B (de)	1981-12-28
JPS5414976A (en)	1979-02-03
FI64581B (fi)	1983-08-31
WO1979000023A1 (en)	1979-01-25
ATA483778A (de)	1981-05-15
FI782115A7 (fi)	1979-01-05
NL7807246A (nl)	1979-01-08
SE7707707L (sv)	1979-01-05

Legal Events

Date	Code	Title	Description
2004-08-31	MM	Patent lapsed	Owner name: ASTRA LAEKEMEDEL AKTIEBOLAG

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CZ163797A3 (cs)	1998-02-18	Způsob výroby dichloridu kyseliny 5-amino-2,4,6-trijodisoftalové
US3867403A (en)	1975-02-18	1,2-dialkyl-3,5-diphenylpyrazolium salts
CS208793B2 (en)	1981-09-15	Method of making the very pure derivatives of the pyraz
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SU999967A3 (ru)	1983-02-23	Способ получени 6-N-замещенных 6-амино-3-пиридазинилгидразинов или их солей
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CA1119179A (en)	1982-03-02	Process for preparing n-tritylimidazole compounds
FI57930C (fi)	1980-11-10	Nytt saett att framstaella bensamider
KR100343948B1 (ko)	2002-07-24	피페라지닐에틸 트리아졸 화합물 및 그 제조방법
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