DD141674B1 - Verfahren zur herstellung der kristallinen alpha-form von 1-(4-amino-6,7-dimethoxy-2-chinazolinyl)-4-(2-furoyl)-piperazin-hydrochlorid - Google Patents

Verfahren zur herstellung der kristallinen alpha-form von 1-(4-amino-6,7-dimethoxy-2-chinazolinyl)-4-(2-furoyl)-piperazin-hydrochlorid Download PDF

Info

Publication number: DD141674B1
Authority: DD; German Democratic Republic
Prior art keywords: amino; dimethoxy; furoyl; quinazolinyl; piperazine hydrochloride
Prior art date: 1979-03-29

Application number

DD21188479A

Other languages

German (de)

English (en)

Other versions

DD141674A1 (de

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.)

1979-03-29

Filing date

1979-03-29

Publication date

1982-06-30

1979-03-29 Application filed filed Critical

1979-03-29 Priority to DD21188479A priority Critical patent/DD141674B1/de

1980-02-12 Priority to YU36180A priority patent/YU41908B/xx

1980-02-27 Priority to CS137480A priority patent/CS224469B1/cs

1980-02-28 Priority to SU807771089A priority patent/SU1206277A1/ru

1980-03-26 Priority to RO105233A priority patent/RO83455B/ro

1980-03-26 Priority to RO105234A priority patent/RO83442B/ro

1980-03-26 Priority to RO80100627A priority patent/RO79381A/fr

1980-03-27 Priority to PL24061080A priority patent/PL129723B1/pl

1980-03-27 Priority to PL24061180A priority patent/PL129719B1/pl

1980-03-27 Priority to PL22305180A priority patent/PL128496B1/pl

1980-03-28 Priority to HU74180A priority patent/HU182796B/hu

1980-05-14 Publication of DD141674A1 publication Critical patent/DD141674A1/de

1982-06-30 Publication of DD141674B1 publication Critical patent/DD141674B1/de

1983-02-07 Priority to YU26883A priority patent/YU42069B/xx

1983-02-07 Priority to YU26783A priority patent/YU42068B/xx

Links

238000004519 manufacturing process Methods 0.000 title claims description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 18
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 18
WFXFYZULCQKPIP-UHFFFAOYSA-N prazosin hydrochloride Chemical compound [H+].[Cl-].N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(CC1)CCN1C(=O)C1=CC=CO1 WFXFYZULCQKPIP-UHFFFAOYSA-N 0.000 claims description 15
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 14
-1 4-amino-6 , 7-dimethoxy-2-quinazolinyl Chemical group 0.000 claims description 12
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 12
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
239000002904 solvent Substances 0.000 claims description 9
239000000203 mixture Substances 0.000 claims description 8
238000010438 heat treatment Methods 0.000 claims description 7
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 5
239000012453 solvate Substances 0.000 claims description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 3
150000001298 alcohols Chemical class 0.000 claims description 3
150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 3
150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 3
238000001816 cooling Methods 0.000 claims description 3
150000002170 ethers Chemical class 0.000 claims description 3
150000002576 ketones Chemical class 0.000 claims description 3
125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 3
230000015572 biosynthetic process Effects 0.000 claims description 2
FMFUHCXDFVDINI-UHFFFAOYSA-N furan-2-yl(piperazin-1-yl)methanone;hydrochloride Chemical compound Cl.C=1C=COC=1C(=O)N1CCNCC1 FMFUHCXDFVDINI-UHFFFAOYSA-N 0.000 claims description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
239000013078 crystal Substances 0.000 description 7
238000000034 method Methods 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 5
239000002002 slurry Substances 0.000 description 4
150000001875 compounds Chemical class 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
238000004566 IR spectroscopy Methods 0.000 description 2
230000001476 alcoholic effect Effects 0.000 description 2
239000002585 base Substances 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
229910000041 hydrogen chloride Inorganic materials 0.000 description 2
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
238000002156 mixing Methods 0.000 description 2
229960002386 prazosin hydrochloride Drugs 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
239000000047 product Substances 0.000 description 2
238000000746 purification Methods 0.000 description 2
239000011877 solvent mixture Substances 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
WHFMXUGKCZILJK-UHFFFAOYSA-N CO.Cl.N1CCNCC1 Chemical compound CO.Cl.N1CCNCC1 WHFMXUGKCZILJK-UHFFFAOYSA-N 0.000 description 1
206010020772 Hypertension Diseases 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
239000012458 free base Substances 0.000 description 1
MSQACBWWAIBWIC-UHFFFAOYSA-N hydron;piperazine;chloride Chemical compound Cl.C1CNCCN1 MSQACBWWAIBWIC-UHFFFAOYSA-N 0.000 description 1
238000011835 investigation Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
IENZQIKPVFGBNW-UHFFFAOYSA-N prazosin Chemical compound N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(CC1)CCN1C(=O)C1=CC=CO1 IENZQIKPVFGBNW-UHFFFAOYSA-N 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000007493 shaping process Methods 0.000 description 1
239000000725 suspension Substances 0.000 description 1
230000009466 transformation Effects 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

DD21188479A 1979-03-29 1979-03-29 Verfahren zur herstellung der kristallinen alpha-form von 1-(4-amino-6,7-dimethoxy-2-chinazolinyl)-4-(2-furoyl)-piperazin-hydrochlorid DD141674B1 (de)

Priority Applications (13)

Application Number	Priority Date	Filing Date	Title
DD21188479A DD141674B1 (de)	1979-03-29	1979-03-29	Verfahren zur herstellung der kristallinen alpha-form von 1-(4-amino-6,7-dimethoxy-2-chinazolinyl)-4-(2-furoyl)-piperazin-hydrochlorid
YU36180A YU41908B (en)	1979-03-29	1980-02-12	Process for proucing the crystalline form of 1-(4-amino-6,7-dimethoxy-2-quinazoliyl)-4-(2-furoyl)-piperazine hydrochloride
CS137480A CS224469B1 (en)	1979-03-29	1980-02-27	Method of l-/-amino-6,7-dimethoxy-2-quinazolinyl/-4-/2-furoyl/-piperazine in crystallic alpha form-l
SU807771089A SU1206277A1 (ru)	1979-03-29	1980-02-28	Способ получени кристаллической @ -формы гидрохлорида 1-/4-амино-6,7-диметокси-2-хиназолинил/-4-/2-фуроил/-пиперазина
RO105233A RO83455B (ro)	1979-03-29	1980-03-26	Procedeu pentru prepararea formei cristaline alfa a clorhidratului de1-(4-amino-6, 7-dimetoxi-2-chinazolinil)-4-(2-furoil)-piperazina
RO105234A RO83442B (ro)	1979-03-29	1980-03-26	Procedeu pentru prepararea formei alfa a clorhidratului de 1-(4-amino-6, 7-dimetoxi-2-chinazolinil)-4-(2-furoil)-piperazina
RO80100627A RO79381A (fr)	1979-03-29	1980-03-26	Procede de preparation d'une forme cristaline alpha du chlorhydrate 1(4-amino-6,7-dimethoxy-2-quinazolynile)-4-(2-furoile)-piperazine
PL24061080A PL129723B1 (en)	1979-03-29	1980-03-27	Process for preparing crystalline form of 1-/4-amino-6,7-dimethoxy-2-quinazolinyl/-4-/2-furoyl/-piperazine alpha-hydrochloride
PL24061180A PL129719B1 (en)	1979-03-29	1980-03-27	Process for preparing crystalline form of 1-/4-amino-6,7-dimethoxy-2-quinazolinyl/-4-/2-furoyl/-piperazine alpha-hydrochloride
PL22305180A PL128496B1 (en)	1979-03-29	1980-03-27	Process for preparing crystalline form of 1-/4-amino-6,7-dimethoxy-2-quinazolinyl/-4-/2-furoyl/-piperazine dihydrochloride
HU74180A HU182796B (en)	1979-03-29	1980-03-28	Process for preparing the crystallinic alpha form of 1-/4-amino-6,7-dimethoxy-2-quinazolinyl/-4-/2-furoyl/-piperazine hydrochloride
YU26883A YU42069B (en)	1979-03-29	1983-02-07	Process for the manufacture of the crystalline alpha - from of 1-(4-amino-6,7-dimethoxy-2-quinazolinye)-4-(2-furoyl)-piperazine hydrochloride
YU26783A YU42068B (en)	1979-03-29	1983-02-07	Process for the manufacture of the crystal alpha-from of 1(4-amino-dimethoxy-2-quinazolinyl)-4-(2-furoyl)-piperazine hydrochlride

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DD21188479A DD141674B1 (de)	1979-03-29	1979-03-29	Verfahren zur herstellung der kristallinen alpha-form von 1-(4-amino-6,7-dimethoxy-2-chinazolinyl)-4-(2-furoyl)-piperazin-hydrochlorid

Publications (2)

Publication Number	Publication Date
DD141674A1 DD141674A1 (de)	1980-05-14
DD141674B1 true DD141674B1 (de)	1982-06-30

Family

ID=5517404

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD21188479A DD141674B1 (de)	1979-03-29	1979-03-29	Verfahren zur herstellung der kristallinen alpha-form von 1-(4-amino-6,7-dimethoxy-2-chinazolinyl)-4-(2-furoyl)-piperazin-hydrochlorid

Country Status (7)

Country	Link
CS (1)	CS224469B1 (fr)
DD (1)	DD141674B1 (fr)
HU (1)	HU182796B (fr)
PL (3)	PL128496B1 (fr)
RO (3)	RO83455B (fr)
SU (1)	SU1206277A1 (fr)
YU (3)	YU41908B (fr)

1979
- 1979-03-29 DD DD21188479A patent/DD141674B1/de unknown
1980
- 1980-02-12 YU YU36180A patent/YU41908B/xx unknown
- 1980-02-27 CS CS137480A patent/CS224469B1/cs unknown
- 1980-02-28 SU SU807771089A patent/SU1206277A1/ru active
- 1980-03-26 RO RO105233A patent/RO83455B/ro unknown
- 1980-03-26 RO RO105234A patent/RO83442B/ro unknown
- 1980-03-26 RO RO80100627A patent/RO79381A/fr unknown
- 1980-03-27 PL PL22305180A patent/PL128496B1/pl unknown
- 1980-03-27 PL PL24061080A patent/PL129723B1/pl unknown
- 1980-03-27 PL PL24061180A patent/PL129719B1/pl unknown
- 1980-03-28 HU HU74180A patent/HU182796B/hu unknown
1983
- 1983-02-07 YU YU26883A patent/YU42069B/xx unknown
- 1983-02-07 YU YU26783A patent/YU42068B/xx unknown

Also Published As

Publication number	Publication date
RO83455A (fr)	1984-02-21
RO83455B (ro)	1984-02-28
SU1206277A1 (ru)	1986-01-23
YU36180A (en)	1983-06-30
PL129719B1 (en)	1984-06-30
CS224469B1 (en)	1984-01-16
YU42068B (en)	1988-04-30
PL129723B1 (en)	1984-06-30
HU182796B (en)	1984-03-28
RO83442B (ro)	1984-02-28
YU42069B (en)	1988-04-30
RO83442A (fr)	1984-02-21
RO79381A (fr)	1982-06-25
YU41908B (en)	1988-02-29
PL128496B1 (en)	1984-01-31
PL223051A1 (fr)	1980-12-15
YU26883A (en)	1983-10-31
DD141674A1 (de)	1980-05-14
YU26783A (en)	1984-04-30

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