NO862138L - Analogifremgangsmaate for fremstilling av terapeutisk aktive n-fenyl-4-fenyl-1-piperazincarboxamidiner og beslektede forbindelser. - Google Patents

Analogifremgangsmaate for fremstilling av terapeutisk aktive n-fenyl-4-fenyl-1-piperazincarboxamidiner og beslektede forbindelser.

Info

Publication number: NO862138L
Authority: NO; Norway
Prior art keywords: hydrogen; alkyl; formula; compound according; piperazinecarboxamidine
Prior art date: 1985-05-30

Application number

NO862138A

Other languages

English (en)

Norwegian (no)

Inventor

Jean-Claude Pascal

Original Assignee

Syntex Lab

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.)

1985-05-30

Filing date

1986-05-29

Publication date

1986-12-01

1986-05-29 Application filed by Syntex Lab filed Critical Syntex Lab

1986-12-01 Publication of NO862138L publication Critical patent/NO862138L/no

Links

150000001875 compounds Chemical class 0.000 title claims description 134
238000002360 preparation method Methods 0.000 title claims description 23
238000000034 method Methods 0.000 title claims description 19
230000001225 therapeutic effect Effects 0.000 title claims 2
239000002253 acid Substances 0.000 claims description 80
229910052739 hydrogen Inorganic materials 0.000 claims description 64
239000001257 hydrogen Substances 0.000 claims description 64
-1 -OH Chemical group 0.000 claims description 52
150000003839 salts Chemical class 0.000 claims description 41
150000002431 hydrogen Chemical class 0.000 claims description 38
150000002148 esters Chemical class 0.000 claims description 26
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 23
150000002367 halogens Chemical class 0.000 claims description 15
125000000217 alkyl group Chemical group 0.000 claims description 14
229910052736 halogen Inorganic materials 0.000 claims description 14
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 13
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 11
239000000460 chlorine Substances 0.000 claims description 11
229910052801 chlorine Inorganic materials 0.000 claims description 11
239000000546 pharmaceutical excipient Substances 0.000 claims description 11
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
125000003545 alkoxy group Chemical group 0.000 claims description 9
125000001589 carboacyl group Chemical group 0.000 claims description 9
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 9
HBGHJWNGKZSGQY-UHFFFAOYSA-N n'-(3,5-dichlorophenyl)-4-(4-hydroxy-2-methoxyphenyl)piperazine-1-carboximidamide Chemical compound COC1=CC(O)=CC=C1N1CCN(C(N)=NC=2C=C(Cl)C=C(Cl)C=2)CC1 HBGHJWNGKZSGQY-UHFFFAOYSA-N 0.000 claims description 9
239000000825 pharmaceutical preparation Substances 0.000 claims description 9
239000012458 free base Substances 0.000 claims description 8
CTQJQDJECZVMQZ-UHFFFAOYSA-N n'-(3,5-dichlorophenyl)-4-(2-methoxyphenyl)piperazine-1-carboximidamide Chemical compound COC1=CC=CC=C1N1CCN(C(N)=NC=2C=C(Cl)C=C(Cl)C=2)CC1 CTQJQDJECZVMQZ-UHFFFAOYSA-N 0.000 claims description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
238000012546 transfer Methods 0.000 claims description 8
241000124008 Mammalia Species 0.000 claims description 7
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 6
206010003119 arrhythmia Diseases 0.000 claims description 6
230000006793 arrhythmia Effects 0.000 claims description 6
125000001424 substituent group Chemical group 0.000 claims description 6
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
LNLHBFVYXUXLFX-UHFFFAOYSA-N 4-(2-methoxyphenyl)-n'-(2-methylpropyl)-n-phenylpiperazine-1-carboximidamide Chemical compound COC1=CC=CC=C1N1CCN(C(NC=2C=CC=CC=2)=NCC(C)C)CC1 LNLHBFVYXUXLFX-UHFFFAOYSA-N 0.000 claims description 3
IJEPCVKPPXQPBQ-UHFFFAOYSA-N n'-(3,4-dichlorophenyl)-4-(2-methoxyphenyl)piperazine-1-carboximidamide Chemical compound COC1=CC=CC=C1N1CCN(C(N)=NC=2C=C(Cl)C(Cl)=CC=2)CC1 IJEPCVKPPXQPBQ-UHFFFAOYSA-N 0.000 claims description 3
NRKGVSYVKJHVRF-UHFFFAOYSA-N n'-(3,5-dichlorophenyl)-4-(4-fluorophenyl)piperazine-1-carboximidamide Chemical compound C1=CC(F)=CC=C1N1CCN(C(=N)NC=2C=C(Cl)C=C(Cl)C=2)CC1 NRKGVSYVKJHVRF-UHFFFAOYSA-N 0.000 claims description 3
RBOMQXYVSYEKPG-UHFFFAOYSA-N n-(3,4-dichlorophenyl)-4-(2-methoxyphenyl)-n'-(2-methylpropyl)piperazine-1-carboximidamide Chemical compound COC1=CC=CC=C1N1CCN(C(NC=2C=C(Cl)C(Cl)=CC=2)=NCC(C)C)CC1 RBOMQXYVSYEKPG-UHFFFAOYSA-N 0.000 claims description 3
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
229910052731 fluorine Inorganic materials 0.000 claims description 2
239000011737 fluorine Substances 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
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150000004702 methyl esters Chemical class 0.000 description 41
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 38
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VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 8
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150000001448 anilines Chemical class 0.000 description 6
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238000001816 cooling Methods 0.000 description 6
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125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 5
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125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
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BZGNKKZWBCFYBQ-UHFFFAOYSA-N piperazin-1-ylmethanimine Chemical class N=CN1CCNCC1 BZGNKKZWBCFYBQ-UHFFFAOYSA-N 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/20—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
- C07D295/215—Radicals derived from nitrogen analogues of carbonic acid
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Engineering & Computer Science (AREA)
Cardiology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Heart & Thoracic Surgery (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

NO862138A 1985-05-30 1986-05-29 Analogifremgangsmaate for fremstilling av terapeutisk aktive n-fenyl-4-fenyl-1-piperazincarboxamidiner og beslektede forbindelser. NO862138L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US06/739,393 US4713382A (en)	1985-05-30	1985-05-30	N-phenyl-4-phenyl-1-piperazinecarboxamidines and related compounds as antiarrhythmic agents

Publications (1)

Publication Number	Publication Date
NO862138L true NO862138L (no)	1986-12-01

Family

ID=24972082

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO862138A NO862138L (no)	1985-05-30	1986-05-29	Analogifremgangsmaate for fremstilling av terapeutisk aktive n-fenyl-4-fenyl-1-piperazincarboxamidiner og beslektede forbindelser.

Country Status (16)

Country	Link
US (1)	US4713382A (fi)
EP (1)	EP0204265A1 (fi)
JP (1)	JPS61280486A (fi)
KR (1)	KR860008999A (fi)
CN (1)	CN86103798A (fi)
AU (1)	AU5805086A (fi)
DD (1)	DD247452A5 (fi)
DK (1)	DK253586A (fi)
ES (1)	ES8708132A1 (fi)
FI (1)	FI862279A (fi)
GR (1)	GR861370B (fi)
HU (1)	HU195201B (fi)
IL (1)	IL78963A0 (fi)
NO (1)	NO862138L (fi)
PT (1)	PT82675B (fi)
ZA (1)	ZA864023B (fi)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP1231208A3 (en) *	1991-08-14	2003-12-10	Procter & Gamble Pharmaceuticals	4-oxocyclic ureas useful as antiarrhythmic and antifibrillatory agents
JP6397407B2 (ja)	2012-07-19	2018-09-26	ドレクセルユニバーシティ	細胞タンパク質ホメオスタシスを調節するためのシグマ受容体リガンド
WO2019089902A1 (en)	2017-11-01	2019-05-09	Drexel University	Compounds, compositions, and methods for treating diseases

Family Cites Families (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA574981A (en) *		1959-04-28	H. Brown Edwin	Fluid pressure bearing and seal for centrifugal pump
GB948766A (en) *	1959-10-20	1964-02-05	May & Baker Ltd	Trifluoromethylphenylpiperazine derivatives
US3655667A (en) *	1968-04-04	1972-04-11	Smith Kline French Lab	1-(2-benzoylcyclopropylmethyl)-4-phenylpiperazines
PH12016A (en) *	1972-09-22	1978-10-06	Rorer Inc William H	Amidinoureas
US3793322A (en) *	1972-12-15	1974-02-19	Usv Pharma Corp	1,4-disubstituted piperazines
US3976643A (en) *	1973-07-13	1976-08-24	William H. Rorer, Inc.	Guanidines
US3961056A (en) *	1974-02-11	1976-06-01	The Upjohn Company	Substituted morpholine guanidines for the treatment of arrhythmic conditions
GB1514907A (en) *	1975-05-30	1978-06-21	Rorer Inc William H	Process for the preparation of substituted phenylguanidines and substituted phenylguanidines when thus prepared
US4211867A (en) *	1976-03-19	1980-07-08	Mcneil Laboratories, Incorporated	Nitrogen heterocyclic carboximidamide compounds
US4138561A (en) *	1977-09-30	1979-02-06	Bristol-Myers Company	Cyanocarboxamidines and quinazoline process
EP0005385B1 (fr) *	1978-04-27	1982-09-01	LAROCHE NAVARRON S.A. Société dite:	Dérivés de la pipérazine méthanimine, leur procédé de préparation et leurs applications en thérapeutique
CH643549A5 (de) *	1979-08-25	1984-06-15	Merz & Co	N-(trimethoxybenzyl)-n'-phenylpiperazine.
ZA81160B (en) *	1980-01-31	1982-02-24	Laroche Navarron Sa	Piperazine derivatives of theophylline

1985
- 1985-05-30 US US06/739,393 patent/US4713382A/en not_active Expired - Fee Related
1986
- 1986-05-28 PT PT82675A patent/PT82675B/pt unknown
- 1986-05-28 GR GR861370A patent/GR861370B/el unknown
- 1986-05-29 FI FI862279A patent/FI862279A/fi not_active Application Discontinuation
- 1986-05-29 ES ES555440A patent/ES8708132A1/es not_active Expired
- 1986-05-29 ZA ZA864023A patent/ZA864023B/xx unknown
- 1986-05-29 NO NO862138A patent/NO862138L/no unknown
- 1986-05-29 HU HU862258A patent/HU195201B/hu unknown
- 1986-05-29 JP JP61125592A patent/JPS61280486A/ja active Pending
- 1986-05-29 KR KR1019860004227A patent/KR860008999A/ko not_active Application Discontinuation
- 1986-05-29 AU AU58050/86A patent/AU5805086A/en not_active Abandoned
- 1986-05-29 IL IL78963A patent/IL78963A0/xx unknown
- 1986-05-29 EP EP86107310A patent/EP0204265A1/en not_active Withdrawn
- 1986-05-29 DK DK253586A patent/DK253586A/da not_active Application Discontinuation
- 1986-05-29 CN CN198686103798A patent/CN86103798A/zh active Pending
- 1986-05-30 DD DD86290764A patent/DD247452A5/de unknown

Also Published As

Publication number	Publication date
FI862279A0 (fi)	1986-05-29
IL78963A0 (en)	1986-09-30
GR861370B (en)	1986-09-17
ES555440A0 (es)	1987-10-16
ZA864023B (en)	1988-01-27
DK253586A (da)	1986-12-01
ES8708132A1 (es)	1987-10-16
AU5805086A (en)	1986-12-04
FI862279A (fi)	1986-12-01
US4713382A (en)	1987-12-15
KR860008999A (ko)	1986-12-19
EP0204265A1 (en)	1986-12-10
HU195201B (en)	1988-04-28
DD247452A5 (de)	1987-07-08
DK253586D0 (da)	1986-05-29
CN86103798A (zh)	1987-06-10
PT82675B (en)	1987-09-29
PT82675A (en)	1986-06-01
JPS61280486A (ja)	1986-12-11
HUT41016A (en)	1987-03-30

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