CY1255A - Long-acting parenteral compositions of haloperidol and bromperidol derivatives - Google Patents

Long-acting parenteral compositions of haloperidol and bromperidol derivatives Download PDF

Info

Publication number: CY1255A
Authority: CY; Cyprus
Prior art keywords: composition; haloperidol; bromperidol; long; administration
Prior art date: 1979-06-28

Application number

CY1255A

Other languages

English (en)

Original Assignee

Janssen Pharmaceutica Nv

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.)

1979-06-28

Filing date

1980-06-03

Publication date

1984-08-31

1980-06-03 Application filed by Janssen Pharmaceutica Nv filed Critical Janssen Pharmaceutica Nv

1984-08-31 Publication of CY1255A publication Critical patent/CY1255A/en

Links

239000000203 mixture Substances 0.000 title claims description 29
LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical group C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 title description 23
RKLNONIVDFXQRX-UHFFFAOYSA-N Bromperidol Chemical class C1CC(O)(C=2C=CC(Br)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 RKLNONIVDFXQRX-UHFFFAOYSA-N 0.000 title description 11
229960003878 haloperidol Drugs 0.000 title description 11
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims description 18
230000000506 psychotropic effect Effects 0.000 claims description 7
239000008159 sesame oil Substances 0.000 claims description 7
235000011803 sesame oil Nutrition 0.000 claims description 7
235000019445 benzyl alcohol Nutrition 0.000 claims description 6
150000001954 decanoic acid esters Chemical class 0.000 claims description 5
239000003755 preservative agent Substances 0.000 claims description 5
230000002335 preservative effect Effects 0.000 claims description 5
238000007918 intramuscular administration Methods 0.000 claims description 4
238000007920 subcutaneous administration Methods 0.000 claims description 4
239000004480 active ingredient Substances 0.000 claims description 3
125000001309 chloro group Chemical group Cl* 0.000 claims description 3
239000002904 solvent Substances 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 2
230000000845 anti-microbial effect Effects 0.000 claims description 2
238000007911 parenteral administration Methods 0.000 claims description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
239000004599 antimicrobial Substances 0.000 claims 1
229910052801 chlorine Inorganic materials 0.000 claims 1
239000000460 chlorine Substances 0.000 claims 1
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
BLDQVNWZPYYSRH-UHFFFAOYSA-N piperidin-1-yl decanoate Chemical compound CCCCCCCCCC(=O)ON1CCCCC1 BLDQVNWZPYYSRH-UHFFFAOYSA-N 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
229960004037 bromperidol Drugs 0.000 description 8
238000002560 therapeutic procedure Methods 0.000 description 7
150000001875 compounds Chemical class 0.000 description 5
230000000694 effects Effects 0.000 description 5
150000002148 esters Chemical class 0.000 description 5
238000000034 method Methods 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
GUTXTARXLVFHDK-UHFFFAOYSA-N Haloperidol decanoate Chemical compound C1CC(OC(=O)CCCCCCCCC)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 GUTXTARXLVFHDK-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
206010047700 Vomiting Diseases 0.000 description 3
ZINCPWWBSRSXBH-UHFFFAOYSA-N [4-(4-bromophenyl)-1-[4-(4-fluorophenyl)-4-oxobutyl]piperidin-4-yl] decanoate Chemical compound C1CC(OC(=O)CCCCCCCCC)(C=2C=CC(Br)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 ZINCPWWBSRSXBH-UHFFFAOYSA-N 0.000 description 3
IPIVAXLHTVNRBS-UHFFFAOYSA-N decanoyl chloride Chemical compound CCCCCCCCCC(Cl)=O IPIVAXLHTVNRBS-UHFFFAOYSA-N 0.000 description 3
239000002895 emetic Substances 0.000 description 3
229960005007 haloperidol decanoate Drugs 0.000 description 3
238000002347 injection Methods 0.000 description 3
239000007924 injection Substances 0.000 description 3
LKPFBGKZCCBZDK-UHFFFAOYSA-N n-hydroxypiperidine Chemical class ON1CCCCC1 LKPFBGKZCCBZDK-UHFFFAOYSA-N 0.000 description 3
239000003921 oil Substances 0.000 description 3
235000019198 oils Nutrition 0.000 description 3
239000004089 psychotropic agent Substances 0.000 description 3
SKYZYDSNJIOXRL-BTQNPOSSSA-N (6ar)-6-methyl-5,6,6a,7-tetrahydro-4h-dibenzo[de,g]quinoline-10,11-diol;hydrochloride Chemical compound Cl.C([C@H]1N(C)CC2)C3=CC=C(O)C(O)=C3C3=C1C2=CC=C3 SKYZYDSNJIOXRL-BTQNPOSSSA-N 0.000 description 2
241000282472 Canis lupus familiaris Species 0.000 description 2
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
229960004046 apomorphine Drugs 0.000 description 2
VMWNQDUVQKEIOC-CYBMUJFWSA-N apomorphine Chemical compound C([C@H]1N(C)CC2)C3=CC=C(O)C(O)=C3C3=C1C2=CC=C3 VMWNQDUVQKEIOC-CYBMUJFWSA-N 0.000 description 2
229960003990 apomorphine hydrochloride Drugs 0.000 description 2
125000001246 bromo group Chemical group Br* 0.000 description 2
229960004284 bromperidol decanoate Drugs 0.000 description 2
238000004440 column chromatography Methods 0.000 description 2
239000003480 eluent Substances 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
230000007794 irritation Effects 0.000 description 2
239000008194 pharmaceutical composition Substances 0.000 description 2
230000002035 prolonged effect Effects 0.000 description 2
239000000243 solution Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000000725 suspension Substances 0.000 description 2
229960002341 trifluperidol Drugs 0.000 description 2
GPMXUUPHFNMNDH-UHFFFAOYSA-N trifluperidol Chemical compound C1CC(O)(C=2C=C(C=CC=2)C(F)(F)F)CCN1CCCC(=O)C1=CC=C(F)C=C1 GPMXUUPHFNMNDH-UHFFFAOYSA-N 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 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
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
239000000654 additive Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
230000037396 body weight Effects 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
230000001684 chronic effect Effects 0.000 description 1
238000001816 cooling Methods 0.000 description 1
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 1
GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 1
230000008034 disappearance Effects 0.000 description 1
230000002964 excitative effect Effects 0.000 description 1
230000006698 induction Effects 0.000 description 1
239000007972 injectable composition Substances 0.000 description 1
230000005923 long-lasting effect Effects 0.000 description 1
230000007774 longterm Effects 0.000 description 1
238000012423 maintenance Methods 0.000 description 1
239000012071 phase Substances 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
HDOWRFHMPULYOA-UHFFFAOYSA-N piperidin-4-ol Chemical class OC1CCNCC1 HDOWRFHMPULYOA-UHFFFAOYSA-N 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
208000020016 psychiatric disease Diseases 0.000 description 1
229940001470 psychoactive drug Drugs 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000011084 recovery Methods 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
230000002936 tranquilizing effect Effects 0.000 description 1
ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
230000008673 vomiting Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/52—Oxygen atoms attached in position 4 having an aryl radical as the second substituent in position 4
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Anesthesiology (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (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)
Hydrogenated Pyridines (AREA)
Medicinal Preparation (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

CY1255A 1979-06-28 1980-06-03 Long-acting parenteral compositions of haloperidol and bromperidol derivatives CY1255A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP8082679A JPS568318A (en)	1979-06-28	1979-06-28	Non oral long acting composition of haloperidol and bromperidol derivative

Publications (1)

Publication Number	Publication Date
CY1255A true CY1255A (en)	1984-08-31

Family

ID=13729223

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CY1255A CY1255A (en)	1979-06-28	1980-06-03	Long-acting parenteral compositions of haloperidol and bromperidol derivatives

Country Status (9)

Country	Link
JP (1)	JPS568318A (fr)
BE (1)	BE883994A (fr)
CY (1)	CY1255A (fr)
DE (1)	DE3024305A1 (fr)
FR (1)	FR2460932A1 (fr)
GB (1)	GB2054371B (fr)
HK (1)	HK83384A (fr)
KE (1)	KE3427A (fr)
NL (1)	NL190775C (fr)

Families Citing this family (21)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB8621892D0 (en) *	1986-09-11	1986-10-15	Lundbeck & Co As H	Organic compound
DK238190D0 (da) *	1990-10-03	1990-10-03	Lundbeck & Co As H	Depotderivater
ATE188375T1 (de) *	1992-11-17	2000-01-15	Yoshitomi Pharmaceutical	Ein antipsychotikum enthaltende mikrokugel zur verzögerten freisetzung und verfahren für ihre herstellung
WO1998018769A1 (fr) *	1996-10-31	1998-05-07	The United States Of America, Represented By The Secretary, Department Of Health And Human Services	Derives a liberation prolongee d'analogues hydroxyles de 1-[2[bis(aryl)methoxy]ethyl]-piperazines et -homopiperazines substituees et leur utilisation comme antagonistes non competitifs du recaptage de la dopamine
RU2178297C1 (ru) *	2001-02-02	2002-01-20	Открытое акционерное общество "Химико-фармацевтический комбинат "Акрихин"	Фармацевтическая композиция, обладающая антипсихотическим и противорвотным действием, и способ ее получения
JP2008519840A (ja)	2004-11-10	2008-06-12	ジェンザイム・コーポレイション	糖尿病の処置方法
WO2007134086A2 (fr)	2006-05-09	2007-11-22	Genzyme Corporation	Méthodes pour traiter une maladie de foie adipeux
EP2594562B1 (fr)	2007-05-31	2016-07-20	Genzyme Corporation	Inhibiteurs de glucosylcéramide synthase de type 2-acylaminopropanol
KR101640263B1 (ko)	2007-10-05	2016-07-15	젠자임 코포레이션	세라마이드 유도체로 다낭성 신장질환을 치료하는 방법
JP2011529500A (ja)	2008-07-28	2011-12-08	ジェンザイムコーポレーション	虚脱性糸球体症および他の糸球体疾患の処置のためのグルコシルセラミドシンターゼ阻害
US8309593B2 (en)	2008-10-03	2012-11-13	Genzyme Corporation	2-acylaminopropoanol-type glucosylceramide synthase inhibitors
US9034867B2 (en)	2011-03-18	2015-05-19	Alkermes Pharma Ireland Limited	Pharmaceutical compositions comprising sorbitan esters
CN103301461B (zh) *	2012-03-08	2018-09-07	江苏豪森药业集团有限公司	一种长效注射制剂及其制备方法和用途
WO2013142205A1 (fr)	2012-03-19	2013-09-26	Alkermes Pharma Ireland Limited	Compositions pharmaceutiques comprenant de l'alcool benzylique
WO2013142198A1 (fr)	2012-03-19	2013-09-26	Alkermes Pharma Ireland Limited	Compositions pharmaceutiques comprenant des esters d'acides gras
JP6219918B2 (ja)	2012-03-19	2017-10-25	アルカームスファーマアイルランドリミテッド	グリセロールエステルを含む医薬組成物
EP3718536A1 (fr)	2012-09-19	2020-10-07	Alkermes Pharma Ireland Limited	Compositions pharmaceutiques présentant une stabilité améliorée au stockage
EP3119399A4 (fr)	2014-03-20	2017-09-27	Alkermes Pharma Ireland Limited	Formulations d'aripiprazole présentant des vitesses d'injection plus élevées
CA3092335A1 (fr)	2018-03-05	2019-09-12	Alkermes Pharma Ireland Limited	Strategie de dosage d'aripiprazole
CN113117092A (zh) *	2020-01-14	2021-07-16	中国科学院上海药物研究所	一种非水缓释递药系统
HUP2100259A1 (hu)	2021-07-07	2023-01-28	Richter Gedeon Nyrt	Cariprazine tartalmú szabályozott hatóanyag-leadású injekciós készítmények

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3408356A (en) *	1965-08-31	1968-10-29	Squibb & Sons Inc	Long chain esters of 4'-fluoro-4-[4-hydroxy-4-(alpha, alpha, alpha-trifluorotolyl)piperi-dino]butyrophenone and the like
DE1695194A1 (de) *	1966-07-11	1971-03-18	Hoffmann La Roche	Verfahren zur Herstellung von Piperidinderivaten
US3850935A (en) *	1971-10-16	1974-11-26	Sumitomo Chemical Co	Process for producing piperidine derivatives by degrading quaternary piperidinium salts

1979
- 1979-06-28 JP JP8082679A patent/JPS568318A/ja active Pending
1980
- 1980-06-03 CY CY1255A patent/CY1255A/en unknown
- 1980-06-03 GB GB8018117A patent/GB2054371B/en not_active Expired
- 1980-06-20 NL NL8003583A patent/NL190775C/xx not_active IP Right Cessation
- 1980-06-25 BE BE0/201165A patent/BE883994A/fr not_active IP Right Cessation
- 1980-06-27 DE DE19803024305 patent/DE3024305A1/de active Granted
- 1980-06-27 FR FR8014443A patent/FR2460932A1/fr active Granted
1984
- 1984-07-20 KE KE3427A patent/KE3427A/xx unknown
- 1984-11-01 HK HK833/84A patent/HK83384A/xx not_active IP Right Cessation

Also Published As

Publication number	Publication date
NL190775B (nl)	1994-03-16
NL8003583A (nl)	1980-12-30
KE3427A (en)	1984-08-10
GB2054371A (en)	1981-02-18
FR2460932B1 (fr)	1984-11-16
DE3024305C2 (fr)	1989-12-07
FR2460932A1 (fr)	1981-01-30
BE883994A (fr)	1980-12-29
HK83384A (en)	1984-11-09
JPS568318A (en)	1981-01-28
DE3024305A1 (de)	1981-01-22
GB2054371B (en)	1983-08-03
NL190775C (nl)	1994-08-16

Publication	Publication Date	Title
GB2054371A (en)	1981-02-18	Long-acting parenteral compositions of haloperidol and bromperidol derivatives
DE2431178C2 (de)	1985-10-24	Piperazinderivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneipräparate
WO1992001675A3 (fr)	1992-08-06	Composes bis-aryle bicycliques substitues ayant une activite antagoniste selective sur le leukotriene b4, leur preparation et utilisation dans des compositions pharmaceutiques
DE3200304A1 (de)	1982-08-26	3-aminopropoxyaryl-derivate, ihre herstellung und sie enthaltende arzneimittel
US4855307A (en)	1989-08-08	Acetic acid ester of haloperidol
HK1006020B (en)	1999-02-05	Method of improving sleep
DE2944037C2 (fr)	1988-04-14
DE2538424A1 (de)	1977-03-03	Neue oxazolidinone, verfahren zu deren herstellung und diese verbindungen enthaltende arzneimittel
EP0027895A1 (fr)	1981-05-06	Pipéridines substituées par des groupes 1-(2-(alkyl et arylsulfonyl)-2-propényl et propyl) et compositions pharmaceutiques et antimicrobiennes les contenant
DE3317289A1 (de)	1983-11-24	2(1h).pyridinon-derivate, ihre herstellung und sie enthaltende pharmazeutische zubereitungen
DE1134079B (de)	1962-08-02	Verfahren zur Herstellung von N-Fluoracetyl und N-Chloracetylpiperazinen
CA2489723A1 (fr)	2003-12-24	Nouveaux derives d'aryl-{4-halogeno-4-[(heteroaryl-methylamino)-methyl]-piperidin-1-yl}-methanone, leur procede de preparation et leur utilisation a titre de medicaments
CA1181402A (fr)	1985-01-22	Derives substitues de la 2-amino-3,4-dihydropyridine; preparation et utilisation en medecine
DE2131330A1 (de)	1972-01-05	Imidazo-[1,2-a]-benzimidazolderivate und Verfahren zur Herstellung derselben
DE3850222T2 (de)	1994-09-22	1,4-Disubstituierte-piperidinyl-Verbindungen.
LAPPIN	1958	Cyclization of 2-Aminopyridine derivatives. III. Reaction of some 2-aminopyridines with alkyl acrylates and alkyl 3-halopropionates
DE2040231C3 (de)	1979-04-12	4-Aryl-l-(4,4-diaryl-butyl)-4hydröxypiperidine, ihre Herstellung und Verwendung
US3180867A (en)	1965-04-27	Piperazine derivatives
DE3650311T2 (de)	1995-10-12	Verwendung von Quinazolinen zur Herstellung eines Arzneimittels zur Behandlung und Vorbeugung von Arrhythmie.
SU1189339A3 (ru)	1985-10-30	Способ получени производных 2-оксиметилхиноксалин-1,4-диоксида
US3278382A (en)	1966-10-11	2-amino-5-aryloxazoline compositions and methods of using same
US4206217A (en)	1980-06-03	3-[4-(1,3-Diazacycloalken-2-yl)-phenyl]-1,2-benzisothiazoles, their manufacture, and drugs containing these compounds
IE35608B1 (en)	1976-03-31	Halogen-substituted phenylalkylamines and their derivatives
DE2253134C3 (de)	1976-10-07	Salze substituierter 2-Anilinonicotinsäuren mit Lysin
HU191600B (en)	1987-03-30	Process for preparing /2-amino-ethyl/-pyridine or-pyrazine derivatives