DD229402A5 - Verfahren zur herstellung von piperidinion-derivaten, die als myocard-schutz eine antiarrhytmische aktivitaet ausweisen - Google Patents

Verfahren zur herstellung von piperidinion-derivaten, die als myocard-schutz eine antiarrhytmische aktivitaet ausweisen Download PDF

Info

Publication number: DD229402A5
Authority: DD; German Democratic Republic
Prior art keywords: alkyl group; group; carbon atoms; hydrogen; formula
Prior art date: 1982-11-08

Application number

DD83270121A

Other languages

German (de)

English (en)

Inventor

Claude Bernhart

Werner Cautreels

Patrick Gautier

Original Assignee

Sanofi Sa

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.)

1982-11-08

Filing date

1983-11-07

Publication date

1985-11-06

1983-11-07 Application filed by Sanofi Sa filed Critical Sanofi Sa

1985-11-06 Publication of DD229402A5 publication Critical patent/DD229402A5/de

Links

238000000034 method Methods 0.000 title claims abstract description 13
230000000694 effects Effects 0.000 title description 5
238000004519 manufacturing process Methods 0.000 title description 2
239000003416 antiarrhythmic agent Substances 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 17
125000000217 alkyl group Chemical group 0.000 claims abstract description 15
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 11
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
239000001257 hydrogen Substances 0.000 claims abstract description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 8
238000002360 preparation method Methods 0.000 claims abstract description 7
CNMOHEDUVVUVPP-UHFFFAOYSA-N piperidine-2,3-dione Chemical group O=C1CCCNC1=O CNMOHEDUVVUVPP-UHFFFAOYSA-N 0.000 claims abstract description 4
125000004076 pyridyl group Chemical group 0.000 claims abstract description 3
239000002904 solvent Substances 0.000 claims description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
238000006243 chemical reaction Methods 0.000 claims description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
239000002253 acid Substances 0.000 claims description 4
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 claims description 4
150000002825 nitriles Chemical class 0.000 claims description 4
229910052757 nitrogen Inorganic materials 0.000 claims description 3
230000029936 alkylation Effects 0.000 claims description 2
238000005804 alkylation reaction Methods 0.000 claims description 2
229910052799 carbon Inorganic materials 0.000 claims description 2
239000012442 inert solvent Substances 0.000 claims description 2
241000251730 Chondrichthyes Species 0.000 claims 1
239000003245 coal Substances 0.000 claims 1
238000010438 heat treatment Methods 0.000 claims 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
230000003288 anthiarrhythmic effect Effects 0.000 abstract description 6
239000003814 drug Substances 0.000 abstract description 4
210000004165 myocardium Anatomy 0.000 abstract description 2
229940053994 hypnotics and sedatives piperidinedione derivative Drugs 0.000 abstract 1
230000005923 long-lasting effect Effects 0.000 abstract 1
150000005458 piperidinediones Chemical class 0.000 abstract 1
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
239000000243 solution Substances 0.000 description 10
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 6
239000000203 mixture Substances 0.000 description 6
206010003119 arrhythmia Diseases 0.000 description 5
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 4
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000012312 sodium hydride Substances 0.000 description 3
229910000104 sodium hydride Inorganic materials 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
GBFWRNRCKSYGEW-UHFFFAOYSA-N 1-hydroxypiperidin-2-ol Chemical class OC1CCCCN1O GBFWRNRCKSYGEW-UHFFFAOYSA-N 0.000 description 2
241000282472 Canis lupus familiaris Species 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
230000002159 abnormal effect Effects 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
238000009833 condensation Methods 0.000 description 2
230000005494 condensation Effects 0.000 description 2
238000001816 cooling Methods 0.000 description 2
239000013078 crystal Substances 0.000 description 2
229940043279 diisopropylamine Drugs 0.000 description 2
QVDYYQXUNAQSNI-UHFFFAOYSA-N ethyl acetate;pentane Chemical compound CCCCC.CCOC(C)=O QVDYYQXUNAQSNI-UHFFFAOYSA-N 0.000 description 2
239000000284 extract Substances 0.000 description 2
229910052500 inorganic mineral Chemical class 0.000 description 2
239000007788 liquid Substances 0.000 description 2
239000011707 mineral Chemical class 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
230000002035 prolonged effect Effects 0.000 description 2
230000033764 rhythmic process Effects 0.000 description 2
238000003756 stirring Methods 0.000 description 2
LEWXPHFUQZGJBR-UHFFFAOYSA-N 3-[2-[di(propan-2-yl)amino]ethyl]-4,4,5,5-tetramethyl-3-pyridin-2-ylpiperidine-2,6-dione Chemical compound C=1C=CC=NC=1C1(CCN(C(C)C)C(C)C)C(=O)NC(=O)C(C)(C)C1(C)C LEWXPHFUQZGJBR-UHFFFAOYSA-N 0.000 description 1
RNCVSWWWYHOYDS-UHFFFAOYSA-N 3-[2-[di(propan-2-yl)amino]ethyl]-4,5,5-trimethyl-3-pyridin-2-ylpiperidine-2,6-dione Chemical compound C=1C=CC=NC=1C1(CCN(C(C)C)C(C)C)C(C)C(C)(C)C(=O)NC1=O RNCVSWWWYHOYDS-UHFFFAOYSA-N 0.000 description 1
AWSBGTCINOQWGE-UHFFFAOYSA-N 3-methyl-2-pyridin-2-ylbut-2-enenitrile Chemical compound CC(C)=C(C#N)C1=CC=CC=N1 AWSBGTCINOQWGE-UHFFFAOYSA-N 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
238000005481 NMR spectroscopy Methods 0.000 description 1
208000007536 Thrombosis Diseases 0.000 description 1
206010047281 Ventricular arrhythmia Diseases 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
238000010171 animal model Methods 0.000 description 1
210000001367 artery Anatomy 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
208000035475 disorder Diseases 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000000499 gel Substances 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
230000000302 ischemic effect Effects 0.000 description 1
LRDFRRGEGBBSRN-UHFFFAOYSA-N isobutyronitrile Chemical compound CC(C)C#N LRDFRRGEGBBSRN-UHFFFAOYSA-N 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
-1 methyl-substituted morpholino Chemical group 0.000 description 1
230000002107 myocardial effect Effects 0.000 description 1
208000010125 myocardial infarction Diseases 0.000 description 1
DBVADBHSJCWFKI-UHFFFAOYSA-N n-(2-chloroethyl)-n-propan-2-ylpropan-2-amine Chemical compound CC(C)N(C(C)C)CCCl DBVADBHSJCWFKI-UHFFFAOYSA-N 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
230000001575 pathological effect Effects 0.000 description 1
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
KNCYXPMJDCCGSJ-UHFFFAOYSA-N piperidine-2,6-dione Chemical class O=C1CCCC(=O)N1 KNCYXPMJDCCGSJ-UHFFFAOYSA-N 0.000 description 1
230000000750 progressive effect Effects 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
231100000161 signs of toxicity Toxicity 0.000 description 1
150000003385 sodium Chemical class 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000000725 suspension Substances 0.000 description 1
230000002861 ventricular Effects 0.000 description 1
206010047302 ventricular tachycardia Diseases 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- 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
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/57—Nitriles

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Cardiology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
Animal Behavior & Ethology (AREA)
Heart & Thoracic Surgery (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Plural Heterocyclic Compounds (AREA)
Hydrogenated Pyridines (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Pyridine Compounds (AREA)
Solid-Sorbent Or Filter-Aiding Compositions (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

DD83270121A 1982-11-08 1983-11-07 Verfahren zur herstellung von piperidinion-derivaten, die als myocard-schutz eine antiarrhytmische aktivitaet ausweisen DD229402A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR8218706A FR2535721A1 (fr)	1982-11-08	1982-11-08	Derives de la piperidinedione protecteurs du myocarde presentant une acticite antiarythmique, leur procede de preparation et les medicaments qui contiennent lesdits derives

Publications (1)

Publication Number	Publication Date
DD229402A5 true DD229402A5 (de)	1985-11-06

Family

ID=9279000

Family Applications (3)

Application Number	Title	Priority Date	Filing Date
DD83270121A DD229402A5 (de)	1982-11-08	1983-11-07	Verfahren zur herstellung von piperidinion-derivaten, die als myocard-schutz eine antiarrhytmische aktivitaet ausweisen
DD83270120A DD229407A5 (de)	1982-11-08	1983-11-07	Verfahren zur herstellung von piperidindion-derivaten, die als myocard-schutz eine antiarrhytmische aktivitaet aufweisen
DD83256411A DD219770A5 (de)	1982-11-08	1983-11-07	Verfahren zur herstellung von piperidindion-derivaten

Family Applications After (2)

Application Number	Title	Priority Date	Filing Date
DD83270120A DD229407A5 (de)	1982-11-08	1983-11-07	Verfahren zur herstellung von piperidindion-derivaten, die als myocard-schutz eine antiarrhytmische aktivitaet aufweisen
DD83256411A DD219770A5 (de)	1982-11-08	1983-11-07	Verfahren zur herstellung von piperidindion-derivaten

Country Status (29)

Country	Link
US (1)	US4721710A (cs)
EP (1)	EP0110755B1 (cs)
JP (1)	JPS59161377A (cs)
KR (1)	KR900006721B1 (cs)
AT (1)	ATE22561T1 (cs)
AU (1)	AU565519B2 (cs)
CA (1)	CA1221967A (cs)
CS (1)	CS244681B2 (cs)
DD (3)	DD229402A5 (cs)
DE (1)	DE3366623D1 (cs)
DK (1)	DK511383A (cs)
ES (1)	ES8406070A1 (cs)
FI (1)	FI79536C (cs)
FR (1)	FR2535721A1 (cs)
GR (1)	GR78747B (cs)
HU (1)	HU191494B (cs)
IE (1)	IE56209B1 (cs)
IL (1)	IL70099A (cs)
MA (1)	MA19948A1 (cs)
NO (1)	NO159852C (cs)
NZ (1)	NZ206177A (cs)
OA (1)	OA07582A (cs)
PH (1)	PH20421A (cs)
PL (3)	PL139946B1 (cs)
PT (1)	PT77607B (cs)
SG (1)	SG1989G (cs)
SU (3)	SU1333237A3 (cs)
YU (3)	YU221183A (cs)
ZA (1)	ZA838065B (cs)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4668689A (en) *	1984-07-19	1987-05-26	National Research Development Corporation	Glutarimide derivatives for treating oestrogen-dependent tumors
US5238947A (en) *	1990-04-12	1993-08-24	University Of Georgia Research Foundation, Inc.	Synthetic piperidinediones with cytostatic activity
US5463063A (en) *	1993-07-02	1995-10-31	Celgene Corporation	Ring closure of N-phthaloylglutamines
DE19703763C1 (de) *	1997-02-01	1998-10-01	Gruenenthal Gmbh	Thalidomidanaloge Verbindungen aus der Klasse der Piperidin-2,6-Dione
DK2710007T3 (da)	2011-05-17	2020-01-27	Principia Biopharma Inc	Kinasehæmmere
AU2012255860C1 (en)	2011-05-17	2015-12-10	Principia Biopharma Inc.	Tyrosine kinase inhibitors
WO2012158795A1 (en)	2011-05-17	2012-11-22	Principia Biopharma Inc.	Pyrazolopyrimidine derivatives as tyrosine kinase inhibitors
SMT201900344T1 (it)	2012-09-10	2019-07-11	Principia Biopharma Inc	Composti di pirazolopirimidina come inibitori di chinasi
US8957080B2 (en)	2013-04-09	2015-02-17	Principia Biopharma Inc.	Tyrosine kinase inhibitors
CN112353806A (zh)	2014-02-21	2021-02-12	普林斯匹亚生物制药公司	Btk抑制剂的盐和固体形式
SG11201704808VA (en)	2014-12-18	2017-07-28	Principia Biopharma Inc	Treatment of pemphigus
US20180305350A1 (en)	2015-06-24	2018-10-25	Principia Biopharma Inc.	Tyrosine kinase inhibitors
IL263815B (en)	2016-06-29	2022-07-01	Principia Biopharma Inc	Modified release formulations of 2-[3-[4-amino-3-(2-fluoro-4-phenoxy-phenyl)pyrazolo[4,3-d]pyrimidin-1-yl]piperidine-1-carbonyl]-4 -Methyl-4-[4-(Oxtan-3-yl)piperazin-1-yl)pent-2-ananitrile
AU2020365951B2 (en)	2019-10-14	2026-07-16	Principia Biopharma Inc.	Methods for treating immune thrombocytopenia by administering (R)-2-[3-[4-amino-3-(2-fluoro-4-phenoxy-phenyl)pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carbonyl]-4-methyl-4-[4-(oxetan-3-yl)piperazin-1-yl]pent-2-enenitrile
KR102993352B1 (ko)	2019-12-20	2026-07-22	프린시피아 바이오파마, 인코퍼레이티드	2-[3-[4-아미노-3-(2-플루오로-4-페녹시-페닐)피라졸로[3,4-d]피리미딘-1-일]피페리딘-1-카르보닐]-4-메틸-4-[4-(옥세탄-3-일)피페라진-1-일]펜트-2-에네니트릴의 고체 형태
WO2021150723A1 (en)	2020-01-22	2021-07-29	Principia Biopharma Inc.	Crystalline forms of 2-[3-[4-amino-3-(2-fluoro-4-phenoxy-phenyl)-1h-pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carbonyl]-4-methyl-4-[4-(oxetan-3-yl)piperazin-1-yl]pent-2-enenitrile

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2664424A (en) *		1953-12-29		Dioxo-piperidines
GB1455687A (en) *	1972-12-28	1976-11-17	Aspro Nicholas Ltd	Pharmacologically active 3-phenyl-3-aminoalkyl-2,6-dioxo-hydro genated pyridines
FR2467200A1 (fr) *	1979-10-11	1981-04-17	Clin Midy	Derives du pyrrole actifs sur les troubles du rythme cardiovasculaire

1982
- 1982-11-08 FR FR8218706A patent/FR2535721A1/fr active Granted
1983
- 1983-10-28 ZA ZA838065A patent/ZA838065B/xx unknown
- 1983-10-31 IL IL70099A patent/IL70099A/xx unknown
- 1983-11-02 AU AU20898/83A patent/AU565519B2/en not_active Ceased
- 1983-11-04 GR GR72874A patent/GR78747B/el unknown
- 1983-11-04 PT PT77607A patent/PT77607B/pt not_active IP Right Cessation
- 1983-11-04 DE DE8383402142T patent/DE3366623D1/de not_active Expired
- 1983-11-04 EP EP83402142A patent/EP0110755B1/fr not_active Expired
- 1983-11-04 AT AT83402142T patent/ATE22561T1/de not_active IP Right Cessation
- 1983-11-04 IE IE2581/83A patent/IE56209B1/xx unknown
- 1983-11-05 SU SU833661804A patent/SU1333237A3/ru active
- 1983-11-07 MA MA20168A patent/MA19948A1/fr unknown
- 1983-11-07 NZ NZ206177A patent/NZ206177A/en unknown
- 1983-11-07 DD DD83270121A patent/DD229402A5/de not_active IP Right Cessation
- 1983-11-07 NO NO834057A patent/NO159852C/no unknown
- 1983-11-07 DD DD83270120A patent/DD229407A5/de not_active IP Right Cessation
- 1983-11-07 DD DD83256411A patent/DD219770A5/de not_active IP Right Cessation
- 1983-11-08 CS CS838220A patent/CS244681B2/cs unknown
- 1983-11-08 PH PH29800A patent/PH20421A/en unknown
- 1983-11-08 ES ES527091A patent/ES8406070A1/es not_active Expired
- 1983-11-08 YU YU02211/83A patent/YU221183A/xx unknown
- 1983-11-08 CA CA000440675A patent/CA1221967A/en not_active Expired
- 1983-11-08 FI FI834087A patent/FI79536C/fi not_active IP Right Cessation
- 1983-11-08 JP JP58209772A patent/JPS59161377A/ja active Pending
- 1983-11-08 PL PL1983244462A patent/PL139946B1/pl unknown
- 1983-11-08 KR KR1019830005288A patent/KR900006721B1/ko not_active Expired
- 1983-11-08 OA OA58153A patent/OA07582A/xx unknown
- 1983-11-08 PL PL1983249749A patent/PL140992B1/pl unknown
- 1983-11-08 DK DK511383A patent/DK511383A/da not_active Application Discontinuation
- 1983-11-08 PL PL1983249750A patent/PL140021B1/pl unknown
- 1983-11-08 HU HU833827A patent/HU191494B/hu not_active IP Right Cessation
1984
- 1984-09-06 SU SU843786907A patent/SU1316558A3/ru active
- 1984-09-06 SU SU843786916A patent/SU1333238A3/ru active
1985
- 1985-11-26 YU YU01841/85A patent/YU184185A/xx unknown
- 1985-11-26 YU YU01842/85A patent/YU184285A/xx unknown
1986
- 1986-03-10 US US06/838,255 patent/US4721710A/en not_active Expired - Fee Related
1989
- 1989-01-11 SG SG19/89A patent/SG1989G/en unknown

Also Published As

Publication number	Publication date
CA1221967A (en)	1987-05-19
ES527091A0 (es)	1984-07-01
EP0110755A1 (fr)	1984-06-13
FI79536C (fi)	1990-01-10
GR78747B (cs)	1984-10-02
NO159852C (no)	1989-02-15
PT77607B (fr)	1986-03-18
ES8406070A1 (es)	1984-07-01
CS244681B2 (en)	1986-08-14
IE56209B1 (en)	1991-05-22
AU565519B2 (en)	1987-09-17
KR840006641A (ko)	1984-12-01
US4721710A (en)	1988-01-26
OA07582A (fr)	1985-03-31
PH20421A (en)	1987-01-05
ZA838065B (en)	1984-06-27
DD219770A5 (de)	1985-03-13
YU221183A (en)	1986-06-30
SU1333238A3 (ru)	1987-08-23
ATE22561T1 (de)	1986-10-15
PL140992B1 (en)	1987-06-30
AU2089883A (en)	1984-05-17
DK511383A (da)	1984-05-09
FR2535721A1 (fr)	1984-05-11
FI834087L (fi)	1984-05-09
YU184185A (en)	1986-06-30
PT77607A (fr)	1983-12-01
HU191494B (en)	1987-02-27
NO159852B (no)	1988-11-07
PL249749A1 (en)	1985-03-12
FI834087A0 (fi)	1983-11-08
NO834057L (no)	1984-05-09
FR2535721B1 (cs)	1985-05-17
IL70099A0 (en)	1984-01-31
JPS59161377A (ja)	1984-09-12
SG1989G (en)	1989-06-02
KR900006721B1 (ko)	1990-09-20
DK511383D0 (da)	1983-11-08
SU1333237A3 (ru)	1987-08-23
PL140021B1 (en)	1987-03-31
IL70099A (en)	1987-10-20
YU184285A (en)	1986-06-30
EP0110755B1 (fr)	1986-10-01
PL249750A1 (en)	1985-03-12
PL139946B1 (en)	1987-03-31
IE832581L (en)	1984-05-08
PL244462A1 (en)	1985-02-13
NZ206177A (en)	1985-11-08
SU1316558A3 (ru)	1987-06-07
FI79536B (fi)	1989-09-29
DE3366623D1 (en)	1986-11-06
DD229407A5 (de)	1985-11-06
MA19948A1 (fr)	1984-07-01

Legal Events

Date	Code	Title	Description
1997-08-14	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
DE1695556C3 (de)	1981-06-25	3-Alkyl-1,2,3,4,4a,9-hexahydropyrazino[1,2-f]morphanthridinderivate
DE2558501C2 (cs)	1987-07-16
DE69107250T2 (de)	1995-09-21	Neue 4-Aminobuttersäurederivate, Verfahren zu ihrer Herstellung und diese enthaltende Arzneizubereitungen.
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DD227963A5 (de)	1985-10-02	Verfahren zur herstellung von 1-benzyl-aminoalkyl-pyrrolidinone
EP0047923B1 (de)	1984-05-09	Isochinolinderivate, Verfahren zu ihrer Herstellung und sie enthaltende pharmazeutische Zubereitungen
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DD219770A5 (de)	1985-03-13	Verfahren zur herstellung von piperidindion-derivaten
DE69627344T2 (de)	2003-12-04	N-(2,4-dioxo-2,3,4,5-tetrahydro-1h-1,5-benzodiazepin-3-yl)-3-amide
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DE69002338T2 (de)	1993-12-16	Pyrrolidin-Derivate und ihre pharmazeutische Verwendung.
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DE2007345A1 (de)	1970-09-17	Neue substituierte Hexahydroimidazochinoline und deren Säureanlagerungssalze
DE68905363T2 (de)	1993-08-05	Heterotetracyclische laktamderivate, verfahren zu ihrer herstellung und pharmazeutische zubereitungen, die sie enthalten.
DE3723648A1 (de)	1989-01-26	Indol-derivate, ihre herstellung und sie enthaltende arzneimittel
DD205682A5 (de)	1984-01-04	Verfahren zur herstellung von (-)-2-(1-(2,6-dichlorphenoxy)-ethyl)-1,3-diazacyclopent-2-en und seinen salzen
DE2359816C2 (cs)	1987-08-27
EP0266336B1 (de)	1991-05-15	Neue 1-/ 3-(2-Dialkylaminoäthoxy)-2-thienyl/-3-phenyl-1-propanone und ihre Säureadditionssalze und Verfahren zu deren Herstellung und sie enthaltende pharmazeutische Zusammensetzungen
DD153549A5 (de)	1982-01-13	Verfahren zur herstellung von pyridinderivaten
DE3813416A1 (de)	1989-11-02	3,4-dihydroxypyrrolidin-2-on-derivate, verfahren zu ihrer herstellung, diese enthaltende mittel und ihre verwendung sowie die bei der herstellung anfallenden neuen zwischenprodukte
DE2023829C3 (de)	1979-06-21	Kernsubstituierte 3-Phenoxy-lphenoxyalkyl-amino-propan-2-oIe, Verfahren zu ihrer Herstellung sowie Arzneimittel
DD231567A5 (de)	1986-01-02	Verfahren zur herstellung von gamma-butyrolacton-derivaten, die als myocard-schutz eine antiarrhythmische wirkung aufweisen
DE69632206T2 (de)	2005-04-28	(2-piperidin-1-yl-4-substituierte)-4-amino-2-chinazolin-derivate mit antihypertensiver wirkung, verfahren zu ihrer herstellung und ihrem pharmazeutischen gebrauch
EP0269985A2 (de)	1988-06-08	Neue 1-Aryloxy-3-amino-2-propanole, ihre Herstellung und Verwendung
CH615181A5 (en)	1980-01-15	Process for the preparation of novel ergolene derivatives