WO1984002906A1 - New amino derivatives of 2- adn-(2,2,5,5-tetramethyl-3-pyrrolin-3-carbonyl) bd - Google Patents
New amino derivatives of 2- adn-(2,2,5,5-tetramethyl-3-pyrrolin-3-carbonyl) bd Download PDFInfo
- Publication number
- WO1984002906A1 WO1984002906A1 PCT/HU1984/000004 HU8400004W WO8402906A1 WO 1984002906 A1 WO1984002906 A1 WO 1984002906A1 HU 8400004 W HU8400004 W HU 8400004W WO 8402906 A1 WO8402906 A1 WO 8402906A1
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- WO
- WIPO (PCT)
- Prior art keywords
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- eine
- die
- mit
- Prior art date
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- 150000001412 amines Chemical class 0.000 title abstract 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 2
- 229910052763 palladium Inorganic materials 0.000 claims 1
- 125000003917 carbamoyl group Chemical class [H]N([H])C(*)=O 0.000 abstract description 4
- 125000003545 alkoxy group Chemical group 0.000 abstract description 2
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 229910052757 nitrogen Inorganic materials 0.000 abstract 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 abstract 2
- 125000004429 atom Chemical group 0.000 abstract 2
- 229910052799 carbon Inorganic materials 0.000 abstract 2
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 2
- 125000003277 amino group Chemical group 0.000 abstract 1
- 230000003288 anthiarrhythmic effect Effects 0.000 abstract 1
- 239000003416 antiarrhythmic agent Substances 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000004104 aryloxy group Chemical group 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 239000000825 pharmaceutical preparation Substances 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 230000009466 transformation Effects 0.000 abstract 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- 239000000243 solution Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- UYBWIEGTWASWSR-UHFFFAOYSA-N 1,3-diaminopropan-2-ol Chemical compound NCC(O)CN UYBWIEGTWASWSR-UHFFFAOYSA-N 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 5
- XFSBVAOIAHNAPC-UHFFFAOYSA-N Aconitin Natural products CCN1CC(C(CC2OC)O)(COC)C3C(OC)C(C(C45)(OC(C)=O)C(O)C6OC)C1C32C4CC6(O)C5OC(=O)C1=CC=CC=C1 XFSBVAOIAHNAPC-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 208000000418 Premature Cardiac Complexes Diseases 0.000 description 3
- XFSBVAOIAHNAPC-NPVHKAFCSA-N aconitin Chemical compound O([C@H]1[C@]2(O)C[C@H]3[C@@]45[C@H]6[C@@H]([C@@]([C@H]31)(OC(C)=O)[C@@H](O)[C@@H]2OC)[C@H](OC)[C@@H]4[C@]([C@@H](C[C@@H]5OC)O)(COC)CN6CC)C(=O)C1=CC=CC=C1 XFSBVAOIAHNAPC-NPVHKAFCSA-N 0.000 description 3
- 206010003119 arrhythmia Diseases 0.000 description 3
- 238000001802 infusion Methods 0.000 description 3
- SMSQRKIBWOTIMI-UHFFFAOYSA-N 3,5-dibromo-2,2,6,6-tetramethylpiperidin-4-one Chemical compound CC1(C)NC(C)(C)C(Br)C(=O)C1Br SMSQRKIBWOTIMI-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- LOUPRKONTZGTKE-LHHVKLHASA-N quinidine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@H]2[C@@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-LHHVKLHASA-N 0.000 description 2
- 229960001404 quinidine Drugs 0.000 description 2
- -1 Aethyl Chemical group 0.000 description 1
- 240000007124 Brassica oleracea Species 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 206010022998 Irritability Diseases 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- CODNYICXDISAEA-UHFFFAOYSA-N bromine monochloride Chemical compound BrCl CODNYICXDISAEA-UHFFFAOYSA-N 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229960004279 formaldehyde Drugs 0.000 description 1
- 235000019256 formaldehyde Nutrition 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- OETHQSJEHLVLGH-UHFFFAOYSA-N metformin hydrochloride Chemical compound Cl.CN(C)C(=N)N=C(N)N OETHQSJEHLVLGH-UHFFFAOYSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002861 ventricular Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member 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
-
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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
- C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Heart & Thoracic Surgery (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE8484900529T DE3473443D1 (en) | 1983-01-20 | 1984-01-20 | New amino derivatives of 2- (n-(2,2,5,5-tetramethyl-3-pyrrolin-or pyrrolidine-3-carbonyl)) |
| AT84900529T ATE36526T1 (de) | 1983-01-20 | 1984-01-20 | Neue 2- (n-(2,2,5,5-tetramethyl-3-pyrrolinbzw.pyrrolidin-3-carbonyl))-amino-derivate. |
| DK447284A DK166776B1 (da) | 1983-01-20 | 1984-09-19 | 2,2,5,5-tetramethyl(pyrrolin eller pyrrolidin)-3-yl-carbonylaminoderivater, fremgangsmaade til deres fremstilling og farmaceutiske praeparater indeholdende dem |
| FI843667A FI71127C (fi) | 1983-01-20 | 1984-09-19 | Foerfarande foer framstaellning av som hjaertlaekemedel anvaendbara 2,2,5,5-tetrametylpyrrolin- och -pyrrolidin-3-karboxylsyraamidderivat |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU83178A HU189214B (en) | 1983-01-20 | 1983-01-20 | Process for preparing pyrroline and pyrrolidine carboxamide derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO1984002906A1 true WO1984002906A1 (en) | 1984-08-02 |
Family
ID=10948332
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/HU1984/000004 WO1984002906A1 (en) | 1983-01-20 | 1984-01-20 | New amino derivatives of 2- adn-(2,2,5,5-tetramethyl-3-pyrrolin-3-carbonyl) bd |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4731376A (forum.php) |
| EP (1) | EP0134795B1 (forum.php) |
| JP (1) | JPS60500668A (forum.php) |
| DE (1) | DE3473443D1 (forum.php) |
| DK (1) | DK166776B1 (forum.php) |
| FI (1) | FI71127C (forum.php) |
| HU (1) | HU189214B (forum.php) |
| SU (1) | SU1333236A3 (forum.php) |
| WO (1) | WO1984002906A1 (forum.php) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998034609A1 (en) * | 1997-02-10 | 1998-08-13 | Icn Hungary R.T. | Cardioprotective products |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3473442D1 (de) * | 1983-01-21 | 1988-09-22 | Alkaloida Vegyeszeti Gyar | New alkyl diamine derivatives |
| US5047555A (en) * | 1988-12-13 | 1991-09-10 | Tanabe Seiyaku Co., Ltd. | 4-aminophenol derivatives and processes for preparing the same |
| TWI243162B (en) * | 2000-11-10 | 2005-11-11 | Taisho Pharmaceutical Co Ltd | Cyanopyrrolidine derivatives |
| US6827226B2 (en) * | 2002-12-09 | 2004-12-07 | Wmc Holdings Incorporated | Storage apparatus for sportboards with variable widths |
| WO2012028959A1 (en) | 2010-08-31 | 2012-03-08 | Pablo Villoslada | Agonists of neurotrophin receptors and their use as medicaments |
| CN107835802B (zh) | 2015-09-04 | 2022-04-22 | Dic株式会社 | 稳定剂化合物、液晶组合物和显示元件 |
| US10633590B2 (en) | 2015-09-04 | 2020-04-28 | Dic Corporation | Liquid crystal composition and liquid crystal display device including the same |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH336068A (de) * | 1955-04-06 | 1959-02-15 | Bofors Ab | Verfahren zur Herstellung von Amiden von N-Alkyl-piperidin-monocarbonsäuren oder N-Alkyl-pyrrolidin-a-monocarbonsäuren |
| US3299097A (en) * | 1963-04-29 | 1967-01-17 | Upjohn Co | 4-alkylhygric acid hydrazides |
| GB1057290A (en) * | 1962-12-17 | 1967-02-01 | Geigy Ag J R | New pyrrolidine derivatives |
| GB1160527A (en) * | 1965-10-18 | 1969-08-06 | Upjohn Co | Process for Producing Non-N-Alkylated Pyrrolidines and Substituted Pyrrolidines |
| US3624081A (en) * | 1967-02-15 | 1971-11-30 | Sterling Drug Inc | 1-acyl-2-ethylidenepyrrol-idine-3-carboxamides |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE109345C (forum.php) * | ||||
| DE109346C (forum.php) * | ||||
| US3020288A (en) * | 1962-02-06 | Hypotensive compounds | ||
| DE109347C (forum.php) * | ||||
| GB190004799A (en) * | 1900-03-13 | 1900-05-19 | George William Johnson | The Manufacture of Para-amidophenyl Glyoxylic Acid, its Substitution Products and Homologues. |
| GB983134A (en) * | 1962-06-13 | 1965-02-10 | American Cyanamid Co | Cyclic nitroxides and process for preparing same |
| US4111901A (en) * | 1977-06-06 | 1978-09-05 | Borg-Warner Corporation | Hindered five-membered nitrogen rings as polyolefin stabilizers |
| US4302383A (en) * | 1980-05-19 | 1981-11-24 | Borg-Warner Chemicals, Inc. | Stabilized olefin polymers |
-
1983
- 1983-01-20 HU HU83178A patent/HU189214B/hu not_active IP Right Cessation
-
1984
- 1984-01-20 JP JP59500631A patent/JPS60500668A/ja active Granted
- 1984-01-20 EP EP84900529A patent/EP0134795B1/de not_active Expired
- 1984-01-20 WO PCT/HU1984/000004 patent/WO1984002906A1/en active IP Right Grant
- 1984-01-20 DE DE8484900529T patent/DE3473443D1/de not_active Expired
- 1984-01-20 US US06/898,723 patent/US4731376A/en not_active Expired - Fee Related
- 1984-09-19 DK DK447284A patent/DK166776B1/da active
- 1984-09-19 FI FI843667A patent/FI71127C/fi not_active IP Right Cessation
- 1984-09-20 SU SU843800100A patent/SU1333236A3/ru active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH336068A (de) * | 1955-04-06 | 1959-02-15 | Bofors Ab | Verfahren zur Herstellung von Amiden von N-Alkyl-piperidin-monocarbonsäuren oder N-Alkyl-pyrrolidin-a-monocarbonsäuren |
| GB1057290A (en) * | 1962-12-17 | 1967-02-01 | Geigy Ag J R | New pyrrolidine derivatives |
| US3299097A (en) * | 1963-04-29 | 1967-01-17 | Upjohn Co | 4-alkylhygric acid hydrazides |
| GB1160527A (en) * | 1965-10-18 | 1969-08-06 | Upjohn Co | Process for Producing Non-N-Alkylated Pyrrolidines and Substituted Pyrrolidines |
| US3624081A (en) * | 1967-02-15 | 1971-11-30 | Sterling Drug Inc | 1-acyl-2-ethylidenepyrrol-idine-3-carboxamides |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998034609A1 (en) * | 1997-02-10 | 1998-08-13 | Icn Hungary R.T. | Cardioprotective products |
Also Published As
| Publication number | Publication date |
|---|---|
| DK447284D0 (da) | 1984-09-19 |
| FI71127B (fi) | 1986-08-14 |
| EP0134795B1 (de) | 1988-08-17 |
| SU1333236A3 (ru) | 1987-08-23 |
| FI843667A0 (fi) | 1984-09-19 |
| FI71127C (fi) | 1986-11-24 |
| DE3473443D1 (en) | 1988-09-22 |
| US4731376A (en) | 1988-03-15 |
| JPH0471067B2 (forum.php) | 1992-11-12 |
| HU189214B (en) | 1986-06-30 |
| DK447284A (da) | 1984-11-20 |
| DK166776B1 (da) | 1993-07-12 |
| EP0134795A1 (en) | 1985-03-27 |
| JPS60500668A (ja) | 1985-05-09 |
| FI843667L (fi) | 1984-09-19 |
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