HU189214B - Process for preparing pyrroline and pyrrolidine carboxamide derivatives - Google Patents
Process for preparing pyrroline and pyrrolidine carboxamide derivatives Download PDFInfo
- Publication number
- HU189214B HU189214B HU83178A HU17883A HU189214B HU 189214 B HU189214 B HU 189214B HU 83178 A HU83178 A HU 83178A HU 17883 A HU17883 A HU 17883A HU 189214 B HU189214 B HU 189214B
- Authority
- HU
- Hungary
- Prior art keywords
- pct
- formula
- group
- substituted
- compounds
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title description 3
- RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical compound C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 title 1
- LCDCPQHFCOBUEF-UHFFFAOYSA-N pyrrolidine-1-carboxamide Chemical class NC(=O)N1CCCC1 LCDCPQHFCOBUEF-UHFFFAOYSA-N 0.000 title 1
- ZVJHJDDKYZXRJI-UHFFFAOYSA-N pyrroline Natural products C1CC=NC1 ZVJHJDDKYZXRJI-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 8
- 150000003839 salts Chemical class 0.000 claims abstract description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 5
- 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 claims description 3
- 238000005984 hydrogenation reaction Methods 0.000 claims description 3
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 230000003197 catalytic effect Effects 0.000 claims 1
- -1 2,6-dimethyl-phenyl Chemical group 0.000 abstract description 2
- 230000003288 anthiarrhythmic effect Effects 0.000 abstract description 2
- 230000000694 effects Effects 0.000 abstract description 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 2
- 239000001257 hydrogen Substances 0.000 abstract description 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 1
- 208000001953 Hypotension Diseases 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 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
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 208000021822 hypotensive Diseases 0.000 abstract 1
- 230000001077 hypotensive effect Effects 0.000 abstract 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- 239000000047 product Substances 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L magnesium sulphate Substances [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- UYBWIEGTWASWSR-UHFFFAOYSA-N 1,3-diaminopropan-2-ol Chemical compound NCC(O)CN UYBWIEGTWASWSR-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 230000000747 cardiac effect Effects 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 125000000950 dibromo group Chemical group Br* 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- ACFYUJLIWIDSFM-UHFFFAOYSA-N 2,2,5,5-tetramethyl-2,5-dihydro-1H-pyrrole-3-carboxamide Chemical compound CC1(C)NC(C)(C)C(C(N)=O)=C1 ACFYUJLIWIDSFM-UHFFFAOYSA-N 0.000 description 1
- FWPHQUJGZVELBK-UHFFFAOYSA-N 2,3-dihydropyrrole-1-carboxamide Chemical class NC(=O)N1CCC=C1 FWPHQUJGZVELBK-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000003416 antiarrhythmic agent Substances 0.000 description 1
- 229940053202 antiepileptics carboxamide derivative Drugs 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- JUGVRRPKIHNDEF-UHFFFAOYSA-N n-(3-amino-2-hydroxypropyl)-2,2,5,5-tetramethyl-1h-pyrrole-3-carboxamide Chemical compound CC1(C)NC(C)(C)C(C(=O)NCC(O)CN)=C1 JUGVRRPKIHNDEF-UHFFFAOYSA-N 0.000 description 1
- HEZPTJMNTYHYPV-UHFFFAOYSA-N n-(3-aminopropyl)-2,2,5,5-tetramethylpyrrolidine-3-carboxamide Chemical compound CC1(C)CC(C(=O)NCCCN)C(C)(C)N1 HEZPTJMNTYHYPV-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU83178A HU189214B (en) | 1983-01-20 | 1983-01-20 | Process for preparing pyrroline and pyrrolidine carboxamide derivatives |
| JP59500631A JPS60500668A (ja) | 1983-01-20 | 1984-01-20 | 心臓病治療用新規薬剤 |
| US06/898,723 US4731376A (en) | 1983-01-20 | 1984-01-20 | 2-(-(2,2,5,5-tetramethyl-3-pyrrolin-3-carbonyl))-amino derivatives |
| 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 |
| EP84900529A EP0134795B1 (de) | 1983-01-20 | 1984-01-20 | Neue 2- (n-(2,2,5,5-tetramethyl-3-pyrrolin-bzw.pyrrolidin-3-carbonyl))-amino-derivate |
| AT84900529T ATE36526T1 (de) | 1983-01-20 | 1984-01-20 | Neue 2- (n-(2,2,5,5-tetramethyl-3-pyrrolinbzw.pyrrolidin-3-carbonyl))-amino-derivate. |
| 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)) |
| 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 |
| 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 |
| SU843800100A SU1333236A3 (ru) | 1983-01-20 | 1984-09-20 | Способ получени производных пирролидина или их солей с неорганической кислотой |
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 |
|---|---|
| HU189214B true HU189214B (en) | 1986-06-30 |
Family
ID=10948332
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU83178A HU189214B (en) | 1983-01-20 | 1983-01-20 | Process for preparing pyrroline and pyrrolidine carboxamide derivatives |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4731376A (en:Method) |
| EP (1) | EP0134795B1 (en:Method) |
| JP (1) | JPS60500668A (en:Method) |
| DE (1) | DE3473443D1 (en:Method) |
| DK (1) | DK166776B1 (en:Method) |
| FI (1) | FI71127C (en:Method) |
| HU (1) | HU189214B (en:Method) |
| SU (1) | SU1333236A3 (en:Method) |
| WO (1) | WO1984002906A1 (en:Method) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1984002907A1 (en) * | 1983-01-21 | 1984-08-02 | 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 |
| HUP9700392A1 (hu) * | 1997-02-10 | 1999-09-28 | ICN Magyarország Részvénytársaság | Egy vagy két hatóanyagot tartalmazó kardioprotektív hatású gyógyszerkészítmények |
| 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 |
| HRP20160553T1 (hr) | 2010-08-31 | 2016-09-23 | Bionure Farma, S.L. | Agonisti receptora neurotrofina i njihova uporaba kao lijekova |
| JP6358398B2 (ja) | 2015-09-04 | 2018-07-18 | Dic株式会社 | 液晶組成物及びそれを使用した液晶表示素子 |
| WO2017038552A1 (ja) * | 2015-09-04 | 2017-03-09 | Dic株式会社 | 安定剤化合物、液晶組成物および表示素子 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE109345C (en:Method) * | ||||
| US3020288A (en) * | 1962-02-06 | Hypotensive compounds | ||
| DE109347C (en:Method) * | ||||
| DE109346C (en:Method) * | ||||
| GB190004799A (en) * | 1900-03-13 | 1900-05-19 | George William Johnson | The Manufacture of Para-amidophenyl Glyoxylic Acid, its Substitution Products and Homologues. |
| 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 |
| GB983134A (en) * | 1962-06-13 | 1965-02-10 | American Cyanamid Co | Cyclic nitroxides and process for preparing same |
| US3250771A (en) * | 1962-12-17 | 1966-05-10 | Geigy Chem Corp | 5-monocarbocyclic aryl-n-lower alkyl-2-pyrrolidine carboxylic acid, esters, amides and derivatives thereof |
| US3299097A (en) * | 1963-04-29 | 1967-01-17 | Upjohn Co | 4-alkylhygric acid hydrazides |
| US3313801A (en) * | 1965-10-18 | 1967-04-11 | Upjohn Co | Process for inhibiting n-alkylation of pyrrolidines and substituted pyrrolidines by microorganisms, and products produced thereby |
| US3624081A (en) * | 1967-02-15 | 1971-11-30 | Sterling Drug Inc | 1-acyl-2-ethylidenepyrrol-idine-3-carboxamides |
| 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 WO PCT/HU1984/000004 patent/WO1984002906A1/en active IP Right Grant
- 1984-01-20 US US06/898,723 patent/US4731376A/en not_active Expired - Fee Related
- 1984-01-20 DE DE8484900529T patent/DE3473443D1/de not_active Expired
- 1984-01-20 EP EP84900529A patent/EP0134795B1/de not_active Expired
- 1984-09-19 FI FI843667A patent/FI71127C/fi not_active IP Right Cessation
- 1984-09-19 DK DK447284A patent/DK166776B1/da active
- 1984-09-20 SU SU843800100A patent/SU1333236A3/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| FI843667L (fi) | 1984-09-19 |
| DK447284A (da) | 1984-11-20 |
| EP0134795A1 (en) | 1985-03-27 |
| US4731376A (en) | 1988-03-15 |
| EP0134795B1 (de) | 1988-08-17 |
| JPS60500668A (ja) | 1985-05-09 |
| JPH0471067B2 (en:Method) | 1992-11-12 |
| DK166776B1 (da) | 1993-07-12 |
| WO1984002906A1 (en) | 1984-08-02 |
| DK447284D0 (da) | 1984-09-19 |
| SU1333236A3 (ru) | 1987-08-23 |
| FI843667A0 (fi) | 1984-09-19 |
| FI71127B (fi) | 1986-08-14 |
| DE3473443D1 (en) | 1988-09-22 |
| FI71127C (fi) | 1986-11-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 | ||
| HPC4 | Succession in title of patentee |
Owner name: ICN ALKALOIDA MAGYARORSZAG RT., HU |
|
| HMM4 | Cancellation of final prot. due to non-payment of fee |