CA1096382A - PROCESSES FOR THE PREPARATION OF NEW ( ,-)-CIS-.alpha.- ¬3-(2,6-DIMETHYL-1-PIPERIDINYL)PROPYL|-.alpha.-PHENYL- 2-PYRIDINEMETHANOL COMPOUNDS - Google Patents
PROCESSES FOR THE PREPARATION OF NEW ( ,-)-CIS-.alpha.- ¬3-(2,6-DIMETHYL-1-PIPERIDINYL)PROPYL|-.alpha.-PHENYL- 2-PYRIDINEMETHANOL COMPOUNDSInfo
- Publication number
- CA1096382A CA1096382A CA297,176A CA297176A CA1096382A CA 1096382 A CA1096382 A CA 1096382A CA 297176 A CA297176 A CA 297176A CA 1096382 A CA1096382 A CA 1096382A
- Authority
- CA
- Canada
- Prior art keywords
- cis
- alpha
- acid
- dimethyl
- propyl
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims abstract description 15
- 238000002360 preparation method Methods 0.000 title description 7
- OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 36
- 150000003839 salts Chemical class 0.000 claims abstract description 22
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims abstract description 12
- GCSHUYKULREZSJ-UHFFFAOYSA-N phenyl(pyridin-2-yl)methanone Chemical compound C=1C=CC=NC=1C(=O)C1=CC=CC=C1 GCSHUYKULREZSJ-UHFFFAOYSA-N 0.000 claims abstract description 6
- JDOZOOBCADNBIJ-UHFFFAOYSA-N lithium;2h-pyridin-2-ide Chemical compound [Li+].C1=CC=N[C-]=C1 JDOZOOBCADNBIJ-UHFFFAOYSA-N 0.000 claims abstract description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 17
- 239000012458 free base Substances 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 230000003301 hydrolyzing effect Effects 0.000 claims 3
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- 239000003416 antiarrhythmic agent Substances 0.000 abstract description 4
- 239000008194 pharmaceutical composition Substances 0.000 abstract description 4
- 206010003119 arrhythmia Diseases 0.000 abstract description 3
- 239000002831 pharmacologic agent Substances 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
- 239000000203 mixture Substances 0.000 description 24
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- -1 piperidine compound Chemical class 0.000 description 6
- 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 6
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- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
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- SDGKUVSVPIIUCF-KNVOCYPGSA-N (2r,6s)-2,6-dimethylpiperidine Chemical compound C[C@H]1CCC[C@@H](C)N1 SDGKUVSVPIIUCF-KNVOCYPGSA-N 0.000 description 3
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- 229960004194 lidocaine Drugs 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- 235000019359 magnesium stearate Nutrition 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 239000003755 preservative agent Substances 0.000 description 3
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- RQFUZUMFPRMVDX-UHFFFAOYSA-N 3-Bromo-1-propanol Chemical compound OCCCBr RQFUZUMFPRMVDX-UHFFFAOYSA-N 0.000 description 2
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- 241000282472 Canis lupus familiaris Species 0.000 description 2
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- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
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- 229940001584 sodium metabisulfite Drugs 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 1
- 229940033663 thimerosal Drugs 0.000 description 1
- 235000012431 wafers Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000009637 wintergreen oil Substances 0.000 description 1
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
- C07D295/16—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
- C07D295/18—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 carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
-
- 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
- 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
- C07D295/08—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 substituted by singly bound oxygen or sulfur atoms
- C07D295/084—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 substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—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 substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/16—Radicals substituted by halogen atoms or nitro radicals
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (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)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/772,203 US4112103A (en) | 1976-04-15 | 1977-02-25 | Antiarrhythmic (+,-)-cis-α-[3-(2,6-dimethyl-1-piperidinyl)propyl]-α-phenyl-2-pyridinemethanols |
| US772,203 | 1977-02-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1096382A true CA1096382A (en) | 1981-02-24 |
Family
ID=25094280
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA297,176A Expired CA1096382A (en) | 1977-02-25 | 1978-02-17 | PROCESSES FOR THE PREPARATION OF NEW ( ,-)-CIS-.alpha.- ¬3-(2,6-DIMETHYL-1-PIPERIDINYL)PROPYL|-.alpha.-PHENYL- 2-PYRIDINEMETHANOL COMPOUNDS |
Country Status (11)
| Country | Link |
|---|---|
| JP (1) | JPS53105479A (en, 2012) |
| AT (1) | AT358040B (en, 2012) |
| BE (1) | BE864033A (en, 2012) |
| CA (1) | CA1096382A (en, 2012) |
| CH (1) | CH635095A5 (en, 2012) |
| DE (1) | DE2806654A1 (en, 2012) |
| DK (1) | DK143229C (en, 2012) |
| ES (1) | ES467100A1 (en, 2012) |
| FR (1) | FR2381761A1 (en, 2012) |
| GB (1) | GB1581096A (en, 2012) |
| PH (1) | PH13125A (en, 2012) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2818914B2 (ja) * | 1991-04-05 | 1998-10-30 | シャープ株式会社 | 多目的スチーム発生器 |
| CN116514770B (zh) * | 2023-05-09 | 2025-02-07 | 郑州大学 | 2-苄基吡啶高效制备吡美诺的方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE757408A (fr) * | 1969-10-13 | 1971-04-13 | Thomae Gmbh Dr K | Nouveaux butanols tertiaires a constituants basiques |
-
1978
- 1978-02-16 BE BE185237A patent/BE864033A/xx not_active IP Right Cessation
- 1978-02-16 DE DE19782806654 patent/DE2806654A1/de active Granted
- 1978-02-17 CA CA297,176A patent/CA1096382A/en not_active Expired
- 1978-02-17 ES ES467100A patent/ES467100A1/es not_active Expired
- 1978-02-17 CH CH177978A patent/CH635095A5/de not_active IP Right Cessation
- 1978-02-17 AT AT117078A patent/AT358040B/de not_active IP Right Cessation
- 1978-02-17 GB GB6493/78A patent/GB1581096A/en not_active Expired
- 1978-02-17 JP JP1665978A patent/JPS53105479A/ja active Granted
- 1978-02-17 PH PH20795A patent/PH13125A/en unknown
- 1978-02-17 FR FR7804568A patent/FR2381761A1/fr active Granted
- 1978-02-17 DK DK73278A patent/DK143229C/da not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| ES467100A1 (es) | 1978-11-01 |
| FR2381761A1 (fr) | 1978-09-22 |
| FR2381761B1 (en, 2012) | 1982-03-26 |
| DK143229B (da) | 1981-07-27 |
| CH635095A5 (en) | 1983-03-15 |
| AT358040B (de) | 1980-08-11 |
| ATA117078A (de) | 1980-01-15 |
| DE2806654A1 (de) | 1978-08-31 |
| DE2806654C2 (en, 2012) | 1987-07-16 |
| DK143229C (da) | 1981-11-30 |
| GB1581096A (en) | 1980-12-10 |
| JPS6257632B2 (en, 2012) | 1987-12-02 |
| PH13125A (en) | 1979-12-12 |
| JPS53105479A (en) | 1978-09-13 |
| DK73278A (da) | 1978-08-26 |
| BE864033A (fr) | 1978-06-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |