CS203940B2 - Process for preparing aryloktahydropyridines - Google Patents
Process for preparing aryloktahydropyridines Download PDFInfo
- Publication number
- CS203940B2 CS203940B2 CS788854A CS885478A CS203940B2 CS 203940 B2 CS203940 B2 CS 203940B2 CS 788854 A CS788854 A CS 788854A CS 885478 A CS885478 A CS 885478A CS 203940 B2 CS203940 B2 CS 203940B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- hydrogen
- formula
- methyl
- trans
- pyrindine
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 38
- 150000003839 salts Chemical class 0.000 claims abstract description 23
- 239000002253 acid Substances 0.000 claims abstract description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 21
- 239000001257 hydrogen Substances 0.000 claims abstract description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 9
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 claims abstract description 8
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- 150000002431 hydrogen Chemical group 0.000 claims abstract description 7
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 22
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- 238000002360 preparation method Methods 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
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- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
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- PGSSVUIUCKDLDY-GJZGRUSLSA-N (4aR,7aR)-2-methyl-4a-phenyl-3,4,5,6,7,7a-hexahydro-1H-cyclopenta[c]pyridine Chemical compound C1([C@]23CCN(C[C@@H]2CCC3)C)=CC=CC=C1 PGSSVUIUCKDLDY-GJZGRUSLSA-N 0.000 claims 1
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- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- XLMALTXPSGQGBX-GCJKJVERSA-N dextropropoxyphene Chemical compound C([C@](OC(=O)CC)([C@H](C)CN(C)C)C=1C=CC=CC=1)C1=CC=CC=C1 XLMALTXPSGQGBX-GCJKJVERSA-N 0.000 description 1
- 229960004193 dextropropoxyphene Drugs 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 206010013663 drug dependence Diseases 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
- 229940093471 ethyl oleate Drugs 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002183 isoquinolinyl group Chemical class C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 210000003141 lower extremity Anatomy 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229960005181 morphine Drugs 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- GQPLMRYTRLFLPF-UHFFFAOYSA-N nitrous oxide Inorganic materials [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 1
- 239000012457 nonaqueous media Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 229940127240 opiate Drugs 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000002895 organic esters Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 208000027753 pain disease Diseases 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
- 229960005489 paracetamol Drugs 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
- HDOWRFHMPULYOA-UHFFFAOYSA-N piperidin-4-ol Chemical compound OC1CCNCC1 HDOWRFHMPULYOA-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 238000013223 sprague-dawley female rat Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 208000011117 substance-related disease Diseases 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 125000004417 unsaturated alkyl group Chemical group 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
-
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
- C07D211/68—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 one double bond between ring members or between a ring member and a non-ring member
- C07D211/70—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 one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pain & Pain Management (AREA)
- Public Health (AREA)
- Rheumatology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Hydrogenated Pyridines (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US86489977A | 1977-12-27 | 1977-12-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS203940B2 true CS203940B2 (en) | 1981-03-31 |
Family
ID=25344312
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS788854A CS203940B2 (en) | 1977-12-27 | 1978-12-22 | Process for preparing aryloktahydropyridines |
Country Status (24)
| Country | Link |
|---|---|
| EP (1) | EP0002937A1 (it) |
| JP (1) | JPS5498770A (it) |
| AR (1) | AR221352A1 (it) |
| AU (1) | AU4286678A (it) |
| BE (1) | BE872990A (it) |
| BG (1) | BG30927A3 (it) |
| CA (1) | CA1105026A (it) |
| CS (1) | CS203940B2 (it) |
| DD (1) | DD141156A5 (it) |
| DK (1) | DK577078A (it) |
| ES (1) | ES476385A1 (it) |
| FI (1) | FI783992A7 (it) |
| FR (1) | FR2413370A1 (it) |
| GB (1) | GB2010806A (it) |
| GR (1) | GR70349B (it) |
| IL (1) | IL56268A0 (it) |
| IT (1) | IT1101682B (it) |
| LU (1) | LU80719A1 (it) |
| NZ (1) | NZ189230A (it) |
| PL (1) | PL117572B1 (it) |
| PT (1) | PT68934A (it) |
| RO (1) | RO75805A (it) |
| SU (1) | SU841586A3 (it) |
| ZA (1) | ZA787156B (it) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4579952A (en) * | 1981-12-28 | 1986-04-01 | E. I. Du Pont De Nemours And Company | Intermediates for octahydrobenzofuro[3,2-e]isoquinolines |
| US4537963A (en) * | 1981-12-28 | 1985-08-27 | E. I. Du Pont De Nemours And Company | Intermediates for octahydrobenzofuro[3,2-E]isoquinolines |
| US4415736A (en) * | 1981-12-28 | 1983-11-15 | E. I. Du Pont De Nemours & Co. | Certain tetrahydropyridine intermediates |
| FR2617481B1 (fr) * | 1987-07-03 | 1989-11-10 | Roussel Uclaf | Nouveaux derives de la tetrahydropyridine, leur procede de preparation et les intermediaires de preparation, leur application comme medicaments et les compositions pharmaceutiques les renfermant |
| HUE028983T2 (en) | 2010-05-06 | 2017-01-30 | Vertex Pharma | Heterocyclic chromene-spirocyclic piperidine amides as ion channel modulators |
| HRP20160382T8 (hr) | 2011-02-02 | 2016-10-21 | Vertex Pharmaceuticals Incorporated | Pirolopirazin-spirociklični piperidin amidi kao modulatori ionskih kanala |
| CN103443105A (zh) | 2011-02-18 | 2013-12-11 | 沃泰克斯药物股份有限公司 | 作为离子通道调节剂的苯并二氢吡喃-螺环哌啶酰胺 |
| MX347982B (es) | 2011-03-14 | 2017-05-22 | Vertex Pharma | Morfolina-piperidina espirociclica-amidas como moduladores de canales ionicos. |
| AU2014287471C1 (en) * | 2013-07-10 | 2019-11-28 | Vertex Pharmaceuticals Incorporated | Fused piperidine amides as modulators of ion channels |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA734895B (en) * | 1972-07-20 | 1974-06-26 | Du Pont | Analgesigs and/or narcotic antagonists |
| DE2351599A1 (de) * | 1972-07-20 | 1974-01-31 | Du Pont | 4a-aryl-trans-decahydrochinoline und verfahren zu ihrer herstellung |
| PT67194B (en) * | 1976-11-02 | 1979-03-23 | Lilly Co Eli | Process for preparing 4a-aryl-octahydro-1h-2-pyrindines |
-
1978
- 1978-12-19 NZ NZ189230A patent/NZ189230A/xx unknown
- 1978-12-19 BG BG041785A patent/BG30927A3/xx unknown
- 1978-12-19 PT PT68934A patent/PT68934A/pt unknown
- 1978-12-19 PL PL1978211919A patent/PL117572B1/pl unknown
- 1978-12-20 RO RO7895989A patent/RO75805A/ro unknown
- 1978-12-20 AR AR274886A patent/AR221352A1/es active
- 1978-12-20 GR GR57949A patent/GR70349B/el unknown
- 1978-12-20 ZA ZA787156A patent/ZA787156B/xx unknown
- 1978-12-20 CA CA318,284A patent/CA1105026A/en not_active Expired
- 1978-12-21 IL IL56268A patent/IL56268A0/xx unknown
- 1978-12-21 GB GB7849437A patent/GB2010806A/en not_active Withdrawn
- 1978-12-21 FR FR7835977A patent/FR2413370A1/fr not_active Withdrawn
- 1978-12-21 EP EP78300879A patent/EP0002937A1/en not_active Withdrawn
- 1978-12-22 IT IT31268/78A patent/IT1101682B/it active
- 1978-12-22 BE BE1009211A patent/BE872990A/xx unknown
- 1978-12-22 CS CS788854A patent/CS203940B2/cs unknown
- 1978-12-22 DK DK577078A patent/DK577078A/da not_active Application Discontinuation
- 1978-12-22 AU AU42866/78A patent/AU4286678A/en active Pending
- 1978-12-22 LU LU80719A patent/LU80719A1/xx unknown
- 1978-12-25 JP JP16448778A patent/JPS5498770A/ja active Pending
- 1978-12-26 SU SU782701053A patent/SU841586A3/ru active
- 1978-12-27 ES ES476385A patent/ES476385A1/es not_active Expired
- 1978-12-27 DD DD78210204A patent/DD141156A5/de unknown
- 1978-12-27 FI FI783992A patent/FI783992A7/fi unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU4286678A (en) | 1979-07-05 |
| JPS5498770A (en) | 1979-08-03 |
| PL117572B1 (en) | 1981-08-31 |
| IL56268A0 (en) | 1979-03-12 |
| DK577078A (da) | 1979-06-28 |
| ES476385A1 (es) | 1979-11-16 |
| DD141156A5 (de) | 1980-04-16 |
| EP0002937A1 (en) | 1979-07-11 |
| ZA787156B (en) | 1980-08-27 |
| NZ189230A (en) | 1981-05-15 |
| GB2010806A (en) | 1979-07-04 |
| BE872990A (fr) | 1979-06-22 |
| FR2413370A1 (fr) | 1979-07-27 |
| PL211919A1 (pl) | 1979-09-10 |
| CA1105026A (en) | 1981-07-14 |
| PT68934A (en) | 1979-01-01 |
| BG30927A3 (bg) | 1981-09-15 |
| SU841586A3 (ru) | 1981-06-23 |
| RO75805A (ro) | 1981-02-28 |
| GR70349B (it) | 1982-09-23 |
| FI783992A7 (fi) | 1979-06-28 |
| LU80719A1 (fr) | 1979-04-13 |
| AR221352A1 (es) | 1981-01-30 |
| IT1101682B (it) | 1985-10-07 |
| IT7831268A0 (it) | 1978-12-22 |
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