CA1071210A - Trans-hexahydro-pyrido-indole-2-alkanols,-alkanones,-alkanonitriles,-alkanoic acids and esters - Google Patents
Trans-hexahydro-pyrido-indole-2-alkanols,-alkanones,-alkanonitriles,-alkanoic acids and estersInfo
- Publication number
- CA1071210A CA1071210A CA275,677A CA275677A CA1071210A CA 1071210 A CA1071210 A CA 1071210A CA 275677 A CA275677 A CA 275677A CA 1071210 A CA1071210 A CA 1071210A
- Authority
- CA
- Canada
- Prior art keywords
- compound
- cycloalkyl
- produced
- formula
- trans
- 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
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- 150000007513 acids Chemical class 0.000 title claims 3
- 150000002148 esters Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 82
- 238000000034 method Methods 0.000 claims description 50
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims description 30
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 21
- 150000003839 salts Chemical class 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
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- 239000001257 hydrogen Substances 0.000 claims description 3
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- 229910052987 metal hydride Inorganic materials 0.000 claims 1
- 150000004681 metal hydrides Chemical class 0.000 claims 1
- 239000003176 neuroleptic agent Substances 0.000 abstract description 5
- 241001465754 Metazoa Species 0.000 abstract description 3
- 239000000543 intermediate Substances 0.000 abstract 1
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- 229910000041 hydrogen chloride Inorganic materials 0.000 description 23
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 21
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- UWTDFICHZKXYAC-UHFFFAOYSA-N boron;oxolane Chemical compound [B].C1CCOC1 UWTDFICHZKXYAC-UHFFFAOYSA-N 0.000 description 3
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- LBLSRDDHGILUJH-UHFFFAOYSA-N 4-(1h-indol-2-yl)butanoic acid Chemical compound C1=CC=C2NC(CCCC(=O)O)=CC2=C1 LBLSRDDHGILUJH-UHFFFAOYSA-N 0.000 description 2
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- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
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- 230000001419 dependent effect Effects 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
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- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
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- 230000005764 inhibitory process Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
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- 239000011630 iodine Chemical group 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 239000000644 isotonic solution Substances 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
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- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
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- FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
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- 230000020477 pH reduction Effects 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 150000002990 phenothiazines Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229950008882 polysorbate Drugs 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
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- 229910052700 potassium Inorganic materials 0.000 description 1
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- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
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- BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 1
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- MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 1
- 208000026451 salivation Diseases 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 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
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
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- 238000003756 stirring Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
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- 150000008163 sugars Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
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- 229940125725 tranquilizer Drugs 0.000 description 1
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- 239000008158 vegetable oil Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed 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
- A61P25/20—Hypnotics; Sedatives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Anesthesiology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biomedical Technology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US67511276A | 1976-04-08 | 1976-04-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1071210A true CA1071210A (en) | 1980-02-05 |
Family
ID=24709111
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA275,677A Expired CA1071210A (en) | 1976-04-08 | 1977-04-06 | Trans-hexahydro-pyrido-indole-2-alkanols,-alkanones,-alkanonitriles,-alkanoic acids and esters |
Country Status (28)
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE7702300L (sv) * | 1976-04-15 | 1977-10-16 | Endo Lab | Reduktionsforlopp |
| US4224329A (en) * | 1979-01-23 | 1980-09-23 | Pfizer Inc. | 2-Substituted-trans-5-aryl-2,3,4,4a,5,9b-hexahydro-1H-pyrido[4,3-b]indoles |
| US4252812A (en) * | 1977-05-23 | 1981-02-24 | Pfizer Inc. | 2-Substituted-trans-5-aryl-2,3,4,4a,5,9b-hexahydro-1H-pyrido[4,3-b]indoles |
| US4267331A (en) * | 1979-01-23 | 1981-05-12 | Pfizer Inc. | Process for the production of 2-substituted pyrido[4,3-b]-indoles |
| US4432978A (en) * | 1979-07-30 | 1984-02-21 | Pfizer Inc. | Hexahydro-trans-pyridoindole |
| US4352807A (en) * | 1979-07-30 | 1982-10-05 | Pfizer Inc. | Hexahydro-trans-pyridoindole neuroleptic agents |
| US4337250A (en) * | 1979-07-30 | 1982-06-29 | Pfizer Inc. | Hexahydro-trans- and tetrahydropyridoindole neuroleptic agents |
| US4431649A (en) * | 1979-07-30 | 1984-02-14 | Pfizer Inc. | Hexahydro-trans- and tetrahydropyridoindole neuroleptic agents |
| US4252811A (en) * | 1979-07-30 | 1981-02-24 | Pfizer Inc. | Hexahydro-trans-pyridoindole neuroleptic agents |
| US4431646A (en) * | 1979-07-30 | 1984-02-14 | Pfizer Inc. | Hexahydro-trans- and tetrahydropyridoindole neuroleptic agents |
| US4427679A (en) | 1981-01-16 | 1984-01-24 | Pfizer Inc. | Hexahydro-trans- and tetrahydropyridoindole neuroleptic agents |
| US5319087A (en) * | 1987-04-16 | 1994-06-07 | Eli Lilly And Company | Piperidine opioid antagonists |
| US4992450A (en) * | 1987-04-16 | 1991-02-12 | Eli Lilly And Company | Piperidine opioid antagonists |
| US4891379A (en) * | 1987-04-16 | 1990-01-02 | Kabushiki Kaisha Kobe Seikosho | Piperidine opioid antagonists |
| US5270328A (en) * | 1991-03-29 | 1993-12-14 | Eli Lilly And Company | Peripherally selective piperidine opioid antagonists |
| US5159081A (en) * | 1991-03-29 | 1992-10-27 | Eli Lilly And Company | Intermediates of peripherally selective n-carbonyl-3,4,4-trisubstituted piperidine opioid antagonists |
| US5250542A (en) * | 1991-03-29 | 1993-10-05 | Eli Lilly And Company | Peripherally selective piperidine carboxylate opioid antagonists |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH303833A (de) * | 1951-04-30 | 1954-12-15 | Bayer Ag | Verfahren zur Herstellung von Derivaten des Tetrahydro-y-carbolins. |
| JPS50126699A (cg-RX-API-DMAC10.html) * | 1974-03-20 | 1975-10-04 |
-
1977
- 1977-03-02 SE SE7702301A patent/SE7702301L/xx not_active Application Discontinuation
- 1977-04-06 GR GR53175A patent/GR63666B/el unknown
- 1977-04-06 PH PH19641A patent/PH13152A/en unknown
- 1977-04-06 ES ES457665A patent/ES457665A1/es not_active Expired
- 1977-04-06 NO NO771242A patent/NO771242L/no unknown
- 1977-04-06 AU AU24012/77A patent/AU516432B2/en not_active Expired
- 1977-04-06 FI FI771088A patent/FI62304C/fi not_active IP Right Cessation
- 1977-04-06 DE DE19772715355 patent/DE2715355A1/de not_active Withdrawn
- 1977-04-06 IE IE724/77A patent/IE45189B1/en unknown
- 1977-04-06 DK DK154877A patent/DK154877A/da not_active IP Right Cessation
- 1977-04-06 PT PT66407A patent/PT66407B/pt unknown
- 1977-04-06 SU SU772468108A patent/SU719503A3/ru active
- 1977-04-06 AT AT242377A patent/AT360533B/de not_active IP Right Cessation
- 1977-04-06 CA CA275,677A patent/CA1071210A/en not_active Expired
- 1977-04-06 AR AR267148A patent/AR218246A1/es active
- 1977-04-07 FR FR7710596A patent/FR2347365A1/fr active Granted
- 1977-04-07 CH CH446877A patent/CH633795A5/de not_active IP Right Cessation
- 1977-04-07 DD DD7700198299A patent/DD132015A5/xx unknown
- 1977-04-07 ZA ZA00772166A patent/ZA772166B/xx unknown
- 1977-04-07 NL NL7703898A patent/NL7703898A/xx not_active Application Discontinuation
- 1977-04-07 NZ NZ183824A patent/NZ183824A/xx unknown
- 1977-04-07 IL IL51840A patent/IL51840A/xx unknown
- 1977-04-08 JP JP3962477A patent/JPS52125197A/ja active Pending
- 1977-04-08 BE BE176568A patent/BE853422A/xx unknown
- 1977-04-08 HU HU77EO342A patent/HU176956B/hu unknown
- 1977-04-08 LU LU77091A patent/LU77091A1/xx unknown
- 1977-04-12 GB GB15071/77A patent/GB1572057A/en not_active Expired
- 1977-12-13 US US05/860,212 patent/US4141980A/en not_active Expired - Lifetime
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