CA1095048A - 2,2-diphenyl-5-(4-substituted-piperidino)-3-trans- pentenenitriles - Google Patents
2,2-diphenyl-5-(4-substituted-piperidino)-3-trans- pentenenitrilesInfo
- Publication number
- CA1095048A CA1095048A CA272,322A CA272322A CA1095048A CA 1095048 A CA1095048 A CA 1095048A CA 272322 A CA272322 A CA 272322A CA 1095048 A CA1095048 A CA 1095048A
- Authority
- CA
- Canada
- Prior art keywords
- diphenyl
- trans
- pentenenitrile
- phenylpiperidino
- formula
- 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
- 150000001875 compounds Chemical class 0.000 claims abstract description 31
- -1 4-substituted piperidine Chemical class 0.000 claims abstract description 11
- 238000000034 method Methods 0.000 claims description 22
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- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- KFZGRZNOAFOEBM-XDHOZWIPSA-N ethyl 1-[(e)-4-cyano-4,4-diphenylbut-2-enyl]-4-phenylpiperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)(C=2C=CC=CC=2)CCN1C\C=C\C(C#N)(C=1C=CC=CC=1)C1=CC=CC=C1 KFZGRZNOAFOEBM-XDHOZWIPSA-N 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000001246 bromo group Chemical group Br* 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- QKHMFBKXTNQCTM-UHFFFAOYSA-N norpethidine Chemical compound C=1C=CC=CC=1C1(C(=O)OCC)CCNCC1 QKHMFBKXTNQCTM-UHFFFAOYSA-N 0.000 claims description 3
- MTMAGCJZJKAGNG-LICLKQGHSA-N (e)-5-(4-hydroxy-4-phenylpiperidin-1-yl)-2,2-diphenylpent-3-enenitrile Chemical compound C1CC(O)(C=2C=CC=CC=2)CCN1C\C=C\C(C#N)(C=1C=CC=CC=1)C1=CC=CC=C1 MTMAGCJZJKAGNG-LICLKQGHSA-N 0.000 claims description 2
- KQKFQBTWXOGINC-UHFFFAOYSA-N 4-phenylpiperidin-4-ol Chemical compound C=1C=CC=CC=1C1(O)CCNCC1 KQKFQBTWXOGINC-UHFFFAOYSA-N 0.000 claims description 2
- 125000002346 iodo group Chemical group I* 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- VGGOMVPLBPAOQR-KPKJPENVSA-N (e)-5-bromo-2,2-diphenylpent-3-enenitrile Chemical compound C=1C=CC=CC=1C(C#N)(/C=C/CBr)C1=CC=CC=C1 VGGOMVPLBPAOQR-KPKJPENVSA-N 0.000 claims 2
- CRFAKUXUEFBXMO-LICLKQGHSA-N 1-[(e)-4-cyano-4,4-diphenylbut-2-enyl]-4-phenylpiperidine-4-carboxylic acid Chemical compound C1CC(C(=O)O)(C=2C=CC=CC=2)CCN1C\C=C\C(C#N)(C=1C=CC=CC=1)C1=CC=CC=C1 CRFAKUXUEFBXMO-LICLKQGHSA-N 0.000 claims 2
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- 235000010355 mannitol Nutrition 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- CQDGTJPVBWZJAZ-UHFFFAOYSA-N monoethyl carbonate Chemical compound CCOC(O)=O CQDGTJPVBWZJAZ-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000013021 overheating Methods 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 230000003389 potentiating effect Effects 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
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000036647 reaction Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000012177 spermaceti Substances 0.000 description 1
- 229940084106 spermaceti Drugs 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 229940078499 tricalcium phosphate Drugs 0.000 description 1
- 229910000391 tricalcium phosphate Inorganic materials 0.000 description 1
- 235000019731 tricalcium phosphate Nutrition 0.000 description 1
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical class [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- 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
- C07D211/06—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 no double bonds between ring members or between ring members and non-ring members
- C07D211/08—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 no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/10—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 no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
- C07D211/14—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 no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/12—Antidiarrhoeals
-
- 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
- C07D211/06—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 no double bonds between ring members or between ring members and non-ring members
- C07D211/36—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 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
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/52—Oxygen atoms attached in position 4 having an aryl radical as the second substituent in position 4
-
- 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
- C07D211/06—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 no double bonds between ring members or between ring members and non-ring members
- C07D211/36—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 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
- C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D211/62—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4
- C07D211/64—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4 having an aryl radical as the second substituent in position 4
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/660,205 US4002618A (en) | 1976-02-23 | 1976-02-23 | 2,2-Diphenyl-5-(4-substituted-piperidino)-3-trans-pentenenitriles |
| US660,205 | 1991-02-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1095048A true CA1095048A (en) | 1981-02-03 |
Family
ID=24648578
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA272,322A Expired CA1095048A (en) | 1976-02-23 | 1977-02-22 | 2,2-diphenyl-5-(4-substituted-piperidino)-3-trans- pentenenitriles |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4002618A (cg-RX-API-DMAC10.html) |
| JP (1) | JPS52125172A (cg-RX-API-DMAC10.html) |
| CA (1) | CA1095048A (cg-RX-API-DMAC10.html) |
| DE (1) | DE2707520A1 (cg-RX-API-DMAC10.html) |
| FR (1) | FR2342964A1 (cg-RX-API-DMAC10.html) |
| GB (1) | GB1526382A (cg-RX-API-DMAC10.html) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1332236C (en) * | 1985-10-11 | 1994-10-04 | Lourens Wals | ,--diaryl-4-aryl-4-hydroxy-1-piperidinebutanamide, n-oxides |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1129955A (en) * | 1966-03-03 | 1968-10-09 | Wyeth John & Brother Ltd | Unsaturated nitriles and esters and derivatives thereof |
| US3539579A (en) * | 1967-11-22 | 1970-11-10 | Janssen Pharm | 1 - (3 - cyano - 3,3 - diphenyl - propyl) - 4- phenyl - piperidine - 4 - carboxylic acid esters |
| GB1356117A (en) * | 1970-12-16 | 1974-06-12 | Searle & Co | 1-3-cyano-3,3-diphenylpropyl-4-phenylpiperidine-4-carboxylic acid derivatives |
| US3847926A (en) * | 1972-07-20 | 1974-11-12 | Searle & Co | Process for the production of diphenoxylate,its derivatives and its salts using an aqueous dmf solvent system |
| US3790581A (en) * | 1972-08-17 | 1974-02-05 | Searle & Co | N-(1-(3-cyano-3,3-bis(optionally substituted phenyl)propyl)-4-phenylpiperidine-4-carbonyloxy)succinimides |
-
1976
- 1976-02-23 US US05/660,205 patent/US4002618A/en not_active Expired - Lifetime
-
1977
- 1977-02-22 GB GB7498/77A patent/GB1526382A/en not_active Expired
- 1977-02-22 DE DE19772707520 patent/DE2707520A1/de not_active Withdrawn
- 1977-02-22 CA CA272,322A patent/CA1095048A/en not_active Expired
- 1977-02-23 JP JP1908577A patent/JPS52125172A/ja active Pending
- 1977-02-23 FR FR7705297A patent/FR2342964A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| DE2707520A1 (de) | 1977-08-25 |
| US4002618A (en) | 1977-01-11 |
| FR2342964B1 (cg-RX-API-DMAC10.html) | 1978-11-17 |
| FR2342964A1 (fr) | 1977-09-30 |
| GB1526382A (en) | 1978-09-27 |
| JPS52125172A (en) | 1977-10-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry | ||
| MKEX | Expiry |
Effective date: 19980203 |