GB974711A - Improved 1-aryl-ªÏ-(4-alkoxy-4-arylpiperidino) derivatives of 1-alkanols and 1-alkanones - Google Patents
Improved 1-aryl-ªÏ-(4-alkoxy-4-arylpiperidino) derivatives of 1-alkanols and 1-alkanonesInfo
- Publication number
- GB974711A GB974711A GB10904/62A GB1090462A GB974711A GB 974711 A GB974711 A GB 974711A GB 10904/62 A GB10904/62 A GB 10904/62A GB 1090462 A GB1090462 A GB 1090462A GB 974711 A GB974711 A GB 974711A
- Authority
- GB
- United Kingdom
- Prior art keywords
- prepared
- phenyl
- aryl
- alkoxy
- tolyl
- 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
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 4
- -1 methoxy phenyl Chemical group 0.000 abstract 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- 238000010438 heat treatment Methods 0.000 abstract 3
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 abstract 3
- KQKFQBTWXOGINC-UHFFFAOYSA-N 4-phenylpiperidin-4-ol Chemical compound C=1C=CC=CC=1C1(O)CCNCC1 KQKFQBTWXOGINC-UHFFFAOYSA-N 0.000 abstract 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 abstract 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 abstract 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 abstract 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 abstract 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 abstract 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract 2
- 125000001475 halogen functional group Chemical group 0.000 abstract 2
- 229910000042 hydrogen bromide Inorganic materials 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- LHRYYSNFHJCZDT-UHFFFAOYSA-N 4-(4-methylphenyl)-1,2,3,6-tetrahydropyridine Chemical compound C1=CC(C)=CC=C1C1=CCNCC1 LHRYYSNFHJCZDT-UHFFFAOYSA-N 0.000 abstract 1
- ROVFPVLWAFHGKT-UHFFFAOYSA-N 4-bromo-4-phenylpiperidine;hydrobromide Chemical compound [Br-].C=1C=CC=CC=1C1(Br)CC[NH2+]CC1 ROVFPVLWAFHGKT-UHFFFAOYSA-N 0.000 abstract 1
- PPXQKVKQJDWZFN-UHFFFAOYSA-N 4-methoxy-4-phenylpiperidin-1-ium;chloride Chemical compound Cl.C=1C=CC=CC=1C1(OC)CCNCC1 PPXQKVKQJDWZFN-UHFFFAOYSA-N 0.000 abstract 1
- OMPXTQYWYRWWPH-UHFFFAOYSA-N 4-phenyl-1,2,3,6-tetrahydropyridine Chemical compound C1NCCC(C=2C=CC=CC=2)=C1 OMPXTQYWYRWWPH-UHFFFAOYSA-N 0.000 abstract 1
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 abstract 1
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Natural products CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 abstract 1
- FNOWGQOGRAFLQP-UHFFFAOYSA-N Cl.C1(=CC=C(C=C1)N1CCC(CC1)OC)C Chemical compound Cl.C1(=CC=C(C=C1)N1CCC(CC1)OC)C FNOWGQOGRAFLQP-UHFFFAOYSA-N 0.000 abstract 1
- 239000007818 Grignard reagent Substances 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 abstract 1
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 abstract 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 abstract 1
- 150000008062 acetophenones Chemical class 0.000 abstract 1
- 235000019270 ammonium chloride Nutrition 0.000 abstract 1
- 229940125681 anticonvulsant agent Drugs 0.000 abstract 1
- 239000001961 anticonvulsive agent Substances 0.000 abstract 1
- 229960005070 ascorbic acid Drugs 0.000 abstract 1
- 235000010323 ascorbic acid Nutrition 0.000 abstract 1
- 239000011668 ascorbic acid Substances 0.000 abstract 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 125000001207 fluorophenyl group Chemical group 0.000 abstract 1
- 150000004795 grignard reagents Chemical class 0.000 abstract 1
- 229940093915 gynecological organic acid Drugs 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 abstract 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 abstract 1
- 150000007522 mineralic acids Chemical class 0.000 abstract 1
- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 abstract 1
- 150000007524 organic acids Chemical class 0.000 abstract 1
- 235000005985 organic acids Nutrition 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- 125000001544 thienyl group Chemical group 0.000 abstract 1
- 229930192474 thiophene Natural products 0.000 abstract 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 abstract 1
- 125000003944 tolyl group Chemical group 0.000 abstract 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 abstract 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
-
- 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
- C07D211/48—Oxygen atoms attached in position 4 having an acyclic carbon atom attached 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
- C07D211/40—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
- C07D211/68—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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/92—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with a hetero atom directly attached to the ring nitrogen atom
- C07D211/96—Sulfur atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US97423A US3122555A (en) | 1961-03-22 | 1961-03-22 | 1-aryl-omega-(4-alkoxy-4-arylpiperidino) derivatives of 1-alkanols and 1-alkanones |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB974711A true GB974711A (en) | 1964-11-11 |
Family
ID=22263264
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB10904/62A Expired GB974711A (en) | 1961-03-22 | 1962-03-21 | Improved 1-aryl-ªÏ-(4-alkoxy-4-arylpiperidino) derivatives of 1-alkanols and 1-alkanones |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3122555A (en, 2012) |
| BE (1) | BE615410A (en, 2012) |
| BR (1) | BR6237377D0 (en, 2012) |
| DE (1) | DE1545451A1 (en, 2012) |
| FR (1) | FR1797M (en, 2012) |
| GB (1) | GB974711A (en, 2012) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3965257A (en) * | 1972-01-28 | 1976-06-22 | Richardson-Merrell Inc. | Compositions and methods for the treatment of the symptoms of histamine induced allergic reactions |
| US4216325A (en) * | 1978-07-11 | 1980-08-05 | A. H. Robins Company, Inc. | 4-(p-Fluorobenzoyl)-1-[3-(p-fluorobenzoyl)propyl]piperidine |
| DE2950064A1 (de) * | 1979-12-13 | 1981-06-19 | Basf Ag, 6700 Ludwigshafen | Piperidinderivate von 3-hydroxythiophen-2-carbonsaeure und -estern, ihre herstellung und diese enthaltende pharmazeutische zubereitungen |
| GB8321157D0 (en) * | 1983-08-05 | 1983-09-07 | Fordonal Sa | Piperidine derivatives |
| US5272160A (en) * | 1989-05-17 | 1993-12-21 | Pfizer Inc | 2-piperidino-1-alkanol derivatives as antiischemic agents |
| WO1990014087A1 (en) * | 1989-05-17 | 1990-11-29 | Pfizer Inc. | 2-piperidino-1-alkanol derivatives as antiischemic agents |
| US5527912A (en) * | 1991-10-23 | 1996-06-18 | Pfizer Inc. | Intermediates for 2-piperidino-1-alkanol derivatives |
| US5710168A (en) * | 1991-10-23 | 1998-01-20 | Pfizer Inc. | 2-piperidino-1-alkanol derivatives as neuroprotective agents |
| EP0714292A4 (en) * | 1993-06-23 | 1996-10-09 | Cambridge Neuroscience Inc | SIGMA RECEPTOR LIGANDS AND THEIR USE |
| US6025355A (en) | 1997-05-19 | 2000-02-15 | Cambridge Neuroscience, Inc. | Pharmaceutically active compounds and methods of use |
| US6242198B1 (en) | 1996-07-25 | 2001-06-05 | Cambridge Neuroscience, Inc. | Methods of treatment of eye trauma and disorders |
| US6756389B2 (en) * | 1996-08-09 | 2004-06-29 | Cambridge Neuroscience, Inc. | Pharmaceutically active compounds and methods of use |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2962501A (en) * | 1956-09-19 | 1960-11-29 | Merck & Co Inc | 1-substituted propyl piperidines and processes of preparing same |
| US2932646A (en) * | 1957-08-30 | 1960-04-12 | Lakeside Lab Inc | Nu-amino-nitrogen containing heterocyclic compounds |
| US2973363A (en) * | 1959-03-26 | 1961-02-28 | Paul Adriaan J Janssen | 1-(2-thenoyl)alkyl-4-arylpiperidin-4-ols |
-
0
- BE BE615410D patent/BE615410A/xx unknown
-
1961
- 1961-03-22 US US97423A patent/US3122555A/en not_active Expired - Lifetime
-
1962
- 1962-03-20 DE DE19621545451 patent/DE1545451A1/de active Pending
- 1962-03-21 GB GB10904/62A patent/GB974711A/en not_active Expired
- 1962-03-21 FR FR891806A patent/FR1797M/fr active Active
- 1962-03-22 BR BR137377/62A patent/BR6237377D0/pt unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BR6237377D0 (pt) | 1973-05-17 |
| DE1545451A1 (de) | 1969-05-22 |
| BE615410A (en, 2012) | |
| US3122555A (en) | 1964-02-25 |
| FR1797M (fr) | 1963-04-29 |
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