IE35778L - 4 - [4 -(ó - hydroxybenzyl) piperidino] - 4'¹fluorobutylprophenone derivatives - Google Patents
4 - [4 -(ó - hydroxybenzyl) piperidino] - 4'¹fluorobutylprophenone derivativesInfo
- Publication number
- IE35778L IE35778L IE711361A IE136171A IE35778L IE 35778 L IE35778 L IE 35778L IE 711361 A IE711361 A IE 711361A IE 136171 A IE136171 A IE 136171A IE 35778 L IE35778 L IE 35778L
- Authority
- IE
- Ireland
- Prior art keywords
- phenyl
- followed
- substituted
- reduction
- fluorobutyrophenone
- Prior art date
Links
- 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 title 1
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000000468 ketone group Chemical group 0.000 abstract 2
- 238000006722 reduction reaction Methods 0.000 abstract 2
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 abstract 1
- MBNBAODMHRPUKN-UHFFFAOYSA-N 2-fluoro-1-phenylbutan-1-one Chemical class CCC(F)C(=O)C1=CC=CC=C1 MBNBAODMHRPUKN-UHFFFAOYSA-N 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 1
- 239000007818 Grignard reagent Substances 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 238000010531 catalytic reduction reaction Methods 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Chemical group 0.000 abstract 1
- 229910052731 fluorine Inorganic materials 0.000 abstract 1
- 239000011737 fluorine Chemical group 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000000546 pharmaceutical excipient Substances 0.000 abstract 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 abstract 1
- -1 phenyl Grignard reagent Chemical class 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- DUZLYYVHAOTWSF-UHFFFAOYSA-N phenyl(piperidin-4-yl)methanol Chemical class C=1C=CC=CC=1C(O)C1CCNCC1 DUZLYYVHAOTWSF-UHFFFAOYSA-N 0.000 abstract 1
- BGUWFUQJCDRPTL-UHFFFAOYSA-N pyridine-4-carbaldehyde Chemical compound O=CC1=CC=NC=C1 BGUWFUQJCDRPTL-UHFFFAOYSA-N 0.000 abstract 1
- GPHQHTOMRSGBNZ-UHFFFAOYSA-N pyridine-4-carbonitrile Chemical compound N#CC1=CC=NC=C1 GPHQHTOMRSGBNZ-UHFFFAOYSA-N 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 230000002936 tranquilizing effect Effects 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 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
- C07D211/08—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
- C07D211/18—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 substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/20—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 substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
- C07D211/22—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 substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
1314955 Fluorobutyrophenone derivatives RICHARDSON-MERRELL Inc 27 Oct 1971 [27 Nov 1970] 49942/71 Heading C2C Novel compounds of the Formula I wherein R is hydrogen, chlorine, bromine, fluorine, C 1-4 alkyl or alkoxy, C 1-3 alkylthio, trifluoro methyl, phenyl, or phenoxy and salts thereof may be prepared by (a) condensing an appropriately substituted α-phenyl 4-piperidinemethanol with a 4-halo-4<SP>1</SP>-fluorobutyrophenone or (b) condensing an appropriately substituted 4-piperidylphenone with a 2-(3- halopropyl)-2-(p-fluorophenyl)-dioxolane to give an α-phenyl-1-{3-[2-(p-fluorophenyl) dioxolan- 2-yl]} propyl piperidyl ketone, followed by reduction of the keto group to give an α-phenyl- 1 - { 3 - [2 - (pfluorophenyl) dioxolan - 2 - yl]}- propyl-4-piperidinemethanol followed by hydrolysis of the dioxolane ring to form a keto group. The intermediate substituted α-phenyl-4- piperidine methanols may be prepared by (a) reduction of the corresponding ketone, (b) reacting a substituted phenyl Grignard reagent with 4-pyridine carboxaldehyde or 4-cyanopyridine followed by catalytic reduction of the intermediate. Pharmaceutical compositions of the compounds I show tranquillizing activity when administered orally or parenterally with the usual excipients.
[GB1314955A]
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US9349570A | 1970-11-27 | 1970-11-27 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE35778L true IE35778L (en) | 1972-05-27 |
| IE35778B1 IE35778B1 (en) | 1976-05-26 |
Family
ID=22239276
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE1361/71A IE35778B1 (en) | 1970-11-27 | 1971-10-27 | 4-(4-(alpha-hydroxybenzyl)piperidino)-4'-fluorobutyrophenone derivatives |
Country Status (16)
| Country | Link |
|---|---|
| JP (1) | JPS5623985B2 (en) |
| BE (1) | BE775593A (en) |
| CA (1) | CA957376A (en) |
| CH (1) | CH562215A5 (en) |
| DE (1) | DE2158136C2 (en) |
| DK (1) | DK135895B (en) |
| ES (1) | ES397370A1 (en) |
| FR (1) | FR2115451B1 (en) |
| GB (1) | GB1314955A (en) |
| IE (1) | IE35778B1 (en) |
| IL (1) | IL38079A (en) |
| NL (1) | NL175411C (en) |
| NO (1) | NO135248C (en) |
| PH (1) | PH9306A (en) |
| SE (1) | SE369900B (en) |
| ZA (1) | ZA717147B (en) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE7409245L (en) * | 1973-07-19 | 1975-01-20 | Robins Co Inc A H | |
| US4246268A (en) * | 1979-02-09 | 1981-01-20 | Richardson-Merrell Inc. | Neuroleptic-4-(naphthylmethyl)piperidine derivatives |
| IE49998B1 (en) * | 1979-08-06 | 1986-01-22 | Merrell Dow Pharma | 4-(naphthalenyloxy)piperidine derivatives |
| US4284636A (en) * | 1979-09-04 | 1981-08-18 | Richardson-Merrell Inc. | Cinnamoylpiperidinobutyrophenone antipsychotic agents |
| US4283404A (en) * | 1979-09-04 | 1981-08-11 | Richardson-Merrell Inc. | Aroylethenylpiperidinobutyrophenone antipsychotic agents |
| ZA806501B (en) * | 1979-10-27 | 1981-10-28 | Richardson Merrell Inc | 4-(4-alkyl-aroyl-1-piperidino)butyrophenone antipsychotic agents |
| ZA864772B (en) * | 1985-07-02 | 1987-02-25 | Merrell Dow Pharma | Novel chemical compounds |
| US4783471A (en) * | 1985-07-02 | 1988-11-08 | Merrell Dow Pharmaceuticals Inc. | N-aralkyl piperidine methanol derivatives and the uses thereof |
| IL117149A0 (en) * | 1995-02-23 | 1996-06-18 | Schering Corp | Muscarinic antagonists |
| WO2006031764A2 (en) * | 2004-09-13 | 2006-03-23 | Bayer Cropscience Ag | Processes for prepating n-(substituted arylmethyl)-4-(disubstituted methyl)piperidines and intermediates |
-
1971
- 1971-10-26 ZA ZA717147A patent/ZA717147B/en unknown
- 1971-10-27 IE IE1361/71A patent/IE35778B1/en unknown
- 1971-10-27 GB GB4994271A patent/GB1314955A/en not_active Expired
- 1971-10-29 CA CA126,448A patent/CA957376A/en not_active Expired
- 1971-11-04 IL IL38079A patent/IL38079A/en unknown
- 1971-11-16 PH PH13014*UA patent/PH9306A/en unknown
- 1971-11-17 CH CH1670071A patent/CH562215A5/xx not_active IP Right Cessation
- 1971-11-18 JP JP9200371A patent/JPS5623985B2/ja not_active Expired
- 1971-11-19 BE BE775593A patent/BE775593A/en not_active IP Right Cessation
- 1971-11-24 NO NO4318/71A patent/NO135248C/no unknown
- 1971-11-24 SE SE15032/71A patent/SE369900B/xx unknown
- 1971-11-24 DE DE2158136A patent/DE2158136C2/en not_active Expired
- 1971-11-25 NL NLAANVRAGE7116194,A patent/NL175411C/en not_active IP Right Cessation
- 1971-11-26 DK DK582171AA patent/DK135895B/en not_active IP Right Cessation
- 1971-11-26 ES ES397370A patent/ES397370A1/en not_active Expired
- 1971-11-26 FR FR7142529A patent/FR2115451B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE2158136C2 (en) | 1982-11-18 |
| DK135895C (en) | 1977-12-12 |
| BE775593A (en) | 1972-03-16 |
| ES397370A1 (en) | 1974-05-16 |
| FR2115451A1 (en) | 1972-07-07 |
| PH9306A (en) | 1975-08-18 |
| IE35778B1 (en) | 1976-05-26 |
| IL38079A (en) | 1974-10-22 |
| NL175411C (en) | 1984-11-01 |
| NL7116194A (en) | 1972-05-30 |
| JPS5623985B2 (en) | 1981-06-03 |
| ZA717147B (en) | 1972-07-26 |
| CH562215A5 (en) | 1975-05-30 |
| DK135895B (en) | 1977-07-11 |
| SE369900B (en) | 1974-09-23 |
| CA957376A (en) | 1974-11-05 |
| GB1314955A (en) | 1973-04-26 |
| NL175411B (en) | 1984-06-01 |
| NO135248B (en) | 1976-11-29 |
| DE2158136A1 (en) | 1972-05-31 |
| FR2115451B1 (en) | 1975-02-07 |
| IL38079A0 (en) | 1972-01-27 |
| NO135248C (en) | 1977-03-09 |
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