GB1131534A - Novel piperidino-butyrophenones and a process for the manufacture thereof - Google Patents
Novel piperidino-butyrophenones and a process for the manufacture thereofInfo
- Publication number
- GB1131534A GB1131534A GB31596/67A GB3159667A GB1131534A GB 1131534 A GB1131534 A GB 1131534A GB 31596/67 A GB31596/67 A GB 31596/67A GB 3159667 A GB3159667 A GB 3159667A GB 1131534 A GB1131534 A GB 1131534A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- hydroxypiperidine
- give
- formula
- benzyl
- 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
- VFLPICJWFQLLSY-UHFFFAOYSA-N 1-phenyl-2-piperidin-1-ylbutan-1-one Chemical class C=1C=CC=CC=1C(=O)C(CC)N1CCCCC1 VFLPICJWFQLLSY-UHFFFAOYSA-N 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 4
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 abstract 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 2
- HDOWRFHMPULYOA-UHFFFAOYSA-N piperidin-4-ol Chemical compound OC1CCNCC1 HDOWRFHMPULYOA-UHFFFAOYSA-N 0.000 abstract 2
- 150000003839 salts Chemical group 0.000 abstract 2
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 abstract 1
- DPGVNSSUGNJERF-UHFFFAOYSA-N 1-benzyl-4-cyclopropylpiperidin-4-ol Chemical compound C(C1=CC=CC=C1)N1CCC(CC1)(O)C1CC1 DPGVNSSUGNJERF-UHFFFAOYSA-N 0.000 abstract 1
- SJZKULRDWHPHGG-UHFFFAOYSA-N 1-benzylpiperidin-4-one Chemical compound C1CC(=O)CCN1CC1=CC=CC=C1 SJZKULRDWHPHGG-UHFFFAOYSA-N 0.000 abstract 1
- AWNUCKUARQPKNM-UHFFFAOYSA-N 4-cyclohexylpiperidin-4-ol Chemical compound C1CCCCC1C1(O)CCNCC1 AWNUCKUARQPKNM-UHFFFAOYSA-N 0.000 abstract 1
- AHIDHDSSUAYXBC-UHFFFAOYSA-N 4-cyclopropylpiperidin-4-ol Chemical compound C1CC1C1(O)CCNCC1 AHIDHDSSUAYXBC-UHFFFAOYSA-N 0.000 abstract 1
- KQKFQBTWXOGINC-UHFFFAOYSA-N 4-phenylpiperidin-4-ol Chemical compound C=1C=CC=CC=1C1(O)CCNCC1 KQKFQBTWXOGINC-UHFFFAOYSA-N 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- -1 alkyl lithium Chemical compound 0.000 abstract 1
- 229940035676 analgesics Drugs 0.000 abstract 1
- 239000000730 antalgic agent Substances 0.000 abstract 1
- 239000002260 anti-inflammatory agent Substances 0.000 abstract 1
- 229940121363 anti-inflammatory agent Drugs 0.000 abstract 1
- 230000001754 anti-pyretic effect Effects 0.000 abstract 1
- 239000002221 antipyretic Substances 0.000 abstract 1
- 229940125716 antipyretic agent Drugs 0.000 abstract 1
- 239000002775 capsule Substances 0.000 abstract 1
- 238000005661 deetherification reaction Methods 0.000 abstract 1
- 239000000839 emulsion Substances 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 229910052744 lithium Inorganic materials 0.000 abstract 1
- YSQFBLFEYNOIBW-UHFFFAOYSA-N lithium;cyclopropane Chemical compound [Li+].C1C[CH-]1 YSQFBLFEYNOIBW-UHFFFAOYSA-N 0.000 abstract 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 229910003446 platinum oxide Inorganic materials 0.000 abstract 1
- 229940125723 sedative agent Drugs 0.000 abstract 1
- 239000000932 sedative agent Substances 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- 239000000725 suspension Substances 0.000 abstract 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
- C07D211/36—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
-
- 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
- C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
Abstract
1,131,534. Piperidino-butyrophenones. F. HOFFMANN-LA ROCHE & CO., A.G. 10 July, 1967 [11 July, 1966], No. 31596/67. Heading C2C. Novel compounds of the formula and their acid addition and quaternary salts where R 1 is C 1-7 alkyl, C 3-6 cycloalkyl, (C 3-6 cycloalkyl) - (C 1-7 alkyl), C 1-7 hydroxyalkyl or (C 1-7 alkoxy)C 1-7 alkyl, R 2 is acyl and X is halogen are prepared by reacting a 4-hydroxy piperidine of the formula with a compound of the formula where Y is a leaving group and then optionally subjecting the (C 1-7 alkoxy) C 1-7 alkyl group, if present, to ether cleavage to give a C 1-7 hydroxyalkyl group and optionally acylating the hydroxy group. The 4-hydroxypiperidines are made (a) by hydrogenating 4-hydroxy-4-phenylpiperidine in the presence of platinum oxide to give 4- cyclohexyl - 4 - hydroxypiperidine, (b) by reacting an alkyl lithium or cyclopropyl lithium with 1-benzyl-4-piperidone to give a 4-alkyl-1- benzyl - 4 - hydrorypiperidine or 1 - benzyl - 4 - cyclopropyl-4-hydroxypiperidine and then hydrogenating these compounds in the presence of palladium on charcoal to give 4-alkyl-4-hydroxypiperidine or 4 - cyclopropyl - 4 - hydroxypiperidine and (c) 1-benzy]-4-[3-(1,1-dimethylpropoxy)-propyl]-4-hydroxypiperidine is hydrogenated in the presence of palladium on charcoal to give 4-[3-(1,1-dimethylpropory)-propyl]- 4-hydroxypiperidine. Pharmaceutical compositions effective as analgesics, sedatives, antipyretics and anti-inflammatory agents comprise one of the novel compounds of the above formula or an acid addition or quaternary salt as the active ingredient and a carrier and are administered as tablets, dragÚes, capsules, solutions, suspensions or emulsions.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US56396266A | 1966-07-11 | 1966-07-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1131534A true GB1131534A (en) | 1968-10-23 |
Family
ID=24252613
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB31596/67A Expired GB1131534A (en) | 1966-07-11 | 1967-07-10 | Novel piperidino-butyrophenones and a process for the manufacture thereof |
Country Status (7)
| Country | Link |
|---|---|
| BE (1) | BE701114A (en) |
| DE (1) | DE1695194A1 (en) |
| ES (1) | ES342860A1 (en) |
| FR (1) | FR7229M (en) |
| GB (1) | GB1131534A (en) |
| GR (1) | GR36824B (en) |
| NL (1) | NL6709605A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4855307A (en) * | 1986-09-11 | 1989-08-08 | H. Lundbeck A/S | Acetic acid ester of haloperidol |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI52216C (en) * | 1969-07-16 | 1977-07-11 | Sumitomo Chemical Co | Process for the preparation of gamma-piperidinobutyrophenone derivatives. |
| JPS568318A (en) * | 1979-06-28 | 1981-01-28 | Janssen Pharmaceutica Nv | Non oral long acting composition of haloperidol and bromperidol derivative |
-
1967
- 1967-07-01 DE DE19671695194 patent/DE1695194A1/en active Pending
- 1967-07-07 FR FR113484A patent/FR7229M/fr not_active Expired
- 1967-07-08 GR GR670136824A patent/GR36824B/en unknown
- 1967-07-10 BE BE701114D patent/BE701114A/xx unknown
- 1967-07-10 GB GB31596/67A patent/GB1131534A/en not_active Expired
- 1967-07-10 ES ES342860A patent/ES342860A1/en not_active Expired
- 1967-07-11 NL NL6709605A patent/NL6709605A/xx unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4855307A (en) * | 1986-09-11 | 1989-08-08 | H. Lundbeck A/S | Acetic acid ester of haloperidol |
Also Published As
| Publication number | Publication date |
|---|---|
| GR36824B (en) | 1969-03-12 |
| BE701114A (en) | 1968-01-10 |
| NL6709605A (en) | 1968-01-12 |
| FR7229M (en) | 1969-09-01 |
| ES342860A1 (en) | 1968-09-01 |
| DE1695194A1 (en) | 1971-03-18 |
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