IL29374A - Substituted 1-(4-oxo-4-phenyl-butyl)-piperidines - Google Patents
Substituted 1-(4-oxo-4-phenyl-butyl)-piperidinesInfo
- Publication number
- IL29374A IL29374A IL2937468A IL2937468A IL29374A IL 29374 A IL29374 A IL 29374A IL 2937468 A IL2937468 A IL 2937468A IL 2937468 A IL2937468 A IL 2937468A IL 29374 A IL29374 A IL 29374A
- Authority
- IL
- Israel
- Prior art keywords
- formula
- acid addition
- substituted
- compounds
- process according
- Prior art date
Links
- WLTFPYVGECWXFO-UHFFFAOYSA-N 1-phenyl-4-piperidin-1-ylbutan-1-one Chemical class C=1C=CC=CC=1C(=O)CCCN1CCCCC1 WLTFPYVGECWXFO-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- 229910001516 alkali metal iodide Inorganic materials 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 3
- 239000008101 lactose Substances 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 239000008107 starch Substances 0.000 description 3
- 235000019698 starch Nutrition 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- ROLMZTIHUMKEAI-UHFFFAOYSA-N 4,5-difluoro-2-hydroxybenzonitrile Chemical compound OC1=CC(F)=C(F)C=C1C#N ROLMZTIHUMKEAI-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 230000000202 analgesic effect Effects 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- FRKDEDBRSLDGIX-UHFFFAOYSA-N methanesulfonate;piperidin-1-ium Chemical compound CS([O-])(=O)=O.C1CC[NH2+]CC1 FRKDEDBRSLDGIX-UHFFFAOYSA-N 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000829 suppository Substances 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 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 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229940041476 lactose 100 mg Drugs 0.000 description 1
- 229910001511 metal iodide Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 230000003533 narcotic effect Effects 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 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
- C07D211/18—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
- C07D211/30—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 doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom
- C07D211/32—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 doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom by oxygen atoms
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (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)
- Plural Heterocyclic Compounds (AREA)
Description
Subs SOHN 27814 29374 2 This invention consists in new substituted of general formula wherein is an group having or carbon and is bromine or a methyl or methoxy and their acid addition salts The invention also provides a process for the ration of compounds of formula I wherein a sponding secondary piperidine of the formula is reacted with a of the formula 29374 2 where and the meanings as above and is a hydroxy or group and formula is a methoxy this is replaced in the reaction duct by a hydroxy The reaction is in the presence of a suitable solvent and a such as sodium appropriately at a temperature between 30 and The reactants may be in a molecular ratio of but it is preferable to use the of formula III in To accelerate the reaction small quantities of metal iodide be As solvent an alcohol or a mixture of and hydrofuran is The compounds of formula I obtained may be converted into their physiologically unobjectionable addition for example by treatment with an inorganic or organic as a mineral citric or ascorbic new compounds of formula I possess valuable codynamic In they have a strong analgesic action without narcotic e they have a much stronger analgesic action than have the structurally very similar disclosed in US speci on of the 0 The test terms of are tabulated in the Table US specification Present Invention R H 16 H Br GH Br The hew compounds according to the invention can be processed preparations of all usual for pharmaceutical such for coated solutions solutions for thus prepared is a reactio such as described for in the literature resulting lated in the can be in a manner corresponding to the cited literature references and saponified to the invention is illustrated by the following 1 of of sodium bicarbonate and g of together with g of sodium iodide are boiled under in of formsmide and 175 of n for 25 it is evaporated by a rotatio evaporator and poured into ml of the crude base separates solid It is sucked with water and dried 21 g of base is dissolved with quantity of hanesulphonic acid 50 ml of ethanol while heating and is mixed with ether until it becomes just On cooling the solution yields g of ό with a melting point of 162 zation 23 g of the pure substance of 163 In an analogous manner the following compounds sere Example Melting Point of hydrochloride 2 01 229 230 3 Br 207 4 192 193 6 165 7 158 161 8 168 3 171 9 112 182 184 of A piperidine 5 mg lactose corn starch 45 colloidal silicic acid 2 soluble starch 5 magnesium 3 200 piperidine hydrochloride 75 lactose 100 mg starch colloidal silicic 2 sag soluble starch 5 mg magnesium 3 active ingredient is mixed with part of the excipients with a solution soluble After the granulate dried the remaining excipients are added and the mixture is into EXAMPLE B piperidine lactose 4 ad active ingredient and lactose mixed and the mixture is homogeneously suspended in the molten suppository fhe suspension is poured into moulds to form suppositories of weight C piperidine methanesulphonate 35 mg p sodium chloride 5 mg bidistilled water ad ml piperidine methanesulphonate 50 mg sodium chloride 7 rag water ml D piperidine hydrochloride g methyl g propyl 8 insufficientOCRQuality
Claims (1)
1. CLAIMS Substituted the general formula wherein is an alkyl group having or 3 carbon and is broaiine or a methyl or methoxy and their addition and its acid addition and its acid addition Pharmaceutical containing as an active ingredient from 10 to preferably 50 150 of according to Claim 2 or or an acid addition salt process for the preparation of compounds claimed in or wherein a corresponding secondary dine the formula 9 is reacted with a of the formula where and have the same in Claim 1 and is hydroxy or hoxy group if II is a this is replaced in the reaction product by a hydroxy A process according to Claim wherein the compound of Formula III is used in excess over the stoichiometrically A process according to Claim 5 or wherein the reaction is performed in an organic solvent a mixture of dimethyl formamide A process according to any of Claims 5 to wherein a small amount of alkali metal iodide is to the reactio A process for pr paration of compounds as claimed in Claims 2 or substantially as described herein with reference to the insufficientOCRQuality
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB0090912 | 1967-01-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IL29374A true IL29374A (en) | 1971-07-28 |
Family
ID=6985550
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL2937468A IL29374A (en) | 1967-01-26 | 1968-01-25 | Substituted 1-(4-oxo-4-phenyl-butyl)-piperidines |
Country Status (11)
| Country | Link |
|---|---|
| BE (1) | BE709966A (en) |
| CH (1) | CH496701A (en) |
| DE (1) | DE1670187A1 (en) |
| DK (1) | DK120192B (en) |
| ES (1) | ES349732A1 (en) |
| FR (2) | FR7256M (en) |
| GB (1) | GB1148427A (en) |
| IL (1) | IL29374A (en) |
| NL (1) | NL6800967A (en) |
| SE (1) | SE333569B (en) |
| YU (1) | YU18068A (en) |
-
1967
- 1967-01-26 DE DE19671670187 patent/DE1670187A1/en active Pending
-
1968
- 1968-01-23 NL NL6800967A patent/NL6800967A/xx unknown
- 1968-01-23 CH CH99668A patent/CH496701A/en not_active IP Right Cessation
- 1968-01-25 IL IL2937468A patent/IL29374A/en unknown
- 1968-01-25 DK DK29968A patent/DK120192B/en unknown
- 1968-01-25 ES ES349732A patent/ES349732A1/en not_active Expired
- 1968-01-25 YU YU18068A patent/YU18068A/en unknown
- 1968-01-26 GB GB431968A patent/GB1148427A/en not_active Expired
- 1968-01-26 FR FR137661A patent/FR7256M/fr not_active Expired
- 1968-01-26 SE SE106068A patent/SE333569B/xx unknown
- 1968-01-26 BE BE709966D patent/BE709966A/xx unknown
- 1968-01-26 FR FR1568084D patent/FR1568084A/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR7256M (en) | 1969-09-08 |
| NL6800967A (en) | 1968-07-29 |
| GB1148427A (en) | 1969-04-10 |
| FR1568084A (en) | 1969-05-23 |
| DK120192B (en) | 1971-04-26 |
| CH496701A (en) | 1970-09-30 |
| BE709966A (en) | 1968-07-26 |
| SE333569B (en) | 1971-03-22 |
| DE1670187A1 (en) | 1971-01-21 |
| YU18068A (en) | 1973-10-31 |
| ES349732A1 (en) | 1969-11-01 |
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