GB1448571A - 4-4-alkoxy-4-alkyl-piperidino-4-fluoro-btuyrophenones - Google Patents
4-4-alkoxy-4-alkyl-piperidino-4-fluoro-btuyrophenonesInfo
- Publication number
- GB1448571A GB1448571A GB424673A GB424673A GB1448571A GB 1448571 A GB1448571 A GB 1448571A GB 424673 A GB424673 A GB 424673A GB 424673 A GB424673 A GB 424673A GB 1448571 A GB1448571 A GB 1448571A
- Authority
- GB
- United Kingdom
- Prior art keywords
- prepared
- reacting
- methyl
- compound
- alkyl
- 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 abstract 5
- SJZKULRDWHPHGG-UHFFFAOYSA-N 1-benzylpiperidin-4-one Chemical compound C1CC(=O)CCN1CC1=CC=CC=C1 SJZKULRDWHPHGG-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- 229910010082 LiAlH Inorganic materials 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 abstract 2
- -1 chlorobutoxy compound Chemical class 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
- UYXKYGWEXGLKKV-UHFFFAOYSA-N 4-(1-benzyl-4-methylpiperidin-4-yl)oxybutan-1-ol Chemical compound C1CC(C)(OCCCCO)CCN1CC1=CC=CC=C1 UYXKYGWEXGLKKV-UHFFFAOYSA-N 0.000 abstract 1
- LJBAFRBWVNZZBY-UHFFFAOYSA-N 4-butoxy-4-methylpiperidine Chemical compound CCCCOC1(C)CCNCC1 LJBAFRBWVNZZBY-UHFFFAOYSA-N 0.000 abstract 1
- DTROZRPXWPUWEY-UHFFFAOYSA-N 4-methoxy-4-propan-2-ylpiperidine Chemical compound COC1(C(C)C)CCNCC1 DTROZRPXWPUWEY-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
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 230000002152 alkylating effect Effects 0.000 abstract 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 abstract 1
- 229910052782 aluminium Inorganic materials 0.000 abstract 1
- 239000004411 aluminium 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
- 239000003874 central nervous system depressant Substances 0.000 abstract 1
- 125000004122 cyclic group Chemical group 0.000 abstract 1
- 230000000911 decarboxylating effect Effects 0.000 abstract 1
- 238000006114 decarboxylation reaction Methods 0.000 abstract 1
- SJUXLKYJKQBZLM-UHFFFAOYSA-N ethyl 3-(4-fluorophenyl)-3-oxopropanoate Chemical compound CCOC(=O)CC(=O)C1=CC=C(F)C=C1 SJUXLKYJKQBZLM-UHFFFAOYSA-N 0.000 abstract 1
- 229960003750 ethyl chloride Drugs 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 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
- 238000011065 in-situ storage Methods 0.000 abstract 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- ZIULUUPYEQPRAQ-UHFFFAOYSA-L magnesium;fluorobenzene;dibromide Chemical compound [Mg+2].[Br-].[Br-].FC1=CC=CC=C1 ZIULUUPYEQPRAQ-UHFFFAOYSA-L 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- LMHHRCOWPQNFTF-UHFFFAOYSA-N s-propan-2-yl azepane-1-carbothioate Chemical compound CC(C)SC(=O)N1CCCCCC1 LMHHRCOWPQNFTF-UHFFFAOYSA-N 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/10—Spiro-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Psychiatry (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biomedical Technology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pain & Pain Management (AREA)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
1448571 1 - (p - Fluorobenzoylpropyl)- 4- alkoxy - 4 - alkyl - piperidines FERROSAN AB 22 Jan 1974 [26 Jan 1973] 4246/73 Heading C2C Novel compounds I in which R 1 and R 2 are C 1-5 alkyl are prepared by reacting a 4-C 1-5 alkyl-4-C 1-5 alkoxy-piperidine with γ-halo-p-fluorobutyrophenone. Compound I (R 1 = R 2 = ethyl) is also prepared by reacting p-fluorobenzene magnesium bromide with γ - (4 - ethyl - 4 - ethoxy - piperdino)- butyronitrile and hydrolysing and decarboxylating the intermediate formed in situ. Compound I (R 1 = iso-propyl, R 2 = methyl) is also prepared by reacting #-(p-fluorobenzoyl)-propionic acid chloride with 4-isopropyl-4-methoxy piperidine, reducing with LiAlH 4 to form 1-[4- p - fluorophenyl - 4 - hydroxy - buytl] - 4 - isopropyl-4-methoxypiperidine and oxidizing the alcohol to a ketone using aluminium isopropylate. Compound I (R 1 = methyl, R 2 = butoxy) is also prepared by ethyl p-fluoro-benzoylacetate and #-(4-butoxy-4-methyl-piperidino)- ethylchloride in the presence of sodium followed by hydrolysis and decarboxylation. 4 - C 1-5 alkyl - 4 - C 1-5 alkoxy - piperidines are prepared by reacting 1-benzyl-4-piperidone with R 1 MgBr followed by alkylating the alcohol and dibenzylation. 4-Butoxy-4-methyl-piperidine is also prepared by reacting 1-benzyl-4-piperidone with butane-1,4-diol to form a cyclic ketal which is reacted with CH 3 MgBr to form 4-[(1-benzyl- 4 - methyl - 4 - piperidyl)oxy] - butanol which is reacted with thionyl chloride to form the chlorobutoxy compound which is reduced using LiAlH 4 to the butoxy compound and dibenzylated. Compounds I are CNS depressants and form with a carrier a pharmaceutical composition which may be administered orally or parenterally.
Priority Applications (14)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB424673A GB1448571A (en) | 1973-01-26 | 1973-01-26 | 4-4-alkoxy-4-alkyl-piperidino-4-fluoro-btuyrophenones |
| SE7400710A SE399253B (en) | 1973-01-26 | 1974-01-18 | PROCEDURE FOR THE PREPARATION OF PHARMACOLOGICALLY ACTIVE GAMMA PIPERIDINOBUTYROPHENONES |
| CH215177A CH602646A5 (en) | 1973-01-26 | 1974-01-22 | |
| CH82674A CH592060A5 (en) | 1973-01-26 | 1974-01-22 | |
| DE2403231A DE2403231A1 (en) | 1973-01-26 | 1974-01-24 | NEW BASIC KETONE AND METHOD FOR PRODUCING THEM |
| CA190,813A CA1014159A (en) | 1973-01-26 | 1974-01-24 | .gamma.-(4-ALKYL-4-ALKOXY-PIPERIDINO)-P-FLUORO-4-BUTYROPHONONES |
| AT57974*#A AT333279B (en) | 1973-01-26 | 1974-01-24 | Process for the preparation of new basic ketones and their salts |
| BE140178A BE810162A (en) | 1973-01-26 | 1974-01-25 | NEW BASIC KETONES |
| FR7402471A FR2215225B1 (en) | 1973-01-26 | 1974-01-25 | |
| JP49010867A JPS5212714B2 (en) | 1973-01-26 | 1974-01-25 | |
| LU69245A LU69245A1 (en) | 1973-01-26 | 1974-01-25 | |
| NL7401102A NL7401102A (en) | 1973-01-26 | 1974-01-28 | |
| US05/633,268 US4070473A (en) | 1973-01-26 | 1975-11-19 | Piperidino-butyrophenones |
| AT69376A AT336019B (en) | 1973-01-26 | 1976-02-02 | Process for the preparation of new basic ketones and their salts |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB424673A GB1448571A (en) | 1973-01-26 | 1973-01-26 | 4-4-alkoxy-4-alkyl-piperidino-4-fluoro-btuyrophenones |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1448571A true GB1448571A (en) | 1976-09-08 |
Family
ID=9773488
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB424673A Expired GB1448571A (en) | 1973-01-26 | 1973-01-26 | 4-4-alkoxy-4-alkyl-piperidino-4-fluoro-btuyrophenones |
Country Status (11)
| Country | Link |
|---|---|
| JP (1) | JPS5212714B2 (en) |
| AT (1) | AT333279B (en) |
| BE (1) | BE810162A (en) |
| CA (1) | CA1014159A (en) |
| CH (2) | CH592060A5 (en) |
| DE (1) | DE2403231A1 (en) |
| FR (1) | FR2215225B1 (en) |
| GB (1) | GB1448571A (en) |
| LU (1) | LU69245A1 (en) |
| NL (1) | NL7401102A (en) |
| SE (1) | SE399253B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5927252U (en) * | 1982-08-12 | 1984-02-20 | 株式会社サンゴ | Concrete foundation for slopes |
| MX2007000441A (en) * | 2004-10-01 | 2007-03-07 | Pedro Jose Zubiaurre Alberdi | Handle-fixing system for a hand tool or utensil. |
-
1973
- 1973-01-26 GB GB424673A patent/GB1448571A/en not_active Expired
-
1974
- 1974-01-18 SE SE7400710A patent/SE399253B/en unknown
- 1974-01-22 CH CH82674A patent/CH592060A5/xx not_active IP Right Cessation
- 1974-01-22 CH CH215177A patent/CH602646A5/xx not_active IP Right Cessation
- 1974-01-24 CA CA190,813A patent/CA1014159A/en not_active Expired
- 1974-01-24 DE DE2403231A patent/DE2403231A1/en active Pending
- 1974-01-24 AT AT57974*#A patent/AT333279B/en not_active IP Right Cessation
- 1974-01-25 LU LU69245A patent/LU69245A1/xx unknown
- 1974-01-25 FR FR7402471A patent/FR2215225B1/fr not_active Expired
- 1974-01-25 JP JP49010867A patent/JPS5212714B2/ja not_active Expired
- 1974-01-25 BE BE140178A patent/BE810162A/en unknown
- 1974-01-28 NL NL7401102A patent/NL7401102A/xx not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| NL7401102A (en) | 1974-07-30 |
| JPS5212714B2 (en) | 1977-04-08 |
| BE810162A (en) | 1974-05-16 |
| JPS49101384A (en) | 1974-09-25 |
| CH602646A5 (en) | 1978-07-31 |
| CA1014159A (en) | 1977-07-19 |
| DE2403231A1 (en) | 1974-08-01 |
| CH592060A5 (en) | 1977-10-14 |
| LU69245A1 (en) | 1974-04-10 |
| AT333279B (en) | 1976-11-10 |
| FR2215225A1 (en) | 1974-08-23 |
| SE399253B (en) | 1978-02-06 |
| FR2215225B1 (en) | 1976-10-22 |
| ATA57974A (en) | 1976-03-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |