ES388754A1 - A procedure for the preparation of new derivatives of azetidinol. (Machine-translation by Google Translate, not legally binding) - Google Patents
A procedure for the preparation of new derivatives of azetidinol. (Machine-translation by Google Translate, not legally binding)Info
- Publication number
- ES388754A1 ES388754A1 ES388754A ES388754A ES388754A1 ES 388754 A1 ES388754 A1 ES 388754A1 ES 388754 A ES388754 A ES 388754A ES 388754 A ES388754 A ES 388754A ES 388754 A1 ES388754 A1 ES 388754A1
- Authority
- ES
- Spain
- Prior art keywords
- azetidinol
- compounds
- give
- phenyl
- benzoyl
- 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
- ZQQSYPZAPHRXRY-UHFFFAOYSA-N 1-hydroxyazetidine Chemical class ON1CCC1 ZQQSYPZAPHRXRY-UHFFFAOYSA-N 0.000 title 1
- 238000000034 method Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 6
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- 230000005494 condensation Effects 0.000 abstract 3
- 238000009833 condensation Methods 0.000 abstract 3
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 125000001475 halogen functional group Chemical group 0.000 abstract 2
- BSGLMZJRZWDLPH-UHFFFAOYSA-N (1-benzoylazetidin-3-yl) benzoate Chemical compound C(C1=CC=CC=C1)(=O)N1CC(C1)OC(C1=CC=CC=C1)=O BSGLMZJRZWDLPH-UHFFFAOYSA-N 0.000 abstract 1
- LZXZKGIUNYSRJR-UHFFFAOYSA-N (3-hydroxy-3-phenylazetidin-1-yl)-phenylmethanone Chemical compound C1C(O)(C=2C=CC=CC=2)CN1C(=O)C1=CC=CC=C1 LZXZKGIUNYSRJR-UHFFFAOYSA-N 0.000 abstract 1
- MQPNDHHRMVRTCE-UHFFFAOYSA-N (3-hydroxyazetidin-1-yl)-phenylmethanone Chemical compound C1C(O)CN1C(=O)C1=CC=CC=C1 MQPNDHHRMVRTCE-UHFFFAOYSA-N 0.000 abstract 1
- FCWANJOYOGQLDS-UHFFFAOYSA-N 1-benzoylazetidin-3-one Chemical compound C=1C=CC=CC=1C(=O)N1CC(=O)C1 FCWANJOYOGQLDS-UHFFFAOYSA-N 0.000 abstract 1
- BCCJGJCXMIOABO-UHFFFAOYSA-N 3-phenylazetidin-3-ol Chemical compound C=1C=CC=CC=1C1(O)CNC1 BCCJGJCXMIOABO-UHFFFAOYSA-N 0.000 abstract 1
- 125000004423 acyloxy group Chemical group 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000001118 alkylidene group Chemical group 0.000 abstract 1
- 229940035676 analgesics Drugs 0.000 abstract 1
- 239000000730 antalgic agent Substances 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- GMWFCJXSQQHBPI-UHFFFAOYSA-N azetidin-3-ol Chemical compound OC1CNC1 GMWFCJXSQQHBPI-UHFFFAOYSA-N 0.000 abstract 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 abstract 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 abstract 1
- 125000000392 cycloalkenyl group Chemical group 0.000 abstract 1
- 125000001188 haloalkyl group Chemical group 0.000 abstract 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 238000007911 parenteral administration Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000000546 pharmaceutical excipient Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/04—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/06—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Novel compounds I in which R 1 is OH or hydroxy etherified or esterified by a pharmaceutically acceptable moiety R 2 is aryl optionally substituted by OH, alkyl, cycloalkyl, alkoxy, halo or haloalkyl R 3 and R 4 are H, alkyl, cycloalkyl or aryl and R 5 is alkyl, cycloalkyl, alkenyl, cycloalkenyl or aralkyl, all of which may be substituted by OH, alkoxy, acyloxy or halo and their salts are prepared (1) by reaction of compounds II with R 7 -R 5 (R 6 and R, are reactive groups) (2) by condensation of compounds IV with oxo compounds R 8 -CO-R 9 followed by reduction of the condensate to give I where R 5 is CHR 8 R 9 (3) reducing a double bond in starting compounds differing from compounds I in that they contain one or more non-aromatic double bonds and (4) subjecting compounds R 5 -NR 14 (R 15 ) (R 11 is H or and R 16 is an acid radical which is eliminated R 15 is H or R 18 C00R 19 R 18 is alkylidene, R 19 is alkyl) either when R 14 is H to condensation with R 17 CH(R 3 )-CR 1 R 2 -CH(R 4 )-R 17 (R 17 is a radical derived from an acid, which radical is eliminated during reaction) or when R 14 is -CHR 3 -CR 1 R 2 -CHR 4 R 16 to intramolecular condensation. Intermediates isolated are those prepared in the following sequence: 3-azetidinol is reacted with benzoyl chloride to give 1-benzoyl-3- benzoyloxyazetidine which is then reacted with KOH to give 1-benzoyl-3-azetidinol which is then oxidized to 1-benzoyl-azetidin-3-one which is then reacted with C 6 H 5 MgBr to give 1 - benzoyl - 3 - phenyl - 3 - azetidinol which is then refluxed with NaOH to give 3-phenyl-3- azetidinol (which may also be prepared by catalytic hydrogenation of 1-([alpha]-phenethyl)-3-phenyl-3-azetidinol) which is then acetylated to give 1 - acetyl - 3 - acetoxy - 3 - phenyl - azetidiec. 1 -Benzcyl-3-phenyl-3-azetidinol is prepared by U.V. irradiation of N-methyl-[alpha]-benzamidoacetophenone. Pharmaceutical compositions comprise a compound I together with a suitable excipient for oral or parenteral administration as analgesics.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US74120568A | 1968-06-28 | 1968-06-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES388754A1 true ES388754A1 (en) | 1973-05-16 |
Family
ID=24979786
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES368859A Expired ES368859A1 (en) | 1968-06-28 | 1969-06-27 | A procedure for the preparation of new derivatives of azetidinol. (Machine-translation by Google Translate, not legally binding) |
| ES388752A Expired ES388752A1 (en) | 1968-06-28 | 1971-03-01 | A PROCEDURE FOR THE PREPARATION OF NEW DERIVATIVES OF AZETIDINOL. |
| ES388754A Expired ES388754A1 (en) | 1968-06-28 | 1971-03-01 | A procedure for the preparation of new derivatives of azetidinol. (Machine-translation by Google Translate, not legally binding) |
| ES388753A Expired ES388753A1 (en) | 1968-06-28 | 1971-03-01 | A procedure for the preparation of new derivatives of azetidinol. (Machine-translation by Google Translate, not legally binding) |
Family Applications Before (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES368859A Expired ES368859A1 (en) | 1968-06-28 | 1969-06-27 | A procedure for the preparation of new derivatives of azetidinol. (Machine-translation by Google Translate, not legally binding) |
| ES388752A Expired ES388752A1 (en) | 1968-06-28 | 1971-03-01 | A PROCEDURE FOR THE PREPARATION OF NEW DERIVATIVES OF AZETIDINOL. |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES388753A Expired ES388753A1 (en) | 1968-06-28 | 1971-03-01 | A procedure for the preparation of new derivatives of azetidinol. (Machine-translation by Google Translate, not legally binding) |
Country Status (10)
| Country | Link |
|---|---|
| BE (1) | BE735313A (en) |
| CA (1) | CA957382A (en) |
| CH (2) | CH511227A (en) |
| DE (1) | DE1932985A1 (en) |
| DK (1) | DK122126B (en) |
| ES (4) | ES368859A1 (en) |
| FR (1) | FR2014404A1 (en) |
| GB (1) | GB1266587A (en) |
| NL (1) | NL6909923A (en) |
| NO (1) | NO128960B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2009317155A1 (en) * | 2008-11-24 | 2010-05-27 | Nsab, Filial Af Neurosearch Sweden Ab, Sverige | Novel 3-phenyl-azetidine derivatives useful as modulators of cortical catecholaminergic neurotransmission |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1332511A (en) * | 1959-12-09 | 1963-07-19 | Lepetit Spa | Process for the preparation of novel n-alkylazetidines |
-
1969
- 1969-06-26 CH CH983869A patent/CH511227A/en not_active IP Right Cessation
- 1969-06-26 CH CH899671D patent/CH524598A/en not_active IP Right Cessation
- 1969-06-27 NO NO269069A patent/NO128960B/no unknown
- 1969-06-27 GB GB1266587D patent/GB1266587A/en not_active Expired
- 1969-06-27 BE BE735313D patent/BE735313A/xx unknown
- 1969-06-27 FR FR6921710A patent/FR2014404A1/fr not_active Withdrawn
- 1969-06-27 CA CA055,643A patent/CA957382A/en not_active Expired
- 1969-06-27 NL NL6909923A patent/NL6909923A/xx unknown
- 1969-06-27 DK DK351069A patent/DK122126B/en unknown
- 1969-06-27 ES ES368859A patent/ES368859A1/en not_active Expired
- 1969-06-28 DE DE19691932985 patent/DE1932985A1/en active Pending
-
1971
- 1971-03-01 ES ES388752A patent/ES388752A1/en not_active Expired
- 1971-03-01 ES ES388754A patent/ES388754A1/en not_active Expired
- 1971-03-01 ES ES388753A patent/ES388753A1/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE1932985A1 (en) | 1970-01-02 |
| FR2014404A1 (en) | 1970-04-17 |
| DK122126B (en) | 1972-01-24 |
| ES368859A1 (en) | 1971-07-16 |
| ES388752A1 (en) | 1973-05-16 |
| ES388753A1 (en) | 1973-05-16 |
| NL6909923A (en) | 1969-12-30 |
| CA957382A (en) | 1974-11-05 |
| CH524598A (en) | 1972-06-30 |
| GB1266587A (en) | 1972-03-15 |
| NO128960B (en) | 1974-02-04 |
| BE735313A (en) | 1969-12-29 |
| CH511227A (en) | 1971-08-15 |
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