AU6496790A - New 1,3,4-trisubstituted 2-azetidinone derivatives, useful as intermediates for the synthesis of beta-lactams, and process for their asymmetric synthesis - Google Patents
New 1,3,4-trisubstituted 2-azetidinone derivatives, useful as intermediates for the synthesis of beta-lactams, and process for their asymmetric synthesisInfo
- Publication number
- AU6496790A AU6496790A AU64967/90A AU6496790A AU6496790A AU 6496790 A AU6496790 A AU 6496790A AU 64967/90 A AU64967/90 A AU 64967/90A AU 6496790 A AU6496790 A AU 6496790A AU 6496790 A AU6496790 A AU 6496790A
- Authority
- AU
- Australia
- Prior art keywords
- radical
- denotes
- optionally substituted
- synthesis
- intermediates
- 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.)
- Granted
Links
- -1 1,3,4-trisubstituted 2-azetidinone Chemical class 0.000 title abstract 15
- 239000000543 intermediate Substances 0.000 title abstract 2
- 238000011914 asymmetric synthesis Methods 0.000 title 1
- 230000015572 biosynthetic process Effects 0.000 title 1
- 238000000034 method Methods 0.000 title 1
- 238000003786 synthesis reaction Methods 0.000 title 1
- 150000003952 β-lactams Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 3
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 abstract 2
- WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 abstract 2
- JEVCWSUVFOYBFI-UHFFFAOYSA-N cyanyl Chemical compound N#[C] JEVCWSUVFOYBFI-UHFFFAOYSA-N 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- ORTFAQDWJHRMNX-UHFFFAOYSA-M oxidooxomethyl Chemical compound [O-][C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-M 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract 1
- 150000005840 aryl radicals Chemical class 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 125000000113 cyclohexyl group Chemical class [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract 1
- 125000001511 cyclopentyl group Chemical class [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 abstract 1
- 150000004252 dithioacetals Chemical group 0.000 abstract 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
-
- 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
- C07D205/08—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 with one oxygen atom directly attached in position 2, e.g. beta-lactams
Abstract
Compounds of formula I, consisting of the combination of formulae IA and IB: <IMAGE> in which: R1 denotes a hydrogen atom, a halogen atom, an alkyl radical, a trifluoromethyl radical, an alkoxy radical, a phenyl or benzyl radical (which are optionally substituted), a benzyloxy radical, a cyano radical, an alkoxycarbonyl radical, a carboxyl radical or an alkylamino radical, R2, different from R1, denotes a hydrogen atom, a halogen atom, an alkyl radical, a trifluoromethyl radical, an alkoxy radical, a phenyl or benzyl radical (which are optionally substituted), a benzyloxy radical, a cyano radical, an alkoxycarbonyl radical, a carboxyl radical or an alkylamino radical, each R3 denotes an alkyl radical or the two R3s form together and with the atoms of the dithioacetal functional group to which they are attached a 5- to 7-membered ring, R4 denotes an optionally substituted phenyl radical, a naphthyl radical or a furyl radical, each of R5 and R6, which are identical or different, denotes a hydrogen atom, an alkyl radical or an aryl radical (optionally substituted), and each R7 denotes a methyl radical or the two R7s form together and with the carbon atom to which they are attached a cyclohexane nucleus or a cyclopentane nucleus. The compounds of formula IA and IB are intermediates which are useful for the preparation of compounds of formulae XA and XB: Original abstract incomplete.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8913969A FR2653429B1 (en) | 1989-10-25 | 1989-10-25 | NOVEL DERIVATIVES OF AZETIDIN-2-ONE, 1,3,4-TRISUBSTITUES, INTERMEDIATES USEFUL FOR THE SYNTHESIS OF BETA-LACTAMS, AND THEIR ASYMMETRIC SYNTHESIS PROCESS. |
| FR8913969 | 1989-10-25 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU6496790A true AU6496790A (en) | 1991-05-02 |
| AU635975B2 AU635975B2 (en) | 1993-04-08 |
Family
ID=9386756
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU64967/90A Ceased AU635975B2 (en) | 1989-10-25 | 1990-10-24 | New 1,3,4-trisubstituted 2-azetidinone derivatives, useful as intermediates for the synthesis of beta-lactams, and process for their asymmetric synthesis |
Country Status (14)
| Country | Link |
|---|---|
| EP (1) | EP0425378B1 (en) |
| JP (1) | JPH0725731B2 (en) |
| AT (1) | ATE113058T1 (en) |
| AU (1) | AU635975B2 (en) |
| CA (1) | CA2028458A1 (en) |
| DE (1) | DE69013461T2 (en) |
| DK (1) | DK0425378T3 (en) |
| ES (1) | ES2064692T3 (en) |
| FR (1) | FR2653429B1 (en) |
| IE (1) | IE903554A1 (en) |
| NZ (1) | NZ235529A (en) |
| OA (1) | OA09319A (en) |
| PT (1) | PT95671A (en) |
| ZA (1) | ZA908130B (en) |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4384998A (en) * | 1981-03-30 | 1983-05-24 | Merck & Co., Inc. | Synthesis of thienamycin from D-glucose |
| US4777252A (en) * | 1987-08-13 | 1988-10-11 | E. R. Squibb & Sons, Inc. | 2-oxo-1-[[(substituted sulfonyl)amino]-carbonyl]azetidines |
| DE3854215T2 (en) * | 1987-09-22 | 1995-12-21 | Shionogi Seiyaku Kk | Alkenylsilylazetidinone intermediates for carbapenems. |
-
1989
- 1989-10-25 FR FR8913969A patent/FR2653429B1/en not_active Expired - Lifetime
-
1990
- 1990-10-01 NZ NZ235529A patent/NZ235529A/en unknown
- 1990-10-04 IE IE355490A patent/IE903554A1/en unknown
- 1990-10-11 ZA ZA908130A patent/ZA908130B/en unknown
- 1990-10-24 CA CA002028458A patent/CA2028458A1/en not_active Abandoned
- 1990-10-24 JP JP2286939A patent/JPH0725731B2/en not_active Expired - Lifetime
- 1990-10-24 AU AU64967/90A patent/AU635975B2/en not_active Ceased
- 1990-10-24 PT PT95671A patent/PT95671A/en not_active Application Discontinuation
- 1990-10-25 AT AT90403003T patent/ATE113058T1/en not_active IP Right Cessation
- 1990-10-25 ES ES90403003T patent/ES2064692T3/en not_active Expired - Lifetime
- 1990-10-25 EP EP90403003A patent/EP0425378B1/en not_active Expired - Lifetime
- 1990-10-25 OA OA59874A patent/OA09319A/en unknown
- 1990-10-25 DK DK90403003.8T patent/DK0425378T3/en active
- 1990-10-25 DE DE69013461T patent/DE69013461T2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CA2028458A1 (en) | 1991-04-26 |
| ZA908130B (en) | 1991-07-31 |
| DE69013461D1 (en) | 1994-11-24 |
| EP0425378B1 (en) | 1994-10-19 |
| EP0425378A1 (en) | 1991-05-02 |
| PT95671A (en) | 1991-09-13 |
| ES2064692T3 (en) | 1995-02-01 |
| NZ235529A (en) | 1992-08-26 |
| AU635975B2 (en) | 1993-04-08 |
| OA09319A (en) | 1992-09-15 |
| IE903554A1 (en) | 1991-05-08 |
| ATE113058T1 (en) | 1994-11-15 |
| FR2653429B1 (en) | 1991-12-20 |
| DE69013461T2 (en) | 1995-05-18 |
| DK0425378T3 (en) | 1995-02-27 |
| JPH0725731B2 (en) | 1995-03-22 |
| FR2653429A1 (en) | 1991-04-26 |
| JPH03151382A (en) | 1991-06-27 |
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