JPS57197280A - Preparation of 2-thioxopenam derivative - Google Patents
Preparation of 2-thioxopenam derivativeInfo
- Publication number
- JPS57197280A JPS57197280A JP56082828A JP8282881A JPS57197280A JP S57197280 A JPS57197280 A JP S57197280A JP 56082828 A JP56082828 A JP 56082828A JP 8282881 A JP8282881 A JP 8282881A JP S57197280 A JPS57197280 A JP S57197280A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound shown
- give
- compound
- reacted
- 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
- LRZDMDHBDMOGRY-SCSAIBSYSA-N (5r)-3-sulfanylidene-4-thia-1-azabicyclo[3.2.0]heptan-7-one Chemical class S1C(=S)CN2C(=O)C[C@H]21 LRZDMDHBDMOGRY-SCSAIBSYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 8
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000002947 alkylene group Chemical group 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- 125000006239 protecting group Chemical group 0.000 abstract 2
- ULIIBMACXKPVBZ-NFJWQWPMSA-N (4-nitrophenyl)methyl (5r)-7-oxo-3-sulfanylidene-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate Chemical compound C1=CC([N+](=O)[O-])=CC=C1COC(=O)C1C(=S)S[C@H]2N1C(=O)C2 ULIIBMACXKPVBZ-NFJWQWPMSA-N 0.000 abstract 1
- 125000004442 acylamino group Chemical group 0.000 abstract 1
- 125000004423 acyloxy group Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 abstract 1
- 230000000844 anti-bacterial effect Effects 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 230000002140 halogenating effect Effects 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- -1 penam compound Chemical class 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 125000005389 trialkylsiloxy group Chemical group 0.000 abstract 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Abstract
NEW MATERIAL:A compound shown by the formulaI[R1 is H, alkyl, alkoxy, or group shown by the formula R3A-(R3 is OH, alkoxy, acyloxy, trialkylsilyloxy, SH, alkylthio, NH2, acylamino, etc.; A is alkylene which may contain CF3 or phenyl group); R2 is H or carboxyl-protecting group] and its salt.
EXAMPLE: 2-Thioxopenam-3-carboxylic acid p-nitrobenzyl ester.
USE: An intermediate for a penam compound having improved antibacterial activity.
PROCESS: A compound shown by the formula 2 (R4 is H, alkyl, etc.: R5 is lower alkyl; R6 is protecting group) is treated with a base, reacted with CS2, and then with a compound shown by the formula 3 (B is lower alkylene, etc.; X is halogen), to give a compound shown by the formula 4. This compound is reacted with a halogenating agent to give a compound shown by the formula 5(Y is halogen), which is reacted with a base to give a compound shown by the formula 6. If necessary, the protecting group is eliminated to give another compound shown by the formulaI.
COPYRIGHT: (C)1982,JPO&Japio
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP56082828A JPS57197280A (en) | 1981-05-30 | 1981-05-30 | Preparation of 2-thioxopenam derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP56082828A JPS57197280A (en) | 1981-05-30 | 1981-05-30 | Preparation of 2-thioxopenam derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS57197280A true JPS57197280A (en) | 1982-12-03 |
| JPH0154354B2 JPH0154354B2 (en) | 1989-11-17 |
Family
ID=13785252
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP56082828A Granted JPS57197280A (en) | 1981-05-30 | 1981-05-30 | Preparation of 2-thioxopenam derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS57197280A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4595539A (en) * | 1983-06-10 | 1986-06-17 | Pfizer Inc. | Preparation of penem derivatives and azetidinone intermediates |
| US4619783A (en) * | 1983-06-10 | 1986-10-28 | Pfizer Inc. | Process and intermediates for the preparation of penem derivatives |
| US4725678A (en) * | 1983-06-10 | 1988-02-16 | Pfizer Inc. | Azetidinone intermediates for the preparation of penem derivatives |
-
1981
- 1981-05-30 JP JP56082828A patent/JPS57197280A/en active Granted
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4595539A (en) * | 1983-06-10 | 1986-06-17 | Pfizer Inc. | Preparation of penem derivatives and azetidinone intermediates |
| US4619783A (en) * | 1983-06-10 | 1986-10-28 | Pfizer Inc. | Process and intermediates for the preparation of penem derivatives |
| US4725678A (en) * | 1983-06-10 | 1988-02-16 | Pfizer Inc. | Azetidinone intermediates for the preparation of penem derivatives |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0154354B2 (en) | 1989-11-17 |
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