ES8405761A1 - Azetidinone derivatives - Google Patents
Azetidinone derivativesInfo
- Publication number
- ES8405761A1 ES8405761A1 ES518720A ES518720A ES8405761A1 ES 8405761 A1 ES8405761 A1 ES 8405761A1 ES 518720 A ES518720 A ES 518720A ES 518720 A ES518720 A ES 518720A ES 8405761 A1 ES8405761 A1 ES 8405761A1
- Authority
- ES
- Spain
- Prior art keywords
- image
- general formula
- defined above
- new
- thienamycin
- 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
- MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical class O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 3
- WKDDRNSBRWANNC-ATRFCDNQSA-N Thienamycin Chemical compound C1C(SCCN)=C(C(O)=O)N2C(=O)[C@H]([C@H](O)C)[C@H]21 WKDDRNSBRWANNC-ATRFCDNQSA-N 0.000 abstract 2
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 abstract 1
- WKDDRNSBRWANNC-UHFFFAOYSA-N Thienamycin Natural products C1C(SCCN)=C(C(O)=O)N2C(=O)C(C(O)C)C21 WKDDRNSBRWANNC-UHFFFAOYSA-N 0.000 abstract 1
- 125000003368 amide group Chemical group 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 125000006243 carbonyl protecting group Chemical group 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- XXTZHYXQVWRADW-UHFFFAOYSA-N diazomethanone Chemical compound [N]N=C=O XXTZHYXQVWRADW-UHFFFAOYSA-N 0.000 abstract 1
- -1 heterocyclic acetic acid compounds Chemical class 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 239000000825 pharmaceutical preparation Substances 0.000 abstract 1
- 125000006239 protecting group Chemical group 0.000 abstract 1
- 230000008707 rearrangement Effects 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member 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
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/273—2-Pyrrolidones 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 other ring carbon atoms
- C07D207/277—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D207/28—2-Pyrrolidone-5- carboxylic acids; Functional derivatives thereof, e.g. esters, nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D411/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms
- C07D411/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D411/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
New heterocyclic acetic acid compounds of the general formula (I), < IMAGE > wherein Y<1> and Y<2> form together a removable carbonyl protecting group, and R is a removable amido protecting group, are prepared in the way that a compound of the general formula (II), < IMAGE > wherein R, Y<1> and Y<2> are as defined above, is activated on the carboxy group and then reacted with diazomethane, and the resulting new compound of the general formula (II), < IMAGE > wherein R, Y<1> and Y<2> are as defined above, is subjected to diazoketone rearrangement in the presence of water. The new compounds according to the invention can be incorporated into pharmaceutical preparations and are valuable intermediates in the synthesis of thienamycin and thienamycin analogues.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
HU814012A HU184495B (en) | 1981-12-30 | 1981-12-30 | Process for preparing new azetidinone-acetic acids |
Publications (2)
Publication Number | Publication Date |
---|---|
ES8405761A1 true ES8405761A1 (en) | 1984-06-16 |
ES518720A0 ES518720A0 (en) | 1984-06-16 |
Family
ID=10966505
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ES518720A Granted ES518720A0 (en) | 1981-12-30 | 1982-12-30 | PROCEDURE FOR THE PREPARATION OF TRANS-1- (1,3-DISUSTITUTED-4-OXO-2-ACETIDINYL ACID DERIVATIVES. |
Country Status (19)
Country | Link |
---|---|
JP (1) | JPS58118566A (en) |
AT (1) | AT379147B (en) |
AU (1) | AU554739B2 (en) |
BE (1) | BE895489A (en) |
CA (1) | CA1189865A (en) |
CH (1) | CH655926A5 (en) |
DE (1) | DE3248672A1 (en) |
ES (1) | ES518720A0 (en) |
FI (1) | FI824516L (en) |
FR (1) | FR2518998B1 (en) |
GB (1) | GB2112393B (en) |
GR (1) | GR78428B (en) |
HU (1) | HU184495B (en) |
IT (1) | IT1210968B (en) |
LU (1) | LU84568A1 (en) |
NL (1) | NL8205064A (en) |
PL (1) | PL137593B1 (en) |
SE (1) | SE453083B (en) |
ZA (1) | ZA829593B (en) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
HU190404B (en) * | 1982-07-30 | 1986-09-29 | Richter Gedeon Vegyeszeti Gyar Rt,Hu | Process for preparing amino-lactone-carboxylic acid |
HU187424B (en) * | 1982-11-05 | 1986-01-28 | Richter Gedeon Vegyeszeti Gyar Rt,Hu | Process for preparing new azetidinyl-acetic acids |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
PT71553B (en) * | 1979-07-23 | 1981-12-14 | Merck & Co Inc | Process for the preparation of thienamycin and intermediates |
JPS57167964A (en) * | 1981-04-09 | 1982-10-16 | Toyama Chem Co Ltd | Preparation of (4r)-3-substituted-4-(substituted or unsubstituted carboxymethyl)-2-azetidinone derivative |
JPS57176982A (en) * | 1981-04-24 | 1982-10-30 | Shionogi & Co Ltd | Dioxolanylazetidinone compound, its preparation and use |
-
1981
- 1981-12-30 HU HU814012A patent/HU184495B/en not_active IP Right Cessation
-
1982
- 1982-12-10 AT AT0450782A patent/AT379147B/en not_active IP Right Cessation
- 1982-12-24 JP JP57235006A patent/JPS58118566A/en active Pending
- 1982-12-28 BE BE1/10676A patent/BE895489A/en not_active IP Right Cessation
- 1982-12-29 SE SE8207475A patent/SE453083B/en not_active IP Right Cessation
- 1982-12-29 LU LU84568A patent/LU84568A1/en unknown
- 1982-12-29 FR FR8221978A patent/FR2518998B1/en not_active Expired
- 1982-12-29 CH CH7602/82A patent/CH655926A5/en not_active IP Right Cessation
- 1982-12-30 ZA ZA829593A patent/ZA829593B/en unknown
- 1982-12-30 GB GB08236917A patent/GB2112393B/en not_active Expired
- 1982-12-30 AU AU91968/82A patent/AU554739B2/en not_active Ceased
- 1982-12-30 GR GR70183A patent/GR78428B/el unknown
- 1982-12-30 PL PL1982239885A patent/PL137593B1/en unknown
- 1982-12-30 NL NL8205064A patent/NL8205064A/en not_active Application Discontinuation
- 1982-12-30 ES ES518720A patent/ES518720A0/en active Granted
- 1982-12-30 IT IT8225060A patent/IT1210968B/en active
- 1982-12-30 DE DE19823248672 patent/DE3248672A1/en not_active Withdrawn
- 1982-12-30 CA CA000418739A patent/CA1189865A/en not_active Expired
- 1982-12-30 FI FI824516A patent/FI824516L/en not_active Application Discontinuation
Also Published As
Publication number | Publication date |
---|---|
SE8207475D0 (en) | 1982-12-29 |
BE895489A (en) | 1983-06-28 |
ZA829593B (en) | 1983-10-26 |
CA1189865A (en) | 1985-07-02 |
LU84568A1 (en) | 1984-10-22 |
JPS58118566A (en) | 1983-07-14 |
SE8207475L (en) | 1983-07-01 |
PL137593B1 (en) | 1986-06-30 |
GB2112393B (en) | 1985-08-14 |
NL8205064A (en) | 1983-07-18 |
GB2112393A (en) | 1983-07-20 |
FR2518998A1 (en) | 1983-07-01 |
DE3248672A1 (en) | 1983-07-07 |
AT379147B (en) | 1985-11-25 |
PL239885A1 (en) | 1984-01-02 |
AU9196882A (en) | 1983-07-07 |
AU554739B2 (en) | 1986-09-04 |
HU184495B (en) | 1984-08-28 |
IT1210968B (en) | 1989-09-29 |
ES518720A0 (en) | 1984-06-16 |
FR2518998B1 (en) | 1986-02-28 |
CH655926A5 (en) | 1986-05-30 |
FI824516L (en) | 1983-07-01 |
FI824516A0 (en) | 1982-12-30 |
ATA450782A (en) | 1985-04-15 |
IT8225060A0 (en) | 1982-12-30 |
SE453083B (en) | 1988-01-11 |
GR78428B (en) | 1984-09-27 |
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