# US 5,703,243 A · Intermediates for pyrrolidylthiocarbapenem derivative > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 5,703,243 A - Document ID: US5703243A - Status: Granted - Kind: A - Application number: 08/574,863 - Filed: 1995-12-19 - Granted: 1997-12-30 - Earliest claimed: 1991-08-20 - Assignees: Shionogi Seiyaku Kabushiki Kaisha - Inventors: Yasuhiro Nishitani; Tadashi Irie; Yutaka Nishino - Web page: https://patentgrep.com/patent/US5703243A ## CPC - C07D 207/273: 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 - A61P 31/04: Antibacterial agents - C07C 307/04: Diamides of sulfuric acids - C07D 207/12: Oxygen or sulfur atoms - C07D 477/02: Preparation (by microbiological processes C12P17/18) - C07D 477/14: with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached in position 3 - C07D 477/20: Sulfur atoms - C07D 501/00: Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula: [IMAGE cpc-sch-C07D-0993.gif] , e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring - C08L 63/00: Compositions of epoxy resins; Compositions of derivatives of epoxy resins - Y02P 20/55: Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups - C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08) - A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS - C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS - C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06) - Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS ## Abstract A pyrrolidylthiocarbapenem derivative represented by Formula I is provided: ##STR1## wherein R.sup.1 is hydrogen or lower alkyl; R.sup.2, R.sup.3 and R.sup.4 are hydrogen, lower alkyl which can be substituted or an amino protecting group independently, or R.sup.2 and R.sup.3 together with a nitrogen atom to which R.sup.2 and R.sup.3 are bonded form a saturated or unsaturated cyclic group, or R.sup.2 and R.sup.4, or R.sup.3 and R.sup.4 together with two nitrogen atoms and one sulfur atom in the sufamide group form a saturated or unsaturated cyclic group; each cyclic group can further include at least one atom selected from the group consisting of oxygen, sulfur and nitrogen, and each cyclic group can be substituted; X.sup.1 is hydrogen or a hydroxy protecting group; X.sup.2 is hydrogen, a carboxy protecting group, an ammonio group, an alkali metal or an alkaline-earth metal; and Y.sup.2 is hydrogen or an amino protecting group. ## Claims ### Claim 1 A pyrrolidine derivative represented by Formula II: ##STR45## wherein R.sup.2, R.sup.3 and R.sup.4 are hydrogen, lower alkyl which can be substituted, or an amino protecting group independently, or R.sup.2 and R.sup.3 together with a nitrogen atom to which R.sup.2 and R.sup.3 are bonded form a saturated or unsaturated cyclic group, or R.sup.2 and R.sup.4, or R.sup.3 and R.sup.4 together with two nitrogen atoms and one sulfur atom in the sufamide group form a saturated or unsaturated cyclic group; each cyclic group can further include at least one atom selected from the group consisting of oxygen, sulfur and nitrogen, and each cyclic group can be substituted; Y.sup.1 is hydrogen or a mercapto protecting group; and Y.sup.2 is hydrogen or an amino protecting group. ### Claim 2 (depends on 1) A pyrrolidine derivative according to claim 1, wherein R.sup.4 is hydrogen. ### Claim 3 (depends on 1) A pyrrolidine derivative according to claim 1, wherein each of R.sup.2 and R.sup.3 is hydrogen, R.sup.4 is an amino protecting group, Y.sup.1 is hydrogen, and Y.sup.2 is an amino protecting group. ### Claim 4 (depends on 1) A pyrrolidine derivative according to claim 1, wherein each of R.sup.2 and R.sup.3 is hydrogen, R.sup.4 is t-butyloxycarbonyl, Y.sup.1 is hydrogen, and Y.sup.2 is t-butyloxycarbonyl. ### Claim 5 (depends on 1) A pyrrolidine derivative according to claim 1, wherein R.sup.2 and R.sup.3 together with a nitrogen atom to which R.sup.2 and R.sup.3 are bonded form a saturated or unsaturated cyclic group. ### Claim 6 (depends on 1) A pyrrolidine derivative according to claim 1, wherein R.sup.2 and R.sup.4 together with two nitrogen atoms and one sulfur atom in the sulfamide group form a saturated or unsaturated cyclic group. ### Claim 7 (depends on 1) A pyrrolidine derivative according to claim 1, wherein R.sup.3 and R.sup.4 together with two nitrogen atoms and one sulfur atom in the sulfamide group form a saturated or unsaturated cyclic group. ### Claim 8 (depends on 1) A pyrrolidine derivative according to claim 1, wherein R.sup.2, R.sup.3 and R.sup.4 are independently selected from hydrogen, hydroxy substituted lower alkyl, amino substituted lower alkyl, alkoxy substituted lower alkyl, acylamino substituted lower alkyl, lower alkylamino substituted lower alkyl, carbamoyl substituted lower alkyl, lower alkylcarbamoyl substituted lower alkyl, carbamoyloxy substituted lower alkyl, lower alkylcarbamoyloxy substituted lower alkyl, and cyano substituted lower alkyl. ### Claim 9 (depends on 1) A pyrrolidine derivative according to claim 1, wherein at least one of R.sup.2, R.sup.3 and R.sup.4 is a lower alkyl which can be substituted, and the lower alkyl comprises 1 to 6 carbon atoms. ### Claim 10 A pyrrolidine derivative represented by Formula II: ##STR46## wherein R.sup.2, R.sup.3 and R.sup.4 are hydrogen, lower alkyl which can be substituted, or an amino protecting group independently; Y.sup.1 is hydrogen or a mercapto protecting group; and Y.sup.2 is hydrogen or an amino protecting group. ### Claim 11 (depends on 10) A pyrrolidine derivative according to claim 10, wherein R.sup.2, R.sup.3 and R.sup.4 are independently selected from hydrogen, hydroxy substituted lower alkyl, amino substituted lower alkyl, alkoxy substituted lower alkyl, acylamino substituted lower alkyl, lower alkylamino substituted lower alkyl, carbamoyl substituted lower alkyl, lower alkylcarbamoyl substituted lower alkyl, carbamoyloxy substituted lower alkyl, lower alkylcarbamoyloxy substituted lower alkyl, and cyano substituted lower alkyl. ### Claim 12 (depends on 10) A pyrrolidine derivative according to claim 10, wherein at least one of R.sup.2, R.sup.3 and R.sup.4 is a lower alkyl which can be substituted, and the lower alkyl comprises 1 to 6 carbon atoms. ### Claim 13 (depends on 10) A pyrrolidine derivative according to claim 10, wherein R.sup.4 is hydrogen. ### Claim 14 A pyrrolidine derivative represented by Formula II: ##STR47## wherein R.sup.2, R.sup.3 and R.sup.4 are independently hydrogen, or an amino protecting group, or an R.sup.2 and R.sup.3 together with a nitrogen atom to which R.sup.2 and R.sup.3 are bonded form a saturated or unsaturated cyclic group, or R.sup.2 and R.sup.4, or R.sup.3 and R.sup.4 together with two nitrogen atoms and one sulfur atom in the sulfamide group form a saturated or unsaturated cyclic group; each cyclic group can further include at least one atom selected from the group consisting of oxygen, sulfur and nitrogen, and each cyclic group can be substituted; Y.sup.1 is hydrogen or a mercapto protecting group; and Y.sup.2 is hydrogen or an amino protecting group. ### Claim 15 (depends on 14) A pyrrolidine derivative according to claim 14, wherein R.sup.2 and R.sup.3 together with a nitrogen atom to which R.sup.2 and R.sup.3 are bonded form a saturated or unsaturated cyclic group. ### Claim 16 (depends on 14) A pyrrolidine derivative according to claim 14, wherein R.sup.2 and R.sup.4 together with two nitrogen atoms and one sulfur atom in the sulfamide group form a saturated or unsaturated cyclic group. ### Claim 17 (depends on 14) A pyrrolidine derivative according to claim 14, wherein at least one R.sup.2 and R.sup.3, R.sup.2 and R.sup.4 and R.sup.3 and R.sup.4 form a saturated or unsaturated cyclic group, and the saturated or unsaturated cyclic group is selected from 1,1-dioxothiadiazinyl; 1,1-dioxodihydrothiadiazinyl; 1,1,3-trioxodihydrothiadiazinyl; 1,1-dioxothiadiazolizinyl; 1,1-dioxothiadiazolinyl; 1,1,3-trioxothiadiazolinyl. ### Claim 18 (depends on 14) A pyrrolidine derivative according to claim 14, wherein R.sup.4 is hydrogen.