JPS62249983A - Azetidinode disulfide derivative - Google Patents
Azetidinode disulfide derivativeInfo
- Publication number
- JPS62249983A JPS62249983A JP61094272A JP9427286A JPS62249983A JP S62249983 A JPS62249983 A JP S62249983A JP 61094272 A JP61094272 A JP 61094272A JP 9427286 A JP9427286 A JP 9427286A JP S62249983 A JPS62249983 A JP S62249983A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- dibromo
- solvent
- compound
- acid
- 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.)
- Pending
Links
- 150000002019 disulfides Chemical class 0.000 title 1
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 3
- 150000003536 tetrazoles Chemical class 0.000 claims abstract description 3
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims abstract 2
- 239000000126 substance Substances 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 125000006239 protecting group Chemical group 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract description 24
- 150000001875 compounds Chemical class 0.000 abstract description 19
- 239000002904 solvent Substances 0.000 abstract description 10
- 239000002253 acid Substances 0.000 abstract description 8
- 238000002360 preparation method Methods 0.000 abstract description 7
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 abstract description 6
- 108090000204 Dipeptidase 1 Proteins 0.000 abstract description 3
- 102000006635 beta-lactamase Human genes 0.000 abstract description 3
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 abstract description 3
- 230000002401 inhibitory effect Effects 0.000 abstract description 3
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 abstract description 2
- 229940054266 2-mercaptobenzothiazole Drugs 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 150000003462 sulfoxides Chemical class 0.000 abstract 1
- -1 azetidinone disulfide derivatives Chemical class 0.000 description 25
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
- 238000000862 absorption spectrum Methods 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 235000010288 sodium nitrite Nutrition 0.000 description 3
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 2
- 239000005695 Ammonium acetate Substances 0.000 description 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 235000019257 ammonium acetate Nutrition 0.000 description 2
- 229940043376 ammonium acetate Drugs 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- RAFAYWADRVMWFA-UHFFFAOYSA-N 4,6-dimethyl-1h-pyrimidine-2-thione Chemical compound CC1=CC(C)=NC(S)=N1 RAFAYWADRVMWFA-UHFFFAOYSA-N 0.000 description 1
- HFNGYHHRRMSKEU-UHFFFAOYSA-N 4-Methoxybenzyl acetate Chemical compound COC1=CC=C(COC(C)=O)C=C1 HFNGYHHRRMSKEU-UHFFFAOYSA-N 0.000 description 1
- GGDMPKORYIWJCV-UHFFFAOYSA-N 4-methyl-3-sulfanyl-2h-tetrazole Chemical compound CN1C=NNN1S GGDMPKORYIWJCV-UHFFFAOYSA-N 0.000 description 1
- 229930186147 Cephalosporin Natural products 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- 108091006629 SLC13A2 Proteins 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- JAWMENYCRQKKJY-UHFFFAOYSA-N [3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-ylmethyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl]-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]methanone Chemical compound N1N=NC=2CN(CCC=21)CC1=NOC2(C1)CCN(CC2)C(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F JAWMENYCRQKKJY-UHFFFAOYSA-N 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 125000005041 acyloxyalkyl group Chemical group 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 229940124587 cephalosporin Drugs 0.000 description 1
- 150000001780 cephalosporins Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- CVJHVJHLJYPOSS-UHFFFAOYSA-N oxolane;zinc Chemical compound [Zn].C1CCOC1 CVJHVJHLJYPOSS-UHFFFAOYSA-N 0.000 description 1
- 150000002960 penicillins Chemical class 0.000 description 1
- 230000035479 physiological effects, processes and functions Effects 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- WHMDPDGBKYUEMW-UHFFFAOYSA-N pyridine-2-thiol Chemical compound SC1=CC=CC=N1 WHMDPDGBKYUEMW-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000006000 trichloroethyl group Chemical group 0.000 description 1
- 239000008096 xylene Substances 0.000 description 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
Landscapes
- Plural Heterocyclic Compounds (AREA)
Abstract
Description
【発明の詳細な説明】
産業上の利用分野
本発明は新規なアゼチジノンジスルフィド誘導体に関す
る。DETAILED DESCRIPTION OF THE INVENTION Field of the Invention The present invention relates to novel azetidinone disulfide derivatives.
従来の技術
本発明のアゼチジノンジスルフィド誘導体は文献等に未
載の新規化合物である。Prior Art The azetidinone disulfide derivative of the present invention is a new compound that has not been described in any literature.
発明が解決しようとする問題点
本発明は、後記するようにβ−ラクタマーゼ阻害作用を
有する化合物の製造中間体として有用な化合物を提供す
ることを目的とする。Problems to be Solved by the Invention The purpose of the present invention is to provide a compound useful as an intermediate for producing a compound having β-lactamase inhibitory activity, as described later.
問題点を解決するための手段
上記目的は、下記一般式（１）で表わされるアゼチジノ
ンジスルフィド誘導体により達成される。Means for Solving the Problems The above object is achieved by an azetidinone disulfide derivative represented by the following general formula (1).
即ち本発明は、一般式
（式中、Ｒ１は置換基として炭素数１〜４のアルキル基
を有することのあるベンゾチアゾール、テトラゾール、
チアジアゾール、ピリジル又はビリミジル基を、Ｒ２は
カルボキシル保護基を示す）で表わされるアゼチジノン
ジスルフィド誘導体に係る。That is, the present invention provides compounds of the general formula (wherein R1 may have an alkyl group having 1 to 4 carbon atoms as a substituent), benzothiazole, tetrazole,
The present invention relates to an azetidinone disulfide derivative represented by a thiadiazole, pyridyl or birimidyl group, and R2 represents a carboxyl protecting group.
上記一般式（１）で表わされる本発明化合物は、後記参
考例に示される様に、一般式
（式中、Ｘは塩素原子又は臭素原子を示す。Ｒ２は前記
に同じ。）で表わされる新規な化合物を経て、特開昭５
８−１８５５８９号に開示された一般式（式中、Ｒ２は
前記に同じ。）で表わされるβ−ラクタマーゼ阻害作用
を有する化合物を製造する際の中間体として有用である
。The compound of the present invention represented by the above general formula (1) is a novel compound represented by the general formula (wherein, After the development of compounds,
It is useful as an intermediate in the production of a compound having a β-lactamase inhibitory action represented by the general formula disclosed in No. 8-185589 (wherein R2 is the same as above).
前記一般式（１）においてＲ，で表わされる各複素環上
に有することのある置換基である炭素数１〜４のアルキ
ル基としては、メチル、エチル、プロピル、イソプロピ
ル、ブチル、５ｅＣ−ブチル、ｔｅｒｔ−ブチル基を挙
げることができ、これらアルキル基は上記複素環に１〜
Ｂ ４１Ｉ！１ｌｂＦ！換しうる。Examples of the alkyl group having 1 to 4 carbon atoms which may be a substituent on each heterocycle represented by R in the general formula (1) include methyl, ethyl, propyl, isopropyl, butyl, 5eC-butyl, A tert-butyl group can be mentioned, and these alkyl groups have 1 to 1 to
B41I! 1lbF! Can be exchanged.
上記においてＲ２で示されるカルボキシル保護基として
は、従来公知のものでよく、具体的には、例えば特開昭
４９−８１８８０号公報及びエッチ・イー・フライン編
セファロスポリン アンド ペニシリンズ、ケミストリ
ー アンド バイオロジー（１９７２年 アカデミツク
プレス発行）に記載のものをいずれも使用できる。好ま
しいＲ２基としては、例えばメチル、エチル、プロピル
、ブチル、ｔｅｒｔ−ブチル、トリクロロエチル等の置
換又は非置換アルキル基、ベンジル、ジフェニルメチル
、ｐ−二トロベンジル等の１ｕ換又は非置換アラルキル
基、アセトキシメチル、アセトキシエチル、プロピオニ
ルオキシエチル、ピバロイルオキシエチル、ビバロイル
ナキシプロビル、ベンゾイルオキシメチル、ベンゾイル
オキシエチル、ベンジルカルボニルオキシメチル、シク
ロヘキシルカルボニルオキシメチル等のアシルオキシア
ルキル基、メトキシメチル、エトキシメチル、ベンジル
オキシメチル等のアルコキシアルキル基、その他テトラ
ヒドロピラニル、ジメチルアミノエチル、ジメチルクロ
ロシリル、トリクロロシリル基等が例示される。The carboxyl protecting group represented by R2 in the above may be a conventionally known one, and specifically, for example, JP-A-49-81880 and Cephalosporins and Penicillins, Chemistry and Bio, edited by H.E. Any of those described in Physiology (1972, published by Academic Press) can be used. Preferred R2 groups include, for example, substituted or unsubstituted alkyl groups such as methyl, ethyl, propyl, butyl, tert-butyl, and trichloroethyl, 1u-substituted or unsubstituted aralkyl groups such as benzyl, diphenylmethyl, p-nitrobenzyl, and acetoxy. Acyloxyalkyl groups such as methyl, acetoxyethyl, propionyloxyethyl, pivaloyloxyethyl, bivaloylnaxyprovil, benzoyloxymethyl, benzoyloxyethyl, benzylcarbonyloxymethyl, cyclohexylcarbonyloxymethyl, methoxymethyl, ethoxymethyl, Examples include alkoxyalkyl groups such as benzyloxymethyl, and other groups such as tetrahydropyranyl, dimethylaminoethyl, dimethylchlorosilyl, and trichlorosilyl groups.
本発明誘導体（１）は、下記反応工程式に従って製造で
きる。The derivative (1) of the present invention can be produced according to the following reaction scheme.
〈反応工程式〉
（ＩＶ）
（式中、Ｒ１及びＲ２は前記に同じ。）即ち、一般式（
ＩＶ）で表わされるペニシラン酸スルホキシド誘導体を
通常１〜１．５倍モル程度の一般４一
式■で表わされるメルカプト誘導体と反応させることに
より一般式（Ｉ）で表わされるアゼチジノンジスルフィ
ド誘導体を得る。一般式（１ｖ）で表わされる化合物は
公知の化合物であり、ジャーナル オブケミカル ソサ
エティー（Ｊ、 Ｏｈｅｍ、 Ｓｏａ、）（１９６９）
＊２１２８〜２１２７に記載されている。反応は適当な
溶媒中で、加熱することによって行なわれる。使用され
る溶媒としては、テトラヒドロフラン、ジオキサン等の
エーテル類、ベンゼン、トルエン、キシレン等の芳香族
炭化水素類、クロロホルム、四塩化炭素、ジクロロエタ
ン等のハロゲン化炭化水素等を例示できる。反応は、通
常５０〜１５０ ”Ｃ程度の温度で、通常０．５〜１０
時間程度で完結する。<Reaction process formula> (IV) (In the formula, R1 and R2 are the same as above.) That is, the general formula (
The azetidinone disulfide derivative represented by general formula (I) is obtained by reacting the penicillanic acid sulfoxide derivative represented by IV) with a mercapto derivative represented by general formula 4 (1) in an amount usually about 1 to 1.5 times the mole. The compound represented by general formula (1v) is a known compound, and is published in the Journal of Chemical Society (J, Ohem, Soa, 1969).
*Described in 2128-2127. The reaction is carried out in a suitable solvent by heating. Examples of the solvent used include ethers such as tetrahydrofuran and dioxane, aromatic hydrocarbons such as benzene, toluene and xylene, and halogenated hydrocarbons such as chloroform, carbon tetrachloride and dichloroethane. The reaction is usually carried out at a temperature of about 50 to 150"C, usually 0.5 to 10"C.
It will be completed in about an hour.
反応終了後は、常法により生成物を単離できる。After the reaction is complete, the product can be isolated by conventional methods.
一般式（ＩＶ）で表わされる化合物の製造例については
後記参考例で示す。Production examples of the compound represented by the general formula (IV) will be shown in Reference Examples below.
実施例
以下、実施例及び参考例を挙げて、本発明をより具体的
に説明する。EXAMPLES Hereinafter, the present invention will be explained in more detail with reference to Examples and Reference Examples.
参考例１
６．６−ジプロモー２β−クロロメチル−２ａ−メチル
ペナム−８α−カルボン酸ベンズヒドリルエステルの製
造
８．８−ジブロモ−４−（ベンゾチアゾール−２−イル
）ジチオ−２−オキソアゼチジン−１−（２−イソプロ
ペニル）酢酸ベンズヒドリルエステル６、Ｂ１１をジク
ロロメタン４０ ｍｌｌに浴解し、１２％塩酸１７ ｍ
ｌを加えた後水冷撹拌下亜硝酸ナトリウム１．２６Ｆの
水溶液ｔ ｏ ｍｌを滴下した。滴下後、室温にもどし
同温にて４．５時間撹拌した。反応液を飽和食塩水で洗
浄後硫酸マグネシウムで乾燥した。溶媒を減圧上濃縮後
、残渣をシリカゲルカラムクロマトグラフィーに付しく
展開溶媒；ベンゼン：クロロホルム＝８ ： １ ）目
的化合物である油状物を８．８８ＳＦ得た（収率７６％
）。Reference Example 1 Production of 6.6-dibromo-2β-chloromethyl-2a-methylpenam-8α-carboxylic acid benzhydryl ester 8.8-dibromo-4-(benzothiazol-2-yl)dithio-2-oxoazetidine-1- (2-isopropenyl)acetic acid benzhydryl ester 6, B11 was dissolved in 40 ml of dichloromethane, and 17 ml of 12% hydrochloric acid was added.
After adding 1.0 ml of an aqueous solution of 1.26 F sodium nitrite while stirring under water cooling, t0 ml of an aqueous solution of sodium nitrite was added dropwise. After dropping, the mixture was returned to room temperature and stirred at the same temperature for 4.5 hours. The reaction solution was washed with saturated brine and dried over magnesium sulfate. After concentrating the solvent under reduced pressure, the residue was subjected to silica gel column chromatography (developing solvent: benzene:chloroform = 8:1) to obtain 8.88 SF of an oily substance (yield: 76%), which is the target compound.
).
赤外吸収スペクトル（Ｎａ０Ｊｉ’ ）νｍａｘ（Ｃｍ
）＝１８１０．１７６０゜核磁気共鳴スペクトル（
ＣＤ０１ａ ）δ（ｐｐｍ ）＝７．８５ （１０Ｈ，
Ｂ ）、６．９４ （ＩＥ［、ｓ ）、５．８５（Ｉｎ
、ｓ）、５．１６（ＩＨ，Ｅｌ）、８．６８，８．５２
（各ＩＨ，ＡＢ、Ｊ＝１２）、１．３１ （８Ｈ，Ｓ
）。Infrared absorption spectrum (Na0Ji') νmax (Cm
) = 1810.1760° nuclear magnetic resonance spectrum (
CD01a) δ (ppm) = 7.85 (10H,
B ), 6.94 (IE[,s ), 5.85 (In
, s), 5.16 (IH, El), 8.68, 8.52
(each IH, AB, J=12), 1.31 (8H, S
).
実施例１
８．３−ジブロモ−４−（ベンゾチアゾール−２−イル
）ジチオ−２−オキソアゼチジン−１−（２−イソプロ
ペニル）酢酸ベンズヒドリルエステルの製造
６．６−ジブロモペニシラン酸ベンズヒドリルエステル
−１−オキシド５．５９，２−メルカプトベンゾチアゾ
ール１．７ｇをトルエン８０ｍ１中、８０分間加熱還流
した。減圧下トルエンを留去し、得られた残渣にクロロ
ホルム−メタノール−エーテルを加えて目的物６．４６
ｆを得た。Example 1 8. Preparation of 3-dibromo-4-(benzothiazol-2-yl)dithio-2-oxoazetidine-1-(2-isopropenyl)acetic acid benzhydryl ester 6.6-Dibromopenicilanic acid benzhydryl ester -1-oxide 5.59, 1.7 g of 2-mercaptobenzothiazole was heated under reflux for 80 minutes in 80 ml of toluene. Toluene was distilled off under reduced pressure, and chloroform-methanol-ether was added to the resulting residue to obtain the desired product 6.46.
I got f.
核磁気共鳴スペクトル（ＯＤＭａ ）
δ（１）ｐｍ） ＝ １．９０ （８Ｈ，Ｓ ）、４．
９２〜５．１７（８Ｈ，ｍ）、５．８２（ＩＨ，ｓ）、
６．９４（１１（ＩＳ）、７．２５〜７．５５（１２Ｈ
，ｍ）、’１．’ｌ ８〜７．９５ （２Ｉ−Ｉ、 ｍ
）。Nuclear magnetic resonance spectrum (ODMa) δ(1)pm) = 1.90 (8H,S), 4.
92-5.17 (8H, m), 5.82 (IH, s),
6.94 (11 (IS), 7.25-7.55 (12H)
, m), '1. 'l 8~7.95 (2I-I, m
).
実施例２
８．８−ジブロモ−４−（ベンゾチアゾール−２−イル
）ジチオ−２−オキソアゼチジン−１−（２−イソプロ
ペニル）酢酸ｐ−メトキシベンジルエステルの製造
６．６−ジブロモペニシラン酸ｐ−メトキシベンジルエ
ステル−１−オキシド１２．２１Ｊ、２−メルカプトベ
ンゾチアゾール４．１１をトルエン１５０ｍ１中、１時
間加熱還流した。減圧下トルエンを留去し、得られた残
渣にエーテルを加えて目的物を１１．２ダ得た。Example 2 Preparation of 8.8-dibromo-4-(benzothiazol-2-yl)dithio-2-oxoazetidine-1-(2-isopropenyl)acetic acid p-methoxybenzyl ester 6.6-dibromopenicillanic acid p 12.21 J of -methoxybenzyl ester-1-oxide and 4.11 J of 2-mercaptobenzothiazole were heated under reflux for 1 hour in 150 ml of toluene. Toluene was distilled off under reduced pressure, and ether was added to the resulting residue to obtain 11.2 days of the desired product.
核磁気共鳴スペクトル（ＯＤＯｌｇ ）δ（ｐｌ）ｍ）
＝ １．９０ （８Ｈ，ｓ ）、８．７４（８Ｈ，８
）、４．９５〜５．１９ （５Ｈ，ｍ ）、５．８２（
ＩＨ，ｓ）、６．８０ （２Ｈ，ｄ、 Ｊ＝８．８Ｈｚ
）、７．２１〜７．５８ （４Ｈ，ｍ ）、７．７５〜
７．９７ （２Ｈ，ｍ ）。Nuclear magnetic resonance spectrum (ODOlg)δ(pl)m)
= 1.90 (8H, s ), 8.74 (8H, 8
), 4.95-5.19 (5H, m ), 5.82 (
IH,s), 6.80 (2H,d, J=8.8Hz
), 7.21~7.58 (4H,m), 7.75~
7.97 (2H,m).
実施例８
８．８−ジブロモ−４（１−メチルテトラゾール−２−
イル）ジチオ−２−オキソアゼチジン−１−（２−イソ
プロペニル）酢酸ｐ−ニトロベンジルエステルの製造
６．６−ジブロモペニシラン酸ｐ−ニトロベンジルエス
テル−１−オキシド０．２２５ｆ、２−メルカプト−１
−メチルテトラゾール０．０５８ｆをベンゼンｌｏ ｍ
ｌｌｌｌ中間時間加熱還流。減圧下＃編し目的化合物で
ある油状物をｏ、２９５ｐＰ４ｔこ。Example 8 8.8-dibromo-4(1-methyltetrazole-2-
Preparation of p-nitrobenzyl dithio-2-oxoazetidine-1-(2-isopropenyl)acetic acid 6.6-Dibromopenicillanic acid p-nitrobenzyl ester-1-oxide 0.225f, 2-mercapto-1
-Methyltetrazole 0.058f in benzene lo m
Heat to reflux for an intermediate time. The target compound, an oily substance, was prepared under reduced pressure at 295 pP4t.
核磁気共鳴スペクトル（ＣＤ０１ｅ ）δ（ｐｐｍ）
＝ １．８９ （、８Ｈ，８）、４．０８（８Ｈ，８）
、５．０５（２Ｈ，Ｂ）、６．１８〜５．１８（１ａ、
ｍ）、５．２９ （２Ｈ，ｓ ）、５．８８（ｔｎ、ｓ
）、７．５’＋ （２１（、ｄ、 Ｊ＝８．８七）、８
．１９ （２Ｈ，ｄ、Ｊ＝８．８Ｈｚ）。Nuclear magnetic resonance spectrum (CD01e) δ (ppm)
= 1.89 (, 8H, 8), 4.08 (8H, 8)
, 5.05 (2H, B), 6.18-5.18 (1a,
m), 5.29 (2H,s), 5.88 (tn,s
), 7.5'+ (21(, d, J=8.87), 8
．． 19 (2H, d, J=8.8Hz).
実施例４
８．８−ジブロモ−４−（５−メチル−１，８，４−チ
アジアゾール−２−イル）ジチオ−２−オキソアゼチジ
ン−１−（２−イソプロペニル）酢酸ｐ−ニトロベンジ
ルエステルの製造
６．６−ジブロモペニシラン酸ｐ−ニトロベンジルエス
テル−１−オキシド０．１０２ｆ、２−メルカプト−５
−メチル−１，８，４−チアジアゾール０．０２６Ｆを
トルエン２ ｍｌｌ中、２．５時間加熱還流した。溶媒
を減圧上濃縮し、目的物である油状物を０．１２１Ｆ得
た。Example 4 Preparation of 8.8-dibromo-4-(5-methyl-1,8,4-thiadiazol-2-yl)dithio-2-oxoazetidine-1-(2-isopropenyl)acetic acid p-nitrobenzyl ester 6.6-Dibromopenicillanic acid p-nitrobenzyl ester-1-oxide 0.102f, 2-mercapto-5
-Methyl-1,8,4-thiadiazole 0.026F was heated under reflux in 2 ml of toluene for 2.5 hours. The solvent was concentrated under reduced pressure to obtain the desired oily substance at 0.121F.
核磁気共鳴スペクトル（０ＤＣｌａ ）δ（ｐｐｍ）
＝ １．９１ （８Ｈ，ｓ ）、２．８０（８Ｈ，ｓ）
、５．０１〜５．０６（２Ｈ，ｍ）、５．２１〜５．２
８ （１１（、ｍ ）、５．８４ （２Ｈ，ｓ ）、５
．８８ （ＩＨ，ｓ ）、７．５５ （２Ｈ，ｃｌ、
Ｊ＝８．６Ｈｚ）、８．２１ （２Ｈ，ｃｌ 、 Ｊ
＝８．６Ｈｚ）。Nuclear magnetic resonance spectrum (0DCla) δ (ppm)
= 1.91 (8H,s), 2.80 (8H,s)
, 5.01-5.06 (2H, m), 5.21-5.2
8 (11(,m), 5.84 (2H,s), 5
．． 88 (IH,s), 7.55 (2H,cl,
J = 8.6Hz), 8.21 (2H, cl, J
=8.6Hz).
実施例５
８．８−ジブロモ−４（ピリジン−２−イル）ジチオ−
２−オキソアゼチジン−１−（２−イソプロペニル）酢
酸ｐ−二トロベンジルエステルの製造
６．６−ジブロモペニシラン酸ｐ−ニトロベンジルエス
テル−１−オキシドｏ、ｔｏｐと２−メルカプトピリジ
ン０．０２８Ｆをトルエン５ ｍｌｌ中 １時間加熱還
流した。溶媒を減圧上濃縮し、目的化合物である油状物
を０．１１ Ｆ得た。Example 5 8.8-dibromo-4(pyridin-2-yl)dithio-
Preparation of 2-oxoazetidine-1-(2-isopropenyl)acetic acid p-nitrobenzyl ester 6. 6-Dibromopenicillanic acid p-nitrobenzyl ester-1-oxide o,top and 2-mercaptopyridine 0.028F The mixture was heated under reflux in 5 ml of toluene for 1 hour. The solvent was concentrated under reduced pressure to obtain an oily substance having a concentration of 0.11 F, which was the target compound.
核磁気共鳴スペクトル（０ＤＯＡ！ａ ）δ（ｐｐｍ）
＝ １．９１ （８Ｈ，Ｓ ）、５．００（２Ｈ，ｓ
）、５．１９〜５．２１ （ｌ Ｈｅ ｍ ）、５．８
０（２Ｈｅ ｓ ）、５．５８ （ＬＨ，Ｅｌ ）、７
．１０〜７．２６ （２Ｈ，ｍ ）、７．４７〜７．６
９（２Ｈ＊ ｍ ）、８．２０ （２Ｈ，ｄ、 Ｊ＝８
．８ ）、８．４７〜８．５８ （２Ｈ，ｍ ）。Nuclear magnetic resonance spectrum (0DOA!a) δ (ppm)
= 1.91 (8H,S), 5.00 (2H,s
), 5.19-5.21 (l He m ), 5.8
0 (2He s ), 5.58 (LH, El ), 7
．． 10-7.26 (2H, m), 7.47-7.6
9 (2H*m), 8.20 (2H, d, J=8
．． 8), 8.47-8.58 (2H, m).
実施例６
８．８−ジブロモ−４（４，６−シメチルビリミジンー
２−イル）ジチオ−２−オキソアゼチジン−１−（２−
イソプロペニルｌｌ：酸ｐ−二トロペンジルエステルの
製造
６．６−ジブロモペニシラン酸ｐ−ニトロベンジルエス
テル−１−オキシド０．１ ＯｆＩと４，６−シメチル
ー２−メルカプトピリミジン０．０８０ｆを）ルエン５
ｍｌｌｌｌ中間時間加熱還流。減圧上濃縮し目的化合
物である油状物を０．１０ ｇ得た。Example 6 8.8-Dibromo-4(4,6-dimethylpyrimidin-2-yl)dithio-2-oxoazetidine-1-(2-
Isopropenyl 1: Preparation of acid p-nitrobenzyl ester 6.6-dibromopenicillanic acid p-nitrobenzyl ester-1-oxide 0.1 OfI and 4,6-dimethyl-2-mercaptopyrimidine 0.080f) Luen 5
Heat to reflux for an intermediate time. The mixture was concentrated under reduced pressure to obtain 0.10 g of an oily substance, which was the target compound.
核磁気共鳴スペクトル（０ＤＯｌＢ ）δ（ｐｐｍ）
＝ １．９２ （８Ｈ，ｓ ）、２．４８（６Ｈ，ｓ）
、５．００〜５．０７ （２Ｈ，ｍ ）、５．１９〜５
．２４ （ＬＨ，ｍ ）、５．８１（２Ｈ，ｓ）、５．
５５（ＬＨ，ｓ ）、６．８８（ＬＨ，ｓ）、７．５４
（２Ｈ，ｄ、 Ｊ＝８．８ ）、８．２０（２Ｈ，ｄ
、 Ｊ＝８．８ ）。Nuclear magnetic resonance spectrum (0DOlB) δ (ppm)
= 1.92 (8H,s), 2.48 (6H,s)
, 5.00-5.07 (2H, m), 5.19-5
．． 24 (LH, m ), 5.81 (2H, s), 5.
55 (LH, s), 6.88 (LH, s), 7.54
(2H, d, J=8.8), 8.20 (2H, d
, J=8.8).
参考例２
６．６−ジプロモー２β−クロロメチル−’ｌａ−メチ
ルペナム−８ａ−カルボン酸ベンズヒドリルエステルの
製造
８．３−ジブロモ−４−（ベンゾチアゾール−２−イル
）ジチオ−２−オキソアゼチジン−１−（２−イソプロ
ペニル）酢酸ベンズヒドリルエステル６８２Ｆをジクロ
ロメタン４９ ｍｌに浴解し、１２％塩酸１７ ｍｌｌ
を加えた後水冷撹拌下亜硝酸ナトリウム１．２６Ｆの水
溶９１０ ｍｌを滴下した。滴下後、室温にもどし同温
にて４．５時間撹拌した。Reference Example 2 Production of 6.6-dibromo-2β-chloromethyl-'la-methylpenam-8a-carboxylic acid benzhydryl ester 8.3-dibromo-4-(benzothiazol-2-yl)dithio-2-oxoazetidine-1 -(2-isopropenyl)acetic acid benzhydryl ester 682F was dissolved in 49 ml of dichloromethane, and 17 ml of 12% hydrochloric acid was added.
After that, 910 ml of a 1.26F aqueous solution of sodium nitrite was added dropwise while stirring while cooling with water. After dropping, the mixture was returned to room temperature and stirred at the same temperature for 4.5 hours.
反応液に水を加え有機層を分液し、水、飽和重曹水、飽
和食塩水で洗浄後硫酸マグネシウムで乾燥した。溶媒を
減圧上濃縮後、残渣をシリカゲルカラムクロマトグラフ
ィーに付しく展開溶媒；ベンゼン：クロロホルム＝８：
１）目的化合物である油状物を８．８８Ｆ得た（収率７
６％）。Water was added to the reaction solution, and the organic layer was separated, washed with water, saturated aqueous sodium bicarbonate, and saturated brine, and dried over magnesium sulfate. After concentrating the solvent under reduced pressure, the residue was subjected to silica gel column chromatography using developing solvent: benzene:chloroform=8:
1) 8.88F of the target compound oil was obtained (yield: 7
6%).
赤外吸収スペクトル（ＮａＣ１）
ｖ ｍａｙ：、 （Ｃｍ ） ” １８１０．１７６
０゜核磁気共鳴スペクトル（ＯＤＯ＃ａ ）δ（ｐｐｍ
） ＝ ７．８５ （１０Ｈ，ｓ ）、６．９４ （Ｉ
Ｈ，Ｅｌ）、５．８５ （ＩＨ，ｓ 、）、５．１６（
ＩＨ，ｓ）、８．６８，８．５２（各ＩＨ，ＡＢ、Ｊ＝
１２）、１．８１（８Ｈ，ｓ）。Infrared absorption spectrum (NaC1) v may:, (Cm) ” 1810.176
0° nuclear magnetic resonance spectrum (ODO#a) δ (ppm
) = 7.85 (10H,s), 6.94 (I
H, El), 5.85 (IH, s,), 5.16 (
IH, s), 8.68, 8.52 (each IH, AB, J=
12), 1.81 (8H, s).
参考例８
２β−クロロメチル−２α−メチルペナム−８α−カル
ボン酸ベンズヒドリルエステルの製造６．６−ジプロモ
ー２β−クロロメチル−２α−メチルペナム−３α−カ
ルボン酸ベンズヒドリルエステル０．５６ｆ、酢酸アン
モニウム０．８４ ｆをテトラハイドロフラン６ ｍｌ
Ｎ Ｈｚ０２ ｍ（ｌ に俗解し、水冷撹拌下に亜鉛
０２６ｆを加えた。室温にもどして１時間撹拌した後、
反応液を濾過した。Ｐ液を塩化メチレン２０−で抽出し
、抽出液はＩＭ酢酸アンモニウム水溶液１０ｍＪ？で洗
浄し、硫酸マグネシウムで乾燥した。溶媒を減圧下に留
去し、残渣を０．８２Ｌ！得た。Reference Example 8 Production of 2β-chloromethyl-2α-methylpenam-8α-carboxylic acid benzhydryl ester 6.6-dipromo 2β-chloromethyl-2α-methylpenam-3α-carboxylic acid benzhydryl ester 0.56f, ammonium acetate 0. 84 f and 6 ml of tetrahydrofuran
Zinc 026f was added under water cooling and stirring. After returning to room temperature and stirring for 1 hour,
The reaction solution was filtered. The P solution was extracted with 20-methylene chloride, and the extract was mixed with 10 mJ of IM ammonium acetate aqueous solution. and dried over magnesium sulfate. The solvent was distilled off under reduced pressure, leaving a residue of 0.82L! Obtained.
赤外吸収スペクトル（０ＨＯＩＩｓ ）ｍ−１−
シｍａｘ−１７８５．１７４５゜
核磁気共鳴スペクトル（ＯＤＯ＃ａ ）δ（ｐｐｍ）＝
１．８８（８Ｈｓ ｓ）、８．１１ （ＩＨ，ＡＢＸ。Infrared absorption spectrum (0HOIIs) m-1-simax-1785.1745° Nuclear magnetic resonance spectrum (ODO#a) δ (ppm) =
1.88 (8Hs s), 8.11 (IH, ABX.
ＪＡＢ ＝ １６．０ Ｈｚ 、 ＪＡＸ ＝ １．８
Ｈｚ ）、８．７６（ＩＨ，ＡＢＸ、 ＪＡＢ＝１６
．０Ｈｚ、 Ｊｎｘ＝４．０Ｈｚ）、８．６０（２Ｈ，
ｓ）、５．１８（ＬＨ，ｓ）、５．８７〜５−４４ （
ＩＨ，ｍ）、６．９４ （ＩＨ，Ｂ ）、７．８５ （
ＩＯＨ，Ｓ ）。JAB = 16.0 Hz, JAX = 1.8
Hz), 8.76 (IH, ABX, JAB=16
．． 0Hz, Jnx=4.0Hz), 8.60(2H,
s), 5.18 (LH, s), 5.87 to 5-44 (
IH, m), 6.94 (IH, B), 7.85 (
IOH,S).
参考例４
２β−アジドメチル−２α−メチルペナム−８α−カル
ボン酸ベンズヒドリルエステルの製造２β−クロルメチ
ル−２α−メチルペナム−３α−カルボン酸ベンズヒド
リルエステル２．４４’のジメチルホルムアミド溶液ｉ
ｏ ｏ ｍｌ中に、アジ化ナトリウム２．８８ｆの水
溶液を加え、室温で４時間撹拌した。反応混合物を水に
注ぎ、エーテル抽出した。エーテル層を水洗後、濃縮し
て、２，２ｆの油状物質を得た（収率８９％）。Reference Example 4 Production of 2β-azidomethyl-2α-methylpenam-8α-carboxylic acid benzhydryl ester Dimethylformamide solution of 2β-chloromethyl-2α-methylpenam-3α-carboxylic acid benzhydryl ester 2.44′ i
An aqueous solution of 2.88 f of sodium azide was added to the solution, and the mixture was stirred at room temperature for 4 hours. The reaction mixture was poured into water and extracted with ether. The ether layer was washed with water and concentrated to obtain 2,2f oil (yield: 89%).
赤外吸収スペクトル（５Ｌシヨール）
νｍａｘ（Ｃｍ ）＝２１２０１１８１２．１７６５゜
核磁気共鳴スペクトル（ＯＤＯｌｇ ）δ（ｐｐｍ ）
；１．８０ （８Ｈｅ Ｂ ）、８．２５（２Ｈ，ｍ
）、８．４２（ＩＨ，ｉ、８．６８ （ＩＨ，ｄ ）、
４．７５（ＬＨ，ｓ）、４．７６（ＬＨ，ｍ）、７．０
０（ＩＨ，ｓ）、７．４０ （１０ｆ（、ｓ）。Infrared absorption spectrum (5L sill) νmax (Cm) = 212011812.1765° Nuclear magnetic resonance spectrum (ODOlg) δ (ppm)
;1.80 (8He B ), 8.25 (2H, m
), 8.42 (IH,i, 8.68 (IH,d ),
4.75 (LH, s), 4.76 (LH, m), 7.0
0(IH,s), 7.40 (10f(,s).
参考例５
２β−アジドメチル−２ａ−メチルペナム−８ａ−カル
ボン酸−１，１−ジオキシドベンズヒドリルエステルの
製造
２β−アジドメチル−２α−メチルペナム−８α−カル
ボン酸ベンズヒドリルエステル２．２２Ｆ。Reference Example 5 Production of 2β-azidomethyl-2a-methylpenam-8a-carboxylic acid-1,1-dioxide benzhydryl ester 2β-azidomethyl-2α-methylpenam-8α-carboxylic acid benzhydryl ester 2.22F.
過マンガン酸カリウム１．９Ｆを酢酸’１５ｍ１．水１
２ｍｇの混合溶媒に加えた。室温で４時間撹拌後、氷水
を加えて、生じた沈殿物を炉取、水洗した。Add 1.9F of potassium permanganate to 15ml of acetic acid. water 1
It was added to 2 mg of mixed solvent. After stirring at room temperature for 4 hours, ice water was added, and the resulting precipitate was filtered out and washed with water.
これをエーテルに溶解し、炭酸水素ナトリウム水溶液で
洗浄後、濃縮して、目的とする化合物１．４９ｆを得た
（収率６２．２％）。This was dissolved in ether, washed with an aqueous sodium bicarbonate solution, and then concentrated to obtain the target compound 1.49f (yield 62.2%).
赤外吸収スペクトル（ヌジョール）
νｍａｘ（Ｃｍ ）＝２１２０．１８１２．１７６５゜
核磁気共鳴スペクトル（０ＤＯｈ ）
δ（ｐｐｍ） ＝ １．１８ （８Ｈ，ｓ ）、８．５
０（２Ｈ，ｄ）、８．７２（ＩＨ，ｄ）、８．９３ （
ＩＩ−Ｉ、 ｃｌ ）、４．６０（ＩＪｍ）、４．６５
（１１（、Ｓ ）、７．００ （ＩＨ，ｓ ）、７．
８６ （ＩＯＨ，ｓ ）。Infrared absorption spectrum (Nujol) νmax (Cm) = 2120.1812.1765° Nuclear magnetic resonance spectrum (0DOh) δ (ppm) = 1.18 (8H, s), 8.5
0 (2H, d), 8.72 (IH, d), 8.93 (
II-I, cl), 4.60 (IJm), 4.65
(11(,S), 7.00 (IH,s), 7.
86 (IOH,s).
（以上）(that's all)
Claims (1)
基を有することのあるベンゾチアゾール、テトラゾール
、チアジアゾール、ピリジル又はピリミジル基を、Ｒ＿
２はカルボキシル保護基を示す）で表わされるアゼチジ
ノンジスルフィド誘導体。(1) General formula ▲ Numerical formula, chemical formula, table, etc. ▼ (In the formula, R_1 is a benzothiazole, tetrazole, thiadiazole, pyridyl, or pyrimidyl group that may have an alkyl group with 1 to 4 carbon atoms as a substituent, R_
2 represents a carboxyl protecting group).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61094272A JPS62249983A (en) | 1986-04-22 | 1986-04-22 | Azetidinode disulfide derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61094272A JPS62249983A (en) | 1986-04-22 | 1986-04-22 | Azetidinode disulfide derivative |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS62249983A true JPS62249983A (en) | 1987-10-30 |
Family
ID=14105634
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61094272A Pending JPS62249983A (en) | 1986-04-22 | 1986-04-22 | Azetidinode disulfide derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62249983A (en) |
-
1986
- 1986-04-22 JP JP61094272A patent/JPS62249983A/en active Pending
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