JPS6372679A - Production of imidazole derivative - Google Patents
Production of imidazole derivativeInfo
- Publication number
- JPS6372679A JPS6372679A JP61217767A JP21776786A JPS6372679A JP S6372679 A JPS6372679 A JP S6372679A JP 61217767 A JP61217767 A JP 61217767A JP 21776786 A JP21776786 A JP 21776786A JP S6372679 A JPS6372679 A JP S6372679A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- donor
- compound expressed
- formaldehyde
- ammonia
- 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
- 238000004519 manufacturing process Methods 0.000 title claims description 11
- 150000002460 imidazoles Chemical class 0.000 title claims description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 36
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 24
- 150000001875 compounds Chemical class 0.000 claims abstract description 16
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 11
- 239000000126 substance Substances 0.000 claims 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract description 12
- 229960001380 cimetidine Drugs 0.000 abstract description 8
- 238000006243 chemical reaction Methods 0.000 abstract description 5
- 239000002994 raw material Substances 0.000 abstract description 5
- 230000000767 anti-ulcer Effects 0.000 abstract description 2
- 239000002798 polar solvent Substances 0.000 abstract description 2
- 238000010992 reflux Methods 0.000 abstract description 2
- OVLUBEIAVGIZEN-UHFFFAOYSA-N 1-cyano-3-[2-(2,3-dioxobutylsulfanyl)ethyl]-2-methylguanidine Chemical compound N#CNC(=NC)NCCSCC(=O)C(C)=O OVLUBEIAVGIZEN-UHFFFAOYSA-N 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- CCGSUNCLSOWKJO-UHFFFAOYSA-N cimetidine Chemical compound N#CNC(=N/C)\NCCSCC1=NC=N[C]1C CCGSUNCLSOWKJO-UHFFFAOYSA-N 0.000 abstract 1
- AAOVKJBEBIDNHE-UHFFFAOYSA-N diazepam Chemical compound N=1CC(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 AAOVKJBEBIDNHE-UHFFFAOYSA-N 0.000 abstract 1
- 230000000246 remedial effect Effects 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 238000000034 method Methods 0.000 description 9
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
- AQIXAKUUQRKLND-UHFFFAOYSA-N cimetidine Chemical compound N#C/N=C(/NC)NCCSCC=1N=CNC=1C AQIXAKUUQRKLND-UHFFFAOYSA-N 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 5
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 235000019270 ammonium chloride Nutrition 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- 239000004020 conductor Substances 0.000 description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000003472 neutralizing effect Effects 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 2
- 235000019345 sodium thiosulphate Nutrition 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 1
- XXJGBENTLXFVFI-UHFFFAOYSA-N 1-amino-methylene Chemical compound N[CH2] XXJGBENTLXFVFI-UHFFFAOYSA-N 0.000 description 1
- PDWPOXKSTFGRIT-UHFFFAOYSA-N 4-(chloromethyl)-5-methyl-1h-imidazole;hydrochloride Chemical compound Cl.CC=1NC=NC=1CCl PDWPOXKSTFGRIT-UHFFFAOYSA-N 0.000 description 1
- -1 4-methyl-5-imidazolyl Chemical group 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- 102000003710 Histamine H2 Receptors Human genes 0.000 description 1
- 108090000050 Histamine H2 Receptors Proteins 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- MGJURKDLIJVDEO-UHFFFAOYSA-N formaldehyde;hydrate Chemical compound O.O=C MGJURKDLIJVDEO-UHFFFAOYSA-N 0.000 description 1
- 230000027119 gastric acid secretion Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 230000002747 voluntary effect Effects 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【発明の詳細な説明】
本発明は、イミダゾール誘導体の製造方法に関し、更に
詳細には、
式（１）
で表わされるＮ−シアノード−メチル−マー〔２−（５
−メチル−４−イミダゾリルメチルチオ）エチル〕グア
ニジンの新規な製造方法に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for producing an imidazole derivative, and more particularly, to a method for producing an imidazole derivative, and more specifically, the present invention relates to a method for producing an imidazole derivative, and more particularly, to a method for producing an imidazole derivative, N-cyanode-methyl-mer [2-(5
-Methyl-4-imidazolylmethylthio)ethyl] A novel method for producing guanidine.
本発明方法で製造される式（１）で表わされる化合物は
、一般名金シメチシンといい、ヒスタミンＨ２受容体拮
抗゛作用に基づく胃酸分泌抑制作用を示し、抗潰瘍治療
剤として広く使用されている。The compound represented by formula (1) produced by the method of the present invention is commonly called gold cimetisine, exhibits gastric acid secretion suppressing action based on histamine H2 receptor antagonism, and is widely used as an anti-ulcer therapeutic agent. .
シメチジンの製法については従来から徳々の方法が報告
されている。米国特許第４，０１３，６７８号における
製法によれば、シメチジンは塩基の存在下、４−クロロ
メチル−５−メチルイミダゾール塩酸塩ｔ−Ｎ−シアノ
ード−メチル−ｙ−（２−メルカ！トエチル）グアニジ
ンと反応させて製造されている。又、ドイツ特許第２．
２１１．４５４号には、式、Ｈａ ｔ −ＣＨ２−Ｑ
Ｃ式中、Ｑは脱離基、Ｈ＠ｔは４−メチル−５−イミ
ダゾリル基を示す）で表わされる化合物とＨ８ＣＨ２Ｃ
Ｈ２ＮＨ２を反応させて、式、Ｈ＠ ｔＣＨ２ＳＣＨ２
ＣＨ２ＮＨ２で表わされる化合物を得、次いでこれ金、
はアリール基を示す）で表わ石れる化合物を反応させシ
メチジンを得ている。As for the production method of cimetidine, Tokutoshi's method has been reported so far. According to the process in U.S. Pat. No. 4,013,678, cimetidine is converted into 4-chloromethyl-5-methylimidazole hydrochloride t-N-cyano-methyl-y-(2-merca!toethyl) in the presence of a base. It is produced by reacting with guanidine. Also, German Patent No. 2.
No. 211.454 contains the formula, Hat -CH2-Q
A compound represented by the formula C (where Q is a leaving group and H@t is a 4-methyl-5-imidazolyl group) and H8CH2C
React H2NH2 to form the formula H@tCH2SCH2
A compound represented by CH2NH2 was obtained, and this was then reacted with a compound represented by gold (indicates an aryl group) to obtain cimetidine.
しかしながらこれらの製造法は原料の問題や反応工程の
煩雑さなど多くの問題点があった。However, these production methods have many problems such as problems with raw materials and complicated reaction steps.
そこで本発明者は、上記の欠点を解決すべく鋭意研究し
、本発明を完成し九。Therefore, the present inventor conducted extensive research to solve the above-mentioned drawbacks and completed the present invention.
即ち、本発明は、
式（ｎ）、
（ｎ）
で表わされる化合物に、ホルムアルデヒド又はホルムア
ルデヒド供与体及びアンモニア又はアンモニア供与棒金
反応させることを特徴とする、式（１）
で表わされるイミメゾール肪導体の製造法に関する。That is, the present invention provides an imimezole fatty conductor represented by formula (1), which is characterized in that a compound represented by formula (n) or (n) is reacted with formaldehyde or a formaldehyde donor and ammonia or an ammonia donor bar. Concerning the manufacturing method.
本発明方法において用いられるホルムアンプヒト供与体
としては、例えばパラホルムアルデヒド、ホＡ／ｆｆリ
ン、トリオキサンなどがあげられ、アンモニア供与体と
しては、例えば、塩化アンモニウム、酢酸アンモニウム
、テトラメチレンへキサミン、リン酸二水素アンモニウ
ムなどがあげられる。Examples of the formamp human donor used in the method of the present invention include paraformaldehyde, foA/ff phosphorus, trioxane, etc., and examples of the ammonia donor include ammonium chloride, ammonium acetate, tetramethylenehexamine, phosphorus, etc. Examples include ammonium dihydrogen acid.
式（Ｉ）の化合物とホルムアルデヒド又はホルムアルデ
ヒド供与体及びアンモニア又はアンモニア供与体との反
応は、極性溶媒、例えば、酢酸、アＶコール、水あるい
はこれらの混合物が好ましく、室温から還流温度で行う
ことができる。The reaction of the compound of formula (I) with formaldehyde or a formaldehyde donor and ammonia or an ammonia donor is preferably carried out in a polar solvent, such as acetic acid, alcohol, water or a mixture thereof, and can be carried out at room temperature to reflux temperature. can.
本発明方法における原料である式（ｎ）の化合物は、た
とえば
で示される方法によシ得ることができる。The compound of formula (n) which is a raw material in the method of the present invention can be obtained, for example, by the method shown below.
できる。（ＵＳ ２，８２１．５５５ ）又、本発明方
法では
で合成される化合物と、次亜硫酸ナトリウムを作用させ
るかは触媒でホルムアルデヒドを作用させた後、過剰の
ホルムアルデヒド又はホルムアルデヒド供与体及びアン
モニア又はアンモニア供与棒金反応させることによシシ
メチジンを得ることができる。can. (US 2,821.555) In addition, in the method of the present invention, the compound synthesized by is reacted with sodium hyposulfite or formaldehyde with a catalyst, and then excess formaldehyde or formaldehyde donor and ammonia or ammonia donor are reacted. Cicimetidine can be obtained by a rolling reaction.
によシ合成できる。（ＪＡ、Ｃ３−互５４３８（”５３
） 。It can be synthesized easily. (JA, C3-mutual 5438 ("53
).
Ｂｕｌｌ、Ｃｈ＠ｍ、 Ｓｅａ、 Ｊｐｍ−３９、２５
１７（’６６ ） ）従って本発明方法は従来方法に比
べ反応工程が短縮され、簡便で良好な収率でシメチジン
を得ることができ工業的ＫＷ用な方法である。Bull, Ch@m, Sea, Jpm-39, 25
17 ('66)) Therefore, the method of the present invention has shorter reaction steps than the conventional method, and can obtain cimetidine in a simple and good yield, making it a method suitable for industrial KW.
以下に本発明の実施例１示し、本発明を更に詳細に説明
する。Example 1 of the present invention will be shown below to explain the present invention in more detail.
実施例１
２Ｎ酢酸（３５ｄ）中にＮ−シアノード−メチル−Ｎ’
−（２−Ｃ（２，３−ジオキソプナル）チオ〕エナル）
グアニシン２．２８＆（１０ミリモル）、塩化アンモニ
ウム０．８Ｉｌ（１５ミリモル）及びノ９ラホルムアル
デヒド０．４５．９（１５ミリモル）１−７０℃で１．
５時間攪拌し友、溶媒を減圧留去し、残渣を２ Ｎ Ｎ
ａＯＨで中和した後、さらに減圧留去し、残渣をメタノ
ールに溶解した。不純物をセライト濾過で除き、減圧貿
去後シリカｒルカラム（クロロホルム−メタノール）Ｋ
かけ得られ九粉末をアセトニトリルよシ再結晶し、１．
２３ ＩＩのシメチジンを白色結晶性粉末として得た。Example 1 N-cyano-methyl-N' in 2N acetic acid (35d)
-(2-C(2,3-dioxopnal)thio]enal)
Guanisine 2.28 (10 mmol), ammonium chloride 0.8 Il (15 mmol) and formaldehyde 0.45.9 (15 mmol) at 1-70°C.
After stirring for 5 hours, the solvent was distilled off under reduced pressure, and the residue was diluted with 2 N
After neutralizing with aOH, the residue was further distilled off under reduced pressure and the residue was dissolved in methanol. Impurities were removed by celite filtration, and after vacuum removal, silica column (chloroform-methanol) K
The resulting powder was recrystallized from acetonitrile, and 1.
Cimetidine 23 II was obtained as a white crystalline powder.
これは標品とｍｐ。This is the standard item and mp.
ＩＲ，及び ）［ＮＭＲによって一致し′ｎｉ認し友。IR, and ) [confirmed by NMR.
実施例２
Ｎ−シアノ−「−メチＡ＝−Ｎ”−（［２−（２−オキ
シイばノー３−オキソブチル）チオ〕エチル）グアニジ
ン２．５７．９（１０ミリモル）を水５−、エタノール
５ｉｄの混合溶媒中に加え、次亜硫酸ナトリウム３．４
８５’（２０ミリモル）ｔ−加え、４０℃で２時間攪拌
した。さらに酢酸４−を加えた後、塩化アンモニウム０
．８ＩＩ（１５ミリモル）及ヒパラホルムアルデヒド０
．４５９（１５ミリモル）ヲ加え７０℃で２時間攪拌し
た。ｒ６媒を減圧留去し、残直にクロロホルム／メタノ
ール（１／１）？ａ液３０−を加え九。不溶物をセライ
ト濾過で除き、溶媒を減圧留去後、シリカグルカラム（
クロロホルム−メタノール）で精製し、得られた粉末を
アセトニトリルよシ再結晶して０．９２１のシメチジン
を白色結晶性粉末として得た。Example 2 2.57.9 (10 mmol) of N-cyano-"-methyA=-N"-([2-(2-oxyivano-3-oxobutyl)thio]ethyl)guanidine was dissolved in 5- of water and ethanol. 5id mixed solvent, sodium hyposulfite 3.4
85' (20 mmol) was added and stirred at 40°C for 2 hours. After adding more acetic acid 4-, ammonium chloride 0
．． 8II (15 mmol) and hyparaformaldehyde 0
．． 459 (15 mmol) was added and stirred at 70°C for 2 hours. The r6 medium was distilled off under reduced pressure, and the residue was directly diluted with chloroform/methanol (1/1). Add 30- of liquid a.9. Insoluble materials were removed by celite filtration, the solvent was distilled off under reduced pressure, and a silica glu column (
The resulting powder was recrystallized from acetonitrile to obtain 0.921 cimetidine as a white crystalline powder.
実施例３
Ｎ−シアノ−ｙ−メチシーＮ”−（［２−（２−オキシ
イζノー３−オキソグチル）チオ〕エチル）グアニジン
２．５７ＩＣ１０ミリモル）を３Ｎ−ＨＯ２１０ｍ及び
メタノール１０ｍの混合溶媒中に加え、３７ｓホルムア
にテヒド水溶液１０−を加え、４０−４５℃で５時間攪
拌した。反応混合物を冷却し、３ Ｎ−ＮａＯＨで中和
した後、塩化アンモニウム１．６Ｎ（３０ミリモル）を
加え、さらにアンモニアガス會室温で２時間吹き込んだ
。溶媒を減圧留去し、残渣にクロロホルム／メタノ−ν
（１／１）溶液３０−を加え友。不溶物をセライト−過
で除き、溶媒を減圧留去後シリカゲルカラム（クロロホ
ルム−メタノール）で精製した。得られたａ′Ｒ色粉末
をアセトニトリルより再結晶し、白色結晶性粉末のシメ
チジンを得た。Example 3 N-cyano-y-methicyN''-([2-(2-oxy-ζ-no-3-oxobutyl)thio]ethyl)guanidine (2.57 IC, 10 mmol) was added to a mixed solvent of 210 m of 3N-HO and 10 m of methanol. , 10 - of tehyde aqueous solution was added to 37s formua and stirred at 40-45°C for 5 hours. After cooling the reaction mixture and neutralizing with 3N-NaOH, 1.6N (30 mmol) of ammonium chloride was added, and further Ammonia gas was bubbled in at room temperature for 2 hours.The solvent was distilled off under reduced pressure, and the residue was dissolved in chloroform/methanol-ν.
(1/1) Add solution 30-. Insoluble matters were removed by filtration through Celite, and the solvent was distilled off under reduced pressure, followed by purification with a silica gel column (chloroform-methanol). The obtained a'R color powder was recrystallized from acetonitrile to obtain cimetidine as a white crystalline powder.
実施例４
Ｎ−シアノード−メチル−シー（［２−（２−オキシイ
ミノ−３−オキソブチル）チオ〕エチル）グアニジン２
．５７Ｆ（１０ミリモＡ／）を３Ｎ−１（ＣｊｌＯ−及
びメタノール１０ゴの混合Ｍ媒中に加え、３７％ホルム
アルデヒド水浴液１Ｏ−ｔ−加え４０−４５℃で５時間
攪拌した。反応混合物を冷却し、アンモニアガス金室温
で２時間吹き込んだ、溶媒を減圧留去し、残渣にクロロ
ホルム／メタノール（１／１）浴液３０−を加え穴。不
溶物をセライト濾過で除き、溶媒を減圧留去後シリカグ
ルカラム（クロロホルム−メタノール）で特製した。得
られた微黄色粉末をアセトニトリルより再結晶し、白色
結晶性粉末のシメチジ／を得文。Example 4 N-cyano-methyl-cy([2-(2-oxyimino-3-oxobutyl)thio]ethyl)guanidine 2
．． 57F (10 mmA/) was added to a mixed M medium of 3N-1 (CjlO- and methanol 10g), 10-t- of 37% formaldehyde water bath solution was added, and the mixture was stirred at 40-45°C for 5 hours.The reaction mixture was cooled. Then, ammonia gas was blown in at room temperature for 2 hours, the solvent was distilled off under reduced pressure, and 30 mm of chloroform/methanol (1/1) bath solution was added to the residue. It was then specially prepared using a silica glucolumn (chloroform-methanol).The obtained slightly yellow powder was recrystallized from acetonitrile to obtain Shimetidji/ as a white crystalline powder.
手続補正書（自発）
昭和６１年１１月１ 日
特許庁長官 黒 １）明 雄 殿
１、事件の表示
昭和６１年特許願第２１７７６７号
λ発明の名称
イミメゾール誌導体の製造法
３、補正ｔする者
事件との関係 特許出願人
住所 東京都千代田区岩本町２丁目２番３号４、補正命
令の日付 自 発
６、補正の内容Procedural amendment (voluntary) November 1, 1985 Commissioner of the Japan Patent Office Black 1) Mr. Yu Akira 1, Indication of the case 1986 Patent Application No. 217767 λ Name of the invention Immezol magazine Manufacturing method of conductor 3, Amendment t Patent applicant address: 2-2-3-4, Iwamoto-cho, Chiyoda-ku, Tokyo Date of amendment order: Initiator 6 Contents of amendment
Claims (1)
れか一方がＯで、他方はＯ又はＮＯＨを示す。）で表わ
される化合物に、ホルムアルデヒド又はホルムアルデヒ
ド供与体及びアンモニア又はアンモニア供与体を反応さ
せることを特徴とする、式 ▲数式、化学式、表等があります▼ で表わされるイミダゾール誘導体の製造法。[Claims] Formaldehyde or formaldehyde donor to a compound represented by the formula ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (In the formula, either A or B is O and the other is O or NOH.) A method for producing an imidazole derivative represented by the formula ▲There are mathematical formulas, chemical formulas, tables, etc.▼, which is characterized by reacting ammonia and an ammonia donor.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61217767A JPS6372679A (en) | 1986-09-16 | 1986-09-16 | Production of imidazole derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61217767A JPS6372679A (en) | 1986-09-16 | 1986-09-16 | Production of imidazole derivative |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS6372679A true JPS6372679A (en) | 1988-04-02 |
Family
ID=16709412
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61217767A Pending JPS6372679A (en) | 1986-09-16 | 1986-09-16 | Production of imidazole derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6372679A (en) |
-
1986
- 1986-09-16 JP JP61217767A patent/JPS6372679A/en active Pending
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