JPS62175666A - Urobilinogen composition - Google Patents
Urobilinogen compositionInfo
- Publication number
- JPS62175666A JPS62175666A JP1994986A JP1994986A JPS62175666A JP S62175666 A JPS62175666 A JP S62175666A JP 1994986 A JP1994986 A JP 1994986A JP 1994986 A JP1994986 A JP 1994986A JP S62175666 A JPS62175666 A JP S62175666A
- Authority
- JP
- Japan
- Prior art keywords
- catalyst
- raney
- urobilinogen
- composition
- bilirubin
- 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
- OBHRVMZSZIDDEK-UHFFFAOYSA-N urobilinogen Chemical compound CCC1=C(C)C(=O)NC1CC1=C(C)C(CCC(O)=O)=C(CC2=C(C(C)=C(CC3C(=C(CC)C(=O)N3)C)N2)CCC(O)=O)N1 OBHRVMZSZIDDEK-UHFFFAOYSA-N 0.000 title claims abstract description 92
- 239000000203 mixture Substances 0.000 title claims abstract description 34
- BPYKTIZUTYGOLE-IFADSCNNSA-N Bilirubin Chemical compound N1C(=O)C(C)=C(C=C)\C1=C\C1=C(C)C(CCC(O)=O)=C(CC2=C(C(C)=C(\C=C/3C(=C(C=C)C(=O)N\3)C)N2)CCC(O)=O)N1 BPYKTIZUTYGOLE-IFADSCNNSA-N 0.000 claims abstract description 32
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims abstract description 26
- 239000003054 catalyst Substances 0.000 claims abstract description 22
- 239000007868 Raney catalyst Substances 0.000 claims abstract description 21
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims abstract description 12
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims abstract description 9
- 238000004108 freeze drying Methods 0.000 claims description 12
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 7
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical group [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims description 5
- 238000000034 method Methods 0.000 abstract description 7
- 238000007710 freezing Methods 0.000 abstract description 6
- 230000008014 freezing Effects 0.000 abstract description 6
- 238000001035 drying Methods 0.000 abstract description 5
- 238000004519 manufacturing process Methods 0.000 abstract description 5
- 229910052751 metal Inorganic materials 0.000 abstract description 4
- 239000002184 metal Substances 0.000 abstract description 4
- 229910045601 alloy Inorganic materials 0.000 abstract description 3
- 239000000956 alloy Substances 0.000 abstract description 3
- 239000000706 filtrate Substances 0.000 abstract description 3
- 239000000843 powder Substances 0.000 abstract description 3
- 239000007787 solid Substances 0.000 abstract description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 3
- 239000003513 alkali Substances 0.000 abstract description 2
- 239000012670 alkaline solution Substances 0.000 abstract description 2
- 239000007864 aqueous solution Substances 0.000 abstract description 2
- 239000003518 caustics Substances 0.000 abstract description 2
- 238000011109 contamination Methods 0.000 abstract 1
- 230000007613 environmental effect Effects 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 238000012360 testing method Methods 0.000 description 7
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
- 229910052782 aluminium Inorganic materials 0.000 description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 5
- 210000002700 urine Anatomy 0.000 description 5
- 238000007796 conventional method Methods 0.000 description 4
- 239000000546 pharmaceutical excipient Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000003912 environmental pollution Methods 0.000 description 3
- 229910052742 iron Inorganic materials 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229910052759 nickel Inorganic materials 0.000 description 3
- 229910052697 platinum Inorganic materials 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 229910052720 vanadium Inorganic materials 0.000 description 3
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 3
- 229910000881 Cu alloy Inorganic materials 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- MJGFBOZCAJSGQW-UHFFFAOYSA-N mercury sodium Chemical compound [Na].[Hg] MJGFBOZCAJSGQW-UHFFFAOYSA-N 0.000 description 2
- 229910001023 sodium amalgam Inorganic materials 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- APKVZMHTQNVEDV-UHFFFAOYSA-N 14,16-Diepimer-i-Urobilinogen Natural products CCC1=C(C)C(Cc2[nH]c(Cc3[nH]c(CC4NC(=O)C(=C4C)CC)c(C)c3CCC(=O)O)c(CCC(=O)O)c2C)NC1=O APKVZMHTQNVEDV-UHFFFAOYSA-N 0.000 description 1
- BGNGWHSBYQYVRX-UHFFFAOYSA-N 4-(dimethylamino)benzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C=C1 BGNGWHSBYQYVRX-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 206010056375 Bile duct obstruction Diseases 0.000 description 1
- 206010008635 Cholestasis Diseases 0.000 description 1
- KSQFFJKKJAEKTB-UHFFFAOYSA-N D-Urobilinogen Chemical compound CCC1=C(C)C(=O)NC1CC1=C(C)C(CCC(O)=O)=C(CC2=C(C(C)=C(CC3C(=C(C=C)C(=O)N3)C)N2)CCC(O)=O)N1 KSQFFJKKJAEKTB-UHFFFAOYSA-N 0.000 description 1
- 229910000990 Ni alloy Inorganic materials 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 238000011088 calibration curve Methods 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000002949 hemolytic effect Effects 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 208000019423 liver disease Diseases 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- VKGRRZVYCXLHII-UHFFFAOYSA-N stercobilinogen Chemical compound CCC1C(C)C(=O)NC1CC1=C(C)C(CCC(O)=O)=C(CC2=C(C(C)=C(CC3C(C(CC)C(=O)N3)C)N2)CCC(O)=O)N1 VKGRRZVYCXLHII-UHFFFAOYSA-N 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
Landscapes
- Investigating Or Analysing Biological Materials (AREA)
- Pyrrole Compounds (AREA)
Abstract
Description
【発明の詳細な説明】
〈産業上の利用分野〉
本発明はウロビリノーゲン組成物に関し、詳しくは、ラ
ニー触媒とりわけラニーニッケル触媒、ラニー銅触媒、
ラニー鉄触媒を用いてビリルビンを還元し、これを凍結
乾燥してなる安定なウロビリノーゲン組成物に関する。DETAILED DESCRIPTION OF THE INVENTION <Industrial Application Field> The present invention relates to urobilinogen compositions, and more particularly, to Raney catalysts, particularly Raney nickel catalysts, Raney copper catalysts,
The present invention relates to a stable urobilinogen composition obtained by reducing bilirubin using a Raney iron catalyst and freeze-drying the reduced bilirubin.
〈従来の技術〉
ウロビリノーゲンは、生体内においては腸内細菌によっ
てビリルビンが還元されて生成される。<Prior Art> Urobilinogen is produced in vivo by the reduction of bilirubin by intestinal bacteria.
通常、健常者でも尿中に微量のウロビリノーゲンが排泄
され、臨床検査では肝疾患や溶血性疾患あるいは胆管閉
塞などの検査方法として尿ウロビリノーゲンの検査が古
くから知られている。このようなウロビリノーゲンを人
工的に生成する方法として、従来、ナトリウムアマルガ
ムやバナジウム、或いは白金を触媒に用いてビリルビン
を還元する方法が知られている。Normally, even healthy people excrete trace amounts of urobilinogen in the urine, and urine urobilinogen testing has long been known as a clinical test for liver disease, hemolytic disease, bile duct obstruction, and other conditions. As a method of artificially producing such urobilinogen, a method of reducing bilirubin using sodium amalgam, vanadium, or platinum as a catalyst is conventionally known.
〈発明が解決しようとする問題点〉
しかし、これら従来の方法でウロビリノーゲンを生成す
る場合、次のような問題があった。すなわち、ナトリウ
ムアマルガムを触媒に用いる方法では廃棄物の水銀によ
る環境汚染の問題があった。またバナジウムや白金を触
媒に用いる方法では高価で特殊な設備を必要とした。特
に、これら従来の方法によって生成されたウロビリノー
ゲンは非常に不安定で酸化されやすく、尿ウロビリノー
ゲン測定用のコントロール等の臨床検査用として用いる
ことができなかった。<Problems to be Solved by the Invention> However, when urobilinogen is produced using these conventional methods, there are the following problems. That is, the method using sodium amalgam as a catalyst has the problem of environmental pollution due to mercury in the waste. Furthermore, methods using vanadium or platinum as catalysts required expensive and special equipment. In particular, urobilinogen produced by these conventional methods is very unstable and easily oxidized, and cannot be used for clinical tests such as controls for urine urobilinogen measurement.
そこで本発明は上記従来技術の欠点を解消し、環境汚染
の問題なく安全に且つ安価に製造できると共に特に臨床
検査の分野等においても十分好適に使用できる安定なウ
ロビリノーゲン組成物の提供を目的とする。SUMMARY OF THE INVENTION Therefore, the present invention aims to solve the above-mentioned drawbacks of the prior art, and to provide a stable urobilinogen composition that can be produced safely and inexpensively without problems of environmental pollution, and can be used particularly suitably in the field of clinical testing. .
〈問題点を解決するための手段〉
本発明者らは上記目的に鑑み、従来からの問題を解決す
べく鋭意研究した結果、ラニー触媒を用いてビリルビン
を還元し、これを凍結乾燥することにより、廃棄物によ
る環境汚染の心配がなく安全に且つ高価な設備も不要で
安価に製造でき、特に性状が非常に安定であるウロビリ
ノーゲン組成物を得ることができることを見出し、本発
明に到達した。<Means for Solving the Problems> In view of the above objectives, the present inventors conducted intensive research to solve the conventional problems, and as a result, the present inventors reduced bilirubin using a Raney catalyst and freeze-dried it. We have discovered that it is possible to obtain a urobilinogen composition that is safe and inexpensive to produce without worrying about environmental pollution due to waste, does not require expensive equipment, and has particularly stable properties, and has arrived at the present invention.
すなわち、本発明は、ラニー（Ｒａｎｅｙ）触媒とりわ
けラニーニッケル触媒、ラニー銅触媒、ラニー鉄触媒を
用いてビリルビンを還元し、これを凍結乾燥してなるウ
ロビリノーゲン組成物をその構成とする。That is, the present invention comprises a urobilinogen composition obtained by reducing bilirubin using a Raney catalyst, particularly a Raney nickel catalyst, a Raney copper catalyst, or a Raney iron catalyst, and freeze-drying the reduced bilirubin.
本発明に用いられるラニー触媒は、ラニー（Ｒａｎｅｙ
）によって発明され、一般にラニー触媒として文献に掲
載されている触媒で、合金をカセイアルカリ等で処理し
て得られる金属触媒である。また本発明におけるラニー
触媒においては、合金される金属の種類はとくに限定さ
れるものではないが、ニッケルとアルミニウムの合金か
ら作られるラニーニッケル触媒、銅とアルミニウムの合
金から作られるラニー銅触媒、鉄とアルミニウムの合金
から作られるラニー鉄触媒等が還元効率上好ましい。そ
してこれらラニーニッケル触媒、ラニー銅触媒、ラニー
鉄触媒において、ニッケル、銅、鉄のそれぞれの含有率
はとくに限定されないが、３０％〜６０％程度の含有率
が好ましい。それ以上では触媒能が弱くなり、それ以下
では粉砕されにくいからである。The Raney catalyst used in the present invention is a Raney catalyst used in the present invention.
), and is generally described in literature as a Raney catalyst, and is a metal catalyst obtained by treating an alloy with caustic alkali or the like. In addition, in the Raney catalyst of the present invention, the types of alloyed metals are not particularly limited, but include a Raney nickel catalyst made from an alloy of nickel and aluminum, a Raney copper catalyst made from an alloy of copper and aluminum, and a Raney catalyst made from an alloy of copper and aluminum. A Runny iron catalyst made from an alloy of aluminum and aluminum is preferable in terms of reduction efficiency. In these Raney nickel catalysts, Raney copper catalysts, and Raney iron catalysts, the content of each of nickel, copper, and iron is not particularly limited, but the content is preferably about 30% to 60%. This is because if the amount is more than that, the catalytic ability will be weakened, and if it is less than that, it will be difficult to crush.
本発明において、凍結乾燥とは、水溶液を凍結させ、凍
結状態のまま真空上水分を直接昇華させて乾燥すること
をいう。凍結温度、真空度、乾燥温度はとくに限定され
ないが、たとえば凍結時の品温を一１０℃〜−４０℃、
真空度を０．２〜０．Ｉ Ｔｏｒｒ（トール）、乾燥温
度を４０℃〜２５℃として凍結乾燥することができる。In the present invention, freeze-drying refers to freezing an aqueous solution and drying it by directly sublimating water in a vacuum in a frozen state. The freezing temperature, degree of vacuum, and drying temperature are not particularly limited, but for example, the temperature of the product during freezing may be -10°C to -40°C,
The degree of vacuum is 0.2-0. Freeze-drying can be carried out at I Torr and drying temperature of 40°C to 25°C.
本発明におけるウロビリノーゲン組成物とは、ビリルビ
ンを還元することによって得られる数種（類の異性体、
例えばｄ−ウロビリノーゲン、ｉ −ウロビリノーゲン
、ｌ−ウロビリノーゲン等を含む混合物としてのウロビ
リノーゲンの意味である。The urobilinogen composition in the present invention refers to several types (isomers, etc.) obtained by reducing bilirubin.
Urobilinogen is meant as a mixture containing, for example, d-urobilinogen, i-urobilinogen, l-urobilinogen, and the like.
本発明のウロビリノーゲン組成物は凍結乾燥によって得
られるものであり、その物理的集合状態は固体粉末状で
ある。この点従来方法よって得られているウロビリノー
ゲンはいずれも液体状態のものであり、その物理的集合
状態が両者において全く異なる。The urobilinogen composition of the present invention is obtained by freeze-drying, and its physical aggregated state is in the form of a solid powder. In this respect, both urobilinogens obtained by conventional methods are in a liquid state, and their physical aggregation states are completely different.
本発明のウロビリノーゲン組成物は、例えば、ビリルビ
ンをアルカリ性溶液等で溶解し、これを冷却しなからラ
ニー触媒を加えて反応させ、その濾過液を凍結乾燥する
ことにより製造できる。ここで、冷却しながらというの
は、ラニー触媒を加えて反応させることによって得られ
るウロビリノーゲン組成物が直ちに別のものになってし
まうことのないような温度で反応させるという意味であ
る。勿論ラニー触媒についての条件や凍結乾燥について
の条件は特に限定されるものではない。また反応に関与
しないものであれば、賦形剤を凍結乾燥前に添加しても
よい。賦形剤を含むウロビリノーゲン組成物は凍結乾燥
後の仕上がりが良好である。賦形剤としては、ｉｔ！ｉ
、多ｔｉ類及びそれらの分解物、蛋白質、合成高分子化
合物等から適当に選択して用いることができる。本発明
はこのような賦形剤を含むウロビリノーゲン組成物もそ
の範囲に包含する。The urobilinogen composition of the present invention can be produced, for example, by dissolving bilirubin in an alkaline solution or the like, cooling the solution, adding a Raney catalyst to cause a reaction, and freeze-drying the filtrate. Here, "while cooling" means that the reaction is carried out at such a temperature that the urobilinogen composition obtained by adding and reacting the Raney catalyst does not immediately become different. Of course, the conditions for the Raney catalyst and the conditions for freeze-drying are not particularly limited. Further, excipients may be added before lyophilization as long as they do not participate in the reaction. Urobilinogen compositions containing excipients have a good finish after freeze-drying. As an excipient, it! i
, polytidines and their decomposition products, proteins, synthetic polymer compounds, and the like. The present invention also encompasses urobilinogen compositions containing such excipients.
なお、製造時におい才は、空気との接触及び温度の上昇
をさけ、また遮光の状態で行うのが品質上好ましいが、
実際には短時間で製造が完了するので必ずしもそのよう
な条件を完全に確保しておく必要はない。In addition, during manufacturing, it is preferable to avoid contact with air and rise in temperature, and to do so in a state where it is shielded from light.
In reality, since manufacturing is completed in a short time, it is not necessary to completely ensure such conditions.
本発明の組成物がウロビリノーゲンを含有していること
は臨床検査で用いられる尿ウロビリノーゲン検出試薬で
あるエールリッヒ試薬で確認できる。The fact that the composition of the present invention contains urobilinogen can be confirmed using Ehrlich's reagent, which is a urine urobilinogen detection reagent used in clinical tests.
従来、ウロビリノーゲンは液状で得られるためか、非常
に不安定で、冷蔵庫で保存しても１日たつと１０％以上
が別物質に変化してしまうことから、臨床検査用等とし
ての実用性がなかった。 本発明のウロビリノーゲン組
成物は、凍結乾燥により固体粉末として生成され、その
性状が長期間安定であることが後述の実施例から確認さ
れている〈発明の効果〉
以上の構成よりなる本発明のウロビリノーゲン組成物は
、非常に安定である。さらに水銀等を使用しないので従
来の方法により得られるウロビリノーゲンに比べて公害
等の問題がなく安全に製造できる。またバナジウムや白
金を用いる場合のように高価な設備を必要とせず、安価
に製造することができる。よって、本発明のウロビリノ
ーゲン組成物は尿ウロビリノーゲン測定用のコントロー
ルとして或いはその他の臨床検査用に実用することがで
き、その際、保存が非常に容易で、データを正確に得る
ことができ、またそれら検査を安価に行うことが可能と
なる。Conventionally, urobilinogen is extremely unstable, perhaps because it is obtained in liquid form, and even if stored in the refrigerator, more than 10% of it will change to a different substance within a day, making it impractical for clinical testing. There wasn't. The urobilinogen composition of the present invention is produced as a solid powder by freeze-drying, and its properties are confirmed to be stable for a long period of time from the Examples described below. The composition is very stable. Furthermore, since mercury and the like are not used, it can be produced safely without problems such as pollution, compared to urobilinogen obtained by conventional methods. Further, unlike the case of using vanadium or platinum, expensive equipment is not required and it can be manufactured at low cost. Therefore, the urobilinogen composition of the present invention can be used as a control for urine urobilinogen measurement or for other clinical tests, and in this case, it can be stored very easily, data can be obtained accurately, and It becomes possible to perform inspections at low cost.
〈実施例〉
以下に本発明の実施例を示すが、本発明はこれら実施例
に限定されるのではない。<Examples> Examples of the present invention are shown below, but the present invention is not limited to these Examples.
実施例１
ビリルビン１００ｍｇを０．４規定の水酸化ナトリウム
溶液１００ｍ１溶解し、１０℃以下に冷却しながらニッ
ケル含量５０％のラニーニッケル触媒６ｇを加えて１時
間攪拌する。これを濾過して得た濾液を褐色のバイアル
瓶に小分けして凍結乾燥した。凍結乾燥の条件は、真空
度をＯ，１５Ｔｏｒｒ、品温を凍結時−２０℃、速乾時
２５℃に設定した。得られたウロビリノーゲン組成物を
精製水で溶解して１０倍に希釈し、これをヘンリーらの
改良法で定量したところ、ウロビリノーゲン濃度として
９．５工−ルリツヒ単位／ｄｉであった。すなわち、ビ
リルビンから９５％の生成率でウロビリノーゲン組成物
を得ることができた。また上記１０倍に希釈した液を更
に１００倍まで段階に希釈し、同様に定量して検量線を
作成したところ直線性が得られた。Example 1 100 mg of bilirubin is dissolved in 100 ml of 0.4N sodium hydroxide solution, and while cooling to below 10° C., 6 g of Raney nickel catalyst having a nickel content of 50% is added and stirred for 1 hour. The filtrate obtained by filtration was divided into brown vials and freeze-dried. The freeze-drying conditions were a vacuum degree of O, 15 Torr, and a product temperature of -20°C during freezing and 25°C during quick drying. The obtained urobilinogen composition was dissolved in purified water, diluted 10 times, and quantified using the improved method of Henry et al., and the urobilinogen concentration was 9.5 engineering-Rurrich units/di. That is, a urobilinogen composition could be obtained from bilirubin at a production rate of 95%. Furthermore, when the above-mentioned 10-fold diluted solution was further diluted stepwise up to 100-fold and quantified in the same manner to create a calibration curve, linearity was obtained.
実施例２
ニッケル含量４０％のラニーニッケル触媒を用いて、実
施例１と同様の条件でウロビリノーゲン組成物を得た。Example 2 A urobilinogen composition was obtained under the same conditions as in Example 1 using a Raney nickel catalyst with a nickel content of 40%.
その結果、同様に９５％の生成率でウロビリノーゲン組
成物を得ることができた。As a result, it was possible to obtain a urobilinogen composition with a production rate of 95%.
実施例３
銅含量５０％のラニー銅触媒を用いて実施例１と同様の
方法でウロビリノーゲン組成物を得た。生成率は９５％
であった。Example 3 A urobilinogen composition was obtained in the same manner as in Example 1 using a Raney copper catalyst with a copper content of 50%. Generation rate is 95%
Met.
実施例４
鉄含量５０％のラニー鉄触媒を用いて、実施例１と同様
にしてウロビリノーゲン組成物を得た。生成率は４０％
であった。Example 4 A urobilinogen composition was obtained in the same manner as in Example 1 using a Raney iron catalyst with an iron content of 50%. Generation rate is 40%
Met.
実施例５
実施例１で得た得たウロビリノーゲン組成物を引き続き
、バイアル瓶に入れたまま（遮光状態）、真空下（実施
例１における真空度のまま）、３７°Ｃに保持し、これ
をヘンリーらの改良法で定量して、その含有量の減少割
合を計った。その結果ウロビリノーゲン組成物の含有量
低下は２週間経過しても測定上認められなかった。Example 5 The urobilinogen composition obtained in Example 1 was kept in a vial (light-shielded) at 37°C under vacuum (the degree of vacuum was the same as in Example 1). It was quantified using the improved method of Henry et al., and the rate of decrease in its content was measured. As a result, no decrease in the content of the urobilinogen composition was observed even after two weeks had passed.
実施例２．３．４で得たウロビリノーゲン組成物の場合
も同様であった。The same was true for the urobilinogen composition obtained in Example 2.3.4.
次に従来帯られる液状のウロビリノーゲンを用いて、同
様の条件でその含有量の減少割合を測定した。その結果
、従来のウロビリノーゲンは１時間の保持で含有量が９
０％以上減少、すなわち９０％以上が別物質に変化して
しまった。Next, using conventional liquid urobilinogen, the rate of decrease in its content was measured under the same conditions. As a result, the content of conventional urobilinogen was reduced to 9 after one hour of retention.
It has decreased by more than 0%, that is, more than 90% has changed to a different substance.
Claims (4)
凍結乾燥してなるウロビリノーゲン組成物(1) Urobilinogen composition obtained by reducing bilirubin using a Raney catalyst and freeze-drying it.
の範囲第１項記載のウロビリノーゲン組成物(2) The urobilinogen composition according to claim 1, wherein the Raney catalyst is a Raney nickel catalyst.
第１項記載のウロビリノーゲン組成物(3) The urobilinogen composition according to claim 1, wherein the Raney catalyst is a Raney copper catalyst.
第１項記載のウロビリノーゲン組成物(4) The urobilinogen composition according to claim 1, wherein the Raney catalyst is a Raney iron catalyst.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1994986A JPH0623756B2 (en) | 1986-01-30 | 1986-01-30 | Urobilinogen composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1994986A JPH0623756B2 (en) | 1986-01-30 | 1986-01-30 | Urobilinogen composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62175666A true JPS62175666A (en) | 1987-08-01 |
| JPH0623756B2 JPH0623756B2 (en) | 1994-03-30 |
Family
ID=12013455
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1994986A Expired - Lifetime JPH0623756B2 (en) | 1986-01-30 | 1986-01-30 | Urobilinogen composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0623756B2 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0753742A1 (en) * | 1995-07-10 | 1997-01-15 | Bayer Corporation | Stable liquid urobilinogen control composition |
| KR101470734B1 (en) * | 2012-05-15 | 2014-12-08 | 스미토모 덴소 가부시키가이샤 | Crimp terminal and waterproof termination |
-
1986
- 1986-01-30 JP JP1994986A patent/JPH0623756B2/en not_active Expired - Lifetime
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0753742A1 (en) * | 1995-07-10 | 1997-01-15 | Bayer Corporation | Stable liquid urobilinogen control composition |
| US5866424A (en) * | 1995-07-10 | 1999-02-02 | Bayer Corporation | Stable liquid urobilinogen control composition |
| KR101470734B1 (en) * | 2012-05-15 | 2014-12-08 | 스미토모 덴소 가부시키가이샤 | Crimp terminal and waterproof termination |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0623756B2 (en) | 1994-03-30 |
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