JPS63183528A - Malignant tumor remedy - Google Patents
Malignant tumor remedyInfo
- Publication number
- JPS63183528A JPS63183528A JP62279414A JP27941487A JPS63183528A JP S63183528 A JPS63183528 A JP S63183528A JP 62279414 A JP62279414 A JP 62279414A JP 27941487 A JP27941487 A JP 27941487A JP S63183528 A JPS63183528 A JP S63183528A
- Authority
- JP
- Japan
- Prior art keywords
- ebselen
- remedy
- malignant tumor
- tumors
- pharmaceutical
- 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
- 201000011510 cancer Diseases 0.000 title claims description 7
- DYEFUKCXAQOFHX-UHFFFAOYSA-N Ebselen Chemical compound [se]1C2=CC=CC=C2C(=O)N1C1=CC=CC=C1 DYEFUKCXAQOFHX-UHFFFAOYSA-N 0.000 claims description 13
- 229950010033 ebselen Drugs 0.000 claims description 12
- 239000003814 drug Substances 0.000 claims description 8
- 229940124597 therapeutic agent Drugs 0.000 claims description 2
- 206010028980 Neoplasm Diseases 0.000 description 14
- 239000013543 active substance Substances 0.000 description 8
- 241001465754 Metazoa Species 0.000 description 6
- VOXZDWNPVJITMN-ZBRFXRBCSA-N 17β-estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 VOXZDWNPVJITMN-ZBRFXRBCSA-N 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 229940079593 drug Drugs 0.000 description 3
- 229960005309 estradiol Drugs 0.000 description 3
- 229930182833 estradiol Natural products 0.000 description 3
- 229940011871 estrogen Drugs 0.000 description 3
- 239000000262 estrogen Substances 0.000 description 3
- 210000003734 kidney Anatomy 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- 239000000824 cytostatic agent Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000007943 implant Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 210000000056 organ Anatomy 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- DYAVFTICFASTKQ-UHFFFAOYSA-N 2-methylselanyl-n-phenylbenzamide Chemical compound C[Se]C1=CC=CC=C1C(=O)NC1=CC=CC=C1 DYAVFTICFASTKQ-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 241000699800 Cricetinae Species 0.000 description 1
- 206010011878 Deafness Diseases 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 241000699673 Mesocricetus auratus Species 0.000 description 1
- 241000283984 Rodentia Species 0.000 description 1
- 206010039491 Sarcoma Diseases 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 230000010261 cell growth Effects 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000008570 general process Effects 0.000 description 1
- 230000034659 glycolysis Effects 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 241000411851 herbal medicine Species 0.000 description 1
- 238000010562 histological examination Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- KEBHLNDPKPIPLI-UHFFFAOYSA-N hydron;2-(3h-inden-4-yloxymethyl)morpholine;chloride Chemical compound Cl.C=1C=CC=2C=CCC=2C=1OCC1CNCCO1 KEBHLNDPKPIPLI-UHFFFAOYSA-N 0.000 description 1
- 229920003132 hydroxypropyl methylcellulose phthalate Polymers 0.000 description 1
- 229940031704 hydroxypropyl methylcellulose phthalate Drugs 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 208000032839 leukemia Diseases 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 230000002062 proliferating effect Effects 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 238000001243 protein synthesis Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 230000014616 translation Effects 0.000 description 1
- 230000005748 tumor development Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Steroid Compounds (AREA)
Abstract
(57)【要約】本公報は電子出願前の出願データであるた
め要約のデータは記録されません。(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.
Description
【発明の詳細な説明】
本発明は、悪性腫瘍の治療のためのエブセレン（Ｅｂｓ
ｅｌｅｎ）の新規な用途、この活性物質を含む製剤、お
よび癌の治療薬の製造のためのこの化合物の使用に関す
る。DETAILED DESCRIPTION OF THE INVENTION The present invention provides ebselen (Ebs) for the treatment of malignant tumors.
elen), preparations containing this active substance, and the use of this compound for the manufacture of medicaments for the treatment of cancer.
最近の数十年間に、癌、肉腫、白血病および腫瘍の名の
もとに分類されることのある腫瘍の治療のための物質の
開発には、甚だしい発展がなされている。多くの化合物
が合成され、考えられ得るあらゆる種類の化学物質がそ
れらの腫瘍抑制特性に関して調査されている。しかしな
がら、これまで知られている物質はいずれも特に癌に対
する活性物質ではあるけれでも、細胞に対して幾分かの
一般的な毒性を有し、従って細胞の成長を抑制ずる化合
物である。癌細胞は、通常、これらの細胞増殖抑制剤に
よってかなりの程度に損傷されるけれども、癌細胞は正
常細胞よりもより大きい成長および増殖速度を有し、従
ってより高い蛋白質合成および解糖を示す。しかしなが
ら、これらの薬剤の生体における他の増殖組織に対する
有害な副作用には特定されていない作用もあり、従って
真の治療薬はまだ存在しない。In recent decades, tremendous progress has been made in the development of substances for the treatment of tumors, which may be classified under the names of cancers, sarcomas, leukemias and tumors. Many compounds have been synthesized and all possible types of chemicals are being investigated for their tumor suppressing properties. However, all the substances known so far are compounds which, although they are particularly active substances against cancer, have some general toxicity towards cells and therefore inhibit cell growth. Although cancer cells are usually damaged to a significant extent by these cytostatic agents, cancer cells have greater growth and proliferation rates than normal cells and therefore exhibit higher protein synthesis and glycolysis. However, there are also unspecified harmful side effects of these drugs on other proliferating tissues in the body, and therefore no true therapeutic agent yet exists.
今や、エブセレンが極めて特効のある腫瘍抑制作用を有
するということが予期せず見出されたのである。It has now been unexpectedly discovered that ebselen has extremely potent tumor-inhibiting effects.
エブセレン（２−フェニル−１，２−ベンズイソセレナ
ゾール−３（２Ｈ）−オン／ｌＮＮ−＋Ｊスト１１ｋＬ
５１）は、リウマチ症の治療に用いることのできる公知
の化合物（ＤＢ−ＰＳ３０２７０７３）であり、例えば
、Ｒ，ＷｅｂｅｒおよびＭ、Ｒｅｎ５ｏｎ＋Ｂｕｌｌｅ
ｔｉｎ ｄｅ ｌａ Ｓｏｃ、 ＣｈｉＩＩｌ
、 ｄｅ Ｆｒａｎｃｅ ％ １９７６年（
７／８） 、１１２４〜１１２６頁の方法により、２−
メチルセレノ−Ｎ−フェニルベンズアミドを五塩化燐と
反応させ、次いで加水分解することによって、製造され
る。この物質の良好な適合性は、エブセレンが特に無毒
性（ＬＤｓｏ≧４６００ ｎｇ／ｋｇ、経口、ラット）
であるから、特に顕著である。Ebselen (2-phenyl-1,2-benzisoselenazol-3(2H)-one/lNN-+Jst 11kL
51) is a known compound (DB-PS3027073) that can be used for the treatment of rheumatism, for example, R, Weber and M, Ren5on+Bulle.
tin de la Soc, ChiIIIl
, de France% 1976 (
7/8), pp. 1124-1126, 2-
It is produced by reacting methylseleno-N-phenylbenzamide with phosphorus pentachloride followed by hydrolysis. The good compatibility of this substance is due to the fact that ebselen is particularly non-toxic (LDso ≥4600 ng/kg, oral, rat).
Therefore, it is particularly remarkable.
エブセレンの予期しない抗腫瘍効力は、Ｊ、Ｇ。Unexpected antitumor efficacy of ebselen J, G.
Ｌｉｅｈｒ他により開発されたモデル（Ｊ、Ｇ、 Ｌｉ
ｅｈｒおよびり、Ｅ、５ｉｒｄａｓｋｕ 、 ”Ｅｓｔ
ｒｏｇｅｎ ｄｅｐｅｎｄｅｎｔ ｋｉｄｎｅｙｔｕｍ
ｏｕｒｓ”ｓ １１巻、Ｔｉ５ｓｕｅ ｃｕｌｔｕｒｅ
ｏｆ ｅｐｉｔｈｅｌｊｕｍｃｅｌｌｓ ％ Ｍａｒ
ｉｅ Ｔａｕｂ編、Ｐｌｅｎｕｍ、 Ｐｕｂｌ、 ｃｏ
ｒｐ、、１９８５年、２０５〜２３４頁）において見出
された。The model developed by Liehr et al. (J, G, Li
ehr and ri, E, 5irdask, “Est
rogen dependent kidneytum
ours"s volume 11, Ti5sue culture
of epitheljumcells % Mar
ie Taub, Plenum, Publ, co.
rp, 1985, pp. 205-234).
４〜６週令の雄のシリアハムスターを、皮下エストラジ
オール埋植（９０％エストラジオールおよび１０％コレ
ステロール）により処置した。エストロゲンにより処置
したハムスターおよび未処置ハムスターを表１に示すよ
うに４つの群に分けた。乾燥重量当たり０．１５％のエ
ブセレンを添加した（約１０５■／ｋｇ）げっ書類飼料
を、エブセレンにより処理された動物に与えた。パルプ
状のコンシスチンシーを得るためにこの飼料に水を加え
た。３力月後、エストロゲンで処理された動物に、同一
重量および同一組成の追加の埋植を行った。１９６日後
、動物を殺し、腎臓および他の器官を取り出した。腎臓
を長さ方向に分割した。腎臓および幾つかの他の器官の
それぞれの半分を顕微鏡による組織学的検査のためにホ
ルマリン中に入れた。おおざっばな調査で見ることので
きる顕微鏡的腫瘍を表１に示す。Male Syrian hamsters, 4-6 weeks old, were treated with subcutaneous estradiol implants (90% estradiol and 10% cholesterol). Estrogen treated and untreated hamsters were divided into four groups as shown in Table 1. A rodent diet supplemented with 0.15% ebselen by dry weight (approximately 105 μg/kg) was fed to the ebselen-treated animals. Water was added to this feed to obtain a pulpy consistency. Three months later, the estrogen-treated animals received additional implants of the same weight and composition. After 196 days, the animals were sacrificed and the kidneys and other organs were removed. Kidneys were divided lengthwise. Each half of the kidney and several other organs were placed in formalin for microscopic histological examination. Microscopic tumors that can be seen on cursory examination are shown in Table 1.
処 理 腫瘍を有する動物数（動物数
） （試験された動物数）未処理
（５） ０ （５）エストラジオール
（５） ５ （５）この実験が示すように
、エブセレンは腫瘍の治療に極めて特効のある作用を有
する。誘発された腫瘍は通常、移植された腫瘍よりも細
胞増殖抑制剤に対する感受性がはるかに小さいので、特
に腫瘍の発達の一般的なプロセスがヒトにおけるプロセ
スに極めて類似しているので、これらの結果はヒトに対
する成功の可能性を判断するときに有利である。Treatment Number of animals with tumors (Number of animals) (Number of animals tested) Untreated
(5) 0 (5) Estradiol (5) 5 (5) As this experiment shows, ebselen has a very specific effect in the treatment of tumors. These results are important because induced tumors are typically much less sensitive to cytostatic drugs than transplanted tumors, especially since the general process of tumor development is very similar to that in humans. Advantageous when determining the likelihood of success in humans.
本発明は、また、エブセレンを活性物質として含む製薬
製剤に関する。本発明に係る製薬製剤は、腸内、経口、
直腸または非経口投与のためのものであり、製薬活性物
質を単独で含むかまたは製薬用途に通常の賦形剤ととも
に含む。有利には、活性物質の製薬製剤は所望の投与方
法に適合された個々の投与形で、例えば、錠剤、糖剤、
カプセル、生薬、顆粒、溶液、乳剤または懸濁剤の形に
ある。The invention also relates to pharmaceutical formulations containing ebselen as active substance. The pharmaceutical preparation according to the present invention can be administered enterally, orally,
For rectal or parenteral administration, they contain the pharmaceutically active substance alone or together with excipients customary for pharmaceutical use. Advantageously, the pharmaceutical preparations of the active substances are in individual dosage forms adapted to the desired method of administration, for example tablets, dragees,
In the form of capsules, herbal medicines, granules, solutions, emulsions or suspensions.
この物質の投与量は１日当たり通常１０〜２０００■、
好ましくは３０〜３００■であり、１回の投与であって
もよく、あるいは数回の投与であってもよく、好ましく
は日に２〜３回の投与である。The dosage of this substance is usually 10 to 2000 ■ per day,
The dose is preferably 30 to 300 μm, and may be administered once or several times, preferably 2 to 3 times a day.
本発明に係る薬剤の製造を下記の例によって詳しく説明
する。The preparation of the medicament according to the invention will be explained in detail by the following examples.
公知の方法により製造された本発明に係る薬剤の製薬形
。１５０ｎＲの活性物質を含む５００■の錠剤。Pharmaceutical forms of the medicament according to the invention manufactured by known methods. 500 μ tablets containing 150 nR of active substance.
エブセレン １５０■ラクトース
２５０■結晶セルロース
５０■カルシウムカルボキシメチルセル
ロース３０■
ステアリン酸マグネシウム ２０■勇１
公知の方法により製造された本発明に係る薬剤の製薬形
。１００■の活性物質を含む３００■の錠剤。Ebselen 150■Lactose 250■Crystalline cellulose
50■ Calcium carboxymethyl cellulose 30■ Magnesium stearate 20■Yu 1 Pharmaceutical form of the drug according to the present invention manufactured by a known method. 300 ■ tablets containing 100 ■ active substance.
エブセレン １００■微品性セル
ロース １５０■ＣｕｔｉｎａＯＨＲ２
０Ｎ
ヒドロキシプロピルメチルセルロースフタレート
３０■Ｍ［別
公知の方法により製造された本発明に係る薬剤の製薬形
。５０■の活性物質を含むカプセル。Ebselen 100■Microcellulose 150■CutinaOHR2
0N Hydroxypropyl methylcellulose phthalate
30μM [Pharmaceutical form of the drug according to the present invention produced by another known method. Capsules containing 50 μ of active substance.
Claims (1)
治療剤。1. A therapeutic agent for malignant tumors containing Ebselen.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3638124A DE3638124C2 (en) | 1986-11-08 | 1986-11-08 | New pharmaceutical use of Ebselen |
| DE3638124.1 | 1986-11-08 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63183528A true JPS63183528A (en) | 1988-07-28 |
| JPH0625059B2 JPH0625059B2 (en) | 1994-04-06 |
Family
ID=6313486
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62279414A Expired - Lifetime JPH0625059B2 (en) | 1986-11-08 | 1987-11-06 | Malignant tumor therapeutic agent |
Country Status (3)
| Country | Link |
|---|---|
| JP (1) | JPH0625059B2 (en) |
| KR (1) | KR950008767B1 (en) |
| DE (1) | DE3638124C2 (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1996033712A1 (en) * | 1995-04-25 | 1996-10-31 | Daiichi Pharmaceutical Co., Ltd. | Remedy for acquired immunodeficiency syndrome |
| JP2005090954A (en) * | 2003-09-19 | 2005-04-07 | Beru Ag | Pressure glow plug for diesel engine |
| JP2005519991A (en) * | 2001-06-08 | 2005-07-07 | 北京大学 | Benzoisoselenazole derivatives having anti-inflammatory, antiviral and antithrombotic activity and their use |
| JP2008533021A (en) * | 2005-03-08 | 2008-08-21 | サウンド ファーマシューティカルズ インコーポレイテッド | Methods and compositions for treating cancer |
| US7671211B1 (en) | 1999-03-31 | 2010-03-02 | Arne Holmgren | Substrates for thioredoxin reductase |
| JP2010280615A (en) * | 2009-06-04 | 2010-12-16 | Gunma Univ | Migration inhibitor for cancer treatment |
| US11013730B1 (en) | 2014-09-12 | 2021-05-25 | Thioredoxin Systems Ab | Composition comprising selenazol or thiazalone derivatives and silver and method of treatment therewith |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4024885C2 (en) * | 1990-08-06 | 2002-07-18 | Nattermann A & Cie | Use of 2-phenyl-1,2-benzisoselenazol-3 (2H) -one |
| PT826370E (en) * | 1996-08-27 | 2002-10-31 | Nattermann A & Cie | PHARMACEUTICAL PREPARATION CONTAINING 2-PHENYL-1,2-BENZOISOELENAZOL-3 (2H) -ONE FOR THE TREATMENT OF ALZHEIMER'S DISEASE |
| JP2000016935A (en) | 1998-07-01 | 2000-01-18 | Dai Ichi Seiyaku Co Ltd | Cyclooxygenase inhibitor |
| WO2003045334A2 (en) | 2001-11-29 | 2003-06-05 | Sound Pharmaceuticals Incorporated | Methods and compositions for ameliorating the undesirable effects of chemotherapy |
| AU2003202219B2 (en) | 2002-01-04 | 2008-10-23 | Sound Pharmaceuticals Incorporated | Methods for treating hearing loss |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3027073C2 (en) * | 1980-07-17 | 1985-03-07 | A. Nattermann & Cie GmbH, 5000 Köln | Pharmaceutical preparations containing 2-phenyl-1,2-benzisoselenazol-3 (2H) -one |
-
1986
- 1986-11-08 DE DE3638124A patent/DE3638124C2/en not_active Expired - Lifetime
-
1987
- 1987-11-03 KR KR1019870012297A patent/KR950008767B1/en not_active IP Right Cessation
- 1987-11-06 JP JP62279414A patent/JPH0625059B2/en not_active Expired - Lifetime
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1996033712A1 (en) * | 1995-04-25 | 1996-10-31 | Daiichi Pharmaceutical Co., Ltd. | Remedy for acquired immunodeficiency syndrome |
| US7671211B1 (en) | 1999-03-31 | 2010-03-02 | Arne Holmgren | Substrates for thioredoxin reductase |
| JP2005519991A (en) * | 2001-06-08 | 2005-07-07 | 北京大学 | Benzoisoselenazole derivatives having anti-inflammatory, antiviral and antithrombotic activity and their use |
| JP2005090954A (en) * | 2003-09-19 | 2005-04-07 | Beru Ag | Pressure glow plug for diesel engine |
| JP2008533021A (en) * | 2005-03-08 | 2008-08-21 | サウンド ファーマシューティカルズ インコーポレイテッド | Methods and compositions for treating cancer |
| JP2010280615A (en) * | 2009-06-04 | 2010-12-16 | Gunma Univ | Migration inhibitor for cancer treatment |
| US11013730B1 (en) | 2014-09-12 | 2021-05-25 | Thioredoxin Systems Ab | Composition comprising selenazol or thiazalone derivatives and silver and method of treatment therewith |
Also Published As
| Publication number | Publication date |
|---|---|
| DE3638124C2 (en) | 1996-09-05 |
| JPH0625059B2 (en) | 1994-04-06 |
| KR880005928A (en) | 1988-07-21 |
| DE3638124A1 (en) | 1988-05-11 |
| KR950008767B1 (en) | 1995-08-08 |
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