CA1296277C - Sels de compose de germanium organique et medicament en renfermant - Google Patents

Sels de compose de germanium organique et medicament en renfermant

Info

Publication number: CA1296277C
Authority: CA; Canada
Prior art keywords: salt; compound; group; basic; organogermanium
Prior art date: 1986-04-09
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.): Expired - Lifetime

Application number

CA000546248A

Other languages

English (en)

Inventor

Hiroshi Satoh

Kohei Miyao

Norihiro Kakimoto

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Asai Germanium Research Institute Co Ltd

Original Assignee

Asai Germanium Research Institute Co Ltd

Priority date (The priority date 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 date listed.)

1986-04-09

Filing date

1987-09-08

Publication date

1992-02-25

1986-04-09 Priority to JP61081875A priority Critical patent/JPS62252794A/ja

1987-09-08 Application filed by Asai Germanium Research Institute Co Ltd filed Critical Asai Germanium Research Institute Co Ltd

1987-09-08 Priority to CA000546248A priority patent/CA1296277C/fr

1992-02-25 Application granted granted Critical

1992-02-25 Publication of CA1296277C publication Critical patent/CA1296277C/fr

2009-02-25 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

150000003839 salts Chemical class 0.000 title claims abstract description 55
239000003814 drug Substances 0.000 title claims abstract description 24
-1 organogermanium compound Chemical class 0.000 title claims description 10
150000001875 compounds Chemical class 0.000 claims abstract description 33
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 5
125000000217 alkyl group Chemical group 0.000 claims abstract description 4
125000003118 aryl group Chemical group 0.000 claims abstract description 4
125000004434 sulfur atom Chemical group 0.000 claims abstract description 4
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims abstract description 3
239000002246 antineoplastic agent Substances 0.000 claims abstract description 3
229910052760 oxygen Inorganic materials 0.000 claims abstract description 3
239000001301 oxygen Substances 0.000 claims abstract description 3
229910052717 sulfur Inorganic materials 0.000 claims abstract description 3
235000010335 lysozyme Nutrition 0.000 claims description 17
102000016943 Muramidase Human genes 0.000 claims description 12
108010014251 Muramidase Proteins 0.000 claims description 12
108010062010 N-Acetylmuramoyl-L-alanine Amidase Proteins 0.000 claims description 12
229960000274 lysozyme Drugs 0.000 claims description 12
239000004325 lysozyme Substances 0.000 claims description 12
235000001014 amino acid Nutrition 0.000 claims description 11
150000001413 amino acids Chemical class 0.000 claims description 11
XEABSBMNTNXEJM-UHFFFAOYSA-N propagermanium Chemical compound OC(=O)CC[Ge](=O)O[Ge](=O)CCC(O)=O XEABSBMNTNXEJM-UHFFFAOYSA-N 0.000 claims description 11
239000000203 mixture Substances 0.000 claims description 10
KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims description 6
230000000259 anti-tumor effect Effects 0.000 claims description 6
230000008512 biological response Effects 0.000 claims description 5
239000007788 liquid Substances 0.000 claims description 5
239000003607 modifier Substances 0.000 claims description 5
239000013078 crystal Substances 0.000 claims description 4
239000003085 diluting agent Substances 0.000 claims description 4
239000004615 ingredient Substances 0.000 claims description 3
125000004430 oxygen atom Chemical group O* 0.000 claims description 3
229940126589 solid medicine Drugs 0.000 claims description 3
235000019766 L-Lysine Nutrition 0.000 claims description 2
239000004472 Lysine Substances 0.000 claims description 2
229940079593 drug Drugs 0.000 abstract description 15
125000000082 organogermanium group Chemical class 0.000 abstract description 15
239000000367 immunologic factor Substances 0.000 abstract description 4
241000700159 Rattus Species 0.000 description 9
229940024606 amino acid Drugs 0.000 description 8
239000007864 aqueous solution Substances 0.000 description 8
239000000243 solution Substances 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
230000000694 effects Effects 0.000 description 7
229910052739 hydrogen Inorganic materials 0.000 description 7
239000000126 substance Substances 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
241000699670 Mus sp. Species 0.000 description 5
239000002253 acid Substances 0.000 description 5
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
150000002291 germanium compounds Chemical class 0.000 description 4
238000002329 infrared spectrum Methods 0.000 description 4
241001465754 Metazoa Species 0.000 description 3
238000013019 agitation Methods 0.000 description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
229910052732 germanium Inorganic materials 0.000 description 3
GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical group [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 3
206010073071 hepatocellular carcinoma Diseases 0.000 description 3
239000007924 injection Substances 0.000 description 3
238000002347 injection Methods 0.000 description 3
150000007529 inorganic bases Chemical class 0.000 description 3
239000000843 powder Substances 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
239000000725 suspension Substances 0.000 description 3
206010003445 Ascites Diseases 0.000 description 2
102000014150 Interferons Human genes 0.000 description 2
108010050904 Interferons Proteins 0.000 description 2
HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
239000000654 additive Substances 0.000 description 2
125000004429 atom Chemical group 0.000 description 2
210000004369 blood Anatomy 0.000 description 2
239000008280 blood Substances 0.000 description 2
239000011575 calcium Substances 0.000 description 2
239000002775 capsule Substances 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
239000001768 carboxy methyl cellulose Substances 0.000 description 2
210000004027 cell Anatomy 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
239000010419 fine particle Substances 0.000 description 2
239000008187 granular material Substances 0.000 description 2
230000001939 inductive effect Effects 0.000 description 2
229940079322 interferon Drugs 0.000 description 2
210000002540 macrophage Anatomy 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
230000004048 modification Effects 0.000 description 2
238000012986 modification Methods 0.000 description 2
210000000822 natural killer cell Anatomy 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
238000007911 parenteral administration Methods 0.000 description 2
230000009467 reduction Effects 0.000 description 2
239000011734 sodium Substances 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
210000002784 stomach Anatomy 0.000 description 2
230000004083 survival effect Effects 0.000 description 2
208000024891 symptom Diseases 0.000 description 2
239000003826 tablet Substances 0.000 description 2
IQULGZQMMPRBLA-UHFFFAOYSA-N 2-carboxyethylgermanium Chemical compound OC(=O)CC[Ge] IQULGZQMMPRBLA-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
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
108090000790 Enzymes Proteins 0.000 description 1
102000004190 Enzymes Human genes 0.000 description 1
206010020751 Hypersensitivity Diseases 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical compound OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 description 1
229930064664 L-arginine Natural products 0.000 description 1
235000014852 L-arginine Nutrition 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
206010027476 Metastases Diseases 0.000 description 1
241000699666 Mus <mouse, genus> Species 0.000 description 1
241001494479 Pecora Species 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
230000003213 activating effect Effects 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000037396 body weight Effects 0.000 description 1
239000000872 buffer Substances 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
230000003913 calcium metabolism Effects 0.000 description 1
235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
239000008112 carboxymethyl-cellulose Substances 0.000 description 1
230000008859 change Effects 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000006071 cream Substances 0.000 description 1
230000003111 delayed effect Effects 0.000 description 1
229940088598 enzyme Drugs 0.000 description 1
210000003743 erythrocyte Anatomy 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000000945 filler Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
230000002496 gastric effect Effects 0.000 description 1
ZRALSGWEFCBTJO-UHFFFAOYSA-N guanidine group Chemical group NC(=N)N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
229960002885 histidine Drugs 0.000 description 1
125000002883 imidazolyl group Chemical group 0.000 description 1
125000001841 imino group Chemical group [H]N=* 0.000 description 1
230000028993 immune response Effects 0.000 description 1
238000001802 infusion Methods 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
229910017053 inorganic salt Inorganic materials 0.000 description 1
239000003456 ion exchange resin Substances 0.000 description 1
229920003303 ion-exchange polymer Polymers 0.000 description 1
239000008101 lactose Substances 0.000 description 1
230000005923 long-lasting effect Effects 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
230000009401 metastasis Effects 0.000 description 1
238000000034 method Methods 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
238000002156 mixing Methods 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
231100000956 nontoxicity Toxicity 0.000 description 1
239000002674 ointment Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
229920001184 polypeptide Polymers 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
102000004196 processed proteins & peptides Human genes 0.000 description 1
108090000765 processed proteins & peptides Proteins 0.000 description 1
239000000047 product Substances 0.000 description 1
150000005599 propionic acid derivatives Chemical class 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
238000011160 research Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
WPLOVIFNBMNBPD-ATHMIXSHSA-N subtilin Chemical compound CC1SCC(NC2=O)C(=O)NC(CC(N)=O)C(=O)NC(C(=O)NC(CCCCN)C(=O)NC(C(C)CC)C(=O)NC(=C)C(=O)NC(CCCCN)C(O)=O)CSC(C)C2NC(=O)C(CC(C)C)NC(=O)C1NC(=O)C(CCC(N)=O)NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C1NC(=O)C(=C/C)/NC(=O)C(CCC(N)=O)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)CNC(=O)C(NC(=O)C(NC(=O)C2NC(=O)CNC(=O)C3CCCN3C(=O)C(NC(=O)C3NC(=O)C(CC(C)C)NC(=O)C(=C)NC(=O)C(CCC(O)=O)NC(=O)C(NC(=O)C(CCCCN)NC(=O)C(N)CC=4C5=CC=CC=C5NC=4)CSC3)C(C)SC2)C(C)C)C(C)SC1)CC1=CC=CC=C1 WPLOVIFNBMNBPD-ATHMIXSHSA-N 0.000 description 1
238000013268 sustained release Methods 0.000 description 1
239000012730 sustained-release form Substances 0.000 description 1
238000012360 testing method Methods 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000004614 tumor growth Effects 0.000 description 1
210000003462 vein Anatomy 0.000 description 1

Landscapes

Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

CA000546248A 1986-04-09 1987-09-08 Sels de compose de germanium organique et medicament en renfermant Expired - Lifetime CA1296277C (fr)

Priority Applications (2)

Application Number	Priority Date	Filing Date	Title
JP61081875A JPS62252794A (ja)	1986-04-09	1986-04-09	有機ゲルマニウム化合物及びそれを含む薬剤
CA000546248A CA1296277C (fr)	1986-04-09	1987-09-08	Sels de compose de germanium organique et medicament en renfermant

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP61081875A JPS62252794A (ja)	1986-04-09	1986-04-09	有機ゲルマニウム化合物及びそれを含む薬剤
CA000546248A CA1296277C (fr)	1986-04-09	1987-09-08	Sels de compose de germanium organique et medicament en renfermant

Publications (1)

Publication Number	Publication Date
CA1296277C true CA1296277C (fr)	1992-02-25

Family

ID=25671495

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000546248A Expired - Lifetime CA1296277C (fr)	1986-04-09	1987-09-08	Sels de compose de germanium organique et medicament en renfermant

Country Status (2)

Country	Link
JP (1)	JPS62252794A (fr)
CA (1)	CA1296277C (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH01139587A (ja) *	1987-11-27	1989-06-01	Sanwa Kagaku Kenkyusho Co Ltd	３−オキシゲルミルプロピオン酸ポリマーの塩基性アミノ酸及び有機アミン塩、その製法及び該化合物を有効成分とする免疫賦活剤
JPH01149723A (ja) *	1987-12-07	1989-06-12	Asai Gerumaniumu Kenkyusho:Kk	骨芽細胞活性化剤

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5844677A (ja) *	1981-09-09	1983-03-15	富士通株式会社	プリント板直載形同軸コネクタ
JPS59141587A (ja) *	1983-01-31	1984-08-14	インダストリアル・テクノロジ−・リサ−チ・インスチチユ−ト	有機ゲルマニウムプロピオン酸誘導体の製造方法
JPS59196068A (ja) *	1983-04-20	1984-11-07	Yuko Hochido	ゲルマニウム入り卵

1986
- 1986-04-09 JP JP61081875A patent/JPS62252794A/ja active Pending
1987
- 1987-09-08 CA CA000546248A patent/CA1296277C/fr not_active Expired - Lifetime

Also Published As

Publication number	Publication date
JPS62252794A (ja)	1987-11-04

Legal Events

Date	Code	Title	Description
1999-02-25	MKLA	Lapsed

Publication	Publication Date	Title
EP0491708B1 (fr)	1997-09-24	Separation d'aminoarginine, utilisee pour bloquer la formation d'oxyde nitrique dans le corps
EP0138420B1 (fr)	1989-11-29	Compositions pharmaceutiques contenant des dérivés de 1-hydroxypyrid-2-one
JPH07501539A (ja)	1995-02-16	Ｎ，ｎ’−ジアセチルシスチンの有機塩
JPS5912650B2 (ja)	1984-03-24	フエニル脂肪族飽和カルボン酸の塩類の製造法
JPH02500275A (ja)	1990-02-01	潰瘍の予防のための方法及び組成物
JPH06500316A (ja)	1994-01-13	化合物
JPH03501970A (ja)	1991-05-09	Ｓ‐アデノシル‐ｌ‐メチオニン（ｓａｍ）のアシル化タウリン誘導体との親油性塩
JPH0662407B2 (ja)	1994-08-17	安定化された３―オキシゲルミルプロピオン酸ポリマーを有効成分とする免疫調整剤
US4973553A (en)	1990-11-27	Salt or organogermanium compound and medicine containing the same
US5550249A (en)	1996-08-27	Water soluble derivatives of biotin and related therapeutical compositions
EP0154009A1 (fr)	1985-09-11	Utilisation d'un diuretique de type thiazide pour la manufacture d'un médicament antihypertenseur non-diuretique
US5739167A (en)	1998-04-14	Desferrioxamine-B salts and their use as orally effective iron chelators
CA1296277C (fr)	1992-02-25	Sels de compose de germanium organique et medicament en renfermant
EP0207436A2 (fr)	1987-01-07	Sels cytidine-diphosphocholine convenant particulièrement pour l'utilisation par voie orale
JPS60120995A (ja)	1985-06-28	新規アミノ酸誘導体の製法
KR970008107B1 (ko)	1997-05-21	항간질환성 조성물
US4847282A (en)	1989-07-11	Mucolytic acetylcysteine salts
JP2569060B2 (ja)	1997-01-08	グルタミルシスティン誘導体、その製造法およびそれを有効成分とする組織グルタチオンレベル向上剤
GB2211187A (en)	1989-06-28	Tromethamine salt of 1-methyl-¼-oxo-alpha-(phenylcarbamoyl)-2-pyrrolepropio- nitrile
KR930007994B1 (ko)	1993-08-25	유기 게르마늄 화합물의 염 및 이를 포함하는 약제
JPS62252793A (ja)	1987-11-04	有機ゲルマニウム化合物及びそれを含む薬剤
EP0335745A1 (fr)	1989-10-04	Procédé de préparation de pyridin-4-ones
JPH02250896A (ja)	1990-10-08	３―ピログルタミル―チアゾリジン―４―カルボン酸誘導体
KR100372188B1 (ko)	2003-05-12	3-[2-[4-(3-클로로-2-메틸페닐)-1-피레라지닐]에틸]-5,6-디메톡시-1-(4-이미다졸릴메틸)-1h-인다졸이염산염의결정및이의제조방법
US3821224A (en)	1974-06-28	Magnesium orotate glycinate and its complex compound with magnesium glycinate and their preparation