JPS6241485B2 - - Google Patents

Info

Publication number: JPS6241485B2
Authority: JP; Japan
Prior art keywords: ethylhexyl; mpr; group; oxybutyramide; oxybutyramides
Prior art date: 1979-03-24
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

Application number

JP3488379A

Other languages

English (en)

Japanese (ja)

Other versions

JPS55127320A (en

Inventor

Kenichi Sasaki

Shinobu Yoshizawa

Masaaki Saito

Junzo Nabeshima

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.)

Lion Corp

Original Assignee

Lion Corp

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.)

1979-03-24

Filing date

1979-03-24

Publication date

1987-09-03

1979-03-24 Application filed by Lion Corp filed Critical Lion Corp

1979-03-24 Priority to JP3488379A priority Critical patent/JPS55127320A/ja

1980-10-02 Publication of JPS55127320A publication Critical patent/JPS55127320A/ja

1987-09-03 Publication of JPS6241485B2 publication Critical patent/JPS6241485B2/ja

Status Granted legal-status Critical Current

Links

GLVAUDGFNGKCSF-UHFFFAOYSA-N mercaptopurine Chemical compound S=C1NC=NC2=C1NC=N2 GLVAUDGFNGKCSF-UHFFFAOYSA-N 0.000 claims description 51
229960001428 mercaptopurine Drugs 0.000 claims description 26
NKGPJODWTZCHGF-KQYNXXCUSA-N 6-thioinosinic acid Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C2=NC=NC(S)=C2N=C1 NKGPJODWTZCHGF-KQYNXXCUSA-N 0.000 claims description 23
239000002246 antineoplastic agent Substances 0.000 claims description 6
125000002947 alkylene group Chemical group 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
150000003839 salts Chemical class 0.000 claims description 3
150000001340 alkali metals Chemical group 0.000 claims description 2
150000001342 alkaline earth metals Chemical group 0.000 claims description 2
125000003277 amino group Chemical group 0.000 claims description 2
150000001991 dicarboxylic acids Chemical class 0.000 claims description 2
150000002148 esters Chemical class 0.000 claims description 2
125000000524 functional group Chemical group 0.000 claims description 2
125000004430 oxygen atom Chemical group O* 0.000 claims description 2
150000001875 compounds Chemical class 0.000 claims 1
NWIBSHFKIJFRCO-WUDYKRTCSA-N Mytomycin Chemical compound C1N2C(C(C(C)=C(N)C3=O)=O)=C3[C@@H](COC(N)=O)[C@@]2(OC)[C@@H]2[C@H]1N2 NWIBSHFKIJFRCO-WUDYKRTCSA-N 0.000 description 16
206010028980 Neoplasm Diseases 0.000 description 12
230000000259 anti-tumor effect Effects 0.000 description 12
229960004857 mitomycin Drugs 0.000 description 8
239000007787 solid Substances 0.000 description 8
-1 2-ethylhexyl Chemical group 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
230000004663 cell proliferation Effects 0.000 description 6
230000002401 inhibitory effect Effects 0.000 description 6
239000002504 physiological saline solution Substances 0.000 description 6
201000009030 Carcinoma Diseases 0.000 description 5
NKGPJODWTZCHGF-UHFFFAOYSA-N 9-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3h-purine-6-thione Chemical compound OC1C(O)C(CO)OC1N1C(NC=NC2=S)=C2N=C1 NKGPJODWTZCHGF-UHFFFAOYSA-N 0.000 description 4
229940041181 antineoplastic drug Drugs 0.000 description 4
201000011510 cancer Diseases 0.000 description 4
238000007796 conventional method Methods 0.000 description 4
241000699670 Mus sp. Species 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
230000037396 body weight Effects 0.000 description 3
210000004027 cell Anatomy 0.000 description 3
229940079593 drug Drugs 0.000 description 3
239000003814 drug Substances 0.000 description 3
230000000694 effects Effects 0.000 description 3
238000011156 evaluation Methods 0.000 description 3
238000002347 injection Methods 0.000 description 3
239000007924 injection Substances 0.000 description 3
238000000034 method Methods 0.000 description 3
239000000203 mixture Substances 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 2
AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 description 2
108010010803 Gelatin Proteins 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
241000699666 Mus <mouse, genus> Species 0.000 description 2
230000001093 anti-cancer Effects 0.000 description 2
239000002585 base Substances 0.000 description 2
239000012153 distilled water Substances 0.000 description 2
210000003414 extremity Anatomy 0.000 description 2
238000009472 formulation Methods 0.000 description 2
229920000159 gelatin Polymers 0.000 description 2
239000008273 gelatin Substances 0.000 description 2
235000019322 gelatine Nutrition 0.000 description 2
235000011852 gelatine desserts Nutrition 0.000 description 2
235000010445 lecithin Nutrition 0.000 description 2
239000000787 lecithin Substances 0.000 description 2
229940067606 lecithin Drugs 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
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 2
229920000053 polysorbate 80 Polymers 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
230000035755 proliferation Effects 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
239000000243 solution Substances 0.000 description 2
239000000829 suppository Substances 0.000 description 2
210000000689 upper leg Anatomy 0.000 description 2
JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 1
ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 1
244000215068 Acacia senegal Species 0.000 description 1
206010003445 Ascites Diseases 0.000 description 1
229920002261 Corn starch Polymers 0.000 description 1
CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 description 1
229920000084 Gum arabic Polymers 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
FBOZXECLQNJBKD-ZDUSSCGKSA-N L-methotrexate Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 FBOZXECLQNJBKD-ZDUSSCGKSA-N 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
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
235000004443 Ricinus communis Nutrition 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
239000000205 acacia gum Substances 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
229940009456 adriamycin Drugs 0.000 description 1
CEGOLXSVJUTHNZ-UHFFFAOYSA-K aluminium tristearate Chemical compound [Al+3].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CEGOLXSVJUTHNZ-UHFFFAOYSA-K 0.000 description 1
229940063655 aluminum stearate Drugs 0.000 description 1
238000010171 animal model Methods 0.000 description 1
210000003423 ankle Anatomy 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
239000008280 blood Substances 0.000 description 1
238000009395 breeding Methods 0.000 description 1
230000001488 breeding effect Effects 0.000 description 1
WTBQLHRVRKXSPX-UHFFFAOYSA-N butoctamide Chemical compound CCCCC(CC)CNC(=O)CC(C)O WTBQLHRVRKXSPX-UHFFFAOYSA-N 0.000 description 1
229950006519 butoctamide Drugs 0.000 description 1
159000000007 calcium salts Chemical class 0.000 description 1
230000009702 cancer cell proliferation Effects 0.000 description 1
239000002775 capsule Substances 0.000 description 1
210000001175 cerebrospinal fluid Anatomy 0.000 description 1
229940110456 cocoa butter Drugs 0.000 description 1
235000019868 cocoa butter Nutrition 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
229960004397 cyclophosphamide Drugs 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
239000007884 disintegrant Substances 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
238000001647 drug administration Methods 0.000 description 1
230000002900 effect on cell Effects 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
230000001804 emulsifying effect Effects 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
229940014259 gelatin Drugs 0.000 description 1
239000007902 hard capsule Substances 0.000 description 1
210000003630 histaminocyte Anatomy 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
229940071826 hydroxyethyl cellulose Drugs 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
239000008101 lactose Substances 0.000 description 1
235000019860 lauric fat Nutrition 0.000 description 1
239000007788 liquid Substances 0.000 description 1
210000003141 lower extremity Anatomy 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
201000006512 mast cell neoplasm Diseases 0.000 description 1
208000006971 mastocytoma Diseases 0.000 description 1
229960000485 methotrexate Drugs 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
229960002900 methylcellulose Drugs 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
238000002156 mixing Methods 0.000 description 1
210000003205 muscle Anatomy 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
235000013772 propylene glycol Nutrition 0.000 description 1
RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
239000007901 soft capsule Substances 0.000 description 1
239000001593 sorbitan monooleate Substances 0.000 description 1
235000011069 sorbitan monooleate Nutrition 0.000 description 1
229940035049 sorbitan monooleate Drugs 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
235000010356 sorbitol Nutrition 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
239000008399 tap water Substances 0.000 description 1
235000020679 tap water Nutrition 0.000 description 1
238000002054 transplantation Methods 0.000 description 1
210000004881 tumor cell Anatomy 0.000 description 1
230000005760 tumorsuppression Effects 0.000 description 1
238000005303 weighing Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

JP3488379A 1979-03-24 1979-03-24 Carcinostatic agent Granted JPS55127320A (en)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP3488379A JPS55127320A (en)	1979-03-24	1979-03-24	Carcinostatic agent

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP3488379A JPS55127320A (en)	1979-03-24	1979-03-24	Carcinostatic agent

Publications (2)

Publication Number	Publication Date
JPS55127320A JPS55127320A (en)	1980-10-02
JPS6241485B2 true JPS6241485B2 (de)	1987-09-03

Family

ID=12426530

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP3488379A Granted JPS55127320A (en)	1979-03-24	1979-03-24	Carcinostatic agent

Country Status (1)

Country	Link
JP (1)	JPS55127320A (de)

1979
- 1979-03-24 JP JP3488379A patent/JPS55127320A/ja active Granted

Also Published As

Publication number	Publication date
JPS55127320A (en)	1980-10-02

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US4438138A (en)	1984-03-20	Reduction of cholesterol with meta-chloro α-t-butylaminopropiophenone
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EP0171227A1 (de)	1986-02-12	Verwendung von Propiophenon-Verbindung
US4088778A (en)	1978-05-09	Method for the treatment of hypertension
JPWO1992004028A1 (ja)	1992-09-03	抗腫瘍効果増強剤及び抗腫瘍剤
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US1166208A (en)	1915-12-28	Physiologically-active base.