JPH0260648B2 - - Google Patents
Info
- Publication number
- JPH0260648B2 JPH0260648B2 JP55037150A JP3715080A JPH0260648B2 JP H0260648 B2 JPH0260648 B2 JP H0260648B2 JP 55037150 A JP55037150 A JP 55037150A JP 3715080 A JP3715080 A JP 3715080A JP H0260648 B2 JPH0260648 B2 JP H0260648B2
- Authority
- JP
- Japan
- Prior art keywords
- carboxylic acid
- thiazolidine
- compound
- group
- tumor
- 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.)
- Expired - Lifetime
Links
- -1 2-substituted thiazolidine-4-carboxylic acid Chemical class 0.000 claims description 6
- 239000002246 antineoplastic agent Substances 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 206010028980 Neoplasm Diseases 0.000 description 9
- 238000002347 injection Methods 0.000 description 8
- 239000007924 injection Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000002775 capsule Substances 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- 241000699670 Mus sp. Species 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 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 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 230000000259 anti-tumor effect Effects 0.000 description 3
- 150000003935 benzaldehydes Chemical class 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000008101 lactose Substances 0.000 description 3
- IAVREABSGIHHMO-UHFFFAOYSA-N 3-hydroxybenzaldehyde Chemical compound OC1=CC=CC(C=O)=C1 IAVREABSGIHHMO-UHFFFAOYSA-N 0.000 description 2
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 2
- 206010003445 Ascites Diseases 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 229960002433 cysteine Drugs 0.000 description 2
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 2
- 235000018417 cysteine Nutrition 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 238000011081 inoculation Methods 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
- 239000000203 mixture Substances 0.000 description 2
- FXLOVSHXALFLKQ-UHFFFAOYSA-N p-tolualdehyde Chemical compound CC1=CC=C(C=O)C=C1 FXLOVSHXALFLKQ-UHFFFAOYSA-N 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 239000002504 physiological saline solution Substances 0.000 description 2
- 210000002345 respiratory system Anatomy 0.000 description 2
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- QIJRTFXNRTXDIP-UHFFFAOYSA-N (1-carboxy-2-sulfanylethyl)azanium;chloride;hydrate Chemical compound O.Cl.SCC(N)C(O)=O QIJRTFXNRTXDIP-UHFFFAOYSA-N 0.000 description 1
- APAUAYLVDHNFBF-UHFFFAOYSA-N 2-(2-hydroxyphenyl)-1,3-thiazolidine-4-carboxylic acid Chemical compound N1C(C(=O)O)CSC1C1=CC=CC=C1O APAUAYLVDHNFBF-UHFFFAOYSA-N 0.000 description 1
- TWPYJYQNZHPNGQ-UHFFFAOYSA-N 2-(4-hydroxyphenyl)-1,3-thiazolidine-4-carboxylic acid Chemical compound N1C(C(=O)O)CSC1C1=CC=C(O)C=C1 TWPYJYQNZHPNGQ-UHFFFAOYSA-N 0.000 description 1
- HTRWLFRKMUVNPG-UHFFFAOYSA-N 2-(4-methylphenyl)-1,3-thiazolidine-4-carboxylic acid Chemical compound C1=CC(C)=CC=C1C1SCC(C(O)=O)N1 HTRWLFRKMUVNPG-UHFFFAOYSA-N 0.000 description 1
- PKZJLOCLABXVMC-UHFFFAOYSA-N 2-Methoxybenzaldehyde Chemical compound COC1=CC=CC=C1C=O PKZJLOCLABXVMC-UHFFFAOYSA-N 0.000 description 1
- 239000001431 2-methylbenzaldehyde Substances 0.000 description 1
- AVPYQKSLYISFPO-UHFFFAOYSA-N 4-chlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1 AVPYQKSLYISFPO-UHFFFAOYSA-N 0.000 description 1
- UOQXIWFBQSVDPP-UHFFFAOYSA-N 4-fluorobenzaldehyde Chemical compound FC1=CC=C(C=O)C=C1 UOQXIWFBQSVDPP-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 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
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 229940024606 amino acid Drugs 0.000 description 1
- 235000001014 amino acid Nutrition 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 210000000436 anus Anatomy 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 229960001305 cysteine hydrochloride Drugs 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000003203 everyday effect Effects 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- WFWLQNSHRPWKFK-ZCFIWIBFSA-N tegafur Chemical compound O=C1NC(=O)C(F)=CN1[C@@H]1OCCC1 WFWLQNSHRPWKFK-ZCFIWIBFSA-N 0.000 description 1
- 229960001674 tegafur Drugs 0.000 description 1
- 150000003548 thiazolidines Chemical class 0.000 description 1
- DZLNHFMRPBPULJ-UHFFFAOYSA-N thioproline Chemical class OC(=O)C1CSCN1 DZLNHFMRPBPULJ-UHFFFAOYSA-N 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- 230000005760 tumorsuppression Effects 0.000 description 1
Landscapes
- Thiazole And Isothizaole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3715080A JPS56133216A (en) | 1980-03-24 | 1980-03-24 | Antitumor agent |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3715080A JPS56133216A (en) | 1980-03-24 | 1980-03-24 | Antitumor agent |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS56133216A JPS56133216A (en) | 1981-10-19 |
| JPH0260648B2 true JPH0260648B2 (zh) | 1990-12-17 |
Family
ID=12489576
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3715080A Granted JPS56133216A (en) | 1980-03-24 | 1980-03-24 | Antitumor agent |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS56133216A (zh) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57128625A (en) * | 1981-01-30 | 1982-08-10 | Rikagaku Kenkyusho | Carcinostatic |
| EA030611B1 (ru) * | 2013-03-15 | 2018-08-31 | Кэнсер Рисерч Текнолоджи, Ллк | Способы и композиции для модуляции гамма-глутамилового цикла |
| KR101793544B1 (ko) | 2015-12-30 | 2017-11-03 | 엘에스산전 주식회사 | 회로차단기의 이송장치 |
-
1980
- 1980-03-24 JP JP3715080A patent/JPS56133216A/ja active Granted
Non-Patent Citations (1)
| Title |
|---|
| J.MED.CHEM=1976 * |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS56133216A (en) | 1981-10-19 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US6355661B1 (en) | Methods for treatment of sickle cell anemia | |
| CZ2002724A3 (cs) | Farmaceutický přípravek obsahující derivát benzamidu se zlepąenou rozpustností a orální absorptivitou | |
| EP0424028B1 (en) | S(+)-ibuprofen-L-amino acid and S(+)-ibuprofen-D-amino acid as onset hastened enhanced analgesics | |
| WO1999002158A1 (fr) | Compositions medicinales stables, contenant des derives de 4,5-epoxymorphinane | |
| BG99609A (bg) | Ново арилпропионово производство,метод за неговото получаване и използването му като аналгетично средство | |
| US20030022923A1 (en) | Methods for treatment of sickle cell anemia | |
| HU209308B (en) | Process for producing codeine salt of substituted carboxylic acid | |
| EP0226591B1 (en) | Anti-tumor compositions containing the reaction product of a cytotoxic aldehyde with penicillamine and their use for the manufacture of medicaments | |
| EP0399051B1 (en) | Polyvalent antiinflammatory agent | |
| JP3253302B2 (ja) | ３−ジアルキルアミノエトキシベンゾイル−ベンゾフランを含有する非経口溶液 | |
| EP0357403A2 (en) | Substituted beta-diketones | |
| JPS6248678B2 (zh) | ||
| JPH0260648B2 (zh) | ||
| JPS5925377A (ja) | メトロニダゾ−ルとｎ，ｎ−ジメチルグリシンとのエステルおよびその酸付加湿 | |
| CN1044400A (zh) | 哌啶子基链烷醇衍生物的液体药物组合物 | |
| US4968673A (en) | Use of a thromboxane receptor antagonist in renal diseases and dysfunction | |
| JPH0365338B2 (zh) | ||
| US4942171A (en) | The compound, 6-(1-imidazolyl methyl)-5,6,7,8-tetrahydronaphthalene-2-carboxylic acid and salts thereof having antidiabetic activity | |
| JP2020183415A (ja) | 発泡剤を含む抗微生物組成物 | |
| JP4130700B2 (ja) | 抗腫瘍剤含有組成物 | |
| US3852454A (en) | Treatment of rheumatoid arthritis | |
| US3459854A (en) | Tetracycline cyclohexyl sulphamate and process for preparation | |
| CA1328613C (en) | Hypotensive agent comprising 4' ethyl-2-methyl-3-piperidinopropiophenone | |
| JPH0633242B2 (ja) | 有機ゲルマニウム化合物を有効成分とする肝炎の治療剤 | |
| JPH0372468A (ja) | トリアゾール化合物及びこれを含有する抗真菌剤 |