JPS62120388A - Ｓｆ−２３７０物質ハロゲン化誘導体とその製造法 - Google Patents
Ｓｆ−２３７０物質ハロゲン化誘導体とその製造法Info
- Publication number
- JPS62120388A JPS62120388A JP25765285A JP25765285A JPS62120388A JP S62120388 A JPS62120388 A JP S62120388A JP 25765285 A JP25765285 A JP 25765285A JP 25765285 A JP25765285 A JP 25765285A JP S62120388 A JPS62120388 A JP S62120388A
- Authority
- JP
- Japan
- Prior art keywords
- substance
- formula
- atom
- chlorine
- bromine
- 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
- 239000000126 substance Substances 0.000 title claims abstract description 62
- 238000004519 manufacturing process Methods 0.000 title claims description 12
- 150000001875 compounds Chemical class 0.000 claims abstract description 14
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 12
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 9
- 229910052740 iodine Inorganic materials 0.000 claims abstract description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
- 230000002140 halogenating effect Effects 0.000 claims abstract description 4
- KOZFSFOOLUUIGY-SOLYNIJKSA-N K-252a Chemical compound C12=C3N4C5=CC=CC=C5C3=C3CNC(=O)C3=C2C2=CC=CC=C2N1[C@H]1C[C@@](C(=O)OC)(O)[C@]4(C)O1 KOZFSFOOLUUIGY-SOLYNIJKSA-N 0.000 claims abstract description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 11
- 239000000460 chlorine Substances 0.000 claims description 9
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 2
- KOZFSFOOLUUIGY-UHFFFAOYSA-N K252a Natural products C12=C3N4C5=CC=CC=C5C3=C3CNC(=O)C3=C2C2=CC=CC=C2N1C1CC(C(=O)OC)(O)C4(C)O1 KOZFSFOOLUUIGY-UHFFFAOYSA-N 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 11
- 230000003115 biocidal effect Effects 0.000 abstract description 3
- 239000003795 chemical substances by application Substances 0.000 abstract description 3
- 238000005658 halogenation reaction Methods 0.000 abstract description 3
- 239000012442 inert solvent Substances 0.000 abstract description 3
- 239000000463 material Substances 0.000 abstract description 3
- 239000003242 anti bacterial agent Substances 0.000 abstract description 2
- 229940121375 antifungal agent Drugs 0.000 abstract description 2
- 239000003429 antifungal agent Substances 0.000 abstract 1
- 239000002220 antihypertensive agent Substances 0.000 abstract 1
- 239000004599 antimicrobial Substances 0.000 abstract 1
- 239000002934 diuretic Substances 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- 241000700159 Rattus Species 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 239000000741 silica gel Substances 0.000 description 8
- 229910002027 silica gel Inorganic materials 0.000 description 8
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 7
- 239000010931 gold Substances 0.000 description 7
- 229910052737 gold Inorganic materials 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 230000000844 anti-bacterial effect Effects 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 210000002700 urine Anatomy 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 5
- 208000004880 Polyuria Diseases 0.000 description 5
- 230000036772 blood pressure Effects 0.000 description 5
- 238000000354 decomposition reaction Methods 0.000 description 5
- 230000001882 diuretic effect Effects 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- 229910052736 halogen Inorganic materials 0.000 description 5
- 150000002367 halogens Chemical class 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- 206010020772 Hypertension Diseases 0.000 description 4
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
- 230000000843 anti-fungal effect Effects 0.000 description 4
- 230000003276 anti-hypertensive effect Effects 0.000 description 4
- 239000004020 conductor Substances 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000001819 mass spectrum Methods 0.000 description 4
- 238000004809 thin layer chromatography Methods 0.000 description 4
- 244000215068 Acacia senegal Species 0.000 description 3
- 229920000084 Gum arabic Polymers 0.000 description 3
- 239000000205 acacia gum Substances 0.000 description 3
- 235000010489 acacia gum Nutrition 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 238000005273 aeration Methods 0.000 description 3
- 230000004531 blood pressure lowering effect Effects 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 230000001631 hypertensive effect Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 230000002485 urinary effect Effects 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 2
- LQZMLBORDGWNPD-UHFFFAOYSA-N N-iodosuccinimide Chemical compound IN1C(=O)CCC1=O LQZMLBORDGWNPD-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 241000209140 Triticum Species 0.000 description 2
- 235000021307 Triticum Nutrition 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 230000007059 acute toxicity Effects 0.000 description 2
- 231100000403 acute toxicity Toxicity 0.000 description 2
- 230000001580 bacterial effect Effects 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 229940125904 compound 1 Drugs 0.000 description 2
- 229940125782 compound 2 Drugs 0.000 description 2
- 239000013058 crude material Substances 0.000 description 2
- 239000002178 crystalline material Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000002024 ethyl acetate extract Substances 0.000 description 2
- OAMZXMDZZWGPMH-UHFFFAOYSA-N ethyl acetate;toluene Chemical compound CCOC(C)=O.CC1=CC=CC=C1 OAMZXMDZZWGPMH-UHFFFAOYSA-N 0.000 description 2
- 230000029142 excretion Effects 0.000 description 2
- 230000001077 hypotensive effect Effects 0.000 description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 2
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 230000001766 physiological effect Effects 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000013587 production medium Substances 0.000 description 2
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- PPKPKFIWDXDAGC-IHWYPQMZSA-N (z)-1,2-dichloroprop-1-ene Chemical compound C\C(Cl)=C\Cl PPKPKFIWDXDAGC-IHWYPQMZSA-N 0.000 description 1
- WKFYEWXSRFQOKX-UHFFFAOYSA-N 1,4-dioxane;toluene Chemical compound C1COCCO1.CC1=CC=CC=C1 WKFYEWXSRFQOKX-UHFFFAOYSA-N 0.000 description 1
- ZESRJSPZRDMNHY-YFWFAHHUSA-N 11-deoxycorticosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 ZESRJSPZRDMNHY-YFWFAHHUSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 241000187361 Actinomadura sp. Species 0.000 description 1
- JBMKAUGHUNFTOL-UHFFFAOYSA-N Aldoclor Chemical class C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NC=NS2(=O)=O JBMKAUGHUNFTOL-UHFFFAOYSA-N 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 208000001953 Hypotension Diseases 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 241000191938 Micrococcus luteus Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 241000238413 Octopus Species 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 241000205407 Polygonum Species 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000003466 anti-cipated effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 210000001367 artery Anatomy 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 238000004166 bioassay Methods 0.000 description 1
- 238000009530 blood pressure measurement Methods 0.000 description 1
- 229940041514 candida albicans extract Drugs 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- SKCNIGRBPJIUBQ-UHFFFAOYSA-N chloroform;ethyl acetate Chemical compound ClC(Cl)Cl.CCOC(C)=O SKCNIGRBPJIUBQ-UHFFFAOYSA-N 0.000 description 1
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 230000036461 convulsion Effects 0.000 description 1
- 210000004748 cultured cell Anatomy 0.000 description 1
- ZESRJSPZRDMNHY-UHFFFAOYSA-N de-oxy corticosterone Natural products O=C1CCC2(C)C3CCC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 ZESRJSPZRDMNHY-UHFFFAOYSA-N 0.000 description 1
- 229940119740 deoxycorticosterone Drugs 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000003651 drinking water Substances 0.000 description 1
- 235000020188 drinking water Nutrition 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- DMDGGSIALPNSEE-UHFFFAOYSA-N hydroflumethiazide Chemical compound C1=C(C(F)(F)F)C(S(=O)(=O)N)=CC2=C1NCNS2(=O)=O DMDGGSIALPNSEE-UHFFFAOYSA-N 0.000 description 1
- 229960003313 hydroflumethiazide Drugs 0.000 description 1
- 208000021822 hypotensive Diseases 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 150000002500 ions Chemical group 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- -1 phosphoric acid imide Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 238000011218 seed culture Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000010902 straw Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 239000003451 thiazide diuretic agent Substances 0.000 description 1
- 241001446247 uncultured actinomycete Species 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000012138 yeast extract Substances 0.000 description 1
Landscapes
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP25765285A JPS62120388A (ja) | 1985-11-19 | 1985-11-19 | Ｓｆ−２３７０物質ハロゲン化誘導体とその製造法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP25765285A JPS62120388A (ja) | 1985-11-19 | 1985-11-19 | Ｓｆ−２３７０物質ハロゲン化誘導体とその製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62120388A true JPS62120388A (ja) | 1987-06-01 |
| JPH0215555B2 JPH0215555B2 (enrdf_load_stackoverflow) | 1990-04-12 |
Family
ID=17309220
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP25765285A Granted JPS62120388A (ja) | 1985-11-19 | 1985-11-19 | Ｓｆ−２３７０物質ハロゲン化誘導体とその製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62120388A (enrdf_load_stackoverflow) |
Cited By (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63295588A (ja) * | 1987-01-22 | 1988-12-01 | Kyowa Hakko Kogyo Co Ltd | 生理活性物質ｋ−２５２の誘導体 |
| US4877776A (en) * | 1987-12-24 | 1989-10-31 | Kyowa Hakko Kogyo Co., Ltd. | K-252 compounds |
| US4923986A (en) * | 1987-03-09 | 1990-05-08 | Kyowa Hakko Kogyo Co., Ltd. | Derivatives of physiologically active substance K-252 |
| WO1994006799A1 (fr) * | 1992-09-21 | 1994-03-31 | Kyowa Hakko Kogyo Co., Ltd. | Remede contre la thrombopenie |
| WO1994016706A1 (en) | 1993-01-28 | 1994-08-04 | Neorx Corporation | Therapeutic inhibitors of vascular smooth muscle cells |
| US5599808A (en) * | 1994-02-18 | 1997-02-04 | Cephalon, Inc. | Aqueous indolocarbazole solutions |
| US5618809A (en) * | 1989-12-14 | 1997-04-08 | Schering Corporation | Indolocarbazoles from saccharothrix aerocolonigenes copiosa subsp. nov SCC 1951 ATCC 53856 |
| US5621101A (en) * | 1992-07-24 | 1997-04-15 | Cephalon, Inc. | Protein kinase inhibitors for treatment of neurological disorders |
| US5741808A (en) * | 1992-07-24 | 1998-04-21 | Cephalon, Inc. | Protein kinase inhibitors for treatmen of neurological disorders |
| US6184217B1 (en) | 1996-06-25 | 2001-02-06 | Cephalon, Inc. | Use of K-252a derivative |
| US6200968B1 (en) | 1998-08-06 | 2001-03-13 | Cephalon, Inc. | Particle-forming compositions containing fused pyrrolocarbazoles |
| US6306849B1 (en) | 1996-06-03 | 2001-10-23 | Cephalon, Inc. | Selected derivatives of K-252a |
| US6875865B1 (en) | 1996-06-03 | 2005-04-05 | Cephalon, Inc. | Selected derivatives of K-252a |
| EP2098230A1 (en) | 1997-03-31 | 2009-09-09 | Boston Scientific Scimed Limited | Use of cytoskeletal inhibitors in crystalline form for the inhibition or prevention of restenosis |
| US7795246B2 (en) | 1998-08-06 | 2010-09-14 | Cephalon, Inc. | Particle-forming compositions containing fused pyrrolocarbazoles |
| EP2292225A1 (en) | 1997-03-31 | 2011-03-09 | Boston Scientific Scimed Limited | Dosage form comprising taxol in crystalline form |
-
1985
- 1985-11-19 JP JP25765285A patent/JPS62120388A/ja active Granted
Cited By (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63295588A (ja) * | 1987-01-22 | 1988-12-01 | Kyowa Hakko Kogyo Co Ltd | 生理活性物質ｋ−２５２の誘導体 |
| US4923986A (en) * | 1987-03-09 | 1990-05-08 | Kyowa Hakko Kogyo Co., Ltd. | Derivatives of physiologically active substance K-252 |
| US4877776A (en) * | 1987-12-24 | 1989-10-31 | Kyowa Hakko Kogyo Co., Ltd. | K-252 compounds |
| US5618809A (en) * | 1989-12-14 | 1997-04-08 | Schering Corporation | Indolocarbazoles from saccharothrix aerocolonigenes copiosa subsp. nov SCC 1951 ATCC 53856 |
| US5741808A (en) * | 1992-07-24 | 1998-04-21 | Cephalon, Inc. | Protein kinase inhibitors for treatmen of neurological disorders |
| US5756494A (en) * | 1992-07-24 | 1998-05-26 | Cephalon, Inc. | Protein kinase inhibitors for treatment of neurological disorders |
| US5621101A (en) * | 1992-07-24 | 1997-04-15 | Cephalon, Inc. | Protein kinase inhibitors for treatment of neurological disorders |
| WO1994006799A1 (fr) * | 1992-09-21 | 1994-03-31 | Kyowa Hakko Kogyo Co., Ltd. | Remede contre la thrombopenie |
| WO1994016706A1 (en) | 1993-01-28 | 1994-08-04 | Neorx Corporation | Therapeutic inhibitors of vascular smooth muscle cells |
| EP2324829A1 (en) | 1993-01-28 | 2011-05-25 | Boston Scientific Limited | Therapeutic inhibitors of vascular smooth muscle cells |
| US5599808A (en) * | 1994-02-18 | 1997-02-04 | Cephalon, Inc. | Aqueous indolocarbazole solutions |
| US6306849B1 (en) | 1996-06-03 | 2001-10-23 | Cephalon, Inc. | Selected derivatives of K-252a |
| US6875865B1 (en) | 1996-06-03 | 2005-04-05 | Cephalon, Inc. | Selected derivatives of K-252a |
| US6184217B1 (en) | 1996-06-25 | 2001-02-06 | Cephalon, Inc. | Use of K-252a derivative |
| EP2098230A1 (en) | 1997-03-31 | 2009-09-09 | Boston Scientific Scimed Limited | Use of cytoskeletal inhibitors in crystalline form for the inhibition or prevention of restenosis |
| EP2292225A1 (en) | 1997-03-31 | 2011-03-09 | Boston Scientific Scimed Limited | Dosage form comprising taxol in crystalline form |
| US6200968B1 (en) | 1998-08-06 | 2001-03-13 | Cephalon, Inc. | Particle-forming compositions containing fused pyrrolocarbazoles |
| US7795246B2 (en) | 1998-08-06 | 2010-09-14 | Cephalon, Inc. | Particle-forming compositions containing fused pyrrolocarbazoles |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0215555B2 (enrdf_load_stackoverflow) | 1990-04-12 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPS62120388A (ja) | Ｓｆ−２３７０物質ハロゲン化誘導体とその製造法 | |
| DE69129193T2 (de) | Triterpenderivat | |
| JPS6123192B2 (enrdf_load_stackoverflow) | ||
| JPS61103890A (ja) | ６−０−メチルエリスロマイシンａ誘導体 | |
| Puthiyapurayil et al. | Synthesis, spectral characterization and biological evaluation of a novel series of 6-arylsubstituted-3-[2-(4-substitutedphenyl) propan-2-yl]-7H-[1, 2, 4] triazolo [3, 4-b][1, 3, 4] thiadiazines | |
| EP0296975A1 (fr) | Dérivés du diméthyl-2,2 chromannol-3, procédé d'obtention et compositions pharmaceutiques les contenant | |
| CN106749494A (zh) | 具有肿瘤耐药逆转活性的α‑常春藤皂苷元衍生物及其制备方法和用途 | |
| CN113698378A (zh) | 一类萘醌类化合物及其制备与杀螨、杀菌用途 | |
| US4233333A (en) | 4,5-Dimethyl-thieno[3,2-d]isothiazolo-3(2H)-one-1,1-dioxides, compositions, and methods of use as a sweetener | |
| CN113788831A (zh) | 二氢吲嗪并吡咯酮衍生物及类似物及其合成方法 | |
| JPH0327534B2 (enrdf_load_stackoverflow) | ||
| CN106995450A (zh) | 一种雷公藤甲素衍生物及其制备方法和用途 | |
| CN114097804B (zh) | 一种二氨基嘧啶类化合物在防治农业病原菌中的用途 | |
| CN112300118B (zh) | 一种苯并噻喃二酮化合物及其制备方法和应用 | |
| KR100399589B1 (ko) | 신규 퀴놀린디온 유도체, 이의 제조방법 및 이를 포함하는약학적 조성물 | |
| CN107652338B (zh) | 糖偶联-1,2,3-三氮唑取代的多环芳烃衍生物在制备抗癌药物的用途 | |
| Katayama et al. | Anti-cancer activities of pyrazolo [1, 5-a] indole derivatives | |
| JP4038245B2 (ja) | 新規なフェナンスリジニウム誘導体 | |
| US5668168A (en) | 1,2-dithiin antiinfective agents | |
| US3641146A (en) | Halocolchicine derivatives | |
| DE1670377B2 (de) | Verfahren zur herstellung von rifamycinderivaten | |
| CZ282419B6 (cs) | Způsob výroby benzo/c/fenantridiniových derivátů a nové sloučeniny připravené tímto způsobem | |
| CN107641141B (zh) | 糖偶联-1,2,3-三氮唑取代的多环芳烃衍生物及制备方法 | |
| JPS6024102B2 (ja) | ５−フルオロウラシル誘導体の製法 | |
| CN103554125A (zh) | 4α-酰氧基-2′(2′,6′),2α-多卤代鬼臼毒素衍生物及制备和应用 |