NO854112L - Substans, materialblanding og fremgangsmaate for anvendelse av denne. - Google Patents

Substans, materialblanding og fremgangsmaate for anvendelse av denne.

Info

Publication number: NO854112L
Authority: NO; Norway
Prior art keywords: acid; cox; pancratistatin; coch; active ingredient
Prior art date: 1984-02-17

Application number

NO854112A

Other languages

English (en)

Norwegian (no)

Inventor

George R Pettit

Original Assignee

Univ Arizona

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.)

1984-02-17

Filing date

1985-10-16

Publication date

1985-10-16

1985-10-16 Application filed by Univ Arizona filed Critical Univ Arizona

1985-10-16 Publication of NO854112L publication Critical patent/NO854112L/no

Links

238000000034 method Methods 0.000 title claims description 31
239000000126 substance Substances 0.000 title claims description 15
239000000203 mixture Substances 0.000 title description 9
VREZDOWOLGNDPW-ALTGWBOUSA-N Pancratistatin Chemical compound C1=C2[C@H]3[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O)[C@@H]3NC(=O)C2=C(O)C2=C1OCO2 VREZDOWOLGNDPW-ALTGWBOUSA-N 0.000 claims abstract description 43
VREZDOWOLGNDPW-MYVCAWNPSA-N Pancratistatin Natural products O=C1N[C@H]2[C@H](O)[C@H](O)[C@H](O)[C@H](O)[C@@H]2c2c1c(O)c1OCOc1c2 VREZDOWOLGNDPW-MYVCAWNPSA-N 0.000 claims abstract description 40
VREZDOWOLGNDPW-UHFFFAOYSA-N pancratistatine Natural products C1=C2C3C(O)C(O)C(O)C(O)C3NC(=O)C2=C(O)C2=C1OCO2 VREZDOWOLGNDPW-UHFFFAOYSA-N 0.000 claims abstract description 40
230000000118 anti-neoplastic effect Effects 0.000 claims abstract description 10
239000002253 acid Substances 0.000 claims abstract description 9
239000004480 active ingredient Substances 0.000 claims description 50
238000002360 preparation method Methods 0.000 claims description 34
201000010099 disease Diseases 0.000 claims description 15
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 15
230000001613 neoplastic effect Effects 0.000 claims description 15
239000000825 pharmaceutical preparation Substances 0.000 claims description 9
YYDLFVZOIDOGSO-KKBFJBPOSA-N Lycoricidine Chemical compound C1=C2C3=C[C@H](O)[C@@H](O)[C@@H](O)[C@@H]3NC(=O)C2=CC2=C1OCO2 YYDLFVZOIDOGSO-KKBFJBPOSA-N 0.000 claims description 7
LZAZURSABQIKGB-UHFFFAOYSA-N Narciclasine Tetraacetat Natural products C1=C2C3=CC(O)C(O)C(O)C3NC(=O)C2=C(O)C2=C1OCO2 LZAZURSABQIKGB-UHFFFAOYSA-N 0.000 claims description 7
230000037396 body weight Effects 0.000 claims description 7
231100000252 nontoxic Toxicity 0.000 claims description 5
230000003000 nontoxic effect Effects 0.000 claims description 5
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 25
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 18
239000000843 powder Substances 0.000 description 16
239000002552 dosage form Substances 0.000 description 15
IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 14
239000003826 tablet Substances 0.000 description 14
239000002775 capsule Substances 0.000 description 13
-1 glycoside derivatives of pancratistatin Chemical class 0.000 description 13
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
239000000725 suspension Substances 0.000 description 12
239000002609 medium Substances 0.000 description 11
239000004615 ingredient Substances 0.000 description 10
239000000243 solution Substances 0.000 description 10
240000005062 Hymenocallis littoralis Species 0.000 description 9
206010028980 Neoplasm Diseases 0.000 description 7
239000013078 crystal Substances 0.000 description 7
239000007903 gelatin capsule Substances 0.000 description 7
125000004435 hydrogen atom Chemical group [H]* 0.000 description 7
239000002904 solvent Substances 0.000 description 7
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
201000011510 cancer Diseases 0.000 description 6
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
239000000047 product Substances 0.000 description 6
239000000829 suppository Substances 0.000 description 6
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 5
229920005654 Sephadex Polymers 0.000 description 5
239000012507 Sephadex™ Substances 0.000 description 5
239000008346 aqueous phase Substances 0.000 description 5
150000001875 compounds Chemical class 0.000 description 5
238000001914 filtration Methods 0.000 description 5
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239000007787 solid Substances 0.000 description 5
230000003595 spectral effect Effects 0.000 description 5
230000001225 therapeutic effect Effects 0.000 description 5
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
241000196324 Embryophyta Species 0.000 description 4
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 4
239000003480 eluent Substances 0.000 description 4
239000011159 matrix material Substances 0.000 description 4
235000000346 sugar Nutrition 0.000 description 4
239000006188 syrup Substances 0.000 description 4
235000020357 syrup Nutrition 0.000 description 4
ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical class CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 4
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 3
208000028018 Lymphocytic leukaemia Diseases 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000011149 active material Substances 0.000 description 3
239000000443 aerosol Substances 0.000 description 3
230000001093 anti-cancer Effects 0.000 description 3
239000002246 antineoplastic agent Substances 0.000 description 3
239000007900 aqueous suspension Substances 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
239000011248 coating agent Substances 0.000 description 3
238000000576 coating method Methods 0.000 description 3
239000003085 diluting agent Substances 0.000 description 3
239000006185 dispersion Substances 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
238000011049 filling Methods 0.000 description 3
238000002955 isolation Methods 0.000 description 3
208000003747 lymphoid leukemia Diseases 0.000 description 3
239000000463 material Substances 0.000 description 3
238000002844 melting Methods 0.000 description 3
229920000609 methyl cellulose Polymers 0.000 description 3
239000001923 methylcellulose Substances 0.000 description 3
235000010981 methylcellulose Nutrition 0.000 description 3
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 3
239000012071 phase Substances 0.000 description 3
238000003825 pressing Methods 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
238000003756 stirring Methods 0.000 description 3
238000004809 thin layer chromatography Methods 0.000 description 3
AFPHTEQTJZKQAQ-UHFFFAOYSA-N 3-nitrobenzoic acid Chemical compound OC(=O)C1=CC=CC([N+]([O-])=O)=C1 AFPHTEQTJZKQAQ-UHFFFAOYSA-N 0.000 description 2
ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 2
ZEYHEAKUIGZSGI-UHFFFAOYSA-N 4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1 ZEYHEAKUIGZSGI-UHFFFAOYSA-N 0.000 description 2
OTLNPYWUJOZPPA-UHFFFAOYSA-N 4-nitrobenzoic acid Chemical compound OC(=O)C1=CC=C([N+]([O-])=O)C=C1 OTLNPYWUJOZPPA-UHFFFAOYSA-N 0.000 description 2
JOOXCMJARBKPKM-UHFFFAOYSA-N 4-oxopentanoic acid Chemical compound CC(=O)CCC(O)=O JOOXCMJARBKPKM-UHFFFAOYSA-N 0.000 description 2
HCJMNOSIAGSZBM-UHFFFAOYSA-N 6-methylsalicylic acid Chemical compound CC1=CC=CC(O)=C1C(O)=O HCJMNOSIAGSZBM-UHFFFAOYSA-N 0.000 description 2
241000416162 Astragalus gummifer Species 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
239000005711 Benzoic acid Substances 0.000 description 2
239000004215 Carbon black (E152) Substances 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
YVHAIVPPUIZFBA-UHFFFAOYSA-N Cyclopentylacetic acid Chemical compound OC(=O)CC1CCCC1 YVHAIVPPUIZFBA-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
108010010803 Gelatin Proteins 0.000 description 2
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
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 2
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
229920001615 Tragacanth Polymers 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
ZCHPKWUIAASXPV-UHFFFAOYSA-N acetic acid;methanol Chemical compound OC.CC(O)=O ZCHPKWUIAASXPV-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
125000002252 acyl group Chemical group 0.000 description 2
150000007933 aliphatic carboxylic acids Chemical class 0.000 description 2
125000003545 alkoxy group Chemical group 0.000 description 2
RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 2
235000010233 benzoic acid Nutrition 0.000 description 2
230000008033 biological extinction Effects 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
239000002021 butanolic extract Substances 0.000 description 2
238000004364 calculation method Methods 0.000 description 2
235000014633 carbohydrates Nutrition 0.000 description 2
150000001720 carbohydrates Chemical class 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
239000000470 constituent Substances 0.000 description 2
238000012937 correction Methods 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical compound OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 description 2
LJOODBDWMQKMFB-UHFFFAOYSA-N cyclohexylacetic acid Chemical compound OC(=O)CC1CCCCC1 LJOODBDWMQKMFB-UHFFFAOYSA-N 0.000 description 2
JBDSSBMEKXHSJF-UHFFFAOYSA-N cyclopentanecarboxylic acid Chemical compound OC(=O)C1CCCC1 JBDSSBMEKXHSJF-UHFFFAOYSA-N 0.000 description 2
229940127089 cytotoxic agent Drugs 0.000 description 2
DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
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238000010828 elution Methods 0.000 description 2
239000000284 extract Substances 0.000 description 2
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239000000796 flavoring agent Substances 0.000 description 2
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238000002329 infrared spectrum Methods 0.000 description 2
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HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
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LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 2
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238000001953 recrystallisation Methods 0.000 description 2
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239000000080 wetting agent Substances 0.000 description 2
238000002424 x-ray crystallography Methods 0.000 description 2
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238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
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GHUXGGOHYSFQKT-UHFFFAOYSA-N 2-bromo-6-methylcyclohexane-1-carboxylic acid Chemical compound CC1CCCC(Br)C1C(O)=O GHUXGGOHYSFQKT-UHFFFAOYSA-N 0.000 description 1
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UOYCVJQBIVUXEK-UHFFFAOYSA-N 2-chlorocyclohexane-1-carboxylic acid Chemical compound OC(=O)C1CCCCC1Cl UOYCVJQBIVUXEK-UHFFFAOYSA-N 0.000 description 1
JDEFPFLTCXIVDH-UHFFFAOYSA-N 2-cyanopropanoic acid Chemical compound N#CC(C)C(O)=O JDEFPFLTCXIVDH-UHFFFAOYSA-N 0.000 description 1
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AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 description 1
229960000310 isoleucine Drugs 0.000 description 1
VDBNYAPERZTOOF-UHFFFAOYSA-N isoquinolin-1(2H)-one Chemical compound C1=CC=C2C(=O)NC=CC2=C1 VDBNYAPERZTOOF-UHFFFAOYSA-N 0.000 description 1
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
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235000019359 magnesium stearate Nutrition 0.000 description 1
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
229960002510 mandelic acid Drugs 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
235000013310 margarine Nutrition 0.000 description 1
239000003264 margarine Substances 0.000 description 1
201000001441 melanoma Diseases 0.000 description 1
GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
230000003278 mimic effect Effects 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
238000000465 moulding Methods 0.000 description 1
WWECJGLXBSQKRF-UHFFFAOYSA-N n,n-dimethylformamide;methanol Chemical compound OC.CN(C)C=O WWECJGLXBSQKRF-UHFFFAOYSA-N 0.000 description 1
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 1
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
229940042126 oral powder Drugs 0.000 description 1
229940100692 oral suspension Drugs 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
229960003104 ornithine Drugs 0.000 description 1
IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
239000002245 particle Substances 0.000 description 1
238000005192 partition Methods 0.000 description 1
235000019271 petrolatum Nutrition 0.000 description 1
239000008024 pharmaceutical diluent Substances 0.000 description 1
RZFVLEJOHSLEFR-UHFFFAOYSA-N phenanthridone Chemical compound C1=CC=C2C(O)=NC3=CC=CC=C3C2=C1 RZFVLEJOHSLEFR-UHFFFAOYSA-N 0.000 description 1
COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 1
XNERWVPQCYSMLC-UHFFFAOYSA-N phenylpropiolic acid Chemical compound OC(=O)C#CC1=CC=CC=C1 XNERWVPQCYSMLC-UHFFFAOYSA-N 0.000 description 1
231100000614 poison Toxicity 0.000 description 1
230000007096 poisonous effect Effects 0.000 description 1
238000005498 polishing Methods 0.000 description 1
230000002335 preservative effect Effects 0.000 description 1
238000012545 processing Methods 0.000 description 1
239000001294 propane Substances 0.000 description 1
239000003380 propellant Substances 0.000 description 1
239000011253 protective coating Substances 0.000 description 1
JUJWROOIHBZHMG-RALIUCGRSA-N pyridine-d5 Chemical compound [2H]C1=NC([2H])=C([2H])C([2H])=C1[2H] JUJWROOIHBZHMG-RALIUCGRSA-N 0.000 description 1
229940107700 pyruvic acid Drugs 0.000 description 1
229940100618 rectal suppository Drugs 0.000 description 1
239000006215 rectal suppository Substances 0.000 description 1
238000011160 research Methods 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
230000007017 scission Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000004208 shellac Substances 0.000 description 1
ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
229940113147 shellac Drugs 0.000 description 1
235000013874 shellac Nutrition 0.000 description 1
JXOHGGNKMLTUBP-HSUXUTPPSA-N shikimic acid Chemical compound O[C@@H]1CC(C(O)=O)=C[C@@H](O)[C@H]1O JXOHGGNKMLTUBP-HSUXUTPPSA-N 0.000 description 1
JXOHGGNKMLTUBP-JKUQZMGJSA-N shikimic acid Natural products O[C@@H]1CC(C(O)=O)=C[C@H](O)[C@@H]1O JXOHGGNKMLTUBP-JKUQZMGJSA-N 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000002002 slurry Substances 0.000 description 1
208000000587 small cell lung carcinoma Diseases 0.000 description 1
239000007921 spray Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
230000001954 sterilising effect Effects 0.000 description 1
238000004659 sterilization and disinfection Methods 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
230000009897 systematic effect Effects 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
125000005031 thiocyano group Chemical group S(C#N)* 0.000 description 1
ODBLHEXUDAPZAU-UHFFFAOYSA-N threo-D-isocitric acid Natural products OC(=O)C(O)C(C(O)=O)CC(O)=O ODBLHEXUDAPZAU-UHFFFAOYSA-N 0.000 description 1
FGMPLJWBKKVCDB-UHFFFAOYSA-N trans-L-hydroxy-proline Natural products ON1CCCC1C(O)=O FGMPLJWBKKVCDB-UHFFFAOYSA-N 0.000 description 1
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
238000002211 ultraviolet spectrum Methods 0.000 description 1
238000009827 uniform distribution Methods 0.000 description 1
229940120293 vaginal suppository Drugs 0.000 description 1
239000006216 vaginal suppository Substances 0.000 description 1
235000016788 valerian Nutrition 0.000 description 1
239000004474 valine Substances 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
239000008215 water for injection Substances 0.000 description 1
239000001993 wax Substances 0.000 description 1
238000005303 weighing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Medicines Containing Plant Substances (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Detergent Compositions (AREA)
Compositions Of Macromolecular Compounds (AREA)
Medicinal Preparation (AREA)

NO854112A 1984-02-17 1985-10-16 Substans, materialblanding og fremgangsmaate for anvendelse av denne. NO854112L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US06/581,188 US4985436A (en)	1984-02-17	1984-02-17	Composition of matter for inhibiting leukemias and sarcomas

Publications (1)

Publication Number	Publication Date
NO854112L true NO854112L (no)	1985-10-16

Family

ID=24324233

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO854112A NO854112L (no)	1984-02-17	1985-10-16	Substans, materialblanding og fremgangsmaate for anvendelse av denne.

Country Status (11)

Country	Link
US (2)	US4985436A (de)
EP (1)	EP0175709B1 (de)
JP (1)	JPH0699436B2 (de)
KR (1)	KR900004003B1 (de)
AT (1)	ATE78481T1 (de)
AU (1)	AU571948B2 (de)
CA (1)	CA1297108C (de)
DE (1)	DE3586381T2 (de)
IT (1)	IT1221760B (de)
NO (1)	NO854112L (de)
WO (1)	WO1985003708A1 (de)

Families Citing this family (18)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5001140A (en) *	1989-04-17	1991-03-19	Hoffmann-La Roche Inc.	Cycloalkylthiazoles
US5180733A (en) *	1990-03-30	1993-01-19	Abbott Laboratories	Biogenic amine uptake inhibitors
HU220357B (hu) *	1992-02-28	2001-12-28	Autoimmune Inc.	Eljárás és készítmények autoimmun betegségek kezelésére bystander antigén alkalmazásával
US5529989A (en) *	1995-01-09	1996-06-25	Arizona Board Of Regents Acting On Behalf Of Arizona State University	Pancratistatin prodrug
MXPA02008014A (es)	2000-02-18	2004-04-05	New York Medical College	Composiciones inhibidoras de tumores de 1-nitroacridina.
US6495719B2 (en) *	2001-03-27	2002-12-17	Circagen Pharmaceutical	Histone deacetylase inhibitors
US7312247B2 (en)	2001-03-27	2007-12-25	Errant Gene Therapeutics, Llc	Histone deacetylase inhibitors
US8026280B2 (en)	2001-03-27	2011-09-27	Errant Gene Therapeutics, Llc	Histone deacetylase inhibitors
US7842727B2 (en) *	2001-03-27	2010-11-30	Errant Gene Therapeutics, Llc	Histone deacetylase inhibitors
CA2486303C (en) *	2002-05-22	2013-04-30	Errant Gene Therapeutics, Llc	Histone deacetylase inhibitors based on alpha-ketoepoxide compounds
AU2003291097A1 (en) *	2002-11-20	2004-06-15	Errant Gene Therapeutics, Llc	Treatment of lung cells with histone deacetylase inhibitors
EP1990346A3 (de) *	2002-12-09	2009-02-18	ARIZONA BOARD OF REGENTS, A BODY CORPORATE OF THE STATE OF ARIZONA acting for and on behalf of ARIZONA STATE UNIVERSITY	Verfahren zur Herstellung von Narcistatin Prodrugs
US20050261246A1 (en) *	2004-03-05	2005-11-24	The Arizona Board Of Regents	Methods for treating inflammatory and autoimmune diseases
WO2006052916A2 (en) *	2004-11-08	2006-05-18	Errant Gene Therapeutics, Inc.	Histone deacetylase inhibitors
FR2934266B1 (fr) *	2008-07-28	2010-09-17	Pf Medicament	Derives azotes de la pancratistatine
WO2016130969A1 (en)	2015-02-13	2016-08-18	George Robert Pettit	Silstatin compounds
CN106543194A (zh) *	2015-09-22	2017-03-29	孙青*	水仙环素衍生物及其制备与在制备抗肿瘤药物中的应用
US11629167B2 (en)	2017-11-09	2023-04-18	Arizona Board Of Regents On Behalf Of Arizona State University	Betulastatin compounds

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3583993A (en) *	1967-03-28	1971-06-08	Shionogi & Co	Plant growth regulating substances,lycoricidins
US3588993A (en) *	1969-03-21	1971-06-29	Kay Mfg Corp	Apparatus and method for feeding nested coil springs in rows

1984
- 1984-02-17 US US06/581,188 patent/US4985436A/en not_active Expired - Lifetime
1985
- 1985-02-13 CA CA000474222A patent/CA1297108C/en not_active Expired - Lifetime
- 1985-02-19 JP JP60501020A patent/JPH0699436B2/ja not_active Expired - Fee Related
- 1985-02-19 EP EP85901227A patent/EP0175709B1/de not_active Expired - Lifetime
- 1985-02-19 AU AU39978/85A patent/AU571948B2/en not_active Ceased
- 1985-02-19 DE DE8585901227T patent/DE3586381T2/de not_active Expired - Lifetime
- 1985-02-19 WO PCT/US1985/000237 patent/WO1985003708A1/en not_active Ceased
- 1985-02-19 AT AT85901227T patent/ATE78481T1/de active
- 1985-08-14 IT IT21938/85A patent/IT1221760B/it active
- 1985-10-16 NO NO854112A patent/NO854112L/no unknown
- 1985-10-17 KR KR8570260A patent/KR900004003B1/ko not_active Expired
1987
- 1987-01-06 US US07/000,589 patent/US4866071A/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
JPH0699436B2 (ja)	1994-12-07
AU3997885A (en)	1985-09-10
ATE78481T1 (de)	1992-08-15
WO1985003708A1 (en)	1985-08-29
US4866071A (en)	1989-09-12
AU571948B2 (en)	1988-04-28
CA1297108C (en)	1992-03-10
EP0175709A4 (de)	1986-07-24
DE3586381D1 (de)	1992-08-27
EP0175709A1 (de)	1986-04-02
IT1221760B (it)	1990-07-12
DE3586381T2 (de)	1993-01-21
EP0175709B1 (de)	1992-07-22
US4985436A (en)	1991-01-15
KR900004003B1 (en)	1990-06-07
JPS61501986A (ja)	1986-09-11
IT8521938A0 (it)	1985-08-14

Publication	Publication Date	Title
NO854112L (no)	1985-10-16	Substans, materialblanding og fremgangsmaate for anvendelse av denne.
EP0109811B1 (de)	1986-06-04	Bryozoan-Antibiotika
US6713480B2 (en)	2004-03-30	Phenylahistin and the phenylahistin analogs, a new class of anti-tumor compounds
EP0264173B1 (de)	1992-01-15	Bryostatine
JPS61197585A (ja)	1986-09-01	新規なブリオスタチン４〜８
JP3430322B2 (ja)	2003-07-28	スポンギスタチン５、７、８及び９
JPH04279589A (ja)	1992-10-05	新規スクアレンシンテターゼ阻害剤
WO1993016065A1 (en)	1993-08-19	Cholesterol lowering compounds
US3973608A (en)	1976-08-10	Microbial production of certain isoflavones
JPH0687861A (ja)	1994-03-29	ネリスタチン１
PT98901A (pt)	1992-08-31	Processo para a preparacao de dioxabiciclo-octanos uteis como inibidores da esqualeno-sintetase
Tian et al.	2022	New diketopiperazine alkaloid and polyketides from marine-derived fungus Penicillium sp. TW58-16 with antibacterial activity against Helicobacter pylori
JP3639973B2 (ja)	2005-04-20	スポンギスタチン６
JPH0457678B2 (de)	1992-09-14
US6403636B1 (en)	2002-06-11	Xanthone compounds, their preparation and use as medicament
WO1999043314A9 (en)	2001-03-01	Farnesyl-protein transferase inhibitors
CZ290320B6 (cs)	2002-07-17	Alkaloidy z Mappia foetida, způsob jejich výroby, jejich pouľití k výrobě farmaceutických prostředků a farmaceutické prostředky s jejich obsahem
US3970641A (en)	1976-07-20	Antibiotic 27,706 RP and salt thereof
Karasawa et al.	2015	Determination of the absolute configuration of the novel anti-trypanosomal iridoid molucidin isolated from Morinda lucida by X-ray analysis
DK166085B (da)	1993-03-08	Antineoplastiske phenanthridoner, farmaceutiske praeparater indeholdende disse samt deres anvendelse til fremstilling af et farmaceutisk praeparat til behandling af en vaert, som er angrebet af en neoplastisk sygdom
JPH02104582A (ja)	1990-04-17	ロリニアスタチン１
CN112300182A (zh)	2021-02-02	莲花氏烷型生物碱类化合物及其制备方法和用途
JPH0959275A (ja)	1997-03-04	新規物質トリプロスタチン、その製造方法、細胞周期阻害剤および抗腫瘍剤
CN109336891B (zh)	2020-04-10	5-（呋喃-2’-羰基）-2,3-二氢-1h-吡咯嗪-7-羧酸及其衍生物
CN120829353A (zh)	2025-10-24	一种顺反式Diels-Alder加合物及其制备方法和应用