NO843739L - Polyhydroksybenzosyrederivater. - Google Patents

Polyhydroksybenzosyrederivater.

Info

Publication number: NO843739L
Authority: NO; Norway
Prior art keywords: compound; administered; compound according; trihydroxybenzamidoxime; hydroxyl groups
Prior art date: 1983-05-23

Application number

NO843739A

Other languages

English (en)

Norwegian (no)

Inventor

Galen L Wampler

Howard Elford

Original Assignee

Riet Bartholomeus Van T

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.)

1983-05-23

Filing date

1984-09-19

Publication date

1984-12-06

1984-09-19 Application filed by Riet Bartholomeus Van T filed Critical Riet Bartholomeus Van T

1984-12-06 Publication of NO843739L publication Critical patent/NO843739L/no

Links

150000001875 compounds Chemical class 0.000 claims description 73
238000000034 method Methods 0.000 claims description 31
206010028980 Neoplasm Diseases 0.000 claims description 21
102000000505 Ribonucleotide Reductases Human genes 0.000 claims description 13
108010041388 Ribonucleotide Reductases Proteins 0.000 claims description 13
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
208000032839 leukemia Diseases 0.000 claims description 11
241000124008 Mammalia Species 0.000 claims description 8
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims description 7
239000002253 acid Substances 0.000 claims description 6
JOAASNKBYBFGDN-UHFFFAOYSA-N chembl1214554 Chemical compound ON=C(N)C1=CC=C(O)C(O)=C1 JOAASNKBYBFGDN-UHFFFAOYSA-N 0.000 claims description 6
BZMWYVQJKXCMQK-UHFFFAOYSA-N 2,3,4,5,6-pentahydroxybenzonitrile Chemical compound OC1=C(O)C(O)=C(C#N)C(O)=C1O BZMWYVQJKXCMQK-UHFFFAOYSA-N 0.000 claims description 5
FCMKUVQNNKLVHF-UHFFFAOYSA-N 2,3,4,5-tetrahydroxybenzonitrile Chemical compound OC1=CC(C#N)=C(O)C(O)=C1O FCMKUVQNNKLVHF-UHFFFAOYSA-N 0.000 claims description 5
MSLJYSGFUMYUDX-UHFFFAOYSA-N Trimidox Chemical compound ON=C(N)C1=CC(O)=C(O)C(O)=C1 MSLJYSGFUMYUDX-UHFFFAOYSA-N 0.000 claims description 5
150000003839 salts Chemical class 0.000 claims description 5
AWUHRASXGNMZBQ-UHFFFAOYSA-N N',3,4-trihydroxybenzenecarboximidamide hydrochloride Chemical compound Cl.ON=C(N)C1=CC=C(O)C(O)=C1 AWUHRASXGNMZBQ-UHFFFAOYSA-N 0.000 claims description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
238000011282 treatment Methods 0.000 claims description 4
230000015572 biosynthetic process Effects 0.000 claims description 3
230000002401 inhibitory effect Effects 0.000 claims description 3
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
ISSNOTRNQLZNJI-UHFFFAOYSA-N 2,3,4,5-tetrahydroxybenzamide Chemical compound NC(=O)C1=CC(O)=C(O)C(O)=C1O ISSNOTRNQLZNJI-UHFFFAOYSA-N 0.000 claims description 2
KBKNXSNOQYLIRI-UHFFFAOYSA-N N',3,4,5-tetrahydroxybenzenecarboximidamide hydrochloride Chemical compound Cl.ON=C(N)C1=CC(O)=C(O)C(O)=C1 KBKNXSNOQYLIRI-UHFFFAOYSA-N 0.000 claims description 2
201000010099 disease Diseases 0.000 claims description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 2
YKILLPJZPZOZSV-UHFFFAOYSA-N 3,4-dihydroxybenzenecarboximidamide Chemical compound NC(=N)C1=CC=C(O)C(O)=C1 YKILLPJZPZOZSV-UHFFFAOYSA-N 0.000 claims 3
230000000719 anti-leukaemic effect Effects 0.000 claims 2
239000002552 dosage form Substances 0.000 claims 1
238000001727 in vivo Methods 0.000 claims 1
238000007911 parenteral administration Methods 0.000 claims 1
239000000546 pharmaceutical excipient Substances 0.000 claims 1
239000000825 pharmaceutical preparation Substances 0.000 claims 1
239000002516 radical scavenger Substances 0.000 abstract description 5
229940123457 Free radical scavenger Drugs 0.000 abstract description 4
229940127395 Ribonucleotide Reductase Inhibitors Drugs 0.000 abstract description 2
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
-1 hydroxy-substituted benzamidines Chemical class 0.000 description 24
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 21
239000000243 solution Substances 0.000 description 17
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
238000002360 preparation method Methods 0.000 description 15
150000002825 nitriles Chemical class 0.000 description 14
238000004458 analytical method Methods 0.000 description 13
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
238000006243 chemical reaction Methods 0.000 description 12
239000000203 mixture Substances 0.000 description 11
238000000354 decomposition reaction Methods 0.000 description 10
238000001704 evaporation Methods 0.000 description 10
230000008020 evaporation Effects 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
239000011541 reaction mixture Substances 0.000 description 9
238000001953 recrystallisation Methods 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 8
241000699670 Mus sp. Species 0.000 description 8
210000004027 cell Anatomy 0.000 description 8
229940079593 drug Drugs 0.000 description 8
239000003814 drug Substances 0.000 description 8
239000003039 volatile agent Substances 0.000 description 8
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 7
238000001914 filtration Methods 0.000 description 7
239000011877 solvent mixture Substances 0.000 description 7
239000007858 starting material Substances 0.000 description 7
230000000875 corresponding effect Effects 0.000 description 6
230000007760 free radical scavenging Effects 0.000 description 6
238000004519 manufacturing process Methods 0.000 description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
230000004083 survival effect Effects 0.000 description 6
OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 6
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
102000004190 Enzymes Human genes 0.000 description 5
108090000790 Enzymes Proteins 0.000 description 5
241001465754 Metazoa Species 0.000 description 5
239000007864 aqueous solution Substances 0.000 description 5
201000011510 cancer Diseases 0.000 description 5
230000000694 effects Effects 0.000 description 5
238000002474 experimental method Methods 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
239000000047 product Substances 0.000 description 5
239000000725 suspension Substances 0.000 description 5
GPXIMVVEQNCDGW-UHFFFAOYSA-N 2,3,4-trihydroxybenzonitrile Chemical compound OC1=CC=C(C#N)C(O)=C1O GPXIMVVEQNCDGW-UHFFFAOYSA-N 0.000 description 4
PGKWKZZRJYUEMR-UHFFFAOYSA-N 2-hydroxy-3,4,5-trimethoxybenzamide Chemical compound COC1=CC(C(N)=O)=C(O)C(OC)=C1OC PGKWKZZRJYUEMR-UHFFFAOYSA-N 0.000 description 4
235000011437 Amygdalus communis Nutrition 0.000 description 4
VSNHCAURESNICA-UHFFFAOYSA-N Hydroxyurea Chemical compound NC(=O)NO VSNHCAURESNICA-UHFFFAOYSA-N 0.000 description 4
YPDCARQCUJAWLA-UHFFFAOYSA-N N',2,3,4-tetrahydroxybenzenecarboximidamide Chemical compound ON=C(N)C1=CC=C(O)C(O)=C1O YPDCARQCUJAWLA-UHFFFAOYSA-N 0.000 description 4
241000220304 Prunus dulcis Species 0.000 description 4
235000020224 almond Nutrition 0.000 description 4
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
229910000041 hydrogen chloride Inorganic materials 0.000 description 4
229960001330 hydroxycarbamide Drugs 0.000 description 4
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
150000003254 radicals Chemical class 0.000 description 4
GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 4
238000012360 testing method Methods 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
238000004448 titration Methods 0.000 description 4
RBQIPEJXQPQFJX-UHFFFAOYSA-N 3,4,5-trihydroxybenzamide Chemical compound NC(=O)C1=CC(O)=C(O)C(O)=C1 RBQIPEJXQPQFJX-UHFFFAOYSA-N 0.000 description 3
OHCQBZQVFIBAIV-UHFFFAOYSA-N 3,4,5-trihydroxybenzonitrile Chemical compound OC1=CC(C#N)=CC(O)=C1O OHCQBZQVFIBAIV-UHFFFAOYSA-N 0.000 description 3
ZNBNBTIDJSKEAM-UHFFFAOYSA-N 4-[7-hydroxy-2-[5-[5-[6-hydroxy-6-(hydroxymethyl)-3,5-dimethyloxan-2-yl]-3-methyloxolan-2-yl]-5-methyloxolan-2-yl]-2,8-dimethyl-1,10-dioxaspiro[4.5]decan-9-yl]-2-methyl-3-propanoyloxypentanoic acid Chemical compound C1C(O)C(C)C(C(C)C(OC(=O)CC)C(C)C(O)=O)OC11OC(C)(C2OC(C)(CC2)C2C(CC(O2)C2C(CC(C)C(O)(CO)O2)C)C)CC1 ZNBNBTIDJSKEAM-UHFFFAOYSA-N 0.000 description 3
OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 3
150000001408 amides Chemical class 0.000 description 3
MXOQNVMDKHLYCZ-UHFFFAOYSA-N benzamidoxime Chemical class ON=C(N)C1=CC=CC=C1 MXOQNVMDKHLYCZ-UHFFFAOYSA-N 0.000 description 3
229910000378 hydroxylammonium sulfate Inorganic materials 0.000 description 3
239000003112 inhibitor Substances 0.000 description 3
238000011081 inoculation Methods 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
230000003287 optical effect Effects 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
238000010992 reflux Methods 0.000 description 3
230000010076 replication Effects 0.000 description 3
239000000126 substance Substances 0.000 description 3
WCBPJVKVIMMEQC-UHFFFAOYSA-N 1,1-diphenyl-2-(2,4,6-trinitrophenyl)hydrazine Chemical group [O-][N+](=O)C1=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C1NN(C=1C=CC=CC=1)C1=CC=CC=C1 WCBPJVKVIMMEQC-UHFFFAOYSA-N 0.000 description 2
ZPJYPVNIXKKWAU-UHFFFAOYSA-N 2,3,4,5,6-pentamethoxybenzonitrile Chemical compound COC1=C(OC)C(OC)=C(C#N)C(OC)=C1OC ZPJYPVNIXKKWAU-UHFFFAOYSA-N 0.000 description 2
HZNQSWJZTWOTKM-UHFFFAOYSA-N 2,3,4-trimethoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C(OC)=C1OC HZNQSWJZTWOTKM-UHFFFAOYSA-N 0.000 description 2
QITQDRKYQSXESA-UHFFFAOYSA-N 2-hydroxy-3,4,5-trimethoxybenzoic acid;hydrate Chemical compound O.COC1=CC(C(O)=O)=C(O)C(OC)=C1OC QITQDRKYQSXESA-UHFFFAOYSA-N 0.000 description 2
JTNCEQNHURODLX-UHFFFAOYSA-N 2-phenylethanimidamide Chemical class NC(=N)CC1=CC=CC=C1 JTNCEQNHURODLX-UHFFFAOYSA-N 0.000 description 2
SJSOFNCYXJUNBT-UHFFFAOYSA-N 3,4,5-trimethoxybenzoic acid Chemical compound COC1=CC(C(O)=O)=CC(OC)=C1OC SJSOFNCYXJUNBT-UHFFFAOYSA-N 0.000 description 2
IBGBGRVKPALMCQ-UHFFFAOYSA-N 3,4-dihydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1O IBGBGRVKPALMCQ-UHFFFAOYSA-N 0.000 description 2
NUWHYWYSMAPBHK-UHFFFAOYSA-N 3,4-dihydroxybenzonitrile Chemical compound OC1=CC=C(C#N)C=C1O NUWHYWYSMAPBHK-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical class NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
208000028018 Lymphocytic leukaemia Diseases 0.000 description 2
TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
108091028664 Ribonucleotide Proteins 0.000 description 2
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
238000002835 absorbance Methods 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
239000000908 ammonium hydroxide Substances 0.000 description 2
230000000118 anti-neoplastic effect Effects 0.000 description 2
230000000259 anti-tumor effect Effects 0.000 description 2
238000003556 assay Methods 0.000 description 2
239000003610 charcoal Substances 0.000 description 2
OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 2
230000006378 damage Effects 0.000 description 2
239000005547 deoxyribonucleotide Substances 0.000 description 2
125000002637 deoxyribonucleotide group Chemical group 0.000 description 2
238000011161 development Methods 0.000 description 2
239000007789 gas Substances 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
230000005764 inhibitory process Effects 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
208000003747 lymphoid leukemia Diseases 0.000 description 2
NNICRUQPODTGRU-UHFFFAOYSA-N mandelonitrile Chemical compound N#CC(O)C1=CC=CC=C1 NNICRUQPODTGRU-UHFFFAOYSA-N 0.000 description 2
GXYVISXLFBQBKH-UHFFFAOYSA-N n',2-dihydroxy-2-phenylethanimidamide Chemical compound ON=C(N)C(O)C1=CC=CC=C1 GXYVISXLFBQBKH-UHFFFAOYSA-N 0.000 description 2
FVYBAJYRRIYNBN-UHFFFAOYSA-N n'-hydroxy-2-phenylethanimidamide Chemical class ON=C(N)CC1=CC=CC=C1 FVYBAJYRRIYNBN-UHFFFAOYSA-N 0.000 description 2
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
150000002923 oximes Chemical class 0.000 description 2
230000002829 reductive effect Effects 0.000 description 2
239000002336 ribonucleotide Substances 0.000 description 2
125000002652 ribonucleotide group Chemical group 0.000 description 2
235000010265 sodium sulphite Nutrition 0.000 description 2
238000006467 substitution reaction Methods 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
230000001988 toxicity Effects 0.000 description 2
231100000419 toxicity Toxicity 0.000 description 2
QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical class O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
SINUYZQKBLIHOZ-UHFFFAOYSA-N 2,3,4,5,6-pentahydroxybenzamide Chemical compound NC(=O)C1=C(O)C(O)=C(O)C(O)=C1O SINUYZQKBLIHOZ-UHFFFAOYSA-N 0.000 description 1
DNPDDXUUYSMLKD-UHFFFAOYSA-N 2,3,4,5,6-pentamethoxybenzamide Chemical compound COC1=C(OC)C(OC)=C(C(N)=O)C(OC)=C1OC DNPDDXUUYSMLKD-UHFFFAOYSA-N 0.000 description 1
WFRPMPXETUEEEL-UHFFFAOYSA-N 2,3,4,6-tetrahydroxybenzonitrile Chemical compound OC1=CC(O)=C(C#N)C(O)=C1O WFRPMPXETUEEEL-UHFFFAOYSA-N 0.000 description 1
CRNPKFLXFKSNEW-UHFFFAOYSA-N 2,3,4-trihydroxybenzamide Chemical compound NC(=O)C1=CC=C(O)C(O)=C1O CRNPKFLXFKSNEW-UHFFFAOYSA-N 0.000 description 1
DMGOOMWJYNWCBN-UHFFFAOYSA-N 2,3,4-trihydroxybenzonitrile;hydrate Chemical compound O.OC1=CC=C(C#N)C(O)=C1O DMGOOMWJYNWCBN-UHFFFAOYSA-N 0.000 description 1
NPFQPSKKBQGCKB-UHFFFAOYSA-N 2,3,5,6-tetrahydroxybenzonitrile Chemical compound OC1=CC(O)=C(O)C(C#N)=C1O NPFQPSKKBQGCKB-UHFFFAOYSA-N 0.000 description 1
SRLTVIITBRPPCB-UHFFFAOYSA-N 2,3,5-trimethoxybenzoic acid Chemical compound COC1=CC(OC)=C(OC)C(C(O)=O)=C1 SRLTVIITBRPPCB-UHFFFAOYSA-N 0.000 description 1
IIUJCQYKTGNRHH-UHFFFAOYSA-N 2,4-dihydroxybenzamide Chemical compound NC(=O)C1=CC=C(O)C=C1O IIUJCQYKTGNRHH-UHFFFAOYSA-N 0.000 description 1
WDKIHNKPXHYPDH-UHFFFAOYSA-N 2-(2,3,4,5-tetrahydroxyphenyl)acetamide Chemical compound NC(=O)CC1=CC(O)=C(O)C(O)=C1O WDKIHNKPXHYPDH-UHFFFAOYSA-N 0.000 description 1
BCXCZGJJJIXPCP-UHFFFAOYSA-N 2-(2,3,4-trihydroxyphenyl)acetamide Chemical compound NC(=O)CC1=CC=C(O)C(O)=C1O BCXCZGJJJIXPCP-UHFFFAOYSA-N 0.000 description 1
AHEGCVAZYHXFKB-UHFFFAOYSA-N 2-(2,3,5-trihydroxyphenyl)ethanimidamide Chemical compound NC(=N)CC1=CC(O)=CC(O)=C1O AHEGCVAZYHXFKB-UHFFFAOYSA-N 0.000 description 1
SMRAJKANWACYNO-UHFFFAOYSA-N 2-(2,3-dihydroxyphenyl)acetamide Chemical compound NC(=O)CC1=CC=CC(O)=C1O SMRAJKANWACYNO-UHFFFAOYSA-N 0.000 description 1
UPAPCDWRDJOKLU-UHFFFAOYSA-N 2-(3,4,5-trihydroxyphenyl)acetamide Chemical compound NC(=O)CC1=CC(O)=C(O)C(O)=C1 UPAPCDWRDJOKLU-UHFFFAOYSA-N 0.000 description 1
KWQVATMODKRUEZ-UHFFFAOYSA-N 2-(3,4-dihydroxyphenyl)-n',2-dihydroxyethanimidamide Chemical compound ON=C(N)C(O)C1=CC=C(O)C(O)=C1 KWQVATMODKRUEZ-UHFFFAOYSA-N 0.000 description 1
PFBVIDZIRYKFQF-UHFFFAOYSA-N 2-(3,4-dihydroxyphenyl)-n',2-dihydroxyethanimidamide;hydrate Chemical compound O.ON=C(N)C(O)C1=CC=C(O)C(O)=C1 PFBVIDZIRYKFQF-UHFFFAOYSA-N 0.000 description 1
PGXUFOSNLJVHBH-UHFFFAOYSA-N 2-(3,5-dihydroxyphenyl)acetamide Chemical compound NC(=O)CC1=CC(O)=CC(O)=C1 PGXUFOSNLJVHBH-UHFFFAOYSA-N 0.000 description 1
JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 1
AUVPVHYYPCTFAV-UHFFFAOYSA-N 2-bromo-3,4,5-trimethoxybenzoic acid Chemical compound COC1=CC(C(O)=O)=C(Br)C(OC)=C1OC AUVPVHYYPCTFAV-UHFFFAOYSA-N 0.000 description 1
MJZXQRQWAWCETQ-UHFFFAOYSA-N 2-hydroxy-3,4,5-trimethoxybenzoic acid Chemical compound COC1=CC(C(O)=O)=C(O)C(OC)=C1OC MJZXQRQWAWCETQ-UHFFFAOYSA-N 0.000 description 1
DUZRNUWKVXKOID-UHFFFAOYSA-N 2-hydroxy-3,4,5-trimethoxybenzonitrile Chemical compound COC1=CC(C#N)=C(O)C(OC)=C1OC DUZRNUWKVXKOID-UHFFFAOYSA-N 0.000 description 1
LSBDFXRDZJMBSC-UHFFFAOYSA-N 2-phenylacetamide Chemical class NC(=O)CC1=CC=CC=C1 LSBDFXRDZJMBSC-UHFFFAOYSA-N 0.000 description 1
IWPZKOJSYQZABD-UHFFFAOYSA-N 3,4,5-trimethoxybenzoic acid Natural products COC1=CC(OC)=CC(C(O)=O)=C1 IWPZKOJSYQZABD-UHFFFAOYSA-N 0.000 description 1
PCYGLFXKCBFGPC-UHFFFAOYSA-N 3,4-Dihydroxy hydroxymethyl benzene Natural products OCC1=CC=C(O)C(O)=C1 PCYGLFXKCBFGPC-UHFFFAOYSA-N 0.000 description 1
PLYYMFBDRBSPJZ-UHFFFAOYSA-N 3,5-dihydroxybenzamide Chemical compound NC(=O)C1=CC(O)=CC(O)=C1 PLYYMFBDRBSPJZ-UHFFFAOYSA-N 0.000 description 1
206010003445 Ascites Diseases 0.000 description 1
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 1
238000011765 DBA/2 mouse Methods 0.000 description 1
208000001382 Experimental Melanoma Diseases 0.000 description 1
206010061218 Inflammation Diseases 0.000 description 1
239000002841 Lewis acid Substances 0.000 description 1
FZKWXDBVCGROTJ-UHFFFAOYSA-N NC(=O)CC1=C(O)C=C(O)C(O)=C1O Chemical compound NC(=O)CC1=C(O)C=C(O)C(O)=C1O FZKWXDBVCGROTJ-UHFFFAOYSA-N 0.000 description 1
BLSAOOFJSYAAHH-UHFFFAOYSA-N NC(=O)CC1=CC(O)=C(O)C=C1O Chemical compound NC(=O)CC1=CC(O)=C(O)C=C1O BLSAOOFJSYAAHH-UHFFFAOYSA-N 0.000 description 1
YKRHSYLVLVOCRP-UHFFFAOYSA-N OC1=C(C(N)=NO)C=CC=C1O.OC1=C(C(=O)N)C=C(C(=C1)O)O Chemical compound OC1=C(C(N)=NO)C=CC=C1O.OC1=C(C(=O)N)C=C(C(=C1)O)O YKRHSYLVLVOCRP-UHFFFAOYSA-N 0.000 description 1
241000276498 Pollachius virens Species 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
239000003929 acidic solution Substances 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
229940059260 amidate Drugs 0.000 description 1
150000001409 amidines Chemical class 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
238000013459 approach Methods 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
210000003567 ascitic fluid Anatomy 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
229940054066 benzamide antipsychotics Drugs 0.000 description 1
150000003936 benzamides Chemical class 0.000 description 1
150000003937 benzamidines Chemical class 0.000 description 1
230000031018 biological processes and functions Effects 0.000 description 1
230000033228 biological regulation Effects 0.000 description 1
230000006696 biosynthetic metabolic pathway Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
230000001413 cellular effect Effects 0.000 description 1
KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
SFZULDYEOVSIKM-UHFFFAOYSA-N chembl321317 Chemical compound C1=CC(C(=N)NO)=CC=C1C1=CC=C(C=2C=CC(=CC=2)C(=N)NO)O1 SFZULDYEOVSIKM-UHFFFAOYSA-N 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000002512 chemotherapy Methods 0.000 description 1
210000001072 colon Anatomy 0.000 description 1
208000029742 colonic neoplasm Diseases 0.000 description 1
239000000470 constituent Substances 0.000 description 1
BWFPGXWASODCHM-UHFFFAOYSA-N copper monosulfide Chemical compound [Cu]=S BWFPGXWASODCHM-UHFFFAOYSA-N 0.000 description 1
230000002596 correlated effect Effects 0.000 description 1
239000013078 crystal Substances 0.000 description 1
229940076286 cupric acetate Drugs 0.000 description 1
FTDHDKPUHBLBTL-SHYZEUOFSA-K dCDP(3-) Chemical compound O=C1N=C(N)C=CN1[C@@H]1O[C@H](COP([O-])(=O)OP([O-])([O-])=O)[C@@H](O)C1 FTDHDKPUHBLBTL-SHYZEUOFSA-K 0.000 description 1
230000007423 decrease Effects 0.000 description 1
230000017858 demethylation Effects 0.000 description 1
238000010520 demethylation reaction Methods 0.000 description 1
238000013461 design Methods 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
VHJLVAABSRFDPM-QWWZWVQMSA-N dithiothreitol Chemical compound SC[C@@H](O)[C@H](O)CS VHJLVAABSRFDPM-QWWZWVQMSA-N 0.000 description 1
238000004980 dosimetry Methods 0.000 description 1
238000006911 enzymatic reaction Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
YKWNUSJLICDQEO-UHFFFAOYSA-N ethoxyethane;propan-2-ol Chemical compound CC(C)O.CCOCC YKWNUSJLICDQEO-UHFFFAOYSA-N 0.000 description 1
239000002024 ethyl acetate extract Substances 0.000 description 1
ANFZRGMDGDYNGA-UHFFFAOYSA-N ethyl acetate;propan-2-ol Chemical compound CC(C)O.CCOC(C)=O ANFZRGMDGDYNGA-UHFFFAOYSA-N 0.000 description 1
NPUKDXXFDDZOKR-LLVKDONJSA-N etomidate Chemical compound CCOC(=O)C1=CN=CN1[C@H](C)C1=CC=CC=C1 NPUKDXXFDDZOKR-LLVKDONJSA-N 0.000 description 1
239000012065 filter cake Substances 0.000 description 1
235000013373 food additive Nutrition 0.000 description 1
239000002778 food additive Substances 0.000 description 1
239000005452 food preservative Substances 0.000 description 1
235000019249 food preservative Nutrition 0.000 description 1
239000012458 free base Substances 0.000 description 1
239000003574 free electron Substances 0.000 description 1
ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
238000011534 incubation Methods 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
238000004255 ion exchange chromatography Methods 0.000 description 1
150000002617 leukotrienes Chemical class 0.000 description 1
150000007517 lewis acids Chemical class 0.000 description 1
150000002632 lipids Chemical class 0.000 description 1
230000004132 lipogenesis Effects 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229910001629 magnesium chloride Inorganic materials 0.000 description 1
201000001441 melanoma Diseases 0.000 description 1
230000000684 melanotic effect Effects 0.000 description 1
230000008018 melting Effects 0.000 description 1
238000002844 melting Methods 0.000 description 1
SSDAYUCIUSMMRO-UHFFFAOYSA-N methyl 2-hydroxy-3,4,5-trimethoxybenzoate Chemical compound COC(=O)C1=CC(OC)=C(OC)C(OC)=C1O SSDAYUCIUSMMRO-UHFFFAOYSA-N 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
150000004682 monohydrates Chemical class 0.000 description 1
230000001613 neoplastic effect Effects 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
239000003223 protective agent Substances 0.000 description 1
238000006338 pulse radiolysis reaction Methods 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
230000009467 reduction Effects 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
238000000926 separation method Methods 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
239000004289 sodium hydrogen sulphite Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000000758 substrate Substances 0.000 description 1
238000010189 synthetic method Methods 0.000 description 1
YUKQRDCYNOVPGJ-UHFFFAOYSA-N thioacetamide Chemical compound CC(N)=S YUKQRDCYNOVPGJ-UHFFFAOYSA-N 0.000 description 1
DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 1
230000009466 transformation Effects 0.000 description 1
230000007704 transition Effects 0.000 description 1
238000002054 transplantation Methods 0.000 description 1
210000004881 tumor cell Anatomy 0.000 description 1
BSOLAQMZTBVZLA-UHFFFAOYSA-N tyrosinyl radical Chemical compound OC(=O)C(N)CC1=CC=C([O])C=C1 BSOLAQMZTBVZLA-UHFFFAOYSA-N 0.000 description 1
230000003442 weekly effect Effects 0.000 description 1
238000005303 weighing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/32—Oximes
- C07C251/34—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C259/00—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
- C07C259/12—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. N-hydroxyamidines
- C07C259/14—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. N-hydroxyamidines having carbon atoms of hydroxamidine groups bound to hydrogen atoms or to acyclic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C259/00—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
- C07C259/12—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. N-hydroxyamidines
- C07C259/18—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. N-hydroxyamidines having carbon atoms of hydroxamidine groups bound to carbon atoms of six-membered aromatic rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
Oncology (AREA)
Hematology (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
Chemical And Physical Treatments For Wood And The Like (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Detergent Compositions (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Fats And Perfumes (AREA)
Laminated Bodies (AREA)

NO843739A 1983-05-23 1984-09-19 Polyhydroksybenzosyrederivater. NO843739L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US06/497,370 US4623659A (en)	1983-05-23	1983-05-23	Polyhydroxybenzoic acid derivatives

Publications (1)

Publication Number	Publication Date
NO843739L true NO843739L (no)	1984-12-06

Family

ID=23976584

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO843739A NO843739L (no)	1983-05-23	1984-09-19	Polyhydroksybenzosyrederivater.

Country Status (13)

Country	Link
US (1)	US4623659A (de)
EP (1)	EP0144396B1 (de)
JP (2)	JPS60501409A (de)
KR (1)	KR920004187B1 (de)
AT (1)	ATE59553T1 (de)
AU (1)	AU589111B2 (de)
CA (1)	CA1339221C (de)
DE (1)	DE3483822D1 (de)
DK (1)	DK13785A (de)
FI (1)	FI843681A (de)
IT (1)	IT1209548B (de)
NO (1)	NO843739L (de)
WO (1)	WO1984004676A1 (de)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2740133A (en) *	1951-03-01	1956-04-03	Seng Co	Detachable footboard for a bed
US5183828A (en) *	1983-05-23	1993-02-02	Riet Bartholomeus Van T	Polyhydroxybenzoic acid derivatives
US4942253A (en) *	1983-05-23	1990-07-17	Riet Bartholomeus Van T	Polyhydroxybenzoic acid derivatives
EP0610444B1 (de) *	1991-10-31	2003-01-29	ELFORD, Howard L.	Verwendung eines polyhydroxybenzamids oder dessen Derivat zur Herstellung eines Medikaments für die Behandlung von viralen Infektionen
US5350770A (en) *	1992-07-28	1994-09-27	Elford Howard L	Therapeutic process for the treatment of septic shock
US6028111A (en) *	1996-03-08	2000-02-22	Oxigene, Inc.	Compositions and use of benzamides and nicotinamides as anti-inflammatory agents
US6713517B1 (en)	1996-03-08	2004-03-30	Oxigene, Inc.	Use of aryl N-substituted carboxamides directly and as radio-and chemosensitizers for killing tumor and cancer cells and novel compounds for such use
WO1998041202A1 (en) *	1997-03-20	1998-09-24	The Government Of The United States Of America, Represented By The Secretary, Department Of Health And Human Services	Hydroxybenzoate metabolites and hydroxybenzoate analogues as protectors against oxidative stress and chemotherapeutic drug cytotoxicity, cardiotoxicity and extravasation tissue injury
US6924308B1 (en) *	1997-07-30	2005-08-02	Howard L. Elford	Therapeutic process for inhibiting NF-κB
US6516479B1 (en) *	2000-06-02	2003-02-11	Burke Mobility Products, Inc.	Foldable rehabilitation bed for accommodating an obese person
CA2520228A1 (en) *	2003-03-26	2004-10-07	Bayer Cropscience Gmbh	Use of aromatic compounds as safeners
US8029815B2 (en) *	2004-04-28	2011-10-04	Elford Howard L	Methods for treating or preventing restenosis and other vascular proliferative disorders
EP2030615A3 (de)	2007-08-13	2009-12-02	ELFORD, Howard L.	Ribonukleotidreduktase-Inhibitoren zur Verwendung für die Behandlung oder Vorbeugung von Nervenentzündung- oder Autoimmunerkrankungen

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB358279A (en) *	1930-10-07	1931-10-08	Ig Farbenindustrie Ag	Process for inhibiting the development of micro organisms
US2849480A (en)	1956-10-05	1958-08-26	Kreuchunas Algird	Process for the preparation of 2, 3, 6-trihydroxybenzoic acid and derivatives
US3629443A (en)	1967-11-29	1971-12-21	Orsymonde	Therapeutic composition containing a mandelamidine derivative
GB1243186A (en) *	1967-11-29	1971-08-18	Orsymonde	Improvements in or relating to mandelamidine derivatives
US4263322A (en) *	1979-03-01	1981-04-21	Riet Bartholomeus Van T	Hydroxy benzohydroxamic acids and benzamides
US4236322A (en)	1979-03-15	1980-12-02	Hastings Allen M	Apparatus for and method of drying items by open air and solar energy

1983
- 1983-05-23 US US06/497,370 patent/US4623659A/en not_active Expired - Lifetime
1984
- 1984-05-21 DE DE8484902270T patent/DE3483822D1/de not_active Expired - Lifetime
- 1984-05-21 WO PCT/US1984/000755 patent/WO1984004676A1/en active IP Right Grant
- 1984-05-21 AT AT84902270T patent/ATE59553T1/de not_active IP Right Cessation
- 1984-05-21 JP JP59502128A patent/JPS60501409A/ja active Granted
- 1984-05-21 AU AU30130/84A patent/AU589111B2/en not_active Expired
- 1984-05-21 EP EP84902270A patent/EP0144396B1/de not_active Expired - Lifetime
- 1984-05-23 KR KR1019840002882A patent/KR920004187B1/ko not_active IP Right Cessation
- 1984-05-23 IT IT8421068A patent/IT1209548B/it active
- 1984-05-23 CA CA000454910A patent/CA1339221C/en not_active Expired - Lifetime
- 1984-09-19 NO NO843739A patent/NO843739L/no unknown
- 1984-09-20 FI FI843681A patent/FI843681A/fi not_active Application Discontinuation
1985
- 1985-01-11 DK DK13785A patent/DK13785A/da not_active Application Discontinuation
1992
- 1992-02-26 JP JP4039794A patent/JPH0578299A/ja active Pending

Also Published As

Publication number	Publication date
AU589111B2 (en)	1989-10-05
JPH0578299A (ja)	1993-03-30
FI843681A (fi)	1984-11-24
KR920004187B1 (ko)	1992-05-30
JPH051780B2 (de)	1993-01-11
DK13785D0 (da)	1985-01-11
EP0144396A1 (de)	1985-06-19
US4623659A (en)	1986-11-18
EP0144396A4 (de)	1986-08-21
IT8421068A0 (it)	1984-05-23
CA1339221C (en)	1997-08-05
EP0144396B1 (de)	1991-01-02
ATE59553T1 (de)	1991-01-15
DE3483822D1 (de)	1991-02-07
JPS60501409A (ja)	1985-08-29
FI843681A0 (fi)	1984-09-20
WO1984004676A1 (en)	1984-12-06
DK13785A (da)	1985-01-11
IT1209548B (it)	1989-08-30
AU3013084A (en)	1984-12-18
KR850001160A (ko)	1985-03-16

Publication	Publication Date	Title
NO843739L (no)	1984-12-06	Polyhydroksybenzosyrederivater.
CS277018B6 (en)	1992-11-18	Process for preparing novel pharmacologically active derivatives of catechol
US20070238781A1 (en)	2007-10-11	Compounds for the modulation of the glykolysis-enzyme-and/or of the transaminase-complex
WO1999028291A1 (en)	1999-06-10	Bishydroxyureas as inhibitors of the 5-lipoxygenase
US4263322A (en)	1981-04-21	Hydroxy benzohydroxamic acids and benzamides
CS229941B2 (en)	1984-07-16	Production method of aminated pyridazine derivatives
Neelakantan et al.	1958	α-Hydroxylamino Nitriles and α-Hydroxylamino Acids1, 2
US4448730A (en)	1984-05-15	Hydroxybenzohydroxamic acids, benzamides and esters and related compounds as ribonucleotide reductase inhibitors
US5183828A (en)	1993-02-02	Polyhydroxybenzoic acid derivatives
US4272538A (en)	1981-06-09	5-Nitro-imidazole with antiprotozoic activity
McKay et al.	1956	Amino Acids. II. Synthesis of Cyclic Guanidino Acids1
US4942253A (en)	1990-07-17	Polyhydroxybenzoic acid derivatives
US4022907A (en)	1977-05-10	Pharmaceutical compositions containing 1,3-dithiacycloalkylidene malonates
NO131930B (de)	1975-05-20
US4080466A (en)	1978-03-21	Pharmaceutical compositions containing 4-hydroxyl-1,3-dithiolan-2-ylidene malonates
EP0041827B1 (de)	1984-03-21	Eine N-(Benzyliden)aminomethyl-cyclohexan-carbonsäure
US3149153A (en)	1964-09-15	3'-substituted-3, 5-diiodothyronine and salts thereof
EP0172059B1 (de)	1988-04-20	Oxaazaphosphorin-Derivate, Verfahren zu deren Herstellung und sie enthaltende pharmazeutische Zubereitungen
IE58187B1 (en)	1993-07-28	Novel allylic amines
NO165917B (no)	1991-01-21	Analogifremgangsmaate for fremstilling av terapeutisk aktivt diamino-2,2-difluorhex-5-yn.
WO2023031683A1 (en)	2023-03-09	2,4-dioxo-1,2,3,4-tetrahydropyrimidine derivatives and their use in the treatment of tumors
US4661510A (en)	1987-04-28	α-allenic-α-amino acids as enzyme inhibitors
RU2043352C1 (ru)	1995-09-10	2-пропил-3- (5-нитрофурфулиден)амино- 4(3н)-хиназолинон, проявляющий противостафилококковую и анальгетическую активность
IE853327L (en)	1986-06-30	Allylic amines
WO1991008201A1 (fr)	1991-06-13	Derives d'(hetero) arylmethyloxy-4 phenyl diazole, leur procede de preparation et leur application en therapeutique