PL41069B1 - - Google Patents

Info

Publication number

PL41069B1

PL41069B1 PL41069A PL4106955A PL41069B1 PL 41069 B1 PL41069 B1 PL 41069B1 PL 41069 A PL41069 A PL 41069A PL 4106955 A PL4106955 A PL 4106955A PL 41069 B1 PL41069 B1 PL 41069B1

Authority

PL

Poland

Prior art keywords

bis

hydroxycoumarin

chromonyl

methane

derivatives

Prior art date

1955-04-18

Links

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• 239000000126 substance Substances 0.000 claims description 8
• 238000000034 method Methods 0.000 claims description 5
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 4
• OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 2
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 2
• 239000003146 anticoagulant agent Substances 0.000 claims description 2
• 229940127219 anticoagulant drug Drugs 0.000 claims description 2
• 235000019253 formic acid Nutrition 0.000 claims description 2
• 125000005907 alkyl ester group Chemical group 0.000 claims 1
• 238000007363 ring formation reaction Methods 0.000 claims 1
• VXIXUWQIVKSKSA-UHFFFAOYSA-N 4-hydroxycoumarin Chemical class C1=CC=CC2=C1OC(=O)C=C2O VXIXUWQIVKSKSA-UHFFFAOYSA-N 0.000 description 5
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
• 230000000694 effects Effects 0.000 description 3
• 238000003786 synthesis reaction Methods 0.000 description 3
• JGLMVXWAHNTPRF-CMDGGOBGSA-N CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O Chemical compound CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O JGLMVXWAHNTPRF-CMDGGOBGSA-N 0.000 description 2
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
• 241000700159 Rattus Species 0.000 description 2
• 230000015572 biosynthetic process Effects 0.000 description 2
• 238000006243 chemical reaction Methods 0.000 description 2
• 239000000203 mixture Substances 0.000 description 2
• 239000011734 sodium Substances 0.000 description 2
• 159000000000 sodium salts Chemical class 0.000 description 2
• 238000003419 tautomerization reaction Methods 0.000 description 2
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
• IMQJXJOIQBIHAM-UHFFFAOYSA-N 4-hydroxy-3-[[3-(2-oxopropyl)phenyl]methyl]chromen-2-one Chemical compound CC(=O)CC1=CC=CC(CC=2C(OC3=CC=CC=C3C=2O)=O)=C1 IMQJXJOIQBIHAM-UHFFFAOYSA-N 0.000 description 1
• QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
• 229930003448 Vitamin K Natural products 0.000 description 1
• 239000002253 acid Substances 0.000 description 1
• 230000002429 anti-coagulating effect Effects 0.000 description 1
• FBPJRNBLWSMDII-UHFFFAOYSA-N azanium;butan-1-ol;hydroxide Chemical compound [NH4+].[OH-].CCCCO FBPJRNBLWSMDII-UHFFFAOYSA-N 0.000 description 1
• 230000023555 blood coagulation Effects 0.000 description 1
• 238000010276 construction Methods 0.000 description 1
• 230000008094 contradictory effect Effects 0.000 description 1
• 229960000956 coumarin Drugs 0.000 description 1
• 125000000332 coumarinyl group Chemical group O1C(=O)C(=CC2=CC=CC=C12)* 0.000 description 1
• 238000001514 detection method Methods 0.000 description 1
• DOBMPNYZJYQDGZ-UHFFFAOYSA-N dicoumarol Chemical compound C1=CC=CC2=C1OC(=O)C(CC=1C(OC3=CC=CC=C3C=1O)=O)=C2O DOBMPNYZJYQDGZ-UHFFFAOYSA-N 0.000 description 1
• WBJINCZRORDGAQ-UHFFFAOYSA-N ethyl formate Chemical compound CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
• 238000001914 filtration Methods 0.000 description 1
• 238000009472 formulation Methods 0.000 description 1
• 239000000463 material Substances 0.000 description 1
• 239000000155 melt Substances 0.000 description 1
• 238000002156 mixing Methods 0.000 description 1
• 238000004816 paper chromatography Methods 0.000 description 1
• SHUZOJHMOBOZST-UHFFFAOYSA-N phylloquinone Natural products CC(C)CCCCC(C)CCC(C)CCCC(=CCC1=C(C)C(=O)c2ccccc2C1=O)C SHUZOJHMOBOZST-UHFFFAOYSA-N 0.000 description 1
• 239000002574 poison Substances 0.000 description 1
• 231100000614 poison Toxicity 0.000 description 1
• 230000003389 potentiating effect Effects 0.000 description 1
• 238000002360 preparation method Methods 0.000 description 1
• 230000002035 prolonged effect Effects 0.000 description 1
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
• 150000003839 salts Chemical class 0.000 description 1
• 239000002002 slurry Substances 0.000 description 1
• 229910052708 sodium Inorganic materials 0.000 description 1
• 230000009967 tasteless effect Effects 0.000 description 1
• 230000001225 therapeutic effect Effects 0.000 description 1
• 230000001988 toxicity Effects 0.000 description 1
• 231100000419 toxicity Toxicity 0.000 description 1
• 235000019168 vitamin K Nutrition 0.000 description 1
• 239000011712 vitamin K Substances 0.000 description 1
• 150000003721 vitamin K derivatives Chemical class 0.000 description 1
• 229940046010 vitamin k Drugs 0.000 description 1