NO864514L - Fremgangsmaate for fremstilling av nye thiazoloner. - Google Patents
Fremgangsmaate for fremstilling av nye thiazoloner.Info
- Publication number
- NO864514L NO864514L NO864514A NO864514A NO864514L NO 864514 L NO864514 L NO 864514L NO 864514 A NO864514 A NO 864514A NO 864514 A NO864514 A NO 864514A NO 864514 L NO864514 L NO 864514L
- Authority
- NO
- Norway
- Prior art keywords
- group
- alkyl
- thiazolone
- prepared
- optionally substituted
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 13
- 238000004519 manufacturing process Methods 0.000 title 1
- -1 cyano, carboxy Chemical group 0.000 claims description 8
- IHDKBHLTKNUCCW-UHFFFAOYSA-N 1,3-thiazole 1-oxide Chemical compound O=S1C=CN=C1 IHDKBHLTKNUCCW-UHFFFAOYSA-N 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- MOIPGXQKZSZOQX-UHFFFAOYSA-N carbonyl bromide Chemical compound BrC(Br)=O MOIPGXQKZSZOQX-UHFFFAOYSA-N 0.000 claims description 3
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000002883 imidazolyl group Chemical group 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 150000003567 thiocyanates Chemical class 0.000 claims description 3
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical group [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000004354 sulfur functional group Chemical group 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims 1
- 230000002378 acidificating effect Effects 0.000 claims 1
- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 claims 1
- 229940116357 potassium thiocyanate Drugs 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- 150000004763 sulfides Chemical class 0.000 claims 1
- 206010019280 Heart failures Diseases 0.000 abstract description 14
- 239000000496 cardiotonic agent Substances 0.000 abstract description 7
- 230000002107 myocardial effect Effects 0.000 abstract description 7
- 230000003177 cardiotonic effect Effects 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 description 27
- 230000000747 cardiac effect Effects 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 241000208011 Digitalis Species 0.000 description 6
- 230000002861 ventricular Effects 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 5
- 210000002216 heart Anatomy 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 230000037396 body weight Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 3
- 241000282472 Canis lupus familiaris Species 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 239000007943 implant Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000007911 parenteral administration Methods 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 231100000331 toxic Toxicity 0.000 description 3
- 230000002588 toxic effect Effects 0.000 description 3
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 229920002261 Corn starch Polymers 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 241001465754 Metazoa Species 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 206010070863 Toxicity to various agents Diseases 0.000 description 2
- 230000001746 atrial effect Effects 0.000 description 2
- 230000017531 blood circulation Effects 0.000 description 2
- 230000031709 bromination Effects 0.000 description 2
- 238000005893 bromination reaction Methods 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000008120 corn starch Substances 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000001802 infusion Methods 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 210000005240 left ventricle Anatomy 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000010561 standard procedure Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- 230000000304 vasodilatating effect Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 description 1
- KEULVWAKELXUMI-UHFFFAOYSA-N 1-bromo-1-pyridin-4-ylbutan-2-one Chemical compound CCC(=O)C(Br)C1=CC=NC=C1 KEULVWAKELXUMI-UHFFFAOYSA-N 0.000 description 1
- DLJPPXQWDKTOHE-UHFFFAOYSA-N 2-phenyl-1,3-thiazole 1-oxide Chemical class O=S1C=CN=C1C1=CC=CC=C1 DLJPPXQWDKTOHE-UHFFFAOYSA-N 0.000 description 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- MEAPRSDUXBHXGD-UHFFFAOYSA-N 3-chloro-n-(4-propan-2-ylphenyl)propanamide Chemical compound CC(C)C1=CC=C(NC(=O)CCCl)C=C1 MEAPRSDUXBHXGD-UHFFFAOYSA-N 0.000 description 1
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- AEGKKLKPZJVHEN-UHFFFAOYSA-N 4-ethyl-5-pyridin-4-yl-3h-1,3-thiazol-2-one Chemical compound N1=C(O)SC(C=2C=CN=CC=2)=C1CC AEGKKLKPZJVHEN-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 240000002470 Amphicarpaea bracteata Species 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 206010007559 Cardiac failure congestive Diseases 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 208000000059 Dyspnea Diseases 0.000 description 1
- 206010013975 Dyspnoeas Diseases 0.000 description 1
- 241000283086 Equidae Species 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 241000272496 Galliformes Species 0.000 description 1
- 241000287828 Gallus gallus 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
- 206010058558 Hypoperfusion Diseases 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 240000007472 Leucaena leucocephala Species 0.000 description 1
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- IPCRBOOJBPETMF-UHFFFAOYSA-N N-acetylthiourea Chemical compound CC(=O)NC(N)=S IPCRBOOJBPETMF-UHFFFAOYSA-N 0.000 description 1
- 206010031123 Orthopnoea Diseases 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- 241000286209 Phasianidae Species 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 241000288906 Primates Species 0.000 description 1
- 208000010378 Pulmonary Embolism Diseases 0.000 description 1
- 206010037423 Pulmonary oedema Diseases 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 241000282887 Suidae Species 0.000 description 1
- 208000001871 Tachycardia Diseases 0.000 description 1
- 206010047139 Vasoconstriction Diseases 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 229960001126 alginic acid Drugs 0.000 description 1
- 150000004781 alginic acids Chemical class 0.000 description 1
- 125000005236 alkanoylamino group Chemical group 0.000 description 1
- 125000004644 alkyl sulfinyl group Chemical group 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 208000007502 anemia Diseases 0.000 description 1
- 239000003416 antiarrhythmic agent Substances 0.000 description 1
- 210000000709 aorta Anatomy 0.000 description 1
- 206010003119 arrhythmia Diseases 0.000 description 1
- 230000006793 arrhythmia Effects 0.000 description 1
- 230000004872 arterial blood pressure Effects 0.000 description 1
- 210000001367 artery Anatomy 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 229920002988 biodegradable polymer Polymers 0.000 description 1
- 239000004621 biodegradable polymer Substances 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 210000001715 carotid artery Anatomy 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 210000000038 chest Anatomy 0.000 description 1
- 235000013330 chicken meat Nutrition 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 230000002996 emotional effect Effects 0.000 description 1
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- 206010016256 fatigue Diseases 0.000 description 1
- 210000001105 femoral artery Anatomy 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 230000004217 heart function Effects 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000003601 intercostal effect Effects 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 210000004731 jugular vein Anatomy 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 210000005246 left atrium Anatomy 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 208000010125 myocardial infarction Diseases 0.000 description 1
- 208000031225 myocardial ischemia Diseases 0.000 description 1
- 210000004165 myocardium Anatomy 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-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
- 210000000056 organ Anatomy 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 208000012144 orthopnea Diseases 0.000 description 1
- 125000004043 oxo group Chemical group O=* 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 229960001412 pentobarbital Drugs 0.000 description 1
- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000037081 physical activity Effects 0.000 description 1
- 230000004962 physiological condition Effects 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- DPLVEEXVKBWGHE-UHFFFAOYSA-N potassium sulfide Chemical compound [S-2].[K+].[K+] DPLVEEXVKBWGHE-UHFFFAOYSA-N 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 229960004604 propranolol hydrochloride Drugs 0.000 description 1
- AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol hydrochloride Natural products C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 210000005241 right ventricle Anatomy 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229920000260 silastic Polymers 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 239000004945 silicone rubber Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007892 solid unit dosage form Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 210000001562 sternum Anatomy 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 208000037905 systemic hypertension Diseases 0.000 description 1
- 230000006794 tachycardia Effects 0.000 description 1
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- 229940124549 vasodilator Drugs 0.000 description 1
- 239000003071 vasodilator agent Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/34—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/36—Sulfur atoms
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Heart & Thoracic Surgery (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Steroid Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Crystals, And After-Treatments Of Crystals (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polyurethanes Or Polyureas (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/797,579 US4670450A (en) | 1985-11-13 | 1985-11-13 | Cardiotonic thiazolones |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO864514D0 NO864514D0 (no) | 1986-11-12 |
| NO864514L true NO864514L (no) | 1987-05-14 |
Family
ID=25171231
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO864514A NO864514L (no) | 1985-11-13 | 1986-11-12 | Fremgangsmaate for fremstilling av nye thiazoloner. |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US4670450A (da) |
| EP (1) | EP0223178B1 (da) |
| JP (1) | JPS62114977A (da) |
| KR (1) | KR900000370B1 (da) |
| CN (1) | CN86107814A (da) |
| AT (1) | ATE79617T1 (da) |
| AU (1) | AU596616B2 (da) |
| CA (1) | CA1276936C (da) |
| DE (1) | DE3686473T2 (da) |
| DK (1) | DK540586A (da) |
| ES (1) | ES2034953T3 (da) |
| FI (1) | FI864597A (da) |
| GR (1) | GR3005481T3 (da) |
| HU (1) | HUT45035A (da) |
| IE (1) | IE58295B1 (da) |
| IL (1) | IL80584A0 (da) |
| NO (1) | NO864514L (da) |
| NZ (1) | NZ218238A (da) |
| PH (1) | PH22390A (da) |
| PT (1) | PT83733B (da) |
| ZA (1) | ZA868504B (da) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4927939A (en) * | 1985-10-15 | 1990-05-22 | Merrell Dow Pharmaceuticals | Cardiotonic aroylthiazolones |
| US4734422A (en) * | 1985-10-15 | 1988-03-29 | Merrell Dow Pharmaceuticals Inc. | Cardiotonic aroylthiazolones and the use thereof |
| US4868182A (en) * | 1986-11-05 | 1989-09-19 | Merrell Dow Pharmaceuticals Inc. | Enhancement of prazosin |
| US4866182A (en) * | 1988-02-18 | 1989-09-12 | Merrell Dow Pharmaceuticals Inc. | Cardiotonic alkanoyl and aroyl oxazolones |
| US4990519A (en) * | 1988-10-24 | 1991-02-05 | Merrell Dow Pharmaceuticals | Method of using quinolyloxazole-2-ones as proteinkinase C inhibitors |
| US4886811A (en) * | 1988-10-24 | 1989-12-12 | Merrell Dow Pharmaceuticals | Qunolyloxazole-2-ones useful as proteinkinase C inhibitors |
| US4999431A (en) * | 1988-10-24 | 1991-03-12 | Merrell Dow Pharmaceuticals | Process for preparing quinoline aldehyde and ketone derivatives |
| ATE180475T1 (de) * | 1990-09-21 | 1999-06-15 | Rohm & Haas | Dihydropyridazinone und pyridazinone als fungizide |
| ES2106874T3 (es) * | 1991-05-14 | 1997-11-16 | Merrell Pharma Inc | Inhibicion de metastasis en pacientes que padecen un cancer con la ayuda de piridiniloxazol-2-onas. |
| CN1038249C (zh) * | 1991-08-28 | 1998-05-06 | 罗姆和哈斯公司 | 含有二氢哒嗪酮及其相关化合物的杀菌组合物 |
| EP1268474A2 (en) | 2000-03-30 | 2003-01-02 | Takeda Chemical Industries, Ltd. | Substituted 1,3-thiazole compounds, their production and use |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3538104A (en) * | 1969-02-28 | 1970-11-03 | Geigy Chem Corp | Pyridyl-2-imidazolones |
| SU427015A1 (ru) * | 1972-04-21 | 1974-05-05 | В. М. Дзиомко , А. В. Иващенко | Способ получения замещенных 4-оксазолин-2-онов |
| GB1435139A (en) * | 1972-08-17 | 1976-05-12 | Sumitomo Chemical Co | Thiazole derivatives |
| JPS5238559B2 (da) * | 1972-08-17 | 1977-09-29 | ||
| US3897410A (en) * | 1973-06-04 | 1975-07-29 | Dow Chemical Co | Rapid setting non-elastomeric polyurethane compositions prepared in the presence of a mixture of liquid modifiers |
| JPS5111763A (en) * | 1974-07-16 | 1976-01-30 | Sankyo Co | 55 chikan 44 okisazorin 22 onno seizoho |
| JPS5811867B2 (ja) * | 1974-11-06 | 1983-03-04 | 東京田辺製薬株式会社 | ５，５−ジメチル−４−フエニルオキサゾリジン−２−オン誘導体の製造方法 |
| DD127812A1 (de) * | 1976-09-14 | 1977-10-12 | Joerg Beger | Verfahren zur herstellung von 2-mercapto und 2-alkylmercaptothiazolen |
| DE2714880A1 (de) * | 1977-04-02 | 1978-10-26 | Hoechst Ag | Cephemderivate und verfahren zu ihrer herstellung |
| IT1109002B (it) * | 1977-09-22 | 1985-12-16 | Menarini Sas | Derivati del 2 oxazolidone e loro metodi di preparazione |
| JPS57134417A (en) * | 1981-02-14 | 1982-08-19 | Meiji Seika Kaisha Ltd | Cardiotonic agent |
| US4649146A (en) * | 1983-01-31 | 1987-03-10 | Fujisawa Pharmaceutical Co., Ltd. | Thiazole derivatives and pharmaceutical composition comprising the same |
| US4532250A (en) * | 1983-11-23 | 1985-07-30 | American Hospital Supply Corporation | 5-Heteroarylimidazol-2-ones having cardiotonic activity |
| US4623651A (en) * | 1985-10-15 | 1986-11-18 | Merrell Dow Pharmaceuticals Inc. | Cardiotonic heterocyclocarbonyl- and acetyl-thiazolones |
| US4698353A (en) * | 1985-11-13 | 1987-10-06 | Merrell Dow Pharmaceuticals Inc. | Cardiotonic heterocyclic oxazolones |
-
1985
- 1985-11-13 US US06/797,579 patent/US4670450A/en not_active Expired - Lifetime
-
1986
- 1986-11-07 ZA ZA868504A patent/ZA868504B/xx unknown
- 1986-11-07 AU AU64933/86A patent/AU596616B2/en not_active Ceased
- 1986-11-07 CA CA000522446A patent/CA1276936C/en not_active Expired - Lifetime
- 1986-11-10 EP EP86115563A patent/EP0223178B1/en not_active Expired - Lifetime
- 1986-11-10 ES ES198686115563T patent/ES2034953T3/es not_active Expired - Lifetime
- 1986-11-10 AT AT86115563T patent/ATE79617T1/de not_active IP Right Cessation
- 1986-11-10 NZ NZ218238A patent/NZ218238A/xx unknown
- 1986-11-10 DE DE8686115563T patent/DE3686473T2/de not_active Expired - Fee Related
- 1986-11-10 PH PH34456A patent/PH22390A/en unknown
- 1986-11-11 IL IL80584A patent/IL80584A0/xx not_active IP Right Cessation
- 1986-11-11 HU HU864654A patent/HUT45035A/hu unknown
- 1986-11-12 PT PT83733A patent/PT83733B/pt not_active IP Right Cessation
- 1986-11-12 FI FI864597A patent/FI864597A/fi not_active Application Discontinuation
- 1986-11-12 KR KR1019860009532A patent/KR900000370B1/ko not_active IP Right Cessation
- 1986-11-12 IE IE299186A patent/IE58295B1/en not_active IP Right Cessation
- 1986-11-12 NO NO864514A patent/NO864514L/no unknown
- 1986-11-12 DK DK540586A patent/DK540586A/da not_active Application Discontinuation
- 1986-11-12 CN CN198686107814A patent/CN86107814A/zh active Pending
- 1986-11-13 JP JP61268803A patent/JPS62114977A/ja active Pending
-
1992
- 1992-08-20 GR GR920401821T patent/GR3005481T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ZA868504B (en) | 1987-06-24 |
| GR3005481T3 (da) | 1993-05-24 |
| KR870004971A (ko) | 1987-06-02 |
| FI864597A0 (fi) | 1986-11-12 |
| DE3686473D1 (de) | 1992-09-24 |
| FI864597A (fi) | 1987-05-14 |
| PT83733B (pt) | 1988-08-17 |
| AU596616B2 (en) | 1990-05-10 |
| PH22390A (en) | 1988-08-12 |
| DK540586A (da) | 1987-05-14 |
| DK540586D0 (da) | 1986-11-12 |
| ES2034953T3 (es) | 1993-04-16 |
| IE862991L (en) | 1987-05-13 |
| AU6493386A (en) | 1987-05-21 |
| JPS62114977A (ja) | 1987-05-26 |
| US4670450A (en) | 1987-06-02 |
| KR900000370B1 (ko) | 1990-01-25 |
| EP0223178A1 (en) | 1987-05-27 |
| EP0223178B1 (en) | 1992-08-19 |
| NZ218238A (en) | 1989-07-27 |
| ATE79617T1 (de) | 1992-09-15 |
| PT83733A (en) | 1986-12-01 |
| IL80584A0 (en) | 1987-02-27 |
| CA1276936C (en) | 1990-11-27 |
| DE3686473T2 (de) | 1993-01-28 |
| IE58295B1 (en) | 1993-08-25 |
| NO864514D0 (no) | 1986-11-12 |
| HUT45035A (en) | 1988-05-30 |
| CN86107814A (zh) | 1987-09-30 |
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