SK55790A3 - Substituted pyridazinones or dihydropyridazinones, method and intermediates for their preparation and pharmaceutical compositions on their base - Google Patents

Substituted pyridazinones or dihydropyridazinones, method and intermediates for their preparation and pharmaceutical compositions on their base Download PDF

Info

Publication number: SK55790A3
Authority: SK; Slovakia
Prior art keywords: phenyl; formula; dihydropyridazin; compound; alkyl
Prior art date: 1989-02-11

Application number

SK557-90A

Other languages

English (en)

Slovak (sk)

Other versions

SK280411B6 (sk

Inventor

Heimo O Haikala

Erkki J Honkanen

Kari K Lonnberg

Pentti T Nore

Jarmo J Pystynen

Anne M Luiro

Aino K Pippuri

Original Assignee

Orion Yhtymae Oy

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.)

1989-02-11

Filing date

1990-02-06

Publication date

2000-02-14

1990-02-06 Application filed by Orion Yhtymae Oy filed Critical Orion Yhtymae Oy

2000-02-14 Publication of SK55790A3 publication Critical patent/SK55790A3/sk

2000-02-14 Publication of SK280411B6 publication Critical patent/SK280411B6/sk

Links

238000000034 method Methods 0.000 title claims description 12
238000002360 preparation method Methods 0.000 title claims description 8
AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical class OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 title claims description 7
239000000543 intermediate Substances 0.000 title claims description 5
239000008194 pharmaceutical composition Substances 0.000 title claims 2
150000001875 compounds Chemical class 0.000 claims abstract description 91
125000000217 alkyl group Chemical group 0.000 claims abstract description 41
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 20
239000001257 hydrogen Substances 0.000 claims abstract description 18
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 12
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 9
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 8
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 7
229910052736 halogen Inorganic materials 0.000 claims abstract description 6
150000002367 halogens Chemical class 0.000 claims abstract description 6
150000002431 hydrogen Chemical class 0.000 claims abstract description 6
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 6
206010019280 Heart failures Diseases 0.000 claims abstract description 4
125000005518 carboxamido group Chemical group 0.000 claims abstract description 4
125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 3
229910052760 oxygen Inorganic materials 0.000 claims abstract description 3
125000004076 pyridyl group Chemical group 0.000 claims abstract description 3
229910052717 sulfur Inorganic materials 0.000 claims abstract description 3
150000002391 heterocyclic compounds Chemical class 0.000 claims abstract 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 77
125000004432 carbon atom Chemical group C* 0.000 claims description 28
150000003839 salts Chemical class 0.000 claims description 18
-1 bicyclic aryl radical Chemical class 0.000 claims description 13
125000002950 monocyclic group Chemical group 0.000 claims description 11
ORSUMIZRRGPJBR-UHFFFAOYSA-N 4,5-dihydro-1h-pyridazin-6-one Chemical compound O=C1CCC=NN1 ORSUMIZRRGPJBR-UHFFFAOYSA-N 0.000 claims description 8
125000005236 alkanoylamino group Chemical group 0.000 claims description 8
239000012442 inert solvent Substances 0.000 claims description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
239000003814 drug Substances 0.000 claims description 6
125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims description 6
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 5
125000003545 alkoxy group Chemical group 0.000 claims description 4
229910052799 carbon Inorganic materials 0.000 claims description 4
125000000753 cycloalkyl group Chemical group 0.000 claims description 4
230000008569 process Effects 0.000 claims description 4
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 4
230000002378 acidificating effect Effects 0.000 claims description 3
239000004480 active ingredient Substances 0.000 claims description 3
125000005090 alkenylcarbonyl group Chemical group 0.000 claims description 3
125000003282 alkyl amino group Chemical group 0.000 claims description 3
125000002877 alkyl aryl group Chemical group 0.000 claims description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 3
229910052757 nitrogen Inorganic materials 0.000 claims description 3
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
239000000546 pharmaceutical excipient Substances 0.000 claims description 3
239000000825 pharmaceutical preparation Substances 0.000 claims description 3
125000001424 substituent group Chemical group 0.000 claims description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
150000001350 alkyl halides Chemical class 0.000 claims description 2
125000004658 aryl carbonyl amino group Chemical group 0.000 claims description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
239000000460 chlorine Substances 0.000 claims description 2
125000001841 imino group Chemical group [H]N=* 0.000 claims description 2
150000007529 inorganic bases Chemical class 0.000 claims description 2
150000007530 organic bases Chemical class 0.000 claims description 2
239000001301 oxygen Substances 0.000 claims description 2
229940124531 pharmaceutical excipient Drugs 0.000 claims description 2
125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 2
239000011593 sulfur Substances 0.000 claims description 2
239000002253 acid Substances 0.000 claims 12
RWNZIIWZNOPSDB-UHFFFAOYSA-N 4-methyl-4,5-dihydro-1h-pyridazin-6-one Chemical compound CC1CC(=O)NN=C1 RWNZIIWZNOPSDB-UHFFFAOYSA-N 0.000 claims 2
239000003937 drug carrier Substances 0.000 claims 2
125000005418 aryl aryl group Chemical group 0.000 claims 1
LKERBMNFAFRUNH-UHFFFAOYSA-N diethyl 2-[[4-(6-oxo-4,5-dihydro-1h-pyridazin-3-yl)anilino]methylidene]propanedioate Chemical compound C1=CC(NC=C(C(=O)OCC)C(=O)OCC)=CC=C1C1=NNC(=O)CC1 LKERBMNFAFRUNH-UHFFFAOYSA-N 0.000 claims 1
230000002526 effect on cardiovascular system Effects 0.000 claims 1
125000005843 halogen group Chemical group 0.000 claims 1
GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims 1
125000003118 aryl group Chemical group 0.000 abstract description 4
125000002252 acyl group Chemical group 0.000 abstract description 2
125000003435 aroyl group Chemical group 0.000 abstract description 2
206010007559 Cardiac failure congestive Diseases 0.000 abstract 1
125000005842 heteroatom Chemical group 0.000 abstract 1
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 abstract 1
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 76
235000010288 sodium nitrite Nutrition 0.000 description 38
XMTUHSIIBGFSTQ-UHFFFAOYSA-N 3-(4-aminophenyl)-4,5-dihydro-1h-pyridazin-6-one Chemical compound C1=CC(N)=CC=C1C1=NNC(=O)CC1 XMTUHSIIBGFSTQ-UHFFFAOYSA-N 0.000 description 22
239000000243 solution Substances 0.000 description 19
239000011575 calcium Substances 0.000 description 18
CUONGYYJJVDODC-UHFFFAOYSA-N malononitrile Chemical compound N#CCC#N CUONGYYJJVDODC-UHFFFAOYSA-N 0.000 description 16
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 15
229910052791 calcium Inorganic materials 0.000 description 15
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
230000005764 inhibitory process Effects 0.000 description 9
239000000203 mixture Substances 0.000 description 7
210000004165 myocardium Anatomy 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
241000700199 Cavia porcellus Species 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
230000000747 cardiac effect Effects 0.000 description 6
230000007246 mechanism Effects 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
238000010992 reflux Methods 0.000 description 6
AIXAANGOTKPUOY-UHFFFAOYSA-N carbachol Chemical compound [Cl-].C[N+](C)(C)CCOC(N)=O AIXAANGOTKPUOY-UHFFFAOYSA-N 0.000 description 5
230000003177 cardiotonic effect Effects 0.000 description 5
238000002474 experimental method Methods 0.000 description 5
WRZLFEZKVVYIHQ-UHFFFAOYSA-N 5-[2-(4-aminophenyl)ethenyl]-1,3,4-thiadiazinan-2-one Chemical compound C1=CC(N)=CC=C1C=CC1NNC(=O)SC1 WRZLFEZKVVYIHQ-UHFFFAOYSA-N 0.000 description 4
YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 4
229960004484 carbachol Drugs 0.000 description 4
230000008602 contraction Effects 0.000 description 4
229940079593 drug Drugs 0.000 description 4
229960002164 pimobendan Drugs 0.000 description 4
GLBJJMFZWDBELO-UHFFFAOYSA-N pimobendane Chemical compound C1=CC(OC)=CC=C1C1=NC2=CC=C(C=3C(CC(=O)NN=3)C)C=C2N1 GLBJJMFZWDBELO-UHFFFAOYSA-N 0.000 description 4
239000002904 solvent Substances 0.000 description 4
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 3
239000000654 additive Substances 0.000 description 3
206010003119 arrhythmia Diseases 0.000 description 3
125000002619 bicyclic group Chemical group 0.000 description 3
230000001964 calcium overload Effects 0.000 description 3
230000000694 effects Effects 0.000 description 3
238000009472 formulation Methods 0.000 description 3
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
PZRHRDRVRGEVNW-UHFFFAOYSA-N milrinone Chemical compound N1C(=O)C(C#N)=CC(C=2C=CN=CC=2)=C1C PZRHRDRVRGEVNW-UHFFFAOYSA-N 0.000 description 3
229960003574 milrinone Drugs 0.000 description 3
210000003540 papillary muscle Anatomy 0.000 description 3
229910000027 potassium carbonate Inorganic materials 0.000 description 3
230000036316 preload Effects 0.000 description 3
239000000829 suppository Substances 0.000 description 3
239000003826 tablet Substances 0.000 description 3
230000024883 vasodilation Effects 0.000 description 3
125000006701 (C1-C7) alkyl group Chemical group 0.000 description 2
GDMRFHZLKNYRRO-UHFFFAOYSA-N 3-(4-aminophenyl)-4-methyl-4,5-dihydro-1h-pyridazin-6-one Chemical compound CC1CC(=O)NN=C1C1=CC=C(N)C=C1 GDMRFHZLKNYRRO-UHFFFAOYSA-N 0.000 description 2
MMDFKVYPOQFQHP-UHFFFAOYSA-N 4-methyl-1h-pyridazin-6-one Chemical compound CC=1C=NNC(=O)C=1 MMDFKVYPOQFQHP-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
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
108090000790 Enzymes Proteins 0.000 description 2
102000004190 Enzymes Human genes 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
108010044467 Isoenzymes Proteins 0.000 description 2
102000004861 Phosphoric Diester Hydrolases Human genes 0.000 description 2
108090001050 Phosphoric Diester Hydrolases Proteins 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 2
TVLQBBHUNDMTEC-UHFFFAOYSA-N adibendan Chemical compound N=1C=2C=C3C(C)(C)C(=O)NC3=CC=2NC=1C1=CC=NC=C1 TVLQBBHUNDMTEC-UHFFFAOYSA-N 0.000 description 2
229950004648 adibendan Drugs 0.000 description 2
230000006793 arrhythmia Effects 0.000 description 2
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238000006243 chemical reaction Methods 0.000 description 2
230000000052 comparative effect Effects 0.000 description 2
238000001816 cooling Methods 0.000 description 2
239000013078 crystal Substances 0.000 description 2
DGJMPUGMZIKDRO-UHFFFAOYSA-N cyanoacetamide Chemical compound NC(=O)CC#N DGJMPUGMZIKDRO-UHFFFAOYSA-N 0.000 description 2
230000001419 dependent effect Effects 0.000 description 2
150000001989 diazonium salts Chemical class 0.000 description 2
231100000673 dose–response relationship Toxicity 0.000 description 2
239000008298 dragée Substances 0.000 description 2
230000010534 mechanism of action Effects 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
LTYGNZSVLXJALQ-UHFFFAOYSA-N o-ethyl n-aminocarbamothioate Chemical compound CCOC(=S)NN LTYGNZSVLXJALQ-UHFFFAOYSA-N 0.000 description 2
230000002035 prolonged effect Effects 0.000 description 2
150000003254 radicals Chemical class 0.000 description 2
210000001908 sarcoplasmic reticulum Anatomy 0.000 description 2
208000024891 symptom Diseases 0.000 description 2
PRXQMYGDDZPSBF-UHFFFAOYSA-N 1-chloro-4-(4-nitrophenyl)but-3-en-2-one Chemical compound [O-][N+](=O)C1=CC=C(C=CC(=O)CCl)C=C1 PRXQMYGDDZPSBF-UHFFFAOYSA-N 0.000 description 1
CVBUKMMMRLOKQR-UHFFFAOYSA-N 1-phenylbutane-1,3-dione Chemical compound CC(=O)CC(=O)C1=CC=CC=C1 CVBUKMMMRLOKQR-UHFFFAOYSA-N 0.000 description 1
LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 1
GULMALYPRWHMKP-UHFFFAOYSA-N 2-(4-aminophenyl)-4h-1,3,4-oxadiazin-5-one Chemical compound C1=CC(N)=CC=C1C1=NNC(=O)CO1 GULMALYPRWHMKP-UHFFFAOYSA-N 0.000 description 1
KGIWPGKKIFFMKP-UHFFFAOYSA-N 2-(ethoxymethylidene)-3-hydroxybutanedinitrile Chemical compound CCOC=C(C#N)C(O)C#N KGIWPGKKIFFMKP-UHFFFAOYSA-N 0.000 description 1
BMVSAKPRNWZCPG-UHFFFAOYSA-N 2-pyridin-4-ylacetonitrile Chemical compound N#CCC1=CC=NC=C1 BMVSAKPRNWZCPG-UHFFFAOYSA-N 0.000 description 1
SDXAWLJRERMRKF-UHFFFAOYSA-N 3,5-dimethyl-1h-pyrazole Chemical compound CC=1C=C(C)NN=1 SDXAWLJRERMRKF-UHFFFAOYSA-N 0.000 description 1
KHMOVPDXDPIXKK-UHFFFAOYSA-N 3-(4-amino-2-hydroxyphenyl)-4,5-dihydro-1H-pyridazin-6-one Chemical compound OC1=CC(N)=CC=C1C1=NNC(=O)CC1 KHMOVPDXDPIXKK-UHFFFAOYSA-N 0.000 description 1
GOAZSGLSVJVOLX-UHFFFAOYSA-N 3-(4-aminophenyl)-1h-pyridazin-6-one Chemical compound C1=CC(N)=CC=C1C1=NNC(=O)C=C1 GOAZSGLSVJVOLX-UHFFFAOYSA-N 0.000 description 1
HTAWAXPFBGGDAO-UHFFFAOYSA-N 3-(4-aminophenyl)-2,5-dihydro-1h-1,2,4-triazin-6-one Chemical compound C1=CC(N)=CC=C1C1=NNC(=O)CN1 HTAWAXPFBGGDAO-UHFFFAOYSA-N 0.000 description 1
NWUOGOISBQCNKQ-UHFFFAOYSA-N 3-(4-aminophenyl)-4-methyl-1h-pyridazin-6-one Chemical compound CC1=CC(=O)NN=C1C1=CC=C(N)C=C1 NWUOGOISBQCNKQ-UHFFFAOYSA-N 0.000 description 1
WDTDPPXBFNJALR-UHFFFAOYSA-N 3-(4-aminophenyl)-5-methyl-4,5-dihydro-1h-pyridazin-6-one Chemical compound N1C(=O)C(C)CC(C=2C=CC(N)=CC=2)=N1 WDTDPPXBFNJALR-UHFFFAOYSA-N 0.000 description 1
SJQPJNBNOXRCKA-UHFFFAOYSA-N 3-(4-hydrazinylphenyl)-4,5-dihydro-1h-pyridazin-6-one;hydrochloride Chemical compound Cl.C1=CC(NN)=CC=C1C1=NNC(=O)CC1 SJQPJNBNOXRCKA-UHFFFAOYSA-N 0.000 description 1
ITTXGKOHFZJUEX-UHFFFAOYSA-N 3-(ethoxymethylidene)pentane-2,4-dione Chemical compound CCOC=C(C(C)=O)C(C)=O ITTXGKOHFZJUEX-UHFFFAOYSA-N 0.000 description 1
MKHSTHIOMSVDJT-UHFFFAOYSA-N 3-[2-(4-aminophenyl)ethenyl]-4-methyl-1h-pyridazin-6-one Chemical compound CC1=CC(=O)NN=C1C=CC1=CC=C(N)C=C1 MKHSTHIOMSVDJT-UHFFFAOYSA-N 0.000 description 1
HLMWLVGDSWQOAQ-UHFFFAOYSA-N 3-[2-(4-aminophenyl)ethenyl]-4-methyl-4,5-dihydro-1h-pyridazin-6-one Chemical compound CC1CC(=O)NN=C1C=CC1=CC=C(N)C=C1 HLMWLVGDSWQOAQ-UHFFFAOYSA-N 0.000 description 1
SKTDBOZQYSFHTA-UHFFFAOYSA-N 3-[2-(4-aminophenyl)ethyl]-4-methyl-4,5-dihydro-1h-pyridazin-6-one Chemical compound CC1CC(=O)NN=C1CCC1=CC=C(N)C=C1 SKTDBOZQYSFHTA-UHFFFAOYSA-N 0.000 description 1
DJIKKSBLYQHLNJ-UHFFFAOYSA-N 3-[[4-(6-oxo-4,5-dihydro-1h-pyridazin-3-yl)anilino]methylidene]pentane-2,4-dione Chemical compound C1=CC(NC=C(C(=O)C)C(C)=O)=CC=C1C1=NNC(=O)CC1 DJIKKSBLYQHLNJ-UHFFFAOYSA-N 0.000 description 1
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235000019738 Limestone Nutrition 0.000 description 1
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QQXLDOJGLXJCSE-UHFFFAOYSA-N N-methylnortropinone Natural products C1C(=O)CC2CCC1N2C QQXLDOJGLXJCSE-UHFFFAOYSA-N 0.000 description 1
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QIZDQFOVGFDBKW-DHBOJHSNSA-N Pseudotropine Natural products OC1C[C@@H]2[N+](C)[C@H](C1)CC2 QIZDQFOVGFDBKW-DHBOJHSNSA-N 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
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108010037543 Type 3 Cyclic Nucleotide Phosphodiesterases Proteins 0.000 description 1
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230000009471 action Effects 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
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230000002152 alkylating effect Effects 0.000 description 1
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GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 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
239000000480 calcium channel blocker Substances 0.000 description 1
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229940125692 cardiovascular agent Drugs 0.000 description 1
239000000969 carrier Substances 0.000 description 1
210000000170 cell membrane Anatomy 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
FOCAUTSVDIKZOP-UHFFFAOYSA-M chloroacetate Chemical compound [O-]C(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-M 0.000 description 1
230000004087 circulation Effects 0.000 description 1
239000003086 colorant Substances 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
HJSLFCCWAKVHIW-UHFFFAOYSA-N cyclohexane-1,3-dione Chemical compound O=C1CCCC(=O)C1 HJSLFCCWAKVHIW-UHFFFAOYSA-N 0.000 description 1
125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
LTMHNWPUDSTBKD-UHFFFAOYSA-N diethyl 2-(ethoxymethylidene)propanedioate Chemical compound CCOC=C(C(=O)OCC)C(=O)OCC LTMHNWPUDSTBKD-UHFFFAOYSA-N 0.000 description 1
DBKKFIIYQGGHJO-UHFFFAOYSA-N diethyl 2-oxopropanedioate Chemical compound CCOC(=O)C(=O)C(=O)OCC DBKKFIIYQGGHJO-UHFFFAOYSA-N 0.000 description 1
ZSANYRMTSBBUCA-UHFFFAOYSA-N diethyl 3-oxopentanedioate Chemical compound CCOC(=O)CC(=O)CC(=O)OCC ZSANYRMTSBBUCA-UHFFFAOYSA-N 0.000 description 1
125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical compound CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 description 1
FTKASJMIPSSXBP-UHFFFAOYSA-N ethyl 2-nitroacetate Chemical compound CCOC(=O)C[N+]([O-])=O FTKASJMIPSSXBP-UHFFFAOYSA-N 0.000 description 1
QVLJLWHOILVHJJ-UHFFFAOYSA-N ethyl 2-pyridin-4-ylacetate Chemical compound CCOC(=O)CC1=CC=NC=C1 QVLJLWHOILVHJJ-UHFFFAOYSA-N 0.000 description 1
XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
206010016256 fatigue Diseases 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
230000006870 function Effects 0.000 description 1
210000001035 gastrointestinal tract Anatomy 0.000 description 1
125000003106 haloaryl group Chemical group 0.000 description 1
230000035876 healing Effects 0.000 description 1
230000004217 heart function Effects 0.000 description 1
230000000004 hemodynamic effect Effects 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
NYQCKFLLTCINSJ-UHFFFAOYSA-N hydron;3-[4-(pyridin-4-ylamino)phenyl]-4,5-dihydro-1h-pyridazin-6-one;chloride Chemical compound Cl.N1C(=O)CCC(C=2C=CC(NC=3C=CN=CC=3)=CC=2)=N1 NYQCKFLLTCINSJ-UHFFFAOYSA-N 0.000 description 1
239000005555 hypertensive agent Substances 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
230000003834 intracellular effect Effects 0.000 description 1
230000008316 intracellular mechanism Effects 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
210000003041 ligament Anatomy 0.000 description 1
239000006028 limestone Substances 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
239000011159 matrix material Substances 0.000 description 1
VJRQHDWUJNFGEN-WAYWQWQTSA-N methyl (z)-3-amino-2,4-dicyanobut-2-enoate Chemical compound COC(=O)C(\C#N)=C(/N)CC#N VJRQHDWUJNFGEN-WAYWQWQTSA-N 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
210000002464 muscle smooth vascular Anatomy 0.000 description 1
NTMXFHGYWJIAAE-UHFFFAOYSA-N n,n-diethyl-3-oxobutanamide Chemical compound CCN(CC)C(=O)CC(C)=O NTMXFHGYWJIAAE-UHFFFAOYSA-N 0.000 description 1
LVVRMMUOLOBAKP-UHFFFAOYSA-N n-[4-(4-chloro-3-oxobut-1-enyl)phenyl]acetamide Chemical compound CC(=O)NC1=CC=C(C=CC(=O)CCl)C=C1 LVVRMMUOLOBAKP-UHFFFAOYSA-N 0.000 description 1
HUFLBECWUQKWOD-UHFFFAOYSA-N n-[4-[2-(2-oxo-1,3,4-thiadiazinan-5-yl)ethenyl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1C=CC1NNC(=O)SC1 HUFLBECWUQKWOD-UHFFFAOYSA-N 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
230000008693 nausea Effects 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
230000001151 other effect Effects 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
239000012071 phase Substances 0.000 description 1
239000002570 phosphodiesterase III inhibitor Substances 0.000 description 1
IJAPPYDYQCXOEF-UHFFFAOYSA-N phthalazin-1(2H)-one Chemical compound C1=CC=C2C(=O)NN=CC2=C1 IJAPPYDYQCXOEF-UHFFFAOYSA-N 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
150000003230 pyrimidines Chemical class 0.000 description 1
238000012216 screening Methods 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
210000002966 serum Anatomy 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
238000002798 spectrophotometry method Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
IMCGHZIGRANKHV-AJNGGQMLSA-N tert-butyl (3s,5s)-2-oxo-5-[(2s,4s)-5-oxo-4-propan-2-yloxolan-2-yl]-3-propan-2-ylpyrrolidine-1-carboxylate Chemical compound O1C(=O)[C@H](C(C)C)C[C@H]1[C@H]1N(C(=O)OC(C)(C)C)C(=O)[C@H](C(C)C)C1 IMCGHZIGRANKHV-AJNGGQMLSA-N 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
230000001225 therapeutic effect Effects 0.000 description 1
150000003573 thiols Chemical class 0.000 description 1
231100000167 toxic agent Toxicity 0.000 description 1
CYHOMWAPJJPNMW-JIGDXULJSA-N tropine Chemical compound C1[C@@H](O)C[C@H]2CC[C@@H]1N2C CYHOMWAPJJPNMW-JIGDXULJSA-N 0.000 description 1
208000023577 vascular insufficiency disease Diseases 0.000 description 1
230000025033 vasoconstriction Effects 0.000 description 1
229940124549 vasodilator Drugs 0.000 description 1
239000003071 vasodilator agent Substances 0.000 description 1
230000002861 ventricular Effects 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/15—Six-membered rings
- C07D285/16—Thiadiazines; Hydrogenated thiadiazines
- 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
- 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
- A61P9/08—Vasodilators for multiple indications
- 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
- A61P9/12—Antihypertensives
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/04—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having less than three double bonds between ring members or between ring members and non-ring members
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having 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
- C07D237/14—Oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/26—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings condensed with carbocyclic rings or ring systems
- C07D237/30—Phthalazines
- C07D237/32—Phthalazines with oxygen atoms directly attached to carbon atoms of the nitrogen-containing ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
- C07D253/02—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 not condensed with other rings
- C07D253/06—1,2,4-Triazines
- C07D253/065—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members
- C07D253/07—1,2,4-Triazines having 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D273/00—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00
- C07D273/02—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00 having two nitrogen atoms and only one oxygen atom
- C07D273/04—Six-membered rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Cardiology (AREA)
General Health & Medical Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Heart & Thoracic Surgery (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Hospice & Palliative Care (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Compounds Of Unknown Constitution (AREA)
Detergent Compositions (AREA)
Pyridine Compounds (AREA)
Saccharide Compounds (AREA)
Cephalosporin Compounds (AREA)

SK557-90A 1989-02-11 1990-02-06 Substituované pyridazinóny alebo dihydropyridazinó SK280411B6 (sk)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB898903130A GB8903130D0 (en)	1989-02-11	1989-02-11	Substituted pyridazinones

Publications (2)

Publication Number	Publication Date
SK55790A3 true SK55790A3 (en)	2000-02-14
SK280411B6 SK280411B6 (sk)	2000-02-14

Family

ID=10651554

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK557-90A SK280411B6 (sk)	1989-02-11	1990-02-06	Substituované pyridazinóny alebo dihydropyridazinó

Country Status (24)

Country	Link
US (2)	US5019575A (fr)
EP (1)	EP0383449B1 (fr)
JP (1)	JP3011955B2 (fr)
CN (1)	CN1036265C (fr)
AT (1)	ATE127456T1 (fr)
AU (1)	AU619648B2 (fr)
CA (1)	CA2009678C (fr)
CZ (1)	CZ286036B6 (fr)
DD (1)	DD293112A5 (fr)
DE (1)	DE69022078T2 (fr)
DK (1)	DK0383449T3 (fr)
ES (1)	ES2078939T3 (fr)
FI (1)	FI96511C (fr)
GB (2)	GB8903130D0 (fr)
GR (1)	GR3017510T3 (fr)
HU (2)	HU206692B (fr)
LT (1)	LT3769B (fr)
LU (1)	LU90921I2 (fr)
NO (2)	NO178067C (fr)
NZ (1)	NZ232257A (fr)
PT (1)	PT93111B (fr)
RU (3)	RU2048467C1 (fr)
SK (1)	SK280411B6 (fr)
ZA (1)	ZA90681B (fr)

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB8824458D0 (en) *	1988-10-19	1988-11-23	Orion Yhtymae Oy	Substituted pyridazinones
IE62890B1 (en) *	1988-12-06	1995-03-08	Hafslund Nycomed Pharma	New piperazinylalkyl-3(2h)-pyridazinones process for the preparation thereof and the use thereof as agents lowering blood pressure
GB8903130D0 (en) *	1989-02-11	1989-03-30	Orion Yhtymae Oy	Substituted pyridazinones
GB2251615B (en) *	1991-01-03	1995-02-08	Orion Yhtymae Oy	(-)-[[4-(1,4,5,6-tetrahydro-4-methyl-6-oxo-3-pyridazinyl)phenyl]hydrazono]pro panedinitrile
GB2266841A (en) *	1992-05-06	1993-11-17	Orion Yhtymae Oy	Compounds for use as anti-ischemic medicaments
DE4239540A1 (de) *	1992-11-25	1994-05-26	Asta Medica Ag	Neue heterocyclische Verbindungen mit antiasthmatischer/antiallergischer, entzündungshemmender, positiv inotroper und blutdrucksenkender Wirkung
TW309520B (fr) *	1994-04-26	1997-07-01	Mitsubishi Chem Corp
DE19514568A1 (de)	1995-04-20	1996-10-24	Merck Patent Gmbh	Arylalkyl-pyridazinone
GB9606474D0 (en) *	1996-03-27	1996-06-05	Orion Yhytmo Oy	Method for obtaining pure enantiomers of a pyridazinone derivative
GB9626472D0 (en)	1996-12-20	1997-02-05	Aperia Anita C	New use of comt inhibitors
FI973804A7 (fi) *	1997-09-26	1999-03-27	Orion Yhtymae Oy	Levosimendaanin oraalisia koostumuksia
FI980901A7 (fi)	1998-04-23	1999-10-24	Orion Yhtymae Oyj	Levosimendaania säädellysti vapauttavia oraalisia koostumuksia
FI105389B (fi) *	1998-04-23	2000-08-15	Orion Yhtymae Oyj	Menetelmä levosimendaaniannon siedettävyyden seuraamiseksi
FI980902A7 (fi)	1998-04-23	1999-10-24	Orion Yhtymae Oyj	Levosimendaanin stabiileja koostumuksia
FI104718B (fi) *	1998-06-18	2000-03-31	Orion Yhtymae Oyj	[[4-(2-atsido-3-metyyli-5-oksotetrahydrofuran-2-yyli)fenyyli]hydratsono]propaanidinitriili käytettäväksi referenssiaineena levosimendaanierien analyysissä
FI20000577A0 (fi)	2000-03-13	2000-03-13	Orion Yhtymae Oy	Pyridatsinyylifenyylihydratsoneja
FI20002525A7 (fi) *	2000-11-17	2002-05-18	Orion Yhtymae Oyj	Tulehduksenvastaisia aineita
WO2002072099A1 (fr) *	2001-03-14	2002-09-19	Mitsubishi Pharma Corporation	Agent therapeutique et / ou prophylactique pour la cardiopathie ischemique diabetique
JPWO2004087641A1 (ja) *	2003-03-31	2006-06-29	第一製薬株式会社	ヒドラゾン誘導体
DE102004011512B4 (de)	2004-03-08	2022-01-13	Boehringer Ingelheim Vetmedica Gmbh	Pharmazeutische Zubereitung enthaltend Pimobendan
EP1579862A1 (fr)	2004-03-25	2005-09-28	Boehringer Ingelheim Vetmedica Gmbh	Utilisation des inhibiteurs de PDE III pour la réduction de la taille du coeur chez des mammifères souffrant d'insufficances cardiaques
US8980894B2 (en)	2004-03-25	2015-03-17	Boehringer Ingelheim Vetmedica Gmbh	Use of PDE III inhibitors for the treatment of asymptomatic (occult) heart failure
AU2005249498B2 (en) *	2004-05-28	2010-06-24	Orion Corporation	Methods for treating a mammal before, during and after cardiac arrest
HUE033546T2 (hu)	2005-11-14	2017-12-28	Boehringer Ingelheim Vetmedica Gmbh	Pimobendán alkalmazása aszimptómás (rejtett) szívelégtelenség kezelésére
UA95644C2 (ru)	2006-07-25	2011-08-25	Сефалон, Инк.	Пиридазиноновые производные, фармацевтическая композиция и способ лечения заболеваний
EP1920785A1 (fr)	2006-11-07	2008-05-14	Boehringer Ingelheim Vetmedica Gmbh	Préparation liquide contenant un complexe du pimobendane et de la cyclodextrine
FR2917975B1 (fr)	2007-06-26	2009-10-16	Ceva Sante Animale Sa	Compositions et traitement de l'insuffisance cardiaque chez les animaux mammiferes non humains
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1989
- 1989-02-11 GB GB898903130A patent/GB8903130D0/en active Pending
1990
- 1990-01-24 NO NO900336A patent/NO178067C/no not_active IP Right Cessation
- 1990-01-26 GB GB9001853A patent/GB2228004B/en not_active Expired - Lifetime
- 1990-01-26 NZ NZ232257A patent/NZ232257A/en unknown
- 1990-01-29 DE DE69022078T patent/DE69022078T2/de not_active Expired - Lifetime
- 1990-01-29 AT AT90300875T patent/ATE127456T1/de active
- 1990-01-29 EP EP90300875A patent/EP0383449B1/fr not_active Expired - Lifetime
- 1990-01-29 DK DK90300875.3T patent/DK0383449T3/da active
- 1990-01-29 ES ES90300875T patent/ES2078939T3/es not_active Expired - Lifetime
- 1990-01-30 ZA ZA90681A patent/ZA90681B/xx unknown
- 1990-02-06 SK SK557-90A patent/SK280411B6/sk not_active IP Right Cessation
- 1990-02-06 CZ CS90557A patent/CZ286036B6/cs not_active IP Right Cessation
- 1990-02-08 AU AU49296/90A patent/AU619648B2/en not_active Expired
- 1990-02-08 FI FI900613A patent/FI96511C/fi active Protection Beyond IP Right Term
- 1990-02-09 HU HU913501D patent/HU206692B/hu unknown
- 1990-02-09 DD DD90337728A patent/DD293112A5/de not_active IP Right Cessation
- 1990-02-09 HU HU90747A patent/HU204797B/hu unknown
- 1990-02-09 PT PT93111A patent/PT93111B/pt not_active IP Right Cessation
- 1990-02-09 CA CA002009678A patent/CA2009678C/fr not_active Expired - Lifetime
- 1990-02-09 JP JP2031339A patent/JP3011955B2/ja not_active Expired - Lifetime
- 1990-02-09 RU SU904743235A patent/RU2048467C1/ru active
- 1990-02-09 US US07/477,530 patent/US5019575A/en not_active Expired - Lifetime
- 1990-02-10 CN CN90100645A patent/CN1036265C/zh not_active Expired - Lifetime
1991
- 1991-03-15 US US07/670,338 patent/US5122524A/en not_active Expired - Lifetime
- 1991-05-05 RU SU914895242A patent/RU1836362C/ru active
1992
- 1992-06-29 RU SU925011896A patent/RU2068844C1/ru active
1993
- 1993-09-28 LT LTIP1233A patent/LT3769B/lt not_active IP Right Cessation
1995
- 1995-09-22 GR GR950402628T patent/GR3017510T3/el unknown
2001
- 2001-11-19 NO NO2001020C patent/NO2001020I1/no unknown
2002
- 2002-05-17 LU LU90921C patent/LU90921I2/en unknown

Also Published As

Publication number	Publication date
CA2009678C (fr)	1998-08-11
HU204797B (en)	1992-02-28
ES2078939T3 (es)	1996-01-01
NO900336L (no)	1990-08-13
HU900747D0 (en)	1990-04-28
ZA90681B (en)	1990-10-31
EP0383449A3 (fr)	1991-07-03
FI96511B (fi)	1996-03-29
US5019575A (en)	1991-05-28
PT93111B (pt)	1996-01-31
LU90921I2 (en)	2002-07-17
GB2228004B (en)	1992-07-15
ATE127456T1 (de)	1995-09-15
HUT59384A (en)	1992-05-28
JPH02288868A (ja)	1990-11-28
LTIP1233A (en)	1995-04-25
CN1036265C (zh)	1997-10-29
EP0383449A2 (fr)	1990-08-22
SK280411B6 (sk)	2000-02-14
DD293112A5 (de)	1991-08-22
CZ286036B6 (cs)	1999-12-15
GB8903130D0 (en)	1989-03-30
LT3769B (en)	1996-03-25
FI900613A0 (fi)	1990-02-08
US5122524A (en)	1992-06-16
EP0383449B1 (fr)	1995-09-06
DE69022078T2 (de)	1996-02-22
HU206692B (en)	1992-12-28
NO900336D0 (no)	1990-01-24
NZ232257A (en)	1991-03-26
GB2228004A (en)	1990-08-15
CZ55790A3 (cs)	1999-10-13
RU2068844C1 (ru)	1996-11-10
RU2048467C1 (ru)	1995-11-20
AU619648B2 (en)	1992-01-30
PT93111A (pt)	1990-08-31
GB9001853D0 (en)	1990-03-28
DE69022078D1 (de)	1995-10-12
HUT53090A (en)	1990-09-28
CA2009678A1 (fr)	1990-08-11
HU913501D0 (en)	1992-02-28
DK0383449T3 (da)	1996-01-02
NO178067C (no)	1996-01-17
FI96511C (fi)	1996-07-10
CN1044811A (zh)	1990-08-22
NO178067B (no)	1995-10-09
AU4929690A (en)	1990-08-16
NO2001020I1 (no)	2001-12-03
JP3011955B2 (ja)	2000-02-21
GR3017510T3 (en)	1995-12-31
RU1836362C (ru)	1993-08-23

Legal Events

Date	Code	Title	Description
2010-04-07	MK4A	Patent expired	Expiry date: 20100206

Publication	Publication Date	Title
SK55790A3 (en)	2000-02-14	Substituted pyridazinones or dihydropyridazinones, method and intermediates for their preparation and pharmaceutical compositions on their base
EP1471065B1 (fr)	2008-02-27	Nouveau compose 1,2,4-triazole
BRPI0711538A2 (pt)	2011-11-01	compostos farmacêuticos
JP2972377B2 (ja)	1999-11-08	カテコール誘導体、その薬学的に許容しうる塩およびエステルならびにそれらを含有する医薬組成物
EP0132375B1 (fr)	1989-06-21	Dihydropyridines comme agents anti-ischaémiques et anti-hypertensifs
KR20050070036A (ko)	2005-07-05	Ｌ형 칼슘 채널을 차단하는 동시에 3형포스포디에스테라제의 활성을 억제할 수 있는디히드로피리딘 화합물
EP0077983B1 (fr)	1987-04-29	Dérivés de triazine, leur procédé de préparation et les compositions pharmaceutiques les contenant
US5185332A (en)	1993-02-09	Thiadiazines and pharmaceutical compositions thereof as well as method of use
CA1326851C (fr)	1994-02-08	Oxadiazolyl-1,4-dihydropyridines et analogues de celles-ci
CA2048668A1 (fr)	1991-06-30	Derive d'ethynylphenyl, procede de preparation et medicament contre les maladies circulatoires contenant ce produit comme principe actif
JPS62169779A (ja)	1987-07-25	ジヒドロピリジン系の抗虚血薬および降圧薬
JPS61167683A (ja)	1986-07-29	ジヒドロピリジン抗虚血および抗高血圧剤
HK1067132B (en)	2012-10-05	1,2,4-triazole compound
JPS617276A (ja)	1986-01-13	ジヒドロピリジン抗虚血および降圧剤
JPH0321552B2 (fr)	1991-03-22