DD293112A5 - Heterocyclische verbindungen - Google Patents

Heterocyclische verbindungen Download PDF

Info

Publication number: DD293112A5
Authority: DD; German Democratic Republic
Prior art keywords: phenyl; dihydropyridazine; dihydro; formula; lower alkyl
Prior art date: 1989-02-11

Application number

DD90337728A

Other languages

German (de)

English (en)

Inventor

Heimo O Haikala

Erkki J Honkanen

Kari K Loennberg

Pentti T Nore

Jarmo J Pystynen

Anne M Luiro

Aino K Pippuri

Original Assignee

��`��@��k��

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

1990-02-09

Publication date

1991-08-22

1990-02-09 Application filed by ��`��@��k�� filed Critical ��`��@��k��

1991-08-22 Publication of DD293112A5 publication Critical patent/DD293112A5/de

Links

150000002391 heterocyclic compounds Chemical class 0.000 title claims abstract description 6
150000001875 compounds Chemical class 0.000 claims abstract description 72
125000000217 alkyl group Chemical group 0.000 claims abstract description 29
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 18
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
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 8
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 7
206010019280 Heart failures Diseases 0.000 claims abstract description 6
150000002431 hydrogen Chemical class 0.000 claims abstract description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 6
206010007559 Cardiac failure congestive Diseases 0.000 claims abstract description 5
125000003118 aryl group Chemical group 0.000 claims abstract description 5
229910052736 halogen Inorganic materials 0.000 claims abstract description 5
125000002252 acyl group Chemical group 0.000 claims abstract description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 4
125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 3
125000003435 aroyl group Chemical group 0.000 claims abstract description 3
150000002367 halogens Chemical class 0.000 claims abstract description 3
125000005842 heteroatom 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
125000005518 carboxamido group Chemical group 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 62
UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 claims description 33
-1 (ethoxycarbonyl) -methylidenehydrazino Chemical group 0.000 claims description 20
238000002360 preparation method Methods 0.000 claims description 18
238000000034 method Methods 0.000 claims description 17
150000003839 salts Chemical class 0.000 claims description 13
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 12
239000002904 solvent Substances 0.000 claims description 9
230000003177 cardiotonic effect Effects 0.000 claims description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
239000000203 mixture Substances 0.000 claims description 5
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 4
125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims description 4
239000000543 intermediate Substances 0.000 claims description 3
230000002378 acidificating effect Effects 0.000 claims description 2
150000001350 alkyl halides Chemical class 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
239000012442 inert solvent Substances 0.000 claims description 2
150000007529 inorganic bases Chemical class 0.000 claims description 2
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 2
150000007530 organic bases Chemical class 0.000 claims description 2
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 2
239000002253 acid Substances 0.000 claims 10
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 claims 1
239000002220 antihypertensive agent Substances 0.000 claims 1
229940030600 antihypertensive agent Drugs 0.000 claims 1
239000000496 cardiotonic agent Substances 0.000 claims 1
IJAPPYDYQCXOEF-UHFFFAOYSA-N phthalazin-1(2H)-one Chemical compound C1=CC=C2C(=O)NN=CC2=C1 IJAPPYDYQCXOEF-UHFFFAOYSA-N 0.000 claims 1
229940124549 vasodilator Drugs 0.000 claims 1
239000003071 vasodilator agent Substances 0.000 claims 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
238000002844 melting Methods 0.000 description 49
230000008018 melting Effects 0.000 description 49
235000010288 sodium nitrite Nutrition 0.000 description 38
239000011575 calcium Substances 0.000 description 19
239000000243 solution Substances 0.000 description 17
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 16
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
229910052791 calcium Inorganic materials 0.000 description 16
CUONGYYJJVDODC-UHFFFAOYSA-N malononitrile Chemical compound N#CCC#N CUONGYYJJVDODC-UHFFFAOYSA-N 0.000 description 16
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
230000005764 inhibitory process Effects 0.000 description 8
239000000047 product Substances 0.000 description 8
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
238000000354 decomposition reaction Methods 0.000 description 6
239000003814 drug Substances 0.000 description 6
229940079593 drug Drugs 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 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
229960004484 carbachol Drugs 0.000 description 5
125000004432 carbon atom Chemical group C* 0.000 description 5
230000007246 mechanism Effects 0.000 description 5
YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 4
238000002474 experimental method Methods 0.000 description 4
239000004615 ingredient Substances 0.000 description 4
210000004165 myocardium Anatomy 0.000 description 4
238000010992 reflux Methods 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
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
230000000747 cardiac effect Effects 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
210000001087 myotubule Anatomy 0.000 description 3
210000003540 papillary muscle Anatomy 0.000 description 3
230000036581 peripheral resistance Effects 0.000 description 3
229960002164 pimobendan Drugs 0.000 description 3
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 3
229910000027 potassium carbonate Inorganic materials 0.000 description 3
239000000829 suppository Substances 0.000 description 3
239000003826 tablet Substances 0.000 description 3
230000036977 tonic contraction Effects 0.000 description 3
RLTVZXVAXHWWPK-UHFFFAOYSA-N 4-(4,5-dihydropyridazin-3-yl)aniline Chemical compound NC1=CC=C(C=C1)C=1CCC=NN=1 RLTVZXVAXHWWPK-UHFFFAOYSA-N 0.000 description 2
MSBBRPWMFCLWFB-UHFFFAOYSA-N 4-(4-methyl-4,5-dihydropyridazin-3-yl)aniline Chemical compound NC1=CC=C(C=C1)C=1C(CC=NN1)C MSBBRPWMFCLWFB-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
102000002585 Contractile Proteins Human genes 0.000 description 2
108010068426 Contractile Proteins Proteins 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
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
230000009471 action Effects 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
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
230000003185 calcium uptake Effects 0.000 description 2
239000002775 capsule Substances 0.000 description 2
210000004027 cell Anatomy 0.000 description 2
239000011248 coating agent Substances 0.000 description 2
238000000576 coating method Methods 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
230000010339 dilation Effects 0.000 description 2
231100000673 dose–response relationship Toxicity 0.000 description 2
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 2
239000003112 inhibitor Substances 0.000 description 2
230000014759 maintenance of location Effects 0.000 description 2
230000010534 mechanism of action Effects 0.000 description 2
LNWHCOPMPXKPNZ-UHFFFAOYSA-N o-methyl n-aminocarbamothioate Chemical compound COC(=S)NN LNWHCOPMPXKPNZ-UHFFFAOYSA-N 0.000 description 2
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 2
150000003254 radicals Chemical class 0.000 description 2
210000005241 right ventricle Anatomy 0.000 description 2
230000035945 sensitivity Effects 0.000 description 2
208000024891 symptom Diseases 0.000 description 2
230000007306 turnover Effects 0.000 description 2
230000002792 vascular Effects 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
SGTNSNPWRIOYBX-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile Chemical compound C1=C(OC)C(OC)=CC=C1CCN(C)CCCC(C#N)(C(C)C)C1=CC=C(OC)C(OC)=C1 SGTNSNPWRIOYBX-UHFFFAOYSA-N 0.000 description 1
OEICGMPRFOJHKO-UHFFFAOYSA-N 2-(ethoxymethylidene)propanedinitrile Chemical compound CCOC=C(C#N)C#N OEICGMPRFOJHKO-UHFFFAOYSA-N 0.000 description 1
JXPDNDHCMMOJPC-UHFFFAOYSA-N 2-hydroxybutanedinitrile Chemical compound N#CC(O)CC#N JXPDNDHCMMOJPC-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
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 1
CVWMNAWLNRRPOL-UHFFFAOYSA-N 3-phenylbutan-2-one Chemical compound CC(=O)C(C)C1=CC=CC=C1 CVWMNAWLNRRPOL-UHFFFAOYSA-N 0.000 description 1
FDVBXYYRRHGGSA-UHFFFAOYSA-N 4-(4-aminophenyl)-2h-phthalazin-1-one Chemical compound C1=CC(N)=CC=C1C1=NNC(=O)C2=CC=CC=C12 FDVBXYYRRHGGSA-UHFFFAOYSA-N 0.000 description 1
102000000584 Calmodulin Human genes 0.000 description 1
108010041952 Calmodulin Proteins 0.000 description 1
241000282465 Canis Species 0.000 description 1
SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
208000000059 Dyspnea Diseases 0.000 description 1
206010013975 Dyspnoeas Diseases 0.000 description 1
108010044467 Isoenzymes Proteins 0.000 description 1
238000005684 Liebig rearrangement reaction Methods 0.000 description 1
RGSMSCMOSISCFL-UHFFFAOYSA-N NC1=CC=C(C=C1)C1=NN=CC(C1)C Chemical compound NC1=CC=C(C=C1)C1=NN=CC(C1)C RGSMSCMOSISCFL-UHFFFAOYSA-N 0.000 description 1
206010028813 Nausea Diseases 0.000 description 1
IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
206010030113 Oedema Diseases 0.000 description 1
102000004861 Phosphoric Diester Hydrolases Human genes 0.000 description 1
108090001050 Phosphoric Diester Hydrolases Proteins 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
102000010861 Type 3 Cyclic Nucleotide Phosphodiesterases Human genes 0.000 description 1
108010037543 Type 3 Cyclic Nucleotide Phosphodiesterases Proteins 0.000 description 1
206010047139 Vasoconstriction Diseases 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
239000003513 alkali Substances 0.000 description 1
125000005236 alkanoylamino group Chemical group 0.000 description 1
125000003342 alkenyl group Chemical group 0.000 description 1
125000005090 alkenylcarbonyl group Chemical group 0.000 description 1
125000004171 alkoxy aryl group Chemical group 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000003282 alkyl amino group Chemical group 0.000 description 1
125000002877 alkyl aryl group Chemical group 0.000 description 1
125000004448 alkyl carbonyl group Chemical group 0.000 description 1
125000005119 alkyl cycloalkyl group Chemical group 0.000 description 1
230000002152 alkylating effect Effects 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
206010003119 arrhythmia Diseases 0.000 description 1
125000004658 aryl carbonyl amino group Chemical group 0.000 description 1
125000005129 aryl carbonyl group Chemical group 0.000 description 1
125000002619 bicyclic group Chemical group 0.000 description 1
230000022900 cardiac muscle contraction Effects 0.000 description 1
239000000969 carrier Substances 0.000 description 1
210000000170 cell membrane Anatomy 0.000 description 1
230000008859 change Effects 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
230000008602 contraction Effects 0.000 description 1
125000000753 cycloalkyl group Chemical group 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
239000006185 dispersion Substances 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
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IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical compound CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 description 1
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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
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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
230000003834 intracellular effect Effects 0.000 description 1
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125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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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
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
125000002950 monocyclic group Chemical group 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
125000001624 naphthyl group Chemical group 0.000 description 1
230000008693 nausea Effects 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
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239000000546 pharmaceutical excipient Substances 0.000 description 1
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230000003389 potentiating effect Effects 0.000 description 1
230000002035 prolonged effect Effects 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
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JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
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239000013589 supplement Substances 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
238000010998 test method Methods 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
150000003573 thiols Chemical class 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
230000001960 triggered effect Effects 0.000 description 1
238000000870 ultraviolet spectroscopy Methods 0.000 description 1
230000025033 vasoconstriction Effects 0.000 description 1
229960001722 verapamil Drugs 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)
Pyridine Compounds (AREA)
Compounds Of Unknown Constitution (AREA)
Detergent Compositions (AREA)
Saccharide Compounds (AREA)
Cephalosporin Compounds (AREA)

DD90337728A 1989-02-11 1990-02-09 Heterocyclische verbindungen DD293112A5 (de)

Applications Claiming Priority (1)

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

Publications (1)

Publication Number	Publication Date
DD293112A5 true DD293112A5 (de)	1991-08-22

Family

ID=10651554

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD90337728A DD293112A5 (de)	1989-02-11	1990-02-09	Heterocyclische verbindungen

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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GB8824458D0 (en) *	1988-10-19	1988-11-23	Orion Yhtymae Oy	Substituted pyridazinones
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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
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
FI980901A7 (fi)	1998-04-23	1999-10-24	Orion Yhtymae Oyj	Levosimendaania säädellysti vapauttavia oraalisia 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
CA2521056A1 (fr) *	2003-03-31	2004-10-14	Daiichi Pharmaceutical Co., Ltd.	Derive d'hydrazone
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
DK1951227T3 (en)	2005-11-14	2017-07-10	Boehringer Ingelheim Vetmedica Gmbh	APPLICATION OF PIMOBENDAN TO TREAT ASYMPTOMATIC (OCCULT) HEART FAILURE
EP2502918B1 (fr)	2006-07-25	2015-03-25	Cephalon, Inc.	Dérivés de pyridazinone
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
CA2645772A1 (fr) *	2007-12-05	2009-06-05	Tagawa Greenhouse Enterprises, Llc	Support pliable et methodes
WO2010060874A1 (fr)	2008-11-25	2010-06-03	Boehringer Ingelheim Vetmedica Gmbh	Inhibiteurs de phosphodiestérase de type iii (pde iii) ou agents sensibilisateurs au ca2+ pour le traitement d'une cardiomyopathie hypertrophique
US10398705B2 (en)	2012-03-15	2019-09-03	Boehringer Ingelheim Vetmedica Gmbh	Pharmaceutical tablet formulation for the veterinary medical sector, method of production and use thereof
ES2684776T3 (es) *	2013-01-18	2018-10-04	Bristol-Myers Squibb Company	Ftalazinonas e isoquinolinonas como inhibidores de ROCK
AU2014292086B2 (en)	2013-07-19	2019-08-08	Boehringer Ingelheim Vetmedica Gmbh	Preserved etherified cyclodextrin derivatives containing liquid aqueous pharmaceutical composition
MX375936B (es)	2013-12-04	2025-03-07	Boehringer Ingelheim Vetmedica Gmbh	Composiciones farmaceuticas mejoradas de pimobendan.
US10537570B2 (en)	2016-04-06	2020-01-21	Boehringer Ingelheim Vetmedica Gmbh	Use of pimobendan for the reduction of heart size and/or the delay of onset of clinical symptoms in patients with asymptomatic heart failure due to mitral valve disease
EP3424908A1 (fr)	2017-07-07	2019-01-09	Melody Healthcare Pvt. Ltd.	Procédé de préparation de levosimendan
KR102128509B1 (ko) *	2018-12-19	2020-07-01	한국과학기술연구원	말단 아민기에 아릴 또는 헤테로아릴기가 치환된 신규한 히드라존 유도체 및 이의 용도
CN111548310B (zh) *	2020-05-12	2021-07-02	成都欣捷高新技术开发股份有限公司	一种左西孟旦钠晶型及其制备方法
KR102356644B1 (ko) *	2020-06-19	2022-01-28	한국과학기술연구원	신규한 옥소피리다지닐-페닐-카르보노하이드라조노일 디시아나이드 화합물 및 이의 용도
US11760730B2 (en)	2021-01-11	2023-09-19	Navinta, Llc	Process for the preparation of high purity Levosimendan

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DE3531658A1 (de)	1985-09-05	1987-03-12	Boehringer Mannheim Gmbh	Heterocyclisch substituierte indole, zwischenprodukte, verfahren zu ihrer herstellung und arzneimittel
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IT1208003B (it) *	1987-01-08	1989-06-01	Isf Spa	Procedimento per preparare derivati alcossi alchiliden, idrazino, piridazinici.
DE3706427A1 (de) *	1987-02-27	1988-09-08	Boehringer Mannheim Gmbh	Neue substituierte 3h-indole, zwischenprodukte, verfahren zu ihrer herstellung sowie arzneimittel
DE3728491A1 (de) *	1987-08-26	1989-03-09	Heumann Pharma Gmbh & Co	Dihydropyridazinon-derivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
JP2717687B2 (ja) *	1988-02-13	1998-02-18	日本曹達株式会社	ピリダジノン誘導体及びその製造方法
GB8903130D0 (en) *	1989-02-11	1989-03-30	Orion Yhtymae Oy	Substituted pyridazinones

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 NZ NZ232257A patent/NZ232257A/en unknown
- 1990-01-26 GB GB9001853A patent/GB2228004B/en not_active Expired - Lifetime
- 1990-01-29 AT AT90300875T patent/ATE127456T1/de active
- 1990-01-29 DK DK90300875.3T patent/DK0383449T3/da active
- 1990-01-29 DE DE69022078T patent/DE69022078T2/de not_active Expired - Lifetime
- 1990-01-29 EP EP90300875A patent/EP0383449B1/fr not_active Expired - Lifetime
- 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 FI FI900613A patent/FI96511C/fi active Protection Beyond IP Right Term
- 1990-02-08 AU AU49296/90A patent/AU619648B2/en not_active Expired
- 1990-02-09 HU HU913501D patent/HU206692B/hu unknown
- 1990-02-09 JP JP2031339A patent/JP3011955B2/ja not_active Expired - Lifetime
- 1990-02-09 US US07/477,530 patent/US5019575A/en not_active Expired - Lifetime
- 1990-02-09 PT PT93111A patent/PT93111B/pt not_active IP Right Cessation
- 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 RU SU904743235A patent/RU2048467C1/ru active
- 1990-02-09 CA CA002009678A patent/CA2009678C/fr 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
NO178067B (no)	1995-10-09
RU1836362C (ru)	1993-08-23
CA2009678A1 (fr)	1990-08-11
NZ232257A (en)	1991-03-26
NO2001020I1 (no)	2001-12-03
NO178067C (no)	1996-01-17
ZA90681B (en)	1990-10-31
FI96511C (fi)	1996-07-10
CN1044811A (zh)	1990-08-22
HU206692B (en)	1992-12-28
HU204797B (en)	1992-02-28
LU90921I2 (en)	2002-07-17
GR3017510T3 (en)	1995-12-31
DE69022078T2 (de)	1996-02-22
RU2068844C1 (ru)	1996-11-10
EP0383449B1 (fr)	1995-09-06
HU913501D0 (en)	1992-02-28
ATE127456T1 (de)	1995-09-15
AU4929690A (en)	1990-08-16
HU900747D0 (en)	1990-04-28
EP0383449A3 (fr)	1991-07-03
DE69022078D1 (de)	1995-10-12
LTIP1233A (en)	1995-04-25
US5122524A (en)	1992-06-16
RU2048467C1 (ru)	1995-11-20
AU619648B2 (en)	1992-01-30
EP0383449A2 (fr)	1990-08-22
FI96511B (fi)	1996-03-29
LT3769B (en)	1996-03-25
HUT53090A (en)	1990-09-28
US5019575A (en)	1991-05-28
NO900336L (no)	1990-08-13
GB2228004A (en)	1990-08-15
GB2228004B (en)	1992-07-15
CN1036265C (zh)	1997-10-29
CZ55790A3 (cs)	1999-10-13
GB9001853D0 (en)	1990-03-28
NO900336D0 (no)	1990-01-24
SK55790A3 (en)	2000-02-14
PT93111B (pt)	1996-01-31
ES2078939T3 (es)	1996-01-01
JP3011955B2 (ja)	2000-02-21
HUT59384A (en)	1992-05-28
SK280411B6 (sk)	2000-02-14
DK0383449T3 (da)	1996-01-02
JPH02288868A (ja)	1990-11-28
CZ286036B6 (cs)	1999-12-15
GB8903130D0 (en)	1989-03-30
PT93111A (pt)	1990-08-31
CA2009678C (fr)	1998-08-11
FI900613A0 (fi)	1990-02-08

Legal Events

Date	Code	Title	Description
2001-12-06	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
DE69022078T2 (de)	1996-02-22	Pyridazinon Derivate und Verfahren zur deren Herstellung.
DE60315516T2 (de)	2008-04-17	Pyridazinon-derivate als cdk2-hemmer
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