SK36596A3 - Pyrido £3,2-e|pyrazinones with antiasthmatic effectivness and producing method thereof - Google Patents

Pyrido £3,2-e|pyrazinones with antiasthmatic effectivness and producing method thereof Download PDF

Info

Publication number: SK36596A3
Authority: SK; Slovakia
Prior art keywords: optionally substituted; amino; substituted; optionally; compounds
Prior art date: 1995-03-24

Application number

SK365-96A

Other languages

English (en)

Slovak (sk)

Inventor

Tm Fgen Norbert H

Thomas Buechner

Ute Achterrath-Tuckermann

Stefan Szelenyi

Bernhard Kutscher

Original Assignee

Asta Medica Ag

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.)

1995-03-24

Filing date

1996-03-19

Publication date

1997-02-05

1996-03-19 Application filed by Asta Medica Ag filed Critical Asta Medica Ag

1997-02-05 Publication of SK36596A3 publication Critical patent/SK36596A3/sk

Links

238000000034 method Methods 0.000 title claims description 15
230000001088 anti-asthma Effects 0.000 title claims 3
239000000924 antiasthmatic agent Substances 0.000 title claims 3
229910052799 carbon Inorganic materials 0.000 claims abstract description 30
125000004104 aryloxy group Chemical group 0.000 claims abstract description 22
125000003118 aryl group Chemical group 0.000 claims abstract description 21
125000001072 heteroaryl group Chemical group 0.000 claims abstract description 17
125000005553 heteroaryloxy group Chemical group 0.000 claims abstract description 17
150000003839 salts Chemical class 0.000 claims abstract description 15
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 14
125000000217 alkyl group Chemical group 0.000 claims abstract description 13
125000003545 alkoxy group Chemical group 0.000 claims abstract description 7
150000001875 compounds Chemical class 0.000 claims description 45
-1 amino, substituted amino groups Chemical group 0.000 claims description 25
229910052736 halogen Inorganic materials 0.000 claims description 21
150000002367 halogens Chemical class 0.000 claims description 21
229910052717 sulfur Inorganic materials 0.000 claims description 21
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
229910052739 hydrogen Inorganic materials 0.000 claims description 12
238000004519 manufacturing process Methods 0.000 claims description 8
238000002360 preparation method Methods 0.000 claims description 8
DCBOUXKSNFDXER-UHFFFAOYSA-N 1h-pyrido[2,3-b]pyrazin-2-one Chemical class C1=CC=C2NC(=O)C=NC2=N1 DCBOUXKSNFDXER-UHFFFAOYSA-N 0.000 claims description 6
230000003266 anti-allergic effect Effects 0.000 claims description 4
239000000969 carrier Substances 0.000 claims description 4
239000003054 catalyst Substances 0.000 claims description 4
239000003085 diluting agent Substances 0.000 claims description 4
239000000546 pharmaceutical excipient Substances 0.000 claims description 3
239000000825 pharmaceutical preparation Substances 0.000 claims description 3
150000007513 acids Chemical class 0.000 claims description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
239000003814 drug Substances 0.000 claims 2
239000013543 active substance Substances 0.000 claims 1
150000007514 bases Chemical class 0.000 claims 1
239000003795 chemical substances by application Substances 0.000 claims 1
229910052757 nitrogen Inorganic materials 0.000 abstract description 5
125000003342 alkenyl group Chemical group 0.000 abstract 2
125000000304 alkynyl group Chemical group 0.000 abstract 2
125000000753 cycloalkyl group Chemical group 0.000 abstract 2
125000001475 halogen functional group Chemical group 0.000 abstract 2
JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 abstract 1
125000003302 alkenyloxy group Chemical group 0.000 abstract 1
125000005133 alkynyloxy group Chemical group 0.000 abstract 1
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 41
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 33
235000002639 sodium chloride Nutrition 0.000 description 16
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
229910052783 alkali metal Inorganic materials 0.000 description 12
239000002904 solvent Substances 0.000 description 12
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 11
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
230000000694 effects Effects 0.000 description 9
238000003756 stirring Methods 0.000 description 9
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
230000005764 inhibitory process Effects 0.000 description 8
206010014950 Eosinophilia Diseases 0.000 description 7
108090001050 Phosphoric Diester Hydrolases Proteins 0.000 description 7
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125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 7
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
239000000203 mixture Substances 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
239000000243 solution Substances 0.000 description 6
125000001424 substituent group Chemical group 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 5
125000006519 CCH3 Chemical group 0.000 description 5
241000700198 Cavia Species 0.000 description 5
108010058846 Ovalbumin Proteins 0.000 description 5
125000004432 carbon atom Chemical group C* 0.000 description 5
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238000002844 melting Methods 0.000 description 5
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XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
ZOOGRGPOEVQQDX-UUOKFMHZSA-N 3',5'-cyclic GMP Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=C(NC2=O)N)=C2N=C1 ZOOGRGPOEVQQDX-UUOKFMHZSA-N 0.000 description 4
241001465754 Metazoa Species 0.000 description 4
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JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
150000001340 alkali metals Chemical class 0.000 description 4
150000004945 aromatic hydrocarbons Chemical class 0.000 description 4
239000002585 base Substances 0.000 description 4
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 4
150000003254 radicals Chemical class 0.000 description 4
239000012312 sodium hydride Substances 0.000 description 4
229910000104 sodium hydride Inorganic materials 0.000 description 4
239000007858 starting material Substances 0.000 description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 3
WTESJUPOZCQOBL-UHFFFAOYSA-N 13-ethyl-4-methoxy-11-methyl-2,4,8,13-tetrazatricyclo[7.4.0.02,6]trideca-1(9),5,7,10-tetraen-12-one Chemical compound N12CN(OC)C=C2C=NC2=C1N(CC)C(=O)C(C)=C2 WTESJUPOZCQOBL-UHFFFAOYSA-N 0.000 description 3
108010044467 Isoenzymes Proteins 0.000 description 3
239000003513 alkali Substances 0.000 description 3
150000001408 amides Chemical group 0.000 description 3
208000006673 asthma Diseases 0.000 description 3
125000001309 chloro group Chemical group Cl* 0.000 description 3
238000001816 cooling Methods 0.000 description 3
239000002270 dispersing agent Substances 0.000 description 3
229960001340 histamine Drugs 0.000 description 3
238000000338 in vitro Methods 0.000 description 3
150000007522 mineralic acids Chemical class 0.000 description 3
125000004433 nitrogen atom Chemical group N* 0.000 description 3
150000007524 organic acids Chemical class 0.000 description 3
235000005985 organic acids Nutrition 0.000 description 3
230000000144 pharmacologic effect Effects 0.000 description 3
229910000027 potassium carbonate Inorganic materials 0.000 description 3
230000003389 potentiating effect Effects 0.000 description 3
238000000746 purification Methods 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
239000000758 substrate Substances 0.000 description 3
JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 2
AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 2
OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
241000700199 Cavia porcellus Species 0.000 description 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
229920005654 Sephadex Polymers 0.000 description 2
239000012507 Sephadex™ Substances 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
229910000288 alkali metal carbonate Inorganic materials 0.000 description 2
150000008041 alkali metal carbonates Chemical class 0.000 description 2
229910000102 alkali metal hydride Inorganic materials 0.000 description 2
150000008046 alkali metal hydrides Chemical class 0.000 description 2
150000008044 alkali metal hydroxides Chemical class 0.000 description 2
239000013566 allergen Substances 0.000 description 2
WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 2
239000005557 antagonist Substances 0.000 description 2
238000003556 assay Methods 0.000 description 2
239000011230 binding agent Substances 0.000 description 2
NDTCXABJQNJPCF-UHFFFAOYSA-N chlorocyclopentane Chemical compound ClC1CCCC1 NDTCXABJQNJPCF-UHFFFAOYSA-N 0.000 description 2
229940117389 dichlorobenzene Drugs 0.000 description 2
210000003979 eosinophil Anatomy 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
230000006870 function Effects 0.000 description 2
150000008282 halocarbons Chemical class 0.000 description 2
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 2
229960001317 isoprenaline Drugs 0.000 description 2
AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 2
125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
210000000056 organ Anatomy 0.000 description 2
WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 2
239000008194 pharmaceutical composition Substances 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
239000008096 xylene Substances 0.000 description 2
QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 1
ISTJMQSHILQAEC-UHFFFAOYSA-N 2-methyl-3-pentanol Chemical compound CCC(O)C(C)C ISTJMQSHILQAEC-UHFFFAOYSA-N 0.000 description 1
108010054479 3',5'-Cyclic-AMP Phosphodiesterases Proteins 0.000 description 1
102000001707 3',5'-Cyclic-AMP Phosphodiesterases Human genes 0.000 description 1
NPFVRBCDMFKOPY-UHFFFAOYSA-N 3-(4-imidazol-1-ylthiophen-2-yl)-4-methyl-4,5-dihydro-1h-pyridazin-6-one Chemical compound CC1CC(=O)NN=C1C1=CC(N2C=NC=C2)=CS1 NPFVRBCDMFKOPY-UHFFFAOYSA-N 0.000 description 1
102000004008 5'-Nucleotidase Human genes 0.000 description 1
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WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
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241000271537 Crotalus atrox Species 0.000 description 1
102000004190 Enzymes Human genes 0.000 description 1
108090000790 Enzymes Proteins 0.000 description 1
102000018899 Glutamate Receptors Human genes 0.000 description 1
108010027915 Glutamate Receptors Proteins 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
208000001953 Hypotension Diseases 0.000 description 1
101000909851 Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv) cAMP/cGMP dual specificity phosphodiesterase Rv0805 Proteins 0.000 description 1
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102000011017 Type 4 Cyclic Nucleotide Phosphodiesterases Human genes 0.000 description 1
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PJRYVTGCPZXGEY-UHFFFAOYSA-N ac1l53vz Chemical compound O=C1N(CCC)C2=CC=C(OC)N=C2N2C1=C(C)N=C2CC PJRYVTGCPZXGEY-UHFFFAOYSA-N 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
125000002947 alkylene group Chemical group 0.000 description 1
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GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
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239000007795 chemical reaction product Substances 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
210000000172 cytosol Anatomy 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
230000002461 excitatory amino acid Effects 0.000 description 1
239000003257 excitatory amino acid Substances 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
108010025843 glutamine receptor Proteins 0.000 description 1
125000000623 heterocyclic group Chemical group 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
239000001257 hydrogen Substances 0.000 description 1
208000021822 hypotensive Diseases 0.000 description 1
230000001077 hypotensive effect Effects 0.000 description 1
HOFSPGAYXKNFAM-UHFFFAOYSA-N imidazo[4,5-f]quinoxalin-2-one Chemical class C1=CN=C2C3=NC(=O)N=C3C=CC2=N1 HOFSPGAYXKNFAM-UHFFFAOYSA-N 0.000 description 1
239000012535 impurity Substances 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
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238000002347 injection Methods 0.000 description 1
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150000007529 inorganic bases Chemical class 0.000 description 1
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125000002346 iodo group Chemical group I* 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
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NZWOPGCLSHLLPA-UHFFFAOYSA-N methacholine Chemical compound C[N+](C)(C)CC(C)OC(C)=O NZWOPGCLSHLLPA-UHFFFAOYSA-N 0.000 description 1
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239000002571 phosphodiesterase inhibitor Substances 0.000 description 1
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UQDJGEHQDNVPGU-UHFFFAOYSA-N serine phosphoethanolamine Chemical compound [NH3+]CCOP([O-])(=O)OCC([NH3+])C([O-])=O UQDJGEHQDNVPGU-UHFFFAOYSA-N 0.000 description 1
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NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
LLYYNOVSVPBRGV-MVNKZKPCSA-N valnemulin Chemical compound CC(C)[C@@H](N)C(=O)NCC(C)(C)SCC(=O)O[C@@H]1C[C@@](C)(C=C)[C@@H](O)[C@H](C)[C@@]23CC[C@@H](C)[C@]1(C)[C@@H]2C(=O)CC3 LLYYNOVSVPBRGV-MVNKZKPCSA-N 0.000 description 1
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HJMQDJPMQIHLPB-UHFFFAOYSA-N zardaverine Chemical compound C1=C(OC(F)F)C(OC)=CC(C2=NNC(=O)C=C2)=C1 HJMQDJPMQIHLPB-UHFFFAOYSA-N 0.000 description 1
229950001080 zardaverine Drugs 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
- C07D471/14—Ortho-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
- C07D487/14—Ortho-condensed systems

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
Pulmonology (AREA)
Medicinal Chemistry (AREA)
Engineering & Computer Science (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Immunology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

SK365-96A 1995-03-24 1996-03-19 Pyrido £3,2-e|pyrazinones with antiasthmatic effectivness and producing method thereof SK36596A3 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19510965A DE19510965A1 (de)	1995-03-24	1995-03-24	Neue Pyrido/3,2-e/pyrazinone mit antiasthmatischer Wirksamkeit und Verfahren zu deren Herstellung

Publications (1)

Publication Number	Publication Date
SK36596A3 true SK36596A3 (en)	1997-02-05

Family

ID=7757727

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK365-96A SK36596A3 (en)	1995-03-24	1996-03-19	Pyrido £3,2-e\|pyrazinones with antiasthmatic effectivness and producing method thereof

Country Status (30)

Country	Link
US (1)	US5723463A (pl)
EP (1)	EP0736532B1 (pl)
JP (1)	JP4124280B2 (pl)
KR (1)	KR100401395B1 (pl)
CN (1)	CN1058968C (pl)
AR (1)	AR002039A1 (pl)
AT (1)	ATE217624T1 (pl)
AU (1)	AU697908B2 (pl)
BR (1)	BR9601093A (pl)
CA (1)	CA2172472C (pl)
CZ (1)	CZ290784B6 (pl)
DE (2)	DE19510965A1 (pl)
DK (1)	DK0736532T3 (pl)
ES (1)	ES2174989T3 (pl)
HR (1)	HRP960129B1 (pl)
HU (1)	HUP9600731A3 (pl)
IL (1)	IL117621A (pl)
MX (1)	MX9601069A (pl)
NO (1)	NO307091B1 (pl)
NZ (1)	NZ286232A (pl)
PL (1)	PL184800B1 (pl)
PT (1)	PT736532E (pl)
RU (1)	RU2143433C1 (pl)
SG (1)	SG43249A1 (pl)
SI (1)	SI0736532T1 (pl)
SK (1)	SK36596A3 (pl)
TR (1)	TR199600217A2 (pl)
TW (1)	TW426682B (pl)
UA (1)	UA45319C2 (pl)
ZA (1)	ZA962270B (pl)

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AU2009304293B2 (en)	2008-10-16	2012-04-26	Addex Pharma S.A.	Indole and benzomorpholine derivatives as modulators of metabotropic glutamate receptors
BRPI0921333A2 (pt)	2008-11-28	2015-12-29	Addex Pharmaceuticals Sa	derivados de indol e benzoxazina como moduladores de receptores de glutamato metabotrópicos
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NZ596078A (en)	2009-05-12	2013-06-28	Janssen Pharmaceuticals Inc	1,2,4-TRIAZOLO [4,3-a] PYRIDINE DERIVATIVES AND THEIR USE FOR THE TREATMENT OR PREVENTION OF NEUROLOGICAL AND PSYCHIATRIC DISORDERS
EA020671B1 (ru)	2009-05-12	2014-12-30	Янссен Фармасьютикалз, Инк.	ПРОИЗВОДНЫЕ 1,2,4-ТРИАЗОЛО[4,3-a]ПИРИДИНА И ИХ ПРИМЕНЕНИЕ В КАЧЕСТВЕ ПОЛОЖИТЕЛЬНЫХ АЛЛОСТЕРИЧЕСКИХ МОДУЛЯТОРОВ РЕЦЕПТОРОВ mGluR2
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CN103298810B (zh)	2010-11-08	2016-03-16	杨森制药公司	1,2,4-三唑并[4,3-a]吡啶衍生物及其作为MGLUR2受体的正变构调节剂的用途
JO3368B1 (ar)	2013-06-04	2019-03-13	Janssen Pharmaceutica Nv	مركبات 6، 7- ثاني هيدرو بيرازولو [5،1-a] بيرازين- 4 (5 يد)- اون واستخدامها بصفة منظمات تفارغية سلبية لمستقبلات ميجلور 2
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1995
- 1995-03-24 DE DE19510965A patent/DE19510965A1/de not_active Withdrawn
1996
- 1996-02-29 UA UA96020799A patent/UA45319C2/uk unknown
- 1996-03-04 TW TW085102634A patent/TW426682B/zh not_active IP Right Cessation
- 1996-03-12 ES ES96103855T patent/ES2174989T3/es not_active Expired - Lifetime
- 1996-03-12 EP EP96103855A patent/EP0736532B1/de not_active Expired - Lifetime
- 1996-03-12 CZ CZ1996747A patent/CZ290784B6/cs not_active IP Right Cessation
- 1996-03-12 DK DK96103855T patent/DK0736532T3/da active
- 1996-03-12 AT AT96103855T patent/ATE217624T1/de not_active IP Right Cessation
- 1996-03-12 DE DE59609201T patent/DE59609201D1/de not_active Expired - Fee Related
- 1996-03-12 PT PT96103855T patent/PT736532E/pt unknown
- 1996-03-12 SI SI9630473T patent/SI0736532T1/xx unknown
- 1996-03-19 SK SK365-96A patent/SK36596A3/sk unknown
- 1996-03-20 HR HR960129A patent/HRP960129B1/xx not_active IP Right Cessation
- 1996-03-20 TR TR96/00217A patent/TR199600217A2/xx unknown
- 1996-03-20 ZA ZA962270A patent/ZA962270B/xx unknown
- 1996-03-21 SG SG1996006425A patent/SG43249A1/en unknown
- 1996-03-21 NZ NZ286232A patent/NZ286232A/en unknown
- 1996-03-22 BR BR9601093A patent/BR9601093A/pt not_active Application Discontinuation
- 1996-03-22 CA CA002172472A patent/CA2172472C/en not_active Expired - Fee Related
- 1996-03-22 NO NO961173A patent/NO307091B1/no not_active IP Right Cessation
- 1996-03-22 MX MX9601069A patent/MX9601069A/es not_active IP Right Cessation
- 1996-03-22 JP JP06671296A patent/JP4124280B2/ja not_active Expired - Fee Related
- 1996-03-22 HU HU9600731A patent/HUP9600731A3/hu unknown
- 1996-03-22 CN CN96103169A patent/CN1058968C/zh not_active Expired - Fee Related
- 1996-03-22 AR ARP960101871A patent/AR002039A1/es not_active Application Discontinuation
- 1996-03-22 IL IL11762196A patent/IL117621A/xx not_active IP Right Cessation
- 1996-03-22 KR KR1019960007810A patent/KR100401395B1/ko not_active Expired - Fee Related
- 1996-03-22 AU AU48257/96A patent/AU697908B2/en not_active Ceased
- 1996-03-22 PL PL96313434A patent/PL184800B1/pl unknown
- 1996-03-25 US US08/621,315 patent/US5723463A/en not_active Expired - Lifetime
- 1996-03-25 RU RU96105827/04A patent/RU2143433C1/ru not_active IP Right Cessation

Also Published As

Publication number	Publication date
HRP960129A2 (en)	1997-08-31
ZA962270B (en)	1996-09-30
SG43249A1 (en)	1997-10-17
NO961173L (no)	1996-09-25
PL184800B1 (pl)	2002-12-31
DE59609201D1 (de)	2002-06-20
PT736532E (pt)	2002-10-31
KR100401395B1 (ko)	2003-12-24
MX9601069A (es)	1997-02-28
HU9600731D0 (en)	1996-05-28
AU4825796A (en)	1996-10-03
EP0736532A1 (de)	1996-10-09
NZ286232A (en)	1996-10-28
RU2143433C1 (ru)	1999-12-27
CN1058968C (zh)	2000-11-29
CN1140173A (zh)	1997-01-15
AR002039A1 (es)	1998-01-07
ATE217624T1 (de)	2002-06-15
DE19510965A1 (de)	1996-09-26
AU697908B2 (en)	1998-10-22
ES2174989T3 (es)	2002-11-16
TR199600217A2 (tr)	1996-10-21
NO961173D0 (no)	1996-03-22
HRP960129B1 (en)	2002-12-31
UA45319C2 (uk)	2002-04-15
CA2172472A1 (en)	1996-09-25
PL313434A1 (en)	1996-09-30
TW426682B (en)	2001-03-21
KR960034204A (ko)	1996-10-22
SI0736532T1 (en)	2002-08-31
BR9601093A (pt)	1998-01-06
CZ290784B6 (cs)	2002-10-16
JP4124280B2 (ja)	2008-07-23
NO307091B1 (no)	2000-02-07
CA2172472C (en)	2000-01-18
HUP9600731A3 (en)	1997-04-28
US5723463A (en)	1998-03-03
DK0736532T3 (da)	2002-09-02
CZ74796A3 (en)	1996-10-16
EP0736532B1 (de)	2002-05-15
IL117621A0 (en)	1996-07-23
IL117621A (en)	1999-05-09
HUP9600731A2 (en)	1997-01-28
JPH08269059A (ja)	1996-10-15

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