IL98872A - 6-(2-arylpyrazolo [1, 5-a] pyridin-3-YL 2,3-dihydropyridazin-3-one derivatives processes for the preparation thereof and pharmaceutical compositions containing them - Google Patents

6-(2-arylpyrazolo [1, 5-a] pyridin-3-YL 2,3-dihydropyridazin-3-one derivatives processes for the preparation thereof and pharmaceutical compositions containing them

Info

Publication number: IL98872A
Authority: IL; Israel
Prior art keywords: alkyl; compound; salt; alkylamino; formula
Prior art date: 1990-07-18

Application number

IL9887291A

Other languages

English (en)

Other versions

IL98872A0 (en

Inventor

Youichi Shiokawa

Atsushi Akahane

Hirohito Katayama

Takafumi Mitsunaga

Original Assignee

Fujisawa Pharmaceutical Co

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.)

1990-07-18

Filing date

1991-07-17

Publication date

1996-12-05

1991-07-17 Application filed by Fujisawa Pharmaceutical Co filed Critical Fujisawa Pharmaceutical Co

1992-07-15 Publication of IL98872A0 publication Critical patent/IL98872A0/xx

1996-12-05 Publication of IL98872A publication Critical patent/IL98872A/en

Links

239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 10
238000000034 method Methods 0.000 title abstract description 30
230000008569 process Effects 0.000 title abstract description 25
238000002360 preparation method Methods 0.000 title abstract description 24
BOUGPDHDAYIVND-UHFFFAOYSA-N 2-pyridin-3-ylpyridazin-3-one Chemical class O=C1C=CC=NN1C1=CC=CN=C1 BOUGPDHDAYIVND-UHFFFAOYSA-N 0.000 title description 2
-1 pyrazolopyridine compound Chemical class 0.000 claims abstract description 282
125000000217 alkyl group Chemical group 0.000 claims abstract description 157
150000003839 salts Chemical class 0.000 claims abstract description 114
125000003282 alkyl amino group Chemical group 0.000 claims abstract description 64
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 49
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 38
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 38
125000001424 substituent group Chemical group 0.000 claims abstract description 32
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 24
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 21
125000003342 alkenyl group Chemical group 0.000 claims abstract description 7
239000004480 active ingredient Substances 0.000 claims abstract description 5
239000003937 drug carrier Substances 0.000 claims abstract description 4
239000000546 pharmaceutical excipient Substances 0.000 claims abstract description 4
150000001875 compounds Chemical class 0.000 claims description 121
125000003831 tetrazolyl group Chemical group 0.000 claims description 21
239000003814 drug Substances 0.000 claims description 20
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
125000003545 alkoxy group Chemical group 0.000 claims description 10
125000005186 naphthyloxy group Chemical group C1(=CC=CC2=CC=CC=C12)O* 0.000 claims description 9
125000002757 morpholinyl group Chemical group 0.000 claims description 8
125000005936 piperidyl group Chemical group 0.000 claims description 8
206010030113 Oedema Diseases 0.000 claims description 7
238000003379 elimination reaction Methods 0.000 claims description 6
231100000417 nephrotoxicity Toxicity 0.000 claims description 6
125000000160 oxazolidinyl group Chemical group 0.000 claims description 6
125000004193 piperazinyl group Chemical group 0.000 claims description 6
125000004076 pyridyl group Chemical group 0.000 claims description 6
208000001647 Renal Insufficiency Diseases 0.000 claims description 5
201000006370 kidney failure Diseases 0.000 claims description 5
125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 5
206010033645 Pancreatitis Diseases 0.000 claims description 4
125000005972 dihydrochromenyl group Chemical group 0.000 claims description 4
125000006239 protecting group Chemical group 0.000 claims description 4
206010002383 Angina Pectoris Diseases 0.000 claims description 3
208000000575 Arteriosclerosis Obliterans Diseases 0.000 claims description 3
239000004593 Epoxy Substances 0.000 claims description 3
201000005569 Gout Diseases 0.000 claims description 3
206010019280 Heart failures Diseases 0.000 claims description 3
206010020772 Hypertension Diseases 0.000 claims description 3
201000001431 Hyperuricemia Diseases 0.000 claims description 3
206010061216 Infarction Diseases 0.000 claims description 3
208000030831 Peripheral arterial occlusive disease Diseases 0.000 claims description 3
208000007536 Thrombosis Diseases 0.000 claims description 3
208000032109 Transient ischaemic attack Diseases 0.000 claims description 3
206010008118 cerebral infarction Diseases 0.000 claims description 3
208000026106 cerebrovascular disease Diseases 0.000 claims description 3
238000007333 cyanation reaction Methods 0.000 claims description 3
238000005755 formation reaction Methods 0.000 claims description 3
230000007574 infarction Effects 0.000 claims description 3
201000005060 thrombophlebitis Diseases 0.000 claims description 3
201000010875 transient cerebral ischemia Diseases 0.000 claims description 3
208000020401 Depressive disease Diseases 0.000 claims description 2
206010029164 Nephrotic syndrome Diseases 0.000 claims description 2
208000008589 Obesity Diseases 0.000 claims description 2
208000025865 Ulcer Diseases 0.000 claims description 2
208000006673 asthma Diseases 0.000 claims description 2
238000006297 dehydration reaction Methods 0.000 claims description 2
206010012601 diabetes mellitus Diseases 0.000 claims description 2
208000030603 inherited susceptibility to asthma Diseases 0.000 claims description 2
208000024714 major depressive disease Diseases 0.000 claims description 2
201000003995 melancholia Diseases 0.000 claims description 2
201000008383 nephritis Diseases 0.000 claims description 2
208000009928 nephrosis Diseases 0.000 claims description 2
231100001027 nephrosis Toxicity 0.000 claims description 2
235000020824 obesity Nutrition 0.000 claims description 2
239000000296 purinergic P1 receptor antagonist Substances 0.000 claims description 2
231100000397 ulcer Toxicity 0.000 claims description 2
125000001475 halogen functional group Chemical group 0.000 claims 2
238000004519 manufacturing process Methods 0.000 claims 2
PSDPQRITXCPIJU-UHFFFAOYSA-N 6-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)-2-(2-piperidin-1-ylethyl)pyridazin-3-one Chemical compound O=C1C=CC(C2=C3C=CC=CN3N=C2C=2C=CC=CC=2)=NN1CCN1CCCCC1 PSDPQRITXCPIJU-UHFFFAOYSA-N 0.000 claims 1
206010062016 Immunosuppression Diseases 0.000 claims 1
206010061876 Obstruction Diseases 0.000 claims 1
230000001506 immunosuppresive effect Effects 0.000 claims 1
125000004104 aryloxy group Chemical group 0.000 abstract description 13
125000003118 aryl group Chemical group 0.000 abstract description 5
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 69
238000006243 chemical reaction Methods 0.000 description 57
239000000203 mixture Substances 0.000 description 50
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 49
101150041968 CDC13 gene Proteins 0.000 description 42
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 42
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 42
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 36
LENLQGBLVGGAMF-UHFFFAOYSA-N tributyl([1,2,4]triazolo[1,5-a]pyridin-6-yl)stannane Chemical compound C1=C([Sn](CCCC)(CCCC)CCCC)C=CC2=NC=NN21 LENLQGBLVGGAMF-UHFFFAOYSA-N 0.000 description 34
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 25
239000011575 calcium Substances 0.000 description 25
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 23
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 21
239000000243 solution Substances 0.000 description 21
239000002904 solvent Substances 0.000 description 21
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 20
239000002253 acid Substances 0.000 description 20
239000011541 reaction mixture Substances 0.000 description 20
ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 19
229940079593 drug Drugs 0.000 description 18
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 15
229910052757 nitrogen Inorganic materials 0.000 description 15
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
125000004433 nitrogen atom Chemical group N* 0.000 description 14
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 13
OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 description 12
239000007864 aqueous solution Substances 0.000 description 12
239000003054 catalyst Substances 0.000 description 12
125000002911 monocyclic heterocycle group Chemical group 0.000 description 12
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 11
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
239000002585 base Substances 0.000 description 11
239000000741 silica gel Substances 0.000 description 11
229910002027 silica gel Inorganic materials 0.000 description 11
239000011780 sodium chloride Substances 0.000 description 11
238000004440 column chromatography Methods 0.000 description 10
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 10
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 10
FFBHFFJDDLITSX-UHFFFAOYSA-N benzyl N-[2-hydroxy-4-(3-oxomorpholin-4-yl)phenyl]carbamate Chemical compound OC1=C(NC(=O)OCC2=CC=CC=C2)C=CC(=C1)N1CCOCC1=O FFBHFFJDDLITSX-UHFFFAOYSA-N 0.000 description 9
239000012044 organic layer Substances 0.000 description 9
238000001953 recrystallisation Methods 0.000 description 9
229920006395 saturated elastomer Polymers 0.000 description 9
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
125000005843 halogen group Chemical group 0.000 description 8
125000004430 oxygen atom Chemical group O* 0.000 description 8
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
241001465754 Metazoa Species 0.000 description 7
230000009471 action Effects 0.000 description 7
239000003480 eluent Substances 0.000 description 7
239000000284 extract Substances 0.000 description 7
229910052943 magnesium sulfate Inorganic materials 0.000 description 7
235000019341 magnesium sulphate Nutrition 0.000 description 7
238000006722 reduction reaction Methods 0.000 description 7
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
239000002126 C01EB10 - Adenosine Substances 0.000 description 6
SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 6
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
229960005305 adenosine Drugs 0.000 description 6
229910052783 alkali metal Inorganic materials 0.000 description 6
125000005236 alkanoylamino group Chemical group 0.000 description 6
239000000538 analytical sample Substances 0.000 description 6
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 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
125000001400 nonyl 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])C([H])([H])[H] 0.000 description 6
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 6
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
239000002244 precipitate Substances 0.000 description 6
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 5
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 5
241000700159 Rattus Species 0.000 description 5
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
230000002411 adverse Effects 0.000 description 5
125000005907 alkyl ester group Chemical group 0.000 description 5
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
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 5
230000007062 hydrolysis Effects 0.000 description 5
238000006460 hydrolysis reaction Methods 0.000 description 5
239000010410 layer Substances 0.000 description 5
125000004043 oxo group Chemical group O=* 0.000 description 5
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 5
238000010992 reflux Methods 0.000 description 5
239000012312 sodium hydride Substances 0.000 description 5
229910000104 sodium hydride Inorganic materials 0.000 description 5
229910052717 sulfur Inorganic materials 0.000 description 5
239000000725 suspension Substances 0.000 description 5
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical class CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 5
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
125000004423 acyloxy group Chemical group 0.000 description 4
125000004466 alkoxycarbonylamino group Chemical group 0.000 description 4
BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 4
239000003638 chemical reducing agent Substances 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
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 4
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
229910052736 halogen Inorganic materials 0.000 description 4
150000002367 halogens Chemical class 0.000 description 4
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
229910000041 hydrogen chloride Inorganic materials 0.000 description 4
239000007788 liquid Substances 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
229910052697 platinum Inorganic materials 0.000 description 4
238000000746 purification Methods 0.000 description 4
230000009467 reduction Effects 0.000 description 4
238000010998 test method Methods 0.000 description 4
210000002700 urine Anatomy 0.000 description 4
238000010792 warming Methods 0.000 description 4
238000005303 weighing Methods 0.000 description 4
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 3
DRTQHJPVMGBUCF-UCVXFZOQSA-N 1-[(2s,3s,4s,5s)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione Chemical compound O[C@H]1[C@H](O)[C@H](CO)O[C@@H]1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-UCVXFZOQSA-N 0.000 description 3
PANHWSAHZYVEIV-UHFFFAOYSA-N 2-[2-[(2-hydroxy-3-naphthalen-1-yloxypropyl)amino]ethyl]-6-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)pyridazin-3-one Chemical compound C=1C=CC2=CC=CC=C2C=1OCC(O)CNCCN(C(C=C1)=O)N=C1C(=C1C=CC=CN1N=1)C=1C1=CC=CC=C1 PANHWSAHZYVEIV-UHFFFAOYSA-N 0.000 description 3
WEMSWDZYORDDGX-UHFFFAOYSA-N 2-[2-[6-oxo-3-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)pyridazin-1-yl]ethyl]isoindole-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1CCN(C(C=C1)=O)N=C1C(=C1C=CC=CN1N=1)C=1C1=CC=CC=C1 WEMSWDZYORDDGX-UHFFFAOYSA-N 0.000 description 3
125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 3
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 3
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
125000004442 acylamino group Chemical group 0.000 description 3
125000004656 alkyl sulfonylamino group Chemical group 0.000 description 3
125000004391 aryl sulfonyl group Chemical group 0.000 description 3
KXHPPCXNWTUNSB-UHFFFAOYSA-M benzyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1=CC=CC=C1 KXHPPCXNWTUNSB-UHFFFAOYSA-M 0.000 description 3
238000010531 catalytic reduction reaction Methods 0.000 description 3
229910017052 cobalt Inorganic materials 0.000 description 3
239000010941 cobalt Substances 0.000 description 3
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 3
238000001816 cooling Methods 0.000 description 3
229910052802 copper Inorganic materials 0.000 description 3
239000010949 copper Substances 0.000 description 3
230000001882 diuretic effect Effects 0.000 description 3
230000000694 effects Effects 0.000 description 3
238000010828 elution Methods 0.000 description 3
150000002148 esters Chemical group 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
238000007918 intramuscular administration Methods 0.000 description 3
238000001990 intravenous administration Methods 0.000 description 3
229910052763 palladium Inorganic materials 0.000 description 3
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 3
230000008327 renal blood flow Effects 0.000 description 3
239000000523 sample Substances 0.000 description 3
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
238000003756 stirring Methods 0.000 description 3
125000004434 sulfur atom Chemical group 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
KJYGNRVNNRBBRM-UHFFFAOYSA-N 2-(2-aminoethyl)-6-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)pyridazin-3-one Chemical compound C1=CC(=O)N(CCN)N=C1C1=C2C=CC=CN2N=C1C1=CC=CC=C1 KJYGNRVNNRBBRM-UHFFFAOYSA-N 0.000 description 2
RWLXWSVSPDSYGJ-UHFFFAOYSA-N 2-(2-hydroxyethyl)-6-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)pyridazin-3-one Chemical compound C1=CC(=O)N(CCO)N=C1C1=C2C=CC=CN2N=C1C1=CC=CC=C1 RWLXWSVSPDSYGJ-UHFFFAOYSA-N 0.000 description 2
UJEQVJCMGDIOJH-UHFFFAOYSA-N 2-(2-morpholin-4-ylethyl)-6-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)pyridazin-3-one;hydrochloride Chemical compound Cl.O=C1C=CC(C2=C3C=CC=CN3N=C2C=2C=CC=CC=2)=NN1CCN1CCOCC1 UJEQVJCMGDIOJH-UHFFFAOYSA-N 0.000 description 2
HZWFFIYCXGUWSJ-UHFFFAOYSA-N 2-(5-bromopentyl)-6-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)pyridazin-3-one Chemical compound C1=CC(=O)N(CCCCCBr)N=C1C1=C2C=CC=CN2N=C1C1=CC=CC=C1 HZWFFIYCXGUWSJ-UHFFFAOYSA-N 0.000 description 2
IBTQITCWKCLLSR-UHFFFAOYSA-N 2-[2-(dimethylamino)ethyl]-6-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)pyridazin-3-one;hydrochloride Chemical compound Cl.C1=CC(=O)N(CCN(C)C)N=C1C1=C2C=CC=CN2N=C1C1=CC=CC=C1 IBTQITCWKCLLSR-UHFFFAOYSA-N 0.000 description 2
LMFNUFIZISKISG-UHFFFAOYSA-N 2-[2-[6-oxo-3-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)pyridazin-1-yl]ethylamino]acetic acid Chemical compound C1=CC(=O)N(CCNCC(=O)O)N=C1C1=C2C=CC=CN2N=C1C1=CC=CC=C1 LMFNUFIZISKISG-UHFFFAOYSA-N 0.000 description 2
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FCZCIXQGZOUIDN-UHFFFAOYSA-N ethyl 2-diethoxyphosphinothioyloxyacetate Chemical compound CCOC(=O)COP(=S)(OCC)OCC FCZCIXQGZOUIDN-UHFFFAOYSA-N 0.000 description 1
PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
210000003191 femoral vein Anatomy 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
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238000005658 halogenation reaction Methods 0.000 description 1
210000002837 heart atrium Anatomy 0.000 description 1
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125000005842 heteroatom Chemical group 0.000 description 1
235000003642 hunger Nutrition 0.000 description 1
229910000042 hydrogen bromide Inorganic materials 0.000 description 1
ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
125000002632 imidazolidinyl group Chemical group 0.000 description 1
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150000003949 imides Chemical class 0.000 description 1
125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
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239000003112 inhibitor Substances 0.000 description 1
229940125396 insulin Drugs 0.000 description 1
229910000765 intermetallic Inorganic materials 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
125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 description 1
125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
125000000842 isoxazolyl group Chemical group 0.000 description 1
210000003734 kidney Anatomy 0.000 description 1
230000004130 lipolysis Effects 0.000 description 1
230000003137 locomotive effect Effects 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
159000000003 magnesium salts Chemical class 0.000 description 1
239000000463 material Substances 0.000 description 1
125000005905 mesyloxy group Chemical group 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
TWXDDNPPQUTEOV-FVGYRXGTSA-N methamphetamine hydrochloride Chemical compound Cl.CN[C@@H](C)CC1=CC=CC=C1 TWXDDNPPQUTEOV-FVGYRXGTSA-N 0.000 description 1
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
125000002950 monocyclic group Chemical group 0.000 description 1
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
230000004899 motility Effects 0.000 description 1
125000005146 naphthylsulfonyl group Chemical group C1(=CC=CC2=CC=CC=C12)S(=O)(=O)* 0.000 description 1
229910000480 nickel oxide Inorganic materials 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
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230000003000 nontoxic effect Effects 0.000 description 1
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210000000056 organ Anatomy 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
125000001715 oxadiazolyl group Chemical group 0.000 description 1
125000002971 oxazolyl group Chemical group 0.000 description 1
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GNRSAWUEBMWBQH-UHFFFAOYSA-N oxonickel Chemical compound [Ni]=O GNRSAWUEBMWBQH-UHFFFAOYSA-N 0.000 description 1
HBEQXAKJSGXAIQ-UHFFFAOYSA-N oxopalladium Chemical compound [Pd]=O HBEQXAKJSGXAIQ-UHFFFAOYSA-N 0.000 description 1
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910003445 palladium oxide Inorganic materials 0.000 description 1
239000008188 pellet Substances 0.000 description 1
125000002958 pentadecyl 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])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
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239000002304 perfume Substances 0.000 description 1
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125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
239000008363 phosphate buffer Substances 0.000 description 1
XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
239000002504 physiological saline solution Substances 0.000 description 1
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
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125000003367 polycyclic group Chemical group 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 1
229940116357 potassium thiocyanate Drugs 0.000 description 1
239000000843 powder Substances 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
125000006308 propyl amino group Chemical group 0.000 description 1
239000003368 psychostimulant agent Substances 0.000 description 1
125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
125000003373 pyrazinyl group Chemical group 0.000 description 1
125000003226 pyrazolyl group Chemical group 0.000 description 1
125000004942 pyridazin-6-yl group Chemical group N1=NC=CC=C1* 0.000 description 1
NDRLPYIMWROJBG-UHFFFAOYSA-M pyridin-1-ium-1-amine;iodide Chemical compound [I-].N[N+]1=CC=CC=C1 NDRLPYIMWROJBG-UHFFFAOYSA-M 0.000 description 1
150000003222 pyridines Chemical class 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
125000000719 pyrrolidinyl group Chemical group 0.000 description 1
125000001422 pyrrolinyl group Chemical group 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
210000002254 renal artery Anatomy 0.000 description 1
230000029058 respiratory gaseous exchange Effects 0.000 description 1
DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000009518 sodium iodide Nutrition 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
VGTPCRGMBIAPIM-UHFFFAOYSA-M sodium thiocyanate Chemical compound [Na+].[S-]C#N VGTPCRGMBIAPIM-UHFFFAOYSA-M 0.000 description 1
MYXJYAIKMQJHIB-UHFFFAOYSA-M sodium;benzenesulfinate;dihydrate Chemical compound O.O.[Na+].[O-]S(=O)C1=CC=CC=C1 MYXJYAIKMQJHIB-UHFFFAOYSA-M 0.000 description 1
239000007787 solid Substances 0.000 description 1
208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
238000013222 sprague-dawley male rat Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
230000000087 stabilizing effect Effects 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
229960002317 succinimide Drugs 0.000 description 1
150000003461 sulfonyl halides Chemical class 0.000 description 1
239000000829 suppository Substances 0.000 description 1
125000001113 thiadiazolyl group Chemical group 0.000 description 1
125000001984 thiazolidinyl group Chemical group 0.000 description 1
125000002769 thiazolinyl group Chemical group 0.000 description 1
230000008719 thickening Effects 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
229910052718 tin Inorganic materials 0.000 description 1
239000011135 tin Substances 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
210000003437 trachea Anatomy 0.000 description 1
125000001425 triazolyl group Chemical group 0.000 description 1
ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
229910052721 tungsten Inorganic materials 0.000 description 1
125000002948 undecyl 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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229910052720 vanadium Inorganic materials 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
229920001567 vinyl ester resin Polymers 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Classifications

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- C07D471/02—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 two hetero rings
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- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
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Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Bioinformatics & Cheminformatics (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Engineering & Computer Science (AREA)
Diabetes (AREA)
Hematology (AREA)
Biomedical Technology (AREA)
Obesity (AREA)
Neurosurgery (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Neurology (AREA)
Pain & Pain Management (AREA)
Endocrinology (AREA)
Immunology (AREA)
Rheumatology (AREA)
Urology & Nephrology (AREA)
Emergency Medicine (AREA)
Psychiatry (AREA)
Pulmonology (AREA)
Vascular Medicine (AREA)
Child & Adolescent Psychology (AREA)
Physical Education & Sports Medicine (AREA)
Reproductive Health (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Plural Heterocyclic Compounds (AREA)

IL9887291A 1990-07-18 1991-07-17 6-(2-arylpyrazolo [1, 5-a] pyridin-3-YL 2,3-dihydropyridazin-3-one derivatives processes for the preparation thereof and pharmaceutical compositions containing them IL98872A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB909015764A GB9015764D0 (en)	1990-07-18	1990-07-18	Pyrazolopyridine compound and processes for preparation thereof

Publications (2)

Publication Number	Publication Date
IL98872A0 IL98872A0 (en)	1992-07-15
IL98872A true IL98872A (en)	1996-12-05

Family

ID=10679258

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL9887291A IL98872A (en)	1990-07-18	1991-07-17	6-(2-arylpyrazolo [1, 5-a] pyridin-3-YL 2,3-dihydropyridazin-3-one derivatives processes for the preparation thereof and pharmaceutical compositions containing them

Country Status (20)

Country	Link
US (1)	US5204346A (de)
EP (1)	EP0467248B1 (de)
JP (1)	JP3123562B2 (de)
KR (1)	KR100219957B1 (de)
CN (1)	CN1042730C (de)
AT (1)	ATE172731T1 (de)
AU (1)	AU651353B2 (de)
CA (1)	CA2047283C (de)
DE (1)	DE69130412T2 (de)
DK (1)	DK0467248T3 (de)
ES (1)	ES2121760T3 (de)
FI (1)	FI96688C (de)
GB (1)	GB9015764D0 (de)
HU (1)	HU218666B (de)
IE (1)	IE912427A1 (de)
IL (1)	IL98872A (de)
NO (1)	NO178697C (de)
PH (1)	PH30486A (de)
PT (1)	PT98358B (de)
ZA (1)	ZA915376B (de)

Families Citing this family (37)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5338743A (en) *	1988-06-06	1994-08-16	Fujisawa Pharmaceutical Co., Ltd.	New use of the adenosine antagonist
ATE211384T1 (de) *	1991-01-29	2002-01-15	Fujisawa Pharmaceutical Co	Verwendung von adenosinantagonisten zur vorbeugung und behandlung von pankreatitis und ulcera
DE4237656A1 (de) *	1992-06-13	1993-12-16	Merck Patent Gmbh	Benzimidazolderivate
CN1046724C (zh) *	1993-12-29	1999-11-24	藤泽药品工业株式会社	吡唑并吡啶化合物、含有它们的药物组合物、及其制法与用途
DE69731948D1 (de) *	1996-04-25	2005-01-20	Fujisawa Pharmaceutical Co	Mittel zur vorbeugung und heilung ischämischer darmlesion und ileus
AUPO111096A0 (en) *	1996-07-18	1996-08-08	Fujisawa Pharmaceutical Co., Ltd.	New compound
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1990
- 1990-07-18 GB GB909015764A patent/GB9015764D0/en active Pending
1991
- 1991-07-09 PH PH42760A patent/PH30486A/en unknown
- 1991-07-10 ZA ZA915376A patent/ZA915376B/xx unknown
- 1991-07-11 IE IE242791A patent/IE912427A1/en not_active Application Discontinuation
- 1991-07-13 DE DE69130412T patent/DE69130412T2/de not_active Expired - Fee Related
- 1991-07-13 DK DK91111715T patent/DK0467248T3/da active
- 1991-07-13 EP EP91111715A patent/EP0467248B1/de not_active Expired - Lifetime
- 1991-07-13 AT AT91111715T patent/ATE172731T1/de not_active IP Right Cessation
- 1991-07-13 ES ES91111715T patent/ES2121760T3/es not_active Expired - Lifetime
- 1991-07-15 US US07/729,688 patent/US5204346A/en not_active Expired - Fee Related
- 1991-07-16 JP JP03268125A patent/JP3123562B2/ja not_active Expired - Fee Related
- 1991-07-16 AU AU80468/91A patent/AU651353B2/en not_active Ceased
- 1991-07-17 CA CA002047283A patent/CA2047283C/en not_active Expired - Fee Related
- 1991-07-17 IL IL9887291A patent/IL98872A/en not_active IP Right Cessation
- 1991-07-17 HU HU397/91A patent/HU218666B/hu not_active IP Right Cessation
- 1991-07-17 FI FI913446A patent/FI96688C/fi active
- 1991-07-17 NO NO912805A patent/NO178697C/no unknown
- 1991-07-17 PT PT98358A patent/PT98358B/pt not_active IP Right Cessation
- 1991-07-17 CN CN91105592A patent/CN1042730C/zh not_active Expired - Fee Related
- 1991-07-18 KR KR1019910012195A patent/KR100219957B1/ko not_active Expired - Fee Related

Also Published As

Publication number	Publication date
CA2047283C (en)	2002-07-02
NO178697B (no)	1996-02-05
NO912805D0 (no)	1991-07-17
GB9015764D0 (en)	1990-09-05
ZA915376B (en)	1992-04-29
ES2121760T3 (es)	1998-12-16
PT98358B (pt)	1999-01-29
IL98872A0 (en)	1992-07-15
CN1059143A (zh)	1992-03-04
FI913446A0 (fi)	1991-07-17
DE69130412T2 (de)	1999-04-22
JP3123562B2 (ja)	2001-01-15
DE69130412D1 (de)	1998-12-03
ATE172731T1 (de)	1998-11-15
EP0467248A3 (en)	1992-03-11
FI96688B (fi)	1996-04-30
AU8046891A (en)	1992-01-23
US5204346A (en)	1993-04-20
FI913446L (fi)	1992-01-19
EP0467248B1 (de)	1998-10-28
FI96688C (fi)	1996-08-12
CA2047283A1 (en)	1992-01-19
NO178697C (no)	1996-05-15
KR100219957B1 (ko)	1999-09-01
NO912805L (no)	1992-01-20
HU912397D0 (en)	1991-12-30
HU218666B (hu)	2000-10-28
PH30486A (en)	1997-05-28
IE912427A1 (en)	1992-01-29
HUT58735A (en)	1992-03-30
KR920002603A (ko)	1992-02-28
DK0467248T3 (da)	1999-07-05
CN1042730C (zh)	1999-03-31
EP0467248A2 (de)	1992-01-22
AU651353B2 (en)	1994-07-21
JPH04253978A (ja)	1992-09-09
PT98358A (pt)	1992-05-29

Legal Events

Date	Code	Title
1997-06-10	FF	Patent granted
1998-01-04	KB	Patent renewed
2001-10-31	KB	Patent renewed
2006-02-21	HC	Change of name of proprietor(s)
2006-04-10	MM9K	Patent not in force due to non-payment of renewal fees

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