BG104803A - N-/(заместени петчленни ди- или триаза - диненаситени пръстенни) карбонил / гуанидинови производни за лечение на исхемия - Google Patents

N-/(заместени петчленни ди- или триаза - диненаситени пръстенни) карбонил / гуанидинови производни за лечение на исхемия Download PDF

Info

Publication number: BG104803A
Authority: BG; Bulgaria
Prior art keywords: mono; alkyl; compound; pharmaceutically acceptable; optionally
Prior art date: 1998-02-27

Application number

BG104803A

Other languages

Bulgarian (bg)

English (en)

Inventor

Ernest Hamanaka

- PEREZ Angel GUZMAN

Roger Ruggeri

Ronald WESTER

Christian MULARSKI

Original Assignee

Pfizer Products Inc.

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.)

1998-02-27

Filing date

2000-09-27

Publication date

2001-05-31

2000-09-27 Application filed by Pfizer Products Inc. filed Critical Pfizer Products Inc.

2001-05-31 Publication of BG104803A publication Critical patent/BG104803A/bg

Links

208000028867 ischemia Diseases 0.000 title claims abstract description 29
238000011282 treatment Methods 0.000 title claims description 17
150000002357 guanidines Chemical class 0.000 title description 5
229940083094 guanine derivative acting on arteriolar smooth muscle Drugs 0.000 title description 4
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 title description 2
238000000034 method Methods 0.000 claims abstract description 99
230000000451 tissue damage Effects 0.000 claims abstract description 29
231100000827 tissue damage Toxicity 0.000 claims abstract description 29
239000003112 inhibitor Substances 0.000 claims abstract description 22
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 14
150000001875 compounds Chemical class 0.000 claims description 625
229910052757 nitrogen Inorganic materials 0.000 claims description 397
-1 (Ci ^ alkoxy- Chemical group 0.000 claims description 278
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 264
150000003839 salts Chemical class 0.000 claims description 258
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 194
125000000217 alkyl group Chemical group 0.000 claims description 166
125000004356 hydroxy functional group Chemical group O* 0.000 claims description 145
125000003282 alkyl amino group Chemical group 0.000 claims description 130
229940002612 prodrug Drugs 0.000 claims description 116
239000000651 prodrug Substances 0.000 claims description 116
229920006395 saturated elastomer Polymers 0.000 claims description 116
125000004414 alkyl thio group Chemical group 0.000 claims description 114
125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 109
229910052760 oxygen Inorganic materials 0.000 claims description 103
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 100
239000001301 oxygen Substances 0.000 claims description 100
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 95
125000001424 substituent group Chemical group 0.000 claims description 94
229910052717 sulfur Inorganic materials 0.000 claims description 94
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 92
239000011593 sulfur Chemical group 0.000 claims description 92
125000005842 heteroatom Chemical group 0.000 claims description 91
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 91
125000003545 alkoxy group Chemical group 0.000 claims description 90
125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims description 86
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 85
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 84
125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims description 83
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 83
125000005236 alkanoylamino group Chemical group 0.000 claims description 82
125000001589 carboacyl group Chemical group 0.000 claims description 82
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 80
125000002619 bicyclic group Chemical group 0.000 claims description 78
125000005843 halogen group Chemical group 0.000 claims description 78
125000005422 alkyl sulfonamido group Chemical group 0.000 claims description 77
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 75
125000001153 fluoro group Chemical group F* 0.000 claims description 71
235000019000 fluorine Nutrition 0.000 claims description 68
229910052799 carbon Inorganic materials 0.000 claims description 65
125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 63
125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 63
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 62
125000004423 acyloxy group Chemical group 0.000 claims description 57
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 52
125000004093 cyano group Chemical group *C#N 0.000 claims description 51
125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 49
FUQOTYRCMBZFOL-UHFFFAOYSA-N 5-chloro-1H-indole-2-carboxylic acid Chemical compound ClC1=CC=C2NC(C(=O)O)=CC2=C1 FUQOTYRCMBZFOL-UHFFFAOYSA-N 0.000 claims description 44
ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 44
241000124008 Mammalia Species 0.000 claims description 44
239000000203 mixture Substances 0.000 claims description 41
229910052739 hydrogen Inorganic materials 0.000 claims description 37
241000282414 Homo sapiens Species 0.000 claims description 36
239000001257 hydrogen Substances 0.000 claims description 34
239000002904 solvent Substances 0.000 claims description 34
125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims description 30
125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 29
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 29
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 27
206010056740 Genital discharge Diseases 0.000 claims description 26
239000003288 aldose reductase inhibitor Substances 0.000 claims description 25
CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 22
SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 22
125000000714 pyrimidinyl group Chemical group 0.000 claims description 22
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 21
239000002253 acid Substances 0.000 claims description 21
125000004076 pyridyl group Chemical group 0.000 claims description 21
239000003937 drug carrier Substances 0.000 claims description 20
125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 20
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 20
125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims description 19
239000002552 dosage form Substances 0.000 claims description 19
125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 19
125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 19
229940118148 Aldose reductase inhibitor Drugs 0.000 claims description 18
125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 claims description 18
125000004619 benzopyranyl group Chemical group O1C(C=CC2=C1C=CC=C2)* 0.000 claims description 18
125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 18
230000000747 cardiac effect Effects 0.000 claims description 18
125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims description 18
125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims description 17
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 17
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 claims description 16
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 16
230000001225 therapeutic effect Effects 0.000 claims description 16
125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 14
WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 claims description 14
125000004399 C1-C4 alkenyl group Chemical group 0.000 claims description 13
239000003085 diluting agent Substances 0.000 claims description 13
125000006709 (C5-C7) cycloalkenyl group Chemical group 0.000 claims description 12
ROJNYKZWTOHRNU-UHFFFAOYSA-N 2-chloro-4,5-difluoro-n-[[2-methoxy-5-(methylcarbamoylamino)phenyl]carbamoyl]benzamide Chemical compound CNC(=O)NC1=CC=C(OC)C(NC(=O)NC(=O)C=2C(=CC(F)=C(F)C=2)Cl)=C1 ROJNYKZWTOHRNU-UHFFFAOYSA-N 0.000 claims description 12
125000001041 indolyl group Chemical group 0.000 claims description 12
125000001624 naphthyl group Chemical group 0.000 claims description 12
239000002327 cardiovascular agent Substances 0.000 claims description 11
229940125692 cardiovascular agent Drugs 0.000 claims description 11
239000003795 chemical substances by application Substances 0.000 claims description 11
125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 10
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 10
125000002950 monocyclic group Chemical group 0.000 claims description 10
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 10
239000002126 C01EB10 - Adenosine Substances 0.000 claims description 8
229960005305 adenosine Drugs 0.000 claims description 8
125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 8
125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 8
125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims description 8
125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 8
150000002148 esters Chemical class 0.000 claims description 8
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 8
230000001476 alcoholic effect Effects 0.000 claims description 7
125000005874 benzothiadiazolyl group Chemical group 0.000 claims description 7
238000007675 cardiac surgery Methods 0.000 claims description 7
230000002490 cerebral effect Effects 0.000 claims description 7
239000001103 potassium chloride Substances 0.000 claims description 7
235000011164 potassium chloride Nutrition 0.000 claims description 7
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
MNQZXJOMYWMBOU-UHFFFAOYSA-N glyceraldehyde Chemical compound OCC(O)C=O MNQZXJOMYWMBOU-UHFFFAOYSA-N 0.000 claims description 6
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 5
CNAUCBNUTUGRDC-UHFFFAOYSA-N 5-cyclopropyl-1-[2-(trifluoromethyl)phenyl]pyrazole-4-carboxylic acid Chemical compound OC(=O)C=1C=NN(C=2C(=CC=CC=2)C(F)(F)F)C=1C1CC1 CNAUCBNUTUGRDC-UHFFFAOYSA-N 0.000 claims description 5
NWYHYJVRSBVTGC-UHFFFAOYSA-N 5-ethyl-1-quinolin-5-ylpyrazole-4-carboxylic acid Chemical compound CCC1=C(C(O)=O)C=NN1C1=CC=CC2=NC=CC=C12 NWYHYJVRSBVTGC-UHFFFAOYSA-N 0.000 claims description 5
ZEDQLIICZORELY-UHFFFAOYSA-N 5-methyl-1-quinolin-6-ylpyrazole-4-carboxylic acid Chemical compound CC1=C(C(O)=O)C=NN1C1=CC=C(N=CC=C2)C2=C1 ZEDQLIICZORELY-UHFFFAOYSA-N 0.000 claims description 5
239000005541 ACE inhibitor Substances 0.000 claims description 5
206010053567 Coagulopathies Diseases 0.000 claims description 5
229940044094 angiotensin-converting-enzyme inhibitor Drugs 0.000 claims description 5
125000003118 aryl group Chemical group 0.000 claims description 5
239000002876 beta blocker Substances 0.000 claims description 5
229940097320 beta blocking agent Drugs 0.000 claims description 5
230000035602 clotting Effects 0.000 claims description 5
239000008024 pharmaceutical diluent Substances 0.000 claims description 5
239000008063 pharmaceutical solvent Substances 0.000 claims description 5
238000001356 surgical procedure Methods 0.000 claims description 5
HYNXFOPOJQHNAI-UHFFFAOYSA-N 1-isoquinolin-5-yl-3-methylpyrazole-4-carboxylic acid Chemical compound C1=C(C(O)=O)C(C)=NN1C1=CC=CC2=CN=CC=C12 HYNXFOPOJQHNAI-UHFFFAOYSA-N 0.000 claims description 4
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 4
IWLPHHUXVUATBQ-UHFFFAOYSA-N 2-isoquinolin-5-yl-5-methyltriazole-4-carboxylic acid Chemical compound N1=C(C(O)=O)C(C)=NN1C1=CC=CC2=CN=CC=C12 IWLPHHUXVUATBQ-UHFFFAOYSA-N 0.000 claims description 4
125000004539 5-benzimidazolyl group Chemical group N1=CNC2=C1C=CC(=C2)* 0.000 claims description 4
YDCGVASFVACWKF-NRFANRHFSA-N 5-chloro-1h-indole-2-carboxylic acid [1-(4-fluorobenzyl)-2-(4-hydroxypiperidin-1yl)-2-oxoethyl]amide Chemical compound C1CC(O)CCN1C(=O)[C@@H](NC(=O)C=1NC2=CC=C(Cl)C=C2C=1)CC1=CC=C(F)C=C1 YDCGVASFVACWKF-NRFANRHFSA-N 0.000 claims description 4
KLLOIWZUJAJGPU-IBGZPJMESA-N 5-chloro-n-[(2s)-1-(3-hydroxyazetidin-1-yl)-1-oxo-3-phenylpropan-2-yl]-1h-indole-2-carboxamide Chemical compound C1C(O)CN1C(=O)[C@@H](NC(=O)C=1NC2=CC=C(Cl)C=C2C=1)CC1=CC=CC=C1 KLLOIWZUJAJGPU-IBGZPJMESA-N 0.000 claims description 4
DJKMYENTBUQHNM-FQEVSTJZSA-N 5-chloro-n-[(2s)-1-(3-hydroxyiminopyrrolidin-1-yl)-1-oxo-3-phenylpropan-2-yl]-1h-indole-2-carboxamide Chemical compound C1C(=NO)CCN1C(=O)[C@@H](NC(=O)C=1NC2=CC=C(Cl)C=C2C=1)CC1=CC=CC=C1 DJKMYENTBUQHNM-FQEVSTJZSA-N 0.000 claims description 4
FTMFRKISBMECSW-SLFFLAALSA-N 5-chloro-n-[(2s)-1-[(3r,4s)-3,4-dihydroxypyrrolidin-1-yl]-1-oxo-3-phenylpropan-2-yl]-1h-indole-2-carboxamide Chemical compound C1[C@@H](O)[C@@H](O)CN1C(=O)[C@@H](NC(=O)C=1NC2=CC=C(Cl)C=C2C=1)CC1=CC=CC=C1 FTMFRKISBMECSW-SLFFLAALSA-N 0.000 claims description 4
JPXQQFCADYJMMN-UHFFFAOYSA-N 5-chloro-n-[2-(1,1-dioxo-1,3-thiazolidin-3-yl)-2-oxoethyl]-1h-indole-2-carboxamide Chemical compound C=1C2=CC(Cl)=CC=C2NC=1C(=O)NCC(=O)N1CCS(=O)(=O)C1 JPXQQFCADYJMMN-UHFFFAOYSA-N 0.000 claims description 4
WAAVFJWSRFFSSW-BETUJISGSA-N 5-chloro-n-[2-[(3s,4r)-3,4-dihydroxypyrrolidin-1-yl]-2-oxoethyl]-1h-indole-2-carboxamide Chemical compound C1[C@@H](O)[C@@H](O)CN1C(=O)CNC(=O)C1=CC2=CC(Cl)=CC=C2N1 WAAVFJWSRFFSSW-BETUJISGSA-N 0.000 claims description 4
WSLKLYKPUZWAQW-UHFFFAOYSA-N 5-cyclopropyl-1-quinolin-5-ylpyrazole-4-carboxylic acid Chemical compound OC(=O)C=1C=NN(C=2C3=CC=CN=C3C=CC=2)C=1C1CC1 WSLKLYKPUZWAQW-UHFFFAOYSA-N 0.000 claims description 4
GOZINTPHLXUATQ-UHFFFAOYSA-N 5-cyclopropyl-1-quinolin-8-ylpyrazole-4-carboxylic acid Chemical compound OC(=O)C=1C=NN(C=2C3=NC=CC=C3C=CC=2)C=1C1CC1 GOZINTPHLXUATQ-UHFFFAOYSA-N 0.000 claims description 4
PTVBGVLITQPZTD-UHFFFAOYSA-N 5-cyclopropyl-n-(diaminomethylidene)-1-(2,6-dichlorophenyl)pyrazole-4-carboxamide Chemical compound NC(=N)NC(=O)C=1C=NN(C=2C(=CC=CC=2Cl)Cl)C=1C1CC1 PTVBGVLITQPZTD-UHFFFAOYSA-N 0.000 claims description 4
YZLNQKMWEXOAPY-UHFFFAOYSA-N 5-cyclopropyl-n-(diaminomethylidene)-1-phenylpyrazole-4-carboxamide Chemical compound NC(=N)NC(=O)C=1C=NN(C=2C=CC=CC=2)C=1C1CC1 YZLNQKMWEXOAPY-UHFFFAOYSA-N 0.000 claims description 4
XAMARBFYCUIBJA-UHFFFAOYSA-N 5-methyl-2-naphthalen-1-yltriazole-4-carboxylic acid Chemical compound N1=C(C(O)=O)C(C)=NN1C1=CC=CC2=CC=CC=C12 XAMARBFYCUIBJA-UHFFFAOYSA-N 0.000 claims description 4
ILKNSPWBNNHYMC-UHFFFAOYSA-N 5-methyl-2-quinolin-5-yltriazole-4-carboxylic acid Chemical group N1=C(C(O)=O)C(C)=NN1C1=CC=CC2=NC=CC=C12 ILKNSPWBNNHYMC-UHFFFAOYSA-N 0.000 claims description 4
BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 claims description 4
229940127291 Calcium channel antagonist Drugs 0.000 claims description 4
GJSURZIOUXUGAL-UHFFFAOYSA-N Clonidine Chemical compound ClC1=CC=CC(Cl)=C1NC1=NCCN1 GJSURZIOUXUGAL-UHFFFAOYSA-N 0.000 claims description 4
229960001138 acetylsalicylic acid Drugs 0.000 claims description 4
239000000480 calcium channel blocker Substances 0.000 claims description 4
150000001805 chlorine compounds Chemical class 0.000 claims description 4
229960002896 clonidine Drugs 0.000 claims description 4
IZEKFCXSFNUWAM-UHFFFAOYSA-N dipyridamole Chemical compound C=12N=C(N(CCO)CCO)N=C(N3CCCCC3)C2=NC(N(CCO)CCO)=NC=1N1CCCCC1 IZEKFCXSFNUWAM-UHFFFAOYSA-N 0.000 claims description 4
229960002768 dipyridamole Drugs 0.000 claims description 4
239000002934 diuretic Substances 0.000 claims description 4
229910052731 fluorine Inorganic materials 0.000 claims description 4
229930182470 glycoside Natural products 0.000 claims description 4
150000002338 glycosides Chemical class 0.000 claims description 4
150000002431 hydrogen Chemical class 0.000 claims description 4
229960002816 potassium chloride Drugs 0.000 claims description 4
IENZQIKPVFGBNW-UHFFFAOYSA-N prazosin Chemical compound N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(CC1)CCN1C(=O)C1=CC=CO1 IENZQIKPVFGBNW-UHFFFAOYSA-N 0.000 claims description 4
229960001289 prazosin Drugs 0.000 claims description 4
239000000296 purinergic P1 receptor antagonist Substances 0.000 claims description 4
230000002537 thrombolytic effect Effects 0.000 claims description 4
125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 3
125000006564 (C4-C8) cycloalkyl group Chemical group 0.000 claims description 3
LFXTUZDNFLZCNR-UHFFFAOYSA-N 5-cyclopropyl-n-(diaminomethylidene)-1-[2-(trifluoromethyl)phenyl]pyrazole-4-carboxamide Chemical compound NC(=N)NC(=O)C=1C=NN(C=2C(=CC=CC=2)C(F)(F)F)C=1C1CC1 LFXTUZDNFLZCNR-UHFFFAOYSA-N 0.000 claims description 3
GDXBRVCQGGKXJY-UHFFFAOYSA-N 5-cyclopropyl-n-(diaminomethylidene)-1-quinolin-5-ylpyrazole-4-carboxamide Chemical compound NC(N)=NC(=O)C=1C=NN(C=2C3=CC=CN=C3C=CC=2)C=1C1CC1 GDXBRVCQGGKXJY-UHFFFAOYSA-N 0.000 claims description 3
LFOAPSAWYUILCY-UHFFFAOYSA-N 5-cyclopropyl-n-(diaminomethylidene)-1-quinolin-8-ylpyrazole-4-carboxamide Chemical compound NC(=N)NC(=O)C=1C=NN(C=2C3=NC=CC=C3C=CC=2)C=1C1CC1 LFOAPSAWYUILCY-UHFFFAOYSA-N 0.000 claims description 3
HDPFDIUJHFATNN-UHFFFAOYSA-N 5-methyl-1-naphthalen-1-ylpyrazole-4-carboxylic acid Chemical compound CC1=C(C(O)=O)C=NN1C1=CC=CC2=CC=CC=C12 HDPFDIUJHFATNN-UHFFFAOYSA-N 0.000 claims description 3
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
239000002593 adenosine A3 receptor agonist Substances 0.000 claims description 3
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
239000011737 fluorine Substances 0.000 claims description 3
230000002440 hepatic effect Effects 0.000 claims description 3
125000004537 indazol-5-yl group Chemical group N1N=CC2=CC(=CC=C12)* 0.000 claims description 3
230000000968 intestinal effect Effects 0.000 claims description 3
230000002685 pulmonary effect Effects 0.000 claims description 3
230000002207 retinal effect Effects 0.000 claims description 3
210000001032 spinal nerve Anatomy 0.000 claims description 3
230000003393 splenic effect Effects 0.000 claims description 3
230000002792 vascular Effects 0.000 claims description 3
HGOICVLVWODJMV-UHFFFAOYSA-N 1-(2,1,3-benzothiadiazol-4-yl)-n-(diaminomethylidene)-3-methylpyrazole-4-carboxamide Chemical compound C1=C(C(=O)NC(N)=N)C(C)=NN1C1=CC=CC2=NSN=C12 HGOICVLVWODJMV-UHFFFAOYSA-N 0.000 claims description 2
JVGJINYQXKIBDT-UHFFFAOYSA-N 1-(2-bromophenyl)-5-cyclopropyl-n-(diaminomethylidene)pyrazole-4-carboxamide Chemical compound NC(=N)NC(=O)C=1C=NN(C=2C(=CC=CC=2)Br)C=1C1CC1 JVGJINYQXKIBDT-UHFFFAOYSA-N 0.000 claims description 2
ZJQFENWMXOATQM-UHFFFAOYSA-N 1-(2-chloro-4-methylsulfonylphenyl)-5-cyclopropyl-n-(diaminomethylidene)pyrazole-4-carboxamide Chemical compound ClC1=CC(S(=O)(=O)C)=CC=C1N1C(C2CC2)=C(C(=O)NC(N)=N)C=N1 ZJQFENWMXOATQM-UHFFFAOYSA-N 0.000 claims description 2
DZXZXYVVTHIODU-UHFFFAOYSA-N 1-(2-chloro-5-methoxyphenyl)-5-cyclopropyl-n-(diaminomethylidene)pyrazole-4-carboxamide Chemical compound COC1=CC=C(Cl)C(N2C(=C(C(=O)NC(N)=N)C=N2)C2CC2)=C1 DZXZXYVVTHIODU-UHFFFAOYSA-N 0.000 claims description 2
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BINSRSZWKJTYQD-UHFFFAOYSA-N 1-(2-chloro-5-sulfamoylphenyl)-5-cyclopropyl-n-(diaminomethylidene)pyrazole-4-carboxamide Chemical compound NC(=N)NC(=O)C=1C=NN(C=2C(=CC=C(C=2)S(N)(=O)=O)Cl)C=1C1CC1 BINSRSZWKJTYQD-UHFFFAOYSA-N 0.000 claims description 2
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210000002307 prostate Anatomy 0.000 description 1
125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
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HSSLDCABUXLXKM-UHFFFAOYSA-N resorufin Chemical compound C1=CC(=O)C=C2OC3=CC(O)=CC=C3N=C21 HSSLDCABUXLXKM-UHFFFAOYSA-N 0.000 description 1
230000002441 reversible effect Effects 0.000 description 1
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125000006413 ring segment Chemical group 0.000 description 1
CDAISMWEOUEBRE-UHFFFAOYSA-N scyllo-inosotol Natural products OC1C(O)C(O)C(O)C(O)C1O CDAISMWEOUEBRE-UHFFFAOYSA-N 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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150000003335 secondary amines Chemical class 0.000 description 1
239000012679 serum free medium Substances 0.000 description 1
230000035939 shock Effects 0.000 description 1
210000000329 smooth muscle myocyte Anatomy 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000012453 solvate Substances 0.000 description 1
229960002370 sotalol Drugs 0.000 description 1
ZBMZVLHSJCTVON-UHFFFAOYSA-N sotalol Chemical compound CC(C)NCC(O)C1=CC=C(NS(C)(=O)=O)C=C1 ZBMZVLHSJCTVON-UHFFFAOYSA-N 0.000 description 1
ZVGYIXBHESYHCE-UHFFFAOYSA-N spiro[6H-quinoline-5,4'-imidazolidine] Chemical compound N1=CC=CC2=C1C=CCC21NCNC1 ZVGYIXBHESYHCE-UHFFFAOYSA-N 0.000 description 1
238000013222 sprague-dawley male rat Methods 0.000 description 1
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239000010935 stainless steel Substances 0.000 description 1
238000012289 standard assay Methods 0.000 description 1
229960005322 streptomycin Drugs 0.000 description 1
229960001052 streptozocin Drugs 0.000 description 1
ZSJLQEPLLKMAKR-GKHCUFPYSA-N streptozocin Chemical compound O=NN(C)C(=O)N[C@H]1[C@@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O ZSJLQEPLLKMAKR-GKHCUFPYSA-N 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
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230000035488 systolic blood pressure Effects 0.000 description 1
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 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000005329 tetralinyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
238000009210 therapy by ultrasound Methods 0.000 description 1
125000003777 thiepinyl group Chemical group 0.000 description 1
125000004568 thiomorpholinyl group Chemical group 0.000 description 1
230000036962 time dependent Effects 0.000 description 1
XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
LUBHDINQXIHVLS-UHFFFAOYSA-N tolrestat Chemical compound OC(=O)CN(C)C(=S)C1=CC=CC2=C(C(F)(F)F)C(OC)=CC=C21 LUBHDINQXIHVLS-UHFFFAOYSA-N 0.000 description 1
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JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
229910052722 tritium Inorganic materials 0.000 description 1
229960000281 trometamol Drugs 0.000 description 1
210000003462 vein Anatomy 0.000 description 1
230000002861 ventricular Effects 0.000 description 1
SXONDGSPUVNZLO-UHFFFAOYSA-N zenarestat Chemical compound O=C1N(CC(=O)O)C2=CC(Cl)=CC=C2C(=O)N1CC1=CC=C(Br)C=C1F SXONDGSPUVNZLO-UHFFFAOYSA-N 0.000 description 1
229950006343 zenarestat Drugs 0.000 description 1
229950005346 zopolrestat Drugs 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/428—Thiazoles condensed with carbocyclic rings
- A—HUMAN NECESSITIES
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- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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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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- A61P9/12—Antihypertensives
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
- C07D249/06—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles with aryl radicals directly attached to ring atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- 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
- C07D401/04—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 directly linked by a ring-member-to-ring-member bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Epidemiology (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Urology & Nephrology (AREA)
Diabetes (AREA)
Vascular Medicine (AREA)
Biomedical Technology (AREA)
Endocrinology (AREA)
Hematology (AREA)
Obesity (AREA)
Emergency Medicine (AREA)
Physical Education & Sports Medicine (AREA)
Surgery (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Plural Heterocyclic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Steroid Compounds (AREA)

BG104803A 1998-02-27 2000-09-27 N-/(заместени петчленни ди- или триаза - диненаситени пръстенни) карбонил / гуанидинови производни за лечение на исхемия BG104803A (bg)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US7636298P	1998-02-27	1998-02-27
PCT/IB1999/000206 WO1999043663A1 (en)	1998-02-27	1999-02-05	N-[(substituted five-membered di- or triaza diunsaturated ring)carbonyl] guanidine derivatives for the treatment of ischemia

Publications (1)

Publication Number	Publication Date
BG104803A true BG104803A (bg)	2001-05-31

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ID=22131525

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BG104803A BG104803A (bg)	1998-02-27	2000-09-27	N-/(заместени петчленни ди- или триаза - диненаситени пръстенни) карбонил / гуанидинови производни за лечение на исхемия

Country Status (39)

Country	Link
US (2)	US6492401B1 (es)
EP (2)	EP1454902A1 (es)
JP (2)	JP2002504546A (es)
KR (4)	KR100407903B1 (es)
CN (1)	CN1289326A (es)
AP (1)	AP9901478A0 (es)
AR (1)	AR015526A1 (es)
AT (1)	ATE286034T1 (es)
AU (1)	AU739403B2 (es)
BG (1)	BG104803A (es)
BR (1)	BR9908332A (es)
CA (1)	CA2321642A1 (es)
CO (1)	CO4980897A1 (es)
DE (1)	DE69922930T2 (es)
DK (1)	DK1056729T3 (es)
DZ (1)	DZ2729A1 (es)
EA (1)	EA003603B1 (es)
ES (1)	ES2237080T3 (es)
GT (1)	GT199900022A (es)
HR (2)	HRP20000550A2 (es)
HU (1)	HUP0204418A3 (es)
ID (1)	ID25505A (es)
IL (1)	IL136588A0 (es)
IS (1)	IS5548A (es)
NO (1)	NO20004192D0 (es)
NZ (1)	NZ504769A (es)
OA (1)	OA11450A (es)
PA (1)	PA8468401A1 (es)
PE (1)	PE20000334A1 (es)
PL (1)	PL342444A1 (es)
PT (1)	PT1056729E (es)
SI (1)	SI1056729T1 (es)
SK (1)	SK12342000A3 (es)
TN (1)	TNSN99028A1 (es)
TR (1)	TR200002480T2 (es)
TW (1)	TWI226329B (es)
WO (1)	WO1999043663A1 (es)
YU (1)	YU46200A (es)
ZA (1)	ZA991578B (es)

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FR2795726A1 (fr) *	1999-06-30	2001-01-05	Aventis Cropscience Sa	Nouveaux pyrazoles fongicides
UA72002C2 (en) *	1999-10-29	2005-01-17	Pfizer Prod Inc	Inhibitors crystals of sodium-hydrogen exchange of 1 type, a method for the preparation thereof (variants), a pharmaceuticalcomposition based thereon and a method for the reduction of tissue damage
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YU54202A (sh)	2000-01-18	2006-01-16	Agouron Pharmaceuticals Inc.	Jedinjenja indazola, farmaceutske smeše i postupci za stimulisanje i inhibiranje ćelijske proliferacije
HN2001000008A (es)	2000-01-21	2003-12-11	Inc Agouron Pharmaceuticals	Compuesto de amida y composiciones farmaceuticas para inhibir proteinquinasas, y su modo de empleo
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US6555569B2 (en) *	2000-03-07	2003-04-29	Pfizer Inc.	Use of heteroaryl substituted N-(indole-2-carbonyl-) amides for treatment of infection
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CA2398446A1 (en)	2000-04-18	2001-10-25	Agouron Pharmaceuticals, Inc.	Pyrazoles for inhibiting protein kinases
OA12256A (en) *	2000-04-28	2003-11-06	Pfizer Prod Inc	Sodium-hydrogen exchanger type 1 inhibitor (NHE-1).
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IL144507A0 (en) *	2000-07-31	2002-05-23	Pfizer Prod Inc	Use of glycogen phosphorylase inhibitors to inhibit tumor growth
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YU51903A (sh) *	2001-01-31	2006-05-25	Pfizer Products Inc.	Enolati inhibitora izmene natrijum-vodonik tipa-1
WO2002098429A1 (en) *	2001-06-07	2002-12-12	Pfizer Products Inc.	Ethanolamine, diethanolamine or triethanolamine salt of zopolrestat
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1999
- 1999-02-05 KR KR10-2002-7017553A patent/KR100407903B1/ko not_active Expired - Fee Related
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- 1999-02-05 PL PL99342444A patent/PL342444A1/xx not_active Application Discontinuation
- 1999-02-05 ES ES99901083T patent/ES2237080T3/es not_active Expired - Lifetime
- 1999-02-05 CA CA002321642A patent/CA2321642A1/en not_active Abandoned
- 1999-02-05 AU AU20706/99A patent/AU739403B2/en not_active Ceased
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- 1999-02-05 EP EP04008203A patent/EP1454902A1/en not_active Withdrawn
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- 1999-02-05 CN CN99802628A patent/CN1289326A/zh active Pending
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- 1999-02-23 PE PE1999000156A patent/PE20000334A1/es not_active Application Discontinuation
- 1999-02-24 TN TNTNSN99028A patent/TNSN99028A1/fr unknown
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2000
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- 2000-08-22 NO NO20004192A patent/NO20004192D0/no not_active Application Discontinuation
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2002
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2004
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Also Published As

Publication number	Publication date
EP1056729A1 (en)	2000-12-06
ID25505A (id)	2000-10-05
AU2070699A (en)	1999-09-15
CO4980897A1 (es)	2000-11-27
KR20030078886A (ko)	2003-10-08
JP2002504546A (ja)	2002-02-12
WO1999043663A1 (en)	1999-09-02
NZ504769A (en)	2005-04-29
PL342444A1 (en)	2001-06-04
IL136588A0 (en)	2001-06-14
DK1056729T3 (da)	2005-04-11
AU739403B2 (en)	2001-10-11
IS5548A (is)	2000-06-27
KR100407903B1 (ko)	2003-12-01
KR100449600B1 (ko)	2004-09-21
EP1056729B1 (en)	2004-12-29
ZA991578B (en)	2000-08-28
JP2005041879A (ja)	2005-02-17
BR9908332A (pt)	2000-11-07
HUP0204418A2 (hu)	2003-04-28
AR015526A1 (es)	2001-05-02
HRP20010666A2 (en)	2001-10-31
NO20004192L (no)	2000-08-22
SI1056729T1 (en)	2005-04-30
DE69922930T2 (de)	2005-12-29
KR20030083004A (ko)	2003-10-23
KR20030009548A (ko)	2003-01-29
DE69922930D1 (de)	2005-02-03
AP9901478A0 (en)	1999-03-31
PE20000334A1 (es)	2000-05-13
US6974813B2 (en)	2005-12-13
CA2321642A1 (en)	1999-09-02
KR20010041397A (ko)	2001-05-15
TWI226329B (en)	2005-01-11
CN1289326A (zh)	2001-03-28
EP1454902A1 (en)	2004-09-08
GT199900022A (es)	2000-08-15
US6492401B1 (en)	2002-12-10
HRP20000550A2 (en)	2001-02-28
HUP0204418A3 (en)	2003-10-28
SK12342000A3 (sk)	2001-03-12
ES2237080T3 (es)	2005-07-16
YU46200A (sh)	2003-02-28
TNSN99028A1 (fr)	2005-11-10
EA003603B1 (ru)	2003-06-26
PT1056729E (pt)	2005-04-29
PA8468401A1 (es)	2000-09-29
US20030149043A1 (en)	2003-08-07
ATE286034T1 (de)	2005-01-15
NO20004192D0 (no)	2000-08-22
TR200002480T2 (tr)	2000-12-21
OA11450A (en)	2003-12-04
EA200000789A1 (ru)	2001-02-26
DZ2729A1 (fr)	2005-03-01

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