ZA200103498B - Imidazo[4,5-C-]-pyridine-4-one derivative with factor Xa inhibiting effect. - Google Patents
Imidazo[4,5-C-]-pyridine-4-one derivative with factor Xa inhibiting effect. Download PDFInfo
- Publication number
- ZA200103498B ZA200103498B ZA200103498A ZA200103498A ZA200103498B ZA 200103498 B ZA200103498 B ZA 200103498B ZA 200103498 A ZA200103498 A ZA 200103498A ZA 200103498 A ZA200103498 A ZA 200103498A ZA 200103498 B ZA200103498 B ZA 200103498B
- Authority
- ZA
- South Africa
- Prior art keywords
- formula
- compounds
- physiologically acceptable
- substance
- composition
- Prior art date
Links
- 108010074860 Factor Xa Proteins 0.000 title claims description 14
- 230000002401 inhibitory effect Effects 0.000 title description 3
- -1 7-amidinonaphth-2- ylmethyl Chemical group 0.000 claims description 59
- 150000001875 compounds Chemical class 0.000 claims description 35
- 238000000034 method Methods 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 20
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 18
- 208000007536 Thrombosis Diseases 0.000 claims description 9
- 235000010290 biphenyl Nutrition 0.000 claims description 9
- 239000004305 biphenyl Substances 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000001624 naphthyl group Chemical group 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000006239 protecting group Chemical group 0.000 claims description 6
- 206010002383 Angina Pectoris Diseases 0.000 claims description 5
- 206010003210 Arteriosclerosis Diseases 0.000 claims description 5
- 206010008190 Cerebrovascular accident Diseases 0.000 claims description 5
- 206010061218 Inflammation Diseases 0.000 claims description 5
- 206010022562 Intermittent claudication Diseases 0.000 claims description 5
- 208000006011 Stroke Diseases 0.000 claims description 5
- 238000002399 angioplasty Methods 0.000 claims description 5
- 208000011775 arteriosclerosis disease Diseases 0.000 claims description 5
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 230000004054 inflammatory process Effects 0.000 claims description 5
- 208000021156 intermittent vascular claudication Diseases 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 208000010125 myocardial infarction Diseases 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 208000037803 restenosis Diseases 0.000 claims description 5
- 125000003277 amino group Chemical group 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical class O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 2
- 125000004185 ester group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 238000007327 hydrogenolysis reaction Methods 0.000 claims description 2
- 230000003301 hydrolyzing effect Effects 0.000 claims description 2
- 239000003112 inhibitor Substances 0.000 claims description 2
- 150000004866 oxadiazoles Chemical class 0.000 claims description 2
- 238000003797 solvolysis reaction Methods 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims 8
- 239000000126 substance Substances 0.000 claims 8
- 239000000825 pharmaceutical preparation Substances 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- 239000007788 liquid Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 230000005764 inhibitory process Effects 0.000 description 12
- 108090000190 Thrombin Proteins 0.000 description 9
- 229960004072 thrombin Drugs 0.000 description 9
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 6
- 108010054265 Factor VIIa Proteins 0.000 description 5
- 230000002785 anti-thrombosis Effects 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 108010048049 Factor IXa Proteins 0.000 description 4
- 230000002429 anti-coagulating effect Effects 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 208000035475 disorder Diseases 0.000 description 4
- 229940012414 factor viia Drugs 0.000 description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 230000009424 thromboembolic effect Effects 0.000 description 4
- 206010053567 Coagulopathies Diseases 0.000 description 3
- 230000004913 activation Effects 0.000 description 3
- 230000023555 blood coagulation Effects 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 230000035602 clotting Effects 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000000338 in vitro Methods 0.000 description 3
- 238000001727 in vivo Methods 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 2
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 2
- GCNTZFIIOFTKIY-UHFFFAOYSA-N 4-hydroxypyridine Chemical compound OC1=CC=NC=C1 GCNTZFIIOFTKIY-UHFFFAOYSA-N 0.000 description 2
- 108010039209 Blood Coagulation Factors Proteins 0.000 description 2
- 102000015081 Blood Coagulation Factors Human genes 0.000 description 2
- 108010014173 Factor X Proteins 0.000 description 2
- 102000009123 Fibrin Human genes 0.000 description 2
- 108010073385 Fibrin Proteins 0.000 description 2
- BWGVNKXGVNDBDI-UHFFFAOYSA-N Fibrin monomer Chemical compound CNC(=O)CNC(=O)CN BWGVNKXGVNDBDI-UHFFFAOYSA-N 0.000 description 2
- 108091005804 Peptidases Proteins 0.000 description 2
- 239000004365 Protease Substances 0.000 description 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 2
- 239000003114 blood coagulation factor Substances 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 229950003499 fibrin Drugs 0.000 description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 125000005919 1,2,2-trimethylpropyl group Chemical group 0.000 description 1
- 125000006218 1-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006219 1-ethylpentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005808 2,4,6-trimethoxyphenyl group Chemical group [H][#6]-1=[#6](-[#8]C([H])([H])[H])-[#6](-*)=[#6](-[#8]C([H])([H])[H])-[#6]([H])=[#6]-1-[#8]C([H])([H])[H] 0.000 description 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 description 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- 125000005916 2-methylpentyl group Chemical group 0.000 description 1
- 125000004362 3,4,5-trichlorophenyl group Chemical group [H]C1=C(Cl)C(Cl)=C(Cl)C([H])=C1* 0.000 description 1
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 1
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 description 1
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 description 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
- 125000005917 3-methylpentyl group Chemical group 0.000 description 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 1
- 125000006306 4-iodophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1I 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229940123583 Factor Xa inhibitor Drugs 0.000 description 1
- 108010049003 Fibrinogen Proteins 0.000 description 1
- 102000008946 Fibrinogen Human genes 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- RAXXELZNTBOGNW-UHFFFAOYSA-O Imidazolium Chemical compound C1=C[NH+]=CN1 RAXXELZNTBOGNW-UHFFFAOYSA-O 0.000 description 1
- 102000035195 Peptidases Human genes 0.000 description 1
- 108010094028 Prothrombin Proteins 0.000 description 1
- 102100027378 Prothrombin Human genes 0.000 description 1
- 102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 description 1
- 108010022999 Serine Proteases Proteins 0.000 description 1
- 102000012479 Serine Proteases Human genes 0.000 description 1
- 108010000499 Thromboplastin Proteins 0.000 description 1
- 102000002262 Thromboplastin Human genes 0.000 description 1
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 1
- 239000003146 anticoagulant agent Substances 0.000 description 1
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- HUXULLJDEXUMOP-UHFFFAOYSA-N carbamimidoyl fluoride Chemical compound NC(F)=N HUXULLJDEXUMOP-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229940012952 fibrinogen Drugs 0.000 description 1
- 239000011737 fluorine Substances 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
- 150000004677 hydrates Chemical class 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- UHNHTTIUNATJKL-UHFFFAOYSA-N n-methylmethanesulfonamide Chemical group CNS(C)(=O)=O UHNHTTIUNATJKL-UHFFFAOYSA-N 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000003884 phenylalkyl group Chemical group 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
- 229940039716 prothrombin Drugs 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003607 serino group Chemical class [H]N([H])[C@]([H])(C(=O)[*])C(O[H])([H])[H] 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 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
- C07D471/02—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
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19845153A DE19845153A1 (de) | 1998-10-01 | 1998-10-01 | Imidazo[4,5]-pyridin-4-on-derivate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200103498B true ZA200103498B (en) | 2002-08-13 |
Family
ID=7883005
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200103498A ZA200103498B (en) | 1998-10-01 | 2001-04-30 | Imidazo[4,5-C-]-pyridine-4-one derivative with factor Xa inhibiting effect. |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US6492384B1 (fr) |
| EP (1) | EP1117664A1 (fr) |
| JP (1) | JP2002526542A (fr) |
| KR (1) | KR20010074980A (fr) |
| CN (1) | CN1324358A (fr) |
| AR (1) | AR020688A1 (fr) |
| AU (1) | AU752574B2 (fr) |
| BR (1) | BR9914213A (fr) |
| CA (1) | CA2346033A1 (fr) |
| DE (1) | DE19845153A1 (fr) |
| HU (1) | HUP0104164A3 (fr) |
| ID (1) | ID29466A (fr) |
| MY (1) | MY130736A (fr) |
| NO (1) | NO20011638L (fr) |
| PL (1) | PL346542A1 (fr) |
| SK (1) | SK4282001A3 (fr) |
| WO (1) | WO2000020416A1 (fr) |
| ZA (1) | ZA200103498B (fr) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6858616B2 (en) | 1998-12-23 | 2005-02-22 | Bristol-Myers Squibb Pharma Company | Nitrogen containing heterobicycles as factor Xa inhibitors |
| ATE280171T1 (de) | 1998-12-23 | 2004-11-15 | Bristol Myers Squibb Pharma Co | Stickstoffhaltige heterobicyclen als faktor-xa- hemmer |
| JP2004501918A (ja) * | 2000-06-23 | 2004-01-22 | ブリストル−マイヤーズ スクイブ ファーマ カンパニー | Ｘａ因子阻害剤としての１−（ヘテロアリール−フェニル）−縮合ピラゾール誘導体 |
| EP1414449A4 (fr) | 2001-05-22 | 2005-04-06 | Bristol Myers Squibb Co | Inhibiteurs bicycliques du facteur xa |
| EP1472254A4 (fr) * | 2002-02-08 | 2006-02-15 | Glsynthesis Inc | Purine et composes antibacteriens isosteres |
| GB0215293D0 (en) | 2002-07-03 | 2002-08-14 | Rega Foundation | Viral inhibitors |
| PT1569912E (pt) | 2002-12-03 | 2015-09-15 | Pharmacyclics Llc | Derivados 2-(2-hidroxibifenil-3-il)-1h-benzoimidazole-5- carboxamidina como inibidores do fator viia |
| US7135469B2 (en) * | 2003-03-18 | 2006-11-14 | Bristol Myers Squibb, Co. | Linear chain substituted monocyclic and bicyclic derivatives as factor Xa inhibitors |
| AU2004309390B2 (en) * | 2003-12-22 | 2011-06-02 | Gilead Sciences, Inc. | Imidazo[4,5-c]pyridine compounds and methods of antiviral treatment |
| US7381732B2 (en) | 2004-10-26 | 2008-06-03 | Bristol-Myers Squibb Company | Pyrazolobenzamides and derivatives as factor Xa inhibitors |
| JP2008524335A (ja) * | 2004-12-21 | 2008-07-10 | ギリアド サイエンシズ， インコーポレイテッド | イミダゾ［４，５−ｃ］ピリジン化合物および抗ウイルス処置法 |
| EP1942898B2 (fr) | 2005-09-14 | 2014-05-14 | Takeda Pharmaceutical Company Limited | Inhibiteurs de la dipeptidyl peptidase permettant de traiter le diabete |
| JP5122462B2 (ja) | 2005-09-16 | 2013-01-16 | 武田薬品工業株式会社 | ジペプチジルペプチダーゼ阻害剤 |
| TW200734338A (en) * | 2006-01-16 | 2007-09-16 | Organon Nv | 6-Phenyl-1H-imidazo [4,5-c] pyridine-4-carbonitrile derivatives |
| WO2007112347A1 (fr) | 2006-03-28 | 2007-10-04 | Takeda Pharmaceutical Company Limited | Inhibiteurs de la dipeptidyl peptidase |
| ES2339298T3 (es) * | 2006-07-07 | 2010-05-18 | Gilead Sciences, Inc. | Compuesto de piridazina novedoso y uso del mismo. |
| TW200838536A (en) | 2006-11-29 | 2008-10-01 | Takeda Pharmaceutical | Polymorphs of succinate salt of 2-[6-(3-amino-piperidin-1-yl)-3-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-ylmethy]-4-fluor-benzonitrile and methods of use therefor |
| UA99466C2 (en) | 2007-07-06 | 2012-08-27 | Гилиад Сайенсиз, Инк. | Crystalline pyridazine compound |
| WO2011031935A1 (fr) | 2009-09-11 | 2011-03-17 | Glsynthesis Inc. | Anti-bactériens sélectifs pour des infections par clostridium difficile |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE574846C (de) * | 1933-04-21 | Wilhelm Germann | Schienenbefestigung unter Verwendung von Schienenfuehrungsleisten | |
| DE602521C (de) * | 1934-09-10 | Wilhelm Stoeckicht Dipl Ing | Umlaufraederwechselgetriebe, insbesondere fuer Kraftfahrzeuge | |
| DE546449C (de) * | 1932-03-12 | Mueller Paul | Verbindung von Belagblechen | |
| DE595151C (de) * | 1934-04-04 | Buderus Eisenwerk | Verfahren und Vorrichtung zum Regeln des Gewichts von in Schleudergussmaschinen herzustellenden Rohren | |
| DE505893C (de) * | 1926-08-07 | 1930-08-26 | Medizinische Produkte Ag F | Verfahren zur Herstellung von Eiweiss-Halogen-Schwefelverbindungen |
| DE564960C (de) * | 1931-05-13 | 1932-11-24 | Siemens Schuckertwerke Akt Ges | Einrichtung zur Anpassung der Drehzahlregelung, insbesondere von Dampfturbinen, an veraenderte Betriebsverhaeltnisse |
| DE628556C (de) * | 1932-12-07 | 1936-04-08 | Wolf Johannes Mueller Dr | Verfahren zur Herstellung von insbesondere hochkonzentrierten Wasserglasloesungen |
| DE702013C (de) * | 1933-07-17 | 1941-01-29 | Union Oil Co | Verfahren zur Abscheidung von Paraffin aus paraffinhaltigen OElen |
| US5798364A (en) * | 1992-03-26 | 1998-08-25 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Imidazopyridines |
| DE4110019C2 (de) | 1991-03-27 | 2000-04-13 | Merck Patent Gmbh | Imidazopyridine, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Zubereitungen |
| DE4140519A1 (de) * | 1991-12-09 | 1993-06-17 | Merck Patent Gmbh | Benzofurane |
| DE4211474A1 (de) | 1992-04-06 | 1993-10-07 | Merck Patent Gmbh | Imidazopyridine |
| DE4305602A1 (de) * | 1992-06-17 | 1993-12-23 | Merck Patent Gmbh | Imidazopyridine |
| DE4236026A1 (de) * | 1992-10-24 | 1994-04-28 | Merck Patent Gmbh | Imidazopyridine |
| DE4242459A1 (de) * | 1992-12-16 | 1994-06-23 | Merck Patent Gmbh | Imidazopyridine |
| DE4318813A1 (de) * | 1993-06-07 | 1994-12-08 | Merck Patent Gmbh | Imidazopyridine |
| DE4432860A1 (de) | 1994-09-15 | 1996-03-21 | Merck Patent Gmbh | Imidazopyridine |
| NZ333696A (en) | 1996-07-08 | 2000-06-23 | Du Pont Pharm Co | Amidinoindoles, amidinoazoles, and analogs thereof as inhibitors of trypsin like protease enzymes like thrombin and Xa factor |
-
1998
- 1998-10-01 DE DE19845153A patent/DE19845153A1/de not_active Withdrawn
-
1999
- 1999-09-09 EP EP99946151A patent/EP1117664A1/fr not_active Withdrawn
- 1999-09-09 US US09/806,418 patent/US6492384B1/en not_active Expired - Fee Related
- 1999-09-09 AU AU58618/99A patent/AU752574B2/en not_active Ceased
- 1999-09-09 KR KR1020017002922A patent/KR20010074980A/ko not_active Application Discontinuation
- 1999-09-09 ID IDW20010909A patent/ID29466A/id unknown
- 1999-09-09 WO PCT/EP1999/006655 patent/WO2000020416A1/fr not_active Application Discontinuation
- 1999-09-09 PL PL99346542A patent/PL346542A1/xx unknown
- 1999-09-09 BR BR9914213-9A patent/BR9914213A/pt not_active IP Right Cessation
- 1999-09-09 CN CN99811601A patent/CN1324358A/zh active Pending
- 1999-09-09 SK SK428-2001A patent/SK4282001A3/sk unknown
- 1999-09-09 CA CA002346033A patent/CA2346033A1/fr not_active Abandoned
- 1999-09-09 HU HU0104164A patent/HUP0104164A3/hu unknown
- 1999-09-09 JP JP2000574528A patent/JP2002526542A/ja active Pending
- 1999-09-28 MY MYPI99004187A patent/MY130736A/en unknown
- 1999-10-01 AR ARP990104991A patent/AR020688A1/es not_active Application Discontinuation
-
2001
- 2001-03-30 NO NO20011638A patent/NO20011638L/no not_active Application Discontinuation
- 2001-04-30 ZA ZA200103498A patent/ZA200103498B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AR020688A1 (es) | 2002-05-22 |
| KR20010074980A (ko) | 2001-08-09 |
| EP1117664A1 (fr) | 2001-07-25 |
| HUP0104164A2 (hu) | 2002-04-29 |
| NO20011638D0 (no) | 2001-03-30 |
| NO20011638L (no) | 2001-03-30 |
| DE19845153A1 (de) | 2000-04-06 |
| MY130736A (en) | 2007-07-31 |
| CN1324358A (zh) | 2001-11-28 |
| WO2000020416A1 (fr) | 2000-04-13 |
| AU5861899A (en) | 2000-04-26 |
| PL346542A1 (en) | 2002-02-11 |
| SK4282001A3 (en) | 2002-10-08 |
| HUP0104164A3 (en) | 2002-08-28 |
| US6492384B1 (en) | 2002-12-10 |
| CA2346033A1 (fr) | 2000-04-13 |
| BR9914213A (pt) | 2001-06-26 |
| JP2002526542A (ja) | 2002-08-20 |
| ID29466A (id) | 2001-08-30 |
| AU752574B2 (en) | 2002-09-26 |
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