ZA200203278B - Benzamidine derivatives. - Google Patents
Benzamidine derivatives. Download PDFInfo
- Publication number
- ZA200203278B ZA200203278B ZA200203278A ZA200203278A ZA200203278B ZA 200203278 B ZA200203278 B ZA 200203278B ZA 200203278 A ZA200203278 A ZA 200203278A ZA 200203278 A ZA200203278 A ZA 200203278A ZA 200203278 B ZA200203278 B ZA 200203278B
- Authority
- ZA
- South Africa
- Prior art keywords
- group
- pharmaceutically acceptable
- acceptable salt
- benzamidine derivative
- hydrogen atom
- Prior art date
Links
- 150000003937 benzamidines Chemical class 0.000 title claims description 45
- -1 1-acetimidoylpyrrolidin-3-yl group Chemical group 0.000 claims description 277
- 125000000217 alkyl group Chemical group 0.000 claims description 44
- 150000003839 salts Chemical class 0.000 claims description 36
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 29
- 125000003545 alkoxy group Chemical group 0.000 claims description 26
- 229910052799 carbon Inorganic materials 0.000 claims description 25
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 21
- 238000011282 treatment Methods 0.000 claims description 21
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 19
- 229910052731 fluorine Inorganic materials 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 19
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
- 230000002265 prevention Effects 0.000 claims description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
- 229910052801 chlorine Inorganic materials 0.000 claims description 15
- 125000001153 fluoro group Chemical group F* 0.000 claims description 15
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 12
- 208000015294 blood coagulation disease Diseases 0.000 claims description 10
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 9
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 125000002252 acyl group Chemical group 0.000 claims description 7
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 7
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 6
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 5
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 5
- 125000000350 glycoloyl group Chemical group O=C([*])C([H])([H])O[H] 0.000 claims description 5
- 208000007536 Thrombosis Diseases 0.000 claims description 4
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 206010008118 cerebral infarction Diseases 0.000 claims description 3
- 208000026106 cerebrovascular disease Diseases 0.000 claims description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 3
- 208000010125 myocardial infarction Diseases 0.000 claims description 3
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims 18
- 239000000126 substance Substances 0.000 claims 17
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 5
- BVPDYEMZSMSMSB-UHFFFAOYSA-N sulfamoyl acetate Chemical compound CC(=O)OS(N)(=O)=O BVPDYEMZSMSMSB-UHFFFAOYSA-N 0.000 claims 4
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 2
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims 2
- 230000003836 peripheral circulation Effects 0.000 claims 2
- 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 claims 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims 1
- 239000003146 anticoagulant agent Substances 0.000 description 6
- 108010074860 Factor Xa Proteins 0.000 description 5
- 229940127219 anticoagulant drug Drugs 0.000 description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 229940123583 Factor Xa inhibitor Drugs 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 238000002560 therapeutic procedure Methods 0.000 description 3
- PJVWKTKQMONHTI-UHFFFAOYSA-N warfarin Chemical compound OC=1C2=CC=CC=C2OC(=O)C=1C(CC(=O)C)C1=CC=CC=C1 PJVWKTKQMONHTI-UHFFFAOYSA-N 0.000 description 3
- 229960005080 warfarin Drugs 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 2
- 108090000190 Thrombin Proteins 0.000 description 2
- 229940122388 Thrombin inhibitor Drugs 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 230000023555 blood coagulation Effects 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 230000015271 coagulation Effects 0.000 description 2
- 238000005345 coagulation Methods 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 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 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 2
- 125000001148 pentyloxycarbonyl group Chemical group 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 229960004072 thrombin Drugs 0.000 description 2
- 239000003868 thrombin inhibitor Substances 0.000 description 2
- 125000005918 1,2-dimethylbutyl group Chemical group 0.000 description 1
- ILROLYQPRYHHFG-UHFFFAOYSA-N 1-$l^{1}-oxidanylprop-2-en-1-one Chemical group [O]C(=O)C=C ILROLYQPRYHHFG-UHFFFAOYSA-N 0.000 description 1
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 description 1
- YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 1
- 125000000143 2-carboxyethyl group Chemical group [H]OC(=O)C([H])([H])C([H])([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
- 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
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 1
- 125000005917 3-methylpentyl group Chemical group 0.000 description 1
- SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 101710081722 Antitrypsin Proteins 0.000 description 1
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241000761389 Copa Species 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108010074105 Factor Va Proteins 0.000 description 1
- 102000009123 Fibrin Human genes 0.000 description 1
- 108010073385 Fibrin Proteins 0.000 description 1
- 108010049003 Fibrinogen Proteins 0.000 description 1
- 102000008946 Fibrinogen Human genes 0.000 description 1
- 208000032843 Hemorrhage Diseases 0.000 description 1
- 208000030831 Peripheral arterial occlusive disease Diseases 0.000 description 1
- 108010094028 Prothrombin Proteins 0.000 description 1
- 102100027378 Prothrombin Human genes 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
- 229930003448 Vitamin K Natural products 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 230000001475 anti-trypsic effect Effects 0.000 description 1
- 229960004676 antithrombotic agent Drugs 0.000 description 1
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910001424 calcium ion Inorganic materials 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 229940088598 enzyme Drugs 0.000 description 1
- 230000006624 extrinsic pathway Effects 0.000 description 1
- 229940012952 fibrinogen Drugs 0.000 description 1
- 125000003104 hexanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005935 hexyloxycarbonyl group Chemical group 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000005929 isobutyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])OC(*)=O 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
- 125000005932 isopentyloxycarbonyl group Chemical group 0.000 description 1
- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
- 125000004998 naphthylethyl group Chemical group C1(=CC=CC2=CC=CC=C12)CC* 0.000 description 1
- 230000014508 negative regulation of coagulation Effects 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
- 230000037361 pathway Effects 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000004346 phenylpentyl group Chemical group C1(=CC=CC=C1)CCCCC* 0.000 description 1
- 125000004344 phenylpropyl group Chemical group 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- SHUZOJHMOBOZST-UHFFFAOYSA-N phylloquinone Natural products CC(C)CCCCC(C)CCC(C)CCCC(=CCC1=C(C)C(=O)c2ccccc2C1=O)C SHUZOJHMOBOZST-UHFFFAOYSA-N 0.000 description 1
- 238000010837 poor prognosis Methods 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
- 229940039716 prothrombin Drugs 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
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 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
- 230000001960 triggered effect Effects 0.000 description 1
- 239000002753 trypsin inhibitor Substances 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000019168 vitamin K Nutrition 0.000 description 1
- 239000011712 vitamin K Substances 0.000 description 1
- 150000003721 vitamin K derivatives Chemical class 0.000 description 1
- 229940046010 vitamin k Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
-
- 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)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Heart & Thoracic Surgery (AREA)
- Vascular Medicine (AREA)
- Cardiology (AREA)
- Urology & Nephrology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Manufacture Of Alloys Or Alloy Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP30719299 | 1999-10-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200203278B true ZA200203278B (en) | 2003-08-26 |
Family
ID=17966162
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200203278A ZA200203278B (en) | 1999-10-28 | 2002-04-24 | Benzamidine derivatives. |
Country Status (26)
| Country | Link |
|---|---|
| US (3) | US6555556B1 (hu) |
| EP (1) | EP1245564B1 (hu) |
| KR (1) | KR100642953B1 (hu) |
| CN (2) | CN1572882A (hu) |
| AT (1) | ATE322479T1 (hu) |
| AU (1) | AU776193B2 (hu) |
| BR (1) | BR0015120A (hu) |
| CA (1) | CA2389156C (hu) |
| CY (1) | CY1106116T1 (hu) |
| CZ (1) | CZ20021432A3 (hu) |
| DE (1) | DE60027204T2 (hu) |
| DK (1) | DK1245564T3 (hu) |
| ES (1) | ES2261248T3 (hu) |
| HK (1) | HK1047431B (hu) |
| HU (1) | HUP0203161A3 (hu) |
| IL (2) | IL149306A0 (hu) |
| MX (1) | MXPA02004218A (hu) |
| NO (1) | NO323147B1 (hu) |
| NZ (1) | NZ518581A (hu) |
| PL (1) | PL354619A1 (hu) |
| PT (1) | PT1245564E (hu) |
| RU (1) | RU2222529C2 (hu) |
| TR (1) | TR200201654T2 (hu) |
| TW (1) | TWI226886B (hu) |
| WO (1) | WO2001030756A1 (hu) |
| ZA (1) | ZA200203278B (hu) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2222529C2 (ru) * | 1999-10-28 | 2004-01-27 | Санкио Компани, Лимитед | Производные бензамидина |
| CN1610666A (zh) * | 2001-04-05 | 2005-04-27 | 三共株式会社 | 苄脒衍生物 |
| WO2002089803A1 (en) * | 2001-05-07 | 2002-11-14 | Sankyo Company, Limited | Composition for iontophoresis |
| WO2003078389A1 (fr) * | 2002-03-15 | 2003-09-25 | Kissei Pharmaceutical Co., Ltd. | Nouveaux cristaux de derive de 5-hydroxycarbamimidoyl-2-hydroxybenzenesulfonamide |
| ES2333739T3 (es) * | 2004-11-23 | 2010-02-26 | Dong Wha Pharmaceutical Co., Ltd. | Sal de n-hidroxi-4-(5-(4-(5-isopropil-2-metil-1,3-tiazol-4-il)fenoxi) pentoxi)benzamidina con acido 2-metanosulfonico. |
| CN103159620A (zh) * | 2013-03-28 | 2013-06-19 | 广西师范大学 | 一种2-羟基间苯二甲酸的制备方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA928276B (en) | 1991-10-31 | 1993-05-06 | Daiichi Seiyaku Co | Aromatic amidine derivates and salts thereof. |
| US5731324A (en) * | 1993-07-22 | 1998-03-24 | Eli Lilly And Company | Glycoprotein IIb/IIIa antagonists |
| ZA951617B (en) * | 1994-03-04 | 1997-02-27 | Lilly Co Eli | Antithrombotic agents. |
| AU688628B2 (en) | 1994-12-02 | 1998-03-12 | Yamanouchi Pharmaceutical Co., Ltd. | Novel amidinonaphthyl derivative or salt thereof |
| PT906094E (pt) * | 1996-01-02 | 2003-11-28 | Aventis Pharma Inc | Amidas substituidas n-¬(aminoiminometil ou aminometil) fenil|propilo |
| ES2188979T3 (es) * | 1996-09-12 | 2003-07-01 | Schering Ag | Derivados de benzamidina sustituidos con derivados de aminoacidos ciclicos e hidroxiacidos ciclicos, y su uso como anti-coagulantes. |
| TW542822B (en) * | 1997-01-17 | 2003-07-21 | Ajinomoto Kk | Benzamidine derivatives |
| JP2003522733A (ja) | 1999-02-11 | 2003-07-29 | コア セラピューティクス，インコーポレイティド | Ｘａ因子の阻害剤としてのアルケニルおよびアルキニル化合物 |
| US6350761B1 (en) * | 1999-07-30 | 2002-02-26 | Berlex Laboratories, Inc. | Benzenamine derivatives as anti-coagulants |
| RU2222529C2 (ru) * | 1999-10-28 | 2004-01-27 | Санкио Компани, Лимитед | Производные бензамидина |
-
2000
- 2000-10-25 RU RU2002111343/04A patent/RU2222529C2/ru not_active IP Right Cessation
- 2000-10-25 CZ CZ20021432A patent/CZ20021432A3/cs unknown
- 2000-10-25 PL PL00354619A patent/PL354619A1/xx unknown
- 2000-10-25 KR KR1020027005382A patent/KR100642953B1/ko not_active Expired - Fee Related
- 2000-10-25 CN CNA2004100634713A patent/CN1572882A/zh active Pending
- 2000-10-25 DE DE60027204T patent/DE60027204T2/de not_active Expired - Lifetime
- 2000-10-25 IL IL14930600A patent/IL149306A0/xx active IP Right Grant
- 2000-10-25 BR BR0015120-3A patent/BR0015120A/pt not_active Application Discontinuation
- 2000-10-25 NZ NZ518581A patent/NZ518581A/en unknown
- 2000-10-25 MX MXPA02004218A patent/MXPA02004218A/es active IP Right Grant
- 2000-10-25 DK DK00970070T patent/DK1245564T3/da active
- 2000-10-25 CA CA002389156A patent/CA2389156C/en not_active Expired - Fee Related
- 2000-10-25 AU AU79574/00A patent/AU776193B2/en not_active Ceased
- 2000-10-25 WO PCT/JP2000/007469 patent/WO2001030756A1/ja active IP Right Grant
- 2000-10-25 HU HU0203161A patent/HUP0203161A3/hu unknown
- 2000-10-25 AT AT00970070T patent/ATE322479T1/de not_active IP Right Cessation
- 2000-10-25 TR TR2002/01654T patent/TR200201654T2/xx unknown
- 2000-10-25 CN CNB008178003A patent/CN1293052C/zh not_active Expired - Fee Related
- 2000-10-25 ES ES00970070T patent/ES2261248T3/es not_active Expired - Lifetime
- 2000-10-25 EP EP00970070A patent/EP1245564B1/en not_active Expired - Lifetime
- 2000-10-25 PT PT00970070T patent/PT1245564E/pt unknown
- 2000-10-27 TW TW089122706A patent/TWI226886B/zh not_active IP Right Cessation
-
2002
- 2002-04-23 IL IL149306A patent/IL149306A/en not_active IP Right Cessation
- 2002-04-24 ZA ZA200203278A patent/ZA200203278B/en unknown
- 2002-04-25 US US10/132,042 patent/US6555556B1/en not_active Expired - Fee Related
- 2002-04-26 NO NO20021990A patent/NO323147B1/no not_active IP Right Cessation
- 2002-11-06 US US10/288,838 patent/US20040010009A1/en not_active Abandoned
- 2002-12-05 HK HK02108844.9A patent/HK1047431B/zh not_active IP Right Cessation
-
2003
- 2003-11-07 US US10/704,355 patent/US20040248981A1/en not_active Abandoned
-
2006
- 2006-07-04 CY CY20061100927T patent/CY1106116T1/el unknown
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