ZA200007039B - Biphenyl derivatives. - Google Patents

Biphenyl derivatives. Download PDF

Info

Publication number: ZA200007039B
Authority: ZA; South Africa
Prior art keywords: formula; compounds; physiologically acceptable; acceptable salts; coor
Prior art date: 1998-04-30

Application number

ZA200007039A

Other languages

English (en)

Inventor

Dieter Dorsch

Werner Mederski

Hanns Wurziger

Sabine Bernotat-Danielowski

Horst Juraszyk

Joachim Gante

Hans-Peter Buchstaller

Guido Melzer

Original Assignee

Merck Patent Gmbh

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.)

1998-04-30

Filing date

2000-11-29

Publication date

2002-02-28

2000-11-29 Application filed by Merck Patent Gmbh filed Critical Merck Patent Gmbh

2002-02-28 Publication of ZA200007039B publication Critical patent/ZA200007039B/en

Links

ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 title description 5
-1 4-amidinophenoxymethyl Chemical group 0.000 claims description 77
150000001875 compounds Chemical class 0.000 claims description 30
150000003839 salts Chemical class 0.000 claims description 18
238000000034 method Methods 0.000 claims description 16
108010074860 Factor Xa Proteins 0.000 claims description 9
208000007536 Thrombosis Diseases 0.000 claims description 8
239000003814 drug Substances 0.000 claims description 7
229910052731 fluorine Inorganic materials 0.000 claims description 7
125000001624 naphthyl group Chemical group 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
206010002383 Angina Pectoris Diseases 0.000 claims description 6
206010003210 Arteriosclerosis Diseases 0.000 claims description 6
206010008190 Cerebrovascular accident Diseases 0.000 claims description 6
206010061218 Inflammation Diseases 0.000 claims description 6
206010022562 Intermittent claudication Diseases 0.000 claims description 6
208000006011 Stroke Diseases 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 6
238000002399 angioplasty Methods 0.000 claims description 6
208000011775 arteriosclerosis disease Diseases 0.000 claims description 6
125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 6
230000004054 inflammatory process Effects 0.000 claims description 6
208000021156 intermittent vascular claudication Diseases 0.000 claims description 6
208000010125 myocardial infarction Diseases 0.000 claims description 6
125000006239 protecting group Chemical group 0.000 claims description 6
208000037803 restenosis Diseases 0.000 claims description 6
229910052794 bromium Inorganic materials 0.000 claims description 5
229910052801 chlorine Inorganic materials 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 5
238000002360 preparation method Methods 0.000 claims description 5
125000003277 amino group Chemical group 0.000 claims description 4
239000003795 chemical substances by application Substances 0.000 claims description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
239000002253 acid Substances 0.000 claims description 3
229910052740 iodine Inorganic materials 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
125000003178 carboxy group Chemical group [H]OC(*)=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
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
238000007327 hydrogenolysis reaction Methods 0.000 claims description 2
230000003301 hydrolyzing effect Effects 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
150000004866 oxadiazoles Chemical class 0.000 claims description 2
125000004430 oxygen atom Chemical group O* 0.000 claims description 2
125000004434 sulfur atom Chemical group 0.000 claims description 2
239000000203 mixture Substances 0.000 claims 5
239000000126 substance Substances 0.000 claims 5
239000000825 pharmaceutical preparation Substances 0.000 claims 3
ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims 2
239000007788 liquid Substances 0.000 claims 2
QAIJMAFUGWSUFR-UHFFFAOYSA-N 3-[(3-carbamimidoylphenoxy)methyl]-5-(3-carbamimidoylphenyl)benzoic acid Chemical compound NC(=N)C1=CC=CC(OCC=2C=C(C=C(C=2)C(O)=O)C=2C=C(C=CC=2)C(N)=N)=C1 QAIJMAFUGWSUFR-UHFFFAOYSA-N 0.000 claims 1
XVWGCWQAXSLVAX-UHFFFAOYSA-N 3-[3-[(3-carbamimidoylphenoxy)methyl]phenyl]benzenecarboximidamide Chemical compound NC(=N)C1=CC=CC(OCC=2C=C(C=CC=2)C=2C=C(C=CC=2)C(N)=N)=C1 XVWGCWQAXSLVAX-UHFFFAOYSA-N 0.000 claims 1
CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims 1
SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims 1
239000007789 gas Substances 0.000 claims 1
239000003112 inhibitor Substances 0.000 claims 1
239000000546 pharmaceutical excipient Substances 0.000 claims 1
239000007787 solid Substances 0.000 claims 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
150000003254 radicals Chemical class 0.000 description 5
239000000460 chlorine Substances 0.000 description 4
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
208000035475 disorder Diseases 0.000 description 4
230000009424 thromboembolic effect Effects 0.000 description 4
125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 3
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
108090000190 Thrombin Proteins 0.000 description 3
125000002252 acyl group Chemical group 0.000 description 3
230000002785 anti-thrombosis Effects 0.000 description 3
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 3
230000005764 inhibitory process Effects 0.000 description 3
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 3
229960004072 thrombin Drugs 0.000 description 3
125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 description 2
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 2
125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 2
125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 description 2
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 2
125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 2
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
108091005804 Peptidases Proteins 0.000 description 2
239000004365 Protease Substances 0.000 description 2
230000002429 anti-coagulating effect Effects 0.000 description 2
239000003146 anticoagulant agent Substances 0.000 description 2
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
235000010290 biphenyl Nutrition 0.000 description 2
239000004305 biphenyl Substances 0.000 description 2
230000023555 blood coagulation Effects 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 2
125000006125 ethylsulfonyl group Chemical group 0.000 description 2
239000011737 fluorine Substances 0.000 description 2
150000004677 hydrates Chemical class 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
238000005259 measurement Methods 0.000 description 2
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 2
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 2
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 2
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 2
230000002265 prevention Effects 0.000 description 2
239000012453 solvate Substances 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
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
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 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
125000005917 3-methylpentyl group Chemical group 0.000 description 1
125000006306 4-iodophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1I 0.000 description 1
206010053567 Coagulopathies Diseases 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
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
230000004913 activation Effects 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
238000006243 chemical reaction Methods 0.000 description 1
230000035602 clotting Effects 0.000 description 1
125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
150000004683 dihydrates Chemical class 0.000 description 1
230000000694 effects Effects 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
230000023597 hemostasis Effects 0.000 description 1
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 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
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
238000000338 in vitro Methods 0.000 description 1
238000001727 in vivo Methods 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
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([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
150000004682 monohydrates Chemical class 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
125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 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
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 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
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
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
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 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

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C257/00—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines
- C07C257/10—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines
- C07C257/18—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines having carbon atoms of amidino groups bound to carbon atoms of six-membered aromatic rings
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- 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
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/20—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups containing any of the groups, X being a hetero atom, Y being any atom, e.g. acylguanidines
- C07C279/22—Y being a hydrogen or a carbon atom, e.g. benzoylguanidines

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Life Sciences & Earth Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Hematology (AREA)
Vascular Medicine (AREA)
Urology & Nephrology (AREA)
Diabetes (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

ZA200007039A 1998-04-30 2000-11-29 Biphenyl derivatives. ZA200007039B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19819548A DE19819548A1 (de)	1998-04-30	1998-04-30	Biphenylderivate

Publications (1)

Publication Number	Publication Date
ZA200007039B true ZA200007039B (en)	2002-02-28

Family

ID=7866421

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
ZA200007039A ZA200007039B (en)	1998-04-30	2000-11-29	Biphenyl derivatives.

Country Status (19)

Country	Link
US (1)	US6380430B1 (zh)
EP (1)	EP1076643A1 (zh)
JP (1)	JP2002513780A (zh)
KR (1)	KR20010052249A (zh)
CN (1)	CN1299343A (zh)
AR (1)	AR019264A1 (zh)
AU (1)	AU750472B2 (zh)
BR (1)	BR9910021A (zh)
CA (1)	CA2328732A1 (zh)
DE (1)	DE19819548A1 (zh)
HU (1)	HUP0102220A3 (zh)
ID (1)	ID27152A (zh)
NO (1)	NO20005435L (zh)
PL (1)	PL343598A1 (zh)
RU (1)	RU2219166C2 (zh)
SK (1)	SK15962000A3 (zh)
UA (1)	UA58593C2 (zh)
WO (1)	WO1999057096A1 (zh)
ZA (1)	ZA200007039B (zh)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AU773156B2 (en) *	1999-01-28	2004-05-20	Teijin Limited	Release-regulating preparations
DE19945302A1 (de) *	1999-09-22	2001-03-29	Merck Patent Gmbh	Biphenylderivate als NHE-3-Inhibitoren
DE10027024A1 (de) *	2000-05-31	2001-12-06	Merck Patent Gmbh	Carbaminsäureester
EP1296977A1 (en) *	2000-06-23	2003-04-02	Bristol-Myers Squibb Pharma Company	Heteroaryl-phenyl substituted factor xa inhibitors
DE10037146A1 (de) *	2000-07-29	2002-02-07	Merck Patent Gmbh	Acetamidderivate
SI1569912T1 (sl)	2002-12-03	2015-09-30	Pharmacyclics Llc	Derivati 2-(2-hidroksibifenil-3-il)-1h-benzoimidazol-5-karboksamidina kot inhibitorji faktorja viia
US7534894B2 (en)	2003-09-25	2009-05-19	Wyeth	Biphenyloxy-acids
CN103012200B (zh) *	2011-09-20	2014-12-17	北京大学	具有β-分泌酶抑制功能的化合物及其制备方法与应用

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5922697B2 (ja) *	1976-01-13	1984-05-28	エーザイ株式会社	ビス−（メタ−アミジノフエノキシ）−化合物
US4086244A (en)	1976-12-10	1978-04-25	E. R. Squibb & Sons, Inc.	Amidines
DE4102024A1 (de)	1991-01-24	1992-07-30	Thomae Gmbh Dr K	Biphenylderivate, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung
DE4219158A1 (de)	1992-06-11	1993-12-16	Thomae Gmbh Dr K	Biphenylderivate, diese Verbindungen enthaltende Arzneimittel und Verfahren zu ihrer Herstellung
PL316438A1 (en)	1995-11-20	1997-05-26	Hoechst Ag	Novel substituted derivatives of benzoyloguanidine, method of obtaining them, their application in production of pharmaceutic and diagnostic agents and pharmaceutic agent as such
GB9600063D0 (en)	1996-01-03	1996-03-06	Fujisawa Pharmaceutical Co	Guaridine derivatives

1998
- 1998-04-30 DE DE19819548A patent/DE19819548A1/de not_active Withdrawn
1999
- 1999-04-12 RU RU2000129159/04A patent/RU2219166C2/ru not_active IP Right Cessation
- 1999-04-12 AU AU38154/99A patent/AU750472B2/en not_active Ceased
- 1999-04-12 WO PCT/EP1999/002457 patent/WO1999057096A1/de not_active Application Discontinuation
- 1999-04-12 SK SK1596-2000A patent/SK15962000A3/sk unknown
- 1999-04-12 PL PL99343598A patent/PL343598A1/xx unknown
- 1999-04-12 CN CN99805661A patent/CN1299343A/zh active Pending
- 1999-04-12 EP EP99920646A patent/EP1076643A1/de not_active Withdrawn
- 1999-04-12 US US09/674,267 patent/US6380430B1/en not_active Expired - Fee Related
- 1999-04-12 CA CA002328732A patent/CA2328732A1/en not_active Abandoned
- 1999-04-12 ID IDW20002341A patent/ID27152A/id unknown
- 1999-04-12 HU HU0102220A patent/HUP0102220A3/hu unknown
- 1999-04-12 KR KR1020007011315A patent/KR20010052249A/ko not_active Application Discontinuation
- 1999-04-12 BR BR9910021-5A patent/BR9910021A/pt not_active IP Right Cessation
- 1999-04-12 JP JP2000547066A patent/JP2002513780A/ja active Pending
- 1999-04-30 AR ARP990102014A patent/AR019264A1/es not_active Application Discontinuation
- 1999-12-04 UA UA2000116686A patent/UA58593C2/uk unknown
2000
- 2000-10-27 NO NO20005435A patent/NO20005435L/no not_active Application Discontinuation
- 2000-11-29 ZA ZA200007039A patent/ZA200007039B/en unknown

Also Published As

Publication number	Publication date
DE19819548A1 (de)	1999-11-04
HUP0102220A2 (hu)	2001-10-28
ID27152A (id)	2001-03-08
SK15962000A3 (sk)	2001-05-10
KR20010052249A (ko)	2001-06-25
AU3815499A (en)	1999-11-23
HUP0102220A3 (en)	2002-11-28
UA58593C2 (uk)	2003-08-15
NO20005435D0 (no)	2000-10-27
EP1076643A1 (de)	2001-02-21
US6380430B1 (en)	2002-04-30
PL343598A1 (en)	2001-08-27
AR019264A1 (es)	2002-02-13
CA2328732A1 (en)	1999-11-11
WO1999057096A1 (de)	1999-11-11
AU750472B2 (en)	2002-07-18
RU2219166C2 (ru)	2003-12-20
NO20005435L (no)	2000-10-27
JP2002513780A (ja)	2002-05-14
BR9910021A (pt)	2000-12-26
CN1299343A (zh)	2001-06-13

Publication	Publication Date	Title
ZA200103498B (en)	2002-08-13	Imidazo[4,5-C-]-pyridine-4-one derivative with factor Xa inhibiting effect.
ZA200007039B (en)	2002-02-28	Biphenyl derivatives.
Bannai et al.	1982	Transport of cystine and cysteine and cell growth in cultured human diploid fibroblasts: effect of glutamate and homocysteate
CA2387529A1 (en)	2001-03-29	Biphenyl derivatives as nhe-3 inhibitors
US7589126B2 (en)	2009-09-15	5-amidino-2-hydroxybenzenesulfonamide derivatives, pharmaceutical compositions containing the same and intermediates for their preparation
CA1067404A (en)	1979-12-04	Mucolytic mercaptoacylamidobenzoic and benzenesulfonic acid compounds and process
ZA200106454B (en)	2002-11-06	Imidazo[4,5-c]-pyridine-4-on-derivatives.
SI9620136B (en)	2005-08-31	Substituted n-/(aminoiminomethyl or aminomethyl)phenyl/-propyl amides
WO2009080835A1 (en)	2009-07-02	Thyromimetric compounds in treatment of disease related to sonic hedgehog signalling
GB1476106A (en)	1977-06-10	Araliphatic nitrogen compounds processes for their preparation and pharmaceutical compositions containing them
CA2451206A1 (en)	2003-01-09	Urea derivatives with antiproteolytic activity
Mehdi et al.	1990	The inhibition of human neutrophil elastase and cathepsin G by peptidyl 1, 2-dicarbonyl derivatives
IE870690L (en)	1987-09-17	Diphenyl-methane derivatives
US6638977B1 (en)	2003-10-28	Plasminogen activator inhibitor antagonists
CZ20022783A3 (cs)	2002-11-13	Derivát aminosulfonylbifenylu, jeho pouľití a farmaceutický prostředek, který ho obsahuje
KR20020047310A (ko)	2002-06-21	Ｎ-구아니디노알킬아미드, 이의 제조방법, 이의 용도 및이를 포함하는 약제학적 조성물
IE850518L (en)	1985-09-02	Guanidine derivatives.
JPH11140040A (ja)	1999-05-25	３−アミジノフェニルエーテル誘導体、活性化血液凝固第ｘ因子阻害剤およびそれらの製造中間体
WO2001030775A1 (en)	2001-05-03	Novel indole compounds
ZA200102565B (en)	2002-06-28	2-oxo-2h-quinoline derivatives.
US4468378A (en)	1984-08-28	Oxysulfonic derivative of copolymer of acrolein and acrylic acid and direct action anticoagulant on its basis
JPS6253510B2 (zh)	1987-11-10
CN117843157A (zh)	2024-04-09	一种长效缓释型阻垢剂及其制备方法
CN112239447A (zh)	2021-01-19	二羟基二甲基异色满-3-甲酰极性氨基酸,其制备,抗栓活性和应用
GB1343594A (en)	1974-01-10	Thiono-phosphoric-phosphonic- acid esters and ester amides a process for their preparation and their use as insecticides and acaridides