HRP970671A2 - Novel heterocyclically substituted benzamides and their use - Google Patents

Novel heterocyclically substituted benzamides and their use

Info

Publication number: HRP970671A2
Authority: HR; Croatia
Prior art keywords: alkyl; formula; phenyl; hydrogen; heterocyclic substituted
Prior art date: 1996-12-09

Application number

HR19650975.0A

Other languages

English (en)

Croatian (hr)

Inventor

Hans-Joerg Treiber

Original Assignee

Hans-Joerg Treiber

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.)

1996-12-09

Filing date

1997-12-08

Publication date

1998-10-31

1997-12-08 Application filed by Hans-Joerg Treiber filed Critical Hans-Joerg Treiber

1998-10-31 Publication of HRP970671A2 publication Critical patent/HRP970671A2/hr

Links

150000003936 benzamides Chemical class 0.000 title claims description 25
229940054066 benzamide antipsychotics Drugs 0.000 title claims description 20
108010032088 Calpain Proteins 0.000 claims description 28
102000007590 Calpain Human genes 0.000 claims description 28
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 27
239000001257 hydrogen Substances 0.000 claims description 25
229910052739 hydrogen Inorganic materials 0.000 claims description 25
125000000623 heterocyclic group Chemical group 0.000 claims description 24
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 24
239000003814 drug Substances 0.000 claims description 16
229940079593 drug Drugs 0.000 claims description 15
239000000460 chlorine Substances 0.000 claims description 14
229910052794 bromium Inorganic materials 0.000 claims description 12
229910052801 chlorine Inorganic materials 0.000 claims description 12
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 12
229910052731 fluorine Inorganic materials 0.000 claims description 12
238000002360 preparation method Methods 0.000 claims description 12
125000000896 monocarboxylic acid group Chemical group 0.000 claims description 11
201000010099 disease Diseases 0.000 claims description 10
238000004519 manufacturing process Methods 0.000 claims description 10
KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 9
208000014674 injury Diseases 0.000 claims description 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
230000000694 effects Effects 0.000 claims description 7
208000028867 ischemia Diseases 0.000 claims description 7
208000015122 neurodegenerative disease Diseases 0.000 claims description 6
230000006378 damage Effects 0.000 claims description 5
230000008733 trauma Effects 0.000 claims description 5
208000024827 Alzheimer disease Diseases 0.000 claims description 4
208000023105 Huntington disease Diseases 0.000 claims description 4
208000027418 Wounds and injury Diseases 0.000 claims description 4
230000004770 neurodegeneration Effects 0.000 claims description 4
150000003839 salts Chemical class 0.000 claims description 4
208000002177 Cataract Diseases 0.000 claims description 3
208000013875 Heart injury Diseases 0.000 claims description 3
206010061218 Inflammation Diseases 0.000 claims description 3
230000004054 inflammatory process Effects 0.000 claims description 3
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
208000003890 Coronary Vasospasm Diseases 0.000 claims description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
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206010061481 Renal injury Diseases 0.000 claims description 2
206010063897 Renal ischaemia Diseases 0.000 claims description 2
208000025747 Rheumatic disease Diseases 0.000 claims description 2
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238000002399 angioplasty Methods 0.000 claims description 2
210000004204 blood vessel Anatomy 0.000 claims description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
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 claims 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 claims description 2
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
239000002852 cysteine proteinase inhibitor Substances 0.000 claims description 2
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239000011737 fluorine Chemical group 0.000 claims description 2
125000001041 indolyl group Chemical group 0.000 claims description 2
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125000001624 naphthyl group Chemical group 0.000 claims description 2
230000035755 proliferation Effects 0.000 claims description 2
125000004076 pyridyl group Chemical group 0.000 claims description 2
208000037803 restenosis Diseases 0.000 claims description 2
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125000001424 substituent group Chemical group 0.000 claims description 2
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IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 52
239000000543 intermediate Substances 0.000 description 31
150000001875 compounds Chemical class 0.000 description 29
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239000003112 inhibitor Substances 0.000 description 23
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
238000000034 method Methods 0.000 description 20
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ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
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238000006243 chemical reaction Methods 0.000 description 16
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239000002253 acid Substances 0.000 description 14
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 14
238000005160 1H NMR spectroscopy Methods 0.000 description 13
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OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
150000001299 aldehydes Chemical class 0.000 description 8
125000005605 benzo group Chemical group 0.000 description 8
239000011575 calcium Substances 0.000 description 8
229910052791 calcium Inorganic materials 0.000 description 8
VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical compound OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 description 8
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239000002244 precipitate Substances 0.000 description 7
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VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
150000007513 acids Chemical class 0.000 description 6
239000000872 buffer Substances 0.000 description 6
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
ZDVQNKMYFPSYRE-UHFFFAOYSA-N n-oxobenzamide Chemical class O=NC(=O)C1=CC=CC=C1 ZDVQNKMYFPSYRE-UHFFFAOYSA-N 0.000 description 6
108090000765 processed proteins & peptides Proteins 0.000 description 6
238000003786 synthesis reaction Methods 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
150000001298 alcohols Chemical class 0.000 description 5
150000001408 amides Chemical class 0.000 description 5
230000030833 cell death Effects 0.000 description 5
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239000003960 organic solvent Substances 0.000 description 5
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WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
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150000001412 amines Chemical class 0.000 description 4
150000001735 carboxylic acids Chemical class 0.000 description 4
CFEPCPHKICBCJV-UHFFFAOYSA-N ethyl 4-isocyanatobenzoate Chemical compound CCOC(=O)C1=CC=C(N=C=O)C=C1 CFEPCPHKICBCJV-UHFFFAOYSA-N 0.000 description 4
229930195712 glutamate Natural products 0.000 description 4
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125000000468 ketone group Chemical group 0.000 description 4
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ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 3
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Classifications

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- 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
- 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
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/58—[b]- or [c]-condensed
- C07D209/62—Naphtho [c] pyrroles; Hydrogenated naphtho [c] pyrroles
- C07D209/66—Naphtho [c] pyrroles; Hydrogenated naphtho [c] pyrroles with oxygen atoms in positions 1 and 3
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/95—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in positions 2 and 4
- C07D239/96—Two oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D475/00—Heterocyclic compounds containing pteridine ring systems
- C07D475/02—Heterocyclic compounds containing pteridine ring systems with an oxygen atom directly attached in position 4

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HR19650975.0A 1996-12-09 1997-12-08 Novel heterocyclically substituted benzamides and their use HRP970671A2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19650975A DE19650975A1 (de)	1996-12-09	1996-12-09	Neue heterocyclisch substituierte Benzamide und deren Anwendung

Publications (1)

Publication Number	Publication Date
HRP970671A2 true HRP970671A2 (en)	1998-10-31

Family

ID=7814035

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
HR19650975.0A HRP970671A2 (en)	1996-12-09	1997-12-08	Novel heterocyclically substituted benzamides and their use

Country Status (24)

Country	Link
US (2)	US6172072B1 (de)
EP (1)	EP0946509A1 (de)
JP (1)	JP2001505889A (de)
KR (1)	KR20000057445A (de)
CN (1)	CN1239949A (de)
AR (1)	AR010339A1 (de)
AU (1)	AU742732B2 (de)
BG (1)	BG63388B1 (de)
BR (1)	BR9713884A (de)
CA (1)	CA2273988A1 (de)
CO (1)	CO4910161A1 (de)
CZ (1)	CZ292391B6 (de)
DE (1)	DE19650975A1 (de)
HR (1)	HRP970671A2 (de)
HU (1)	HUP0000496A3 (de)
ID (1)	ID22490A (de)
IL (1)	IL129358A0 (de)
NO (1)	NO992770L (de)
NZ (1)	NZ335066A (de)
SK (1)	SK56699A3 (de)
TR (1)	TR199901282T2 (de)
TW (1)	TW420666B (de)
WO (1)	WO1998025899A1 (de)
ZA (1)	ZA9710979B (de)

Families Citing this family (28)

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Publication number	Priority date	Publication date	Assignee	Title
HRP20000788A2 (en) *	1998-04-20	2001-06-30	Basf Ag	Novel heterocyclically substituted amides with cysteine protease-inhibiting effect
FR2800737B1 (fr) *	1999-11-05	2006-06-30	Sod Conseils Rech Applic	Nouveaux composes heterocycliques et leur application a titre de medicaments
ES2259617T3 (es)	1999-11-05	2006-10-16	Societe De Conseils De Recherches Et D'applications Scientifiques (S.C.R.A.S.)	Compuestos heterociclicos y su aplicacion como medicamentos.
GB0031302D0 (en) *	2000-12-21	2001-01-31	Glaxo Group Ltd	Napthalene derivatives
KR100962972B1 (ko)	2002-07-26	2010-06-09	주식회사유한양행	1-페닐피페리딘-3-온 유도체 및 그의 제조방법
DE60329316D1 (de)	2002-11-12	2009-10-29	Merck & Co Inc	Phenylcarboxamide als beta-sekretase-hemmer zur behandlung von alzheimer
WO2005019188A1 (ja) *	2003-08-22	2005-03-03	Takeda Pharmaceutical Company Limited	縮合ピリミジン誘導体およびその用途
US7320992B2 (en) *	2003-08-25	2008-01-22	Amgen Inc.	Substituted 2,3-dihydro-1h-isoindol-1-one derivatives and methods of use
FR2863268B1 (fr) *	2003-12-09	2006-02-24	Sod Conseils Rech Applic	Nouveaux derives du 2-hydroxytetrahydrofuranne et leur application a titre de medicaments
BRPI0418026A (pt) *	2003-12-22	2007-04-17	Ajinomoto Kk	derivados de fenilalanina ou sais farmaceuticamente aceitáveis destes, composição farmacêutica, antagonista de alfa4 integrina, e, agente terapêutico ou agente preventivo para doenças
GB0416730D0 (en)	2004-07-27	2004-09-01	Novartis Ag	Organic compounds
US20070010537A1 (en) *	2004-08-20	2007-01-11	Kazumasa Hamamura	Fused pyramidine derivative and use thereof
GB0507298D0 (en)	2005-04-11	2005-05-18	Novartis Ag	Organic compounds
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1996
- 1996-12-09 DE DE19650975A patent/DE19650975A1/de not_active Withdrawn
1997
- 1997-11-28 EP EP97952007A patent/EP0946509A1/de not_active Withdrawn
- 1997-11-28 BR BR9713884-3A patent/BR9713884A/pt not_active IP Right Cessation
- 1997-11-28 AU AU55580/98A patent/AU742732B2/en not_active Ceased
- 1997-11-28 KR KR1019990705071A patent/KR20000057445A/ko not_active Withdrawn
- 1997-11-28 CZ CZ19991743A patent/CZ292391B6/cs not_active IP Right Cessation
- 1997-11-28 CN CN97180437A patent/CN1239949A/zh active Pending
- 1997-11-28 IL IL12935897A patent/IL129358A0/xx unknown
- 1997-11-28 CA CA002273988A patent/CA2273988A1/en not_active Abandoned
- 1997-11-28 JP JP52615598A patent/JP2001505889A/ja active Pending
- 1997-11-28 WO PCT/EP1997/006653 patent/WO1998025899A1/de not_active Ceased
- 1997-11-28 ID IDW990486D patent/ID22490A/id unknown
- 1997-11-28 SK SK566-99A patent/SK56699A3/sk unknown
- 1997-11-28 US US09/308,350 patent/US6172072B1/en not_active Expired - Fee Related
- 1997-11-28 NZ NZ335066A patent/NZ335066A/xx unknown
- 1997-11-28 HU HU0000496A patent/HUP0000496A3/hu unknown
- 1997-11-28 TR TR1999/01282T patent/TR199901282T2/xx unknown
- 1997-12-08 TW TW086118462A patent/TW420666B/zh active
- 1997-12-08 HR HR19650975.0A patent/HRP970671A2/hr not_active Application Discontinuation
- 1997-12-08 ZA ZA9710979A patent/ZA9710979B/xx unknown
- 1997-12-09 AR ARP970105766A patent/AR010339A1/es not_active Application Discontinuation
- 1997-12-09 CO CO97071820A patent/CO4910161A1/es unknown
1999
- 1999-05-12 BG BG103399A patent/BG63388B1/bg unknown
- 1999-06-08 NO NO992770A patent/NO992770L/no unknown
2000
- 2000-09-21 US US09/666,304 patent/US6436949B1/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
US6172072B1 (en)	2001-01-09
US6436949B1 (en)	2002-08-20
JP2001505889A (ja)	2001-05-08
BR9713884A (pt)	2000-02-29
TR199901282T2 (xx)	1999-10-21
AU742732B2 (en)	2002-01-10
CZ292391B6 (cs)	2003-09-17
WO1998025899A1 (de)	1998-06-18
HUP0000496A3 (en)	2002-11-28
NO992770D0 (no)	1999-06-08
SK56699A3 (en)	1999-10-08
BG103399A (en)	2000-01-31
NO992770L (no)	1999-06-08
NZ335066A (en)	2000-03-27
AU5558098A (en)	1998-07-03
ID22490A (id)	1999-10-21
CO4910161A1 (es)	2000-04-24
IL129358A0 (en)	2000-02-17
EP0946509A1 (de)	1999-10-06
TW420666B (en)	2001-02-01
BG63388B1 (bg)	2001-12-29
CN1239949A (zh)	1999-12-29
HUP0000496A2 (hu)	2000-09-28
ZA9710979B (en)	1999-06-18
KR20000057445A (ko)	2000-09-15
DE19650975A1 (de)	1998-06-10
AR010339A1 (es)	2000-06-07
CZ174399A3 (cs)	1999-08-11
CA2273988A1 (en)	1998-06-18

Legal Events

Date	Code	Title
1998-10-31	A1OB	Publication of a patent application
1999-04-30	AIPI	Request for the grant of a patent on the basis of a substantive examination of a patent application
2008-01-23	ODBC	Application rejected

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US6630493B1 (en)	2003-10-07	Heterocyclically substituted amides, their preparation and use
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HRP20000777A2 (en)	2001-06-30	New substituted benzamides, their production and use
JP2011063604A (ja)	2011-03-31	新規の複素環式の置換されたアミド、その製造および使用
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HRP20000787A2 (en)	2001-08-31	New substituted amides, their production and their use
HK1037371A (en)	2002-02-08	Novel heterocyclically substituted amides with cysteine protease-inhibiting effect
MXPA00010274A (en)	2001-07-31	Novel heterocyclically substituted amides with cysteine protease-inhibiting effect
CZ208499A3 (cs)	2000-09-13	Ketobenzamidy a jejich použití
CZ20003867A3 (cs)	2001-01-17	Amidy a jejich použití
MXPA00009755A (en)	2001-07-09	New substituted amides, their production and their use
CZ20003843A3 (cs)	2001-01-17	Amidy a jejich použití