SK15962001A3 - Heterocyklicky substituované benzimidazoly, ich príprava a použitie - Google Patents

Heterocyklicky substituované benzimidazoly, ich príprava a použitie Download PDF

Info

Publication number: SK15962001A3
Authority: SK; Slovakia
Prior art keywords: alkyl; benzimidazole; carboxamide; hydrogen; phenyl
Prior art date: 1999-05-07

Application number

SK1596-2001A

Other languages

English (en)

Slovak (sk)

Inventor

Wilfried Lubisch

Michael Kock

Thomas H�GER

Roland Grandel

Uta Holzenkamp

Sabine Schult

Reinhold M�LLER

Original Assignee

Basf Aktiengesellschaft

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.)

1999-05-07

Filing date

2000-04-27

Publication date

2002-06-04

2000-04-27 Application filed by Basf Aktiengesellschaft filed Critical Basf Aktiengesellschaft

2002-06-04 Publication of SK15962001A3 publication Critical patent/SK15962001A3/sk

Links

238000004519 manufacturing process Methods 0.000 title claims abstract description 17
150000001556 benzimidazoles Chemical class 0.000 title abstract description 22
239000003814 drug Substances 0.000 claims abstract description 17
-1 chloro, fluoro, bromo, iodo Chemical group 0.000 claims description 88
150000001875 compounds Chemical class 0.000 claims description 47
229910052739 hydrogen Inorganic materials 0.000 claims description 41
239000001257 hydrogen Substances 0.000 claims description 41
150000003254 radicals Chemical class 0.000 claims description 34
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 28
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 27
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 25
238000011282 treatment Methods 0.000 claims description 23
150000002431 hydrogen Chemical class 0.000 claims description 21
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 20
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 19
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 14
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 14
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 13
KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 12
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 12
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 12
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 10
230000006378 damage Effects 0.000 claims description 10
125000001153 fluoro group Chemical group F* 0.000 claims description 10
229930192474 thiophene Natural products 0.000 claims description 9
FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 8
206010010904 Convulsion Diseases 0.000 claims description 8
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 8
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 8
125000000623 heterocyclic group Chemical group 0.000 claims description 7
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 6
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 6
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 6
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
229910052794 bromium Inorganic materials 0.000 claims description 6
239000000460 chlorine Substances 0.000 claims description 6
229910052801 chlorine Inorganic materials 0.000 claims description 6
229910052731 fluorine Inorganic materials 0.000 claims description 6
239000011737 fluorine Substances 0.000 claims description 6
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 6
208000028867 ischemia Diseases 0.000 claims description 6
PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 6
229920006395 saturated elastomer Polymers 0.000 claims description 6
HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 5
206010028980 Neoplasm Diseases 0.000 claims description 5
125000000217 alkyl group Chemical group 0.000 claims description 5
238000011321 prophylaxis Methods 0.000 claims description 5
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 4
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 4
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
210000001367 artery Anatomy 0.000 claims description 4
RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 claims description 4
XSCHRSMBECNVNS-UHFFFAOYSA-N benzopyrazine Natural products N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 4
IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 4
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 4
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 4
CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 4
208000015122 neurodegenerative disease Diseases 0.000 claims description 4
229910052760 oxygen Inorganic materials 0.000 claims description 4
125000004076 pyridyl group Chemical group 0.000 claims description 4
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208000006011 Stroke Diseases 0.000 claims description 3
230000009089 cytolysis Effects 0.000 claims description 3
206010012601 diabetes mellitus Diseases 0.000 claims description 3
206010015037 epilepsy Diseases 0.000 claims description 3
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239000000651 prodrug Substances 0.000 claims description 3
229940002612 prodrug Drugs 0.000 claims description 3
206010039073 rheumatoid arthritis Diseases 0.000 claims description 3
238000002054 transplantation Methods 0.000 claims description 3
FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical compound C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 claims description 2
BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 claims description 2
FTAHXMZRJCZXDL-UHFFFAOYSA-N 3-piperideine Chemical compound C1CC=CCN1 FTAHXMZRJCZXDL-UHFFFAOYSA-N 0.000 claims description 2
GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical compound C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 claims description 2
KKJUPNGICOCCDW-UHFFFAOYSA-N 7-N,N-Dimethylamino-1,2,3,4,5-pentathiocyclooctane Chemical compound CN(C)C1CSSSSSC1 KKJUPNGICOCCDW-UHFFFAOYSA-N 0.000 claims description 2
206010002329 Aneurysm Diseases 0.000 claims description 2
208000033001 Complex partial seizures Diseases 0.000 claims description 2
206010019196 Head injury Diseases 0.000 claims description 2
206010027476 Metastases Diseases 0.000 claims description 2
206010063897 Renal ischaemia Diseases 0.000 claims description 2
208000025747 Rheumatic disease Diseases 0.000 claims description 2
206010000891 acute myocardial infarction Diseases 0.000 claims description 2
125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 2
125000003118 aryl group Chemical group 0.000 claims description 2
ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims description 2
QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 claims description 2
239000012964 benzotriazole Substances 0.000 claims description 2
125000002619 bicyclic group Chemical group 0.000 claims description 2
230000000740 bleeding effect Effects 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
230000003683 cardiac damage Effects 0.000 claims description 2
239000012050 conventional carrier Substances 0.000 claims description 2
210000004351 coronary vessel Anatomy 0.000 claims description 2
210000003709 heart valve Anatomy 0.000 claims description 2
125000005842 heteroatom Chemical group 0.000 claims 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 claims description 2
208000014674 injury Diseases 0.000 claims description 2
GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical compound C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 claims description 2
230000007576 microinfarct Effects 0.000 claims description 2
208000031225 myocardial ischemia Diseases 0.000 claims description 2
125000004043 oxo group Chemical group O=* 0.000 claims description 2
230000036961 partial effect Effects 0.000 claims description 2
230000002093 peripheral effect Effects 0.000 claims description 2
LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical compound C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 claims description 2
XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 claims description 2
238000002271 resection Methods 0.000 claims description 2
230000000250 revascularization Effects 0.000 claims description 2
229910052717 sulfur Inorganic materials 0.000 claims description 2
210000003478 temporal lobe Anatomy 0.000 claims description 2
230000008733 trauma Effects 0.000 claims description 2
AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims 2
230000003961 neuronal insult Effects 0.000 claims 2
208000024827 Alzheimer disease Diseases 0.000 claims 1
208000023105 Huntington disease Diseases 0.000 claims 1
208000018737 Parkinson disease Diseases 0.000 claims 1
206010062237 Renal impairment Diseases 0.000 claims 1
206010040047 Sepsis Diseases 0.000 claims 1
206010040070 Septic Shock Diseases 0.000 claims 1
208000037892 acute myocardial injury Diseases 0.000 claims 1
230000000747 cardiac effect Effects 0.000 claims 1
JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims 1
230000036303 septic shock Effects 0.000 claims 1
102000012338 Poly(ADP-ribose) Polymerases Human genes 0.000 abstract description 55
108010061844 Poly(ADP-ribose) Polymerases Proteins 0.000 abstract description 55
229920000776 Poly(Adenosine diphosphate-ribose) polymerase Polymers 0.000 abstract description 38
239000003112 inhibitor Substances 0.000 abstract description 17
102100023712 Poly [ADP-ribose] polymerase 1 Human genes 0.000 abstract 2
JJDMKDXGNVJWCD-UHFFFAOYSA-N 1h-benzimidazole-4-carboxamide Chemical class NC(=O)C1=CC=CC2=C1N=CN2 JJDMKDXGNVJWCD-UHFFFAOYSA-N 0.000 description 71
239000000243 solution Substances 0.000 description 58
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 53
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 50
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 48
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 48
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238000003786 synthesis reaction Methods 0.000 description 46
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238000005160 1H NMR spectroscopy Methods 0.000 description 35
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239000000047 product Substances 0.000 description 23
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 22
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
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238000006243 chemical reaction Methods 0.000 description 13
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IBLCGSGGDXQWDY-UHFFFAOYSA-N tert-butyl 2-[3-(diethylamino)propylamino]pyridine-4-carboxylate Chemical compound CCN(CC)CCCNC1=CC(C(=O)OC(C)(C)C)=CC=N1 IBLCGSGGDXQWDY-UHFFFAOYSA-N 0.000 description 1
FPUSSPQEUANTGI-UHFFFAOYSA-N tert-butyl 2-chloropyridine-4-carboxylate Chemical compound CC(C)(C)OC(=O)C1=CC=NC(Cl)=C1 FPUSSPQEUANTGI-UHFFFAOYSA-N 0.000 description 1
FMFVWFOLGYTRBX-UHFFFAOYSA-N tert-butyl 6-bromopyridine-2-carboxylate Chemical compound CC(C)(C)OC(=O)C1=CC=CC(Br)=N1 FMFVWFOLGYTRBX-UHFFFAOYSA-N 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
150000003557 thiazoles Chemical class 0.000 description 1
235000010384 tocopherol Nutrition 0.000 description 1
239000011732 tocopherol Substances 0.000 description 1
229960001295 tocopherol Drugs 0.000 description 1
229930003799 tocopherol Natural products 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
230000009466 transformation Effects 0.000 description 1
238000000844 transformation Methods 0.000 description 1
GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
- 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
- A61P25/08—Antiepileptics; Anticonvulsants
- A61P25/10—Antiepileptics; Anticonvulsants for petit-mal
- 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
- A61P25/16—Anti-Parkinson drugs
- 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
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
- 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
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/18—Benzimidazoles; Hydrogenated benzimidazoles with aryl radicals directly attached in position 2
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Diabetes (AREA)
Pain & Pain Management (AREA)
Rheumatology (AREA)
Emergency Medicine (AREA)
Hematology (AREA)
Physical Education & Sports Medicine (AREA)
Psychology (AREA)
Hospice & Palliative Care (AREA)
Psychiatry (AREA)
Orthopedic Medicine & Surgery (AREA)
Immunology (AREA)
Endocrinology (AREA)
Urology & Nephrology (AREA)
Obesity (AREA)
Communicable Diseases (AREA)
Oncology (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Pyridine Compounds (AREA)

SK1596-2001A 1999-05-07 2000-04-27 Heterocyklicky substituované benzimidazoly, ich príprava a použitie SK15962001A3 (sk)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE19920936A DE19920936A1 (de)	1999-05-07	1999-05-07	Heterozyklisch substituierte Benzimidazole, deren Herstellung und Anwendung
PCT/EP2000/003813 WO2000068206A1 (fr)	1999-05-07	2000-04-27	Benzimidazoles substitues par voie heterocyclique, leur production et leur application

Publications (1)

Publication Number	Publication Date
SK15962001A3 true SK15962001A3 (sk)	2002-06-04

Family

ID=7907219

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK1596-2001A SK15962001A3 (sk)	1999-05-07	2000-04-27	Heterocyklicky substituované benzimidazoly, ich príprava a použitie

Country Status (27)

Country	Link
US (1)	US6696437B1 (fr)
EP (1)	EP1177178B1 (fr)
JP (1)	JP4004737B2 (fr)
KR (1)	KR20010112477A (fr)
CN (1)	CN1353695A (fr)
AR (1)	AR029161A1 (fr)
AT (1)	ATE286029T1 (fr)
AU (1)	AU4558400A (fr)
BG (1)	BG106035A (fr)
BR (1)	BR0010342A (fr)
CA (1)	CA2371645C (fr)
CO (1)	CO5170517A1 (fr)
DE (2)	DE19920936A1 (fr)
DK (1)	DK1177178T3 (fr)
ES (1)	ES2235869T3 (fr)
HK (1)	HK1046281A1 (fr)
HU (1)	HUP0202970A2 (fr)
IL (1)	IL146147A0 (fr)
MY (1)	MY122771A (fr)
NO (1)	NO20015362D0 (fr)
PL (1)	PL351558A1 (fr)
PT (1)	PT1177178E (fr)
SK (1)	SK15962001A3 (fr)
TR (1)	TR200103221T2 (fr)
UA (1)	UA68436C2 (fr)
WO (1)	WO2000068206A1 (fr)
ZA (1)	ZA200108609B (fr)

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1999
- 1999-05-07 DE DE19920936A patent/DE19920936A1/de not_active Withdrawn
2000
- 2000-04-27 DE DE50009118T patent/DE50009118D1/de not_active Expired - Lifetime
- 2000-04-27 CA CA002371645A patent/CA2371645C/fr not_active Expired - Fee Related
- 2000-04-27 JP JP2000617186A patent/JP4004737B2/ja not_active Expired - Fee Related
- 2000-04-27 WO PCT/EP2000/003813 patent/WO2000068206A1/fr not_active Ceased
- 2000-04-27 UA UA2001128419A patent/UA68436C2/uk unknown
- 2000-04-27 PL PL00351558A patent/PL351558A1/xx not_active Application Discontinuation
- 2000-04-27 IL IL14614700A patent/IL146147A0/xx unknown
- 2000-04-27 EP EP00927088A patent/EP1177178B1/fr not_active Expired - Lifetime
- 2000-04-27 HK HK02107871.7A patent/HK1046281A1/zh unknown
- 2000-04-27 BR BR0010342-0A patent/BR0010342A/pt not_active IP Right Cessation
- 2000-04-27 KR KR1020017014145A patent/KR20010112477A/ko not_active Ceased
- 2000-04-27 ES ES00927088T patent/ES2235869T3/es not_active Expired - Lifetime
- 2000-04-27 AT AT00927088T patent/ATE286029T1/de active
- 2000-04-27 TR TR2001/03221T patent/TR200103221T2/xx unknown
- 2000-04-27 PT PT00927088T patent/PT1177178E/pt unknown
- 2000-04-27 HU HU0202970A patent/HUP0202970A2/hu unknown
- 2000-04-27 CN CN00808364A patent/CN1353695A/zh active Pending
- 2000-04-27 AU AU45584/00A patent/AU4558400A/en not_active Abandoned
- 2000-04-27 DK DK00927088T patent/DK1177178T3/da active
- 2000-04-27 US US09/959,632 patent/US6696437B1/en not_active Expired - Lifetime
- 2000-04-27 SK SK1596-2001A patent/SK15962001A3/sk unknown
- 2000-05-05 AR ARP000102178A patent/AR029161A1/es unknown
- 2000-05-05 MY MYPI20001934A patent/MY122771A/en unknown
- 2000-05-05 CO CO00032472A patent/CO5170517A1/es not_active Application Discontinuation
2001
- 2001-10-19 ZA ZA200108609A patent/ZA200108609B/en unknown
- 2001-10-22 BG BG106035A patent/BG106035A/xx unknown
- 2001-11-02 NO NO20015362A patent/NO20015362D0/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
BR0010342A (pt)	2002-05-28
UA68436C2 (en)	2004-08-16
PL351558A1 (en)	2003-05-05
HK1046281A1 (zh)	2003-01-03
TR200103221T2 (tr)	2002-04-22
CN1353695A (zh)	2002-06-12
JP2002544199A (ja)	2002-12-24
CA2371645A1 (fr)	2000-11-16
EP1177178B1 (fr)	2004-12-29
MY122771A (en)	2006-05-31
JP4004737B2 (ja)	2007-11-07
AU4558400A (en)	2000-11-21
BG106035A (en)	2002-06-28
DE19920936A1 (de)	2000-11-09
EP1177178A1 (fr)	2002-02-06
DK1177178T3 (da)	2005-05-02
IL146147A0 (en)	2002-07-25
PT1177178E (pt)	2005-05-31
KR20010112477A (ko)	2001-12-20
US6696437B1 (en)	2004-02-24
DE50009118D1 (de)	2005-02-03
NO20015362L (no)	2001-11-02
HUP0202970A2 (hu)	2002-12-28
WO2000068206A1 (fr)	2000-11-16
CA2371645C (fr)	2007-04-17
CO5170517A1 (es)	2002-06-27
AR029161A1 (es)	2003-06-18
NO20015362D0 (no)	2001-11-02
ZA200108609B (en)	2002-10-21
ATE286029T1 (de)	2005-01-15
ES2235869T3 (es)	2005-07-16

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