UA68436C2 - Heterocycle-substituted benzimidazoles, pharmaceutical composition and method of treatment - Google Patents
Heterocycle-substituted benzimidazoles, pharmaceutical composition and method of treatment Download PDFInfo
- Publication number
- UA68436C2 UA68436C2 UA2001128419A UA2001128419A UA68436C2 UA 68436 C2 UA68436 C2 UA 68436C2 UA 2001128419 A UA2001128419 A UA 2001128419A UA 2001128419 A UA2001128419 A UA 2001128419A UA 68436 C2 UA68436 C2 UA 68436C2
- Authority
- UA
- Ukraine
- Prior art keywords
- carbon atoms
- alkyl
- amide
- benzimidazole
- carboxylic acid
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 20
- 150000001556 benzimidazoles Chemical class 0.000 title abstract description 22
- 239000008194 pharmaceutical composition Chemical class 0.000 title 1
- 125000004432 carbon atom Chemical group C* 0.000 claims description 77
- -1 hl or Chemical compound 0.000 claims description 67
- 125000000217 alkyl group Chemical group 0.000 claims description 49
- 239000001257 hydrogen Substances 0.000 claims description 41
- 229910052739 hydrogen Inorganic materials 0.000 claims description 41
- 150000001875 compounds 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 31
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 29
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 24
- 150000002431 hydrogen Chemical class 0.000 claims description 22
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 19
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 18
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 18
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 18
- 229910052794 bromium Inorganic materials 0.000 claims description 18
- 229910052731 fluorine Inorganic materials 0.000 claims description 18
- 239000011737 fluorine Substances 0.000 claims description 18
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 18
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 17
- 239000000460 chlorine Substances 0.000 claims description 17
- 229910052801 chlorine Inorganic materials 0.000 claims description 17
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 16
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 15
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 14
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 13
- 239000013543 active substance Substances 0.000 claims description 13
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 12
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 12
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 11
- 206010010904 Convulsion Diseases 0.000 claims description 9
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 9
- 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
- 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
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 7
- 125000000623 heterocyclic group Chemical group 0.000 claims description 7
- 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
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
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- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 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
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- 206010028980 Neoplasm Diseases 0.000 claims description 5
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 5
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 5
- 229940126601 medicinal product Drugs 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 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
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 4
- 208000035475 disorder Diseases 0.000 claims description 4
- 206010015037 epilepsy Diseases 0.000 claims description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-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
- 230000004770 neurodegeneration Effects 0.000 claims description 4
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 4
- 230000002265 prevention Effects 0.000 claims description 4
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 4
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- 125000004122 cyclic group Chemical group 0.000 claims description 3
- 230000009089 cytolysis Effects 0.000 claims description 3
- 206010012601 diabetes mellitus Diseases 0.000 claims description 3
- 210000003734 kidney Anatomy 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 229940002612 prodrug Drugs 0.000 claims description 3
- 239000000651 prodrug Substances 0.000 claims description 3
- 206010039073 rheumatoid arthritis Diseases 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
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- 206010000891 acute myocardial infarction Diseases 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
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- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 claims description 2
- 125000000612 phthaloyl group Chemical group C(C=1C(C(=O)*)=CC=CC1)(=O)* 0.000 claims description 2
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims description 2
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- KKJUPNGICOCCDW-UHFFFAOYSA-N 7-N,N-Dimethylamino-1,2,3,4,5-pentathiocyclooctane Chemical compound CN(C)C1CSSSSSC1 KKJUPNGICOCCDW-UHFFFAOYSA-N 0.000 claims 1
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- 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
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Landscapes
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- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Diabetes (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Communicable Diseases (AREA)
- Psychology (AREA)
- Heart & Thoracic Surgery (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Oncology (AREA)
- Cardiology (AREA)
- Urology & Nephrology (AREA)
- Immunology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyridine Compounds (AREA)
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 (de) | 1999-05-07 | 2000-04-27 | Heterozyklisch substituierte benzimidazole, deren herstellung und anwendung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA68436C2 true UA68436C2 (en) | 2004-08-16 |
Family
ID=7907219
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UA2001128419A UA68436C2 (en) | 1999-05-07 | 2000-04-27 | Heterocycle-substituted benzimidazoles, pharmaceutical composition and method of treatment |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US6696437B1 (da) |
| EP (1) | EP1177178B1 (da) |
| JP (1) | JP4004737B2 (da) |
| KR (1) | KR20010112477A (da) |
| CN (1) | CN1353695A (da) |
| AR (1) | AR029161A1 (da) |
| AT (1) | ATE286029T1 (da) |
| AU (1) | AU4558400A (da) |
| BG (1) | BG106035A (da) |
| BR (1) | BR0010342A (da) |
| CA (1) | CA2371645C (da) |
| CO (1) | CO5170517A1 (da) |
| DE (2) | DE19920936A1 (da) |
| DK (1) | DK1177178T3 (da) |
| ES (1) | ES2235869T3 (da) |
| HK (1) | HK1046281A1 (da) |
| HU (1) | HUP0202970A2 (da) |
| IL (1) | IL146147A0 (da) |
| MY (1) | MY122771A (da) |
| NO (1) | NO20015362D0 (da) |
| PL (1) | PL351558A1 (da) |
| PT (1) | PT1177178E (da) |
| SK (1) | SK15962001A3 (da) |
| TR (1) | TR200103221T2 (da) |
| UA (1) | UA68436C2 (da) |
| WO (1) | WO2000068206A1 (da) |
| ZA (1) | ZA200108609B (da) |
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| US7064215B2 (en) | 2001-07-03 | 2006-06-20 | Chiron Corporation | Indazole benzimidazole compounds |
| WO2003066629A2 (en) * | 2002-02-06 | 2003-08-14 | Vertex Pharmaceuticals Incorporated | Heteroaryl compounds useful as inhibitors of gsk-3 |
| DE10227668A1 (de) * | 2002-06-20 | 2004-01-08 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Arzneimittel zur Behandlung des systemic inflammatory response syndrome |
| WO2004013333A2 (de) | 2002-07-26 | 2004-02-12 | Basf Plant Science Gmbh | Revertierung der negativ-selektiven wirkung von negativen markerproteinen als selektionsverfahren |
| ATE425753T1 (de) | 2002-08-02 | 2009-04-15 | Genesoft Pharmaceuticals Inc | Biaryl-verbindungen mit antiinfektiver wirkung |
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| WO2004024655A2 (en) | 2002-09-12 | 2004-03-25 | Avanir Pharmaceuticals | Phenyl-indole compounds for modulating ige and inhibiting cellular proliferation |
| TW200424188A (en) | 2002-10-01 | 2004-11-16 | Mitsubishi Pharma Corp | Isoquinoline compound and pharmaceutical use thereof |
| EP1562931A2 (en) | 2002-10-25 | 2005-08-17 | Genesoft Pharmaceuticals, Inc. | Anti-infective biaryl compounds |
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| JP2006509027A (ja) | 2002-12-10 | 2006-03-16 | オーシェント ファーマシューティカルズ コーポレーション | （ピロールカルボキサミド）−（ベンズアミド）−（イミダゾールカルボキサミド）モチーフを有する抗菌化合物 |
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| TW201500358A (zh) | 2010-12-16 | 2015-01-01 | 赫夫門羅氏藥廠股份有限公司 | 三環ｐｉ３ｋ抑制劑化合物及其使用方法 |
| RU2013138835A (ru) | 2011-02-09 | 2015-03-20 | Ф. Хоффманн-Ля Рош Аг | Гетероциклические соединения в качестве ингибиторов pi3 киназы |
| KR101827444B1 (ko) * | 2012-02-01 | 2018-02-08 | 제일약품주식회사 | 트리사이클로 유도체 화합물의 신규한 결정형 산부가염 또는 이의 수화물 및 이의 제조방법 |
| KR20160042811A (ko) | 2013-03-20 | 2016-04-20 | 압토스 바이오사이언시스 인코포레이티드 | 2-치환 이미다조[4,5-d]페난쓰롤린 유도체 및 암 치료에 있어서의 이의 용도 |
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| WO2014198241A1 (en) * | 2013-06-14 | 2014-12-18 | Sunshine Lake Pharma Co., Ltd. | Thio-1,2,4-triazole derivatives and method for preparing the same |
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| CN103936719A (zh) * | 2014-05-14 | 2014-07-23 | 中国药科大学 | 苯并咪唑类衍生物制备方法及用途 |
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| CN105712937B (zh) * | 2016-02-28 | 2019-02-22 | 河北宁格生物医药科技有限公司 | 一种治疗转移性肿瘤的化合物及其用途 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA885929B (en) * | 1987-08-25 | 1989-04-26 | Oxi Gene Inc | Agents for use in tumor or cancer cell killing therapy |
| EP0841924B1 (en) * | 1995-08-02 | 2002-10-02 | Newcastle University Ventures Limited | Benzimidazole compounds |
| JP4373497B2 (ja) * | 1996-06-19 | 2009-11-25 | ローン−プーラン・ロレ・リミテツド | 置換されたアザビシクロ化合物、ならびにｔｎｆおよびサイクリックａｍｐホスホジエステラーゼ産生の阻害剤としてのそれらの使用 |
| IL142917A0 (en) * | 1998-11-03 | 2002-04-21 | Basf Ag | Substituted 2-phenylbenzimidazoles, the production thereof and their use |
| HRP20010451A2 (en) * | 1998-11-17 | 2003-04-30 | Basf Ag | 2-phenylbenzimidazoles and 2-phenylindoles, and production and use thereof |
| TR200101498T2 (tr) * | 1998-11-27 | 2001-11-21 | Basf Aktiengesellschaft | İkameli benzimidazoller ve parp inhibitörleri olarak kullanımları |
-
1999
- 1999-05-07 DE DE19920936A patent/DE19920936A1/de not_active Withdrawn
-
2000
- 2000-04-27 AT AT00927088T patent/ATE286029T1/de active
- 2000-04-27 UA UA2001128419A patent/UA68436C2/uk unknown
- 2000-04-27 DK DK00927088T patent/DK1177178T3/da active
- 2000-04-27 CA CA002371645A patent/CA2371645C/en not_active Expired - Fee Related
- 2000-04-27 TR TR2001/03221T patent/TR200103221T2/xx unknown
- 2000-04-27 SK SK1596-2001A patent/SK15962001A3/sk unknown
- 2000-04-27 BR BR0010342-0A patent/BR0010342A/pt not_active IP Right Cessation
- 2000-04-27 WO PCT/EP2000/003813 patent/WO2000068206A1/de not_active Ceased
- 2000-04-27 ES ES00927088T patent/ES2235869T3/es not_active Expired - Lifetime
- 2000-04-27 CN CN00808364A patent/CN1353695A/zh active Pending
- 2000-04-27 KR KR1020017014145A patent/KR20010112477A/ko not_active Ceased
- 2000-04-27 HK HK02107871.7A patent/HK1046281A1/zh unknown
- 2000-04-27 PL PL00351558A patent/PL351558A1/xx not_active Application Discontinuation
- 2000-04-27 PT PT00927088T patent/PT1177178E/pt unknown
- 2000-04-27 US US09/959,632 patent/US6696437B1/en not_active Expired - Lifetime
- 2000-04-27 IL IL14614700A patent/IL146147A0/xx unknown
- 2000-04-27 DE DE50009118T patent/DE50009118D1/de not_active Expired - Lifetime
- 2000-04-27 JP JP2000617186A patent/JP4004737B2/ja not_active Expired - Fee Related
- 2000-04-27 EP EP00927088A patent/EP1177178B1/de not_active Expired - Lifetime
- 2000-04-27 AU AU45584/00A patent/AU4558400A/en not_active Abandoned
- 2000-04-27 HU HU0202970A patent/HUP0202970A2/hu unknown
- 2000-05-05 MY MYPI20001934A patent/MY122771A/en unknown
- 2000-05-05 CO CO00032472A patent/CO5170517A1/es not_active Application Discontinuation
- 2000-05-05 AR ARP000102178A patent/AR029161A1/es unknown
-
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 |
|---|---|
| KR20010112477A (ko) | 2001-12-20 |
| BR0010342A (pt) | 2002-05-28 |
| HK1046281A1 (zh) | 2003-01-03 |
| DE50009118D1 (de) | 2005-02-03 |
| AR029161A1 (es) | 2003-06-18 |
| EP1177178A1 (de) | 2002-02-06 |
| MY122771A (en) | 2006-05-31 |
| NO20015362L (no) | 2001-11-02 |
| CN1353695A (zh) | 2002-06-12 |
| CO5170517A1 (es) | 2002-06-27 |
| JP2002544199A (ja) | 2002-12-24 |
| ES2235869T3 (es) | 2005-07-16 |
| AU4558400A (en) | 2000-11-21 |
| DK1177178T3 (da) | 2005-05-02 |
| SK15962001A3 (sk) | 2002-06-04 |
| ZA200108609B (en) | 2002-10-21 |
| IL146147A0 (en) | 2002-07-25 |
| WO2000068206A1 (de) | 2000-11-16 |
| PT1177178E (pt) | 2005-05-31 |
| US6696437B1 (en) | 2004-02-24 |
| CA2371645A1 (en) | 2000-11-16 |
| DE19920936A1 (de) | 2000-11-09 |
| JP4004737B2 (ja) | 2007-11-07 |
| BG106035A (en) | 2002-06-28 |
| EP1177178B1 (de) | 2004-12-29 |
| PL351558A1 (en) | 2003-05-05 |
| TR200103221T2 (tr) | 2002-04-22 |
| CA2371645C (en) | 2007-04-17 |
| NO20015362D0 (no) | 2001-11-02 |
| ATE286029T1 (de) | 2005-01-15 |
| HUP0202970A2 (hu) | 2002-12-28 |
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