SK9892001A3 - Substituted 2-aryl-3-(heteroaryl)-imidazo[1,2-a]pyrimidines, and related pharmaceutical compositions and methods - Google Patents

Substituted 2-aryl-3-(heteroaryl)-imidazo[1,2-a]pyrimidines, and related pharmaceutical compositions and methods Download PDF

Info

Publication number: SK9892001A3
Authority: SK; Slovakia
Prior art keywords: compound; pyrimidin; amine; imidazo; formula
Prior art date: 1999-11-10

Application number

SK989-2001A

Other languages

English (en)

Slovak (sk)

Inventor

John H Dodd

James R Henry

Kenneth C Rupert

Original Assignee

Ortho Mcneil Pharm Inc

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.)

1999-11-10

Filing date

2000-10-27

Publication date

2002-04-04

2000-10-27 Application filed by Ortho Mcneil Pharm Inc filed Critical Ortho Mcneil Pharm Inc

2002-04-04 Publication of SK9892001A3 publication Critical patent/SK9892001A3/sk

Links

239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 12
238000000034 method Methods 0.000 title claims description 35
150000001875 compounds Chemical class 0.000 claims abstract description 122
102000004127 Cytokines Human genes 0.000 claims abstract description 14
108090000695 Cytokines Proteins 0.000 claims abstract description 14
230000002757 inflammatory effect Effects 0.000 claims abstract description 13
238000004519 manufacturing process Methods 0.000 claims abstract description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 39
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 27
-1 C 1-5 -alkoxy Chemical group 0.000 claims description 24
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 22
WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 19
229910052736 halogen Inorganic materials 0.000 claims description 18
150000002367 halogens Chemical class 0.000 claims description 18
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 15
230000000694 effects Effects 0.000 claims description 14
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
230000008569 process Effects 0.000 claims description 12
125000000623 heterocyclic group Chemical group 0.000 claims description 11
238000002360 preparation method Methods 0.000 claims description 10
239000003937 drug carrier Substances 0.000 claims description 8
206010039073 rheumatoid arthritis Diseases 0.000 claims description 8
WRIKHQLVHPKCJU-UHFFFAOYSA-N sodium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([Na])[Si](C)(C)C WRIKHQLVHPKCJU-UHFFFAOYSA-N 0.000 claims description 8
206010006895 Cachexia Diseases 0.000 claims description 7
125000003118 aryl group Chemical group 0.000 claims description 7
230000002401 inhibitory effect Effects 0.000 claims description 6
150000003839 salts Chemical class 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 5
229910052739 hydrogen Inorganic materials 0.000 claims description 5
BOJQXJHNUIWISM-UHFFFAOYSA-N imidazo[1,2-a]pyrimidin-7-amine Chemical compound N1=C(N)C=CN2C=CN=C21 BOJQXJHNUIWISM-UHFFFAOYSA-N 0.000 claims description 5
230000001404 mediated effect Effects 0.000 claims description 5
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
208000011231 Crohn disease Diseases 0.000 claims description 4
229910052799 carbon Inorganic materials 0.000 claims description 4
125000004076 pyridyl group Chemical group 0.000 claims description 4
125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 4
208000001132 Osteoporosis Diseases 0.000 claims description 3
206010040070 Septic Shock Diseases 0.000 claims description 3
210000001744 T-lymphocyte Anatomy 0.000 claims description 3
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 3
230000036303 septic shock Effects 0.000 claims description 3
229910052727 yttrium Inorganic materials 0.000 claims description 3
125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims description 2
DDRVSYCEZPPEJX-UHFFFAOYSA-N 2-(3-chloro-4-fluorophenyl)-3-pyridin-4-ylimidazo[1,2-a]pyrimidin-7-amine Chemical compound N1=C2N=C(N)C=CN2C(C=2C=CN=CC=2)=C1C1=CC=C(F)C(Cl)=C1 DDRVSYCEZPPEJX-UHFFFAOYSA-N 0.000 claims description 2
KVSJCXDUYDCCHX-UHFFFAOYSA-N 2-(3-chlorophenyl)-3-pyridin-4-ylimidazo[1,2-a]pyrimidin-7-amine Chemical compound N1=C2N=C(N)C=CN2C(C=2C=CN=CC=2)=C1C1=CC=CC(Cl)=C1 KVSJCXDUYDCCHX-UHFFFAOYSA-N 0.000 claims description 2
NDPHZWCAOHKRIE-UHFFFAOYSA-N 2-(3-fluorophenyl)-3-(2-methylsulfanylpyrimidin-4-yl)imidazo[1,2-a]pyrimidin-7-amine Chemical compound CSC1=NC=CC(C=2N3C=CC(N)=NC3=NC=2C=2C=C(F)C=CC=2)=N1 NDPHZWCAOHKRIE-UHFFFAOYSA-N 0.000 claims description 2
YQSFQNMEKQXOET-UHFFFAOYSA-N 2-(3-fluorophenyl)-3-pyridin-4-ylimidazo[1,2-a]pyrimidin-7-amine Chemical compound N1=C2N=C(N)C=CN2C(C=2C=CN=CC=2)=C1C1=CC=CC(F)=C1 YQSFQNMEKQXOET-UHFFFAOYSA-N 0.000 claims description 2
BVOXXCFSYHFTLW-UHFFFAOYSA-N 2-(4-fluorophenyl)-3-(2-methylsulfanylpyrimidin-4-yl)imidazo[1,2-a]pyrimidin-7-amine Chemical compound CSC1=NC=CC(C=2N3C=CC(N)=NC3=NC=2C=2C=CC(F)=CC=2)=N1 BVOXXCFSYHFTLW-UHFFFAOYSA-N 0.000 claims description 2
SYIUIQQRCPIBEM-INIZCTEOSA-N 2-(4-fluorophenyl)-3-[3-[[(1s)-1-phenylethyl]amino]pyridin-4-yl]imidazo[1,2-a]pyrimidin-7-amine Chemical compound N([C@@H](C)C=1C=CC=CC=1)C1=CN=CC=C1C(N1C=CC(N)=NC1=N1)=C1C1=CC=C(F)C=C1 SYIUIQQRCPIBEM-INIZCTEOSA-N 0.000 claims description 2
SXRLSMDAMBCWBT-UHFFFAOYSA-N 2-(4-fluorophenyl)-3-pyridin-4-ylimidazo[1,2-a]pyrimidin-7-amine Chemical compound N1=C2N=C(N)C=CN2C(C=2C=CN=CC=2)=C1C1=CC=C(F)C=C1 SXRLSMDAMBCWBT-UHFFFAOYSA-N 0.000 claims description 2
RFKYUEFCPXYIHY-UHFFFAOYSA-N 2-(4-fluorophenyl)-3-pyrimidin-4-ylimidazo[1,2-a]pyrimidin-7-amine Chemical compound N1=C2N=C(N)C=CN2C(C=2N=CN=CC=2)=C1C1=CC=C(F)C=C1 RFKYUEFCPXYIHY-UHFFFAOYSA-N 0.000 claims description 2
SXMGPKIFJDLHQD-UHFFFAOYSA-N 2-(4-fluorophenyl)-3-quinolin-4-ylimidazo[1,2-a]pyrimidin-7-amine Chemical compound N1=C2N=C(N)C=CN2C(C=2C3=CC=CC=C3N=CC=2)=C1C1=CC=C(F)C=C1 SXMGPKIFJDLHQD-UHFFFAOYSA-N 0.000 claims description 2
OUYMDMNELLLCOG-UHFFFAOYSA-N 2-phenyl-3-(2-piperidin-1-ylpyrimidin-4-yl)imidazo[1,2-a]pyrimidin-7-amine Chemical compound N1=C2N=C(N)C=CN2C(C=2N=C(N=CC=2)N2CCCCC2)=C1C1=CC=CC=C1 OUYMDMNELLLCOG-UHFFFAOYSA-N 0.000 claims description 2
KFEQXUZWOONGQK-INIZCTEOSA-N 2-phenyl-3-[2-[[(1s)-1-phenylethyl]amino]pyrimidin-4-yl]imidazo[1,2-a]pyrimidin-7-amine Chemical compound N([C@@H](C)C=1C=CC=CC=1)C(N=1)=NC=CC=1C(N1C=CC(N)=NC1=N1)=C1C1=CC=CC=C1 KFEQXUZWOONGQK-INIZCTEOSA-N 0.000 claims description 2
UEHYGDWDWNUCSG-UHFFFAOYSA-N 2-phenyl-3-pyridin-4-ylimidazo[1,2-a]pyrimidin-7-amine Chemical compound N1=C2N=C(N)C=CN2C(C=2C=CN=CC=2)=C1C1=CC=CC=C1 UEHYGDWDWNUCSG-UHFFFAOYSA-N 0.000 claims description 2
CECKFLSHKDGWGQ-UHFFFAOYSA-N 2-phenyl-3-pyrimidin-4-ylimidazo[1,2-a]pyrimidin-7-amine Chemical compound N1=C2N=C(N)C=CN2C(C=2N=CN=CC=2)=C1C1=CC=CC=C1 CECKFLSHKDGWGQ-UHFFFAOYSA-N 0.000 claims description 2
YGBTVRUWFYRCNE-UHFFFAOYSA-N 3-(2-methoxypyrimidin-4-yl)-2-phenylimidazo[1,2-a]pyrimidin-7-amine Chemical compound COC1=NC=CC(C=2N3C=CC(N)=NC3=NC=2C=2C=CC=CC=2)=N1 YGBTVRUWFYRCNE-UHFFFAOYSA-N 0.000 claims description 2
WYGVFMIQQCLMNX-UHFFFAOYSA-N 3-(2-methylsulfanylpyrimidin-4-yl)-2-phenylimidazo[1,2-a]pyrimidin-7-amine Chemical compound CSC1=NC=CC(C=2N3C=CC(N)=NC3=NC=2C=2C=CC=CC=2)=N1 WYGVFMIQQCLMNX-UHFFFAOYSA-N 0.000 claims description 2
LPWNNMVXRWQSBS-UHFFFAOYSA-N 3-(2-methylsulfonylpyrimidin-4-yl)-2-[3-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrimidin-7-amine Chemical compound CS(=O)(=O)C1=NC=CC(C=2N3C=CC(N)=NC3=NC=2C=2C=C(C=CC=2)C(F)(F)F)=N1 LPWNNMVXRWQSBS-UHFFFAOYSA-N 0.000 claims description 2
RNWWNLBSAXIAMZ-UHFFFAOYSA-N 3-(2-methylsulfonylpyrimidin-4-yl)-2-phenylimidazo[1,2-a]pyrimidin-7-amine Chemical compound CS(=O)(=O)C1=NC=CC(C=2N3C=CC(N)=NC3=NC=2C=2C=CC=CC=2)=N1 RNWWNLBSAXIAMZ-UHFFFAOYSA-N 0.000 claims description 2
UGOQPKUREUTQEZ-UHFFFAOYSA-N 3-[2-(benzylamino)pyridin-4-yl]-2-(4-fluorophenyl)imidazo[1,2-a]pyrimidin-7-amine Chemical compound N1=C2N=C(N)C=CN2C(C=2C=C(NCC=3C=CC=CC=3)N=CC=2)=C1C1=CC=C(F)C=C1 UGOQPKUREUTQEZ-UHFFFAOYSA-N 0.000 claims description 2
KKPXTSJLILQNDB-UHFFFAOYSA-N 3-[2-(benzylamino)pyridin-4-yl]-2-[3-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrimidin-7-amine Chemical compound N1=C2N=C(N)C=CN2C(C=2C=C(NCC=3C=CC=CC=3)N=CC=2)=C1C1=CC=CC(C(F)(F)F)=C1 KKPXTSJLILQNDB-UHFFFAOYSA-N 0.000 claims description 2
BRDJBMICYVWWGS-UHFFFAOYSA-N 3-[2-[(4-methoxyphenyl)methylamino]pyrimidin-4-yl]-2-phenylimidazo[1,2-a]pyrimidin-7-amine Chemical compound C1=CC(OC)=CC=C1CNC1=NC=CC(C=2N3C=CC(N)=NC3=NC=2C=2C=CC=CC=2)=N1 BRDJBMICYVWWGS-UHFFFAOYSA-N 0.000 claims description 2
FYTHWTYFVMCJNL-HNNXBMFYSA-N 3-[2-[[(1s)-1-cyclohexylethyl]amino]pyrimidin-4-yl]-2-(4-fluorophenyl)imidazo[1,2-a]pyrimidin-7-amine Chemical compound N([C@@H](C)C1CCCCC1)C(N=1)=NC=CC=1C(N1C=CC(N)=NC1=N1)=C1C1=CC=C(F)C=C1 FYTHWTYFVMCJNL-HNNXBMFYSA-N 0.000 claims description 2
NQNOOPZIWTUKRT-HNNXBMFYSA-N 3-[2-[[(1s)-1-phenylethyl]amino]pyrimidin-4-yl]-2-[3-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrimidin-7-amine Chemical compound N([C@@H](C)C=1C=CC=CC=1)C(N=1)=NC=CC=1C(N1C=CC(N)=NC1=N1)=C1C1=CC=CC(C(F)(F)F)=C1 NQNOOPZIWTUKRT-HNNXBMFYSA-N 0.000 claims description 2
INWFAMVJSJKINH-UHFFFAOYSA-N 3-pyridin-4-yl-2-[3-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrimidin-7-amine Chemical compound N1=C2N=C(N)C=CN2C(C=2C=CN=CC=2)=C1C1=CC=CC(C(F)(F)F)=C1 INWFAMVJSJKINH-UHFFFAOYSA-N 0.000 claims description 2
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201000001320 Atherosclerosis Diseases 0.000 claims description 2
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206010033645 Pancreatitis Diseases 0.000 claims description 2
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201000004681 Psoriasis Diseases 0.000 claims description 2
239000007868 Raney catalyst Substances 0.000 claims description 2
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims description 2
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QRDAPCMJAOQZSU-KQQUZDAGSA-N (e)-3-[4-[(e)-3-(3-fluorophenyl)-3-oxoprop-1-enyl]-1-methylpyrrol-2-yl]-n-hydroxyprop-2-enamide Chemical compound C1=C(\C=C\C(=O)NO)N(C)C=C1\C=C\C(=O)C1=CC=CC(F)=C1 QRDAPCMJAOQZSU-KQQUZDAGSA-N 0.000 claims 3
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PHDIJLFSKNMCMI-ITGJKDDRSA-N (3R,4S,5R,6R)-6-(hydroxymethyl)-4-(8-quinolin-6-yloxyoctoxy)oxane-2,3,5-triol Chemical compound OC[C@@H]1[C@H]([C@@H]([C@H](C(O1)O)O)OCCCCCCCCOC=1C=C2C=CC=NC2=CC=1)O PHDIJLFSKNMCMI-ITGJKDDRSA-N 0.000 claims 2
CYSWUSAYJNCAKA-FYJFLYSWSA-N ClC1=C(C=CC=2N=C(SC=21)OCC)OC1=CC=C(C=N1)/C=C/[C@H](C)NC(C)=O Chemical compound ClC1=C(C=CC=2N=C(SC=21)OCC)OC1=CC=C(C=N1)/C=C/[C@H](C)NC(C)=O CYSWUSAYJNCAKA-FYJFLYSWSA-N 0.000 claims 2
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HBENZIXOGRCSQN-VQWWACLZSA-N (1S,2S,6R,14R,15R,16R)-5-(cyclopropylmethyl)-16-[(2S)-2-hydroxy-3,3-dimethylpentan-2-yl]-15-methoxy-13-oxa-5-azahexacyclo[13.2.2.12,8.01,6.02,14.012,20]icosa-8(20),9,11-trien-11-ol Chemical compound N1([C@@H]2CC=3C4=C(C(=CC=3)O)O[C@H]3[C@@]5(OC)CC[C@@]2([C@@]43CC1)C[C@@H]5[C@](C)(O)C(C)(C)CC)CC1CC1 HBENZIXOGRCSQN-VQWWACLZSA-N 0.000 claims 1
VPMIAOSOTOODMY-KJAPKAAFSA-N (4r)-6-[(e)-2-[6-tert-butyl-4-(4-fluorophenyl)-2-propan-2-ylpyridin-3-yl]ethenyl]-4-hydroxyoxan-2-one Chemical compound C([C@H](O)C1)C(=O)OC1/C=C/C=1C(C(C)C)=NC(C(C)(C)C)=CC=1C1=CC=C(F)C=C1 VPMIAOSOTOODMY-KJAPKAAFSA-N 0.000 claims 1
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229940107700 pyruvic acid Drugs 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
230000028327 secretion Effects 0.000 description 1
230000011664 signaling Effects 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
230000000638 stimulation Effects 0.000 description 1
239000000126 substance Substances 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
238000010189 synthetic method Methods 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
238000007910 systemic administration Methods 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
OBRVWKVGULVSOR-UHFFFAOYSA-N tert-butyl 2-(benzylamino)-4-methyl-2h-pyridine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1C=CC(C)=CC1NCC1=CC=CC=C1 OBRVWKVGULVSOR-UHFFFAOYSA-N 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1
238000011200 topical administration Methods 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
230000009385 viral infection Effects 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000002699 waste material Substances 0.000 description 1
238000005303 weighing Methods 0.000 description 1
125000005023 xylyl group Chemical group 0.000 description 1
229940124629 β-receptor antagonist Drugs 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
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- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
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- 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

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Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Medicinal Chemistry (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Veterinary Medicine (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Immunology (AREA)
Physical Education & Sports Medicine (AREA)
Rheumatology (AREA)
Biomedical Technology (AREA)
Virology (AREA)
Orthopedic Medicine & Surgery (AREA)
Diabetes (AREA)
Communicable Diseases (AREA)
Neurosurgery (AREA)
Neurology (AREA)
Oncology (AREA)
Heart & Thoracic Surgery (AREA)
Dermatology (AREA)
Pain & Pain Management (AREA)
Cardiology (AREA)
Pulmonology (AREA)
Vascular Medicine (AREA)
Endocrinology (AREA)
Transplantation (AREA)
Hospice & Palliative Care (AREA)
Obesity (AREA)
Hematology (AREA)
Psychiatry (AREA)
Urology & Nephrology (AREA)
Emergency Medicine (AREA)

SK989-2001A 1999-11-10 2000-10-27 Substituted 2-aryl-3-(heteroaryl)-imidazo[1,2-a]pyrimidines, and related pharmaceutical compositions and methods SK9892001A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US16470099P	1999-11-10	1999-11-10
PCT/US2000/029875 WO2001034605A1 (en)	1999-11-10	2000-10-27	SUBSTITUTED 2-ARYL-3-(HETEROARYL)-IMIDAZO[1,2-a]PYRIMIDINES, AND RELATED PHARMACEUTICAL COMPOSITIONS AND METHODS

Publications (1)

Publication Number	Publication Date
SK9892001A3 true SK9892001A3 (en)	2002-04-04

Family

ID=22595694

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK989-2001A SK9892001A3 (en)	1999-11-10	2000-10-27	Substituted 2-aryl-3-(heteroaryl)-imidazo[1,2-a]pyrimidines, and related pharmaceutical compositions and methods

Country Status (27)

Country	Link
US (1)	US6610697B1 (de)
EP (1)	EP1140939B1 (de)
JP (1)	JP2003513977A (de)
KR (1)	KR20010089805A (de)
CN (1)	CN1255406C (de)
AR (1)	AR026410A1 (de)
AT (1)	ATE288915T1 (de)
AU (1)	AU784484B2 (de)
BG (1)	BG65106B1 (de)
BR (1)	BR0007447A (de)
CA (1)	CA2361139A1 (de)
CZ (1)	CZ20012494A3 (de)
DE (1)	DE60018037T2 (de)
ES (1)	ES2237470T3 (de)
HK (1)	HK1043591B (de)
HU (1)	HUP0200207A3 (de)
ID (1)	ID29514A (de)
IL (1)	IL144238A (de)
MX (1)	MXPA01007019A (de)
NO (1)	NO320422B1 (de)
NZ (1)	NZ512957A (de)
PL (1)	PL348924A1 (de)
PT (1)	PT1140939E (de)
RU (1)	RU2264403C2 (de)
SK (1)	SK9892001A3 (de)
UA (1)	UA70350C2 (de)
WO (1)	WO2001034605A1 (de)

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2000
- 2000-10-27 RU RU2001122339/04A patent/RU2264403C2/ru not_active IP Right Cessation
- 2000-10-27 CA CA002361139A patent/CA2361139A1/en not_active Abandoned
- 2000-10-27 NZ NZ512957A patent/NZ512957A/en unknown
- 2000-10-27 US US09/698,448 patent/US6610697B1/en not_active Expired - Lifetime
- 2000-10-27 AT AT00976710T patent/ATE288915T1/de not_active IP Right Cessation
- 2000-10-27 JP JP2001536552A patent/JP2003513977A/ja active Pending
- 2000-10-27 HU HU0200207A patent/HUP0200207A3/hu unknown
- 2000-10-27 CN CNB008045682A patent/CN1255406C/zh not_active Expired - Fee Related
- 2000-10-27 SK SK989-2001A patent/SK9892001A3/sk unknown
- 2000-10-27 UA UA2001075135A patent/UA70350C2/uk unknown
- 2000-10-27 CZ CZ20012494A patent/CZ20012494A3/cs unknown
- 2000-10-27 MX MXPA01007019A patent/MXPA01007019A/es active IP Right Grant
- 2000-10-27 AU AU14445/01A patent/AU784484B2/en not_active Ceased
- 2000-10-27 DE DE60018037T patent/DE60018037T2/de not_active Expired - Fee Related
- 2000-10-27 ES ES00976710T patent/ES2237470T3/es not_active Expired - Lifetime
- 2000-10-27 BR BR0007447-0A patent/BR0007447A/pt not_active IP Right Cessation
- 2000-10-27 WO PCT/US2000/029875 patent/WO2001034605A1/en not_active Ceased
- 2000-10-27 EP EP00976710A patent/EP1140939B1/de not_active Expired - Lifetime
- 2000-10-27 PT PT00976710T patent/PT1140939E/pt unknown
- 2000-10-27 KR KR1020017008715A patent/KR20010089805A/ko not_active Ceased
- 2000-10-27 PL PL00348924A patent/PL348924A1/xx not_active IP Right Cessation
- 2000-10-27 HK HK02105224.5A patent/HK1043591B/zh not_active IP Right Cessation
- 2000-10-27 ID IDW00200101720A patent/ID29514A/id unknown
- 2000-11-09 AR ARP000105910A patent/AR026410A1/es not_active Application Discontinuation
2001
- 2001-07-10 IL IL144238A patent/IL144238A/en not_active IP Right Cessation
- 2001-07-10 NO NO20013419A patent/NO320422B1/no not_active Application Discontinuation
- 2001-07-17 BG BG105712A patent/BG65106B1/bg unknown

Also Published As

Publication number	Publication date
HUP0200207A2 (hu)	2002-05-29
DE60018037T2 (de)	2006-01-12
AU1444501A (en)	2001-06-06
AR026410A1 (es)	2003-02-12
US6610697B1 (en)	2003-08-26
KR20010089805A (ko)	2001-10-08
HUP0200207A3 (en)	2004-07-28
HK1043591B (zh)	2006-12-29
ID29514A (id)	2001-09-06
EP1140939B1 (de)	2005-02-09
ATE288915T1 (de)	2005-02-15
NO20013419D0 (no)	2001-07-10
CZ20012494A3 (cs)	2001-10-17
UA70350C2 (en)	2004-10-15
PT1140939E (pt)	2005-05-31
IL144238A (en)	2007-03-08
CN1342162A (zh)	2002-03-27
BG65106B1 (bg)	2007-02-28
ES2237470T3 (es)	2005-08-01
EP1140939A1 (de)	2001-10-10
BG105712A (en)	2002-06-28
AU784484B2 (en)	2006-04-13
RU2264403C2 (ru)	2005-11-20
CN1255406C (zh)	2006-05-10
NZ512957A (en)	2005-01-28
BR0007447A (pt)	2002-04-09
NO320422B1 (no)	2005-12-05
JP2003513977A (ja)	2003-04-15
PL348924A1 (en)	2002-06-17
MXPA01007019A (es)	2002-09-18
WO2001034605A1 (en)	2001-05-17
NO20013419L (no)	2001-08-27
DE60018037D1 (de)	2005-03-17
HK1043591A1 (en)	2002-09-20
CA2361139A1 (en)	2001-05-17

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