UA64713C2 - Похідні азолідиндіону, спосіб їх одержання (варіанти), фармацевтичні композиції на їх основі, спосіб попередження або лікування, спосіб зниження рівня глюкози і проміжна сполука - Google Patents

Похідні азолідиндіону, спосіб їх одержання (варіанти), фармацевтичні композиції на їх основі, спосіб попередження або лікування, спосіб зниження рівня глюкози і проміжна сполука Download PDF

Info

Publication number: UA64713C2
Authority: UA; Ukraine
Prior art keywords: denotes; group; oxo; dihydro; compound
Prior art date: 1996-12-31

Application number

UA98126783A

Other languages

English (en)

Russian (ru)

Ukrainian (uk)

Inventor

Відіа Бхушан Лорей

Брадж Бхушан Лорей

Рао Бхеема Параселлі

Ранга Мадхаван Гуррам

Раджагопалан Рамануджам

Ранджан Чакрабарті

Сарма К.С. Пакала

Original Assignee

Reddys Lab Ltd Dr

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.)

1996-12-31

Filing date

1997-06-30

Publication date

2004-03-15

1996-12-31 Priority claimed from US08/777,627 external-priority patent/US5885997A/en

1997-06-30 Application filed by Reddys Lab Ltd Dr filed Critical Reddys Lab Ltd Dr

2004-03-15 Publication of UA64713C2 publication Critical patent/UA64713C2/uk

Links

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239000008103 glucose Substances 0.000 title claims description 5
230000002265 prevention Effects 0.000 title claims description 4
QFYXSLAAXZTRLG-UHFFFAOYSA-N pyrrolidine-2,3-dione Chemical class O=C1CCNC1=O QFYXSLAAXZTRLG-UHFFFAOYSA-N 0.000 title abstract description 11
238000004519 manufacturing process Methods 0.000 title description 5
150000003839 salts Chemical class 0.000 claims abstract description 82
239000012453 solvate Substances 0.000 claims abstract description 17
238000006243 chemical reaction Methods 0.000 claims description 114
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125000000217 alkyl group Chemical group 0.000 claims description 59
229910052739 hydrogen Inorganic materials 0.000 claims description 56
239000001257 hydrogen Substances 0.000 claims description 55
229910052757 nitrogen Inorganic materials 0.000 claims description 51
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 48
239000000243 solution Substances 0.000 claims description 47
239000002253 acid Substances 0.000 claims description 41
ZOBPZXTWZATXDG-UHFFFAOYSA-N 1,3-thiazolidine-2,4-dione Chemical compound O=C1CSC(=O)N1 ZOBPZXTWZATXDG-UHFFFAOYSA-N 0.000 claims description 40
125000004433 nitrogen atom Chemical group N* 0.000 claims description 39
229910052736 halogen Inorganic materials 0.000 claims description 33
150000002367 halogens Chemical class 0.000 claims description 33
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 32
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IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 27
125000003118 aryl group Chemical group 0.000 claims description 27
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NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 18
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QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 17
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125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 16
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125000001072 heteroaryl group Chemical group 0.000 claims description 12
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125000004442 acylamino group Chemical group 0.000 claims description 10
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125000005647 linker group Chemical group 0.000 claims description 10
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229910052783 alkali metal Inorganic materials 0.000 claims description 9
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 9
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125000004183 alkoxy alkyl group Chemical group 0.000 claims description 8
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206010012601 diabetes mellitus Diseases 0.000 claims description 8
125000004475 heteroaralkyl group Chemical group 0.000 claims description 8
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UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 8
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125000004414 alkyl thio group Chemical group 0.000 claims description 7
230000015572 biosynthetic process Effects 0.000 claims description 7
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
239000000945 filler Substances 0.000 claims description 7
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208000035475 disorder Diseases 0.000 claims description 6
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239000003937 drug carrier Substances 0.000 claims description 5
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
150000003626 triacylglycerols Chemical class 0.000 claims description 5
201000001320 Atherosclerosis Diseases 0.000 claims description 4
208000024172 Cardiovascular disease Diseases 0.000 claims description 4
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125000000000 cycloalkoxy group Chemical group 0.000 claims description 4
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125000004957 naphthylene group Chemical group 0.000 claims description 4
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 4
239000000843 powder Substances 0.000 claims description 4
125000000542 sulfonic acid group Chemical group 0.000 claims description 4
125000004001 thioalkyl group Chemical group 0.000 claims description 4
208000007342 Diabetic Nephropathies Diseases 0.000 claims description 3
206010018364 Glomerulonephritis Diseases 0.000 claims description 3
206010027525 Microalbuminuria Diseases 0.000 claims description 3
206010029164 Nephrotic syndrome Diseases 0.000 claims description 3
125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 3
125000005334 azaindolyl group Chemical group N1N=C(C2=CC=CC=C12)* 0.000 claims description 3
125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 3
239000002775 capsule Substances 0.000 claims description 3
239000003153 chemical reaction reagent Substances 0.000 claims description 3
208000029078 coronary artery disease Diseases 0.000 claims description 3
208000033679 diabetic kidney disease Diseases 0.000 claims description 3
206010061989 glomerulosclerosis Diseases 0.000 claims description 3
201000009925 nephrosclerosis Diseases 0.000 claims description 3
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
230000008289 pathophysiological mechanism Effects 0.000 claims description 3
239000006188 syrup Substances 0.000 claims description 3
235000020357 syrup Nutrition 0.000 claims description 3
229910052727 yttrium Inorganic materials 0.000 claims description 3
125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 2
208000002705 Glucose Intolerance Diseases 0.000 claims description 2
150000008064 anhydrides Chemical class 0.000 claims description 2
229910052799 carbon Inorganic materials 0.000 claims description 2
125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 2
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims description 2
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239000011734 sodium Substances 0.000 claims description 2
230000009466 transformation Effects 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims 19
208000032928 Dyslipidaemia Diseases 0.000 claims 1
101000939500 Homo sapiens UBX domain-containing protein 11 Proteins 0.000 claims 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
208000017170 Lipid metabolism disease Diseases 0.000 claims 1
SSURCGGGQUWIHH-UHFFFAOYSA-N NNON Chemical compound NNON SSURCGGGQUWIHH-UHFFFAOYSA-N 0.000 claims 1
102100029645 UBX domain-containing protein 11 Human genes 0.000 claims 1
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims 1
235000021588 free fatty acids Nutrition 0.000 claims 1
230000002140 halogenating effect Effects 0.000 claims 1
MXBFSAYTTZBUBY-UHFFFAOYSA-N n-chlorohydroxylamine Chemical compound ONCl MXBFSAYTTZBUBY-UHFFFAOYSA-N 0.000 claims 1
GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 claims 1
229910052708 sodium Inorganic materials 0.000 claims 1
239000000203 mixture Substances 0.000 abstract description 56
230000003178 anti-diabetic effect Effects 0.000 abstract description 5
239000003472 antidiabetic agent Substances 0.000 abstract description 5
238000002360 preparation method Methods 0.000 description 108
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 100
238000005481 NMR spectroscopy Methods 0.000 description 83
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 78
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 66
239000002904 solvent Substances 0.000 description 64
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 60
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 50
239000002585 base Substances 0.000 description 45
230000008018 melting Effects 0.000 description 35
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XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 34
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 33
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 31
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 30
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
239000011541 reaction mixture Substances 0.000 description 29
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 27
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229960000583 acetic acid Drugs 0.000 description 22
150000007513 acids Chemical class 0.000 description 21
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LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 16
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CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
239000000284 extract Substances 0.000 description 12
239000003054 catalyst Substances 0.000 description 11
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 10
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239000011261 inert gas Substances 0.000 description 9
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XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 8
229910052740 iodine Inorganic materials 0.000 description 8
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
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238000002425 crystallisation Methods 0.000 description 5
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/34—One oxygen atom
- C07D239/36—One oxygen atom as doubly bound oxygen atom or as unsubstituted hydroxy radical
- 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
- 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
- A61P3/06—Antihyperlipidemics
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
- 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
- C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
- C07D239/88—Oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/34—Oxygen atoms
- 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
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Diabetes (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Life Sciences & Earth Sciences (AREA)
Hematology (AREA)
Obesity (AREA)
Engineering & Computer Science (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Pharmacology & Pharmacy (AREA)
Bioinformatics & Cheminformatics (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Emergency Medicine (AREA)
Endocrinology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

UA98126783A 1996-12-31 1997-06-30 Похідні азолідиндіону, спосіб їх одержання (варіанти), фармацевтичні композиції на їх основі, спосіб попередження або лікування, спосіб зниження рівня глюкози і проміжна сполука UA64713C2 (uk)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US08/777,627 US5885997A (en)	1996-07-01	1996-12-31	Heterocyclic compounds, process for their preparation and pharmaceutical compositions containing them and their use in the treatment of diabetes and related diseases
PCT/US1997/011522 WO1997041097A2 (en)	1996-12-31	1997-06-30	Novel heterocyclic compounds process for their preparation and pharmaceutical compositions containing them and their use in the treatment of diabetes and related diseases

Publications (1)

Publication Number	Publication Date
UA64713C2 true UA64713C2 (uk)	2004-03-15

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Application Number	Title	Priority Date	Filing Date
UA98126783A UA64713C2 (uk)	1996-12-31	1997-06-30	Похідні азолідиндіону, спосіб їх одержання (варіанти), фармацевтичні композиції на їх основі, спосіб попередження або лікування, спосіб зниження рівня глюкози і проміжна сполука

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EP (1)	EP0958296B1 (de)
JP (1)	JP4339402B2 (de)
CN (1)	CN1190434C (de)
AT (1)	ATE246190T1 (de)
DE (1)	DE69723869T2 (de)
DK (1)	DK0958296T3 (de)
ES (1)	ES2199366T3 (de)
HU (1)	HUP0301101A3 (de)
IL (2)	IL127296A (de)
NO (1)	NO313699B1 (de)
PL (1)	PL192664B1 (de)
PT (1)	PT958296E (de)
RU (1)	RU2200161C2 (de)
UA (1)	UA64713C2 (de)
WO (1)	WO1997041097A2 (de)

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- 1997-06-30 DE DE69723869T patent/DE69723869T2/de not_active Expired - Lifetime
- 1997-06-30 RU RU98123195/04A patent/RU2200161C2/ru active
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Publication number	Publication date
PL342608A1 (en)	2001-06-18
CN1190434C (zh)	2005-02-23
EP0958296A1 (de)	1999-11-24
IL142649A (en)	2004-12-15
HK1026204A1 (en)	2000-12-08
HUP0301101A2 (hu)	2003-12-29
DK0958296T3 (da)	2003-08-18
WO1997041097A2 (en)	1997-11-06
PT958296E (pt)	2003-11-28
DE69723869D1 (de)	2003-09-04
IL127296A (en)	2003-01-12
HUP0301101A3 (en)	2009-03-30
NO313699B1 (no)	2002-11-18
RU2200161C2 (ru)	2003-03-10
IL127296A0 (en)	1999-09-22
IL142649A0 (en)	2002-03-10
DE69723869T2 (de)	2004-04-22
PL192664B1 (pl)	2006-11-30
ATE246190T1 (de)	2003-08-15
JP2002515874A (ja)	2002-05-28
ES2199366T3 (es)	2004-02-16
CN1275982A (zh)	2000-12-06
NO986055D0 (no)	1998-12-22
NO986055L (no)	1998-12-22
EP0958296B1 (de)	2003-07-30
JP4339402B2 (ja)	2009-10-07

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