HUP0303643A2 - Szteroid vegyületek, ezek felhasználása meiosis szabályozására alkalmas gyógyszerkészítmény előállítására és eljárás ezen vegyületek előállítására - Google Patents
Szteroid vegyületek, ezek felhasználása meiosis szabályozására alkalmas gyógyszerkészítmény előállítására és eljárás ezen vegyületek előállítására Download PDFInfo
- Publication number
- HUP0303643A2 HUP0303643A2 HU0303643A HUP0303643A HUP0303643A2 HU P0303643 A2 HUP0303643 A2 HU P0303643A2 HU 0303643 A HU0303643 A HU 0303643A HU P0303643 A HUP0303643 A HU P0303643A HU P0303643 A2 HUP0303643 A2 HU P0303643A2
- Authority
- HU
- Hungary
- Prior art keywords
- group
- pregna
- methyl
- formula
- substituted
- Prior art date
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- -1 Steroid compounds Chemical class 0.000 title claims abstract description 221
- 150000001875 compounds Chemical class 0.000 title claims description 98
- 238000002360 preparation method Methods 0.000 title claims description 65
- 238000000034 method Methods 0.000 title claims description 38
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 24
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 79
- 210000000287 oocyte Anatomy 0.000 claims abstract description 60
- 230000021121 meiosis Effects 0.000 claims abstract description 52
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 23
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 19
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 19
- 150000003431 steroids Chemical group 0.000 claims abstract description 19
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 16
- 125000003277 amino group Chemical group 0.000 claims abstract description 13
- 125000003118 aryl group Chemical group 0.000 claims abstract description 10
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims abstract description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
- 239000001257 hydrogen Substances 0.000 claims abstract description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 58
- 125000000217 alkyl group Chemical group 0.000 claims description 35
- 230000002829 reductive effect Effects 0.000 claims description 31
- 125000003342 alkenyl group Chemical group 0.000 claims description 19
- 230000008569 process Effects 0.000 claims description 19
- 125000002947 alkylene group Chemical group 0.000 claims description 17
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 16
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 150000001721 carbon Chemical group 0.000 claims description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
- 230000004720 fertilization Effects 0.000 claims description 14
- 125000000623 heterocyclic group Chemical group 0.000 claims description 14
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 14
- RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical group C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims description 13
- 230000001105 regulatory effect Effects 0.000 claims description 13
- 238000006268 reductive amination reaction Methods 0.000 claims description 12
- 229910052717 sulfur Inorganic materials 0.000 claims description 11
- 125000004434 sulfur atom Chemical group 0.000 claims description 11
- 238000001727 in vivo Methods 0.000 claims description 10
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 10
- 125000004122 cyclic group Chemical group 0.000 claims description 9
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 8
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 8
- 241000124008 Mammalia Species 0.000 claims description 8
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- 125000005843 halogen group Chemical group 0.000 claims description 8
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 8
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 7
- 230000033228 biological regulation Effects 0.000 claims description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 5
- 125000002252 acyl group Chemical group 0.000 claims description 5
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 150000007522 mineralic acids Chemical class 0.000 claims description 5
- 125000003172 aldehyde group Chemical group 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
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- 150000001412 amines Chemical class 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
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- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 claims description 4
- ZNWOYQVXPIEQRC-HOFZUOGSSA-N (8s,9s,10r,13s,14s,17r)-17-[(2s)-1-hydroxypropan-2-yl]-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@@H](CO)C)[C@@]1(C)CC2 ZNWOYQVXPIEQRC-HOFZUOGSSA-N 0.000 claims description 3
- MZAGXDHQGXUDDX-JSRXJHBZSA-N (e,2z)-4-ethyl-2-hydroxyimino-5-nitrohex-3-enamide Chemical compound [O-][N+](=O)C(C)C(/CC)=C/C(=N/O)/C(N)=O MZAGXDHQGXUDDX-JSRXJHBZSA-N 0.000 claims description 3
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 claims description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
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- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
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- 238000005804 alkylation reaction Methods 0.000 claims description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
- 230000031709 bromination Effects 0.000 claims description 3
- 238000005893 bromination reaction Methods 0.000 claims description 3
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
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- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 3
- 238000007269 dehydrobromination reaction Methods 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims description 3
- 125000000593 indol-1-yl group Chemical group [H]C1=C([H])C([H])=C2N([*])C([H])=C([H])C2=C1[H] 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 150000002825 nitriles Chemical class 0.000 claims description 3
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000004353 pyrazol-1-yl group Chemical group [H]C1=NN(*)C([H])=C1[H] 0.000 claims description 3
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 2
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 2
- 230000002254 contraceptive effect Effects 0.000 claims description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N iso-butene Natural products CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 2
- 125000000468 ketone group Chemical group 0.000 claims description 2
- 230000000269 nucleophilic effect Effects 0.000 claims description 2
- 238000010534 nucleophilic substitution reaction Methods 0.000 claims description 2
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 2
- 150000001993 dienes Chemical class 0.000 claims 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
- 125000004254 isoquinolin-1-yl group Chemical group [H]C1=C([H])C2=C([H])C([H])=C([H])C([H])=C2C(*)=N1 0.000 claims 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 34
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- 239000007921 spray Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 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
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000002381 testicular Effects 0.000 description 1
- UQCWXKSHRQJGPH-UHFFFAOYSA-M tetrabutylazanium;fluoride;hydrate Chemical compound O.[F-].CCCC[N+](CCCC)(CCCC)CCCC UQCWXKSHRQJGPH-UHFFFAOYSA-M 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 239000012581 transferrin Substances 0.000 description 1
- 125000004417 unsaturated alkyl group Chemical group 0.000 description 1
- 210000004291 uterus Anatomy 0.000 description 1
- 229940044950 vaginal gel Drugs 0.000 description 1
- 239000000029 vaginal gel Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
- C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
- C07J41/005—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 the 17-beta position being substituted by an uninterrupted chain of only two carbon atoms, e.g. pregnane derivatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/08—Drugs for genital or sexual disorders; Contraceptives for gonadal disorders or for enhancing fertility, e.g. inducers of ovulation or of spermatogenesis
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J43/00—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C07J43/003—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton not condensed
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Reproductive Health (AREA)
- Endocrinology (AREA)
- Gynecology & Obstetrics (AREA)
- Pregnancy & Childbirth (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP01250108A EP1245572A1 (en) | 2001-03-26 | 2001-03-26 | Aminosterol compounds, their use in the preparation of meiosis-regulating medicaments and method for their preparation |
| PCT/EP2002/003148 WO2002079220A2 (en) | 2001-03-26 | 2002-03-20 | Aminosterol compounds, their use in the preparation of meiosis-regulating medicaments and method for their preparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HUP0303643A2 true HUP0303643A2 (hu) | 2004-03-01 |
Family
ID=8181575
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU0303643A HUP0303643A2 (hu) | 2001-03-26 | 2002-03-20 | Szteroid vegyületek, ezek felhasználása meiosis szabályozására alkalmas gyógyszerkészítmény előállítására és eljárás ezen vegyületek előállítására |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US6916921B2 (https=) |
| EP (2) | EP1245572A1 (https=) |
| JP (1) | JP2004534011A (https=) |
| KR (1) | KR20030088043A (https=) |
| CN (1) | CN1332975C (https=) |
| AU (1) | AU2002315260B2 (https=) |
| BR (1) | BR0208381A (https=) |
| CA (1) | CA2438210A1 (https=) |
| CZ (1) | CZ20032578A3 (https=) |
| HU (1) | HUP0303643A2 (https=) |
| IL (1) | IL157272A0 (https=) |
| MX (1) | MXPA03008199A (https=) |
| NO (1) | NO20034273L (https=) |
| PL (1) | PL369576A1 (https=) |
| RU (1) | RU2289587C2 (https=) |
| UA (1) | UA75130C2 (https=) |
| WO (1) | WO2002079220A2 (https=) |
| ZA (1) | ZA200308271B (https=) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1514874A1 (en) * | 2003-07-28 | 2005-03-16 | Schering Aktiengesellschaft | Thiomorpholino steroid compounds, the use thereof for the preparation of meiosis regulating medicaments and method for the preparation thereof |
| KR100689260B1 (ko) * | 2005-05-24 | 2007-03-02 | 삼원산업주식회사 | 항산화성 스틸벤계 형광증백제 및 이의 합성방법 |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1095167A (en) * | 1963-12-05 | 1967-12-13 | Shalom Sarel | Amino-steroids |
| US3419661A (en) * | 1964-01-13 | 1968-12-31 | Univ Missouri | Oral contraceptive for birds |
| DE1643004A1 (de) * | 1967-02-07 | 1971-04-08 | Schering Ag | Bisnorcholenderivate und Verfahren zu ihrer Herstellung |
| DE1930473A1 (de) * | 1969-06-14 | 1970-12-17 | Schering Ag | 22-N-substituierte (20R)-23,24-dinor-cholanderivate |
| US5716777A (en) | 1994-06-23 | 1998-02-10 | Novo Nordisk A/S | Regulation of meiosis using sterols |
| HUP9800731A3 (en) * | 1995-03-06 | 2000-03-28 | Novo Nordisk As | Stimulation of meiosis |
| CA2224866A1 (en) | 1995-06-23 | 1997-01-09 | Novo Nordisk A/S | Meiosis regulating compounds |
| JP2001506656A (ja) | 1996-12-20 | 2001-05-22 | ノボ ノルディスク アクティーゼルスカブ | 減数分裂調節化合物 |
| WO1999058549A1 (en) * | 1998-05-13 | 1999-11-18 | Novo Nordisk A/S | Meiosis regulating compounds |
| EP1098652A2 (en) | 1998-05-26 | 2001-05-16 | Schering Aktiengesellschaft | Treatment of infertility with camp-increasing compounds alone or in combination with at least one meiosis-stimulating compound |
| CN1353617A (zh) | 1999-02-24 | 2002-06-12 | 诺沃挪第克公司 | 不孕症的治疗 |
| AU2794000A (en) | 1999-02-24 | 2000-09-14 | Novo Nordisk A/S | Treatment of infertility |
| CZ20012671A3 (cs) | 1999-02-26 | 2002-01-16 | Novo Nordisk A/S | Způsob in vitro oplodnění s pouľitím kultivačního média obsahujícího sterol aktivující meiosu |
| CA2382908A1 (en) | 1999-09-16 | 2001-03-22 | Novo Nordisk A/S | Composition for ivf |
| WO2001062260A2 (en) | 2000-02-25 | 2001-08-30 | Schering Aktiengesellschaft | Improvement of implantation rate |
| ATE386495T1 (de) * | 2001-02-06 | 2008-03-15 | Novo Nordisk As | Behältnis mit niedrigem sauerstoffgehalt, das ff- mas enthält |
| US6988613B2 (en) * | 2001-02-06 | 2006-01-24 | Novo Nordisk A/S | Composition for IVF |
-
2001
- 2001-03-26 EP EP01250108A patent/EP1245572A1/en not_active Withdrawn
-
2002
- 2002-03-20 IL IL15727202A patent/IL157272A0/xx unknown
- 2002-03-20 MX MXPA03008199A patent/MXPA03008199A/es active IP Right Grant
- 2002-03-20 KR KR10-2003-7012456A patent/KR20030088043A/ko not_active Ceased
- 2002-03-20 CA CA002438210A patent/CA2438210A1/en not_active Abandoned
- 2002-03-20 HU HU0303643A patent/HUP0303643A2/hu unknown
- 2002-03-20 EP EP02740430A patent/EP1401856A2/en not_active Withdrawn
- 2002-03-20 WO PCT/EP2002/003148 patent/WO2002079220A2/en not_active Ceased
- 2002-03-20 BR BR0208381-7A patent/BR0208381A/pt not_active IP Right Cessation
- 2002-03-20 CN CNB028073673A patent/CN1332975C/zh not_active Expired - Fee Related
- 2002-03-20 RU RU2003130228/04A patent/RU2289587C2/ru not_active IP Right Cessation
- 2002-03-20 AU AU2002315260A patent/AU2002315260B2/en not_active Ceased
- 2002-03-20 UA UA2003109610A patent/UA75130C2/uk unknown
- 2002-03-20 JP JP2002577844A patent/JP2004534011A/ja active Pending
- 2002-03-20 CZ CZ20032578A patent/CZ20032578A3/cs unknown
- 2002-03-20 PL PL02369576A patent/PL369576A1/xx not_active Application Discontinuation
- 2002-03-26 US US10/105,939 patent/US6916921B2/en not_active Expired - Fee Related
-
2003
- 2003-09-25 NO NO20034273A patent/NO20034273L/no not_active Application Discontinuation
- 2003-10-23 ZA ZA200308271A patent/ZA200308271B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| RU2003130228A (ru) | 2005-04-10 |
| ZA200308271B (en) | 2005-01-24 |
| PL369576A1 (en) | 2005-05-02 |
| IL157272A0 (en) | 2004-02-19 |
| JP2004534011A (ja) | 2004-11-11 |
| CA2438210A1 (en) | 2002-10-10 |
| WO2002079220A2 (en) | 2002-10-10 |
| NO20034273L (no) | 2003-11-25 |
| NO20034273D0 (no) | 2003-09-25 |
| CZ20032578A3 (cs) | 2003-12-17 |
| UA75130C2 (en) | 2006-03-15 |
| CN1332975C (zh) | 2007-08-22 |
| US6916921B2 (en) | 2005-07-12 |
| EP1245572A1 (en) | 2002-10-02 |
| AU2002315260B2 (en) | 2008-04-03 |
| WO2002079220A3 (en) | 2003-10-16 |
| CN1543473A (zh) | 2004-11-03 |
| MXPA03008199A (es) | 2004-01-29 |
| US20020188143A1 (en) | 2002-12-12 |
| KR20030088043A (ko) | 2003-11-15 |
| HK1070900A1 (en) | 2005-06-30 |
| RU2289587C2 (ru) | 2006-12-20 |
| EP1401856A2 (en) | 2004-03-31 |
| BR0208381A (pt) | 2004-06-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FD9A | Lapse of provisional protection due to non-payment of fees |