UA78058C2 - Pyrrolidine derivative as oxitocin antagonists - Google Patents
Pyrrolidine derivative as oxitocin antagonists Download PDFInfo
- Publication number
- UA78058C2 UA78058C2 UA20041210895A UA20041210895A UA78058C2 UA 78058 C2 UA78058 C2 UA 78058C2 UA 20041210895 A UA20041210895 A UA 20041210895A UA 20041210895 A UA20041210895 A UA 20041210895A UA 78058 C2 UA78058 C2 UA 78058C2
- Authority
- UA
- Ukraine
- Prior art keywords
- group
- biphenyl
- pyrrolidin
- formula
- ylcarbonyl
- Prior art date
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- FKCMADOPPWWGNZ-YUMQZZPRSA-N [(2r)-1-[(2s)-2-amino-3-methylbutanoyl]pyrrolidin-2-yl]boronic acid Chemical compound CC(C)[C@H](N)C(=O)N1CCC[C@H]1B(O)O FKCMADOPPWWGNZ-YUMQZZPRSA-N 0.000 title claims abstract description 26
- 239000005557 antagonist Substances 0.000 title description 6
- 239000000203 mixture Substances 0.000 claims abstract description 76
- 208000005107 Premature Birth Diseases 0.000 claims abstract description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 21
- 206010036590 Premature baby Diseases 0.000 claims abstract description 18
- 206010013935 Dysmenorrhoea Diseases 0.000 claims abstract description 14
- 150000003839 salts Chemical class 0.000 claims abstract description 14
- 208000005171 Dysmenorrhea Diseases 0.000 claims abstract description 13
- 230000002265 prevention Effects 0.000 claims abstract description 7
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 154
- -1 sulfonyloxy group Chemical group 0.000 claims description 56
- 101800000989 Oxytocin Proteins 0.000 claims description 50
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- 229960001723 oxytocin Drugs 0.000 claims description 50
- XNOPRXBHLZRZKH-DSZYJQQASA-N oxytocin Chemical compound C([C@H]1C(=O)N[C@H](C(N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CSSC[C@H](N)C(=O)N1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC(C)C)C(=O)NCC(N)=O)=O)[C@@H](C)CC)C1=CC=C(O)C=C1 XNOPRXBHLZRZKH-DSZYJQQASA-N 0.000 claims description 45
- 125000003118 aryl group Chemical group 0.000 claims description 34
- 125000001072 heteroaryl group Chemical group 0.000 claims description 31
- 238000000034 method Methods 0.000 claims description 29
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- 230000000694 effects Effects 0.000 claims description 23
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 19
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 15
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
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- QGKLPGKXAVVPOJ-UHFFFAOYSA-N pyrrolidin-3-one Chemical compound O=C1CCNC1 QGKLPGKXAVVPOJ-UHFFFAOYSA-N 0.000 claims description 15
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- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 9
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 8
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- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
- 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 claims description 7
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- 230000027455 binding Effects 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
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- 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 1
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- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- SBMSLRMNBSMKQC-UHFFFAOYSA-N pyrrolidin-1-amine Chemical class NN1CCCC1 SBMSLRMNBSMKQC-UHFFFAOYSA-N 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 238000005932 reductive alkylation reaction Methods 0.000 description 1
- 230000002040 relaxant effect Effects 0.000 description 1
- 201000004193 respiratory failure Diseases 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 230000005070 ripening Effects 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 229960002052 salbutamol Drugs 0.000 description 1
- 238000003345 scintillation counting Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 230000003248 secreting effect Effects 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 238000010956 selective crystallization Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 150000003385 sodium Chemical class 0.000 description 1
- DVWOYOSIEJRHKW-UIRZNSHLSA-M sodium (2S)-2-[[(2S)-2-[[(4,4-difluorocyclohexyl)-phenylmethoxy]carbonylamino]-4-methylpentanoyl]amino]-1-hydroxy-3-[(3S)-2-oxopyrrolidin-3-yl]propane-1-sulfonate Chemical compound FC1(CCC(CC1)C(OC(=O)N[C@H](C(=O)N[C@H](C(S(=O)(=O)[O-])O)C[C@H]1C(NCC1)=O)CC(C)C)C1=CC=CC=C1)F.[Na+] DVWOYOSIEJRHKW-UIRZNSHLSA-M 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 230000008925 spontaneous activity Effects 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000012089 stop solution Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 230000006794 tachycardia Effects 0.000 description 1
- 235000015523 tannic acid Nutrition 0.000 description 1
- 229940033123 tannic acid Drugs 0.000 description 1
- 229920002258 tannic acid Polymers 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229960000195 terbutaline Drugs 0.000 description 1
- BNWCETAHAJSBFG-UHFFFAOYSA-N tert-butyl 2-bromoacetate Chemical compound CC(C)(C)OC(=O)CBr BNWCETAHAJSBFG-UHFFFAOYSA-N 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
- 150000003512 tertiary amines Chemical class 0.000 description 1
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 150000003555 thioacetals Chemical class 0.000 description 1
- 229940125712 tocolytic agent Drugs 0.000 description 1
- 239000003675 tocolytic agent Substances 0.000 description 1
- 230000003195 tocolytic effect Effects 0.000 description 1
- 210000003437 trachea Anatomy 0.000 description 1
- BJBUEDPLEOHJGE-IMJSIDKUSA-N trans-3-hydroxy-L-proline Chemical compound O[C@H]1CC[NH2+][C@@H]1C([O-])=O BJBUEDPLEOHJGE-IMJSIDKUSA-N 0.000 description 1
- 125000004953 trihalomethyl group Chemical group 0.000 description 1
- 239000001226 triphosphate Substances 0.000 description 1
- 235000011178 triphosphate Nutrition 0.000 description 1
- UNXRWKVEANCORM-UHFFFAOYSA-N triphosphoric acid Chemical compound OP(O)(=O)OP(O)(=O)OP(O)(O)=O UNXRWKVEANCORM-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 229960000281 trometamol Drugs 0.000 description 1
- 230000001228 trophic effect Effects 0.000 description 1
- 230000002227 vasoactive effect Effects 0.000 description 1
- 229960003726 vasopressin Drugs 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 230000035899 viability Effects 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000012800 visualization Methods 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- 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
- A61P15/06—Antiabortive agents; Labour repressants
-
- 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
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/10—Drugs for disorders of the endocrine system of the posterior pituitary hormones, e.g. oxytocin, ADH
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- 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
- C07D403/06—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 linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Diabetes (AREA)
- Gynecology & Obstetrics (AREA)
- Pregnancy & Childbirth (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP02100784 | 2002-07-05 | ||
| PCT/EP2003/050286 WO2004005249A1 (en) | 2002-07-05 | 2003-07-04 | Pyrrolidine derivatives as oxytocin antagonists |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA78058C2 true UA78058C2 (en) | 2007-02-15 |
Family
ID=30011225
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UA20041210895A UA78058C2 (en) | 2002-07-05 | 2003-04-07 | Pyrrolidine derivative as oxitocin antagonists |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US7115754B2 (de) |
| EP (1) | EP1532109B1 (de) |
| JP (1) | JP4851085B2 (de) |
| CN (1) | CN1330633C (de) |
| AT (1) | ATE442354T1 (de) |
| BR (1) | BR0312586A (de) |
| CA (1) | CA2487532C (de) |
| DE (1) | DE60329189D1 (de) |
| EA (1) | EA008479B1 (de) |
| ES (1) | ES2330841T3 (de) |
| HK (1) | HK1076107A1 (de) |
| HR (1) | HRP20041208A2 (de) |
| IL (1) | IL166103A0 (de) |
| MX (1) | MXPA05000326A (de) |
| NO (1) | NO20050612L (de) |
| PL (1) | PL374666A1 (de) |
| RS (1) | RS115804A (de) |
| UA (1) | UA78058C2 (de) |
| WO (1) | WO2004005249A1 (de) |
| ZA (1) | ZA200409820B (de) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CZ20033475A3 (en) * | 2001-06-18 | 2004-05-12 | Appliedáresearchásystemsáarsáholdingán@V | Pyrrolidine oxadiazole- and thiadiazole oxime derivatives being oxytocin receptor antagonists. |
| US10722645B2 (en) | 2011-12-21 | 2020-07-28 | Deka Products Limited Partnership | Syringe pump, and related method and system |
| EP2845850A1 (de) * | 2013-09-10 | 2015-03-11 | ObsEva S.A. | Pyrrolidinderivate als Oxytocin/Vasopressin-V1a-Rezeptorantagonisten |
| EP2886107A1 (de) * | 2013-12-17 | 2015-06-24 | ObsEva S.A. | Orale Formulierungen von Pyrrolydinderivaten |
| CN106795110A (zh) * | 2014-07-02 | 2017-05-31 | 奥布赛瓦股份公司 | 治疗ot‑r活性相关的病症的方法中可用的晶体(3z，5s)‑5‑(羟甲基)‑1‑[(2’‑甲基‑1，1’‑联苯‑4‑基)羰基]吡咯烷‑3‑酮o‑甲基肟 |
| EP3037101B1 (de) | 2014-12-22 | 2019-03-06 | Ferring B.V. | Oxytocinrezeptorantagonistentherapie in der Lutealphase für Implantation und Schwangerschaft bei mit Technologien zur unterstützten Fortpflanzung behandelten Frauen |
| IL284912B (en) | 2016-01-04 | 2022-07-01 | Merck Serono Sa | L-Valinate derivative of hydroxypropylthiazolidine carboxamide and salt form, crystalline polymorph thereof |
| CA3031252A1 (en) | 2016-07-21 | 2018-01-25 | ObsEva S.A. | Oxytocin antagonist dosing regimens for promoting embryo implantation and preventing miscarriage |
| CN114667141A (zh) | 2019-09-03 | 2022-06-24 | 奥布赛瓦股份公司 | 用于促进胚胎移植和预防流产的催产素拮抗剂给药方案 |
| US20230102503A1 (en) | 2020-02-10 | 2023-03-30 | ObsEva S.A. | Biomarkers for oxytocin receptor antagonist therapy |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6329418B1 (en) | 1998-04-14 | 2001-12-11 | The Procter & Gamble Company | Substituted pyrrolidine hydroxamate metalloprotease inhibitors |
| ES2261404T3 (es) * | 2000-03-27 | 2006-11-16 | Applied Research Systems Ars Holding N.V. | Derivados de pirrolidina utiles como inhibidores de bax. |
-
2003
- 2003-04-07 UA UA20041210895A patent/UA78058C2/uk unknown
- 2003-07-04 RS YUP-1158/04A patent/RS115804A/sr unknown
- 2003-07-04 BR BR0312586-6A patent/BR0312586A/pt not_active IP Right Cessation
- 2003-07-04 WO PCT/EP2003/050286 patent/WO2004005249A1/en active Application Filing
- 2003-07-04 ES ES03762692T patent/ES2330841T3/es not_active Expired - Lifetime
- 2003-07-04 US US10/518,543 patent/US7115754B2/en not_active Expired - Lifetime
- 2003-07-04 PL PL03374666A patent/PL374666A1/xx not_active Application Discontinuation
- 2003-07-04 DE DE60329189T patent/DE60329189D1/de not_active Expired - Lifetime
- 2003-07-04 EA EA200500133A patent/EA008479B1/ru not_active IP Right Cessation
- 2003-07-04 JP JP2004518783A patent/JP4851085B2/ja not_active Expired - Fee Related
- 2003-07-04 CA CA2487532A patent/CA2487532C/en not_active Expired - Fee Related
- 2003-07-04 CN CNB038204010A patent/CN1330633C/zh not_active Expired - Fee Related
- 2003-07-04 AT AT03762692T patent/ATE442354T1/de not_active IP Right Cessation
- 2003-07-04 EP EP03762692A patent/EP1532109B1/de not_active Expired - Lifetime
- 2003-07-04 MX MXPA05000326A patent/MXPA05000326A/es active IP Right Grant
-
2004
- 2004-12-03 ZA ZA200409820A patent/ZA200409820B/en unknown
- 2004-12-23 HR HR20041208A patent/HRP20041208A2/xx not_active Application Discontinuation
-
2005
- 2005-01-03 IL IL16610305A patent/IL166103A0/xx unknown
- 2005-02-03 NO NO20050612A patent/NO20050612L/no not_active Application Discontinuation
- 2005-11-17 HK HK05110274A patent/HK1076107A1/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CA2487532A1 (en) | 2004-01-15 |
| CN1330633C (zh) | 2007-08-08 |
| EP1532109B1 (de) | 2009-09-09 |
| CN1678576A (zh) | 2005-10-05 |
| US20060004020A1 (en) | 2006-01-05 |
| CA2487532C (en) | 2011-03-08 |
| DE60329189D1 (de) | 2009-10-22 |
| AU2003254498A1 (en) | 2004-01-23 |
| IL166103A0 (en) | 2006-01-15 |
| US7115754B2 (en) | 2006-10-03 |
| ATE442354T1 (de) | 2009-09-15 |
| RS115804A (en) | 2007-02-05 |
| NO20050612L (no) | 2005-02-03 |
| EA008479B1 (ru) | 2007-06-29 |
| PL374666A1 (en) | 2005-10-31 |
| ES2330841T3 (es) | 2009-12-16 |
| HK1076107A1 (en) | 2006-01-06 |
| EA200500133A1 (ru) | 2005-08-25 |
| WO2004005249A1 (en) | 2004-01-15 |
| HRP20041208A2 (en) | 2005-06-30 |
| JP2005533828A (ja) | 2005-11-10 |
| ZA200409820B (en) | 2006-07-26 |
| BR0312586A (pt) | 2005-04-12 |
| MXPA05000326A (es) | 2005-03-31 |
| JP4851085B2 (ja) | 2012-01-11 |
| EP1532109A1 (de) | 2005-05-25 |
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