RU2003107560A - Соль пептида (варианты), способ ее получения и применение, фармацевтическая композиция и способ ее получения - Google Patents
Соль пептида (варианты), способ ее получения и применение, фармацевтическая композиция и способ ее получения Download PDFInfo
- Publication number
- RU2003107560A RU2003107560A RU2003107560/04A RU2003107560A RU2003107560A RU 2003107560 A RU2003107560 A RU 2003107560A RU 2003107560/04 A RU2003107560/04 A RU 2003107560/04A RU 2003107560 A RU2003107560 A RU 2003107560A RU 2003107560 A RU2003107560 A RU 2003107560A
- Authority
- RU
- Russia
- Prior art keywords
- peptide
- salt
- acid
- producing
- diluent
- Prior art date
Links
- 108090000765 processed proteins & peptides Proteins 0.000 title claims 12
- 150000003839 salts Chemical class 0.000 title claims 10
- 239000008194 pharmaceutical composition Substances 0.000 title claims 3
- 238000004519 manufacturing process Methods 0.000 title 2
- 238000000034 method Methods 0.000 claims 8
- 239000002253 acid Substances 0.000 claims 5
- 239000003085 diluting agent Substances 0.000 claims 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims 4
- 108700008462 cetrorelix Proteins 0.000 claims 3
- 229960003230 cetrorelix Drugs 0.000 claims 3
- SBNPWPIBESPSIF-MHWMIDJBSA-N cetrorelix Chemical compound C([C@@H](C(=O)N[C@H](CCCNC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N1[C@@H](CCC1)C(=O)N[C@H](C)C(N)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](CC=1C=NC=CC=1)NC(=O)[C@@H](CC=1C=CC(Cl)=CC=1)NC(=O)[C@@H](CC=1C=C2C=CC=CC2=CC=1)NC(C)=O)C1=CC=C(O)C=C1 SBNPWPIBESPSIF-MHWMIDJBSA-N 0.000 claims 3
- WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 claims 3
- OFQNFLLLCMQNEP-KQCGYNJJSA-N chembl2106408 Chemical compound C([C@@H](C(=O)N[C@@H](CCCCNC(/NCC)=N\CC)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N1[C@@H](CCC1)C(=O)N[C@H](C)C(N)=O)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CC=1C=CC(Cl)=CC=1)NC(=O)[C@@H](CC=1C=C2C=CC=CC2=CC=1)NC(C)=O)C1=CC=C(O)C=C1 OFQNFLLLCMQNEP-KQCGYNJJSA-N 0.000 claims 2
- 108700027435 detirelix Proteins 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 229940124531 pharmaceutical excipient Drugs 0.000 claims 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims 2
- WGWPBHBZVYAVTQ-HQDLIPOVSA-N (2r)-1-[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-acetamido-3-naphthalen-2-ylpropanoyl]amino]-3-(4-chlorophenyl)propanoyl]amino]-3-pyridin-3-ylpropanoyl]amino]-3-hydroxypropanoyl]-methylamino]-3-(4-hydroxyphenyl)propanoyl]amino Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCC(N)C(C)C)C(=O)N1[C@H](CCC1)C(=O)N[C@@H](C)C(N)=O)NC(=O)[C@H](CC=1C=CC(O)=CC=1)N(C)C(=O)[C@H](CO)NC(=O)[C@H](CC=1C=NC=CC=1)NC(=O)[C@H](CC=1C=CC(Cl)=CC=1)NC(=O)[C@H](CC=1C=C2C=CC=CC2=CC=1)NC(C)=O)CCC(N)C(=O)C1=CC=NC=C1 WGWPBHBZVYAVTQ-HQDLIPOVSA-N 0.000 claims 1
- NOENHWMKHNSHGX-IZOOSHNJSA-N (2s)-1-[(2s)-2-[[(2s)-2-[[(2r)-2-[[(2r)-2-[[(2s)-2-[[(2r)-2-[[(2s)-2-[[(2r)-2-acetamido-3-naphthalen-2-ylpropanoyl]amino]-3-(4-chlorophenyl)propanoyl]amino]-3-pyridin-3-ylpropanoyl]amino]-3-hydroxypropanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-6-(ca Chemical compound C([C@H](C(=O)N[C@H](CCCCNC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCCNC(C)C)C(=O)N1[C@@H](CCC1)C(=O)N[C@H](C)C(N)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](CC=1C=NC=CC=1)NC(=O)[C@H](CC=1C=CC(Cl)=CC=1)NC(=O)[C@@H](CC=1C=C2C=CC=CC2=CC=1)NC(C)=O)C1=CC=C(O)C=C1 NOENHWMKHNSHGX-IZOOSHNJSA-N 0.000 claims 1
- WDYSQADGBBEGRQ-APSDYLPASA-N (2s)-2-[[(2r)-2-[[(2s)-2-[[(2s)-2-[[(2r)-2-[[(2r)-2-[[(2r)-2-acetamido-3-naphthalen-2-ylpropanoyl]amino]-3-(4-chlorophenyl)propanoyl]amino]-3-(1h-indol-3-yl)propanoyl]amino]-3-hydroxypropanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-3-[(2r,3r,4r,5r,6s) Chemical compound C([C@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCN=C(N)N)C(=O)N1[C@@H](CCC1)C(=O)NNC(N)=O)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@@H](CC=1C=CC(Cl)=CC=1)NC(=O)[C@@H](CC=1C=C2C=CC=CC2=CC=1)NC(C)=O)O[C@@H]1O[C@@H](C)[C@H](O)[C@@H](O)[C@H]1O WDYSQADGBBEGRQ-APSDYLPASA-N 0.000 claims 1
- 108010046892 A 75998 Proteins 0.000 claims 1
- 241000124008 Mammalia Species 0.000 claims 1
- 235000021355 Stearic acid Nutrition 0.000 claims 1
- 108010023617 abarelix Proteins 0.000 claims 1
- AIWRTTMUVOZGPW-HSPKUQOVSA-N abarelix Chemical compound C([C@@H](C(=O)N[C@H](CC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCCNC(C)C)C(=O)N1[C@@H](CCC1)C(=O)N[C@H](C)C(N)=O)N(C)C(=O)[C@H](CO)NC(=O)[C@@H](CC=1C=NC=CC=1)NC(=O)[C@@H](CC=1C=CC(Cl)=CC=1)NC(=O)[C@@H](CC=1C=C2C=CC=CC2=CC=1)NC(C)=O)C1=CC=C(O)C=C1 AIWRTTMUVOZGPW-HSPKUQOVSA-N 0.000 claims 1
- 229960002184 abarelix Drugs 0.000 claims 1
- 108010070670 antarelix Proteins 0.000 claims 1
- -1 azalin B Chemical compound 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 229950003747 detirelix Drugs 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000012467 final product Substances 0.000 claims 1
- 238000004108 freeze drying Methods 0.000 claims 1
- 108700032141 ganirelix Proteins 0.000 claims 1
- 229960003794 ganirelix Drugs 0.000 claims 1
- GJNXBNATEDXMAK-PFLSVRRQSA-N ganirelix Chemical compound C([C@@H](C(=O)N[C@H](CCCCN=C(NCC)NCC)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCCN=C(NCC)NCC)C(=O)N1[C@@H](CCC1)C(=O)N[C@H](C)C(N)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](CC=1C=NC=CC=1)NC(=O)[C@@H](CC=1C=CC(Cl)=CC=1)NC(=O)[C@@H](CC=1C=C2C=CC=CC2=CC=1)NC(C)=O)C1=CC=C(O)C=C1 GJNXBNATEDXMAK-PFLSVRRQSA-N 0.000 claims 1
- 108010083551 iturelix Proteins 0.000 claims 1
- QRYFGTULTGLGHU-NBERXCRTSA-N iturelix Chemical compound C([C@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCCNC(C)C)C(=O)N1[C@@H](CCC1)C(=O)N[C@H](C)C(N)=O)NC(=O)[C@H](CCCCNC(=O)C=1C=NC=CC=1)NC(=O)[C@H](CO)NC(=O)[C@@H](CC=1C=NC=CC=1)NC(=O)[C@@H](CC=1C=CC(Cl)=CC=1)NC(=O)[C@@H](CC=1C=C2C=CC=CC2=CC=1)NC(C)=O)CCCNC(=O)C1=CC=CN=C1 QRYFGTULTGLGHU-NBERXCRTSA-N 0.000 claims 1
- 150000007522 mineralic acids Chemical class 0.000 claims 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims 1
- 150000007524 organic acids Chemical class 0.000 claims 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims 1
- 238000007911 parenteral administration Methods 0.000 claims 1
- 108010092834 ramorelix Proteins 0.000 claims 1
- 229950000277 ramorelix Drugs 0.000 claims 1
- 229960004889 salicylic acid Drugs 0.000 claims 1
- 239000008117 stearic acid Substances 0.000 claims 1
- 229950011372 teverelix Drugs 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
- C07K1/107—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length by chemical modification of precursor peptides
- C07K1/113—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length by chemical modification of precursor peptides without change of the primary structure
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/08—Drugs for disorders of the urinary system of the prostate
-
- 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
- A61P35/00—Antineoplastic agents
-
- 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
- A61P5/02—Drugs for disorders of the endocrine system of the hypothalamic hormones, e.g. TRH, GnRH, CRH, GRH, somatostatin
-
- 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
- A61P5/02—Drugs for disorders of the endocrine system of the hypothalamic hormones, e.g. TRH, GnRH, CRH, GRH, somatostatin
- A61P5/04—Drugs for disorders of the endocrine system of the hypothalamic hormones, e.g. TRH, GnRH, CRH, GRH, somatostatin for decreasing, blocking or antagonising the activity of the hypothalamic hormones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/04—Linear peptides containing only normal peptide links
- C07K7/23—Luteinising hormone-releasing hormone [LHRH]; Related peptides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Endocrinology (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Genetics & Genomics (AREA)
- Biophysics (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Biochemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Analytical Chemistry (AREA)
- Diabetes (AREA)
- Urology & Nephrology (AREA)
- Reproductive Health (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Medicinal Preparation (AREA)
Claims (10)
1. Способ получения соли пептида, отличающийся тем, что исходную кислотно-аддитивную соль основного пептида в присутствии подходящего разбавителя обрабатывают смешанным ионообменником или смесью кислотного и основного ионообменников с образованием свободного основного пептида, затем ионообменник удаляют и свободный основный пептид обрабатывают неорганической или органической кислотой с образованием конечного продукта, требуемой кислотно-аддитивной соли пептида, а затем удаляют разбавитель.
2. Способ по п.1, отличающийся тем, что в качестве исходной соли пептида используют соль цетрореликса, тевереликса, абареликса, ганиреликса, азалина В, антида, А-75998, детиреликса, рамореликса, RS-68439.
3. Способ по п.1 или 2, отличающийся тем, что в качестве кислоты выбирают эмбоновую кислоту, стеариновую кислоту или салициловую кислоту.
4. Способ по одному из пп.1-3, отличающийся тем, что в качестве пептида используют цетрореликс, а в качестве кислоты - эмбоновую кислоту при мольном соотношении цетрореликса и эмбоновой кислоты 2:1.
5. Способ по одному из пп.1-4, отличающийся тем, что разбавитель удаляют посредством лиофилизации.
6. Соль пептида, полученная с использованием способа по пп.1-5.
7. Лиофилизированная соль пептида, полученная с использованием способа по п.5.
8. Фармацевтическая композиция, отличающаяся тем, что она содержит соль пептида по п.6 или 7 в смеси с фармацевтическими вспомогательными веществами, носителями и/или наполнителями.
9. Способ получения фармацевтической композиции по п.8, отличающийся тем, что фармацевтические вспомогательные вещества, носители и/или наполнители добавляют полностью или частично перед удалением разбавителя.
10. Применение соли пептида по п.6 или 7 в качестве лекарственного средства для парентерального введения млекопитающим.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10040700A DE10040700A1 (de) | 2000-08-17 | 2000-08-17 | Salze von biologisch aktiven Peptiden, ihre Herstellung und Verwendung |
| DE10040700.5 | 2000-08-17 | ||
| CA002355573A CA2355573A1 (en) | 2000-08-17 | 2001-08-22 | Method for the synthesis of peptide salts, their use and the pharmaceutical preparations, containing peptide salts |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2003107560A true RU2003107560A (ru) | 2005-01-27 |
| RU2266296C2 RU2266296C2 (ru) | 2005-12-20 |
Family
ID=27805895
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2003107560/04A RU2266296C2 (ru) | 2000-08-17 | 2001-08-09 | Способ получения фармацевтической композиции пептида-антагониста lhrh |
Country Status (30)
| Country | Link |
|---|---|
| US (1) | US6780972B2 (ru) |
| EP (1) | EP1309607B1 (ru) |
| JP (1) | JP2004506647A (ru) |
| CN (1) | CN1187369C (ru) |
| AR (1) | AR030371A1 (ru) |
| AT (1) | ATE280779T1 (ru) |
| AU (2) | AU1043902A (ru) |
| BG (1) | BG107612A (ru) |
| BR (1) | BR0113296A (ru) |
| CA (1) | CA2355573A1 (ru) |
| CZ (1) | CZ2003688A3 (ru) |
| DE (2) | DE10040700A1 (ru) |
| DK (1) | DK1309607T3 (ru) |
| EE (1) | EE200300065A (ru) |
| ES (1) | ES2230371T3 (ru) |
| HK (1) | HK1058366A1 (ru) |
| HU (1) | HUP0300738A3 (ru) |
| IL (1) | IL154150A0 (ru) |
| MX (1) | MXPA03001448A (ru) |
| NO (1) | NO20030618L (ru) |
| NZ (1) | NZ524023A (ru) |
| PL (1) | PL204496B1 (ru) |
| PT (1) | PT1309607E (ru) |
| RU (1) | RU2266296C2 (ru) |
| SI (1) | SI1309607T1 (ru) |
| SK (1) | SK3032003A3 (ru) |
| TW (1) | TWI236910B (ru) |
| UA (1) | UA74005C2 (ru) |
| WO (1) | WO2002014347A2 (ru) |
| ZA (1) | ZA200300777B (ru) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6828415B2 (en) * | 1993-02-19 | 2004-12-07 | Zentaris Gmbh | Oligopeptide lyophilisate, their preparation and use |
| US7098305B2 (en) * | 2001-09-06 | 2006-08-29 | Ardana Bioscience Limited | Sustained release of microcrystalline peptide suspensions |
| EP1674082A1 (de) * | 2004-12-22 | 2006-06-28 | Zentaris GmbH | Verfahren zur Herstellung von sterilen Suspensionen oder Lyophilisaten schwerlöslicher basischer Peptidkomplexe, diese enthaltende pharmazeutische Formulierungen sowie ihre Verwendung als Arzneimittel |
| RU2525661C2 (ru) * | 2012-11-15 | 2014-08-20 | Федеральное государственное бюджетное учреждение "Научно-исследовательский институт вакцин и сывороток им. И.И. Мечникова" Российской академии медицинских наук (ФГБУ "НИИВС им. И.И. Мечникова" РАМН) | Способ получения высокотитражной антимикробной сыворотки для оценки антигенной активности противостафилококковых вакцин |
| CN107056894B (zh) * | 2017-05-26 | 2021-07-20 | 济南康和医药科技有限公司 | 一种片段法固相合成醋酸加尼瑞克的方法 |
| EP3590526A1 (en) * | 2018-07-05 | 2020-01-08 | Antev Limited | A lyophilization process and a teverelix-tfa lyophilizate obtained thereby |
| CN114249800A (zh) * | 2020-09-22 | 2022-03-29 | 深圳市星银医药有限公司 | 一种双羟萘酸多肽药物的制备方法 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4431635A (en) * | 1979-06-13 | 1984-02-14 | Coy David Howard | LH-RH Antagonists |
| EP0041286B1 (en) * | 1980-06-02 | 1984-08-15 | Andrew Victor Schally | Lh-rh antagonists |
| US4800191A (en) * | 1987-07-17 | 1989-01-24 | Schally Andrew Victor | LHRH antagonists |
| DE4305225A1 (de) * | 1993-02-19 | 1994-08-25 | Asta Medica Ag | Neues Herstellverfahren für Cetrorelix Lyophilisat |
| JP2944419B2 (ja) * | 1993-05-10 | 1999-09-06 | ノバルティス アクチエンゲゼルシャフト | 持続性遊離組成物中の薬理学的活性成分の安定 |
| CA2178592C (en) * | 1993-12-09 | 2009-07-28 | Jurgen Engel | Long-acting injection suspensions and a process for their preparation |
| DE4342092B4 (de) * | 1993-12-09 | 2007-01-11 | Zentaris Gmbh | Langwirkende Injektionssuspension und Verfahren zur Herstellung |
| US6054432A (en) * | 1996-09-12 | 2000-04-25 | Asta Medica Aktiengesellschaft | Means for treating prostate hypertrophy and prostate cancer |
| EP1048301A4 (en) * | 1998-01-16 | 2005-03-09 | Takeda Chemical Industries Ltd | COMPOSITIONS WITH DELAYED ACTIVE INGREDIENTS, PROCESS FOR THEIR PREPARATION AND THEIR USE |
-
2000
- 2000-08-17 DE DE10040700A patent/DE10040700A1/de not_active Withdrawn
-
2001
- 2001-08-09 AU AU1043902A patent/AU1043902A/xx active Pending
- 2001-08-09 RU RU2003107560/04A patent/RU2266296C2/ru not_active IP Right Cessation
- 2001-08-09 HU HU0300738A patent/HUP0300738A3/hu unknown
- 2001-08-09 PL PL359495A patent/PL204496B1/pl not_active IP Right Cessation
- 2001-08-09 DE DE50104316T patent/DE50104316D1/de not_active Expired - Lifetime
- 2001-08-09 EP EP01978273A patent/EP1309607B1/de not_active Expired - Lifetime
- 2001-08-09 AU AU2002210439A patent/AU2002210439B2/en not_active Ceased
- 2001-08-09 WO PCT/EP2001/009219 patent/WO2002014347A2/de active IP Right Grant
- 2001-08-09 JP JP2002519484A patent/JP2004506647A/ja active Pending
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Effective date: 20100810 |