CH615661A5 - - Google Patents
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- CH615661A5 CH615661A5 CH294775A CH294775A CH615661A5 CH 615661 A5 CH615661 A5 CH 615661A5 CH 294775 A CH294775 A CH 294775A CH 294775 A CH294775 A CH 294775A CH 615661 A5 CH615661 A5 CH 615661A5
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- Switzerland
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- leu
- tyr
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- 238000000034 method Methods 0.000 claims description 42
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/10—Tetrapeptides
- C07K5/1002—Tetrapeptides with the first amino acid being neutral
- C07K5/1005—Tetrapeptides with the first amino acid being neutral and aliphatic
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S930/00—Peptide or protein sequence
- Y10S930/01—Peptide or protein sequence
- Y10S930/13—Luteinizing hormone-releasing hormone; related peptides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Biophysics (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Life Sciences & Earth Sciences (AREA)
- Endocrinology (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2744274A JPS5726506B2 (enExample) | 1974-03-08 | 1974-03-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH615661A5 true CH615661A5 (enExample) | 1980-02-15 |
Family
ID=12221217
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH294775A CH615661A5 (enExample) | 1974-03-08 | 1975-03-07 |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US3972859A (enExample) |
| JP (1) | JPS5726506B2 (enExample) |
| AT (1) | AT348693B (enExample) |
| BE (1) | BE826430A (enExample) |
| CA (1) | CA1072953A (enExample) |
| CH (1) | CH615661A5 (enExample) |
| CS (1) | CS186284B2 (enExample) |
| DE (1) | DE2509783C2 (enExample) |
| DK (1) | DK149862C (enExample) |
| ES (1) | ES435405A1 (enExample) |
| FI (1) | FI60859C (enExample) |
| FR (1) | FR2262995B1 (enExample) |
| GB (1) | GB1498048A (enExample) |
| HU (1) | HU174077B (enExample) |
| NL (1) | NL181658C (enExample) |
| NO (1) | NO145691C (enExample) |
| SE (1) | SE420718B (enExample) |
| ZA (1) | ZA751306B (enExample) |
Families Citing this family (106)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2438350C3 (de) * | 1974-08-09 | 1979-06-13 | Hoechst Ag, 6000 Frankfurt | Peptide mit starker LH-RH/FSH-RH-Wirkung, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Zubereitungen |
| AU497512B2 (en) * | 1975-04-15 | 1978-12-14 | Ici Australia Limited | Nona and deca-peptides |
| US4215038A (en) * | 1978-10-16 | 1980-07-29 | The Salk Institute For Biological Studies | Peptides which inhibit gonadal function |
| US4234571A (en) * | 1979-06-11 | 1980-11-18 | Syntex (U.S.A.) Inc. | Nonapeptide and decapeptide derivatives of luteinizing hormone releasing hormone |
| US4318905A (en) * | 1980-06-23 | 1982-03-09 | Syntex (U.S.A.) Inc. | Nonapeptide and decapeptide agonists of luteinizing hormone releasing hormone containing heterocyclic amino acid residues |
| ZA815447B (en) * | 1980-08-29 | 1982-08-25 | Salk Inst For Biological Studi | Peptides affecting gonadal function |
| US4675189A (en) * | 1980-11-18 | 1987-06-23 | Syntex (U.S.A.) Inc. | Microencapsulation of water soluble active polypeptides |
| PH19942A (en) * | 1980-11-18 | 1986-08-14 | Sintex Inc | Microencapsulation of water soluble polypeptides |
| IE52535B1 (en) * | 1981-02-16 | 1987-12-09 | Ici Plc | Continuous release pharmaceutical compositions |
| AU549053B2 (en) * | 1981-12-28 | 1986-01-09 | Beckman Instruments, Inc. | Synthetic peptides having pituitary growth hormone releasing activity |
| JPS58125819U (ja) * | 1982-02-19 | 1983-08-26 | 名伸電機株式会社 | 積算電力量計用パツキン |
| US4581169A (en) * | 1982-12-21 | 1986-04-08 | Syntex (U.S.A.) Inc. | Nona-peptide and deca-peptide analogs of LHRH, useful as LHRH antagonists |
| US4481190A (en) * | 1982-12-21 | 1984-11-06 | Syntex (U.S.A.) Inc. | Nonapeptide and decapeptide analogs of LHRH useful as LHRH antagonists |
| US4667014A (en) * | 1983-03-07 | 1987-05-19 | Syntex (U.S.A.) Inc. | Nonapeptide and decapeptide analogs of LHRH, useful as LHRH antagonists |
| US4663435A (en) * | 1982-12-06 | 1987-05-05 | Merck & Co., Inc. | Bridged cyclic hexapeptide somatostatin analogs |
| US4581168A (en) * | 1983-02-21 | 1986-04-08 | Sanofi | Synthesis of hpGRF (Somatocrinin) in liquid phase and intermediate peptides |
| US4530920A (en) * | 1983-11-07 | 1985-07-23 | Syntex (U.S.A.) Inc. | Nonapeptide and decapeptide analogs of LHRH, useful as LHRH agonist |
| US4897268A (en) * | 1987-08-03 | 1990-01-30 | Southern Research Institute | Drug delivery system and method of making the same |
| JP2653255B2 (ja) | 1990-02-13 | 1997-09-17 | 武田薬品工業株式会社 | 長期徐放型マイクロカプセル |
| CA2050425A1 (en) | 1990-09-03 | 1992-03-04 | Yoshiaki Uda | Pharmaceutical composition and its mucous use |
| NZ240214A (en) | 1990-10-16 | 1993-02-25 | Takeda Chemical Industries Ltd | Polymer compositions comprising a polylactic acid and a copolymer of glycolic acid and a hydroxycarboxylic acid; use as carrier for prolonged release pharmaceutical compositions of water soluble drugs |
| US6011068A (en) * | 1991-08-23 | 2000-01-04 | Nps Pharmaceuticals, Inc. | Calcium receptor-active molecules |
| US6313146B1 (en) | 1991-08-23 | 2001-11-06 | Nps Pharmaceuticals, Inc. | Calcium receptor-active molecules |
| US5763569A (en) * | 1991-08-23 | 1998-06-09 | The Brigham And Women's Hospital, Inc | Calcium receptor-active molecules |
| US5688938A (en) * | 1991-08-23 | 1997-11-18 | The Brigham & Women's Hospital, Inc. | Calcium receptor-active molecules |
| US6031003A (en) * | 1991-08-23 | 2000-02-29 | Nps Pharmaceuticals, Inc. | Calcium receptor-active molecules |
| US5518730A (en) * | 1992-06-03 | 1996-05-21 | Fuisz Technologies Ltd. | Biodegradable controlled release flash flow melt-spun delivery system |
| ES2110573T3 (es) | 1992-08-07 | 1998-02-16 | Takeda Chemical Industries Ltd | Produccion de microcapsulas de farmacos solubles en agua. |
| US5962314A (en) * | 1993-02-23 | 1999-10-05 | Nps Pharmaceuticals, Inc. | Calcium receptor-active molecules |
| US20040259113A1 (en) * | 1993-07-22 | 2004-12-23 | Mayo Foundation For Medical Education And Research, Hybritech Incorporated | Method for detection of metastatic prostate cancer |
| US5516639A (en) * | 1993-07-22 | 1996-05-14 | Mayo Foundation For Medical Education And Research | Antibodies specific for human prostate glandular kallkrein |
| US6103237A (en) * | 1993-07-22 | 2000-08-15 | Hybritech Incorporated | Stable variant hK2 polypeptide |
| CA2143044C (en) * | 1994-02-21 | 2005-04-12 | Yasutaka Igari | Matrix for sustained-release preparation |
| EP0804593A1 (en) * | 1994-05-10 | 1997-11-05 | Mayo Foundation For Medical Education And Research | Recombinant hk2 polypeptide |
| US6117455A (en) | 1994-09-30 | 2000-09-12 | Takeda Chemical Industries, Ltd. | Sustained-release microcapsule of amorphous water-soluble pharmaceutical active agent |
| NZ297157A (en) | 1994-10-21 | 1999-08-30 | Nps Pharma Inc | Amine derivatives with calcium ion receptor activity; medicaments containing such compounds |
| US5837281A (en) | 1995-03-17 | 1998-11-17 | Takeda Chemical Industries, Ltd. | Stabilized interface for iontophoresis |
| CA2192782C (en) | 1995-12-15 | 2008-10-14 | Nobuyuki Takechi | Production of microspheres |
| CA2192773C (en) | 1995-12-15 | 2008-09-23 | Hiroaki Okada | Production of sustained-release preparation for injection |
| AU731146C (en) | 1996-05-01 | 2005-02-03 | Nps Pharmaceuticals, Inc. | Inorganic ion receptor-active compounds |
| US5908400A (en) * | 1996-06-20 | 1999-06-01 | Hisamitsu Pharmaceutical Co., Inc. | Device structure for iontophoresis |
| US6479263B1 (en) | 1996-11-14 | 2002-11-12 | Baylor College Of Medicine | Method for detection of micrometastatic prostate cancer |
| US6235486B1 (en) | 1997-06-20 | 2001-05-22 | Mayo Foundation For Medical Education & Research | Method for detection of breast cancer |
| US6737408B1 (en) | 1997-08-07 | 2004-05-18 | University Of Cincinnati | Compounds for control of appetite, blood pressure, cardiovascular response, libido, and circadian rhythm |
| US6087128A (en) | 1998-02-12 | 2000-07-11 | Ndsu Research Foundation | DNA encoding an avian E. coli iss |
| US6803448B1 (en) * | 1998-07-22 | 2004-10-12 | Vanderbilt University | GBS toxin receptor |
| US8609614B2 (en) * | 1998-07-22 | 2013-12-17 | Vanderbilt University | GBS toxin receptor compositions and methods of use |
| US6339062B1 (en) * | 1998-11-23 | 2002-01-15 | Inkine Pharmaceutical Company, Inc. | Retroinverso polypeptides that mimic or inhibit thrombospondin activity |
| AUPR074500A0 (en) * | 2000-10-13 | 2000-11-09 | Monash University | Treatment of t cell disorders |
| US20050020524A1 (en) * | 1999-04-15 | 2005-01-27 | Monash University | Hematopoietic stem cell gene therapy |
| US20070274946A1 (en) * | 1999-04-15 | 2007-11-29 | Norwood Immunoloty, Ltd. | Tolerance to Graft Prior to Thymic Reactivation |
| US20050042679A1 (en) * | 1999-04-15 | 2005-02-24 | Monash University | Diagnostic indicator of thymic function |
| US20040258672A1 (en) * | 1999-04-15 | 2004-12-23 | Monash University | Graft acceptance through manipulation of thymic regeneration |
| US20040241842A1 (en) * | 1999-04-15 | 2004-12-02 | Monash University | Stimulation of thymus for vaccination development |
| US20040259803A1 (en) * | 1999-04-15 | 2004-12-23 | Monash University | Disease prevention by reactivation of the thymus |
| US20040265285A1 (en) * | 1999-04-15 | 2004-12-30 | Monash University | Normalization of defective T cell responsiveness through manipulation of thymic regeneration |
| EP1203014B1 (en) * | 1999-08-06 | 2004-10-13 | Genentech, Inc. | Peptide antagonists of factor viia |
| US6407211B1 (en) * | 1999-12-17 | 2002-06-18 | Mayo Foundation For Medical Education And Research | Chimeric natriuretic peptides |
| ES2270893T3 (es) | 1999-12-24 | 2007-04-16 | Genentech, Inc. | Procedimiento y composiciones para prolongar la vida media de compuestos bioactivos. |
| US20060228364A1 (en) * | 1999-12-24 | 2006-10-12 | Genentech, Inc. | Serum albumin binding peptides for tumor targeting |
| US20040001827A1 (en) * | 2002-06-28 | 2004-01-01 | Dennis Mark S. | Serum albumin binding peptides for tumor targeting |
| EP1757311B1 (en) | 1999-12-24 | 2009-02-11 | Genentech, Inc. | Methods and compositions for prolonging elimination half-times of bioactive compounds |
| US20050287153A1 (en) * | 2002-06-28 | 2005-12-29 | Genentech, Inc. | Serum albumin binding peptides for tumor targeting |
| US20060088512A1 (en) * | 2001-10-15 | 2006-04-27 | Monash University | Treatment of T cell disorders |
| US7164002B2 (en) | 2002-02-06 | 2007-01-16 | Genentech, Inc. | FVIIa antagonists |
| CN100475271C (zh) | 2003-08-20 | 2009-04-08 | 加利福尼亚大学董事会 | 具有抑制生长激素释放活性的促生长素抑制素类似物 |
| CN101048425B (zh) * | 2003-09-18 | 2012-12-26 | 雷文生物技术公司 | Kid3及与其结合的kid3抗体 |
| US20080279812A1 (en) * | 2003-12-05 | 2008-11-13 | Norwood Immunology, Ltd. | Disease Prevention and Vaccination Prior to Thymic Reactivation |
| JP4390568B2 (ja) * | 2004-01-19 | 2009-12-24 | 富士通株式会社 | 遅延測定システム |
| KR101295139B1 (ko) * | 2004-06-07 | 2013-08-12 | 레이븐 바이오테크놀로지스, 인코퍼레이티드 | 트랜스페린 리셉터 항체 |
| BRPI0516577A (pt) * | 2004-10-05 | 2008-09-16 | Genentech Inc | agentes terapêuticos com toxicidade diminuìda |
| US7687242B2 (en) * | 2005-01-12 | 2010-03-30 | Raven Biotechnologies, Inc. | KID31 and antibodies that bind thereto |
| JP2008538173A (ja) * | 2005-01-31 | 2008-10-16 | レイベン バイオテクノロジーズ，インコーポレイティド | Ｌｕｃａ２およびそれに結合する抗体 |
| WO2006084075A2 (en) | 2005-02-02 | 2006-08-10 | Raven Biotechnologies, Inc. | Adam-9 modulators |
| US20060171952A1 (en) * | 2005-02-02 | 2006-08-03 | Mather Jennie P | JAM-3 and antibodies that bind thereto |
| EP1846455A4 (en) * | 2005-02-03 | 2010-02-17 | Raven Biotechnologies Inc | ANTIBODY TO THE ONKOSTATIN M RECEPTOR |
| EP1790656A1 (en) * | 2005-11-25 | 2007-05-30 | Nanokem S.A. | Solution-phase synthesis of leuprolide |
| US20070197445A1 (en) * | 2006-01-18 | 2007-08-23 | University Of Cincinnati | Compounds for control of appetite |
| WO2008066691A2 (en) * | 2006-11-08 | 2008-06-05 | Macrogenics West, Inc. | Tes7 and antibodies that bind thereto |
| ES2414879T4 (es) | 2009-04-20 | 2013-10-30 | Allergan, Inc. | Hidrogeles de fibroína de seda y usos de éstos |
| PL219569B1 (pl) | 2010-02-19 | 2015-05-29 | Peptaderm Spółka Z Ograniczoną Odpowiedzialnością | Cykliczne tetrapeptydy i ich zastosowanie |
| PH12012501751A1 (en) | 2010-03-04 | 2012-11-12 | Macrogenics Inc | Antibodies reactive with b7-h3, immunologically active fragments thereof and uses thereof |
| ME03447B (me) | 2010-03-04 | 2020-01-20 | Macrogenics Inc | Anтitela reakтivna sa b7-нз, njihovi imunološki akтivni fragmenтi i upotreba |
| MX369220B (es) | 2011-05-21 | 2019-10-31 | Macrogenics Inc | Moleculas que enlazan cd3 capaces de enlazar a cd3 humano y no humano. |
| EP2557163A1 (en) | 2011-08-12 | 2013-02-13 | SymbioGruppe GmbH & Co KG | Bacterially formed microcin S, a new antimicrobial peptide, effective against pathogenic microorganisms, e.g. enterohemorrhagic Escherichia coli (EHEC) |
| KR20140068087A (ko) | 2011-08-23 | 2014-06-05 | 프레지던트 앤드 펠로우즈 오브 하바드 칼리지 | 펩티드 나노입자 및 이의 용도 |
| CN107090028A (zh) | 2011-08-30 | 2017-08-25 | 梅约医学教育与研究基金会 | 利钠多肽 |
| US9611305B2 (en) | 2012-01-06 | 2017-04-04 | Mayo Foundation For Medical Education And Research | Treating cardiovascular or renal diseases |
| US9487587B2 (en) | 2013-03-05 | 2016-11-08 | Macrogenics, Inc. | Bispecific molecules that are immunoreactive with immune effector cells of a companion animal that express an activating receptor and cells that express B7-H3 and uses thereof |
| BR112015022790A8 (pt) | 2013-03-14 | 2020-01-21 | Univ Duke | molécula biespecífica, composição farmacêutica, método de tratamento de uma infecção por vírus latente em um indivíduo em necessidade de tal tratamento, método de tratamento de uma infecção por vírus persistente em um indivíduo em necessidade de tal tratamento, método de tratamento de uma infecção por vírus inativo em um indivíduo em necessidade de tal tratamento, método para exterminar uma célula que contém um genoma viral, e, método para exterminar uma célula que expressa uma proteína viral |
| CA2911613A1 (en) | 2013-03-29 | 2014-10-02 | Centre National De La Recherche Scientifique (Cnrs) | Cgrp receptor agonist for hiv treatment or prevention |
| WO2015184207A1 (en) | 2014-05-29 | 2015-12-03 | Macrogenics, Inc. | Tri-specific binding molecules that specifically bind to multiple cancer antigens and methods of use thereof |
| SG11201702544WA (en) | 2014-09-29 | 2017-04-27 | Univ Duke | Bispecific molecules comprising an hiv-1 envelope targeting arm |
| TWI773646B (zh) | 2015-06-08 | 2022-08-11 | 美商宏觀基因股份有限公司 | 結合lag-3的分子和其使用方法 |
| IL287916B2 (en) | 2015-07-30 | 2023-09-01 | Macrogenics Inc | Molecules that bind pd-1 and methods of using them |
| KR20250079249A (ko) | 2015-10-08 | 2025-06-04 | 마크로제닉스, 인크. | 암 치료를 위한 조합 치료법 |
| KR102815803B1 (ko) | 2015-12-02 | 2025-06-05 | 주식회사 에스티사이언스 | 당화된 btla(b- 및 t-림프구 약화인자)에 특이적인 항체 |
| SG11201804839WA (en) | 2015-12-14 | 2018-07-30 | Macrogenics Inc | Bispecific molecules having immunoreactivity with pd-1 and ctla-4, and methods of use thereof |
| WO2017180813A1 (en) | 2016-04-15 | 2017-10-19 | Macrogenics, Inc. | Novel b7-h3 binding molecules, antibody drug conjugates thereof and methods of use thereof |
| US10111929B1 (en) | 2017-04-07 | 2018-10-30 | Ez Ip, Llc | Growth hormone releasing factor analogs and uses |
| US20220411511A1 (en) | 2019-09-26 | 2022-12-29 | Stcube & Co. | Antibodies specific to glycosylated ctla-4 and methods of use thereof |
| KR20220088438A (ko) | 2019-10-09 | 2022-06-27 | 주식회사 에스티큐브앤컴퍼니 | 글리코실화된 lag3에 대해 특이적인 항체 및 이의 사용 방법 |
| US11596665B2 (en) | 2020-06-23 | 2023-03-07 | Chanda Zaveri | Skin lightening formulations |
| US11951203B2 (en) | 2020-08-26 | 2024-04-09 | Chanda Zaveri | Deep wrinkle vanishing compositions |
| US11793746B2 (en) | 2020-10-01 | 2023-10-24 | Chanda Zaveri | Intense skin hydration systems and methods |
| US20220110852A1 (en) | 2020-10-14 | 2022-04-14 | Chanda Zaveri | Pigment Stabilizers |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3835108A (en) * | 1972-02-15 | 1974-09-10 | American Home Prod | Process for preparing the releasing hormone of luteinizing hormone(lh)and of follicle stimulating hormone(fsh),salts and compositions thereof,and intermediates therefor |
| US3896104A (en) * | 1974-05-22 | 1975-07-22 | American Home Prod | P-glu-his-trp-ser-tyr-d-lys-leu-arg-pro-gly-nh' 2 'and intermediates |
-
1974
- 1974-03-08 JP JP2744274A patent/JPS5726506B2/ja not_active Expired
-
1975
- 1975-02-24 AT AT138075A patent/AT348693B/de not_active IP Right Cessation
- 1975-03-03 CA CA221,126A patent/CA1072953A/en not_active Expired
- 1975-03-03 ZA ZA00751306A patent/ZA751306B/xx unknown
- 1975-03-04 NL NLAANVRAGE7502564,A patent/NL181658C/xx not_active IP Right Cessation
- 1975-03-04 US US05/555,126 patent/US3972859A/en not_active Expired - Lifetime
- 1975-03-05 CS CS7500001485A patent/CS186284B2/cs unknown
- 1975-03-06 FR FR7507065A patent/FR2262995B1/fr not_active Expired
- 1975-03-06 DE DE2509783A patent/DE2509783C2/de not_active Expired
- 1975-03-06 SE SE7502520A patent/SE420718B/xx not_active IP Right Cessation
- 1975-03-07 HU HU75TA1346A patent/HU174077B/hu unknown
- 1975-03-07 GB GB9539/75A patent/GB1498048A/en not_active Expired
- 1975-03-07 DK DK092775A patent/DK149862C/da not_active IP Right Cessation
- 1975-03-07 ES ES435405A patent/ES435405A1/es not_active Expired
- 1975-03-07 BE BE154128A patent/BE826430A/xx not_active IP Right Cessation
- 1975-03-07 CH CH294775A patent/CH615661A5/de not_active IP Right Cessation
- 1975-03-07 NO NO750763A patent/NO145691C/no unknown
- 1975-03-10 FI FI750682A patent/FI60859C/fi not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| NO145691C (no) | 1982-05-12 |
| FI750682A7 (enExample) | 1975-09-09 |
| ZA751306B (en) | 1976-01-28 |
| HU174077B (hu) | 1979-10-28 |
| GB1498048A (en) | 1978-01-18 |
| FR2262995B1 (enExample) | 1978-07-28 |
| DK149862C (da) | 1987-06-15 |
| JPS50121277A (enExample) | 1975-09-23 |
| DK149862B (da) | 1986-10-13 |
| ATA138075A (de) | 1978-07-15 |
| CS186284B2 (en) | 1978-11-30 |
| US3972859A (en) | 1976-08-03 |
| JPS5726506B2 (enExample) | 1982-06-04 |
| CA1072953A (en) | 1980-03-04 |
| NO750763L (enExample) | 1975-09-09 |
| AU7859475A (en) | 1976-08-26 |
| SE420718B (sv) | 1981-10-26 |
| FI60859B (fi) | 1981-12-31 |
| DE2509783C2 (de) | 1983-02-17 |
| NL181658B (nl) | 1987-05-04 |
| SE7502520L (enExample) | 1975-09-09 |
| AT348693B (de) | 1979-02-26 |
| NO145691B (no) | 1982-02-01 |
| FR2262995A1 (enExample) | 1975-10-03 |
| NL7502564A (nl) | 1975-09-10 |
| BE826430A (fr) | 1975-09-08 |
| DE2509783A1 (de) | 1975-09-11 |
| FI60859C (fi) | 1982-04-13 |
| DK92775A (enExample) | 1975-09-09 |
| NL181658C (nl) | 1987-10-01 |
| ES435405A1 (es) | 1976-12-01 |
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Legal Events
| Date | Code | Title | Description |
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| PFA | Name/firm changed |
Owner name: TAKEDA CHEMICAL INDUSTRIES, LTD |
|
| PL | Patent ceased | ||
| PL | Patent ceased |