AU2014212095B2 - Methods for producing diketopiperazines and compositions containing diketopiperazines - Google Patents
Methods for producing diketopiperazines and compositions containing diketopiperazines Download PDFInfo
- Publication number
- AU2014212095B2 AU2014212095B2 AU2014212095A AU2014212095A AU2014212095B2 AU 2014212095 B2 AU2014212095 B2 AU 2014212095B2 AU 2014212095 A AU2014212095 A AU 2014212095A AU 2014212095 A AU2014212095 A AU 2014212095A AU 2014212095 B2 AU2014212095 B2 AU 2014212095B2
- Authority
- AU
- Australia
- Prior art keywords
- albumin
- dkp
- stream
- pct
- rich
- Prior art date
- Legal status (The legal status 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 status listed.)
- Ceased
Links
- 238000000034 method Methods 0.000 title claims abstract description 41
- 239000000203 mixture Substances 0.000 title claims abstract description 12
- RVLCUCVJZVRNDC-IMJSIDKUSA-N 2-[(2s,5s)-5-methyl-3,6-dioxopiperazin-2-yl]acetic acid Chemical compound C[C@@H]1NC(=O)[C@H](CC(O)=O)NC1=O RVLCUCVJZVRNDC-IMJSIDKUSA-N 0.000 claims abstract description 53
- 108010038239 aspartyl-alanyl-diketopiperazine Proteins 0.000 claims abstract description 52
- 102000009027 Albumins Human genes 0.000 claims abstract description 49
- 108010088751 Albumins Proteins 0.000 claims abstract description 49
- 238000010438 heat treatment Methods 0.000 claims abstract 4
- 108091006905 Human Serum Albumin Proteins 0.000 claims description 45
- 102000008100 Human Serum Albumin Human genes 0.000 claims description 45
- 238000012545 processing Methods 0.000 claims description 21
- 238000006243 chemical reaction Methods 0.000 claims description 11
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 10
- 230000008569 process Effects 0.000 claims description 10
- 238000011534 incubation Methods 0.000 claims description 9
- 238000005194 fractionation Methods 0.000 claims description 7
- 238000004128 high performance liquid chromatography Methods 0.000 claims description 5
- 238000009295 crossflow filtration Methods 0.000 claims description 4
- 238000001914 filtration Methods 0.000 claims description 4
- FRYNKYFGZFGPPR-OTECBHTOSA-N (2s)-2-aminobutanedioic acid;(2s)-2-aminopropanoic acid;piperazine-2,3-dione Chemical compound C[C@H](N)C(O)=O.O=C1NCCNC1=O.OC(=O)[C@@H](N)CC(O)=O FRYNKYFGZFGPPR-OTECBHTOSA-N 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 239000011780 sodium chloride Substances 0.000 claims description 3
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 2
- -1 Nacetyltryptophan Chemical compound 0.000 claims description 2
- BPKIGYQJPYCAOW-FFJTTWKXSA-I calcium;potassium;disodium;(2s)-2-hydroxypropanoate;dichloride;dihydroxide;hydrate Chemical compound O.[OH-].[OH-].[Na+].[Na+].[Cl-].[Cl-].[K+].[Ca+2].C[C@H](O)C([O-])=O BPKIGYQJPYCAOW-FFJTTWKXSA-I 0.000 claims description 2
- 229940079710 sodium acetyltryptophanate Drugs 0.000 claims description 2
- 229960005480 sodium caprylate Drugs 0.000 claims description 2
- BYKRNSHANADUFY-UHFFFAOYSA-M sodium octanoate Chemical compound [Na+].CCCCCCCC([O-])=O BYKRNSHANADUFY-UHFFFAOYSA-M 0.000 claims description 2
- UQSHZBSQKMVQBS-UHFFFAOYSA-M sodium;2-acetamido-3-(1h-indol-3-yl)propanoate Chemical compound [Na+].C1=CC=C2C(CC(NC(=O)C)C([O-])=O)=CNC2=C1 UQSHZBSQKMVQBS-UHFFFAOYSA-M 0.000 claims description 2
- 238000007865 diluting Methods 0.000 claims 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 claims 1
- 229920001612 Hydroxyethyl starch Polymers 0.000 claims 1
- 229940050526 hydroxyethylstarch Drugs 0.000 claims 1
- 238000004949 mass spectrometry Methods 0.000 claims 1
- 229960002446 octanoic acid Drugs 0.000 claims 1
- 101000930822 Giardia intestinalis Dipeptidyl-peptidase 4 Proteins 0.000 abstract description 52
- 230000001225 therapeutic effect Effects 0.000 abstract description 10
- 230000015572 biosynthetic process Effects 0.000 abstract description 6
- 108090000765 processed proteins & peptides Proteins 0.000 abstract description 4
- 102000004190 Enzymes Human genes 0.000 abstract description 3
- 108090000790 Enzymes Proteins 0.000 abstract description 3
- 102000004196 processed proteins & peptides Human genes 0.000 abstract description 3
- 102000004169 proteins and genes Human genes 0.000 abstract description 2
- 108090000623 proteins and genes Proteins 0.000 abstract description 2
- 238000011282 treatment Methods 0.000 abstract description 2
- 102000016622 Dipeptidyl Peptidase 4 Human genes 0.000 abstract 2
- 125000001429 N-terminal alpha-amino-acid group Chemical group 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 102100025012 Dipeptidyl peptidase 4 Human genes 0.000 description 52
- 230000000694 effects Effects 0.000 description 33
- 239000000243 solution Substances 0.000 description 31
- 239000003112 inhibitor Substances 0.000 description 9
- 239000012131 assay buffer Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- 238000003556 assay Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000012986 modification Methods 0.000 description 4
- 230000004048 modification Effects 0.000 description 4
- JNTMAZFVYNDPLB-PEDHHIEDSA-N (2S,3S)-2-[[[(2S)-1-[(2S,3S)-2-amino-3-methyl-1-oxopentyl]-2-pyrrolidinyl]-oxomethyl]amino]-3-methylpentanoic acid Chemical compound CC[C@H](C)[C@H](N)C(=O)N1CCC[C@H]1C(=O)N[C@@H]([C@@H](C)CC)C(O)=O JNTMAZFVYNDPLB-PEDHHIEDSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 235000007164 Oryza sativa Nutrition 0.000 description 3
- 102000035195 Peptidases Human genes 0.000 description 3
- 108091005804 Peptidases Proteins 0.000 description 3
- 108010054812 diprotin A Proteins 0.000 description 3
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 2
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 2
- 239000007995 HEPES buffer Substances 0.000 description 2
- 101000684208 Homo sapiens Prolyl endopeptidase FAP Proteins 0.000 description 2
- 240000007594 Oryza sativa Species 0.000 description 2
- 239000004365 Protease Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 230000008033 biological extinction Effects 0.000 description 2
- 229940098773 bovine serum albumin Drugs 0.000 description 2
- 210000004899 c-terminal region Anatomy 0.000 description 2
- 239000003593 chromogenic compound Substances 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 238000000132 electrospray ionisation Methods 0.000 description 2
- 230000007515 enzymatic degradation Effects 0.000 description 2
- 230000007717 exclusion Effects 0.000 description 2
- 238000012544 monitoring process Methods 0.000 description 2
- 238000007619 statistical method Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 239000003643 water by type Substances 0.000 description 2
- VBBFIBMVFSUUBP-MERQFXBCSA-N (2S)-1-(2-aminoacetyl)-N-(4-nitrophenyl)pyrrolidine-2-carboxamide hydrochloride Chemical compound Cl.NCC(=O)N1CCC[C@H]1C(=O)NC1=CC=C([N+]([O-])=O)C=C1 VBBFIBMVFSUUBP-MERQFXBCSA-N 0.000 description 1
- QIVBCDIJIAJPQS-HLTLGYGQSA-N (2s)-2-amino-3-(2,4,5,6,7-pentadeuterio-1h-indol-3-yl)propanoic acid Chemical compound [2H]C1=C([2H])C([2H])=C2C(C[C@H](N)C(O)=O)=C([2H])NC2=C1[2H] QIVBCDIJIAJPQS-HLTLGYGQSA-N 0.000 description 1
- 206010067484 Adverse reaction Diseases 0.000 description 1
- DVUFTQLHHHJEMK-IMJSIDKUSA-N Asp-Ala Chemical compound OC(=O)[C@H](C)NC(=O)[C@@H](N)CC(O)=O DVUFTQLHHHJEMK-IMJSIDKUSA-N 0.000 description 1
- 208000023275 Autoimmune disease Diseases 0.000 description 1
- 238000000665 Cohn process Methods 0.000 description 1
- 208000028399 Critical Illness Diseases 0.000 description 1
- 102000004127 Cytokines Human genes 0.000 description 1
- 108090000695 Cytokines Proteins 0.000 description 1
- 101000908391 Homo sapiens Dipeptidyl peptidase 4 Proteins 0.000 description 1
- 208000002720 Malnutrition Diseases 0.000 description 1
- 206010029164 Nephrotic syndrome Diseases 0.000 description 1
- 241000209094 Oryza Species 0.000 description 1
- 206010033645 Pancreatitis Diseases 0.000 description 1
- 101150057615 Syn gene Proteins 0.000 description 1
- 230000006838 adverse reaction Effects 0.000 description 1
- 125000003295 alanine group Chemical group N[C@@H](C)C(=O)* 0.000 description 1
- VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 1
- 238000005349 anion exchange Methods 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 229960000074 biopharmaceutical Drugs 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000001952 enzyme assay Methods 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 210000002950 fibroblast Anatomy 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 235000003642 hunger Nutrition 0.000 description 1
- 230000002519 immonomodulatory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 230000001071 malnutrition Effects 0.000 description 1
- 235000000824 malnutrition Nutrition 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 208000015380 nutritional deficiency disease Diseases 0.000 description 1
- 238000009928 pasteurization Methods 0.000 description 1
- 206010034674 peritonitis Diseases 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 230000004962 physiological condition Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 235000019833 protease Nutrition 0.000 description 1
- 235000019419 proteases Nutrition 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 238000000575 proteomic method Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000012465 retentate Substances 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 230000037351 starvation Effects 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000010977 unit operation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- C07K14/435—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
- C07K14/76—Albumins
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
- A61K38/05—Dipeptides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/16—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- A61K38/17—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
- A61K38/38—Albumins
- A61K38/385—Serum albumin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P21/00—Preparation of peptides or proteins
- C12P21/06—Preparation of peptides or proteins produced by the hydrolysis of a peptide bond, e.g. hydrolysate products
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Zoology (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Gastroenterology & Hepatology (AREA)
- Biochemistry (AREA)
- Genetics & Genomics (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Molecular Biology (AREA)
- Wood Science & Technology (AREA)
- Immunology (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Toxicology (AREA)
- Biophysics (AREA)
- General Engineering & Computer Science (AREA)
- Microbiology (AREA)
- Biotechnology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Physics & Mathematics (AREA)
- Analytical Chemistry (AREA)
- General Physics & Mathematics (AREA)
- Pathology (AREA)
- Medicinal Preparation (AREA)
- Biomedical Technology (AREA)
- Electrochemistry (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361759922P | 2013-02-01 | 2013-02-01 | |
| US61/759,922 | 2013-02-01 | ||
| PCT/US2014/014478 WO2014121210A1 (en) | 2013-02-01 | 2014-02-03 | Methods for producing diketopiperazines and compositions containing diketopiperazines |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2014212095A1 AU2014212095A1 (en) | 2015-09-10 |
| AU2014212095B2 true AU2014212095B2 (en) | 2018-07-26 |
Family
ID=51263032
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2014212095A Ceased AU2014212095B2 (en) | 2013-02-01 | 2014-02-03 | Methods for producing diketopiperazines and compositions containing diketopiperazines |
Country Status (15)
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2381775T3 (es) | 2000-08-04 | 2012-05-31 | Dmi Biosciences, Inc. | Procedimiento del uso de dicetopiperazinas y composición que las contiene |
| CN101947306B (zh) | 2003-05-15 | 2014-06-18 | 安皮奥制药股份有限公司 | T-细胞介导的疾病的治疗 |
| JP5856843B2 (ja) | 2008-05-27 | 2016-02-10 | アンピオ ファーマシューティカルズ，インコーポレイテッド | ジケトピペラジンを用いた医薬組成物 |
| KR102032400B1 (ko) | 2011-10-10 | 2019-10-15 | 앰피오 파마슈티컬스 인코퍼레이티드 | 퇴행성 관절 질환의 치료 |
| EP2765968A4 (en) | 2011-10-10 | 2015-01-21 | Ampio Pharmaceuticals Inc | IMPLANTABLE MEDICINE PRODUCTS WITH INCREASED IMMUNO TOLERANCE AND PROCESSING AND IMPLANTATION METHODS |
| SG10201605205VA (en) | 2011-10-28 | 2016-08-30 | Ampio Pharmaceuticals Inc | Treatment of rhinitis |
| KR20150132508A (ko) | 2013-03-15 | 2015-11-25 | 앰피오 파마슈티컬스 인코퍼레이티드 | 줄기세포의 가동화, 회귀, 증식 및 분화를 위한 조성물 및 이의 사용 방법 |
| EP4066836A1 (en) | 2014-08-18 | 2022-10-05 | Ampio Pharmaceuticals, Inc. | Treatment of joint conditions |
| EP3310375A4 (en) * | 2015-06-22 | 2019-02-20 | Ampio Pharmaceuticals, Inc. | USE OF LOW-MOLECULAR FRACTIONS OF HUMAN SERUMALBUMINE IN THE TREATMENT OF ILLNESSES |
| US10456423B2 (en) | 2016-06-13 | 2019-10-29 | SMART SURGICAL, Inc. | Compositions for biological systems and methods for preparing and using the same |
| US10426796B2 (en) | 2016-06-13 | 2019-10-01 | SMART SURGICAL, Inc. | Compositions for biological systems and methods for preparing and using the same |
| WO2021016186A1 (en) * | 2019-07-19 | 2021-01-28 | University Of Utah Research Foundation | Rapid sperm separation based on sperm morphology and motility |
| WO2021163693A1 (en) * | 2020-02-16 | 2021-08-19 | Pur Biologics, Inc. | Methods of manufacturing extracellular matrix using aspartyl alanyl diketopiperazine (da-dkp) |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE765030A (fr) * | 1970-04-02 | 1971-08-16 | Snam Progetti | Composes contenant un noyau de dicetopiperazine et leur procedede fabrication |
| US5561115A (en) * | 1994-08-10 | 1996-10-01 | Bayer Corporation | Low temperature albumin fractionation using sodium caprylate as a partitioning agent |
| US5811241A (en) * | 1995-09-13 | 1998-09-22 | Cortech, Inc. | Method for preparing and identifying N-substitued 1,4-piperazines and N-substituted 1,4-piperazinediones |
| JP2000005569A (ja) * | 1998-06-24 | 2000-01-11 | Asahi Chem Ind Co Ltd | 直列多段濾過法 |
| ES2381775T3 (es) * | 2000-08-04 | 2012-05-31 | Dmi Biosciences, Inc. | Procedimiento del uso de dicetopiperazinas y composición que las contiene |
| CN101279094A (zh) * | 2003-05-15 | 2008-10-08 | Dmi生物科学公司 | T-细胞介导的疾病的治疗 |
| CN101947306B (zh) * | 2003-05-15 | 2014-06-18 | 安皮奥制药股份有限公司 | T-细胞介导的疾病的治疗 |
| US7790039B2 (en) * | 2003-11-24 | 2010-09-07 | Northwest Biotherapeutics, Inc. | Tangential flow filtration devices and methods for stem cell enrichment |
| US20050197496A1 (en) * | 2004-03-04 | 2005-09-08 | Gtc Biotherapeutics, Inc. | Methods of protein fractionation using high performance tangential flow filtration |
| CA2576963C (en) * | 2004-08-20 | 2015-02-17 | Prometic Biosciences Ltd. | Sequential protein isolation and purification schemes by affinity chromatography |
| CN102741280B (zh) * | 2009-10-30 | 2015-12-02 | 诺维信生物制药丹麦公司 | 白蛋白变体 |
| WO2012174472A1 (en) * | 2011-06-17 | 2012-12-20 | Mannkind Corporation | High capacity diketopiperazine microparticles |
| EP2765968A4 (en) * | 2011-10-10 | 2015-01-21 | Ampio Pharmaceuticals Inc | IMPLANTABLE MEDICINE PRODUCTS WITH INCREASED IMMUNO TOLERANCE AND PROCESSING AND IMPLANTATION METHODS |
| KR102032400B1 (ko) * | 2011-10-10 | 2019-10-15 | 앰피오 파마슈티컬스 인코퍼레이티드 | 퇴행성 관절 질환의 치료 |
| SG10201605205VA (en) * | 2011-10-28 | 2016-08-30 | Ampio Pharmaceuticals Inc | Treatment of rhinitis |
-
2014
- 2014-02-03 HK HK16102846.4A patent/HK1214772A1/zh unknown
- 2014-02-03 MX MX2015009908A patent/MX2015009908A/es unknown
- 2014-02-03 KR KR1020157023636A patent/KR20150114984A/ko not_active Withdrawn
- 2014-02-03 JP JP2015556207A patent/JP6387019B2/ja not_active Expired - Fee Related
- 2014-02-03 BR BR112015017958A patent/BR112015017958A2/pt not_active IP Right Cessation
- 2014-02-03 CN CN201480015923.2A patent/CN105188737A/zh active Pending
- 2014-02-03 EA EA201500783A patent/EA030414B1/ru not_active IP Right Cessation
- 2014-02-03 AU AU2014212095A patent/AU2014212095B2/en not_active Ceased
- 2014-02-03 CA CA2900050A patent/CA2900050A1/en not_active Abandoned
- 2014-02-03 SG SG11201505715RA patent/SG11201505715RA/en unknown
- 2014-02-03 WO PCT/US2014/014478 patent/WO2014121210A1/en not_active Ceased
- 2014-02-03 SG SG10201706213RA patent/SG10201706213RA/en unknown
- 2014-02-03 US US14/765,018 patent/US20150366932A1/en not_active Abandoned
- 2014-02-03 EP EP14745933.3A patent/EP2950811A4/en not_active Withdrawn
-
2015
- 2015-07-23 IL IL240125A patent/IL240125A0/en unknown
- 2015-07-31 PH PH12015501705A patent/PH12015501705A1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU2014212095A1 (en) | 2015-09-10 |
| KR20150114984A (ko) | 2015-10-13 |
| JP2016511238A (ja) | 2016-04-14 |
| HK1214772A1 (zh) | 2016-08-05 |
| JP6387019B2 (ja) | 2018-09-05 |
| SG10201706213RA (en) | 2017-09-28 |
| US20150366932A1 (en) | 2015-12-24 |
| IL240125A0 (en) | 2015-09-24 |
| CA2900050A1 (en) | 2014-08-07 |
| SG11201505715RA (en) | 2015-08-28 |
| MX2015009908A (es) | 2015-09-24 |
| WO2014121210A1 (en) | 2014-08-07 |
| CN105188737A (zh) | 2015-12-23 |
| BR112015017958A2 (pt) | 2017-07-11 |
| PH12015501705A1 (en) | 2015-10-12 |
| EA201500783A1 (ru) | 2016-05-31 |
| EP2950811A1 (en) | 2015-12-09 |
| EP2950811A4 (en) | 2016-06-08 |
| EA030414B1 (ru) | 2018-08-31 |
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