NO311223B1 - Uretaner og ureaer som induserer cytokin-produksjon, fremgangsmåte for fremstilling derav samt farmasöytisk preparatinneholdende slik forbindelse - Google Patents
Uretaner og ureaer som induserer cytokin-produksjon, fremgangsmåte for fremstilling derav samt farmasöytisk preparatinneholdende slik forbindelse Download PDFInfo
- Publication number
- NO311223B1 NO311223B1 NO19941786A NO941786A NO311223B1 NO 311223 B1 NO311223 B1 NO 311223B1 NO 19941786 A NO19941786 A NO 19941786A NO 941786 A NO941786 A NO 941786A NO 311223 B1 NO311223 B1 NO 311223B1
- Authority
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- Norway
- Prior art keywords
- carboxy
- amino
- carbonyl
- alanine
- lysyl
- Prior art date
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- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 1
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- 230000011132 hemopoiesis Effects 0.000 description 1
- UCVODTZQZHMTPN-UHFFFAOYSA-N heptanoyl chloride Chemical compound CCCCCCC(Cl)=O UCVODTZQZHMTPN-UHFFFAOYSA-N 0.000 description 1
- 125000000268 heptanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
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- 210000000265 leukocyte Anatomy 0.000 description 1
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- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- GMKMEZVLHJARHF-SYDPRGILSA-N meso-2,6-diaminopimelic acid Chemical compound [O-]C(=O)[C@@H]([NH3+])CCC[C@@H]([NH3+])C([O-])=O GMKMEZVLHJARHF-SYDPRGILSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- NDBQJIBNNUJNHA-DFWYDOINSA-N methyl (2s)-2-amino-3-hydroxypropanoate;hydrochloride Chemical compound Cl.COC(=O)[C@@H](N)CO NDBQJIBNNUJNHA-DFWYDOINSA-N 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 230000003278 mimic effect Effects 0.000 description 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
- CJPMSUUANYLPET-UHFFFAOYSA-N n-[3-[[5-cyclopropyl-2-(4-morpholin-4-ylanilino)pyrimidin-4-yl]amino]propyl]cyclobutanecarboxamide Chemical compound C1CCC1C(=O)NCCCNC(C(=CN=1)C2CC2)=NC=1NC(C=C1)=CC=C1N1CCOCC1 CJPMSUUANYLPET-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229910052757 nitrogen Chemical group 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- SJYNFBVQFBRSIB-UHFFFAOYSA-N norbornadiene Chemical compound C1=CC2C=CC1C2 SJYNFBVQFBRSIB-UHFFFAOYSA-N 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 238000006864 oxidative decomposition reaction Methods 0.000 description 1
- NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
- 108010090259 pimelautide Proteins 0.000 description 1
- 229950004124 pimelautide Drugs 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 150000003140 primary amides Chemical class 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000006268 reductive amination reaction Methods 0.000 description 1
- 238000010405 reoxidation reaction Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229950003733 romurtide Drugs 0.000 description 1
- 108700033545 romurtide Proteins 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 238000013207 serial dilution Methods 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 238000012353 t test Methods 0.000 description 1
- LRBQNJMCXXYXIU-NRMVVENXSA-N tannic acid Chemical compound OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@@H]2[C@H]([C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-NRMVVENXSA-N 0.000 description 1
- 229940033123 tannic acid Drugs 0.000 description 1
- 235000015523 tannic acid Nutrition 0.000 description 1
- 229920002258 tannic acid Polymers 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- MHYGQXWCZAYSLJ-UHFFFAOYSA-N tert-butyl-chloro-diphenylsilane Chemical compound C=1C=CC=CC=1[Si](Cl)(C(C)(C)C)C1=CC=CC=C1 MHYGQXWCZAYSLJ-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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000004797 therapeutic response Effects 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 239000003104 tissue culture media Substances 0.000 description 1
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- OKKJLVBELUTLKV-FIBGUPNXSA-N trideuteriomethanol Chemical compound [2H]C([2H])([2H])O OKKJLVBELUTLKV-FIBGUPNXSA-N 0.000 description 1
- UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
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
- C07K5/06—Dipeptides
- C07K5/06104—Dipeptides with the first amino acid being acidic
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
-
- 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
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/04—Immunostimulants
-
- 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
- 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
- C07K5/06—Dipeptides
- C07K5/06086—Dipeptides with the first amino acid being basic
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Molecular Biology (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Genetics & Genomics (AREA)
- Virology (AREA)
- Immunology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- AIDS & HIV (AREA)
- Tropical Medicine & Parasitology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Polyurethanes Or Polyureas (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/063,174 US5312831A (en) | 1993-05-12 | 1993-05-12 | Urethanes and ureas that induce cytokine production |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO941786D0 NO941786D0 (no) | 1994-05-11 |
| NO941786L NO941786L (no) | 1994-11-14 |
| NO311223B1 true NO311223B1 (no) | 2001-10-29 |
Family
ID=22047440
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19941786A NO311223B1 (no) | 1993-05-12 | 1994-05-11 | Uretaner og ureaer som induserer cytokin-produksjon, fremgangsmåte for fremstilling derav samt farmasöytisk preparatinneholdende slik forbindelse |
Country Status (26)
| Country | Link |
|---|---|
| US (6) | US5312831A (hu) |
| EP (1) | EP0652228B1 (hu) |
| JP (1) | JP3583469B2 (hu) |
| KR (1) | KR100296543B1 (hu) |
| CN (1) | CN1094943C (hu) |
| AT (1) | ATE144533T1 (hu) |
| AU (1) | AU669064B2 (hu) |
| CA (1) | CA2123261A1 (hu) |
| CZ (1) | CZ290445B6 (hu) |
| DE (1) | DE69400798T2 (hu) |
| DK (1) | DK0652228T3 (hu) |
| ES (1) | ES2094004T3 (hu) |
| FI (1) | FI942186A (hu) |
| GR (1) | GR3022253T3 (hu) |
| HU (1) | HU219768B (hu) |
| IL (1) | IL109602A (hu) |
| NO (1) | NO311223B1 (hu) |
| NZ (1) | NZ260507A (hu) |
| PH (1) | PH30182A (hu) |
| PL (1) | PL179984B1 (hu) |
| RU (1) | RU2135515C1 (hu) |
| SG (1) | SG43071A1 (hu) |
| SI (1) | SI0652228T1 (hu) |
| SK (1) | SK281120B6 (hu) |
| TW (1) | TW380129B (hu) |
| ZA (1) | ZA943266B (hu) |
Families Citing this family (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE1007183A3 (fr) * | 1993-06-18 | 1995-04-18 | Solvay | Ureines derivees d'alpha, omega-diaminoacides et procede pour leur preparation. |
| WO1996025157A1 (en) * | 1995-02-17 | 1996-08-22 | Smithkline Beecham Corporation | Il-8 receptor antagonists |
| US6005008A (en) * | 1996-02-16 | 1999-12-21 | Smithkline Beecham Corporation | IL-8 receptor antagonists |
| US6262113B1 (en) | 1996-03-20 | 2001-07-17 | Smithkline Beecham Corporation | IL-8 receptor antagonists |
| US6211373B1 (en) | 1996-03-20 | 2001-04-03 | Smithkline Beecham Corporation | Phenyl urea antagonists of the IL-8 receptor |
| AU3409197A (en) * | 1996-06-27 | 1998-01-14 | Smithkline Beecham Corporation | Il-8 receptor antagonists |
| EP0915651A4 (en) | 1996-06-27 | 2001-10-24 | Smithkline Beecham Corp | IL-8 RECEPTOR ANTAGONISTS |
| EP0939634A4 (en) * | 1996-08-15 | 2001-02-21 | Smithkline Beecham Corp | IL-8 RECEPTOR ANTAGONISTS |
| WO1999050238A1 (fr) * | 1998-03-26 | 1999-10-07 | Santen Pharmaceutical Co., Ltd. | Nouveaux derives d'uree |
| US7465754B1 (en) | 1999-09-15 | 2008-12-16 | Wyeth | Method of potentiating chemotherapy and treating solid tumors |
| US7048922B2 (en) * | 2002-05-29 | 2006-05-23 | Demao Yang | Stimulation of hematopoiesis by ex vivo activated immune cells |
| US7332158B2 (en) | 2002-05-29 | 2008-02-19 | Demao Yang | Compositions and treatments for myelosuppression by ex vivo activated immune cells |
| TW200418812A (en) * | 2002-10-29 | 2004-10-01 | Smithkline Beecham Corp | IL-8 receptor antagonists |
| US20060057121A1 (en) * | 2004-09-10 | 2006-03-16 | Demao Yang | Compositions and treatments using ex vivo activated cells for myelosuppressed patients |
| UA98456C2 (en) * | 2006-04-21 | 2012-05-25 | Смитклайн Бичам Корпорейшн | Il-8 receptor antagonists |
| US8097626B2 (en) * | 2006-04-21 | 2012-01-17 | Glaxosmithkline Llc | IL-8 receptor antagonists |
| TW200817006A (en) * | 2006-06-23 | 2008-04-16 | Smithkline Beecham Corp | IL-8 receptor antagonist |
| CA2868058C (en) | 2012-03-30 | 2019-12-17 | Givaudan S.A. | N-acylated methionine derivatives as food flavouring compounds |
| WO2013149035A2 (en) | 2012-03-30 | 2013-10-03 | Givaudan S.A. | Improvements in or relating to organic compounds |
| CN104244734B (zh) | 2012-03-30 | 2018-04-03 | 奇华顿股份有限公司 | 作为食品加香化合物的n‑酰化1‑氨基环烷基羧酸 |
| US10836712B2 (en) | 2012-03-30 | 2020-11-17 | Givaudan S.A. | Organic compounds |
| EP2830441B1 (en) | 2012-03-30 | 2019-11-13 | Givaudan SA | N-acyl derivatives of gamma amino-butyric acid as food flavouring compounds |
| CA2868073C (en) | 2012-03-30 | 2020-12-29 | Givaudan S.A. | N-acyl proline derivatives as food flavouring compounds |
| BR112014023941B1 (pt) | 2012-03-30 | 2020-07-14 | Givaudan S.A. | Composição flavorizante em pó, bem como composições comestíveis de petisco e refresco em pó compreendendo a mesma |
| WO2013149025A1 (en) * | 2012-03-30 | 2013-10-03 | Givaudan, S., A. | N-acyl serine derivatives as food flavouring compounds |
| CN105636457B (zh) | 2013-10-02 | 2020-03-10 | 奇华顿股份有限公司 | 具有味道改进特性的有机化合物 |
| US11122826B2 (en) | 2013-10-02 | 2021-09-21 | Givaudan Sa | Organic compounds |
| WO2015050534A1 (en) | 2013-10-02 | 2015-04-09 | Givaudan S.A. | Organic compounds |
| EP3057447B1 (en) | 2013-10-02 | 2017-12-06 | Givaudan S.A. | Organic compounds having taste-modifying properties |
| WO2015050535A1 (en) | 2013-10-02 | 2015-04-09 | Givaudan S.A. | Organic compounds |
| GB201317424D0 (en) * | 2013-10-02 | 2013-11-13 | Givaudan Sa | Improvements in or relating to organic compounds |
| WO2015050537A1 (en) | 2013-10-02 | 2015-04-09 | Givaudan S.A. | Organic compounds |
| EP3057444B1 (en) | 2013-10-02 | 2017-12-06 | Givaudan SA | Organic compounds having taste-modifying properties |
| CA3072735A1 (en) | 2017-08-21 | 2019-02-28 | Celgene Corporation | Processes for the preparation of (s)-tert-butyl 4,5-diamino-5-oxopentanoate |
| CN109601739B (zh) * | 2019-01-17 | 2022-10-14 | 河南湾流生物科技有限公司 | 一种复合氨基酸饲料添加剂及其制备方法 |
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|---|---|---|---|---|
| GB2033906B (en) * | 1978-10-19 | 1982-12-01 | Anvar | Water-soluble compounds derived from extracts of streptomyces stimulosus process for their production and compositions containing them |
| US4349466A (en) * | 1978-11-14 | 1982-09-14 | Fujisawa Pharmaceutical Co | Peptide, process for preparation thereof and use thereof |
| US4725582A (en) * | 1978-11-14 | 1988-02-16 | Fujisawa Pharmaceutical Company, Ltd. | Peptide, process for preparation thereof and use thereof |
| FR2460290A1 (fr) * | 1979-06-29 | 1981-01-23 | Rhone Poulenc Ind | Nouveaux tetra- ou pentapeptides, leur preparation et les medicaments qui les contiennent |
| EP0663826B1 (en) * | 1991-09-27 | 1998-12-23 | Board Of Regents The University Of Texas System | Amino acids containing parenteral formulations for the treatment of hypotension and related pathologies |
-
1993
- 1993-05-12 US US08/063,174 patent/US5312831A/en not_active Expired - Lifetime
-
1994
- 1994-03-14 US US08/213,303 patent/US5545662A/en not_active Expired - Lifetime
- 1994-04-20 SG SG1996003270A patent/SG43071A1/en unknown
- 1994-04-20 EP EP94106123A patent/EP0652228B1/en not_active Expired - Lifetime
- 1994-04-20 DE DE69400798T patent/DE69400798T2/de not_active Expired - Fee Related
- 1994-04-20 AT AT94106123T patent/ATE144533T1/de not_active IP Right Cessation
- 1994-04-20 DK DK94106123.6T patent/DK0652228T3/da active
- 1994-04-20 ES ES94106123T patent/ES2094004T3/es not_active Expired - Lifetime
- 1994-04-20 SI SI9430017T patent/SI0652228T1/xx not_active IP Right Cessation
- 1994-04-22 CZ CZ1994981A patent/CZ290445B6/cs not_active IP Right Cessation
- 1994-04-28 SK SK491-94A patent/SK281120B6/sk unknown
- 1994-05-06 HU HU9401444A patent/HU219768B/hu not_active IP Right Cessation
- 1994-05-09 JP JP11953294A patent/JP3583469B2/ja not_active Expired - Fee Related
- 1994-05-09 IL IL10960294A patent/IL109602A/xx not_active IP Right Cessation
- 1994-05-10 CA CA002123261A patent/CA2123261A1/en not_active Abandoned
- 1994-05-11 AU AU63043/94A patent/AU669064B2/en not_active Ceased
- 1994-05-11 ZA ZA943266A patent/ZA943266B/xx unknown
- 1994-05-11 PH PH48247A patent/PH30182A/en unknown
- 1994-05-11 FI FI942186A patent/FI942186A/fi not_active Application Discontinuation
- 1994-05-11 NZ NZ260507A patent/NZ260507A/en unknown
- 1994-05-11 PL PL94303396A patent/PL179984B1/pl not_active IP Right Cessation
- 1994-05-11 RU RU94016389A patent/RU2135515C1/ru not_active IP Right Cessation
- 1994-05-11 NO NO19941786A patent/NO311223B1/no unknown
- 1994-05-11 KR KR1019940010317A patent/KR100296543B1/ko not_active IP Right Cessation
- 1994-05-12 CN CN94105671A patent/CN1094943C/zh not_active Expired - Fee Related
- 1994-08-13 TW TW083107431A patent/TW380129B/zh not_active IP Right Cessation
-
1995
- 1995-05-25 US US08/449,878 patent/US5602275A/en not_active Expired - Lifetime
- 1995-05-25 US US08/451,099 patent/US5616612A/en not_active Expired - Lifetime
- 1995-05-25 US US08/449,968 patent/US5658945A/en not_active Expired - Lifetime
- 1995-05-25 US US08/451,085 patent/US5633280A/en not_active Expired - Lifetime
-
1997
- 1997-01-09 GR GR970400020T patent/GR3022253T3/el unknown
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