JPH0717503B2 - ミリストイル化を伴う疾患の治療を意図する薬効のある生成物を得るためのｎ−ミリストイル−（ｓ）−フェニルアラニンの使用 - Google Patents
ミリストイル化を伴う疾患の治療を意図する薬効のある生成物を得るためのｎ−ミリストイル−（ｓ）−フェニルアラニンの使用Info
- Publication number
- JPH0717503B2 JPH0717503B2 JP3007188A JP718891A JPH0717503B2 JP H0717503 B2 JPH0717503 B2 JP H0717503B2 JP 3007188 A JP3007188 A JP 3007188A JP 718891 A JP718891 A JP 718891A JP H0717503 B2 JPH0717503 B2 JP H0717503B2
- Authority
- JP
- Japan
- Prior art keywords
- myristoyl
- phenylalanine
- myristoylation
- treatment
- diseases associated
- 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.)
- Expired - Lifetime
Links
- GFNNQTYRJPFJGX-NRFANRHFSA-N (2s)-3-phenyl-2-(tetradecanoylamino)propanoic acid Chemical compound CCCCCCCCCCCCCC(=O)N[C@H](C(O)=O)CC1=CC=CC=C1 GFNNQTYRJPFJGX-NRFANRHFSA-N 0.000 title claims abstract description 11
- 238000011282 treatment Methods 0.000 title abstract description 4
- 201000010099 disease Diseases 0.000 title abstract description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title abstract description 3
- 230000007498 myristoylation Effects 0.000 title description 5
- 229940126601 medicinal product Drugs 0.000 title 1
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 9
- 201000011510 cancer Diseases 0.000 claims abstract description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 2
- 231100000252 nontoxic Toxicity 0.000 claims description 2
- 230000003000 nontoxic effect Effects 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 208000030507 AIDS Diseases 0.000 abstract description 2
- 210000004027 cell Anatomy 0.000 description 12
- 230000000694 effects Effects 0.000 description 11
- 108090000623 proteins and genes Proteins 0.000 description 10
- 102000004190 Enzymes Human genes 0.000 description 9
- 108090000790 Enzymes Proteins 0.000 description 9
- 108010016306 Glycylpeptide N-tetradecanoyltransferase Proteins 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 9
- 235000018102 proteins Nutrition 0.000 description 9
- 102000004169 proteins and genes Human genes 0.000 description 9
- 239000003112 inhibitor Substances 0.000 description 6
- 230000003013 cytotoxicity Effects 0.000 description 5
- 231100000135 cytotoxicity Toxicity 0.000 description 5
- 230000005764 inhibitory process Effects 0.000 description 5
- 230000035800 maturation Effects 0.000 description 5
- 108090000765 processed proteins & peptides Proteins 0.000 description 5
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 4
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 4
- TUNFSRHWOTWDNC-UHFFFAOYSA-N Myristic acid Natural products CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- 230000001131 transforming effect Effects 0.000 description 4
- TWJNQYPJQDRXPH-UHFFFAOYSA-N 2-cyanobenzohydrazide Chemical compound NNC(=O)C1=CC=CC=C1C#N TWJNQYPJQDRXPH-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 235000021360 Myristic acid Nutrition 0.000 description 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
- 230000010261 cell growth Effects 0.000 description 3
- 230000010307 cell transformation Effects 0.000 description 3
- 239000002609 medium Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- 241001430294 unidentified retrovirus Species 0.000 description 3
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 2
- 239000004471 Glycine Substances 0.000 description 2
- DYUGTPXLDJQBRB-UHFFFAOYSA-N N-myristoylglycine Chemical class CCCCCCCCCCCCCC(=O)NCC(O)=O DYUGTPXLDJQBRB-UHFFFAOYSA-N 0.000 description 2
- 102000004022 Protein-Tyrosine Kinases Human genes 0.000 description 2
- 108090000412 Protein-Tyrosine Kinases Proteins 0.000 description 2
- 229940100514 Syk tyrosine kinase inhibitor Drugs 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 229940024606 amino acid Drugs 0.000 description 2
- 235000001014 amino acid Nutrition 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 230000012010 growth Effects 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 208000032839 leukemia Diseases 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 210000001589 microsome Anatomy 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
- 239000006190 sub-lingual tablet Substances 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 2
- 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 1
- PZCXJTZUYUTKQH-CEOVSRFSSA-N 2-aminoacetic acid (2S)-2-aminopropanoic acid (2S)-2,4-diamino-4-oxobutanoic acid Chemical compound NCC(O)=O.C[C@H](N)C(O)=O.OC(=O)[C@@H](N)CC(N)=O PZCXJTZUYUTKQH-CEOVSRFSSA-N 0.000 description 1
- 239000004475 Arginine Substances 0.000 description 1
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
- 102000004631 Calcineurin Human genes 0.000 description 1
- 108010042955 Calcineurin Proteins 0.000 description 1
- RGJOEKWQDUBAIZ-IBOSZNHHSA-N CoASH Chemical compound O[C@@H]1[C@H](OP(O)(O)=O)[C@@H](COP(O)(=O)OP(O)(=O)OCC(C)(C)[C@@H](O)C(=O)NCCC(=O)NCCS)O[C@H]1N1C2=NC=NC(N)=C2N=C1 RGJOEKWQDUBAIZ-IBOSZNHHSA-N 0.000 description 1
- 102000005870 Coenzyme A Ligases Human genes 0.000 description 1
- 102000008130 Cyclic AMP-Dependent Protein Kinases Human genes 0.000 description 1
- 108010049894 Cyclic AMP-Dependent Protein Kinases Proteins 0.000 description 1
- 239000007995 HEPES buffer Substances 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 108010011449 Long-chain-fatty-acid-CoA ligase Proteins 0.000 description 1
- 108010038807 Oligopeptides Chemical class 0.000 description 1
- 102000015636 Oligopeptides Human genes 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
- 241000589516 Pseudomonas Species 0.000 description 1
- 239000012980 RPMI-1640 medium Substances 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- PMZXXNPJQYDFJX-UHFFFAOYSA-N acetonitrile;2,2,2-trifluoroacetic acid Chemical compound CC#N.OC(=O)C(F)(F)F PMZXXNPJQYDFJX-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- 239000012620 biological material Substances 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 231100000315 carcinogenic Toxicity 0.000 description 1
- 230000004663 cell proliferation Effects 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- RGJOEKWQDUBAIZ-UHFFFAOYSA-N coenzime A Natural products OC1C(OP(O)(O)=O)C(COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)OC1N1C2=NC=NC(N)=C2N=C1 RGJOEKWQDUBAIZ-UHFFFAOYSA-N 0.000 description 1
- 239000005516 coenzyme A Substances 0.000 description 1
- 229940093530 coenzyme a Drugs 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000001472 cytotoxic effect Effects 0.000 description 1
- KDTSHFARGAKYJN-UHFFFAOYSA-N dephosphocoenzyme A Natural products OC1C(O)C(COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)OC1N1C2=NC=NC(N)=C2N=C1 KDTSHFARGAKYJN-UHFFFAOYSA-N 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 210000002472 endoplasmic reticulum Anatomy 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012091 fetal bovine serum Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 239000007903 gelatin capsule 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
- 125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 239000012139 lysis buffer Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 238000004452 microanalysis Methods 0.000 description 1
- 229940105132 myristate Drugs 0.000 description 1
- 125000001419 myristoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- DUAFKXOFBZQTQE-QSGBVPJFSA-N myristoyl-CoA Chemical compound O[C@@H]1[C@H](OP(O)(O)=O)[C@@H](COP(O)(=O)OP(O)(=O)OCC(C)(C)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)CCCCCCCCCCCCC)O[C@H]1N1C2=NC=NC(N)=C2N=C1 DUAFKXOFBZQTQE-QSGBVPJFSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000001177 retroviral effect Effects 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- QOISWWBTZMFUEL-NSHDSACASA-N tert-butyl (2s)-2-amino-3-phenylpropanoate Chemical compound CC(C)(C)OC(=O)[C@@H](N)CC1=CC=CC=C1 QOISWWBTZMFUEL-NSHDSACASA-N 0.000 description 1
- PRRZBLSCLSGLIT-DEOSSOPVSA-N tert-butyl (2s)-3-phenyl-2-(tetradecanoylamino)propanoate Chemical compound CCCCCCCCCCCCCC(=O)N[C@H](C(=O)OC(C)(C)C)CC1=CC=CC=C1 PRRZBLSCLSGLIT-DEOSSOPVSA-N 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 229940100445 wheat starch Drugs 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/005—Enzyme inhibitors
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/20—Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Virology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Molecular Biology (AREA)
- Tropical Medicine & Parasitology (AREA)
- AIDS & HIV (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9000834A FR2657259A1 (fr) | 1990-01-25 | 1990-01-25 | Utilisation de la n-myristoyl-(s)-phenylalanine pour l'obtention de medicaments destines au traitement des maladies faisant intervenir la myristoylation. |
| FR9000834 | 1990-01-25 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH04210916A JPH04210916A (ja) | 1992-08-03 |
| JPH0717503B2 true JPH0717503B2 (ja) | 1995-03-01 |
Family
ID=9393082
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3007188A Expired - Lifetime JPH0717503B2 (ja) | 1990-01-25 | 1991-01-24 | ミリストイル化を伴う疾患の治療を意図する薬効のある生成物を得るためのｎ−ミリストイル−（ｓ）−フェニルアラニンの使用 |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US5164414A (enExample) |
| EP (1) | EP0443891B1 (enExample) |
| JP (1) | JPH0717503B2 (enExample) |
| AT (1) | ATE94387T1 (enExample) |
| AU (1) | AU633395B2 (enExample) |
| CA (1) | CA2034861A1 (enExample) |
| DE (1) | DE69100364T2 (enExample) |
| DK (1) | DK0443891T3 (enExample) |
| ES (1) | ES2060310T3 (enExample) |
| FR (1) | FR2657259A1 (enExample) |
| IE (1) | IE65573B1 (enExample) |
| OA (1) | OA09478A (enExample) |
| PT (1) | PT96571A (enExample) |
| ZA (1) | ZA91574B (enExample) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2672598A1 (fr) * | 1991-02-11 | 1992-08-14 | Adir | Nouveaux inhibiteurs de n-myristoyltransferase, leur procede de preparation et les compositions pharmaceutiques qui les contiennent. |
| US5599947A (en) * | 1993-01-14 | 1997-02-04 | G. D. Searle & Co. | Fatty acid analogs and prodrugs |
| US5859052A (en) * | 1993-01-14 | 1999-01-12 | G. D. Searle & Co. | Fatty acid analogs and prodrugs |
| US6127393A (en) * | 1995-12-29 | 2000-10-03 | Novactyl, Inc. | Antiproliferative, antiinfective, antiinflammatory, autologous immunization agent and method |
| US6407125B1 (en) | 1995-12-29 | 2002-06-18 | Novactyl, Inc. | Pharmacological agent and method of treatment |
| US6743771B2 (en) | 1995-12-29 | 2004-06-01 | Novactyl, Inc. | Methods and compositions for controlling protein assembly or aggregation |
| US6579891B1 (en) | 1995-12-29 | 2003-06-17 | Novactyl, Inc. | Agent and method for prevention and treatment of cancer in animals |
| US6441009B1 (en) | 1998-08-01 | 2002-08-27 | Novactyl, Inc. | Agent and method of preventing and treating heavy metal exposure and toxicity |
| EP1220669A4 (en) * | 1999-10-13 | 2004-12-08 | Marco A Chacon | THERAPEUTIC MEASURE TO IMPROVE THE EFFECT OF A CALORY RESTRICTION |
| US6403618B1 (en) | 2000-02-15 | 2002-06-11 | Novactyl, Inc. | Agent and method for controlling angiogenesis |
| WO2003007876A2 (en) * | 2001-06-25 | 2003-01-30 | University Of Massachusetts | N-fatty acid-amino acid conjugates and therapeutic uses |
| DE10353806A1 (de) * | 2003-11-14 | 2005-07-07 | Bundesrepublik Deutschland, vertreten durch das Bundesministerium für Gesundheit, dieses vertreten durch das Robert-Koch-Institut, vertreten durch seinen Präsidenten | Verwendung von Aminosäure- und Zucker-Amphiphilen zur Inaktivierung von lipidumhüllten Viren |
| US7544714B2 (en) * | 2004-07-16 | 2009-06-09 | University Of Massachusetts | Lipid-amino acid conjugates and methods of use |
| IL172896A0 (en) * | 2005-12-29 | 2006-06-11 | Yeda Res & Dev | Cxcr4 inhibition |
| MX368261B (es) | 2011-07-22 | 2019-09-25 | Pacylex Pharmaceuticals Inc | Letalidad sintetica y el tratamiento de cancer. |
| SG11201405413SA (en) | 2012-03-30 | 2014-10-30 | Givaudan Sa | N-acyl derivatives of gamma amino - butyric acid and and beta alanine as food flavouring compounds |
| CN104219964B (zh) | 2012-03-30 | 2016-09-21 | 奇华顿股份有限公司 | 作为食品加香化合物的n-酰基脯氨酸衍生物 |
| US10856563B2 (en) | 2012-03-30 | 2020-12-08 | Givaudan S.A. | N-acyl-amino acid derivatives for improvement of the flavor profile of edible compositions |
| JP6320367B2 (ja) | 2012-03-30 | 2018-05-09 | ジボダン エス エー | 食品フレーバー付与化合物としてのｎ−アシル化メチオニン誘導体 |
| JP6248092B2 (ja) | 2012-03-30 | 2017-12-13 | ジボダン エス エー | 食品フレーバー付与化合物としてのｎ−アシル化１−アミノシクロアルキルカルボン酸 |
| US10582715B2 (en) | 2012-03-30 | 2020-03-10 | Givaudan Sa | Powder flavour composition |
| BR122020006518B1 (pt) | 2012-03-30 | 2022-02-22 | Givaudan Sa | Composição de sabor |
| KR102496892B1 (ko) * | 2012-10-30 | 2023-02-06 | 페이실렉스 파마슈티컬스 인코포레이티드 | 암의 합성치사 및 치료 |
| EP3057448B1 (en) | 2013-10-02 | 2017-12-06 | Givaudan S.A. | Organic compounds having taste-modifying properties |
| EP3057446B1 (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 |
| WO2015048991A1 (en) | 2013-10-02 | 2015-04-09 | Givaudan Sa | Organic compounds having taste-modifying properties |
| GB201317424D0 (en) | 2013-10-02 | 2013-11-13 | Givaudan Sa | Improvements in or relating to organic compounds |
| EP3057447B1 (en) | 2013-10-02 | 2017-12-06 | Givaudan S.A. | Organic compounds having taste-modifying properties |
| CN105636934B (zh) | 2013-10-02 | 2019-03-29 | 奇华顿股份有限公司 | N-酰化的2-氨基异丁酸化合物和包含它们的香味组合物 |
| WO2015048990A1 (en) | 2013-10-02 | 2015-04-09 | Givaudan Sa | Organic compounds having taste-modifying properties |
| EP3325662B1 (en) | 2015-07-17 | 2023-08-30 | Pacylex Pharmaceuticals Inc. | Epigenetic silencing of nmt2 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4778877A (en) * | 1986-08-07 | 1988-10-18 | Washington University | Novel inhibitor peptides II |
| US4778878A (en) * | 1986-08-07 | 1988-10-18 | Washington University | Novel inhibitor peptides I |
-
1990
- 1990-01-25 FR FR9000834A patent/FR2657259A1/fr active Granted
-
1991
- 1991-01-24 JP JP3007188A patent/JPH0717503B2/ja not_active Expired - Lifetime
- 1991-01-24 IE IE24291A patent/IE65573B1/en not_active IP Right Cessation
- 1991-01-24 PT PT96571A patent/PT96571A/pt not_active Application Discontinuation
- 1991-01-24 US US07/645,124 patent/US5164414A/en not_active Expired - Fee Related
- 1991-01-24 CA CA002034861A patent/CA2034861A1/fr not_active Abandoned
- 1991-01-25 EP EP91400163A patent/EP0443891B1/fr not_active Expired - Lifetime
- 1991-01-25 ES ES91400163T patent/ES2060310T3/es not_active Expired - Lifetime
- 1991-01-25 AU AU69987/91A patent/AU633395B2/en not_active Ceased
- 1991-01-25 DE DE91400163T patent/DE69100364T2/de not_active Expired - Fee Related
- 1991-01-25 DK DK91400163.1T patent/DK0443891T3/da active
- 1991-01-25 OA OA59940A patent/OA09478A/xx unknown
- 1991-01-25 ZA ZA91574A patent/ZA91574B/xx unknown
- 1991-01-25 AT AT91400163T patent/ATE94387T1/de active
Also Published As
| Publication number | Publication date |
|---|---|
| IE65573B1 (en) | 1995-11-01 |
| EP0443891B1 (fr) | 1993-09-15 |
| EP0443891A1 (fr) | 1991-08-28 |
| ES2060310T3 (es) | 1994-11-16 |
| ZA91574B (en) | 1991-11-27 |
| AU633395B2 (en) | 1993-01-28 |
| PT96571A (pt) | 1991-10-15 |
| DE69100364T2 (de) | 1994-04-21 |
| DE69100364D1 (de) | 1993-10-21 |
| OA09478A (fr) | 1992-11-15 |
| US5164414A (en) | 1992-11-17 |
| FR2657259A1 (fr) | 1991-07-26 |
| AU6998791A (en) | 1991-08-01 |
| FR2657259B1 (enExample) | 1994-08-19 |
| DK0443891T3 (da) | 1993-12-27 |
| JPH04210916A (ja) | 1992-08-03 |
| CA2034861A1 (fr) | 1991-07-26 |
| IE910242A1 (en) | 1991-07-31 |
| ATE94387T1 (de) | 1993-10-15 |
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