NO851495L - Syntese av cyklopropanaminosyrer og -peptider - Google Patents
Syntese av cyklopropanaminosyrer og -peptiderInfo
- Publication number
- NO851495L NO851495L NO851495A NO851495A NO851495L NO 851495 L NO851495 L NO 851495L NO 851495 A NO851495 A NO 851495A NO 851495 A NO851495 A NO 851495A NO 851495 L NO851495 L NO 851495L
- Authority
- NO
- Norway
- Prior art keywords
- amino acid
- cyclopropyl
- peptide
- stereospecific
- acid
- Prior art date
Links
- 108090000765 processed proteins & peptides Proteins 0.000 title claims description 105
- 239000002253 acid Substances 0.000 title claims description 51
- 102000004196 processed proteins & peptides Human genes 0.000 title description 37
- 230000015572 biosynthetic process Effects 0.000 title description 24
- 238000003786 synthesis reaction Methods 0.000 title description 24
- 150000007513 acids Chemical class 0.000 title description 5
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- 235000001014 amino acid Nutrition 0.000 claims description 103
- 230000000707 stereoselective effect Effects 0.000 claims description 71
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- -1 3-indolyl Chemical group 0.000 claims description 47
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- 125000003118 aryl group Chemical group 0.000 claims description 43
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 36
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- 230000008569 process Effects 0.000 claims description 31
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 23
- 239000003765 sweetening agent Substances 0.000 claims description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 18
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 18
- 229910052736 halogen Inorganic materials 0.000 claims description 18
- 150000002367 halogens Chemical group 0.000 claims description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims description 18
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- 210000004899 c-terminal region Anatomy 0.000 claims description 17
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 17
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- VSDUZFOSJDMAFZ-VIFPVBQESA-N methyl L-phenylalaninate Chemical compound COC(=O)[C@@H](N)CC1=CC=CC=C1 VSDUZFOSJDMAFZ-VIFPVBQESA-N 0.000 claims description 10
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- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 claims description 9
- UQBOJOOOTLPNST-UHFFFAOYSA-N Dehydroalanine Chemical class NC(=C)C(O)=O UQBOJOOOTLPNST-UHFFFAOYSA-N 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
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- 239000005864 Sulphur Chemical group 0.000 claims description 7
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- 231100000252 nontoxic Toxicity 0.000 claims description 7
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- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 claims description 7
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 6
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- 239000004474 valine Substances 0.000 claims description 6
- ULAUUWLHNYSRAV-NSHDSACASA-N (2s)-2-(cyclopropylamino)-3-phenylpropanoic acid Chemical compound C([C@@H](C(=O)O)NC1CC1)C1=CC=CC=C1 ULAUUWLHNYSRAV-NSHDSACASA-N 0.000 claims description 5
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 claims description 5
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- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 claims description 5
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- 239000000126 substance Substances 0.000 claims description 4
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- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000004104 aryloxy group Chemical group 0.000 claims description 3
- 125000002883 imidazolyl group Chemical group 0.000 claims description 3
- 125000001909 leucine group Chemical group [H]N(*)C(C(*)=O)C([H])([H])C(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 125000001500 prolyl group Chemical group [H]N1C([H])(C(=O)[*])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 3
- 125000001493 tyrosinyl group Chemical group [H]OC1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 claims description 3
- 125000005907 alkyl ester group Chemical group 0.000 claims description 2
- 150000005215 alkyl ethers Chemical class 0.000 claims description 2
- 108010069205 aspartyl-phenylalanine Proteins 0.000 claims description 2
- 150000004702 methyl esters Chemical class 0.000 claims description 2
- VHVYIBZNLBAVEM-YFKPBYRVSA-N (2s)-2-(cyclopropylamino)butanedioic acid Chemical compound OC(=O)C[C@@H](C(O)=O)NC1CC1 VHVYIBZNLBAVEM-YFKPBYRVSA-N 0.000 claims 4
- 125000000487 histidyl group Chemical group [H]N([H])C(C(=O)O*)C([H])([H])C1=C([H])N([H])C([H])=N1 0.000 claims 4
- OJNDWNWAHYLTHO-ZDUSSCGKSA-N (2s)-2-(cyclopropylamino)-3-(1h-indol-3-yl)propanoic acid Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)O)C1CC1 OJNDWNWAHYLTHO-ZDUSSCGKSA-N 0.000 claims 2
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- 239000000796 flavoring agent Substances 0.000 claims 2
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- DKVOTNPNNGKMQP-ZETCQYMHSA-N (2s)-2-(cyclopropylamino)-3-methylbutanoic acid Chemical compound CC(C)[C@@H](C(O)=O)NC1CC1 DKVOTNPNNGKMQP-ZETCQYMHSA-N 0.000 claims 1
- LRLIEDUIPVZCKP-QMMMGPOBSA-N (2s)-2-(cyclopropylamino)-4-methylpentanoic acid Chemical compound CC(C)C[C@@H](C(O)=O)NC1CC1 LRLIEDUIPVZCKP-QMMMGPOBSA-N 0.000 claims 1
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- WSDQIHATCCOMLH-UHFFFAOYSA-N phenyl n-(3,5-dichlorophenyl)carbamate Chemical compound ClC1=CC(Cl)=CC(NC(=O)OC=2C=CC=CC=2)=C1 WSDQIHATCCOMLH-UHFFFAOYSA-N 0.000 claims 1
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- 239000000243 solution Substances 0.000 description 127
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 1
- 208000013403 hyperactivity Diseases 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229960004502 levodopa Drugs 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 235000013622 meat product Nutrition 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 229930182817 methionine Natural products 0.000 description 1
- JOYFPXGYOIROJG-AWEZNQCLSA-N methyl (2s)-2-(cyclopentylamino)-3-phenylpropanoate Chemical compound C([C@@H](C(=O)OC)NC1CCCC1)C1=CC=CC=C1 JOYFPXGYOIROJG-AWEZNQCLSA-N 0.000 description 1
- HGVNLOSOAISYIT-KBPBESRZSA-N methyl (2s)-2-[[(2s)-2-amino-3-phenylpropanoyl]amino]-4-methylpentanoate Chemical compound COC(=O)[C@H](CC(C)C)NC(=O)[C@@H](N)CC1=CC=CC=C1 HGVNLOSOAISYIT-KBPBESRZSA-N 0.000 description 1
- 125000004492 methyl ester group Chemical group 0.000 description 1
- 235000020124 milk-based beverage Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- FZFLTDNAHASQQC-RVDMUPIBSA-N n-[(e)-benzylideneamino]-4-methylbenzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N\N=C\C1=CC=CC=C1 FZFLTDNAHASQQC-RVDMUPIBSA-N 0.000 description 1
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 1
- 150000002832 nitroso derivatives Chemical class 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 229940127240 opiate Drugs 0.000 description 1
- LDCYZAJDBXYCGN-UHFFFAOYSA-N oxitriptan Natural products C1=C(O)C=C2C(CC(N)C(O)=O)=CNC2=C1 LDCYZAJDBXYCGN-UHFFFAOYSA-N 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 238000006303 photolysis reaction Methods 0.000 description 1
- 230000015843 photosynthesis, light reaction Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003219 pyrazolines Chemical class 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000029865 regulation of blood pressure Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 235000012045 salad Nutrition 0.000 description 1
- 229940043230 sarcosine Drugs 0.000 description 1
- UQDJGEHQDNVPGU-UHFFFAOYSA-N serine phosphoethanolamine Chemical compound [NH3+]CCOP([O-])(=O)OCC([NH3+])C([O-])=O UQDJGEHQDNVPGU-UHFFFAOYSA-N 0.000 description 1
- 125000003607 serino group Chemical group [H]N([H])[C@]([H])(C(=O)[*])C(O[H])([H])[H] 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 235000019605 sweet taste sensations Nutrition 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 238000007910 systemic administration Methods 0.000 description 1
- 230000009967 tasteless effect Effects 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
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 235000014101 wine Nutrition 0.000 description 1
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/30—Artificial sweetening agents
- A23L27/31—Artificial sweetening agents containing amino acids, nucleotides, peptides or derivatives
- A23L27/32—Artificial sweetening agents containing amino acids, nucleotides, peptides or derivatives containing dipeptides or derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/44—Oxygen and nitrogen or sulfur and nitrogen atoms
-
- 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
- C07K14/665—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans derived from pro-opiomelanocortin, pro-enkephalin or pro-dynorphin
- C07K14/70—Enkephalins
- C07K14/702—Enkephalins with at least 1 amino acid in D-form
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/02—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link
- C07K5/0227—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing the (partial) peptide sequence -Phe-His-NH-(X)2-C(=0)-, e.g. Renin-inhibitors with n = 2 - 6; for n > 6 see C07K5/06 - C07K5/10
-
- 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
- C07K5/06008—Dipeptides with the first amino acid being neutral
- C07K5/06078—Dipeptides with the first amino acid being neutral and aromatic or cycloaliphatic
-
- 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
- C07K5/06113—Asp- or Asn-amino acid
-
- 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
- C07K5/08—Tripeptides
- C07K5/0802—Tripeptides with the first amino acid being neutral
- C07K5/0804—Tripeptides with the first amino acid being neutral and aliphatic
- C07K5/081—Tripeptides with the first amino acid being neutral and aliphatic the side chain containing O or S as heteroatoms, e.g. Cys, Ser
-
- 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
- C07K5/08—Tripeptides
- C07K5/0821—Tripeptides with the first amino acid being heterocyclic, e.g. His, Pro, Trp
-
- 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
- C07K5/101—Tetrapeptides with the first amino acid being neutral and aliphatic the side chain containing 2 to 4 carbon atoms, e.g. Val, Ile, Leu
-
- 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
- C07K7/14—Angiotensins: Related peptides
-
- 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
- C07K7/18—Kallidins; Bradykinins; Related peptides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Medicinal Chemistry (AREA)
- Genetics & Genomics (AREA)
- General Health & Medical Sciences (AREA)
- Biophysics (AREA)
- Engineering & Computer Science (AREA)
- Gastroenterology & Hepatology (AREA)
- Zoology (AREA)
- Toxicology (AREA)
- Polymers & Plastics (AREA)
- Food Science & Technology (AREA)
- Nutrition Science (AREA)
- Vascular Medicine (AREA)
- Peptides Or Proteins (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US52380883A | 1983-08-16 | 1983-08-16 | |
| US63609184A | 1984-08-03 | 1984-08-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO851495L true NO851495L (no) | 1985-04-15 |
Family
ID=27061274
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO851495A NO851495L (no) | 1983-08-16 | 1985-04-15 | Syntese av cyklopropanaminosyrer og -peptider |
Country Status (11)
| Country | Link |
|---|---|
| EP (1) | EP0135429B1 (fr) |
| AU (1) | AU579835B2 (fr) |
| DE (1) | DE3485587D1 (fr) |
| DK (1) | DK171385A (fr) |
| FI (1) | FI851508A0 (fr) |
| HU (1) | HUT38914A (fr) |
| MX (1) | MX7527E (fr) |
| NO (1) | NO851495L (fr) |
| OA (1) | OA08010A (fr) |
| PT (1) | PT79088B (fr) |
| WO (1) | WO1985000809A1 (fr) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3575761D1 (de) * | 1984-11-02 | 1990-03-08 | Toyota Motor Co Ltd | Scharniermechanismus fuer eine kraftfahrzeugseitentuer. |
| JPS63500211A (ja) * | 1984-12-11 | 1988-01-28 | ユニバーシティ オブ ジョージャ リサーチ ファウンデーション インコーポレーテッド | 熱安定化されたペプチド甘味剤 |
| WO1986003944A1 (fr) * | 1985-01-03 | 1986-07-17 | Joyce Patrick J | Succedane du sel de table comprenant un peptide thermostabilise |
| AU6224086A (en) * | 1985-08-09 | 1987-03-05 | University Of Georgia Research Foundation, Inc., The | Stabilized peptide sweetening agents |
| CS277405B6 (en) * | 1986-06-12 | 1993-03-17 | Vyzk Ustav Farm Biochem Sp | Peptides with 1-amino-1-cycloalkane carboxylic acid |
| WO1988007053A1 (fr) * | 1987-03-09 | 1988-09-22 | The Upjohn Company | Inhibiteurs de la rennine contenant un acide amino cyclopropylique ou un cycloalkyle de transition analogue |
| FR2652082B1 (fr) * | 1989-09-15 | 1991-11-22 | Rhone Poulenc Chimie | Procede de preparation de l'acide-1 cyclopropanecarboxylique ou d'un de ses sels, produits de depart et leurs procedes de preparation. |
| US5629020A (en) * | 1994-04-22 | 1997-05-13 | Emisphere Technologies, Inc. | Modified amino acids for drug delivery |
| AU3129493A (en) * | 1991-11-12 | 1993-06-15 | Promega Corporation | Non-radioactive enzyme assay |
| US6358504B1 (en) | 1997-02-07 | 2002-03-19 | Emisphere Technologies, Inc. | Compounds and compositions for delivering active agents |
| US5773647A (en) * | 1997-02-07 | 1998-06-30 | Emisphere Technologies, Inc. | Compounds and compositions for delivering active agents |
| TWI328457B (en) * | 2003-03-18 | 2010-08-11 | Suntory Holdings Ltd | Angiotensin-converting enzyme inhibitory peptides |
| US9101160B2 (en) | 2005-11-23 | 2015-08-11 | The Coca-Cola Company | Condiments with high-potency sweetener |
| US8017168B2 (en) | 2006-11-02 | 2011-09-13 | The Coca-Cola Company | High-potency sweetener composition with rubisco protein, rubiscolin, rubiscolin derivatives, ace inhibitory peptides, and combinations thereof, and compositions sweetened therewith |
| CN114436731B (zh) * | 2022-01-10 | 2023-07-11 | 北京航天试验技术研究所 | 一种环丙烷衍生物的制备方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3050559A (en) * | 1962-08-21 | Substituted phenylcyclopropylamjnes | ||
| DK326477A (da) * | 1976-07-27 | 1978-01-28 | Reckitt & Colmann Prod Ltd | Kemiske forbindelser og fremgangsmade til fremstilling af samme |
| DE2936038A1 (de) * | 1979-09-06 | 1981-03-26 | Bayer Ag, 51373 Leverkusen | Verfahren zur herstellung von 1-aminocyclopropan-carbonsaeure und deren derivaten |
| US4273704A (en) * | 1979-12-03 | 1981-06-16 | G. D. Searle & Co. | N-Adamantane-substituted tetrapeptide amides |
-
1984
- 1984-08-13 EP EP84401665A patent/EP0135429B1/fr not_active Expired - Lifetime
- 1984-08-13 MX MX84101989U patent/MX7527E/es unknown
- 1984-08-13 DE DE8484401665T patent/DE3485587D1/de not_active Expired - Lifetime
- 1984-08-14 WO PCT/US1984/001278 patent/WO1985000809A1/fr active Application Filing
- 1984-08-14 AU AU33142/84A patent/AU579835B2/en not_active Ceased
- 1984-08-14 PT PT79088A patent/PT79088B/pt unknown
- 1984-08-14 HU HU843555A patent/HUT38914A/hu unknown
-
1985
- 1985-04-12 OA OA58570BISD patent/OA08010A/fr unknown
- 1985-04-15 NO NO851495A patent/NO851495L/no unknown
- 1985-04-15 FI FI851508A patent/FI851508A0/fi not_active Application Discontinuation
- 1985-04-16 DK DK171385A patent/DK171385A/da active IP Right Grant
Also Published As
| Publication number | Publication date |
|---|---|
| PT79088A (en) | 1984-09-01 |
| EP0135429B1 (fr) | 1992-03-18 |
| WO1985000809A1 (fr) | 1985-02-28 |
| FI851508L (fi) | 1985-04-15 |
| PT79088B (en) | 1986-08-14 |
| FI851508A0 (fi) | 1985-04-15 |
| HUT38914A (en) | 1986-07-28 |
| OA08010A (fr) | 1987-01-31 |
| AU579835B2 (en) | 1988-12-15 |
| DK171385D0 (da) | 1985-04-16 |
| DK171385A (da) | 1985-04-16 |
| EP0135429A1 (fr) | 1985-03-27 |
| AU3314284A (en) | 1985-03-12 |
| DE3485587D1 (de) | 1992-04-23 |
| MX7527E (es) | 1989-07-25 |
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