NL8800100A - Nieuwe peptidederivaten en werkwijzen voor het bereiden en toepassen van deze derivaten. - Google Patents
Nieuwe peptidederivaten en werkwijzen voor het bereiden en toepassen van deze derivaten. Download PDFInfo
- Publication number
- NL8800100A NL8800100A NL8800100A NL8800100A NL8800100A NL 8800100 A NL8800100 A NL 8800100A NL 8800100 A NL8800100 A NL 8800100A NL 8800100 A NL8800100 A NL 8800100A NL 8800100 A NL8800100 A NL 8800100A
- Authority
- NL
- Netherlands
- Prior art keywords
- group
- cyclohexyl
- amido
- boc
- formula
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 30
- 108090000765 processed proteins & peptides Proteins 0.000 title description 3
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- 125000001072 heteroaryl group Chemical group 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
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- RDBGTZORXXSAAR-ZDUSSCGKSA-N (2S)-2-(3-cyclohexylpropanoylamino)hexanoic acid Chemical compound C1(CCCCC1)CCC(=O)N[C@@H](CCCC)C(=O)O RDBGTZORXXSAAR-ZDUSSCGKSA-N 0.000 claims description 4
- 206010020772 Hypertension Diseases 0.000 claims description 4
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 claims description 4
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- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 claims description 4
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- 229910052799 carbon Inorganic materials 0.000 claims description 4
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 claims description 4
- 125000002757 morpholinyl group Chemical group 0.000 claims description 4
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- 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 claims description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
- APVPOHHVBBYQAV-UHFFFAOYSA-N n-(4-aminophenyl)sulfonyloctadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 APVPOHHVBBYQAV-UHFFFAOYSA-N 0.000 claims description 3
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- HJHSDOOIPJGRSK-QMMMGPOBSA-N (2s)-2-(hexylamino)propanoic acid Chemical group CCCCCCN[C@@H](C)C(O)=O HJHSDOOIPJGRSK-QMMMGPOBSA-N 0.000 claims 1
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- WMNIIAXXRKVVBE-UHFFFAOYSA-N dichloromethane 1-hydroxybenzotriazole Chemical compound ClCCl.ON1N=NC2=C1C=CC=C2 WMNIIAXXRKVVBE-UHFFFAOYSA-N 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 230000009088 enzymatic function Effects 0.000 description 1
- 239000002532 enzyme inhibitor Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 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 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- FMKOJHQHASLBPH-UHFFFAOYSA-N isopropyl iodide Chemical compound CC(C)I FMKOJHQHASLBPH-UHFFFAOYSA-N 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- XONPDZSGENTBNJ-UHFFFAOYSA-N molecular hydrogen;sodium Chemical class [Na].[H][H] XONPDZSGENTBNJ-UHFFFAOYSA-N 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- HNHVTXYLRVGMHD-UHFFFAOYSA-N n-butyl isocyanate Chemical compound CCCCN=C=O HNHVTXYLRVGMHD-UHFFFAOYSA-N 0.000 description 1
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- RJQRCOMHVBLQIH-UHFFFAOYSA-M pentane-1-sulfonate Chemical compound CCCCCS([O-])(=O)=O RJQRCOMHVBLQIH-UHFFFAOYSA-M 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- UAJUXJSXCLUTNU-UHFFFAOYSA-N pranlukast Chemical compound C=1C=C(OCCCCC=2C=CC=CC=2)C=CC=1C(=O)NC(C=1)=CC=C(C(C=2)=O)C=1OC=2C=1N=NNN=1 UAJUXJSXCLUTNU-UHFFFAOYSA-N 0.000 description 1
- 229960004583 pranlukast Drugs 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 229960001922 sodium perborate Drugs 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- YKLJGMBLPUQQOI-UHFFFAOYSA-M sodium;oxidooxy(oxo)borane Chemical compound [Na+].[O-]OB=O YKLJGMBLPUQQOI-UHFFFAOYSA-M 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 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
- FPTGBBAFSZCUQE-NWDGAFQWSA-N tert-butyl (2S,3R)-4,4-diamino-2-(cyclohexylmethyl)-3-hydroxybutanoate Chemical compound NC([C@@H]([C@H](CC1CCCCC1)C(=O)OC(C)(C)C)O)N FPTGBBAFSZCUQE-NWDGAFQWSA-N 0.000 description 1
- QGEWBYFWVUVRRW-LAGVYOHYSA-N tert-butyl (2S,3R)-4-amino-2-(cyclohexylmethyl)-3-hydroxy-4-nitrobutanoate Chemical compound C(=O)(OC(C)(C)C)[C@H]([C@H](C([N+](=O)[O-])N)O)CC1CCCCC1 QGEWBYFWVUVRRW-LAGVYOHYSA-N 0.000 description 1
- GEJXYTQIQZSRFZ-GJZGRUSLSA-N tert-butyl (2S,3S)-4,4-diamino-2-(cyclohexylmethyl)-3-hydroxy-5-oxo-5-(propan-2-ylamino)pentanoate Chemical compound C(=O)(OC(C)(C)C)[C@H]([C@@H](C(C(NC(C)C)=O)(N)N)O)CC1CCCCC1 GEJXYTQIQZSRFZ-GJZGRUSLSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- AAJVCQPQGWUYMD-QMMMGPOBSA-N tert-butyl n-[(2s)-4-methylsulfanyl-1-oxobutan-2-yl]carbamate Chemical compound CSCC[C@@H](C=O)NC(=O)OC(C)(C)C AAJVCQPQGWUYMD-QMMMGPOBSA-N 0.000 description 1
- 238000001926 trapping method 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- 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
- C07K5/06191—Dipeptides containing heteroatoms different from O, S, or N
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biophysics (AREA)
- Biochemistry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Cardiology (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE3701526 | 1987-01-21 | ||
DE3701526 | 1987-01-21 | ||
DE3707339 | 1987-03-07 | ||
DE3707339 | 1987-03-07 |
Publications (1)
Publication Number | Publication Date |
---|---|
NL8800100A true NL8800100A (nl) | 1988-08-16 |
Family
ID=25851692
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NL8800100A NL8800100A (nl) | 1987-01-21 | 1988-01-18 | Nieuwe peptidederivaten en werkwijzen voor het bereiden en toepassen van deze derivaten. |
Country Status (13)
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DE3733296A1 (de) * | 1987-10-02 | 1989-04-20 | Merck Patent Gmbh | Aminosaeurederivate |
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JP2524814B2 (ja) * | 1988-08-25 | 1996-08-14 | キッセイ薬品工業株式会社 | α―ヒドロキシ―β―アミノ酸の製造方法 |
CA2010531A1 (en) * | 1989-03-06 | 1990-09-06 | Werner Neidhart | Amino acid derivatives |
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RU2146668C1 (ru) * | 1992-08-25 | 2000-03-20 | Джи Ди Сирл энд Компани | Сульфонилалканоиламино-гидроксиэтиламино-сульфонамидное соединение, фармацевтические композиции и способы лечения и ингибирования ретровирусных протеаз |
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CA1245217A (en) * | 1981-12-10 | 1988-11-22 | Joshua S. Boger | Renin inhibitory peptides having phe su13 xx deletion |
JPS60163899A (ja) * | 1984-02-03 | 1985-08-26 | Sankyo Co Ltd | レニン阻害ペプチド類 |
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DK356085A (da) * | 1984-08-06 | 1986-02-07 | Upjohn Co | Reninhaemmende peptid eller et farmaceutisk acceptabelt syreadditionssalt deraf |
US4727060A (en) * | 1984-11-13 | 1988-02-23 | Ciba-Geigy Corporation | Novel 5-amino-4-hydroxyvaleryl derivatives |
EP0184855A3 (en) * | 1984-12-14 | 1989-05-03 | Abbott Laboratories | Resin inhibiting compounds |
KR870005013A (ko) * | 1985-11-29 | 1987-06-04 | 가와무라 요시부미 | 레닌-억제 올리고펩티드, 그의 제조방법 및 용도 |
DE3601248A1 (de) * | 1986-01-17 | 1987-07-23 | Hoechst Ag | Substituierte 4-amino-3-hydroxybuttersaeure-derivate, verfahren zu deren herstellung, diese enthaltende mittel und ihre verwendung |
-
1988
- 1988-01-18 CH CH157/88A patent/CH676988A5/de not_active IP Right Cessation
- 1988-01-18 NL NL8800100A patent/NL8800100A/nl not_active Application Discontinuation
- 1988-01-18 GB GB8801040A patent/GB2200115B/en not_active Expired - Lifetime
- 1988-01-19 DK DK022588A patent/DK22588A/da not_active Application Discontinuation
- 1988-01-19 IL IL85136A patent/IL85136A0/xx unknown
- 1988-01-19 AU AU10375/88A patent/AU1037588A/en not_active Abandoned
- 1988-01-19 FR FR8800636A patent/FR2609716A1/fr not_active Withdrawn
- 1988-01-19 MY MYPI88000039A patent/MY102311A/en unknown
- 1988-01-19 BE BE8800067A patent/BE1002212A5/fr not_active IP Right Cessation
- 1988-01-20 SE SE8800169A patent/SE8800169L/xx not_active Application Discontinuation
- 1988-01-20 KR KR1019880000498A patent/KR880009041A/ko not_active Withdrawn
- 1988-01-20 JP JP63010571A patent/JPS6419053A/ja active Pending
- 1988-01-21 IT IT47556/88A patent/IT1219811B/it active
Also Published As
Publication number | Publication date |
---|---|
CH676988A5 (enrdf_load_stackoverflow) | 1991-03-28 |
DK22588A (da) | 1988-07-22 |
BE1002212A5 (fr) | 1990-10-16 |
IT1219811B (it) | 1990-05-24 |
GB2200115B (en) | 1990-11-14 |
IL85136A0 (en) | 1988-06-30 |
MY102311A (en) | 1992-05-28 |
SE8800169L (sv) | 1988-07-22 |
GB8801040D0 (en) | 1988-02-17 |
GB2200115A (en) | 1988-07-27 |
JPS6419053A (en) | 1989-01-23 |
AU1037588A (en) | 1988-09-01 |
FR2609716A1 (fr) | 1988-07-22 |
IT8847556A0 (it) | 1988-01-21 |
SE8800169D0 (sv) | 1988-01-20 |
KR880009041A (ko) | 1988-09-13 |
DK22588D0 (da) | 1988-01-19 |
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BV | The patent application has lapsed |