JPH0325437B2 - - Google Patents

Info

Publication number: JPH0325437B2
Authority: JP; Japan
Prior art keywords: compound; reaction; acid; lys; salts
Prior art date: 1980-10-27
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

Application number

JP56172658A

Other languages

English (en)

Japanese (ja)

Other versions

JPS57114556A (en

Inventor

Yoshio Kuroda

Hideko Iguchi

Masanobu Kosaka

Hatsuo Aoki

Hiroshi Imanaka

Yoshihiko Kitaura

Osamu Nakaguchi

Keiji Henmi

Matsuhiko Araya

Shuichi Takeno

Tatsu Okada

Hirokazu Tanaka

Shinji Hashimoto

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Fujisawa Pharmaceutical Co Ltd

Original Assignee

Fujisawa Pharmaceutical Co Ltd

Priority date (The priority date 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 date listed.)

1980-10-27

Filing date

1981-10-27

Publication date

1991-04-05

1980-10-27 Priority claimed from US201241A external-priority patent/US4322341A/en

1981-10-27 Application filed by Fujisawa Pharmaceutical Co Ltd filed Critical Fujisawa Pharmaceutical Co Ltd

1982-07-16 Publication of JPS57114556A publication Critical patent/JPS57114556A/ja

1991-04-05 Publication of JPH0325437B2 publication Critical patent/JPH0325437B2/ja

Status Granted legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 claims description 25
-1 n-octanoyl Chemical group 0.000 claims description 21
150000003839 salts Chemical class 0.000 claims description 11
229910052739 hydrogen Inorganic materials 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
125000003696 stearoyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims description 2
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 2
238000000034 method Methods 0.000 description 11
238000006243 chemical reaction Methods 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
108090000765 processed proteins & peptides Proteins 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
241000699670 Mus sp. Species 0.000 description 6
239000002253 acid Substances 0.000 description 6
239000002904 solvent Substances 0.000 description 6
208000035473 Communicable disease Diseases 0.000 description 5
238000003379 elimination reaction Methods 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
239000004480 active ingredient Substances 0.000 description 4
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
210000004027 cell Anatomy 0.000 description 4
238000007796 conventional method Methods 0.000 description 4
239000013078 crystal Substances 0.000 description 4
238000004519 manufacturing process Methods 0.000 description 4
239000000203 mixture Substances 0.000 description 4
239000008194 pharmaceutical composition Substances 0.000 description 4
230000003449 preventive effect Effects 0.000 description 4
238000006722 reduction reaction Methods 0.000 description 4
239000007787 solid Substances 0.000 description 4
239000000243 solution Substances 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
230000001093 anti-cancer Effects 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
238000001816 cooling Methods 0.000 description 3
239000004615 ingredient Substances 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
125000006239 protecting group Chemical group 0.000 description 3
239000007858 starting material Substances 0.000 description 3
239000000126 substance Substances 0.000 description 3
230000002194 synthesizing effect Effects 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
206010028980 Neoplasm Diseases 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
150000008065 acid anhydrides Chemical class 0.000 description 2
230000004913 activation Effects 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
230000001580 bacterial effect Effects 0.000 description 2
239000002585 base Substances 0.000 description 2
238000006664 bond formation reaction Methods 0.000 description 2
201000011510 cancer Diseases 0.000 description 2
238000010531 catalytic reduction reaction Methods 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
239000006260 foam Substances 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
239000002504 physiological saline solution Substances 0.000 description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
230000004083 survival effect Effects 0.000 description 2
239000000725 suspension Substances 0.000 description 2
NHBKXEKEPDILRR-UHFFFAOYSA-N 2,3-bis(butanoylsulfanyl)propyl butanoate Chemical compound CCCC(=O)OCC(SC(=O)CCC)CSC(=O)CCC NHBKXEKEPDILRR-UHFFFAOYSA-N 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
101100313763 Arabidopsis thaliana TIM22-2 gene Proteins 0.000 description 1
241000894006 Bacteria Species 0.000 description 1
229920002261 Corn starch Polymers 0.000 description 1
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical class C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
241000588724 Escherichia coli Species 0.000 description 1
201000008808 Fibrosarcoma Diseases 0.000 description 1
241000192125 Firmicutes Species 0.000 description 1
241000233866 Fungi Species 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
108010076876 Keratins Proteins 0.000 description 1
102000011782 Keratins Human genes 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
229930195725 Mannitol Natural products 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
PPQNQXQZIWHJRB-UHFFFAOYSA-N Methylcholanthrene Chemical compound C1=CC=C2C3=CC4=CC=C(C)C(CC5)=C4C5=C3C=CC2=C1 PPQNQXQZIWHJRB-UHFFFAOYSA-N 0.000 description 1
241000699666 Mus <mouse, genus> Species 0.000 description 1
NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 1
229910002651 NO3 Inorganic materials 0.000 description 1
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
HEMHJVSKTPXQMS-DYCDLGHISA-M Sodium hydroxide-d Chemical compound [Na+].[2H][O-] HEMHJVSKTPXQMS-DYCDLGHISA-M 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
239000013543 active substance Substances 0.000 description 1
125000003295 alanine group Chemical group N[C@@H](C)C(=O)* 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
230000003110 anti-inflammatory effect Effects 0.000 description 1
150000001540 azides Chemical class 0.000 description 1
239000003899 bactericide agent Substances 0.000 description 1
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
230000037396 body weight Effects 0.000 description 1
159000000007 calcium salts Chemical class 0.000 description 1
239000002775 capsule Substances 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000007810 chemical reaction solvent Substances 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
239000008119 colloidal silica Substances 0.000 description 1
239000003086 colorant Substances 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
GXGAKHNRMVGRPK-UHFFFAOYSA-N dimagnesium;dioxido-bis[[oxido(oxo)silyl]oxy]silane Chemical compound [Mg+2].[Mg+2].[O-][Si](=O)O[Si]([O-])([O-])O[Si]([O-])=O GXGAKHNRMVGRPK-UHFFFAOYSA-N 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
239000003814 drug Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
238000010828 elution Methods 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
150000002169 ethanolamines Chemical class 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
239000000945 filler Substances 0.000 description 1
238000009472 formulation Methods 0.000 description 1
239000003205 fragrance Substances 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
239000008103 glucose 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
150000004820 halides Chemical class 0.000 description 1
231100001261 hazardous Toxicity 0.000 description 1
238000002513 implantation Methods 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000012669 liquid formulation Substances 0.000 description 1
125000001288 lysyl group Chemical group 0.000 description 1
239000000391 magnesium silicate Substances 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
229940099273 magnesium trisilicate Drugs 0.000 description 1
229910000386 magnesium trisilicate Inorganic materials 0.000 description 1
235000019793 magnesium trisilicate Nutrition 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
239000002609 medium Substances 0.000 description 1
GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
230000000813 microbial effect Effects 0.000 description 1
244000000010 microbial pathogen Species 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
239000011259 mixed solution Substances 0.000 description 1
239000012046 mixed solvent Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000006072 paste Substances 0.000 description 1
239000008188 pellet Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000002335 preservative effect Effects 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000013589 supplement Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000013077 target material Substances 0.000 description 1
239000012085 test solution Substances 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
210000000115 thoracic cavity Anatomy 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
238000002054 transplantation Methods 0.000 description 1
239000006150 trypticase soy agar Substances 0.000 description 1
210000004881 tumor cell Anatomy 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1

Landscapes

Saccharide Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Peptides Or Proteins (AREA)

JP56172658A 1980-10-27 1981-10-27 Novel peptide compound and its preparation Granted JPS57114556A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US201241A US4322341A (en)	1980-05-13	1980-10-27	Peptide, process for preparation thereof and use thereof

Publications (2)

Publication Number	Publication Date
JPS57114556A JPS57114556A (en)	1982-07-16
JPH0325437B2 true JPH0325437B2 (xx)	1991-04-05

Family

ID=22745059

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP56172658A Granted JPS57114556A (en)	1980-10-27	1981-10-27	Novel peptide compound and its preparation

Country Status (1)

Country	Link
JP (1)	JPS57114556A (xx)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH068313B2 (ja) *	1983-02-08	1994-02-02	藤沢薬品工業株式会社	新規アシルグルタミルリジン誘導体
JP4949557B2 (ja) *	1999-03-17	2012-06-13	ノヴォノルディスクアー／エス	ペプチドのアシル化方法及び新規アシル化剤
US7273921B2 (en)	2002-09-25	2007-09-25	Novo Nordisk A/S	Method for producing acylated peptides
JP5217546B2 (ja) *	2007-07-03	2013-06-19	Ｊｓｒ株式会社	アミノ酸−ｎ−カルボキシ無水物の製造法
JP5217547B2 (ja) *	2007-07-03	2013-06-19	Ｊｓｒ株式会社	アミノ酸−ｎ−カルボキシ無水物の製造法
JP5217545B2 (ja) *	2008-03-19	2013-06-19	Ｊｓｒ株式会社	アミノ酸−ｎ−カルボキシ無水物の製造法

Citations (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5576850A (en) *	1978-10-19	1980-06-10	Anvar	Waterrsoluble compounds derived from extract of streptomyces stimulosus*their manufactures and immunologic adjuvant composition
JPS5585552A (en) *	1978-11-14	1980-06-27	Fujisawa Pharmaceut Co Ltd	New lactyltetrapeptide
JPS5636440A (en) *	1979-06-29	1981-04-09	Rhone Poulenc Ind	Tetrapeptide and pentapeptide* manufacture thereof and composition containing them
JPS5645447A (en) *	1979-06-29	1981-04-25	Rhone Poulenc Ind	Tripeptides* their manufacture and composition containing them

1981
- 1981-10-27 JP JP56172658A patent/JPS57114556A/ja active Granted

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5576850A (en) *	1978-10-19	1980-06-10	Anvar	Waterrsoluble compounds derived from extract of streptomyces stimulosus*their manufactures and immunologic adjuvant composition
JPS5585552A (en) *	1978-11-14	1980-06-27	Fujisawa Pharmaceut Co Ltd	New lactyltetrapeptide
JPS5636440A (en) *	1979-06-29	1981-04-09	Rhone Poulenc Ind	Tetrapeptide and pentapeptide* manufacture thereof and composition containing them
JPS5645447A (en) *	1979-06-29	1981-04-25	Rhone Poulenc Ind	Tripeptides* their manufacture and composition containing them

Also Published As

Publication number	Publication date
JPS57114556A (en)	1982-07-16

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JPH0325437B2 (xx)	1991-04-05
DE68927630T2 (de)	1997-06-12	Analoge von Peptrolsubstraten
WO1988008715A1 (en)	1988-11-17	Method of tumor inhibition in warm-blooded animals
JPS63101353A (ja)	1988-05-06	新規のアミノ酸誘導体、その製法及びこれら誘導体を含む薬剤組成物
JPH0548234B2 (xx)	1993-07-20
JPS6089488A (ja)	1985-05-20	新規アミノ酸誘導体の製法
AU2019246728A1 (en)	2020-08-27	Dipeptide piperidine derivatives
DE2609154A1 (de)	1976-09-16	Histidin-derivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
EP0271443B1 (de)	1990-10-17	N,N'-Disubstituierte Harnstoffe und Verfahren zu ihrer Herstellung
JPH05504146A (ja)	1993-07-01	シクロアルキル置換グルタルアミド降圧剤
JPH0613552B2 (ja)	1994-02-23	新規なペプタイド、その医薬として許容される塩、およびその製造法
JPS60214768A (ja)	1985-10-28	オリゴペプチド化合物
US4493794A (en)	1985-01-15	Peptide, process for preparation thereof and use thereof
JPH068313B2 (ja)	1994-02-02	新規アシルグルタミルリジン誘導体
JPH0651709B2 (ja)	1994-07-06	新規ホスフィン酸誘導体およびそれを有効成分とする脳循環代謝改善剤
JPH0832704B2 (ja)	1996-03-29	プロリルエンドペプチダーゼ阻害剤
US4399066A (en)	1983-08-16	Novel peptide, process for preparation thereof and use thereof
US4497729A (en)	1985-02-05	Peptide, process for preparation thereof and use thereof
US4476050A (en)	1984-10-09	Peptide, process for preparation thereof and use thereof
JPH0651677B2 (ja)	1994-07-06	ジペプチド誘導体及びその製法並びに用途