JPS62160B2 - - Google Patents

Info

Publication number: JPS62160B2
Authority: JP; Japan
Prior art keywords: amide; residue; nucleoside; pentapeptide; phenylalanyl
Prior art date: 1977-05-26
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

Application number

JP52061492A

Other languages

English (en)

Japanese (ja)

Other versions

JPS53147092A (en

Inventor

Noboru Yanaihara

Mitsuru Hirohashi

Mitsuo Nakamura

Eisuke Mizusawa

Machiko Igarashi

Bonpei Yasui

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.)

Funai Pharmaceutical Industries Ltd

Original Assignee

Funai Pharmaceutical Industries 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.)

1977-05-26

Filing date

1977-05-26

Publication date

1987-01-06

1977-05-26 Application filed by Funai Pharmaceutical Industries Ltd filed Critical Funai Pharmaceutical Industries Ltd

1977-05-26 Priority to JP6149277A priority Critical patent/JPS53147092A/ja

1978-12-21 Publication of JPS53147092A publication Critical patent/JPS53147092A/ja

1987-01-06 Publication of JPS62160B2 publication Critical patent/JPS62160B2/ja

Status Granted legal-status Critical Current

Links

150000001408 amides Chemical class 0.000 claims description 37
239000002777 nucleoside Substances 0.000 claims description 29
150000003833 nucleoside derivatives Chemical class 0.000 claims description 28
150000003839 salts Chemical class 0.000 claims description 23
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 15
125000000741 isoleucyl group Chemical group [H]N([H])C(C(C([H])([H])[H])C([H])([H])C([H])([H])[H])C(=O)O* 0.000 claims description 14
COLNVLDHVKWLRT-QMMMGPOBSA-N phenylalanine group Chemical group N[C@@H](CC1=CC=CC=C1)C(=O)O COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 claims description 14
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 14
125000003277 amino group Chemical group 0.000 claims description 10
238000001816 cooling Methods 0.000 claims description 9
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 claims description 8
150000001875 compounds Chemical class 0.000 claims description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
GSYTVXOARWSQSV-BYPYZUCNSA-N L-methioninamide Chemical compound CSCC[C@H](N)C(N)=O GSYTVXOARWSQSV-BYPYZUCNSA-N 0.000 claims description 6
125000001118 alkylidene group Chemical group 0.000 claims description 5
238000006243 chemical reaction Methods 0.000 claims description 5
125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 3
BTPZGMBOGFTHFA-CQJMVLFOSA-N (2s)-n-[(2s)-1-amino-4-methylsulfanyl-1-oxobutan-2-yl]-2-[[2-[[(2s)-2-[[(2s)-2-amino-3-phenylpropanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]acetyl]amino]-4-methylpentanamide Chemical compound C([C@@H](C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(N)=O)NC(=O)[C@@H](N)CC=1C=CC=CC=1)C1=CC=C(O)C=C1 BTPZGMBOGFTHFA-CQJMVLFOSA-N 0.000 claims description 2
125000003835 nucleoside group Chemical group 0.000 claims description 2
238000000034 method Methods 0.000 claims 2
ASFAFOSQXBRFMV-LJQANCHMSA-N 3-n-(2-benzyl-1,3-dihydroxypropan-2-yl)-1-n-[(1r)-1-(4-fluorophenyl)ethyl]-5-[methyl(methylsulfonyl)amino]benzene-1,3-dicarboxamide Chemical compound N([C@H](C)C=1C=CC(F)=CC=1)C(=O)C(C=1)=CC(N(C)S(C)(=O)=O)=CC=1C(=O)NC(CO)(CO)CC1=CC=CC=C1 ASFAFOSQXBRFMV-LJQANCHMSA-N 0.000 claims 1
RLXSTJVYBMNHEP-UWVGGRQHSA-N Gly-L-Leu-L-Met-NH2 Chemical compound CSCC[C@@H](C(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)CN RLXSTJVYBMNHEP-UWVGGRQHSA-N 0.000 claims 1
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 56
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
239000002904 solvent Substances 0.000 description 7
238000000921 elemental analysis Methods 0.000 description 6
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 5
ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-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
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 4
238000010511 deprotection reaction Methods 0.000 description 4
150000002148 esters Chemical class 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
239000000203 mixture Substances 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
230000003276 anti-hypertensive effect Effects 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
235000019253 formic acid Nutrition 0.000 description 2
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
-1 polyethylene Polymers 0.000 description 2
108090000765 processed proteins & peptides Proteins 0.000 description 2
125000006239 protecting group Chemical group 0.000 description 2
238000012360 testing method Methods 0.000 description 2
QDZOEBFLNHCSSF-PFFBOGFISA-N (2S)-2-[[(2R)-2-[[(2S)-1-[(2S)-6-amino-2-[[(2S)-1-[(2R)-2-amino-5-carbamimidamidopentanoyl]pyrrolidine-2-carbonyl]amino]hexanoyl]pyrrolidine-2-carbonyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-N-[(2R)-1-[[(2S)-1-[[(2R)-1-[[(2S)-1-[[(2S)-1-amino-4-methyl-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]pentanediamide Chemical compound C([C@@H](C(=O)N[C@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(N)=O)NC(=O)[C@@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCCN)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](N)CCCNC(N)=N)C1=CC=CC=C1 QDZOEBFLNHCSSF-PFFBOGFISA-N 0.000 description 1
OHKLEIJCOJXRTB-JKUQZMGJSA-N (2s,3s,5r)-5-(5-fluoro-2,4-dioxopyrimidin-1-yl)-3-hydroxyoxolane-2-carboxylic acid Chemical compound O1[C@H](C(O)=O)[C@@H](O)C[C@@H]1N1C(=O)NC(=O)C(F)=C1 OHKLEIJCOJXRTB-JKUQZMGJSA-N 0.000 description 1
LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
206010002091 Anaesthesia Diseases 0.000 description 1
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
239000004471 Glycine Substances 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
241000283973 Oryctolagus cuniculus Species 0.000 description 1
239000004698 Polyethylene Substances 0.000 description 1
102100024304 Protachykinin-1 Human genes 0.000 description 1
101800003906 Substance P Proteins 0.000 description 1
238000002835 absorbance Methods 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000008065 acid anhydrides Chemical class 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
GFFGJBXGBJISGV-UHFFFAOYSA-N adenyl group Chemical group N1=CN=C2N=CNC2=C1N GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
229940024606 amino acid Drugs 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
230000037005 anaesthesia Effects 0.000 description 1
230000004872 arterial blood pressure Effects 0.000 description 1
150000001540 azides Chemical class 0.000 description 1
230000004531 blood pressure lowering effect Effects 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
210000001168 carotid artery common Anatomy 0.000 description 1
OJYGBLRPYBAHRT-IPQSZEQASA-N chloralose Chemical compound O1[C@H](C(Cl)(Cl)Cl)O[C@@H]2[C@@H](O)[C@@H]([C@H](O)CO)O[C@@H]21 OJYGBLRPYBAHRT-IPQSZEQASA-N 0.000 description 1
229950009941 chloralose Drugs 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
239000000470 constituent Substances 0.000 description 1
UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 1
125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 description 1
239000012634 fragment Substances 0.000 description 1
229910000042 hydrogen bromide Inorganic materials 0.000 description 1
230000001077 hypotensive effect Effects 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
NTISAKGPIGTIJJ-UHFFFAOYSA-N leucyl-methionine Chemical compound CSCCC(C(O)=O)NC(=O)C(N)CC(C)C NTISAKGPIGTIJJ-UHFFFAOYSA-N 0.000 description 1
108010091871 leucylmethionine Proteins 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
238000010647 peptide synthesis reaction Methods 0.000 description 1
239000003880 polar aprotic solvent Substances 0.000 description 1
229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000010998 test method Methods 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
210000003462 vein Anatomy 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
238000005303 weighing Methods 0.000 description 1

Landscapes

Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Peptides Or Proteins (AREA)

JP6149277A 1977-05-26 1977-05-26 Novel nucleotidepentapeptideamide and process for preparing same Granted JPS53147092A (en)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP6149277A JPS53147092A (en)	1977-05-26	1977-05-26	Novel nucleotidepentapeptideamide and process for preparing same

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP6149277A JPS53147092A (en)	1977-05-26	1977-05-26	Novel nucleotidepentapeptideamide and process for preparing same

Publications (2)

Publication Number	Publication Date
JPS53147092A JPS53147092A (en)	1978-12-21
JPS62160B2 true JPS62160B2 (de)	1987-01-06

Family

ID=13172637

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP6149277A Granted JPS53147092A (en)	1977-05-26	1977-05-26	Novel nucleotidepentapeptideamide and process for preparing same

Country Status (1)

Country	Link
JP (1)	JPS53147092A (de)

1977
- 1977-05-26 JP JP6149277A patent/JPS53147092A/ja active Granted

Also Published As

Publication number	Publication date
JPS53147092A (en)	1978-12-21

Publication	Publication Date	Title
US3450693A (en)	1969-06-17	Method of synthesizing adenosine,2',3'-o-isopropylidene-adenosine and intermediates thereof
CA1060435A (en)	1979-08-14	Peptides
JP2002503212A (ja)	2002-01-29	単環式ヌクレオシド、その類似体および使用
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US4060603A (en)	1977-11-29	Histidine derivatives
MXPA01012038A (es)	2002-05-06	Agonistas receptores de la adenosina a1 oralmente activos.
CH429754A (de)	1967-02-15	Verfahren zur Herstellung eines neuen Hexapeptids
JPS6139960B2 (de)	1986-09-06
JPH0127061B2 (de)	1989-05-26
YAJIMA et al.	1971	Studies on Peptides. XXXIII. Nε-β, β, β-Trichloroethyloxycarbonyllysine
RU2091389C1 (ru)	1997-09-27	Пептид, обладающий иммуномодулирующей активностью
JPS61191695A (ja)	1986-08-26	新規ペプタイド
JPS5951935B2 (ja)	1984-12-17	新規なペプチドおよびその製造法
JPS6035359B2 (ja)	1985-08-14	新規なヘキサペプチドアミド及びその製法
JPS636080B2 (de)	1988-02-08
JPH0414120B2 (de)	1992-03-11
Hřebabecký et al.	1997	Preparation of thymidine-4'-C-carboxylic acid and its derivatives
JPS6035360B2 (ja)	1985-08-14	新規なヘプタペプチドアミド及びその製法
JPS6136760B2 (de)	1986-08-20
JP2646459B2 (ja)	1997-08-27	Ｎ▲上６▼，ｎ▲上６▼―ジ置換ーアデノシン―３′，５′―環状リン酸又はその塩及びその製造方法
KR810000584B1 (ko)	1981-06-03	뉴클레오시드의 제조방법
Rosenthal et al.	1978	9-[3-acetamido-3-C-(carboxymethyl)-3-deoxy-32, 2-lactone-α (andβ)-D-xylofuranosyl] adenine-analogs of the nucleoside moiety of the polyoxins