JPS6136760B2 - - Google Patents

Info

Publication number: JPS6136760B2
Authority: JP; Japan
Prior art keywords: formula; decapeptide; asp; pyridine; boc
Prior art date: 1978-02-23
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

JP54008112A

Other languages

English (en)

Japanese (ja)

Other versions

JPS55100348A (en

Inventor

Garanteino Mauro

De Kasuteiryoone Roberuto

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.)

Pfizer Italia SRL

Original Assignee

Farmitalia Carlo Erba SRL

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.)

1978-02-23

Filing date

1979-01-25

Publication date

1986-08-20

1979-01-25 Application filed by Farmitalia Carlo Erba SRL filed Critical Farmitalia Carlo Erba SRL

1980-07-31 Publication of JPS55100348A publication Critical patent/JPS55100348A/ja

1986-08-20 Publication of JPS6136760B2 publication Critical patent/JPS6136760B2/ja

Status Granted legal-status Critical Current

Links

ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 58
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 15
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 13
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
238000000034 method Methods 0.000 claims description 8
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 8
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical class N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 6
238000006243 chemical reaction Methods 0.000 claims description 6
238000007796 conventional method Methods 0.000 claims description 6
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 claims description 5
150000001413 amino acids Chemical class 0.000 claims description 5
239000002585 base Substances 0.000 claims description 5
239000003795 chemical substances by application Substances 0.000 claims description 5
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 4
RGYLYUZOGHTBRF-BIHRQFPBSA-N tetragastrin Chemical compound C([C@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@@H](NC(=O)[C@@H](N)CC=1C2=CC=CC=C2NC=1)CCSC)C(N)=O)C1=CC=CC=C1 RGYLYUZOGHTBRF-BIHRQFPBSA-N 0.000 claims description 4
108010010737 Ceruletide Proteins 0.000 claims description 3
150000003973 alkyl amines Chemical class 0.000 claims description 3
239000012736 aqueous medium Substances 0.000 claims description 3
YRALAIOMGQZKOW-HYAOXDFASA-N ceruletide Chemical compound C([C@@H](C(=O)N[C@H](C(=O)NCC(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(N)=O)[C@@H](C)O)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H]1NC(=O)CC1)C1=CC=C(OS(O)(=O)=O)C=C1 YRALAIOMGQZKOW-HYAOXDFASA-N 0.000 claims description 3
229960001706 ceruletide Drugs 0.000 claims description 3
230000008878 coupling Effects 0.000 claims description 3
238000010168 coupling process Methods 0.000 claims description 3
238000005859 coupling reaction Methods 0.000 claims description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
150000002460 imidazoles Chemical class 0.000 claims description 3
150000007530 organic bases Chemical class 0.000 claims description 3
150000003222 pyridines Chemical class 0.000 claims description 3
150000003839 salts Chemical class 0.000 claims description 3
YRALAIOMGQZKOW-UHFFFAOYSA-N sulfated caerulein Natural products C=1C=CC=CC=1CC(C(N)=O)NC(=O)C(CC(O)=O)NC(=O)C(CCSC)NC(=O)C(CC=1C2=CC=CC=C2NC=1)NC(=O)CNC(=O)C(C(C)O)NC(=O)C(NC(=O)C(CC(O)=O)NC(=O)C(CCC(N)=O)NC(=O)C1NC(=O)CC1)CC1=CC=C(OS(O)(=O)=O)C=C1 YRALAIOMGQZKOW-UHFFFAOYSA-N 0.000 claims description 3
230000001180 sulfating effect Effects 0.000 claims description 3
239000004471 Glycine Substances 0.000 claims description 2
OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 claims description 2
239000000470 constituent Substances 0.000 claims description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 2
QAOWNCQODCNURD-UHFFFAOYSA-L sulfate group Chemical group S(=O)(=O)([O-])[O-] QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 2
239000000010 aprotic solvent Substances 0.000 claims 2
229910052783 alkali metal Inorganic materials 0.000 claims 1
150000001340 alkali metals Chemical class 0.000 claims 1
OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 12
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 11
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
239000002904 solvent Substances 0.000 description 9
OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 8
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 8
238000002425 crystallisation Methods 0.000 description 7
230000008025 crystallization Effects 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
150000001875 compounds Chemical class 0.000 description 6
238000009833 condensation Methods 0.000 description 6
230000005494 condensation Effects 0.000 description 6
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
239000000243 solution Substances 0.000 description 6
DDROKKYSSQPXQO-FWEHEUNISA-N (3s)-4-[[(2s)-1-amino-1-oxo-3-phenylpropan-2-yl]amino]-3-[[(2s)-2-[[(2s)-3-(1h-indol-3-yl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]-4-methylsulfanylbutanoyl]amino]-4-oxobutanoic acid Chemical compound C([C@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)OC(C)(C)C)CCSC)C(N)=O)C1=CC=CC=C1 DDROKKYSSQPXQO-FWEHEUNISA-N 0.000 description 5
238000000354 decomposition reaction Methods 0.000 description 5
238000004519 manufacturing process Methods 0.000 description 5
238000002360 preparation method Methods 0.000 description 5
108090000765 processed proteins & peptides Proteins 0.000 description 5
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
235000019253 formic acid Nutrition 0.000 description 4
230000007062 hydrolysis Effects 0.000 description 4
238000006460 hydrolysis reaction Methods 0.000 description 4
239000000543 intermediate Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
230000019635 sulfation Effects 0.000 description 4
238000005670 sulfation reaction Methods 0.000 description 4
-1 t-butyloxycarbonyl Chemical group 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
125000003277 amino group Chemical group 0.000 description 3
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
239000000203 mixture Substances 0.000 description 3
239000000047 product Substances 0.000 description 3
125000006239 protecting group Chemical group 0.000 description 3
238000007127 saponification reaction Methods 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
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
108010033276 Peptide Fragments Proteins 0.000 description 2
102000007079 Peptide Fragments Human genes 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
238000009826 distribution Methods 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
239000012535 impurity Substances 0.000 description 2
150000007529 inorganic bases Chemical class 0.000 description 2
239000002609 medium Substances 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
238000010189 synthetic method Methods 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
CNBUSIJNWNXLQQ-NSHDSACASA-N (2s)-3-(4-hydroxyphenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid Chemical compound CC(C)(C)OC(=O)N[C@H](C(O)=O)CC1=CC=C(O)C=C1 CNBUSIJNWNXLQQ-NSHDSACASA-N 0.000 description 1
LLHOYOCAAURYRL-RITPCOANSA-N (2s,3r)-3-hydroxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoic acid Chemical compound C[C@@H](O)[C@@H](C(O)=O)NC(=O)OC(C)(C)C LLHOYOCAAURYRL-RITPCOANSA-N 0.000 description 1
KPAUJSXYKQJSSO-UWVGGRQHSA-N (3s)-4-[[(2s)-1-amino-1-oxo-3-phenylpropan-2-yl]amino]-3-azaniumyl-4-oxobutanoate Chemical compound OC(=O)C[C@H](N)C(=O)N[C@H](C(N)=O)CC1=CC=CC=C1 KPAUJSXYKQJSSO-UWVGGRQHSA-N 0.000 description 1
VRPJIFMKZZEXLR-UHFFFAOYSA-N 2-[(2-methylpropan-2-yl)oxycarbonylamino]acetic acid Chemical compound CC(C)(C)OC(=O)NCC(O)=O VRPJIFMKZZEXLR-UHFFFAOYSA-N 0.000 description 1
WFIYPADYPQQLNN-UHFFFAOYSA-N 2-[2-(4-bromopyrazol-1-yl)ethyl]isoindole-1,3-dione Chemical compound C1=C(Br)C=NN1CCN1C(=O)C2=CC=CC=C2C1=O WFIYPADYPQQLNN-UHFFFAOYSA-N 0.000 description 1
FBPINGSGHKXIQA-UHFFFAOYSA-N 2-amino-3-(2-carboxyethylsulfanyl)propanoic acid Chemical compound OC(=O)C(N)CSCCC(O)=O FBPINGSGHKXIQA-UHFFFAOYSA-N 0.000 description 1
OBSIQMZKFXFYLV-UHFFFAOYSA-N 2-amino-3-phenylpropanamide Chemical compound NC(=O)C(N)CC1=CC=CC=C1 OBSIQMZKFXFYLV-UHFFFAOYSA-N 0.000 description 1
239000005725 8-Hydroxyquinoline Substances 0.000 description 1
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 1
QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 description 1
229960000583 acetic acid Drugs 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000008065 acid anhydrides Chemical class 0.000 description 1
238000010306 acid treatment Methods 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
239000012670 alkaline solution Substances 0.000 description 1
150000001540 azides Chemical class 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000011033 desalting Methods 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
238000007865 diluting Methods 0.000 description 1
150000004656 dimethylamines Chemical class 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
WHQSYGRFZMUQGQ-UHFFFAOYSA-N n,n-dimethylformamide;hydrate Chemical compound O.CN(C)C=O WHQSYGRFZMUQGQ-UHFFFAOYSA-N 0.000 description 1
GHNKHMFBYWBBDX-UHFFFAOYSA-N n-cyclohexyl-n'-morpholin-4-ylmethanediimine Chemical compound C1CCCCC1N=C=NN1CCOCC1 GHNKHMFBYWBBDX-UHFFFAOYSA-N 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
229960003540 oxyquinoline Drugs 0.000 description 1
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
238000000746 purification Methods 0.000 description 1
MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
230000006340 racemization Effects 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000001308 synthesis method Methods 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
125000000341 threoninyl group Chemical group [H]OC([H])(C([H])([H])[H])C([H])(N([H])[H])C(*)=O 0.000 description 1
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
125000000430 tryptophan group Chemical group [H]N([H])C(C(=O)O*)C([H])([H])C1=C([H])N([H])C2=C([H])C([H])=C([H])C([H])=C12 0.000 description 1
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 description 1
238000010626 work up procedure Methods 0.000 description 1

Classifications

- 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
- C07K14/575—Hormones
- C07K14/595—Gastrins; Cholecystokinins [CCK]

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Gastroenterology & Hepatology (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Biophysics (AREA)
Zoology (AREA)
Biochemistry (AREA)
Toxicology (AREA)
General Health & Medical Sciences (AREA)
Genetics & Genomics (AREA)
Medicinal Chemistry (AREA)
Molecular Biology (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Endocrinology (AREA)
Peptides Or Proteins (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

JP811279A 1978-02-23 1979-01-25 Novel manufacture of ceruletide Granted JPS55100348A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB721578		1978-02-23

Publications (2)

Publication Number	Publication Date
JPS55100348A JPS55100348A (en)	1980-07-31
JPS6136760B2 true JPS6136760B2 (de)	1986-08-20

Family

ID=9828842

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP811279A Granted JPS55100348A (en)	1978-02-23	1979-01-25	Novel manufacture of ceruletide

Country Status (5)

Country	Link
JP (1)	JPS55100348A (de)
BE (1)	BE873272A (de)
DE (1)	DE2902015A1 (de)
GB (1)	GB2016478B (de)
IT (1)	IT1207202B (de)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS6377829U (de) *	1986-11-10	1988-05-23
JPH01220769A (ja) *	1988-02-26	1989-09-04	Nippon Isueede Kk	転車及びその製造方法

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH0235760B2 (ja) *	1982-05-27	1990-08-13	Shionogi & Co	Serureinnoshinkiseizoho
JPS5967254A (ja) *	1982-10-08	1984-04-16	Shionogi & Co Ltd	セルレイン中間体の製造法

1979
- 1979-01-02 BE BE192731A patent/BE873272A/xx not_active IP Right Cessation
- 1979-01-19 DE DE19792902015 patent/DE2902015A1/de active Granted
- 1979-01-25 JP JP811279A patent/JPS55100348A/ja active Granted
- 1979-02-22 IT IT7920415A patent/IT1207202B/it active Protection Beyond IP Right Term
- 1979-05-01 GB GB7915154A patent/GB2016478B/en not_active Expired

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS6377829U (de) *	1986-11-10	1988-05-23
JPH01220769A (ja) *	1988-02-26	1989-09-04	Nippon Isueede Kk	転車及びその製造方法

Also Published As

Publication number	Publication date
DE2902015C2 (de)	1987-08-27
BE873272A (fr)	1979-05-02
GB2016478B (en)	1982-06-30
DE2902015A1 (de)	1979-08-30
JPS55100348A (en)	1980-07-31
IT1207202B (it)	1989-05-17
IT7920415A0 (it)	1979-02-22
GB2016478A (en)	1979-09-26

Publication	Publication Date	Title
US4507235A (en)	1985-03-26	Method for preparing peptides and intermediate products
US4330466A (en)	1982-05-18	Process for the production of cholecystokinin-pancreozymin C-terminal peptide amide sulfate esters
CH645342A5 (de)	1984-09-28	Biologisch aktive peptide.
US4242329A (en)	1980-12-30	Bradykinin-inhibiting tripeptide derivatives
JPH11505515A (ja)	1999-05-21	ペプチドと、その製造方法
EP0122818B1 (de)	1987-10-07	Synthese von hpGRF (Somatocrinin) in flüssiger Phase und mittlere Peptide
JPS6317839B2 (de)	1988-04-15
EP0171315B1 (de)	1989-01-18	Verfahren zur Herstellung von hGRF (Somatocrinin) in flüssiger Phase und Peptidezwischenverbindungen
JPS6136760B2 (de)	1986-08-20
CH636598A5 (de)	1983-06-15	Verfahren zur herstellung neuer psychopharmakologisch aktiver peptide.
DE1643345B2 (de)	1975-02-13	Glucagonderivat und Verfahren zur Herstellung von Glucagon
LU85710A1 (fr)	1986-07-17	Nouveaux derives de la gonadoliberine et procede pour leur preparation
DE2245459A1 (de)	1973-03-22	Verfahren zur herstellung eines tetrapeptid-derivates
CH658661A5 (de)	1986-11-28	Peptidverbindungen.
JPS5921656A (ja)	1984-02-03	ポリペプチド誘導体
DE2327396A1 (de)	1973-12-13	Synthetisches polypeptid und verfahren zur herstellung desselben
US3280098A (en)	1966-10-18	Process of producing peptides and products obtained thereby
US4102878A (en)	1978-07-25	Process for the preparation of the cholecystokinin-pancreozymin octapeptide amide sulfate ester
US3948971A (en)	1976-04-06	N-protected-α-amino acid compounds
US5212287A (en)	1993-05-18	Pentapeptide synthesis
Stewart	1967	Peptide syntheses with the 2, 4, 6-trimethylbenzyl esters of L-asparagine and L-glutamine
PT758342E (pt)	2000-04-28	Nova substancia activa peptidica e sua preparacao
US3230211A (en)	1966-01-18	8-p-fluoro-l-phenylanyl bradykinin
US3767639A (en)	1973-10-23	Process for the preparation of secretin
CA1182110A (en)	1985-02-05	Physiologically active tetrapeptides

JPS6136760B2 - - Google Patents

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