NL8301965A - Analogen van neurohypofysiaire hormonen met remmende effecten alsmede farmaceutische preparaten, die deze analogen bevatten. - Google Patents

Analogen van neurohypofysiaire hormonen met remmende effecten alsmede farmaceutische preparaten, die deze analogen bevatten. Download PDF

Info

Publication number: NL8301965A
Authority: NL; Netherlands
Prior art keywords: water; dimethylformamide; ether; solution; added
Prior art date: 1982-06-03

Application number

NL8301965A

Other languages

English (en)

Dutch (nl)

Original Assignee

Ceskoslovenska Akademie Ved

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.)

1982-06-03

Filing date

1983-06-02

Publication date

1984-01-02

1982-06-03 Priority claimed from CS824128A external-priority patent/CS229893B1/cs

1982-08-26 Priority claimed from CS620682A external-priority patent/CS229896B1/cs

1983-06-02 Application filed by Ceskoslovenska Akademie Ved filed Critical Ceskoslovenska Akademie Ved

1984-01-02 Publication of NL8301965A publication Critical patent/NL8301965A/nl

Links

229940088597 hormone Drugs 0.000 title claims description 7
239000005556 hormone Substances 0.000 title claims description 7
239000000825 pharmaceutical preparation Substances 0.000 title claims description 4
230000000694 effects Effects 0.000 title description 3
KBZOIRJILGZLEJ-LGYYRGKSSA-N argipressin Chemical compound C([C@H]1C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CSSC[C@@H](C(N[C@@H](CC=2C=CC(O)=CC=2)C(=O)N1)=O)N)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCN=C(N)N)C(=O)NCC(N)=O)C1=CC=CC=C1 KBZOIRJILGZLEJ-LGYYRGKSSA-N 0.000 claims description 32
229960003726 vasopressin Drugs 0.000 claims description 20
GXBMIBRIOWHPDT-UHFFFAOYSA-N Vasopressin Natural products N1C(=O)C(CC=2C=C(O)C=CC=2)NC(=O)C(N)CSSCC(C(=O)N2C(CCC2)C(=O)NC(CCCN=C(N)N)C(=O)NCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(CCC(N)=O)NC(=O)C1CC1=CC=CC=C1 GXBMIBRIOWHPDT-UHFFFAOYSA-N 0.000 claims description 19
108010004977 Vasopressins Proteins 0.000 claims description 19
102000002852 Vasopressins Human genes 0.000 claims description 19
239000004472 Lysine Substances 0.000 claims description 18
XNOPRXBHLZRZKH-DSZYJQQASA-N oxytocin Chemical compound C([C@H]1C(=O)N[C@H](C(N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CSSC[C@H](N)C(=O)N1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC(C)C)C(=O)NCC(N)=O)=O)[C@@H](C)CC)C1=CC=C(O)C=C1 XNOPRXBHLZRZKH-DSZYJQQASA-N 0.000 claims description 16
101800000989 Oxytocin Proteins 0.000 claims description 12
XNOPRXBHLZRZKH-UHFFFAOYSA-N Oxytocin Natural products N1C(=O)C(N)CSSCC(C(=O)N2C(CCC2)C(=O)NC(CC(C)C)C(=O)NCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(CCC(N)=O)NC(=O)C(C(C)CC)NC(=O)C1CC1=CC=C(O)C=C1 XNOPRXBHLZRZKH-UHFFFAOYSA-N 0.000 claims description 12
102100031951 Oxytocin-neurophysin 1 Human genes 0.000 claims description 12
229960001723 oxytocin Drugs 0.000 claims description 12
230000002401 inhibitory effect Effects 0.000 claims description 10
KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical class NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims description 7
235000018417 cysteine Nutrition 0.000 claims description 5
XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 claims description 5
AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 claims 1
ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 claims 1
COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 claims 1
ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 claims 1
AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 claims 1
229960000310 isoleucine Drugs 0.000 claims 1
COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 claims 1
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 168
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 126
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 118
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 56
239000000243 solution Substances 0.000 description 51
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 41
OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 26
-1 polymethylene chain Polymers 0.000 description 26
238000003756 stirring Methods 0.000 description 26
239000011541 reaction mixture Substances 0.000 description 24
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 23
XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 description 23
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 22
235000001014 amino acid Nutrition 0.000 description 20
150000001413 amino acids Chemical class 0.000 description 20
230000003647 oxidation Effects 0.000 description 20
238000007254 oxidation reaction Methods 0.000 description 20
238000004458 analytical method Methods 0.000 description 19
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
150000001408 amides Chemical class 0.000 description 18
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 16
150000002148 esters Chemical class 0.000 description 16
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 15
239000003208 petroleum Substances 0.000 description 15
150000001875 compounds Chemical class 0.000 description 14
HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-UHFFFAOYSA-N 0.000 description 12
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 9
238000004108 freeze drying Methods 0.000 description 9
229910052708 sodium Inorganic materials 0.000 description 9
239000011734 sodium Substances 0.000 description 9
239000002253 acid Substances 0.000 description 8
229910021529 ammonia Inorganic materials 0.000 description 7
235000019270 ammonium chloride Nutrition 0.000 description 7
238000009835 boiling Methods 0.000 description 7
238000001997 free-flow electrophoresis Methods 0.000 description 7
238000002523 gelfiltration Methods 0.000 description 7
239000003112 inhibitor Substances 0.000 description 7
239000004471 Glycine Substances 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 6
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
230000008018 melting Effects 0.000 description 6
238000002844 melting Methods 0.000 description 6
238000000034 method Methods 0.000 description 6
OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 5
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
108090000765 processed proteins & peptides Proteins 0.000 description 4
230000001270 agonistic effect Effects 0.000 description 3
150000001450 anions Chemical class 0.000 description 3
125000000896 monocarboxylic acid group Chemical group 0.000 description 3
AWDBHOZBRXWRKS-UHFFFAOYSA-N tetrapotassium;iron(6+);hexacyanide Chemical compound [K+].[K+].[K+].[K+].[Fe+6].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] AWDBHOZBRXWRKS-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
206010011732 Cyst Diseases 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
230000021736 acetylation Effects 0.000 description 2
238000006640 acetylation reaction Methods 0.000 description 2
230000029936 alkylation Effects 0.000 description 2
238000005804 alkylation reaction Methods 0.000 description 2
230000004071 biological effect Effects 0.000 description 2
208000031513 cyst Diseases 0.000 description 2
235000019253 formic acid Nutrition 0.000 description 2
238000004128 high performance liquid chromatography Methods 0.000 description 2
238000000338 in vitro Methods 0.000 description 2
238000011835 investigation Methods 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
239000000203 mixture Substances 0.000 description 2
NMHMNPHRMNGLLB-UHFFFAOYSA-N phloretic acid Chemical compound OC(=O)CCC1=CC=C(O)C=C1 NMHMNPHRMNGLLB-UHFFFAOYSA-N 0.000 description 2
YYBHQXPUCZWZNK-LBPRGKRZSA-N (2S)-2-[2,2-dimethylpropanoyloxy(methyl)amino]-3-(4-hydroxyphenyl)propanoic acid Chemical compound CC(C)(C)C(=O)ON(C)[C@H](C(O)=O)CC1=CC=C(O)C=C1 YYBHQXPUCZWZNK-LBPRGKRZSA-N 0.000 description 1
LVYWYLGWSVIFEV-ZDUSSCGKSA-N (2s)-3-(2-nitrophenyl)-2-(phenylsulfanylamino)propanoic acid Chemical compound C([C@@H](C(=O)O)NSC=1C=CC=CC=1)C1=CC=CC=C1[N+]([O-])=O LVYWYLGWSVIFEV-ZDUSSCGKSA-N 0.000 description 1
SCYCMFQAMTUOEU-LURJTMIESA-N (2s)-4-amino-2-[(2-nitrophenyl)sulfanylazaniumyl]-4-oxobutanoate Chemical compound NC(=O)C[C@@H](C(O)=O)NSC1=CC=CC=C1[N+]([O-])=O SCYCMFQAMTUOEU-LURJTMIESA-N 0.000 description 1
GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 1
IFSRDOWEJUBRDO-ZVDAKTGKSA-N 2-[[(2s)-2-[[(2s)-1-[(2r)-2-[[(2s)-4-amino-2-[[(2s)-5-amino-2-[[(2s,3s)-2-amino-3-methylpentanoyl]amino]-5-oxopentanoyl]amino]-4-oxobutanoyl]amino]-3-benzylsulfanylpropanoyl]pyrrolidine-2-carbonyl]amino]-4-methylpentanoyl]amino]acetic acid Chemical compound C([C@H](NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](N)[C@@H](C)CC)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC(C)C)C(=O)NCC(O)=O)SCC1=CC=CC=C1 IFSRDOWEJUBRDO-ZVDAKTGKSA-N 0.000 description 1
DKIDEFUBRARXTE-UHFFFAOYSA-N 3-mercaptopropanoic acid Chemical group OC(=O)CCS DKIDEFUBRARXTE-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
101150065749 Churc1 gene Proteins 0.000 description 1
BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 1
102000004190 Enzymes Human genes 0.000 description 1
108090000790 Enzymes Proteins 0.000 description 1
229910002651 NO3 Inorganic materials 0.000 description 1
102100038239 Protein Churchill Human genes 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
239000008351 acetate buffer Substances 0.000 description 1
MHLMRBVCMNDOCW-UHFFFAOYSA-N acetic acid;butan-1-ol;hydrate Chemical compound O.CC(O)=O.CCCCO MHLMRBVCMNDOCW-UHFFFAOYSA-N 0.000 description 1
NJUISRMVIKYYCN-UHFFFAOYSA-N acetic acid;chloroform;methanol;hydrate Chemical compound O.OC.CC(O)=O.ClC(Cl)Cl NJUISRMVIKYYCN-UHFFFAOYSA-N 0.000 description 1
235000011114 ammonium hydroxide Nutrition 0.000 description 1
210000001124 body fluid Anatomy 0.000 description 1
SAKUKAQFBMDKGX-UHFFFAOYSA-N butan-1-ol;2-pyridin-2-ylacetic acid;hydrate Chemical compound O.CCCCO.OC(=O)CC1=CC=CC=N1 SAKUKAQFBMDKGX-UHFFFAOYSA-N 0.000 description 1
125000000151 cysteine group Chemical group N[C@@H](CS)C(=O)* 0.000 description 1
238000011161 development Methods 0.000 description 1
238000001962 electrophoresis Methods 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
HQVFCQRVQFYGRJ-UHFFFAOYSA-N formic acid;hydrate Chemical compound O.OC=O HQVFCQRVQFYGRJ-UHFFFAOYSA-N 0.000 description 1
JEGUKCSWCFPDGT-UHFFFAOYSA-N h2o hydrate Chemical compound O.O JEGUKCSWCFPDGT-UHFFFAOYSA-N 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000000960 hypophysis hormone Substances 0.000 description 1
238000005462 in vivo assay Methods 0.000 description 1
108010064235 lysylglycine Proteins 0.000 description 1
239000000463 material Substances 0.000 description 1
GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
238000012261 overproduction Methods 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
230000001575 pathological effect Effects 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
GAPYKZAARZMMGP-UHFFFAOYSA-N pyridin-1-ium;acetate Chemical compound CC(O)=O.C1=CC=NC=C1 GAPYKZAARZMMGP-UHFFFAOYSA-N 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
238000012360 testing method Methods 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
238000001665 trituration Methods 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
210000004291 uterus Anatomy 0.000 description 1

Classifications

- 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
- C07K7/16—Oxytocins; Vasopressins; Related peptides
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S930/00—Peptide or protein sequence
- Y10S930/01—Peptide or protein sequence
- Y10S930/15—Oxytocin or vasopressin; related peptides

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Genetics & Genomics (AREA)
Biochemistry (AREA)
Biophysics (AREA)
General Health & Medical Sciences (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Molecular Biology (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Life Sciences & Earth Sciences (AREA)
Peptides Or Proteins (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

NL8301965A 1982-06-03 1983-06-02 Analogen van neurohypofysiaire hormonen met remmende effecten alsmede farmaceutische preparaten, die deze analogen bevatten. NL8301965A (nl)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
CS824128A CS229893B1 (cs)	1982-06-03	1982-06-03	Analogy oxytocinu a vasopresinu s inhibičními účinky a způsob jejich výroby
CS412882		1982-06-03
CS620682A CS229896B1 (cs)	1982-08-26	1982-08-26	Analogy vasopresinu a způsob jejich výroby
CS620682		1982-08-26

Publications (1)

Publication Number	Publication Date
NL8301965A true NL8301965A (nl)	1984-01-02

Family

ID=25745957

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL8301965A NL8301965A (nl)	1982-06-03	1983-06-02	Analogen van neurohypofysiaire hormonen met remmende effecten alsmede farmaceutische preparaten, die deze analogen bevatten.

Country Status (10)

Country	Link
US (1)	US4508645A (fr)
BE (1)	BE896943A (fr)
CH (1)	CH658061A5 (fr)
DE (1)	DE3320189A1 (fr)
DK (1)	DK233183A (fr)
FR (1)	FR2528036A1 (fr)
GB (1)	GB2122622B (fr)
IT (1)	IT1164260B (fr)
NL (1)	NL8301965A (fr)
SE (1)	SE8303091L (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4711877A (en) *	1985-09-18	1987-12-08	Smithkline Beckman Corporation	6-pen-vasopressin compounds
WO1987002676A1 (fr) *	1985-10-25	1987-05-07	Gibson-Stephens Neuropharmaceuticals, Inc.	Antagonistes de l'oxytocine a conformation limitee presentant des activites biologiques prolongees
US5055448A (en) *	1987-06-25	1991-10-08	Medical College Of Ohio	Linear derivatives of arginine vasopressin antagonists
US5562812A (en) *	1995-04-03	1996-10-08	The Penn State Research Foundation	Free flow electrophoresis device for biomolecule purification and separation in zero and one G

1983
- 1983-05-25 DK DK233183A patent/DK233183A/da not_active Application Discontinuation
- 1983-06-01 SE SE8303091A patent/SE8303091L/xx not_active Application Discontinuation
- 1983-06-02 FR FR8309146A patent/FR2528036A1/fr not_active Withdrawn
- 1983-06-02 BE BE0/210921A patent/BE896943A/fr not_active IP Right Cessation
- 1983-06-02 NL NL8301965A patent/NL8301965A/nl not_active Application Discontinuation
- 1983-06-02 CH CH3030/83A patent/CH658061A5/de not_active IP Right Cessation
- 1983-06-02 IT IT21431/83A patent/IT1164260B/it active
- 1983-06-03 US US06/500,773 patent/US4508645A/en not_active Expired - Fee Related
- 1983-06-03 GB GB08315273A patent/GB2122622B/en not_active Expired
- 1983-06-03 DE DE3320189A patent/DE3320189A1/de not_active Withdrawn

Also Published As

Publication number	Publication date
DK233183D0 (da)	1983-05-25
IT1164260B (it)	1987-04-08
SE8303091L (sv)	1983-12-04
US4508645A (en)	1985-04-02
GB2122622B (en)	1986-01-08
IT8321431A0 (it)	1983-06-02
GB8315273D0 (en)	1983-07-06
CH658061A5 (de)	1986-10-15
DE3320189A1 (de)	1983-12-08
FR2528036A1 (fr)	1983-12-09
SE8303091D0 (sv)	1983-06-01
DK233183A (da)	1983-12-04
GB2122622A (en)	1984-01-18
BE896943A (fr)	1983-10-03

Legal Events

Date	Code	Title	Description
1985-01-01	A85	Still pending on 85-01-01
1988-02-01	BV	The patent application has lapsed

Publication	Publication Date	Title
CA1185235A (fr)	1985-04-09	Antagonistes de l'action antidiuretique et (ou) vasoconstrictrice de l'arginine-vasopressine
Katayama et al.	2013	The phenacyl group as an efficient thiol protecting group in a peptide condensation reaction by the thioester method
Mayer et al.	1995	An alternative solid-phase approach to C1-oxytocin
Lebl et al.	1985	Oxytocin analogues with inhibitory properties, containing in position 2 a hydrophobic amino acid of D-configuration
US4508645A (en)	1985-04-02	Analogs of neurohypophysial hormones with inhibition effects
US4368150A (en)	1983-01-11	Method for protecting guanidino group and restoring the same
Milne et al.	1968	Peptide synthesis via oxidation of N-acylamino acid phenylhydrazides. III. Dialanylinsulin and (bisphenylalanyl) insulin
BODANSZKY et al.	1981	SYNTHESIS OF 8‐L‐TRYPTOPHAN‐OXYTOCIN AND DETERMINATION OF ONE OF ITS CONFORMATIONAL PARAMETERS
EP0078498B1 (fr)	1986-01-15	Méthode pour protéger et débloquer le groupe amino
Yasunobu et al.	1971	Amino-and carboxyl-terminal amino acid sequences of the Peptostreptococcus elsdenii and Clostridium pasteurianum flavodoxins
NL8301663A (nl)	1983-12-01	Analogen van neurohypofysiaire hormonen met remmende eigenschappen.
RU2063979C1 (ru)	1996-07-20	Пептиды последовательности окситоцина
Schafer et al.	1971	Amino-acids and peptides. Part XXXII. A simplified synthesis of bradykinin by use of the picolyl ester method
Žertová et al.	1990	The analogs of 8-D-homoarginine-vasopressin with p-substituted phenylalanine in position 2; Synthesis and some biological properties
Jones Jr et al.	1980	N-Acetyl-[2-(O-methyl) tyrosine] arginine-vasopressin, an interesting antagonist of the vasopressor response to vasopressin
Žertová et al.	1992	Amino and deamino analogs of 8-D-homoarginin-vasopressin with modified tyrosine in position 2: synthesis and some biological properties
Hlaváček et al.	1989	The effect of non-coded amino acids on the degradation of oxytocin analogs with α-chymotrypsin
Krchňák et al.	1979	Effect of methylation of the hydroxyl group of tyrosine in [1-β-mercaptopropionic acid, 8-D-arginine] vasopressin on its biological effects
EP0001075B1 (fr)	1980-11-26	Chaîne A de l'insuline humaine, partiellement protégée, et procédé pour son obtention
ROY et al.	1986	Desaminopenicillamine tocinoic acid derivatives‐inhibitors of oxytocin
Lebl et al.	1982	Analogues of neurohypophysial hormones, containing tert-leucine: Synthesis and properties
Žertová et al.	1993	The Analogs of [D-Har 8] Vasopressin with Di-and Trisubstituted Phenylalanine in Position 2; Synthesis and Some Biological Properties
US20030013659A1 (en)	2003-01-16	Halovir, an antiviral marine natural product, and derivatives thereof
Tomislav et al.	0	OXYTOCIN ANALOGUES WITH INHIBITORY PROPERTIES, CONTAINING IN POSITION 2 A HYDROPHOBIC AMINO ACID OF D-CONFIGURATION
Procházka et al.	1980	L-Cystathionine derivatives for the synthesis of peptides