NL8301320A - Analogen van vasopressine. - Google Patents

Analogen van vasopressine. Download PDF

Info

Publication number: NL8301320A
Authority: NL; Netherlands
Prior art keywords: solution; dimethylformamide; analogs; compound; vasopressin
Prior art date: 1982-04-20

Application number

NL8301320A

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.)

1982-04-20

Filing date

1983-04-15

Publication date

1983-11-16

1982-04-20 Priority claimed from CS822803A external-priority patent/CS230315B1/cs

1982-11-19 Priority claimed from CS830182A external-priority patent/CS231749B1/cs

1983-04-15 Application filed by Ceskoslovenska Akademie Ved filed Critical Ceskoslovenska Akademie Ved

1983-11-16 Publication of NL8301320A publication Critical patent/NL8301320A/nl

Links

JLTCWSBVQSZVLT-CDIPANDDSA-N (2s)-n-[(2s)-6-amino-1-[(2-amino-2-oxoethyl)amino]-1-oxohexan-2-yl]-1-[(4r,7s,10s,13s,16s,19r)-19-amino-7-(2-amino-2-oxoethyl)-10-(3-amino-3-oxopropyl)-13-benzyl-16-[(4-hydroxyphenyl)methyl]-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentazacycloicosan Chemical compound NCCCC[C@@H](C(=O)NCC(N)=O)NC(=O)[C@@H]1CCCN1C(=O)[C@H]1NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC=2C=CC=CC=2)NC(=O)[C@H](CC=2C=CC(O)=CC=2)NC(=O)[C@@H](N)CSSC1.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 JLTCWSBVQSZVLT-CDIPANDDSA-N 0.000 title 1
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 10
150000001413 amino acids Chemical class 0.000 claims description 7
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 6
108010004977 Vasopressins Proteins 0.000 claims description 6
102000002852 Vasopressins Human genes 0.000 claims description 6
229960003726 vasopressin Drugs 0.000 claims description 6
AHLPHDHHMVZTML-UHFFFAOYSA-N Orn-delta-NH2 Natural products NCCCC(N)C(O)=O AHLPHDHHMVZTML-UHFFFAOYSA-N 0.000 claims description 2
CCTIOCVIZPCTGO-BYPYZUCNSA-N phosphoarginine Chemical compound OC(=O)[C@@H](N)CCCNC(=N)NP(O)(O)=O CCTIOCVIZPCTGO-BYPYZUCNSA-N 0.000 claims 2
239000000825 pharmaceutical preparation Substances 0.000 claims 1
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 63
239000000243 solution Substances 0.000 description 26
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
-1 benzyl ester Chemical class 0.000 description 18
150000001875 compounds Chemical class 0.000 description 17
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
229910052757 nitrogen Inorganic materials 0.000 description 12
238000002360 preparation method Methods 0.000 description 12
229910052799 carbon Inorganic materials 0.000 description 11
229910052739 hydrogen Inorganic materials 0.000 description 11
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 9
239000000047 product Substances 0.000 description 9
239000011541 reaction mixture Substances 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
230000000694 effects Effects 0.000 description 8
229910052717 sulfur Inorganic materials 0.000 description 8
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
235000001014 amino acid Nutrition 0.000 description 6
BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 6
229940088597 hormone Drugs 0.000 description 6
239000005556 hormone Substances 0.000 description 6
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 6
229910000041 hydrogen chloride Inorganic materials 0.000 description 6
239000000203 mixture Substances 0.000 description 6
ODKSFYDXXFIFQN-SCSAIBSYSA-N D-arginine Chemical compound OC(=O)[C@H](N)CCCNC(N)=N ODKSFYDXXFIFQN-SCSAIBSYSA-N 0.000 description 5
239000002253 acid Substances 0.000 description 5
238000000034 method Methods 0.000 description 5
ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical compound OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 description 4
238000004458 analytical method Methods 0.000 description 4
238000002523 gelfiltration Methods 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-UHFFFAOYSA-N 0.000 description 3
241000700159 Rattus Species 0.000 description 3
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
150000001540 azides Chemical class 0.000 description 3
230000008018 melting Effects 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000003647 oxidation Effects 0.000 description 3
238000007254 oxidation reaction Methods 0.000 description 3
239000007858 starting material Substances 0.000 description 3
238000012360 testing method Methods 0.000 description 3
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
230000004071 biological effect Effects 0.000 description 2
238000003776 cleavage reaction Methods 0.000 description 2
229940125890 compound Ia Drugs 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
238000001962 electrophoresis Methods 0.000 description 2
230000002124 endocrine Effects 0.000 description 2
230000002255 enzymatic effect Effects 0.000 description 2
239000012467 final product Substances 0.000 description 2
QEWYKACRFQMRMB-UHFFFAOYSA-N fluoroacetic acid Chemical compound OC(=O)CF QEWYKACRFQMRMB-UHFFFAOYSA-N 0.000 description 2
BEBCJVAWIBVWNZ-UHFFFAOYSA-N glycinamide Chemical group NCC(N)=O BEBCJVAWIBVWNZ-UHFFFAOYSA-N 0.000 description 2
150000003951 lactams Chemical class 0.000 description 2
239000007788 liquid Substances 0.000 description 2
239000000463 material Substances 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
108090000765 processed proteins & peptides Proteins 0.000 description 2
230000007017 scission Effects 0.000 description 2
239000000126 substance Substances 0.000 description 2
230000003191 uterotonic effect Effects 0.000 description 2
KFNRNFXZFIRNEO-LLVKDONJSA-N (2r)-5-(diaminomethylideneazaniumyl)-2-[(4-methylphenyl)sulfonylamino]pentanoate Chemical compound CC1=CC=C(S(=O)(=O)N[C@H](CCCN=C(N)N)C(O)=O)C=C1 KFNRNFXZFIRNEO-LLVKDONJSA-N 0.000 description 1
ZVSQNFDSXRIAHI-VIFPVBQESA-N (2s)-1-(2-nitrophenyl)sulfanylpyrrolidine-2-carboxylic acid Chemical compound OC(=O)[C@@H]1CCCN1SC1=CC=CC=C1[N+]([O-])=O ZVSQNFDSXRIAHI-VIFPVBQESA-N 0.000 description 1
ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
102400000059 Arg-vasopressin Human genes 0.000 description 1
101800001144 Arg-vasopressin Proteins 0.000 description 1
239000004475 Arginine Substances 0.000 description 1
JQJPBYFTQAANLE-UHFFFAOYSA-N Butyl nitrite Chemical compound CCCCON=O JQJPBYFTQAANLE-UHFFFAOYSA-N 0.000 description 1
102100030953 Cleavage and polyadenylation specificity factor subunit 4 Human genes 0.000 description 1
229930028154 D-arginine Natural products 0.000 description 1
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 1
101000727105 Homo sapiens Cleavage and polyadenylation specificity factor subunit 4 Proteins 0.000 description 1
229930064664 L-arginine Natural products 0.000 description 1
235000014852 L-arginine Nutrition 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
235000011114 ammonium hydroxide Nutrition 0.000 description 1
238000010171 animal model Methods 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
230000002686 anti-diuretic effect Effects 0.000 description 1
229940124538 antidiuretic agent Drugs 0.000 description 1
239000003160 antidiuretic agent Substances 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
210000003169 central nervous system Anatomy 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
238000005660 chlorination reaction Methods 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
230000000875 corresponding effect Effects 0.000 description 1
239000012043 crude product Substances 0.000 description 1
235000018417 cysteine Nutrition 0.000 description 1
XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 1
230000004665 defense response Effects 0.000 description 1
238000010612 desalination reaction Methods 0.000 description 1
238000011161 development Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
OJAGAAVUZKMVGX-UHFFFAOYSA-N ethyl acetate;pyridine Chemical compound CCOC(C)=O.C1=CC=NC=C1 OJAGAAVUZKMVGX-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
125000000404 glutamine group Chemical group N[C@@H](CCC(N)=O)C(=O)* 0.000 description 1
NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
230000007786 learning performance Effects 0.000 description 1
230000005923 long-lasting effect Effects 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
238000012423 maintenance Methods 0.000 description 1
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
NFLWUMRGJYTJIN-UHFFFAOYSA-N n-[1-[(2-amino-2-oxoethyl)amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]-1-[7-(2-amino-2-oxoethyl)-10-(3-amino-3-oxopropyl)-13-benzyl-16-[(4-hydroxyphenyl)methyl]-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentazacycloicosane-4-carbonyl]pyrrolidi Chemical compound N1C(=O)C(CC=2C=CC(O)=CC=2)NC(=O)CCSSCC(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(=O)N)NC(=O)C1CC1=CC=CC=C1 NFLWUMRGJYTJIN-UHFFFAOYSA-N 0.000 description 1
FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 description 1
229960003104 ornithine Drugs 0.000 description 1
AHLPHDHHMVZTML-BYPYZUCNSA-N ornithyl group Chemical group N[C@@H](CCCN)C(=O)O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000007793 ph indicator Substances 0.000 description 1
229920001184 polypeptide Polymers 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
102000004196 processed proteins & peptides Human genes 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
230000004044 response Effects 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
230000035939 shock Effects 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
238000003756 stirring Methods 0.000 description 1
HNKJADCVZUBCPG-UHFFFAOYSA-N thioanisole Chemical compound CSC1=CC=CC=C1 HNKJADCVZUBCPG-UHFFFAOYSA-N 0.000 description 1
210000003813 thumb Anatomy 0.000 description 1
ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 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

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

NL8301320A 1982-04-20 1983-04-15 Analogen van vasopressine. NL8301320A (nl)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
CS280382		1982-04-20
CS822803A CS230315B1 (cs)	1982-04-20	1982-04-20	Analogy vasopresinu a způsob jejich výroby
CS830182A CS231749B1 (cs)	1982-11-19	1982-11-19	Analog vasopresinu a způsob jeho výroby
CS830182		1982-11-19

Publications (1)

Publication Number	Publication Date
NL8301320A true NL8301320A (nl)	1983-11-16

Family

ID=25745688

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL8301320A NL8301320A (nl)	1982-04-20	1983-04-15	Analogen van vasopressine.

Country Status (11)

Country	Link
US (1)	US4482486A (de)
JP (1)	JPS6485999A (de)
BE (1)	BE896504A (de)
CH (1)	CH653345A5 (de)
DE (1)	DE3314357A1 (de)
DK (1)	DK153883A (de)
FR (1)	FR2525215B1 (de)
GB (1)	GB2121049B (de)
IT (1)	IT1164189B (de)
NL (1)	NL8301320A (de)
SE (1)	SE460050B (de)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4714696A (en) *	1984-01-26	1987-12-22	Medical College Of Ohio	Novel derivatives of arginine vasopressin antagonists
PH21037A (en) *	1984-03-07	1987-06-30	Smithkline Beckman Corp	Des-proline vasopressin antagonists
US4661472A (en) *	1985-05-09	1987-04-28	The Salk Institute For Biological Studies	GnRH antagonists IX
US4711877A (en) *	1985-09-18	1987-12-08	Smithkline Beckman Corporation	6-pen-vasopressin compounds
US4760052A (en) *	1986-01-16	1988-07-26	Smithkline Beckman Corporation	1,6-dicarba-vasopressin compounds
US6028168A (en) *	1991-08-09	2000-02-22	Winfried Kolbeck	Lanthionine bridged peptides
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
US6903075B1 (en)	1997-05-29	2005-06-07	Merck & Co., Inc.	Heterocyclic amide compounds as cell adhesion inhibitors
WO1999064395A1 (en) *	1998-06-11	1999-12-16	Merck & Co., Inc.	Heterocyclic amide compounds as cell adhesion inhibitors
JO3371B1 (ar)	2013-07-26	2019-03-13	Ferring Bv	ناهضات مستقبل فاسوبريسين 2

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NL6509712A (de) *	1964-07-27	1966-01-28
CH495957A (de) *	1966-09-15	1970-09-15	Ceskoslovenska Akademie Ved	Verfahren zur Herstellung eines antidiuretisch wirksamen Polypeptids
NL167323C (nl) *	1970-09-26	1981-12-16	Organon Nv	Werkwijze ter bereiding van een psychofarmacologisch preparaat.
US4261980A (en) *	1980-05-16	1981-04-14	Vega Laboratories, Inc.	Method for prophylaxis and/or treatment of sickle cell disease
US4399125A (en) *	1981-03-24	1983-08-16	Maurice Manning	Novel antagonists of the antidiuretic action of arginine vasopressin

1983
- 1983-04-07 DK DK153883A patent/DK153883A/da not_active Application Discontinuation
- 1983-04-11 GB GB08309736A patent/GB2121049B/en not_active Expired
- 1983-04-14 SE SE8302075A patent/SE460050B/sv not_active IP Right Cessation
- 1983-04-15 NL NL8301320A patent/NL8301320A/nl not_active Application Discontinuation
- 1983-04-19 CH CH2098/83A patent/CH653345A5/de not_active IP Right Cessation
- 1983-04-19 BE BE0/210584A patent/BE896504A/fr not_active IP Right Cessation
- 1983-04-19 FR FR8306357A patent/FR2525215B1/fr not_active Expired
- 1983-04-19 IT IT20677/83A patent/IT1164189B/it active
- 1983-04-20 US US06/486,863 patent/US4482486A/en not_active Expired - Fee Related
- 1983-04-20 DE DE19833314357 patent/DE3314357A1/de not_active Ceased
1988
- 1988-06-15 JP JP63145941A patent/JPS6485999A/ja active Pending

Also Published As

Publication number	Publication date
IT1164189B (it)	1987-04-08
GB2121049A (en)	1983-12-14
SE460050B (sv)	1989-09-04
JPS6485999A (en)	1989-03-30
US4482486A (en)	1984-11-13
DK153883A (da)	1983-10-21
IT8320677A0 (it)	1983-04-19
SE8302075L (sv)	1983-10-21
SE8302075D0 (sv)	1983-04-14
CH653345A5 (de)	1985-12-31
DK153883D0 (da)	1983-04-07
BE896504A (fr)	1983-08-16
FR2525215B1 (fr)	1986-02-28
GB2121049B (en)	1985-04-17
GB8309736D0 (en)	1983-05-18
DE3314357A1 (de)	1983-10-27
FR2525215A1 (fr)	1983-10-21

Publication	Publication Date	Title
KR0173478B1 (ko)	1999-02-01	부갑상선 호르몬 길항물질
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