DE2452279A1 - Neue analoga des deamino-vasopressins mit modifizierter disulfidischer bruecke und ihr herstellungsverfahren - Google Patents
Neue analoga des deamino-vasopressins mit modifizierter disulfidischer bruecke und ihr herstellungsverfahrenInfo
- Publication number
- DE2452279A1 DE2452279A1 DE19742452279 DE2452279A DE2452279A1 DE 2452279 A1 DE2452279 A1 DE 2452279A1 DE 19742452279 DE19742452279 DE 19742452279 DE 2452279 A DE2452279 A DE 2452279A DE 2452279 A1 DE2452279 A1 DE 2452279A1
- Authority
- DE
- Germany
- Prior art keywords
- ether
- chg
- group
- vasopressin
- amide
- Prior art date
- 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.)
- Withdrawn
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 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 class 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 title claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 16
- 229910052799 carbon Inorganic materials 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 7
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims description 6
- 125000006239 protecting group Chemical group 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- ZRALSGWEFCBTJO-UHFFFAOYSA-N guanidine group Chemical group NC(=N)N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 3
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- 230000003213 activating effect Effects 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical group O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 claims 1
- 238000007363 ring formation reaction Methods 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 90
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 53
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 42
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 34
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 22
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 22
- 239000000047 product Substances 0.000 description 21
- 150000001408 amides Chemical class 0.000 description 20
- 229910052757 nitrogen Inorganic materials 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 235000001014 amino acid Nutrition 0.000 description 15
- 150000001413 amino acids Chemical group 0.000 description 15
- 230000000694 effects Effects 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- 238000004458 analytical method Methods 0.000 description 14
- 239000011541 reaction mixture Substances 0.000 description 14
- 150000001875 compounds Chemical class 0.000 description 12
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 12
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 11
- 229960003726 vasopressin Drugs 0.000 description 11
- 239000002904 solvent Substances 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 9
- 238000001035 drying Methods 0.000 description 9
- 229940088597 hormone Drugs 0.000 description 9
- 239000005556 hormone Substances 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- 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 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- 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 description 7
- 108010004977 Vasopressins Proteins 0.000 description 7
- 102000002852 Vasopressins Human genes 0.000 description 7
- 238000009826 distribution Methods 0.000 description 7
- 150000003951 lactams Chemical class 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 230000004071 biological effect Effects 0.000 description 6
- MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 6
- 238000004108 freeze drying Methods 0.000 description 6
- 230000002686 anti-diuretic effect Effects 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000013067 intermediate product Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000005192 partition Methods 0.000 description 4
- 210000004291 uterus Anatomy 0.000 description 4
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 3
- 239000004471 Glycine Substances 0.000 description 3
- 208000032843 Hemorrhage Diseases 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 3
- HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229920001429 chelating resin Polymers 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 238000001514 detection method Methods 0.000 description 3
- 235000019439 ethyl acetate Nutrition 0.000 description 3
- 210000003608 fece Anatomy 0.000 description 3
- 238000001997 free-flow electrophoresis Methods 0.000 description 3
- 230000002496 gastric effect Effects 0.000 description 3
- 239000010871 livestock manure Substances 0.000 description 3
- 230000008719 thickening Effects 0.000 description 3
- 239000004475 Arginine Substances 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 101800000989 Oxytocin Proteins 0.000 description 2
- 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 description 2
- 102100031951 Oxytocin-neurophysin 1 Human genes 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 102100026383 Vasopressin-neurophysin 2-copeptin Human genes 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 229940124538 antidiuretic agent Drugs 0.000 description 2
- 239000003160 antidiuretic agent Substances 0.000 description 2
- 230000036772 blood pressure Effects 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 235000018417 cysteine Nutrition 0.000 description 2
- 125000000151 cysteine group Chemical group N[C@@H](CS)C(=O)* 0.000 description 2
- 201000010064 diabetes insipidus Diseases 0.000 description 2
- 230000002255 enzymatic effect Effects 0.000 description 2
- 238000002523 gelfiltration Methods 0.000 description 2
- 230000000004 hemodynamic effect Effects 0.000 description 2
- PSGAAPLEWMOORI-PEINSRQWSA-N medroxyprogesterone acetate Chemical compound C([C@@]12C)CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2CC[C@]2(C)[C@@](OC(C)=O)(C(C)=O)CC[C@H]21 PSGAAPLEWMOORI-PEINSRQWSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 210000004165 myocardium Anatomy 0.000 description 2
- FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 description 2
- -1 nitrobenzenesulfenyl Chemical group 0.000 description 2
- 229960001723 oxytocin Drugs 0.000 description 2
- 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 description 2
- 230000002035 prolonged effect Effects 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000001226 reprecipitation Methods 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 230000003191 uterotonic effect Effects 0.000 description 2
- 239000005526 vasoconstrictor agent Substances 0.000 description 2
- ZYGRWJVRLNJIMR-NSHDSACASA-N (2s)-5-azaniumyl-2-(phenylmethoxycarbonylamino)pentanoate Chemical compound NCCC[C@@H](C(O)=O)NC(=O)OCC1=CC=CC=C1 ZYGRWJVRLNJIMR-NSHDSACASA-N 0.000 description 1
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 102100021277 Beta-secretase 2 Human genes 0.000 description 1
- 101710150190 Beta-secretase 2 Proteins 0.000 description 1
- 150000008575 L-amino acids Chemical group 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 108010010056 Terlipressin Proteins 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000008351 acetate buffer Substances 0.000 description 1
- MTEUMURLJRZUKD-UHFFFAOYSA-N acetic acid;butan-1-ol;pyridine;hydrate Chemical compound O.CC(O)=O.CCCCO.C1=CC=NC=C1 MTEUMURLJRZUKD-UHFFFAOYSA-N 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- 230000002763 arrhythmic effect Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 125000002228 disulfide group Chemical group 0.000 description 1
- UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 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
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000035873 hypermotility Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 230000006651 lactation Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000000709 neurohypophysis hormone Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000036513 peripheral conductance Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 230000002265 prevention Effects 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
- 230000009467 reduction Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- BENFXAYNYRLAIU-QSVFAHTRSA-N terlipressin 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](NC(=O)CNC(=O)CNC(=O)CN)CSSC1 BENFXAYNYRLAIU-QSVFAHTRSA-N 0.000 description 1
- 229960003813 terlipressin Drugs 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
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- 210000003932 urinary bladder Anatomy 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- PJVWKTKQMONHTI-UHFFFAOYSA-N warfarin Chemical compound OC=1C2=CC=CC=C2OC(=O)C=1C(CC(=O)C)C1=CC=CC=C1 PJVWKTKQMONHTI-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/10—Tetrapeptides
- C07K5/1002—Tetrapeptides with the first amino acid being neutral
- C07K5/1005—Tetrapeptides with the first amino acid being neutral and aliphatic
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
-
- 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
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
-
- 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)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biophysics (AREA)
- Biochemistry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Pharmacology & Pharmacy (AREA)
- Diabetes (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Endocrinology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS7700A CS171787B1 (enExample) | 1973-11-09 | 1973-11-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2452279A1 true DE2452279A1 (de) | 1975-05-15 |
Family
ID=5426587
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19742452279 Withdrawn DE2452279A1 (de) | 1973-11-09 | 1974-11-04 | Neue analoga des deamino-vasopressins mit modifizierter disulfidischer bruecke und ihr herstellungsverfahren |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US3980631A (enExample) |
| JP (1) | JPS5411319B2 (enExample) |
| AR (1) | AR207765A1 (enExample) |
| BE (1) | BE822062A (enExample) |
| CA (1) | CA1020547A (enExample) |
| CH (1) | CH610879A5 (enExample) |
| CS (1) | CS171787B1 (enExample) |
| DE (1) | DE2452279A1 (enExample) |
| DK (1) | DK567474A (enExample) |
| FR (1) | FR2250751B1 (enExample) |
| GB (1) | GB1440859A (enExample) |
| IN (1) | IN140167B (enExample) |
| IT (1) | IT1056739B (enExample) |
| NL (1) | NL7414490A (enExample) |
| SE (1) | SE419753B (enExample) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4235881A (en) * | 1978-12-04 | 1980-11-25 | Cort Joseph H | Method for producing high potency factor VIII |
| US4285858A (en) * | 1979-10-30 | 1981-08-25 | Mt. Sinai School Of Medicine Of The City University Of N.Y. | Vasopressin analogs |
| US4481191A (en) * | 1983-03-30 | 1984-11-06 | The Regents Of The University Of California | Method for controlling blood pressure |
| US4829051A (en) * | 1983-04-05 | 1989-05-09 | Vega Laboratories, Inc. | N-substituted derivatives of 1-desaminovasopressin |
| US4483794A (en) * | 1983-05-10 | 1984-11-20 | Ceskoslovenska Akademie Ved | Analogs of neurohypophysial hormones |
| US4551445A (en) * | 1983-10-14 | 1985-11-05 | The Medical College Of Ohio | Derivatives of arginine vasopressin antagonists |
| US4714696A (en) * | 1984-01-26 | 1987-12-22 | Medical College Of Ohio | Novel derivatives of arginine vasopressin antagonists |
| IE58407B1 (en) * | 1984-04-13 | 1993-09-22 | Akzo Nv | Peptides |
| US4760052A (en) * | 1986-01-16 | 1988-07-26 | Smithkline Beckman Corporation | 1,6-dicarba-vasopressin compounds |
| EP0300036A4 (en) * | 1987-01-30 | 1989-06-14 | Biomed Res Consultants Ltd | PHARMACEUTICAL COMPOSITIONS BASED ON VASOPRESSIN. |
| US4786631A (en) * | 1988-03-18 | 1988-11-22 | University Of Florida | Novel arginine vasopressin-binding peptides |
| US6028168A (en) | 1991-08-09 | 2000-02-22 | Winfried Kolbeck | Lanthionine bridged peptides |
| AU2237095A (en) * | 1994-04-01 | 1995-10-23 | Arcturus Pharmaceutical Corporation | Method for delivering biologically active materials using a thioester or thioether prodrug |
| 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 |
| PT2381923T (pt) | 2008-12-22 | 2018-11-13 | Serenity Pharmaceuticals Llc | Administração intranasal de desmopressina |
| US20100160214A1 (en) * | 2008-12-22 | 2010-06-24 | Serenity Pharmaceuticals Corporation | Desmopressin composition |
| ES2638815T5 (en) | 2009-06-18 | 2025-06-26 | Acerus Pharmaceuticals Usa Llc | Safe desmopressin administration |
-
1973
- 1973-11-09 CS CS7700A patent/CS171787B1/cs unknown
-
1974
- 1974-01-01 AR AR256291A patent/AR207765A1/es active
- 1974-09-19 SE SE7411817A patent/SE419753B/xx unknown
- 1974-10-02 IT IT28019/74A patent/IT1056739B/it active
- 1974-10-07 US US05/512,429 patent/US3980631A/en not_active Expired - Lifetime
- 1974-10-08 IN IN2260/CAL/74A patent/IN140167B/en unknown
- 1974-10-14 FR FR7434405A patent/FR2250751B1/fr not_active Expired
- 1974-10-14 GB GB4451774A patent/GB1440859A/en not_active Expired
- 1974-10-16 JP JP11916874A patent/JPS5411319B2/ja not_active Expired
- 1974-10-31 DK DK567474A patent/DK567474A/da unknown
- 1974-11-04 CA CA213,092A patent/CA1020547A/en not_active Expired
- 1974-11-04 DE DE19742452279 patent/DE2452279A1/de not_active Withdrawn
- 1974-11-06 NL NL7414490A patent/NL7414490A/xx not_active Application Discontinuation
- 1974-11-07 CH CH1490974A patent/CH610879A5/xx not_active IP Right Cessation
- 1974-11-12 BE BE150394A patent/BE822062A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CH610879A5 (enExample) | 1979-05-15 |
| SE419753B (sv) | 1981-08-24 |
| CA1020547A (en) | 1977-11-08 |
| JPS5088085A (enExample) | 1975-07-15 |
| US3980631A (en) | 1976-09-14 |
| JPS5411319B2 (enExample) | 1979-05-14 |
| FR2250751A1 (enExample) | 1975-06-06 |
| FR2250751B1 (enExample) | 1979-05-11 |
| GB1440859A (en) | 1976-06-30 |
| NL7414490A (nl) | 1975-05-13 |
| IT1056739B (it) | 1982-02-20 |
| SE7411817L (enExample) | 1975-05-12 |
| DK567474A (enExample) | 1975-07-07 |
| IN140167B (enExample) | 1976-09-25 |
| CS171787B1 (enExample) | 1976-11-29 |
| BE822062A (fr) | 1975-03-03 |
| AR207765A1 (es) | 1976-10-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8141 | Disposal/no request for examination |