CS230614B1 - Analogues of realising factor for luteining and folliculstimulated hormon - Google Patents
Analogues of realising factor for luteining and folliculstimulated hormon Download PDFInfo
- Publication number
- CS230614B1 CS230614B1 CS825868A CS586882A CS230614B1 CS 230614 B1 CS230614 B1 CS 230614B1 CS 825868 A CS825868 A CS 825868A CS 586882 A CS586882 A CS 586882A CS 230614 B1 CS230614 B1 CS 230614B1
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- pro
- arg
- tle
- leu
- solution
- Prior art date
Links
- 125000006239 protecting group Chemical group 0.000 claims abstract description 5
- 229940088597 hormone Drugs 0.000 claims abstract description 4
- 239000005556 hormone Substances 0.000 claims abstract description 4
- 230000001456 gonadotroph Effects 0.000 claims abstract 2
- 230000004936 stimulating effect Effects 0.000 claims 1
- 239000003814 drug Substances 0.000 abstract description 4
- 102000012673 Follicle Stimulating Hormone Human genes 0.000 abstract description 3
- 108010079345 Follicle Stimulating Hormone Proteins 0.000 abstract description 3
- 102000009151 Luteinizing Hormone Human genes 0.000 abstract description 3
- 108010073521 Luteinizing Hormone Proteins 0.000 abstract description 3
- 229940028334 follicle stimulating hormone Drugs 0.000 abstract description 3
- 229940040129 luteinizing hormone Drugs 0.000 abstract description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 18
- 239000000047 product Substances 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- 230000000694 effects Effects 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 239000012071 phase Substances 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- 150000001413 amino acids Chemical class 0.000 description 9
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
- 108090000765 processed proteins & peptides Proteins 0.000 description 8
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 7
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 7
- 102000004196 processed proteins & peptides Human genes 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 238000004811 liquid chromatography Methods 0.000 description 6
- 230000004071 biological effect Effects 0.000 description 5
- 239000006260 foam Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000006467 substitution reaction Methods 0.000 description 5
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 4
- 230000005526 G1 to G0 transition Effects 0.000 description 4
- HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000001514 detection method Methods 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 239000004475 Arginine Substances 0.000 description 2
- 241000283690 Bos taurus Species 0.000 description 2
- JQJPBYFTQAANLE-UHFFFAOYSA-N Butyl nitrite Chemical compound CCCCON=O JQJPBYFTQAANLE-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000000556 agonist Substances 0.000 description 2
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 150000001540 azides Chemical class 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 229940124558 contraceptive agent Drugs 0.000 description 2
- 239000003433 contraceptive agent Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000010612 desalination reaction Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000016087 ovulation Effects 0.000 description 2
- 229910052763 palladium Inorganic materials 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
- 239000008363 phosphate buffer Substances 0.000 description 2
- 230000003389 potentiating effect Effects 0.000 description 2
- 239000003488 releasing hormone Substances 0.000 description 2
- 230000001850 reproductive effect Effects 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 2
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 2
- 239000003039 volatile agent Substances 0.000 description 2
- JXGVXCZADZNAMJ-NSHDSACASA-N (2s)-1-phenylmethoxycarbonylpyrrolidine-2-carboxylic acid Chemical compound OC(=O)[C@@H]1CCCN1C(=O)OCC1=CC=CC=C1 JXGVXCZADZNAMJ-NSHDSACASA-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
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- MOMFXATYAINJML-UHFFFAOYSA-N 2-Acetylthiazole Chemical group CC(=O)C1=NC=CS1 MOMFXATYAINJML-UHFFFAOYSA-N 0.000 description 1
- VTKWFWXOVZIATL-NPPUSCPJSA-N 2-[[(2s)-3-(4h-imidazol-4-yl)-2-[[(2s)-5-oxopyrrolidine-2-carbonyl]amino]propanoyl]amino]acetic acid Chemical compound C([C@@H](C(=O)NCC(=O)O)NC(=O)[C@H]1NC(=O)CC1)C1C=NC=N1 VTKWFWXOVZIATL-NPPUSCPJSA-N 0.000 description 1
- JLLYLQLDYORLBB-UHFFFAOYSA-N 5-bromo-n-methylthiophene-2-sulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(Br)S1 JLLYLQLDYORLBB-UHFFFAOYSA-N 0.000 description 1
- FCSKOFQQCWLGMV-UHFFFAOYSA-N 5-{5-[2-chloro-4-(4,5-dihydro-1,3-oxazol-2-yl)phenoxy]pentyl}-3-methylisoxazole Chemical compound O1N=C(C)C=C1CCCCCOC1=CC=C(C=2OCCN=2)C=C1Cl FCSKOFQQCWLGMV-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- 125000002059 L-arginyl group Chemical group O=C([*])[C@](N([H])[H])([H])C([H])([H])C([H])([H])C([H])([H])N([H])C(=N[H])N([H])[H] 0.000 description 1
- SENJXOPIZNYLHU-UHFFFAOYSA-N L-leucyl-L-arginine Natural products CC(C)CC(N)C(=O)NC(C(O)=O)CCCN=C(N)N SENJXOPIZNYLHU-UHFFFAOYSA-N 0.000 description 1
- RNKSNIBMTUYWSH-YFKPBYRVSA-N L-prolylglycine Chemical compound [O-]C(=O)CNC(=O)[C@@H]1CCC[NH2+]1 RNKSNIBMTUYWSH-YFKPBYRVSA-N 0.000 description 1
- SENJXOPIZNYLHU-IUCAKERBSA-N Leu-Arg Chemical compound CC(C)C[C@H](N)C(=O)N[C@H](C(O)=O)CCCN=C(N)N SENJXOPIZNYLHU-IUCAKERBSA-N 0.000 description 1
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 description 1
- 101710119110 Prolactin-1 Proteins 0.000 description 1
- 241000473945 Theria <moth genus> Species 0.000 description 1
- HPYDSVWYXXKHRD-VIFPVBQESA-N Tyr-Gly Chemical compound [O-]C(=O)CNC(=O)[C@@H]([NH3+])CC1=CC=C(O)C=C1 HPYDSVWYXXKHRD-VIFPVBQESA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 238000005349 anion exchange Methods 0.000 description 1
- 210000004198 anterior pituitary gland Anatomy 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
- 238000004166 bioassay Methods 0.000 description 1
- 239000000872 buffer Substances 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
- 201000011510 cancer Diseases 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 235000013365 dairy product Nutrition 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000000994 depressogenic effect Effects 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 230000002124 endocrine Effects 0.000 description 1
- 239000002024 ethyl acetate extract Substances 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- BEBCJVAWIBVWNZ-UHFFFAOYSA-N glycinamide Chemical group NCC(N)=O BEBCJVAWIBVWNZ-UHFFFAOYSA-N 0.000 description 1
- 230000002710 gonadal effect Effects 0.000 description 1
- ZRALSGWEFCBTJO-UHFFFAOYSA-N guanidine group Chemical group NC(=N)N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 1
- 244000309465 heifer Species 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- 210000003016 hypothalamus Anatomy 0.000 description 1
- 208000000509 infertility Diseases 0.000 description 1
- 230000036512 infertility Effects 0.000 description 1
- 231100000535 infertility Toxicity 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 230000026045 iodination Effects 0.000 description 1
- 238000006192 iodination reaction Methods 0.000 description 1
- 108010000761 leucylarginine Proteins 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- APBBAQCENVXUHL-UHFFFAOYSA-N n,n-diethylethanamine;2,2,2-trifluoroacetic acid Chemical compound CCN(CC)CC.OC(=O)C(F)(F)F APBBAQCENVXUHL-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 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
- 208000025661 ovarian cyst Diseases 0.000 description 1
- 208000015124 ovarian disease Diseases 0.000 description 1
- 239000006174 pH buffer Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 108010029020 prolylglycine Proteins 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 108010022711 pyroglutamyl-histidyl-glycine Proteins 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000003307 slaughter Methods 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 238000010532 solid phase synthesis reaction Methods 0.000 description 1
- 230000021595 spermatogenesis Effects 0.000 description 1
- 239000003270 steroid hormone Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 1
- 108010017949 tyrosyl-glycyl-glycine Proteins 0.000 description 1
- 238000005406 washing Methods 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
- C07K7/23—Luteinising hormone-releasing hormone [LHRH]; Related peptides
-
- 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
-
- 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
- Y10S930/11—Gonadotropin; related 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
- Y10S930/13—Luteinizing hormone-releasing hormone; related peptides
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Endocrinology (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Diabetes (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Medicinal Preparation (AREA)
- Steroid Compounds (AREA)
Priority Applications (14)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS825868A CS230614B1 (en) | 1982-08-06 | 1982-08-06 | Analogues of realising factor for luteining and folliculstimulated hormon |
| AT0271583A AT387026B (de) | 1982-08-06 | 1983-07-26 | Verfahren zur herstellung von neuen lh-fsh-releasingfaktoranaloga |
| SE8304158A SE456345B (sv) | 1982-08-06 | 1983-07-27 | Luteiniserings- och follikelstimulerande hormoner frigorande faktoranaloger med hog gonadotropisk verkan samt ett forfarande for framstellning derav |
| FR8312707A FR2531952B1 (fr) | 1982-08-06 | 1983-08-02 | Analogues a forte activite gonadotrope du facteur liberant l'hormone luteinisante et l'hormone folliculostimulante et leur procede de preparation |
| IT22397/83A IT1165473B (it) | 1982-08-06 | 1983-08-02 | Analoghi,ad elevata attivita' gonadotropa,di fattori che liberano ormone luteinizante e ormone follicolo-stimolante,e processo per la loro preparazione |
| GB08320922A GB2125408B (en) | 1982-08-06 | 1983-08-03 | Luteinizing and follicle-stimulating hormones releasing factor analogs |
| BE0/211294A BE897455A (fr) | 1982-08-06 | 1983-08-03 | Analogues du facteur liberant des hormones luteininsantes et stimulant les follicules ces analogues exercant une haute activite gomadotrope de meme que leur procede de preparation |
| DE19833328235 DE3328235A1 (de) | 1982-08-06 | 1983-08-04 | Gonadotrop hochwirksame synthetische analoga der releasingfaktoren der hormone lh und fsh und verfahren zu ihrer herstellung |
| JP58141977A JPS5959654A (ja) | 1982-08-06 | 1983-08-04 | ホルモン放出因子類似体及びその製造方法 |
| CA000434011A CA1206959A (fr) | 1982-08-06 | 1983-08-05 | Hormone luteinisante et folliculostimuline liberant des facteurs analogues a une activite gonadotrope elevee et procede de preparation |
| CH4271/83A CH658662A5 (de) | 1982-08-06 | 1983-08-05 | Gonadotrop hochwirksame luteinierungs- und follikelstimulierungshormon-liberationsfaktoranaloge und verfahren zu deren herstellung. |
| HU832783A HU192962B (en) | 1982-08-06 | 1983-08-05 | Process for producing analogues with strong gonadotripic activity of factor the general formula /i/ of hormone releasing luteinizing and estron-stimulating hormones |
| YU1633/83A YU45144B (en) | 1982-08-06 | 1983-08-05 | Process for making new nonapeptides with high gonadotropic activity |
| US06/521,108 US4512923A (en) | 1982-08-06 | 1983-08-08 | Luteinizing and follicle stimulating hormones and process for the preparation thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS825868A CS230614B1 (en) | 1982-08-06 | 1982-08-06 | Analogues of realising factor for luteining and folliculstimulated hormon |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS230614B1 true CS230614B1 (en) | 1984-08-13 |
Family
ID=5404451
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS825868A CS230614B1 (en) | 1982-08-06 | 1982-08-06 | Analogues of realising factor for luteining and folliculstimulated hormon |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US4512923A (fr) |
| JP (1) | JPS5959654A (fr) |
| AT (1) | AT387026B (fr) |
| BE (1) | BE897455A (fr) |
| CA (1) | CA1206959A (fr) |
| CH (1) | CH658662A5 (fr) |
| CS (1) | CS230614B1 (fr) |
| DE (1) | DE3328235A1 (fr) |
| FR (1) | FR2531952B1 (fr) |
| GB (1) | GB2125408B (fr) |
| HU (1) | HU192962B (fr) |
| IT (1) | IT1165473B (fr) |
| SE (1) | SE456345B (fr) |
| YU (1) | YU45144B (fr) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU194280B (en) * | 1985-10-22 | 1988-01-28 | Richter Gedeon Vegyeszet | Process for producing new gonadoliberin analogues of high effectivity and pharmaceutical compositions containing them |
| US4762717A (en) * | 1986-03-21 | 1988-08-09 | The General Hospital Corporation | Continuous delivery of luteinizing hormone releasing hormone compositions in combination with sex steroid delivery for use as a contraceptive |
| DE4305225A1 (de) * | 1993-02-19 | 1994-08-25 | Asta Medica Ag | Neues Herstellverfahren für Cetrorelix Lyophilisat |
| US6828415B2 (en) * | 1993-02-19 | 2004-12-07 | Zentaris Gmbh | Oligopeptide lyophilisate, their preparation and use |
| CA2192782C (fr) | 1995-12-15 | 2008-10-14 | Nobuyuki Takechi | Production de microsphere |
| CA2192773C (fr) | 1995-12-15 | 2008-09-23 | Hiroaki Okada | Obtention d'une preparation a liberation prolongee pour injection |
| US5972895A (en) * | 1996-12-11 | 1999-10-26 | A. Glenn Braswell | Composition and method for increasing growth hormone levels |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT347054B (de) * | 1973-09-29 | 1978-12-11 | Takeda Chemical Industries Ltd | Verfahren zur herstellung von neuen nonapeptidamid-derivaten |
| GB1532211A (en) * | 1974-10-25 | 1978-11-15 | Wellcome Found | Lh-rh peptide analogues |
| US4101537A (en) * | 1977-04-07 | 1978-07-18 | Parke, Davis & Company | Octapeptides and methods for their production |
| US4124577A (en) * | 1977-06-13 | 1978-11-07 | Warner-Lambert | Nonapeptides and methods for their production |
| IT1149971B (it) * | 1979-06-11 | 1986-12-10 | Syntex Inc | Derivati nonapeptide e decapeptide dell'ormone che rilascia l'ormone luteinizzante |
-
1982
- 1982-08-06 CS CS825868A patent/CS230614B1/cs unknown
-
1983
- 1983-07-26 AT AT0271583A patent/AT387026B/de not_active IP Right Cessation
- 1983-07-27 SE SE8304158A patent/SE456345B/sv not_active IP Right Cessation
- 1983-08-02 IT IT22397/83A patent/IT1165473B/it active
- 1983-08-02 FR FR8312707A patent/FR2531952B1/fr not_active Expired
- 1983-08-03 BE BE0/211294A patent/BE897455A/fr unknown
- 1983-08-03 GB GB08320922A patent/GB2125408B/en not_active Expired
- 1983-08-04 DE DE19833328235 patent/DE3328235A1/de not_active Ceased
- 1983-08-04 JP JP58141977A patent/JPS5959654A/ja active Pending
- 1983-08-05 CA CA000434011A patent/CA1206959A/fr not_active Expired
- 1983-08-05 YU YU1633/83A patent/YU45144B/xx unknown
- 1983-08-05 HU HU832783A patent/HU192962B/hu unknown
- 1983-08-05 CH CH4271/83A patent/CH658662A5/de not_active IP Right Cessation
- 1983-08-08 US US06/521,108 patent/US4512923A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| IT8322397A1 (it) | 1985-02-02 |
| JPS5959654A (ja) | 1984-04-05 |
| DE3328235A1 (de) | 1984-04-05 |
| YU45144B (en) | 1992-03-10 |
| CH658662A5 (de) | 1986-11-28 |
| GB2125408A (en) | 1984-03-07 |
| ATA271583A (de) | 1988-04-15 |
| IT1165473B (it) | 1987-04-22 |
| YU163383A (en) | 1986-06-30 |
| FR2531952B1 (fr) | 1988-07-22 |
| US4512923A (en) | 1985-04-23 |
| GB8320922D0 (en) | 1983-09-07 |
| CA1206959A (fr) | 1986-07-02 |
| SE8304158D0 (sv) | 1983-07-27 |
| IT8322397A0 (it) | 1983-08-02 |
| FR2531952A1 (fr) | 1984-02-24 |
| HU192962B (en) | 1987-08-28 |
| BE897455A (fr) | 1983-12-01 |
| GB2125408B (en) | 1986-06-18 |
| SE8304158L (sv) | 1984-02-07 |
| SE456345B (sv) | 1988-09-26 |
| AT387026B (de) | 1988-11-25 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR930008095B1 (ko) | Lhrh 길항제로서 유용한 lhrh의 노나펩타이드 및 데카펩타이드 동족체 | |
| KR910002550B1 (ko) | Lhrh의 노나펩타이드 및 데카펩타이드 동족체 및 이의 제조방법 | |
| US3992365A (en) | Agonist analogues of luteinizing hormone releasing hormone | |
| US4317815A (en) | LH-RH Antagonists | |
| FI60553C (fi) | Foerfarande foer framstaellning av ovulationsframkallande nonapeptidamidderivat | |
| SE437993B (sv) | Sett att framstella en polypeptid med luliberin-agonist-egenskaper | |
| SI8011553A8 (sl) | Postopek za pripravo nonapeptidnih in dekapeptidnih derivatov hormonov za sproščanje luteinizirajočega hormona | |
| HU213098B (en) | Process for producing decapeptides antagonistic to hormone for releazing lutheinizing-hormone and pharmaceutical compositions containing them as active components | |
| EP0192492B1 (fr) | Peptides contenant une chaîne latérale cétone aliphatique-aromatique | |
| EP0081877B1 (fr) | Antagonistes de LH-RH | |
| CA1057743A (fr) | Composes analogues de type lh-rh | |
| CS230614B1 (en) | Analogues of realising factor for luteining and folliculstimulated hormon | |
| AU662496B2 (en) | LHRH-antagonists | |
| US4721775A (en) | Effective peptides related to the luteinizing hormone releasing hormone from L-amino acids | |
| Yanaihara et al. | Synthesis and biological evaluation of LH-and FSH-releasing hormone and its analogs | |
| US3888838A (en) | Decapeptide having luteinizing hormone (lh)-and follicle stimulating hormone (fsh)-releasing activity, salts and compositions thereof, a process for preparing same, and intermediates therefor | |
| US4083967A (en) | Nona- and decapeptides | |
| HU185427B (en) | Process for preparing antagonists of hormone releasing luteinizing hormone | |
| US4111923A (en) | Octapeptides and methods for their production | |
| US4261887A (en) | Peptide compositions | |
| US4948873A (en) | Gonadoliberine analogues of high activity | |
| JP2672677B2 (ja) | Lhrh同族体 | |
| Burov et al. | Synthesis of biologically active analogs of luliberin with shortened amino acid sequences | |
| Sivanandaiah et al. | Improved solid phase synthesis of luteinizing hormone releasing hormone analogues using 9-fluorenylmethyloxycarbonyl amino acid active esters and catalytic transfer hydrogenation with minimal side-chain protection and their biological activities | |
| JPS59501985A (ja) | 生殖腺機能に影響を及ぼすペプチド類 |