SE456345B - Luteiniserings- och follikelstimulerande hormoner frigorande faktoranaloger med hog gonadotropisk verkan samt ett forfarande for framstellning derav - Google Patents

Luteiniserings- och follikelstimulerande hormoner frigorande faktoranaloger med hog gonadotropisk verkan samt ett forfarande for framstellning derav

Info

Publication number: SE456345B
Authority: SE; Sweden
Prior art keywords: pro; arg; solution; trp; leu
Prior art date: 1982-08-06

Application number

SE8304158A

Other languages

English (en)

Swedish (sv)

Other versions

SE8304158D0 (sv

SE8304158L (sv

Inventor

M Flegel

J Pospisek

J Picha

D Pichova

M Krojidlo

J Kolinsky

Original Assignee

Spofa Vereinigte Pharma Werke

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.)

1982-08-06

Filing date

1983-07-27

Publication date

1988-09-26

1983-07-27 Application filed by Spofa Vereinigte Pharma Werke filed Critical Spofa Vereinigte Pharma Werke

1983-07-27 Publication of SE8304158D0 publication Critical patent/SE8304158D0/xx

1984-02-07 Publication of SE8304158L publication Critical patent/SE8304158L/xx

1988-09-26 Publication of SE456345B publication Critical patent/SE456345B/sv

Links

238000000034 method Methods 0.000 title claims description 13
229940088597 hormone Drugs 0.000 title claims 2
239000005556 hormone Substances 0.000 title claims 2
230000001456 gonadotroph Effects 0.000 title 1
230000000977 initiatory effect Effects 0.000 title 1
230000004936 stimulating effect Effects 0.000 title 1
239000000047 product Substances 0.000 claims description 21
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 16
150000001875 compounds Chemical class 0.000 claims description 12
108090000765 processed proteins & peptides Proteins 0.000 claims description 11
125000006239 protecting group Chemical group 0.000 claims description 10
238000004811 liquid chromatography Methods 0.000 claims description 7
CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 claims description 6
238000006243 chemical reaction Methods 0.000 claims description 5
238000002360 preparation method Methods 0.000 claims description 5
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 3
238000000746 purification Methods 0.000 claims description 3
230000008030 elimination Effects 0.000 claims description 2
238000003379 elimination reaction Methods 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
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230000001681 protective effect Effects 0.000 claims 2
101100203596 Caenorhabditis elegans sol-1 gene Proteins 0.000 claims 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
239000002253 acid Substances 0.000 claims 1
239000007795 chemical reaction product Substances 0.000 claims 1
229910052739 hydrogen Inorganic materials 0.000 claims 1
239000001257 hydrogen Substances 0.000 claims 1
238000002955 isolation Methods 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
239000000243 solution Substances 0.000 description 22
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
239000000203 mixture Substances 0.000 description 14
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
239000012071 phase Substances 0.000 description 12
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 10
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
150000001413 amino acids Chemical class 0.000 description 9
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XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 4
HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-UHFFFAOYSA-N 0.000 description 4
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JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 3
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239000002243 precursor Substances 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
150000003254 radicals Chemical group 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
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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
NPDBDJFLKKQMCM-SCSAIBSYSA-N (2s)-2-amino-3,3-dimethylbutanoic acid Chemical compound CC(C)(C)[C@H](N)C(O)=O NPDBDJFLKKQMCM-SCSAIBSYSA-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
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
OVBRGKZTKQSNRM-JTRKXDDTSA-N 2-[[(9s,12s,15s,21s,30s,33s)-9-[(3-amino-4-hydroxyphenyl)methyl]-33-(2-amino-2-oxoethyl)-21-carbamoyl-12-(2-methylpropyl)-8,11,14,17,19,23,29,32,35-nonaoxo-30-propan-2-yl-19$l^{4}-thia-7,10,13,16,22,28,31,34-octazaspiro[5.29]pentatriacontan-15-yl]methyl]p Chemical compound N([C@@H](CC(N)=O)C(=O)N[C@H](C(=O)NCCCCC(=O)N[C@H](C[S+]([O-])CC(=O)N[C@@H](CC(C(O)=O)C(O)=O)C(=O)N[C@H](C(N[C@@H](CC=1C=C(N)C(O)=CC=1)C(=O)N1)=O)CC(C)C)C(N)=O)C(C)C)C(=O)C21CCCCC2 OVBRGKZTKQSNRM-JTRKXDDTSA-N 0.000 description 1
JPZXHKDZASGCLU-GFCCVEGCSA-N 3-(2-Naphthyl)-D-Alanine Chemical compound C1=CC=CC2=CC(C[C@@H](N)C(O)=O)=CC=C21 JPZXHKDZASGCLU-GFCCVEGCSA-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
239000004475 Arginine Substances 0.000 description 1
241000283690 Bos taurus Species 0.000 description 1
DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 1
150000008574 D-amino acids Chemical class 0.000 description 1
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 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
206010028980 Neoplasm Diseases 0.000 description 1
101150006914 TRP1 gene Proteins 0.000 description 1
LVTKHGUGBGNBPL-UHFFFAOYSA-N Trp-P-1 Chemical compound N1C2=CC=CC=C2C2=C1C(C)=C(N)N=C2C LVTKHGUGBGNBPL-UHFFFAOYSA-N 0.000 description 1
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239000013543 active substance Substances 0.000 description 1
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ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
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WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
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230000001419 dependent effect Effects 0.000 description 1
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238000011161 development Methods 0.000 description 1
MQYQOVYIJOLTNX-UHFFFAOYSA-N dichloromethane;n,n-dimethylformamide Chemical compound ClCCl.CN(C)C=O MQYQOVYIJOLTNX-UHFFFAOYSA-N 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000009977 dual effect Effects 0.000 description 1
238000010828 elution Methods 0.000 description 1
230000002124 endocrine Effects 0.000 description 1
230000007515 enzymatic degradation Effects 0.000 description 1
SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 description 1
NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
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239000012634 fragment Substances 0.000 description 1
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125000000524 functional group Chemical group 0.000 description 1
DXMZNKNJOBUNRO-UHFFFAOYSA-N glycyl radical Chemical group N[CH]C(O)=O DXMZNKNJOBUNRO-UHFFFAOYSA-N 0.000 description 1
210000002149 gonad Anatomy 0.000 description 1
125000002795 guanidino group Chemical group C(N)(=N)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
230000006698 induction Effects 0.000 description 1
230000036512 infertility Effects 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
230000002045 lasting effect Effects 0.000 description 1
108010000761 leucylarginine Proteins 0.000 description 1
230000002503 metabolic effect Effects 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
GINQYTLDMNFGQP-UHFFFAOYSA-N n,n-dimethylformamide;methylsulfinylmethane Chemical compound CS(C)=O.CN(C)C=O GINQYTLDMNFGQP-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
238000009806 oophorectomy Methods 0.000 description 1
208000025661 ovarian cyst Diseases 0.000 description 1
208000015124 ovarian disease Diseases 0.000 description 1
239000008363 phosphate buffer Substances 0.000 description 1
239000008055 phosphate buffer solution Substances 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000004237 preparative chromatography Methods 0.000 description 1
229940097325 prolactin Drugs 0.000 description 1
108010029020 prolylglycine Proteins 0.000 description 1
239000003223 protective agent Substances 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
239000013014 purified material Substances 0.000 description 1
239000012264 purified product Substances 0.000 description 1
108010087791 pyroglutamylhistidine Proteins 0.000 description 1
230000002829 reductive effect Effects 0.000 description 1
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150000003839 salts Chemical class 0.000 description 1
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230000021595 spermatogenesis Effects 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000003270 steroid hormone Substances 0.000 description 1
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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)

SE8304158A 1982-08-06 1983-07-27 Luteiniserings- och follikelstimulerande hormoner frigorande faktoranaloger med hog gonadotropisk verkan samt ett forfarande for framstellning derav SE456345B (sv)

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 (3)

Publication Number	Publication Date
SE8304158D0 SE8304158D0 (sv)	1983-07-27
SE8304158L SE8304158L (sv)	1984-02-07
SE456345B true SE456345B (sv)	1988-09-26

Family

ID=5404451

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
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

Country Status (14)

Country	Link
US (1)	US4512923A (de)
JP (1)	JPS5959654A (de)
AT (1)	AT387026B (de)
BE (1)	BE897455A (de)
CA (1)	CA1206959A (de)
CH (1)	CH658662A5 (de)
CS (1)	CS230614B1 (de)
DE (1)	DE3328235A1 (de)
FR (1)	FR2531952B1 (de)
GB (1)	GB2125408B (de)
HU (1)	HU192962B (de)
IT (1)	IT1165473B (de)
SE (1)	SE456345B (de)
YU (1)	YU45144B (de)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
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 (en)	1995-12-15	2008-10-14	Nobuyuki Takechi	Production of microspheres
CA2192773C (en)	1995-12-15	2008-09-23	Hiroaki Okada	Production of sustained-release preparation for injection
US5972895A (en) *	1996-12-11	1999-10-26	A. Glenn Braswell	Composition and method for increasing growth hormone levels

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* Cited by examiner, † Cited by third party
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CS180644B2 (en) *	1973-09-29	1978-01-31	Takeda Chemical Industries Ltd	Process for preparing nonapeptides
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 FR FR8312707A patent/FR2531952B1/fr not_active Expired
- 1983-08-02 IT IT22397/83A patent/IT1165473B/it active
- 1983-08-03 GB GB08320922A patent/GB2125408B/en not_active Expired
- 1983-08-03 BE BE0/211294A patent/BE897455A/fr unknown
- 1983-08-04 DE DE19833328235 patent/DE3328235A1/de not_active Ceased
- 1983-08-04 JP JP58141977A patent/JPS5959654A/ja active Pending
- 1983-08-05 HU HU832783A patent/HU192962B/hu unknown
- 1983-08-05 CH CH4271/83A patent/CH658662A5/de not_active IP Right Cessation
- 1983-08-05 YU YU1633/83A patent/YU45144B/xx unknown
- 1983-08-05 CA CA000434011A patent/CA1206959A/en not_active Expired
- 1983-08-08 US US06/521,108 patent/US4512923A/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
US4512923A (en)	1985-04-23
IT8322397A1 (it)	1985-02-02
FR2531952B1 (fr)	1988-07-22
JPS5959654A (ja)	1984-04-05
GB2125408A (en)	1984-03-07
BE897455A (fr)	1983-12-01
CH658662A5 (de)	1986-11-28
SE8304158D0 (sv)	1983-07-27
DE3328235A1 (de)	1984-04-05
AT387026B (de)	1988-11-25
CS230614B1 (en)	1984-08-13
YU163383A (en)	1986-06-30
GB8320922D0 (en)	1983-09-07
IT1165473B (it)	1987-04-22
HU192962B (en)	1987-08-28
ATA271583A (de)	1988-04-15
IT8322397A0 (it)	1983-08-02
CA1206959A (en)	1986-07-02
SE8304158L (sv)	1984-02-07
YU45144B (en)	1992-03-10
FR2531952A1 (fr)	1984-02-24
GB2125408B (en)	1986-06-18

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