JPS6330318B2 - - Google Patents
Info
- Publication number
- JPS6330318B2 JPS6330318B2 JP56098125A JP9812581A JPS6330318B2 JP S6330318 B2 JPS6330318 B2 JP S6330318B2 JP 56098125 A JP56098125 A JP 56098125A JP 9812581 A JP9812581 A JP 9812581A JP S6330318 B2 JPS6330318 B2 JP S6330318B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- oxytocin
- amino
- phenylalanine
- compound
- 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.)
- Expired
Links
- 150000001875 compounds Chemical class 0.000 claims description 28
- 238000004519 manufacturing process Methods 0.000 claims description 13
- XNOPRXBHLZRZKH-DSZYJQQASA-N oxytocin Chemical class C([C@H]1C(=O)N[C@H](C(N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CSSC[C@H](N)C(=O)N1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC(C)C)C(=O)NCC(N)=O)=O)[C@@H](C)CC)C1=CC=C(O)C=C1 XNOPRXBHLZRZKH-DSZYJQQASA-N 0.000 claims description 13
- MRNKEVGKBFIFET-AHCPCVRLSA-N (2s)-n-[(2s)-1-[(2-amino-2-oxoethyl)amino]-4-methyl-1-oxopentan-2-yl]-1-[(4s,7s,10s,16s)-7-(2-amino-2-oxoethyl)-10-(3-amino-3-oxopropyl)-13-[(2s)-butan-2-yl]-16-[(4-hydroxyphenyl)methyl]-6,9,12,15,18-pentaoxo-1-thia-5,8,11,14,17-pentazacycloicosane-4-carb Chemical compound C([C@H]1C(=O)NC(C(N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCSCCC(=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 MRNKEVGKBFIFET-AHCPCVRLSA-N 0.000 claims description 12
- 125000003277 amino group Chemical group 0.000 claims description 12
- 108700042417 deamino-6-carba- oxytocin Proteins 0.000 claims description 12
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical group OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 claims description 9
- 150000001413 amino acids Chemical class 0.000 claims description 9
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 claims description 9
- 238000006798 ring closing metathesis reaction Methods 0.000 claims description 9
- 150000002148 esters Chemical group 0.000 claims description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 7
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 4
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Chemical group O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 4
- 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 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- 239000011734 sodium Substances 0.000 claims description 3
- QBETWIZYARXLPZ-YFKPBYRVSA-N (2s)-2-amino-4-(2-carboxyethylsulfanyl)butanoic acid Chemical group OC(=O)[C@@H](N)CCSCCC(O)=O QBETWIZYARXLPZ-YFKPBYRVSA-N 0.000 claims description 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
- 230000003213 activating effect Effects 0.000 claims description 2
- 125000006239 protecting group Chemical group 0.000 claims description 2
- COLNVLDHVKWLRT-MRVPVSSYSA-N D-phenylalanine Chemical group OC(=O)[C@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-MRVPVSSYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 239000000047 product Substances 0.000 description 17
- 239000000243 solution Substances 0.000 description 11
- 239000000203 mixture Substances 0.000 description 10
- 229960001723 oxytocin Drugs 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- 238000002844 melting Methods 0.000 description 9
- 238000002523 gelfiltration Methods 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- 101800000989 Oxytocin Proteins 0.000 description 6
- 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 6
- 102100031951 Oxytocin-neurophysin 1 Human genes 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 6
- 238000004108 freeze drying Methods 0.000 description 6
- 230000001452 natriuretic effect Effects 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical class C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical class O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 230000004071 biological effect Effects 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- -1 2,4,5-trichlorophenyl ester Chemical class 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 230000001747 exhibiting effect Effects 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 108090000765 processed proteins & peptides Proteins 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- QCTLZQOZRYILCE-AWEZNQCLSA-N (2S)-3-(4-methyl-2-nitrophenyl)-2-(phenylsulfanylamino)propanoic acid Chemical compound [N+](=O)([O-])C1=C(C[C@H](NSC2=CC=CC=C2)C(=O)O)C=CC(=C1)C QCTLZQOZRYILCE-AWEZNQCLSA-N 0.000 description 1
- RMYPEYHEPIZYDJ-JTQLQIEISA-N (2s)-2-azaniumyl-3-(4-ethoxyphenyl)propanoate Chemical compound CCOC1=CC=C(C[C@H](N)C(O)=O)C=C1 RMYPEYHEPIZYDJ-JTQLQIEISA-N 0.000 description 1
- LVYWYLGWSVIFEV-ZDUSSCGKSA-N (2s)-3-(2-nitrophenyl)-2-(phenylsulfanylamino)propanoic acid Chemical compound C([C@@H](C(=O)O)NSC=1C=CC=CC=1)C1=CC=CC=C1[N+]([O-])=O LVYWYLGWSVIFEV-ZDUSSCGKSA-N 0.000 description 1
- RRONHWAVOYADJL-HNNXBMFYSA-N (2s)-3-phenyl-2-(phenylmethoxycarbonylamino)propanoic acid Chemical group C([C@@H](C(=O)O)NC(=O)OCC=1C=CC=CC=1)C1=CC=CC=C1 RRONHWAVOYADJL-HNNXBMFYSA-N 0.000 description 1
- LHJGJYXLEPZJPM-UHFFFAOYSA-N 2,4,5-trichlorophenol Chemical compound OC1=CC(Cl)=C(Cl)C=C1Cl LHJGJYXLEPZJPM-UHFFFAOYSA-N 0.000 description 1
- HTCSFFGLRQDZDE-UHFFFAOYSA-N 2-azaniumyl-2-phenylpropanoate Chemical compound OC(=O)C(N)(C)C1=CC=CC=C1 HTCSFFGLRQDZDE-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- JKPIMTGQMWPPHS-HNNXBMFYSA-N CCC1=CC(=C(C=C1)C[C@@H](C(=O)O)NSC2=CC=CC=C2)[N+](=O)[O-] Chemical compound CCC1=CC(=C(C=C1)C[C@@H](C(=O)O)NSC2=CC=CC=C2)[N+](=O)[O-] JKPIMTGQMWPPHS-HNNXBMFYSA-N 0.000 description 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 230000002686 anti-diuretic effect Effects 0.000 description 1
- GRDMQWRBLJZFML-UHFFFAOYSA-N bis(4-nitrophenyl) sulfite Chemical compound C1=CC([N+](=O)[O-])=CC=C1OS(=O)OC1=CC=C([N+]([O-])=O)C=C1 GRDMQWRBLJZFML-UHFFFAOYSA-N 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000007385 chemical modification Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000004064 dysfunction Effects 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 125000004185 ester group Chemical group 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
- 238000001997 free-flow electrophoresis Methods 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 238000001641 gel filtration chromatography Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- BEBCJVAWIBVWNZ-UHFFFAOYSA-N glycinamide Chemical compound NCC(N)=O BEBCJVAWIBVWNZ-UHFFFAOYSA-N 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
- 230000001965 increasing effect Effects 0.000 description 1
- 230000001983 lactogenic effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 239000013080 microcrystalline material Substances 0.000 description 1
- 239000000709 neurohypophysis hormone Substances 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
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229940068189 posterior pituitary hormone Drugs 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 125000001493 tyrosinyl group Chemical group [H]OC1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 description 1
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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Genetics & Genomics (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Life Sciences & Earth Sciences (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS804465A CS216722B1 (en) | 1980-06-24 | 1980-06-24 | Oxytocine analogues and method of making the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5753448A JPS5753448A (en) | 1982-03-30 |
| JPS6330318B2 true JPS6330318B2 (en, 2012) | 1988-06-17 |
Family
ID=5387463
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP56098125A Granted JPS5753448A (en) | 1980-06-24 | 1981-06-24 | Oxytocin analogue and manufacture |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS5753448A (en, 2012) |
| CA (1) | CA1179328A (en, 2012) |
| CH (1) | CH649090A5 (en, 2012) |
| CS (1) | CS216722B1 (en, 2012) |
| DE (1) | DE3124818A1 (en, 2012) |
| FR (1) | FR2485527B1 (en, 2012) |
| GB (1) | GB2078755B (en, 2012) |
| IT (1) | IT1136670B (en, 2012) |
| SE (1) | SE448303B (en, 2012) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2121052B (en) * | 1982-05-10 | 1985-08-14 | Ceskoslovenska Akademie Ved | Analogues of neurohypophysial hormones with inhibitory properties |
| JPS60198113A (ja) * | 1984-03-21 | 1985-10-07 | 松下電器産業株式会社 | 柑橘類の果汁絞り器 |
| JPS60166706U (ja) * | 1984-04-13 | 1985-11-06 | ナショナル住宅産業株式会社 | 外壁パネルの固定構造 |
| ZA87275B (en) * | 1986-01-16 | 1988-08-31 | Smithkline Beckman Corp | Polypeptide compounds |
| AT398767B (de) * | 1988-05-26 | 1995-01-25 | Gebro Broschek Gmbh | Verfahren zur reinigung eines rohpeptids mittels präparativer mitteldruckflüssigkeitschromatographie |
| US5225528A (en) * | 1990-02-27 | 1993-07-06 | Merck & Co., Inc. | Cyclic hexapeptide oxytocin antagonists |
| RU2125062C1 (ru) * | 1997-04-10 | 1999-01-20 | Государственный научный центр вирусологии и биотехнологии "Вектор" | Защищенные производные окситоцина |
| TWI463990B (zh) * | 2009-09-21 | 2014-12-11 | Ferring Bv | 催產素受體促進劑 |
| CN111454333B (zh) * | 2019-01-22 | 2023-06-27 | 南京济群医药科技股份有限公司 | 一种高纯度缩宫素的制备方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CS194980B1 (en) * | 1976-07-16 | 1979-12-31 | Joseph H Cort | Agent for current induction,fertilization facilitating and milkability increasing at mammals,especially at utility cattle |
-
1980
- 1980-06-24 CS CS804465A patent/CS216722B1/cs unknown
-
1981
- 1981-06-16 SE SE8103778A patent/SE448303B/sv not_active IP Right Cessation
- 1981-06-17 IT IT22390/81A patent/IT1136670B/it active
- 1981-06-18 GB GB8118815A patent/GB2078755B/en not_active Expired
- 1981-06-19 CH CH4086/81A patent/CH649090A5/de not_active IP Right Cessation
- 1981-06-23 CA CA000380428A patent/CA1179328A/en not_active Expired
- 1981-06-23 FR FR8112293A patent/FR2485527B1/fr not_active Expired
- 1981-06-24 DE DE19813124818 patent/DE3124818A1/de not_active Withdrawn
- 1981-06-24 JP JP56098125A patent/JPS5753448A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| GB2078755B (en) | 1984-01-18 |
| CA1179328A (en) | 1984-12-11 |
| FR2485527B1 (fr) | 1985-08-02 |
| JPS5753448A (en) | 1982-03-30 |
| CH649090A5 (de) | 1985-04-30 |
| FR2485527A1 (fr) | 1981-12-31 |
| IT8122390A0 (it) | 1981-06-17 |
| GB2078755A (en) | 1982-01-13 |
| DE3124818A1 (de) | 1982-04-08 |
| SE8103778L (sv) | 1981-12-25 |
| SE448303B (sv) | 1987-02-09 |
| CS216722B1 (en) | 1982-11-26 |
| IT1136670B (it) | 1986-09-03 |
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