FR2482093A1 - Nouveaux derives d'ocytocine et compositions pharmaceutiques contenant ces derives - Google Patents
Nouveaux derives d'ocytocine et compositions pharmaceutiques contenant ces derives Download PDFInfo
- Publication number
- FR2482093A1 FR2482093A1 FR8105751A FR8105751A FR2482093A1 FR 2482093 A1 FR2482093 A1 FR 2482093A1 FR 8105751 A FR8105751 A FR 8105751A FR 8105751 A FR8105751 A FR 8105751A FR 2482093 A1 FR2482093 A1 FR 2482093A1
- Authority
- FR
- France
- Prior art keywords
- oxytocin
- derivatives
- radical
- tyrosine
- contractions
- 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.)
- Granted
Links
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 9
- -1 RADICAL MERCAPTO Chemical class 0.000 claims abstract description 11
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims abstract description 4
- 150000003254 radicals Chemical class 0.000 claims abstract description 3
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 claims description 6
- 239000000654 additive Substances 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims description 3
- 229930195725 Mannitol Natural products 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 3
- 239000000594 mannitol Substances 0.000 claims description 3
- 235000010355 mannitol Nutrition 0.000 claims description 3
- 230000000996 additive effect Effects 0.000 claims description 2
- 239000012266 salt solution Substances 0.000 claims 1
- 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 abstract description 43
- 230000000694 effects Effects 0.000 abstract description 31
- 229960001723 oxytocin Drugs 0.000 abstract description 25
- 101800000989 Oxytocin Proteins 0.000 abstract description 20
- 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 abstract description 20
- 102100031951 Oxytocin-neurophysin 1 Human genes 0.000 abstract description 20
- 210000004291 uterus Anatomy 0.000 abstract description 17
- 208000036029 Uterine contractions during pregnancy Diseases 0.000 abstract description 10
- 230000002401 inhibitory effect Effects 0.000 abstract description 9
- 230000005764 inhibitory process Effects 0.000 abstract 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 abstract description 7
- 108010004977 Vasopressins Proteins 0.000 abstract description 7
- 102000002852 Vasopressins Human genes 0.000 abstract description 7
- 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 abstract description 7
- 229960003726 vasopressin Drugs 0.000 abstract description 7
- 230000002269 spontaneous effect Effects 0.000 abstract description 6
- 239000003814 drug Substances 0.000 abstract description 4
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 230000008602 contraction Effects 0.000 description 12
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 11
- 239000000556 agonist Substances 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 11
- 210000001519 tissue Anatomy 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 8
- 239000005557 antagonist Substances 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
- 238000002474 experimental method Methods 0.000 description 7
- 241000700159 Rattus Species 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 108090000765 processed proteins & peptides Proteins 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 229920005654 Sephadex Polymers 0.000 description 4
- 230000037396 body weight Effects 0.000 description 4
- 238000010586 diagram Methods 0.000 description 4
- 238000001727 in vivo Methods 0.000 description 4
- 239000003112 inhibitor Substances 0.000 description 4
- 210000000754 myometrium Anatomy 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- BJFIDCADFRDPIO-DZCXQCEKSA-N (2S)-N-[(2S)-6-amino-1-[(2-amino-2-oxoethyl)amino]-1-oxohexan-2-yl]-1-[[(4R,7S,10S,13S,16S,19R)-19-amino-7-(2-amino-2-oxoethyl)-10-(3-amino-3-oxopropyl)-16-[(4-hydroxyphenyl)methyl]-6,9,12,15,18-pentaoxo-13-(phenylmethyl)-1,2-dithia-5,8,11,14,17-pentazacycloeicos-4-yl]-oxomethyl]-2-pyrrolidinecarboxamide Chemical compound NCCCC[C@@H](C(=O)NCC(N)=O)NC(=O)[C@@H]1CCCN1C(=O)[C@H]1NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC=2C=CC=CC=2)NC(=O)[C@H](CC=2C=CC(O)=CC=2)NC(=O)[C@@H](N)CSSC1 BJFIDCADFRDPIO-DZCXQCEKSA-N 0.000 description 3
- BOLUZPBFHZSEQD-JTQLQIEISA-N (2s)-2-amino-3-(2-ethyl-4-hydroxyphenyl)propanoic acid Chemical compound CCC1=CC(O)=CC=C1C[C@H](N)C(O)=O BOLUZPBFHZSEQD-JTQLQIEISA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 238000012404 In vitro experiment Methods 0.000 description 3
- 108010048179 Lypressin Proteins 0.000 description 3
- 239000012507 Sephadex™ Substances 0.000 description 3
- 230000003042 antagnostic effect Effects 0.000 description 3
- 239000012634 fragment Substances 0.000 description 3
- 238000001802 infusion Methods 0.000 description 3
- 229960003837 lypressin Drugs 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 230000004118 muscle contraction Effects 0.000 description 3
- 210000000056 organ Anatomy 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- NDBNSZKHDMXOJE-UHFFFAOYSA-N 3-benzylsulfanylpropanoic acid Chemical compound OC(=O)CCSCC1=CC=CC=C1 NDBNSZKHDMXOJE-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
- 244000025254 Cannabis sativa Species 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 208000005171 Dysmenorrhea Diseases 0.000 description 2
- 206010013935 Dysmenorrhoea Diseases 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 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 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 125000003047 N-acetyl group Chemical group 0.000 description 2
- 208000002193 Pain Diseases 0.000 description 2
- 239000012891 Ringer solution Substances 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000001110 calcium chloride Substances 0.000 description 2
- 235000011148 calcium chloride Nutrition 0.000 description 2
- 229910001628 calcium chloride Inorganic materials 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 230000012173 estrus Effects 0.000 description 2
- 238000002523 gelfiltration Methods 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 210000003205 muscle Anatomy 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 230000036407 pain Effects 0.000 description 2
- 239000002504 physiological saline solution Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 230000000284 resting effect Effects 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- 230000003191 uterotonic effect Effects 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- LJRDOKAZOAKLDU-UDXJMMFXSA-N (2s,3s,4r,5r,6r)-5-amino-2-(aminomethyl)-6-[(2r,3s,4r,5s)-5-[(1r,2r,3s,5r,6s)-3,5-diamino-2-[(2s,3r,4r,5s,6r)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-hydroxycyclohexyl]oxy-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]oxyoxane-3,4-diol;sulfuric ac Chemical compound OS(O)(=O)=O.N[C@@H]1[C@@H](O)[C@H](O)[C@H](CN)O[C@@H]1O[C@H]1[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](N)C[C@@H](N)[C@@H]2O)O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)N)O[C@@H]1CO LJRDOKAZOAKLDU-UDXJMMFXSA-N 0.000 description 1
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- WPWHSFAFEBZWBB-UHFFFAOYSA-N 1-butyl radical Chemical compound [CH2]CCC WPWHSFAFEBZWBB-UHFFFAOYSA-N 0.000 description 1
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- 229940127291 Calcium channel antagonist Drugs 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 239000007836 KH2PO4 Substances 0.000 description 1
- 208000007101 Muscle Cramp Diseases 0.000 description 1
- 108010070873 Posterior Pituitary Hormones Proteins 0.000 description 1
- 102000005320 Posterior Pituitary Hormones Human genes 0.000 description 1
- 208000006399 Premature Obstetric Labor Diseases 0.000 description 1
- 206010036595 Premature delivery Diseases 0.000 description 1
- 206010036600 Premature labour Diseases 0.000 description 1
- 208000005392 Spasm Diseases 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 235000001014 amino acid Nutrition 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000035606 childbirth Effects 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000006957 competitive inhibition Effects 0.000 description 1
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 1
- 235000018417 cysteine Nutrition 0.000 description 1
- 125000000151 cysteine group Chemical group N[C@@H](CS)C(=O)* 0.000 description 1
- 230000009615 deamination Effects 0.000 description 1
- 238000006481 deamination reaction Methods 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229960004756 ethanol Drugs 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000009802 hysterectomy Methods 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 230000003821 menstrual periods Effects 0.000 description 1
- 230000005906 menstruation Effects 0.000 description 1
- XELZGAJCZANUQH-UHFFFAOYSA-N methyl 1-acetylthieno[3,2-c]pyrazole-5-carboxylate Chemical compound CC(=O)N1N=CC2=C1C=C(C(=O)OC)S2 XELZGAJCZANUQH-UHFFFAOYSA-N 0.000 description 1
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
- 235000019796 monopotassium phosphate Nutrition 0.000 description 1
- 229940094443 oxytocics prostaglandins Drugs 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 238000009595 pap smear Methods 0.000 description 1
- 229960001639 penicillamine Drugs 0.000 description 1
- 230000036470 plasma concentration Effects 0.000 description 1
- GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 208000026440 premature labor Diseases 0.000 description 1
- UFUASNAHBMBJIX-UHFFFAOYSA-N propan-1-one Chemical compound CC[C]=O UFUASNAHBMBJIX-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003180 prostaglandins Chemical class 0.000 description 1
- 239000000018 receptor agonist Substances 0.000 description 1
- 229940044601 receptor agonist Drugs 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 230000006965 reversible inhibition Effects 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 210000000952 spleen Anatomy 0.000 description 1
- 230000008925 spontaneous activity Effects 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- IDELNEDBPWKHGK-UHFFFAOYSA-N thiobutabarbital Chemical compound CCC(C)C1(CC)C(=O)NC(=S)NC1=O IDELNEDBPWKHGK-UHFFFAOYSA-N 0.000 description 1
- 239000003643 water by type Substances 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Biophysics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biochemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Reproductive Health (AREA)
- Endocrinology (AREA)
- Urology & Nephrology (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE8002222A SE430885B (sv) | 1980-03-24 | 1980-03-24 | Oxytocin-derivat |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2482093A1 true FR2482093A1 (fr) | 1981-11-13 |
| FR2482093B1 FR2482093B1 (OSRAM) | 1984-11-09 |
Family
ID=20340577
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8105751A Granted FR2482093A1 (fr) | 1980-03-24 | 1981-03-23 | Nouveaux derives d'ocytocine et compositions pharmaceutiques contenant ces derives |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US4402942A (OSRAM) |
| JP (1) | JPS56150050A (OSRAM) |
| BE (1) | BE887970A (OSRAM) |
| CH (1) | CH646139A5 (OSRAM) |
| DE (1) | DE3108323C2 (OSRAM) |
| FR (1) | FR2482093A1 (OSRAM) |
| GB (1) | GB2074582B (OSRAM) |
| IT (1) | IT1136574B (OSRAM) |
| NL (1) | NL8101191A (OSRAM) |
| SE (1) | SE430885B (OSRAM) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE8207277L (sv) * | 1982-12-21 | 1984-06-22 | Ferring Ab | Vasotocin-derivat |
| DE10075020I2 (de) * | 1982-12-21 | 2003-01-09 | Ferring Ab | Vasotocinderivate |
| US4483794A (en) * | 1983-05-10 | 1984-11-20 | Ceskoslovenska Akademie Ved | Analogs of neurohypophysial hormones |
| US4624943A (en) * | 1985-03-20 | 1986-11-25 | Smithkline Beckman Corporation | Aromatic basic-tailed vasopressin antagonists |
| US5225528A (en) * | 1990-02-27 | 1993-07-06 | Merck & Co., Inc. | Cyclic hexapeptide oxytocin antagonists |
| DE4042008A1 (de) * | 1990-12-22 | 1992-06-25 | Schering Ag | Vasopressin-derivate |
| US5830848A (en) * | 1992-10-09 | 1998-11-03 | The Regents Of The University Of California | Method and agents for inducement of endogenous nitric oxide synthase for control and management of labor during pregnancy |
| RU2125062C1 (ru) * | 1997-04-10 | 1999-01-20 | Государственный научный центр вирусологии и биотехнологии "Вектор" | Защищенные производные окситоцина |
| US6797845B1 (en) | 1999-11-22 | 2004-09-28 | Dow Global Technologies Inc. | Process for vinyl chloride manufacture from ethane and ethylene with immediate HCl recovery from reactor effluent |
| US6680415B1 (en) * | 1999-11-22 | 2004-01-20 | Dow Global Technologies Inc. | Oxyhalogenation process using catalyst having porous rare earth halide support |
| US6933417B1 (en) | 1999-11-22 | 2005-08-23 | Dow Global Technologies Inc. | Process for vinyl chloride manufacture from ethane and ethylene with partial CHl recovery from reactor effluent |
| US6909024B1 (en) * | 1999-11-22 | 2005-06-21 | The Dow Chemical Company | Process for the conversion of ethylene to vinyl chloride and novel catalyst compositions useful for such process |
| SE0100684D0 (sv) * | 2001-02-28 | 2001-02-28 | Kerstin Uvnaes Moberg | New subject-matter |
| KR100886284B1 (ko) * | 2001-05-23 | 2009-03-04 | 다우 글로벌 테크놀로지스 인크. | Ｃ3＋ 탄화수소의 산화성 할로겐화 및 임의의 탈수소화 |
| US20040152929A1 (en) * | 2002-05-08 | 2004-08-05 | Clarke William D | Process for vinyl chloride manufacture from ethane and ethylene with air feed and alternative hcl processing methods |
| US7722733B2 (en) | 2004-03-29 | 2010-05-25 | Baxter International Inc. | Method for sterile connection of tubing |
| TWI463990B (zh) * | 2009-09-21 | 2014-12-11 | Ferring Bv | 催產素受體促進劑 |
| CN107106641B (zh) | 2014-10-31 | 2021-12-21 | 葛兰素史密斯克莱知识产权发展有限公司 | 粉末制剂 |
| JP6933322B2 (ja) | 2016-01-04 | 2021-09-08 | メルク セローノ エス．エー． | ヒドロキシプロピルチアゾリジンカルボキサミド誘導体のｌ−バリネート及びその塩形態、結晶多形 |
| CA3031252A1 (en) | 2016-07-21 | 2018-01-25 | ObsEva S.A. | Oxytocin antagonist dosing regimens for promoting embryo implantation and preventing miscarriage |
| JP7390031B2 (ja) * | 2018-12-27 | 2023-12-01 | 国立大学法人金沢大学 | オキシトシン誘導体及びその使用 |
| KR20220075340A (ko) | 2019-09-03 | 2022-06-08 | 옵스에파 에스에이 | 배아 착상을 촉진하고 유산을 예방하기 위한 옥시토신 길항제 투여 요법 |
| AU2021218895A1 (en) | 2020-02-10 | 2022-09-15 | ObsEva S.A. | Biomarkers for oxytocin receptor antagonist therapy |
| EP4243817A1 (en) | 2020-11-16 | 2023-09-20 | Xoma (Us) Llc | Compositions and methods for the treatment or prevention of preterm labor |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1463865A (fr) * | 1964-07-27 | 1966-07-22 | Ceskoslovenska Akademie Ved | Procédé pour la préparation des dérivés cycliques de peptides ainsi que les produits conformes à ceux obtenus par le présent procédé ou procédé similaire |
| FR2358160A1 (fr) * | 1976-07-16 | 1978-02-10 | Ceskoslovenska Akademie Ved | Produit destine a declencher la parturition, a faciliter la fecondation et a augmenter la lactation chez la femme et chez les mammiferes, notamment le betail |
-
1980
- 1980-03-24 SE SE8002222A patent/SE430885B/sv not_active IP Right Cessation
-
1981
- 1981-02-27 US US06/238,715 patent/US4402942A/en not_active Expired - Fee Related
- 1981-03-03 CH CH140781A patent/CH646139A5/de not_active IP Right Cessation
- 1981-03-04 GB GB8106843A patent/GB2074582B/en not_active Expired
- 1981-03-05 DE DE3108323A patent/DE3108323C2/de not_active Expired
- 1981-03-11 NL NL8101191A patent/NL8101191A/nl not_active Application Discontinuation
- 1981-03-16 BE BE0/204141A patent/BE887970A/fr not_active IP Right Cessation
- 1981-03-23 JP JP4227581A patent/JPS56150050A/ja active Pending
- 1981-03-23 FR FR8105751A patent/FR2482093A1/fr active Granted
- 1981-03-24 IT IT20684/81A patent/IT1136574B/it active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1463865A (fr) * | 1964-07-27 | 1966-07-22 | Ceskoslovenska Akademie Ved | Procédé pour la préparation des dérivés cycliques de peptides ainsi que les produits conformes à ceux obtenus par le présent procédé ou procédé similaire |
| FR2358160A1 (fr) * | 1976-07-16 | 1978-02-10 | Ceskoslovenska Akademie Ved | Produit destine a declencher la parturition, a faciliter la fecondation et a augmenter la lactation chez la femme et chez les mammiferes, notamment le betail |
Non-Patent Citations (2)
| Title |
|---|
| CA1975 * |
| CA1981 * |
Also Published As
| Publication number | Publication date |
|---|---|
| SE8002222L (sv) | 1981-09-25 |
| JPS56150050A (en) | 1981-11-20 |
| GB2074582B (en) | 1983-07-06 |
| GB2074582A (en) | 1981-11-04 |
| DE3108323C2 (de) | 1983-11-24 |
| IT8120684A0 (it) | 1981-03-24 |
| FR2482093B1 (OSRAM) | 1984-11-09 |
| SE430885B (sv) | 1983-12-19 |
| CH646139A5 (de) | 1984-11-15 |
| BE887970A (fr) | 1981-07-16 |
| US4402942A (en) | 1983-09-06 |
| DE3108323A1 (de) | 1981-12-24 |
| IT1136574B (it) | 1986-09-03 |
| NL8101191A (nl) | 1981-10-16 |
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