SI8011553A8 - Postopek za pripravo nonapeptidnih in dekapeptidnih derivatov hormonov za sproščanje luteinizirajočega hormona - Google Patents
Postopek za pripravo nonapeptidnih in dekapeptidnih derivatov hormonov za sproščanje luteinizirajočega hormona Download PDFInfo
- Publication number
- SI8011553A8 SI8011553A8 SI8011553A SI8011553A SI8011553A8 SI 8011553 A8 SI8011553 A8 SI 8011553A8 SI 8011553 A SI8011553 A SI 8011553A SI 8011553 A SI8011553 A SI 8011553A SI 8011553 A8 SI8011553 A8 SI 8011553A8
- Authority
- SI
- Slovenia
- Prior art keywords
- naphthyl
- acid
- pyro
- alanyl
- ser
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 38
- 238000002360 preparation method Methods 0.000 title claims description 18
- 230000008569 process Effects 0.000 title claims description 15
- 239000000579 Gonadotropin-Releasing Hormone Substances 0.000 title abstract description 4
- 108700012941 GNRH1 Proteins 0.000 title 1
- 150000003839 salts Chemical class 0.000 claims abstract description 54
- 150000001875 compounds Chemical class 0.000 claims abstract description 46
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 claims abstract description 38
- -1 biphenylyl Chemical group 0.000 claims abstract description 37
- BEBCJVAWIBVWNZ-UHFFFAOYSA-N glycinamide Chemical compound NCC(N)=O BEBCJVAWIBVWNZ-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000002253 acid Substances 0.000 claims description 44
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 26
- 229920005989 resin Polymers 0.000 claims description 18
- 239000011347 resin Substances 0.000 claims description 18
- 239000007788 liquid Substances 0.000 claims description 11
- 239000007787 solid Substances 0.000 claims description 10
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 claims description 8
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 6
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 4
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 claims description 4
- MNCMBBIFTVWHIP-UHFFFAOYSA-N 1-anthracen-9-yl-2,2,2-trifluoroethanone Chemical group C1=CC=C2C(C(=O)C(F)(F)F)=C(C=CC=C3)C3=CC2=C1 MNCMBBIFTVWHIP-UHFFFAOYSA-N 0.000 claims description 3
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 3
- 102000009151 Luteinizing Hormone Human genes 0.000 claims description 2
- 108010073521 Luteinizing Hormone Proteins 0.000 claims description 2
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- 125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 claims description 2
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims description 2
- 229940040129 luteinizing hormone Drugs 0.000 claims description 2
- 238000007098 aminolysis reaction Methods 0.000 claims 1
- 239000012351 deprotecting agent Substances 0.000 claims 1
- 125000001998 leucyl group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 abstract description 20
- XLXSAKCOAKORKW-AQJXLSMYSA-N gonadorelin Chemical compound C([C@@H](C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N1[C@@H](CCC1)C(=O)NCC(N)=O)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@H]1NC(=O)CC1)C1=CC=C(O)C=C1 XLXSAKCOAKORKW-AQJXLSMYSA-N 0.000 abstract description 14
- 125000001624 naphthyl group Chemical group 0.000 abstract description 7
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 6
- 125000000753 cycloalkyl group Chemical group 0.000 abstract description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract description 4
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 abstract description 4
- 125000001153 fluoro group Chemical group F* 0.000 abstract description 4
- 239000001257 hydrogen Substances 0.000 abstract description 4
- 101000904177 Clupea pallasii Gonadoliberin-1 Proteins 0.000 abstract description 3
- 101000857870 Squalus acanthias Gonadoliberin Proteins 0.000 abstract description 3
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 abstract description 3
- 150000008574 D-amino acids Chemical group 0.000 abstract description 2
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 abstract description 2
- 239000000556 agonist Substances 0.000 abstract description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 2
- 125000001909 leucine group Chemical group [H]N(*)C(C(*)=O)C([H])([H])C(C([H])([H])[H])C([H])([H])[H] 0.000 abstract description 2
- 125000000430 tryptophan group Chemical group [H]N([H])C(C(=O)O*)C([H])([H])C1=C([H])N([H])C2=C([H])C([H])=C([H])C([H])=C12 0.000 abstract description 2
- 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 abstract description 2
- 125000000405 phenylalanyl group Chemical group 0.000 abstract 2
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 abstract 1
- 125000000741 isoleucyl group Chemical group [H]N([H])C(C(C([H])([H])[H])C([H])([H])C([H])([H])[H])C(=O)O* 0.000 abstract 1
- 125000005561 phenanthryl group Chemical group 0.000 abstract 1
- 230000003389 potentiating effect Effects 0.000 abstract 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 37
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 35
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 33
- 239000000243 solution Substances 0.000 description 33
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 24
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 21
- 229960003767 alanine Drugs 0.000 description 21
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 16
- 239000000460 chlorine Substances 0.000 description 16
- 239000000203 mixture Substances 0.000 description 16
- 102000004196 processed proteins & peptides Human genes 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 230000000694 effects Effects 0.000 description 14
- QNAYBMKLOCPYGJ-UHFFFAOYSA-N D-alpha-Ala Natural products CC([NH3+])C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-N 0.000 description 13
- 238000009472 formulation Methods 0.000 description 13
- 239000002244 precipitate Substances 0.000 description 13
- 229920001184 polypeptide Polymers 0.000 description 12
- QNAYBMKLOCPYGJ-UWTATZPHSA-N L-Alanine Natural products C[C@@H](N)C(O)=O QNAYBMKLOCPYGJ-UWTATZPHSA-N 0.000 description 10
- 244000000231 Sesamum indicum Species 0.000 description 10
- 229940024606 amino acid Drugs 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000003921 oil Substances 0.000 description 10
- 235000019198 oils Nutrition 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 235000001014 amino acid Nutrition 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- 238000002560 therapeutic procedure Methods 0.000 description 9
- 150000001413 amino acids Chemical class 0.000 description 8
- 229960000583 acetic acid Drugs 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- 229940088597 hormone Drugs 0.000 description 7
- 239000005556 hormone Substances 0.000 description 7
- 239000012071 phase Substances 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- 239000000052 vinegar Substances 0.000 description 7
- 235000021419 vinegar Nutrition 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 6
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
- 235000011054 acetic acid Nutrition 0.000 description 6
- 235000004279 alanine Nutrition 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 238000005859 coupling reaction Methods 0.000 description 6
- 239000007924 injection Substances 0.000 description 6
- 238000002347 injection Methods 0.000 description 6
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
- 230000016087 ovulation Effects 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 150000001408 amides Chemical class 0.000 description 5
- DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 description 5
- 230000008878 coupling Effects 0.000 description 5
- 238000010168 coupling process Methods 0.000 description 5
- 239000000499 gel Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 4
- 108010010803 Gelatin Proteins 0.000 description 4
- 229910004373 HOAc Inorganic materials 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 4
- HWDVTQAXQJQROO-UHFFFAOYSA-N cyclopropylazanide Chemical compound [NH-]C1CC1 HWDVTQAXQJQROO-UHFFFAOYSA-N 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 239000012530 fluid Substances 0.000 description 4
- 239000008273 gelatin Substances 0.000 description 4
- 229920000159 gelatin Polymers 0.000 description 4
- 235000019322 gelatine Nutrition 0.000 description 4
- 235000011852 gelatine desserts Nutrition 0.000 description 4
- 230000006698 induction Effects 0.000 description 4
- 208000000509 infertility Diseases 0.000 description 4
- 230000036512 infertility Effects 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- 125000006239 protecting group Chemical group 0.000 description 4
- 230000002829 reductive effect Effects 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- 238000007920 subcutaneous administration Methods 0.000 description 4
- MJIBOYFUEIDNPI-HBNMXAOGSA-L zinc 5-[2,3-dihydroxy-5-[(2R,3R,4S,5R,6S)-4,5,6-tris[[3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyl)oxybenzoyl]oxy]-2-[[3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyl)oxybenzoyl]oxymethyl]oxan-3-yl]oxycarbonylphenoxy]carbonyl-3-hydroxybenzene-1,2-diolate Chemical class [Zn++].Oc1cc(cc(O)c1O)C(=O)Oc1cc(cc(O)c1O)C(=O)OC[C@H]1O[C@@H](OC(=O)c2cc(O)c(O)c(OC(=O)c3cc(O)c(O)c(O)c3)c2)[C@H](OC(=O)c2cc(O)c(O)c(OC(=O)c3cc(O)c(O)c(O)c3)c2)[C@@H](OC(=O)c2cc(O)c(O)c(OC(=O)c3cc(O)c(O)c(O)c3)c2)[C@@H]1OC(=O)c1cc(O)c(O)c(OC(=O)c2cc(O)c([O-])c([O-])c2)c1 MJIBOYFUEIDNPI-HBNMXAOGSA-L 0.000 description 4
- KIPSRYDSZQRPEA-UHFFFAOYSA-N 2,2,2-trifluoroethanamine Chemical compound NCC(F)(F)F KIPSRYDSZQRPEA-UHFFFAOYSA-N 0.000 description 3
- 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 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 229910052788 barium Inorganic materials 0.000 description 3
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 3
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 229910017052 cobalt Inorganic materials 0.000 description 3
- 239000010941 cobalt Substances 0.000 description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 239000012458 free base Substances 0.000 description 3
- 231100000535 infertility Toxicity 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 229910052759 nickel Inorganic materials 0.000 description 3
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 3
- 210000002826 placenta Anatomy 0.000 description 3
- 239000000829 suppository Substances 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- 229910052725 zinc Inorganic materials 0.000 description 3
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 2
- TUSDEZXZIZRFGC-UHFFFAOYSA-N 1-O-galloyl-3,6-(R)-HHDP-beta-D-glucose Natural products OC1C(O2)COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC1C(O)C2OC(=O)C1=CC(O)=C(O)C(O)=C1 TUSDEZXZIZRFGC-UHFFFAOYSA-N 0.000 description 2
- OFYAYGJCPXRNBL-UHFFFAOYSA-N 2-azaniumyl-3-naphthalen-1-ylpropanoate Chemical compound C1=CC=C2C(CC(N)C(O)=O)=CC=CC2=C1 OFYAYGJCPXRNBL-UHFFFAOYSA-N 0.000 description 2
- RDIKFPRVLJLMER-BQBZGAKWSA-N Ala-Leu Chemical compound CC(C)C[C@@H](C(O)=O)NC(=O)[C@H](C)N RDIKFPRVLJLMER-BQBZGAKWSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 239000004475 Arginine Substances 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- 239000001263 FEMA 3042 Substances 0.000 description 2
- HKTRDWYCAUTRRL-YUMQZZPRSA-N Glu-His Chemical compound OC(=O)CC[C@H](N)C(=O)N[C@H](C(O)=O)CC1=CN=CN1 HKTRDWYCAUTRRL-YUMQZZPRSA-N 0.000 description 2
- 239000004471 Glycine Substances 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
- QNAYBMKLOCPYGJ-REOHCLBHSA-M L-alaninate Chemical compound C[C@H](N)C([O-])=O QNAYBMKLOCPYGJ-REOHCLBHSA-M 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 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
- 241000124008 Mammalia Species 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- LRBQNJMCXXYXIU-PPKXGCFTSA-N Penta-digallate-beta-D-glucose Natural products OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@@H]2[C@H]([C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-PPKXGCFTSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
- MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- MYVYPSWUSKCCHG-JQWIXIFHSA-N Trp-Ser Chemical compound C1=CC=C2C(C[C@H](N)C(=O)N[C@@H](CO)C(O)=O)=CNC2=C1 MYVYPSWUSKCCHG-JQWIXIFHSA-N 0.000 description 2
- 159000000021 acetate salts Chemical class 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 230000000274 adsorptive effect Effects 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- QNAYBMKLOCPYGJ-UHFFFAOYSA-M alaninate Chemical compound CC(N)C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-M 0.000 description 2
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 125000002837 carbocyclic group Chemical group 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- 230000004087 circulation Effects 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- MYRTYDVEIRVNKP-UHFFFAOYSA-N divinylbenzene Substances C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- 235000013399 edible fruits Nutrition 0.000 description 2
- 230000035558 fertility Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000011010 flushing procedure Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 150000004688 heptahydrates Chemical class 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 210000003016 hypothalamus Anatomy 0.000 description 2
- 201000001881 impotence Diseases 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 210000002414 leg Anatomy 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000001630 malic acid Substances 0.000 description 2
- 235000011090 malic acid Nutrition 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000004810 partition chromatography Methods 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
- 230000026234 pro-estrus Effects 0.000 description 2
- 229940092597 prolia Drugs 0.000 description 2
- 210000002307 prostate Anatomy 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000011669 selenium Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000008159 sesame oil Substances 0.000 description 2
- 235000011803 sesame oil Nutrition 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 230000001629 suppression Effects 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 235000015523 tannic acid Nutrition 0.000 description 2
- 229920002258 tannic acid Polymers 0.000 description 2
- LRBQNJMCXXYXIU-NRMVVENXSA-N tannic acid Chemical compound OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@@H]2[C@H]([C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-NRMVVENXSA-N 0.000 description 2
- 229940033123 tannic acid Drugs 0.000 description 2
- 239000011975 tartaric acid Substances 0.000 description 2
- 235000002906 tartaric acid Nutrition 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- RWQNBRDOKXIBIV-UHFFFAOYSA-N thymine Chemical compound CC1=CNC(=O)NC1=O RWQNBRDOKXIBIV-UHFFFAOYSA-N 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- 150000003751 zinc Chemical class 0.000 description 2
- IYLGZMTXKJYONK-ACLXAEORSA-N (12s,15r)-15-hydroxy-11,16-dioxo-15,20-dihydrosenecionan-12-yl acetate Chemical compound O1C(=O)[C@](CC)(O)C[C@@H](C)[C@](C)(OC(C)=O)C(=O)OCC2=CCN3[C@H]2[C@H]1CC3 IYLGZMTXKJYONK-ACLXAEORSA-N 0.000 description 1
- KHHIGWRTNILXLL-OAHLLOKOSA-N (2r)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-naphthalen-1-ylpropanoic acid Chemical compound C1=CC=C2C(C[C@@H](NC(=O)OC(C)(C)C)C(O)=O)=CC=CC2=C1 KHHIGWRTNILXLL-OAHLLOKOSA-N 0.000 description 1
- UJSYFXJFBPRSFQ-UHFFFAOYSA-N 1,1,2,2,2-pentafluoroethanamine Chemical compound NC(F)(F)C(F)(F)F UJSYFXJFBPRSFQ-UHFFFAOYSA-N 0.000 description 1
- BECXNUZQZGFCTL-UHFFFAOYSA-N 1,1,2,2,2-pentafluoroethylsilane Chemical compound [SiH3]C(C(F)(F)F)(F)F BECXNUZQZGFCTL-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- SFRUVBWDAJNXSB-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;but-1-enylbenzene Chemical compound CCC=CC1=CC=CC=C1.C=CC1=CC=CC=C1C=C SFRUVBWDAJNXSB-UHFFFAOYSA-N 0.000 description 1
- NZUJVPMLKRFSQS-UHFFFAOYSA-N 1,3,5-tributyl-2-(chloromethyl)benzene Chemical compound CCCCC1=CC(CCCC)=C(CCl)C(CCCC)=C1 NZUJVPMLKRFSQS-UHFFFAOYSA-N 0.000 description 1
- HIZVCIIORGCREW-UHFFFAOYSA-N 1,4-dioxene Chemical compound C1COC=CO1 HIZVCIIORGCREW-UHFFFAOYSA-N 0.000 description 1
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 1
- ZMYIIHDQURVDRB-UHFFFAOYSA-N 1-phenylethenylbenzene Chemical group C=1C=CC=CC=1C(=C)C1=CC=CC=C1 ZMYIIHDQURVDRB-UHFFFAOYSA-N 0.000 description 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- GHXNRYVDXNZXID-UHFFFAOYSA-N 2,2-diethylbutanoic acid Chemical compound CCC(CC)(CC)C(O)=O GHXNRYVDXNZXID-UHFFFAOYSA-N 0.000 description 1
- GLWFDTWIDROQIY-UHFFFAOYSA-N 2-amino-3-(9h-fluoren-2-yl)propanoic acid Chemical compound C1=CC=C2C3=CC=C(CC(N)C(O)=O)C=C3CC2=C1 GLWFDTWIDROQIY-UHFFFAOYSA-N 0.000 description 1
- IXSDAIHAHNXSEH-UHFFFAOYSA-N 2-amino-3-anthracen-2-ylpropanoic acid Chemical compound C1=CC=CC2=CC3=CC(CC(N)C(O)=O)=CC=C3C=C21 IXSDAIHAHNXSEH-UHFFFAOYSA-N 0.000 description 1
- JPZXHKDZASGCLU-UHFFFAOYSA-N 2-azaniumyl-3-naphthalen-2-ylpropanoate Chemical compound C1=CC=CC2=CC(CC(N)C(O)=O)=CC=C21 JPZXHKDZASGCLU-UHFFFAOYSA-N 0.000 description 1
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 1
- ODHCTXKNWHHXJC-VKHMYHEASA-N 5-oxo-L-proline Chemical compound OC(=O)[C@@H]1CCC(=O)N1 ODHCTXKNWHHXJC-VKHMYHEASA-N 0.000 description 1
- PBXYLMVLLSYZLN-UHFFFAOYSA-N 5beta-Ranol Natural products OC1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)CCO)C)C1(C)C(O)C2 PBXYLMVLLSYZLN-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- BSFODEXXVBBYOC-UHFFFAOYSA-N 8-[4-(dimethylamino)butan-2-ylamino]quinolin-6-ol Chemical compound C1=CN=C2C(NC(CCN(C)C)C)=CC(O)=CC2=C1 BSFODEXXVBBYOC-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 102000009027 Albumins Human genes 0.000 description 1
- 108010088751 Albumins Proteins 0.000 description 1
- LQJAALCCPOTJGB-YUMQZZPRSA-N Arg-Pro Chemical compound NC(N)=NCCC[C@H](N)C(=O)N1CCC[C@H]1C(O)=O LQJAALCCPOTJGB-YUMQZZPRSA-N 0.000 description 1
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 208000035484 Cellulite Diseases 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- 241000694440 Colpidium aqueous Species 0.000 description 1
- 206010011469 Crying Diseases 0.000 description 1
- 241000065675 Cyclops Species 0.000 description 1
- 206010011732 Cyst Diseases 0.000 description 1
- 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 description 1
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 1
- QIVBCDIJIAJPQS-SECBINFHSA-N D-tryptophane Chemical compound C1=CC=C2C(C[C@@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-SECBINFHSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 244000236655 Diospyros kaki Species 0.000 description 1
- 235000008597 Diospyros kaki Nutrition 0.000 description 1
- 102100025027 E3 ubiquitin-protein ligase TRIM69 Human genes 0.000 description 1
- UOACKFBJUYNSLK-XRKIENNPSA-N Estradiol Cypionate Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H](C4=CC=C(O)C=C4CC3)CC[C@@]21C)C(=O)CCC1CCCC1 UOACKFBJUYNSLK-XRKIENNPSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 1
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 1
- RGHNJXZEOKUKBD-SQOUGZDYSA-N Gluconic acid Natural products OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 1
- 201000005569 Gout Diseases 0.000 description 1
- 101000830203 Homo sapiens E3 ubiquitin-protein ligase TRIM69 Proteins 0.000 description 1
- 206010020880 Hypertrophy Diseases 0.000 description 1
- 206010062767 Hypophysitis Diseases 0.000 description 1
- 229920004459 Kel-F® PCTFE Polymers 0.000 description 1
- 125000003412 L-alanyl group Chemical group [H]N([H])[C@@](C([H])([H])[H])(C(=O)[*])[H] 0.000 description 1
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 description 1
- MRAUNPAHJZDYCK-BYPYZUCNSA-N L-nitroarginine Chemical compound OC(=O)[C@@H](N)CCCNC(=N)N[N+]([O-])=O MRAUNPAHJZDYCK-BYPYZUCNSA-N 0.000 description 1
- 125000003798 L-tyrosyl group Chemical group [H]N([H])[C@]([H])(C(=O)[*])C([H])([H])C1=C([H])C([H])=C(O[H])C([H])=C1[H] 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-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
- 241000721701 Lynx Species 0.000 description 1
- 101150051213 MAOA gene Proteins 0.000 description 1
- 241001068914 Melicope knudsenii Species 0.000 description 1
- 241001077660 Molo Species 0.000 description 1
- 241000237502 Ostreidae Species 0.000 description 1
- 241000282320 Panthera leo Species 0.000 description 1
- 206010049752 Peau d'orange Diseases 0.000 description 1
- 229920002230 Pectic acid Polymers 0.000 description 1
- 239000004264 Petrolatum Substances 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 229920000954 Polyglycolide Polymers 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 206010060862 Prostate cancer Diseases 0.000 description 1
- 208000004403 Prostatic Hyperplasia Diseases 0.000 description 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 description 1
- 235000011034 Rubus glaucus Nutrition 0.000 description 1
- 244000235659 Rubus idaeus Species 0.000 description 1
- 235000009122 Rubus idaeus Nutrition 0.000 description 1
- 235000012377 Salvia columbariae var. columbariae Nutrition 0.000 description 1
- 240000005481 Salvia hispanica Species 0.000 description 1
- 235000001498 Salvia hispanica Nutrition 0.000 description 1
- DYAHQFWOVKZOOW-UHFFFAOYSA-N Sarin Chemical compound CC(C)OP(C)(F)=O DYAHQFWOVKZOOW-UHFFFAOYSA-N 0.000 description 1
- 244000007853 Sarothamnus scoparius Species 0.000 description 1
- GMBQZIIUCVWOCD-WWASVFFGSA-N Sarsapogenine Chemical compound O([C@@H]1[C@@H]([C@]2(CC[C@@H]3[C@@]4(C)CC[C@H](O)C[C@H]4CC[C@H]3[C@@H]2C1)C)[C@@H]1C)[C@]11CC[C@H](C)CO1 GMBQZIIUCVWOCD-WWASVFFGSA-N 0.000 description 1
- 240000005499 Sasa Species 0.000 description 1
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 1
- 240000006394 Sorghum bicolor Species 0.000 description 1
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 1
- NHUHCSRWZMLRLA-UHFFFAOYSA-N Sulfisoxazole Chemical compound CC1=NOC(NS(=O)(=O)C=2C=CC(N)=CC=2)=C1C NHUHCSRWZMLRLA-UHFFFAOYSA-N 0.000 description 1
- 229920002253 Tannate Polymers 0.000 description 1
- 206010043183 Teething Diseases 0.000 description 1
- 241001255854 Teras Species 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
- 101150046432 Tril gene Proteins 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 description 1
- TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 description 1
- WLXDNZNRANJXCS-UHFFFAOYSA-N [B].[F].[F].[F] Chemical compound [B].[F].[F].[F] WLXDNZNRANJXCS-UHFFFAOYSA-N 0.000 description 1
- 239000004015 abortifacient agent Substances 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 229910000086 alane Inorganic materials 0.000 description 1
- 125000001980 alanyl group Chemical group 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
- 229960001126 alginic acid Drugs 0.000 description 1
- 150000004781 alginic acids Chemical class 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 125000002078 anthracen-1-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C([*])=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 125000000748 anthracen-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C([H])=C([*])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 230000002513 anti-ovulatory effect Effects 0.000 description 1
- 239000000427 antigen Substances 0.000 description 1
- 230000000890 antigenic effect Effects 0.000 description 1
- 102000036639 antigens Human genes 0.000 description 1
- 108091007433 antigens Proteins 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 230000003190 augmentative effect Effects 0.000 description 1
- WUPZNKGVDMHMBS-UHFFFAOYSA-N azane;dihydrate Chemical compound [NH4+].[NH4+].[OH-].[OH-] WUPZNKGVDMHMBS-UHFFFAOYSA-N 0.000 description 1
- 210000003323 beak Anatomy 0.000 description 1
- 230000006399 behavior Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- DFFDSQBEGQFJJU-UHFFFAOYSA-M butyl carbonate Chemical compound CCCCOC([O-])=O DFFDSQBEGQFJJU-UHFFFAOYSA-M 0.000 description 1
- 210000004899 c-terminal region Anatomy 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
- 235000013539 calcium stearate Nutrition 0.000 description 1
- 239000008116 calcium stearate Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 230000036232 cellulite Effects 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 235000014167 chia Nutrition 0.000 description 1
- UUAGAQFQZIEFAH-UHFFFAOYSA-N chlorotrifluoroethylene Chemical compound FC(F)=C(F)Cl UUAGAQFQZIEFAH-UHFFFAOYSA-N 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- OTAFHZMPRISVEM-UHFFFAOYSA-N chromone Chemical compound C1=CC=C2C(=O)C=COC2=C1 OTAFHZMPRISVEM-UHFFFAOYSA-N 0.000 description 1
- ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 239000003433 contraceptive agent Substances 0.000 description 1
- 230000002254 contraceptive effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013256 coordination polymer Substances 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 239000013058 crude material Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 150000001913 cyanates Chemical class 0.000 description 1
- WVIIMZNLDWSIRH-UHFFFAOYSA-N cyclohexylcyclohexane Chemical group C1CCCCC1C1CCCCC1 WVIIMZNLDWSIRH-UHFFFAOYSA-N 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- OZYHLCOUAISLLG-UHFFFAOYSA-N cyclopropyl acetate Chemical compound CC(=O)OC1CC1 OZYHLCOUAISLLG-UHFFFAOYSA-N 0.000 description 1
- 208000031513 cyst Diseases 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- 238000009795 derivation Methods 0.000 description 1
- 230000027046 diestrus Effects 0.000 description 1
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
- MGHPNCMVUAKAIE-UHFFFAOYSA-N diphenylmethanamine Chemical compound C=1C=CC=CC=1C(N)C1=CC=CC=C1 MGHPNCMVUAKAIE-UHFFFAOYSA-N 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- ODCCJTMPMUFERV-UHFFFAOYSA-N ditert-butyl carbonate Chemical compound CC(C)(C)OC(=O)OC(C)(C)C ODCCJTMPMUFERV-UHFFFAOYSA-N 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000006196 drop Substances 0.000 description 1
- 238000007908 dry granulation Methods 0.000 description 1
- 210000005069 ears Anatomy 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000011067 equilibration Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000012173 estrus Effects 0.000 description 1
- HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 description 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- RZTAMFZIAATZDJ-UHFFFAOYSA-N felodipine Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1C1=CC=CC(Cl)=C1Cl RZTAMFZIAATZDJ-UHFFFAOYSA-N 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- MUJOIMFVNIBMKC-UHFFFAOYSA-N fludioxonil Chemical compound C=12OC(F)(F)OC2=CC=CC=1C1=CNC=C1C#N MUJOIMFVNIBMKC-UHFFFAOYSA-N 0.000 description 1
- 230000004907 flux Effects 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000000174 gluconic acid Substances 0.000 description 1
- 235000012208 gluconic acid Nutrition 0.000 description 1
- 229930182470 glycoside Natural products 0.000 description 1
- 150000002338 glycosides Chemical class 0.000 description 1
- 230000002710 gonadal effect Effects 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 1
- 235000012907 honey Nutrition 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
- 230000002209 hydrophobic effect Effects 0.000 description 1
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 239000012678 infectious agent Substances 0.000 description 1
- 231100000546 inhibition of ovulation Toxicity 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 239000003407 interleukin 1 receptor blocking agent Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000004255 ion exchange chromatography Methods 0.000 description 1
- 238000005040 ion trap Methods 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 210000003127 knee Anatomy 0.000 description 1
- 238000009940 knitting Methods 0.000 description 1
- 108010034602 l-phenylalanyl sarcosine Proteins 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 230000001665 lethal effect Effects 0.000 description 1
- 239000006193 liquid solution Substances 0.000 description 1
- 239000006194 liquid suspension Substances 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 230000000938 luteal effect Effects 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 235000013575 mashed potatoes Nutrition 0.000 description 1
- 230000035800 maturation Effects 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 229910000372 mercury(II) sulfate Inorganic materials 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- GFQKFGQPVBTZOV-UHFFFAOYSA-N n-ethyl-2,2,2-trifluoroethanamine Chemical compound CCNCC(F)(F)F GFQKFGQPVBTZOV-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- YZMHQCWXYHARLS-UHFFFAOYSA-N naphthalene-1,2-disulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(S(=O)(=O)O)=CC=C21 YZMHQCWXYHARLS-UHFFFAOYSA-N 0.000 description 1
- KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 1
- 239000007923 nasal drop Substances 0.000 description 1
- 229940100662 nasal drops Drugs 0.000 description 1
- 239000005445 natural material Substances 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- SPIFDSWFDKNERT-UHFFFAOYSA-N nickel;hydrate Chemical compound O.[Ni] SPIFDSWFDKNERT-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000011275 oncology therapy Methods 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 208000025661 ovarian cyst Diseases 0.000 description 1
- 230000000624 ovulatory effect Effects 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 235000020636 oyster Nutrition 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
- 210000003254 palate Anatomy 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 230000000803 paradoxical effect Effects 0.000 description 1
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 1
- 230000001175 peptic effect Effects 0.000 description 1
- 238000010647 peptide synthesis reaction Methods 0.000 description 1
- 230000003836 peripheral circulation Effects 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 229940066842 petrolatum Drugs 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229960005382 phenolphthalein Drugs 0.000 description 1
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 210000003635 pituitary gland Anatomy 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000010318 polygalacturonic acid Substances 0.000 description 1
- 229920002643 polyglutamic acid Polymers 0.000 description 1
- 239000004633 polyglycolic acid Substances 0.000 description 1
- 150000007519 polyprotic acids Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- GRJJQCWNZGRKAU-UHFFFAOYSA-N pyridin-1-ium;fluoride Chemical compound F.C1=CC=NC=C1 GRJJQCWNZGRKAU-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000011514 reflex Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001850 reproductive effect Effects 0.000 description 1
- IYLGZMTXKJYONK-UHFFFAOYSA-N ruwenine Natural products O1C(=O)C(CC)(O)CC(C)C(C)(OC(C)=O)C(=O)OCC2=CCN3C2C1CC3 IYLGZMTXKJYONK-UHFFFAOYSA-N 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 238000012163 sequencing technique Methods 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 238000005549 size reduction Methods 0.000 description 1
- CBXWGGFGZDVPNV-UHFFFAOYSA-N so4-so4 Chemical compound OS(O)(=O)=O.OS(O)(=O)=O CBXWGGFGZDVPNV-UHFFFAOYSA-N 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- OTNVGWMVOULBFZ-UHFFFAOYSA-N sodium;hydrochloride Chemical compound [Na].Cl OTNVGWMVOULBFZ-UHFFFAOYSA-N 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 238000010532 solid phase synthesis reaction Methods 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- FZUJWWOKDIGOKH-UHFFFAOYSA-N sulfuric acid hydrochloride Chemical compound Cl.OS(O)(=O)=O FZUJWWOKDIGOKH-UHFFFAOYSA-N 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 230000000153 supplemental effect Effects 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 239000007916 tablet composition Substances 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 210000001550 testis Anatomy 0.000 description 1
- 229960003604 testosterone Drugs 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000010257 thawing Methods 0.000 description 1
- 229940113082 thymine Drugs 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 230000036346 tooth eruption Effects 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000759 toxicological effect Toxicity 0.000 description 1
- HSTZMXCBWJGKHG-CUYWLFDKSA-N trans-piceid Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(\C=C\C=2C=CC(O)=CC=2)=C1 HSTZMXCBWJGKHG-CUYWLFDKSA-N 0.000 description 1
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- MYMLGBAVNHFRJS-UHFFFAOYSA-N trifluoromethanamine Chemical compound NC(F)(F)F MYMLGBAVNHFRJS-UHFFFAOYSA-N 0.000 description 1
- 238000009966 trimming Methods 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 235000002374 tyrosine Nutrition 0.000 description 1
- 229940116269 uric acid Drugs 0.000 description 1
- 210000001215 vagina Anatomy 0.000 description 1
- 238000011121 vaginal smear Methods 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 230000007332 vesicle formation Effects 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 238000005550 wet granulation Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- MBMQEIFVQACCCH-QBODLPLBSA-N zearalenone Chemical compound O=C1O[C@@H](C)CCCC(=O)CCC\C=C\C2=CC(O)=CC(O)=C21 MBMQEIFVQACCCH-QBODLPLBSA-N 0.000 description 1
- 229910000859 α-Fe Inorganic materials 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
- C07K7/06—Linear peptides containing only normal peptide links having 5 to 11 amino acids
-
- 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
- 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
- Y10S930/12—Growth hormone, growth factor other than t-cell or b-cell growth factor, and growth hormone releasing factor; 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
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biophysics (AREA)
- Biochemistry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Molecular Biology (AREA)
- Endocrinology (AREA)
- Genetics & Genomics (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Diabetes (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/047,661 US4234571A (en) | 1979-06-11 | 1979-06-11 | Nonapeptide and decapeptide derivatives of luteinizing hormone releasing hormone |
| FR7927754A FR2458538A1 (fr) | 1979-06-11 | 1979-11-09 | Derives nonapeptidiques et decapeptidiques de l'hormone liberant l'hormone luteinisante, leur procede de production et composition pharmaceutique les contenant |
| YU1553/80A YU42217B (en) | 1979-06-11 | 1980-06-11 | Process for obtaining nonapeptidic and decapeptidic derivatives of hormone for releasing luteinisating hormone |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SI8011553A8 true SI8011553A8 (sl) | 1998-02-28 |
Family
ID=21950237
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SI8011553A SI8011553A8 (sl) | 1979-06-11 | 1980-06-11 | Postopek za pripravo nonapeptidnih in dekapeptidnih derivatov hormonov za sproščanje luteinizirajočega hormona |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4234571A (OSRAM) |
| JP (3) | JPS55164663A (OSRAM) |
| KR (1) | KR840001921B1 (OSRAM) |
| AT (1) | ATE9089T1 (OSRAM) |
| FR (1) | FR2458538A1 (OSRAM) |
| HU (1) | HU185379B (OSRAM) |
| LU (1) | LU88272I2 (OSRAM) |
| MX (1) | MX9203594A (OSRAM) |
| NO (1) | NO1994006I1 (OSRAM) |
| SI (1) | SI8011553A8 (OSRAM) |
| SU (2) | SU1681733A3 (OSRAM) |
| ZA (1) | ZA803453B (OSRAM) |
Families Citing this family (77)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2465486A1 (fr) * | 1979-09-21 | 1981-03-27 | Roussel Uclaf | Nouvelle application utilisant la lh-rh ou des agonistes |
| US5389613A (en) * | 1979-09-21 | 1995-02-14 | Roussel Uclaf | Method of treating prostate adenocarcinoma, prostate benign hypertrophia and endometriosis |
| US4409208A (en) * | 1980-04-15 | 1983-10-11 | The Salk Institute For Biological Studies | GnRH antagonists |
| WO1982000004A1 (en) * | 1980-06-26 | 1982-01-07 | Salk Inst For Biological Studi | Contraceptive treatment of male mammals |
| US4382922A (en) * | 1980-08-29 | 1983-05-10 | The Salk Institute For Biological Studies | Peptides affecting gonadal function |
| US4419347A (en) * | 1980-10-06 | 1983-12-06 | Syntex (U.S.A.) Inc. | Nonapeptide and decapeptide analogs of LHRH, useful as LHRH antagonists |
| US4341767A (en) * | 1980-10-06 | 1982-07-27 | Syntex Inc. | Nonapeptide and decapeptide analogs of LHRH, useful as LHRH antagonists |
| PH19942A (en) * | 1980-11-18 | 1986-08-14 | Sintex Inc | Microencapsulation of water soluble polypeptides |
| US4675189A (en) * | 1980-11-18 | 1987-06-23 | Syntex (U.S.A.) Inc. | Microencapsulation of water soluble active polypeptides |
| US5366734A (en) * | 1981-02-16 | 1994-11-22 | Zeneca Limited | Continuous release pharmaceutical compositions |
| IE52535B1 (en) * | 1981-02-16 | 1987-12-09 | Ici Plc | Continuous release pharmaceutical compositions |
| JPS58125819U (ja) * | 1982-02-19 | 1983-08-26 | 名伸電機株式会社 | 積算電力量計用パツキン |
| HU185535B (en) * | 1982-05-25 | 1985-02-28 | Mta Koezponti Hivatala | Process for preparing new gonadoliberin derivatives |
| US4619914A (en) * | 1983-03-10 | 1986-10-28 | The Salk Institute For Biological Studies | GNRH antagonists IIIB |
| CH661206A5 (fr) * | 1983-09-23 | 1987-07-15 | Debiopharm Sa | Procede pour la preparation d'un medicament destine au traitement de maladies hormonodependantes. |
| JPS60100516A (ja) * | 1983-11-04 | 1985-06-04 | Takeda Chem Ind Ltd | 徐放型マイクロカプセルの製造法 |
| US4547370A (en) * | 1983-11-29 | 1985-10-15 | The Salk Institute For Biological Studies | GnRH Antagonists |
| US4652550A (en) * | 1984-05-21 | 1987-03-24 | The Salk Institute For Biological Studies | GnRH antagonists VII |
| US4632979A (en) * | 1984-06-18 | 1986-12-30 | Tulane Educational Fund | Therapeutic LHRH analogs |
| US4760053A (en) * | 1984-08-02 | 1988-07-26 | Fernand Labrie | Combination therapy for selected sex steroid dependent cancers |
| US4565804A (en) * | 1984-09-07 | 1986-01-21 | The Salk Institute For Biological Studies | GnRH Antagonists VI |
| EP0181110A3 (en) * | 1984-10-22 | 1988-05-11 | Kissei Pharmaceutical Co. Ltd. | Histidine derivatives as renin inhibitors |
| DE3445669A1 (de) * | 1984-12-14 | 1986-06-19 | Boehringer Mannheim Gmbh, 6800 Mannheim | Neue pyrrolo-benzimidazole, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| EP0190891A3 (en) * | 1985-01-31 | 1988-04-20 | Kissei Pharmaceutical Co. Ltd. | Novel amino acid derivatives |
| ATE61935T1 (de) * | 1985-02-07 | 1991-04-15 | Takeda Chemical Industries Ltd | Verfahren zur herstellung von mikrokapseln. |
| US4642332A (en) * | 1985-04-26 | 1987-02-10 | The Board Of Regents, The University Of Texas System | Effective hormonal peptides: D-3-Pal6 -LHRH |
| US4656247A (en) * | 1985-04-26 | 1987-04-07 | Board Of Regents, The University Of Texas System | Effective hormonal peptides: D-3-QA1 6-LHRH |
| EP0206807A3 (en) * | 1985-06-28 | 1988-01-20 | Kissei Pharmaceutical Co. Ltd. | Novel amino acid derivatives |
| US4853463A (en) * | 1985-09-04 | 1989-08-01 | Kissei Pharmaceutical Co., Ltd. | Amino acid derivatives |
| 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 |
| JPS6322081A (ja) * | 1986-07-11 | 1988-01-29 | Kissei Pharmaceut Co Ltd | 新規なアミノ酸誘導体 |
| US4761398A (en) * | 1986-08-18 | 1988-08-02 | Embrex, Inc. | Method of inducing birds to molt |
| US5028430A (en) * | 1987-05-08 | 1991-07-02 | Syntex (U.S.A.) Inc. | Delivery systems for the controlled administration of LHRH analogs |
| US4897268A (en) * | 1987-08-03 | 1990-01-30 | Southern Research Institute | Drug delivery system and method of making the same |
| NZ228285A (en) * | 1988-03-11 | 1991-08-27 | Teikoku Seiyaku Kk | Pharmaceutical composition comprising a polypeptide and adapted for intravaginal administration |
| JP2672677B2 (ja) * | 1989-02-09 | 1997-11-05 | タツプ・フアーマシユーテイカルズ・インコーポレイテツド | Lhrh同族体 |
| JPH02235975A (ja) * | 1989-03-09 | 1990-09-18 | Masaya Takinami | 粘着シート |
| US6156731A (en) * | 1989-05-10 | 2000-12-05 | G. D. Searle & Co. | Polypeptide composition for oral administration |
| US5232707A (en) * | 1989-07-10 | 1993-08-03 | Syntex (U.S.A.) Inc. | Solvent extraction process |
| JP2911496B2 (ja) * | 1989-09-11 | 1999-06-23 | 帝國製薬株式会社 | 生理活性ポリペプチド含有高吸収性経膣剤 |
| US5169932A (en) * | 1989-10-30 | 1992-12-08 | The Salk Institute For Biological Studies | Gnrh analogs |
| US5580957A (en) * | 1989-10-30 | 1996-12-03 | The Salk Institute For Biological Studies | GnRH analogs |
| JP2653255B2 (ja) | 1990-02-13 | 1997-09-17 | 武田薬品工業株式会社 | 長期徐放型マイクロカプセル |
| US5212288A (en) * | 1990-02-20 | 1993-05-18 | Syntex (U.S.A.) Inc. | Temporary minimal protection synthesis of serine-containing polypeptides |
| US6353030B1 (en) | 1990-08-01 | 2002-03-05 | Novartis Ag | Relating to organic compounds |
| JPH05117604A (ja) * | 1990-11-01 | 1993-05-14 | Koopack Kk | 粘着シールによる表示製品 |
| US5744450A (en) | 1991-03-14 | 1998-04-28 | The Salk Institute For Biological Studies | GnRH analogs |
| IL101074A (en) * | 1991-03-14 | 1997-09-30 | Salk Inst For Biological Studi | GnRH ANALOGS AND THEIR PREPARATION |
| DE4117507A1 (de) * | 1991-05-24 | 1992-11-26 | Schering Ag | Verfahren zur herstellung von n(pfeil hoch)6(pfeil hoch)-substituierten lysin-derivaten |
| US5518730A (en) | 1992-06-03 | 1996-05-21 | Fuisz Technologies Ltd. | Biodegradable controlled release flash flow melt-spun delivery system |
| TW333456B (en) * | 1992-12-07 | 1998-06-11 | Takeda Pharm Ind Co Ltd | A pharmaceutical composition of sustained-release preparation the invention relates to a pharmaceutical composition of sustained-release preparation which comprises a physiologically active peptide. |
| CA2192773C (en) | 1995-12-15 | 2008-09-23 | Hiroaki Okada | Production of sustained-release preparation for injection |
| CA2192782C (en) | 1995-12-15 | 2008-10-14 | Nobuyuki Takechi | Production of microspheres |
| WO1999007874A1 (en) * | 1996-06-13 | 1999-02-18 | Itoham Foods Inc. | Process for producing lh-rh derivatives |
| US5916582A (en) * | 1996-07-03 | 1999-06-29 | Alza Corporation | Aqueous formulations of peptides |
| US6458357B1 (en) * | 1997-09-09 | 2002-10-01 | Myelos Corporation | Retro-inverso neurotrophic and analgesic peptides |
| US6242421B1 (en) | 1997-11-06 | 2001-06-05 | Richard Lloyd Bowen | Methods for preventing and treating Alzheimer's disease |
| US6117441A (en) * | 1998-07-02 | 2000-09-12 | The Population Council, Inc. | Silicone core long term androgen delivery implant |
| US7112341B1 (en) | 1999-04-13 | 2006-09-26 | Nektar Therapeutics | Pulmonary administration of dry powder formulations for treating infertility |
| US20040241842A1 (en) * | 1999-04-15 | 2004-12-02 | Monash University | Stimulation of thymus for vaccination development |
| US20070274946A1 (en) * | 1999-04-15 | 2007-11-29 | Norwood Immunoloty, Ltd. | Tolerance to Graft Prior to Thymic Reactivation |
| US20050020524A1 (en) * | 1999-04-15 | 2005-01-27 | Monash University | Hematopoietic stem cell gene therapy |
| AUPR074500A0 (en) * | 2000-10-13 | 2000-11-09 | Monash University | Treatment of t cell disorders |
| US20040265285A1 (en) * | 1999-04-15 | 2004-12-30 | Monash University | Normalization of defective T cell responsiveness through manipulation of thymic regeneration |
| US20040259803A1 (en) * | 1999-04-15 | 2004-12-23 | Monash University | Disease prevention by reactivation of the thymus |
| AR023940A1 (es) | 2000-05-03 | 2002-09-04 | Eriochem Sa | Procedimiento para la produccion de microcapsulas de liberacion prolongada de peptidos solubles en agua |
| US20060088512A1 (en) * | 2001-10-15 | 2006-04-27 | Monash University | Treatment of T cell disorders |
| US20060287282A1 (en) * | 2001-06-25 | 2006-12-21 | Steiner Mitchell S | Compositions comprising a SARM ad GnRH agonist or a GnRH antagonist, and methods of use thereof |
| EP1444988A4 (en) | 2001-11-13 | 2007-04-25 | Takeda Pharmaceutical | CANCER AGENT |
| US20030144203A1 (en) * | 2001-12-19 | 2003-07-31 | Voyager Pharmaceutical Corporation | Methods for slowing senescence and treating and preventing diseases associated with senescence |
| GB0307777D0 (en) * | 2003-04-04 | 2003-05-07 | Medical Res Council | Conjugate compounds |
| AU2004235744A1 (en) * | 2003-05-01 | 2004-11-18 | Archimedes Development Limited | Nasal administration of the LH-RH analog leuprolide |
| GB0320806D0 (en) | 2003-09-05 | 2003-10-08 | Astrazeneca Ab | Therapeutic treatment |
| US20080279812A1 (en) * | 2003-12-05 | 2008-11-13 | Norwood Immunology, Ltd. | Disease Prevention and Vaccination Prior to Thymic Reactivation |
| RU2522634C2 (ru) * | 2012-07-31 | 2014-07-20 | Общество с ограниченной ответственностью "Научно-производственное предприятие "ИнБио Текс" | Способ получения трудногорючих полимерных изделий на основе полиэтилентерефталата с биоцидными свойствами |
| WO2021110609A1 (en) * | 2019-12-05 | 2021-06-10 | Bcn Peptides, S.A. | Peptides for the treatment of cancer and/or metastasis |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5314072B2 (OSRAM) * | 1973-09-29 | 1978-05-15 | ||
| JPS5726506B2 (OSRAM) * | 1974-03-08 | 1982-06-04 | ||
| JPS50142563A (OSRAM) * | 1974-04-26 | 1975-11-17 | ||
| DE2438350C3 (de) * | 1974-08-09 | 1979-06-13 | Hoechst Ag, 6000 Frankfurt | Peptide mit starker LH-RH/FSH-RH-Wirkung, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Zubereitungen |
| US4018726A (en) * | 1975-06-12 | 1977-04-19 | Andrew Victor Schally | [D-Phe6 ]-LH-RH and intermediates therefor |
| US4010125A (en) * | 1975-06-12 | 1977-03-01 | Schally Andrew Victor | [D-Trp6 ]-LH-RH and intermediates therefor |
| NZ181036A (en) * | 1975-06-12 | 1978-12-18 | A Schally | Luteinising hormone releasing hormone analogues and intermediates therefor |
| US4005194A (en) * | 1975-06-23 | 1977-01-25 | Abbott Laboratories | Treatment of prostatic hyperplasia |
| GB1542703A (en) * | 1975-10-29 | 1979-03-21 | Parke Davis & Co | Nonapeptides and methods for their production |
| US3992530A (en) * | 1975-12-08 | 1976-11-16 | American Home Products Corporation | [D-2-(1,4-Cyclohexadienyl)gly]6 -des-gly10 -lrh nonapeptide amides |
| US4071622A (en) * | 1976-02-11 | 1978-01-31 | Abbott Laboratories | Treatment of a mammary or DMBA inducible tumor |
| DE2617646C2 (de) * | 1976-04-22 | 1986-07-31 | Hoechst Ag, 6230 Frankfurt | Nonapeptid-amide und Decapeptid-amide mit Gonadoliberin-Wirkung, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende pharmazeutische Präparate |
| GB1524747A (en) * | 1976-05-11 | 1978-09-13 | Ici Ltd | Polypeptide |
| US4089946A (en) * | 1976-06-07 | 1978-05-16 | American Home Products Corporation | Claudogenic-interceptive nonapeptides |
| US4143133A (en) * | 1977-10-03 | 1979-03-06 | American Home Products Corporation | Claudogenic-interceptive nonapeptides |
| JPS5855137B2 (ja) * | 1977-10-07 | 1983-12-08 | 武田薬品工業株式会社 | ポリペプチドの製造法 |
-
1979
- 1979-06-11 US US06/047,661 patent/US4234571A/en not_active Expired - Lifetime
- 1979-11-09 FR FR7927754A patent/FR2458538A1/fr active Granted
- 1979-11-10 JP JP14595879A patent/JPS55164663A/ja active Granted
-
1980
- 1980-06-10 LU LU88272C patent/LU88272I2/xx unknown
- 1980-06-10 HU HU801458A patent/HU185379B/hu unknown
- 1980-06-10 ZA ZA00803453A patent/ZA803453B/xx unknown
- 1980-06-10 AT AT80103222T patent/ATE9089T1/de active
- 1980-06-10 SU SU802929801A patent/SU1681733A3/ru active
- 1980-06-10 KR KR1019800002276A patent/KR840001921B1/ko not_active Expired
- 1980-06-11 SI SI8011553A patent/SI8011553A8/sl unknown
-
1983
- 1983-05-30 SU SU833597664A patent/SU1428205A3/ru active
-
1988
- 1988-02-25 JP JP63043256A patent/JPS63264498A/ja active Granted
- 1988-06-15 JP JP63145979A patent/JPS6425794A/ja active Granted
-
1992
- 1992-06-26 MX MX9203594A patent/MX9203594A/es unknown
-
1994
- 1994-07-29 NO NO1994006C patent/NO1994006I1/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NO1994006I1 (no) | 1994-07-29 |
| KR840001921B1 (ko) | 1984-10-25 |
| FR2458538A1 (fr) | 1981-01-02 |
| MX9203594A (es) | 1992-07-01 |
| LU88272I2 (OSRAM) | 1994-02-03 |
| SU1681733A3 (ru) | 1991-09-30 |
| JPS6356238B2 (OSRAM) | 1988-11-07 |
| JPH0371438B2 (OSRAM) | 1991-11-13 |
| JPS63264498A (ja) | 1988-11-01 |
| US4234571A (en) | 1980-11-18 |
| FR2458538B1 (OSRAM) | 1984-10-19 |
| SU1428205A3 (ru) | 1988-09-30 |
| JPS55164663A (en) | 1980-12-22 |
| ATE9089T1 (de) | 1984-09-15 |
| HU185379B (en) | 1985-01-28 |
| KR830002804A (ko) | 1983-05-30 |
| JPH0371439B2 (OSRAM) | 1991-11-13 |
| ZA803453B (en) | 1982-01-27 |
| JPS6425794A (en) | 1989-01-27 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| SI8011553A8 (sl) | Postopek za pripravo nonapeptidnih in dekapeptidnih derivatov hormonov za sproščanje luteinizirajočega hormona | |
| JP7179241B1 (ja) | 環状ペプチド化合物の医薬用途 | |
| DE69108738T2 (de) | Nonapeptide als bombesinantagonisten. | |
| US6472505B1 (en) | Peptide parathyroid hormone analogs | |
| DE3883789T2 (de) | Polypeptidverbindungen mit wachstumshormonfreisetzender aktivität. | |
| AU675274B2 (en) | Reduced size LHRH analogs | |
| AU2009311645B2 (en) | CXCR4 receptor compounds | |
| CZ315594A3 (en) | Peptide of glucagon type, insulinotropic derivatives, process of their preparation, pharmaceutical composition containing such compounds and use | |
| JP2004514651A (ja) | グレリン類似体 | |
| JPH11509201A (ja) | 副甲状腺ホルモンの類似体 | |
| HUP0003592A2 (hu) | LH-RH peptid analógok, alkalmazásuk, és ezeket tartalmazó gyógyászati készítmények | |
| JP2008521840A5 (OSRAM) | ||
| JP3801867B2 (ja) | 改善された溶解特性を有する新規のlhrhアンタゴニスト | |
| BG98426A (bg) | Пептиди с органо-защитна активност,метод за тяхното получаване и приложението им за лечение | |
| JPH07507330A (ja) | ポリペプチドのボンベシン拮抗物質 | |
| TW585873B (en) | Antagonistic analogs of GH-RH inhibiting IGF-I and -II | |
| JPH06502618A (ja) | 新規な合成grf類似物 | |
| JPS6022720B2 (ja) | ペプチドおよびその製法 | |
| NO177713B (no) | Analogifremgangsmåte ved fremstilling av hemoreguleringspeptider | |
| KR100244624B1 (ko) | 황체 형성 호르몬 방출 호르몬(lhrh) 길항제 및 이를 함유하는 약제학적 조성물 | |
| JPS61210099A (ja) | 新規な成長ホルモン放出性ペプチド | |
| JP6412170B2 (ja) | オキシトシンアゴニストとしてのペプチド | |
| EP3647319B1 (en) | Peptide compound, application thereof and composition containing same | |
| US4111923A (en) | Octapeptides and methods for their production | |
| DE60125959T2 (de) | Unterscheidung zwischen gnrh-i und gnrh-ii |