CS411591A3 - Pharmaceutical composition and its application for mastocarcinoma treatment - Google Patents

Pharmaceutical composition and its application for mastocarcinoma treatment Download PDF

Info

Publication number: CS411591A3
Authority: CS; Czechoslovakia
Prior art keywords: group; carbon atoms; alkyl; atom; phe
Prior art date: 1987-07-10

Application number

CS914115A

Other languages

Czech (cs)

English (en)

Inventor

Thomas Dr Cavanak

Alan Dr Harris

Original Assignee

Sandoz Ltd

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1987-07-10

Filing date

1991-12-27

Publication date

1992-06-17

1987-07-10 Priority claimed from GB878716324A external-priority patent/GB8716324D0/en

1987-07-10 Priority claimed from GB878716326A external-priority patent/GB8716326D0/en

1991-12-27 Application filed by Sandoz Ltd filed Critical Sandoz Ltd

1992-06-17 Publication of CS411591A3 publication Critical patent/CS411591A3/cs

Links

239000008194 pharmaceutical composition Substances 0.000 title claims description 49
238000011282 treatment Methods 0.000 title claims description 16
125000004432 carbon atom Chemical group C* 0.000 claims description 87
150000001875 compounds Chemical class 0.000 claims description 71
125000000217 alkyl group Chemical group 0.000 claims description 60
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 42
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 36
NHXLMOGPVYXJNR-ATOGVRKGSA-N somatostatin Chemical class C([C@H]1C(=O)N[C@H](C(N[C@@H](CO)C(=O)N[C@@H](CSSC[C@@H](C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CC=2C3=CC=CC=C3NC=2)C(=O)N[C@@H](CCCCN)C(=O)N[C@H](C(=O)N1)[C@@H](C)O)NC(=O)CNC(=O)[C@H](C)N)C(O)=O)=O)[C@H](O)C)C1=CC=CC=C1 NHXLMOGPVYXJNR-ATOGVRKGSA-N 0.000 claims description 28
206010006187 Breast cancer Diseases 0.000 claims description 22
208000026310 Breast neoplasm Diseases 0.000 claims description 22
239000001257 hydrogen Substances 0.000 claims description 20
229910052739 hydrogen Inorganic materials 0.000 claims description 20
-1 hydroxy, amino Chemical group 0.000 claims description 20
125000003277 amino group Chemical group 0.000 claims description 18
239000004310 lactic acid Substances 0.000 claims description 18
235000014655 lactic acid Nutrition 0.000 claims description 18
125000003545 alkoxy group Chemical group 0.000 claims description 17
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
125000001424 substituent group Chemical group 0.000 claims description 16
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 15
125000003884 phenylalkyl group Chemical group 0.000 claims description 15
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 14
229910052717 sulfur Inorganic materials 0.000 claims description 14
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
229910052799 carbon Inorganic materials 0.000 claims description 11
125000005843 halogen group Chemical group 0.000 claims description 11
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
150000003839 salts Chemical class 0.000 claims description 11
229940075620 somatostatin analogue Drugs 0.000 claims description 11
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical group [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 10
125000004434 sulfur atom Chemical group 0.000 claims description 9
150000001413 amino acids Chemical class 0.000 claims description 8
239000000203 mixture Substances 0.000 claims description 8
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical group OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims description 7
229930195725 Mannitol Natural products 0.000 claims description 7
239000003136 dopamine receptor stimulating agent Substances 0.000 claims description 7
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
229910052736 halogen Inorganic materials 0.000 claims description 7
150000002367 halogens Chemical class 0.000 claims description 7
239000000594 mannitol Substances 0.000 claims description 7
235000010355 mannitol Nutrition 0.000 claims description 7
229910052757 nitrogen Inorganic materials 0.000 claims description 7
UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 7
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
235000001014 amino acid Nutrition 0.000 claims description 6
239000003795 chemical substances by application Substances 0.000 claims description 6
238000000034 method Methods 0.000 claims description 6
229930182832 D-phenylalanine Natural products 0.000 claims description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
239000002253 acid Substances 0.000 claims description 5
235000008206 alpha-amino acids Nutrition 0.000 claims description 5
229910052801 chlorine Inorganic materials 0.000 claims description 5
239000011780 sodium chloride Substances 0.000 claims description 5
239000011593 sulfur Substances 0.000 claims description 5
125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 4
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 4
125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 4
108010016626 Dipeptides Proteins 0.000 claims description 4
125000003275 alpha amino acid group Chemical group 0.000 claims description 4
150000001370 alpha-amino acid derivatives Chemical class 0.000 claims description 4
125000000539 amino acid group Chemical group 0.000 claims description 4
125000004429 atom Chemical group 0.000 claims description 4
125000001309 chloro group Chemical group Cl* 0.000 claims description 4
238000002360 preparation method Methods 0.000 claims description 4
235000017557 sodium bicarbonate Nutrition 0.000 claims description 4
229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
FUOOLUPWFVMBKG-UHFFFAOYSA-N 2-Aminoisobutyric acid Chemical group CC(C)(N)C(O)=O FUOOLUPWFVMBKG-UHFFFAOYSA-N 0.000 claims description 3
125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 3
150000007514 bases Chemical class 0.000 claims description 3
150000002148 esters Chemical class 0.000 claims description 3
229910052731 fluorine Inorganic materials 0.000 claims description 3
229920001542 oligosaccharide Polymers 0.000 claims description 3
150000002482 oligosaccharides Chemical class 0.000 claims description 3
230000008707 rearrangement Effects 0.000 claims description 3
IYKLZBIWFXPUCS-VIFPVBQESA-N (2s)-2-(naphthalen-1-ylamino)propanoic acid Chemical compound C1=CC=C2C(N[C@@H](C)C(O)=O)=CC=CC2=C1 IYKLZBIWFXPUCS-VIFPVBQESA-N 0.000 claims description 2
125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 2
COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 claims description 2
125000004103 aminoalkyl group Chemical group 0.000 claims description 2
125000004181 carboxyalkyl group Chemical group 0.000 claims description 2
125000001153 fluoro group Chemical group F* 0.000 claims description 2
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
239000011734 sodium Substances 0.000 claims description 2
239000008223 sterile water Substances 0.000 claims description 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
KDXKERNSBIXSRK-RXMQYKEDSA-N D-lysine group Chemical group N[C@H](CCCCN)C(=O)O KDXKERNSBIXSRK-RXMQYKEDSA-N 0.000 claims 1
PQNASZJZHFPQLE-LURJTMIESA-N N(6)-methyl-L-lysine Chemical compound CNCCCC[C@H](N)C(O)=O PQNASZJZHFPQLE-LURJTMIESA-N 0.000 claims 1
JWBLQDDHSDGEGR-DRZSPHRISA-N Phe-Ile Chemical group CC[C@H](C)[C@@H](C(O)=O)NC(=O)[C@@H](N)CC1=CC=CC=C1 JWBLQDDHSDGEGR-DRZSPHRISA-N 0.000 claims 1
DZHDVYLBNKMLMB-ZFWWWQNUSA-N Trp-Lys Chemical compound C1=CC=C2C(C[C@H](N)C(=O)N[C@@H](CCCCN)C(O)=O)=CNC2=C1 DZHDVYLBNKMLMB-ZFWWWQNUSA-N 0.000 claims 1
NLWCSMOXNKBRLC-WDSOQIARSA-N Trp-Lys-Val Chemical compound [H]N[C@@H](CC1=CNC2=C1C=CC=C2)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C(C)C)C(O)=O NLWCSMOXNKBRLC-WDSOQIARSA-N 0.000 claims 1
239000000556 agonist Substances 0.000 claims 1
150000001371 alpha-amino acids Chemical class 0.000 claims 1
150000001412 amines Chemical group 0.000 claims 1
229940125890 compound Ia Drugs 0.000 claims 1
SFDJOSRHYKHMOK-UHFFFAOYSA-N nitramide Chemical compound N[N+]([O-])=O SFDJOSRHYKHMOK-UHFFFAOYSA-N 0.000 claims 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
DEQANNDTNATYII-OULOTJBUSA-N (4r,7s,10s,13r,16s,19r)-10-(4-aminobutyl)-19-[[(2r)-2-amino-3-phenylpropanoyl]amino]-16-benzyl-n-[(2r,3r)-1,3-dihydroxybutan-2-yl]-7-[(1r)-1-hydroxyethyl]-13-(1h-indol-3-ylmethyl)-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentazacycloicosane-4-carboxa Chemical compound C([C@@H](N)C(=O)N[C@H]1CSSC[C@H](NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCCCN)NC(=O)[C@@H](CC=2C3=CC=CC=C3NC=2)NC(=O)[C@H](CC=2C=CC=CC=2)NC1=O)C(=O)N[C@H](CO)[C@H](O)C)C1=CC=CC=C1 DEQANNDTNATYII-OULOTJBUSA-N 0.000 description 9
108010016076 Octreotide Proteins 0.000 description 9
229960002700 octreotide Drugs 0.000 description 9
238000012360 testing method Methods 0.000 description 9
108090000765 processed proteins & peptides Proteins 0.000 description 8
206010028980 Neoplasm Diseases 0.000 description 7
230000004044 response Effects 0.000 description 7
238000007920 subcutaneous administration Methods 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
125000004122 cyclic group Chemical group 0.000 description 5
238000002347 injection Methods 0.000 description 5
239000007924 injection Substances 0.000 description 5
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
230000001419 dependent effect Effects 0.000 description 4
230000003902 lesion Effects 0.000 description 4
206010061289 metastatic neoplasm Diseases 0.000 description 4
150000003254 radicals Chemical class 0.000 description 4
239000000126 substance Substances 0.000 description 4
206010000599 Acromegaly Diseases 0.000 description 3
COLNVLDHVKWLRT-MRVPVSSYSA-N D-phenylalanine Chemical compound OC(=O)[C@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-MRVPVSSYSA-N 0.000 description 3
BKRGVLQUQGGVSM-KBXCAEBGSA-N Revanil Chemical compound C1=CC(C=2[C@H](N(C)C[C@H](C=2)NC(=O)N(CC)CC)C2)=C3C2=CNC3=C1 BKRGVLQUQGGVSM-KBXCAEBGSA-N 0.000 description 3
102000005157 Somatostatin Human genes 0.000 description 3
108010056088 Somatostatin Proteins 0.000 description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
201000011510 cancer Diseases 0.000 description 3
239000001569 carbon dioxide Substances 0.000 description 3
229910002092 carbon dioxide Inorganic materials 0.000 description 3
238000007796 conventional method Methods 0.000 description 3
238000011156 evaluation Methods 0.000 description 3
229940088597 hormone Drugs 0.000 description 3
239000005556 hormone Substances 0.000 description 3
238000001802 infusion Methods 0.000 description 3
230000004807 localization Effects 0.000 description 3
229910052760 oxygen Inorganic materials 0.000 description 3
239000001301 oxygen Substances 0.000 description 3
229920001184 polypeptide Polymers 0.000 description 3
102000004196 processed proteins & peptides Human genes 0.000 description 3
229960000553 somatostatin Drugs 0.000 description 3
238000010254 subcutaneous injection Methods 0.000 description 3
239000007929 subcutaneous injection Substances 0.000 description 3
NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 description 3
125000004455 (C1-C3) alkylthio group Chemical group 0.000 description 2
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
201000009030 Carcinoma Diseases 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
YYARMJSFDLIDFS-FKBYEOEOSA-N Pro-Phe-Trp Chemical compound [H]N1CCC[C@H]1C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)N[C@@H](CC1=CNC2=C1C=CC=C2)C(O)=O YYARMJSFDLIDFS-FKBYEOEOSA-N 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical class N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
108050001286 Somatostatin Receptor Proteins 0.000 description 2
102000011096 Somatostatin receptor Human genes 0.000 description 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
125000003342 alkenyl group Chemical group 0.000 description 2
125000006615 aromatic heterocyclic group Chemical group 0.000 description 2
230000009286 beneficial effect Effects 0.000 description 2
238000001574 biopsy Methods 0.000 description 2
229960002802 bromocriptine Drugs 0.000 description 2
OZVBMTJYIDMWIL-AYFBDAFISA-N bromocriptine Chemical group C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N[C@]2(C(=O)N3[C@H](C(N4CCC[C@H]4[C@]3(O)O2)=O)CC(C)C)C(C)C)C2)=C3C2=C(Br)NC3=C1 OZVBMTJYIDMWIL-AYFBDAFISA-N 0.000 description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
125000000753 cycloalkyl group Chemical group 0.000 description 2
125000004663 dialkyl amino group Chemical group 0.000 description 2
230000007717 exclusion Effects 0.000 description 2
125000005842 heteroatom Chemical group 0.000 description 2
239000004615 ingredient Substances 0.000 description 2
NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 2
229960003587 lisuride Drugs 0.000 description 2
230000001394 metastastic effect Effects 0.000 description 2
125000004433 nitrogen atom Chemical group N* 0.000 description 2
238000007911 parenteral administration Methods 0.000 description 2
LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 2
239000001632 sodium acetate Substances 0.000 description 2
235000017281 sodium acetate Nutrition 0.000 description 2
230000006641 stabilisation Effects 0.000 description 2
238000011105 stabilization Methods 0.000 description 2
229960004558 terguride Drugs 0.000 description 2
238000002560 therapeutic procedure Methods 0.000 description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
FHSGULRVYLHXFO-FFNFELIASA-N (3s,6s,9s,12r,15s,18s)-9-(4-aminobutyl)-3,15-dibenzyl-6-[(1r)-1-hydroxyethyl]-12-(1h-indol-3-ylmethyl)-1,4,7,10,13,16-hexazabicyclo[16.3.0]henicosane-2,5,8,11,14,17-hexone Chemical compound C([C@H]1C(=O)N[C@H](CC=2C3=CC=CC=C3NC=2)C(=O)N[C@@H](CCCCN)C(=O)N[C@H](C(N[C@@H](CC=2C=CC=CC=2)C(=O)N2CCC[C@H]2C(=O)N1)=O)[C@H](O)C)C1=CC=CC=C1 FHSGULRVYLHXFO-FFNFELIASA-N 0.000 description 1
NPJIOCBFOAHEDO-AVWFULIKSA-N (3s,6s,9s,12r,15s,18s)-9-(4-aminobutyl)-3-benzyl-15-[(4-hydroxyphenyl)methyl]-12-(1h-indol-3-ylmethyl)-1,18-dimethyl-6-propan-2-yl-1,4,7,10,13,16-hexazacyclooctadecane-2,5,8,11,14,17-hexone Chemical compound C([C@H]1C(=O)N[C@H](CC=2C3=CC=CC=C3NC=2)C(=O)N[C@@H](CCCCN)C(=O)N[C@H](C(N[C@@H](CC=2C=CC=CC=2)C(=O)N(C)[C@@H](C)C(=O)N1)=O)C(C)C)C1=CC=C(O)C=C1 NPJIOCBFOAHEDO-AVWFULIKSA-N 0.000 description 1
DIPBYRMTSXMCIM-MOZMXQSSSA-N (6ar,9r,10ar)-n-[(e,2r,3s)-1,3-dihydroxyoctadec-4-en-2-yl]-7-methyl-6,6a,8,9,10,10a-hexahydro-4h-indolo[4,3-fg]quinoline-9-carboxamide Chemical compound C1=CC([C@H]2C[C@H](CN(C)[C@@H]2C2)C(=O)N[C@H](CO)[C@@H](O)/C=C/CCCCCCCCCCCCC)=C3C2=CNC3=C1 DIPBYRMTSXMCIM-MOZMXQSSSA-N 0.000 description 1
125000004209 (C1-C8) alkyl group Chemical group 0.000 description 1
FWWOWPGPERBCNJ-UHFFFAOYSA-N 2-hydroxy-4-(2-hydroxyethoxy)-4-oxobutanoic acid Chemical compound OCCOC(=O)CC(O)C(O)=O FWWOWPGPERBCNJ-UHFFFAOYSA-N 0.000 description 1
FCRJELOYDVBTGW-ILZDJORESA-N 3-[(6ar,9s,10ar)-7-propyl-6,6a,8,9,10,10a-hexahydro-4h-indolo[4,3-fg]quinoline-9-yl]-1,1-diethylurea Chemical compound C1=CC([C@H]2C[C@@H](CN([C@@H]2C2)CCC)NC(=O)N(CC)CC)=C3C2=CNC3=C1 FCRJELOYDVBTGW-ILZDJORESA-N 0.000 description 1
AWFDCTXCTHGORH-HGHGUNKESA-N 6-[4-[(6ar,9r,10ar)-5-bromo-7-methyl-6,6a,8,9,10,10a-hexahydro-4h-indolo[4,3-fg]quinoline-9-carbonyl]piperazin-1-yl]-1-methylpyridin-2-one Chemical group O=C([C@H]1CN([C@H]2[C@@H](C=3C=CC=C4NC(Br)=C(C=34)C2)C1)C)N(CC1)CCN1C1=CC=CC(=O)N1C AWFDCTXCTHGORH-HGHGUNKESA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
206010003445 Ascites Diseases 0.000 description 1
206010055113 Breast cancer metastatic Diseases 0.000 description 1
UMJHAEUVYNEBNP-RXYCCRQDSA-N C([C@H]1C(=O)N[C@H](CC=2C3=CC=CC=C3NC=2)C(=O)N[C@@H](CCCCN)C(=O)N[C@H](C(N[C@@H](CC=2C=CC=CC=2)C(=O)N2CCC[C@H]2C(=O)N1)=O)[C@H](O)C)C1=CC=C(O)C=C1 Chemical compound C([C@H]1C(=O)N[C@H](CC=2C3=CC=CC=C3NC=2)C(=O)N[C@@H](CCCCN)C(=O)N[C@H](C(N[C@@H](CC=2C=CC=CC=2)C(=O)N2CCC[C@H]2C(=O)N1)=O)[C@H](O)C)C1=CC=C(O)C=C1 UMJHAEUVYNEBNP-RXYCCRQDSA-N 0.000 description 1
101710115643 Cathelicidin-1 Proteins 0.000 description 1
206010008342 Cervix carcinoma Diseases 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
IRKLTAKLAFUTLA-KATARQTJSA-N Cys-Thr-Lys Chemical compound C[C@@H](O)[C@H](NC(=O)[C@@H](N)CS)C(=O)N[C@@H](CCCCN)C(O)=O IRKLTAKLAFUTLA-KATARQTJSA-N 0.000 description 1
125000001711 D-phenylalanine group Chemical group [H]N([H])[C@@]([H])(C(=O)[*])C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 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
208000002699 Digestive System Neoplasms Diseases 0.000 description 1
206010061818 Disease progression Diseases 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
108010051696 Growth Hormone Proteins 0.000 description 1
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 1
102000004877 Insulin Human genes 0.000 description 1
108090001061 Insulin Proteins 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
LRQKBLKVPFOOQJ-YFKPBYRVSA-N L-norleucine Chemical group CCCC[C@H]([NH3+])C([O-])=O LRQKBLKVPFOOQJ-YFKPBYRVSA-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
ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 description 1
206010058467 Lung neoplasm malignant Diseases 0.000 description 1
JLVHTNZNKOSCNB-YSVLISHTSA-N Mesulergine Chemical compound C1=CC([C@H]2C[C@@H](CN(C)[C@@H]2C2)NS(=O)(=O)N(C)C)=C3C2=CN(C)C3=C1 JLVHTNZNKOSCNB-YSVLISHTSA-N 0.000 description 1
206010027476 Metastases Diseases 0.000 description 1
PTDAGKJHZBGDKD-OEAJRASXSA-N Phe-Thr-Lys Chemical compound C[C@H]([C@@H](C(=O)N[C@@H](CCCCN)C(=O)O)NC(=O)[C@H](CC1=CC=CC=C1)N)O PTDAGKJHZBGDKD-OEAJRASXSA-N 0.000 description 1
208000002151 Pleural effusion Diseases 0.000 description 1
102100024819 Prolactin Human genes 0.000 description 1
108010057464 Prolactin Proteins 0.000 description 1
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 description 1
102100038803 Somatotropin Human genes 0.000 description 1
JOAHPSVPXZTVEP-YXJHDRRASA-N Terguride Chemical compound C1=CC([C@H]2C[C@@H](CN(C)[C@@H]2C2)NC(=O)N(CC)CC)=C3C2=CNC3=C1 JOAHPSVPXZTVEP-YXJHDRRASA-N 0.000 description 1
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
208000006105 Uterine Cervical Neoplasms Diseases 0.000 description 1
208000009311 VIPoma Diseases 0.000 description 1
238000002441 X-ray diffraction Methods 0.000 description 1
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
PQLVXDKIJBQVDF-UHFFFAOYSA-N acetic acid;hydrate Chemical compound O.CC(O)=O PQLVXDKIJBQVDF-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000009471 action Effects 0.000 description 1
238000009098 adjuvant therapy Methods 0.000 description 1
239000003708 ampul Substances 0.000 description 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
210000000988 bone and bone Anatomy 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
150000001649 bromium compounds Chemical class 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
230000002490 cerebral effect Effects 0.000 description 1
201000010881 cervical cancer Diseases 0.000 description 1
210000003679 cervix uteri Anatomy 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 description 1
238000011254 conventional chemotherapy Methods 0.000 description 1
238000011443 conventional therapy Methods 0.000 description 1
231100000433 cytotoxic Toxicity 0.000 description 1
230000001472 cytotoxic effect Effects 0.000 description 1
230000007812 deficiency Effects 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
238000003745 diagnosis Methods 0.000 description 1
239000001177 diphosphate Substances 0.000 description 1
XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 1
235000011180 diphosphates Nutrition 0.000 description 1
201000010099 disease Diseases 0.000 description 1
230000005750 disease progression Effects 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
229940052760 dopamine agonists Drugs 0.000 description 1
229950006629 dosergoside Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
230000002124 endocrine Effects 0.000 description 1
229940011871 estrogen Drugs 0.000 description 1
239000000262 estrogen Substances 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
238000009472 formulation Methods 0.000 description 1
239000012458 free base Substances 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
230000000574 ganglionic effect Effects 0.000 description 1
230000002496 gastric effect Effects 0.000 description 1
201000010231 gastrointestinal system cancer Diseases 0.000 description 1
230000000762 glandular Effects 0.000 description 1
239000003102 growth factor Substances 0.000 description 1
239000000122 growth hormone Substances 0.000 description 1
238000001794 hormone therapy Methods 0.000 description 1
125000001183 hydrocarbyl group Chemical group 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
125000002883 imidazolyl group Chemical group 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
229940125396 insulin Drugs 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 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
239000003446 ligand Substances 0.000 description 1
230000000670 limiting effect Effects 0.000 description 1
206010025226 lymphangitis Diseases 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
230000003211 malignant effect Effects 0.000 description 1
229950008693 mesulergine Drugs 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
229960004650 metergoline Drugs 0.000 description 1
WZHJKEUHNJHDLS-QTGUNEKASA-N metergoline Chemical compound C([C@H]1CN([C@H]2[C@@H](C=3C=CC=C4N(C)C=C(C=34)C2)C1)C)NC(=O)OCC1=CC=CC=C1 WZHJKEUHNJHDLS-QTGUNEKASA-N 0.000 description 1
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
238000012986 modification Methods 0.000 description 1
BOHDKBGWKRCEIT-VQAQLOKVSA-N n-[[(6ar,10ar)-7-methyl-6,6a,8,10a-tetrahydro-4h-indolo[4,3-fg]quinoline-9-yl]methyl]-n-(2-azidoethyl)methanesulfonamide;(z)-but-2-enedioic acid Chemical compound OC(=O)\C=C/C(O)=O.C1=CC([C@H]2C=C(CN(CCN=[N+]=[N-])S(C)(=O)=O)CN([C@@H]2C2)C)=C3C2=CNC3=C1 BOHDKBGWKRCEIT-VQAQLOKVSA-N 0.000 description 1
BUIMWOLDCCGZKZ-UHFFFAOYSA-N n-hydroxynitramide Chemical compound ON[N+]([O-])=O BUIMWOLDCCGZKZ-UHFFFAOYSA-N 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
238000004806 packaging method and process Methods 0.000 description 1
230000036961 partial effect Effects 0.000 description 1
125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
229960004851 pergolide Drugs 0.000 description 1
YEHCICAEULNIGD-MZMPZRCHSA-N pergolide Chemical compound C1=CC([C@H]2C[C@@H](CSC)CN([C@@H]2C2)CCC)=C3C2=CNC3=C1 YEHCICAEULNIGD-MZMPZRCHSA-N 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000002335 preservative effect Effects 0.000 description 1
208000037821 progressive disease Diseases 0.000 description 1
229940097325 prolactin Drugs 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229950007140 proterguride Drugs 0.000 description 1
125000003226 pyrazolyl group Chemical group 0.000 description 1
238000001959 radiotherapy Methods 0.000 description 1
230000002829 reductive effect Effects 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
230000028327 secretion Effects 0.000 description 1
201000008261 skin carcinoma Diseases 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
229940124530 sulfonamide Drugs 0.000 description 1
238000001356 surgical procedure Methods 0.000 description 1
230000004083 survival effect Effects 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
230000007704 transition Effects 0.000 description 1
210000003462 vein Anatomy 0.000 description 1
230000009278 visceral effect Effects 0.000 description 1
239000008215 water for injection Substances 0.000 description 1
150000003751 zinc Chemical class 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- C07K14/435—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
- C07K14/575—Hormones
- C07K14/655—Somatostatins
- C07K14/6555—Somatostatins at least 1 amino acid in D-form
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/16—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- A61K38/17—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
- A61K38/22—Hormones
- A61K38/31—Somatostatins
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/12—Carboxylic acids; Salts or anhydrides thereof
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2123/00—Preparations for testing in vivo
- 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
- Y10S930/16—Somatostatin; 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
- Y10S930/26—Containing cys-cys disulfide bridge between nonadjacent cysteine residues

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Medicinal Chemistry (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Epidemiology (AREA)
Organic Chemistry (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Engineering & Computer Science (AREA)
Endocrinology (AREA)
Gastroenterology & Hepatology (AREA)
Zoology (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Dermatology (AREA)
Genetics & Genomics (AREA)
Molecular Biology (AREA)
Biophysics (AREA)
Toxicology (AREA)
Biochemistry (AREA)
Oil, Petroleum & Natural Gas (AREA)
Bioinformatics & Cheminformatics (AREA)
Immunology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Peptides Or Proteins (AREA)
Medicinal Preparation (AREA)

CS914115A 1987-07-10 1991-12-27 Pharmaceutical composition and its application for mastocarcinoma treatment CS411591A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB878716324A GB8716324D0 (en)	1987-07-10	1987-07-10	Organic compounds
GB878716326A GB8716326D0 (en)	1987-07-10	1987-07-10	Organic compounds

Publications (1)

Publication Number	Publication Date
CS411591A3 true CS411591A3 (en)	1992-06-17

Family

ID=26292476

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS914115A CS411591A3 (en)	1987-07-10	1991-12-27	Pharmaceutical composition and its application for mastocarcinoma treatment

Country Status (27)

Country	Link
US (2)	US5753618A (da)
JP (1)	JP2578477B2 (da)
AU (1)	AU618270B2 (da)
BE (1)	BE1001079A4 (da)
CA (1)	CA1328402C (da)
CH (1)	CH677449A5 (da)
CS (1)	CS411591A3 (da)
CY (2)	CY1631A (da)
DE (2)	DE3822557C2 (da)
DK (2)	DK174125B1 (da)
ES (1)	ES2010561A6 (da)
FI (1)	FI93308C (da)
FR (1)	FR2617714B1 (da)
GB (1)	GB2208200B (da)
GR (1)	GR1000172B (da)
HK (1)	HK16492A (da)
HU (1)	HU203480B (da)
IE (1)	IE61908B1 (da)
IL (1)	IL87044A0 (da)
LU (1)	LU87268A1 (da)
MY (2)	MY109309A (da)
NL (1)	NL194823C (da)
NO (1)	NO179359C (da)
NZ (1)	NZ225340A (da)
PT (1)	PT87957B (da)
SE (2)	SE503191C2 (da)
SG (1)	SG3692G (da)

Families Citing this family (22)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB8813339D0 (en) *	1988-06-06	1988-07-13	Sandoz Ltd	Improvements in/relating to organic compounds
US5538739A (en) *	1989-07-07	1996-07-23	Sandoz Ltd.	Sustained release formulations of water soluble peptides
PH30995A (en) *	1989-07-07	1997-12-23	Novartis Inc	Sustained release formulations of water soluble peptides.
US5626945A (en) *	1993-09-28	1997-05-06	International Paper Company	Repulpable, water repellant paperboard
US6355613B1 (en) *	1996-07-31	2002-03-12	Peptor Limited	Conformationally constrained backbone cyclized somatostatin analogs
WO1998008528A1 (en) *	1996-08-30	1998-03-05	Biomeasure Incorporated	Method of inhibiting fibrosis with a somatostatin agonist
ES2167189B1 (es) *	1999-12-17	2003-04-01	Lipotec Sa	Formulacion farmaceutica estable para la administracion intravenosa o intramuscular, de principios activos peptidicos
US6316414B1 (en)	2000-07-31	2001-11-13	Dabur Research Foundation	Somatostatin analogs for the treatment of cancer
MXPA03011321A (es) *	2001-06-08	2004-12-06	Conseils De Rech S Et D Aplica	Analogos quimericos de somatostatina-dopamina.
TWI287986B (en) *	2001-12-13	2007-10-11	Novartis Ag	Use of Epothilones for the treatment of the carcinoid syndrome
US20030207811A1 (en) *	2002-05-03	2003-11-06	Schrier Bruce K.	Method of treating retinopathy of prematurity using somatostatin analogs
SI1787658T1 (sl)	2005-11-10	2012-07-31	Chemi Spa	Formulacije z trajnim sproščanjem somatostatin analognih inhibitorjev rastnega hormona
CA2647986C (en) *	2006-03-31	2014-07-08	Erasmus University Medical Center Rotterdam	Compositions for tumor growth control
WO2008039482A2 (en) *	2006-09-26	2008-04-03	The Regents Of The University Of California	Methods and compositions for cancer prevention and treatment
US9517240B2 (en)	2006-09-26	2016-12-13	The Regents Of The University Of California	Methods and compositions for cancer prevention and treatment
US20090325863A1 (en) *	2008-06-13	2009-12-31	Kleinberg David L	Somatostatin analogs and IGF-I inhibition for breast cancer prevention
GB201016433D0 (en)	2010-09-30	2010-11-17	Q Chip Ltd	Apparatus and method for making solid beads
GB201016436D0 (en)	2010-09-30	2010-11-17	Q Chip Ltd	Method of making solid beads
US8629103B2 (en) *	2010-12-02	2014-01-14	New York University	Treatment of non-proliferative cystic disease of the breast
CN103732239A (zh)	2011-06-02	2014-04-16	加利福尼亚大学董事会	利用θ-防御素的炎性蛋白酶的阻断
RU2015120570A (ru)	2012-11-01	2016-12-20	Ипсен Фарма С.А.С.	Аналоги соматостатина и их димеры
TWI523863B (zh)	2012-11-01	2016-03-01	艾普森藥品公司	體抑素－多巴胺嵌合體類似物

Family Cites Families (24)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH621770A5 (en) *	1976-02-23	1981-02-27	Sandoz Ag	Process for the preparation of novel peptide compounds
EP0000053B1 (en) *	1977-06-08	1981-05-27	Merck & Co. Inc.	Somatostatin analogs, process for their preparation and pharmaceutical compositions containing them
LU78191A1 (de) *	1977-09-28	1979-05-25	Ciba Geigy Ag	Verfahren zur herstellung von neuen cyclopeptiden
US4328214A (en) *	1979-07-04	1982-05-04	Ciba-Geigy Corporation	Cyclopeptides and pharmaceutical preparations thereof and also processes for their manufacture
US4900730A (en) *	1981-01-14	1990-02-13	Toyo Jozo Co., Ltd.	Preparation which promotes the absorption of peptides
IE52535B1 (en) *	1981-02-16	1987-12-09	Ici Plc	Continuous release pharmaceutical compositions
JPS57188526A (en) *	1981-05-14	1982-11-19	Takeda Chem Ind Ltd	Peptide-containing pharmaceutical preparation
US4374060A (en) *	1981-07-15	1983-02-15	Merck & Co., Inc.	Process for the preparation of cyclic hexapeptide
EP0083305B1 (de) *	1981-12-24	1985-07-10	Ciba-Geigy Ag	Cyclische Octapeptide und pharmazeutische Präparate davon, sowie Verfahren zur Herstellung derselben und ihre Anwendung
US4522813A (en) *	1983-10-27	1985-06-11	Merck & Co., Inc.	Cyclic hexapeptide somatostatin analogs
CH666035A5 (de) *	1984-12-24	1988-06-30	Sandoz Ag	8-alpha-acylaminoergolene.
US4650787A (en) *	1985-04-25	1987-03-17	Schally Andrew Victor	Biologically active octapeptides
US4725577A (en) *	1985-04-25	1988-02-16	Administrators Of The Tulane Educational Fund	Biologically active lysine containing octapeptides
ZW14486A1 (en) *	1985-07-29	1986-10-22	Smithkline Beckman Corp	Pharmaceutical dosage unit
GR862206B (en) *	1985-09-12	1986-12-31	Univ Tulane	Therapeutic somatostatin analogs
JPH085913B2 (ja) *	1985-09-12	1996-01-24	ザ・アドミニストレ−タ−ズ・オブ・ザ・ツ−レイン・エデユケイシヨナル・フアンド	治療用ソマトスタチン同族体
NL8701143A (nl) *	1986-05-27	1987-12-16	Sandoz Ag	Farmaceutische preparaten.
HU206890B (en) *	1986-10-13	1993-01-28	Sandoz Ag	Process for producing sugar-modified somatostatin peptide derivatives and pharmaceutical compositions containing them as active components
AU639371B2 (en) *	1987-07-10	1993-07-22	Novartis Ag	Method of treating breast cancer
US5187150A (en) *	1987-10-14	1993-02-16	Debiopharm S.A.	Polyester-based composition for the controlled release of polypeptide medicinal substances
AU2284588A (en) *	1988-09-26	1990-03-29	Sandoz Ltd.	Improvements in or relating to organic compounds
MY106120A (en) *	1988-12-05	1995-03-31	Novartis Ag	Peptide derivatives.
US5384309A (en) *	1989-07-17	1995-01-24	Genentech, Inc.	Cyclized peptides and their use as platelet aggregation inhibitors
JPH0532696A (ja) *	1990-09-28	1993-02-09	Takeda Chem Ind Ltd	副甲状腺ホルモン誘導体

1988
- 1988-07-04 DE DE3822557A patent/DE3822557C2/de not_active Expired - Lifetime
- 1988-07-04 DE DE3845000A patent/DE3845000C2/de not_active Expired - Lifetime
- 1988-07-05 CH CH2556/88A patent/CH677449A5/de not_active IP Right Cessation
- 1988-07-06 GB GB8816024A patent/GB2208200B/en not_active Expired - Lifetime
- 1988-07-07 MY MYPI93000569A patent/MY109309A/en unknown
- 1988-07-07 MY MYPI88000750A patent/MY103746A/en unknown
- 1988-07-08 LU LU87268A patent/LU87268A1/fr unknown
- 1988-07-08 IL IL87044A patent/IL87044A0/xx not_active IP Right Cessation
- 1988-07-08 GR GR880100458A patent/GR1000172B/el not_active IP Right Cessation
- 1988-07-08 AU AU18893/88A patent/AU618270B2/en not_active Expired
- 1988-07-08 CA CA000571592A patent/CA1328402C/en not_active Expired - Lifetime
- 1988-07-08 IE IE209188A patent/IE61908B1/en not_active IP Right Cessation
- 1988-07-08 PT PT87957A patent/PT87957B/pt not_active IP Right Cessation
- 1988-07-08 DK DK198803854A patent/DK174125B1/da not_active IP Right Cessation
- 1988-07-08 ES ES8802161A patent/ES2010561A6/es not_active Expired
- 1988-07-08 HU HU883604A patent/HU203480B/hu unknown
- 1988-07-08 FR FR888809439A patent/FR2617714B1/fr not_active Expired - Lifetime
- 1988-07-08 NO NO883054A patent/NO179359C/no not_active IP Right Cessation
- 1988-07-08 NL NL8801734A patent/NL194823C/nl not_active IP Right Cessation
- 1988-07-08 SE SE8802569A patent/SE503191C2/sv not_active IP Right Cessation
- 1988-07-08 NZ NZ225340A patent/NZ225340A/en unknown
- 1988-07-08 FI FI883261A patent/FI93308C/fi active IP Right Grant
- 1988-07-09 JP JP63171703A patent/JP2578477B2/ja not_active Expired - Lifetime
- 1988-07-11 BE BE8800803A patent/BE1001079A4/fr not_active IP Right Cessation
1991
- 1991-12-27 CS CS914115A patent/CS411591A3/cs unknown
1992
- 1992-01-13 SG SG36/92A patent/SG3692G/en unknown
- 1992-02-27 HK HK164/92A patent/HK16492A/xx not_active IP Right Cessation
- 1992-07-10 CY CY1631A patent/CY1631A/en unknown
- 1992-07-10 CY CY1632A patent/CY1632A/en unknown
1993
- 1993-04-20 SE SE19939301290A patent/SE9301290D0/xx not_active Application Discontinuation
1995
- 1995-06-06 US US08/471,706 patent/US5753618A/en not_active Expired - Lifetime
1998
- 1998-02-11 US US09/022,079 patent/US6066616A/en not_active Expired - Fee Related
2001
- 2001-04-04 DK DK200100558A patent/DK174476B1/da not_active IP Right Cessation

Also Published As

Publication number	Publication date
AU1889388A (en)	1989-01-12
SE9301290A0 (sv)	1993-04-20
JPS6431728A (en)	1989-02-02
SE9301290D0 (sv)	1993-04-20
GB8816024D0 (en)	1988-08-10
CA1328402C (en)	1994-04-12
DK200100558A (da)	2001-04-04
NL194823C (nl)	2003-04-03
IL87044A0 (en)	1988-12-30
PT87957B (pt)	1995-03-01
MY109309A (en)	1997-01-31
LU87268A1 (fr)	1989-03-08
FI93308B (fi)	1994-12-15
IE61908B1 (en)	1994-11-30
NL194823B (nl)	2002-12-02
JP2578477B2 (ja)	1997-02-05
JPH0748272A (ja)	1995-02-21
DK174125B1 (da)	2002-07-01
FI883261L (fi)	1989-01-11
FI883261A0 (fi)	1988-07-08
PT87957A (pt)	1989-06-30
DE3822557A1 (de)	1989-01-19
SE8802569L (sv)	1989-01-11
DK385488A (da)	1989-01-11
NO883054L (no)	1989-01-11
SE8802569D0 (sv)	1988-07-08
NO883054D0 (no)	1988-07-08
SG3692G (en)	1992-03-20
MY103746A (en)	1993-09-30
JP2764041B2 (ja)	1998-06-11
HK16492A (en)	1992-03-06
US5753618A (en)	1998-05-19
DK174476B1 (da)	2003-04-14
NO179359C (no)	1996-09-25
FI93308C (fi)	1995-03-27
CY1631A (en)	1992-07-10
HU203480B (en)	1991-08-28
GB2208200B (en)	1991-11-27
AU618270B2 (en)	1991-12-19
GB2208200A (en)	1989-03-15
CH677449A5 (da)	1991-05-31
SE503191C2 (sv)	1996-04-15
NO179359B (no)	1996-06-17
DK385488D0 (da)	1988-07-08
ES2010561A6 (es)	1989-11-16
HUT47865A (en)	1989-04-28
DE3845000C2 (de)	1998-11-19
GR880100458A (en)	1989-04-12
BE1001079A4 (fr)	1989-07-04
US6066616A (en)	2000-05-23
FR2617714B1 (fr)	1991-09-20
DE3822557C2 (de)	1998-07-02
NZ225340A (en)	1991-05-28
IE882091L (en)	1989-01-10
NL8801734A (nl)	1989-02-01
FR2617714A1 (fr)	1989-01-13
CY1632A (en)	1992-07-10
GR1000172B (el)	1991-11-15

Publication	Publication Date	Title
CS411591A3 (en)	1992-06-17	Pharmaceutical composition and its application for mastocarcinoma treatment
Tomassetti et al.	1998	Slow-release lanreotide treatment in endocrine gastrointestinal tumors
AU726731B2 (en)	2000-11-16	Method of inhibiting fibrosis with a somatostatin agonist
KR20240060873A (ko)	2024-05-08	Gip/glp1 작용제 조성물
EP0896544B1 (en)	2003-02-26	Combination of a somatostatin analogue and a rapamycin
AU631547B2 (en)	1992-12-03	Treatment of arthritis
CA2585116A1 (en)	2006-06-29	Sustained release formulation comprising bisphosphonate
WO1999056769A2 (en)	1999-11-11	Inhibition of helicobacter pylori proliferation
KR100195894B1 (ko)	1999-06-15	소마토스타틴 동족체를 함유하는 약학 조성물
GB2239178A (en)	1991-06-26	Somatostatin analogues for the treatment of breast cancer
JP2764041B6 (ja)	2008-05-21	ソマトスタチン類に関する改良
JPH02149528A (ja)	1990-06-08	肺保護剤
WO2002009739A1 (en)	2002-02-07	Treatment of ocular disorders with somatostatin analogues
EP0979098A1 (en)	2000-02-16	Method of treating hyperprolactinemia and prolactinomas
CA2674186A1 (en)	2008-07-10	Use of somatostatin analogs in cluster headache

Legal Events

Date	Code	Title	Description
2000-06-30	PD00	Pending as of 2000-06-30 in czech republic