KR102532912B1 - 자궁 내막증 치료용 인돌의 신규 유도체 - Google Patents
자궁 내막증 치료용 인돌의 신규 유도체 Download PDFInfo
- Publication number
- KR102532912B1 KR102532912B1 KR1020197014596A KR20197014596A KR102532912B1 KR 102532912 B1 KR102532912 B1 KR 102532912B1 KR 1020197014596 A KR1020197014596 A KR 1020197014596A KR 20197014596 A KR20197014596 A KR 20197014596A KR 102532912 B1 KR102532912 B1 KR 102532912B1
- Authority
- KR
- South Korea
- Prior art keywords
- indol
- bromo
- acrylonitrile
- group
- pyridin
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 201000009273 Endometriosis Diseases 0.000 title claims abstract description 55
- 238000011282 treatment Methods 0.000 title claims abstract description 24
- 150000002475 indoles Chemical class 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 50
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 25
- 239000003814 drug Substances 0.000 claims description 23
- 150000003839 salts Chemical class 0.000 claims description 22
- 229940079593 drug Drugs 0.000 claims description 19
- JZGHWJXVINSBOA-VGOFMYFVSA-N 3-[(z)-2-(5-bromo-1h-indol-3-yl)-2-cyanoethenyl]-4-methoxybenzonitrile Chemical compound COC1=CC=C(C#N)C=C1\C=C(/C#N)C1=CNC2=CC=C(Br)C=C12 JZGHWJXVINSBOA-VGOFMYFVSA-N 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- 239000004480 active ingredient Substances 0.000 claims description 6
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 claims description 6
- NGGMYCMLYOUNGM-CSDLUJIJSA-N fumagillin Chemical class C([C@H]([C@H]([C@@H]1[C@]2(C)[C@H](O2)CC=C(C)C)OC)OC(=O)\C=C\C=C\C=C\C=C\C(O)=O)C[C@@]21CO2 NGGMYCMLYOUNGM-CSDLUJIJSA-N 0.000 claims description 4
- 239000000583 progesterone congener Substances 0.000 claims description 4
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims description 3
- 239000000556 agonist Substances 0.000 claims description 3
- 239000004037 angiogenesis inhibitor Substances 0.000 claims description 3
- 229940121369 angiogenesis inhibitor Drugs 0.000 claims description 3
- 239000003433 contraceptive agent Substances 0.000 claims description 3
- 239000003255 cyclooxygenase 2 inhibitor Substances 0.000 claims description 3
- POZRVZJJTULAOH-LHZXLZLDSA-N danazol Chemical compound C1[C@]2(C)[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=CC2=C1C=NO2 POZRVZJJTULAOH-LHZXLZLDSA-N 0.000 claims description 3
- 229960000766 danazol Drugs 0.000 claims description 3
- 229940052760 dopamine agonists Drugs 0.000 claims description 3
- 239000003136 dopamine receptor stimulating agent Substances 0.000 claims description 3
- 239000003102 growth factor Substances 0.000 claims description 3
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims description 3
- 239000002955 immunomodulating agent Substances 0.000 claims description 3
- 229940121354 immunomodulator Drugs 0.000 claims description 3
- 239000003112 inhibitor Substances 0.000 claims description 3
- 229940005483 opioid analgesics Drugs 0.000 claims description 3
- 239000002307 peroxisome proliferator activated receptor agonist Substances 0.000 claims description 3
- 229930000223 plant secondary metabolite Natural products 0.000 claims description 3
- 239000003488 releasing hormone Substances 0.000 claims description 2
- 230000002265 prevention Effects 0.000 abstract description 11
- 229910052736 halogen Inorganic materials 0.000 description 44
- 150000002367 halogens Chemical group 0.000 description 44
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 34
- -1 hydroxy, amino Chemical group 0.000 description 30
- 229910052731 fluorine Inorganic materials 0.000 description 29
- 239000011737 fluorine Substances 0.000 description 29
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 27
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 23
- 150000003254 radicals Chemical class 0.000 description 23
- 229910052794 bromium Inorganic materials 0.000 description 22
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 21
- 229910052801 chlorine Inorganic materials 0.000 description 21
- 239000000460 chlorine Substances 0.000 description 21
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 20
- 125000001072 heteroaryl group Chemical group 0.000 description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 18
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 18
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 description 16
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 13
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 13
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 12
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 11
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 10
- 125000002877 alkyl aryl group Chemical group 0.000 description 10
- 229910052739 hydrogen Inorganic materials 0.000 description 10
- 239000001257 hydrogen Substances 0.000 description 10
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- GOMPBEBFZVSPJK-IZZDOVSWSA-N (z)-2-(5-chloro-1h-indol-3-yl)-3-(4-methoxypyridin-3-yl)prop-2-enenitrile Chemical compound COC1=CC=NC=C1\C=C(/C#N)C1=CNC2=CC=C(Cl)C=C12 GOMPBEBFZVSPJK-IZZDOVSWSA-N 0.000 description 9
- 125000005842 heteroatom Chemical group 0.000 description 9
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 8
- 125000003545 alkoxy group Chemical group 0.000 description 8
- 125000003118 aryl group Chemical group 0.000 description 8
- JZGHWJXVINSBOA-AUWJEWJLSA-N 3-[(e)-2-(5-bromo-1h-indol-3-yl)-2-cyanoethenyl]-4-methoxybenzonitrile Chemical compound COC1=CC=C(C#N)C=C1\C=C(\C#N)C1=CNC2=CC=C(Br)C=C12 JZGHWJXVINSBOA-AUWJEWJLSA-N 0.000 description 7
- 230000003902 lesion Effects 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 description 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
- 150000003852 triazoles Chemical class 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- 125000000623 heterocyclic group Chemical group 0.000 description 6
- 150000002431 hydrogen Chemical class 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- VAOYWUWRWZBMLC-WDZFZDKYSA-N (e)-2-(5-bromo-1h-indol-3-yl)-3-(4-methoxypyridin-3-yl)prop-2-enenitrile Chemical compound COC1=CC=NC=C1\C=C(\C#N)C1=CNC2=CC=C(Br)C=C12 VAOYWUWRWZBMLC-WDZFZDKYSA-N 0.000 description 5
- QTHVXHMNPTVWFU-AUWJEWJLSA-N (e)-2-(5-bromo-1h-indol-3-yl)-3-[4-(furan-3-yl)pyridin-3-yl]prop-2-enenitrile Chemical compound C12=CC(Br)=CC=C2NC=C1\C(C#N)=C/C1=CN=CC=C1C=1C=COC=1 QTHVXHMNPTVWFU-AUWJEWJLSA-N 0.000 description 5
- GOMPBEBFZVSPJK-WDZFZDKYSA-N (e)-2-(5-chloro-1h-indol-3-yl)-3-(4-methoxypyridin-3-yl)prop-2-enenitrile Chemical compound COC1=CC=NC=C1\C=C(\C#N)C1=CNC2=CC=C(Cl)C=C12 GOMPBEBFZVSPJK-WDZFZDKYSA-N 0.000 description 5
- JQWQOZLJYQUISF-BJMVGYQFSA-N (z)-2-(5-bromo-1h-indol-3-yl)-3-(4-chloropyridin-3-yl)prop-2-enenitrile Chemical compound ClC1=CC=NC=C1\C=C(/C#N)C1=CNC2=CC=C(Br)C=C12 JQWQOZLJYQUISF-BJMVGYQFSA-N 0.000 description 5
- VAOYWUWRWZBMLC-IZZDOVSWSA-N (z)-2-(5-bromo-1h-indol-3-yl)-3-(4-methoxypyridin-3-yl)prop-2-enenitrile Chemical compound COC1=CC=NC=C1\C=C(/C#N)C1=CNC2=CC=C(Br)C=C12 VAOYWUWRWZBMLC-IZZDOVSWSA-N 0.000 description 5
- WMSSHJKHSWUQAI-NTEUORMPSA-N (z)-2-(5-bromo-1h-indol-3-yl)-3-[4-(diethylamino)pyridin-3-yl]prop-2-enenitrile Chemical compound CCN(CC)C1=CC=NC=C1\C=C(/C#N)C1=CNC2=CC=C(Br)C=C12 WMSSHJKHSWUQAI-NTEUORMPSA-N 0.000 description 5
- BBOWXMBAJUUQSH-KPKJPENVSA-N (z)-2-(5-bromo-1h-indol-3-yl)-3-[4-(dimethylamino)pyridin-3-yl]prop-2-enenitrile Chemical compound CN(C)C1=CC=NC=C1\C=C(/C#N)C1=CNC2=CC=C(Br)C=C12 BBOWXMBAJUUQSH-KPKJPENVSA-N 0.000 description 5
- JDKJOBNRVIXKFD-VGOFMYFVSA-N (z)-2-(5-bromo-1h-indol-3-yl)-3-[4-(furan-3-yl)-1-oxidopyridin-1-ium-3-yl]prop-2-enenitrile Chemical compound C=1NC2=CC=C(Br)C=C2C=1C(/C#N)=C/C1=C[N+]([O-])=CC=C1C=1C=COC=1 JDKJOBNRVIXKFD-VGOFMYFVSA-N 0.000 description 5
- QTHVXHMNPTVWFU-VGOFMYFVSA-N (z)-2-(5-bromo-1h-indol-3-yl)-3-[4-(furan-3-yl)pyridin-3-yl]prop-2-enenitrile Chemical compound C12=CC(Br)=CC=C2NC=C1\C(C#N)=C\C1=CN=CC=C1C=1C=COC=1 QTHVXHMNPTVWFU-VGOFMYFVSA-N 0.000 description 5
- KOBRTBRFEPIYAT-BJMVGYQFSA-N (z)-2-(5-chloro-1h-indol-3-yl)-3-(4-chloropyridin-3-yl)prop-2-enenitrile Chemical compound C12=CC(Cl)=CC=C2NC=C1\C(C#N)=C\C1=CN=CC=C1Cl KOBRTBRFEPIYAT-BJMVGYQFSA-N 0.000 description 5
- YSHIZIIFDNWGFT-IZZDOVSWSA-N (z)-2-(5-chloro-1h-indol-3-yl)-3-(4-methoxy-1-oxidopyridin-1-ium-3-yl)prop-2-enenitrile Chemical compound COC1=CC=[N+]([O-])C=C1\C=C(/C#N)C1=CNC2=CC=C(Cl)C=C12 YSHIZIIFDNWGFT-IZZDOVSWSA-N 0.000 description 5
- XLHNPODSYJYHMQ-VGOFMYFVSA-N (z)-2-(5-chloro-1h-indol-3-yl)-3-[4-(furan-3-yl)pyridin-3-yl]prop-2-enenitrile Chemical compound C12=CC(Cl)=CC=C2NC=C1\C(C#N)=C\C1=CN=CC=C1C=1C=COC=1 XLHNPODSYJYHMQ-VGOFMYFVSA-N 0.000 description 5
- UILYIDARFPAJEV-KPKJPENVSA-N (z)-2-(5-methoxy-1h-indol-3-yl)-3-(4-methoxypyridin-3-yl)prop-2-enenitrile Chemical compound C12=CC(OC)=CC=C2NC=C1\C(C#N)=C\C1=CN=CC=C1OC UILYIDARFPAJEV-KPKJPENVSA-N 0.000 description 5
- MQVIEEVDTXZLEI-IZZDOVSWSA-N (z)-2-(6-bromo-1h-indol-3-yl)-3-(4-methoxypyridin-3-yl)prop-2-enenitrile Chemical compound COC1=CC=NC=C1\C=C(/C#N)C1=CNC2=CC(Br)=CC=C12 MQVIEEVDTXZLEI-IZZDOVSWSA-N 0.000 description 5
- JZVXOMGTWRCZND-IZZDOVSWSA-N (z)-2-(6-chloro-1h-indol-3-yl)-3-(4-methoxypyridin-3-yl)prop-2-enenitrile Chemical compound COC1=CC=NC=C1\C=C(/C#N)C1=CNC2=CC(Cl)=CC=C12 JZVXOMGTWRCZND-IZZDOVSWSA-N 0.000 description 5
- KDJYDGJCRSUGIY-IZZDOVSWSA-N (z)-2-(6-fluoro-1h-indol-3-yl)-3-(4-methoxypyridin-3-yl)prop-2-enenitrile Chemical compound COC1=CC=NC=C1\C=C(/C#N)C1=CNC2=CC(F)=CC=C12 KDJYDGJCRSUGIY-IZZDOVSWSA-N 0.000 description 5
- UFKKCHYALSLNMI-OVCLIPMQSA-N 3-[(z)-2-(5-bromo-1h-indol-3-yl)-2-cyanoethenyl]-4-(dimethylamino)benzonitrile Chemical compound CN(C)C1=CC=C(C#N)C=C1\C=C(/C#N)C1=CNC2=CC=C(Br)C=C12 UFKKCHYALSLNMI-OVCLIPMQSA-N 0.000 description 5
- DLNUDEHHHGEPNX-AWNIVKPZSA-N 3-[(z)-2-(5-bromo-1h-indol-3-yl)-2-cyanoethenyl]-4-(trifluoromethoxy)benzonitrile Chemical compound FC(F)(F)OC1=CC=C(C#N)C=C1\C=C(/C#N)C1=CNC2=CC=C(Br)C=C12 DLNUDEHHHGEPNX-AWNIVKPZSA-N 0.000 description 5
- FPLXLABOSGYPBR-AWNIVKPZSA-N 3-[(z)-2-(5-chloro-1h-indol-3-yl)-2-cyanoethenyl]-4-(trifluoromethoxy)benzonitrile Chemical compound FC(F)(F)OC1=CC=C(C#N)C=C1\C=C(/C#N)C1=CNC2=CC=C(Cl)C=C12 FPLXLABOSGYPBR-AWNIVKPZSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 241000699670 Mus sp. Species 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 5
- 229940002612 prodrug Drugs 0.000 description 5
- 239000000651 prodrug Substances 0.000 description 5
- 125000001544 thienyl group Chemical group 0.000 description 5
- 125000004014 thioethyl group Chemical group [H]SC([H])([H])C([H])([H])* 0.000 description 5
- 125000004055 thiomethyl group Chemical group [H]SC([H])([H])* 0.000 description 5
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Classifications
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- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4196—1,2,4-Triazoles
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
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- A—HUMAN NECESSITIES
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- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/02—Drugs for genital or sexual disorders; Contraceptives for disorders of the vagina
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Epidemiology (AREA)
- Endocrinology (AREA)
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- Reproductive Health (AREA)
- Pain & Pain Management (AREA)
- Gynecology & Obstetrics (AREA)
- Rheumatology (AREA)
- Diabetes (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP16306389 | 2016-10-24 | ||
| EP16306389.4 | 2016-10-24 | ||
| PCT/EP2017/076990 WO2018077795A1 (en) | 2016-10-24 | 2017-10-23 | New derivatives of indole for the treatment of endometriosis |
Publications (2)
| Publication Number | Publication Date |
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| KR20190065449A KR20190065449A (ko) | 2019-06-11 |
| KR102532912B1 true KR102532912B1 (ko) | 2023-05-15 |
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| CN (1) | CN109863144B (enExample) |
| CA (1) | CA3039918A1 (enExample) |
| IL (1) | IL265584B (enExample) |
| WO (1) | WO2018077795A1 (enExample) |
Families Citing this family (1)
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| CN104854088B (zh) | 2012-12-07 | 2018-02-16 | 生物控制术公司 | 用于治疗癌症、病毒感染和肺病的新型吲哚衍生物 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6335342B1 (en) | 2000-06-19 | 2002-01-01 | Pharmacia & Upjohn S.P.A. | Azaindole derivatives, process for their preparation, and their use as antitumor agents |
| EP1452525A4 (en) * | 2001-10-30 | 2005-01-26 | Nippon Shinyaku Co Ltd | AMIDE DERIVATIVES AND CORRESPONDING MEDICAMENTS |
| US7361764B2 (en) | 2004-07-27 | 2008-04-22 | Sgx Pharmaceuticals, Inc. | Pyrrolo-pyridine kinase modulators |
| EP2266562A1 (en) * | 2009-06-23 | 2010-12-29 | Centre National de la Recherche Scientifique | Use of derivatives of indoles for the treatment of cancer |
| CN104854088B (zh) * | 2012-12-07 | 2018-02-16 | 生物控制术公司 | 用于治疗癌症、病毒感染和肺病的新型吲哚衍生物 |
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2017
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- 2017-10-23 CA CA3039918A patent/CA3039918A1/en active Pending
- 2017-10-23 WO PCT/EP2017/076990 patent/WO2018077795A1/en not_active Ceased
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2019
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Also Published As
| Publication number | Publication date |
|---|---|
| JP7130180B2 (ja) | 2022-09-05 |
| CN109863144A (zh) | 2019-06-07 |
| CN109863144B (zh) | 2021-12-28 |
| US20190275000A1 (en) | 2019-09-12 |
| EP3529243B1 (en) | 2024-02-28 |
| EP3529243C0 (en) | 2024-02-28 |
| US10624876B2 (en) | 2020-04-21 |
| IL265584A (en) | 2019-05-30 |
| KR20190065449A (ko) | 2019-06-11 |
| WO2018077795A1 (en) | 2018-05-03 |
| JP2019531317A (ja) | 2019-10-31 |
| EP3529243A1 (en) | 2019-08-28 |
| IL265584B (en) | 2022-02-01 |
| CA3039918A1 (en) | 2018-05-03 |
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