HRP20191265T1 - Supstituirani 2-tiokso-imidazolidin-4-oni i njihovi spiro analozi, aktivni anti-kancerogeni sastojak, farmaceutska kompozicija, medicinski preparat, metoda za liječenje raka prostate - Google Patents
Supstituirani 2-tiokso-imidazolidin-4-oni i njihovi spiro analozi, aktivni anti-kancerogeni sastojak, farmaceutska kompozicija, medicinski preparat, metoda za liječenje raka prostate Download PDFInfo
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- HRP20191265T1 HRP20191265T1 HRP20191265TT HRP20191265T HRP20191265T1 HR P20191265 T1 HRP20191265 T1 HR P20191265T1 HR P20191265T T HRP20191265T T HR P20191265TT HR P20191265 T HRP20191265 T HR P20191265T HR P20191265 T1 HRP20191265 T1 HR P20191265T1
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- thioxo
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- pharmaceutical composition
- cancer
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- 238000000034 method Methods 0.000 title claims 7
- 239000008194 pharmaceutical composition Substances 0.000 title claims 6
- UGWULZWUXSCWPX-UHFFFAOYSA-N 2-sulfanylideneimidazolidin-4-one Chemical class O=C1CNC(=S)N1 UGWULZWUXSCWPX-UHFFFAOYSA-N 0.000 title claims 3
- 206010060862 Prostate cancer Diseases 0.000 title claims 2
- 208000000236 Prostatic Neoplasms Diseases 0.000 title claims 2
- 230000001093 anti-cancer Effects 0.000 title 1
- 239000004615 ingredient Substances 0.000 title 1
- 125000003003 spiro group Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 9
- 238000004519 manufacturing process Methods 0.000 claims 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 6
- 238000006243 chemical reaction Methods 0.000 claims 5
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims 4
- 206010028980 Neoplasm Diseases 0.000 claims 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 3
- 150000007513 acids Chemical class 0.000 claims 3
- 201000011510 cancer Diseases 0.000 claims 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims 2
- 229940123407 Androgen receptor antagonist Drugs 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- 239000003936 androgen receptor antagonist Substances 0.000 claims 2
- 150000002148 esters Chemical class 0.000 claims 2
- 239000000945 filler Substances 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- LBGGRQJVGBWQGH-GFCCVEGCSA-N (3R)-3-(4-carboxy-3-fluoroanilino)oxolane-3-carboxylic acid Chemical compound C(=O)(O)C1=C(C=C(C=C1)N[C@]1(COCC1)C(=O)O)F LBGGRQJVGBWQGH-GFCCVEGCSA-N 0.000 claims 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 claims 1
- -1 3-dimethylaminopropyl Chemical group 0.000 claims 1
- KYTAJCPQSBEFES-UHFFFAOYSA-N 4-(isothiocyanatomethyl)-2-(trifluoromethyl)benzonitrile Chemical compound FC(F)(F)C1=C(C=CC(CN=C=S)=C1)C#N KYTAJCPQSBEFES-UHFFFAOYSA-N 0.000 claims 1
- KFBBLPVSJVDANZ-OAQYLSRUSA-N 4-[(5R)-3-(4-cyano-3-methylphenyl)-4-oxo-2-sulfanylidene-7-oxa-1,3-diazaspiro[4.4]nonan-1-yl]-2-fluorobenzoic acid Chemical compound CC=1C=C(C=CC=1C#N)N1C(N([C@@]2(C1=O)COCC2)C1=CC(=C(C(=O)O)C=C1)F)=S KFBBLPVSJVDANZ-OAQYLSRUSA-N 0.000 claims 1
- ZQQSRVPOAHYHEL-UHFFFAOYSA-N 4-bromo-2-fluorobenzoic acid Chemical compound OC(=O)C1=CC=C(Br)C=C1F ZQQSRVPOAHYHEL-UHFFFAOYSA-N 0.000 claims 1
- 206010006187 Breast cancer Diseases 0.000 claims 1
- 208000026310 Breast neoplasm Diseases 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 150000001413 amino acids Chemical class 0.000 claims 1
- 235000019270 ammonium chloride Nutrition 0.000 claims 1
- 239000002775 capsule Substances 0.000 claims 1
- BIWDLWGXRSWSAG-XMMPIXPASA-N cyclopropyl 4-[(5R)-3-(4-cyano-3-methylphenyl)-4-oxo-2-sulfanylidene-7-oxa-1,3-diazaspiro[4.4]nonan-1-yl]-2-fluorobenzoate Chemical compound CC=1C=C(C=CC=1C#N)N1C(N([C@@]2(C1=O)COCC2)C1=CC(=C(C(=O)OC2CC2)C=C1)F)=S BIWDLWGXRSWSAG-XMMPIXPASA-N 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 150000005690 diesters Chemical class 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 239000007924 injection Substances 0.000 claims 1
- 238000002347 injection Methods 0.000 claims 1
- 229940127554 medical product Drugs 0.000 claims 1
- IAJYQRRHWIHJHC-CQSZACIVSA-N methyl (3R)-3-(3-fluoro-4-methoxycarbonylanilino)oxolane-3-carboxylate Chemical compound FC=1C=C(C=CC=1C(=O)OC)N[C@]1(COCC1)C(=O)OC IAJYQRRHWIHJHC-CQSZACIVSA-N 0.000 claims 1
- CZPTVGDJHSGLAZ-JOCHJYFZSA-N methyl 4-[(5R)-3-(4-cyano-3-methylphenyl)-4-oxo-2-sulfanylidene-7-oxa-1,3-diazaspiro[4.4]nonan-1-yl]-2-fluorobenzoate Chemical compound CC=1C=C(C=CC=1C#N)N1C(N([C@@]2(C1=O)COCC2)C1=CC(=C(C(=O)OC)C=C1)F)=S CZPTVGDJHSGLAZ-JOCHJYFZSA-N 0.000 claims 1
- FIQZMPMXZHKNHA-XMMPIXPASA-N propan-2-yl 4-[(5R)-3-(4-cyano-3-methylphenyl)-4-oxo-2-sulfanylidene-7-oxa-1,3-diazaspiro[4.4]nonan-1-yl]-2-fluorobenzoate Chemical compound CC=1C=C(C=CC=1C#N)N1C(N([C@@]2(C1=O)COCC2)C1=CC(=C(C(=O)OC(C)C)C=C1)F)=S FIQZMPMXZHKNHA-XMMPIXPASA-N 0.000 claims 1
- 239000003826 tablet Substances 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/86—Oxygen and sulfur atoms, e.g. thiohydantoin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
- A61K31/41—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
- A61K31/4164—1,3-Diazoles
- A61K31/4166—1,3-Diazoles having oxo groups directly attached to the heterocyclic ring, e.g. phenytoin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
- A61K31/41—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
- A61K31/4164—1,3-Diazoles
- A61K31/4188—1,3-Diazoles condensed with other heterocyclic ring systems, e.g. biotin, sorbinil
-
- 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
-
- 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
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
- C07C227/16—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions not involving the amino or carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/52—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C07C229/54—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton with amino and carboxyl groups bound to carbon atoms of the same non-condensed six-membered aromatic ring
- C07C229/60—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton with amino and carboxyl groups bound to carbon atoms of the same non-condensed six-membered aromatic ring with amino and carboxyl groups bound in meta- or para- positions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/18—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/10—Spiro-condensed systems
- C07D491/107—Spiro-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
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- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Furan Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Claims (16)
1. Spojevi koji su (R)-stereoizomeri supstituiranih 2-tiokso-imidazolidin-4-ona koji su prikazani općom formulom 1,
gdje:
R1 je OH, NH2, ili OR4 grupa;
R2 i R3 zajedno su CH2-CH2 grupa;
R4 je C1-C4 alkil ili ciklopropil.
2. Spojevi iz patentnog zahtjeva 1 koja su (R)-stereoizomeri supstituiranih 2-tiokso-imidazolidin-4-ona opće formule 1.1 ili 1.2,
gdje R2, R3, i R4 su kao što je definirano iznad.
3. Spojevi iz patentnog zahtjeva 1 koja su, metil 4-[(R)-3-(3-metil-4-cijanofenil)-4-okso-2-tiokso-7-oksa-1,3-diaza-spiro[4.4]non-1-il]-2-fluorobenzoat 1.1.2, izopropil 4-[(R)-3-(3-metil-4-cijano-fenil)-4-okso-2-tiokso-7-oksa-1,3-diaza-spiro[4.4]non-1-il]-2-fluoro-benzoat 1.1.3, ciklopropil 4-[(R)-3-(3-metil-4-cijano-fenil)-4-okso-2-tiokso-7-oksa-1,3-diaza-spiro[4.4]non-1-il]-2-fluoro-benzoat 1.1.4, 4-[(R)-3-(3-metil-4-cijano-fenil)-4-okso-2-tiokso-7-oksa-1,3-diaza-spiro[4.4]non-1-il]-2-fluoro-benzoeva kiselina 1.2.2, 4-[(R)-3-(3-metil-4-cijano-fenil)-4-okso-2-tiokso-7-oksa-1,3-diaza-spiro[4.4]non-1-il]-2-fluoro-benzamid 1.3.2
4. (R)-3-(4-karboksi-3-fluoro-fenilamino)-tetrahidrofuran-3-karboksilna kiselina 2.2,
ili metil (R)-3-(4-metoksikarbonil-3-fluoro-fenilamino)-tetrahidrofuran-3-karboksilat 2.4
5. Metoda za proizvodnju spojeva koji su prikazani općom formulom 2.2, kao što je definirano u patentnom zahtjevu 4, koji se sastoji u reakciji između (R)-stereoizomera amino kiseline koji su prikazani općom formulom 3.1 i 4-brom-2-fluorobenzoeve kiseline 3.2 u dimetilformamidu u prisustvu CuI i baze,
gdje R2 zajedno sa R3 su CH2-CH2 grupa.
6. Metoda za proizvodnju spojeva koja su prikazana općom formulom 2.4, kao što je definirano u patentnom zahtjevu 4, koji se sastoji u reakciji između (R)-stereoizomera relevantne dikiseline 2.2 i alkohola u prisustvu tionil klorida.
gdje R2 zajedno sa R3 su CH2-CH2grupa.
7. Metoda za proizvodnju spojeva koja su prikazana općom formulom1.1.2,kao što je definirano u patentnom zahtjevu 3, koji se sastoji u reakciji između (R)-stereoizomera relevantnog diestra 2.4 i 4-cijano-3-trifluorometil-benzil izotiocijanata 3.3 pri povišenim temperaturama,
gdje R2 i R3 su kao što je definirano iznad.
8. Metoda za proizvodnju kiselina koje su prikazane formulom 1.2.2, kao što je definirano u patentnom zahtjevu 3, preko alkalne hidrolize (R)-stereoizomera estera koje su prikazane općom formulom 1.1.2, kao što je definirano u patentnom zahtjevu 3.
9. Metoda za proizvodnju estera koji su prikazani općom formulom 1.1, kao što je definirano u patentnom zahtjevu 2, koji se sastoji u reakciji između kiselina koje su prikazane formulom 1.2, kao što je definirano u patentnom zahtjevu 2, i alkohola i tionil klorida.
10. Metoda za proizvodnju amida 1.3.2, kao što je definirano u patentnom zahtjevu 3, koja se sastoji u reakciji između kiselina koje su prikazane općom formulom 1.2, kao što je definirano u patentnom zahtjevu 2, i amonij klorida u prisustvu N-(3-dimetilaminopropil)-N'-etilkarbodiimida, 1- hidroksibenzotriazola i trietilamina u dimetilformamidu.
11. Spoj koje je prikazano formulom 1 prema patentnom zahtjevu 1 koje ima svojstva antagoniste androgenih receptora, kao aktivni sastojak za proizvodnju medicinskog proizvoda za liječenje kancerogene bolesti.
12. Farmaceutska kompozicija za primjenu u liječenju raka koja ima svojstva antagoniste androgenih receptora i sadrži efikasnu količinu spojeva koji su prikazani formulom 1 prema patentnom zahtjevu 1 i inertni punilac ili otapalo.
13. Farmaceutska kompozicija za primjenu prema patentnom zahtjevu 12 u tabletama, kapsulama, injekcijama.
14. Farmaceutska kompozicija za primjenu prema patentnom zahtjevu 12, gdje rak je rak prostate.
15. Farmaceutska kompozicija za primjenu prema patentnom zahtjevu 12, gdje rak je rak dojke.
16. Metoda za proizvodnju farmaceutske kompozicije prema patentnom zahtjevu 12 preko miješanja spojeva koje je prikazano formulom 1 prema patentnom zahtjevu 1 sa inertnim puniocem i/ili otapalom.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| RU2014127705/04A RU2557235C1 (ru) | 2014-07-08 | 2014-07-08 | Замещенные 2-тиоксо-имидазолидин-4-оны и их спироаналоги, противораковый активный компонент, фармацевтическая композиция, лекарственный препарат, способ лечения рака простаты |
| EP15818878.9A EP3168214B1 (en) | 2014-07-08 | 2015-06-26 | Substituted 2-thioxo-imidazolidin-4-ones and spiro analogues thereof, active anti-cancer ingredient, pharmaceutical composition, medicinal preparation, method for treating prostate cancer |
| PCT/RU2015/000395 WO2016007046A1 (ru) | 2014-07-08 | 2015-06-26 | Замещенные 2-тиоксо-имидазолидин-4-оны и их спироаналоги, противораковый активный компонент, фармацевтическая композиция, лекарственный препарат, способ лечения рака простаты |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| HRP20191265T1 true HRP20191265T1 (hr) | 2019-10-18 |
| HRP20191265T8 HRP20191265T8 (hr) | 2019-11-01 |
Family
ID=53611746
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20191265T HRP20191265T8 (hr) | 2014-07-08 | 2019-07-16 | Supstituirani 2-tiokso-imidazolidin-4-oni i njihovi spiro analozi, aktivni anti-kancerogeni sastojak, farmaceutska kompozicija, medicinski preparat, metoda za liječenje raka prostate |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US10450278B2 (hr) |
| EP (1) | EP3168214B1 (hr) |
| JP (1) | JP6581193B2 (hr) |
| KR (1) | KR102171120B1 (hr) |
| AU (1) | AU2015288381B2 (hr) |
| CA (1) | CA2954401C (hr) |
| CY (1) | CY1122231T1 (hr) |
| DK (1) | DK3168214T3 (hr) |
| ES (1) | ES2736507T3 (hr) |
| GE (1) | GEP20207096B (hr) |
| HR (1) | HRP20191265T8 (hr) |
| HU (1) | HUE044317T2 (hr) |
| LT (1) | LT3168214T (hr) |
| PL (1) | PL3168214T3 (hr) |
| PT (1) | PT3168214T (hr) |
| RS (1) | RS59009B1 (hr) |
| RU (1) | RU2557235C1 (hr) |
| SI (1) | SI3168214T1 (hr) |
| TR (1) | TR201910220T4 (hr) |
| UA (1) | UA117626C2 (hr) |
| WO (1) | WO2016007046A1 (hr) |
| ZA (1) | ZA201700922B (hr) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2018009678A1 (en) * | 2016-07-08 | 2018-01-11 | Janssen Pharmaceutica Nv | Substituted hydantoin and thiohydantoin derivatives as androgen receptor antagonists |
| CN107954936B (zh) * | 2016-10-17 | 2021-03-19 | 海创药业股份有限公司 | 一种制备氘代咪唑二酮类化合物的方法 |
| CN109422725A (zh) * | 2017-09-04 | 2019-03-05 | 北京美倍他药物研究有限公司 | ***癌治疗药物 |
| RU2708253C2 (ru) * | 2017-12-05 | 2019-12-05 | Федеральное государственное бюджетное образовательное учреждение высшего образования "Московский государственный университет имени М.В. Ломоносова" (МГУ) | Новые производные арил-тиогидантоина, ингибиторы андрогенового рецептора, способ получения и применения |
| SG11202106506WA (en) * | 2018-12-19 | 2021-07-29 | Celgene Corp | Substituted 3-((3-aminophenyl)amino)piperidine-2,6-dione compounds, compositions thereof, and methods of treatment therewith |
| AU2019403207A1 (en) * | 2018-12-19 | 2021-07-15 | Celgene Corporation | Substituted 3-((3-aminophenyl)amino)piperidine-2,6-dione compounds, compositions thereof, and methods of treatment therewith |
| CN114621109B (zh) * | 2020-12-14 | 2024-04-26 | 成都苑东生物制药股份有限公司 | 一种阿帕他胺的合成方法及其中间体 |
| CN113698310B (zh) * | 2021-08-20 | 2023-03-17 | 江西金丰药业有限公司 | 一种恩杂鲁胺双酯中间体的制备方法 |
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| EP3970721A1 (en) * | 2005-05-13 | 2022-03-23 | The Regents Of The University Of California | Diarylhydantoin compounds as androgen receptor antagonists for treatment of cancer |
| EP2400847B1 (en) * | 2009-02-24 | 2014-12-17 | Medivation Prostate Therapeutics, Inc. | Specific diarylthiohydantoin compounds |
| CN106983749A (zh) * | 2010-02-16 | 2017-07-28 | 亚拉冈制药公司 | 雄激素受体调节剂及其用途 |
| HUE038637T2 (hu) * | 2010-02-24 | 2018-12-28 | Medivation Prostate Therapeutics Llc | Eljárás a diaril-tiohidantoin és a diaril-hidantoin vegyületek szintetizálására |
| RU2434851C1 (ru) * | 2010-07-22 | 2011-11-27 | Александр Васильевич Иващенко | Циклические n, n'-диарилтиомочевины или n, n'-диарилмочевины - антагонисты андрогенных рецепторов, противораковое средство, способ получения и применения |
| RU2520134C1 (ru) * | 2013-02-27 | 2014-06-20 | Общество с ограниченной ответственностью "Авионко" (ООО "Авионко") | Замещенные (r)-3-(4-метилкарбамоил-3-фторфениламино)-тетрагидро-фуран-3-енкарбоновые кислоты и их эфиры, способ их получения и применения |
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| SI3168214T1 (sl) | 2019-09-30 |
| RS59009B1 (sr) | 2019-08-30 |
| GEP20207096B (en) | 2020-04-10 |
| AU2015288381A1 (en) | 2017-03-02 |
| KR20170023184A (ko) | 2017-03-02 |
| PL3168214T3 (pl) | 2019-10-31 |
| PT3168214T (pt) | 2019-07-25 |
| US10450278B2 (en) | 2019-10-22 |
| EP3168214B1 (en) | 2019-04-24 |
| ES2736507T3 (es) | 2020-01-02 |
| HRP20191265T8 (hr) | 2019-11-01 |
| TR201910220T4 (tr) | 2019-07-22 |
| LT3168214T (lt) | 2019-07-25 |
| JP2017522379A (ja) | 2017-08-10 |
| DK3168214T3 (da) | 2019-07-22 |
| JP6581193B2 (ja) | 2019-09-25 |
| EP3168214A1 (en) | 2017-05-17 |
| CA2954401C (en) | 2021-03-02 |
| EP3168214A4 (en) | 2018-02-14 |
| KR102171120B1 (ko) | 2020-10-29 |
| CY1122231T1 (el) | 2020-11-25 |
| CA2954401A1 (en) | 2016-01-14 |
| AU2015288381B2 (en) | 2019-11-07 |
| RU2557235C1 (ru) | 2015-07-20 |
| WO2016007046A1 (ru) | 2016-01-14 |
| US20180179164A1 (en) | 2018-06-28 |
| ZA201700922B (en) | 2019-08-28 |
| UA117626C2 (uk) | 2018-08-27 |
| HUE044317T2 (hu) | 2019-10-28 |
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