CA2761389A1 - Novel prodrugs of steroidal cyp17 inhibitors/antiandrogens - Google Patents
Novel prodrugs of steroidal cyp17 inhibitors/antiandrogens Download PDFInfo
- Publication number
- CA2761389A1 CA2761389A1 CA2761389A CA2761389A CA2761389A1 CA 2761389 A1 CA2761389 A1 CA 2761389A1 CA 2761389 A CA2761389 A CA 2761389A CA 2761389 A CA2761389 A CA 2761389A CA 2761389 A1 CA2761389 A1 CA 2761389A1
- Authority
- CA
- Canada
- Prior art keywords
- compound
- alkyl
- cancer
- group
- alkylaryl
- 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.)
- Abandoned
Links
- 229940124766 Cyp17 inhibitor Drugs 0.000 title claims description 10
- 230000002280 anti-androgenic effect Effects 0.000 title claims description 9
- 239000000051 antiandrogen Substances 0.000 title claims description 9
- 229940002612 prodrug Drugs 0.000 title abstract description 38
- 239000000651 prodrug Substances 0.000 title abstract description 38
- 230000003637 steroidlike Effects 0.000 title abstract description 6
- 229940030495 antiandrogen sex hormone and modulator of the genital system Drugs 0.000 title description 5
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 41
- 238000000034 method Methods 0.000 claims abstract description 32
- 239000003098 androgen Substances 0.000 claims abstract description 28
- 206010060862 Prostate cancer Diseases 0.000 claims abstract description 27
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims abstract description 26
- 239000003814 drug Substances 0.000 claims abstract description 15
- 229940079593 drug Drugs 0.000 claims abstract description 13
- 210000002307 prostate Anatomy 0.000 claims abstract description 9
- 206010006187 Breast cancer Diseases 0.000 claims abstract description 7
- 208000026310 Breast neoplasm Diseases 0.000 claims abstract description 7
- 206010020718 hyperplasia Diseases 0.000 claims abstract description 6
- 150000001875 compounds Chemical class 0.000 claims description 115
- -1 fluoro-C2-C6-alkyl Chemical group 0.000 claims description 42
- 125000003118 aryl group Chemical group 0.000 claims description 41
- 239000000203 mixture Substances 0.000 claims description 41
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 36
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 36
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 34
- 201000011510 cancer Diseases 0.000 claims description 33
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 27
- 125000001072 heteroaryl group Chemical group 0.000 claims description 26
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 22
- 230000002378 acidificating effect Effects 0.000 claims description 21
- 230000004962 physiological condition Effects 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- 150000002367 halogens Chemical class 0.000 claims description 13
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 claims description 12
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 12
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 11
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 11
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 11
- 239000012964 benzotriazole Substances 0.000 claims description 11
- 239000003795 chemical substances by application Substances 0.000 claims description 11
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- GIIGHSIIKVOWKZ-UHFFFAOYSA-N 2h-triazolo[4,5-d]pyrimidine Chemical group N1=CN=CC2=NNN=C21 GIIGHSIIKVOWKZ-UHFFFAOYSA-N 0.000 claims description 10
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 claims description 10
- 208000025609 Urogenital disease Diseases 0.000 claims description 10
- 125000000623 heterocyclic group Chemical group 0.000 claims description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims description 10
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 8
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 8
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 8
- 239000003085 diluting agent Substances 0.000 claims description 8
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000004122 cyclic group Chemical group 0.000 claims description 7
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 7
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 6
- 208000008385 Urogenital Neoplasms Diseases 0.000 claims description 6
- 125000006294 amino alkylene group Chemical group 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 6
- 206010033128 Ovarian cancer Diseases 0.000 claims description 5
- 206010061535 Ovarian neoplasm Diseases 0.000 claims description 5
- 125000003282 alkyl amino group Chemical group 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 239000000556 agonist Substances 0.000 claims description 4
- 239000011230 binding agent Substances 0.000 claims description 4
- 239000007894 caplet Substances 0.000 claims description 4
- 239000002775 capsule Substances 0.000 claims description 4
- 239000000969 carrier Substances 0.000 claims description 4
- 238000002512 chemotherapy Methods 0.000 claims description 4
- 238000001794 hormone therapy Methods 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 238000009169 immunotherapy Methods 0.000 claims description 4
- 239000006186 oral dosage form Substances 0.000 claims description 4
- 238000001959 radiotherapy Methods 0.000 claims description 4
- 238000001356 surgical procedure Methods 0.000 claims description 4
- 239000003826 tablet Substances 0.000 claims description 4
- 208000037964 urogenital cancer Diseases 0.000 claims description 4
- 125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims description 3
- 108700012941 GNRH1 Proteins 0.000 claims description 3
- 239000000579 Gonadotropin-Releasing Hormone Substances 0.000 claims description 3
- 239000004067 bulking agent Substances 0.000 claims description 3
- 229940011871 estrogen Drugs 0.000 claims description 3
- 239000000262 estrogen Substances 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 claims description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-UHFFFAOYSA-N 0.000 claims description 2
- 229940044683 chemotherapy drug Drugs 0.000 claims description 2
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 claims description 2
- ZWRDBWDXRLPESY-UHFFFAOYSA-N n-benzyl-n-ethylethanamine Chemical compound CCN(CC)CC1=CC=CC=C1 ZWRDBWDXRLPESY-UHFFFAOYSA-N 0.000 claims description 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 claims description 2
- ODHXBMXNKOYIBV-UHFFFAOYSA-O triphenylazanium Chemical compound C1=CC=CC=C1[NH+](C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-O 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 11
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 15
- 230000003389 potentiating effect Effects 0.000 abstract description 14
- 238000011282 treatment Methods 0.000 abstract description 13
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- 102000001307 androgen receptors Human genes 0.000 abstract description 10
- 108010080146 androgen receptors Proteins 0.000 abstract description 10
- 241000282414 Homo sapiens Species 0.000 abstract description 7
- 239000003112 inhibitor Substances 0.000 abstract description 6
- 102000004190 Enzymes Human genes 0.000 abstract description 5
- 108090000790 Enzymes Proteins 0.000 abstract description 5
- 239000005557 antagonist Substances 0.000 abstract description 3
- 230000002194 synthesizing effect Effects 0.000 abstract description 2
- 101100298362 Homo sapiens PPIG gene Proteins 0.000 abstract 1
- 102000056262 human PPIG Human genes 0.000 abstract 1
- 238000011275 oncology therapy Methods 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 53
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 29
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 26
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 22
- 229940125898 compound 5 Drugs 0.000 description 21
- 229960000853 abiraterone Drugs 0.000 description 20
- GZOSMCIZMLWJML-VJLLXTKPSA-N abiraterone Chemical compound C([C@H]1[C@H]2[C@@H]([C@]3(CC[C@H](O)CC3=CC2)C)CC[C@@]11C)C=C1C1=CC=CN=C1 GZOSMCIZMLWJML-VJLLXTKPSA-N 0.000 description 20
- 239000000243 solution Substances 0.000 description 19
- 150000002148 esters Chemical class 0.000 description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
- 239000012267 brine Substances 0.000 description 13
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 13
- 235000019341 magnesium sulphate Nutrition 0.000 description 13
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- 235000019439 ethyl acetate Nutrition 0.000 description 12
- 150000003431 steroids Chemical class 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 10
- MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 description 10
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- OJRUSAPKCPIVBY-KQYNXXCUSA-N C1=NC2=C(N=C(N=C2N1[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(CP(=O)(O)O)O)O)O)I)N Chemical compound C1=NC2=C(N=C(N=C2N1[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(CP(=O)(O)O)O)O)O)I)N OJRUSAPKCPIVBY-KQYNXXCUSA-N 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- XUYJLQHKOGNDPB-UHFFFAOYSA-N carboxymethyl phosphonic acid Natural products OC(=O)CP(O)(O)=O XUYJLQHKOGNDPB-UHFFFAOYSA-N 0.000 description 8
- 238000003818 flash chromatography Methods 0.000 description 8
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 7
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 7
- 239000011369 resultant mixture Substances 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 229940125758 compound 15 Drugs 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
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- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 6
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 description 5
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- LVEYOSJUKRVCCF-UHFFFAOYSA-N 1,3-bis(diphenylphosphino)propane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCCP(C=1C=CC=CC=1)C1=CC=CC=C1 LVEYOSJUKRVCCF-UHFFFAOYSA-N 0.000 description 4
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
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- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 4
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
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- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Chemical group 0.000 description 1
- 229960003087 tioguanine Drugs 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-M toluenesulfonate group Chemical group C=1(C(=CC=CC1)S(=O)(=O)[O-])C LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000005208 trialkylammonium group Chemical group 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- QRDQHTJNKPXXRQ-UHFFFAOYSA-N tributyl(pyrimidin-5-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CN=CN=C1 QRDQHTJNKPXXRQ-UHFFFAOYSA-N 0.000 description 1
- 125000002827 triflate group Chemical class FC(S(=O)(=O)O*)(F)F 0.000 description 1
- KYWVDGFGRYJLPE-UHFFFAOYSA-N trimethylazanium;acetate Chemical compound CN(C)C.CC(O)=O KYWVDGFGRYJLPE-UHFFFAOYSA-N 0.000 description 1
- 230000004614 tumor growth Effects 0.000 description 1
- 230000002485 urinary effect Effects 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 235000019786 weight gain Nutrition 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J43/00—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C07J43/003—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton not condensed
-
- 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
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/58—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids containing heterocyclic rings, e.g. danazol, stanozolol, pancuronium or digitogenin
-
- 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
- A61K31/66—Phosphorus compounds
- A61K31/675—Phosphorus compounds having nitrogen as a ring hetero atom, e.g. pyridoxal phosphate
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61N—ELECTROTHERAPY; MAGNETOTHERAPY; RADIATION THERAPY; ULTRASOUND THERAPY
- A61N5/00—Radiation therapy
- A61N5/10—X-ray therapy; Gamma-ray therapy; Particle-irradiation therapy
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/08—Drugs for disorders of the urinary system of the prostate
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
- A61P5/28—Antiandrogens
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- Biomedical Technology (AREA)
- Endocrinology (AREA)
- Urology & Nephrology (AREA)
- Pathology (AREA)
- Radiology & Medical Imaging (AREA)
- Reproductive Health (AREA)
- Diabetes (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US15003109P | 2009-02-05 | 2009-02-05 | |
| US61/150,031 | 2009-02-05 | ||
| PCT/US2010/023391 WO2010091306A1 (en) | 2009-02-05 | 2010-02-05 | Novel prodrugs of steroidal cyp17 inhibitors/antiandrogens |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2761389A1 true CA2761389A1 (en) | 2010-08-12 |
Family
ID=42115803
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2761389A Abandoned CA2761389A1 (en) | 2009-02-05 | 2010-02-05 | Novel prodrugs of steroidal cyp17 inhibitors/antiandrogens |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US20110312916A1 (https=) |
| EP (2) | EP3023433A1 (https=) |
| JP (2) | JP2012516900A (https=) |
| CN (1) | CN102686600A (https=) |
| AU (1) | AU2010210422A1 (https=) |
| BR (1) | BRPI1008745A2 (https=) |
| CA (1) | CA2761389A1 (https=) |
| ES (1) | ES2552087T3 (https=) |
| WO (1) | WO2010091306A1 (https=) |
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|---|---|---|---|---|
| US20100048524A1 (en) | 2008-03-14 | 2010-02-25 | Angela Brodie | Novel C-17-Heteroaryl Steroidal CYP17 Inhibitors/Antiandrogens;Synthesis In Vitro Biological Activities, Pharmacokinetics and Antitumor Activity |
| US8785423B2 (en) * | 2008-04-14 | 2014-07-22 | University Of Maryland, Baltimore | Compositions and methods of inducing endoplasmic reticulum stress response for the treatment of cell proliferative diseases |
| WO2010091306A1 (en) | 2009-02-05 | 2010-08-12 | Tokai Pharmaceuticals | Novel prodrugs of steroidal cyp17 inhibitors/antiandrogens |
| BR112014001440A2 (pt) * | 2011-07-18 | 2017-02-21 | Tokai Pharmaceuticals Inc | novas composições e métodos para o tratamento de câncer de próstata |
| DE102011083725A1 (de) | 2011-09-29 | 2013-04-04 | Bayer Pharma AG | Estra-1,3,5(10),16-tetraen-3-carboxamid-Derivate, Verfahren zu ihrer Herstellung, pharmazeutische Präparate die diese enthalten, sowie deren Verwendung zur Herstellung von Arzneimitteln |
| PH12014500943A1 (en) * | 2011-11-30 | 2014-06-30 | Astrazeneca Ab | Combination treatment of cancer |
| AU2012358219A1 (en) * | 2011-12-22 | 2014-07-10 | Tokai Pharmaceuticals, Inc. | Methods and compositions for combination therapy using P13K/mTOR inhibitors |
| WO2014102833A2 (en) * | 2012-12-31 | 2014-07-03 | Hetero Research Foundation | Process for abiraterone acetate |
| WO2014111815A2 (en) * | 2013-01-18 | 2014-07-24 | Cortendo Ab (Publ) | Abiraterone and analogs thereof for the treatment of diseases associated with cortisol overproduction |
| EA201500851A1 (ru) | 2013-02-21 | 2016-02-29 | Байер Фарма Акциенгезельшафт | ЭСТРА-1,3,5(10),16-ТЕТРАЕН-3-КАРБОКСАМИДЫ ДЛЯ ИНГИБИРОВАНИЯ 17β-ГИДРОКСИСТЕРОИД-ДЕГИДРОГЕНАЗЫ (AKR1C3) |
| KR20150127720A (ko) | 2013-03-14 | 2015-11-17 | 유니버시티 오브 매릴랜드, 발티모어 | 안드로겐 수용체 하향 조절제 및 그의 용도 |
| US9694005B2 (en) | 2013-04-04 | 2017-07-04 | University Of Maryland, Baltimore | Nonsteroidal and steroidal compounds with potent androgen receptor down-regulation and anti prostate cancer activity |
| CA2920317A1 (en) | 2013-08-12 | 2015-02-19 | Tokai Pharmaceuticals, Inc. | Biomarkers for treatment of neoplastic disorders using androgen-targeted therapies |
| CN104017045B (zh) * | 2014-06-23 | 2016-01-13 | 广州艾格生物科技有限公司 | 甾体cyp17抑制剂的新型药物前体及其应用、制备方法 |
| TWI641616B (zh) * | 2014-11-28 | 2018-11-21 | 四川海思科製藥有限公司 | 阿比特龍衍生物及其製備方法和醫藥用途 |
| CN107188922B (zh) * | 2016-03-14 | 2019-12-20 | 四川海思科制药有限公司 | 一种阿比特龙衍生物的盐及其制备方法和医药用途 |
| CN107188921A (zh) * | 2016-03-15 | 2017-09-22 | 四川海思科制药有限公司 | 阿比特龙衍生物的制备方法及其新固态形式和用途 |
| CN107365343A (zh) * | 2016-05-12 | 2017-11-21 | 四川海思科制药有限公司 | 一种苯并咪唑雄甾衍生物及其制备方法和医药用途 |
| ITUA20164043A1 (it) * | 2016-06-01 | 2017-12-01 | Ind Chimica Srl | Processo per la preparazione di 3β-idrossi-17-(1H-benzimidazol-1-il)androsta-5,16-diene |
| WO2017208132A1 (en) * | 2016-06-01 | 2017-12-07 | Industriale Chimica S.R.L. | Process for the preparation of galeterone |
| CN106220705A (zh) * | 2016-07-25 | 2016-12-14 | 厦门市瑞思医药科技有限公司 | 一种2’‑(n,n,n‑三甲基氯化铵基)乙酸阿比特龙酯的合成方法 |
| CN109846826A (zh) * | 2019-01-25 | 2019-06-07 | 湖南华腾制药有限公司 | 醋酸阿比特龙柔性脂质体及其制备方法 |
| JP7644713B2 (ja) * | 2019-03-06 | 2025-03-12 | プロペラ セラピューティクス インコーポレイテッド | アビラテロンプロドラッグ |
| WO2021100019A1 (en) | 2019-11-22 | 2021-05-27 | Suven Life Sciences Limited | Prodrugs of abiraterone |
| CN116583529B (zh) * | 2020-12-12 | 2026-02-13 | 上海喀露蓝科技有限公司 | 阿比特龙衍生物及其制备方法 |
| CN117120034A (zh) | 2021-02-15 | 2023-11-24 | 普洛佩拉治疗公司 | 阿比特龙前药 |
| JP2024511277A (ja) | 2021-02-19 | 2024-03-13 | メビオン・メディカル・システムズ・インコーポレーテッド | 粒子線治療システムのためのガントリー |
| CN113061154B (zh) * | 2021-03-25 | 2022-07-08 | 天津海润家和创新医药研究有限责任公司 | 新型注射用阿比特龙衍生物的制备方法和用途 |
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| ES2552087T3 (es) | 2015-11-25 |
| AU2010210422A8 (en) | 2011-08-25 |
| JP2016034946A (ja) | 2016-03-17 |
| US9359395B2 (en) | 2016-06-07 |
| AU2010210422A1 (en) | 2011-08-18 |
| US20140371181A1 (en) | 2014-12-18 |
| JP2012516900A (ja) | 2012-07-26 |
| US20110312916A1 (en) | 2011-12-22 |
| BRPI1008745A2 (pt) | 2019-09-17 |
| WO2010091306A1 (en) | 2010-08-12 |
| CN102686600A (zh) | 2012-09-19 |
| EP3023433A1 (en) | 2016-05-25 |
| EP2393827B1 (en) | 2015-10-07 |
| EP2393827A1 (en) | 2011-12-14 |
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