JPWO2020180942A5

JPWO2020180942A5 -

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Publication number: JPWO2020180942A5
Authority: JP; Japan
Prior art keywords: abiraterone; oil; pharmaceutically acceptable; decanoate; pharmaceutical composition
Prior art date: 2023-03-09
Legal status : Granted

Application number

JP2021552742A

Other languages

English (en)

Japanese (ja)

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JP2022523819A5 (https=

JP7644713B2 (ja

JP2022523819A (ja

Publication date

2023-03-09

2020-03-04 Application filed filed Critical

2020-03-04 Priority claimed from PCT/US2020/020915 external-priority patent/WO2020180942A1/en

2022-04-26 Publication of JP2022523819A publication Critical patent/JP2022523819A/ja

2023-03-09 Publication of JP2022523819A5 publication Critical patent/JP2022523819A5/ja

2023-03-09 Publication of JPWO2020180942A5 publication Critical patent/JPWO2020180942A5/ja

2025-03-12 Application granted granted Critical

2025-03-12 Publication of JP7644713B2 publication Critical patent/JP7644713B2/ja

Status Active legal-status Critical Current

2040-03-04 Anticipated expiration legal-status Critical

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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 claims description 505
229960000853 abiraterone Drugs 0.000 claims description 487
239000000203 mixture Substances 0.000 claims description 256
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims description 225
238000009472 formulation Methods 0.000 claims description 219
XPCSGTPPHYORKJ-YHXMLEJGSA-N [(3S,8R,9S,10R,13S,14S)-10,13-dimethyl-17-pyridin-3-yl-2,3,4,7,8,9,11,12,14,15-decahydro-1H-cyclopenta[a]phenanthren-3-yl] decanoate Chemical compound [H][C@@]12CC=C(C3=CC=CN=C3)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@H](CC[C@]12C)OC(=O)CCCCCCCCC XPCSGTPPHYORKJ-YHXMLEJGSA-N 0.000 claims description 213
238000000034 method Methods 0.000 claims description 169
239000008194 pharmaceutical composition Substances 0.000 claims description 146
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 130
239000003921 oil Substances 0.000 claims description 115
235000019198 oils Nutrition 0.000 claims description 115
SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 claims description 112
201000010099 disease Diseases 0.000 claims description 111
230000001419 dependent effect Effects 0.000 claims description 109
206010060862 Prostate cancer Diseases 0.000 claims description 93
208000000236 Prostatic Neoplasms Diseases 0.000 claims description 93
208000011580 syndromic disease Diseases 0.000 claims description 92
125000000217 alkyl group Chemical group 0.000 claims description 89
230000036470 plasma concentration Effects 0.000 claims description 85
230000003211 malignant effect Effects 0.000 claims description 82
238000007918 intramuscular administration Methods 0.000 claims description 77
239000002904 solvent Substances 0.000 claims description 77
239000003098 androgen Substances 0.000 claims description 76
235000019445 benzyl alcohol Nutrition 0.000 claims description 75
239000003163 gonadal steroid hormone Substances 0.000 claims description 69
239000002552 dosage form Substances 0.000 claims description 67
239000003862 glucocorticoid Substances 0.000 claims description 67
235000005687 corn oil Nutrition 0.000 claims description 62
239000002285 corn oil Substances 0.000 claims description 62
150000001875 compounds Chemical class 0.000 claims description 61
239000004359 castor oil Substances 0.000 claims description 58
235000019438 castor oil Nutrition 0.000 claims description 58
ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 claims description 58
229960002903 benzyl benzoate Drugs 0.000 claims description 56
239000003814 drug Substances 0.000 claims description 56
JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 claims description 56
150000003839 salts Chemical class 0.000 claims description 53
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239000007927 intramuscular injection Substances 0.000 claims description 40
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HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 38
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125000000753 cycloalkyl group Chemical group 0.000 claims description 28
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125000004432 carbon atom Chemical group C* 0.000 claims description 24
238000007911 parenteral administration Methods 0.000 claims description 22
WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 claims description 22
235000012343 cottonseed oil Nutrition 0.000 claims description 21
239000002385 cottonseed oil Substances 0.000 claims description 21
235000013305 food Nutrition 0.000 claims description 21
239000008159 sesame oil Substances 0.000 claims description 21
235000011803 sesame oil Nutrition 0.000 claims description 21
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 18
239000010495 camellia oil Substances 0.000 claims description 18
239000010491 poppyseed oil Substances 0.000 claims description 18
239000003549 soybean oil Substances 0.000 claims description 18
235000012424 soybean oil Nutrition 0.000 claims description 18
150000003626 triacylglycerols Chemical class 0.000 claims description 18
229960004618 prednisone Drugs 0.000 claims description 17
XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 claims description 17
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 17
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OIGNJSKKLXVSLS-VWUMJDOOSA-N prednisolone Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OIGNJSKKLXVSLS-VWUMJDOOSA-N 0.000 claims description 15
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150000001298 alcohols Chemical class 0.000 claims description 7
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238000011474 orchiectomy Methods 0.000 claims description 7
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239000007864 aqueous solution Substances 0.000 claims description 6
229960003957 dexamethasone Drugs 0.000 claims description 6
UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 claims description 6
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125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
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VHRSUDSXCMQTMA-PJHHCJLFSA-N 6alpha-methylprednisolone Chemical compound C([C@@]12C)=CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2[C@@H](O)C[C@]2(C)[C@@](O)(C(=O)CO)CC[C@H]21 VHRSUDSXCMQTMA-PJHHCJLFSA-N 0.000 claims 2
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MTZQAGJQAFMTAQ-UHFFFAOYSA-N benzoic acid ethyl ester Natural products CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 claims 1
XLXSAKCOAKORKW-AQJXLSMYSA-N gonadorelin Chemical class C([C@@H](C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N1[C@@H](CCC1)C(=O)NCC(N)=O)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@H]1NC(=O)CC1)C1=CC=C(O)C=C1 XLXSAKCOAKORKW-AQJXLSMYSA-N 0.000 claims 1
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JP2021552742A 2019-03-06 2020-03-04 アビラテロンプロドラッグ Active JP7644713B2 (ja)