JPWO2021108288A5 - - Google Patents

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JPWO2021108288A5
JPWO2021108288A5 JP2022530976A JP2022530976A JPWO2021108288A5 JP WO2021108288 A5 JPWO2021108288 A5 JP WO2021108288A5 JP 2022530976 A JP2022530976 A JP 2022530976A JP 2022530976 A JP2022530976 A JP 2022530976A JP WO2021108288 A5 JPWO2021108288 A5 JP WO2021108288A5
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chlorophenyl
cyclohexyl
propanamide
fluoroquinolin
cocrystal
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JP2023504400A (en
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Priority claimed from PCT/US2020/061743 external-priority patent/WO2021108288A1/en
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結晶質（（Ｒ）－Ｎ－（４－クロロフェニル）－２－（（１Ｓ，４Ｓ）－４－（６－フルオロキノリン－４－イル）シクロヘキシル）プロパンアミド塩酸塩一水和物形態Ａ。 Crystalline ((R)-N-(4-chlorophenyl)-2-((1S,4S)-4-(6-fluoroquinolin-4-yl)cyclohexyl)propanamide hydrochloride monohydrate Form A. 実質的に図１：
Figure 2021108288000001
に示すような粉末Ｘ線回折パターンを特徴とする、請求項１に記載の結晶質（（Ｒ）－Ｎ－（４－クロロフェニル）－２－（（１Ｓ，４Ｓ）－４－（６－フルオロキノリン－４－イル）シクロヘキシル）プロパンアミド塩酸塩。 Substantially Figure 1 :
Figure 2021108288000001
The crystalline ((R)-N-(4-chlorophenyl)-2-((1S,4S)-4-(6-fluorophenyl)) according to claim 1, characterized by a powder X-ray diffraction pattern as shown in Quinolin-4-yl)cyclohexyl)propanamide hydrochloride. 結晶質（（Ｒ）－Ｎ－（４－クロロフェニル）－２－（（１Ｓ，４Ｓ）－４－（６－フルオロキノリン－４－イル）シクロヘキシル）プロパンアミド無水塩酸塩形態Ｂ。 Crystalline ((R)-N-(4-chlorophenyl)-2-((1S,4S)-4-(6-fluoroquinolin-4-yl)cyclohexyl)propanamide hydrochloride anhydrous Form B. 実質的に図４：
Figure 2021108288000002
に示すような粉末Ｘ線回折パターンを特徴とする、請求項３に記載の結晶質（（Ｒ）－Ｎ－（４－クロロフェニル）－２－（（１Ｓ，４Ｓ）－４－（６－フルオロキノリン－４－イル）シクロヘキシル）プロパンアミド塩酸塩。 Substantially Figure 4 :
Figure 2021108288000002
The crystalline ((R)-N-(4-chlorophenyl)-2-((1S,4S)-4-(6-fluoro Quinolin-4-yl)cyclohexyl)propanamide hydrochloride. 結晶質（（Ｒ）－Ｎ－（４－クロロフェニル）－２－（（１Ｓ，４Ｓ）－４－（６－フルオロキノリン－４－イル）シクロヘキシル）プロパンアミドエシル酸塩形態Ｃ。 Crystalline ((R)-N-(4-chlorophenyl)-2-((1S,4S)-4-(6-fluoroquinolin-4-yl)cyclohexyl)propanamide esylate Form C. 実質的に図５：
Figure 2021108288000003
に示すような粉末Ｘ線回折パターンを特徴とする、請求項５に記載の結晶質（（Ｒ）－Ｎ－（４－クロロフェニル）－２－（（１Ｓ，４Ｓ）－４－（６－フルオロキノリン－４－イル）シクロヘキシル）プロパンアミドエシル酸塩。 Substantially Figure 5 :
Figure 2021108288000003
The crystalline ((R)-N-(4-chlorophenyl)-2-((1S,4S)-4-(6-fluoro Quinolin-4-yl)cyclohexyl)propanamide esylate. （Ｒ）－Ｎ－（４－クロロフェニル）－２－（（１Ｓ，４Ｓ）－４－（６－フルオロキノリン－４－イル）シクロヘキシル）プロパンアミドの酢酸溶媒和物／塩。 Acetic acid solvate/salt of (R)-N-(4-chlorophenyl)-2-((1S,4S)-4-(6-fluoroquinolin-4-yl)cyclohexyl)propanamide. （Ｒ）－Ｎ－（４－クロロフェニル）－２－（（１Ｓ，４Ｓ）－４－（６－フルオロキノリン－４－イル）シクロヘキシル）プロパンアミドリン酸塩のリン酸塩／共結晶。 Phosphate/cocrystal of (R)-N-(4-chlorophenyl)-2-((1S,4S)-4-(6-fluoroquinolin-4-yl)cyclohexyl)propanamide phosphate. （Ｒ）－Ｎ－（４－クロロフェニル）－２－（（１Ｓ，４Ｓ）－４－（６－フルオロキノリン－４－イル）シクロヘキシル）プロパンアミドナパジシル酸塩／共結晶。 (R)-N-(4-chlorophenyl)-2-((1S,4S)-4-(6-fluoroquinolin-4-yl)cyclohexyl)propanamide napadisylate/cocrystal. （Ｒ）－Ｎ－（４－クロロフェニル）－２－（（１Ｓ，４Ｓ）－４－（６－フルオロキノリン－４－イル）シクロヘキシル）プロパンアミド硫酸塩／共結晶。 (R)-N-(4-chlorophenyl)-2-((1S,4S)-4-(6-fluoroquinolin-4-yl)cyclohexyl)propanamide sulfate/cocrystal. （Ｒ）－Ｎ－（４－クロロフェニル）－２－（（１Ｓ，４Ｓ）－４－（６－フルオロキノリン－４－イル）シクロヘキシル）プロパンアミドベシル酸塩／共結晶。 (R)-N-(4-chlorophenyl)-2-((1S,4S)-4-(6-fluoroquinolin-4-yl)cyclohexyl)propanamide besylate/cocrystal. （Ｒ）－Ｎ－（４－クロロフェニル）－２－（（１Ｓ，４Ｓ）－４－（６－フルオロキノリン－４－イル）シクロヘキシル）プロパンアミドクエン酸塩／共結晶。 (R)-N-(4-chlorophenyl)-2-((1S,4S)-4-(6-fluoroquinolin-4-yl)cyclohexyl)propanamide citrate/cocrystal. （Ｒ）－Ｎ－（４－クロロフェニル）－２－（（１Ｓ，４Ｓ）－４－（６－フルオロキノリン－４－イル）シクロヘキシル）プロパンアミドＬ－リンゴ酸塩／共結晶。 (R)-N-(4-chlorophenyl)-2-((1S,4S)-4-(6-fluoroquinolin-4-yl)cyclohexyl)propanamide L-malate/cocrystal. （Ｒ）－Ｎ－（４－クロロフェニル）－２－（（１Ｓ，４Ｓ）－４－（６－フルオロキノリン－４－イル）シクロヘキシル）プロパンアミドＬ－酒石酸塩／共結晶。 (R)-N-(4-chlorophenyl)-2-((1S,4S)-4-(6-fluoroquinolin-4-yl)cyclohexyl)propanamide L-tartrate/cocrystal. （Ｒ）－Ｎ－（４－クロロフェニル）－２－（（１Ｓ，４Ｓ）－４－（６－フルオロキノリン－４－イル）シクロヘキシル）プロパンアミドフマル酸塩／共結晶。 (R)-N-(4-chlorophenyl)-2-((1S,4S)-4-(6-fluoroquinolin-4-yl)cyclohexyl)propanamide fumarate/cocrystal. （Ｒ）－Ｎ－（４－クロロフェニル）－２－（（１Ｓ，４Ｓ）－４－（６－フルオロキノリン－４－イル）シクロヘキシル）プロパンアミドエジシル酸塩／共結晶。 (R)-N-(4-chlorophenyl)-2-((1S,4S)-4-(6-fluoroquinolin-4-yl)cyclohexyl)propanamide edisylate/cocrystal. （Ｒ）－Ｎ－（４－クロロフェニル）－２－（（１Ｓ，４Ｓ）－４－（６－フルオロキノリン－４－イル）シクロヘキシル）プロパンアミドＬ－酒石酸塩／共結晶。 (R)-N-(4-chlorophenyl)-2-((1S,4S)-4-(6-fluoroquinolin-4-yl)cyclohexyl)propanamide L-tartrate/cocrystal. （Ｒ）－Ｎ－（４－クロロフェニル）－２－（（１Ｓ，４Ｓ）－４－（６－フルオロキノリン－４－イル）シクロヘキシル）プロパンアミドフマル酸塩／共結晶。 (R)-N-(4-chlorophenyl)-2-((1S,4S)-4-(6-fluoroquinolin-4-yl)cyclohexyl)propanamide fumarate/cocrystal. （Ｒ）－Ｎ－（４－クロロフェニル）－２－（（１Ｓ，４Ｓ）－４－（６－フルオロキノリン－４－イル）シクロヘキシル）プロパンアミドＬ－リンゴ酸塩／共結晶。 (R)-N-(4-chlorophenyl)-2-((1S,4S)-4-(6-fluoroquinolin-4-yl)cyclohexyl)propanamide L-malate/cocrystal. （Ｒ）－Ｎ－（４－クロロフェニル）－２－（（１Ｓ，４Ｓ）－４－（６－フルオロキノリン－４－イル）シクロヘキシル）プロパンアミドナパジシル酸塩／共結晶。 (R)-N-(4-chlorophenyl)-2-((1S,4S)-4-(6-fluoroquinolin-4-yl)cyclohexyl)propanamide napadisylate/cocrystal. （Ｒ）－Ｎ－（４－クロロフェニル）－２－（（１Ｓ，４Ｓ）－４－（６－フルオロキノリン－４－イル）シクロヘキシル）プロパンアミドリン酸塩／共結晶。 (R)-N-(4-chlorophenyl)-2-((1S,4S)-4-(6-fluoroquinolin-4-yl)cyclohexyl)propanamide phosphate/cocrystal. （Ｒ）－Ｎ－（４－クロロフェニル）－２－（（１Ｓ，４Ｓ）－４－（６－フルオロキノリン－４－イル）シクロヘキシル）プロパンアミドクエン酸塩／共結晶。 (R)-N-(4-chlorophenyl)-2-((1S,4S)-4-(6-fluoroquinolin-4-yl)cyclohexyl)propanamide citrate/cocrystal. （Ｒ）－Ｎ－（４－クロロフェニル）－２－（（１Ｓ，４Ｓ）－４－（６－フルオロキノリン－４－イル）シクロヘキシル）プロパンアミドトシル酸塩／共結晶。 (R)-N-(4-chlorophenyl)-2-((1S,4S)-4-(6-fluoroquinolin-4-yl)cyclohexyl)propanamide tosylate/cocrystal. 請求項１～２３のいずれか一項に記載の化合物またはそれらの任意の組合せを含む、がんを治療するための医薬組成物。 A pharmaceutical composition for treating cancer comprising a compound according to any one of claims 1 to 23 or any combination thereof. がんが、前立腺、大腸、直腸、膵臓、子宮頸部、胃、子宮内膜、脳、肝臓、膀胱、卵巣、精巣、頭部、頸部、皮膚（黒色腫および基底癌を含む）、中皮ライニング（ｍｅｓｏｔｈｅｌｉａｌ ｌｉｎｉｎｇ）、白血球（リンパ腫および白血病を含む）、食道、***、筋肉、結合組織、肺（小細胞肺癌および非小細胞癌腫を含む）、副腎、甲状腺、腎臓もしくは骨のがんであるか；または膠芽腫、中皮腫、腎細胞癌、胃の癌腫、肉腫（カポジ肉腫を含む）、絨毛癌、皮膚基底細胞癌または睾丸精上皮腫である、請求項２４に記載の医薬組成物。 Cancers of the prostate, colon, rectum, pancreas, cervix, stomach, endometrium, brain, liver, bladder, ovaries, testicles, head, neck, skin (including melanoma and basal cancer), mesothelial lining, white blood cell (including lymphoma and leukemia), esophagus, breast, muscle, connective tissue, lung (including small cell lung cancer and non-small cell carcinoma), adrenal gland, thyroid, kidney or bone cancer or glioblastoma, mesothelioma, renal cell carcinoma, gastric carcinoma, sarcoma (including Kaposi's sarcoma), choriocarcinoma, cutaneous basal cell carcinoma, or testicular seminoma. thing . 免疫チェックポイント阻害剤を併用する、請求項２４に記載の医薬組成物。 The pharmaceutical composition according to claim 24, which is used in combination with an immune checkpoint inhibitor. 免疫チェックポイント阻害剤が、イピリムマブ（ＹＥＲＶＯＹ（商標））、ニボルマブ（ＯＰＤＩＶＯ（商標））、ペムブロリズマブ（ｐｅｍｂｒｏｌｕｚｉｍａｂ）（ＫＥＹＴＲＵＤＡ（商標））またはそれらの組合せである、請求項２４に記載の医薬組成物。 25. The pharmaceutical composition of claim 24, wherein the immune checkpoint inhibitor is ipilimumab (YERVOY™), nivolumab (OPDIVO™), pembroluzimab (KEYTRUDA™) or a combination thereof. 請求項１～２３のいずれか一項に記載の化合物またはそれらの任意の組合せを含む医薬組成物であって、インドールアミン２，３－ジオキシゲナーゼを請求項１～２３のいずれか一項に記載の化合物またはそれらの任意の組合せと接触させて、インドールアミン２，３－ジオキシゲナーゼの活性を調節する医薬組成物。 24. A pharmaceutical composition comprising a compound according to any one of claims 1 to 23 or any combination thereof, wherein an indoleamine 2,3-dioxygenase according to any one of claims 1 to 23 A pharmaceutical composition that modulates the activity of indoleamine 2,3-dioxygenase upon contact with the described compounds or any combination thereof .
JP2022530976A 2019-11-26 2020-11-23 Salt/co-crystal of (R)-N-(4-chlorophenyl)-2-((1S,4S)-4-(6-fluoroquinolin-4-yl)cyclohexyl)propanamide Pending JP2023504400A (en)

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US201962940642P 2019-11-26 2019-11-26
US62/940,642 2019-11-26
PCT/US2020/061743 WO2021108288A1 (en) 2019-11-26 2020-11-23 Salts/cocrystals of (r)-n-(4-chlorophenyl)-2-((1s,4s)-4-(6-fluoroquinolin-4-yl)cyclohexyl)propanamide

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US (1) US20230052523A1 (en)
EP (1) EP4065226A1 (en)
JP (1) JP2023504400A (en)
KR (1) KR20220104794A (en)
CN (1) CN115151306A (en)
AU (1) AU2020393854A1 (en)
BR (1) BR112022009944A2 (en)
CA (1) CA3159071A1 (en)
IL (1) IL293357A (en)
MX (1) MX2022006134A (en)
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