JPWO2021089873A5 - - Google Patents
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- JPWO2021089873A5 JPWO2021089873A5 JP2022526073A JP2022526073A JPWO2021089873A5 JP WO2021089873 A5 JPWO2021089873 A5 JP WO2021089873A5 JP 2022526073 A JP2022526073 A JP 2022526073A JP 2022526073 A JP2022526073 A JP 2022526073A JP WO2021089873 A5 JPWO2021089873 A5 JP WO2021089873A5
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- formula iii
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 18
- 150000001875 compounds Chemical class 0.000 claims 17
- 238000000034 method Methods 0.000 claims 17
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 12
- 239000007822 coupling agent Substances 0.000 claims 11
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 claims 5
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 claims 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 5
- 229910010082 LiAlH Inorganic materials 0.000 claims 5
- 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 5
- BDNKZNFMNDZQMI-UHFFFAOYSA-N 1,3-diisopropylcarbodiimide Chemical compound CC(C)N=C=NC(C)C BDNKZNFMNDZQMI-UHFFFAOYSA-N 0.000 claims 4
- FPIRBHDGWMWJEP-UHFFFAOYSA-N 1-hydroxy-7-azabenzotriazole Chemical compound C1=CN=C2N(O)N=NC2=C1 FPIRBHDGWMWJEP-UHFFFAOYSA-N 0.000 claims 4
- HJBLUNHMOKFZQX-UHFFFAOYSA-N 3-hydroxy-1,2,3-benzotriazin-4-one Chemical compound C1=CC=C2C(=O)N(O)N=NC2=C1 HJBLUNHMOKFZQX-UHFFFAOYSA-N 0.000 claims 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 4
- 239000000654 additive Substances 0.000 claims 4
- 230000000996 additive effect Effects 0.000 claims 4
- BGRWYRAHAFMIBJ-UHFFFAOYSA-N diisopropylcarbodiimide Natural products CC(C)NC(=O)NC(C)C BGRWYRAHAFMIBJ-UHFFFAOYSA-N 0.000 claims 4
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 3
- 239000012445 acidic reagent Substances 0.000 claims 3
- 150000001412 amines Chemical class 0.000 claims 3
- 150000001718 carbodiimides Chemical class 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 238000004128 high performance liquid chromatography Methods 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 239000002904 solvent Substances 0.000 claims 3
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 claims 2
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims 2
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 claims 2
- 229910052805 deuterium Inorganic materials 0.000 claims 2
- 235000019439 ethyl acetate Nutrition 0.000 claims 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N fumaric acid group Chemical group C(\C=C\C(=O)O)(=O)O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims 2
- 239000012535 impurity Substances 0.000 claims 2
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 claims 1
- 241000720974 Protium Species 0.000 claims 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Natural products CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 claims 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
- 239000001530 fumaric acid Substances 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- ROSDSFDQCJNGOL-UHFFFAOYSA-N protonated dimethyl amine Natural products CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 claims 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 1
Claims (17)
ｎは０、１、２、３または４から選択され、
Ｒ １ は、－Ｒ ３ 、－ＯＲ ３ 、－Ｏ（ＣＯ）Ｒ ３ 、－Ｆ、－Ｃｌ、－Ｂｒまたは－Ｉから独立して選択され、しかも
Ｒ ２ およびＲ ３ は、独立して、Ｃ １ －Ｃ ４ アルキルから選択される）
を合成するための方法であって、当該方法がステージ１、ステージ２、および任意にステージ３を含み、ステージ１が、以下の工程：
(i)式Ｉの化合物
ａ）ジイソプロピルカルボジイミド（ＤＩＣ）およびＮ－（３－ジメチルアミノプロピル）－Ｎ’－エチルカルボジイミド（ＥＤＣ）からなるグループから選択されるカルボジイミド；および
ｂ）１－ヒドロキシベンゾトリアゾール、ヒドロキシ－３，４－ジヒドロ－４－オキソ－１，２，３－ベンゾトリアジン、Ｎ－ヒドロキシスクシンイミド、１－ヒドロキシ－７－アザ－１Ｈ－ベンゾトリアゾール、エチル２－シアノ－２－（ヒドロキシミノ）アセテートおよび４－（Ｎ，Ｎ－ジメチルアミノ）ピリジンからなるグループから選択される添加カップリング剤を含む；
(ii)前記の活性化化合物を、式（Ｒ２）２ＮＨを有するアミンと反応させて、式IIの化合物
を含み、
ステージ２が、式IIの化合物をＬｉＡｌＨ４および／またはＬｉＡｌＤ４と反応させることを含み、ＬｉＡｌＨ ４ および／またはＬｉＡｌＤ ４ ：式IIの化合物の比０．５：１～２：１を用いて、式IIIの化合物を生成する、
および任意に、ステージ３が、式IIIの化合物を酸性試薬と反応させて、式IIIの化合物の薬学的に許容される塩を生成することを含む、
式IIIの化合物の合成方法。 Compounds of Formula III:
n is selected from 0, 1, 2, 3 or 4;
R 1 is independently selected from —R 3 , —OR 3 , —O(CO)R 3 , —F, —Cl, —Br or —I, and
R 2 and R 3 are independently selected from C 1 -C 4 alkyl)
comprising stage 1 , stage 2 , and optionally stage 3 , stage 1 comprising the following steps:
(i) a compound of formula I
a) a carbodiimide selected from the group consisting of diisopropylcarbodiimide (DIC) and N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide (EDC); and
b) 1-hydroxybenzotriazole, hydroxy-3,4-dihydro-4-oxo-1,2,3-benzotriazine, N-hydroxysuccinimide, 1-hydroxy-7-aza-1H-benzotriazole, ethyl 2- an additive coupling agent selected from the group consisting of cyano-2-(hydroxymino)acetate and 4-(N,N-dimethylamino)pyridine;
(ii) reacting said activated compound with an amine having the formula (R 2 ) 2 NH to give a compound of formula II;
including
Stage 2 comprises reacting the compound of formula II with LiAlH 4 and/or LiAlD 4 , using a LiAlH 4 and/or LiAlD 4 : compound of formula II ratio of 0.5:1 to 2:1, to produce a compound of formula III,
and optionally, stage 3 comprises reacting the compound of formula III with an acidic reagent to produce a pharmaceutically acceptable salt of the compound of formula III.
Methods of Synthesis of Compounds of Formula III .
式IIIの化合物が、ＨＰＬＣによる２つ以下の不純物ピークを含む、および／またはＨＰＬＣによる不純物ピークが０．２％より大きくない、請求項１～１０のいずれか一項に記載の方法。 the compound of formula III is produced in between 99% and 100% purity by HPLC, and/or
A process according to any one of claims 1 to 10 , wherein the compound of formula III contains no more than two impurity peaks by HPLC and/or no more than 0.2% impurity peaks by HPLC .
（Ａ）式Ｉの化合物またはその薬学的に許容される塩、
（Ｂ）２つ以上のカップリング剤で、当該カップリング剤が、
ａ）ジイソプロピルカルボジイミド（ＤＩＣ）およびＮ－（３－ジメチルアミノプロピル）－Ｎ’－エチルカルボジイミド（ＥＤＣ）からなるグループから選択されるカルボジイミド；および
ｂ）１－ヒドロキシベンゾトリアゾール、ヒドロキシ－３，４－ジヒドロ－４－オキソ－１，２，３－ベンゾトリアジン、Ｎ－ヒドロキシスクシンイミド、１－ヒドロキシ－７－アザ－１Ｈ－ベンゾトリアゾール、エチル２－シアノ－２－（ヒドロキシミノ）アセテートおよび４－（Ｎ，Ｎ－ジメチルアミノ）ピリジンからなるグループから選択される添加カップリング剤を含む；
（Ｃ）式（Ｒ ２ ） ２ ＮＨを有するアミン、
（Ｄ）ＬｉＡｌＨ ４ および／またはＬｉＡｌＤ ４ 、この際、ＬｉＡｌＨ ４ および／またはＬｉＡｌＤ ４ ：式IIの化合物の比は０．５：１～２：１である、および
（Ｅ）任意に、式IIIの化合物の薬学的に許容される塩の製造に適した酸性試薬、
を含み、この際、式IおよびIIIの化合物が、請求項１に記載されたものである、
キット。 A kit suitable for preparing a compound of formula III, said kit comprising:
(A) a compound of Formula I or a pharmaceutically acceptable salt thereof;
(B) two or more coupling agents, wherein the coupling agents are
a) a carbodiimide selected from the group consisting of diisopropylcarbodiimide (DIC) and N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide (EDC); and
b) 1-hydroxybenzotriazole, hydroxy-3,4-dihydro-4-oxo-1,2,3-benzotriazine, N-hydroxysuccinimide, 1-hydroxy-7-aza-1H-benzotriazole, ethyl 2- an additive coupling agent selected from the group consisting of cyano-2-(hydroxymino)acetate and 4-(N,N-dimethylamino)pyridine;
(C) an amine having the formula (R 2 ) 2 NH;
(D) LiAlH 4 and/or LiAlD 4 , wherein the ratio of LiAlH 4 and/or LiAlD 4 to the compound of formula II is from 0.5:1 to 2:1, and
(E) optionally an acidic reagent suitable for the preparation of pharmaceutically acceptable salts of compounds of Formula III;
wherein the compounds of formulas I and III are as defined in claim 1
kit .
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1916210.6 | 2019-11-07 | ||
| GBGB1916210.6A GB201916210D0 (en) | 2019-11-07 | 2019-11-07 | High purity tryptamines and methods of synthesis thereof |
| GB1917320.2 | 2019-11-28 | ||
| GBGB1917320.2A GB201917320D0 (en) | 2019-11-28 | 2019-11-28 | Novel compounds |
| GB2008303.6A GB2585978B (en) | 2019-06-03 | 2020-06-02 | Therapeutic compositions |
| GB2008303.6 | 2020-06-02 | ||
| PCT/EP2020/081503 WO2021089873A1 (en) | 2019-11-07 | 2020-11-09 | Method of synthesis |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2023500532A JP2023500532A (en) | 2023-01-06 |
| JPWO2021089873A5 true JPWO2021089873A5 (en) | 2023-02-02 |
| JP7422473B2 JP7422473B2 (en) | 2024-01-26 |
Family
ID=75849570
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2022526073A Active JP7422473B2 (en) | 2019-11-07 | 2020-11-09 | Synthesis method |
| JP2022526074A Active JP7423131B2 (en) | 2019-11-07 | 2020-11-09 | Compound |
| JP2023202672A Pending JP2024028798A (en) | 2019-11-07 | 2023-11-30 | Compound |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2022526074A Active JP7423131B2 (en) | 2019-11-07 | 2020-11-09 | Compound |
| JP2023202672A Pending JP2024028798A (en) | 2019-11-07 | 2023-11-30 | Compound |
Country Status (18)
| Country | Link |
|---|---|
| US (4) | US11643390B2 (en) |
| EP (3) | EP3873883B1 (en) |
| JP (3) | JP7422473B2 (en) |
| KR (2) | KR20230142817A (en) |
| CN (2) | CN114829341B (en) |
| AU (2) | AU2020378647B2 (en) |
| BR (1) | BR112022008919A2 (en) |
| CA (2) | CA3160334A1 (en) |
| DK (1) | DK3844147T3 (en) |
| ES (2) | ES2920681T3 (en) |
| HR (2) | HRP20230281T1 (en) |
| HU (2) | HUE061482T2 (en) |
| IL (2) | IL292753B2 (en) |
| MX (1) | MX2022005399A (en) |
| NZ (1) | NZ788543A (en) |
| PL (2) | PL3844147T3 (en) |
| PT (2) | PT3873883T (en) |
| WO (2) | WO2021089872A1 (en) |
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| CN116056705A (en) | 2020-08-05 | 2023-05-02 | 巴塞尔大学医院 | Intravenous DMT administration method for DMT assisted psychotherapy |
| US11406619B2 (en) | 2020-08-28 | 2022-08-09 | Small Pharma Ltd | Injectable formulations |
| US20220062237A1 (en) | 2020-08-28 | 2022-03-03 | Small Pharma Ltd | Injectable formulation |
| CN115701994B (en) | 2020-08-28 | 2024-03-08 | 赛本英国有限公司 | Injectable formulations |
| EP4221682A2 (en) | 2020-10-02 | 2023-08-09 | Cybin IRL Limited | Methods for delivery of psychedelic medications by inhalation and systems for performing the methods |
| US11000534B1 (en) | 2020-10-08 | 2021-05-11 | Lennham Pharmaceuticals, Inc. | Deuterated derivatives of psilocybin and uses thereof |
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