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米国特許第４５４３２５６号明細書
国際公開第２００１／０７８７１３号パンフレット
国際公開第０２／１００３７７号パンフレット
国際公開第２００９／０２６９３４，号パンフレット
国際公開第２００９／０２６９３５号パンフレット
国際公開第２０１０／０９７０９２号パンフレット
Ａｌｅｘａｎｄｅｒ ｅｔ Ｃｒｕｔｃｈｅｒ，（１９９０）Ｔｒｅｎｄｓ ｉｎ Ｎｅｕｒｏｓｃｉｅｎｃｅ １３：２６６－７１；
Ｂｉｂｂｉａｎｉ ｅｔ ａｌ．，Ｃｈａｓｅ Ｅｘｐｅｒｉｍｅｎｔａｌ Ｎｅｕｒｏｌｏｇｙ（２００５），１９２：７３－７８；
Ｂｒｕｅｃｋｎｅｒ ａｎｄ ｃｏ－ｗｏｒｋｅｒｓ ｉｎ Ｓｙｎｔｈｅｓｉｓ ２００８，１４：２２２９－２２４６；
Ｃａｍｐｂｅｌｌ ｅｔ ａｌ．，Ｎｅｕｒｏｐｈａｒｍａｃｏｌｏｇｙ（１９８２）；２１（１０）：９５３－９６１；
Ｃａｎｎｏｎ ｅｔ ａｌ．，Ｊ．Ｈｅｔｅｒｏｃｙｃｌｉｃ Ｃｈｅｍ．（１９８０）；１７：１６３３－１６３６；
Ｄｅｌｏｎｇ，（１９９０）Ｔｒｅｎｄｓ ｉｎ Ｎｅｕｒｏｓｃｉｅｎｃｅ １３：２８１－５；
Ｆａｎ ｅｔ ａｌ．，Ｂｉｏｏｒｇ．Ｍｅｄ．Ｃｈｅｍ．Ｌｅｔｔ．２００８，１８：６２３６－６２３９；
Ｇｅｒｆｅｎ ｅｔ ａｌ，Ｓｃｉｅｎｃｅ（１９９０）２５０：１４２９－３２；
Ｇｉａｒｄｉｎａ ａｎｄ Ｗｉｌｌｉａｍｓ；ＣＮＳ Ｄｒｕｇ Ｒｅｖｉｅｗｓ（２００１），Ｖｏｌ．７（３）：３０５－３１６）；
Ｇｒｏｓｓｅｔ ｅｔ ａｌ．，Ａｃｔａ Ｎｅｕｒｏｌ Ｓｃａｎｄ．（２０１３），１２８：１６６－１７１；
Ｈａｕｓｅｒ ｅｔ ａｌ．，Ｍｏｖｅｍｅｎｔ Ｄｉｓｏｒｄｅｒｓ（２０１６），Ｖｏｌ．３２（９）：１３６７－１３７２；
Ｋｏｔｓｕｋｉ ｅｔ ａｌ．，Ｊ．Ｏｒｇ．Ｃｈｅｍ．１９９２，５７：５０３６－５０４０）；
Ｌｉｕ ｅｔ ａｌ．，Ｊ．Ｍｅｄ．Ｃｈｅｍ．（２００６），４９：１４９４－１４９８；
Ｌｉｕ ｅｔ ａｌ．，Ｂｉｏｏｒｇａｎｉｃ Ｍｅｄ．Ｃｈｅｍ．（２００８），１６：３４３８－３４４４；
Ｓ．Ｎｉｓｈｉｍｕｒａ，Ｗｉｌｅｙ ２００１，Ｈａｎｄｂｏｏｋ ｏｆ ｈｅｔｅｒｏｇｅｎｅｏｕｓ ｈｙｄｒｏｇｅｎａｔｉｏｎ；
Ｐｏｅｗｅ ｅｔ ａｌ．，Ｎａｔｕｒｅ Ｒｅｖｉｅｗ，（２０１７）ｖｏｌ ３ ａｒｔｉｃｌｅ １７０１３：１－２１；
Ｓｐｒｅｎｇｅｒ ａｎｄ Ｐｏｅｗｅ，ＣＮＳ Ｄｒｕｇｓ（２０１３），２７：２５９－２７２；
Ｓｏｚｉｏ ｅｔ ａｌ．，Ｅｘｐ．Ｏｐｉｎ．Ｄｒｕｇ Ｄｉｓｃ．（２０１２）；７（５）：３８５－４０６；
Ｓｔａｈｌ ａｎｄ Ｗｅｒｍｕｔｈ（Ｅｄｓ）“Ｈａｎｄｂｏｏｋ ｏｆ Ｐｈａｒｍａｃｅｕｔｉｃａｌ ｓａｌｔｓ．Ｐｒｏｐｅｒｔｉｅｓ，ｓｅｌｅｃｔｉｏｎ，ａｎｄ ｕｓｅ”，Ｗｉｌｅｙ－ＶＣＨ，２００８；
本発明は以下の態様を含み得る。
［１］
以下の式
を有する化合物（Ｉ）を、以下の式
を有する化合物（Ｉｂ）から製造するプロセス。
［２］
化合物（Ｉｂ）が、以下の工程：
工程０）
化合物（Ａ１）を３－クロロプロパン－１－アミンと反応させて、化合物（ａ２ｉ）を得るサブステップ（ｉ）；又は
化合物（ａ６ｉ）をｔｅｒｔ－ブチル２－ブロモアセテート及び亜鉛と反応させて、混合物を形成するサブステップ（Ｓ１）、続いて
サブステップ（Ｓ１）からの前記混合物を酢酸で処理し、続いて
前記混合物を３－クロロプロパン－１－アミン塩酸塩と反応させて化合物（ａ２ｉ）を得る工程；続いて
工程１）
サブステップ（ｉ）又はサブステップ（Ｓ１）で得られる前記化合物（ａ２ｉ）を還元して、化合物（ａ２ｉｉ）を得るサブステップ（ｉｉ）、続いて
Ｌ－酒石酸を使用して化合物（ａ２ｉｉ）を分割し、化合物（Ａ２－ヘミ－Ｌ－酒石酸塩）を得るサブステップ（ｉｉｉ）；又は
サブステップ（ｉ）又はサブステップ（Ｓ１）に続いて、水素及び溶媒の存在下にてキラル触媒を用いて行われる水素化に化合物（ａ２ｉ）をかけて、化合物（Ａ２）を得る工程を含む、サブステップ（ｉｖ）；
を含むプロセスによって、以下の反応スキーム：
に従って製造される、請求項１に記載のプロセス。
［３］
化合物（Ｉｂ）が、以下の工程：
工程０）
化合物（ａ６ｉ）をｔｅｒｔ－ブチル２－ブロモアセテート及び亜鉛と反応させて、混合物を形成するサブステップ（Ｓ１）、続いて
サブステップ（Ｓ１）からの前記混合物を酢酸で処理し、続いて
前記混合物を３－クロロプロパン－１－アミン塩酸塩と反応させて化合物（ａ２ｉ）を得る工程；続いて
工程１）
サブステップ（Ｓ１）で得られる前記化合物（ａ２ｉ）を還元して、化合物（ａ２ｉｉ）を得るサブステップ（ｉｉ）、続いて
Ｌ－酒石酸を使用して化合物（ａ２ｉｉ）を分割し、化合物（Ａ２－ヘミ－Ｌ－酒石酸塩）を得るサブステップ（ｉｉｉ）；
を含むプロセスによって製造される、請求項１及び２のいずれか一項に記載のプロセス。
［４］
以下の式（Ａ２）
の化合物、又はその塩。
［５］
工程１サブステップ（ｉｖ）における前記キラル触媒が、（２Ｓ）－１－［（１Ｓ）－１－［ビス（１，１－ジメチルエチル）フォスフィノ］エチル］－２－（ジフェニルフォスフィノ）フェロセン及びビス（２，５－ノルボルナジエン）ロジウム（Ｉ）テトラフルオロボレートから選択される、請求項２に記載のプロセス。
［６］
工程１サブステップ（ｉｖ）における前記溶媒が、２，２，２－トリフルオロエタノールである、請求項２及び５に記載のプロセス。
［７］
工程１サブステップ（ｉｉ）における前記還元が、ＮａＢＨ
３
ＣＮ、トリアセトキシ水素化ホウ素ナトリウム（ＳＴＡＢ）、ボラン、５－エチル－２－メチルピリジンボラン（ＰＥＭＢ）及びＮａＢＨ
４
からなる群から選択される還元剤の存在下で行われる、請求項１～３のいずれか一項に記載のプロセス。
［８］
工程１サブステップ（ｉｉ）における前記還元が、白金触媒、好ましくは炭素担持白金を使用して行われる、請求項１～３のいずれか一項に記載のプロセス。
［９］
化合物（Ｉｂ）が、以下の工程：
２）還元剤の存在下にて化合物（Ａ２）又は化合物（Ａ２－ヘミ－Ｌ－酒石酸塩）をプロパナールと反応させて、以下の反応スキームａ）又はｂ）
に従って化合物（Ａ３）が得られる、工程を含むプロセスによって製造される、請求項１～３、及び５～９に記載のプロセス。
［１０］
以下の式（Ａ３）
の化合物、又はその塩。
［１１］
化合物（Ｉｂ）が、以下の工程：
３）化合物（Ａ３）を強塩基と反応させて、以下の反応スキーム
に従って化合物Ａ４を得て、続いて
任意に、化合物（Ａ４）又はその塩を単離する工程を含むプロセスによって製造される、請求項１～３、５～９のいずれか一項に記載のプロセス。
［１２］
Ａ４が、以下に示すＨＣｌ塩
として単離される、請求項１１に記載のプロセス。
［１３］
以下の式（Ａ４）
の化合物、又はその塩。
［１４］
化合物（Ｉｂ）が、以下の工程：
４）化合物（Ａ４）の分子内フリーデル－クラフツのアシル化を行い、以下の反応スキーム
に従って化合物（Ａ５）を得て、続いて
任意に、化合物（Ａ５）又はその塩を単離する工程を含むプロセスによって製造される、請求項１～３、５～９、及び１１～１２のいずれか一項に記載のプロセス。
［１５］
以下の式（Ａ５）
の化合物、又はその塩。
［１６］
化合物（Ｉｂ）が、以下の工程：
５）化合物（Ａ５）又はその塩を還元して、以下の反応スキーム
に従って化合物（Ｉｂ）又はその塩が得られる工程を含むプロセスによって製造される、請求項１～３、５～９、１１～１２、及び１４のいずれか一項に記載のプロセス。
［１７］
化合物（Ｉ）が、以下の工程：
６）ＢＣｌ
３
、ＢＢｒ
３
及びＨＢｒからなる群から選択されるルイス酸又はブレンステッド酸と化合物（Ｉｂ）を反応させて、以下の反応スキーム
に従って、化合物（Ｉ）が得られる工程によって化合物（Ｉｂ）から製造される、請求項１～３、５～９、１１～１２、１４、及び１６のいずれか一項に記載のプロセス。
［１８］
以下の式（ａ２ｉ）
の化合物、又はその塩。
［１９］
以下の式（ａ２ｉｉ）
の化合物、又はその塩。
Reference list U.S. Pat. Alexander et Crutcher, (1990) Trends in Neuroscience 13:266-71;
Bibbani et al. , Chase Experimental Neurology (2005), 192:73-78;
Bruckner and co-workers in Synthesis 2008, 14:2229-2246;
Campbell et al. , Neuropharmacology (1982);21(10):953-961;
Cannon et al. , J. Heterocyclic Chem. (1980); 17:1633-1636;
Delong, (1990) Trends in Neuroscience 13:281-5;
Fan et al. , Bioorg. Med. Chem. Lett. 2008, 18:6236-6239;
Gerfen et al, Science (1990) 250:1429-32;
Giardina and Williams; CNS Drug Reviews (2001), Vol. 7(3):305-316);
Grosset et al. , Acta Neurol Scan. (2013), 128:166-171;
Hauser et al. , Movement Disorders (2016), Vol. 32(9):1367-1372;
Kotsuki et al. , J. Org. Chem. 1992, 57:5036-5040);
Liu et al. , J. Med. Chem. (2006), 49:1494-1498;
Liu et al. , Bioorganic Med. Chem. (2008), 16:3438-3444;
S. Nishimura, Wiley 2001, Handbook of heterogeneous hydrogenation;
Poewe et al. , Nature Review, (2017) vol 3 article 17013: 1-21;
Sprenger and Poewe, CNS Drugs (2013), 27:259-272;
Sozio et al. , Exp. Opin. Drug Disc. (2012); 7(5):385-406;
Stahl and Wermuth (Eds) "Handbook of Pharmaceutical salts. Properties, selection, and use", Wiley-VCH, 2008;
The present invention may include the following aspects.
[1]
the formula below
Compound (I) having the formula
A process for producing from compound (Ib) having
[2]
Compound (Ib) was prepared by the following steps:
process 0)
substep (i) of reacting compound (A1) with 3-chloropropan-1-amine to give compound (a2i); or
substep (S1) of reacting compound (a6i) with tert-butyl 2-bromoacetate and zinc to form a mixture, followed by
treating said mixture from sub-step (S1) with acetic acid followed by
reacting the mixture with 3-chloropropan-1-amine hydrochloride to obtain compound (a2i); followed by
process 1)
Substep (ii) of reducing said compound (a2i) obtained in substep (i) or substep (S1) to obtain compound (a2ii), followed by
substep (iii) of resolving compound (a2ii) using L-tartaric acid to give compound (A2-hemi-L-tartrate); or
Sub-step (i) or sub-step (S1) is followed by subjecting compound (a2i) to hydrogenation carried out with a chiral catalyst in the presence of hydrogen and a solvent to obtain compound (A2). , substep (iv);
The following reaction scheme by a process involving:
2. The process of claim 1, manufactured according to.
[3]
Compound (Ib) was prepared by the following steps:
process 0)
substep (S1) of reacting compound (a6i) with tert-butyl 2-bromoacetate and zinc to form a mixture, followed by
treating said mixture from sub-step (S1) with acetic acid followed by
reacting the mixture with 3-chloropropan-1-amine hydrochloride to obtain compound (a2i); followed by
process 1)
substep (ii) of reducing said compound (a2i) obtained in substep (S1) to obtain compound (a2ii), followed by
substep (iii) of resolving compound (a2ii) using L-tartaric acid to give compound (A2-hemi-L-tartrate);
3. The process of any one of claims 1 and 2, manufactured by a process comprising
[4]
The following formula (A2)
or a salt thereof.
[5]
The chiral catalyst in step 1 substep (iv) is (2S)-1-[(1S)-1-[bis(1,1-dimethylethyl)phosphino]ethyl]-2-(diphenylphosphino)ferrocene and 3. The process of claim 2, selected from bis(2,5-norbornadiene)rhodium(I) tetrafluoroborate.
[6]
6. The process of claims 2 and 5, wherein the solvent in step 1 substep (iv) is 2,2,2-trifluoroethanol.
[7]
said reduction in step 1 substep (ii) is selected from the group consisting of NaBH 3 CN, sodium triacetoxyborohydride (STAB), borane, 5-ethyl-2-methylpyridine borane (PEMB) and NaBH 4 A process according to any one of claims 1 to 3, carried out in the presence of a reducing agent.
[8]
A process according to any one of claims 1 to 3, wherein said reduction in step 1 substep (ii) is carried out using a platinum catalyst, preferably platinum on carbon.
[9]
Compound (Ib) was prepared by the following steps:
2) reacting compound (A2) or compound (A2-hemi-L-tartrate) with propanal in the presence of a reducing agent to obtain the following reaction schemes a) or b);
Process according to claims 1-3 and 5-9, produced by a process comprising the step of obtaining compound (A3) according to
[10]
The following formula (A3)
or a salt thereof.
[11]
Compound (Ib) was prepared by the following steps:
3) reacting compound (A3) with a strong base to give the following reaction scheme
Compound A4 is obtained according to followed by
A process according to any one of claims 1-3, 5-9, optionally produced by a process comprising isolating compound (A4) or a salt thereof.
[12]
A4 is the HCl salt shown below
12. The process of claim 11, isolated as
[13]
The following formula (A4)
or a salt thereof.
[14]
Compound (Ib) was prepared by the following steps:
4) Intramolecular Friedel-Crafts acylation of compound (A4) is carried out according to the following reaction scheme
Compound (A5) is obtained according to followed by
The process of any one of claims 1-3, 5-9, and 11-12, optionally produced by a process comprising isolating compound (A5) or a salt thereof.
[15]
The following formula (A5)
or a salt thereof.
[16]
Compound (Ib) was prepared by the following steps:
5) reducing the compound (A5) or a salt thereof to obtain the following reaction scheme
A process according to any one of claims 1-3, 5-9, 11-12 and 14, wherein the compound (Ib) or a salt thereof is obtained according to
[17]
Compound (I) is prepared by the following steps:
6) reacting compound (Ib) with a Lewis acid or Bronsted acid selected from the group consisting of BCl 3 , BBr 3 and HBr to obtain the following reaction scheme
The process of any one of claims 1-3, 5-9, 11-12, 14, and 16, wherein compound (Ib) is prepared by a process whereby compound (I) is obtained according to.
[18]
Equation (a2i) below
or a salt thereof.
[19]
Equation (a2ii) below
or a salt thereof.
Claims (22)
を有する化合物（Ｉ）を、以下の式
を有する化合物（Ｉｂ）から製造するプロセスであって、
化合物（Ｉｂ）が、以下の工程：
工程０）
化合物（Ａ１）を３－クロロプロパン－１－アミンと反応させて、化合物（ａ２ｉ）を得るサブステップ（ｉ）；又は
化合物（ａ６ｉ）をｔｅｒｔ－ブチル２－ブロモアセテート及び亜鉛と反応させて、混合物を形成するサブステップ（Ｓ１）、続いて
サブステップ（Ｓ１）からの前記混合物を酢酸で処理し、続いて
前記混合物を３－クロロプロパン－１－アミン塩酸塩と反応させて化合物（ａ２ｉ）を得る工程；続いて
工程１）
サブステップ（ｉ）又はサブステップ（Ｓ１）で得られる前記化合物（ａ２ｉ）を還元して、化合物（ａ２ｉｉ）を得るサブステップ（ｉｉ）、続いて
Ｌ－酒石酸を使用して化合物（ａ２ｉｉ）を分割し、化合物（Ａ２－ヘミ－Ｌ－酒石酸塩）を得るサブステップ（ｉｉｉ）；又は
サブステップ（ｉ）又はサブステップ（Ｓ１）に続いて、水素及び溶媒の存在下にてキラル触媒を用いて行われる水素化に化合物（ａ２ｉ）をかけて、化合物（Ａ２）を得る工程を含む、サブステップ（ｉｖ）；
を含むプロセスによって、以下の反応スキーム：
に従って製造される、プロセス。 the formula below
Compound (I) having the formula
A process for producing from a compound (Ib) having
Compound (Ib) was prepared by the following steps:
process 0)
substep (i) of reacting compound (A1) with 3-chloropropan-1-amine to give compound (a2i); or
substep (S1) of reacting compound (a6i) with tert-butyl 2-bromoacetate and zinc to form a mixture, followed by
treating said mixture from sub-step (S1) with acetic acid followed by
reacting the mixture with 3-chloropropan-1-amine hydrochloride to obtain compound (a2i); followed by
process 1)
Substep (ii) of reducing said compound (a2i) obtained in substep (i) or substep (S1) to obtain compound (a2ii), followed by
substep (iii) of resolving compound (a2ii) using L-tartaric acid to give compound (A2-hemi-L-tartrate); or
Sub-step (i) or sub-step (S1) is followed by subjecting compound (a2i) to hydrogenation carried out with a chiral catalyst in the presence of hydrogen and a solvent to obtain compound (A2). , substep (iv);
The following reaction scheme by a process involving:
Manufactured according to the process .
工程０）
化合物（ａ６ｉ）をｔｅｒｔ－ブチル２－ブロモアセテート及び亜鉛と反応させて、混合物を形成するサブステップ（Ｓ１）、続いて
サブステップ（Ｓ１）からの前記混合物を酢酸で処理し、続いて
前記混合物を３－クロロプロパン－１－アミン塩酸塩と反応させて化合物（ａ２ｉ）を得る工程；続いて
工程１）
サブステップ（Ｓ１）で得られる前記化合物（ａ２ｉ）を還元して、化合物（ａ２ｉｉ）を得るサブステップ（ｉｉ）、続いて
Ｌ－酒石酸を使用して化合物（ａ２ｉｉ）を分割し、化合物（Ａ２－ヘミ－Ｌ－酒石酸塩）を得るサブステップ（ｉｉｉ）；
を含むプロセスによって製造される、請求項１に記載のプロセス。 Compound (Ib) was prepared by the following steps:
process 0)
substep (S1) of reacting compound (a6i) with tert-butyl 2-bromoacetate and zinc to form a mixture, followed by treating said mixture from substep (S1) with acetic acid, followed by said mixture with 3-chloropropan-1-amine hydrochloride to obtain compound (a2i); followed by step 1)
Substep (ii) of reducing said compound (a2i) obtained in substep (S1) to give compound (a2ii), followed by resolving compound (a2ii) using L-tartaric acid to give compound (A2 - substep (iii) to obtain hemi-L-tartrate);
10. The process of claim 1 manufactured by a process comprising:
の化合物、又はその塩。 The following formula (A2)
or a salt thereof.
２）還元剤の存在下にて化合物（Ａ２）又は化合物（Ａ２－ヘミ－Ｌ－酒石酸塩）をプロパナールと反応させて、以下の反応スキームａ）又はｂ）
に従って化合物（Ａ３）が得られる、工程を含むプロセスによって製造される、請求項１～２、及び４～８のいずれか一項に記載のプロセス。 Compound (Ib) was prepared by the following steps:
2) reacting compound (A2) or compound (A2-hemi-L-tartrate) with propanal in the presence of a reducing agent to obtain the following reaction schemes a) or b);
Process according to any one of claims 1 to 2 and 4 to 8, produced by a process comprising the step of obtaining compound (A3) according to
の化合物、又はその塩。 The following formula (A3)
or a salt thereof.
３）化合物（Ａ３）を強塩基と反応させて、以下の反応スキーム
に従って化合物Ａ４を得て、続いて
任意に、化合物（Ａ４）又はその塩を単離する工程を含むプロセスによって製造される、請求項１～２、及び４～８のいずれか一項に記載のプロセス。 Compound (Ib) was prepared by the following steps:
3) reacting compound (A3) with a strong base to give the following reaction scheme
of any one of claims 1-2 and 4-8 , prepared by a process comprising obtaining compound A4 according to process.
として単離される、請求項１０に記載のプロセス。 A4 is the HCl salt shown below
11. The process of claim 10 , isolated as
の化合物、又はその塩。 The following formula (A4)
or a salt thereof.
４）化合物（Ａ４）の分子内フリーデル－クラフツのアシル化を行い、以下の反応スキーム
に従って化合物（Ａ５）を得て、続いて
任意に、化合物（Ａ５）又はその塩を単離する工程を含むプロセスによって製造される、請求項１～２、４～８、及び１０～１１のいずれか一項に記載のプロセス。 Compound (Ib) was prepared by the following steps:
4) Intramolecular Friedel-Crafts acylation of compound (A4) is carried out according to the following reaction scheme
and optionally isolating compound (A5 ) or a salt thereof according to or the process of paragraph 1.
の化合物、又はその塩。 The following formula (A5)
or a salt thereof.
５）化合物（Ａ５）又はその塩を還元して、以下の反応スキーム
に従って化合物（Ｉｂ）又はその塩が得られる工程を含むプロセスによって製造される、請求項１～２、４～８、１０～１１、及び１３のいずれか一項に記載のプロセス。 Compound (Ib) was prepared by the following steps:
5) reducing the compound (A5) or a salt thereof to obtain the following reaction scheme
Process according to any one of claims 1-2 , 4-8 , 10-11 and 13 , wherein the compound (Ib) or a salt thereof is obtained according to
６）ＢＣｌ３、ＢＢｒ３及びＨＢｒからなる群から選択されるルイス酸又はブレンステッド酸と化合物（Ｉｂ）を反応させて、以下の反応スキーム
に従って、化合物（Ｉ）が得られる工程によって化合物（Ｉｂ）から製造される、請求項１～２、４～８、１０～１１、１３、及び１５のいずれか一項に記載のプロセス。 Compound (I) is prepared by the following steps:
6) reacting compound (Ib) with a Lewis acid or Bronsted acid selected from the group consisting of BCl 3 , BBr 3 and HBr to obtain the following reaction scheme
Process according to any one of claims 1-2 , 4-8 , 10-11 , 13 and 15 , wherein compound (Ib) is prepared by a process whereby compound (I) is obtained according to
の化合物、又はその塩。 Equation (a2i) below
or a salt thereof.
の化合物、又はその塩。
Equation (a2ii) below
or a salt thereof.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DKPA201900600 | 2019-05-20 | ||
| DKPA201900600 | 2019-05-20 | ||
| PCT/EP2020/063913 WO2020234273A1 (en) | 2019-05-20 | 2020-05-19 | A process for the manufacturing of (6ar,10ar)-7-propyl-6,6a,7,8,9,10,10a,11-octahydro-[1,3]dioxolo[4',5':5,6]benzo[1,2-g]quinoline and (4ar,10ar)-1-propyl-1,2,3,4,4a,5,10,10a-octahydro-benzo[g]quinoline-6,7-diol |
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| Publication Number | Publication Date |
|---|---|
| JP2022533155A JP2022533155A (en) | 2022-07-21 |
| JPWO2020234273A5 true JPWO2020234273A5 (en) | 2023-05-22 |
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| Application Number | Title | Priority Date | Filing Date |
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| JP2021568476A Pending JP2022533155A (en) | 2019-05-20 | 2020-05-19 | (6AR, 10AR) -7-propyl-6,6A, 7,8,9,10,10A, 11-octahydro- [1,3] dioxolo [4', 5': 5,6] benzo [1,2] Process for producing -G] quinoline and (4AR, 10AR) -1-propyl-1,2,3,4,4A, 5,10,10A-octahydro-benzo [G] quinoline-6,7-diol |
Country Status (15)
| Country | Link |
|---|---|
| US (3) | US11168056B2 (en) |
| EP (1) | EP3972958A1 (en) |
| JP (1) | JP2022533155A (en) |
| KR (1) | KR20220009949A (en) |
| CN (1) | CN113874355A (en) |
| AR (1) | AR123407A1 (en) |
| AU (1) | AU2020278810A1 (en) |
| BR (1) | BR112021000796A2 (en) |
| CA (1) | CA3140803A1 (en) |
| CL (1) | CL2021003016A1 (en) |
| IL (1) | IL288053A (en) |
| MX (1) | MX2021014016A (en) |
| SG (1) | SG11202112721WA (en) |
| WO (1) | WO2020234273A1 (en) |
| ZA (1) | ZA202109122B (en) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10729710B2 (en) | 2017-11-24 | 2020-08-04 | H. Lundbeck A/S | Catecholamine prodrugs for use in the treatment of Parkinson's disease |
| US11168056B2 (en) | 2019-05-20 | 2021-11-09 | H. Lundbeck A/S | Process for the manufacturing of (6aR,10aR)-7-propyl-6,6a,7,8,9,10,10a,11-octahydro-[1,3]dioxolo[4′,5′:5,6]benzo[1,2-G]quinoline and (4aR,10aR)-1-propyl-1,2,3,4,4a,5,10,10a-octahydro-benzo[G]quinoline-6,7-diol |
| US11130775B2 (en) | 2019-05-20 | 2021-09-28 | H. Lundbeck A/S | Solid forms of (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(((4aR,10aR)-7-hydroxy-1-propyl-1,2,3,4,4A,5,10,10A-octahydrobenzo[g]quinolin-6-yl)oxy)tetrahydro-2H-pyran-2-carboxylic acid |
| US11111263B2 (en) | 2019-05-20 | 2021-09-07 | H. Lundbeck A/S | Process for the manufacture of (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(((4aR,10aR)-7-hydroxy-1-propyl-1,2,3,4,4a,5,10,10a-octahydrobenzo[g]quinolin-6-yl)oxy)tetrahydro-2H-pyran-2-carboxylic acid |
| US11104697B2 (en) | 2019-05-20 | 2021-08-31 | H. Lundbeck A/S | Process for the manufacture of (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(((4AR,10AR)-7-hydroxy-1- propyl-1,2,3,4,4A,5,10,10A-octahydrobenzo[g]quinolin-6-yl)oxy)tetrahydro-2H-pyran-2-carboxylic acid |
| WO2023208865A1 (en) | 2022-04-25 | 2023-11-02 | Integrative Research Laboratories Sweden Ab | NOVEL 1,2,3,4,4a,5,6,7,8,9,10,10a-DODECAHYDROBENZO[G]QUINOLIN-6-OL COMPOUNDS AND USES THEREOF |
| WO2023208869A1 (en) | 2022-04-25 | 2023-11-02 | Integrative Research Laboratories Sweden Ab | NOVEL ESTERS OF 1,2,3,4,4a,5,6,7,8,9,10,10a-DODECAHYDROBENZO[G]QUINOLIN-6-OL COMPOUNDS AND USES THEREOF |
| WO2023208867A1 (en) | 2022-04-25 | 2023-11-02 | Integrative Research Laboratories Sweden Ab | NOVEL 1,2,3,4,4a,5,8,9,10,10a-DECAHYDROBENZO[G]QUINOLIN-6(7H)-ONE COMPOUNDS AND USES THEREOF |
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-
2020
- 2020-05-18 US US16/876,966 patent/US11168056B2/en active Active
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- 2020-05-19 EP EP20728427.4A patent/EP3972958A1/en active Pending
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- 2020-05-19 SG SG11202112721WA patent/SG11202112721WA/en unknown
- 2020-05-19 CN CN202080036363.4A patent/CN113874355A/en active Pending
- 2020-05-19 WO PCT/EP2020/063913 patent/WO2020234273A1/en active Application Filing
- 2020-05-19 KR KR1020217036911A patent/KR20220009949A/en unknown
- 2020-05-19 AU AU2020278810A patent/AU2020278810A1/en active Pending
- 2020-05-19 JP JP2021568476A patent/JP2022533155A/en active Pending
- 2020-05-19 CA CA3140803A patent/CA3140803A1/en active Pending
- 2020-05-19 BR BR112021000796A patent/BR112021000796A2/en unknown
-
2021
- 2021-10-07 US US17/495,997 patent/US11866410B2/en active Active
- 2021-11-11 IL IL288053A patent/IL288053A/en unknown
- 2021-11-15 CL CL2021003016A patent/CL2021003016A1/en unknown
- 2021-11-16 ZA ZA2021/09122A patent/ZA202109122B/en unknown
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2023
- 2023-07-26 US US18/359,136 patent/US20240018107A1/en active Pending
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