JPWO2010143582A1 - フェニルシクロプロピルアミン誘導体及びｌｓｄ１阻害剤 - Google Patents

フェニルシクロプロピルアミン誘導体及びｌｓｄ１阻害剤 Download PDF

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Publication number: JPWO2010143582A1
Authority: JP; Japan
Prior art keywords: bonded; substituent; group; compound; ncl
Prior art date: 2009-06-11
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.): Pending

Application number

JP2011518500A

Other languages

English (en)

Japanese (ja)

Inventor

直樹宮田

孝禎鈴木

理恵上田

民夫水上

隆造佐々木

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

FRONTIER PHARMA INC.

Nagoya City University

EDUCATIONAL CORP KANSAI BUNRI SOUGOUGAKUEN

Original Assignee

FRONTIER PHARMA INC.

Nagoya City University

EDUCATIONAL CORP KANSAI BUNRI SOUGOUGAKUEN

Priority date (The priority date 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 date listed.)

2009-06-11

Filing date

2010-06-03

Publication date

2012-11-22

2010-06-03 Application filed by FRONTIER PHARMA INC., Nagoya City University, EDUCATIONAL CORP KANSAI BUNRI SOUGOUGAKUEN filed Critical FRONTIER PHARMA INC.

2012-11-22 Publication of JPWO2010143582A1 publication Critical patent/JPWO2010143582A1/ja

Status Pending legal-status Critical Current

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AOTWIFLKURJQGE-UHFFFAOYSA-N n-cyclopropylaniline Chemical class C1CC1NC1=CC=CC=C1 AOTWIFLKURJQGE-UHFFFAOYSA-N 0.000 title claims abstract description 22
229940123628 Lysine (K)-specific demethylase 1A inhibitor Drugs 0.000 title claims abstract description 8
150000001875 compounds Chemical class 0.000 claims abstract description 95
125000001424 substituent group Chemical group 0.000 claims abstract description 39
-1 phenyloxy group Chemical group 0.000 claims abstract description 18
150000003839 salts Chemical class 0.000 claims abstract description 12
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 11
125000000217 alkyl group Chemical group 0.000 claims abstract description 9
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 8
239000000651 prodrug Substances 0.000 claims abstract description 8
229940002612 prodrug Drugs 0.000 claims abstract description 8
239000012453 solvate Substances 0.000 claims abstract description 7
239000001257 hydrogen Substances 0.000 claims abstract description 6
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125000002947 alkylene group Chemical group 0.000 claims abstract description 5
125000003545 alkoxy group Chemical group 0.000 claims abstract description 3
125000003282 alkyl amino group Chemical group 0.000 claims abstract description 3
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims abstract description 3
125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 claims abstract description 3
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims abstract description 3
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HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical group NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 claims description 2
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CNEIRVCAPVXEKP-VOTSOKGWSA-N methyl (E)-3-[3-(methoxymethoxy)phenyl]prop-2-enoate Chemical compound COCOC1=CC=CC(\C=C\C(=O)OC)=C1 CNEIRVCAPVXEKP-VOTSOKGWSA-N 0.000 description 6
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NITWSHWHQAQBAW-QPJJXVBHSA-N (E)-4-coumaric acid methyl ester Chemical compound COC(=O)\C=C\C1=CC=C(O)C=C1 NITWSHWHQAQBAW-QPJJXVBHSA-N 0.000 description 5
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
- C07C237/22—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton having nitrogen atoms of amino groups bound to the carbon skeleton of the acid part, further acylated
- 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
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
- 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
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
- A61K31/166—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide having the carbon of a carboxamide group directly attached to the aromatic ring, e.g. procainamide, procarbazine, metoclopramide, labetalol
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C235/18—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having at least one of the singly-bound oxygen atoms further bound to a carbon atom of a six-membered aromatic ring, e.g. phenoxyacetamides
- C07C235/20—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having at least one of the singly-bound oxygen atoms further bound to a carbon atom of a six-membered aromatic ring, e.g. phenoxyacetamides having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring

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Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Pharmacology & Pharmacy (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Epidemiology (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP2017513842A (ja) *	2014-04-11	2017-06-01	武田薬品工業株式会社	シクロプロパンアミン化合物およびその用途

Families Citing this family (46)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2010043721A1 (fr)	2008-10-17	2010-04-22	Oryzon Genomics, S.A.	Inhibiteurs d’oxydases et leur utilisation
US8993808B2 (en)	2009-01-21	2015-03-31	Oryzon Genomics, S.A.	Phenylcyclopropylamine derivatives and their medical use
US8859555B2 (en)	2009-09-25	2014-10-14	Oryzon Genomics S.A.	Lysine Specific Demethylase-1 inhibitors and their use
EP2486002B1 (fr)	2009-10-09	2019-03-27	Oryzon Genomics, S.A.	Acétamides d'hétéroaryl- et aryl-cyclopropylamine substitués et leur utilisation
WO2011106573A2 (fr)	2010-02-24	2011-09-01	Oryzon Genomics, S.A.	Inhibiteurs de la lysine déméthylase utilisés dans le traitement et la prévention de maladies et de troubles associés à hepadnaviridae
US9616058B2 (en)	2010-02-24	2017-04-11	Oryzon Genomics, S.A.	Potent selective LSD1 inhibitors and dual LSD1/MAO-B inhibitors for antiviral use
MX2012012111A (es)	2010-04-19	2013-05-30	Oryzon Genomics Sa	Inhibidores de demetilasa-1 especifica de lisina y su uso.
AU2011244478B2 (en)	2010-04-20	2014-07-17	Fondazione IEO-CCM	Tranylcypromine derivatives as inhibitors of histone demethylase LSD1 and/or LSD2
SI2598482T1 (sl)	2010-07-29	2018-09-28	Oryzon Genomics, S.A.	Inhibitorji demetilaze lsd1 na osnovi arilciklopropilamina in njihova medicinska uporaba
WO2012013727A1 (fr)	2010-07-29	2012-02-02	Oryzon Genomics S.A.	Dérivés de cyclopropylamine utiles en tant qu'inhibiteurs de lsd1
WO2012045883A1 (fr)	2010-10-08	2012-04-12	Oryzon Genomics S.A.	Inhibiteurs d'oxydases de cyclopropylamine
WO2012072713A2 (fr)	2010-11-30	2012-06-07	Oryzon Genomics, S.A.	Inhibiteurs de la déméthylase spécifique de la lysine pour des maladies et troubles liés aux flaviviridés
WO2012107498A1 (fr)	2011-02-08	2012-08-16	Oryzon Genomics S.A.	Inhibiteurs de lysine diméthylase pour des troubles myéloprolifératifs
WO2012107499A1 (fr)	2011-02-08	2012-08-16	Oryzon Genomics S.A.	Inhibiteurs de la lysine déméthylase pour des maladies ou des troubles myéloprolifératifs ou lymphoprolifératifs
JP2012200185A (ja) *	2011-03-24	2012-10-22	Nagoya City Univ	人工多能性幹細胞の樹立効率改善剤及びそれを用いた効率的な人工多能性幹細胞の樹立方法
US20140296255A1 (en)	2011-05-19	2014-10-02	Oryzong Genomics, S.A.	Lysine demethylase inhibitors for thrombosis and cardiovascular diseases
EP2741741A2 (fr)	2011-05-19	2014-06-18	Oryzon Genomics, S.A.	Inhibiteurs de la lysine déméthylase destinés au traitement de maladies ou états inflammatoires
UA114406C2 (uk)	2011-08-09	2017-06-12	Такеда Фармасьютікал Компані Лімітед	Похідні циклопропанаміну як інгібітори lsd1
RS58475B1 (sr)	2011-10-20	2019-04-30	Oryzon Genomics Sa	Jedinjenja (hetero)aril ciklopropilamina kao lsd1 inhibitori
CN107266345B (zh)	2011-10-20	2021-08-17	奥瑞泽恩基因组学股份有限公司	作为lsd1抑制剂的(杂)芳基环丙胺化合物
US9751885B2 (en)	2012-10-12	2017-09-05	Takeda Pharmaceutical Company Limited	Cyclopropanamine compound and use thereof
EP2927212A4 (fr)	2012-11-28	2016-06-08	Univ Kyoto	Inhibiteur sélectif de lsd1 à structure lysine
EP2740474A1 (fr)	2012-12-05	2014-06-11	Instituto Europeo di Oncologia S.r.l.	Dérivés de cyclopropylamine utiles comme inhibiteurs d'histone-déméthylases kdm1a
AU2014306149B2 (en)	2013-08-06	2019-09-19	Imago Biosciences Inc.	KDM1A inhibitors for the treatment of disease
WO2016123387A1 (fr) *	2015-01-30	2016-08-04	Genentech, Inc.	Composés thérapeutiques et leurs utilisations
KR102626978B1 (ko)	2015-02-12	2024-01-18	이마고 바이오사이언시즈 인코포레이티드	질환 치료를 위한 kdm1a 저해제
AU2016250099A1 (en) *	2015-04-14	2017-10-12	Gilead Sciences, Inc.	Methods of treating hepatitis B virus
EP3090998A1 (fr)	2015-05-06	2016-11-09	F. Hoffmann-La Roche AG	Formes solides
AU2016275702A1 (en)	2015-06-12	2017-12-21	Oryzon Genomics, S.A.	Biomarkers associated with LSD1 inhibitors and uses thereof
WO2017013061A1 (fr)	2015-07-17	2017-01-26	Oryzon Genomics, S.A.	Biomarqueurs associés à des inhibiteurs de lsd1 et utilisations de ceux-ci
US11013698B2 (en)	2016-03-15	2021-05-25	Oryzon Genomics S.A.	Combinations of LSD1 inhibitors for the treatment of hematological malignancies
ES3057783T3 (en)	2016-03-15	2026-03-04	Oryzon Genomics Sa	Combinations of lsd1 inhibitors for use in the treatment of neoplastic diseases
WO2017158136A1 (fr)	2016-03-16	2017-09-21	Oryzon Genomics, S.A.	Procédés de détermination de l'engagement d'une cible kdm1a et chimiosondes utiles correspondantes
PL3307267T3 (pl)	2016-06-10	2019-10-31	Oryzon Genomics Sa	Leczenie stwardnienia rozsianego
US11390590B2 (en)	2016-08-16	2022-07-19	Imago Biosciences, Inc.	Methods and processes for the preparation of KDM1A inhibitors
WO2018083189A1 (fr)	2016-11-03	2018-05-11	Oryzon Genomics, S.A.	Biomarqueurs pour déterminer la sensibilité à des inhibiteurs de lsd1
WO2018083138A1 (fr)	2016-11-03	2018-05-11	Oryzon Genomics, S.A.	Biomarqueurs pharmacodynamiques pour traitement du cancer personnalisé à l'aide d'agents de modification épigénétique
SI3661510T1 (sl)	2017-08-03	2025-03-31	Oryzon Genomics, S.A.	Postopki zdravljenja vedenjskih sprememb
KR102684364B1 (ko)	2018-05-11	2024-07-11	이마고 바이오사이언시즈 인코포레이티드	질환의 치료를 위한 kdm1a 저해제
US20220151999A1 (en)	2019-03-20	2022-05-19	Oryzon Genomics, S.A.	Methods of treating attention deficit hyperactivity disorder using kdm1a inhibitors such as the compound vafidemstat
US20220151998A1 (en)	2019-03-20	2022-05-19	Oryzon Genomics, S.A.	Methods of treating borderline personality disorder
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EP4522136A1 (fr)	2022-05-09	2025-03-19	Oryzon Genomics, S.A.	Méthodes de traitement d'une tumeur maligne des gaines des nerfs périphériques (tmgnp) à l'aide d'inhibiteurs de lsd1
WO2024110649A1 (fr)	2022-11-24	2024-05-30	Oryzon Genomics, S.A.	Combinaisons d'inhibiteurs de lsd1 et d'inhibiteurs de ménine pour le traitement du cancer

2010
- 2010-06-03 WO PCT/JP2010/059476 patent/WO2010143582A1/fr not_active Ceased
- 2010-06-03 JP JP2011518500A patent/JPWO2010143582A1/ja active Pending

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JP2017513842A (ja) *	2014-04-11	2017-06-01	武田薬品工業株式会社	シクロプロパンアミン化合物およびその用途

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JPWO2010143582A1 - フェニルシクロプロピルアミン誘導体及びｌｓｄ１阻害剤 - Google Patents

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