JP2012528105A5 - - Google Patents
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- Publication number
- JP2012528105A5 JP2012528105A5 JP2012512338A JP2012512338A JP2012528105A5 JP 2012528105 A5 JP2012528105 A5 JP 2012528105A5 JP 2012512338 A JP2012512338 A JP 2012512338A JP 2012512338 A JP2012512338 A JP 2012512338A JP 2012528105 A5 JP2012528105 A5 JP 2012528105A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- amino
- optionally substituted
- halogen
- hydroxy
- Prior art date
- 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.)
- Granted
Links
- 125000000217 alkyl group Chemical group 0.000 claims 57
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 23
- 150000001875 compounds Chemical class 0.000 claims 20
- 229910052736 halogen Inorganic materials 0.000 claims 19
- 150000002367 halogens Chemical class 0.000 claims 19
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 19
- 125000003545 alkoxy group Chemical group 0.000 claims 18
- -1 azepin-1-yl Chemical group 0.000 claims 18
- 125000001072 heteroaryl group Chemical group 0.000 claims 13
- 125000001424 substituent group Chemical group 0.000 claims 12
- 125000003342 alkenyl group Chemical group 0.000 claims 11
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 10
- 125000004414 alkyl thio group Chemical group 0.000 claims 7
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims 6
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 6
- 125000000304 alkynyl group Chemical group 0.000 claims 6
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 6
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims 5
- 125000005222 heteroarylaminocarbonyl group Chemical group 0.000 claims 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 5
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 4
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 4
- 150000001540 azides Chemical class 0.000 claims 4
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims 4
- 125000005224 heteroarylcarbonylamino group Chemical group 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 4
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 3
- 125000005553 heteroaryloxy group Chemical group 0.000 claims 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 2
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims 2
- 125000006598 aminocarbonylamino group Chemical group 0.000 claims 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 2
- 208000021267 infertility disease Diseases 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 2
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 125000004366 heterocycloalkenyl group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 125000004496 thiazol-5-yl group Chemical group S1C=NC=C1* 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 229930192474 thiophene Natural products 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- XLMSKXASROPJNG-UHFFFAOYSA-N 2-azaniumyl-2-thiophen-2-ylacetate Chemical compound OC(=O)C(N)C1=CC=CS1 XLMSKXASROPJNG-UHFFFAOYSA-N 0.000 description 1
- GUGQQGROXHPINL-UHFFFAOYSA-N 2-oxobutanoyl chloride Chemical compound CCC(=O)C(Cl)=O GUGQQGROXHPINL-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- IQXHVIBINSNOQM-UHFFFAOYSA-N ethyl 8-methoxy-9-propan-2-yloxy-1-thiophen-2-ylimidazo[5,1-a]isoquinoline-3-carboxylate Chemical compound C=12C3=CC(OC(C)C)=C(OC)C=C3C=CN2C(C(=O)OCC)=NC=1C1=CC=CS1 IQXHVIBINSNOQM-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- ZRKMIBVGOMZTAE-UHFFFAOYSA-N n-tert-butyl-8-methoxy-n-methyl-9-(2-methylprop-1-enyl)-1-thiophen-2-ylimidazo[5,1-a]isoquinoline-3-carboxamide Chemical compound C=12C=3C=C(C=C(C)C)C(OC)=CC=3C=CN2C(C(=O)N(C)C(C)(C)C)=NC=1C1=CC=CS1 ZRKMIBVGOMZTAE-UHFFFAOYSA-N 0.000 description 1
- DNSWBPOFBBWYJX-UHFFFAOYSA-N n-tert-butyl-n-ethyl-8-methoxy-9-propan-2-yloxy-1-thiophen-2-yl-5,6-dihydroimidazo[5,1-a]isoquinoline-3-carboxamide Chemical compound C=12C3=CC(OC(C)C)=C(OC)C=C3CCN2C(C(=O)N(CC)C(C)(C)C)=NC=1C1=CC=CS1 DNSWBPOFBBWYJX-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP09161274 | 2009-05-27 | ||
| EP09161274.7 | 2009-05-27 | ||
| PCT/EP2010/057134 WO2010136438A1 (en) | 2009-05-27 | 2010-05-25 | (dihydro) imidazoiso (5, 1-a) quinolines as fsh receptor agonists for the treatment of fertility disorders |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2012528105A JP2012528105A (ja) | 2012-11-12 |
| JP2012528105A5 true JP2012528105A5 (enExample) | 2014-10-09 |
| JP5647675B2 JP5647675B2 (ja) | 2015-01-07 |
Family
ID=42315817
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012512338A Expired - Fee Related JP5647675B2 (ja) | 2009-05-27 | 2010-05-25 | 受胎障害治療用のｆｓｈ受容体アゴニストとしての（ジヒドロ）イミダゾイソ（５，１−ａ）キノリン |
Country Status (8)
| Country | Link |
|---|---|
| EP (1) | EP2435433B1 (enExample) |
| JP (1) | JP5647675B2 (enExample) |
| CN (1) | CN102448961B (enExample) |
| AR (1) | AR076703A1 (enExample) |
| AU (1) | AU2010252007B2 (enExample) |
| CA (1) | CA2763118A1 (enExample) |
| TW (1) | TWI461426B (enExample) |
| WO (1) | WO2010136438A1 (enExample) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2796774T3 (es) | 2011-07-01 | 2020-11-30 | Merck Patent Gmbh | Dihidropirazoles, composiciones farmacéuticas de los mismos y su uso para el tratamiento de trastornos de fertilidad |
| CA2834199C (en) | 2011-07-18 | 2020-01-07 | Merck Patent Gmbh | Benzamides as allosteric modulators of the fsh receptor |
| CN104080784B (zh) | 2012-01-10 | 2017-07-18 | 默克专利有限公司 | 用作卵泡刺激素调节剂的苯甲酰胺衍生物 |
| BR112014019351A8 (pt) * | 2012-02-08 | 2017-07-11 | Merck Patent Gmbh | Análogos de tiazolidinona deuterados como agonistas para o receptor do hormônio folículo estimulante |
| CA2912921C (en) * | 2013-06-24 | 2021-05-18 | Merck Patent Gmbh | Pyrazole compounds as modulators of fshr and uses thereof |
| EP3013823B1 (en) | 2013-06-24 | 2017-11-01 | Merck Patent GmbH | Imidazole compounds as modulators of fshr and uses thereof |
| ME03654B (me) | 2014-02-13 | 2020-07-20 | Incyte Corp | Ciklopropilamini kao lsd1 inhibitori |
| WO2015123437A1 (en) | 2014-02-13 | 2015-08-20 | Incyte Corporation | Cyclopropylamines as lsd1 inhibitors |
| TW201613860A (en) | 2014-02-13 | 2016-04-16 | Incyte Corp | Cyclopropylamines as LSD1 inhibitors |
| PT3105226T (pt) | 2014-02-13 | 2019-11-06 | Incyte Corp | Ciclopropilaminas como inibidores de lsd1 |
| WO2015196335A1 (en) | 2014-06-23 | 2015-12-30 | Tocopherx, Inc. | Pyrazole compounds as modulators of fshr and uses thereof |
| TW201613925A (en) | 2014-07-10 | 2016-04-16 | Incyte Corp | Imidazopyrazines as LSD1 inhibitors |
| WO2016007722A1 (en) | 2014-07-10 | 2016-01-14 | Incyte Corporation | Triazolopyridines and triazolopyrazines as lsd1 inhibitors |
| WO2016007727A1 (en) | 2014-07-10 | 2016-01-14 | Incyte Corporation | Triazolopyridines and triazolopyrazines as lsd1 inhibitors |
| WO2016007731A1 (en) | 2014-07-10 | 2016-01-14 | Incyte Corporation | Imidazopyridines and imidazopyrazines as lsd1 inhibitors |
| AU2016243939B2 (en) | 2015-04-03 | 2020-09-03 | Incyte Holdings Corporation | Heterocyclic compounds as LSD1 inhibitors |
| KR102710120B1 (ko) | 2015-08-12 | 2024-09-27 | 인사이트 홀딩스 코포레이션 | Lsd1 저해제의 염 |
| AR109452A1 (es) | 2016-04-22 | 2018-12-12 | Incyte Corp | Formulación farmacéutica de un inhibidor de lsd1 y método de tratamiento |
| CN106866692A (zh) * | 2017-03-30 | 2017-06-20 | 毛阿龙 | 具有苯并1,4‑二氧杂环己二烯酮结构的fshr拮抗剂的制备方法 |
| WO2020047198A1 (en) | 2018-08-31 | 2020-03-05 | Incyte Corporation | Salts of an lsd1 inhibitor and processes for preparing the same |
| EP4598928A1 (en) * | 2022-10-05 | 2025-08-13 | Radionetics Oncology, Inc. | Follicle-stimulating hormone receptor (fshr) targeted therapeutics and uses thereof |
| KR20250157379A (ko) | 2023-03-08 | 2025-11-04 | 훼링 비.브이. | 소분자 fsh 수용체 조절제 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RO66059A (ro) * | 1973-05-25 | 1981-05-30 | Gruppo Lepetit Spa,It | Procedeu de obtinere a unor derivati de triazolochinoline |
| PH15001A (en) * | 1977-07-25 | 1982-03-22 | Sandoz Ag | Prolactin secretion inhibitors |
| CA2339018A1 (en) * | 1998-08-07 | 2000-02-17 | Applied Research Systems Ars Holding N.V. | Fsh mimetics for the treatment of infertility |
| JP4523273B2 (ja) * | 2001-07-02 | 2010-08-11 | ナームローゼ・フエンノートチヤツプ・オルガノン | テトラヒドロキノリン誘導体 |
| WO2004087211A2 (en) * | 2003-04-01 | 2004-10-14 | Applied Research Systems Ars Holding N.V. | Inhibitors of phosphodiesterases in infertility |
| CA2530316A1 (en) * | 2003-06-30 | 2005-01-13 | Altana Pharma Ag | Pyrrolodihydroisoquinolines as pde10 inhibitors |
| TW200944523A (en) * | 2008-02-08 | 2009-11-01 | Organon Nv | (Dihydro)pyrrolo[2,1-a]isoquinolines |
-
2010
- 2010-05-06 TW TW099114528A patent/TWI461426B/zh not_active IP Right Cessation
- 2010-05-25 EP EP10723991.5A patent/EP2435433B1/en not_active Not-in-force
- 2010-05-25 AU AU2010252007A patent/AU2010252007B2/en not_active Ceased
- 2010-05-25 JP JP2012512338A patent/JP5647675B2/ja not_active Expired - Fee Related
- 2010-05-25 CA CA2763118A patent/CA2763118A1/en not_active Abandoned
- 2010-05-25 WO PCT/EP2010/057134 patent/WO2010136438A1/en not_active Ceased
- 2010-05-25 CN CN201080023361.8A patent/CN102448961B/zh not_active Expired - Fee Related
- 2010-05-26 AR ARP100101803A patent/AR076703A1/es unknown
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