TW202035409A - 單醯基甘油脂肪酶調節劑 - Google Patents
單醯基甘油脂肪酶調節劑 Download PDFInfo
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- TW202035409A TW202035409A TW108135034A TW108135034A TW202035409A TW 202035409 A TW202035409 A TW 202035409A TW 108135034 A TW108135034 A TW 108135034A TW 108135034 A TW108135034 A TW 108135034A TW 202035409 A TW202035409 A TW 202035409A
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- Taiwan
- Prior art keywords
- methyl
- hexahydro
- methanone
- pyrazol
- trifluorophenyl
- Prior art date
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- 102000005398 Monoacylglycerol Lipase Human genes 0.000 title description 3
- 108020002334 Monoacylglycerol lipase Proteins 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 562
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 76
- 201000010099 disease Diseases 0.000 claims abstract description 43
- 208000035475 disorder Diseases 0.000 claims abstract description 33
- 208000002193 Pain Diseases 0.000 claims abstract description 23
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 21
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 18
- 208000020925 Bipolar disease Diseases 0.000 claims abstract description 9
- 208000020401 Depressive disease Diseases 0.000 claims abstract description 7
- 208000028552 Treatment-Resistant Depressive disease Diseases 0.000 claims abstract description 5
- -1 pyridine -2-yl Chemical group 0.000 claims description 478
- 125000000217 alkyl group Chemical group 0.000 claims description 263
- 229910052739 hydrogen Inorganic materials 0.000 claims description 120
- 239000000203 mixture Substances 0.000 claims description 114
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 97
- 102100029814 Monoglyceride lipase Human genes 0.000 claims description 71
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 69
- 150000003839 salts Chemical class 0.000 claims description 69
- 125000001072 heteroaryl group Chemical group 0.000 claims description 58
- 229910052799 carbon Inorganic materials 0.000 claims description 50
- 239000012453 solvate Substances 0.000 claims description 44
- 150000001204 N-oxides Chemical class 0.000 claims description 41
- 125000001188 haloalkyl group Chemical group 0.000 claims description 36
- 125000004550 quinolin-6-yl group Chemical group N1=CC=CC2=CC(=CC=C12)* 0.000 claims description 36
- 125000001424 substituent group Chemical group 0.000 claims description 35
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 34
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 32
- 229910052731 fluorine Inorganic materials 0.000 claims description 29
- 150000002576 ketones Chemical class 0.000 claims description 29
- 229910052757 nitrogen Inorganic materials 0.000 claims description 29
- 229910052801 chlorine Inorganic materials 0.000 claims description 27
- 238000011282 treatment Methods 0.000 claims description 27
- RONWGALEIBILOG-VMJVVOMYSA-N quinine sulfate Chemical compound [H+].[H+].[O-]S([O-])(=O)=O.C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21.C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 RONWGALEIBILOG-VMJVVOMYSA-N 0.000 claims description 23
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 22
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 21
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 21
- 230000000694 effects Effects 0.000 claims description 20
- 125000002619 bicyclic group Chemical group 0.000 claims description 19
- 102000005962 receptors Human genes 0.000 claims description 19
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- 239000000546 pharmaceutical excipient Substances 0.000 claims description 18
- 125000004076 pyridyl group Chemical group 0.000 claims description 18
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 18
- 230000001404 mediated effect Effects 0.000 claims description 17
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 claims description 15
- 238000006467 substitution reaction Methods 0.000 claims description 13
- 201000011510 cancer Diseases 0.000 claims description 12
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 10
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims description 7
- 206010065390 Inflammatory pain Diseases 0.000 claims description 7
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 claims description 5
- 230000000926 neurological effect Effects 0.000 claims description 4
- AZEXWHKOMMASPA-UHFFFAOYSA-N 2-{[4-(1-methyl-4-pyridin-4-yl-1h-pyrazol-3-yl)phenoxy]methyl}quinoline Chemical compound C=1C=C(OCC=2N=C3C=CC=CC3=CC=2)C=CC=1C1=NN(C)C=C1C1=CC=NC=C1 AZEXWHKOMMASPA-UHFFFAOYSA-N 0.000 claims description 3
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 3
- 125000004547 quinazolin-6-yl group Chemical group N1=CN=CC2=CC(=CC=C12)* 0.000 claims description 3
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims description 2
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 2
- CKJNUZNMWOVDFN-UHFFFAOYSA-N methanone Chemical compound O=[CH-] CKJNUZNMWOVDFN-UHFFFAOYSA-N 0.000 claims 396
- 125000001475 halogen functional group Chemical group 0.000 claims 43
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 3
- WMPDAIZRQDCGFH-UHFFFAOYSA-N 3-methoxybenzaldehyde Chemical compound COC1=CC=CC(C=O)=C1 WMPDAIZRQDCGFH-UHFFFAOYSA-N 0.000 claims 2
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 2
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- WWTBZEKOSBFBEM-SPWPXUSOSA-N (2s)-2-[[2-benzyl-3-[hydroxy-[(1r)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]phosphoryl]propanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)O)C(=O)C(CP(O)(=O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1C=CC=CC=1)CC1=CC=CC=C1 WWTBZEKOSBFBEM-SPWPXUSOSA-N 0.000 claims 1
- 125000001617 2,3-dimethoxy phenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C(OC([H])([H])[H])=C1[H] 0.000 claims 1
- TVTJUIAKQFIXCE-HUKYDQBMSA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynyl-1H-purine-6,8-dione Chemical compound NC=1NC(C=2N(C(N(C=2N=1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C)=O TVTJUIAKQFIXCE-HUKYDQBMSA-N 0.000 claims 1
- FFNVQNRYTPFDDP-UHFFFAOYSA-N 2-cyanopyridine Chemical compound N#CC1=CC=CC=N1 FFNVQNRYTPFDDP-UHFFFAOYSA-N 0.000 claims 1
- CSDSSGBPEUDDEE-UHFFFAOYSA-N 2-formylpyridine Chemical compound O=CC1=CC=CC=N1 CSDSSGBPEUDDEE-UHFFFAOYSA-N 0.000 claims 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- GIIWGCBLYNDKBO-UHFFFAOYSA-N Quinoline 1-oxide Chemical compound C1=CC=C2[N+]([O-])=CC=CC2=C1 GIIWGCBLYNDKBO-UHFFFAOYSA-N 0.000 claims 1
- METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 claims 1
- 125000005605 benzo group Chemical group 0.000 claims 1
- 229940126208 compound 22 Drugs 0.000 claims 1
- 229940125851 compound 27 Drugs 0.000 claims 1
- QPOWUYJWCJRLEE-UHFFFAOYSA-N dipyridin-2-ylmethanone Chemical compound C=1C=CC=NC=1C(=O)C1=CC=CC=N1 QPOWUYJWCJRLEE-UHFFFAOYSA-N 0.000 claims 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- 125000004254 isoquinolin-1-yl group Chemical group [H]C1=C([H])C2=C([H])C([H])=C([H])C([H])=C2C(*)=N1 0.000 claims 1
- 125000004551 isoquinolin-3-yl group Chemical group C1=NC(=CC2=CC=CC=C12)* 0.000 claims 1
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims 1
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims 1
- 125000004546 quinazolin-4-yl group Chemical group N1=CN=C(C2=CC=CC=C12)* 0.000 claims 1
- 125000004549 quinolin-4-yl group Chemical group N1=CC=C(C2=CC=CC=C12)* 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 65
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
- C07D471/18—Bridged systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
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- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Epidemiology (AREA)
- Ophthalmology & Optometry (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
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| EP (1) | EP3856179A1 (https=) |
| JP (2) | JP7413368B2 (https=) |
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| MA (1) | MA53722A (https=) |
| MX (1) | MX2021003661A (https=) |
| TW (1) | TW202035409A (https=) |
| WO (1) | WO2020065614A1 (https=) |
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| MY205440A (en) | 2018-09-28 | 2024-10-21 | Janssen Pharmaceutica Nv | Monoacylglycerol lipase modulators |
| JP7697934B2 (ja) | 2019-09-30 | 2025-06-24 | ヤンセン ファーマシューティカ エヌ．ベー． | 放射線標識されたｍｇｌ ｐｅｔリガンド |
| BR112022019077A2 (pt) * | 2020-03-26 | 2022-12-27 | Janssen Pharmaceutica Nv | Moduladores da monoacilglicerol lipase |
| CA3242372A1 (en) | 2021-12-29 | 2023-07-06 | Psy Therapeutics, Inc. | Inhibiting monoacylglycerol lipase (magl) |
| CN118451068A (zh) | 2021-12-30 | 2024-08-06 | 上海翰森生物医药科技有限公司 | 三并环类衍生物抑制剂、其制备方法和应用 |
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| US4812462A (en) | 1986-04-01 | 1989-03-14 | Warner-Lambert Company | 4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-6-carboxylic acid analogs having antihypertensive activity |
| US4816463A (en) | 1986-04-01 | 1989-03-28 | Warner-Lambert Company | Substituted diimidazo [1,5-a: 4',5'-d]pyridines having antihypertensive activity |
| CA2093125C (en) | 1990-10-02 | 2003-12-16 | Warner-Lambert Company | Angiotensin ii antagonists |
| CA2493637A1 (en) | 2002-07-25 | 2004-02-12 | Manuela Villa | Bicyclo-pyrazoles active as kinase inhibitors, process for their preparation and pharmaceutical compositions comprising them |
| EP1526852A1 (en) | 2002-07-25 | 2005-05-04 | Pharmacia Italia S.p.A. | Bicyclo-pyrazoles active as kinase inhibitors, process for their preparation and pharmaceutical compositions comprising them |
| GB0312609D0 (en) | 2003-06-02 | 2003-07-09 | Astrazeneca Ab | Novel compounds |
| AR045037A1 (es) | 2003-07-10 | 2005-10-12 | Aventis Pharma Sa | Tetrahidro-1h-pirazolo [3,4-c] piridinas sustituidas, composiciones que las contienen y su utilizacion. |
| FR2857363B1 (fr) | 2003-07-10 | 2007-09-07 | Aventis Pharma Sa | 4,5,6,7-tetrahydro-1h-pyrazolo[3,4-c] pyridines substituees compositions les contenant et utilisation |
| EP1784188B1 (en) | 2004-08-23 | 2010-07-14 | Merck Sharp & Dohme Corp. | Fused triazole derivatives as dipeptidyl peptidase-iv inhibitors for the treatment or prevention of diabetes |
| WO2006080884A1 (en) | 2005-01-27 | 2006-08-03 | Astrazeneca Ab | Novel biaromatic compounds, inhibitors of the p2x7-receptor |
| US7402596B2 (en) | 2005-03-24 | 2008-07-22 | Renovis, Inc. | Bicycloheteroaryl compounds as P2X7 modulators and uses thereof |
| WO2006110516A1 (en) | 2005-04-11 | 2006-10-19 | Abbott Laboratories | Acylhydrazide p2x7 antagonists and uses thereof |
| US7943617B2 (en) | 2006-11-27 | 2011-05-17 | Bristol-Myers Squibb Company | Heterobicyclic compounds useful as kinase inhibitors |
| FR2915197B1 (fr) | 2007-04-18 | 2009-06-12 | Sanofi Aventis Sa | Derives de triazolopyridine-carboxamides, leur preparation et leur application therapeutique. |
| KR20100023040A (ko) | 2007-06-21 | 2010-03-03 | 쉐링 코포레이션 | 폴리사이클릭 구아닌 유도체 및 이의 용도 |
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-
2019
- 2019-09-27 KR KR1020217012861A patent/KR20210069079A/ko active Pending
- 2019-09-27 TW TW108135034A patent/TW202035409A/zh unknown
- 2019-09-27 MX MX2021003661A patent/MX2021003661A/es unknown
- 2019-09-27 EP EP19780428.9A patent/EP3856179A1/en active Pending
- 2019-09-27 US US16/586,263 patent/US20200102311A1/en not_active Abandoned
- 2019-09-27 MA MA053722A patent/MA53722A/fr unknown
- 2019-09-27 JP JP2021517338A patent/JP7413368B2/ja active Active
- 2019-09-27 AU AU2019349962A patent/AU2019349962A1/en not_active Abandoned
- 2019-09-27 WO PCT/IB2019/058241 patent/WO2020065614A1/en not_active Ceased
- 2019-09-27 CN CN201980078966.8A patent/CN113164458B/zh active Active
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| CA3111309A1 (en) | 2020-04-02 |
| JP7413368B2 (ja) | 2024-01-15 |
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| JP2024038151A (ja) | 2024-03-19 |
| MX2021003661A (es) | 2021-08-19 |
| WO2020065614A1 (en) | 2020-04-02 |
| CN113164458B (zh) | 2024-09-13 |
| US11597728B2 (en) | 2023-03-07 |
| EP3856179A1 (en) | 2021-08-04 |
| MA53722A (fr) | 2022-03-30 |
| US20230242531A1 (en) | 2023-08-03 |
| US20200102311A1 (en) | 2020-04-02 |
| CN113164458A (zh) | 2021-07-23 |
| KR20210069079A (ko) | 2021-06-10 |
| US20220315583A1 (en) | 2022-10-06 |
| JP2022502440A (ja) | 2022-01-11 |
| AU2019349962A1 (en) | 2021-03-18 |
| BR112021005936A2 (pt) | 2021-06-29 |
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