ES2536319T3 - Compuestos bicíclicos como inhibidores de acetil-CoA carboxilasa (ACC) - Google Patents
Compuestos bicíclicos como inhibidores de acetil-CoA carboxilasa (ACC)Info
- Publication number
- ES2536319T3 ES2536319T3 ES11802168.2T ES11802168T ES2536319T3 ES 2536319 T3 ES2536319 T3 ES 2536319T3 ES 11802168 T ES11802168 T ES 11802168T ES 2536319 T3 ES2536319 T3 ES 2536319T3
- Authority
- ES
- Spain
- Prior art keywords
- compound
- optionally substituted
- group
- reaction
- ring
- 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.)
- Active
Links
- 125000002619 bicyclic group Chemical group 0.000 title claims abstract description 40
- 239000003112 inhibitor Substances 0.000 title description 25
- 102000000452 Acetyl-CoA carboxylase Human genes 0.000 title description 20
- 108010016219 Acetyl-CoA carboxylase Proteins 0.000 title description 20
- 108010018763 Biotin carboxylase Proteins 0.000 title description 20
- 150000001875 compounds Chemical class 0.000 claims abstract description 850
- 125000005843 halogen group Chemical group 0.000 claims abstract description 178
- 125000001424 substituent group Chemical group 0.000 claims abstract description 167
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 128
- 125000003118 aryl group Chemical group 0.000 claims abstract description 76
- 150000003839 salts Chemical class 0.000 claims abstract description 66
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 50
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract description 33
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 33
- 125000006574 non-aromatic ring group Chemical group 0.000 claims abstract description 32
- 125000004429 atom Chemical group 0.000 claims abstract description 21
- 125000003277 amino group Chemical group 0.000 claims abstract description 19
- 229910002091 carbon monoxide Inorganic materials 0.000 claims abstract description 17
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 16
- 239000003795 chemical substances by application Substances 0.000 claims description 87
- 238000004519 manufacturing process Methods 0.000 claims description 87
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 48
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 44
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- 125000003710 aryl alkyl group Chemical group 0.000 claims description 35
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- 125000004093 cyano group Chemical group *C#N 0.000 claims description 22
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 22
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- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 16
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- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 13
- ADHDEZRLSWZHKE-LBPRGKRZSA-N n-[(2s)-1-[6-(6-ethoxy-1,3-benzoxazol-2-yl)pyridin-3-yl]oxypropan-2-yl]acetamide Chemical compound O1C2=CC(OCC)=CC=C2N=C1C1=CC=C(OC[C@H](C)NC(C)=O)C=N1 ADHDEZRLSWZHKE-LBPRGKRZSA-N 0.000 claims description 3
- CBRJFLKXQUUGQV-LBPRGKRZSA-N n-[(2s)-1-[6-[6-(cyclopropylmethoxy)-1,3-benzoxazol-2-yl]-5-fluoropyridin-3-yl]oxypropan-2-yl]acetamide Chemical compound FC1=CC(OC[C@H](C)NC(C)=O)=CN=C1C(OC1=C2)=NC1=CC=C2OCC1CC1 CBRJFLKXQUUGQV-LBPRGKRZSA-N 0.000 claims description 3
- ZAAOFSTVMJFFPI-ZDUSSCGKSA-N n-[(2s)-1-[6-[6-(cyclopropylmethoxy)-1,3-benzoxazol-2-yl]pyridin-3-yl]oxypropan-2-yl]acetamide Chemical compound N1=CC(OC[C@H](C)NC(C)=O)=CC=C1C(OC1=C2)=NC1=CC=C2OCC1CC1 ZAAOFSTVMJFFPI-ZDUSSCGKSA-N 0.000 claims description 3
- 229940121373 acetyl-coa carboxylase inhibitor Drugs 0.000 claims description 2
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- 125000000623 heterocyclic group Chemical group 0.000 description 35
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 33
- 150000002825 nitriles Chemical class 0.000 description 32
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- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 description 27
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- 229940079593 drug Drugs 0.000 description 27
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 25
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 19
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- 239000003153 chemical reaction reagent Substances 0.000 description 18
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 18
- 239000003446 ligand Substances 0.000 description 18
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 17
- 239000012190 activator Substances 0.000 description 17
- 238000005804 alkylation reaction Methods 0.000 description 17
- 238000005859 coupling reaction Methods 0.000 description 17
- 230000001590 oxidative effect Effects 0.000 description 17
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 16
- 239000011261 inert gas Substances 0.000 description 16
- 238000006722 reduction reaction Methods 0.000 description 16
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 16
- 125000005915 C6-C14 aryl group Chemical group 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- 150000004982 aromatic amines Chemical class 0.000 description 15
- 230000003197 catalytic effect Effects 0.000 description 15
- 239000003638 chemical reducing agent Substances 0.000 description 15
- 230000002140 halogenating effect Effects 0.000 description 15
- 125000006717 (C3-C10) cycloalkenyl group Chemical group 0.000 description 14
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 14
- 150000003512 tertiary amines Chemical class 0.000 description 14
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 description 13
- 206010028980 Neoplasm Diseases 0.000 description 13
- 238000007112 amidation reaction Methods 0.000 description 13
- 238000001990 intravenous administration Methods 0.000 description 13
- 150000007524 organic acids Chemical class 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 12
- 208000001145 Metabolic Syndrome Diseases 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
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- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 description 11
- 206010020772 Hypertension Diseases 0.000 description 11
- 230000037396 body weight Effects 0.000 description 11
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 11
- 150000007529 inorganic bases Chemical class 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- 125000004433 nitrogen atom Chemical group N* 0.000 description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 11
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
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- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 10
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- 206010056997 Impaired fasting glucose Diseases 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
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- 150000004703 alkoxides Chemical class 0.000 description 9
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 9
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- SEDZOYHHAIAQIW-UHFFFAOYSA-N trimethylsilyl azide Chemical compound C[Si](C)(C)N=[N+]=[N-] SEDZOYHHAIAQIW-UHFFFAOYSA-N 0.000 description 1
- UJMBCXLDXJUMFB-UHFFFAOYSA-K trisodium;5-oxo-1-(4-sulfonatophenyl)-4-[(4-sulfonatophenyl)diazenyl]-4h-pyrazole-3-carboxylate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)C1=NN(C=2C=CC(=CC=2)S([O-])(=O)=O)C(=O)C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 UJMBCXLDXJUMFB-UHFFFAOYSA-K 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/42—Oxazoles
- A61K31/423—Oxazoles condensed with carbocyclic rings
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- A61P9/12—Antihypertensives
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
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- Pharmacology & Pharmacy (AREA)
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- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Endocrinology (AREA)
- Emergency Medicine (AREA)
- Hospice & Palliative Care (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Epidemiology (AREA)
- Child & Adolescent Psychology (AREA)
- Neurology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2010266097 | 2010-11-30 | ||
| JP2010266097 | 2010-11-30 | ||
| JP2011175330 | 2011-08-10 | ||
| JP2011175330 | 2011-08-10 | ||
| PCT/JP2011/078010 WO2012074126A1 (en) | 2010-11-30 | 2011-11-29 | Bicyclic compound |
Publications (1)
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|---|---|
| ES2536319T3 true ES2536319T3 (es) | 2015-05-22 |
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| ES11802168.2T Active ES2536319T3 (es) | 2010-11-30 | 2011-11-29 | Compuestos bicíclicos como inhibidores de acetil-CoA carboxilasa (ACC) |
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| EP (1) | EP2649062B1 (OSRAM) |
| JP (1) | JP5824517B2 (OSRAM) |
| KR (1) | KR20140001965A (OSRAM) |
| CN (1) | CN103347872B (OSRAM) |
| AR (1) | AR084032A1 (OSRAM) |
| AU (1) | AU2011337565A1 (OSRAM) |
| BR (1) | BR112013013417A2 (OSRAM) |
| CA (1) | CA2819400A1 (OSRAM) |
| CL (1) | CL2013001520A1 (OSRAM) |
| CO (1) | CO6751239A2 (OSRAM) |
| CR (1) | CR20130281A (OSRAM) |
| DO (1) | DOP2013000118A (OSRAM) |
| EA (1) | EA201390794A1 (OSRAM) |
| EC (1) | ECSP13012719A (OSRAM) |
| ES (1) | ES2536319T3 (OSRAM) |
| MA (1) | MA34713B1 (OSRAM) |
| MX (1) | MX2013006113A (OSRAM) |
| PE (1) | PE20140161A1 (OSRAM) |
| PH (1) | PH12013501099A1 (OSRAM) |
| SG (1) | SG190925A1 (OSRAM) |
| TW (1) | TW201242951A (OSRAM) |
| UY (1) | UY33756A (OSRAM) |
| WO (1) | WO2012074126A1 (OSRAM) |
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| KR20130094211A (ko) | 2010-04-27 | 2013-08-23 | 다케다 야쿠힌 고교 가부시키가이샤 | 바이시클릭 화합물 유도체 및 이의 ａｃｃ 저해제로서의 용도 |
| US9133129B2 (en) | 2011-10-24 | 2015-09-15 | Takeda Pharmaceutical Company Limited | Bicyclic compound |
| WO2014088983A1 (en) | 2012-12-07 | 2014-06-12 | Merck Sharp & Dohme Corp. | Regioselective n-2 arylation of indazoles |
| PL403149A1 (pl) * | 2013-03-14 | 2014-09-15 | Celon Pharma Spółka Akcyjna | Nowe związki pochodne pirazolilobenzo[d]imidazolu |
| AU2014262636A1 (en) | 2013-05-10 | 2015-11-26 | Gilead Apollo, Llc | ACC inhibitors and uses thereof |
| WO2014182945A1 (en) * | 2013-05-10 | 2014-11-13 | Nimbus Apollo, Inc. | Acc inhibitors and uses thereof |
| MX2015015421A (es) | 2013-05-10 | 2016-06-21 | Nimbus Apollo Inc | Inhibidores de acetil-coa carboxilasa (acc) y usos de los mismos. |
| US10208044B2 (en) | 2013-05-10 | 2019-02-19 | Gilead Apollo, Llc | ACC inhibitors and uses thereof |
| CN105530940A (zh) | 2013-09-12 | 2016-04-27 | 辉瑞大药厂 | 乙酰辅酶a羧化酶抑制剂用于治疗寻常痤疮的用途 |
| AP2016009176A0 (en) | 2013-11-14 | 2016-04-30 | Cadila Healthcare Ltd | Novel heterocyclic compounds |
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- 2011-11-29 PE PE2013001328A patent/PE20140161A1/es not_active Application Discontinuation
- 2011-11-29 TW TW100143674A patent/TW201242951A/zh unknown
- 2011-11-29 CA CA2819400A patent/CA2819400A1/en not_active Abandoned
- 2011-11-29 ES ES11802168.2T patent/ES2536319T3/es active Active
- 2011-11-29 SG SG2013041546A patent/SG190925A1/en unknown
- 2011-11-29 PH PH1/2013/501099A patent/PH12013501099A1/en unknown
- 2011-11-29 KR KR1020137016850A patent/KR20140001965A/ko not_active Withdrawn
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| CN103347872B (zh) | 2014-12-24 |
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| AU2011337565A1 (en) | 2013-07-11 |
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| CO6751239A2 (es) | 2013-09-16 |
| EA201390794A1 (ru) | 2013-11-29 |
| CA2819400A1 (en) | 2012-06-07 |
| BR112013013417A2 (pt) | 2019-09-24 |
| MA34713B1 (fr) | 2013-12-03 |
| JP2013545718A (ja) | 2013-12-26 |
| AU2011337565A2 (en) | 2013-07-11 |
| KR20140001965A (ko) | 2014-01-07 |
| DOP2013000118A (es) | 2013-09-30 |
| JP5824517B2 (ja) | 2015-11-25 |
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