ZA200508298B - 1,2,4-oxadiazole benzoic acid compounds - Google Patents
1,2,4-oxadiazole benzoic acid compounds Download PDFInfo
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- ZA200508298B ZA200508298B ZA200508298A ZA200508298A ZA200508298B ZA 200508298 B ZA200508298 B ZA 200508298B ZA 200508298 A ZA200508298 A ZA 200508298A ZA 200508298 A ZA200508298 A ZA 200508298A ZA 200508298 B ZA200508298 B ZA 200508298B
- Authority
- ZA
- South Africa
- Prior art keywords
- substituted
- unsubstituted
- benzoic acid
- phenyl
- oxadiazol
- Prior art date
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- SNGNHEIIYFNIIL-UHFFFAOYSA-N benzoic acid;1,2,4-oxadiazole Chemical class C=1N=CON=1.OC(=O)C1=CC=CC=C1 SNGNHEIIYFNIIL-UHFFFAOYSA-N 0.000 title description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 76
- 150000001875 compounds Chemical class 0.000 claims description 71
- -1 3-(4-pyridinyl)propyl Chemical group 0.000 claims description 63
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 59
- 125000003118 aryl group Chemical group 0.000 claims description 58
- 125000001072 heteroaryl group Chemical group 0.000 claims description 49
- 125000003342 alkenyl group Chemical group 0.000 claims description 41
- 229910052739 hydrogen Inorganic materials 0.000 claims description 40
- 239000001257 hydrogen Substances 0.000 claims description 40
- 238000013519 translation Methods 0.000 claims description 31
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 30
- 125000000304 alkynyl group Chemical group 0.000 claims description 28
- 201000010099 disease Diseases 0.000 claims description 28
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 28
- 229910052736 halogen Inorganic materials 0.000 claims description 25
- 150000002367 halogens Chemical class 0.000 claims description 25
- 108020004999 messenger RNA Proteins 0.000 claims description 22
- 125000003545 alkoxy group Chemical group 0.000 claims description 20
- 125000004104 aryloxy group Chemical group 0.000 claims description 19
- 125000000623 heterocyclic group Chemical group 0.000 claims description 19
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 18
- 230000002028 premature Effects 0.000 claims description 18
- 206010028980 Neoplasm Diseases 0.000 claims description 16
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
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- 150000003839 salts Chemical class 0.000 claims description 12
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
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- 239000002775 capsule Substances 0.000 claims description 4
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- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims 31
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 7
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 7
- 201000009030 Carcinoma Diseases 0.000 claims 4
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- 125000000143 2-carboxyethyl group Chemical group [H]OC(=O)C([H])([H])C([H])([H])* 0.000 claims 3
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims 3
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims 2
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 2
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 2
- RAJNKNCXTQPGPD-UHFFFAOYSA-N 3-[5-(3-methylphenyl)-1,2,4-oxadiazol-3-yl]benzoic acid Chemical compound CC1=CC=CC(C=2ON=C(N=2)C=2C=C(C=CC=2)C(O)=O)=C1 RAJNKNCXTQPGPD-UHFFFAOYSA-N 0.000 claims 2
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 2
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 2
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- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims 1
- ZVSKGVUGNOBFJY-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethyl 3-[5-(2-fluorophenyl)-1,2,4-oxadiazol-3-yl]benzoate Chemical compound COCCOCCOC(=O)C1=CC=CC(C=2N=C(ON=2)C=2C(=CC=CC=2)F)=C1 ZVSKGVUGNOBFJY-UHFFFAOYSA-N 0.000 claims 1
- PJZPMDCCJSXOLI-UHFFFAOYSA-N 2-[2-(2-methoxyethoxy)ethoxy]ethyl 3-[5-(2-fluorophenyl)-1,2,4-oxadiazol-3-yl]benzoate Chemical compound COCCOCCOCCOC(=O)C1=CC=CC(C=2N=C(ON=2)C=2C(=CC=CC=2)F)=C1 PJZPMDCCJSXOLI-UHFFFAOYSA-N 0.000 claims 1
- BPLNJRLLVYRUTL-UHFFFAOYSA-N 2-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]ethyl 3-[5-(2-fluorophenyl)-1,2,4-oxadiazol-3-yl]benzoate Chemical compound COCCOCCOCCOCCOC(=O)C1=CC=CC(C=2N=C(ON=2)C=2C(=CC=CC=2)F)=C1 BPLNJRLLVYRUTL-UHFFFAOYSA-N 0.000 claims 1
- ZHNRXVGRDOIYAP-UHFFFAOYSA-N 2-[2-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]ethoxy]ethyl 3-[5-(2-fluorophenyl)-1,2,4-oxadiazol-3-yl]benzoate Chemical compound COCCOCCOCCOCCOCCOC(=O)C1=CC=CC(C=2N=C(ON=2)C=2C(=CC=CC=2)F)=C1 ZHNRXVGRDOIYAP-UHFFFAOYSA-N 0.000 claims 1
- WHRUUXRXOASLIZ-UHFFFAOYSA-N 2-[2-[2-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethyl 3-[5-(2-fluorophenyl)-1,2,4-oxadiazol-3-yl]benzoate Chemical compound OCCOCCOCCOCCOCCOCCOC(=O)C1=CC=CC(C=2N=C(ON=2)C=2C(=CC=CC=2)F)=C1 WHRUUXRXOASLIZ-UHFFFAOYSA-N 0.000 claims 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
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- LQUCAOSQNCELGO-UHFFFAOYSA-N 3-(5-benzyl-1,2,4-oxadiazol-3-yl)benzoic acid Chemical compound OC(=O)C1=CC=CC(C=2N=C(CC=3C=CC=CC=3)ON=2)=C1 LQUCAOSQNCELGO-UHFFFAOYSA-N 0.000 claims 1
- MDTTZNKKHLLRCQ-UHFFFAOYSA-N 3-(5-butyl-1,2,4-oxadiazol-3-yl)benzoic acid Chemical compound O1C(CCCC)=NC(C=2C=C(C=CC=2)C(O)=O)=N1 MDTTZNKKHLLRCQ-UHFFFAOYSA-N 0.000 claims 1
- VNQGCDZJVLQLGK-UHFFFAOYSA-N 3-(5-cyclobutyl-1,2,4-oxadiazol-3-yl)benzoic acid Chemical compound OC(=O)C1=CC=CC(C=2N=C(ON=2)C2CCC2)=C1 VNQGCDZJVLQLGK-UHFFFAOYSA-N 0.000 claims 1
- WEXBMDZIXNBKMO-UHFFFAOYSA-N 3-(5-cyclohexyl-1,2,4-oxadiazol-3-yl)benzoic acid Chemical compound OC(=O)C1=CC=CC(C=2N=C(ON=2)C2CCCCC2)=C1 WEXBMDZIXNBKMO-UHFFFAOYSA-N 0.000 claims 1
- DMURCCIISLZCGG-UHFFFAOYSA-N 3-(5-cyclopentyl-1,2,4-oxadiazol-3-yl)benzoic acid Chemical compound OC(=O)C1=CC=CC(C=2N=C(ON=2)C2CCCC2)=C1 DMURCCIISLZCGG-UHFFFAOYSA-N 0.000 claims 1
- BINCAUXZQKKNIA-UHFFFAOYSA-N 3-(5-cyclopropyl-1,2,4-oxadiazol-3-yl)benzoic acid Chemical compound OC(=O)C1=CC=CC(C=2N=C(ON=2)C2CC2)=C1 BINCAUXZQKKNIA-UHFFFAOYSA-N 0.000 claims 1
- DFUGCJDEZGHOQR-UHFFFAOYSA-N 3-(5-naphthalen-1-yl-1,2,4-oxadiazol-3-yl)benzoic acid Chemical compound OC(=O)C1=CC=CC(C=2N=C(ON=2)C=2C3=CC=CC=C3C=CC=2)=C1 DFUGCJDEZGHOQR-UHFFFAOYSA-N 0.000 claims 1
- AAEOJWLYUFDYTA-UHFFFAOYSA-N 3-(5-prop-1-enyl-1,2,4-oxadiazol-3-yl)benzoic acid Chemical compound O1C(C=CC)=NC(C=2C=C(C=CC=2)C(O)=O)=N1 AAEOJWLYUFDYTA-UHFFFAOYSA-N 0.000 claims 1
- LWUZJUHOIOFIQR-UHFFFAOYSA-N 3-(5-propan-2-yl-1,2,4-oxadiazol-3-yl)benzoic acid Chemical compound O1C(C(C)C)=NC(C=2C=C(C=CC=2)C(O)=O)=N1 LWUZJUHOIOFIQR-UHFFFAOYSA-N 0.000 claims 1
- FBGJCNLBJGAZTD-UHFFFAOYSA-N 3-(5-pyridin-3-yl-1,2,4-oxadiazol-3-yl)benzoic acid Chemical compound OC(=O)C1=CC=CC(C=2N=C(ON=2)C=2C=NC=CC=2)=C1 FBGJCNLBJGAZTD-UHFFFAOYSA-N 0.000 claims 1
- QJZYKOFYERZLHY-UHFFFAOYSA-N 3-(5-pyridin-4-yl-1,2,4-oxadiazol-3-yl)benzoic acid Chemical compound OC(=O)C1=CC=CC(C=2N=C(ON=2)C=2C=CN=CC=2)=C1 QJZYKOFYERZLHY-UHFFFAOYSA-N 0.000 claims 1
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- IKNFAOPFEAGWDX-UHFFFAOYSA-N 3-(5-thiophen-2-yl-1,2,4-oxadiazol-3-yl)benzoic acid Chemical compound OC(=O)C1=CC=CC(C=2N=C(ON=2)C=2SC=CC=2)=C1 IKNFAOPFEAGWDX-UHFFFAOYSA-N 0.000 claims 1
- ZHZDPBNZQDGTBI-UHFFFAOYSA-N 3-[5-(1,2-oxazol-5-yl)-1,2,4-oxadiazol-3-yl]benzoic acid Chemical compound OC(=O)C1=CC=CC(C=2N=C(ON=2)C=2ON=CC=2)=C1 ZHZDPBNZQDGTBI-UHFFFAOYSA-N 0.000 claims 1
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- AINHBIIYHNZEBU-UHFFFAOYSA-N 3-[5-(1-benzothiophen-2-yl)-1,2,4-oxadiazol-3-yl]benzoic acid Chemical compound OC(=O)C1=CC=CC(C=2N=C(ON=2)C=2SC3=CC=CC=C3C=2)=C1 AINHBIIYHNZEBU-UHFFFAOYSA-N 0.000 claims 1
- GGQJDTHMZZQPGA-UHFFFAOYSA-N 3-[5-(1-phenylpropyl)-1,2,4-oxadiazol-3-yl]benzoic acid Chemical compound C=1C=CC=CC=1C(CC)C(ON=1)=NC=1C1=CC=CC(C(O)=O)=C1 GGQJDTHMZZQPGA-UHFFFAOYSA-N 0.000 claims 1
- PNZMEGXHZNMRSZ-UHFFFAOYSA-N 3-[5-(2,1,3-benzoxadiazol-5-yl)-1,2,4-oxadiazol-3-yl]benzoic acid Chemical compound OC(=O)C1=CC=CC(C=2N=C(ON=2)C2=CC3=NON=C3C=C2)=C1 PNZMEGXHZNMRSZ-UHFFFAOYSA-N 0.000 claims 1
- CCNPNNZNAXNSKM-UHFFFAOYSA-N 3-[5-(2,3-difluorophenyl)-1,2,4-oxadiazol-3-yl]benzoic acid Chemical compound OC(=O)C1=CC=CC(C=2N=C(ON=2)C=2C(=C(F)C=CC=2)F)=C1 CCNPNNZNAXNSKM-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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- C07D285/14—Thiadiazoles; Hydrogenated thiadiazoles condensed with carbocyclic rings or ring systems
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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
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- 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
- C07D413/10—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 linked by a carbon chain containing aromatic rings
Landscapes
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- Ophthalmology & Optometry (AREA)
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US46198803P | 2003-04-11 | 2003-04-11 |
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| ZA200508298B true ZA200508298B (en) | 2007-01-31 |
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| ZA200508298A ZA200508298B (en) | 2003-04-11 | 2004-04-09 | 1,2,4-oxadiazole benzoic acid compounds |
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- 2010-02-17 US US12/707,404 patent/US8017636B2/en not_active Expired - Lifetime
- 2010-03-08 US US12/719,443 patent/US8227494B2/en not_active Expired - Lifetime
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2011
- 2011-07-15 JP JP2011156613A patent/JP5436500B2/ja not_active Expired - Fee Related
- 2011-08-18 US US13/212,221 patent/US8163782B2/en not_active Expired - Fee Related
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2012
- 2012-03-23 US US13/427,932 patent/US8299105B2/en not_active Expired - Fee Related
- 2012-06-22 US US13/530,139 patent/US8486982B2/en not_active Expired - Fee Related
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2013
- 2013-03-11 IL IL225161A patent/IL225161A/en active IP Right Grant
- 2013-06-19 US US13/921,269 patent/US8796322B2/en not_active Expired - Lifetime
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2014
- 2014-06-18 US US14/307,747 patent/US8975287B2/en not_active Expired - Lifetime
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2015
- 2015-01-16 CY CY20151100039T patent/CY1115870T1/el unknown
- 2015-01-28 US US14/607,132 patent/US9205088B2/en not_active Expired - Lifetime
- 2015-02-03 NO NO2015002C patent/NO2015002I1/no not_active IP Right Cessation
- 2015-04-16 HU HUS1500021C patent/HUS1500021I1/hu unknown
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- 2015-04-20 LU LU92698C patent/LU92698I2/xx unknown
- 2015-04-20 BE BE2015C025C patent/BE2015C025I2/fr unknown
- 2015-04-21 FR FR15C0030C patent/FR15C0030I2/fr active Active
- 2015-11-13 US US14/940,345 patent/US9861617B2/en not_active Expired - Lifetime
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2017
- 2017-05-03 CY CY20171100480T patent/CY1119001T1/el unknown
- 2017-12-04 US US15/830,405 patent/US10071081B2/en not_active Expired - Lifetime
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2018
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2020
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2021
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2022
- 2022-09-13 CY CY20221100605T patent/CY1125544T1/el unknown
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