ZA200606321B - New compounds, methods for their preparation and use thereof - Google Patents
New compounds, methods for their preparation and use thereof Download PDFInfo
- Publication number
- ZA200606321B ZA200606321B ZA200606321A ZA200606321A ZA200606321B ZA 200606321 B ZA200606321 B ZA 200606321B ZA 200606321 A ZA200606321 A ZA 200606321A ZA 200606321 A ZA200606321 A ZA 200606321A ZA 200606321 B ZA200606321 B ZA 200606321B
- Authority
- ZA
- South Africa
- Prior art keywords
- benzoic acid
- hydrogen
- propionylamino
- trifluoromethyl
- phenoxy
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 103
- 238000000034 method Methods 0.000 title description 29
- 238000002360 preparation method Methods 0.000 title description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 8
- 230000037396 body weight Effects 0.000 claims abstract description 6
- 239000005711 Benzoic acid Substances 0.000 claims description 42
- 229910052739 hydrogen Inorganic materials 0.000 claims description 33
- -1 NR4Rs Chemical group 0.000 claims description 32
- 239000001257 hydrogen Substances 0.000 claims description 32
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 150000001767 cationic compounds Chemical class 0.000 claims description 13
- 229910001411 inorganic cation Inorganic materials 0.000 claims description 13
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 150000002431 hydrogen Chemical group 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 239000000243 solution Substances 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims description 6
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 6
- QHQLZVRWZXWVFL-UHFFFAOYSA-N 2-(cyclopropanecarbonylamino)-5-[[2-(trifluoromethyl)phenyl]methoxy]benzoic acid Chemical compound C=1C=C(NC(=O)C2CC2)C(C(=O)O)=CC=1OCC1=CC=CC=C1C(F)(F)F QHQLZVRWZXWVFL-UHFFFAOYSA-N 0.000 claims description 4
- 101100294115 Caenorhabditis elegans nhr-4 gene Proteins 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- 239000000725 suspension Substances 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- BDBGGFWRMDJZOA-UHFFFAOYSA-N 5-[3,5-bis(trifluoromethyl)phenoxy]-2-(propanoylamino)benzoic acid Chemical compound C1=C(C(O)=O)C(NC(=O)CC)=CC=C1OC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 BDBGGFWRMDJZOA-UHFFFAOYSA-N 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 239000002775 capsule Substances 0.000 claims description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
- 239000000839 emulsion Substances 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
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- 239000012049 topical pharmaceutical composition Substances 0.000 claims description 2
- QSLPNSWXUQHVLP-UHFFFAOYSA-N $l^{1}-sulfanylmethane Chemical compound [S]C QSLPNSWXUQHVLP-UHFFFAOYSA-N 0.000 claims 2
- 102000007399 Nuclear hormone receptor Human genes 0.000 claims 2
- 108020005497 Nuclear hormone receptor Proteins 0.000 claims 2
- OKPYGWHZGORUTD-UHFFFAOYSA-N 2-(propanoylamino)-5-[[2-(trifluoromethyl)phenyl]methoxy]benzoic acid Chemical compound C1=C(C(O)=O)C(NC(=O)CC)=CC=C1OCC1=CC=CC=C1C(F)(F)F OKPYGWHZGORUTD-UHFFFAOYSA-N 0.000 claims 1
- 125000004888 n-propyl amino group Chemical group [H]N(*)C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
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- 150000002148 esters Chemical group 0.000 description 28
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- 108010052167 Dihydroorotate Dehydrogenase Proteins 0.000 description 19
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- 239000007858 starting material Substances 0.000 description 13
- 238000003756 stirring Methods 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 238000004587 chromatography analysis Methods 0.000 description 7
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 7
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- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical class NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 6
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- VHOGYURTWQBHIL-UHFFFAOYSA-N leflunomide Chemical compound O1N=CC(C(=O)NC=2C=CC(=CC=2)C(F)(F)F)=C1C VHOGYURTWQBHIL-UHFFFAOYSA-N 0.000 description 6
- 229960000681 leflunomide Drugs 0.000 description 6
- VAMXMNNIEUEQDV-UHFFFAOYSA-N methyl anthranilate Chemical compound COC(=O)C1=CC=CC=C1N VAMXMNNIEUEQDV-UHFFFAOYSA-N 0.000 description 6
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- 239000011734 sodium Substances 0.000 description 5
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- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 4
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- FBWADIKARMIWNM-UHFFFAOYSA-N N-3,5-dichloro-4-hydroxyphenyl-1,4-benzoquinone imine Chemical compound C1=C(Cl)C(O)=C(Cl)C=C1N=C1C=CC(=O)C=C1 FBWADIKARMIWNM-UHFFFAOYSA-N 0.000 description 4
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- DRTQHJPVMGBUCF-XVFCMESISA-N Uridine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-XVFCMESISA-N 0.000 description 4
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- VOTKXCXOVRJNGP-UHFFFAOYSA-N methyl 5-(2-aminophenyl)sulfanyl-2-(propanoylamino)benzoate Chemical compound C1=C(C(=O)OC)C(NC(=O)CC)=CC=C1SC1=CC=CC=C1N VOTKXCXOVRJNGP-UHFFFAOYSA-N 0.000 description 4
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- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
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- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
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- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 3
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- UFIVEPVSAGBUSI-UHFFFAOYSA-N dihydroorotic acid Chemical compound OC(=O)C1CC(=O)NC(=O)N1 UFIVEPVSAGBUSI-UHFFFAOYSA-N 0.000 description 3
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- GFCQKFQQZDIYJW-UHFFFAOYSA-N methyl 5-(2-aminophenoxy)-2-(propanoylamino)benzoate Chemical compound C1=C(C(=O)OC)C(NC(=O)CC)=CC=C1OC1=CC=CC=C1N GFCQKFQQZDIYJW-UHFFFAOYSA-N 0.000 description 3
- JFMWCXWCXLYKRY-UHFFFAOYSA-N methyl 5-hydroxy-2-(propanoylamino)benzoate Chemical compound CCC(=O)NC1=CC=C(O)C=C1C(=O)OC JFMWCXWCXLYKRY-UHFFFAOYSA-N 0.000 description 3
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- MEPLUSPZRYYTTI-UHFFFAOYSA-N 2-(cyclopropanecarbonylamino)-5-hydroxybenzoic acid Chemical compound OC(=O)C1=CC(O)=CC=C1NC(=O)C1CC1 MEPLUSPZRYYTTI-UHFFFAOYSA-N 0.000 description 2
- LKUKTEVOLRLWAI-UHFFFAOYSA-N 2-(propanoylamino)-5-[2-(propylamino)phenoxy]benzoic acid Chemical compound CCCNC1=CC=CC=C1OC1=CC=C(NC(=O)CC)C(C(O)=O)=C1 LKUKTEVOLRLWAI-UHFFFAOYSA-N 0.000 description 2
- IXDHIJVFTDQATJ-UHFFFAOYSA-N 2-(propanoylamino)-5-[2-(trifluoromethoxy)phenyl]sulfanylbenzoic acid Chemical compound C1=C(C(O)=O)C(NC(=O)CC)=CC=C1SC1=CC=CC=C1OC(F)(F)F IXDHIJVFTDQATJ-UHFFFAOYSA-N 0.000 description 2
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- YGASXVZXXXSXMH-UHFFFAOYSA-N methyl 2-acetamido-5-[2-(2,5-dimethoxyphenyl)ethyl]benzoate Chemical compound C1=C(NC(C)=O)C(C(=O)OC)=CC(CCC=2C(=CC=C(OC)C=2)OC)=C1 YGASXVZXXXSXMH-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
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- C07C233/54—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of a saturated carbon skeleton
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- C07C275/32—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by singly-bound oxygen atoms
- C07C275/34—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by singly-bound oxygen atoms having nitrogen atoms of urea groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
- C07C275/36—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by singly-bound oxygen atoms having nitrogen atoms of urea groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring with at least one of the oxygen atoms further bound to a carbon atom of a six-membered aromatic ring, e.g. N-aryloxyphenylureas
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- C07D207/06—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with radicals, containing only hydrogen and carbon atoms, attached to ring carbon atoms
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- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
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- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/10—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
- C07D211/14—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
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- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/096—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/14—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D295/155—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
-
- 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)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
- Diabetes (AREA)
- Rheumatology (AREA)
- Transplantation (AREA)
- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- Neurology (AREA)
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- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Dermatology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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SE0400234A SE0400234D0 (sv) | 2004-02-06 | 2004-02-06 | New compounds, methods for their preparation and use thereof |
Publications (1)
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ZA200606321B true ZA200606321B (en) | 2008-01-30 |
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ID=31885234
Family Applications (1)
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ZA200606321A ZA200606321B (en) | 2004-02-06 | 2005-02-04 | New compounds, methods for their preparation and use thereof |
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US (1) | US7074831B2 (ja) |
EP (1) | EP1720825B1 (ja) |
JP (2) | JP5280634B2 (ja) |
KR (1) | KR101167142B1 (ja) |
CN (1) | CN1914152B (ja) |
AT (1) | ATE400547T1 (ja) |
AU (1) | AU2005210052B2 (ja) |
BR (1) | BRPI0507390A (ja) |
CA (1) | CA2552942A1 (ja) |
DE (1) | DE602005008016D1 (ja) |
ES (1) | ES2310333T3 (ja) |
IL (1) | IL176707A (ja) |
NO (1) | NO20063974L (ja) |
NZ (1) | NZ548619A (ja) |
PL (1) | PL1720825T3 (ja) |
RU (1) | RU2006132071A (ja) |
SE (1) | SE0400234D0 (ja) |
WO (1) | WO2005075410A1 (ja) |
ZA (1) | ZA200606321B (ja) |
Families Citing this family (30)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7407955B2 (en) | 2002-08-21 | 2008-08-05 | Boehringer Ingelheim Pharma Gmbh & Co., Kg | 8-[3-amino-piperidin-1-yl]-xanthines, the preparation thereof and their use as pharmaceutical compositions |
US7999132B2 (en) * | 2004-12-07 | 2011-08-16 | Toyama Chemical Co., Ltd. | Anthranilic acid derivative or salt thereof |
PE20080251A1 (es) | 2006-05-04 | 2008-04-25 | Boehringer Ingelheim Int | Usos de inhibidores de dpp iv |
EP1852108A1 (en) | 2006-05-04 | 2007-11-07 | Boehringer Ingelheim Pharma GmbH & Co.KG | DPP IV inhibitor formulations |
CN102838599A (zh) | 2006-05-04 | 2012-12-26 | 贝林格尔.英格海姆国际有限公司 | 多晶型 |
ES2319596B1 (es) | 2006-12-22 | 2010-02-08 | Laboratorios Almirall S.A. | Nuevos derivados de los acidos amino-nicotinico y amino-isonicotinico. |
AU2008213147A1 (en) * | 2007-02-06 | 2008-08-14 | Chelsea Therapeutics, Inc. | New compounds, methods for their preparation and use thereof |
ES2315185B1 (es) * | 2007-08-10 | 2010-01-13 | Laboratorios Almirall S.A. | Nuevos derivados del acido azabifenilaminobenzoico. |
UY31272A1 (es) * | 2007-08-10 | 2009-01-30 | Almirall Lab | Nuevos derivados de ácido azabifenilaminobenzoico |
US7866852B2 (en) * | 2007-08-29 | 2011-01-11 | Texas Instruments Incorporated | Heat sinks for cooling LEDs in projectors |
PE20140960A1 (es) | 2008-04-03 | 2014-08-15 | Boehringer Ingelheim Int | Formulaciones que comprenden un inhibidor de dpp4 |
EP2135610A1 (en) * | 2008-06-20 | 2009-12-23 | Laboratorios Almirall, S.A. | Combination comprising DHODH inhibitors and methotrexate |
BRPI0916997A2 (pt) | 2008-08-06 | 2020-12-15 | Boehringer Ingelheim International Gmbh | Inibidor de dpp-4 e seu uso |
US20200155558A1 (en) | 2018-11-20 | 2020-05-21 | Boehringer Ingelheim International Gmbh | Treatment for diabetes in patients with insufficient glycemic control despite therapy with an oral antidiabetic drug |
EP2239256A1 (en) | 2009-03-13 | 2010-10-13 | Almirall, S.A. | Sodium salt of 5-cyclopropyl-2-{[2-(2,6-difluorophenyl)pyrimidin-5-yl]amino}benzoic acid as DHODH inhibitor |
EP2414328B1 (en) * | 2009-04-02 | 2021-05-26 | Merck Serono S.A. | Dihydroorotate dehydrogenase inhibitors |
EP2314577A1 (en) | 2009-10-16 | 2011-04-27 | Almirall, S.A. | Process for manufacturing 2-[(3,5-difluoro-3'-methoxy-1,1'-biphenyl-4-yl)amino]nicotinic acid |
KR102668834B1 (ko) | 2009-11-27 | 2024-05-24 | 베링거 인겔하임 인터내셔날 게엠베하 | 리나글립틴과 같은 dpp-iv 억제제를 사용한 유전자형 검사된 당뇨병 환자의 치료 |
US8778949B2 (en) * | 2010-01-11 | 2014-07-15 | Theravance Biopharma R&D Ip, Llc | 1-(2-phenoxymethylphenyl)piperazine compounds |
US8686048B2 (en) | 2010-05-06 | 2014-04-01 | Rhizen Pharmaceuticals Sa | Immunomodulator and anti-inflammatory compounds |
US9034883B2 (en) | 2010-11-15 | 2015-05-19 | Boehringer Ingelheim International Gmbh | Vasoprotective and cardioprotective antidiabetic therapy |
US10016402B2 (en) | 2011-02-08 | 2018-07-10 | Children's Medical Center Corporation | Methods for treatment of melanoma |
US20140031383A1 (en) | 2011-02-08 | 2014-01-30 | Dana-Farber Cancer Institute, Inc. | Methods for treatment of melanoma |
WO2013171167A1 (en) | 2012-05-14 | 2013-11-21 | Boehringer Ingelheim International Gmbh | A xanthine derivative as dpp -4 inhibitor for use in the treatment of podocytes related disorders and/or nephrotic syndrome |
CN103788020B (zh) * | 2014-01-22 | 2015-11-04 | 苏州明锐医药科技有限公司 | 沃替西汀的制备方法 |
EP4233840A3 (en) | 2016-06-10 | 2023-10-18 | Boehringer Ingelheim International GmbH | Combinations of linagliptin and metformin |
KR20200042906A (ko) * | 2017-08-07 | 2020-04-24 | 고쿠리츠다이가쿠호진 히로시마다이가쿠 | 신규 안트라닐산계 화합물, 및 이것을 사용한 Pin1 저해제, 염증성 질환의 치료제 및 암의 치료제 |
WO2020225330A1 (en) | 2019-05-07 | 2020-11-12 | Universität Hamburg | Dhodh inhibitors and their use as antiviral agents |
EP3992182A1 (en) | 2020-10-28 | 2022-05-04 | Cisbio Bioassays | Europium(iii) complexes as ph sensors |
EP4119138A1 (en) | 2021-07-12 | 2023-01-18 | Universität Hamburg | Dhodh inhibitors and their use as antiviral agents |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2064305A1 (en) | 1970-12-29 | 1972-07-06 | Farbenfabriken Bayer Ag, 5090 Leverkusen | Anthranilic acid esters alkylated on the nucleus |
US4307113A (en) * | 1978-04-20 | 1981-12-22 | Sandoz, Inc. | Anthranilic acid derivatives |
ATE5399T1 (de) | 1980-02-06 | 1983-12-15 | F. Hoffmann-La Roche & Co. Aktiengesellschaft | Verfahren zur herstellung von anthranilsaeurederivaten. |
NO174506B (no) | 1984-10-30 | 1994-02-07 | Usv Pharma Corp | Analogifremgangsmaate ved fremstilling av terapeutisk aktive forbindelser |
HUT60458A (en) * | 1991-02-01 | 1992-09-28 | Sandoz Ag | Process for producing benzyloxyphenyl derivatives and pharmaceutical compositions comprising same |
KR100437580B1 (ko) * | 1995-03-14 | 2004-07-16 | 노파르티스 아게 | 삼치환된페닐유도체 |
WO1997028118A1 (en) | 1996-02-05 | 1997-08-07 | Hoechst Celanese Corporation | Process for preparing anthranilic acids |
MXPA04000224A (es) * | 2001-07-10 | 2005-07-25 | 4Sc Ag | Novedosos compuestos como agentes antiinflamatorios, inmunomoduladores y antiproliferativos. |
DE10254872A1 (de) | 2002-11-25 | 2004-06-03 | Symrise Gmbh & Co. Kg | Anthranilsäureamide und deren Derivate als kosmetische und pharmazeutische Wirkstoffe |
-
2004
- 2004-02-06 SE SE0400234A patent/SE0400234D0/xx unknown
-
2005
- 2005-02-04 BR BRPI0507390-1A patent/BRPI0507390A/pt not_active IP Right Cessation
- 2005-02-04 WO PCT/EP2005/050482 patent/WO2005075410A1/en active IP Right Grant
- 2005-02-04 PL PL05707941T patent/PL1720825T3/pl unknown
- 2005-02-04 US US11/050,430 patent/US7074831B2/en not_active Expired - Fee Related
- 2005-02-04 AT AT05707941T patent/ATE400547T1/de not_active IP Right Cessation
- 2005-02-04 KR KR1020067018184A patent/KR101167142B1/ko not_active IP Right Cessation
- 2005-02-04 RU RU2006132071/04A patent/RU2006132071A/ru not_active Application Discontinuation
- 2005-02-04 ZA ZA200606321A patent/ZA200606321B/en unknown
- 2005-02-04 EP EP05707941A patent/EP1720825B1/en active Active
- 2005-02-04 CN CN2005800038900A patent/CN1914152B/zh not_active Expired - Fee Related
- 2005-02-04 JP JP2006551856A patent/JP5280634B2/ja not_active Expired - Fee Related
- 2005-02-04 DE DE602005008016T patent/DE602005008016D1/de active Active
- 2005-02-04 ES ES05707941T patent/ES2310333T3/es active Active
- 2005-02-04 CA CA002552942A patent/CA2552942A1/en not_active Abandoned
- 2005-02-04 AU AU2005210052A patent/AU2005210052B2/en not_active Ceased
- 2005-02-04 NZ NZ548619A patent/NZ548619A/en unknown
-
2006
- 2006-07-04 IL IL176707A patent/IL176707A/en not_active IP Right Cessation
- 2006-09-05 NO NO20063974A patent/NO20063974L/no not_active Application Discontinuation
-
2012
- 2012-03-12 JP JP2012054181A patent/JP5379876B2/ja not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
JP2007522144A (ja) | 2007-08-09 |
CN1914152B (zh) | 2010-06-09 |
IL176707A (en) | 2011-04-28 |
US20050187297A1 (en) | 2005-08-25 |
AU2005210052A1 (en) | 2005-08-18 |
AU2005210052B2 (en) | 2010-12-23 |
BRPI0507390A (pt) | 2007-07-10 |
JP5379876B2 (ja) | 2013-12-25 |
ES2310333T3 (es) | 2009-01-01 |
CN1914152A (zh) | 2007-02-14 |
EP1720825B1 (en) | 2008-07-09 |
ATE400547T1 (de) | 2008-07-15 |
CA2552942A1 (en) | 2005-08-18 |
JP5280634B2 (ja) | 2013-09-04 |
US7074831B2 (en) | 2006-07-11 |
EP1720825A1 (en) | 2006-11-15 |
JP2012144548A (ja) | 2012-08-02 |
NZ548619A (en) | 2010-06-25 |
IL176707A0 (en) | 2006-10-31 |
WO2005075410A1 (en) | 2005-08-18 |
PL1720825T3 (pl) | 2009-04-30 |
RU2006132071A (ru) | 2008-03-20 |
KR20070042496A (ko) | 2007-04-23 |
NO20063974L (no) | 2006-09-05 |
KR101167142B1 (ko) | 2012-07-23 |
DE602005008016D1 (de) | 2008-08-21 |
SE0400234D0 (sv) | 2004-02-06 |
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