ZA200400161B - Novel vinyl carboxylic acid derivatives and their use as antidiabetics etc. - Google Patents
Novel vinyl carboxylic acid derivatives and their use as antidiabetics etc. Download PDFInfo
- Publication number
- ZA200400161B ZA200400161B ZA200400161A ZA200400161A ZA200400161B ZA 200400161 B ZA200400161 B ZA 200400161B ZA 200400161 A ZA200400161 A ZA 200400161A ZA 200400161 A ZA200400161 A ZA 200400161A ZA 200400161 B ZA200400161 B ZA 200400161B
- Authority
- ZA
- South Africa
- Prior art keywords
- phenyl
- allyloxy
- bis
- acetic acid
- chloro
- Prior art date
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- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical class OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 title description 4
- 230000003178 anti-diabetic effect Effects 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 210
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 120
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 83
- -1 hydroxy, cyano, amino Chemical group 0.000 claims description 80
- 229910052736 halogen Inorganic materials 0.000 claims description 58
- 150000002367 halogens Chemical class 0.000 claims description 58
- 239000000203 mixture Substances 0.000 claims description 58
- 125000003118 aryl group Chemical group 0.000 claims description 43
- 125000001072 heteroaryl group Chemical group 0.000 claims description 37
- 150000003839 salts Chemical class 0.000 claims description 30
- 125000001424 substituent group Chemical group 0.000 claims description 29
- 102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 claims description 23
- 108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 claims description 23
- 238000011282 treatment Methods 0.000 claims description 22
- 239000000556 agonist Substances 0.000 claims description 21
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 18
- 239000008194 pharmaceutical composition Substances 0.000 claims description 17
- 230000002265 prevention Effects 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
- 125000004104 aryloxy group Chemical group 0.000 claims description 14
- 239000004305 biphenyl Substances 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 10
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 9
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 9
- 206010022489 Insulin Resistance Diseases 0.000 claims description 8
- 125000005110 aryl thio group Chemical group 0.000 claims description 8
- 206010012601 diabetes mellitus Diseases 0.000 claims description 8
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 8
- 208000008589 Obesity Diseases 0.000 claims description 7
- 235000020824 obesity Nutrition 0.000 claims description 7
- 208000001145 Metabolic Syndrome Diseases 0.000 claims description 6
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims description 6
- 125000000732 arylene group Chemical group 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- 230000001404 mediated effect Effects 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 208000032928 Dyslipidaemia Diseases 0.000 claims description 5
- 125000002252 acyl group Chemical group 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
- XTKJJTSBXITZND-UHFFFAOYSA-N 2-[3-[3,3-bis(4-bromophenyl)prop-2-enoxy]phenyl]acetic acid Chemical compound OC(=O)CC1=CC=CC(OCC=C(C=2C=CC(Br)=CC=2)C=2C=CC(Br)=CC=2)=C1 XTKJJTSBXITZND-UHFFFAOYSA-N 0.000 claims description 4
- 201000001320 Atherosclerosis Diseases 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 4
- 208000002705 Glucose Intolerance Diseases 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 4
- 201000009104 prediabetes syndrome Diseases 0.000 claims description 4
- 239000012453 solvate Substances 0.000 claims description 4
- 208000011580 syndromic disease Diseases 0.000 claims description 4
- OIHKRDDGCUUDRN-OBGWFSINSA-N 2-[4-[(e)-3-(4-phenoxyphenyl)but-2-enoxy]phenyl]acetic acid Chemical compound C=1C=C(OC=2C=CC=CC=2)C=CC=1C(/C)=C/COC1=CC=C(CC(O)=O)C=C1 OIHKRDDGCUUDRN-OBGWFSINSA-N 0.000 claims description 3
- KFLOAWUJCIVKIB-GHRIWEEISA-N 2-[4-[(e)-3-(9h-fluoren-2-yl)but-2-enoxy]phenyl]propanoic acid Chemical compound C1=CC(C(C(O)=O)C)=CC=C1OC\C=C(/C)C1=CC=C2C3=CC=CC=C3CC2=C1 KFLOAWUJCIVKIB-GHRIWEEISA-N 0.000 claims description 3
- AHVHHKDNTFMYLW-UHFFFAOYSA-N 2-[4-[3,3-bis(4-bromophenyl)prop-2-enoxy]phenyl]acetic acid Chemical compound C1=CC(CC(=O)O)=CC=C1OCC=C(C=1C=CC(Br)=CC=1)C1=CC=C(Br)C=C1 AHVHHKDNTFMYLW-UHFFFAOYSA-N 0.000 claims description 3
- 208000035150 Hypercholesterolemia Diseases 0.000 claims description 3
- 208000017170 Lipid metabolism disease Diseases 0.000 claims description 3
- 239000002552 dosage form Substances 0.000 claims description 3
- BALHWYJTFQLDSV-KNTRCKAVSA-N methyl 2-[4-[(e)-3-(4-phenoxyphenyl)but-2-enoxy]phenyl]acetate Chemical compound C1=CC(CC(=O)OC)=CC=C1OC\C=C(/C)C(C=C1)=CC=C1OC1=CC=CC=C1 BALHWYJTFQLDSV-KNTRCKAVSA-N 0.000 claims description 3
- 125000000335 thiazolyl group Chemical group 0.000 claims description 3
- ZNPVUJSNQYBLAG-GHRIWEEISA-N 2-[3-[(e)-3-[4-(4-bromophenyl)phenyl]but-2-enoxy]phenyl]acetic acid Chemical compound C=1C=C(C=2C=CC(Br)=CC=2)C=CC=1C(/C)=C/COC1=CC=CC(CC(O)=O)=C1 ZNPVUJSNQYBLAG-GHRIWEEISA-N 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
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000004494 ethyl ester group Chemical group 0.000 claims description 2
- QUJDKESJCPQXCF-QGOAFFKASA-N methyl 2-[4-[(e)-3-(9h-fluoren-2-yl)but-2-enoxy]phenyl]acetate Chemical compound C1=CC(CC(=O)OC)=CC=C1OC\C=C(/C)C1=CC=C2C3=CC=CC=C3CC2=C1 QUJDKESJCPQXCF-QGOAFFKASA-N 0.000 claims description 2
- 108020005497 Nuclear hormone receptor Proteins 0.000 claims 2
- 102000006255 nuclear receptors Human genes 0.000 claims 2
- 108020004017 nuclear receptors Proteins 0.000 claims 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 2
- YYFMGAIRBHSELC-SAPNQHFASA-N 2-[4-[(e)-3-[4-(4-bromophenyl)phenyl]but-2-enoxy]phenyl]acetic acid Chemical compound C=1C=C(C=2C=CC(Br)=CC=2)C=CC=1C(/C)=C/COC1=CC=C(CC(O)=O)C=C1 YYFMGAIRBHSELC-SAPNQHFASA-N 0.000 claims 1
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims 1
- 125000006306 4-iodophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1I 0.000 claims 1
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims 1
- 125000001207 fluorophenyl group Chemical group 0.000 claims 1
- OTTRYSUIFFPDED-UHFFFAOYSA-N methyl 2-[4-[3,3-bis(4-bromophenyl)prop-2-enoxy]phenyl]acetate Chemical compound C1=CC(CC(=O)OC)=CC=C1OCC=C(C=1C=CC(Br)=CC=1)C1=CC=C(Br)C=C1 OTTRYSUIFFPDED-UHFFFAOYSA-N 0.000 claims 1
- 238000007911 parenteral administration Methods 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 115
- 238000000034 method Methods 0.000 description 73
- 235000013350 formula milk Nutrition 0.000 description 66
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 62
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 54
- 238000005481 NMR spectroscopy Methods 0.000 description 49
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 48
- 229940093499 ethyl acetate Drugs 0.000 description 37
- 235000019439 ethyl acetate Nutrition 0.000 description 37
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 36
- 239000000243 solution Substances 0.000 description 30
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 25
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 23
- 235000019441 ethanol Nutrition 0.000 description 20
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 20
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- JPZZOCRNTVCBAQ-UHFFFAOYSA-N ethyl 3-[3-[3,3-bis(4-bromophenyl)prop-2-enoxy]phenyl]propanoate Chemical compound CCOC(=O)CCC1=CC=CC(OCC=C(C=2C=CC(Br)=CC=2)C=2C=CC(Br)=CC=2)=C1 JPZZOCRNTVCBAQ-UHFFFAOYSA-N 0.000 description 5
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
- C07C69/734—Ethers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/24—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/16—Radicals substituted by singly bound hetero atoms other than halogen by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
- C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
- C07C2603/18—Fluorenes; Hydrogenated fluorenes
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Diabetes (AREA)
- Heart & Thoracic Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Cardiology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Neurosurgery (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Biomedical Technology (AREA)
- Rheumatology (AREA)
- Neurology (AREA)
- Urology & Nephrology (AREA)
- Dermatology (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Vascular Medicine (AREA)
- Psychiatry (AREA)
- Child & Adolescent Psychology (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DKPA200101154 | 2001-07-30 |
Publications (1)
Publication Number | Publication Date |
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ZA200400161B true ZA200400161B (en) | 2004-08-18 |
Family
ID=8160643
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ZA200400161A ZA200400161B (en) | 2001-07-30 | 2004-01-09 | Novel vinyl carboxylic acid derivatives and their use as antidiabetics etc. |
Country Status (15)
Country | Link |
---|---|
EP (1) | EP1414778A1 (fr) |
JP (1) | JP2004536150A (fr) |
KR (1) | KR20040019087A (fr) |
CN (1) | CN1537093A (fr) |
BR (1) | BR0211414A (fr) |
CA (1) | CA2452665A1 (fr) |
CZ (1) | CZ2004133A3 (fr) |
HU (1) | HUP0401575A2 (fr) |
IL (1) | IL159547A0 (fr) |
MX (1) | MXPA04000891A (fr) |
NO (1) | NO20040389L (fr) |
PL (1) | PL366401A1 (fr) |
RU (1) | RU2004105956A (fr) |
WO (1) | WO2003011807A1 (fr) |
ZA (1) | ZA200400161B (fr) |
Families Citing this family (22)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1688540A (zh) | 2002-09-05 | 2005-10-26 | 诺沃挪第克公司 | 新颖的乙烯基羧酸衍生物以及它们的治疗用途 |
KR20050055790A (ko) * | 2002-10-28 | 2005-06-13 | 노보 노르디스크 에이/에스 | Ppar 매개 질환의 치료에 유용한 신규 화합물 |
PL376718A1 (pl) * | 2002-10-28 | 2006-01-09 | Novo Nordisk A/S | Nowe związki, ich wytwarzanie i stosowanie |
ITRM20030305A1 (it) * | 2003-06-20 | 2004-12-21 | Sigma Tau Ind Farmaceuti | Preparazione di nuovi derivati di acidi fenil o fenossialchil mono e dicarbossilici utili nel trattamento dell'iperglicemia e dell'ipertrigliceridemia tipiche del diabete del tipo ii. |
JP4928941B2 (ja) * | 2003-09-19 | 2012-05-09 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | 4−((フェノキシアルキル)チオ)−フェノキシ酢酸および類似化合物 |
EP1670744B9 (fr) | 2003-09-19 | 2012-09-05 | Janssen Pharmaceutica NV | Acides 4-((phenoxyalkyl)thio)-phenoxyacetiques et analogues |
WO2005105736A1 (fr) * | 2004-05-05 | 2005-11-10 | Novo Nordisk A/S | Nouveaux composes, leur preparation et leur utilisation |
ME02005B (fr) | 2005-09-14 | 2012-08-31 | Takeda Pharmaceuticals Co | Inhibiteurs de la dipeptidyl peptidase permettant de traiter le diabete |
JO3006B1 (ar) | 2005-09-14 | 2016-09-05 | Janssen Pharmaceutica Nv | املاح ليسين مبتكرة من مشتقات حامض 4-((فينوكسي الكيل)ثيو) فينوكسي الخليك |
CA2622642C (fr) | 2005-09-16 | 2013-12-31 | Takeda Pharmaceutical Company Limited | Inhibiteurs de dipeptidylpeptidase |
US7943613B2 (en) | 2005-12-22 | 2011-05-17 | High Point Pharmaceuticals, Llc | Compounds, their preparation and use |
PE20080188A1 (es) | 2006-04-18 | 2008-03-10 | Janssen Pharmaceutica Nv | Derivados del acido benzoazepin-oxi-acetico como agonistas de ppar-delta usados para aumentar hdl-c, reducir ldl-c y reducir colesterol |
KR100693132B1 (ko) * | 2006-06-23 | 2007-03-14 | 동해전장 주식회사 | 정션박스내에 삽입된 릴레이의 동작 검사 장치 |
TW200838536A (en) | 2006-11-29 | 2008-10-01 | Takeda Pharmaceutical | Polymorphs of succinate salt of 2-[6-(3-amino-piperidin-1-yl)-3-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-ylmethy]-4-fluor-benzonitrile and methods of use therefor |
US20120168303A1 (en) * | 2011-01-05 | 2012-07-05 | Sueng-Nien Kao | Salt water activated emergency lighting device |
CN103467406B (zh) * | 2013-09-03 | 2014-12-17 | 浙江医药高等专科学校 | 卤素取代的四氮唑羧酸类化合物、其制备方法和用途 |
CN103467407B (zh) * | 2013-09-03 | 2015-04-22 | 浙江医药高等专科学校 | 四氮唑羧酸类化合物及其用途 |
CN103467405B (zh) * | 2013-09-03 | 2015-01-07 | 浙江医药高等专科学校 | 一类四氮唑羧酸类化合物、其制备方法和用途 |
CN103467408B (zh) * | 2013-09-03 | 2015-01-21 | 浙江医药高等专科学校 | 一类四氮唑羧酸类化合物及其用途 |
CN103467409B (zh) * | 2013-09-03 | 2015-01-07 | 浙江医药高等专科学校 | 取代的四氮唑羧酸类化合物及其用途 |
KR20230054373A (ko) * | 2020-07-22 | 2023-04-24 | 르네오 파마슈티컬스, 인크. | 결정질 ppar-델타 작용제 |
WO2023147309A1 (fr) | 2022-01-25 | 2023-08-03 | Reneo Pharmaceuticals, Inc. | Utilisation d'agonistes ppar-delta dans le traitement d'une maladie |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0098690B1 (fr) * | 1982-06-14 | 1987-09-09 | Takeda Chemical Industries, Ltd. | Dérivés d'acides vinylcarboxyliques, leur préparation et leur utilisation |
AU2652397A (en) * | 1996-05-13 | 1997-12-05 | Nippon Shinyaku Co. Ltd. | Substituted ethylene compounds and drugs |
JP2002542218A (ja) * | 1999-04-20 | 2002-12-10 | ノボ ノルディスク アクティーゼルスカブ | 新規な化合物、それらの製造および使用 |
CA2395298A1 (fr) * | 2000-01-28 | 2001-08-02 | Novo Nordisk A/S | Derives de l'acide propionique et leur utilisation dans le traitement du diabete et de l'obesite |
-
2002
- 2002-07-05 CN CNA028150996A patent/CN1537093A/zh active Pending
- 2002-07-05 CA CA002452665A patent/CA2452665A1/fr not_active Abandoned
- 2002-07-05 CZ CZ2004133A patent/CZ2004133A3/cs unknown
- 2002-07-05 EP EP02745186A patent/EP1414778A1/fr not_active Withdrawn
- 2002-07-05 IL IL15954702A patent/IL159547A0/xx unknown
- 2002-07-05 HU HU0401575A patent/HUP0401575A2/hu unknown
- 2002-07-05 JP JP2003517001A patent/JP2004536150A/ja active Pending
- 2002-07-05 MX MXPA04000891A patent/MXPA04000891A/es unknown
- 2002-07-05 RU RU2004105956/04A patent/RU2004105956A/ru not_active Application Discontinuation
- 2002-07-05 BR BR0211414-3A patent/BR0211414A/pt not_active IP Right Cessation
- 2002-07-05 KR KR10-2004-7001417A patent/KR20040019087A/ko not_active Application Discontinuation
- 2002-07-05 PL PL02366401A patent/PL366401A1/xx not_active Application Discontinuation
- 2002-07-05 WO PCT/DK2002/000471 patent/WO2003011807A1/fr not_active Application Discontinuation
-
2004
- 2004-01-09 ZA ZA200400161A patent/ZA200400161B/en unknown
- 2004-01-29 NO NO20040389A patent/NO20040389L/no not_active Application Discontinuation
Also Published As
Publication number | Publication date |
---|---|
HUP0401575A2 (hu) | 2004-11-29 |
CN1537093A (zh) | 2004-10-13 |
RU2004105956A (ru) | 2005-03-27 |
IL159547A0 (en) | 2004-06-01 |
BR0211414A (pt) | 2004-08-17 |
CA2452665A1 (fr) | 2003-02-13 |
CZ2004133A3 (cs) | 2004-06-16 |
EP1414778A1 (fr) | 2004-05-06 |
WO2003011807A1 (fr) | 2003-02-13 |
PL366401A1 (en) | 2005-01-24 |
MXPA04000891A (es) | 2004-05-21 |
NO20040389L (no) | 2004-01-29 |
KR20040019087A (ko) | 2004-03-04 |
JP2004536150A (ja) | 2004-12-02 |
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