CA2599281A1 - Thiazole derivatives as ppar delta ligands and their manufacturing process - Google Patents
Thiazole derivatives as ppar delta ligands and their manufacturing process Download PDFInfo
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- CA2599281A1 CA2599281A1 CA002599281A CA2599281A CA2599281A1 CA 2599281 A1 CA2599281 A1 CA 2599281A1 CA 002599281 A CA002599281 A CA 002599281A CA 2599281 A CA2599281 A CA 2599281A CA 2599281 A1 CA2599281 A1 CA 2599281A1
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- 150000007979 thiazole derivatives Chemical class 0.000 title claims 14
- 101150014691 PPARA gene Proteins 0.000 title 1
- 239000003446 ligand Substances 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- 102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 claims abstract 4
- 108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 claims abstract 4
- 150000001875 compounds Chemical class 0.000 claims 18
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 8
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 8
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 6
- 239000004480 active ingredient Substances 0.000 claims 6
- 229910052736 halogen Inorganic materials 0.000 claims 6
- 125000005843 halogen group Chemical group 0.000 claims 6
- 238000000034 method Methods 0.000 claims 6
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 5
- 229910052740 iodine Inorganic materials 0.000 claims 5
- 229910052783 alkali metal Inorganic materials 0.000 claims 4
- 150000001340 alkali metals Chemical class 0.000 claims 4
- 125000006244 carboxylic acid protecting group Chemical group 0.000 claims 4
- 239000003795 chemical substances by application Substances 0.000 claims 4
- 229910052801 chlorine Inorganic materials 0.000 claims 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims 4
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 239000002585 base Substances 0.000 claims 3
- 238000006467 substitution reaction Methods 0.000 claims 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 125000005103 alkyl silyl group Chemical group 0.000 claims 2
- 239000007795 chemical reaction product Substances 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 229910017053 inorganic salt Inorganic materials 0.000 claims 2
- 229910052744 lithium Inorganic materials 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 230000009257 reactivity Effects 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 239000011593 sulfur Substances 0.000 claims 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 2
- 150000003568 thioethers Chemical class 0.000 claims 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
- 206010003210 Arteriosclerosis Diseases 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 239000007818 Grignard reagent Substances 0.000 claims 1
- 208000031226 Hyperlipidaemia Diseases 0.000 claims 1
- 208000008589 Obesity Diseases 0.000 claims 1
- 230000003213 activating effect Effects 0.000 claims 1
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 125000005377 alkyl thioxy group Chemical group 0.000 claims 1
- 208000011775 arteriosclerosis disease Diseases 0.000 claims 1
- 125000005128 aryl amino alkyl group Chemical group 0.000 claims 1
- 235000013361 beverage Nutrition 0.000 claims 1
- 150000001733 carboxylic acid esters Chemical class 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 239000002537 cosmetic Substances 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- 238000007336 electrophilic substitution reaction Methods 0.000 claims 1
- 238000010931 ester hydrolysis Methods 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 239000002778 food additive Substances 0.000 claims 1
- 235000013373 food additive Nutrition 0.000 claims 1
- 150000004795 grignard reagents Chemical class 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 235000013402 health food Nutrition 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 claims 1
- 235000020824 obesity Nutrition 0.000 claims 1
- 230000003287 optical effect Effects 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 229910052763 palladium Inorganic materials 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims 1
- 239000013589 supplement Substances 0.000 claims 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 238000001308 synthesis method Methods 0.000 abstract 1
- -1 thiazole derivative compounds Chemical class 0.000 abstract 1
Classifications
-
- 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
- C07D277/26—Radicals substituted by sulfur atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- 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
- C07D417/12—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 linked by a chain containing hetero atoms as chain links
Landscapes
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Diabetes (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Abstract
The present invention relates to novel thiazole derivative compounds having activity for peroxisome prolif erator-activated receptor .delta.
(PPAR.delta.), as well as their intermediates and synthesis methods thereof .
(PPAR.delta.), as well as their intermediates and synthesis methods thereof .
Claims (17)
1. Thiazole derivatives of Formula I as racemates or optical isomers:
wherein A is hydrogen, R2 or R1 is a hydrogen atom, a C1-4 alkyl group, a C1-4 alkyloxy group, a C1-4 alkylthioxy group, a C1-4 alkylamine group, a fluorine atom or a chlorine atom;
M is an integer from 0 to 4;
R2 is a phenol-protecting group selected from among C1-4 lower alkyl groups, allyl groups, alkylsilyl groups, alkylarylsilyl groups and a tetrahydropyranyl group;
R3 groups are different from each other and denote a hydrogen atom, a halogen atom, or a C1-4 alkyl or alkoxy group substituted or unsubstituted with halogen;
N is an integer from 0 to 5;
R4 is R5 is a hydrogen atom, a hydroxyl group or a C1-4 alkyl group;
R6 is a carboxylic acid protecting group having C1-4 alkyl, an allyl group, a hydrogen atom or an alkali metal;
R11 is an arylaminoalkyl group or an alkylaminoalkyl group;
R12 is a halogen atom, a cyano group, or a C1-4 alkyl or alkoxy group substituted with unsubstituted with halogen;
R13 is a hydrogen atom, a halogen atom, a cyano group, a C1-4 alkyl or alkoxy group substituted with unsubstituted with halogen;
o, p and q are each independently an integer from 1 to 5; and r is an integer from 1 to 9.
wherein A is hydrogen, R2 or R1 is a hydrogen atom, a C1-4 alkyl group, a C1-4 alkyloxy group, a C1-4 alkylthioxy group, a C1-4 alkylamine group, a fluorine atom or a chlorine atom;
M is an integer from 0 to 4;
R2 is a phenol-protecting group selected from among C1-4 lower alkyl groups, allyl groups, alkylsilyl groups, alkylarylsilyl groups and a tetrahydropyranyl group;
R3 groups are different from each other and denote a hydrogen atom, a halogen atom, or a C1-4 alkyl or alkoxy group substituted or unsubstituted with halogen;
N is an integer from 0 to 5;
R4 is R5 is a hydrogen atom, a hydroxyl group or a C1-4 alkyl group;
R6 is a carboxylic acid protecting group having C1-4 alkyl, an allyl group, a hydrogen atom or an alkali metal;
R11 is an arylaminoalkyl group or an alkylaminoalkyl group;
R12 is a halogen atom, a cyano group, or a C1-4 alkyl or alkoxy group substituted with unsubstituted with halogen;
R13 is a hydrogen atom, a halogen atom, a cyano group, a C1-4 alkyl or alkoxy group substituted with unsubstituted with halogen;
o, p and q are each independently an integer from 1 to 5; and r is an integer from 1 to 9.
2. The thiazole derivatives of Claim 1, which are represented by Formula VI:
wherein R1 to R5, m and n have the same meanings as defined in Formula I.
wherein R1 to R5, m and n have the same meanings as defined in Formula I.
3. The thiazole derivatives of Claim 1, which are represented by Formula VII:
wherein R1, R3 to R5, m and n have the same meanings as defined in Formula I.
wherein R1, R3 to R5, m and n have the same meanings as defined in Formula I.
4. The thiazole derivatives of Claim 1, which are represented by Formula IX:
wherein R1, R3 to R5, m and n have the same meanings as defined in Formula I, and R6a is a carboxylic acid protecting group having C1-4 alkyl or an allyl group.
wherein R1, R3 to R5, m and n have the same meanings as defined in Formula I, and R6a is a carboxylic acid protecting group having C1-4 alkyl or an allyl group.
5. The thiazole derivatives of Claim 1, which are represented by Formula X:
wherein R1, R3 to R5, m and n have the same meanings as defined in Formula I, and R6b is a hydrogen atom or an alkali metal.
wherein R1, R3 to R5, m and n have the same meanings as defined in Formula I, and R6b is a hydrogen atom or an alkali metal.
6. A method for preparing thiazole derivatives, comprising the steps of:
a) reacting a 4-halogen phenol compound of Formula II
with a phenol-protecting alkylsilyl group in the presence of a base to prepare a compound of Formula III;
b) subjecting the compound of Formula III to halogen-to-lithium substitution, and then to reaction with sulfur and a compound of Formula IV so as to prepare a compound of Formula V; and c) reacting the compound of Formula V with a strong base and an electrophilic compound so as to prepare a compound of Formula VI:
wherein X1 denotes a bromine atom or an iodine atom, X2 denotes a chlorine atom, a bromine atom, an iodine atom, or a leaving group having high reactivity in nucleophilic substitution reaction, and the remainder has the same meanings as defined in Formula I.
a) reacting a 4-halogen phenol compound of Formula II
with a phenol-protecting alkylsilyl group in the presence of a base to prepare a compound of Formula III;
b) subjecting the compound of Formula III to halogen-to-lithium substitution, and then to reaction with sulfur and a compound of Formula IV so as to prepare a compound of Formula V; and c) reacting the compound of Formula V with a strong base and an electrophilic compound so as to prepare a compound of Formula VI:
wherein X1 denotes a bromine atom or an iodine atom, X2 denotes a chlorine atom, a bromine atom, an iodine atom, or a leaving group having high reactivity in nucleophilic substitution reaction, and the remainder has the same meanings as defined in Formula I.
7. The method of Claim 6, which further comprises the step of: d) removing the phenol-protecting silyl group of a compound of Formula VI so as to prepare a compound of Formula VII:
wherein R1 to R5, m and n have the same meanings as defined in Formula I.
wherein R1 to R5, m and n have the same meanings as defined in Formula I.
8. A method for preparing thiazole derivatives, comprising the steps of:
reacting a 4-halogen phenol compound of Formula II with a Grignard reagent, subjecting the reaction product to halogen-to-lithium substitution and then reacting the reaction product with sulfur and the compound of Formula IV
so as to form a thioether compound; and reacting the thioether compound with a strong base without separation and then with an electrophilic compound so as to prepare a compound of Formula VII:
wherein X1 denotes a bromine atom or an iodine atom, X2 denotes a chlorine atom, a bromine atom, an iodine atom, or a leaving group having high reactivity in electrophilic substitution reaction, and R1, R3 to R5, m and n have the same meanings as defined in Formula I.
reacting a 4-halogen phenol compound of Formula II with a Grignard reagent, subjecting the reaction product to halogen-to-lithium substitution and then reacting the reaction product with sulfur and the compound of Formula IV
so as to form a thioether compound; and reacting the thioether compound with a strong base without separation and then with an electrophilic compound so as to prepare a compound of Formula VII:
wherein X1 denotes a bromine atom or an iodine atom, X2 denotes a chlorine atom, a bromine atom, an iodine atom, or a leaving group having high reactivity in electrophilic substitution reaction, and R1, R3 to R5, m and n have the same meanings as defined in Formula I.
9. The method of Claim 7 or 8, which further comprises the step of:
e) reacting the compound of Formula VII with an alkyl halogen acetate of Formula VIII in the presence of an inorganic salt so as to prepare a compound of Formula IX:
wherein R1, R3 to R5, m and n have the same meanings as defined in Formula I, and R6a is a carboxylic acid protecting group having C1-4 alkyl or an allyl group, and X4 is a chlorine atom, a bromine atom or an iodine atom.
e) reacting the compound of Formula VII with an alkyl halogen acetate of Formula VIII in the presence of an inorganic salt so as to prepare a compound of Formula IX:
wherein R1, R3 to R5, m and n have the same meanings as defined in Formula I, and R6a is a carboxylic acid protecting group having C1-4 alkyl or an allyl group, and X4 is a chlorine atom, a bromine atom or an iodine atom.
10. The method of Claim 9, which further comprises the step of:
subjecting the compound of Formula IX to carboxylic acid ester hydrolysis with a water-soluble inorganic salt in an alcohol solution so as to prepare a compound of Formula X:
wherein R1, R3 to R5, m and n have the same meanings as defined in Formula I, R6a is a carboxylic acid protecting group having C1-4 or an allyl group, and R6b is a hydrogen atom or an alkali metal.
subjecting the compound of Formula IX to carboxylic acid ester hydrolysis with a water-soluble inorganic salt in an alcohol solution so as to prepare a compound of Formula X:
wherein R1, R3 to R5, m and n have the same meanings as defined in Formula I, R6a is a carboxylic acid protecting group having C1-4 or an allyl group, and R6b is a hydrogen atom or an alkali metal.
11. The method of Claim 9, which further comprises the step of:
subjecting the compound of Formula IX to allyl ester-to-salt substitution using a metal salt in an organic solvent in the presence of a palladium tetrakistriphenylphosphine catalyst so as to prepare a compound of Formula X:
wherein R1, R3 to R5, m and n have the same meanings as defined in Formula I, and M is an alkali metal.
subjecting the compound of Formula IX to allyl ester-to-salt substitution using a metal salt in an organic solvent in the presence of a palladium tetrakistriphenylphosphine catalyst so as to prepare a compound of Formula X:
wherein R1, R3 to R5, m and n have the same meanings as defined in Formula I, and M is an alkali metal.
12. An agent for treating diabetes, comprising as an active ingredient a thiazole derivative represented by Formula I.
13. An agent for preventing and treating obesity, comprising as an active ingredient a thiazole derivative represented by Formula I.
14. An agent for preventing and treating arteriosclerosis, comprising as an active ingredient a thiazole derivative represented by Formula I.
15. An agent for preventing and treating hyperlipidemia, comprising as an active ingredient a thiazole derivative represented by Formula I.
16. Health food supplement, health beverage, food additive, functional cosmetic and animal feed compositions comprising as an active ingredient a thiazole derivative represented by Formula I.
17. A composition for activating a peroxisome proliferator-activated receptor .delta. (PPAR.delta.), comprising as an active ingredient a thiazole derivative represented by Formula I.
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR20050015663 | 2005-02-25 | ||
| KR10-2005-0015663 | 2005-02-25 | ||
| KR10-2006-0018360 | 2006-02-24 | ||
| KR1020060018360A KR100797798B1 (en) | 2005-02-25 | 2006-02-24 | Peroxysomal Proliferator Activating Receptor Delta Ligand Thiazole Derivatives and Methods for Making the Same |
| PCT/KR2006/000663 WO2006091047A1 (en) | 2005-02-25 | 2006-02-24 | Thiazole derivatives as ppar delta ligands and their manufacturing process |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2599281A1 true CA2599281A1 (en) | 2006-08-31 |
| CA2599281C CA2599281C (en) | 2012-01-17 |
Family
ID=36927652
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2599281A Expired - Fee Related CA2599281C (en) | 2005-02-25 | 2006-02-24 | Thiazole derivatives as ppar delta ligands and their manufacturing process |
Country Status (3)
| Country | Link |
|---|---|
| EP (1) | EP1856072A4 (en) |
| CA (1) | CA2599281C (en) |
| WO (1) | WO2006091047A1 (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2007326114B2 (en) | 2006-12-02 | 2011-08-25 | Seoul National University Industry Foundation | Aryl compounds as PPAR ligands and their use |
| EP2104666A4 (en) * | 2007-01-08 | 2011-05-25 | Seoul Nat Univ Ind Foundation | THIAZOLE COMPOUND (AS PPARdelta) LIGAND AND PHARMACEUTICAL, COSMETIC AND HEALTH FOOD COMPRISED THEREOF |
| WO2011105643A1 (en) * | 2010-02-25 | 2011-09-01 | 서울대학교산학협력단 | Selenalzole derivative having ligand which activates peroxisome proliferator activated receptor (ppar), preparing method thereof and usage of the chemical compounds |
| KR101898610B1 (en) | 2010-08-31 | 2018-09-14 | 서울대학교산학협력단 | Fetal reprogramming of PPARδ agonists |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR9911752A (en) * | 1998-07-01 | 2001-04-03 | Takeda Chemical Industries Ltd | Retinoid-related receptor function regulating agent, oxazole, imidazole and thiazole derivatives, compound, process for regulating retinoid-related receptor function, and use of a derivative |
| CZ20013558A3 (en) * | 1999-04-20 | 2002-05-15 | Novo Nordisk A/S | Compound, pharmaceutical preparation, treatment method, preparation and use thereof |
| GB0031107D0 (en) | 2000-12-20 | 2001-01-31 | Glaxo Group Ltd | Chemical compounds |
| WO2003072100A1 (en) | 2002-02-25 | 2003-09-04 | Eli Lilly And Company | Peroxisome proliferator activated receptor modulators |
| KR100474202B1 (en) | 2002-05-04 | 2005-03-08 | 강헌중 | Process for preparing thiazol derivative and the intermediate compounds for preparing the same |
-
2006
- 2006-02-24 EP EP06716113A patent/EP1856072A4/en not_active Withdrawn
- 2006-02-24 CA CA2599281A patent/CA2599281C/en not_active Expired - Fee Related
- 2006-02-24 WO PCT/KR2006/000663 patent/WO2006091047A1/en active Application Filing
Also Published As
| Publication number | Publication date |
|---|---|
| EP1856072A4 (en) | 2009-10-21 |
| WO2006091047A1 (en) | 2006-08-31 |
| EP1856072A1 (en) | 2007-11-21 |
| CA2599281C (en) | 2012-01-17 |
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| EEER | Examination request | ||
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Effective date: 20160224 |