ZA200309757B - Novel heterocyclic compound and medicinal use thereof. - Google Patents
Novel heterocyclic compound and medicinal use thereof. Download PDFInfo
- Publication number
- ZA200309757B ZA200309757B ZA200309757A ZA200309757A ZA200309757B ZA 200309757 B ZA200309757 B ZA 200309757B ZA 200309757 A ZA200309757 A ZA 200309757A ZA 200309757 A ZA200309757 A ZA 200309757A ZA 200309757 B ZA200309757 B ZA 200309757B
- Authority
- ZA
- South Africa
- Prior art keywords
- tetrahydroisoquinoline
- alkyl
- methyl
- carboxylic acid
- ethoxy
- Prior art date
Links
- 150000002391 heterocyclic compounds Chemical class 0.000 title claims description 59
- 125000000217 alkyl group Chemical group 0.000 claims description 142
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 76
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 59
- 150000003839 salts Chemical class 0.000 claims description 59
- -1 5-methyl-2-styryloxazol-4-yl Chemical group 0.000 claims description 52
- 125000003145 oxazol-4-yl group Chemical group O1C=NC(=C1)* 0.000 claims description 43
- 125000003118 aryl group Chemical group 0.000 claims description 35
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 32
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 28
- 150000001875 compounds Chemical class 0.000 claims description 23
- 125000003342 alkenyl group Chemical group 0.000 claims description 19
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 18
- 239000003795 chemical substances by application Substances 0.000 claims description 16
- 206010022489 Insulin Resistance Diseases 0.000 claims description 15
- 229910052736 halogen Inorganic materials 0.000 claims description 15
- 125000005843 halogen group Chemical group 0.000 claims description 15
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 14
- 229910052717 sulfur Inorganic materials 0.000 claims description 14
- 125000004434 sulfur atom Chemical group 0.000 claims description 14
- 201000010099 disease Diseases 0.000 claims description 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 12
- 238000011321 prophylaxis Methods 0.000 claims description 12
- 238000011282 treatment Methods 0.000 claims description 12
- 102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 claims description 10
- 108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 claims description 10
- 125000004414 alkyl thio group Chemical group 0.000 claims description 10
- 206010012601 diabetes mellitus Diseases 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 10
- 229940124597 therapeutic agent Drugs 0.000 claims description 10
- 206010003210 Arteriosclerosis Diseases 0.000 claims description 8
- 208000002249 Diabetes Complications Diseases 0.000 claims description 8
- 206010012655 Diabetic complications Diseases 0.000 claims description 8
- 208000011775 arteriosclerosis disease Diseases 0.000 claims description 8
- 230000001404 mediated effect Effects 0.000 claims description 8
- 208000011580 syndromic disease Diseases 0.000 claims description 8
- 208000002705 Glucose Intolerance Diseases 0.000 claims description 5
- 208000008589 Obesity Diseases 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 235000020824 obesity Nutrition 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 125000003107 substituted aryl group Chemical group 0.000 claims description 5
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims description 5
- 208000031226 Hyperlipidaemia Diseases 0.000 claims description 4
- 206010061218 Inflammation Diseases 0.000 claims description 4
- 239000000883 anti-obesity agent Substances 0.000 claims description 4
- 239000003472 antidiabetic agent Substances 0.000 claims description 4
- 239000003524 antilipemic agent Substances 0.000 claims description 4
- 229940125710 antiobesity agent Drugs 0.000 claims description 4
- 201000001421 hyperglycemia Diseases 0.000 claims description 4
- 229940126904 hypoglycaemic agent Drugs 0.000 claims description 4
- 230000004054 inflammatory process Effects 0.000 claims description 4
- UWYZHKAOTLEWKK-UHFFFAOYSA-N tetrahydro-isoquinoline Natural products C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 claims description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
- 229920002554 vinyl polymer Polymers 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 239000002260 anti-inflammatory agent Substances 0.000 claims description 3
- 229940121363 anti-inflammatory agent Drugs 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 239000008177 pharmaceutical agent Substances 0.000 claims description 3
- 206010018429 Glucose tolerance impaired Diseases 0.000 claims 3
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 claims 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 5
- 239000008103 glucose Substances 0.000 description 5
- 230000002218 hypoglycaemic effect Effects 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 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 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 239000008280 blood Substances 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 230000000055 hyoplipidemic effect Effects 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- HYAFETHFCAUJAY-UHFFFAOYSA-N pioglitazone Chemical compound N1=CC(CC)=CC=C1CCOC(C=C1)=CC=C1CC1C(=O)NC(=O)S1 HYAFETHFCAUJAY-UHFFFAOYSA-N 0.000 description 3
- ZOBPZXTWZATXDG-UHFFFAOYSA-N 1,3-thiazolidine-2,4-dione Chemical compound O=C1CSC(=O)N1 ZOBPZXTWZATXDG-UHFFFAOYSA-N 0.000 description 2
- 102000004877 Insulin Human genes 0.000 description 2
- 108090001061 Insulin Proteins 0.000 description 2
- YASAKCUCGLMORW-UHFFFAOYSA-N Rosiglitazone Chemical compound C=1C=CC=NC=1N(C)CCOC(C=C1)=CC=C1CC1SC(=O)NC1=O YASAKCUCGLMORW-UHFFFAOYSA-N 0.000 description 2
- 230000003213 activating effect Effects 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 150000004283 biguanides Chemical class 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- 229940125396 insulin Drugs 0.000 description 2
- 230000003914 insulin secretion Effects 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 201000009104 prediabetes syndrome Diseases 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 208000006029 Cardiomegaly Diseases 0.000 description 1
- 208000013016 Hypoglycemia Diseases 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- 229940123464 Thiazolidinedione Drugs 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 208000006443 lactic acidosis Diseases 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 208000019423 liver disease Diseases 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 229960005095 pioglitazone Drugs 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229960004586 rosiglitazone Drugs 0.000 description 1
- 150000003548 thiazolidines Chemical class 0.000 description 1
- GXPHKUHSUJUWKP-UHFFFAOYSA-N troglitazone Chemical compound C1CC=2C(C)=C(O)C(C)=C(C)C=2OC1(C)COC(C=C1)=CC=C1CC1SC(=O)NC1=O GXPHKUHSUJUWKP-UHFFFAOYSA-N 0.000 description 1
- 229960001641 troglitazone Drugs 0.000 description 1
- GXPHKUHSUJUWKP-NTKDMRAZSA-N troglitazone Natural products C([C@@]1(OC=2C(C)=C(C(=C(C)C=2CC1)O)C)C)OC(C=C1)=CC=C1C[C@H]1SC(=O)NC1=O GXPHKUHSUJUWKP-NTKDMRAZSA-N 0.000 description 1
Classifications
-
- 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
- C07D413/12—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 chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
-
- 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
- A61P3/04—Anorexiants; Antiobesity agents
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the nitrogen-containing ring
- C07D217/26—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- 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
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Diabetes (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Child & Adolescent Psychology (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2001161489 | 2001-05-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200309757B true ZA200309757B (en) | 2004-12-22 |
Family
ID=19004756
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200309757A ZA200309757B (en) | 2001-05-29 | 2002-05-27 | Novel heterocyclic compound and medicinal use thereof. |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US7557123B2 (no) |
| EP (1) | EP1403253A4 (no) |
| JP (1) | JP4279136B2 (no) |
| KR (2) | KR100898358B1 (no) |
| CN (1) | CN1242994C (no) |
| AR (1) | AR036036A1 (no) |
| AU (1) | AU2002308889B2 (no) |
| BR (1) | BR0209711A (no) |
| CA (1) | CA2448634A1 (no) |
| CO (1) | CO5540342A2 (no) |
| CZ (1) | CZ20033450A3 (no) |
| HK (1) | HK1069385A1 (no) |
| HU (1) | HUP0401862A3 (no) |
| IL (1) | IL159085A0 (no) |
| MX (1) | MXPA03010811A (no) |
| NO (1) | NO326688B1 (no) |
| NZ (1) | NZ530358A (no) |
| PL (1) | PL367639A1 (no) |
| RU (1) | RU2299197C2 (no) |
| TW (1) | TWI297008B (no) |
| WO (1) | WO2002096880A1 (no) |
| YU (1) | YU94003A (no) |
| ZA (1) | ZA200309757B (no) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR0209735A (pt) | 2001-05-29 | 2004-07-27 | Kyoto Pharma Ind | Derivados heterocìclicos e uso medicinal destes |
| US7816385B2 (en) * | 2002-12-20 | 2010-10-19 | High Point Pharmaceuticals, Llc | Dimeric dicarboxylic acid derivatives, their preparation and use |
| US7718377B2 (en) | 2003-05-29 | 2010-05-18 | Kyoto Pharmaceutical Industries, Ltd. | Insulin resistance curative and method of screening the same |
| TWI359810B (en) | 2004-11-04 | 2012-03-11 | Mitsubishi Tanabe Pharma Corp | Carboxylic acid derivative containing thiazole rin |
| US7790745B2 (en) * | 2005-10-21 | 2010-09-07 | Bristol-Myers Squibb Company | Tetrahydroisoquinoline LXR Modulators |
| WO2007058504A1 (en) * | 2005-11-21 | 2007-05-24 | Lg Life Sciences, Ltd. | Novel compounds as agonist for ppar gamma and ppar alpha, method for preparation of the same, and pharmaceutical composition containing the same |
| WO2012033195A1 (ja) * | 2010-09-10 | 2012-03-15 | 京都薬品工業株式会社 | 複素環化合物 |
| CN102807526B (zh) * | 2011-06-21 | 2015-12-02 | 寿光富康制药有限公司 | 组蛋白去乙酰化酶抑制剂ZYJ-D08a及其差向异构体的制备方法与应用 |
| WO2020013116A1 (ja) * | 2018-07-10 | 2020-01-16 | 京都薬品工業株式会社 | Ｐｔｐ－１ｂ阻害剤およびその用途 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6051189A (ja) * | 1983-08-30 | 1985-03-22 | Sankyo Co Ltd | チアゾリジン誘導体およびその製造法 |
| AR240698A1 (es) * | 1985-01-19 | 1990-09-28 | Takeda Chemical Industries Ltd | Procedimiento para preparar compuestos de 5-(4-(2-(5-etil-2-piridil)-etoxi)benzil)-2,4-tiazolidindiona y sus sales |
| ATE186724T1 (de) * | 1987-09-04 | 1999-12-15 | Beecham Group Plc | Substituierte thiazolidindionderivate |
| US5246943A (en) | 1992-05-19 | 1993-09-21 | Warner-Lambert Company | Substituted 1,2,3,4-tetahydroisoquinolines with angiotensin II receptor antagonist properties |
| GB9604242D0 (en) | 1996-02-28 | 1996-05-01 | Glaxo Wellcome Inc | Chemical compounds |
| EP0925063A4 (en) | 1996-07-01 | 2000-12-27 | Lilly Co Eli | Blood-glucose-lowering and lipid-lowering compounds |
| AU3513497A (en) | 1996-07-01 | 1998-01-21 | Eli Lilly And Company | Hypoglycemic and hypolipidemic compounds |
| GB9817118D0 (en) * | 1998-08-07 | 1998-10-07 | Glaxo Group Ltd | Pharmaceutical compounds |
| CN1215059C (zh) * | 1999-12-03 | 2005-08-17 | 京都药品工业株式会社 | 新的杂环化合物及其盐和它们的医药用途 |
| US20020037897A1 (en) | 2000-08-07 | 2002-03-28 | 3-Dimensional Pharmaceuticals, Inc. | Tetrahydroisoquinoline-3-carboxylic acid alkoxyguanidines as integrin antagonists |
| BR0209735A (pt) * | 2001-05-29 | 2004-07-27 | Kyoto Pharma Ind | Derivados heterocìclicos e uso medicinal destes |
-
2002
- 2002-05-27 NZ NZ530358A patent/NZ530358A/en unknown
- 2002-05-27 CA CA002448634A patent/CA2448634A1/en not_active Abandoned
- 2002-05-27 AU AU2002308889A patent/AU2002308889B2/en not_active Ceased
- 2002-05-27 YU YU94003A patent/YU94003A/sh unknown
- 2002-05-27 ZA ZA200309757A patent/ZA200309757B/en unknown
- 2002-05-27 MX MXPA03010811A patent/MXPA03010811A/es active IP Right Grant
- 2002-05-27 CZ CZ20033450A patent/CZ20033450A3/cs unknown
- 2002-05-27 EP EP02774070A patent/EP1403253A4/en not_active Withdrawn
- 2002-05-27 JP JP2003500060A patent/JP4279136B2/ja not_active Expired - Fee Related
- 2002-05-27 IL IL15908502A patent/IL159085A0/xx unknown
- 2002-05-27 KR KR1020087023698A patent/KR100898358B1/ko not_active IP Right Cessation
- 2002-05-27 US US10/478,862 patent/US7557123B2/en not_active Expired - Fee Related
- 2002-05-27 PL PL02367639A patent/PL367639A1/xx unknown
- 2002-05-27 CN CNB028109643A patent/CN1242994C/zh not_active Expired - Fee Related
- 2002-05-27 RU RU2003137574/04A patent/RU2299197C2/ru not_active IP Right Cessation
- 2002-05-27 KR KR10-2003-7015611A patent/KR20040030647A/ko not_active IP Right Cessation
- 2002-05-27 HU HU0401862A patent/HUP0401862A3/hu unknown
- 2002-05-27 BR BR0209711-7A patent/BR0209711A/pt not_active IP Right Cessation
- 2002-05-27 WO PCT/JP2002/005097 patent/WO2002096880A1/ja active Application Filing
- 2002-05-28 TW TW091111315A patent/TWI297008B/zh active
- 2002-05-29 AR ARP020102002A patent/AR036036A1/es unknown
-
2003
- 2003-11-28 NO NO20035331A patent/NO326688B1/no not_active IP Right Cessation
- 2003-12-29 CO CO03112806A patent/CO5540342A2/es not_active Application Discontinuation
-
2005
- 2005-03-02 HK HK05101815A patent/HK1069385A1/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| RU2003137574A (ru) | 2005-05-20 |
| EP1403253A4 (en) | 2005-03-30 |
| EP1403253A1 (en) | 2004-03-31 |
| JPWO2002096880A1 (ja) | 2004-09-09 |
| TWI297008B (en) | 2008-05-21 |
| WO2002096880A1 (fr) | 2002-12-05 |
| AU2002308889B2 (en) | 2007-09-06 |
| KR20080093076A (ko) | 2008-10-17 |
| PL367639A1 (en) | 2005-03-07 |
| CN1242994C (zh) | 2006-02-22 |
| RU2299197C2 (ru) | 2007-05-20 |
| CO5540342A2 (es) | 2005-07-29 |
| CZ20033450A3 (cs) | 2004-05-12 |
| BR0209711A (pt) | 2004-11-03 |
| NO326688B1 (no) | 2009-01-26 |
| IL159085A0 (en) | 2004-05-12 |
| YU94003A (sh) | 2006-08-17 |
| HUP0401862A3 (en) | 2009-03-30 |
| US7557123B2 (en) | 2009-07-07 |
| US20040220215A1 (en) | 2004-11-04 |
| HUP0401862A2 (hu) | 2004-12-28 |
| HK1069385A1 (en) | 2005-05-20 |
| CN1527819A (zh) | 2004-09-08 |
| KR100898358B1 (ko) | 2009-05-20 |
| JP4279136B2 (ja) | 2009-06-17 |
| CA2448634A1 (en) | 2002-12-05 |
| MXPA03010811A (es) | 2004-02-27 |
| AR036036A1 (es) | 2004-08-04 |
| KR20040030647A (ko) | 2004-04-09 |
| NO20035331D0 (no) | 2003-11-28 |
| NZ530358A (en) | 2005-04-29 |
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