ZA200106440B - Polycyclic thiazole systems and their utilization as anorectics. - Google Patents
Polycyclic thiazole systems and their utilization as anorectics. Download PDFInfo
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- ZA200106440B ZA200106440B ZA200106440A ZA200106440A ZA200106440B ZA 200106440 B ZA200106440 B ZA 200106440B ZA 200106440 A ZA200106440 A ZA 200106440A ZA 200106440 A ZA200106440 A ZA 200106440A ZA 200106440 B ZA200106440 B ZA 200106440B
- Authority
- ZA
- South Africa
- Prior art keywords
- alkyl
- phenyl
- ocf3
- hydrogen
- replaced
- Prior art date
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- 230000001539 anorectic effect Effects 0.000 title claims abstract description 4
- 206010061428 decreased appetite Diseases 0.000 title claims abstract 3
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 title abstract description 5
- 125000003367 polycyclic group Chemical group 0.000 title abstract description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 49
- 150000003839 salts Chemical class 0.000 claims abstract description 18
- 238000000034 method Methods 0.000 claims abstract description 7
- -1 CONHa Chemical group 0.000 claims description 48
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 229910052731 fluorine Inorganic materials 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 17
- 229910052794 bromium Inorganic materials 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 15
- 229910052801 chlorine Inorganic materials 0.000 claims description 14
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 12
- 239000004480 active ingredient Substances 0.000 claims description 11
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 10
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 10
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 10
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 10
- 239000011737 fluorine Substances 0.000 claims description 10
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 9
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 8
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 7
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 7
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 7
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 7
- 229910052740 iodine Inorganic materials 0.000 claims description 7
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 125000002541 furyl group Chemical group 0.000 claims description 6
- 125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 125000001544 thienyl group Chemical group 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 150000005840 aryl radicals Chemical class 0.000 claims description 5
- 238000002156 mixing Methods 0.000 claims description 5
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 4
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
- 125000004190 benzothiazol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N=C(*)SC2=C1[H] 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000004531 indol-5-yl group Chemical group [H]N1C([H])=C([H])C2=C([H])C(*)=C([H])C([H])=C12 0.000 claims description 4
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- 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- 125000001506 1,2,3-triazol-5-yl group Chemical group [H]N1N=NC([H])=C1[*] 0.000 claims description 2
- 125000001305 1,2,4-triazol-3-yl group Chemical group [H]N1N=C([*])N=C1[H] 0.000 claims description 2
- 125000004317 1,3,5-triazin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=N1 0.000 claims description 2
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000004174 2-benzimidazolyl group Chemical group [H]N1C(*)=NC2=C([H])C([H])=C([H])C([H])=C12 0.000 claims description 2
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
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- 125000004539 5-benzimidazolyl group Chemical group N1=CNC2=C1C=CC(=C2)* 0.000 claims description 2
- CWDWFSXUQODZGW-UHFFFAOYSA-N 5-thiazolyl Chemical group [C]1=CN=CS1 CWDWFSXUQODZGW-UHFFFAOYSA-N 0.000 claims description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 2
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- 125000005545 phthalimidyl group Chemical group 0.000 claims description 2
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- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 2
- 125000004526 pyridazin-2-yl group Chemical group N1N(C=CC=C1)* 0.000 claims description 2
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 claims description 2
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 2
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 2
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 2
- 125000001425 triazolyl group Chemical group 0.000 claims description 2
- 125000001414 1,2,4-triazol-5-yl group Chemical group [H]N1N=C([H])N=C1[*] 0.000 claims 1
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- 229940116362 tragacanth Drugs 0.000 description 1
- WTVXIBRMWGUIMI-UHFFFAOYSA-N trifluoro($l^{1}-oxidanylsulfonyl)methane Chemical group [O]S(=O)(=O)C(F)(F)F WTVXIBRMWGUIMI-UHFFFAOYSA-N 0.000 description 1
- CWMFRHBXRUITQE-UHFFFAOYSA-N trimethylsilylacetylene Chemical group C[Si](C)(C)C#C CWMFRHBXRUITQE-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000007762 w/o emulsion Substances 0.000 description 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
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
-
- 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
- A61P3/08—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
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/84—Naphthothiazoles
-
- 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
- C07D417/04—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 directly linked by a ring-member-to-ring-member bond
-
- 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
- C07D417/06—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 carbon chain containing only aliphatic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Diabetes (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Child & Adolescent Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19908533A DE19908533A1 (de) | 1999-02-26 | 1999-02-26 | Polycyclische Thiazol-Systeme, Verfahren zu ihrer Herstellung und Arzneimittel enthaltend diese Verbindungen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200106440B true ZA200106440B (en) | 2002-03-06 |
Family
ID=7899078
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200106440A ZA200106440B (en) | 1999-02-26 | 2001-08-08 | Polycyclic thiazole systems and their utilization as anorectics. |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US6187801B1 (https=) |
| EP (1) | EP1183247B1 (https=) |
| JP (1) | JP4728485B2 (https=) |
| KR (1) | KR20020000545A (https=) |
| CN (1) | CN1149205C (https=) |
| AT (1) | ATE296295T1 (https=) |
| AU (1) | AU762802B2 (https=) |
| BR (1) | BR0008511A (https=) |
| CA (1) | CA2364903A1 (https=) |
| CO (1) | CO5180595A1 (https=) |
| DE (2) | DE19908533A1 (https=) |
| DK (1) | DK1183247T3 (https=) |
| ES (1) | ES2241574T3 (https=) |
| HK (1) | HK1042300B (https=) |
| MY (1) | MY133195A (https=) |
| PT (1) | PT1183247E (https=) |
| TW (1) | TW593294B (https=) |
| WO (1) | WO2000051997A1 (https=) |
| ZA (1) | ZA200106440B (https=) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19908535A1 (de) * | 1999-02-26 | 2000-08-31 | Aventis Pharma Gmbh | Verwendung von polycyclischen Thiazol-Systemen zur Herstellung von Medikamenten zur Prophylaxe oder Behandlung von Obesitas |
| KR100763214B1 (ko) * | 2000-02-26 | 2007-10-08 | 사노피-아벤티스 도이칠란트 게엠베하 | 2 위치에서 설폰아미도 또는 설포노 치환체를 갖는 8,8ａ-디하이드로-인데노[1,2-ｄ]티아졸 유도체, 이의 제조방법 및 이를 포함하는 약제 |
| DE10142663B4 (de) | 2001-08-31 | 2004-08-19 | Aventis Pharma Deutschland Gmbh | C2-Disubstituierte Indan-1-ol-Systeme |
| KR100712171B1 (ko) * | 2004-09-17 | 2007-05-02 | 김진우 | 폐타이어를 이용한 조립식 배관블록 |
| ES2480994T3 (es) | 2008-03-31 | 2014-07-29 | Genentech, Inc. | Compuestos de tipo benzopirano y benzoxepina inhibidores de PI3K y métodos de uso |
| ES2558742T3 (es) | 2009-09-28 | 2016-02-08 | F. Hoffmann-La Roche Ag | Compuestos inhibidores de PI3K de benzoxepina y métodos de uso |
| ES2570569T3 (es) | 2009-09-28 | 2016-05-19 | Hoffmann La Roche | Compuestos de benzoxazepina como inhibidores de la PI3K y métodos de uso |
| WO2012126901A1 (en) | 2011-03-21 | 2012-09-27 | F. Hoffmann-La Roche Ag | Benzoxazepin compounds selective for pi3k p110 delta and methods of use |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2640358A1 (de) * | 1976-09-08 | 1978-03-16 | Hoechst Ag | Thiazolidinderivate und verfahren zu ihrer herstellung |
| NZ281718A (en) * | 1994-03-11 | 1997-08-22 | Yamanouchi Pharma Co Ltd | Heterocyclically-substituted (condensed) thiazoles |
| JPH1179993A (ja) * | 1997-09-05 | 1999-03-23 | Sumitomo Pharmaceut Co Ltd | 免疫抑制剤 |
| DE19831878C2 (de) * | 1998-07-17 | 2001-05-17 | Aventis Pharma Gmbh | Polycyclische Thiazolidin-2-yliden Amine, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| DE19908535A1 (de) * | 1999-02-26 | 2000-08-31 | Aventis Pharma Gmbh | Verwendung von polycyclischen Thiazol-Systemen zur Herstellung von Medikamenten zur Prophylaxe oder Behandlung von Obesitas |
-
1999
- 1999-02-26 DE DE19908533A patent/DE19908533A1/de not_active Withdrawn
-
2000
- 2000-02-05 PT PT00902658T patent/PT1183247E/pt unknown
- 2000-02-05 WO PCT/EP2000/000927 patent/WO2000051997A1/de not_active Ceased
- 2000-02-05 KR KR1020017010874A patent/KR20020000545A/ko not_active Ceased
- 2000-02-05 DE DE50010403T patent/DE50010403D1/de not_active Expired - Lifetime
- 2000-02-05 ES ES00902658T patent/ES2241574T3/es not_active Expired - Lifetime
- 2000-02-05 AT AT00902658T patent/ATE296295T1/de not_active IP Right Cessation
- 2000-02-05 CN CNB008042365A patent/CN1149205C/zh not_active Expired - Fee Related
- 2000-02-05 HK HK02104057.0A patent/HK1042300B/zh not_active IP Right Cessation
- 2000-02-05 JP JP2000602224A patent/JP4728485B2/ja not_active Expired - Fee Related
- 2000-02-05 EP EP00902658A patent/EP1183247B1/de not_active Expired - Lifetime
- 2000-02-05 BR BR0008511-1A patent/BR0008511A/pt not_active IP Right Cessation
- 2000-02-05 AU AU24416/00A patent/AU762802B2/en not_active Ceased
- 2000-02-05 CA CA002364903A patent/CA2364903A1/en not_active Abandoned
- 2000-02-05 DK DK00902658T patent/DK1183247T3/da active
- 2000-02-10 US US09/501,210 patent/US6187801B1/en not_active Expired - Lifetime
- 2000-02-21 CO CO00011822A patent/CO5180595A1/es not_active Application Discontinuation
- 2000-02-25 MY MYPI20000739A patent/MY133195A/en unknown
- 2000-03-20 TW TW089103194A patent/TW593294B/zh not_active IP Right Cessation
-
2001
- 2001-08-08 ZA ZA200106440A patent/ZA200106440B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JP2002538150A (ja) | 2002-11-12 |
| BR0008511A (pt) | 2002-04-02 |
| EP1183247B1 (de) | 2005-05-25 |
| DE50010403D1 (de) | 2005-06-30 |
| AU2441600A (en) | 2000-09-21 |
| ES2241574T3 (es) | 2005-11-01 |
| HK1042300A1 (en) | 2002-08-09 |
| KR20020000545A (ko) | 2002-01-05 |
| CA2364903A1 (en) | 2000-09-08 |
| DE19908533A1 (de) | 2000-08-31 |
| CN1341108A (zh) | 2002-03-20 |
| PT1183247E (pt) | 2005-07-29 |
| AU762802B2 (en) | 2003-07-03 |
| MY133195A (en) | 2007-10-31 |
| ATE296295T1 (de) | 2005-06-15 |
| JP4728485B2 (ja) | 2011-07-20 |
| WO2000051997A1 (de) | 2000-09-08 |
| TW593294B (en) | 2004-06-21 |
| DK1183247T3 (da) | 2005-09-19 |
| HK1042300B (zh) | 2004-12-10 |
| CN1149205C (zh) | 2004-05-12 |
| CO5180595A1 (es) | 2002-07-30 |
| EP1183247A1 (de) | 2002-03-06 |
| US6187801B1 (en) | 2001-02-13 |
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