ZA200106198B - Polycyclic 2-amino-thiazole systems, method for the production thereof and medicament containing said compounds. - Google Patents
Polycyclic 2-amino-thiazole systems, method for the production thereof and medicament containing said compounds. Download PDFInfo
- Publication number
- ZA200106198B ZA200106198B ZA200106198A ZA200106198A ZA200106198B ZA 200106198 B ZA200106198 B ZA 200106198B ZA 200106198 A ZA200106198 A ZA 200106198A ZA 200106198 A ZA200106198 A ZA 200106198A ZA 200106198 B ZA200106198 B ZA 200106198B
- Authority
- ZA
- South Africa
- Prior art keywords
- alkyl
- phenyl
- substituted
- cooh
- ocf3
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 65
- 238000000034 method Methods 0.000 title claims abstract description 15
- RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical compound NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 title abstract description 6
- 125000003367 polycyclic group Chemical group 0.000 title abstract description 5
- 239000003814 drug Substances 0.000 title description 2
- 238000004519 manufacturing process Methods 0.000 title description 2
- 150000003839 salts Chemical class 0.000 claims abstract description 21
- 230000001539 anorectic effect Effects 0.000 claims abstract description 7
- 206010061428 decreased appetite Diseases 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 53
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 46
- -1 CONHz Chemical group 0.000 claims description 45
- 229910052731 fluorine Inorganic materials 0.000 claims description 45
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 44
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 42
- 229910052794 bromium Inorganic materials 0.000 claims description 41
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 37
- 229910052801 chlorine Inorganic materials 0.000 claims description 33
- 229910052739 hydrogen Inorganic materials 0.000 claims description 28
- 229910052740 iodine Inorganic materials 0.000 claims description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 20
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 20
- 125000003342 alkenyl group Chemical group 0.000 claims description 13
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 12
- 239000004480 active ingredient Substances 0.000 claims description 12
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 12
- 239000011737 fluorine Substances 0.000 claims description 12
- 101100294106 Caenorhabditis elegans nhr-3 gene Proteins 0.000 claims description 9
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 9
- 125000004076 pyridyl group Chemical group 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 6
- 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 6
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 6
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 6
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 6
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- 125000001544 thienyl group Chemical group 0.000 claims description 6
- 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 5
- 125000002541 furyl group Chemical group 0.000 claims description 5
- 238000002156 mixing Methods 0.000 claims description 5
- 125000001506 1,2,3-triazol-5-yl group Chemical group [H]N1N=NC([H])=C1[*] 0.000 claims description 4
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 claims description 4
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 4
- 125000001425 triazolyl group Chemical group 0.000 claims description 4
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 3
- 240000005265 Lupinus mutabilis Species 0.000 claims 1
- 235000008755 Lupinus mutabilis Nutrition 0.000 claims 1
- 235000019095 Sechium edule Nutrition 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 31
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 27
- 239000000243 solution Substances 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
- 238000002844 melting Methods 0.000 description 13
- 230000008018 melting Effects 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
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- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
- 229960000583 acetic acid Drugs 0.000 description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
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- 239000008267 milk Substances 0.000 description 5
- 210000004080 milk Anatomy 0.000 description 5
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- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
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- 239000002253 acid Substances 0.000 description 4
- 230000001186 cumulative effect Effects 0.000 description 4
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 4
- CAJDYMAFIOUARK-UHFFFAOYSA-N 1-oxo-2,3-dihydroindene-5-carbonitrile Chemical compound N#CC1=CC=C2C(=O)CCC2=C1 CAJDYMAFIOUARK-UHFFFAOYSA-N 0.000 description 3
- QZPUXCULJWOZPL-UHFFFAOYSA-N 2-(dimethylamino)-4h-indeno[1,2-d][1,3]thiazole-6-carbonitrile;hydrobromide Chemical compound Br.N#CC1=CC=C2C(N=C(S3)N(C)C)=C3CC2=C1 QZPUXCULJWOZPL-UHFFFAOYSA-N 0.000 description 3
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Child & Adolescent Psychology (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19908538A DE19908538A1 (de) | 1999-02-26 | 1999-02-26 | Polycyclische 2-Amino-Thiazol Systeme, Verfahren zu ihrer Herstellung und Arzneimittel enthaltend diese Verbindungen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200106198B true ZA200106198B (en) | 2002-05-03 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200106198A ZA200106198B (en) | 1999-02-26 | 2001-07-27 | Polycyclic 2-amino-thiazole systems, method for the production thereof and medicament containing said compounds. |
Country Status (15)
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|---|---|
| US (1) | US6251922B1 (https=) |
| EP (1) | EP1157015B1 (https=) |
| JP (1) | JP4728484B2 (https=) |
| KR (1) | KR20010102390A (https=) |
| CN (1) | CN1148362C (https=) |
| AT (1) | ATE295357T1 (https=) |
| AU (1) | AU763111B2 (https=) |
| BR (1) | BR0008510A (https=) |
| CA (1) | CA2364900A1 (https=) |
| DE (2) | DE19908538A1 (https=) |
| ES (1) | ES2240070T3 (https=) |
| HK (1) | HK1043117B (https=) |
| PT (1) | PT1157015E (https=) |
| WO (1) | WO2000051995A1 (https=) |
| ZA (1) | ZA200106198B (https=) |
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| DE19908537A1 (de) * | 1999-02-26 | 2000-08-31 | Aventis Pharma Gmbh | Verwendung von polycyclischen 2-Amino-Thiazol Systemen zur Herstellung von Medikamenten zur Prophylaxe oder Behandlung von Obesitas |
| US7732484B2 (en) * | 2000-08-01 | 2010-06-08 | University Of Virginia Patent Foundation | Use of selective adenosine A1 receptor allosteric enhancers to manipulate angiogenesis |
| JP2005529846A (ja) * | 2002-01-16 | 2005-10-06 | ユニバーシティ オブ バージニア パテント ファウンデーション | Ａ１アデノシン受容体の２−アミノチアゾールアロステリックエンハンサ |
| 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 |
| JP5728487B2 (ja) * | 2009-10-29 | 2015-06-03 | ブリストル−マイヤーズ スクイブ カンパニーＢｒｉｓｔｏｌ−Ｍｙｅｒｓ Ｓｑｕｉｂｂ Ｃｏｍｐａｎｙ | 三環式ヘテロ環化合物 |
| WO2012126901A1 (en) | 2011-03-21 | 2012-09-27 | F. Hoffmann-La Roche Ag | Benzoxazepin compounds selective for pi3k p110 delta and methods of use |
| ES2859478T3 (es) | 2016-09-02 | 2021-10-04 | Bristol Myers Squibb Co | Compuestos heterocíclicos tricíclicos sustituidos |
| WO2019032631A1 (en) | 2017-08-09 | 2019-02-14 | Bristol-Myers Squibb Company | Oxime ether compounds |
| US11046646B2 (en) | 2017-08-09 | 2021-06-29 | Bristol-Myers Squibb Company | Alkylphenyl compounds |
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|---|---|---|---|---|
| US4082773A (en) * | 1972-07-03 | 1978-04-04 | E. R. Squibb & Sons, Inc. | Tricyclic tetrahydro naphthaleneols and related compounds |
| DE2640358A1 (de) * | 1976-09-08 | 1978-03-16 | Hoechst Ag | Thiazolidinderivate und verfahren zu ihrer herstellung |
| CA1292226C (en) * | 1986-01-16 | 1991-11-19 | Terumi Hachiya | Indenothiazole derivative and process for preparing the same |
| IE68593B1 (en) | 1989-12-06 | 1996-06-26 | Sanofi Sa | Heterocyclic substituted acylaminothiazoles their preparation and pharmaceutical compositions containing them |
| TW416953B (en) * | 1996-09-25 | 2001-01-01 | Takeda Chemical Industries Ltd | Tricyclic compounds for eliciting a prostaglandin I2 receptor agonistic effect, their production and use |
| AU3289299A (en) * | 1998-02-19 | 1999-09-06 | Tularik Inc. | Antiviral agents |
| 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 |
| DE19908537A1 (de) * | 1999-02-26 | 2000-08-31 | Aventis Pharma Gmbh | Verwendung von polycyclischen 2-Amino-Thiazol Systemen zur Herstellung von Medikamenten zur Prophylaxe oder Behandlung von Obesitas |
-
1999
- 1999-02-26 DE DE19908538A patent/DE19908538A1/de not_active Withdrawn
-
2000
- 2000-02-05 AU AU32782/00A patent/AU763111B2/en not_active Ceased
- 2000-02-05 BR BR0008510-3A patent/BR0008510A/pt not_active IP Right Cessation
- 2000-02-05 CN CNB008042217A patent/CN1148362C/zh not_active Expired - Fee Related
- 2000-02-05 AT AT00910642T patent/ATE295357T1/de not_active IP Right Cessation
- 2000-02-05 ES ES00910642T patent/ES2240070T3/es not_active Expired - Lifetime
- 2000-02-05 JP JP2000602222A patent/JP4728484B2/ja not_active Expired - Fee Related
- 2000-02-05 PT PT00910642T patent/PT1157015E/pt unknown
- 2000-02-05 DE DE50010285T patent/DE50010285D1/de not_active Expired - Lifetime
- 2000-02-05 CA CA002364900A patent/CA2364900A1/en not_active Abandoned
- 2000-02-05 EP EP00910642A patent/EP1157015B1/de not_active Expired - Lifetime
- 2000-02-05 KR KR1020017010839A patent/KR20010102390A/ko not_active Ceased
- 2000-02-05 WO PCT/EP2000/000924 patent/WO2000051995A1/de not_active Ceased
- 2000-02-05 HK HK02104079.4A patent/HK1043117B/zh not_active IP Right Cessation
- 2000-02-10 US US09/501,208 patent/US6251922B1/en not_active Expired - Lifetime
-
2001
- 2001-07-27 ZA ZA200106198A patent/ZA200106198B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| HK1043117B (zh) | 2004-10-08 |
| DE50010285D1 (de) | 2005-06-16 |
| AU763111B2 (en) | 2003-07-10 |
| CN1148362C (zh) | 2004-05-05 |
| JP4728484B2 (ja) | 2011-07-20 |
| BR0008510A (pt) | 2002-02-05 |
| DE19908538A1 (de) | 2000-08-31 |
| ES2240070T3 (es) | 2005-10-16 |
| JP2002538148A (ja) | 2002-11-12 |
| US6251922B1 (en) | 2001-06-26 |
| EP1157015A1 (de) | 2001-11-28 |
| ATE295357T1 (de) | 2005-05-15 |
| PT1157015E (pt) | 2005-08-31 |
| EP1157015B1 (de) | 2005-05-11 |
| KR20010102390A (ko) | 2001-11-15 |
| HK1043117A1 (en) | 2002-09-06 |
| CA2364900A1 (en) | 2000-09-08 |
| WO2000051995A1 (de) | 2000-09-08 |
| AU3278200A (en) | 2000-09-21 |
| CN1344263A (zh) | 2002-04-10 |
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