WO2002051410A3 - Phenylthiazole and thiazoline derivatives and their use as antiparasitics - Google Patents
Phenylthiazole and thiazoline derivatives and their use as antiparasitics Download PDFInfo
- Publication number
- WO2002051410A3 WO2002051410A3 PCT/EP2001/015119 EP0115119W WO02051410A3 WO 2002051410 A3 WO2002051410 A3 WO 2002051410A3 EP 0115119 W EP0115119 W EP 0115119W WO 02051410 A3 WO02051410 A3 WO 02051410A3
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- alkyl
- formula
- heteroaryl
- aryl
- heterocycloalkyl
- Prior art date
Links
- 230000002141 anti-parasite Effects 0.000 title abstract 2
- WYKHSBAVLOPISI-UHFFFAOYSA-N 2-phenyl-1,3-thiazole Chemical compound C1=CSC(C=2C=CC=CC=2)=N1 WYKHSBAVLOPISI-UHFFFAOYSA-N 0.000 title 1
- 229940125687 antiparasitic agent Drugs 0.000 title 1
- 239000003096 antiparasitic agent Substances 0.000 title 1
- 150000003549 thiazolines Chemical class 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 10
- 125000003118 aryl group Chemical group 0.000 abstract 6
- 125000001072 heteroaryl group Chemical group 0.000 abstract 6
- 125000000592 heterocycloalkyl group Chemical group 0.000 abstract 4
- 125000003342 alkenyl group Chemical group 0.000 abstract 3
- 125000000304 alkynyl group Chemical group 0.000 abstract 3
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 3
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 2
- 125000003282 alkyl amino group Chemical group 0.000 abstract 2
- 125000001769 aryl amino group Chemical group 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 2
- -1 (1-8C)alky Chemical group 0.000 abstract 1
- BABDRDGFMLOFMC-UHFFFAOYSA-N 4,5-dihydro-1,3-thiazole 1,3-thiazole Chemical class C1CN=CS1.c1cscn1 BABDRDGFMLOFMC-UHFFFAOYSA-N 0.000 abstract 1
- KXCQDIWJQBSUJF-UHFFFAOYSA-N 4-phenyl-1,3-thiazole Chemical class S1C=NC(C=2C=CC=CC=2)=C1 KXCQDIWJQBSUJF-UHFFFAOYSA-N 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
Classifications
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- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
- A61K31/351—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom not condensed with another ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/426—1,3-Thiazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/427—Thiazoles not condensed and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/472—Non-condensed isoquinolines, e.g. papaverine
- A61K31/4725—Non-condensed isoquinolines, e.g. papaverine containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/517—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with carbocyclic ring systems, e.g. quinazoline, perimidine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
-
- 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
- C07D277/32—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 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 ring carbon atoms
- C07D277/38—Nitrogen atoms
- C07D277/42—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Organic Chemistry (AREA)
- Tropical Medicine & Parasitology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The present invention provides a new class of antiparatisitcs. The compounds found with the present invention are substituted thiazole- and thiazoline derivatives. The present invention is based on the discovery that such compounds have been found to have antiparasitic activity. The present invention relates to 4-phenyl thiazole derivatives of the following general formula (I): X in formula (I) may be N-R6 or a bond. R1 in formula (I) may be (1-8C)alkyl, (2-8C)alkenyl, (2-8C)alkynyl, (3-8C)cycloalkyl, (2-7C)heterocycloalkyl, (6-14C)aryl, (3-13C)heteroaryl, (6-14C)aryl(1-8C)alkyl or (3-13C)heteroaryl(1-8C)alkyl. R2 in formula (I) may be SO¿2?NR?7R8, CONR7R8 or NR7R8 R3 and R4¿ in formula (I) may independently be selected from H, halogen, (1-8C)alkyl, hydroxy, (1-8) alkoxy, cyano, nitro, (1-8C) alkoxycarbonyl, (1-8C)(di)alkylamino and (6-14C)(di)arylamino, or R?3 and R4¿ are joined together in a 5-7 membered carbocyclic or heterocyclic ring. R5 in formula (I) may be a halogen atom, (1-8C)alky, hydroxy, (1-8C)alkoxy, cyano, nitro, (1-8C)alkoxycarbonyl, (1-8C)(di)alkylamino or (6-14C)(di)arylamino. 'n' may be 0-3. R6 in formula (I) may be H or (1-8C)alkyl, (2-8C)alkenyl, (2-8C)alkynyl, (3-8C)cycloalkyl, (2-7C)heterocycloalkyl, (6-14C)aryl, (3-13C)heteroaryl, (6-14C)aryl(1-8C)alkyl or (3-13C)heteroaryl(1-8C)alkyl. R?7 and R8¿ in formula (I) may independently be selected from H, (1-8C)alkyl, (2-8C)alkenyl, (2-8C)alkynyl, (3-8C)cycloalkyl, (2-7C)heterocycloalkyl, (6-14C)aryl, (3-13C)heteroaryl, (6-14C)aryl(1-8C)alkyl and (3-13C)heteroaryl(1-8C)alkyl, or R?7 and R8¿ are joined together in a (2-7C) heterocycloalkyl ring.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP00204739 | 2000-12-22 | ||
EP00204739.7 | 2000-12-22 |
Publications (2)
Publication Number | Publication Date |
---|---|
WO2002051410A2 WO2002051410A2 (en) | 2002-07-04 |
WO2002051410A3 true WO2002051410A3 (en) | 2003-07-31 |
Family
ID=8172519
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2001/015119 WO2002051410A2 (en) | 2000-12-22 | 2001-12-19 | Phenylthiazole and thiazoline derivatives and their use as antiparasitics |
Country Status (1)
Country | Link |
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WO (1) | WO2002051410A2 (en) |
Families Citing this family (26)
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---|---|---|---|---|
KR20080019213A (en) | 2005-05-09 | 2008-03-03 | 아칠리온 파르마세우티칼스 인코포레이티드 | Thiazole compounds and methods of use |
EP2164846A2 (en) | 2007-05-22 | 2010-03-24 | Achillion Pharmaceuticals, Inc. | Heteroaryl substituted thiazoles and their use as antiviral agents. |
CN102579606B (en) * | 2011-01-18 | 2015-03-11 | 瑞普(天津)生物药业有限公司 | Anticoccidial traditional Chinese medicine preparation and preparation method thereof |
EA037918B1 (en) | 2011-12-21 | 2021-06-07 | Новира Терапьютикс, Инк. | Hepatitis b antiviral agents |
UA123256C2 (en) | 2012-08-28 | 2021-03-10 | ЯНССЕН САЙЄНСІЗ АЙРЛЕНД ЮСі | Sulfamoyl-arylamides and the use thereof as medicaments for the treatment of hepatitis b |
HUE034820T2 (en) | 2013-02-28 | 2018-02-28 | Janssen Sciences Ireland Uc | Sulfamoyl-arylamides and the use thereof as medicaments for the treatment of hepatitis b |
WO2014165128A2 (en) | 2013-03-12 | 2014-10-09 | Novira Therapeutics, Inc. | Hepatitis b antiviral agents |
ES2640063T3 (en) | 2013-04-03 | 2017-10-31 | Janssen Sciences Ireland Uc | N-phenyl-carboxamide derivatives and their use as medicines for the treatment of hepatitis B |
JO3603B1 (en) | 2013-05-17 | 2020-07-05 | Janssen Sciences Ireland Uc | Sulphamoylpyrrolamide derivatives and the use thereof as medicaments for the treatment of hepatitis b |
JP6348978B2 (en) | 2013-07-25 | 2018-06-27 | ヤンセン・サイエンシズ・アイルランド・ユーシー | Glyoxamide-substituted pyrrolamide derivatives and their use as pharmaceuticals for treating hepatitis B |
ES2655518T3 (en) | 2013-10-23 | 2018-02-20 | Janssen Sciences Ireland Uc | Carboxamide derivatives and their use as medicines for the treatment of hepatitis B |
US10392349B2 (en) | 2014-01-16 | 2019-08-27 | Novira Therapeutics, Inc. | Azepane derivatives and methods of treating hepatitis B infections |
US9181288B2 (en) | 2014-01-16 | 2015-11-10 | Novira Therapeutics, Inc. | Azepane derivatives and methods of treating hepatitis B infections |
US9169212B2 (en) | 2014-01-16 | 2015-10-27 | Novira Therapeutics, Inc. | Azepane derivatives and methods of treating hepatitis B infections |
KR20160128305A (en) | 2014-02-05 | 2016-11-07 | 노비라 테라퓨틱스, 인코포레이티드 | Combination therapy for treatment of hbv infections |
CN110483484A (en) | 2014-02-06 | 2019-11-22 | 爱尔兰詹森科学公司 | Sulfamoyl pyrrole amides derivative and its purposes for being used to treat hepatitis B as drug |
US10071976B2 (en) * | 2014-03-07 | 2018-09-11 | Sanford Burnham Prebys Medical Discovery Institute | Small molecule fatty acid synthase inhibitors |
US9400280B2 (en) | 2014-03-27 | 2016-07-26 | Novira Therapeutics, Inc. | Piperidine derivatives and methods of treating hepatitis B infections |
US9884831B2 (en) | 2015-03-19 | 2018-02-06 | Novira Therapeutics, Inc. | Azocane and azonane derivatives and methods of treating hepatitis B infections |
US10875876B2 (en) | 2015-07-02 | 2020-12-29 | Janssen Sciences Ireland Uc | Cyclized sulfamoylarylamide derivatives and the use thereof as medicaments for the treatment of hepatitis B |
EP3356328A1 (en) | 2015-09-29 | 2018-08-08 | Novira Therapeutics, Inc. | Crystalline forms of a hepatitis b antiviral agent |
KR20180129943A (en) | 2016-04-15 | 2018-12-05 | 노비라 테라퓨틱스, 인코포레이티드 | Formulations and methods involving capsid assembly inhibitors |
EP3502109A1 (en) * | 2017-12-20 | 2019-06-26 | Consejo Superior De Investigaciones Científicas | Triazole-phenyl-thiazole heterocycles as innovative inhibitors of trypanothione reductase and their use as leishmanicides |
CA3090125A1 (en) | 2018-03-14 | 2019-09-19 | Janssen Sciences Ireland Unlimited Company | Capsid assembly modulator dosing regimen |
CN113454077A (en) | 2019-02-22 | 2021-09-28 | 爱尔兰詹森科学公司 | Amide derivatives for the treatment of HBV infection or HBV-induced diseases |
BR112021021454A2 (en) | 2019-05-06 | 2021-12-21 | Janssen Sciences Ireland Unlimited Co | Amide derivatives useful in the treatment of HBV infection or HBV-induced diseases |
Citations (3)
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---|---|---|---|---|
US3676450A (en) * | 1969-10-30 | 1972-07-11 | Ciba Geigy Corp | -4-(isothi ocyanophenyl)-thiazoles |
JPS58124758A (en) * | 1982-01-20 | 1983-07-25 | Fujisawa Pharmaceut Co Ltd | Benzenesulfonamide derivative |
EP0237695A2 (en) * | 1986-01-17 | 1987-09-23 | MERCK PATENT GmbH | 1,4-Dihydropyridines |
-
2001
- 2001-12-19 WO PCT/EP2001/015119 patent/WO2002051410A2/en not_active Application Discontinuation
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3676450A (en) * | 1969-10-30 | 1972-07-11 | Ciba Geigy Corp | -4-(isothi ocyanophenyl)-thiazoles |
JPS58124758A (en) * | 1982-01-20 | 1983-07-25 | Fujisawa Pharmaceut Co Ltd | Benzenesulfonamide derivative |
EP0237695A2 (en) * | 1986-01-17 | 1987-09-23 | MERCK PATENT GmbH | 1,4-Dihydropyridines |
Non-Patent Citations (10)
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