AR053125A1 - Derivados de dihidroimidazotiazol - Google Patents
Derivados de dihidroimidazotiazolInfo
- Publication number
- AR053125A1 AR053125A1 ARP060100454A ARP060100454A AR053125A1 AR 053125 A1 AR053125 A1 AR 053125A1 AR P060100454 A ARP060100454 A AR P060100454A AR P060100454 A ARP060100454 A AR P060100454A AR 053125 A1 AR053125 A1 AR 053125A1
- Authority
- AR
- Argentina
- Prior art keywords
- dihydroimidazo
- thiazole
- hydroxy
- alkyl
- chlorophenyl
- Prior art date
Links
- 125000005843 halogen group Chemical group 0.000 abstract 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 7
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 6
- 150000001875 compounds Chemical class 0.000 abstract 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 3
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 abstract 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 abstract 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical group C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 abstract 2
- YLXOYZCNZFALTL-UHFFFAOYSA-N 2-chloro-4-(5,6-dihydroimidazo[2,1-b][1,3]thiazol-3-yl)phenol Chemical compound C1=C(Cl)C(O)=CC=C1C1=CSC2=NCCN12 YLXOYZCNZFALTL-UHFFFAOYSA-N 0.000 abstract 2
- 230000005764 inhibitory process Effects 0.000 abstract 2
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 abstract 1
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 abstract 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- 125000006592 (C2-C3) alkenyl group Chemical group 0.000 abstract 1
- VXAAXQGULJDERT-UHFFFAOYSA-N 2-(5,6-dihydroimidazo[2,1-b][1,3]thiazol-3-yl)-4-methylphenol Chemical compound CC1=CC=C(O)C(C=2N3CCN=C3SC=2)=C1 VXAAXQGULJDERT-UHFFFAOYSA-N 0.000 abstract 1
- LXTDUHGYHJHHIY-UHFFFAOYSA-N 2-(5,6-dihydroimidazo[2,1-b][1,3]thiazol-3-yl)-5-methoxyphenol Chemical compound OC1=CC(OC)=CC=C1C1=CSC2=NCCN12 LXTDUHGYHJHHIY-UHFFFAOYSA-N 0.000 abstract 1
- UQLCYTKVFDMDHX-UHFFFAOYSA-N 2-(5,6-dihydroimidazo[2,1-b][1,3]thiazol-3-yl)phenol Chemical compound OC1=CC=CC=C1C1=CSC2=NCCN12 UQLCYTKVFDMDHX-UHFFFAOYSA-N 0.000 abstract 1
- JHAOEAKSOBMXHQ-UHFFFAOYSA-N 3-(2,4-dichlorophenyl)-5,6-dihydroimidazo[2,1-b][1,3]thiazole Chemical compound ClC1=CC(Cl)=CC=C1C1=CSC2=NCCN12 JHAOEAKSOBMXHQ-UHFFFAOYSA-N 0.000 abstract 1
- HWNOKMZOQZEANC-UHFFFAOYSA-N 3-(2,4-difluorophenyl)-5,6-dihydroimidazo[2,1-b][1,3]thiazole Chemical compound FC1=CC(F)=CC=C1C1=CSC2=NCCN12 HWNOKMZOQZEANC-UHFFFAOYSA-N 0.000 abstract 1
- QHELVNRNDCLUGN-UHFFFAOYSA-N 3-(2,4-dimethylphenyl)-5,6-dihydroimidazo[2,1-b][1,3]thiazole Chemical compound CC1=CC(C)=CC=C1C1=CSC2=NCCN12 QHELVNRNDCLUGN-UHFFFAOYSA-N 0.000 abstract 1
- PASFDALJSQGOHG-UHFFFAOYSA-N 3-(2,5-dichlorophenyl)-5,6-dihydroimidazo[2,1-b][1,3]thiazole Chemical compound ClC1=CC=C(Cl)C(C=2N3CCN=C3SC=2)=C1 PASFDALJSQGOHG-UHFFFAOYSA-N 0.000 abstract 1
- IDPAKJLYDMTKMW-UHFFFAOYSA-N 3-(2-chlorophenyl)-5,6-dihydroimidazo[2,1-b][1,3]thiazole Chemical compound ClC1=CC=CC=C1C1=CSC2=NCCN12 IDPAKJLYDMTKMW-UHFFFAOYSA-N 0.000 abstract 1
- JMHKJJNVYMHYEE-UHFFFAOYSA-N 3-(2-methoxyphenyl)-5,6-dihydroimidazo[2,1-b][1,3]thiazole Chemical compound COC1=CC=CC=C1C1=CSC2=NCCN12 JMHKJJNVYMHYEE-UHFFFAOYSA-N 0.000 abstract 1
- VTLSAKMWUSOUNQ-UHFFFAOYSA-N 3-(2-methylphenyl)-5,6-dihydroimidazo[2,1-b][1,3]thiazole Chemical compound CC1=CC=CC=C1C1=CSC2=NCCN12 VTLSAKMWUSOUNQ-UHFFFAOYSA-N 0.000 abstract 1
- MDKLMHODJRVIMW-UHFFFAOYSA-N 3-(3,4-dichlorophenyl)-2-phenyl-5,6-dihydroimidazo[2,1-b][1,3]thiazole Chemical compound C1=C(Cl)C(Cl)=CC=C1C1=C(C=2C=CC=CC=2)SC2=NCCN12 MDKLMHODJRVIMW-UHFFFAOYSA-N 0.000 abstract 1
- GHYNKNDPIZBWPJ-UHFFFAOYSA-N 3-(3,4-dichlorophenyl)-5,6-dihydroimidazo[2,1-b][1,3]thiazole Chemical compound C1=C(Cl)C(Cl)=CC=C1C1=CSC2=NCCN12 GHYNKNDPIZBWPJ-UHFFFAOYSA-N 0.000 abstract 1
- RAVKJULPZQZXHT-UHFFFAOYSA-N 3-(3,4-dimethylphenyl)-5,6-dihydroimidazo[2,1-b][1,3]thiazole Chemical compound C1=C(C)C(C)=CC=C1C1=CSC2=NCCN12 RAVKJULPZQZXHT-UHFFFAOYSA-N 0.000 abstract 1
- VWJJDNBPVIMITE-UHFFFAOYSA-N 3-(3-chloro-4-propoxyphenyl)-5,6-dihydroimidazo[2,1-b][1,3]thiazole Chemical compound C1=C(Cl)C(OCCC)=CC=C1C1=CSC2=NCCN12 VWJJDNBPVIMITE-UHFFFAOYSA-N 0.000 abstract 1
- ANLMHQNDORGZKM-UHFFFAOYSA-N 3-(3-chlorophenyl)-5,6-dihydroimidazo[2,1-b][1,3]thiazole Chemical compound ClC1=CC=CC(C=2N3CCN=C3SC=2)=C1 ANLMHQNDORGZKM-UHFFFAOYSA-N 0.000 abstract 1
- GCPIYTCYJXIPOF-UHFFFAOYSA-N 3-(3-methoxyphenyl)-5,6-dihydroimidazo[2,1-b][1,3]thiazole Chemical compound COC1=CC=CC(C=2N3CCN=C3SC=2)=C1 GCPIYTCYJXIPOF-UHFFFAOYSA-N 0.000 abstract 1
- KVLMKRCTVPYMRK-UHFFFAOYSA-N 3-(3-methylphenyl)-5,6-dihydroimidazo[2,1-b][1,3]thiazole Chemical compound CC1=CC=CC(C=2N3CCN=C3SC=2)=C1 KVLMKRCTVPYMRK-UHFFFAOYSA-N 0.000 abstract 1
- PVPFCMJKVBCGES-UHFFFAOYSA-N 3-(4-bromophenyl)-5,6-dihydroimidazo[2,1-b][1,3]thiazole Chemical compound C1=CC(Br)=CC=C1C1=CSC2=NCCN12 PVPFCMJKVBCGES-UHFFFAOYSA-N 0.000 abstract 1
- NEAURCXWRFTFGK-UHFFFAOYSA-N 3-(4-chlorophenyl)-2-ethyl-5,6-dihydroimidazo[2,1-b][1,3]thiazole Chemical compound N12CCN=C2SC(CC)=C1C1=CC=C(Cl)C=C1 NEAURCXWRFTFGK-UHFFFAOYSA-N 0.000 abstract 1
- FNNKLUDOORPHGR-UHFFFAOYSA-N 3-(4-chlorophenyl)-2-methyl-5,6-dihydroimidazo[2,1-b][1,3]thiazole Chemical compound N12CCN=C2SC(C)=C1C1=CC=C(Cl)C=C1 FNNKLUDOORPHGR-UHFFFAOYSA-N 0.000 abstract 1
- DFKOPKKSCIVOAK-UHFFFAOYSA-N 3-(4-chlorophenyl)-5,6-dihydroimidazo[2,1-b][1,3]thiazole Chemical compound C1=CC(Cl)=CC=C1C1=CSC2=NCCN12 DFKOPKKSCIVOAK-UHFFFAOYSA-N 0.000 abstract 1
- GFKOZTFNBVVIBX-UHFFFAOYSA-N 3-(4-methoxyphenyl)-5,6-dihydroimidazo[2,1-b][1,3]thiazole Chemical compound C1=CC(OC)=CC=C1C1=CSC2=NCCN12 GFKOZTFNBVVIBX-UHFFFAOYSA-N 0.000 abstract 1
- ZSLGTNCOVGLOAD-UHFFFAOYSA-N 3-(4-methylphenyl)-5,6-dihydroimidazo[2,1-b][1,3]thiazole Chemical compound C1=CC(C)=CC=C1C1=CSC2=NCCN12 ZSLGTNCOVGLOAD-UHFFFAOYSA-N 0.000 abstract 1
- OPDZQTXVFCASSY-UHFFFAOYSA-N 3-(5,6-dihydroimidazo[2,1-b][1,3]thiazol-3-yl)phenol Chemical compound OC1=CC=CC(C=2N3CCN=C3SC=2)=C1 OPDZQTXVFCASSY-UHFFFAOYSA-N 0.000 abstract 1
- NMEORCHLDVEQGJ-UHFFFAOYSA-N 3-naphthalen-1-yl-5,6-dihydroimidazo[2,1-b][1,3]thiazole;hydrobromide Chemical compound Br.C1=CC=C2C(C3=CSC=4N3CCN=4)=CC=CC2=C1 NMEORCHLDVEQGJ-UHFFFAOYSA-N 0.000 abstract 1
- WNNBTGLATSKDPB-UHFFFAOYSA-N 3-naphthalen-2-yl-5,6-dihydroimidazo[2,1-b][1,3]thiazole;hydrobromide Chemical compound Br.C1=CC=CC2=CC(C3=CSC=4N3CCN=4)=CC=C21 WNNBTGLATSKDPB-UHFFFAOYSA-N 0.000 abstract 1
- SGFBFQMCAQIRPX-UHFFFAOYSA-N 4-(5,6-dihydroimidazo[2,1-b][1,3]thiazol-3-yl)-2-methoxyphenol Chemical compound C1=C(O)C(OC)=CC(C=2N3CCN=C3SC=2)=C1 SGFBFQMCAQIRPX-UHFFFAOYSA-N 0.000 abstract 1
- LIPVECSLKKZAJY-UHFFFAOYSA-N 4-(5,6-dihydroimidazo[2,1-b][1,3]thiazol-3-yl)-2-methylphenol Chemical compound C1=C(O)C(C)=CC(C=2N3CCN=C3SC=2)=C1 LIPVECSLKKZAJY-UHFFFAOYSA-N 0.000 abstract 1
- URHXFMOERPVENY-UHFFFAOYSA-N 4-(5,6-dihydroimidazo[2,1-b][1,3]thiazol-3-yl)aniline Chemical compound C1=CC(N)=CC=C1C1=CSC2=NCCN12 URHXFMOERPVENY-UHFFFAOYSA-N 0.000 abstract 1
- DFKSLAHGEOVWTN-UHFFFAOYSA-N 4-(5,6-dihydroimidazo[2,1-b][1,3]thiazol-3-yl)benzene-1,2-diol Chemical compound C1=C(O)C(O)=CC=C1C1=CSC2=NCCN12 DFKSLAHGEOVWTN-UHFFFAOYSA-N 0.000 abstract 1
- NNKWQHUSNAWAQJ-UHFFFAOYSA-N 4-(5,6-dihydroimidazo[2,1-b][1,3]thiazol-3-yl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CSC2=NCCN12 NNKWQHUSNAWAQJ-UHFFFAOYSA-N 0.000 abstract 1
- FKMAHAJZNDLUCM-UHFFFAOYSA-N 4-(5,6-dihydroimidazo[2,1-b][1,3]thiazol-3-yl)benzonitrile Chemical compound C1=CC(C#N)=CC=C1C1=CSC2=NCCN12 FKMAHAJZNDLUCM-UHFFFAOYSA-N 0.000 abstract 1
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 abstract 1
- VFLWRBJZVGIOCF-UHFFFAOYSA-N 5-(5,6-dihydroimidazo[2,1-b][1,3]thiazol-3-yl)-2-methoxyphenol Chemical compound C1=C(O)C(OC)=CC=C1C1=CSC2=NCCN12 VFLWRBJZVGIOCF-UHFFFAOYSA-N 0.000 abstract 1
- 102100022738 5-hydroxytryptamine receptor 1A Human genes 0.000 abstract 1
- 101710138638 5-hydroxytryptamine receptor 1A Proteins 0.000 abstract 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 abstract 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 abstract 1
- 208000008589 Obesity Diseases 0.000 abstract 1
- 230000008484 agonism Effects 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000000304 alkynyl group Chemical group 0.000 abstract 1
- 125000002837 carbocyclic group Chemical group 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- -1 cyano, hydroxy Chemical group 0.000 abstract 1
- 125000005842 heteroatom Chemical group 0.000 abstract 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
- 230000000966 norepinephrine reuptake Effects 0.000 abstract 1
- 235000020824 obesity Nutrition 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
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
-
- 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
- A61K31/429—Thiazoles condensed with heterocyclic 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
-
- 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
- A61P9/12—Antihypertensives
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Child & Adolescent Psychology (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
Composicion farmacéutica, proceso para obtener los compuestos que exhiben agonismo de 5-HT1A además de la inhibicion de la recaptacion de la noradrenalina y opcionalmente también la inhibicion de la recaptacion de 5-HT y son de utilidad para el tratamiento de obesidad. Reivindicacion 1: Un compuesto de la formula (1) o una de sus sales farmacéuticamente aceptables, en donde R1 es H, halo, alquilo c1-6 opcionalmente sustituido con uno o varios átomos de halogeno o grupos hidroxi, cicloalquilo C3-6 opcionalmente sustituido con uno o varios átomos de halogeno o gripos hidroxi, alquil C1-2-cicloalquilo C3-6 opcionalmente sustituido con uno o varios átomos de halogeno o grupos hidroxi, alcoxicarbonilo C1-6, ciano, -C=N-OR7, alquenilo C2-6 opcionalmente sustituido con uno o varios átomos de halogeno o grupos hidroxi, en donde el hidroxi no está directamente unido con el C del enlace doble, alquinilo C2-6 opcionalmente sustituido con uno o varios átomos de halogeno o grupos hidroxi, en donde el hidroxi no está directamente unido con el C del enlace triple, (CH2)mNR5R6, alcoxi C1-3, alquiltio C1-3, alcoxi C1-3-alquilo C1-3 o alquiltio C1-3-alquilo C1-3; R2 es un grupo aromático bicíclico de 8 a 10 miembros que opcionalmente contiene hasta 3 heteroátomos seleccionados de N y S, o fenilo, con la condicion de que R2 no sea benzo[b]tiofeno; 2 puede estar opcionalmente sustituido con uno o varios grupos seleccionados de halo, ciano, hidroxi, NR5R6, CONR5R6 o COOR7 o alquilo C1-3, alquenilo C2-3, alquinilo C1-3, cicloalquilo C3-6, alcoxi C1-3, hidroxialquilo C1-3, alcoxialquilo C2-3 o alquil C1-3-S(O)n, cualquiera de os cuales puede estar opcionalmente sustituido con uno o varios átomos de halogeno; o cuando R2 es fenilo, dos sustituyentes en el fenilo pueden unirse para formar un anillo carbocíclico condensado C5-6; R3 y R4 son, de modo independiente, H o alquilo C1-3; R5 y R6 son, de modo independiente, H o alquilo C1-3, o, junto con el N al que están unidos, forman un grupo heterocíclico de 5 o 6 miembros; R7 es H o alquilo C1-3; m es 1, 2 o 3; y n es 0, 1 o 2; con la condicion de que el compuesto no sea: a) bromhidrato de 3-naftalen-1-il-5,6-dihidroimidazo[2,1-b]tiazol; b) bromhidrato de 3-naftalen-2-il-5,6-dihidroimidazo[2,1-b]tiazol; c) 3-(3-cloro-4-propoxifenil)-5,6-dihidroimidazo[2,1-b]tiazol; d) 3-(4-clorofenil)-2-etil-5,6-dihidroimidazo[2,1-b]tiazol; e) 3-(4-clorofenil)-2-metil-5,6-dihidroimidazo[2,1-b]tiazol; f) 3-(3,4- diclorofenil)-5,6-dihidroimidazo[2,1-b]tiazol; g) 3-(2-hidroxi-5-metilfenil)-5,6-dihidroimidazo[2,1-b]tiazol; h) 3-(4-aminofenil)-5,6-dihidroimidazo[2,1-b]tiazol; i) 3-(2-clorofenil)-5,6-dihidroimidazo[2,1-b]tiazol; j) 3-(3-clorofenil)-5,6- dihidroimidazo[2,1-b]tiazol; k) 3-(4-clorofenil)-5,6-dihidroimidazo[2,1-b]tiazol, l) 3-(2,4-diclorofenil)-5,6-dihidroimidazo[2,1-b]tiazol; m) 3-(2,5-diclorofenil)-5,6-dihidroimidazo[2,1-b]tiazol; n) 3-(4-bromofenil)-5,6-dihidroimidazo[2,1-b]tiazol; o) 3-(2,4-difluorofenil)-5,6-dihidroimidazo[2,1-b]tiazol; p) 3-(2-metilfenil)-5,6-dihidroimidazo[2,1-b]tiazol; q) 3-(3-metilfenil)-5,6-dihidroimidazo[2,1-b]tiazol; r) 3-(4-metilfenil)-5,6-dihidroimidazo[2,1-b]tiazol; s) 3-(2,4-dimetilfenil)-5,6- dihidroimidazo[2,1-b]tiazol; t) 3-(3,4-dimetilfenil)-5,6-dihidroimidazo[2,1-b]tiazol; u) 3-(4-cianofenil)-5,6-dihidroimidazo[2,1-b]tiazol; v) 3-(4-carboxifenil)-5,6-dihidroimidazo[2,1-b]tiazol; w) 3-(2-metoxifenil)-5,6-dihidroimidazo[2,1-b]tiazol; x) 3-(3-metoxifenil)-5,6-dihidroimidazo[2,1-b]tiazol; i) 3-(4-metoxifenil)-5,6-dihidroimidazo[2,1-b]tiazol; z) 3-(2hidroxifenil)-5,6-dihidroimidazo[2,1-b]tiazol; aa) 3-(3-hidroxifenil)-5,6-dihidroimidazo[2,1-b]tiazol; ab) 3-(4-hidroxifenil)-5,6- dihidroimidazo[2,1-b]tiazol; ac) 3-(3,4-dihidroxifenil)-5,6-dihidroimidazo[2,1-b]tiazol; ad) 3-(2-hidroxi-4-metoxifenil)-5,6-dihidroimidazo[2,1-b]tiazol; ae) 3-(3-hidroxi-4-metoxifenil)-5,6-dihidroimidazo[2,1-b]tiazol; af) 3-(4-hidroxi-3- metoxifenil)-5,6-dihidroimidazo[2,1-b]tiazol; ag) 3-(4-hidroxi-3-clorofenil)-5,6-dihidroimidazo[2,1-b]tiazol; ah) 3-(4-hidroxi-3-clorofenil)-5,6-dihidroimidazo[2,1-b]tiazol; ah) 3-(4-hidroxi-3-metilfenil)-5,6-dihidroimidazo[2,1-b]tiazol, o ai) 3- (3,4-diclorofenil)-2-fenil-5,6-dihidroimidazo[2,1-b]tiazol.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US65090605P | 2005-02-08 | 2005-02-08 | |
| US68436905P | 2005-05-25 | 2005-05-25 | |
| US76166606P | 2006-01-24 | 2006-01-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR053125A1 true AR053125A1 (es) | 2007-04-25 |
Family
ID=36654712
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP060100454A AR053125A1 (es) | 2005-02-08 | 2006-02-08 | Derivados de dihidroimidazotiazol |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US20090221645A1 (es) |
| EP (1) | EP1851232A2 (es) |
| JP (1) | JP2008530077A (es) |
| KR (1) | KR20070107116A (es) |
| AR (1) | AR053125A1 (es) |
| AU (1) | AU2006212038A1 (es) |
| BR (1) | BRPI0606881A2 (es) |
| CA (1) | CA2597288A1 (es) |
| EA (1) | EA012374B1 (es) |
| IL (1) | IL184996A0 (es) |
| MA (1) | MA29246B1 (es) |
| MX (1) | MX2007009526A (es) |
| NO (1) | NO20073941L (es) |
| NZ (1) | NZ561006A (es) |
| TW (1) | TW200639177A (es) |
| WO (1) | WO2006085118A2 (es) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1923062A1 (en) * | 2006-11-16 | 2008-05-21 | sanofi-aventis | Imidazo[2,1-b]thiazoles and their use as pharmaceuticals |
| GB0916608D0 (en) | 2009-09-22 | 2009-11-04 | Angeletti P Ist Richerche Bio | Therapeutic compounds |
| WO2012120055A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Di- und trisubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| US8828995B2 (en) | 2011-03-08 | 2014-09-09 | Sanofi | Branched oxathiazine derivatives, method for the production thereof, use thereof as medicine and drug containing said derivatives and use thereof |
| EP2766349B1 (de) | 2011-03-08 | 2016-06-01 | Sanofi | Mit carbozyklen oder heterozyklen substituierte oxathiazinderivate, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung |
| US8828994B2 (en) | 2011-03-08 | 2014-09-09 | Sanofi | Di- and tri-substituted oxathiazine derivatives, method for the production thereof, use thereof as medicine and drug containing said derivatives and use thereof |
| WO2012120056A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Tetrasubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| EP2567959B1 (en) | 2011-09-12 | 2014-04-16 | Sanofi | 6-(4-hydroxy-phenyl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| US10421764B2 (en) * | 2015-04-24 | 2019-09-24 | H. Lee Moffitt Cancer Center And Research Institute, Inc. | Mutant KRas inhibitors |
| EP4483875A3 (en) | 2016-05-10 | 2025-04-02 | C4 Therapeutics, Inc. | Spirocyclic degronimers for target protein degradation |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1488314A (fr) * | 1966-04-25 | 1967-07-13 | Chimetron Sarl | Imidazothiazolyl-benzimidazoles |
| CH507982A (de) * | 1968-05-15 | 1971-05-31 | Sandoz Ag | Verfahren zur Herstellung von 2-Chloräthyl-3-phenyl-5, 6-dihydroimidazo(2,1-b)thiazolen bzw. -6,7-dihydro-5H-thiazolo(3,2-a)pyrimidinen |
| CH513918A (de) * | 1968-07-31 | 1971-10-15 | Sandoz Ag | Verfahren zur Herstellung von 2-n-Alkyl-3-phenyl-6,7-dihydro-5H-thiazolo(3,2-a)pyrimidinen bzw. 2-n-Alkyl-3-phenyl-5,6-dihydroimidazo(2,1-b)thiazolen |
| US3671533A (en) * | 1970-01-26 | 1972-06-20 | Sandoz Ag | 2,3,5,6-TETRAHYDROIMIDAZO{8 2,1-b{9 THIAZOLES |
| US4041167A (en) * | 1976-01-19 | 1977-08-09 | Diamond Shamrock Corporation | Antiinflammatory imidazothiazoles |
| GB1556878A (en) * | 1976-01-19 | 1979-11-28 | Diamond Shamrock Corp | Imidazothiazoles |
| FR2643903A1 (fr) * | 1989-03-03 | 1990-09-07 | Union Pharma Scient Appl | Nouveaux derives de benzimidazole, leurs procedes de preparation, intermediaires de synthese, compositions pharmaceutiques les contenant, utiles notamment pour le traitement des maladies cardiovasculaires, et des ulceres duodenaux |
-
2006
- 2006-02-08 JP JP2007554660A patent/JP2008530077A/ja not_active Withdrawn
- 2006-02-08 EA EA200701676A patent/EA012374B1/ru not_active IP Right Cessation
- 2006-02-08 WO PCT/GB2006/050031 patent/WO2006085118A2/en not_active Ceased
- 2006-02-08 AU AU2006212038A patent/AU2006212038A1/en not_active Abandoned
- 2006-02-08 BR BRPI0606881-2A patent/BRPI0606881A2/pt not_active IP Right Cessation
- 2006-02-08 KR KR1020077020626A patent/KR20070107116A/ko not_active Withdrawn
- 2006-02-08 US US11/884,087 patent/US20090221645A1/en not_active Abandoned
- 2006-02-08 TW TW095104231A patent/TW200639177A/zh unknown
- 2006-02-08 AR ARP060100454A patent/AR053125A1/es not_active Application Discontinuation
- 2006-02-08 EP EP06710155A patent/EP1851232A2/en not_active Withdrawn
- 2006-02-08 CA CA002597288A patent/CA2597288A1/en not_active Abandoned
- 2006-02-08 NZ NZ561006A patent/NZ561006A/en not_active IP Right Cessation
- 2006-02-08 MX MX2007009526A patent/MX2007009526A/es not_active Application Discontinuation
-
2007
- 2007-07-27 NO NO20073941A patent/NO20073941L/no not_active Application Discontinuation
- 2007-08-02 IL IL184996A patent/IL184996A0/en unknown
- 2007-08-08 MA MA30130A patent/MA29246B1/fr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BRPI0606881A2 (pt) | 2009-07-21 |
| WO2006085118A3 (en) | 2006-10-19 |
| CA2597288A1 (en) | 2006-08-17 |
| NO20073941L (no) | 2007-11-05 |
| AU2006212038A1 (en) | 2006-08-17 |
| KR20070107116A (ko) | 2007-11-06 |
| IL184996A0 (en) | 2007-12-03 |
| EA200701676A1 (ru) | 2008-02-28 |
| US20090221645A1 (en) | 2009-09-03 |
| WO2006085118A2 (en) | 2006-08-17 |
| MA29246B1 (fr) | 2008-02-01 |
| MX2007009526A (es) | 2007-09-26 |
| NZ561006A (en) | 2010-06-25 |
| TW200639177A (en) | 2006-11-16 |
| EA012374B1 (ru) | 2009-10-30 |
| JP2008530077A (ja) | 2008-08-07 |
| EP1851232A2 (en) | 2007-11-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FA | Abandonment or withdrawal |