AR039367A1 - Compuestos derivados de benzotiazol, nicotina o isonicotina, un proceso para su preparacion, un medicamento que los contiene y uso de los mismos - Google Patents
Compuestos derivados de benzotiazol, nicotina o isonicotina, un proceso para su preparacion, un medicamento que los contiene y uso de los mismosInfo
- Publication number
- AR039367A1 AR039367A1 ARP020104416A ARP020104416A AR039367A1 AR 039367 A1 AR039367 A1 AR 039367A1 AR P020104416 A ARP020104416 A AR P020104416A AR P020104416 A ARP020104416 A AR P020104416A AR 039367 A1 AR039367 A1 AR 039367A1
- Authority
- AR
- Argentina
- Prior art keywords
- lower alkyl
- formula
- compound
- morpholinyl
- cycloalkyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title abstract 25
- 238000000034 method Methods 0.000 title abstract 4
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 title abstract 2
- UEIZUEWXLJOVLD-UHFFFAOYSA-N 3-(1-methylpyrrolidin-3-yl)pyridine Chemical compound C1N(C)CCC1C1=CC=CN=C1 UEIZUEWXLJOVLD-UHFFFAOYSA-N 0.000 title abstract 2
- 229960002715 nicotine Drugs 0.000 title abstract 2
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 title abstract 2
- 229940126601 medicinal product Drugs 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 36
- 125000003545 alkoxy group Chemical group 0.000 abstract 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 6
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 6
- 229910052739 hydrogen Inorganic materials 0.000 abstract 6
- 239000001257 hydrogen Substances 0.000 abstract 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 6
- 125000002757 morpholinyl group Chemical group 0.000 abstract 5
- -1 or is acetidinyl Chemical group 0.000 abstract 4
- 125000003386 piperidinyl group Chemical group 0.000 abstract 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 3
- 229910052794 bromium Chemical group 0.000 abstract 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 3
- 208000024827 Alzheimer disease Diseases 0.000 abstract 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 2
- 241000282326 Felis catus Species 0.000 abstract 2
- 208000018737 Parkinson disease Diseases 0.000 abstract 2
- OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 abstract 2
- 239000001961 anticonvulsive agent Substances 0.000 abstract 2
- 239000000460 chlorine Substances 0.000 abstract 2
- 229910052801 chlorine Inorganic materials 0.000 abstract 2
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 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 abstract 2
- 208000035475 disorder Diseases 0.000 abstract 2
- 239000003814 drug Substances 0.000 abstract 2
- 230000004112 neuroprotection Effects 0.000 abstract 2
- 125000004043 oxo group Chemical group O=* 0.000 abstract 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 208000011117 substance-related disease Diseases 0.000 abstract 2
- 102000007471 Adenosine A2A receptor Human genes 0.000 abstract 1
- 108010085277 Adenosine A2A receptor Proteins 0.000 abstract 1
- 108050000203 Adenosine receptors Proteins 0.000 abstract 1
- 102000009346 Adenosine receptors Human genes 0.000 abstract 1
- 101150051188 Adora2a gene Proteins 0.000 abstract 1
- 208000019901 Anxiety disease Diseases 0.000 abstract 1
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 abstract 1
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 abstract 1
- 239000002126 C01EB10 - Adenosine Substances 0.000 abstract 1
- SRPCCBAOIRMMRV-UHFFFAOYSA-N C1=CC=C2SC=NC2=C1.CN1CCCC1C1=CC=CN=C1 Chemical compound C1=CC=C2SC=NC2=C1.CN1CCCC1C1=CC=CN=C1 SRPCCBAOIRMMRV-UHFFFAOYSA-N 0.000 abstract 1
- 206010010904 Convulsion Diseases 0.000 abstract 1
- 208000020401 Depressive disease Diseases 0.000 abstract 1
- 208000010496 Heart Arrest Diseases 0.000 abstract 1
- 208000023105 Huntington disease Diseases 0.000 abstract 1
- 206010021143 Hypoxia Diseases 0.000 abstract 1
- 208000002193 Pain Diseases 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 229960005305 adenosine Drugs 0.000 abstract 1
- 208000026935 allergic disease Diseases 0.000 abstract 1
- 230000003042 antagnostic effect Effects 0.000 abstract 1
- 230000003556 anti-epileptic effect Effects 0.000 abstract 1
- 229940125681 anticonvulsant agent Drugs 0.000 abstract 1
- 229960003965 antiepileptics Drugs 0.000 abstract 1
- 239000000164 antipsychotic agent Substances 0.000 abstract 1
- 229940005529 antipsychotics Drugs 0.000 abstract 1
- 230000036506 anxiety Effects 0.000 abstract 1
- 208000006673 asthma Diseases 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 abstract 1
- 125000001246 bromo group Chemical group Br* 0.000 abstract 1
- 229930003827 cannabinoid Natural products 0.000 abstract 1
- 239000003557 cannabinoid Substances 0.000 abstract 1
- 229940065144 cannabinoids Drugs 0.000 abstract 1
- 229940045200 cardioprotective agent Drugs 0.000 abstract 1
- 239000012659 cardioprotective agent Substances 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 210000003169 central nervous system Anatomy 0.000 abstract 1
- 229960003920 cocaine Drugs 0.000 abstract 1
- 208000029078 coronary artery disease Diseases 0.000 abstract 1
- 125000000392 cycloalkenyl group Chemical group 0.000 abstract 1
- 230000006735 deficit Effects 0.000 abstract 1
- 201000010099 disease Diseases 0.000 abstract 1
- 230000006806 disease prevention Effects 0.000 abstract 1
- 229940079593 drug Drugs 0.000 abstract 1
- 206010013663 drug dependence Diseases 0.000 abstract 1
- 229960004756 ethanol Drugs 0.000 abstract 1
- 230000007954 hypoxia Effects 0.000 abstract 1
- 208000028867 ischemia Diseases 0.000 abstract 1
- 229940035363 muscle relaxants Drugs 0.000 abstract 1
- 239000003158 myorelaxant agent Substances 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 229940005483 opioid analgesics Drugs 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 230000036407 pain Effects 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 125000004193 piperazinyl group Chemical group 0.000 abstract 1
- 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 abstract 1
- 230000002265 prevention Effects 0.000 abstract 1
- 108020003175 receptors Proteins 0.000 abstract 1
- 102000005962 receptors Human genes 0.000 abstract 1
- 230000000241 respiratory effect Effects 0.000 abstract 1
- 201000000980 schizophrenia Diseases 0.000 abstract 1
- 229940125723 sedative agent Drugs 0.000 abstract 1
- 239000000932 sedative agent Substances 0.000 abstract 1
- 201000009032 substance abuse Diseases 0.000 abstract 1
- 231100000736 substance abuse Toxicity 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
- 239000011593 sulfur Substances 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P11/06—Antiasthmatics
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
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- A61P25/16—Anti-Parkinson drugs
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- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61P25/24—Antidepressants
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- A61P25/32—Alcohol-abuse
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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
- C07D417/14—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 three or more hetero rings
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Psychiatry (AREA)
- Addiction (AREA)
- Pulmonology (AREA)
- Cardiology (AREA)
- Pain & Pain Management (AREA)
- Heart & Thoracic Surgery (AREA)
- Hospice & Palliative Care (AREA)
- Psychology (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Rheumatology (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Immunology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Compuestos derivados de benzotiazol nicotina o isonicotina de fórmula general (1) o (2), en donde: R1 es fenilo, piperidin-1-ilo o morfolinilo; A es -O-; y R es -(CH2)n-N(R'')-C(O)-alquilo inferior, -(C2)n-O-alquilo inferior, -(CH2)n-O-(CH2)n-O-alquilo inferior, alquilo inferior, -(CH2)n-morfolinilo,-(CH2)n-fenilo, -(CH2)n-N(R'')2, -(CH2)n-piridinilo, -(CH2)n-CF3, -(CH2)n-2-oxo-pirrolidinilo o cicloalquilo C4-6; R'' es independientemente uno del otro hidrógeno o alquilo inferior y n es 1 ó 2; ó A es -N(R')-; y R es alquilo inferior, cicloalquilo C4-6, -(CH2)n-O-alquilo inferior, -(CH2)n-piridinilo,-(CH2)n-piperidinilo, -(CH2)n-fenilo, -(CH2)n-N(R'')-C(O)-alquilo inferior, -(CH2)n-morfolinilo, o -(CH2)n-N(R'')2; R' y R'' son independientemente uno del otro hidrógeno o alquilo inferior y n es 1 ó 2; ó A es -CH2-; y R es -N(R'')-(CH2)m-O-alquilo inferior, -N(R'')2, S-alquilo inferior, o es acetidinilo, pirrolidinilo o piperidinilo, que están opcionalmente sustituidos por hidroxilo o alcoxilo inferior o es morfolinilo, -N(R'')-(CH2)m-cicloalquilo C4-6, -N(R'')-(CH2)m-C(O)O-alquilo inferior, -N(R'')-(CH2)m-C(O)OH, -2-oxo-pirrolidinilo, -N(R'')-C(O)O-alquilo inferior, -O(CH2)m-O-alquilo inferior o alcoxilo; R'' es independientemente uno del otro hidrógeno o alquilo inferior y m es 1, 2 ó 3; o A es -S-; y R es alquilo inferior; o A-R son juntos -piperazinilo, sustituido por alquilo inferior, -C(O)-alquilo inferior o un grupo oxo, o es piperidinilo, sustituido por alcoxilo inferior o hidroxilo, o es morfolinilo, sustituido por alquilo inferior, o es cicloalquilo C4-6, -azetidin-1-ilo, opcionalmente sustituido por hidroxilo o alcoxilo inferior, tiomorfolin-1,1-dioxo-tetrahidropirano o 2-oxa-5-aza-biciclo[2.2.1]hept-5-ilo; y las sales farmacéuticamente aceptables de los mismos. Se ha encontrado que los compuestos de fórmula general (1) son ligados del receptor de adenosina. Específicamente, estos compuestos tienen una buena afinidad por el receptor A2A de adenosina y éstos son por lo tanto útiles en el tratamiento de enfermedades relacionadas con este receptor. Estos compuestos son útiles en el control o prevención de enfermedades basadas en la modulación del sistema de la adenosina, tales como la enfermedad de Alzheimer, la enfermedad de Parkinson, la enfermedad de Huntington, neuroprotección, esquizofrenia, ansiedad, dolor, déficits respiratorios, depresión, adicción a las drogas, tales como anfetaminas, cocaína, opioides, etanol, nicotina, canabinoides o contra asma, respuestas alérgicas, hipoxia, isquemia, convulsiones y abuso de sustancias. Además, estos compuestos podrían ser útiles como sedantes, relajantes musculares, antipsicóticos, antiepilépticos, anticonvulsivos y agentes cardioprotectores contra trastornos tales como enfermedad coronaria arterial y paro cardíaco. Las indicaciones más preferibles de acuerdo con la presente son aquellas, que se basan en la actividad antagonista del receptor A2A y que incluye trastornos del sistema nervioso central, por ejemplo el tratamiento o prevención de la enfermedad de Alzheimer, ciertos trastornos depresivos, adición a las drogas, neuroprotección y enfermedad de Parkinson así como ADHD. También se divulga un proceso para su preparación, un medicamento que los contiene y el uso de los mismos. Reivindicación 34: Un proceso para la preparación de un compuesto de fórmula (1) ó (2) tal como se definen en la reivindicación 1, cuyo proceso comprende: a) reacción de un compuesto de fórmula (3) o (4) con un compuesto de fórmula: H-A-R, en presencia de una base para dar un compuesto de fórmula (1) ó (2) en donde R es -(CH2)n-N(R'')-C(O)-alquilo inferior, -(CH2)n-O-alquilo inferior, -(CH2)n-O-(CH2)n-O-alquilo inferior, alquilo inferior, -(CH2)n-morfolinilo, -(CH2)n-fenilo, -(CH2)n-N(R'')2, -(CH2)n-piridinilo, -(CH2)n-CF3, -(CH2)n-2-oxo-pirrolidinilo ó CH4-6-cicloalquilo, Y es cloro o bromo, A es oxígeno ó azufre, y n es 1 ó 2; b) reacción de un compuesto de fórmula (3) ó (4) con un compuesto de fórmula HNRR' para dar un compuesto de fórmula (5) ó (6) en donde R es alquilo inferior, cicloalquilo C4-6, -(CH2)n-O-alquilo inferior, -(CH2)n-piridinilo, -(CH2)n-piperidinilo, -(CH2)n-fenilo, -(CH2)n-N(R'')-C(O)-alquilo inferior, -(CH2)n-morfolinilo ó -(CH2)n-N(R'')2 ó R y R' forman junto con el átomo de N los siguientes grupos: piperazinilo, opcionalmente sustituido con alquilo inferior, C(O)-alquilo inferior ó un grupo oxo, piperidinilo, opcionalmente sustituido por alcoxilo inferior o hidroxilo, morfolinilo, opcionalmente sustituido por alquilo inferior, azetidin-1-ilo, opcionalmente sustituido por hidroxilo o alcoxilo inferior, ó tiomorfolin-1,1-dioxo ó 2-oxa-biciclo[2.21] hept-5-ilo, R' y R'' son independientemente uno del otro hidrógeno o alquilo inferior, Y es cloro o bromo y n es 1 ó 2; ó c) reacción de un compuesto de fórmula (7) ó (8) con un compuesto de fórmula H-R para dar un compuesto de fórmula (9) ó (10) en donde R es -N(R'')-(C2)m-O-alquilo inferior, -N(R'')2, -S-alquilo inferior o es acetidinilo, pirrolidinilo ó piperidinilo, que están opcionalmente sustituidos por hidroxilo ó alcoxilo inferior o es morfolinilo, -N(R'')-(CH2)m-(cicloalquilo C4-6), N(R'')-(CH2)m-C(O)O-alquilo inferior, -N(R'')-(CH2)m-C(O)OH, -2-oxo-pirrolidinilo, -N(R'')-C(O)O-alquilo inferior, -O(CH2)m-O-alquilo inferior o alcoxilo, R'' es independientemente uno del otro hidrógeno o alquilo inferior y m es 1, 2 ó 3, o d) reacción de un compuesto de fórmula (7) ó (8) con un compuesto de fórmula H-O-R para dar un compuesto de fórmula (11) ó (12) en donde R es -(CH2)m-O-alquilo inferior o es alquilo inferior y m es 1, 2 ó 3, ó e) reacción de un compuesto de fórmula (3) ó (4) con un compuesto de fórmula Bu3Sn-A'-R/cat o con B(OH)2-A'-R/cat para dar un compuesto de fórmula (13) ó (14) en donde A'-R son juntos cicloalquenilo C4-6 o dihidopirano e Y es bromo, y entonces reaccionar un compuesto de fórmula (13) ó (14) con hidrógeno y un catalizador para dar el compuesto de fórmula (1) ó (2) en donde A-R son juntos cicloalquilo C4-6 o tetrahidropirano, y si se desea, convertir los compuestos obtenidos en las sales de adición ácida farmacéuticamente aceptables.
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| Application Number | Priority Date | Filing Date | Title |
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| EP01127312 | 2001-11-19 |
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| KR (1) | KR100577110B1 (es) |
| CN (1) | CN100546580C (es) |
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| HR (1) | HRP20040396A2 (es) |
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| US6734179B2 (en) * | 2001-12-12 | 2004-05-11 | Hoffmann-La Roche Inc. | Benzothiazoles |
| US20050119251A1 (en) * | 2001-12-21 | 2005-06-02 | Jian-Min Fu | Nicotinamide derivatives and their use as therapeutic agents |
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| EP2316827B1 (en) | 2003-07-30 | 2016-01-27 | Xenon Pharmaceuticals Inc. | Piperazine derivatives and their use as therapeutic agents |
| CA2539314A1 (en) * | 2003-09-19 | 2005-03-31 | F. Hoffmann-La Roche Ag | Thiazolopyridine derivatives as adenosine receptor ligands |
| US7714009B2 (en) | 2003-10-31 | 2010-05-11 | Takeda Pharmaceutical Company Limited | Nitrogen-containing fused heterocyclic compounds |
| ES2629414T3 (es) | 2003-12-26 | 2017-08-09 | Kyowa Hakko Kirin Co., Ltd. | Derivados de tiazol |
| ATE537830T1 (de) * | 2004-07-06 | 2012-01-15 | Xenon Pharmaceuticals Inc | Nicotinamid derivate und ihre verwendung als therapeutika |
| AU2005263499B2 (en) * | 2004-07-22 | 2010-11-25 | F. Hoffmann-La Roche Ag | Substituted benzothiazoles |
| MX2007000638A (es) * | 2004-07-22 | 2007-03-07 | Hoffmann La Roche | Derivados de benzotiazol. |
| KR100823799B1 (ko) * | 2004-07-22 | 2008-04-21 | 에프. 호프만-라 로슈 아게 | 벤조티아졸 유도체 |
| EP1799667B1 (en) * | 2004-09-20 | 2013-03-20 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as therapeutic agents |
| EP1830837B1 (en) | 2004-09-20 | 2013-09-04 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives for the treatment of diseases mediated by stearoyl-coa desaturase enzymes |
| CA2580845A1 (en) * | 2004-09-20 | 2006-03-30 | Xenon Pharmaceuticals Inc. | Pyridazine derivatives for inhibiting human stearoyl-coa-desaturase |
| CA2580855A1 (en) * | 2004-09-20 | 2006-03-30 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as stearoyl-coa desaturase inhibitors |
| CA2580860A1 (en) * | 2004-09-20 | 2006-03-30 | Xenon Pharmaceuticals Inc. | Pyridine derivatives for inhibiting human stearoyl-coa-desaturase |
| EP1804799B1 (en) * | 2004-09-20 | 2013-08-21 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as stearoyl-coa desaturase inhibitors |
| CN101083986A (zh) * | 2004-09-20 | 2007-12-05 | 泽农医药公司 | 双环杂环衍生物及其作为硬脂酰CoA去饱和酶(SCD)抑制剂的用途 |
| CA2580856A1 (en) * | 2004-09-20 | 2006-03-30 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as stearoyl-coa desaturase inhibitors |
| CN101084212A (zh) * | 2004-09-20 | 2007-12-05 | 泽农医药公司 | 杂环衍生物及其作为硬脂酰CoA去饱和酶介导剂的用途 |
| JP4633123B2 (ja) * | 2004-11-05 | 2011-02-16 | エフ．ホフマン−ラ ロシュ アーゲー | イソニコチン酸誘導体の製造方法 |
| US20060223849A1 (en) * | 2005-03-14 | 2006-10-05 | Mjalli Adnan M | Benzazole derivatives, compositions, and methods of use as beta-secretase inhibitors |
| MX2007015216A (es) * | 2005-06-03 | 2008-02-22 | Xenon Pharmaceuticals Inc | Derivados de aminotiazol y sus usos como agentes terapeuticos. |
| AU2007320906A1 (en) * | 2006-11-13 | 2008-05-22 | Pfizer Products Inc. | Diaryl, dipyridinyl and aryl-pyridinyl derivatives and uses thereof |
| CA2758961A1 (en) | 2009-04-27 | 2010-11-04 | High Point Pharmaceuticals, Llc | Substituted isoquinoline derivatives, pharmaceutical compositions, and methods of use as .beta.-secretase inhibitors |
| TWI548411B (zh) | 2009-04-28 | 2016-09-11 | Kyowa Hakko Kirin Co Ltd | Exercise disorder treatment |
| UA113383C2 (xx) | 2009-09-02 | 2017-01-25 | Терапевтичний агент для лікування тривожних розладів | |
| UA110097C2 (uk) | 2009-09-02 | 2015-11-25 | Терапевтичний агент для лікування розладів настрою | |
| US8450354B2 (en) * | 2010-03-23 | 2013-05-28 | High Point Pharmaceuticals, Llc | Substituted imidazo[1,2-b]pyridazine derivatives, pharmaceutical compositions, and methods of use as β-secretase inhibitors |
| JP5248585B2 (ja) * | 2010-12-15 | 2013-07-31 | ゼノン・ファーマシューティカルズ・インコーポレイテッド | 治療薬としてのニコチンアミド誘導体およびそれらの使用 |
| DE102011005232A1 (de) | 2011-03-08 | 2012-09-13 | AristoCon GmbH & Co. KG | Adenosin und seine Derivate zur Verwendung in der Schmerztherapie |
| KR102160320B1 (ko) | 2012-10-02 | 2020-09-28 | 에피테라퓨틱스 에이피에스 | 히스톤 탈메틸효소의 저해제 |
| WO2020103930A1 (zh) * | 2018-11-22 | 2020-05-28 | 上海科技大学 | 噻唑并环类化合物、其制备方法、中间体和应用 |
| DE102019110904B4 (de) * | 2019-04-26 | 2022-01-20 | Helmholtz-Zentrum Dresden - Rossendorf E. V. | N-(4-methoxy-7-morpholinobenzo[d]thiazol-2-yl)-acetamid-Derivate und deren Verwendung |
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| DE3374550D1 (en) | 1982-12-21 | 1987-12-23 | Johnsen Jorgensen Plastics Ltd | Dispensing container |
| FI91859C (fi) * | 1987-06-17 | 1994-08-25 | Eisai Co Ltd | Analogiamenetelmä antiallergisena aineena aktiivisen bentsotiatsolijohdannaisen valmistamiseksi |
| IL90337A0 (en) * | 1988-05-24 | 1989-12-15 | Pfizer | Aromatic and heterocyclic carboxamide derivatives as antineoplastic agents |
| CA2413086C (en) | 2000-06-21 | 2011-06-28 | Alexander Alanine | Benzothiazole derivatives |
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