CO4900040A1 - Nuevos derivados de acidos alfa-hidroxi su preparacion y aplicacion - Google Patents
Nuevos derivados de acidos alfa-hidroxi su preparacion y aplicacionInfo
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- CO4900040A1 CO4900040A1 CO97018892A CO97018892A CO4900040A1 CO 4900040 A1 CO4900040 A1 CO 4900040A1 CO 97018892 A CO97018892 A CO 97018892A CO 97018892 A CO97018892 A CO 97018892A CO 4900040 A1 CO4900040 A1 CO 4900040A1
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- Prior art keywords
- alkyl
- alkoxy
- alkylthio
- phenyl
- halogen
- Prior art date
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- C07D251/20—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom with no nitrogen atoms directly attached to a ring carbon atom
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- C07D251/22—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to two ring carbon atoms
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Abstract
Derivados de ácidos alfa-hidroxicarboxílicos de la fórmula Ien el cual R es un grupoen el cual R1 tiene el siguiente significado: a) Hidrógeno b) un grupo succinilimido c) un heteroaromato de 5 miembros ligado mediante un átomo de nitrógeno, como pirrolilo, pirazolilo, imirazolilo y triazolilo, el cual puede tener uno hasta dos átomos halógenos o uno hasta dos grupos C1 -C4 -alquilo o uno hasta dos grupos C1 -C4 -alcoxi; d) un grupo donde k asume los valores 0, 1 y 2, p los valores 1, 2, 3 y 4 y R9 representaC1 -C4 -alquilo, C3 -C7 -cicloalquilo, C3 -C6 - alquenilo, C3 -C6 -alquinilo o fenilo eventualmente sustituido, el cual puede estar sustituido por uno o varios de los siguientes radicales: halógeno, nitro, ciano, C1 -C4 -alquilo, C1 -C4 -halogenoalquilo, hidroxi, C1 -C4 -alcoxi, - 2 -C1 -C4 -alquiltio, mercapto, amino, C1 -C4 -alquilamino, C1 -C4 -dialquilamino; e) R1 además un radical OR10 , en el cual R10 significa: hidrógeno, el catión de un metal alcalino como litio, sodio, potasio o el catión de un metal alcalino térreo como calcio, magnesio y bario así como un ión alquilamónico fisiológicamente compatible o el ión amónico; C3 -C8 -cicloalquilo, C1 -C8 -alquilo, CH2 -fenilo que puede estar sustituido por uno o varios de los siguientes radicales: halógeno, nitro, ciano, C1 -C4 -alquilo, C1 -C4 -halogenalquilo, hidroxi, C1 -C4 -alcoxi, mercapto, C1 -C4 -alquiltio, amino, C1 -C4 -alquilamino, C1 -C4 -dialquilamino, Un grupo C3 -C6 -alquenilo o C3 -C6 -alquinilo, pudiendo este grupo tener a su vez uno hasta cinco átomos de halógeno; R10 puede ser además un radical fenilo, el cual puede tener uno hasta cinco átomos de halógeno y/o uno hasta tres de los siguientes radicales: nitro, ciano, C1 -C4 -alquilo, C1 -C4 -halogenalquilo, hidroxi, C1 -C4 -alcoxi, mercapto, C1 -C4 -alquiltio, amino, C1 -C4 -alquilamino, C1 -C4 -dialquilamino; Un heteroaromato de 5 miembros ligado mediante un átomo de nitrógeno que contiene uno a tres átomos de nitrógeno, el cual puede tener uno hasta dos átomos halógenos y/o uno hasta dos de los siguientes radicales: C1 -C4 -alquilo, C1 -C4 -halogenalquilo, C1 -C4 -alcoxi, fenilo, C1 -C4 -halogenalcoxi y/o C1 -C4 -alquiltio. f) R1 además un radicalen el cual R11 significa: C1 -C4 -alquilo, C3 -C6 -alquenilo, C3 -C6 -alquinilo, C3 -C8 -cicloalquilo, pudiendo estos radicales tener un radical C1 -C4 -alcoxi, C1 -C4 -alquiltio y/o fenilo, como se mencionó antes: fenilo, eventualmente sustituido; g) R1 un radical en el cual R12 tiene el mismo significado como R11 ; h) además R1 puede significar pudiendo R13 y R14 ser iguales o diferentes y tener el siguiente significado: hidrógeno, C1 AND#8209;C7 AND#8209;alquilo, C3 AND#8209;C7 AND#8209;cicloalquilo, C3 AND#8209;C7 AND#8209;alquenilo, C3 AND#8209;C7 AND#8209;alquinilo, bencilo, fenilo, eventualmente sustituido,o R13 y R14 forman juntos una cadena C4 AND#8209;C7 AND#8209;alquileno, cerrada en forma de anillo, opcionalmente sustituida, por ejemplo, por C1 AND#8209;C4 AND#8209;alquilo, la cual puede tener un heteroátomo o R un tetrazol o un nitrilo W Nitrógeno, CAND#8209;NO2 , un grupo CH, cuando uno o varios de los sustituyentes R2 , R3 , R15 y/o R16 significan un grupo nitro o cuando X y/o Y significan nitrógeno; R2 Hidrógeno, halógeno, C1 AND#8209;C4 AND#8209;alquilo, C1 AND#8209;C4 AND#8209;halogenalquilo, C1 AND#8209;C4 AND#8209;alcoxi, C1 AND#8209;C4 AND#8209;halogenoalcoxi, hidroxi, mercapto, C1 AND#8209;C4 AND#8209;alquiltio, nitro, amino, C1 AND#8209;C4 AND#8209;alquilamino o C1 AND#8209;C4 AND#8209;dialquilamino, ciano, fenilo, opcionalmente sustituido una hasta tres veces con halógeno, hidroxi, amino, mono o dialquil (C1 AND#8209;C3 )AND#8209;amino, C1 AND#8209;C3 AND#8209;alquilo, C1 AND#8209;C3 AND#8209;alcoxi, mercapto o C1 AND#8209;C3 AND#8209; alquiltio, carboxilo, C1 AND#8209;C3 AND#8209;alquilcarboxilo; un heteroaromato de cinco o seis miembros que contiene uno hasta tres átomos de nitrógeno y/o un átomo de azufre o de oxígeno. Además R2 puede formar con los átomos de carbono vecinos y X un anillo alquileno o alquilideno de 5 a 6 miembros en el cual respectivamente uno o dos átomos de carbono pueden estar reemplazado por un heteroátomo como nitrógeno, azufre u oxígeno y que puede estar uno hasta tres veces sustituido por los siguientes radicales: halógeno, nitro, ciano, hidroxi, mercapto, C1 AND#8209;C3 AND#8209; alquilo, C1 AND#8209;C3 AND#8209;halogenalquilo, C1 AND#8209;C3 AND#8209;alcoxi, C1 AND#8209;C3 AND#8209;alquiltio, amino, C1 AND#8209;C3 AND#8209;alquilamino, C1 AND#8209;C3 AND#8209;dialquilamino; X Significa nitrógeno o CR15 , donde R15 puede ser hidrógeno o C1 AND#8209;C5 AND#8209;alquilo, opcionalmente sustituido uno hasta dos veces con hidroxi o carboxi; C1 AND#8209;C6 AND#8209; alcoxi, C1 AND#8209;C6 AND#8209;alquiltio, fenilo, bencilo, hidroxi, mercapto, nitro, amino, C1 AND#8209;C4 AND#8209;alquilamino, C1 AND#8209;C4 AND#8209;dialquilamino, ciano o carboxi; además CR15 puede estar unido con R2 en un anillo de 5 o 6 miembros, o CR15 puede con R3 y su átomo de carbono vecino formar un anillo alquileno o alquilideno de 5 o 6 miembros, en el cual respectivamente uno o dos átomos de carbono pueden estar remplazados por nitrógeno, oxígeno o azufre, el anillo de 5 o 6 miembros puede opcionalmente estar sustituido una hasta tres veces con los siguientes radicales: Halógeno, nitro, ciano, hidroxi, mercapto, C1 AND#8209;C3 AND#8209;alquilo, C1 AND#8209;C3 AND#8209;halogenalquilo, C1 AND#8209;C3 AND#8209;alcoxi, C1 AND#8209;C3 AND#8209;alquiltio, amino, C1 AND#8209;C3 AND#8209;alquilamino, C1 AND#8209;C3 AND#8209;dialquilamino o carboxi; el nitrógeno en el anillo 5 también puede estar sustituido por un grupo formilo o acetilo; R3 puede tener el mismo significado como R2 , R2 y R3 pueden ser iguales o diferentes; además R puede formar con el átomo de carbono vecino y con X un anillo de 5 o 6 miembros; además R3 puede formar con el átomo de carbono vecino y Y un anillo alquileno o alquilideno de 5 o 6 miembros en el cual respectivamente uno o dos átomos de carbono pueden estar reemplazados por nitrógeno, oxígeno o azufre; el anillo de 5 o 6 miembros puede opcionalmente estar sustituido una hasta tres veces con los siguientes radicales: Halógeno, nitro, ciano, hidroxi, mercapto, C1 AND#8209;C3 AND#8209;alquilo, C1 AND#8209;C3 AND#8209;halogenalquilo, C1 AND#8209;C3 AND#8209;alcoxi, C1 AND#8209;C3 AND#8209;alquiltio, amino, C1 AND#8209;C3 AND#8209;alquilamino, C1 AND#8209;C3 AND#8209;dialquilamino o carboxi; el nitrógeno en el anillo 5 puede estar sustituido también por un grupo o acetilo; Y Nitrógeno o CR16 , donde R16 significa hidrógeno, C1 AND#8209;C5 AND#8209;alquilo, C1 AND#8209;C5 AND#8209;alcoxi, C1 AND#8209;C5 AND#8209;alquiltio, nitro, fenilo, hidroxi, halógeno, ciano, amino, C1 AND#8209;C4 AND#8209;alquilamino, C1 AND#8209;C4 AND#8209;dialquilamino, mercapto o carboxi o CR16 junto con R3 y su átomo vecino de carbono forman un anillo de 5 o 6 miembros; R4 es fenilo, naftilo, dihidro o tetrahidronaftilo, el cual puede estar sustituido por uno o varios de los siguientes radicales: Halógeno, nitro, ciano, hidroxi, C1 AND#8209;C4 AND#8209;alcoxi, C1 AND#8209;C4 AND#8209;halogenalcoxi, fenoxi, fenilo, C1 AND#8209;C4 AND#8209; alquiltio, amino, C1 AND#8209;C4 AND#8209;alquilamino o C1 AND#8209;C4 AND#8209; dialquilamino, pudiendo formar dos radicales en átomos de carbono vecinos junto con estos un anillo de 5 o 6 miembros unido a través de un grupo alquileno o alquilideno, en el cual uno o varios grupos metileno o metilideno pueden estar reemplazados por oxígeno; R5 puede tener el mismo significado que R4 pudiendo R4 y R5 ser iguales o diferentes; R6 Significa hidrógeno, C1 AND#8209;C8 AND#8209;alquilo, C2 AND#8209;C8 AND#8209; alquenilo o C3 AND#8209;C8 AND#8209;alquinilo, pudiendo estos radicales respectivamente estar sustituidos una o varias veces por: halógeno, nitro, ciano, C1 AND#8209;C4 AND#8209; alcoxi, hidroxi, C1 AND#8209;C4 AND#8209;alquiltio, mercapto, C1 AND#8209;C4 AND#8209; halogenalcoxi, carboxi, C1 AND#8209;C4 AND#8209;alquilcarboxi, C1 AND#8209;C4 AND#8209;alquilcarbonilo, amino, C1 AND#8209;C4 AND#8209;alquilamino, C1 AND#8209;C4 AND#8209;dialquilamino, fenilo o naftilo el cual a su vez puede estar sustituido uno o varias veces por: halógeno, nitro, ciano, hidroxi, C1 AND#8209;C4 AND#8209;alcoxi, C1 AND#8209;C4 AND#8209;alquilo, C1 AND#8209;C4 AND#8209;halogenalquilo, C1 AND#8209;C4 AND#8209; halogenalcoxi, mercapto, C1 AND#8209;C4 AND#8209;alquiltio, amino, C1 AND#8209;C4 AND#8209;alquilamino, C1 AND#8209;C4 AND#8209;dialquilamino o fenoxi. Además R6 significa C1 AND#8209;C4 AND#8209;alquilo, que está sustituido por fenilmetoxi o fenoxi en el cual el grupo fenilo puede estar sustituido una o dos veces por halógeno, metilo o metoxi; Además R6 significa también una cadena C1 AND#8209;C8 AND#8209; alquilo, C3 AND#8209;C8 AND#8209;alquenilo o C3 AND#8209;C8 AND#8209;alquinilo que está sustituida por uno de los siguientes radicales:Heteroarilo o heteroariloxi, de 5 o 6 miembros, que contiene uno hasta tres átomos de nitrógeno y/o un átomode azufre o de oxígeno, el cual puede tener unohasta cuatro átomos halógenos y/o uno hasta dos de losiguientes radicales:C1 AND#8209;C4 AND#8209;alquilo, C1 AND#8209;C4 AND#8209;halogenalquilo, C1 AND#8209;C4 AND#8209;alcoxi, C1 AND#8209;C4 AND#8209;halogenalcoxi, C1 AND#8209;C4 AND#8209;alquiltio, fenilo, fenoxi o fenilcarbonilo, pudiendo los radicales de fenilo a su vez contener uno hasta cinco átomos halógenos y/o uno hasta tres de los siguientes radicales: C1 AND#8209;C4 AND#8209;alquilo, C1 AND#8209;C4 AND#8209;halogenalquilo, C1 AND#8209;C4 AND#8209;alcoxi, C1 AND#8209;C4 AND#8209;halogenalcoxi y/o C1 AND#8209;C4 AND#8209; alquiltio; Fenilo, naftilo que a su vez puede estar sustituido una o varias veces por: halógeno, nitro, ciano, hidroxi, C1 AND#8209;C4 AND#8209;alcoxi, C1 AND#8209;C4 AND#8209;alquilo, C1 AND#8209;C4 AND#8209;halogenalquilo, C1 AND#8209;C4 AN
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EP0946524A1 (de) * | 1996-12-18 | 1999-10-06 | Basf Aktiengesellschaft | Heterozyklische carbonsäurederivate, ihre herstellung und verwendung als endothelinrezeptorantagonisten |
US6030975A (en) * | 1997-03-14 | 2000-02-29 | Basf Aktiengesellschaft | Carboxylic acid derivatives, their preparation and use in treating cancer |
DE19726146A1 (de) * | 1997-06-19 | 1998-12-24 | Basf Ag | Neue ß-Amino und ß-Azidopcarbonsäurederivate, ihre Herstellung und Verwendung als Endothelinrezeptorantagonisten |
JP2002507996A (ja) * | 1997-07-03 | 2002-03-12 | デュポン ファーマシューティカルズ カンパニー | 神経学的障害を治療するためのイミダゾピリミジン類およびイミダゾピリジン類 |
DE19743681A1 (de) * | 1997-10-02 | 1999-04-08 | Knoll Ag | Methode zur Verhinderung der Transplantatabstoßung |
JP5187991B2 (ja) | 1997-10-17 | 2013-04-24 | アーク・セラピューティックス・リミテッド | レニン−アンジオテンシン系の阻害剤の使用 |
DE19806438A1 (de) * | 1998-02-17 | 1999-08-19 | Basf Ag | Neue Carbonsäurederivate mit 5-substituiertem Pyrimidinring, ihre Herstellung und Verwendung |
US6124463A (en) * | 1998-07-02 | 2000-09-26 | Dupont Pharmaceuticals | Benzimidazoles as corticotropin release factor antagonists |
US6365589B1 (en) | 1998-07-02 | 2002-04-02 | Bristol-Myers Squibb Pharma Company | Imidazo-pyridines, -pyridazines, and -triazines as corticotropin releasing factor antagonists |
US7566452B1 (en) | 1999-05-04 | 2009-07-28 | New York University | Cancer treatment with endothelin receptor antagonists |
DE10064797A1 (de) * | 2000-12-22 | 2002-06-27 | Knoll Ag | Orale und parenterale pharmazeutische Formulierung, umfassend eine niedermolekulare Thrombininhibitor-Pro-Pharmakon |
EP1243262B1 (en) | 2001-03-20 | 2006-05-31 | Schwarz Pharma Ag | Novel use of a peptide class of compound for treating non-neuropathic inflammatory pain |
EP1243263B1 (en) | 2001-03-21 | 2002-11-27 | Schwarz Pharma Ag | Novel use of a peptide class of compound for treating allodynia or other different types of chronic or phantom pain |
MXPA06011937A (es) | 2004-04-16 | 2007-01-26 | Sanol Arznei Schwarz Gmbh | Uso de compuestos peptidicos para la profilaxis y el tratamiento de dolor de cabeza cronico. |
EP1604656A1 (en) | 2004-06-09 | 2005-12-14 | Schwarz Pharma Ag | Novel use of peptide compounds for treating amyotrophic lateral sclerosis (ALS) |
BRPI0514721A (pt) | 2004-08-27 | 2008-06-24 | Sanol Arznei Schwarz Gmbh | uso de compostos de peptìdeos para tratar dor de cáncer ósseo, dor induzida por quimioterapia e nucleosìdeo |
KR20080111137A (ko) * | 2006-04-13 | 2008-12-22 | 액테리온 파마슈티칼 리미티드 | 초기 단계 특발성 폐 섬유증을 위한 엔도텔린 수용체 대항제 |
SI2462990T1 (sl) | 2006-06-15 | 2014-04-30 | Ucb Pharma Gmbh | Farmacevtski sestavek, ki obsega lakozamid in levetiracetam, s sinergističnim antikonvulzivnim učinkom |
WO2011022694A2 (en) * | 2009-08-20 | 2011-02-24 | University Of Tennessee Research Foundation, The | Furanopyrimidine cannabinoid compounds and related methods of use |
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DE4313412A1 (de) | 1993-04-23 | 1994-10-27 | Basf Ag | 3-(Het)aryl-Carbonsäurederivate, Verfahren und Zwischenprodukte zu ihrer Herstellung |
DE4411225A1 (de) | 1994-03-31 | 1995-10-05 | Basf Ag | Verwendung von Carbonsäurederivaten als Arzneimittel |
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1996
- 1996-04-12 DE DE19614533A patent/DE19614533A1/de not_active Withdrawn
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1997
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- 1997-04-04 KR KR1019980708091A patent/KR20000005369A/ko not_active Application Discontinuation
- 1997-04-04 HU HU9901312A patent/HUP9901312A3/hu unknown
- 1997-04-04 US US09/155,944 patent/US6686369B1/en not_active Expired - Fee Related
- 1997-04-04 EP EP97918110A patent/EP0892787B1/de not_active Expired - Lifetime
- 1997-04-04 IL IL12635097A patent/IL126350A0/xx unknown
- 1997-04-04 WO PCT/EP1997/001688 patent/WO1997038981A1/de not_active Application Discontinuation
- 1997-04-04 UA UA98116020A patent/UA49884C2/uk unknown
- 1997-04-04 AU AU26365/97A patent/AU731579B2/en not_active Ceased
- 1997-04-04 BR BR9708608A patent/BR9708608A/pt not_active IP Right Cessation
- 1997-04-04 PL PL97329241A patent/PL329241A1/xx unknown
- 1997-04-04 CA CA002250757A patent/CA2250757A1/en not_active Abandoned
- 1997-04-04 JP JP9536699A patent/JP2000508326A/ja active Pending
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- 1997-04-11 HR HR19614533.3A patent/HRP970198A2/xx not_active Application Discontinuation
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1998
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Publication number | Publication date |
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AU2636597A (en) | 1997-11-07 |
BG102868A (bg) | 1999-11-30 |
EP0892787A1 (de) | 1999-01-27 |
NO984717L (no) | 1998-10-09 |
ID16501A (id) | 1997-10-02 |
DE19614533A1 (de) | 1997-10-16 |
AR007767A1 (es) | 1999-11-24 |
DE59710272D1 (de) | 2003-07-17 |
CA2250757A1 (en) | 1997-10-23 |
IL126350A0 (en) | 1999-05-09 |
BR9708608A (pt) | 1999-08-03 |
TR199802039T2 (xx) | 1999-01-18 |
HRP970198A2 (en) | 1998-04-30 |
NO984717D0 (no) | 1998-10-09 |
NO311801B1 (no) | 2002-01-28 |
AU731579B2 (en) | 2001-04-05 |
US6686369B1 (en) | 2004-02-03 |
SK134498A3 (en) | 1999-03-12 |
HUP9901312A3 (en) | 2000-06-28 |
NZ332096A (en) | 2000-01-28 |
ATE242770T1 (de) | 2003-06-15 |
PL329241A1 (en) | 1999-03-15 |
UA49884C2 (uk) | 2002-10-15 |
TW425383B (en) | 2001-03-11 |
ZA973097B (en) | 1998-10-12 |
JP2000508326A (ja) | 2000-07-04 |
KR20000005369A (ko) | 2000-01-25 |
EP0892787B1 (de) | 2003-06-11 |
HUP9901312A2 (hu) | 1999-08-30 |
WO1997038981A1 (de) | 1997-10-23 |
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