ES2187064T3 - Derivados de azetidinona para el tratamiento de infecciones por hcmv. - Google Patents
Derivados de azetidinona para el tratamiento de infecciones por hcmv.Info
- Publication number
- ES2187064T3 ES2187064T3 ES98947257T ES98947257T ES2187064T3 ES 2187064 T3 ES2187064 T3 ES 2187064T3 ES 98947257 T ES98947257 T ES 98947257T ES 98947257 T ES98947257 T ES 98947257T ES 2187064 T3 ES2187064 T3 ES 2187064T3
- Authority
- ES
- Spain
- Prior art keywords
- lower alkyl
- phenyl
- het
- alkyl
- substituted
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 241000701024 Human betaherpesvirus 5 Species 0.000 title 1
- MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical class O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 title 1
- 208000015181 infectious disease Diseases 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 8
- 125000003545 alkoxy group Chemical group 0.000 abstract 5
- -1 alkyl radicals Chemical class 0.000 abstract 4
- 125000004432 carbon atom Chemical group C* 0.000 abstract 4
- RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical group C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 abstract 3
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical group CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 abstract 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 3
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical group CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 abstract 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 abstract 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical group C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 abstract 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical group C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 abstract 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 abstract 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 abstract 2
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 2
- 150000003254 radicals Chemical class 0.000 abstract 2
- 125000001424 substituent group Chemical group 0.000 abstract 2
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 abstract 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 2
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical group C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 abstract 1
- RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical group NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 abstract 1
- OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical group C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 abstract 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical group C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 abstract 1
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical group CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 abstract 1
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical group CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 abstract 1
- OMAFFHIGWTVZOH-UHFFFAOYSA-N 1-methyltetrazole Chemical group CN1C=NN=N1 OMAFFHIGWTVZOH-UHFFFAOYSA-N 0.000 abstract 1
- PMCOWOCKUQWYRL-UHFFFAOYSA-N 2,4-dimethylpyrimidine Chemical group CC1=CC=NC(C)=N1 PMCOWOCKUQWYRL-UHFFFAOYSA-N 0.000 abstract 1
- VZWOXDYRBDIHMA-UHFFFAOYSA-N 2-methyl-1,3-thiazole Chemical group CC1=NC=CS1 VZWOXDYRBDIHMA-UHFFFAOYSA-N 0.000 abstract 1
- VRESBNUEIKZECD-UHFFFAOYSA-N 2-methyltetrazole Chemical group CN1N=CN=N1 VRESBNUEIKZECD-UHFFFAOYSA-N 0.000 abstract 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical group C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 abstract 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical group C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 abstract 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical group C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 abstract 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 abstract 1
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical group O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 abstract 1
- 125000002619 bicyclic group Chemical group 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000004122 cyclic group Chemical group 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical group C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- DWVCPSQPTSNMRX-UHFFFAOYSA-N n-methyl-1,3-thiazol-2-amine Chemical group CNC1=NC=CS1 DWVCPSQPTSNMRX-UHFFFAOYSA-N 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 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
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Chemical group COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical group [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 abstract 1
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 abstract 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
- 229930192474 thiophene Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/06—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D205/08—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/20—Antivirals for DNA viruses
- A61P31/22—Antivirals for DNA viruses for herpes viruses
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Virology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Molecular Biology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biotechnology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
Un compuesto de fórmula**(Fórmula)** en donde R1 es hidrógeno o alquilo C1-2; R2 y R3, cada uno independientemente, es hidrógeno, metilo o etilo; R4 es hidrógeno o alquilo inferior; R5 es fenilo, opcionalmente sustituido con un sustituyente seleccionado, independientemente, del grupo que consiste en alquilo inferior, alcoxi inferior; fenil(alquilo inferior), opcionalmente mono- o di-sustituido en su porción fenilo con un sustituyente seleccionado, independientemente, del grupo que consiste en alquilo inferior, alcoxi inferior, nitro, halo, ciano, trifluorometilo y C(O)OR7, en donde R7 es alquilo inferior o fenil(alquilo inferior), Het(alquilo inferior), en donde Het es un heterociclo seleccionado del grupo que consiste en pirrolidina, tetrahidrofurano, tiazolidina, pirrol, 1H-imidazol, 1-metil-1H-imidazol, pirazol, furano, tiofeno, oxazol, isoxazol, tiazol, 2-metiltiazol, 2-aminotiazol, 2-(metilamino)-tiazol, piperidina, 1-metilpiperidina, 1-metil-piperazina, 1, 4-dioxano, morfolina, piridina, piridina-N-óxido, pirimidina, 2, 4dihidroxipirimidina, 2, 4-dimetilpirimidina, 2, 6-dimetilpiridina, 1-metil-1H-tetrazol, 2-metil-2H-tetrazol, benzotiazol, benzoxazol y tiazolo[4, 5-b]-piridina, estando dicho Het opcionalmente mono- o di-sustituido con un grupo alquilo inferior o alcoxi inferior; o R4 y R5, junto con el átomo de nitrógeno al que están unidos, forman un pirrolidino, opcionalmente sustituido con benciloxicarbonilo o fenilo, estando dicho anillo de fenilo opcionalmente mono- o di-sustituido con halo, nitro, ciano o trifluorometilo; X se selecciona del grupo que consiste en O, S, NR8, en donde R8 es H o alquilo inferior; e Y es alquilo C1-10 no cíclico o cíclico; fenilcarbonilo; fenilo o bencilo, opcionalmente mono- o di-sustituido con alquilo inferior o alcoxi inferior, estando dicho anillo de fenilo opcionalmente condensado con un anillo aromático para formar un anillo bicíclico, o Het o CH2-Het, en donde Het es como se define para R5; o, cuando X es NR8, en donde R8 es alquilo inferior e Y es alquilo inferior, X e Y están unidos entre sí para formar un anillo de piperidino; en donde la expresión ¿alquilo inferior¿, tal como se utiliza en esta memoria, ya sea sola o en combinación con otro radical, significa radicales alquilo de cadena lineal o ramificada que contienen hasta seis átomos de carbono; la expresión ¿alcoxi inferior¿, tal como se utiliza en esta memoria, significa radicales alcoxi de cadena lineal que contienen de uno a cuatro átomos de carbono y radicales alcoxi de cadena ramificada que contienen tres a cuatro átomos de carbono, y la expresión ¿cicloalquilo inferior¿, tal como se utiliza en esta memoria, sola o en combinación con otro radical, significa radicales hidrocarbonados cíclicos saturados que contienen tres a siete átomos de carbono.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US6154897P | 1997-10-07 | 1997-10-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2187064T3 true ES2187064T3 (es) | 2003-05-16 |
Family
ID=22036473
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES98947257T Expired - Lifetime ES2187064T3 (es) | 1997-10-07 | 1998-10-06 | Derivados de azetidinona para el tratamiento de infecciones por hcmv. |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US6211170B1 (es) |
| EP (1) | EP1023265B1 (es) |
| JP (1) | JP2001519330A (es) |
| AT (1) | ATE231124T1 (es) |
| AU (1) | AU9426198A (es) |
| CA (1) | CA2301967C (es) |
| DE (1) | DE69810800T2 (es) |
| DK (1) | DK1023265T3 (es) |
| ES (1) | ES2187064T3 (es) |
| WO (1) | WO1999018073A1 (es) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| UA91341C2 (ru) | 2004-07-15 | 2010-07-26 | Амр Текнолоджи, Інк. | Арил- и гетероарилзамещенные тетрагидроизохинолины и их применение для блокирования обратного захвата норэпинефрина, допамина и серотонина |
| GB0608899D0 (en) * | 2006-05-05 | 2006-06-14 | Leuven K U Res & Dev | Novel viral replication inhibitors |
| ES2428326T3 (es) * | 2007-10-04 | 2013-11-07 | Merck Sharp & Dohme Corp. | Derivados de aril sulfona sustituida como bloqueadores de canales de calcio |
| US9156812B2 (en) | 2008-06-04 | 2015-10-13 | Bristol-Myers Squibb Company | Crystalline form of 6-[(4S)-2-methyl-4-(2-naphthyl)-1,2,3,4-tetrahydroisoquinolin-7-yl]pyridazin-3-amine |
| US8815894B2 (en) * | 2009-05-12 | 2014-08-26 | Bristol-Myers Squibb Company | Crystalline forms of (S)-7-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydroisoquinoline and use thereof |
| EP2429295B1 (en) * | 2009-05-12 | 2013-12-25 | Albany Molecular Research, Inc. | Aryl, heteroaryl, and heterocycle substituted tetrahydroisoquinolines and use thereof |
| AU2010247763B2 (en) * | 2009-05-12 | 2015-12-24 | Albany Molecular Research, Inc. | 7-([1,2,4,]triazolo[1,5,-a]pyridin-6-yl)-4-(3,4-dichlorophenyl)-1,2,3,4- tetrahydroisoquinoline and use thereof |
| US9216180B2 (en) | 2012-10-02 | 2015-12-22 | New York University | Pharmaceutical compositions and treatment of genetic diseases associated with nonsense mediated RNA decay |
| AU2019339777B2 (en) | 2018-09-12 | 2022-09-01 | Novartis Ag | Antiviral pyridopyrazinedione compounds |
| AU2020353055B2 (en) | 2019-09-26 | 2024-03-07 | Gilead Sciences, Inc. | Antiviral pyrazolopyridinone compounds |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5229381A (en) | 1983-12-01 | 1993-07-20 | Merck & Co., Inc. | Substituted azetidinones as anti-inflammatory and antidegenerative agents |
| US4680391A (en) | 1983-12-01 | 1987-07-14 | Merck & Co., Inc. | Substituted azetidinones as anti-inflammatory and antidegenerative agents |
| IL89835A0 (en) * | 1988-04-11 | 1989-12-15 | Merck & Co Inc | Substituted azetidinones,their preparation and pharmaceutical compositions containing them |
| EP0377549B1 (en) | 1989-01-03 | 1998-12-09 | Marcos Y. Kleinerman | Remote measurement of physical variables with fiber optic systems |
| US5100880A (en) * | 1991-03-20 | 1992-03-31 | Merck & Co., Inc. | Novel betalactam elastase inhibitors containing phosphorous acid derivatives at the 4-position of the 2-azetidinone |
| US5104862A (en) * | 1991-03-20 | 1992-04-14 | Merck & Co., Inc. | Bethalactam elastase inhibitors containing phosphorous acid derivatives at the 4-position of the 2-azetidinone |
| GB2266527A (en) * | 1992-03-17 | 1993-11-03 | Merck & Co Inc | Substituted azetidinones useful in the treatment of leukemia |
| GB9314350D0 (en) | 1993-07-12 | 1993-08-25 | Zeneca Ltd | Armide derivatives |
| US5900401A (en) * | 1994-03-23 | 1999-05-04 | Tokyo Tanabe Company Limited | Remedy for respiratory-tract viral disease |
-
1998
- 1998-10-06 WO PCT/CA1998/000954 patent/WO1999018073A1/en not_active Ceased
- 1998-10-06 DE DE69810800T patent/DE69810800T2/de not_active Expired - Lifetime
- 1998-10-06 ES ES98947257T patent/ES2187064T3/es not_active Expired - Lifetime
- 1998-10-06 DK DK98947257T patent/DK1023265T3/da active
- 1998-10-06 EP EP98947257A patent/EP1023265B1/en not_active Expired - Lifetime
- 1998-10-06 AU AU94261/98A patent/AU9426198A/en not_active Abandoned
- 1998-10-06 US US09/167,141 patent/US6211170B1/en not_active Expired - Lifetime
- 1998-10-06 JP JP2000514885A patent/JP2001519330A/ja not_active Ceased
- 1998-10-06 AT AT98947257T patent/ATE231124T1/de active
- 1998-10-06 CA CA002301967A patent/CA2301967C/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JP2001519330A (ja) | 2001-10-23 |
| DE69810800D1 (de) | 2003-02-20 |
| WO1999018073A1 (en) | 1999-04-15 |
| ATE231124T1 (de) | 2003-02-15 |
| US6211170B1 (en) | 2001-04-03 |
| EP1023265A1 (en) | 2000-08-02 |
| DK1023265T3 (da) | 2003-02-24 |
| AU9426198A (en) | 1999-04-27 |
| EP1023265B1 (en) | 2003-01-15 |
| DE69810800T2 (de) | 2003-09-18 |
| CA2301967A1 (en) | 1999-04-15 |
| CA2301967C (en) | 2005-05-17 |
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