ES2329553T3 - Pirroloquinolinas y piridoquinolinas sustituidas como agonistas y antagonistas de serotonina. - Google Patents
Pirroloquinolinas y piridoquinolinas sustituidas como agonistas y antagonistas de serotonina. Download PDFInfo
- Publication number
- ES2329553T3 ES2329553T3 ES01994318T ES01994318T ES2329553T3 ES 2329553 T3 ES2329553 T3 ES 2329553T3 ES 01994318 T ES01994318 T ES 01994318T ES 01994318 T ES01994318 T ES 01994318T ES 2329553 T3 ES2329553 T3 ES 2329553T3
- Authority
- ES
- Spain
- Prior art keywords
- alkyl
- substituted
- case
- independently selected
- alkenyl
- 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
- 239000000556 agonist Substances 0.000 title 1
- 239000005557 antagonist Substances 0.000 title 1
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 title 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 18
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 abstract 5
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 abstract 4
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 abstract 4
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 abstract 4
- 125000005843 halogen group Chemical group 0.000 abstract 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 4
- -1 -OH Chemical group 0.000 abstract 3
- 125000005842 heteroatom Chemical group 0.000 abstract 3
- 125000000623 heterocyclic group Chemical group 0.000 abstract 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000002618 bicyclic heterocycle group Chemical group 0.000 abstract 2
- 125000002837 carbocyclic group Chemical group 0.000 abstract 2
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 abstract 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 1
- 125000006592 (C2-C3) alkenyl group Chemical group 0.000 abstract 1
- 125000006593 (C2-C3) alkynyl group Chemical group 0.000 abstract 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 125000000304 alkynyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000002619 bicyclic group Chemical group 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 125000000000 cycloalkoxy group Chemical group 0.000 abstract 1
- 125000004981 cycloalkylmethyl group Chemical group 0.000 abstract 1
- 125000001188 haloalkyl group Chemical group 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 150000003839 salts Chemical group 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
- C07D471/16—Peri-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D498/16—Peri-condensed systems
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Diabetes (AREA)
- Child & Adolescent Psychology (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Anesthesiology (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Nutrition Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Un compuesto de la fórmula (I): **(Ver fórmula)** o un estereoisómero o una forma de sal farmacéuticamente aceptable del mismo, en el que: b es un enlace sencillo, donde los hidrógenos puente son cis o trans; X es -CH2-, R1 se selecciona entre H, alquilo C1-5, alquenilo C2-5, alquinilo C2-5, cicloalquilo C3-6, -(alquil C1-3) cicloalquilo C3-6, -(alquenil C2-3)cicloalquilo C3-6 y -(alquinil C2-3)cicloalquilo C3-6, R6a es H o alquilo C1-4; R6b es H; como alternativa, R6a y R6b se toman juntos para formar =O o =S; R7 y R9, en cada caso, se seleccionan independientemente entre H, halo, -CF3, -OCF3, -OH, -CN, -NO2, alquilo C1-4, alquenilo C2-4, alquinilo C2-4, haloalquilo C1-4, alcoxi C1-4 y (haloalquil C1-4)oxi; R8 se selecciona entre H; fenilo sustituido con O-S R33; y -NR12R13; R12, en cada caso, se selecciona independientemente entre alquilo C1-4 sustituido con 0-1 R12a, alquenilo C2-4 sustituido con 0-1 R12a, alquinilo C2-4 sustituido con 0-1 R12a, cicloalquilo C3-6 sustituido con 0-3 R33, arilo sustituido con 0-5 R33; resto carbocíclico C3-10 sustituido con 0-3 R33 y sistema de anillos heterocíclicos de 5-10 miembros que contiene 1-4 heteroátomos seleccionados entre el grupo constituido por N, O y S sustituido con 0-3 R31; R12a, en cada caso, se selecciona independientemente entre fenilo sustituido con 0-5 R33; resto carbocíclico C3-10 sustituido con 0-3 R33 y sistema de anillos heterocíclicos de 5-10 miembros que contiene de 1-4 heteroátomos seleccionados entre el grupo constituido por N, O y S sustituido con 0-3 R31; R13, en cada caso, se selecciona independientemente entre H, alquilo C1-4, alquenilo C2-4 y alquinilo C2-4; como alternativa, R12 y R13, cuando se unen a N, pueden combinarse para formar un anillo heterocíclico bicíclico de 9 ó 10 miembros que contiene 1-3 heteroátomos seleccionados entre el grupo constituido por N, O y S, donde dicho sistema de anillos heterocíclicos bicíclico está insaturado o parcialmente saturado, donde dicho sistema de anillos heterocíclicos bicíclico está sustituido con 0-3 R16; R16, en cada caso, se selecciona independientemente entre H, OH, halo, CN, NO2, CF3, SO2R45, NR46R47, -C(=O) H, alquilo C1-4, alquenilo C2-4, alquinilo C2-4, haloalquilo C1-4, (haloalquil C1-3)-oxi-, (alquiloxi C1-3)-, y =O; R31, en cada caso, se selecciona independientemente entre H, OH, halo, CF3, SO2R45, NR46R47, alquilo C1-4 y =O; R33, en cada caso, se selecciona independientemente entre H, OH, halo, CN, NO2, CF3, SO2R 45, NR46R47, -C(=O)H, =O, fenilo, alquilo C1-6, alquenilo C2-6, alquinilo C2-6, cicloalquilo C3-6, haloalquilo C1-4, (haloalquil C1-4)-oxi-, (alquiloxi C1-4)-, (alquiltio C1-4)-, (alquil C1-4)-C(=O)-, (alquil C1-4)-C(=O)NH-, (alquil C1-4)-OC(=O)-, (alquil C1-4)-C(=O)O-, (cicloalquil C3-6)-oxi-, (cicloalquilmetil C3-6)-oxi-; alquilo C1-6 sustituido con OH, metoxi, etoxi, propoxi, butoxi, -SO2R45, -NR46R47, NR46R47C(=O)- o (alquil C1-4)CO2-; y alquenilo C2-6 sustituido con OH, metoxi, etoxi, propoxi, butoxi, -SO2R45, -NR46R47, NR46R47C(=O)-, o (alquil C1-4)CO2-; R45 es alquilo C1-4; R46, en cada caso, se selecciona independientemente entre H y alquilo C1-4; R47, en cada caso, se selecciona independientemente entre H, alquilo C1-4, -C(=O)NH(alquilo C1-4), -SO2(alquilo C1-4), -C(=O)O(alquilo C1-4), -C(=O)( alquilo C1-4) y -C(=O)H; n es 1 ó 2; m es 1 ó 2; y n más m es 2, 3 ó 4.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US25674500P | 2000-12-20 | 2000-12-20 | |
| US256745P | 2000-12-20 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| ES2329553T3 true ES2329553T3 (es) | 2009-11-27 |
| ES2329553T4 ES2329553T4 (es) | 2010-12-07 |
Family
ID=22973430
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES01994318T Expired - Lifetime ES2329553T4 (es) | 2000-12-20 | 2001-12-19 | Pirroloquinolinas y piridoquinolinas sustituidas como agonistas y antagonistas de serotonina. |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US6777406B2 (es) |
| EP (1) | EP1399445B9 (es) |
| JP (1) | JP4386639B2 (es) |
| KR (1) | KR20030070590A (es) |
| AT (1) | ATE438646T1 (es) |
| AU (1) | AU2002246726B2 (es) |
| BG (1) | BG107863A (es) |
| BR (1) | BR0116348A (es) |
| CA (1) | CA2432181C (es) |
| CZ (1) | CZ20031707A3 (es) |
| DE (1) | DE60139511D1 (es) |
| EE (1) | EE200300303A (es) |
| ES (1) | ES2329553T4 (es) |
| HU (1) | HUP0303530A3 (es) |
| IL (1) | IL156261A0 (es) |
| IS (1) | IS6851A (es) |
| MX (1) | MXPA03005355A (es) |
| NO (1) | NO20032798L (es) |
| PL (1) | PL366627A1 (es) |
| RU (1) | RU2003121306A (es) |
| SK (1) | SK7032003A3 (es) |
| WO (1) | WO2002059124A2 (es) |
| ZA (1) | ZA200304304B (es) |
Families Citing this family (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR031202A1 (es) | 2000-11-03 | 2003-09-10 | Wyeth Corp | Ciclopenta(b) (1,4)diazepino(6,7,1-hi) indoles y derivados |
| AR031200A1 (es) | 2000-11-03 | 2003-09-10 | Wyeth Corp | Cicloocta [b] [1,4] diazepino [6,7,1-hi] indoles y derivados |
| AR031199A1 (es) | 2000-11-03 | 2003-09-10 | Wyeth Corp | Ciclohepta/b//1,4/diacepino/6,7,1-hi/indoles y derivados |
| TW200307682A (en) | 2002-04-25 | 2003-12-16 | Wyeth Corp | 1,2,3,4,7,8-Hexahydro-6H-[1,4]diazepino[6,7,1-ij]quinoline derivatives as antipsychotic and antiobesity agents |
| TWI312781B (en) | 2002-04-25 | 2009-08-01 | [1,4]diazepino[6,7,1-ij]quinoline derivatives as antipsychotic and antiobesity agents | |
| TW200307540A (en) | 2002-04-25 | 2003-12-16 | Wyeth Corp | [1, 4]Diazocino[7, 8, 1-hi] indole derivatives as antipsychotic and antiobesity agents |
| CL2004000826A1 (es) | 2003-04-25 | 2005-03-04 | Pfizer | Uso de un agonista para el receptor 5-ht2c para preparar un medicamento util en el tratamiento de la incontinencia urinaria provocada por estres, con la condicion de que el agonista no sea 1-[6-cloro-5-(trifluorometil)-2-piridinil]piperazina (org-129 |
| EP2400300A1 (en) | 2004-08-25 | 2011-12-28 | Takeda Pharmaceutical Company Limited | Method of screening preventives/remedies for stress urinary incontinence |
| US7235688B1 (en) | 2004-11-04 | 2007-06-26 | University Of Notre Dame Du Lac | Process for preparing histone deacetylase inhibitors and intermediates thereof |
| US20070021612A1 (en) * | 2004-11-04 | 2007-01-25 | University Of Notre Dame Du Lac | Processes and compounds for preparing histone deacetylase inhibitors and intermediates thereof |
| GT200500317A (es) | 2004-11-05 | 2006-10-27 | Proceso para preparar compuestos de quinolina y productos obtenidos de los mismos | |
| AR054849A1 (es) * | 2005-07-26 | 2007-07-18 | Wyeth Corp | Diazepinoquinolinas, sintesis de las mismas, e intermediarios para obtenerlas |
| TW200734334A (en) * | 2006-01-13 | 2007-09-16 | Wyeth Corp | Treatment of substance abuse |
| CN101410112A (zh) * | 2006-03-24 | 2009-04-15 | 惠氏公司 | 治疗抑郁症的新治疗组合 |
| PE20081192A1 (es) * | 2006-03-24 | 2008-10-07 | Wyeth Corp | Tratamiento del dolor |
| EP2727585A1 (en) | 2006-05-16 | 2014-05-07 | Takeda Pharmaceutical Company Limited | In-vivo screening method |
| CL2008002777A1 (es) * | 2007-09-21 | 2010-01-22 | Wyeth Corp | Metodo de preparacion de compuestos diazepinoquinolinicos quirales por recristalizacion en un sistema de solvente ternario. |
| WO2009063992A1 (ja) | 2007-11-15 | 2009-05-22 | Takeda Pharmaceutical Company Limited | 縮合ピリジン誘導体およびその用途 |
| AU2010303270A1 (en) | 2009-10-09 | 2012-05-03 | Zafgen Corporation | Sulphone compounds for use in the treatment of obesity |
| WO2011071136A1 (ja) | 2009-12-11 | 2011-06-16 | アステラス製薬株式会社 | 線維筋痛症治療剤 |
| US9266896B2 (en) | 2010-07-22 | 2016-02-23 | Zafgen, Inc. | Tricyclic compounds and methods of making and using same |
| MX344238B (es) | 2011-01-26 | 2016-12-07 | Zafgen Inc | Compuestos de tetrazol y métodos para preparar y usar los mismos. |
| US9187494B2 (en) | 2011-05-06 | 2015-11-17 | Zafgen, Inc. | Aryl-substituted tricyclic sulfonamides as methionyl aminopeptidase 2 modulators |
| MX343688B (es) | 2011-05-06 | 2016-11-16 | Zafgen Inc | Compuestos tricíclicos de sulfonamida y pirazolo y métodos para su fabricación y uso. |
| EP2705030B1 (en) | 2011-05-06 | 2016-07-27 | Zafgen, Inc. | Partially saturated tricyclic compounds and methods of making and using same |
| AU2013209719A1 (en) | 2012-01-18 | 2014-08-07 | Zafgen, Inc. | Tricyclic sulfone compounds and methods of making and using same |
| JP6035347B2 (ja) | 2012-01-18 | 2016-11-30 | ザフゲン，インコーポレイテッド | 三環式スルホンアミド化合物ならびにその作製および使用方法 |
| CA2890344A1 (en) | 2012-11-05 | 2014-05-08 | Zafgen, Inc. | Tricyclic compounds for use in the treatment and/or control of obesity |
| EA028367B1 (ru) | 2012-11-05 | 2017-11-30 | Зафджен, Инк. | Способы лечения заболеваний печени |
| BR112015010225A2 (pt) | 2012-11-05 | 2017-07-11 | Zafgen Inc | compostos tricíclicos e seus métodos de produção e utilização |
| HK1215170A1 (zh) | 2012-11-14 | 2016-08-19 | The Johns Hopkins University | 治療精神分裂症的方法和組合物 |
| WO2014137848A1 (en) * | 2013-03-04 | 2014-09-12 | Daya Drug Discoveries, Inc | PENTACYCLIC PYRIDOINDOLOBENZ[b,d]AZEPINE DERIVATIVES AND USES THEREOF |
| WO2015066344A1 (en) | 2013-11-01 | 2015-05-07 | Arena Pharmaceuticals, Inc. | 5-ht2c receptor agonists and compositions and methods of use |
| EP3519816A4 (en) | 2016-09-29 | 2020-05-06 | The Regents of the University of California | Compounds for increasing neural plasticity |
| US20210052600A1 (en) | 2017-12-27 | 2021-02-25 | Takeda Pharmaceutical Company Limited | Therapeutic agents for stress urinary incontinence and incotinence of feces |
| CN113784962B (zh) | 2019-02-27 | 2025-04-25 | 加利福尼亚大学董事会 | 用于治疗脑部疾病的氮杂环庚三烯并-吲哚类和其他杂环 |
| CN109897039B (zh) * | 2019-03-13 | 2021-03-30 | 中国科学院化学研究所 | 一种制备吡咯并[3,2,1-ij]喹啉酮化合物的方法 |
| EP4323359A4 (en) * | 2021-04-13 | 2025-09-03 | Univ California | TETRACYCLIC COMPOUNDS FOR THE TREATMENT OF BRAIN DISORDERS |
| JP2025502615A (ja) | 2021-12-15 | 2025-01-28 | デリックス セラピューティクス，インク． | フェノキシおよびベンジルオキシ置換サイコプラストゲンならびにその使用 |
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| US4238607A (en) | 1972-06-19 | 1980-12-09 | Endo Laboratories Inc. | Pyridopyrrolo benzheterocycles |
| US4013652A (en) | 1972-06-19 | 1977-03-22 | Endo Laboratories, Inc. | Pyridopyrrolobenzoxazine |
| US3914421A (en) | 1972-06-19 | 1975-10-21 | Endo Lab | Pyridopyrrolobenzheterocycles for combatting depression |
| US4115577A (en) | 1972-06-19 | 1978-09-19 | Endo Laboratories, Inc. | Pyridopyrrolobenzheterocycles |
| US4183936A (en) | 1972-06-19 | 1980-01-15 | Endo Laboratories, Inc. | Pyridopyrrolobenzheterocycles |
| US4219550A (en) | 1978-11-09 | 1980-08-26 | E. I. Du Pont De Nemours And Company | Cis- and trans- octahydropyridopyrrolobenzheterocycles |
| HUT61548A (en) * | 1990-08-27 | 1993-01-28 | Sandoz Ag | Process for producing indolonaphthyridine derivatives and pharmaceutical compositions comprising such compounds |
-
2001
- 2001-12-19 IL IL15626101A patent/IL156261A0/xx unknown
- 2001-12-19 DE DE60139511T patent/DE60139511D1/de not_active Expired - Lifetime
- 2001-12-19 PL PL01366627A patent/PL366627A1/xx unknown
- 2001-12-19 JP JP2002559426A patent/JP4386639B2/ja not_active Expired - Fee Related
- 2001-12-19 EP EP01994318A patent/EP1399445B9/en not_active Expired - Lifetime
- 2001-12-19 RU RU2003121306/04A patent/RU2003121306A/ru not_active Application Discontinuation
- 2001-12-19 MX MXPA03005355A patent/MXPA03005355A/es unknown
- 2001-12-19 HU HU0303530A patent/HUP0303530A3/hu unknown
- 2001-12-19 AU AU2002246726A patent/AU2002246726B2/en not_active Ceased
- 2001-12-19 KR KR10-2003-7008267A patent/KR20030070590A/ko not_active Withdrawn
- 2001-12-19 WO PCT/US2001/049380 patent/WO2002059124A2/en not_active Ceased
- 2001-12-19 AT AT01994318T patent/ATE438646T1/de not_active IP Right Cessation
- 2001-12-19 US US10/026,993 patent/US6777406B2/en not_active Expired - Lifetime
- 2001-12-19 BR BR0116348-5A patent/BR0116348A/pt not_active Application Discontinuation
- 2001-12-19 CZ CZ20031707A patent/CZ20031707A3/cs unknown
- 2001-12-19 EE EEP200300303A patent/EE200300303A/xx unknown
- 2001-12-19 ES ES01994318T patent/ES2329553T4/es not_active Expired - Lifetime
- 2001-12-19 SK SK703-2003A patent/SK7032003A3/sk unknown
- 2001-12-19 CA CA002432181A patent/CA2432181C/en not_active Expired - Fee Related
-
2003
- 2003-05-30 BG BG107863A patent/BG107863A/xx unknown
- 2003-06-02 ZA ZA200304304A patent/ZA200304304B/en unknown
- 2003-06-18 IS IS6851A patent/IS6851A/is unknown
- 2003-06-19 NO NO20032798A patent/NO20032798L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| EP1399445B9 (en) | 2010-07-21 |
| NO20032798L (no) | 2003-08-19 |
| ZA200304304B (en) | 2004-09-02 |
| BG107863A (en) | 2004-06-30 |
| EP1399445A2 (en) | 2004-03-24 |
| JP4386639B2 (ja) | 2009-12-16 |
| US6777406B2 (en) | 2004-08-17 |
| CA2432181C (en) | 2009-11-17 |
| AU2002246726B2 (en) | 2007-03-01 |
| KR20030070590A (ko) | 2003-08-30 |
| SK7032003A3 (en) | 2004-04-06 |
| BR0116348A (pt) | 2004-11-23 |
| CZ20031707A3 (cs) | 2003-11-12 |
| CA2432181A1 (en) | 2002-08-01 |
| IL156261A0 (en) | 2004-01-04 |
| WO2002059124A2 (en) | 2002-08-01 |
| HUP0303530A3 (en) | 2012-10-29 |
| IS6851A (is) | 2003-06-18 |
| RU2003121306A (ru) | 2005-03-10 |
| ES2329553T4 (es) | 2010-12-07 |
| HUP0303530A2 (hu) | 2004-01-28 |
| WO2002059124A3 (en) | 2004-01-08 |
| PL366627A1 (en) | 2005-02-07 |
| NO20032798D0 (no) | 2003-06-19 |
| JP2004528290A (ja) | 2004-09-16 |
| EE200300303A (et) | 2003-12-15 |
| MXPA03005355A (es) | 2004-05-27 |
| ATE438646T1 (de) | 2009-08-15 |
| EP1399445B1 (en) | 2009-08-05 |
| US20040092502A1 (en) | 2004-05-13 |
| DE60139511D1 (de) | 2009-09-17 |
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