AR044956A1 - Derivados de pirrolodihidroisoquinolinas, composiciones farmaceuticas que los contienen y su uso en el tratamiento del cancer. - Google Patents
Derivados de pirrolodihidroisoquinolinas, composiciones farmaceuticas que los contienen y su uso en el tratamiento del cancer.Info
- Publication number
- AR044956A1 AR044956A1 ARP040102290A ARP040102290A AR044956A1 AR 044956 A1 AR044956 A1 AR 044956A1 AR P040102290 A ARP040102290 A AR P040102290A AR P040102290 A ARP040102290 A AR P040102290A AR 044956 A1 AR044956 A1 AR 044956A1
- Authority
- AR
- Argentina
- Prior art keywords
- alkyl
- alkoxy
- amino
- halogen
- substituted
- Prior art date
Links
- 206010028980 Neoplasm Diseases 0.000 title abstract 2
- 201000011510 cancer Diseases 0.000 title abstract 2
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 27
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 17
- 125000000217 alkyl group Chemical group 0.000 abstract 12
- 125000003545 alkoxy group Chemical group 0.000 abstract 9
- 229910052736 halogen Inorganic materials 0.000 abstract 9
- 150000002367 halogens Chemical class 0.000 abstract 9
- -1 nitro, amino Chemical group 0.000 abstract 8
- 125000005605 benzo group Chemical group 0.000 abstract 7
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 5
- 229910052739 hydrogen Inorganic materials 0.000 abstract 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 3
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 3
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 125000005842 heteroatom Chemical group 0.000 abstract 2
- 150000004677 hydrates Chemical class 0.000 abstract 2
- 125000001624 naphthyl group Chemical group 0.000 abstract 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract 2
- 229910052760 oxygen Inorganic materials 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 229910052717 sulfur Inorganic materials 0.000 abstract 2
- 125000004760 (C1-C4) alkylsulfonylamino group Chemical group 0.000 abstract 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- IOEPOEDBBPRAEI-UHFFFAOYSA-N 1,2-dihydroisoquinoline Chemical group C1=CC=C2CNC=CC2=C1 IOEPOEDBBPRAEI-UHFFFAOYSA-N 0.000 abstract 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 230000006907 apoptotic process Effects 0.000 abstract 1
- 125000005160 aryl oxy alkyl group Chemical group 0.000 abstract 1
- 125000004657 aryl sulfonyl amino group Chemical group 0.000 abstract 1
- 125000004104 aryloxy group Chemical group 0.000 abstract 1
- 125000004429 atom 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
- 125000002619 bicyclic group Chemical group 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 230000004663 cell proliferation Effects 0.000 abstract 1
- 125000000000 cycloalkoxy group Chemical group 0.000 abstract 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 abstract 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 abstract 1
- 125000005113 hydroxyalkoxy group Chemical group 0.000 abstract 1
- 239000000411 inducer Substances 0.000 abstract 1
- 239000003112 inhibitor Substances 0.000 abstract 1
- 125000002757 morpholinyl group Chemical group 0.000 abstract 1
- 125000003386 piperidinyl group Chemical group 0.000 abstract 1
- 125000004076 pyridyl group Chemical group 0.000 abstract 1
- 125000000714 pyrimidinyl group Chemical group 0.000 abstract 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 abstract 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 abstract 1
Classifications
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- 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
- C07D471/02—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 two hetero rings
- C07D471/04—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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4738—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems
- A61K31/4745—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems condensed with ring systems having nitrogen as a ring hetero atom, e.g. phenantrolines
-
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- 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
- A61P25/22—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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
-
- 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
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/32—Alcohol-abuse
-
- 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
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/36—Opioid-abuse
-
- 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
- A61P35/00—Antineoplastic agents
-
- 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
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/48—Drugs for disorders of the endocrine system of the pancreatic hormones
- A61P5/50—Drugs for disorders of the endocrine system of the pancreatic hormones for increasing or potentiating the activity of insulin
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Psychiatry (AREA)
- Addiction (AREA)
- Diabetes (AREA)
- Endocrinology (AREA)
- Epidemiology (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Emergency Medicine (AREA)
- Psychology (AREA)
- Pain & Pain Management (AREA)
- Reproductive Health (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
Derivados de pirrolodihidroisoquinolina, que son inhibidores eficaces de (hiper) proliferación celular y/o inductores de apoptosis en células cancerosas. Reivindicación 1: Compuestos de la fórmula (1) caracterizados porque R1 es halógeno, nitro, amino, mono- o di-(alquil C1-4)amino, alquilo C1-4, ,hidroxilo, alcoxi C1-4, alcoxi C1-4-alcoxi-C2-4, cicloalcoxi C3-7, cicloalquilmetoxi C3-7 o alcoxi C1-4 completamente o predominantemente sustituido con F; R2 es H, halógeno o alcoxi C1-4, R3 es H o alcoxi C1-4, o R2 y R3 ligados al grupo anular benzo en posición orto entre si forman conjuntamente un puente alquilendioxi C1-2, o R2 y R3 ligados al grupo anular benzo en posición orto entre si forman conjuntamente un puente alquilendioxi C1-2 completamente o predominantemente sustituido con F, R1 y R2 ligados al grupo anular benzo en posición orto entre si forman conjuntamente un puente alquilendioxi C1-2 y R3 es H, o R1 y R2 ligados al grupo anular benzo en posición orto entre si forman conjuntamente un puente alquilendioxi C1-2 completamente o predominantemente sustituido con F y R3 es H; R4 es H, F, Cl. alquilo C1-4, trifluorometilo, ciclopropilo, ciano, alcoxicarbonilo C1-4 o -CH2-O-R411, donde R411 es H, alquilo C1-4, alcoxi C1-4-alquilo C2-4 o (alquil C1-4)carbonilo; R41 es H o alquilo C1-4; R5 es H; R51 es H; o R4 es H, F, Cl, o alquilo C1-4, R41 es H o alquilo C1-4; R5 es H; R51 es H; R6 es alquilo C1-6, amino, formilo o alquilo C1-4 sustituido con R61, donde R61 es (alcoxi C1-4)carbonilo, carboxilo, alcoxi C1-4, hidroxilo, halógeno o -N(R611)R612, donde R611 es H, alquilo C1-4, cicloalquilo C3-7 o cicloalquilo C3-7-alquilo C1-4; R612 es H o alquilo C1-4, o R611 y R612 conjuntamente y con la inclusión del átomo de N al cual están ligados forman un radical Het1, donde Het1 es un radical anular heterocíclico saturado de 5 a 7 miembros que comprende un átomo de N, al cual están ligados R611 y R612, y, opcionalmente, un heteroátomo adicional seleccionado del grupo formado por N, O y S, y opcionalmente sustituido con R613 sobre un átomo anular de N, donde R613 es alquilo C1-4, cicloalquilo C3-7, cicloalquilo C3-7-alquilo C1-4, hidroxi-alquilo C2-4, alcoxi C1-4-alquilo C2-4, (alquil C2-4)amino, mono- o di-(alquil C1-4)amino-alquilo C2-4, formilo, piridilo o pirimidinilo; R7 es fenilo, Het2, fenilo sustituido con R71 y/o R72 y/o R73, Het2 sustituido con R74 y/o R75, naftilo o naftilo sustituido con R76 y/o R77, donde Het2 es un radical heteroarilo de5 a 10 miembros monocíclico o bicíclico fusionado que comprende 1 a 3 heteroátomos, cada uno de los cuales es seleccionado del grupo formado por N, O y S; R71 es hidroxilo, halógeno, nitro, ciano, trifluorometilo, alquilo C1-4, alcoxi C1-4, amino, mono- o di-(alquil C1-4)amino, alquil C1-4-sulfonilamino, arilsulfonilamino, (alcoxi C1-4)carbonilo, carboxilo, alquiltio C1-4, ariloxi-alcoxi C2-4, ariloxi-alquilo C1-4, ariloxi, aril-alcoxi C1-4, arilo, alcoxi C1-4-alcoxi C2-4, alcoxi C1-4-alquilo C1-4, hidroxi-alcoxi 2-4, amino-alcoxi C2-4, mono- o di-(alquil C1-4)amino-alcoxi C2-4 o alcoxi C1-4 completamente o predominantemente sustituido con F, donde arilo es fenilo o fenilo sustituido con R711, donde R711 es halógeno, alquilo C1-4, alcoxi C1-4, nitro o ciano, R72 es halógeno, alquilo C1-4, alcoxi C1-4 o (alcoxi C1-4)carbonilo; R73 es alquilo C1-4 o alcoxi C1-4; R74 es halógeno, alquilo C1-4, trifluorometilo, alcoxi C1-4, ciano, amino, mono- o di-(alquil C1-4)amino, (alcoxi C1-4)carbonilo, morfolino, carboxilo, nitro, fenilo o feniloxi; R75 es alquilo C1-4 o halógeno; R76 es halógeno, hidroxilo, alquilo C1-4, alcoxi C1-4,carboxilo o (alcoxi C1-4)carbonilo; R77 es alquilo C1-4 o alcoxi C1-4; R8 es fenilo, fenilcarbonilo, -C(O)-N(R82)R83 o -C(O)-OR9, donde R82 es H, alquilo C1-4, cicloalquilo C3-7, cicloalquilo C3-7-alquilo C1-4, fenilo o fenil-alquilo C1-4; R83 es H o alquilo C1-4, o R82 y R83 conjuntamente y con inclusión del átomo de N al cual están ligados, forman un radical anular heterocíclico seleccionado del grupo formado por pirrolidinilo, piperidinilo, morfolinilo o N-(alquil C1-4)-piperazinilo; R9 es alquilo C1-4; con la condición, que se excluye este subgrupo de compuestos de fórmula (1), en el cual se aplica la combinación de todas las restricciones a.) a c.) siguientes: a.) el esquema de sustitución del anillo benzo izquierdo sustituido con R1 y/o R2 y/o R3 del grupo dihidroisoquinolina de la estructura de la pirrolodihidroisoquinolina mostrada en la fórmula (1) es como se muestra en estructura (A) donde R´y R" pueden estar ligados a cualquier posición posible del anillo benzo, y R´ es hidroxilo, alcoxi C1-4 o trifluorometoxi, R" es H o alcoxi C1-4, o R´ y R" ligados al grupo anular benzo en posición orto entre sí forman conjuntamente un puente alquilendioxi C1-2, y b.) R4 es H, y R41 es H, y R5 es H, y R51 es H, y c.) R8 es -C(O)-OR9, donde R9 es alquilo C1-4; y las sales, estereoisómeros, hidratos e hidratos de las sales de estos compuestos.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP03014424 | 2003-06-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR044956A1 true AR044956A1 (es) | 2005-10-12 |
Family
ID=33560746
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP040102291A AR045696A1 (es) | 2003-06-30 | 2004-06-30 | Derivados de pirrolodihidroisoquinolinas como inhibidores de pde10 |
| ARP040102290A AR044956A1 (es) | 2003-06-30 | 2004-06-30 | Derivados de pirrolodihidroisoquinolinas, composiciones farmaceuticas que los contienen y su uso en el tratamiento del cancer. |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP040102291A AR045696A1 (es) | 2003-06-30 | 2004-06-30 | Derivados de pirrolodihidroisoquinolinas como inhibidores de pde10 |
Country Status (22)
| Country | Link |
|---|---|
| US (2) | US20060148840A1 (es) |
| EP (2) | EP1641794A1 (es) |
| JP (2) | JP2009513494A (es) |
| KR (1) | KR20060030483A (es) |
| CN (2) | CN1809564A (es) |
| AR (2) | AR045696A1 (es) |
| AT (1) | ATE478868T1 (es) |
| AU (2) | AU2004253690B2 (es) |
| BR (1) | BRPI0411897A (es) |
| CA (2) | CA2530317A1 (es) |
| DE (1) | DE602004028827D1 (es) |
| EA (1) | EA012110B1 (es) |
| IL (1) | IL171997A0 (es) |
| IS (1) | IS8238A (es) |
| MX (2) | MXPA05013822A (es) |
| NO (1) | NO20060202L (es) |
| NZ (1) | NZ544591A (es) |
| RS (2) | RS20050946A (es) |
| TW (2) | TW200510407A (es) |
| UA (1) | UA86591C2 (es) |
| WO (2) | WO2005003129A1 (es) |
| ZA (2) | ZA200509265B (es) |
Families Citing this family (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005003129A1 (en) * | 2003-06-30 | 2005-01-13 | Altana Pharma Ag | Pyrrolodihydroisoquinolines as pde10 inhibitors |
| CA2593750A1 (en) * | 2005-01-12 | 2006-08-31 | Altana Pharma Ag | Novel pyrrolodihydroisoquinolines as pde10 inhibitors |
| AU2006205797A1 (en) * | 2005-01-12 | 2006-07-20 | 4Sc Ag | Pyrrolodihydroisoquinolines as antiproliferative agents |
| AU2007293885A1 (en) | 2006-09-07 | 2008-03-13 | Takeda Gmbh | Combination treatment for diabetes mellitus |
| KR101560844B1 (ko) | 2007-06-04 | 2015-10-15 | 벤-구리온 유니버시티 오브 더 네게브 리서치 앤드 디벨럽먼트 어쏘러티 | 트라이-아릴계 화합물 및 이를 포함하는 조성물 |
| TW200918519A (en) * | 2007-09-19 | 2009-05-01 | Lundbeck & Co As H | Cyanoisoquinoline |
| US7858620B2 (en) | 2007-09-19 | 2010-12-28 | H. Lundbeck A/S | Cyanoisoquinoline |
| TW200944523A (en) * | 2008-02-08 | 2009-11-01 | Organon Nv | (Dihydro)pyrrolo[2,1-a]isoquinolines |
| WO2009108383A2 (en) | 2008-02-29 | 2009-09-03 | Concert Pharmaceuticals, Inc. | Substituted xanthine derivatives |
| US8133897B2 (en) | 2008-06-20 | 2012-03-13 | H. Lundbeck A/S | Phenylimidazole derivatives as PDE10A enzyme inhibitors |
| UA102693C2 (ru) | 2008-06-20 | 2013-08-12 | Х. Луннбек А/С | Производные фенилимидазола как ингибиторы фермента pde10a |
| TWI501965B (zh) * | 2008-06-20 | 2015-10-01 | Lundbeck & Co As H | 作為ｐｄｅ１０ａ酵素抑制劑之新穎苯基咪唑衍生物 |
| US20110053961A1 (en) | 2009-02-27 | 2011-03-03 | Concert Pharmaceuticals, Inc. | Substituted xanthine derivatives |
| TWI461426B (zh) * | 2009-05-27 | 2014-11-21 | Merck Sharp & Dohme | （二氫）咪唑並異〔５，１－ａ〕喹啉類 |
| TWI487705B (zh) | 2009-12-17 | 2015-06-11 | Lundbeck & Co As H | 作為ｐｄｅ１０ａ酵素抑制劑之雜芳香族芳基三唑衍生物 |
| TW201200516A (en) | 2009-12-17 | 2012-01-01 | Lundbeck & Co As H | Phenylimidazole derivatives comprising an ethynylene linker as PDE10A enzyme inhibitors |
| TWI481607B (zh) | 2009-12-17 | 2015-04-21 | Lundbeck & Co As H | 作為ｐｄｅ１０ａ酵素抑制劑的２－芳基咪唑衍生物 |
| TWI485151B (zh) | 2009-12-17 | 2015-05-21 | Lundbeck & Co As H | 作為ｐｄｅ１０ａ酵素抑制劑之雜芳香族苯基咪唑衍生物 |
| TW201215607A (en) | 2010-07-02 | 2012-04-16 | Lundbeck & Co As H | Aryl-and heteroarylamid derivatives as PDE10A enzyme inhibitor |
| TW201206935A (en) | 2010-07-16 | 2012-02-16 | Lundbeck & Co As H | Triazolo-and pyrazoloquinazoline derivatives as PDE10A enzyme inhibitor |
| DE102010042833B4 (de) | 2010-10-22 | 2018-11-08 | Helmholtz-Zentrum Dresden - Rossendorf E.V. | Neue Halogenalkoxychinazoline, deren Herstellung und Verwendung |
| JO3089B1 (ar) | 2010-11-19 | 2017-03-15 | H Lundbeck As | مشتقات ايميدازول كمثبطات لانزيمات pde10a |
| US8772316B2 (en) | 2011-02-18 | 2014-07-08 | Allergan, Inc. | Substituted 6,7-dialkoxy-3-isoquinolinol derivatives as inhibitors of phosphodiesterase 10 (PDE10A) |
| WO2013013052A1 (en) | 2011-07-19 | 2013-01-24 | Concert Pharmaceuticals, Inc. | Substituted xanthine derivatives |
| WO2013045607A1 (en) | 2011-09-30 | 2013-04-04 | H. Lundbeck A/S | Quinazoline linked heteroaromatic tricycle derivatives as pde10a enzyme inhibitors |
| WO2013050527A1 (en) | 2011-10-05 | 2013-04-11 | H. Lundbeck A/S | Quinazoline derivatives as pde10a enzyme inhibitors |
| TWI570124B (zh) | 2011-12-21 | 2017-02-11 | Ｈ 朗德貝克公司 | 作為ｐｄｅ１０ａ酵素抑制劑的喹啉衍生物 |
| WO2013127817A1 (en) | 2012-02-27 | 2013-09-06 | H. Lundbeck A/S | Imidazole derivatives as pde10a enzyme inhibitors |
| WO2014071044A1 (en) | 2012-11-01 | 2014-05-08 | Allergan, Inc. | Substituted 6,7-dialkoxy-3-isoquinoline derivatives as inhibitors of phosphodiesterase 10 (pde10a) |
| CN103059029B (zh) * | 2012-12-28 | 2014-12-10 | 塔里木大学 | 一种六氢吡咯[2,3]并吲哚类化合物及其制备方法和在杀菌活性中的应用 |
| AU2013394970B2 (en) * | 2013-07-25 | 2017-11-23 | Centre National De La Recherche Scientifique | Pyrroloquinoline derivatives as 5-HT6 antagonists, preparation method and use thereof |
| CR20160207A (es) | 2013-11-05 | 2016-08-10 | Ben Gurion Univ Of The Negev Res And Dev Authority | Compuestos para el tratamiento de la diabetes y las complicaciones que surgen de la misma enfermedad |
| US9200016B2 (en) | 2013-12-05 | 2015-12-01 | Allergan, Inc. | Substituted 6, 7-dialkoxy-3-isoquinoline derivatives as inhibitors of phosphodiesterase 10 (PDE 10A) |
| US20170216296A1 (en) | 2014-04-18 | 2017-08-03 | Concert Pharmaceuticals, Inc. | Methods of treating hyperglycemia |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE690792A (es) * | 1966-12-07 | 1967-05-16 | ||
| DE3401018A1 (de) * | 1984-01-13 | 1985-07-18 | Boehringer Ingelheim KG, 6507 Ingelheim | Verfahren zur herstellung von 5,6-dihydro-pyrrolo(2,1-a)isochinolinen |
| FR2761358B1 (fr) * | 1997-03-27 | 1999-05-07 | Adir | Nouveaux composes de n-aryl piperidine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| CA2431326A1 (en) * | 2000-12-13 | 2002-06-20 | Bayer Aktiengesellschaft | Pyrrolo (2.1-a) dihydroisoquinolines and their use as phosphodiesterase 10a inhibitors |
| US20030018047A1 (en) * | 2001-04-20 | 2003-01-23 | Pfizer Inc. | Therapeutic use of selective PDE10 inhibitors |
| IL149106A0 (en) * | 2001-04-20 | 2002-11-10 | Pfizer Prod Inc | Therapeutic use of selective pde10 inhibitors |
| US20030032579A1 (en) * | 2001-04-20 | 2003-02-13 | Pfizer Inc. | Therapeutic use of selective PDE10 inhibitors |
| DE10130151A1 (de) * | 2001-06-22 | 2003-01-02 | Bayer Ag | Neue Verwendung für PDE 10A-Inhibitoren |
| WO2003014115A1 (en) * | 2001-08-06 | 2003-02-20 | Bayer Aktiengesellschaft | 3-substituted pyrrolo (2.1-a) isoquinoline derivatives |
| US20030236276A1 (en) * | 2001-08-06 | 2003-12-25 | Ulrich Niewohner | Pyrrolo[2.1-a]isoquinoline derivatives |
| AU2002366362A1 (en) * | 2001-12-18 | 2003-06-30 | Bayer Aktiengesellschaft | 2-substituted pyrrolo(2.1-a)isoquinolines against cancer |
| WO2005003129A1 (en) * | 2003-06-30 | 2005-01-13 | Altana Pharma Ag | Pyrrolodihydroisoquinolines as pde10 inhibitors |
| CA2593750A1 (en) * | 2005-01-12 | 2006-08-31 | Altana Pharma Ag | Novel pyrrolodihydroisoquinolines as pde10 inhibitors |
| AU2006205797A1 (en) * | 2005-01-12 | 2006-07-20 | 4Sc Ag | Pyrrolodihydroisoquinolines as antiproliferative agents |
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