ZA200509265B - Pyrrolodihydroisoquinolines as PDE10 inhibitors - Google Patents
Pyrrolodihydroisoquinolines as PDE10 inhibitors Download PDFInfo
- Publication number
- ZA200509265B ZA200509265B ZA200509265A ZA200509265A ZA200509265B ZA 200509265 B ZA200509265 B ZA 200509265B ZA 200509265 A ZA200509265 A ZA 200509265A ZA 200509265 A ZA200509265 A ZA 200509265A ZA 200509265 B ZA200509265 B ZA 200509265B
- Authority
- ZA
- South Africa
- Prior art keywords
- hydrogen
- alkyl
- phenyl
- alkoxy
- dimethoxy
- Prior art date
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- 239000003112 inhibitor Substances 0.000 title description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 429
- 239000001257 hydrogen Substances 0.000 claims description 429
- -1 nitro, amino Chemical group 0.000 claims description 300
- 150000002431 hydrogen Chemical group 0.000 claims description 220
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 154
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 141
- 150000001875 compounds Chemical class 0.000 claims description 139
- 229910052736 halogen Inorganic materials 0.000 claims description 111
- 150000002367 halogens Chemical group 0.000 claims description 111
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 105
- 229910052757 nitrogen Inorganic materials 0.000 claims description 93
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 88
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 70
- 125000005605 benzo group Chemical group 0.000 claims description 65
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 64
- 150000003254 radicals Chemical class 0.000 claims description 63
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 61
- 150000003839 salts Chemical class 0.000 claims description 61
- 229910052731 fluorine Inorganic materials 0.000 claims description 56
- 239000011737 fluorine Chemical group 0.000 claims description 56
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- 150000004677 hydrates Chemical class 0.000 claims description 48
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 47
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 30
- 229910052717 sulfur Inorganic materials 0.000 claims description 30
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- 239000011593 sulfur Substances 0.000 claims description 29
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- 125000005842 heteroatom Chemical group 0.000 claims description 28
- 229910052760 oxygen Inorganic materials 0.000 claims description 28
- 239000001301 oxygen Substances 0.000 claims description 28
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- 238000006467 substitution reaction Methods 0.000 claims description 10
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- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 7
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- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000131 cyclopropyloxy group Chemical group C1(CC1)O* 0.000 description 1
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004857 imidazopyridinyl group Chemical group N1C(=NC2=C1C=CC=N2)* 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000004594 isoindolinyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 229960003194 meglumine Drugs 0.000 description 1
- HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
- 125000005244 neohexyl group Chemical group [H]C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000004770 neurodegeneration Effects 0.000 description 1
- 208000015122 neurodegenerative disease Diseases 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 150000007519 polyprotic acids Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 239000003523 serotonin 4 antagonist Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000004571 thiomorpholin-4-yl group Chemical group N1(CCSCC1)* 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 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
- C07D471/02—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)
- Neurology (AREA)
- Neurosurgery (AREA)
- Diabetes (AREA)
- Psychiatry (AREA)
- Addiction (AREA)
- Endocrinology (AREA)
- Epidemiology (AREA)
- Pain & Pain Management (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Psychology (AREA)
- Reproductive Health (AREA)
- Emergency Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP03014424 | 2003-06-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200509265B true ZA200509265B (en) | 2006-10-25 |
Family
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Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
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| ZA200509265A ZA200509265B (en) | 2003-06-30 | 2005-11-16 | Pyrrolodihydroisoquinolines as PDE10 inhibitors |
| ZA200509267A ZA200509267B (en) | 2003-06-30 | 2005-11-16 | Novel pyrrodihydroisoquinoles usefel in the treatment of cancer |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
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| ZA200509267A ZA200509267B (en) | 2003-06-30 | 2005-11-16 | Novel pyrrodihydroisoquinoles usefel in the treatment of cancer |
Country Status (22)
| Country | Link |
|---|---|
| US (2) | US20060148840A1 (sr) |
| EP (2) | EP1641792B1 (sr) |
| JP (2) | JP2009513495A (sr) |
| KR (1) | KR20060030483A (sr) |
| CN (2) | CN1809565A (sr) |
| AR (2) | AR044956A1 (sr) |
| AT (1) | ATE478868T1 (sr) |
| AU (2) | AU2004253694A1 (sr) |
| BR (1) | BRPI0411897A (sr) |
| CA (2) | CA2530316A1 (sr) |
| DE (1) | DE602004028827D1 (sr) |
| EA (1) | EA012110B1 (sr) |
| IL (1) | IL171997A0 (sr) |
| IS (1) | IS8238A (sr) |
| MX (2) | MXPA05013822A (sr) |
| NO (1) | NO20060202L (sr) |
| NZ (1) | NZ544591A (sr) |
| RS (2) | RS20050945A (sr) |
| TW (2) | TW200510407A (sr) |
| UA (1) | UA86591C2 (sr) |
| WO (2) | WO2005003130A1 (sr) |
| ZA (2) | ZA200509265B (sr) |
Families Citing this family (34)
| Publication number | Priority date | Publication date | Assignee | Title |
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| AU2004253694A1 (en) * | 2003-06-30 | 2005-01-13 | 4Sc Ag | Novel pyrrolodihydroisoquinolines useful in the treatment of cancer |
| AU2006205797A1 (en) * | 2005-01-12 | 2006-07-20 | 4Sc Ag | Pyrrolodihydroisoquinolines as antiproliferative agents |
| US20080161338A1 (en) * | 2005-01-12 | 2008-07-03 | Altana Pharma Ag | Novel Pyrrolodihydroisoquinolines as Pde 10 Inhibitors |
| JP2010502670A (ja) | 2006-09-07 | 2010-01-28 | ニコメッド ゲゼルシャフト ミット ベシュレンクテル ハフツング | 真性糖尿病のための組合せ治療 |
| MX2009013354A (es) | 2007-06-04 | 2010-07-06 | Univ Ben Gurion | Compuestos de triarilo y composiciones que los contienen. |
| 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 |
| MX2010009300A (es) | 2008-02-29 | 2010-11-05 | Concert Pharmaceuticals Inc | Derivados de xantina substituidos. |
| 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 |
| US8133897B2 (en) | 2008-06-20 | 2012-03-13 | H. Lundbeck A/S | Phenylimidazole derivatives as PDE10A enzyme inhibitors |
| 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 |
| 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 |
| 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 |
| 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 |
| 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 |
| JP2014510055A (ja) | 2011-02-18 | 2014-04-24 | アラーガン インコーポレイテッド | ホスホジエステラーゼ１０（ｐｄｅ１０ａ）阻害剤としての置換６，７−ジアルコキシ−３−イソキノリノール誘導体 |
| 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 |
| AR089361A1 (es) | 2011-12-21 | 2014-08-20 | Lundbeck & Co As H | Derivados de quinolina como inhibidores de la enzima pde10a |
| 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 |
| LT3027613T (lt) * | 2013-07-25 | 2018-07-25 | Uniwersytet Jagiellonski | Pirolochinolino dariniai kaip 5-ht6 antagonistai, jų gavimas ir panaudojimas |
| CA2928725A1 (en) | 2013-11-05 | 2015-05-14 | Esther Priel | Compounds for the treatment of diabetes and disease complications arising from same |
| US9200016B2 (en) | 2013-12-05 | 2015-12-01 | Allergan, Inc. | Substituted 6, 7-dialkoxy-3-isoquinoline derivatives as inhibitors of phosphodiesterase 10 (PDE 10A) |
| CA2981791A1 (en) | 2014-04-18 | 2015-10-22 | Concert Pharmaceuticals, Inc. | Methods of treating hyperglycemia |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE690792A (sr) * | 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 |
| EP1347973A1 (en) * | 2000-12-13 | 2003-10-01 | 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 |
| US20030032579A1 (en) * | 2001-04-20 | 2003-02-13 | 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 |
| DE10130151A1 (de) * | 2001-06-22 | 2003-01-02 | Bayer Ag | Neue Verwendung für PDE 10A-Inhibitoren |
| WO2003014116A1 (en) * | 2001-08-06 | 2003-02-20 | Bayer Corporation | Pyrrolo[2.1-a]isoquinoline derivatives |
| WO2003014115A1 (en) * | 2001-08-06 | 2003-02-20 | Bayer Aktiengesellschaft | 3-substituted 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 |
| AU2004253694A1 (en) * | 2003-06-30 | 2005-01-13 | 4Sc Ag | Novel pyrrolodihydroisoquinolines useful in the treatment of cancer |
| AU2006205797A1 (en) * | 2005-01-12 | 2006-07-20 | 4Sc Ag | Pyrrolodihydroisoquinolines as antiproliferative agents |
| US20080161338A1 (en) * | 2005-01-12 | 2008-07-03 | Altana Pharma Ag | Novel Pyrrolodihydroisoquinolines as Pde 10 Inhibitors |
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2004
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- 2004-06-30 NZ NZ544591A patent/NZ544591A/xx unknown
- 2004-06-30 TW TW093119589A patent/TW200510407A/zh unknown
- 2004-06-30 AR ARP040102290A patent/AR044956A1/es not_active Application Discontinuation
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- 2004-06-30 CN CNA2004800175231A patent/CN1809565A/zh active Pending
- 2004-06-30 US US10/562,137 patent/US20060148840A1/en not_active Abandoned
- 2004-06-30 AU AU2004253690A patent/AU2004253690B2/en not_active Ceased
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- 2004-06-30 EP EP04766106A patent/EP1641794A1/en not_active Withdrawn
- 2004-06-30 AR ARP040102291A patent/AR045696A1/es not_active Application Discontinuation
- 2004-06-30 US US10/562,149 patent/US20060148838A1/en not_active Abandoned
- 2004-06-30 BR BRPI0411897-9A patent/BRPI0411897A/pt not_active IP Right Cessation
- 2004-06-30 JP JP2006516198A patent/JP2009513495A/ja active Pending
- 2004-06-30 RS YUP-2005/0945A patent/RS20050945A/sr unknown
- 2004-06-30 UA UAA200600505A patent/UA86591C2/ru unknown
- 2004-06-30 AT AT04741932T patent/ATE478868T1/de not_active IP Right Cessation
- 2004-06-30 CA CA002530316A patent/CA2530316A1/en not_active Abandoned
- 2004-06-30 TW TW093119579A patent/TW200510413A/zh unknown
- 2004-06-30 CA CA002530317A patent/CA2530317A1/en not_active Abandoned
- 2004-06-30 JP JP2006516197A patent/JP2009513494A/ja active Pending
- 2004-06-30 WO PCT/EP2004/051307 patent/WO2005003129A1/en active Application Filing
- 2004-06-30 DE DE602004028827T patent/DE602004028827D1/de active Active
- 2004-06-30 CN CNA2004800175104A patent/CN1809564A/zh active Pending
- 2004-06-30 RS YUP-2005/0946A patent/RS20050946A/sr unknown
- 2004-06-30 KR KR1020057024872A patent/KR20060030483A/ko not_active Application Discontinuation
- 2004-06-30 MX MXPA05013822A patent/MXPA05013822A/es unknown
- 2004-06-30 MX MXPA05013553A patent/MXPA05013553A/es active IP Right Grant
- 2004-06-30 EA EA200501928A patent/EA012110B1/ru not_active IP Right Cessation
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2005
- 2005-11-16 ZA ZA200509265A patent/ZA200509265B/en unknown
- 2005-11-16 ZA ZA200509267A patent/ZA200509267B/en unknown
- 2005-11-16 IL IL171997A patent/IL171997A0/en unknown
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2006
- 2006-01-13 NO NO20060202A patent/NO20060202L/no not_active Application Discontinuation
- 2006-01-18 IS IS8238A patent/IS8238A/is unknown
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