HRP20100010T1 - Derivati 1h-indol-piridinkarboksamida i 1h-indol-piperidinkarboksamida i njihova uporaba kao izazivača tirozin hidroksilaze - Google Patents
Derivati 1h-indol-piridinkarboksamida i 1h-indol-piperidinkarboksamida i njihova uporaba kao izazivača tirozin hidroksilaze Download PDFInfo
- Publication number
- HRP20100010T1 HRP20100010T1 HR20100010T HRP20100010T HRP20100010T1 HR P20100010 T1 HRP20100010 T1 HR P20100010T1 HR 20100010 T HR20100010 T HR 20100010T HR P20100010 T HRP20100010 T HR P20100010T HR P20100010 T1 HRP20100010 T1 HR P20100010T1
- Authority
- HR
- Croatia
- Prior art keywords
- branched
- straight
- group
- formula
- alkyl
- Prior art date
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- 239000000411 inducer Substances 0.000 title claims 2
- QVZVCSFCKNTGFD-UHFFFAOYSA-N 1h-indole;piperidine-1-carboxamide Chemical class C1=CC=C2NC=CC2=C1.NC(=O)N1CCCCC1 QVZVCSFCKNTGFD-UHFFFAOYSA-N 0.000 title 1
- UQICWCSUPXHVFI-UHFFFAOYSA-N 1h-indole;pyridine-2-carboxamide Chemical compound C1=CC=C2NC=CC2=C1.NC(=O)C1=CC=CC=N1 UQICWCSUPXHVFI-UHFFFAOYSA-N 0.000 title 1
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 title 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 title 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 46
- 150000001875 compounds Chemical class 0.000 claims abstract 40
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 16
- 125000000217 alkyl group Chemical group 0.000 claims abstract 13
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract 12
- 125000003277 amino group Chemical group 0.000 claims abstract 10
- 125000005843 halogen group Chemical group 0.000 claims abstract 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 9
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 8
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract 7
- 125000006685 (C1-C6) polyhaloalkyl group Chemical group 0.000 claims abstract 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract 5
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims abstract 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 4
- 125000003118 aryl group Chemical group 0.000 claims abstract 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 4
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 4
- 239000001257 hydrogen Substances 0.000 claims abstract 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract 4
- 229910052717 sulfur Inorganic materials 0.000 claims abstract 4
- 125000004103 aminoalkyl group Chemical group 0.000 claims abstract 3
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims abstract 2
- 125000003342 alkenyl group Chemical group 0.000 claims abstract 2
- 229910052736 halogen Inorganic materials 0.000 claims abstract 2
- 150000002367 halogens Chemical class 0.000 claims abstract 2
- 125000004434 sulfur atom Chemical group 0.000 claims abstract 2
- 239000002253 acid Substances 0.000 claims 19
- 150000003839 salts Chemical class 0.000 claims 19
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 18
- 150000001204 N-oxides Chemical class 0.000 claims 9
- -1 hydroxy, amino Chemical group 0.000 claims 7
- 229910052757 nitrogen Inorganic materials 0.000 claims 6
- 125000000623 heterocyclic group Chemical group 0.000 claims 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 4
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 4
- 125000005842 heteroatom Chemical group 0.000 claims 4
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 4
- 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims 4
- 125000002950 monocyclic group Chemical group 0.000 claims 4
- 229920006395 saturated elastomer Polymers 0.000 claims 4
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
- 239000013543 active substance Substances 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000004122 cyclic group Chemical group 0.000 claims 2
- AGKHQCOEYCYYHV-UHFFFAOYSA-N n-(2,3-dihydroindol-1-yl)-1-methyl-3,4-dihydro-2h-pyridine-5-carboxamide Chemical compound CN1CCCC(C(=O)NN2C3=CC=CC=C3CC2)=C1 AGKHQCOEYCYYHV-UHFFFAOYSA-N 0.000 claims 2
- KBFJXJPOPFZTPX-UHFFFAOYSA-N n-indol-1-yl-1-(2-piperidin-1-ylethyl)piperidine-3-carboxamide Chemical class C1=CC2=CC=CC=C2N1NC(=O)C(C1)CCCN1CCN1CCCCC1 KBFJXJPOPFZTPX-UHFFFAOYSA-N 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims 2
- 239000011593 sulfur Substances 0.000 claims 2
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 1
- XWMMAFGFDLLRLX-UHFFFAOYSA-N 1-[2-(dimethylamino)ethyl]-n-indol-1-yl-3,6-dihydro-2h-pyridine-5-carboxamide Chemical compound C1N(CCN(C)C)CCC=C1C(=O)NN1C2=CC=CC=C2C=C1 XWMMAFGFDLLRLX-UHFFFAOYSA-N 0.000 claims 1
- 208000019901 Anxiety disease Diseases 0.000 claims 1
- 208000020401 Depressive disease Diseases 0.000 claims 1
- 208000026139 Memory disease Diseases 0.000 claims 1
- 208000018737 Parkinson disease Diseases 0.000 claims 1
- 108091000117 Tyrosine 3-Monooxygenase Proteins 0.000 claims 1
- 102000048218 Tyrosine 3-monooxygenases Human genes 0.000 claims 1
- HHRFWSALGNYPHA-UHFFFAOYSA-N [N].C1CNCCN1 Chemical group [N].C1CNCCN1 HHRFWSALGNYPHA-UHFFFAOYSA-N 0.000 claims 1
- 230000006978 adaptation Effects 0.000 claims 1
- 230000032683 aging Effects 0.000 claims 1
- 125000003162 alpha-aspartyl group Chemical group 0.000 claims 1
- 125000000337 alpha-glutamyl group Chemical group 0.000 claims 1
- 230000036506 anxiety Effects 0.000 claims 1
- 125000000637 arginyl group Chemical group N[C@@H](CCCNC(N)=N)C(=O)* 0.000 claims 1
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims 1
- 125000001942 asparaginyl group Chemical group 0.000 claims 1
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 125000002711 cysteinyl group Chemical group 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000001939 glutaminyl group Chemical group 0.000 claims 1
- 125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 claims 1
- 125000000487 histidyl group Chemical group [H]N([H])C(C(=O)O*)C([H])([H])C1=C([H])N([H])C([H])=N1 0.000 claims 1
- 125000000741 isoleucyl group Chemical group [H]N([H])C(C(C([H])([H])[H])C([H])([H])C([H])([H])[H])C(=O)O* 0.000 claims 1
- 229950003188 isovaleryl diethylamide Drugs 0.000 claims 1
- 125000001998 leucyl group Chemical group 0.000 claims 1
- 125000001288 lysyl group Chemical group 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- GMDZFNXSVUVGLK-UHFFFAOYSA-N n-(5-chloroindol-1-yl)-1-(2-hydroxyethyl)-3,4-dihydro-2h-pyridine-5-carboxamide Chemical compound OCCN1CCCC(C(=O)NN2C3=CC=C(Cl)C=C3C=C2)=C1 GMDZFNXSVUVGLK-UHFFFAOYSA-N 0.000 claims 1
- KVBDCWMUOPHOEW-UHFFFAOYSA-N n-(5-fluoroindol-1-yl)-1-methyl-3,6-dihydro-2h-pyridine-5-carboxamide Chemical compound C1N(C)CCC=C1C(=O)NN1C2=CC=C(F)C=C2C=C1 KVBDCWMUOPHOEW-UHFFFAOYSA-N 0.000 claims 1
- NJKRDPIHNOWVJI-UHFFFAOYSA-N n-diphenylphosphorylhydroxylamine Chemical compound C=1C=CC=CC=1P(=O)(NO)C1=CC=CC=C1 NJKRDPIHNOWVJI-UHFFFAOYSA-N 0.000 claims 1
- RBTDGGZNVGCRKR-UHFFFAOYSA-N n-indol-1-yl-1-(2-piperidin-1-ylethyl)-3,6-dihydro-2h-pyridine-5-carboxamide Chemical compound C1=CC2=CC=CC=C2N1NC(=O)C(C1)=CCCN1CCN1CCCCC1 RBTDGGZNVGCRKR-UHFFFAOYSA-N 0.000 claims 1
- DLZGWWMQLYAPGY-UHFFFAOYSA-N n-indol-1-yl-1-(3-piperidin-1-ylpropyl)piperidine-3-carboxamide Chemical compound C1=CC2=CC=CC=C2N1NC(=O)C(C1)CCCN1CCCN1CCCCC1 DLZGWWMQLYAPGY-UHFFFAOYSA-N 0.000 claims 1
- SKAREVXDURBUSJ-UHFFFAOYSA-N n-indol-1-yl-1-(4-piperidin-1-ylbut-2-enyl)piperidine-3-carboxamide Chemical compound C1=CC2=CC=CC=C2N1NC(=O)C(C1)CCCN1CC=CCN1CCCCC1 SKAREVXDURBUSJ-UHFFFAOYSA-N 0.000 claims 1
- AMEOVJAYVLBGKO-UHFFFAOYSA-N n-indol-1-yl-1-[2-(4-methylpiperazin-1-yl)ethyl]piperidine-3-carboxamide Chemical compound C1CN(C)CCN1CCN1CC(C(=O)NN2C3=CC=CC=C3C=C2)CCC1 AMEOVJAYVLBGKO-UHFFFAOYSA-N 0.000 claims 1
- BWVZNOZUTQQTCJ-UHFFFAOYSA-N n-indol-1-yl-1-[3-(4-methylpiperazin-1-yl)propyl]piperidine-3-carboxamide Chemical compound C1CN(C)CCN1CCCN1CC(C(=O)NN2C3=CC=CC=C3C=C2)CCC1 BWVZNOZUTQQTCJ-UHFFFAOYSA-N 0.000 claims 1
- OMGBBKBWQPIDOC-UHFFFAOYSA-N n-indol-1-yl-1-[4-(4-methylpiperazin-1-yl)butyl]piperidine-3-carboxamide Chemical compound C1CN(C)CCN1CCCCN1CC(C(=O)NN2C3=CC=CC=C3C=C2)CCC1 OMGBBKBWQPIDOC-UHFFFAOYSA-N 0.000 claims 1
- CVUHMJXJPUNNPV-UHFFFAOYSA-N n-indol-1-yl-1-methyl-3,6-dihydro-2h-pyridine-5-carboxamide Chemical compound C1N(C)CCC=C1C(=O)NN1C2=CC=CC=C2C=C1 CVUHMJXJPUNNPV-UHFFFAOYSA-N 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 230000004770 neurodegeneration Effects 0.000 claims 1
- 208000015122 neurodegenerative disease Diseases 0.000 claims 1
- BVOCPVIXARZNQN-UHFFFAOYSA-N nipecotamide Chemical compound NC(=O)C1CCCNC1 BVOCPVIXARZNQN-UHFFFAOYSA-N 0.000 claims 1
- 231100000252 nontoxic Toxicity 0.000 claims 1
- 230000003000 nontoxic effect Effects 0.000 claims 1
- 238000002638 palliative care Methods 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000000405 phenylalanyl group Chemical group 0.000 claims 1
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 125000001500 prolyl group Chemical group [H]N1C([H])(C(=O)[*])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- ROSDSFDQCJNGOL-UHFFFAOYSA-N protonated dimethyl amine Natural products CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims 1
- 238000000746 purification Methods 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- 125000002072 seryl group Chemical group 0.000 claims 1
- 230000035882 stress Effects 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 1
- LEVOXJAJTGNHDR-UHFFFAOYSA-N tert-butyl 4-[2-[3-(indol-1-ylcarbamoyl)piperidin-1-yl]ethyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1CCN1CC(C(=O)NN2C3=CC=CC=C3C=C2)CCC1 LEVOXJAJTGNHDR-UHFFFAOYSA-N 0.000 claims 1
- 125000001239 threonyl group Chemical group 0.000 claims 1
- 125000002233 tyrosyl group Chemical group 0.000 claims 1
- 125000002114 valyl group Chemical group 0.000 claims 1
- 125000006684 polyhaloalkyl group Polymers 0.000 abstract 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
-
- 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
- A61P25/22—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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Biomedical Technology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Neurosurgery (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Neurology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Epidemiology (AREA)
- Pain & Pain Management (AREA)
- Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0507225A FR2888238B1 (fr) | 2005-07-07 | 2005-07-07 | Nouveaux derives 1h-indole-pyridinecarboxamides et 1h-indole-piperidinecarboxamide, leur procede de preparation et les compositions pharceumatiques qui les contiennent. |
| PCT/FR2006/001610 WO2007006922A2 (fr) | 2005-07-07 | 2006-07-06 | Nouveaux derives 1h-indole-pyridinecarboxamides et 1h-indole-piperidinecarboxamide et leur utilisation comme inducteurs de tyrosine hydroxylase |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20100010T1 true HRP20100010T1 (hr) | 2010-03-31 |
Family
ID=35954102
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20100010T HRP20100010T1 (hr) | 2005-07-07 | 2010-01-08 | Derivati 1h-indol-piridinkarboksamida i 1h-indol-piperidinkarboksamida i njihova uporaba kao izazivača tirozin hidroksilaze |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US20090258883A1 (de) |
| EP (1) | EP1931341B1 (de) |
| JP (1) | JP2009500380A (de) |
| KR (1) | KR20080027925A (de) |
| CN (1) | CN101257905A (de) |
| AR (1) | AR054862A1 (de) |
| AT (1) | ATE447406T1 (de) |
| AU (1) | AU2006268527B2 (de) |
| BR (1) | BRPI0612684A2 (de) |
| CA (1) | CA2614000A1 (de) |
| DE (1) | DE602006010221D1 (de) |
| DK (1) | DK1931341T3 (de) |
| EA (1) | EA014022B1 (de) |
| ES (1) | ES2336250T3 (de) |
| FR (1) | FR2888238B1 (de) |
| GE (1) | GEP20104963B (de) |
| HR (1) | HRP20100010T1 (de) |
| MA (1) | MA29616B1 (de) |
| NO (1) | NO20080677L (de) |
| PL (1) | PL1931341T3 (de) |
| PT (1) | PT1931341E (de) |
| SI (1) | SI1931341T1 (de) |
| UA (1) | UA89544C2 (de) |
| WO (1) | WO2007006922A2 (de) |
| ZA (1) | ZA200800833B (de) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2926077A1 (fr) * | 2008-01-04 | 2009-07-10 | Servier Lab | Nouveaux derives d'1h-indol-1-yl uree, leur procede de preparation et les compositions pharmaceutiques qui les contiennent. |
| EP3202758A1 (de) * | 2016-02-03 | 2017-08-09 | Evonik Degussa GmbH | Reduktive alkylierung von aminen mit orthocarbonsäureestern |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4204998A (en) * | 1974-03-28 | 1980-05-27 | Siegfried Aktiengesellschaft | N-Amino indole derivatives having pharmacological activity |
| ATE115143T1 (de) * | 1987-04-24 | 1994-12-15 | Hoechst Roussel Pharma | N-(pyridinyl)-1h-indol-1-amine, verfahren zu deren herstellung und ihre verwendung als arzneimittel. |
| CA2017621A1 (en) * | 1989-06-23 | 1990-12-23 | Masayuki Kato | Indole derivatives and processes for preparation thereof |
| US5102891A (en) * | 1990-07-23 | 1992-04-07 | Hoechst-Roussel Pharmaceuticals Inc. | 1-(substituted pyridinylamino)-1H-indol-5-yl substituted carbamates |
| US5319096A (en) * | 1992-04-03 | 1994-06-07 | Hoechst-Roussel Pharmaceuticals Inc. | (1H-indol-1-yl)-2-(amino) acetamides and related (1H-indol-1-yl)-(aminoalkyl)amides, pharmaceutical composition and use |
| FR2713644B1 (fr) * | 1993-12-14 | 1996-02-09 | Adir | Nouveaux analogues de l'éburnane, leur procédé de préparation et les compositions pharmaceutiques qui les contiennent. |
| GB9710523D0 (en) * | 1997-05-23 | 1997-07-16 | Smithkline Beecham Plc | Novel compounds |
| US6084098A (en) * | 1999-02-26 | 2000-07-04 | Neurogen Corporation | Benzylpiperazinyl and piperidinyl ethanone derivatives: dopamine receptor subtype specific ligands |
-
2005
- 2005-07-07 FR FR0507225A patent/FR2888238B1/fr not_active Expired - Fee Related
-
2006
- 2006-06-07 UA UAA200801058A patent/UA89544C2/uk unknown
- 2006-07-06 JP JP2008519964A patent/JP2009500380A/ja active Pending
- 2006-07-06 ZA ZA200800833A patent/ZA200800833B/xx unknown
- 2006-07-06 AU AU2006268527A patent/AU2006268527B2/en not_active Ceased
- 2006-07-06 AR ARP060102905A patent/AR054862A1/es unknown
- 2006-07-06 DE DE602006010221T patent/DE602006010221D1/de not_active Expired - Fee Related
- 2006-07-06 GE GEAP200610488A patent/GEP20104963B/en unknown
- 2006-07-06 WO PCT/FR2006/001610 patent/WO2007006922A2/fr active Application Filing
- 2006-07-06 US US11/988,424 patent/US20090258883A1/en not_active Abandoned
- 2006-07-06 SI SI200630492T patent/SI1931341T1/sl unknown
- 2006-07-06 KR KR1020087003060A patent/KR20080027925A/ko active IP Right Grant
- 2006-07-06 EA EA200800208A patent/EA014022B1/ru not_active IP Right Cessation
- 2006-07-06 PT PT06778790T patent/PT1931341E/pt unknown
- 2006-07-06 ES ES06778790T patent/ES2336250T3/es active Active
- 2006-07-06 BR BRPI0612684-7A patent/BRPI0612684A2/pt not_active IP Right Cessation
- 2006-07-06 CA CA002614000A patent/CA2614000A1/fr not_active Abandoned
- 2006-07-06 DK DK06778790.3T patent/DK1931341T3/da active
- 2006-07-06 EP EP06778790A patent/EP1931341B1/de active Active
- 2006-07-06 PL PL06778790T patent/PL1931341T3/pl unknown
- 2006-07-06 AT AT06778790T patent/ATE447406T1/de active
- 2006-07-06 CN CNA2006800324964A patent/CN101257905A/zh active Pending
-
2008
- 2008-01-07 MA MA30553A patent/MA29616B1/fr unknown
- 2008-02-06 NO NO20080677A patent/NO20080677L/no not_active Application Discontinuation
-
2010
- 2010-01-08 HR HR20100010T patent/HRP20100010T1/hr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PT1931341E (pt) | 2009-11-30 |
| GEP20104963B (en) | 2010-04-26 |
| US20090258883A1 (en) | 2009-10-15 |
| MA29616B1 (fr) | 2008-07-01 |
| EP1931341B1 (de) | 2009-11-04 |
| ES2336250T3 (es) | 2010-04-09 |
| WO2007006922A2 (fr) | 2007-01-18 |
| KR20080027925A (ko) | 2008-03-28 |
| CA2614000A1 (fr) | 2007-01-18 |
| ZA200800833B (en) | 2009-04-29 |
| NO20080677L (no) | 2008-02-06 |
| FR2888238B1 (fr) | 2007-09-07 |
| EP1931341A2 (de) | 2008-06-18 |
| ATE447406T1 (de) | 2009-11-15 |
| AU2006268527B2 (en) | 2009-12-24 |
| DK1931341T3 (da) | 2010-03-15 |
| PL1931341T3 (pl) | 2010-06-30 |
| EA014022B1 (ru) | 2010-08-30 |
| WO2007006922A8 (fr) | 2008-01-10 |
| JP2009500380A (ja) | 2009-01-08 |
| SI1931341T1 (sl) | 2010-03-31 |
| DE602006010221D1 (de) | 2009-12-17 |
| FR2888238A1 (fr) | 2007-01-12 |
| EA200800208A1 (ru) | 2008-08-29 |
| BRPI0612684A2 (pt) | 2010-11-30 |
| UA89544C2 (uk) | 2010-02-10 |
| WO2007006922A3 (fr) | 2007-04-05 |
| AR054862A1 (es) | 2007-07-25 |
| AU2006268527A1 (en) | 2007-01-18 |
| CN101257905A (zh) | 2008-09-03 |
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