HRP20100150T1 - N-(arilalkil)-1h-pirolopiridin-2-karboksamidni derivati, njihovo dobivanje i upotreba - Google Patents
N-(arilalkil)-1h-pirolopiridin-2-karboksamidni derivati, njihovo dobivanje i upotreba Download PDFInfo
- Publication number
- HRP20100150T1 HRP20100150T1 HR20100150T HRP20100150T HRP20100150T1 HR P20100150 T1 HRP20100150 T1 HR P20100150T1 HR 20100150 T HR20100150 T HR 20100150T HR P20100150 T HRP20100150 T HR P20100150T HR P20100150 T1 HRP20100150 T1 HR P20100150T1
- Authority
- HR
- Croatia
- Prior art keywords
- pyrrolo
- alkyl
- pyridine
- cycloalkyl
- methyl
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 31
- 150000001875 compounds Chemical class 0.000 claims abstract 28
- -1 C1-C6-fluoroalkoxy Chemical group 0.000 claims abstract 25
- 125000003118 aryl group Chemical group 0.000 claims abstract 22
- 125000002733 (C1-C6) fluoroalkyl group Chemical group 0.000 claims abstract 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 13
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 12
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract 11
- 229910052799 carbon Inorganic materials 0.000 claims abstract 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract 8
- 125000001424 substituent group Chemical group 0.000 claims abstract 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 7
- 125000005843 halogen group Chemical group 0.000 claims abstract 7
- 150000005255 pyrrolopyridines Chemical class 0.000 claims abstract 7
- XWIYUCRMWCHYJR-UHFFFAOYSA-N 1h-pyrrolo[3,2-b]pyridine Chemical group C1=CC=C2NC=CC2=N1 XWIYUCRMWCHYJR-UHFFFAOYSA-N 0.000 claims abstract 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims abstract 6
- 125000004043 oxo group Chemical group O=* 0.000 claims abstract 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract 5
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract 5
- MVXVYAKCVDQRLW-UHFFFAOYSA-N 1h-pyrrolo[2,3-b]pyridine Chemical group C1=CN=C2NC=CC2=C1 MVXVYAKCVDQRLW-UHFFFAOYSA-N 0.000 claims abstract 4
- XLKDJOPOOHHZAN-UHFFFAOYSA-N 1h-pyrrolo[2,3-c]pyridine Chemical group C1=NC=C2NC=CC2=C1 XLKDJOPOOHHZAN-UHFFFAOYSA-N 0.000 claims abstract 4
- SRSKXJVMVSSSHB-UHFFFAOYSA-N 1h-pyrrolo[3,2-c]pyridine Chemical group N1=CC=C2NC=CC2=C1 SRSKXJVMVSSSHB-UHFFFAOYSA-N 0.000 claims abstract 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims abstract 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims abstract 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims abstract 4
- 229910052736 halogen Inorganic materials 0.000 claims abstract 4
- 150000002367 halogens Chemical class 0.000 claims abstract 4
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 4
- 239000001257 hydrogen Substances 0.000 claims abstract 4
- 125000002619 bicyclic group Chemical group 0.000 claims abstract 3
- 150000001721 carbon Chemical group 0.000 claims abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 3
- 125000005842 heteroatom Chemical group 0.000 claims abstract 3
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 3
- 229910052717 sulfur Inorganic materials 0.000 claims abstract 3
- FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical group C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 claims abstract 2
- XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 claims abstract 2
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000004149 thio group Chemical group *S* 0.000 claims abstract 2
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims abstract 2
- 150000003839 salts Chemical class 0.000 claims 9
- 239000012453 solvate Substances 0.000 claims 9
- 239000002253 acid Substances 0.000 claims 7
- 239000002904 solvent Substances 0.000 claims 3
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 2
- 150000001408 amides Chemical class 0.000 claims 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 2
- 229940079593 drug Drugs 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 125000001041 indolyl group Chemical group 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- 125000005493 quinolyl group Chemical group 0.000 claims 2
- 238000010992 reflux Methods 0.000 claims 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims 1
- 208000020401 Depressive disease Diseases 0.000 claims 1
- 208000018522 Gastrointestinal disease Diseases 0.000 claims 1
- 208000007514 Herpes zoster Diseases 0.000 claims 1
- XQFRJNBWHJMXHO-RRKCRQDMSA-N IDUR Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(I)=C1 XQFRJNBWHJMXHO-RRKCRQDMSA-N 0.000 claims 1
- 206010061218 Inflammation Diseases 0.000 claims 1
- 208000002193 Pain Diseases 0.000 claims 1
- 208000003251 Pruritus Diseases 0.000 claims 1
- 201000004681 Psoriasis Diseases 0.000 claims 1
- 108010025083 TRPV1 receptor Proteins 0.000 claims 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims 1
- 125000004622 benzoxazinyl group Chemical group O1NC(=CC2=C1C=CC=C2)* 0.000 claims 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 238000006482 condensation reaction Methods 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- 125000000723 dihydrobenzofuranyl group Chemical group O1C(CC2=C1C=CC=C2)* 0.000 claims 1
- 125000005436 dihydrobenzothiophenyl group Chemical group S1C(CC2=C1C=CC=C2)* 0.000 claims 1
- 125000005434 dihydrobenzoxazinyl group Chemical group O1N(CCC2=C1C=CC=C2)* 0.000 claims 1
- 125000004609 dihydroquinazolinyl group Chemical group N1(CN=CC2=CC=CC=C12)* 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims 1
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims 1
- 230000004054 inflammatory process Effects 0.000 claims 1
- 230000007794 irritation Effects 0.000 claims 1
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 claims 1
- 125000004594 isoindolinyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 claims 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims 1
- 125000005956 isoquinolyl group Chemical group 0.000 claims 1
- 230000007803 itching Effects 0.000 claims 1
- 229940126601 medicinal product Drugs 0.000 claims 1
- 210000004400 mucous membrane Anatomy 0.000 claims 1
- 230000001575 pathological effect Effects 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims 1
- 208000023504 respiratory system disease Diseases 0.000 claims 1
- 125000004434 sulfur atom Chemical group 0.000 claims 1
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 claims 1
- 208000014001 urinary system disease Diseases 0.000 claims 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 3
- 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 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
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- 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
- A61K31/4353—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 ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—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 ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
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- A—HUMAN NECESSITIES
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- 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
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- A61P1/18—Drugs for disorders of the alimentary tract or the digestive system for pancreatic disorders, e.g. pancreatic enzymes
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
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- A—HUMAN NECESSITIES
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- A61P13/00—Drugs for disorders of the urinary system
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- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
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- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/08—Drugs for genital or sexual disorders; Contraceptives for gonadal disorders or for enhancing fertility, e.g. inducers of ovulation or of spermatogenesis
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- 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
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P31/12—Antivirals
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- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Urology & Nephrology (AREA)
- Virology (AREA)
- Dermatology (AREA)
- Pulmonology (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Diabetes (AREA)
- Oncology (AREA)
- Pain & Pain Management (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Communicable Diseases (AREA)
- Cardiology (AREA)
- Molecular Biology (AREA)
- Biotechnology (AREA)
- Heart & Thoracic Surgery (AREA)
- Vascular Medicine (AREA)
- Rheumatology (AREA)
- Ophthalmology & Optometry (AREA)
- Psychiatry (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Gynecology & Obstetrics (AREA)
- Pregnancy & Childbirth (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0507804A FR2888848B1 (fr) | 2005-07-22 | 2005-07-22 | Derives de n-(arylalkyl)-1h-pyrrrolopyridine-2-carboxamides, leur preparation et leur application en therapeutique |
| PCT/FR2006/001767 WO2007010138A2 (fr) | 2005-07-22 | 2006-07-19 | Derives de ν-(arylalkyl)-1h-pyrrolopyridine-2-carboxamides, leur preparation et leur application en therapeutique |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20100150T1 true HRP20100150T1 (hr) | 2010-04-30 |
Family
ID=36039505
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20100150T HRP20100150T1 (hr) | 2005-07-22 | 2010-03-16 | N-(arilalkil)-1h-pirolopiridin-2-karboksamidni derivati, njihovo dobivanje i upotreba |
Country Status (35)
| Country | Link |
|---|---|
| US (2) | US7763636B2 (no) |
| EP (1) | EP1912644B1 (no) |
| JP (1) | JP4938012B2 (no) |
| KR (1) | KR101257969B1 (no) |
| CN (1) | CN101247808B (no) |
| AR (1) | AR057668A1 (no) |
| AT (1) | ATE451923T1 (no) |
| AU (1) | AU2006271518B2 (no) |
| BR (1) | BRPI0614066A2 (no) |
| CA (1) | CA2615676C (no) |
| CR (1) | CR9643A (no) |
| CY (1) | CY1109891T1 (no) |
| DE (1) | DE602006011170D1 (no) |
| DK (1) | DK1912644T3 (no) |
| EA (1) | EA013747B1 (no) |
| EC (1) | ECSP088105A (no) |
| ES (1) | ES2338363T3 (no) |
| FR (1) | FR2888848B1 (no) |
| HR (1) | HRP20100150T1 (no) |
| IL (1) | IL188520A (no) |
| MA (1) | MA29617B1 (no) |
| MX (1) | MX2008001018A (no) |
| MY (1) | MY145062A (no) |
| NI (1) | NI200800021A (no) |
| NO (1) | NO20080394L (no) |
| NZ (1) | NZ564870A (no) |
| PL (1) | PL1912644T3 (no) |
| PT (1) | PT1912644E (no) |
| RS (1) | RS51233B (no) |
| SI (1) | SI1912644T1 (no) |
| TN (1) | TNSN07485A1 (no) |
| TW (1) | TWI386407B (no) |
| UA (1) | UA93881C2 (no) |
| WO (1) | WO2007010138A2 (no) |
| ZA (1) | ZA200800439B (no) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2888847B1 (fr) | 2005-07-22 | 2007-08-31 | Sanofi Aventis Sa | Derives de n-(heteriaryl)-1-heteorarylalkyl-1h-indole-2- carboxamides, leur preparation et application en therapeutique |
| FR2910473B1 (fr) | 2006-12-26 | 2009-02-13 | Sanofi Aventis Sa | Derives de n-(amino-heteroaryl)-1h-pyrrolopyridine-2- carboxamides, leur preparation et leur application en therapeutique. |
| FR2911605B1 (fr) * | 2007-01-19 | 2009-04-17 | Sanofi Aventis Sa | Derives de pyrrolopyridine-2-carbowamides, leur preparation et leur application en therapeutique |
| WO2008157179A2 (en) * | 2007-06-12 | 2008-12-24 | Genentech, Inc. | N-substituted azaindoles and methods of use |
| FR2919610B1 (fr) * | 2007-08-02 | 2009-10-16 | Sanofi Aventis Sa | Derives de n-heteroaryl-carboxamides tricycliques,leur preparation et leur application en therapeutique |
| FR2926556B1 (fr) * | 2008-01-22 | 2010-02-19 | Sanofi Aventis | Derives de carboxamides n-azabicycliques, leur preparation et leur application en therapeutique |
| FR2926554B1 (fr) * | 2008-01-22 | 2010-03-12 | Sanofi Aventis | Derives de carboxamides azabicycliques, leur preparation et leur application en therapeutique |
| FR2926555B1 (fr) | 2008-01-22 | 2010-02-19 | Sanofi Aventis | Derives bicycliques de carboxamides azabicycliques, leur preparation et leur application en therapeutique |
| GB0915892D0 (en) * | 2009-09-10 | 2009-10-14 | Smithkline Beecham Corp | Compounds |
| GB201913756D0 (en) * | 2019-09-24 | 2019-11-06 | Chromatwist Ltd | Contrast agent |
| US20230137893A1 (en) * | 2020-02-05 | 2023-05-04 | The Rockefeller University | PYRROLO[2,3-b]PYRIDINE-3-CARBOXAMIDE COMPOSITIONS AND METHODS FOR AMELIORATING HEARING LOSS |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH08295667A (ja) * | 1995-04-27 | 1996-11-12 | Takeda Chem Ind Ltd | 複素環化合物、その製造法および剤 |
| JP4241970B2 (ja) * | 1998-10-30 | 2009-03-18 | 中外製薬株式会社 | アミド結合を有するインドール誘導体、及びモノ又はジアザインドール誘導体 |
| US6436965B1 (en) * | 2000-03-02 | 2002-08-20 | Merck Frosst Canada & Co. | PDE IV inhibiting amides, compositions and methods of treatment |
| TW200403223A (en) * | 2002-02-15 | 2004-03-01 | Glaxo Group Ltd | Novel compounds |
| AU2003281044A1 (en) * | 2002-07-11 | 2004-02-02 | Takeda Pharmaceutical Company Limited | Pyrrolopyridine derivative and use thereof |
| JP2004091480A (ja) * | 2002-07-11 | 2004-03-25 | Takeda Chem Ind Ltd | ピロロピリジン誘導体およびその用途 |
| JP4909068B2 (ja) * | 2003-02-14 | 2012-04-04 | グラクソ グループ リミテッド | カルボキサミド誘導体 |
| US7544803B2 (en) * | 2004-01-23 | 2009-06-09 | Amgen Inc. | Vanilloid receptor ligands and their use in treatments |
| FR2897061B1 (fr) * | 2006-02-03 | 2010-09-03 | Sanofi Aventis | Derives de n-heteroaryl-carboxamides tricycliques contenant un motif benzimidazole, leur preparation et leur application en therapeutique. |
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