NZ531110A - Novel imidazopyridine compounds with therapeutic effect - Google Patents
Novel imidazopyridine compounds with therapeutic effectInfo
- Publication number
- NZ531110A NZ531110A NZ531110A NZ53111002A NZ531110A NZ 531110 A NZ531110 A NZ 531110A NZ 531110 A NZ531110 A NZ 531110A NZ 53111002 A NZ53111002 A NZ 53111002A NZ 531110 A NZ531110 A NZ 531110A
- Authority
- NZ
- New Zealand
- Prior art keywords
- alkyl
- formula
- compound
- het
- compounds
- Prior art date
Links
- 230000001225 therapeutic effect Effects 0.000 title description 2
- 125000004857 imidazopyridinyl group Chemical class N1C(=NC2=C1C=CC=N2)* 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 97
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 22
- 150000003839 salts Chemical class 0.000 claims abstract description 17
- -1 S Se Inorganic materials 0.000 claims abstract description 16
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 14
- 150000002367 halogens Chemical class 0.000 claims abstract description 14
- 125000003118 aryl group Chemical group 0.000 claims abstract description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 13
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 13
- 125000001424 substituent group Chemical group 0.000 claims abstract description 11
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 10
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims abstract description 10
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 10
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 6
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 6
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 6
- 125000005843 halogen group Chemical group 0.000 claims abstract description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000001301 oxygen Chemical group 0.000 claims abstract description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 59
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 21
- 239000002253 acid Substances 0.000 claims description 18
- 238000002360 preparation method Methods 0.000 claims description 16
- 238000012360 testing method Methods 0.000 claims description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 15
- 230000008569 process Effects 0.000 claims description 13
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 238000011282 treatment Methods 0.000 claims description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
- 239000004480 active ingredient Substances 0.000 claims description 9
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 7
- 230000002496 gastric effect Effects 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 230000005764 inhibitory process Effects 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 125000004076 pyridyl group Chemical group 0.000 claims description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- 125000002541 furyl group Chemical group 0.000 claims description 6
- 239000012442 inert solvent Substances 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000001544 thienyl group Chemical group 0.000 claims description 6
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 5
- 208000017189 Gastrointestinal inflammatory disease Diseases 0.000 claims description 5
- 239000008280 blood Substances 0.000 claims description 5
- 210000004369 blood Anatomy 0.000 claims description 5
- 230000027119 gastric acid secretion Effects 0.000 claims description 5
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 239000002585 base Substances 0.000 claims description 4
- 210000001156 gastric mucosa Anatomy 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 150000003235 pyrrolidines Chemical class 0.000 claims description 4
- 230000003248 secreting effect Effects 0.000 claims description 4
- 230000028327 secretion Effects 0.000 claims description 4
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- 230000002401 inhibitory effect Effects 0.000 claims description 3
- 238000011321 prophylaxis Methods 0.000 claims description 3
- 210000002784 stomach Anatomy 0.000 claims description 3
- 238000002560 therapeutic procedure Methods 0.000 claims description 3
- 239000011592 zinc chloride Substances 0.000 claims description 3
- 235000005074 zinc chloride Nutrition 0.000 claims description 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 2
- 241000590002 Helicobacter pylori Species 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000002841 Lewis acid Substances 0.000 claims description 2
- 241001465754 Metazoa Species 0.000 claims description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 238000004458 analytical method Methods 0.000 claims description 2
- 239000004599 antimicrobial Substances 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
- 239000003153 chemical reaction reagent Substances 0.000 claims description 2
- 230000008878 coupling Effects 0.000 claims description 2
- 238000010168 coupling process Methods 0.000 claims description 2
- 238000005859 coupling reaction Methods 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 229940037467 helicobacter pylori Drugs 0.000 claims description 2
- 208000015181 infectious disease Diseases 0.000 claims description 2
- 150000007517 lewis acids Chemical class 0.000 claims description 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 2
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims description 2
- 241000282472 Canis lupus familiaris Species 0.000 claims 3
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 claims 2
- 230000009885 systemic effect Effects 0.000 claims 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
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- 208000035944 Duodenal fistula Diseases 0.000 claims 1
- 206010065713 Gastric Fistula Diseases 0.000 claims 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
- 230000037396 body weight Effects 0.000 claims 1
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- 230000008030 elimination Effects 0.000 claims 1
- 238000003379 elimination reaction Methods 0.000 claims 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
- 229960001340 histamine Drugs 0.000 claims 1
- 229960004931 histamine dihydrochloride Drugs 0.000 claims 1
- PPZMYIBUHIPZOS-UHFFFAOYSA-N histamine dihydrochloride Chemical compound Cl.Cl.NCCC1=CN=CN1 PPZMYIBUHIPZOS-UHFFFAOYSA-N 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 238000011552 rat model Methods 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- 238000004448 titration Methods 0.000 claims 1
- 125000004437 phosphorous atom Chemical group 0.000 abstract 1
- 229910052698 phosphorus Inorganic materials 0.000 abstract 1
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- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229940045902 sodium stearyl fumarate Drugs 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000005846 sugar alcohols Chemical class 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229960002180 tetracycline Drugs 0.000 description 1
- 229930101283 tetracycline Natural products 0.000 description 1
- 229940040944 tetracyclines Drugs 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 230000036269 ulceration Effects 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
- 239000001993 wax Substances 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
- A61K31/4353—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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE0102808A SE0102808D0 (sv) | 2001-08-22 | 2001-08-22 | New compounds |
| PCT/SE2002/001489 WO2003018582A1 (en) | 2001-08-22 | 2002-08-21 | Novel imidazopyridine compounds with therapeutic effect |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ531110A true NZ531110A (en) | 2005-10-28 |
Family
ID=20285105
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ531110A NZ531110A (en) | 2001-08-22 | 2002-08-21 | Novel imidazopyridine compounds with therapeutic effect |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US20040220209A1 (enExample) |
| EP (1) | EP1421083A1 (enExample) |
| JP (1) | JP2005501870A (enExample) |
| KR (1) | KR20040036723A (enExample) |
| CN (1) | CN100343252C (enExample) |
| AR (1) | AR035465A1 (enExample) |
| BR (1) | BR0211846A (enExample) |
| CA (1) | CA2456350A1 (enExample) |
| HU (1) | HUP0401350A3 (enExample) |
| IL (1) | IL160143A0 (enExample) |
| IS (1) | IS7159A (enExample) |
| MX (1) | MXPA04001402A (enExample) |
| NO (1) | NO20040760L (enExample) |
| NZ (1) | NZ531110A (enExample) |
| PL (1) | PL367971A1 (enExample) |
| RU (1) | RU2294935C2 (enExample) |
| SE (1) | SE0102808D0 (enExample) |
| WO (1) | WO2003018582A1 (enExample) |
| ZA (1) | ZA200401114B (enExample) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE0301904D0 (sv) | 2003-06-26 | 2003-06-26 | Astrazeneca Ab | Novel imidazopyridine compound II with therapeutic effect |
| EP1974730A1 (en) | 2003-11-03 | 2008-10-01 | AstraZeneca AB | Imidazo[1,2-a]pyridine derivatives for use in the treatment of sleep disturbance due to silent gastro-esophageal reflux |
| EP1711498A2 (en) * | 2004-01-26 | 2006-10-18 | Altana Pharma AG | 1,2,4-triazolo¬1,5-a|pyridines as gastric acid secretion inhibitors |
| EA011512B1 (ru) * | 2004-12-17 | 2009-04-28 | Ракуалиа Фарма Инк. | Производные хромана, полезные в качестве антагонистов кислотной помпы |
| GB0513423D0 (en) * | 2005-06-30 | 2005-08-03 | Glaxo Group Ltd | Novel compounds |
| CA2645007A1 (en) * | 2006-03-17 | 2007-09-27 | Raqualia Pharma Inc. | Chromane derivatives |
| WO2008059373A1 (en) * | 2006-11-17 | 2008-05-22 | Raqualia Pharma Inc. | Imidazo [1, 2-a] pyrazine derivatives and their use as acid pump antagonists |
| KR200449743Y1 (ko) * | 2008-03-11 | 2010-08-05 | 주식회사 보루네오가구 | 파티션용 상부 스크린의 고정구조 |
| FI20086158A0 (fi) | 2008-12-03 | 2008-12-03 | Mikael Dahlstroem | Imidatsopyridiinijohdannaiset |
| JP5802898B2 (ja) | 2009-07-09 | 2015-11-04 | ラクオリア創薬株式会社 | 消化管運動異常が関与する疾患を治療するためのアシッドポンプ拮抗剤 |
| DK2480546T3 (en) * | 2009-09-24 | 2015-02-02 | Hoffmann La Roche | Imidazopyridine or imidazopyrimidinderivater as phosphodiesterase inhibitors 10A |
| FR2962437B1 (fr) | 2010-07-06 | 2012-08-17 | Sanofi Aventis | Derives d'imidazopyridine, leur procede de preparation et leur application en therapeutique |
| KR102120513B1 (ko) * | 2013-01-31 | 2020-06-08 | 네오메드 인스티튜트 | 이미다조피리딘 화합물 및 이의 용도 |
| CA2909477A1 (en) * | 2013-04-30 | 2014-11-06 | F. Hoffmann-La Roche Ag | Pd-catalyzed coupling of pyrazole amides |
| CN106279151A (zh) * | 2015-06-26 | 2017-01-04 | 江苏太瑞生诺生物医药科技有限公司 | 5-(2-(8-((2,6-二甲基苄基)氨基)-2,3-二甲基咪唑并[1,2-a]吡啶-6-甲酰胺基)乙氧基)-5-氧代戊酸的固体形式及其制备方法 |
| EP3930722A4 (en) | 2019-02-25 | 2022-12-28 | Bellus Health Cough Inc. | TREATMENT WITH P2X3 MODULATORS |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA81219B (en) * | 1980-01-23 | 1982-01-27 | Schering Corp | Imidazo (1,2-a) pyridines ,process for their preparation and pharmaceutical compositions containing them |
| DE3269604D1 (en) * | 1981-06-26 | 1986-04-10 | Schering Corp | Novel imidazo(1,2-a)pyridines and pyrazines, processes for their preparation and pharmaceutical compositions containing them |
| US4725601A (en) * | 1985-06-04 | 1988-02-16 | Fujisawa Pharmaceutical Co., Ltd. | Certain imidazo[1,2-a]pyridines useful in the treatment of ulcers |
| EP0228006A1 (en) * | 1985-12-16 | 1987-07-08 | Fujisawa Pharmaceutical Co., Ltd. | Imidazopyridine compounds and processes for preparation thereof |
| IL108520A (en) * | 1993-02-15 | 1997-09-30 | Byk Gulden Lomberg Chem Fab | 2, 3, 8-TRISUBSTITUTED IMIDAZO £1, 2-a| PYRIDINE DERIVATIVES, PROCESSES FOR THE PREPARATION THEREOF AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM |
| UA48122C2 (uk) * | 1993-10-11 | 2002-08-15 | Бік Гульден Ломберг Хеміше Фабрік Гмбх | АЛКОКСІАЛКІЛКАРБАМАТИ ІМІДАЗО[1,2-а]ПІРИДИНІВ, СПОСІБ ЇХ ОДЕРЖАННЯ ТА ЛІКАРСЬКИЙ ЗАСІБ НА ЇХ ОСНОВІ |
| PL180278B1 (pl) * | 1994-07-28 | 2001-01-31 | Byk Gulden Lomberg Chem Fab | Nowe imidazopirydyno-azolidynony, sposób ich wytwarzania oraz srodek farmaceutyczny PL PL PL PL PL PL PL |
| SE9801526D0 (sv) * | 1998-04-29 | 1998-04-29 | Astra Ab | New compounds |
| SE9802794D0 (sv) * | 1998-08-21 | 1998-08-21 | Astra Ab | New compounds |
-
2001
- 2001-08-22 SE SE0102808A patent/SE0102808D0/xx unknown
-
2002
- 2002-08-09 AR ARP020103019A patent/AR035465A1/es not_active Application Discontinuation
- 2002-08-21 MX MXPA04001402A patent/MXPA04001402A/es unknown
- 2002-08-21 PL PL02367971A patent/PL367971A1/xx not_active Application Discontinuation
- 2002-08-21 US US10/487,149 patent/US20040220209A1/en not_active Abandoned
- 2002-08-21 CN CNB028160177A patent/CN100343252C/zh not_active Expired - Fee Related
- 2002-08-21 CA CA002456350A patent/CA2456350A1/en not_active Abandoned
- 2002-08-21 JP JP2003523243A patent/JP2005501870A/ja active Pending
- 2002-08-21 IL IL16014302A patent/IL160143A0/xx unknown
- 2002-08-21 KR KR10-2004-7002466A patent/KR20040036723A/ko not_active Ceased
- 2002-08-21 RU RU2004103628/04A patent/RU2294935C2/ru not_active IP Right Cessation
- 2002-08-21 HU HU0401350A patent/HUP0401350A3/hu unknown
- 2002-08-21 NZ NZ531110A patent/NZ531110A/en unknown
- 2002-08-21 BR BR0211846-7A patent/BR0211846A/pt not_active IP Right Cessation
- 2002-08-21 EP EP02759036A patent/EP1421083A1/en not_active Withdrawn
- 2002-08-21 WO PCT/SE2002/001489 patent/WO2003018582A1/en not_active Ceased
-
2004
- 2004-02-11 ZA ZA200401114A patent/ZA200401114B/en unknown
- 2004-02-20 NO NO20040760A patent/NO20040760L/no not_active Application Discontinuation
- 2004-02-20 IS IS7159A patent/IS7159A/is unknown
Also Published As
| Publication number | Publication date |
|---|---|
| RU2294935C2 (ru) | 2007-03-10 |
| BR0211846A (pt) | 2004-09-08 |
| PL367971A1 (en) | 2005-03-07 |
| JP2005501870A (ja) | 2005-01-20 |
| MXPA04001402A (es) | 2004-05-27 |
| CN100343252C (zh) | 2007-10-17 |
| EP1421083A1 (en) | 2004-05-26 |
| NO20040760L (no) | 2004-02-20 |
| WO2003018582A1 (en) | 2003-03-06 |
| IS7159A (is) | 2004-02-20 |
| HUP0401350A3 (en) | 2009-03-02 |
| US20040220209A1 (en) | 2004-11-04 |
| KR20040036723A (ko) | 2004-04-30 |
| ZA200401114B (en) | 2005-06-22 |
| IL160143A0 (en) | 2004-06-20 |
| AR035465A1 (es) | 2004-05-26 |
| SE0102808D0 (sv) | 2001-08-22 |
| CA2456350A1 (en) | 2003-03-06 |
| HUP0401350A2 (hu) | 2004-12-28 |
| RU2004103628A (ru) | 2005-06-27 |
| CN1543464A (zh) | 2004-11-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PSEA | Patent sealed | ||
| RENW | Renewal (renewal fees accepted) |