AU2004213104B2 - Indazolamides with analgesic activity - Google Patents
Indazolamides with analgesic activity Download PDFInfo
- Publication number
- AU2004213104B2 AU2004213104B2 AU2004213104A AU2004213104A AU2004213104B2 AU 2004213104 B2 AU2004213104 B2 AU 2004213104B2 AU 2004213104 A AU2004213104 A AU 2004213104A AU 2004213104 A AU2004213104 A AU 2004213104A AU 2004213104 B2 AU2004213104 B2 AU 2004213104B2
- Authority
- AU
- Australia
- Prior art keywords
- methyl
- acid
- compound
- pharmaceutically acceptable
- indazole
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
Links
- DITBWPUMEUDVLU-UHFFFAOYSA-N 1h-indazole-3-carboxamide Chemical class C1=CC=C2C(C(=O)N)=NNC2=C1 DITBWPUMEUDVLU-UHFFFAOYSA-N 0.000 title claims description 17
- 230000000202 analgesic effect Effects 0.000 title description 8
- 150000001875 compounds Chemical class 0.000 claims description 39
- 150000003839 salts Chemical group 0.000 claims description 25
- 239000002253 acid Substances 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 17
- 208000004454 Hyperalgesia Diseases 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 238000011282 treatment Methods 0.000 claims description 13
- 230000008569 process Effects 0.000 claims description 11
- -1 acetylamino, sulphonylmethyl Chemical group 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims description 10
- 239000003085 diluting agent Substances 0.000 claims description 9
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 9
- 239000011707 mineral Substances 0.000 claims description 9
- 208000035154 Hyperesthesia Diseases 0.000 claims description 8
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- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
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- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
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- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 4
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- 125000003118 aryl group Chemical group 0.000 claims description 4
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- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
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- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims 5
- 238000004519 manufacturing process Methods 0.000 claims 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 101150058580 cls-3 gene Proteins 0.000 claims 1
- QISWSSYWVMIHSJ-UHFFFAOYSA-N n-[[1-(2-anilino-2-oxoethyl)piperidin-4-yl]methyl]-1-propan-2-ylindazole-3-carboxamide Chemical compound C12=CC=CC=C2N(C(C)C)N=C1C(=O)NCC(CC1)CCN1CC(=O)NC1=CC=CC=C1 QISWSSYWVMIHSJ-UHFFFAOYSA-N 0.000 claims 1
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- NIUACBXGITUJJM-UHFFFAOYSA-N n-[[1-[2-(4-hydroxyanilino)-2-oxoethyl]piperidin-4-yl]methyl]-1-propan-2-ylindazole-3-carboxamide Chemical compound C12=CC=CC=C2N(C(C)C)N=C1C(=O)NCC(CC1)CCN1CC(=O)NC1=CC=C(O)C=C1 NIUACBXGITUJJM-UHFFFAOYSA-N 0.000 claims 1
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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
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P23/00—Anaesthetics
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- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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]
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/26—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Anesthesiology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT000287A ITMI20030287A1 (it) | 2003-02-18 | 2003-02-18 | Indazolammidi dotate di attivita' analgesica metodo, per |
| ITMI2003A000287 | 2003-02-18 | ||
| PCT/EP2004/000647 WO2004074275A1 (en) | 2003-02-18 | 2004-01-26 | Indazolamides with analgesic activity |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2004213104A1 AU2004213104A1 (en) | 2004-09-02 |
| AU2004213104B2 true AU2004213104B2 (en) | 2010-07-08 |
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|---|---|---|---|
| AU2004213104A Ceased AU2004213104B2 (en) | 2003-02-18 | 2004-01-26 | Indazolamides with analgesic activity |
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| US (2) | US7632849B2 (enExample) |
| EP (1) | EP1594859B1 (enExample) |
| JP (1) | JP4724651B2 (enExample) |
| KR (1) | KR101108222B1 (enExample) |
| CN (2) | CN100347168C (enExample) |
| AR (1) | AR043186A1 (enExample) |
| AT (1) | ATE471934T1 (enExample) |
| AU (1) | AU2004213104B2 (enExample) |
| CA (1) | CA2511984C (enExample) |
| DE (1) | DE602004027792D1 (enExample) |
| DK (1) | DK1594859T3 (enExample) |
| EA (1) | EA009077B1 (enExample) |
| ES (1) | ES2345983T3 (enExample) |
| GE (1) | GEP20074075B (enExample) |
| IL (1) | IL169285A (enExample) |
| IT (1) | ITMI20030287A1 (enExample) |
| MX (1) | MXPA05008730A (enExample) |
| PL (1) | PL215870B1 (enExample) |
| PT (1) | PT1594859E (enExample) |
| SI (1) | SI1594859T1 (enExample) |
| UA (1) | UA79537C2 (enExample) |
| WO (1) | WO2004074275A1 (enExample) |
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| ITMI20031468A1 (it) * | 2003-07-18 | 2005-01-19 | Acraf | Farmaco ativo nel dolore neuropatico |
| EA010891B9 (ru) * | 2004-06-15 | 2012-08-30 | Пфайзер Инк. | Производные бензимидазолонкарбоновой кислоты |
| PL2105164T3 (pl) * | 2008-03-25 | 2011-05-31 | Affectis Pharmaceuticals Ag | Nowi antagoniści P2X7R i ich zastosowanie |
| US8815892B2 (en) | 2008-03-25 | 2014-08-26 | Affectis Pharmaceuticals Ag | P2X7R antagonists and their use |
| SI2243772T1 (sl) * | 2009-04-14 | 2012-05-31 | Affectis Pharmaceuticals Ag | Novi antagonisti p x r in njihova uporaba |
| US9611249B2 (en) | 2012-02-12 | 2017-04-04 | Aziende Chimiche Riunite Angelini Francesco A.C.R.A.F. S.P.A. | 1H-indazole-3-carboxamide compounds as glycogen synthase kinase 3 beta inhibitors |
| SG10201701171TA (en) * | 2012-02-21 | 2017-04-27 | Acraf | Use of 1h-indazole-3-carboxamide compounds as glycogen synthase kinase 3 beta inhibitors |
| US8889730B2 (en) | 2012-04-10 | 2014-11-18 | Pfizer Inc. | Indole and indazole compounds that activate AMPK |
| CA2905242C (en) | 2013-03-15 | 2016-11-29 | Pfizer Inc. | Indole compounds that activate ampk |
| UA128089C2 (uk) | 2018-05-07 | 2024-04-03 | Ацьєнде Кіміке Ріуніте Анджеліні Франческо - А.Чі.Р.А.Ф. С.П.А. | 1h-індазол-3-карбоксамідні сполуки як інгібітори кінази-3 бета глікогенсинтази |
| CN109336890B (zh) * | 2018-11-17 | 2020-03-20 | 重庆文理学院 | 一种吲唑类衍生物的合成方法及抗肿瘤应用 |
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| US3705175A (en) * | 1969-04-01 | 1972-12-05 | Egyt Gyogyszervegyeszeti Gyar | Indazole-3-carboxylic amides |
| IL117438A (en) | 1995-03-16 | 2001-12-23 | Lilly Co Eli | Indazolecarboxamides, their preparation and pharmaceutical compositions containing them |
| US5654320A (en) * | 1995-03-16 | 1997-08-05 | Eli Lilly And Company | Indazolecarboxamides |
| WO1996038420A1 (en) * | 1995-05-31 | 1996-12-05 | Nisshin Flour Milling Co., Ltd. | Indazole derivatives having monocyclic amino group |
| WO1997017208A1 (fr) * | 1995-11-08 | 1997-05-15 | Toray Industries, Inc. | Plaque planographique originale, sans eau, pour dessin direct |
| NZ334064A (en) | 1996-08-16 | 2000-08-25 | Smithkline Beecham Plc | Process for the preparation of N-[(1-nbutyl-4-piperidyl)methyl] -3,4-dihydro-2H-[1,3]oxazino[3,2-a] indole-10-carboxamide and salts and intermediates in the process |
| IT1291569B1 (it) | 1997-04-15 | 1999-01-11 | Angelini Ricerche Spa | Indazolammidi come agenti serotoninergici |
| US6339087B1 (en) * | 1997-08-18 | 2002-01-15 | Syntex (U.S.A.) Llc | Cyclic amine derivatives-CCR-3 receptor antagonists |
| US6069152A (en) * | 1997-10-07 | 2000-05-30 | Eli Lilly And Company | 5-HT4 agonists and antagonists |
| US6407103B2 (en) * | 1998-04-21 | 2002-06-18 | Bristol-Myers Squibb Pharma Company | Indeno [1,2-c] pyrazol-4-ones and their uses |
| EP1071668B1 (en) * | 1998-04-21 | 2009-06-03 | Bristol-Myers Squibb Pharma Company | 5-aminoindeno[1,2-c]pyrazol-4-ones as anti-cancer and anti-proliferative agents |
-
2003
- 2003-02-18 IT IT000287A patent/ITMI20030287A1/it unknown
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2004
- 2004-01-26 DE DE602004027792T patent/DE602004027792D1/de not_active Expired - Lifetime
- 2004-01-26 CN CNB2004800025681A patent/CN100347168C/zh not_active Expired - Fee Related
- 2004-01-26 GE GEAP20048983A patent/GEP20074075B/en unknown
- 2004-01-26 AT AT04705070T patent/ATE471934T1/de active
- 2004-01-26 ES ES04705070T patent/ES2345983T3/es not_active Expired - Lifetime
- 2004-01-26 JP JP2006501608A patent/JP4724651B2/ja not_active Expired - Fee Related
- 2004-01-26 DK DK04705070.3T patent/DK1594859T3/da active
- 2004-01-26 CA CA2511984A patent/CA2511984C/en not_active Expired - Fee Related
- 2004-01-26 KR KR1020057014055A patent/KR101108222B1/ko not_active Expired - Fee Related
- 2004-01-26 PL PL377236A patent/PL215870B1/pl unknown
- 2004-01-26 AU AU2004213104A patent/AU2004213104B2/en not_active Ceased
- 2004-01-26 EP EP04705070A patent/EP1594859B1/en not_active Expired - Lifetime
- 2004-01-26 SI SI200431488T patent/SI1594859T1/sl unknown
- 2004-01-26 US US10/541,209 patent/US7632849B2/en not_active Expired - Fee Related
- 2004-01-26 EA EA200501164A patent/EA009077B1/ru not_active IP Right Cessation
- 2004-01-26 PT PT04705070T patent/PT1594859E/pt unknown
- 2004-01-26 WO PCT/EP2004/000647 patent/WO2004074275A1/en not_active Ceased
- 2004-01-26 MX MXPA05008730A patent/MXPA05008730A/es active IP Right Grant
- 2004-01-26 CN CN2007101801011A patent/CN101139341B/zh not_active Expired - Fee Related
- 2004-01-26 UA UAA200508163A patent/UA79537C2/uk unknown
- 2004-02-16 AR ARP040100467A patent/AR043186A1/es not_active Application Discontinuation
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2005
- 2005-06-20 IL IL169285A patent/IL169285A/en not_active IP Right Cessation
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2009
- 2009-10-28 US US12/607,463 patent/US8519139B2/en not_active Expired - Fee Related
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