ZA200200177B - Indole derivatives and their use for the treatment of osteoporosis amongst other applications. - Google Patents
Indole derivatives and their use for the treatment of osteoporosis amongst other applications. Download PDFInfo
- Publication number
- ZA200200177B ZA200200177B ZA200200177A ZA200200177A ZA200200177B ZA 200200177 B ZA200200177 B ZA 200200177B ZA 200200177 A ZA200200177 A ZA 200200177A ZA 200200177 A ZA200200177 A ZA 200200177A ZA 200200177 B ZA200200177 B ZA 200200177B
- Authority
- ZA
- South Africa
- Prior art keywords
- formula
- compound
- pharmaceutically acceptable
- indol
- dichloro
- Prior art date
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- 238000011282 treatment Methods 0.000 title claims description 20
- 208000001132 Osteoporosis Diseases 0.000 title claims description 6
- 229940054051 antipsychotic indole derivative Drugs 0.000 title description 2
- 150000002475 indoles Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 85
- 150000003839 salts Chemical class 0.000 claims description 40
- 239000012453 solvate Substances 0.000 claims description 33
- -1 hydroxy, methoxy, ethoxy, propoxy, benzyloxy, carboxyethoxy, hydroxyethoxy Chemical group 0.000 claims description 28
- 229910052739 hydrogen Inorganic materials 0.000 claims description 25
- 239000001257 hydrogen Substances 0.000 claims description 25
- 201000010099 disease Diseases 0.000 claims description 20
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 210000002997 osteoclast Anatomy 0.000 claims description 11
- 125000000623 heterocyclic group Chemical group 0.000 claims description 10
- 150000002431 hydrogen Chemical class 0.000 claims description 10
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 9
- 230000000694 effects Effects 0.000 claims description 7
- 206010028980 Neoplasm Diseases 0.000 claims description 6
- 238000007112 amidation reaction Methods 0.000 claims description 6
- 238000011321 prophylaxis Methods 0.000 claims description 6
- 230000009435 amidation Effects 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 125000003386 piperidinyl group Chemical group 0.000 claims description 5
- CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 claims description 4
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- 230000002491 angiogenic effect Effects 0.000 claims description 4
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- 239000003814 drug Substances 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 229940037467 helicobacter pylori Drugs 0.000 claims description 4
- 208000037797 influenza A Diseases 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 4
- 208000003265 stomatitis Diseases 0.000 claims description 4
- 208000005925 vesicular stomatitis Diseases 0.000 claims description 4
- 241000124008 Mammalia Species 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000006239 protecting group Chemical group 0.000 claims description 2
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- 231100000397 ulcer Toxicity 0.000 claims 3
- 230000003612 virological effect Effects 0.000 claims 3
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 2
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 2
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 2
- FQZJDLJDCHIFIS-UHFFFAOYSA-N 4-(5,6-dichloro-1h-indol-2-yl)-2,5-dimethoxy-n-(1,2,2,6,6-pentamethylpiperidin-4-yl)benzamide Chemical compound COC1=CC(C=2NC3=CC(Cl)=C(Cl)C=C3C=2)=C(OC)C=C1C(=O)NC1CC(C)(C)N(C)C(C)(C)C1 FQZJDLJDCHIFIS-UHFFFAOYSA-N 0.000 claims 1
- VNVUDBDBNZARAF-UHFFFAOYSA-N 4-(5,6-dichloro-1h-indol-2-yl)-3-ethoxy-n-(2,2,6,6-tetramethylpiperidin-4-yl)benzamide Chemical compound C=1C=C(C=2NC3=CC(Cl)=C(Cl)C=C3C=2)C(OCC)=CC=1C(=O)NC1CC(C)(C)NC(C)(C)C1 VNVUDBDBNZARAF-UHFFFAOYSA-N 0.000 claims 1
- QACGTAHQFJDDGA-UHFFFAOYSA-N 4-(5,6-dichloro-1h-indol-2-yl)-3-ethoxy-n-pyridin-3-ylbenzamide Chemical compound C=1C=C(C=2NC3=CC(Cl)=C(Cl)C=C3C=2)C(OCC)=CC=1C(=O)NC1=CC=CN=C1 QACGTAHQFJDDGA-UHFFFAOYSA-N 0.000 claims 1
- XVWQBCXFAYCVTE-UHFFFAOYSA-N 4-(5,6-dichloro-1h-indol-2-yl)-3-hydroxy-n-(2,2,6,6-tetramethylpiperidin-4-yl)benzamide Chemical compound C1C(C)(C)NC(C)(C)CC1NC(=O)C(C=C1O)=CC=C1C1=CC2=CC(Cl)=C(Cl)C=C2N1 XVWQBCXFAYCVTE-UHFFFAOYSA-N 0.000 claims 1
- LBCZIZBNERCLNA-UHFFFAOYSA-N 4-(5,6-dichloro-1h-indol-2-yl)-3-methoxy-n-[3-[4-(3-methoxyphenyl)piperazin-1-yl]propyl]benzamide Chemical compound COC1=CC=CC(N2CCN(CCCNC(=O)C=3C=C(OC)C(C=4NC5=CC(Cl)=C(Cl)C=C5C=4)=CC=3)CC2)=C1 LBCZIZBNERCLNA-UHFFFAOYSA-N 0.000 claims 1
- RRIJSBXUALMIPL-UHFFFAOYSA-N 4-(5,6-dichloro-1h-indol-2-yl)-3-phenylmethoxy-n-(2,2,6,6-tetramethylpiperidin-4-yl)benzamide Chemical compound C1C(C)(C)NC(C)(C)CC1NC(=O)C(C=C1OCC=2C=CC=CC=2)=CC=C1C1=CC2=CC(Cl)=C(Cl)C=C2N1 RRIJSBXUALMIPL-UHFFFAOYSA-N 0.000 claims 1
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- PJJBAZMFVZAAPU-UHFFFAOYSA-N 4-(6-chloro-5-methoxy-1h-indol-2-yl)-3-ethoxy-n-(2,2,6,6-tetramethylpiperidin-4-yl)benzamide Chemical compound C=1C=C(C=2NC3=CC(Cl)=C(OC)C=C3C=2)C(OCC)=CC=1C(=O)NC1CC(C)(C)NC(C)(C)C1 PJJBAZMFVZAAPU-UHFFFAOYSA-N 0.000 claims 1
- 125000002474 dimethylaminoethoxy group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])O* 0.000 claims 1
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- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- RLISWLLILOTWGG-UHFFFAOYSA-N salamidacetic acid Chemical compound NC(=O)C1=CC=CC=C1OCC(O)=O RLISWLLILOTWGG-UHFFFAOYSA-N 0.000 claims 1
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- 125000000217 alkyl group Chemical group 0.000 description 7
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- 239000000010 aprotic solvent Substances 0.000 description 1
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 238000012790 confirmation Methods 0.000 description 1
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- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
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- RRNKTEDWRCQWSN-UHFFFAOYSA-N n-[3-[4-(3-chlorophenyl)piperazin-1-yl]propyl]-4-(5,6-dichloro-1h-indol-2-yl)-2-methoxybenzamide Chemical compound COC1=CC(C=2NC3=CC(Cl)=C(Cl)C=C3C=2)=CC=C1C(=O)NCCCN(CC1)CCN1C1=CC=CC(Cl)=C1 RRNKTEDWRCQWSN-UHFFFAOYSA-N 0.000 description 1
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- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
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- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000012026 peptide coupling reagents Substances 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
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- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 1
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- 239000011591 potassium Substances 0.000 description 1
- 239000012256 powdered iron Substances 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
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- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- AWUCVROLDVIAJX-GSVOUGTGSA-N sn-glycerol 3-phosphate Chemical compound OC[C@@H](O)COP(O)(O)=O AWUCVROLDVIAJX-GSVOUGTGSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
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- 230000000707 stereoselective effect Effects 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
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- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 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
- 125000004001 thioalkyl group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
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- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
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- Biomedical Technology (AREA)
- Molecular Biology (AREA)
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- Pain & Pain Management (AREA)
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- Obesity (AREA)
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- Vascular Medicine (AREA)
- Tropical Medicine & Parasitology (AREA)
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Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9914371.1A GB9914371D0 (en) | 1999-06-18 | 1999-06-18 | Novel compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200200177B true ZA200200177B (en) | 2003-09-23 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200200177A ZA200200177B (en) | 1999-06-18 | 2002-01-09 | Indole derivatives and their use for the treatment of osteoporosis amongst other applications. |
Country Status (30)
| Country | Link |
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| US (2) | US6787550B1 (zh) |
| EP (1) | EP1212317B1 (zh) |
| JP (1) | JP2003503490A (zh) |
| KR (1) | KR100701109B1 (zh) |
| CN (1) | CN1179960C (zh) |
| AR (1) | AR024390A1 (zh) |
| AT (1) | ATE276245T1 (zh) |
| AU (1) | AU768726B2 (zh) |
| BR (1) | BR0011708A (zh) |
| CA (1) | CA2376657A1 (zh) |
| CO (1) | CO5200757A1 (zh) |
| CZ (1) | CZ301697B6 (zh) |
| DE (1) | DE60013859T2 (zh) |
| DK (1) | DK1212317T3 (zh) |
| ES (1) | ES2226870T3 (zh) |
| GB (1) | GB9914371D0 (zh) |
| GC (1) | GC0000341A (zh) |
| HK (2) | HK1048468B (zh) |
| HU (1) | HUP0202049A3 (zh) |
| IL (2) | IL147012A0 (zh) |
| MX (1) | MXPA01013277A (zh) |
| MY (1) | MY129425A (zh) |
| NO (1) | NO322313B1 (zh) |
| NZ (1) | NZ516131A (zh) |
| PL (1) | PL352964A1 (zh) |
| PT (1) | PT1212317E (zh) |
| TR (1) | TR200103683T2 (zh) |
| TW (1) | TWI248440B (zh) |
| WO (1) | WO2001002388A1 (zh) |
| ZA (1) | ZA200200177B (zh) |
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| EP1601251B1 (en) | 2003-02-13 | 2014-11-12 | Wellstat Therapeutics Corporation | Compounds for the treatment of metabolic disorders |
| US20060205751A1 (en) * | 2003-07-15 | 2006-09-14 | Smithkline Beecham Corporation | Novel compounds |
| ITMI20040875A1 (it) * | 2004-04-30 | 2004-07-30 | Ist Naz Stud Cura Dei Tumori | Derivati indolici utili per il trattamento della resistenza agli agenti antitumorali |
| NZ554232A (en) | 2004-09-17 | 2010-09-30 | Idenix Pharmaceuticals Inc | Phosphoindoles as HIV inhibitors |
| WO2006041874A2 (en) * | 2004-10-04 | 2006-04-20 | Myriad Genetics, Inc. | Compounds for alzheimer's disease |
| US7833805B2 (en) * | 2004-10-21 | 2010-11-16 | University Of Cincinnati | Selectively permeable membranes on porous substrates |
| WO2007010723A1 (ja) * | 2005-07-20 | 2007-01-25 | National University Corporation Kanazawa University | トリプトファン誘導体及びその用途 |
| ITRM20050390A1 (it) * | 2005-07-22 | 2007-01-23 | Giuliani Spa | Composti e loro sali specifici per i recettori ppar ed i recettori per l'egf e loro uso in campo medico. |
| ITRM20050389A1 (it) | 2005-07-22 | 2007-01-23 | Giuliani Spa | Composti e loro sali specifici per i recettori ppar ed i recettori per l'egf e loro uso in campo medico. |
| KR20080035700A (ko) | 2005-08-15 | 2008-04-23 | 아이알엠 엘엘씨 | Ｔｐｏ 모방체로서의 화합물 및 조성물 |
| EP1779849A1 (en) * | 2005-10-28 | 2007-05-02 | Nikem Research S.R.L. | V-ATPase inhibitors for the treatment of septic shock |
| EP1779848A1 (en) * | 2005-10-28 | 2007-05-02 | Nikem Research S.R.L. | V-ATPase inhibitors for the treatment of inflammatory and autoimmune diseases |
| AU2007208125B2 (en) | 2006-01-25 | 2012-04-05 | Wellstat Therapeutics Corporation | Compounds for the treatment of metabolic disorders |
| JP2009531280A (ja) | 2006-01-25 | 2009-09-03 | ウェルスタット セラピューティクス コーポレイション | 代謝障害を処置するための化合物 |
| AU2007212104A1 (en) | 2006-02-02 | 2007-08-16 | Wellstat Therapeutics Corporation | Compounds for the treatment of metabolic disorders |
| US8222261B2 (en) * | 2006-07-13 | 2012-07-17 | GlaxoSmithKline, LLC | Chemical compounds |
| EP2078029B1 (en) | 2006-09-29 | 2014-05-14 | IDENIX Pharmaceuticals, Inc. | Enantiomerically pure phosphoindole as hiv inhibitor |
| UA107562C2 (uk) | 2008-12-05 | 2015-01-26 | Спосіб лікування псоріазу | |
| NZ595080A (en) | 2009-02-16 | 2013-09-27 | Giuliani Int Ltd | Methods of treating hair related conditions |
| WO2010144611A2 (en) * | 2009-06-10 | 2010-12-16 | 3-V Biosciences, Inc. | Antivirals that target transporters, carriers, and ion channels |
| JP5902172B2 (ja) * | 2010-09-08 | 2016-04-13 | ブリストル−マイヤーズ スクイブ カンパニーＢｒｉｓｔｏｌ−Ｍｙｅｒｓ Ｓｑｕｉｂｂ Ｃｏｍｐａｎｙ | 広範囲のインフルエンザ抗ウイルス薬としての新規ピペラジン類似体 |
| WO2012045451A1 (en) | 2010-10-05 | 2012-04-12 | Ludwig-Maximilians-Universitaet Muenchen | Novel therapeutic treatment of progranulin-dependent diseases |
| US20120142627A1 (en) * | 2010-12-06 | 2012-06-07 | Emory University | Monophosphate prodrugs of dapd and analogs thereof |
| JP6301844B2 (ja) | 2012-02-09 | 2018-03-28 | ノグラ ファーマ リミテッド | 線維症の処置方法 |
| CN104284655B (zh) | 2012-04-18 | 2017-10-27 | 诺格拉制药有限公司 | 治疗乳糖不耐受的方法 |
| CA3128302A1 (en) | 2019-02-08 | 2020-08-13 | Nogra Pharma Limited | Process of making 3-(4'-aminophenyl)-2-methoxypropionic acid, and analogs and intermediates thereof |
| CN113024432A (zh) * | 2019-12-24 | 2021-06-25 | 上海科胜药物研发有限公司 | 一种氨磺必利药典杂质的制备方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2124511C1 (ru) * | 1993-05-14 | 1999-01-10 | Фармасьютикал Ко., Лтд | Производные пиперазина |
| US5981525A (en) | 1995-01-10 | 1999-11-09 | Smithkline Beecham Corporation | Indole derivatives useful in the treatment of osteoporosis |
| IL127668A0 (en) | 1996-07-09 | 1999-10-28 | Smithkline Beecham Spa | Indole derivatives for the treatment of osteoporosis |
| ES2236971T3 (es) * | 1997-12-24 | 2005-07-16 | Nikem Research S.R.L. | Derivados del indol utiles, entre otras cosas, para el tratamiento de la osteoporosis. |
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1999
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2000
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- 2000-06-16 MX MXPA01013277A patent/MXPA01013277A/es active IP Right Grant
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- 2000-06-16 WO PCT/EP2000/005672 patent/WO2001002388A1/en active IP Right Grant
- 2000-06-16 ES ES00943839T patent/ES2226870T3/es not_active Expired - Lifetime
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- 2000-06-16 JP JP2001507825A patent/JP2003503490A/ja active Pending
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