ZA200504719B - 1-alkyl-3-aminodazoles - Google Patents
1-alkyl-3-aminodazoles Download PDFInfo
- Publication number
- ZA200504719B ZA200504719B ZA200504719A ZA200504719A ZA200504719B ZA 200504719 B ZA200504719 B ZA 200504719B ZA 200504719 A ZA200504719 A ZA 200504719A ZA 200504719 A ZA200504719 A ZA 200504719A ZA 200504719 B ZA200504719 B ZA 200504719B
- Authority
- ZA
- South Africa
- Prior art keywords
- phenyl
- optionally substituted
- ring
- methoxyphenyl
- together form
- Prior art date
Links
- -1 methoxyphenyl Chemical group 0.000 claims description 63
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 38
- 125000000217 alkyl group Chemical group 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 22
- 125000001153 fluoro group Chemical group F* 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 10
- 238000007363 ring formation reaction Methods 0.000 claims description 9
- 230000009935 nitrosation Effects 0.000 claims description 8
- 238000007034 nitrosation reaction Methods 0.000 claims description 8
- 230000009615 deamination Effects 0.000 claims description 6
- 238000006481 deamination reaction Methods 0.000 claims description 6
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 3
- WRSXUNSJGJUKHE-UHFFFAOYSA-N indazole Chemical compound C1=CC=C[C]2C=NN=C21 WRSXUNSJGJUKHE-UHFFFAOYSA-N 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 150000002473 indoazoles Chemical class 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 10
- 239000003960 organic solvent Substances 0.000 description 9
- HLCPWBZNUKCSBN-UHFFFAOYSA-N 2-aminobenzonitrile Chemical compound NC1=CC=CC=C1C#N HLCPWBZNUKCSBN-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 125000004103 aminoalkyl group Chemical group 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000000543 intermediate Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 230000008901 benefit Effects 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 150000004678 hydrides Chemical class 0.000 description 3
- 150000002826 nitrites Chemical class 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- JNNJQGFCEMZAQR-UHFFFAOYSA-N 2-(benzylamino)benzonitrile Chemical compound N#CC1=CC=CC=C1NCC1=CC=CC=C1 JNNJQGFCEMZAQR-UHFFFAOYSA-N 0.000 description 2
- GDHXJNRAJRCGMX-UHFFFAOYSA-N 2-fluorobenzonitrile Chemical compound FC1=CC=CC=C1C#N GDHXJNRAJRCGMX-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 208000010412 Glaucoma Diseases 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 150000003973 alkyl amines Chemical class 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 230000004406 elevated intraocular pressure Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- OWFXIOWLTKNBAP-UHFFFAOYSA-N isoamyl nitrite Chemical compound CC(C)CCON=O OWFXIOWLTKNBAP-UHFFFAOYSA-N 0.000 description 2
- APNSGVMLAYLYCT-UHFFFAOYSA-N isobutyl nitrite Chemical compound CC(C)CON=O APNSGVMLAYLYCT-UHFFFAOYSA-N 0.000 description 2
- XKLJHFLUAHKGGU-UHFFFAOYSA-N nitrous amide Chemical compound ON=N XKLJHFLUAHKGGU-UHFFFAOYSA-N 0.000 description 2
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- IOGXOCVLYRDXLW-UHFFFAOYSA-N tert-butyl nitrite Chemical compound CC(C)(C)ON=O IOGXOCVLYRDXLW-UHFFFAOYSA-N 0.000 description 2
- 239000012414 tert-butyl nitrite Substances 0.000 description 2
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 description 1
- YDTDKKULPWTHRV-UHFFFAOYSA-N 1H-indazol-3-amine Chemical class C1=CC=C2C(N)=NNC2=C1 YDTDKKULPWTHRV-UHFFFAOYSA-N 0.000 description 1
- QVKPEDVUJUZDIB-UHFFFAOYSA-N 2-(2-hydroxypropylamino)benzonitrile Chemical compound CC(O)CNC1=CC=CC=C1C#N QVKPEDVUJUZDIB-UHFFFAOYSA-N 0.000 description 1
- FXWFZIRWWNPPOV-UHFFFAOYSA-N 2-aminobenzaldehyde Chemical compound NC1=CC=CC=C1C=O FXWFZIRWWNPPOV-UHFFFAOYSA-N 0.000 description 1
- HINFZKWHKTZDQX-UHFFFAOYSA-N 2-hydrazinylbenzonitrile Chemical compound NNC1=CC=CC=C1C#N HINFZKWHKTZDQX-UHFFFAOYSA-N 0.000 description 1
- KWSLGOVYXMQPPX-UHFFFAOYSA-N 5-[3-(trifluoromethyl)phenyl]-2h-tetrazole Chemical compound FC(F)(F)C1=CC=CC(C2=NNN=N2)=C1 KWSLGOVYXMQPPX-UHFFFAOYSA-N 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- 241000287227 Fringillidae Species 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical group [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical group [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 150000008043 acidic salts Chemical class 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 230000004493 normal intraocular pressure Effects 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 229910001379 sodium hypophosphite Inorganic materials 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 150000003461 sulfonyl halides Chemical class 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
- C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US43638502P | 2002-12-23 | 2002-12-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200504719B true ZA200504719B (en) | 2006-08-30 |
Family
ID=32682383
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200504719A ZA200504719B (en) | 2002-12-23 | 2005-06-09 | 1-alkyl-3-aminodazoles |
Country Status (12)
| Country | Link |
|---|---|
| US (2) | US20060052613A1 (es) |
| EP (1) | EP1578729A4 (es) |
| JP (1) | JP2006514651A (es) |
| KR (1) | KR20050086927A (es) |
| CN (1) | CN100361977C (es) |
| AU (1) | AU2003303477A1 (es) |
| BR (1) | BR0317665A (es) |
| CA (1) | CA2509833A1 (es) |
| MX (1) | MXPA05006851A (es) |
| PL (1) | PL376084A1 (es) |
| WO (1) | WO2004058725A1 (es) |
| ZA (1) | ZA200504719B (es) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6960579B1 (en) | 1998-05-19 | 2005-11-01 | Alcon Manufacturing, Ltd. | Serotonergic 5HT7 receptor compounds for treating ocular and CNS disorders |
| TW593302B (en) | 2001-12-20 | 2004-06-21 | Alcon Inc | Novel benzodifuranimidazoline and benzofuranimidazoline derivatives and their use for the treatment of glaucoma |
| BR0316775A (pt) | 2002-12-13 | 2005-11-01 | Alcon Inc | Novos análogos de benzopirano e seu uso para o tratamento de glaucoma |
| WO2005053688A1 (en) * | 2003-11-26 | 2005-06-16 | Alcon, Inc. | Substituted furo[2,3-g] indazoles for the treatment of glaucoma |
| US7129257B1 (en) | 2003-12-15 | 2006-10-31 | Alcon, Inc. | Pyrazolo[3,4- e]benzoxazoles for the treatment of glaucoma |
| US7338972B1 (en) | 2003-12-15 | 2008-03-04 | Alcon, Inc. | Substituted 1-alkylamino-1H-indazoles for the treatment of glaucoma |
| US6989445B2 (en) | 2003-12-15 | 2006-01-24 | Alcon, Inc. | Substituted [1,4]oxazino[2,3-g]indazoles for the treatment of glaucoma |
| US7425572B2 (en) | 2004-12-08 | 2008-09-16 | Alcon, Inc. | Use of dioxindoindazoles and dioxoloindazoles for treating glaucoma |
| TW200744567A (en) * | 2005-09-23 | 2007-12-16 | Alcon Inc | Phenylethylamine analogs and their use for treating glaucoma |
| US20070293475A1 (en) * | 2006-06-20 | 2007-12-20 | Alcon Manufacturing Ltd. | Aryl and heteroaryl tetrahydrobenzazepine derivatives and their use for treating glaucoma |
| CN102372675B (zh) * | 2010-08-14 | 2013-12-18 | 王娜 | 6-氯-4-碘吲唑及其制备方法与应用 |
| DE102015012050A1 (de) * | 2015-09-15 | 2017-03-16 | Merck Patent Gmbh | Verbindungen als ASIC-Inhibitoren und deren Verwendungen |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3133081A (en) * | 1964-05-12 | J-aminoindazole derivatives | ||
| DE1770649A1 (de) * | 1968-06-15 | 1971-11-11 | Bayer Ag | Substituierte 3-Amino-indazole |
| US3681382A (en) * | 1969-02-07 | 1972-08-01 | Ciba Geigy Corp | 3-aminoindazoles |
| US3725431A (en) * | 1970-09-23 | 1973-04-03 | Ciba Geigy Corp | 1-aralkyl-3-aminoindazoles |
| US3963739A (en) * | 1972-09-30 | 1976-06-15 | Dynamit Nobel Aktiengesellschaft | 3-Amino-4,5,6-trichloro-7-nitriloindazoles |
| JP3560986B2 (ja) * | 1997-01-13 | 2004-09-02 | 山之内製薬株式会社 | ５―ｈｔ２ｃ受容体作用薬及びアミノアルキルインダゾール誘導体 |
| CA2447482A1 (en) | 2001-06-01 | 2002-12-12 | Alcon, Inc. | Methods of making indazoles |
| WO2002098861A1 (en) * | 2001-06-01 | 2002-12-12 | Alcon, Inc. | Methods of making 1-(2-aminopropyl)-6-hydroxyindazole |
-
2003
- 2003-12-19 JP JP2004563762A patent/JP2006514651A/ja active Pending
- 2003-12-19 KR KR1020057011570A patent/KR20050086927A/ko not_active Application Discontinuation
- 2003-12-19 EP EP03814162A patent/EP1578729A4/en not_active Withdrawn
- 2003-12-19 US US10/539,423 patent/US20060052613A1/en not_active Abandoned
- 2003-12-19 BR BR0317665-7A patent/BR0317665A/pt not_active IP Right Cessation
- 2003-12-19 WO PCT/US2003/040370 patent/WO2004058725A1/en active Application Filing
- 2003-12-19 MX MXPA05006851A patent/MXPA05006851A/es unknown
- 2003-12-19 PL PL03376084A patent/PL376084A1/xx not_active Application Discontinuation
- 2003-12-19 CA CA002509833A patent/CA2509833A1/en not_active Abandoned
- 2003-12-19 AU AU2003303477A patent/AU2003303477A1/en not_active Abandoned
- 2003-12-19 CN CNB2003801074159A patent/CN100361977C/zh not_active Expired - Fee Related
-
2005
- 2005-06-09 ZA ZA200504719A patent/ZA200504719B/en unknown
-
2009
- 2009-02-10 US US12/368,869 patent/US7799930B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US20060052613A1 (en) | 2006-03-09 |
| CN100361977C (zh) | 2008-01-16 |
| US7799930B2 (en) | 2010-09-21 |
| CN1732157A (zh) | 2006-02-08 |
| MXPA05006851A (es) | 2005-08-16 |
| US20090149659A1 (en) | 2009-06-11 |
| KR20050086927A (ko) | 2005-08-30 |
| BR0317665A (pt) | 2005-11-29 |
| AU2003303477A1 (en) | 2004-07-22 |
| JP2006514651A (ja) | 2006-05-11 |
| PL376084A1 (en) | 2005-12-12 |
| EP1578729A1 (en) | 2005-09-28 |
| CA2509833A1 (en) | 2004-07-15 |
| WO2004058725A1 (en) | 2004-07-15 |
| EP1578729A4 (en) | 2007-08-29 |
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