US20060052613A1 - 1-alkyl-3-aminoindazoles - Google Patents
1-alkyl-3-aminoindazoles Download PDFInfo
- Publication number
- US20060052613A1 US20060052613A1 US10/539,423 US53942305A US2006052613A1 US 20060052613 A1 US20060052613 A1 US 20060052613A1 US 53942305 A US53942305 A US 53942305A US 2006052613 A1 US2006052613 A1 US 2006052613A1
- Authority
- US
- United States
- Prior art keywords
- phenyl
- optionally substituted
- ring
- taken together
- methoxyphenyl
- 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.)
- Abandoned
Links
- 0 *N1N=CC2=C([1*])C([2*])=C([3*])C([4*])=C21 Chemical compound *N1N=CC2=C([1*])C([2*])=C([3*])C([4*])=C21 0.000 description 5
- LELXBUHYOPZWNM-PXXFIRSTSA-N C[C@@H](O)CN1N=C(N)C2=CC=C(OCC3=CC=CC=C3)C=C21.C[C@@H](O)CN1N=CC2=CC=C(OCC3=CC=CC=C3)C=C21.C[C@@H](O)CNC1=CC(OCC2=CC=CC=C2)=CC=C1C#N Chemical compound C[C@@H](O)CN1N=C(N)C2=CC=C(OCC3=CC=CC=C3)C=C21.C[C@@H](O)CN1N=CC2=CC=C(OCC3=CC=CC=C3)C=C21.C[C@@H](O)CNC1=CC(OCC2=CC=CC=C2)=CC=C1C#N LELXBUHYOPZWNM-PXXFIRSTSA-N 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
Definitions
- the present invention relates to 1-alkyl-3-aminoindazoles and preferably 1-(hydroxyalkyl)-3-aminoindazoles useful as intermediates for the preparation of 1-alkylindazoles.
- Use of the 1-alkyl-3-aminoindazoles as intermediates avoids unwanted side products and results in enantiomerically pure final pharmaceutically active products.
- Certain (aminoalkyl)indazoles are known to be useful for treating diseases of the central nervous system (WO 98/30548).
- WO 02/098861 A1 and WO 02/098862 A1 disclose methods of preparation of (aminoalkyl)indazoles. Specifically, these applications disclose the conversion of 2-(hydroxyalkyl)aminobenzaldehydes to 1-(hydroxyalkyl)indazoles, which are useful intermediates for the preparation of 1-(aminoalkyl)indazoles.
- the present invention overcomes the above mentioned problems and other drawbacks of the prior art by providing a method, capable of scaleup, to efficiently produce large quantities of 1-(aminoalkyl)indazoles. More specifically, the present invention provides a method of making 1-(aminoalkyl)indazoles in large quantities while avoiding large quantities of undesired isomers or by-products.
- the present invention to relates to a method of making a 1-alkylindazole involving:
- the present invention relates to a method of making a 1-(hydroxyalkyl)indazole involving:
- the present invention relates to 1-alkyl-3-aminoindazoles. More particularly, the present invention relates to the use of 1-alkyl-3-aminoindazoles as intermediates for making 1-alkylindazoles.
- a preferred embodiment of the present invention relates to 1-(hydroxyalkyl)-3-aminoindazoles, and particularly to the use of 1-(hydroxyalkyl)-3-aminoindazoles for making 1-(aminoalkyl)indazoles.
- the 1-(aminoalkyl)indazoles that can be made following the methods of the present invention are preferably enantiomerically pure products which are preferably useful as pharmacologically active products such as in the treatment of glaucoma and/or are useful for lowering and controlling normal or elevated intraocular pressure.
- the methods described herein avoid the problems associated with removal of acetic acid and are capable of scaleup to produce large quantities of material for formulation in pharmaceutical compositions.
- 1-alkylindazoles can be produced by nitrosating a 2-alkylaminobenzonitrile, followed by reduction and cyclization, to form a 1-alkyl-3-aminoindazole. This aminoindazole can then be deaminated to form a 1-alkylindazole.
- R is a C 2 to C 12 (hydroxy)alkyl group optionally substituted with phenyl, methoxyphenyl, (dimethylamino)phenyl, OR 5 , OC( ⁇ O)R 5 , OC( ⁇ O)OR 5 , N(R 5 ) 2 , N(R 5 )C( ⁇ O)R 5 , N(R 5 )C( ⁇ O)OR 5 , or with one or more F atoms;
- R is a C 2 to C 6 (hydroxy)alkyl optionally substituted with phenyl, OR 5 , N(R 5 )C( ⁇ O)R 5 , N(R 5 )C( ⁇ O)OR 5 , or with one or more F atoms;
- the nitrosation can be carried out on a 2-hydroxyalkyl)aminobenzonitrile, followed by reduction and cyclization, to form a 1-(hydroxyalkyl)-3-aminoindazole.
- This 1-(hydroxyalkyl)-3-aminoindazole can then be deaminated to form a 1-(hydroxyalkyl)indazole.
- the steps of nitrosation/reduction-cyclization and deamination are carried out using a readily removable solvent.
- Preferred solvents for use in the methods of the present invention include tetrahydrofuran and methanol.
- This 1-(hydroxyalkyl)indazole can then be further reacted to form a desired 1-(aminoalkyl)indazole which is preferably enantiomerically pure and is preferably a pharmaceutically active product.
- the 1-(hydroxyalkyl)indazole can be reacted with a sulfonyl halide or sulfonic anhydride to form a corresponding sulfonic ester.
- This sulfonic ester can be reacted with a metal azide to yield a 1-(azidoalkyl)indazole which in turn is reacted with a hydrogen source and a catalyst to yield a 1-(aminoalkyl)indazole.
- the hydrogen source is preferably ammonium formate and the catalyst is preferably palladium on charcoal in the presence of an organic solvent, such as ethanol.
- the 2-(hydroxyalkyl)aminobenzonitrile has the formula
- R is a C 2 to C 12 alkyl group substituted with at least one OH group and optionally substituted with phenyl, methoxyphenyl, (dimethylamino)phenyl, OR 5 , OC( ⁇ O)R 5 , OC( ⁇ O)OR 5 , N(R 5 ) 2 , N(R 5 )C( ⁇ O)R 5 , N(R 5 )C( ⁇ O)OR 5 , or with one or more F atoms;
- R 1 , R 2 , R 3 and R 4 are independently H, F, Cl, Br, CF 3 , OH, OR 5 , OC( ⁇ O)R 5 , OC( ⁇ O)OR 5 , N(R 5 ) 2 , N(R 5 )C( ⁇ O)R 5 , N(R 5 )C( ⁇ O)OR 5 , NO 2 , CN, N 3 , SH, S(O) n R 5 , C( ⁇ O)R 5 ,
- R is a C 2 to C 6 alkyl group substituted with at least one OH group and optionally substituted with phenyl, OR 5 , N(R 5 )C( ⁇ O)R 5 , N(R 5 )C( ⁇ O)OR 5 , or with one or more P atoms;
- R 1 , R 2 , R 3 and R 4 are independently H, F, Cl, CF 3 , OR 5 , OC( ⁇ O)R 5 , OC( ⁇ O)OR 5 , N(R 5 ) 2 , N(R 5 )C( ⁇ O)R 5 , N(R 5 )C( ⁇ O)OR 5 , NO 2 , CN, C( ⁇ O)R 5 , COOR 5 , CON(R 5 ) 2 , C 1 to C 6 alkyl optionally substituted with phenyl, C( ⁇ O)R 5 , COOR 5 , CON(R) 2 , CN, OR 5 , OC( ⁇ O)R 5 ,
- the 2-alkylaminobenzonitrile which is used in the methods of the present invention can be prepared by any number of reaction schemes.
- the 2-alkylaminobenzonitrile can be formed by reacting a 2-fluorobenzonitrile with an alkylamine in an organic solvent.
- the alkylamine is a hydroxyalkylamine and the product is a 2-(hydroxyalkyl)aminobenzonitrile.
- a 2-fluorobenzonitrile can be reacted with 1-amino-2-propanol in the presence of an organic solvent to yield the desired 2-(2-hydroxypropyl)aminobenzonitrile.
- reaction schemes can be used to form the desired starting 2-alkylaminobenzonitrile.
- Those skilled in the art in view of the present invention, can form a variety of starting 2-alkylaminobenzonitriles for purposes of the present invention.
- the nitrosation can be accomplished by the addition of at least one organic nitrite or inorganic nitrite preferably in the presence of at least one organic solvent.
- suitable nitrites include, but are not limited to, tert-butyl nitrite, isobutyl nitrite, isoamyl nitrite or sodium nitrite.
- Preferred solvents include, but are not limited to, ethers, and a more preferred solvent is tetrahydrofuran. Combinations or mixtures of two or more nitrites can be used. This would also be true with respect to the other reactants in that combinations or mixtures of various reactants can be used.
- the intermediate nitrosamine is treated with a reducing agent in the presence of an organic solvent to effect reduction with concurrent cyclization, affording a preferred 1-(hydroxyalkyl)-3-aminoindazole.
- a reducing agent is zinc, and the reduction is carried out in the presence of an acidic salt such as ammonium acetate or ammonium chloride.
- the organic solvent is tetrahydrofuran or methanol, or a mixture of tetrahydrofuran and methanol.
- R is a C 2 to C 12 (hydroxy)alkyl group optionally substituted with phenyl, methoxyphenyl, (dimethylamino)phenyl, OR 5 , OC( ⁇ O)R 5 , OC( ⁇ O)OR 5 , N(R 5 ) 2 , N(R 5 )C( ⁇ O)R 5 , N(R 5 )C( ⁇ O)OR 5 , or with one or more F atoms;
- R is a C 2 to C 6 (hydroxy)alkyl group optionally substituted with phenyl, OR 5 , N(R 5 )C( ⁇ O)R 5 , N(R 5 )C( ⁇ O)OR 5 , or with one or more F atoms;
- the deamination of the I-(hydroxyalkyl)-3-aminoindazole can be accomplished by reaction according to general procedures known in the art as described, for example, in March (1992).
- the deamination is accomplished by treatment of the 1-(hydroxyalkyl)-3-aminoindazole with an organic nitrite in the presence of a hydride source and an organic solvent.
- suitable organic nitrites include, but are not limited to, tert-butyl nitrite, isobutyl nitrite, and isoamyl nitrite.
- the hydride source is preferably hypophosphorous acid or sodium hypophosphite. Most preferably the hydride source is hypophosphorous acid.
- the organic solvent may be an alcohol, such as methanol or ethanol, in which case the solvent can also function as a hydride source. Generally, the organic solvent is methanol.
- desired indazoles such as 1-(aminoalkyl)indazoles can be formed.
- the present invention essentially prevents the formation of unwanted isomers thus resulting in improved yields and a process that is less expensive.
- the process of the present invention can start with a racemic 2-(hydroxyalkyl)aminobenzonitrile, or can start with an (R)- or (S)-enantiomerically enriched 2-(hydroxyalkyl)aminobenzonitrile.
- the process of the present invention permits great flexibility in the starting 2-(hydroxyalkyl)aminobenzonitrile, which further permits great flexibility in forming various desired indazoles such 1-(aminoalkyl)indazoles.
- the indazoles which can be formed using the methods of the present invention are useful in, for instance, treating glaucoma and/or lowering or controlling elevated intraocular pressure.
- the preferred process of the present invention uses a 2-alkylaminobenzonitrile in which the alkyl group is substituted by at least one OH group.
- the ability to have an OH group in such a reaction sequence is a great benefit and unexpected since those skilled in the art might expect that the OH group would not survive further processing.
- the method of the present invention allows formation of the desired indazole without the need for a protecting group on the hydroxy substituent.
- the present invention permits the formation of various desirable indazoles, which previous to the present process, were quite difficult to form.
- compositions and/or methods disclosed and claimed herein can be is made and executed without undue experimentation in light of the present disclosure. While the compositions and methods of this invention have been described in terms of preferred embodiments, it will be apparent to those of skill in the art that variations may be applied to the compositions and/or methods and in the steps or in the sequence of steps of the method described herein without departing from the concept, spirit and scope of the invention. More specifically, it will be apparent that certain agents which are both chemically and structurally related may be substituted for the agents described herein to achieve similar results. All such substitutions and modifications apparent to those skilled in the art are deemed to be within the spirit, scope and concept of the invention as defined by the appended claims.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US10/539,423 US20060052613A1 (en) | 2002-12-23 | 2003-12-19 | 1-alkyl-3-aminoindazoles |
US12/368,869 US7799930B2 (en) | 2002-12-23 | 2009-02-10 | 1-alkyl-3-aminoindazoles |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US43638502P | 2002-12-23 | 2002-12-23 | |
PCT/US2003/040370 WO2004058725A1 (en) | 2002-12-23 | 2003-12-19 | 1-alkyl-3-aminoindazoles |
US10/539,423 US20060052613A1 (en) | 2002-12-23 | 2003-12-19 | 1-alkyl-3-aminoindazoles |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US12/368,869 Division US7799930B2 (en) | 2002-12-23 | 2009-02-10 | 1-alkyl-3-aminoindazoles |
Publications (1)
Publication Number | Publication Date |
---|---|
US20060052613A1 true US20060052613A1 (en) | 2006-03-09 |
Family
ID=32682383
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US10/539,423 Abandoned US20060052613A1 (en) | 2002-12-23 | 2003-12-19 | 1-alkyl-3-aminoindazoles |
US12/368,869 Expired - Fee Related US7799930B2 (en) | 2002-12-23 | 2009-02-10 | 1-alkyl-3-aminoindazoles |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US12/368,869 Expired - Fee Related US7799930B2 (en) | 2002-12-23 | 2009-02-10 | 1-alkyl-3-aminoindazoles |
Country Status (12)
Country | Link |
---|---|
US (2) | US20060052613A1 (ko) |
EP (1) | EP1578729A4 (ko) |
JP (1) | JP2006514651A (ko) |
KR (1) | KR20050086927A (ko) |
CN (1) | CN100361977C (ko) |
AU (1) | AU2003303477A1 (ko) |
BR (1) | BR0317665A (ko) |
CA (1) | CA2509833A1 (ko) |
MX (1) | MXPA05006851A (ko) |
PL (1) | PL376084A1 (ko) |
WO (1) | WO2004058725A1 (ko) |
ZA (1) | ZA200504719B (ko) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20070072920A1 (en) * | 2005-09-23 | 2007-03-29 | Alcon, Inc. | Phenylethylamine analogs and their use for treating glaucoma |
US20070135430A1 (en) * | 2003-11-26 | 2007-06-14 | Dantanarayana Anura P | Substituted furo[2,3-g]indazoles for the treatment of glaucoma |
US20070293475A1 (en) * | 2006-06-20 | 2007-12-20 | Alcon Manufacturing Ltd. | Aryl and heteroaryl tetrahydrobenzazepine derivatives and their use for treating glaucoma |
Families Citing this family (9)
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 |
JP2006511556A (ja) | 2002-12-13 | 2006-04-06 | アルコン,インコーポレイテッド | 新規のベンゾピラン類似体及び緑内障の治療のためのそれらの使用 |
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 |
AR046890A1 (es) | 2003-12-15 | 2005-12-28 | Alcon Inc | [1,4] oxazino [2,3-g] indazoles sustituidos para el tratamiento del glaucoma. |
WO2006062839A1 (en) | 2004-12-08 | 2006-06-15 | Alcon, Inc. | Use of dioxindoindazoles and dioxoloindazoles 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 |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3133081A (en) * | 1964-05-12 | J-aminoindazole derivatives | ||
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 |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1770649A1 (de) * | 1968-06-15 | 1971-11-11 | Bayer Ag | Substituierte 3-Amino-indazole |
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 |
AU2002310224B2 (en) | 2001-06-01 | 2007-06-07 | 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 CN CNB2003801074159A patent/CN100361977C/zh not_active Expired - Fee Related
- 2003-12-19 JP JP2004563762A patent/JP2006514651A/ja active Pending
- 2003-12-19 AU AU2003303477A patent/AU2003303477A1/en not_active Abandoned
- 2003-12-19 MX MXPA05006851A patent/MXPA05006851A/es unknown
- 2003-12-19 EP EP03814162A patent/EP1578729A4/en not_active Withdrawn
- 2003-12-19 KR KR1020057011570A patent/KR20050086927A/ko not_active Application Discontinuation
- 2003-12-19 PL PL03376084A patent/PL376084A1/xx not_active Application Discontinuation
- 2003-12-19 BR BR0317665-7A patent/BR0317665A/pt not_active IP Right Cessation
- 2003-12-19 CA CA002509833A patent/CA2509833A1/en not_active Abandoned
- 2003-12-19 US US10/539,423 patent/US20060052613A1/en not_active Abandoned
- 2003-12-19 WO PCT/US2003/040370 patent/WO2004058725A1/en active Application Filing
-
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
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3133081A (en) * | 1964-05-12 | J-aminoindazole derivatives | ||
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 |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20070135430A1 (en) * | 2003-11-26 | 2007-06-14 | Dantanarayana Anura P | Substituted furo[2,3-g]indazoles for the treatment of glaucoma |
US20090012291A1 (en) * | 2003-11-26 | 2009-01-08 | Alcon, Inc. | SUBSTITUTED FURO[2,3-g]INDAZOLES FOR THE TREATMENT OF GLAUCOMA |
US7476687B2 (en) | 2003-11-26 | 2009-01-13 | Alcon, Inc. | Substituted furo[2,3-g]indazoles for the treatment of glaucoma |
US20070072920A1 (en) * | 2005-09-23 | 2007-03-29 | 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 |
Also Published As
Publication number | Publication date |
---|---|
CN1732157A (zh) | 2006-02-08 |
EP1578729A1 (en) | 2005-09-28 |
PL376084A1 (en) | 2005-12-12 |
EP1578729A4 (en) | 2007-08-29 |
MXPA05006851A (es) | 2005-08-16 |
US20090149659A1 (en) | 2009-06-11 |
KR20050086927A (ko) | 2005-08-30 |
CN100361977C (zh) | 2008-01-16 |
BR0317665A (pt) | 2005-11-29 |
CA2509833A1 (en) | 2004-07-15 |
JP2006514651A (ja) | 2006-05-11 |
WO2004058725A1 (en) | 2004-07-15 |
ZA200504719B (en) | 2006-08-30 |
AU2003303477A1 (en) | 2004-07-22 |
US7799930B2 (en) | 2010-09-21 |
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Owner name: ALCON, INC., SWITZERLAND Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:DELGADO, PETER;CONROW, RAYMOND E.;DEAN, W. DENNIS;REEL/FRAME:017248/0459 Effective date: 20050603 |
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STCB | Information on status: application discontinuation |
Free format text: ABANDONED -- FAILURE TO PAY ISSUE FEE |