JP2003513076A5 - - Google Patents
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- Publication number
- JP2003513076A5 JP2003513076A5 JP2001534779A JP2001534779A JP2003513076A5 JP 2003513076 A5 JP2003513076 A5 JP 2003513076A5 JP 2001534779 A JP2001534779 A JP 2001534779A JP 2001534779 A JP2001534779 A JP 2001534779A JP 2003513076 A5 JP2003513076 A5 JP 2003513076A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- amino
- partially
- heteroaryl
- halogenated
- 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.)
- Granted
Links
- 125000000217 alkyl group Chemical group 0.000 description 24
- -1 pyrazole compound Chemical class 0.000 description 24
- 125000001072 heteroaryl group Chemical group 0.000 description 9
- 125000003545 alkoxy group Chemical group 0.000 description 7
- 125000001624 naphthyl group Chemical group 0.000 description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 7
- 229910052736 halogen Inorganic materials 0.000 description 6
- 150000002367 halogens Chemical class 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 125000000623 heterocyclic group Chemical group 0.000 description 5
- 125000002883 imidazolyl group Chemical group 0.000 description 5
- 125000003373 pyrazinyl group Chemical group 0.000 description 5
- 125000003226 pyrazolyl group Chemical group 0.000 description 5
- 125000004076 pyridyl group Chemical group 0.000 description 5
- 125000000714 pyrimidinyl group Chemical group 0.000 description 5
- 125000000168 pyrrolyl group Chemical group 0.000 description 5
- 125000002541 furyl group Chemical group 0.000 description 4
- 125000001786 isothiazolyl group Chemical group 0.000 description 4
- 125000000842 isoxazolyl group Chemical group 0.000 description 4
- 125000002098 pyridazinyl group Chemical group 0.000 description 4
- 125000001544 thienyl group Chemical group 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000006576 di-(C1-C3-alkyl)-aminocarbonyl group Chemical group 0.000 description 2
- 125000005553 heteroaryloxy group Chemical group 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 125000006698 (C1-C3) dialkylamino group Chemical group 0.000 description 1
- 125000000081 (C5-C8) cycloalkenyl group Chemical group 0.000 description 1
- 0 *c1c(*)[n](*)nc1* Chemical compound *c1c(*)[n](*)nc1* 0.000 description 1
- QYCGBAJADAGLLK-UHFFFAOYSA-N 1-(cyclohepten-1-yl)cycloheptene Chemical group C1CCCCC=C1C1=CCCCCC1 QYCGBAJADAGLLK-UHFFFAOYSA-N 0.000 description 1
- VSIYJQNFMOOGCU-UHFFFAOYSA-N 1-(cyclohexen-1-yl)cyclohexene Chemical group C1CCCC(C=2CCCCC=2)=C1 VSIYJQNFMOOGCU-UHFFFAOYSA-N 0.000 description 1
- KAJRUHJCBCZULP-UHFFFAOYSA-N 1-cyclohepta-1,3-dien-1-ylcyclohepta-1,3-diene Chemical compound C1CCC=CC=C1C1=CC=CCCC1 KAJRUHJCBCZULP-UHFFFAOYSA-N 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- ZHGNHOOVYPHPNJ-UHFFFAOYSA-N Amigdalin Chemical compound FC(F)(F)C(=O)OCC1OC(OCC2OC(OC(C#N)C3=CC=CC=C3)C(OC(=O)C(F)(F)F)C(OC(=O)C(F)(F)F)C2OC(=O)C(F)(F)F)C(OC(=O)C(F)(F)F)C(OC(=O)C(F)(F)F)C1OC(=O)C(F)(F)F ZHGNHOOVYPHPNJ-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004599 benzpyrazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
- 125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 description 1
- 125000003678 cyclohexadienyl group Chemical group C1(=CC=CCC1)* 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 125000005046 dihydronaphthyl group Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000004043 oxo group Chemical group O=* 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US16247699P | 1999-10-29 | 1999-10-29 | |
| US60/162,476 | 1999-10-29 | ||
| US19265100P | 2000-03-28 | 2000-03-28 | |
| US60/192,651 | 2000-03-28 | ||
| PCT/US2000/029891 WO2001032627A1 (en) | 1999-10-29 | 2000-10-27 | Process of making substituted pyrazoles |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2003513076A JP2003513076A (ja) | 2003-04-08 |
| JP2003513076A5 true JP2003513076A5 (enExample) | 2007-12-20 |
| JP4861585B2 JP4861585B2 (ja) | 2012-01-25 |
Family
ID=26858795
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001534779A Expired - Fee Related JP4861585B2 (ja) | 1999-10-29 | 2000-10-27 | 置換ピラゾールの合成方法 |
Country Status (11)
| Country | Link |
|---|---|
| EP (1) | EP1235810B1 (enExample) |
| JP (1) | JP4861585B2 (enExample) |
| AT (1) | ATE244704T1 (enExample) |
| AU (1) | AU1445001A (enExample) |
| CA (1) | CA2387762C (enExample) |
| DE (1) | DE60003846T2 (enExample) |
| DK (1) | DK1235810T3 (enExample) |
| ES (1) | ES2202189T3 (enExample) |
| MX (1) | MXPA02004004A (enExample) |
| PT (1) | PT1235810E (enExample) |
| WO (1) | WO2001032627A1 (enExample) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6407238B1 (en) | 1999-10-29 | 2002-06-18 | Boehringer Ingelheim Pharmaceuticals, Inc. | Process of making substituted pyrazoles |
| US6492529B1 (en) | 2000-01-18 | 2002-12-10 | Boehringer Ingelheim Pharmaceuticals, Inc. | Bis pyrazole-1H-pyrazole intermediates and their synthesis |
| EP1362037A1 (en) | 2001-02-15 | 2003-11-19 | Boehringer Ingelheim Pharmaceuticals Inc. | Process for synthesis of heteroaryl-substituted urea compounds useful as antiinflammatory agents |
| DE10315571A1 (de) | 2003-04-05 | 2004-10-14 | Merck Patent Gmbh | Pyrazolverbindungen |
| DE10315573A1 (de) | 2003-04-05 | 2004-10-14 | Merck Patent Gmbh | Substituierte Pyrazole |
| DE10315569A1 (de) * | 2003-04-05 | 2004-10-14 | Merck Patent Gmbh | Substituierte Pyrazolverbindungen |
| WO2007044490A2 (en) | 2005-10-06 | 2007-04-19 | Boehringer Ingelheim International Gmbh | Process for making heteroaryl amine intermediate compounds |
| EP2135865A1 (de) | 2008-06-17 | 2009-12-23 | Bayer CropScience AG | Substituierte 1-(Diazinyl) pyrazol-4-yl-essigsäuren, Verfahren zu deren Herstellung und deren Verwendung als Herbizide und Pflanzenwachstumsregulatoren |
| EP2194052A1 (de) | 2008-12-06 | 2010-06-09 | Bayer CropScience AG | Substituierte 1-(Thiazolyl)- und 1-(Isothiazolyl)pyrazol-4-yl-essigsäuren, Verfahren zu deren Herstellung und deren Verwendung als Herbizide und Pflanzenwachstumsregulatoren |
| WO2011073098A1 (de) | 2009-12-15 | 2011-06-23 | Bayer Cropscience Ag | 1-(heteroaryl)-pyrazol-4-yl-essigsäuren, verfahren zu deren herstellung und deren verwendung als herbizide und pflanzenwachstumsregulatoren |
| AU2019387370A1 (en) | 2018-11-30 | 2021-06-10 | Nuvation Bio Inc. | Pyrrole and pyrazole compounds and methods of use thereof |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4314851A1 (de) * | 1993-05-05 | 1994-11-10 | Huels Chemische Werke Ag | Verfahren zur Herstellung von 3-Amino-5-methylpyrazol |
| NZ333414A (en) * | 1996-06-20 | 2000-05-26 | Monsanto Co | Preparation of substituted 3-aryl-5-haloalkyl-pyrazoles having herbicidal activity |
| US5698708A (en) * | 1996-06-20 | 1997-12-16 | Monsanto Company | Preparation of substituted 3-aryl-5-haloalkyl-pyrazoles having herbicidal activity |
| CA2308428A1 (en) * | 1997-11-03 | 1999-05-14 | Boehringer Ingelheim Pharmaceuticals, Inc. | Aromatic heterocyclic compounds as anti-inflammatory agents |
-
2000
- 2000-10-27 EP EP00976715A patent/EP1235810B1/en not_active Expired - Lifetime
- 2000-10-27 ES ES00976715T patent/ES2202189T3/es not_active Expired - Lifetime
- 2000-10-27 AU AU14450/01A patent/AU1445001A/en not_active Abandoned
- 2000-10-27 WO PCT/US2000/029891 patent/WO2001032627A1/en not_active Ceased
- 2000-10-27 JP JP2001534779A patent/JP4861585B2/ja not_active Expired - Fee Related
- 2000-10-27 MX MXPA02004004A patent/MXPA02004004A/es active IP Right Grant
- 2000-10-27 PT PT00976715T patent/PT1235810E/pt unknown
- 2000-10-27 DK DK00976715T patent/DK1235810T3/da active
- 2000-10-27 CA CA002387762A patent/CA2387762C/en not_active Expired - Fee Related
- 2000-10-27 AT AT00976715T patent/ATE244704T1/de active
- 2000-10-27 DE DE60003846T patent/DE60003846T2/de not_active Expired - Lifetime
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