JP2007513091A5 - - Google Patents
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- Publication number
- JP2007513091A5 JP2007513091A5 JP2006541481A JP2006541481A JP2007513091A5 JP 2007513091 A5 JP2007513091 A5 JP 2007513091A5 JP 2006541481 A JP2006541481 A JP 2006541481A JP 2006541481 A JP2006541481 A JP 2006541481A JP 2007513091 A5 JP2007513091 A5 JP 2007513091A5
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- alkyl
- alkoxy
- hydrogen
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 claims 39
- 150000001875 compounds Chemical class 0.000 claims 33
- -1 R 5 -aryl Chemical group 0.000 claims 17
- 125000000217 alkyl group Chemical group 0.000 claims 16
- 239000012024 dehydrating agents Substances 0.000 claims 13
- 229910052739 hydrogen Inorganic materials 0.000 claims 13
- 239000001257 hydrogen Substances 0.000 claims 13
- 229910052736 halogen Inorganic materials 0.000 claims 11
- 150000002367 halogens Chemical class 0.000 claims 11
- 125000001424 substituent group Chemical group 0.000 claims 11
- 125000003545 alkoxy group Chemical group 0.000 claims 7
- 150000002431 hydrogen Chemical group 0.000 claims 7
- 229910001507 metal halide Inorganic materials 0.000 claims 7
- 150000005309 metal halides Chemical class 0.000 claims 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims 6
- 230000003197 catalytic effect Effects 0.000 claims 6
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 claims 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
- 125000003118 aryl group Chemical group 0.000 claims 5
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 4
- 125000004663 dialkyl amino group Chemical group 0.000 claims 4
- 125000001072 heteroaryl group Chemical group 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 3
- 239000011780 sodium chloride Substances 0.000 claims 3
- GBHCABUWWQUMAJ-UHFFFAOYSA-N 2-hydrazinoethanol Chemical compound NNCCO GBHCABUWWQUMAJ-UHFFFAOYSA-N 0.000 claims 2
- 125000003282 alkyl amino group Chemical group 0.000 claims 2
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 2
- 125000004414 alkyl thio group Chemical group 0.000 claims 2
- 125000002947 alkylene group Chemical group 0.000 claims 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 239000000460 chlorine Substances 0.000 claims 2
- 230000021615 conjugation Effects 0.000 claims 2
- 230000026030 halogenation Effects 0.000 claims 2
- 238000005658 halogenation reaction Methods 0.000 claims 2
- 238000007363 ring formation reaction Methods 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- CTTUQCIBNSCQRH-UHFFFAOYSA-N 2,3,4-trimethylpentan-3-amine Chemical compound CC(C)C(C)(N)C(C)C CTTUQCIBNSCQRH-UHFFFAOYSA-N 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- 101100283604 Caenorhabditis elegans pigk-1 gene Proteins 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 1
- 239000005977 Ethylene Substances 0.000 claims 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000005085 alkoxycarbonylalkoxy group Chemical group 0.000 claims 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 150000001721 carbon Chemical group 0.000 claims 1
- 125000005111 carboxyalkoxy group Chemical group 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 125000005112 cycloalkylalkoxy group Chemical group 0.000 claims 1
- 230000002140 halogenating effect Effects 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000005113 hydroxyalkoxy group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 125000002757 morpholinyl group Chemical group 0.000 claims 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 229910052698 phosphorus Inorganic materials 0.000 claims 1
- 239000011574 phosphorus Substances 0.000 claims 1
- 125000005270 trialkylamine group Chemical group 0.000 claims 1
- 229910052725 zinc Inorganic materials 0.000 claims 1
- 239000011701 zinc Substances 0.000 claims 1
- IIEAJFVQJSLSPU-UHFFFAOYSA-N Nc1nc(Cl)c(C=O)c(NNC(c2ccc[o]2)=O)n1 Chemical compound Nc1nc(Cl)c(C=O)c(NNC(c2ccc[o]2)=O)n1 IIEAJFVQJSLSPU-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US52592503P | 2003-12-01 | 2003-12-01 | |
| PCT/US2004/039847 WO2005054245A2 (en) | 2003-12-01 | 2004-11-29 | Process for preparing substituted 5-amino-pyrazolo-[4,3-e]-1,2,4-triazolo[1,5-c]pyrimidines |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2007513091A JP2007513091A (ja) | 2007-05-24 |
| JP2007513091A5 true JP2007513091A5 (enExample) | 2007-12-20 |
Family
ID=34652398
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006541481A Withdrawn JP2007513091A (ja) | 2003-12-01 | 2004-11-29 | 置換された５−アミノ−ピラゾロ−［４，３−ｅ］−１，２，４−トリアゾロ［１，５−ｃ］ピリミジンを調製するための方法 |
Country Status (8)
| Country | Link |
|---|---|
| US (3) | US7235659B2 (enExample) |
| EP (1) | EP1689749B1 (enExample) |
| JP (1) | JP2007513091A (enExample) |
| AT (1) | ATE377599T1 (enExample) |
| CA (1) | CA2547248A1 (enExample) |
| DE (1) | DE602004009962T2 (enExample) |
| ES (1) | ES2293380T3 (enExample) |
| WO (1) | WO2005054245A2 (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL152726A0 (en) * | 2000-05-26 | 2003-06-24 | Schering Corp | Adenosine a2a receptor antagonists |
| DK1678182T3 (da) * | 2003-10-28 | 2007-06-04 | Schering Corp | Fremgangsmåde til fremstilling af substituerede 5-amino-pyrazolo[4,3-E]-1,2,4-triazolo-[1,5-C]pyrimidiner |
| ATE556712T1 (de) * | 2005-06-07 | 2012-05-15 | Kyowa Hakko Kirin Co Ltd | A2a antagonisten zur behandlung von motorischen störungen |
| ES2273599B1 (es) | 2005-10-14 | 2008-06-01 | Universidad De Barcelona | Compuestos para el tratamiento de la fibrilacion auricular. |
| US8188098B2 (en) | 2008-05-19 | 2012-05-29 | Hoffmann-La Roche Inc. | GPR119 receptor agonists |
| US8343961B2 (en) | 2009-03-31 | 2013-01-01 | Arqule, Inc. | Substituted heterocyclic compounds |
| WO2012127472A1 (en) * | 2011-03-22 | 2012-09-27 | Mapi Pharma Ltd. | Process and intermediates for the preparation of preladenant and related compounds |
| WO2012129381A1 (en) | 2011-03-22 | 2012-09-27 | Concert Pharmaceuticals Inc. | Deuterated preladenant |
| WO2013024474A1 (en) * | 2011-08-18 | 2013-02-21 | Mapi Phrarma Ltd. | Polymorphs of preladenant |
| PE20211768A1 (es) | 2018-11-30 | 2021-09-07 | Merck Sharp & Dohme | Derivados de amino triazolo quinazolina 9-sustituidos como antagonistas del receptor de adenosina, composiciones farmaceuticas y su uso |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1264901B1 (it) * | 1993-06-29 | 1996-10-17 | Schering Plough S P A | Analoghi eterociclici di 1,2,4-triazolo(15-c)pirimidine ad attivita' antagonista per il recettore a2 dell'adenosina |
| IL152726A0 (en) | 2000-05-26 | 2003-06-24 | Schering Corp | Adenosine a2a receptor antagonists |
-
2004
- 2004-11-29 AT AT04812380T patent/ATE377599T1/de not_active IP Right Cessation
- 2004-11-29 EP EP04812380A patent/EP1689749B1/en not_active Expired - Lifetime
- 2004-11-29 WO PCT/US2004/039847 patent/WO2005054245A2/en not_active Ceased
- 2004-11-29 ES ES04812380T patent/ES2293380T3/es not_active Expired - Lifetime
- 2004-11-29 JP JP2006541481A patent/JP2007513091A/ja not_active Withdrawn
- 2004-11-29 DE DE602004009962T patent/DE602004009962T2/de not_active Expired - Lifetime
- 2004-11-29 US US10/999,048 patent/US7235659B2/en not_active Expired - Fee Related
- 2004-11-29 CA CA002547248A patent/CA2547248A1/en not_active Abandoned
-
2007
- 2007-05-17 US US11/804,162 patent/US7507822B2/en not_active Expired - Fee Related
-
2009
- 2009-01-27 US US12/360,570 patent/US20090131663A1/en not_active Abandoned
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