JP2004509839A5 - - Google Patents
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- Publication number
- JP2004509839A5 JP2004509839A5 JP2001580904A JP2001580904A JP2004509839A5 JP 2004509839 A5 JP2004509839 A5 JP 2004509839A5 JP 2001580904 A JP2001580904 A JP 2001580904A JP 2001580904 A JP2001580904 A JP 2001580904A JP 2004509839 A5 JP2004509839 A5 JP 2004509839A5
- Authority
- JP
- Japan
- Prior art keywords
- chromen
- ylmethyl
- pyrimidine
- diamine
- compound according
- 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
- 150000001875 compounds Chemical class 0.000 claims 17
- 239000003814 drug Substances 0.000 claims 5
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 125000000524 functional group Chemical group 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 2
- 229910052794 bromium Inorganic materials 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000006239 protecting group Chemical group 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 229940124530 sulfonamide Drugs 0.000 claims 2
- 150000003456 sulfonamides Chemical class 0.000 claims 2
- BAYDPQRUPRTXJV-UHFFFAOYSA-N 5-[(4-bromo-8-ethoxy-2,2-dimethylchromen-6-yl)methyl]pyrimidine-2,4-diamine Chemical compound C=1C=2C(Br)=CC(C)(C)OC=2C(OCC)=CC=1CC1=CN=C(N)N=C1N BAYDPQRUPRTXJV-UHFFFAOYSA-N 0.000 claims 1
- AWSAHGFHUQXPIF-UHFFFAOYSA-N 5-[(4-bromo-8-ethoxyspiro[chromene-2,1'-cyclobutane]-6-yl)methyl]pyrimidine-2,4-diamine Chemical compound C=1C=2C(Br)=CC3(CCC3)OC=2C(OCC)=CC=1CC1=CN=C(N)N=C1N AWSAHGFHUQXPIF-UHFFFAOYSA-N 0.000 claims 1
- CIEOBODUUABEGI-UHFFFAOYSA-N 5-[(4-bromo-8-methoxy-2,2-dimethylchromen-6-yl)methyl]pyrimidine-2,4-diamine Chemical compound C=1C=2C(Br)=CC(C)(C)OC=2C(OC)=CC=1CC1=CN=C(N)N=C1N CIEOBODUUABEGI-UHFFFAOYSA-N 0.000 claims 1
- KCEXTTYEVBQAAE-UHFFFAOYSA-N 5-[(4-bromo-8-methoxyspiro[chromene-2,4'-oxane]-6-yl)methyl]pyrimidine-2,4-diamine Chemical compound C=1C=2C(Br)=CC3(CCOCC3)OC=2C(OC)=CC=1CC1=CN=C(N)N=C1N KCEXTTYEVBQAAE-UHFFFAOYSA-N 0.000 claims 1
- VSJGJTFTPPQZRO-UHFFFAOYSA-N 5-[(4-chloro-8-methoxy-2,2-dimethylchromen-6-yl)methyl]pyrimidine-2,4-diamine Chemical compound C=1C=2C(Cl)=CC(C)(C)OC=2C(OC)=CC=1CC1=CN=C(N)N=C1N VSJGJTFTPPQZRO-UHFFFAOYSA-N 0.000 claims 1
- SWJJNJQGSMROBJ-UHFFFAOYSA-N 5-[(8-ethoxy-2,2,4-trimethylchromen-6-yl)methyl]pyrimidine-2,4-diamine Chemical compound C=1C=2C(C)=CC(C)(C)OC=2C(OCC)=CC=1CC1=CN=C(N)N=C1N SWJJNJQGSMROBJ-UHFFFAOYSA-N 0.000 claims 1
- XXUYEERDOBVMTA-UHFFFAOYSA-N 5-[(8-ethoxy-2,2-dimethyl-4-propylchromen-6-yl)methyl]pyrimidine-2,4-diamine Chemical compound C1=C2C(CCC)=CC(C)(C)OC2=C(OCC)C=C1CC1=CN=C(N)N=C1N XXUYEERDOBVMTA-UHFFFAOYSA-N 0.000 claims 1
- RICKLMXZWGPFEH-UHFFFAOYSA-N 5-[(8-ethoxy-4-ethyl-2,2-dimethylchromen-6-yl)methyl]pyrimidine-2,4-diamine Chemical compound C=1C=2C(CC)=CC(C)(C)OC=2C(OCC)=CC=1CC1=CN=C(N)N=C1N RICKLMXZWGPFEH-UHFFFAOYSA-N 0.000 claims 1
- UXGWEACVEQDIIR-UHFFFAOYSA-N 5-[(8-methoxy-2,2-dimethyl-4-methylsulfanylchromen-6-yl)methyl]pyrimidine-2,4-diamine Chemical compound C=1C=2C(SC)=CC(C)(C)OC=2C(OC)=CC=1CC1=CN=C(N)N=C1N UXGWEACVEQDIIR-UHFFFAOYSA-N 0.000 claims 1
- LOUYGYYLVYMECR-UHFFFAOYSA-N 5-[[4-(4-fluorophenyl)-8-methoxy-2,2-dimethylchromen-6-yl]methyl]pyrimidine-2,4-diamine Chemical compound C=1C=2C(C=3C=CC(F)=CC=3)=CC(C)(C)OC=2C(OC)=CC=1CC1=CN=C(N)N=C1N LOUYGYYLVYMECR-UHFFFAOYSA-N 0.000 claims 1
- DSDHQJZBYGTHTE-UHFFFAOYSA-N 5-[[8-methoxy-4-(3-methoxyprop-1-ynyl)-2,2-dimethylchromen-6-yl]methyl]pyrimidine-2,4-diamine Chemical compound C1=C2C(C#CCOC)=CC(C)(C)OC2=C(OC)C=C1CC1=CN=C(N)N=C1N DSDHQJZBYGTHTE-UHFFFAOYSA-N 0.000 claims 1
- 125000004008 6 membered carbocyclic group Chemical group 0.000 claims 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 1
- 125000005103 alkyl silyl group Chemical group 0.000 claims 1
- 125000004414 alkyl thio group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 230000000844 anti-bacterial effect Effects 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 125000002837 carbocyclic group Chemical group 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
- 125000005016 hydroxyalkynyl group Chemical group 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP00108945 | 2000-04-27 | ||
| PCT/EP2001/004541 WO2001083476A1 (en) | 2000-04-27 | 2001-04-20 | Chromenylmethyl pyrimidinediamines as antibacterial agents |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2004509839A JP2004509839A (ja) | 2004-04-02 |
| JP2004509839A5 true JP2004509839A5 (https=) | 2005-01-27 |
| JP4033676B2 JP4033676B2 (ja) | 2008-01-16 |
Family
ID=8168565
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001580904A Expired - Fee Related JP4033676B2 (ja) | 2000-04-27 | 2001-04-20 | 抗菌剤としてのクロメニルメチルピリミジンジアミン類 |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US6818649B2 (https=) |
| EP (1) | EP1278742B1 (https=) |
| JP (1) | JP4033676B2 (https=) |
| KR (1) | KR20020093966A (https=) |
| CN (1) | CN1249057C (https=) |
| AT (1) | ATE284882T1 (https=) |
| AU (1) | AU2001252269A1 (https=) |
| BR (1) | BR0110255A (https=) |
| CA (1) | CA2405614A1 (https=) |
| DE (1) | DE60107832T2 (https=) |
| ES (1) | ES2232614T3 (https=) |
| MX (1) | MXPA02010518A (https=) |
| WO (1) | WO2001083476A1 (https=) |
| ZA (1) | ZA200208271B (https=) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI243173B (en) | 1999-11-17 | 2005-11-11 | Akzo Nobel Nv | Spiro[2H-1-benzopyran-2,4'-piperidine] derivatives |
| NZ546834A (en) * | 2003-10-01 | 2010-03-26 | Adolor Corp | Spirocyclic heterocyclic derivatives and methods of their use |
| AU2006206458B2 (en) * | 2005-01-19 | 2012-10-25 | Rigel Pharmaceuticals, Inc. | Prodrugs of 2,4-pyrimidinediamine compounds and their uses |
| US7598261B2 (en) | 2005-03-31 | 2009-10-06 | Adolor Corporation | Spirocyclic heterocyclic derivatives and methods of their use |
| EP1770089A1 (en) * | 2005-10-03 | 2007-04-04 | Institut Pasteur | Pyranodibenzofuran derivatives with antifungal and antibacterial activity |
| US7855194B2 (en) | 2006-03-27 | 2010-12-21 | Hoffmann-La Roche Inc. | Pyrimidine, quinazoline, pteridine and triazine derivatives |
| US7576207B2 (en) | 2006-04-06 | 2009-08-18 | Adolor Corporation | Spirocyclic heterocyclic derivatives and methods of their use |
| CN109134493A (zh) * | 2018-09-19 | 2019-01-04 | 浙江师范大学 | 一种具有抗菌活性的2-氧代色烯并噻吩衍生物及其合成方法和应用 |
| CN109988156B (zh) * | 2019-03-12 | 2021-12-28 | 广东中科药物研究有限公司 | 一种氨基嘧啶化合物 |
| CN112824412B (zh) * | 2019-11-21 | 2022-09-16 | 中国科学院大连化学物理研究所 | 手性1′H-螺[吲哚啉-3,4′-吡喃并[2,3-c]吡唑]-2-酮类化合物 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK0866791T3 (da) * | 1995-12-04 | 2002-04-22 | Arpida Ag | Diaminopyrimidiner, farmaceutiske præparater indeholdende disse og deres anvendelse som antibakterielle midler |
-
2001
- 2001-04-20 KR KR1020027014451A patent/KR20020093966A/ko not_active Ceased
- 2001-04-20 CN CNB018085962A patent/CN1249057C/zh not_active Expired - Fee Related
- 2001-04-20 EP EP01925562A patent/EP1278742B1/en not_active Expired - Lifetime
- 2001-04-20 JP JP2001580904A patent/JP4033676B2/ja not_active Expired - Fee Related
- 2001-04-20 DE DE60107832T patent/DE60107832T2/de not_active Expired - Lifetime
- 2001-04-20 AT AT01925562T patent/ATE284882T1/de not_active IP Right Cessation
- 2001-04-20 AU AU2001252269A patent/AU2001252269A1/en not_active Abandoned
- 2001-04-20 MX MXPA02010518A patent/MXPA02010518A/es unknown
- 2001-04-20 ES ES01925562T patent/ES2232614T3/es not_active Expired - Lifetime
- 2001-04-20 WO PCT/EP2001/004541 patent/WO2001083476A1/en not_active Ceased
- 2001-04-20 US US10/258,777 patent/US6818649B2/en not_active Expired - Fee Related
- 2001-04-20 CA CA002405614A patent/CA2405614A1/en not_active Abandoned
- 2001-04-20 BR BR0110255-9A patent/BR0110255A/pt not_active IP Right Cessation
-
2002
- 2002-10-14 ZA ZA200208271A patent/ZA200208271B/en unknown
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