DE60302152T2 - Diaminothiazole und ihre anwendung als cdk4 inhibitoren - Google Patents
Diaminothiazole und ihre anwendung als cdk4 inhibitoren Download PDFInfo
- Publication number
- DE60302152T2 DE60302152T2 DE60302152T DE60302152T DE60302152T2 DE 60302152 T2 DE60302152 T2 DE 60302152T2 DE 60302152 T DE60302152 T DE 60302152T DE 60302152 T DE60302152 T DE 60302152T DE 60302152 T2 DE60302152 T2 DE 60302152T2
- Authority
- DE
- Germany
- Prior art keywords
- amino
- thiazol
- methanone
- phenylamino
- phenyl
- 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.)
- Expired - Fee Related
Links
- 0 CCCCC(C)(*)N(*)* Chemical compound CCCCC(C)(*)N(*)* 0.000 description 20
- ICGVMRLHGKCQFR-RWPZCVJISA-N CC(C)N(CCOc(cc1)ccc1/N=C/Sc(c(C(CBr)=O)c1)cc2c1OCO2)C(OC(C)(C)C)=O Chemical compound CC(C)N(CCOc(cc1)ccc1/N=C/Sc(c(C(CBr)=O)c1)cc2c1OCO2)C(OC(C)(C)C)=O ICGVMRLHGKCQFR-RWPZCVJISA-N 0.000 description 1
- NCTISUYDJMSUEX-UHFFFAOYSA-N CCC(c1cc(CC)ccc1)=O Chemical compound CCC(c1cc(CC)ccc1)=O NCTISUYDJMSUEX-UHFFFAOYSA-N 0.000 description 1
- YEKXPPDQTMQJNJ-UHFFFAOYSA-N CCCc(cc(cc1)C(CBr)=O)c1O Chemical compound CCCc(cc(cc1)C(CBr)=O)c1O YEKXPPDQTMQJNJ-UHFFFAOYSA-N 0.000 description 1
- XWRKRSUTFXAMKT-UHFFFAOYSA-N CCN(CC1)CC1Oc(cc1)ccc1N Chemical compound CCN(CC1)CC1Oc(cc1)ccc1N XWRKRSUTFXAMKT-UHFFFAOYSA-N 0.000 description 1
- UDMMJJYIAHHNQA-UHFFFAOYSA-N CCN(CCC1)CC1=O Chemical compound CCN(CCC1)CC1=O UDMMJJYIAHHNQA-UHFFFAOYSA-N 0.000 description 1
- LOUNNTIKZZITPP-UHFFFAOYSA-N CCN(CCC1)CC1Oc(cc1)ccc1Nc1nc(N)c(C(C2C=C(C3CC3)C=CC2C)=O)[s]1 Chemical compound CCN(CCC1)CC1Oc(cc1)ccc1Nc1nc(N)c(C(C2C=C(C3CC3)C=CC2C)=O)[s]1 LOUNNTIKZZITPP-UHFFFAOYSA-N 0.000 description 1
- UUUANEYKZSMQIC-UHFFFAOYSA-N CCN(CCC1)CC1Oc(cc1)ccc1[NH+2]O Chemical compound CCN(CCC1)CC1Oc(cc1)ccc1[NH+2]O UUUANEYKZSMQIC-UHFFFAOYSA-N 0.000 description 1
- BNMPEXSTPVGNSL-UHFFFAOYSA-N CCN(CCOc(cc1)ccc1N=S)C(OC(C)(C)C)=O Chemical compound CCN(CCOc(cc1)ccc1N=S)C(OC(C)(C)C)=O BNMPEXSTPVGNSL-UHFFFAOYSA-N 0.000 description 1
- DJXGNVFIMOMZTF-UHFFFAOYSA-N CCOc1cccc(C(C2=C(N)NC(C)(Nc(cc3)ccc3OCCN3CCCC3)S2)=O)c1 Chemical compound CCOc1cccc(C(C2=C(N)NC(C)(Nc(cc3)ccc3OCCN3CCCC3)S2)=O)c1 DJXGNVFIMOMZTF-UHFFFAOYSA-N 0.000 description 1
- QWMCJRIHOYBIPR-UHFFFAOYSA-N CCc(c(F)c1)ccc1C(C)=O Chemical compound CCc(c(F)c1)ccc1C(C)=O QWMCJRIHOYBIPR-UHFFFAOYSA-N 0.000 description 1
- IBIXIAHOAPMZTJ-UHFFFAOYSA-N CCc1cccc(C(c2c(N)nc(Nc(cc3)ccc3OC3CNCCC3)[s]2)=O)c1 Chemical compound CCc1cccc(C(c2c(N)nc(Nc(cc3)ccc3OC3CNCCC3)[s]2)=O)c1 IBIXIAHOAPMZTJ-UHFFFAOYSA-N 0.000 description 1
- NUIRIOMUOLZYKJ-QGZVFWFLSA-N CCc1cccc(C(c2c(N)nc(Nc(cc3)ccc3OC[C@@H](C)N3CCCC3)[s]2)=O)c1 Chemical compound CCc1cccc(C(c2c(N)nc(Nc(cc3)ccc3OC[C@@H](C)N3CCCC3)[s]2)=O)c1 NUIRIOMUOLZYKJ-QGZVFWFLSA-N 0.000 description 1
- VCOJPHPOVDIRJK-LURJTMIESA-N CN1[C@H](CO)CCC1 Chemical compound CN1[C@H](CO)CCC1 VCOJPHPOVDIRJK-LURJTMIESA-N 0.000 description 1
- XRRPICVLXUEXJJ-OYKVQYDMSA-N CN1[C@H](COc(cc2)ccc2NC(NC(SCCCCC2OC=CC2)=N)=S)CCC1 Chemical compound CN1[C@H](COc(cc2)ccc2NC(NC(SCCCCC2OC=CC2)=N)=S)CCC1 XRRPICVLXUEXJJ-OYKVQYDMSA-N 0.000 description 1
- AZPXSGQWBBPMOC-NSHDSACASA-N CN1[C@H](COc(cc2)ccc2N[O-])CCC1 Chemical compound CN1[C@H](COc(cc2)ccc2N[O-])CCC1 AZPXSGQWBBPMOC-NSHDSACASA-N 0.000 description 1
- QJIDJBIONRJFKP-KRWDZBQOSA-N CN1[C@H](COc(cc2)ccc2Nc2nc(N)c(C(c3cc(F)ccc3)=O)[s]2)CCC1 Chemical compound CN1[C@H](COc(cc2)ccc2Nc2nc(N)c(C(c3cc(F)ccc3)=O)[s]2)CCC1 QJIDJBIONRJFKP-KRWDZBQOSA-N 0.000 description 1
- QRVASKBPOGDYNI-SMIJXYDGSA-N C[C@H](C(CCC(c1cccc(C2CC2)c1)=O)Oc(cc1)ccc1NC(NC(SCC1(CCC2)O[C@H]2[C@H](C)C1)=N)=S)N(C)C Chemical compound C[C@H](C(CCC(c1cccc(C2CC2)c1)=O)Oc(cc1)ccc1NC(NC(SCC1(CCC2)O[C@H]2[C@H](C)C1)=N)=S)N(C)C QRVASKBPOGDYNI-SMIJXYDGSA-N 0.000 description 1
- CXWLZHVSBKYCLQ-XAUUPUKJSA-N C[C@H](COC(C=C1)=CC(C)C1Nc1nc(N)c(C(c2ccc(C)c(F)c2)=O)[s]1)N(C)C Chemical compound C[C@H](COC(C=C1)=CC(C)C1Nc1nc(N)c(C(c2ccc(C)c(F)c2)=O)[s]1)N(C)C CXWLZHVSBKYCLQ-XAUUPUKJSA-N 0.000 description 1
- ZIUOGXYQWQLNQL-SECBINFHSA-N C[C@H](COc(cc1)ccc1N)N(C)C Chemical compound C[C@H](COc(cc1)ccc1N)N(C)C ZIUOGXYQWQLNQL-SECBINFHSA-N 0.000 description 1
- PPZSZPJJTNMYIR-LLVKDONJSA-N C[C@H](COc(cc1)ccc1N)N1CCCC1 Chemical compound C[C@H](COc(cc1)ccc1N)N1CCCC1 PPZSZPJJTNMYIR-LLVKDONJSA-N 0.000 description 1
- YXBWIXRRJJSTQG-GFCCVEGCSA-N C[C@H](COc(cc1)ccc1N=C=S)N1CCCC1 Chemical compound C[C@H](COc(cc1)ccc1N=C=S)N1CCCC1 YXBWIXRRJJSTQG-GFCCVEGCSA-N 0.000 description 1
- IIUFLUOSWPNMAX-SJFWKDOISA-N C[C@H](COc(cc1)ccc1NC(NC(N)SC[O]1C2CCC1CC2)=S)N1CCCC1 Chemical compound C[C@H](COc(cc1)ccc1NC(NC(N)SC[O]1C2CCC1CC2)=S)N1CCCC1 IIUFLUOSWPNMAX-SJFWKDOISA-N 0.000 description 1
- OCBGKEHFSSBCHR-CQSZACIVSA-N C[C@H](COc(cc1)ccc1NC(NC(SCC1(CCCC1)O)=N)=S)N(C)C Chemical compound C[C@H](COc(cc1)ccc1NC(NC(SCC1(CCCC1)O)=N)=S)N(C)C OCBGKEHFSSBCHR-CQSZACIVSA-N 0.000 description 1
- ZXXKNRRGATYTGG-SECBINFHSA-N C[C@H](COc(cc1)ccc1N[O-])N(C)C Chemical compound C[C@H](COc(cc1)ccc1N[O-])N(C)C ZXXKNRRGATYTGG-SECBINFHSA-N 0.000 description 1
- NCLDOAPBCXAMNW-OAHLLOKOSA-N C[C@H](COc(cc1)ccc1Nc1nc(N)c(C(c2cc(C3CC3)ccc2)=O)[s]1)N(C)C Chemical compound C[C@H](COc(cc1)ccc1Nc1nc(N)c(C(c2cc(C3CC3)ccc2)=O)[s]1)N(C)C NCLDOAPBCXAMNW-OAHLLOKOSA-N 0.000 description 1
- DPWCZSXNEGNALT-UHFFFAOYSA-N Cc(c(F)c1)ccc1C(Cl)=O Chemical compound Cc(c(F)c1)ccc1C(Cl)=O DPWCZSXNEGNALT-UHFFFAOYSA-N 0.000 description 1
- XUQCONCMPCVUDM-UHFFFAOYSA-N Cc(c(F)c1)ccc1C(O)=O Chemical compound Cc(c(F)c1)ccc1C(O)=O XUQCONCMPCVUDM-UHFFFAOYSA-N 0.000 description 1
- KIMJXVMZUAJFOB-UHFFFAOYSA-N Cc(ccc(C(CCl)=O)c1)c1F Chemical compound Cc(ccc(C(CCl)=O)c1)c1F KIMJXVMZUAJFOB-UHFFFAOYSA-N 0.000 description 1
- OTYZNDKWNPQQJP-UHFFFAOYSA-N Nc(cc1)ccc1OCCN1CCCC1 Chemical compound Nc(cc1)ccc1OCCN1CCCC1 OTYZNDKWNPQQJP-UHFFFAOYSA-N 0.000 description 1
- CVFSHHHSKJDYOE-UHFFFAOYSA-N Nc1c(C(c2ccc3OCOc3c2)=O)[s]c(Nc(cc2)ccc2OCCN2CCOCC2)n1 Chemical compound Nc1c(C(c2ccc3OCOc3c2)=O)[s]c(Nc(cc2)ccc2OCCN2CCOCC2)n1 CVFSHHHSKJDYOE-UHFFFAOYSA-N 0.000 description 1
- AMCOONRENOMFCT-UHFFFAOYSA-N O=C(CBr)c1cc(C2CC2)ccc1 Chemical compound O=C(CBr)c1cc(C2CC2)ccc1 AMCOONRENOMFCT-UHFFFAOYSA-N 0.000 description 1
- ITAQNNGDCNFGID-UHFFFAOYSA-N O=C(CBr)c1cc(F)ccc1 Chemical compound O=C(CBr)c1cc(F)ccc1 ITAQNNGDCNFGID-UHFFFAOYSA-N 0.000 description 1
- QBXCVQVFPVXAGS-UHFFFAOYSA-N O=C(CBr)c1ccc2OCOc2c1 Chemical compound O=C(CBr)c1ccc2OCOc2c1 QBXCVQVFPVXAGS-UHFFFAOYSA-N 0.000 description 1
- WKGAFKNWVGABDG-UHFFFAOYSA-N S=C=Nc(cc1)ccc1OCCN1CCCC1 Chemical compound S=C=Nc(cc1)ccc1OCCN1CCCC1 WKGAFKNWVGABDG-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/38—Nitrogen atoms
- C07D277/42—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US38151302P | 2002-05-17 | 2002-05-17 | |
| US381513P | 2002-05-17 | ||
| PCT/EP2003/004939 WO2003097048A1 (en) | 2002-05-17 | 2003-05-12 | Diaminothiazoles |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60302152D1 DE60302152D1 (de) | 2005-12-08 |
| DE60302152T2 true DE60302152T2 (de) | 2006-07-13 |
Family
ID=29550137
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60302152T Expired - Fee Related DE60302152T2 (de) | 2002-05-17 | 2003-05-12 | Diaminothiazole und ihre anwendung als cdk4 inhibitoren |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US6818663B2 (enExample) |
| EP (1) | EP1507530B1 (enExample) |
| JP (1) | JP4308133B2 (enExample) |
| KR (1) | KR100619515B1 (enExample) |
| CN (1) | CN100400041C (enExample) |
| AR (1) | AR040078A1 (enExample) |
| AT (1) | ATE308323T1 (enExample) |
| AU (1) | AU2003232754B2 (enExample) |
| BR (1) | BR0310081A (enExample) |
| CA (1) | CA2485367A1 (enExample) |
| DE (1) | DE60302152T2 (enExample) |
| ES (1) | ES2251697T3 (enExample) |
| MX (1) | MXPA04011372A (enExample) |
| PL (1) | PL374581A1 (enExample) |
| RU (1) | RU2311414C2 (enExample) |
| WO (1) | WO2003097048A1 (enExample) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2550891A1 (en) * | 2003-12-24 | 2005-07-14 | Bayer Cropscience Gmbh | Plant growth regulation |
| US7211576B2 (en) * | 2004-04-20 | 2007-05-01 | Hoffmann-La Roche Inc. | Diaminothiazoles |
| US7405220B2 (en) | 2004-06-09 | 2008-07-29 | Hoffmann-La Roche Inc. | Pyrazolopyrimidines |
| US7705009B2 (en) * | 2005-11-22 | 2010-04-27 | Hoffman-La Roche Inc. | 4-aminopyrimidine-5-thione derivatives |
| EP2078003B1 (en) | 2006-10-31 | 2017-03-08 | Merck Sharp & Dohme Corp. | Anilinopiperazine derivatives and methods of use thereof |
| PE20080928A1 (es) | 2006-10-31 | 2008-08-15 | Schering Corp | Derivados de anilinopiperazina como inhibidores de proteina quinasa |
| JP5270758B2 (ja) * | 2008-08-12 | 2013-08-21 | エア プロダクツ アンド ケミカルズ インコーポレイテッド | パー(フェニルエチニル)アレーン誘導体を含有するポリマー組成物 |
| WO2012027481A1 (en) * | 2010-08-24 | 2012-03-01 | Gtx, Inc. | Compounds for treatment of cancer |
| EP2780392B1 (en) | 2011-11-18 | 2016-06-29 | Greene, Tweed & Co. | Crosslinking compounds for high glass transition temperature polymers |
| WO2014172479A1 (en) | 2013-04-16 | 2014-10-23 | Memorial Sloan-Kettering Cancer Center | Companion diagnostic for cdk4 inhibitors |
| WO2015051525A1 (en) * | 2013-10-11 | 2015-04-16 | Rhodia Operations | Synthesis of acetal/ketal |
| WO2017156263A1 (en) | 2016-03-09 | 2017-09-14 | Memorial Sloan-Kettering Cancer Center | Enigma and cdh18 as companion diagnostics for cdk4 inhibitors |
| WO2017158147A1 (en) | 2016-03-18 | 2017-09-21 | Savira Pharmaceuticals Gmbh | Pyrimidone derivatives and their use in the treatment, amelioration or prevention of a viral disease |
| WO2018089902A1 (en) * | 2016-11-13 | 2018-05-17 | Apogee Biotechnology Corporation | Diaminothiazole compounds, compositions and methods of use |
| CN110950848B (zh) * | 2018-09-27 | 2024-03-26 | 徐诺药业 | 新型氨基吡唑类衍生物的合成与应用 |
| JP2022530241A (ja) | 2019-04-30 | 2022-06-28 | インスチトゥート デ メディシーナ モリクラール ジョアン ロボ アントゥネス | Cdk阻害剤と組み合わせたrank経路阻害剤 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2714059B1 (fr) * | 1993-12-21 | 1996-03-08 | Sanofi Elf | Dérivés amino ramifiés du thiazole, leurs procédés de préparation et les compositions pharmaceutiques qui les contiennent. |
| SI20324A (sl) * | 1997-10-27 | 2001-02-28 | Agouron Pharmaceuticals, Inc. | Substituirane 4-amino-tiazol-2-il spojine kot cdk inhibitorji |
| UA71971C2 (en) * | 1999-06-04 | 2005-01-17 | Agoron Pharmaceuticals Inc | Diaminothiazoles, composition based thereon, a method for modulation of protein kinases activity, a method for the treatment of diseases mediated by protein kinases |
| WO2002012250A2 (en) * | 2000-08-09 | 2002-02-14 | Agouron Pharmaceuticals, Inc. | Pyrazole-thiazole compounds, pharmaceutical compositions containing them, and methods of their use for inhibiting cyclin-dependent kinases |
| US6756374B2 (en) | 2001-01-22 | 2004-06-29 | Hoffmann-La Roche Inc. | Diaminothiazoles having antiproliferative activity |
-
2003
- 2003-05-05 US US10/429,551 patent/US6818663B2/en not_active Expired - Fee Related
- 2003-05-12 JP JP2004505047A patent/JP4308133B2/ja not_active Expired - Fee Related
- 2003-05-12 EP EP03752731A patent/EP1507530B1/en not_active Expired - Lifetime
- 2003-05-12 RU RU2004137110/04A patent/RU2311414C2/ru active
- 2003-05-12 DE DE60302152T patent/DE60302152T2/de not_active Expired - Fee Related
- 2003-05-12 KR KR1020047018605A patent/KR100619515B1/ko not_active Expired - Fee Related
- 2003-05-12 CA CA002485367A patent/CA2485367A1/en not_active Abandoned
- 2003-05-12 AT AT03752731T patent/ATE308323T1/de not_active IP Right Cessation
- 2003-05-12 MX MXPA04011372A patent/MXPA04011372A/es active IP Right Grant
- 2003-05-12 WO PCT/EP2003/004939 patent/WO2003097048A1/en not_active Ceased
- 2003-05-12 BR BR0310081-2A patent/BR0310081A/pt not_active IP Right Cessation
- 2003-05-12 CN CNB038111314A patent/CN100400041C/zh not_active Expired - Fee Related
- 2003-05-12 AU AU2003232754A patent/AU2003232754B2/en not_active Ceased
- 2003-05-12 ES ES03752731T patent/ES2251697T3/es not_active Expired - Lifetime
- 2003-05-12 PL PL03374581A patent/PL374581A1/xx not_active Application Discontinuation
- 2003-05-15 AR ARP030101692A patent/AR040078A1/es not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| MXPA04011372A (es) | 2005-08-15 |
| ATE308323T1 (de) | 2005-11-15 |
| KR100619515B1 (ko) | 2006-09-08 |
| PL374581A1 (en) | 2005-10-31 |
| RU2004137110A (ru) | 2005-08-20 |
| US20040006058A1 (en) | 2004-01-08 |
| BR0310081A (pt) | 2005-02-15 |
| CA2485367A1 (en) | 2003-11-27 |
| AU2003232754A1 (en) | 2003-12-02 |
| CN100400041C (zh) | 2008-07-09 |
| AR040078A1 (es) | 2005-03-16 |
| US6818663B2 (en) | 2004-11-16 |
| KR20050006261A (ko) | 2005-01-15 |
| EP1507530B1 (en) | 2005-11-02 |
| DE60302152D1 (de) | 2005-12-08 |
| AU2003232754B2 (en) | 2009-03-12 |
| WO2003097048A1 (en) | 2003-11-27 |
| ES2251697T3 (es) | 2006-05-01 |
| CN1652780A (zh) | 2005-08-10 |
| JP2005530783A (ja) | 2005-10-13 |
| JP4308133B2 (ja) | 2009-08-05 |
| RU2311414C2 (ru) | 2007-11-27 |
| EP1507530A1 (en) | 2005-02-23 |
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