JP2006500353A5 - - Google Patents
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- Publication number
- JP2006500353A5 JP2006500353A5 JP2004527753A JP2004527753A JP2006500353A5 JP 2006500353 A5 JP2006500353 A5 JP 2006500353A5 JP 2004527753 A JP2004527753 A JP 2004527753A JP 2004527753 A JP2004527753 A JP 2004527753A JP 2006500353 A5 JP2006500353 A5 JP 2006500353A5
- Authority
- JP
- Japan
- Prior art keywords
- cyano
- pyrazinyl
- urea
- phenyl
- chloro
- 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.)
- Pending
Links
- 150000001875 compounds Chemical class 0.000 claims 21
- 125000000217 alkyl group Chemical group 0.000 claims 17
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 11
- 239000004202 carbamide Substances 0.000 claims 11
- 239000001257 hydrogen Substances 0.000 claims 9
- 229910052739 hydrogen Inorganic materials 0.000 claims 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims 8
- -1 amino, carboxy Chemical group 0.000 claims 7
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 6
- 150000002431 hydrogen Chemical class 0.000 claims 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims 5
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 5
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 5
- 125000003342 alkenyl group Chemical group 0.000 claims 4
- 125000004103 aminoalkyl group Chemical group 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 125000004686 alkyl sulfanyl alkyl group Chemical group 0.000 claims 3
- 125000000304 alkynyl group Chemical group 0.000 claims 3
- 125000001475 halogen functional group Chemical group 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 125000005081 alkoxyalkoxyalkyl group Chemical group 0.000 claims 2
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 125000005160 aryl oxy alkyl group Chemical group 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- PVAQILHDQHGVSP-UHFFFAOYSA-N 1-(5-chloro-2-cyclohex-2-en-1-yloxyphenyl)-3-(5-cyanopyrazin-2-yl)urea Chemical compound C=1N=C(C#N)C=NC=1NC(=O)NC1=CC(Cl)=CC=C1OC1CCCC=C1 PVAQILHDQHGVSP-UHFFFAOYSA-N 0.000 claims 1
- SECYNSPYZHCPIK-UHFFFAOYSA-N 1-(5-chloro-2-cyclopent-3-en-1-yloxyphenyl)-3-(5-cyanopyrazin-2-yl)urea Chemical compound C=1N=C(C#N)C=NC=1NC(=O)NC1=CC(Cl)=CC=C1OC1CC=CC1 SECYNSPYZHCPIK-UHFFFAOYSA-N 0.000 claims 1
- BMZFLFKIZNBUFB-UHFFFAOYSA-N 1-(5-chloro-2-phenacyloxyphenyl)-3-(5-cyanopyrazin-2-yl)urea Chemical compound C=1N=C(C#N)C=NC=1NC(=O)NC1=CC(Cl)=CC=C1OCC(=O)C1=CC=CC=C1 BMZFLFKIZNBUFB-UHFFFAOYSA-N 0.000 claims 1
- LYRRMGQXNDNVPS-UHFFFAOYSA-N 1-[2-(3-aminopropoxy)-5-chlorophenyl]-3-(5-cyanopyrazin-2-yl)urea Chemical compound NCCCOC1=CC=C(Cl)C=C1NC(=O)NC1=CN=C(C#N)C=N1 LYRRMGQXNDNVPS-UHFFFAOYSA-N 0.000 claims 1
- XYCSIMKFHRSWBS-UHFFFAOYSA-N 1-[2-[2-(4-bromophenoxy)ethoxy]-5-chlorophenyl]-3-(5-cyanopyrazin-2-yl)urea Chemical compound C=1N=C(C#N)C=NC=1NC(=O)NC1=CC(Cl)=CC=C1OCCOC1=CC=C(Br)C=C1 XYCSIMKFHRSWBS-UHFFFAOYSA-N 0.000 claims 1
- CWTLRICITVFRIL-RFHHWMCGSA-N 1-[2-[[(1s,4s)-3-bicyclo[2.2.1]heptanyl]methoxy]-5-chlorophenyl]-3-(5-cyanopyrazin-2-yl)urea Chemical compound C1([C@@]2([H])CC[C@@](C2)(C1)[H])COC1=CC=C(Cl)C=C1NC(=O)NC1=CN=C(C#N)C=N1 CWTLRICITVFRIL-RFHHWMCGSA-N 0.000 claims 1
- UOVQGCMOPSZGOP-UHFFFAOYSA-N 1-[2-[benzyl(2-hydroxyethyl)amino]-5-bromophenyl]-3-(5-cyanopyrazin-2-yl)urea Chemical compound C=1C=C(Br)C=C(NC(=O)NC=2N=CC(=NC=2)C#N)C=1N(CCO)CC1=CC=CC=C1 UOVQGCMOPSZGOP-UHFFFAOYSA-N 0.000 claims 1
- NSHVATFCXCSIAN-UHFFFAOYSA-N 1-[2-[benzyl(2-hydroxyethyl)amino]-5-chlorophenyl]-3-(5-cyanopyrazin-2-yl)urea Chemical compound C=1C=C(Cl)C=C(NC(=O)NC=2N=CC(=NC=2)C#N)C=1N(CCO)CC1=CC=CC=C1 NSHVATFCXCSIAN-UHFFFAOYSA-N 0.000 claims 1
- FKQHZPMKUJQFBQ-UHFFFAOYSA-N 1-[2-[bis(2-methoxyethyl)amino]-5-bromophenyl]-3-(5-cyanopyrazin-2-yl)urea Chemical compound COCCN(CCOC)C1=CC=C(Br)C=C1NC(=O)NC1=CN=C(C#N)C=N1 FKQHZPMKUJQFBQ-UHFFFAOYSA-N 0.000 claims 1
- NGJURHJPIBNKHP-UHFFFAOYSA-N 1-[2-[bis(2-methoxyethyl)amino]-5-chlorophenyl]-3-(5-cyanopyrazin-2-yl)urea Chemical compound COCCN(CCOC)C1=CC=C(Cl)C=C1NC(=O)NC1=CN=C(C#N)C=N1 NGJURHJPIBNKHP-UHFFFAOYSA-N 0.000 claims 1
- YFTMNKQWOWZYPP-UHFFFAOYSA-N 1-[5-bromo-2-[(2-hydroxy-2-phenylethyl)-methylamino]phenyl]-3-(5-cyanopyrazin-2-yl)urea Chemical compound C=1C=C(Br)C=C(NC(=O)NC=2N=CC(=NC=2)C#N)C=1N(C)CC(O)C1=CC=CC=C1 YFTMNKQWOWZYPP-UHFFFAOYSA-N 0.000 claims 1
- QXWXEJMOZMDALO-UHFFFAOYSA-N 1-[5-bromo-2-[ethyl(2-methoxyethyl)amino]phenyl]-3-(5-cyanopyrazin-2-yl)urea Chemical compound COCCN(CC)C1=CC=C(Br)C=C1NC(=O)NC1=CN=C(C#N)C=N1 QXWXEJMOZMDALO-UHFFFAOYSA-N 0.000 claims 1
- SECWPIJSHYOZKM-UHFFFAOYSA-N 1-[5-chloro-2-(1-ethoxypropan-2-yloxy)phenyl]-3-(5-cyanopyrazin-2-yl)urea Chemical compound CCOCC(C)OC1=CC=C(Cl)C=C1NC(=O)NC1=CN=C(C#N)C=N1 SECWPIJSHYOZKM-UHFFFAOYSA-N 0.000 claims 1
- FHKIBVIDIBQHBF-UHFFFAOYSA-N 1-[5-chloro-2-(1-methoxypropan-2-yloxy)phenyl]-3-(5-cyanopyrazin-2-yl)urea Chemical compound COCC(C)OC1=CC=C(Cl)C=C1NC(=O)NC1=CN=C(C#N)C=N1 FHKIBVIDIBQHBF-UHFFFAOYSA-N 0.000 claims 1
- JBNRXWLOFSXQPH-UHFFFAOYSA-N 1-[5-chloro-2-(2-cyclohexylethoxy)phenyl]-3-(5-cyanopyrazin-2-yl)urea Chemical compound C=1N=C(C#N)C=NC=1NC(=O)NC1=CC(Cl)=CC=C1OCCC1CCCCC1 JBNRXWLOFSXQPH-UHFFFAOYSA-N 0.000 claims 1
- LXKNXVQJYTVJID-UHFFFAOYSA-N 1-[5-chloro-2-(2-ethoxyethoxy)phenyl]-3-(5-cyanopyrazin-2-yl)urea Chemical compound CCOCCOC1=CC=C(Cl)C=C1NC(=O)NC1=CN=C(C#N)C=N1 LXKNXVQJYTVJID-UHFFFAOYSA-N 0.000 claims 1
- MWFYFELKCFAENX-UHFFFAOYSA-N 1-[5-chloro-2-(2-methoxyethoxy)phenyl]-3-(5-cyanopyrazin-2-yl)urea Chemical compound COCCOC1=CC=C(Cl)C=C1NC(=O)NC1=CN=C(C#N)C=N1 MWFYFELKCFAENX-UHFFFAOYSA-N 0.000 claims 1
- ATMLVTOWEJMISI-UHFFFAOYSA-N 1-[5-chloro-2-(2-methylsulfanylethoxy)phenyl]-3-(5-cyanopyrazin-2-yl)urea Chemical compound CSCCOC1=CC=C(Cl)C=C1NC(=O)NC1=CN=C(C#N)C=N1 ATMLVTOWEJMISI-UHFFFAOYSA-N 0.000 claims 1
- QUQIALMRPMENGJ-UHFFFAOYSA-N 1-[5-chloro-2-(2-propan-2-yloxyethoxy)phenyl]-3-(5-cyanopyrazin-2-yl)urea Chemical compound CC(C)OCCOC1=CC=C(Cl)C=C1NC(=O)NC1=CN=C(C#N)C=N1 QUQIALMRPMENGJ-UHFFFAOYSA-N 0.000 claims 1
- WHSYXEUKLZRABI-UHFFFAOYSA-N 1-[5-chloro-2-(cyclopropylmethoxy)phenyl]-3-(5-cyanopyrazin-2-yl)urea Chemical compound C=1N=C(C#N)C=NC=1NC(=O)NC1=CC(Cl)=CC=C1OCC1CC1 WHSYXEUKLZRABI-UHFFFAOYSA-N 0.000 claims 1
- SMZDIRCVFZTJOH-UHFFFAOYSA-N 1-[5-chloro-2-[(1-methylcyclopropyl)methoxy]phenyl]-3-(5-cyanopyrazin-2-yl)urea Chemical compound C=1C=C(Cl)C=C(NC(=O)NC=2N=CC(=NC=2)C#N)C=1OCC1(C)CC1 SMZDIRCVFZTJOH-UHFFFAOYSA-N 0.000 claims 1
- QTKDJHMPFMGJMG-OLZOCXBDSA-N 1-[5-chloro-2-[(1s,3r)-3-hydroxycyclopentyl]oxyphenyl]-3-(5-cyanopyrazin-2-yl)urea Chemical compound C1[C@H](O)CC[C@@H]1OC1=CC=C(Cl)C=C1NC(=O)NC1=CN=C(C#N)C=N1 QTKDJHMPFMGJMG-OLZOCXBDSA-N 0.000 claims 1
- XDROTNZAWWKOTD-UHFFFAOYSA-N 1-[5-chloro-2-[(2-hydroxy-2-phenylethyl)-methylamino]phenyl]-3-(5-cyanopyrazin-2-yl)urea Chemical compound C=1C=C(Cl)C=C(NC(=O)NC=2N=CC(=NC=2)C#N)C=1N(C)CC(O)C1=CC=CC=C1 XDROTNZAWWKOTD-UHFFFAOYSA-N 0.000 claims 1
- WZDAKTSKZFOPJB-UHFFFAOYSA-N 1-[5-chloro-2-[(2-methylcyclopropyl)methoxy]phenyl]-3-(5-cyanopyrazin-2-yl)urea Chemical compound CC1CC1COC1=CC=C(Cl)C=C1NC(=O)NC1=CN=C(C#N)C=N1 WZDAKTSKZFOPJB-UHFFFAOYSA-N 0.000 claims 1
- URMCAXGZEZUWEG-QXMXGUDHSA-N 1-[5-chloro-2-[(3s,4r)-3,4-dihydroxycyclopentyl]oxyphenyl]-3-(5-cyanopyrazin-2-yl)urea Chemical compound C1[C@@H](O)[C@@H](O)CC1OC1=CC=C(Cl)C=C1NC(=O)NC1=CN=C(C#N)C=N1 URMCAXGZEZUWEG-QXMXGUDHSA-N 0.000 claims 1
- IODANOYNIPFWFE-UHFFFAOYSA-N 1-[5-chloro-2-[1-(dimethylamino)propan-2-yloxy]phenyl]-3-(5-cyanopyrazin-2-yl)urea Chemical compound CN(C)CC(C)OC1=CC=C(Cl)C=C1NC(=O)NC1=CN=C(C#N)C=N1 IODANOYNIPFWFE-UHFFFAOYSA-N 0.000 claims 1
- WABCAIVLMXJPIS-UHFFFAOYSA-N 1-[5-chloro-2-[2-(n-ethyl-3-methylanilino)ethoxy]phenyl]-3-(5-cyanopyrazin-2-yl)urea Chemical compound C=1C=CC(C)=CC=1N(CC)CCOC1=CC=C(Cl)C=C1NC(=O)NC1=CN=C(C#N)C=N1 WABCAIVLMXJPIS-UHFFFAOYSA-N 0.000 claims 1
- OEMOGAOWNWNMAR-UHFFFAOYSA-N 1-[5-chloro-2-[2-[3-(6-methylpyridin-2-yl)propoxy]ethoxy]phenyl]-3-(5-cyanopyrazin-2-yl)urea Chemical compound CC1=CC=CC(CCCOCCOC=2C(=CC(Cl)=CC=2)NC(=O)NC=2N=CC(=NC=2)C#N)=N1 OEMOGAOWNWNMAR-UHFFFAOYSA-N 0.000 claims 1
- GBSMMFHITBMOIH-UHFFFAOYSA-N 1-[5-chloro-2-[3-(dimethylamino)propoxy]phenyl]-3-(5-cyanopyrazin-2-yl)urea Chemical compound CN(C)CCCOC1=CC=C(Cl)C=C1NC(=O)NC1=CN=C(C#N)C=N1 GBSMMFHITBMOIH-UHFFFAOYSA-N 0.000 claims 1
- FWFZPSCKCHHLCM-UHFFFAOYSA-N 1-[5-chloro-2-[ethyl(2-methoxyethyl)amino]phenyl]-3-(5-cyanopyrazin-2-yl)urea Chemical compound COCCN(CC)C1=CC=C(Cl)C=C1NC(=O)NC1=CN=C(C#N)C=N1 FWFZPSCKCHHLCM-UHFFFAOYSA-N 0.000 claims 1
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 1
- 125000001331 3-methylbutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])O* 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 102000001253 Protein Kinase Human genes 0.000 claims 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 1
- 125000005336 allyloxy group Chemical group 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- SHZIWNPUGXLXDT-UHFFFAOYSA-N ethyl hexanoate Chemical group CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 108060006633 protein kinase Proteins 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/218,121 US20040034038A1 (en) | 2002-08-13 | 2002-08-13 | Urea kinase inhibitors |
| PCT/US2003/024474 WO2004014876A1 (en) | 2002-08-13 | 2003-08-05 | Urea derivatives as kinase inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2006500353A JP2006500353A (ja) | 2006-01-05 |
| JP2006500353A5 true JP2006500353A5 (https=) | 2006-10-26 |
Family
ID=31714498
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004527753A Pending JP2006500353A (ja) | 2002-08-13 | 2003-08-05 | キナーゼ阻害剤としての尿素誘導体 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US20040034038A1 (https=) |
| EP (1) | EP1534692A1 (https=) |
| JP (1) | JP2006500353A (https=) |
| CA (1) | CA2494848A1 (https=) |
| MX (1) | MXPA05001724A (https=) |
| WO (1) | WO2004014876A1 (https=) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005072733A1 (en) * | 2004-01-20 | 2005-08-11 | Millennium Pharmaceuticals, Inc. | Dyarylurea compounds as chk-1 inhibitors |
| GB0512324D0 (en) * | 2005-06-16 | 2005-07-27 | Novartis Ag | Organic compounds |
| MX2007000265A (es) * | 2004-07-02 | 2007-07-20 | Icos Corp | Compuestos utiles para inhibir chk1. |
| HRP20100678T1 (hr) | 2005-03-29 | 2011-02-28 | Icos Corporation | Derivati heteroariluree korisni kao inhibitori chk1 |
| GEP20105074B (en) * | 2005-12-21 | 2010-09-10 | Novartis Ag | Pyrimidinyl aryl urea derivatives being fgf inhibitors |
| HU227696B1 (en) * | 2006-04-13 | 2011-12-28 | Egyt Gyogyszervegyeszeti Gyar | Zinc salt of rosuvastatin, process for its preparation and pharmaceutical compositions containing it |
| JP2010510222A (ja) * | 2006-11-17 | 2010-04-02 | シェーリング コーポレイション | 増殖性障害に対する併用療法 |
| US8314108B2 (en) | 2008-12-17 | 2012-11-20 | Eli Lilly And Company | 5-(5-(2-(3-aminopropoxy)-6-methoxyphenyl)-1H-pyrazol-3-ylamino)pyrazine-2-carbonitrile, pharmaceutically acceptable salts thereof, or solvate of salts |
| PA8850801A1 (es) | 2008-12-17 | 2010-07-27 | Lilly Co Eli | Compuestos útiles para inhibir chk1 |
| GB201008005D0 (en) | 2010-05-13 | 2010-06-30 | Sentinel Oncology Ltd | Pharmaceutical compounds |
| EP2970114B1 (en) * | 2013-03-15 | 2019-05-15 | Bristol-Myers Squibb Company | Ido inhibitors |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1213022C (zh) * | 1997-12-22 | 2005-08-03 | 拜尔有限公司 | 用对称和不对称的取代二苯脲抑制raf激酶 |
| EP1140840B1 (en) * | 1999-01-13 | 2006-03-22 | Bayer Pharmaceuticals Corp. | -g(v)-carboxyaryl substituted diphenyl ureas as raf kinase inhibitors |
| KR20020084116A (ko) * | 2000-02-07 | 2002-11-04 | 애보트 게엠베하 운트 콤파니 카게 | 2-벤조티아졸릴 우레아 유도체 및 이의 단백질 키나제억제제로서의 용도 |
| UA76977C2 (en) * | 2001-03-02 | 2006-10-16 | Icos Corp | Aryl- and heteroaryl substituted chk1 inhibitors and their use as radiosensitizers and chemosensitizers |
-
2002
- 2002-08-13 US US10/218,121 patent/US20040034038A1/en not_active Abandoned
-
2003
- 2003-08-05 MX MXPA05001724A patent/MXPA05001724A/es unknown
- 2003-08-05 EP EP03784917A patent/EP1534692A1/en not_active Withdrawn
- 2003-08-05 WO PCT/US2003/024474 patent/WO2004014876A1/en not_active Ceased
- 2003-08-05 CA CA002494848A patent/CA2494848A1/en not_active Abandoned
- 2003-08-05 JP JP2004527753A patent/JP2006500353A/ja active Pending
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