JP2004522755A5 - - Google Patents
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- Publication number
- JP2004522755A5 JP2004522755A5 JP2002562428A JP2002562428A JP2004522755A5 JP 2004522755 A5 JP2004522755 A5 JP 2004522755A5 JP 2002562428 A JP2002562428 A JP 2002562428A JP 2002562428 A JP2002562428 A JP 2002562428A JP 2004522755 A5 JP2004522755 A5 JP 2004522755A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- group
- heteroaryl
- same
- aryl
- 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
- 125000001072 heteroaryl group Chemical group 0.000 claims 133
- 125000000217 alkyl group Chemical group 0.000 claims 130
- 229910052736 halogen Inorganic materials 0.000 claims 96
- 150000002367 halogens Chemical class 0.000 claims 94
- 150000001875 compounds Chemical class 0.000 claims 78
- 229910052739 hydrogen Inorganic materials 0.000 claims 75
- 239000001257 hydrogen Substances 0.000 claims 68
- 125000003118 aryl group Chemical group 0.000 claims 60
- 125000001424 substituent group Chemical group 0.000 claims 59
- 125000000753 cycloalkyl group Chemical group 0.000 claims 58
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 52
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 47
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 41
- -1 benzoimidazolyl Chemical group 0.000 claims 32
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 29
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 claims 26
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 25
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 23
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 23
- 150000003839 salts Chemical class 0.000 claims 23
- 125000001544 thienyl group Chemical group 0.000 claims 23
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical group C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims 22
- 125000000304 alkynyl group Chemical group 0.000 claims 21
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Chemical group C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 20
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 19
- 125000003545 alkoxy group Chemical group 0.000 claims 19
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 19
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 19
- 125000002541 furyl group Chemical group 0.000 claims 17
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical group C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 16
- 125000004076 pyridyl group Chemical group 0.000 claims 15
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 14
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 14
- 125000005842 heteroatom Chemical group 0.000 claims 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 13
- 125000004093 cyano group Chemical group *C#N 0.000 claims 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 12
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 12
- 125000004122 cyclic group Chemical group 0.000 claims 12
- 150000002431 hydrogen Chemical class 0.000 claims 12
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Chemical group C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims 11
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical group C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 11
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims 11
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 10
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 9
- 229910052760 oxygen Inorganic materials 0.000 claims 9
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical group C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 8
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical group C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims 8
- 229910052799 carbon Inorganic materials 0.000 claims 8
- 150000003852 triazoles Chemical group 0.000 claims 8
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 7
- XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 claims 7
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 7
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical group C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims 7
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical group C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims 7
- 229910052757 nitrogen Inorganic materials 0.000 claims 7
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims 7
- 229910052717 sulfur Inorganic materials 0.000 claims 7
- 150000003536 tetrazoles Chemical group 0.000 claims 7
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical group C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims 7
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 claims 6
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims 6
- 125000004104 aryloxy group Chemical group 0.000 claims 6
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims 6
- 125000002950 monocyclic group Chemical group 0.000 claims 6
- 125000002971 oxazolyl group Chemical group 0.000 claims 6
- 125000006413 ring segment Chemical group 0.000 claims 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 6
- 125000005309 thioalkoxy group Chemical group 0.000 claims 6
- VIESAWGOYVNHLV-UHFFFAOYSA-N 1,3-dihydropyrrol-2-one Chemical group O=C1CC=CN1 VIESAWGOYVNHLV-UHFFFAOYSA-N 0.000 claims 5
- 125000003342 alkenyl group Chemical group 0.000 claims 5
- 125000000168 pyrrolyl group Chemical group 0.000 claims 5
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical group C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 claims 4
- HUTNOYOBQPAKIA-UHFFFAOYSA-N 1h-pyrazin-2-one Chemical compound OC1=CN=CC=N1 HUTNOYOBQPAKIA-UHFFFAOYSA-N 0.000 claims 4
- 208000030507 AIDS Diseases 0.000 claims 4
- 125000002619 bicyclic group Chemical group 0.000 claims 4
- 125000001153 fluoro group Chemical group F* 0.000 claims 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 4
- 125000002883 imidazolyl group Chemical group 0.000 claims 4
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Chemical group CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims 4
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Chemical group C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims 4
- 150000002475 indoles Chemical group 0.000 claims 4
- 125000000842 isoxazolyl group Chemical group 0.000 claims 4
- 125000003373 pyrazinyl group Chemical group 0.000 claims 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 4
- 125000000335 thiazolyl group Chemical group 0.000 claims 4
- 125000004306 triazinyl group Chemical group 0.000 claims 4
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 3
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 claims 3
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 3
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 3
- 208000031886 HIV Infections Diseases 0.000 claims 3
- 208000037357 HIV infectious disease Diseases 0.000 claims 3
- 208000036142 Viral infection Diseases 0.000 claims 3
- 125000004429 atom Chemical group 0.000 claims 3
- 150000001721 carbon Chemical group 0.000 claims 3
- 125000005553 heteroaryloxy group Chemical group 0.000 claims 3
- 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 claims 3
- 125000001624 naphthyl group Chemical group 0.000 claims 3
- 125000004193 piperazinyl group Chemical group 0.000 claims 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 3
- 125000005296 thioaryloxy group Chemical group 0.000 claims 3
- 125000005404 thioheteroaryloxy group Chemical group 0.000 claims 3
- 230000009385 viral infection Effects 0.000 claims 3
- 229940126154 HIV entry inhibitor Drugs 0.000 claims 2
- 230000000840 anti-viral effect Effects 0.000 claims 2
- 229960005475 antiinfective agent Drugs 0.000 claims 2
- 239000004599 antimicrobial Substances 0.000 claims 2
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 239000002835 hiv fusion inhibitor Substances 0.000 claims 2
- 239000002955 immunomodulating agent Substances 0.000 claims 2
- 229940121354 immunomodulator Drugs 0.000 claims 2
- 230000002584 immunomodulator Effects 0.000 claims 2
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 2
- 125000001786 isothiazolyl group Chemical group 0.000 claims 2
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 125000005499 phosphonyl group Chemical group 0.000 claims 2
- 150000004885 piperazines Chemical class 0.000 claims 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 2
- 229940124597 therapeutic agent Drugs 0.000 claims 2
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims 2
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 241000700605 Viruses Species 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 150000001538 azepines Chemical class 0.000 claims 1
- 150000001539 azetidines Chemical class 0.000 claims 1
- 150000001541 aziridines Chemical class 0.000 claims 1
- 125000004069 aziridinyl group Chemical group 0.000 claims 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- RUZLIIJDZBWWSA-INIZCTEOSA-N methyl 2-[[(1s)-1-(7-methyl-2-morpholin-4-yl-4-oxopyrido[1,2-a]pyrimidin-9-yl)ethyl]amino]benzoate Chemical group COC(=O)C1=CC=CC=C1N[C@@H](C)C1=CC(C)=CN2C(=O)C=C(N3CCOCC3)N=C12 RUZLIIJDZBWWSA-INIZCTEOSA-N 0.000 claims 1
- 150000002780 morpholines Chemical class 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 150000003053 piperidines Chemical class 0.000 claims 1
- 150000003235 pyrrolidines Chemical class 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
- 241000894007 species Species 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims 1
- 229940124530 sulfonamide Drugs 0.000 claims 1
- 150000003456 sulfonamides Chemical class 0.000 claims 1
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims 1
- 239000011593 sulfur Chemical group 0.000 claims 1
- 230000003612 virological effect Effects 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US26618301P | 2001-02-02 | 2001-02-02 | |
| US31440601P | 2001-08-23 | 2001-08-23 | |
| PCT/US2002/000455 WO2002062423A1 (en) | 2001-02-02 | 2002-01-02 | Composition and antiviral activity of substituted azaindoleoxoacetic piperazine derivatives |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2004522755A JP2004522755A (ja) | 2004-07-29 |
| JP2004522755A5 true JP2004522755A5 (enExample) | 2005-09-22 |
| JP4328527B2 JP4328527B2 (ja) | 2009-09-09 |
Family
ID=26951680
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002562428A Expired - Lifetime JP4328527B2 (ja) | 2001-02-02 | 2002-01-02 | 置換アザインドールオキソアセチックピペラジン誘導体の組成物と抗ウイルス活性 |
Country Status (31)
| Country | Link |
|---|---|
| US (1) | US20030069266A1 (enExample) |
| EP (1) | EP1363705B9 (enExample) |
| JP (1) | JP4328527B2 (enExample) |
| KR (1) | KR20030079979A (enExample) |
| CN (1) | CN100384423C (enExample) |
| AR (1) | AR034292A1 (enExample) |
| BG (1) | BG66359B1 (enExample) |
| BR (1) | BRPI0206636B8 (enExample) |
| CA (1) | CA2437524C (enExample) |
| CY (1) | CY1113194T1 (enExample) |
| CZ (1) | CZ303750B6 (enExample) |
| DK (1) | DK1363705T3 (enExample) |
| EE (1) | EE05424B1 (enExample) |
| ES (1) | ES2387981T3 (enExample) |
| HR (1) | HRP20030694A2 (enExample) |
| HU (1) | HU229305B1 (enExample) |
| IL (2) | IL157029A0 (enExample) |
| IS (1) | IS2912B (enExample) |
| MX (1) | MXPA03006939A (enExample) |
| MY (1) | MY137480A (enExample) |
| NO (1) | NO326510B1 (enExample) |
| NZ (1) | NZ527193A (enExample) |
| PE (1) | PE20020855A1 (enExample) |
| PL (1) | PL364279A1 (enExample) |
| PT (1) | PT1363705E (enExample) |
| RS (1) | RS52489B (enExample) |
| RU (1) | RU2303038C2 (enExample) |
| SK (1) | SK287900B6 (enExample) |
| TW (1) | TWI318978B (enExample) |
| WO (1) | WO2002062423A1 (enExample) |
| ZA (1) | ZA200305885B (enExample) |
Families Citing this family (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6476034B2 (en) * | 2000-02-22 | 2002-11-05 | Bristol-Myers Squibb Company | Antiviral azaindole derivatives |
| US20030207910A1 (en) | 2001-02-02 | 2003-11-06 | Tao Wang | Composition and antiviral activity of substituted azaindoleoxoacetic piperazine derivatives |
| US20040110785A1 (en) * | 2001-02-02 | 2004-06-10 | Tao Wang | Composition and antiviral activity of substituted azaindoleoxoacetic piperazine derivatives |
| US20040162298A1 (en) * | 2002-02-23 | 2004-08-19 | Hsu-Tso Ho | Method of treating HIV infection by preventing interaction of CD4 and gp120 |
| US7348337B2 (en) | 2002-05-28 | 2008-03-25 | Bristol-Myers Squibb Company | Indole, azaindole and related heterocyclic 4-alkenyl piperidine amides |
| US6900206B2 (en) | 2002-06-20 | 2005-05-31 | Bristol-Myers Squibb Company | Indole, azaindole and related heterocyclic sulfonylureido piperazine derivatives |
| ATE441417T1 (de) | 2002-12-20 | 2009-09-15 | Glaxo Group Ltd | Benzoädüazepinderivate für die behandlung von neurologischen krankheiten |
| US20050075364A1 (en) * | 2003-07-01 | 2005-04-07 | Kap-Sun Yeung | Indole, azaindole and related heterocyclic N-substituted piperazine derivatives |
| US20050124623A1 (en) * | 2003-11-26 | 2005-06-09 | Bender John A. | Diazaindole-dicarbonyl-piperazinyl antiviral agents |
| US7745625B2 (en) | 2004-03-15 | 2010-06-29 | Bristol-Myers Squibb Company | Prodrugs of piperazine and substituted piperidine antiviral agents |
| UA88297C2 (ru) * | 2004-03-15 | 2009-10-12 | Бристол-Майэрс Сквибб Компани | Пиперазиновые пролекарства и замещенные пиперидиновые антивирусные средства |
| US20050244458A1 (en) * | 2004-04-30 | 2005-11-03 | Allergan, Inc. | Sustained release intraocular implants and methods for treating ocular neuropathies |
| BRPI0511874A (pt) | 2004-06-09 | 2008-01-15 | Glaxo Group Ltd | derivados da pirrolopiridina |
| JP4989478B2 (ja) | 2004-09-03 | 2012-08-01 | ユーハン・コーポレイション | ピロロ［３，２−ｂ］ピリジン誘導体及びその製造方法 |
| US20060100209A1 (en) * | 2004-11-09 | 2006-05-11 | Chong-Hui Gu | Formulations of 1-(4-benzoyl-piperazin-1-yl)-2-[4-methoxy-7-(3-methyl-[1,2,4]triazol-1-yl)-1H-pyrrolo[2,3-c]pyridin-3-yl]-ethane-1,2-dione |
| US20060100432A1 (en) * | 2004-11-09 | 2006-05-11 | Matiskella John D | Crystalline materials of 1-(4-benzoyl-piperazin-1-yl)-2-[4-methoxy-7-(3-methyl-[1,2,4]triazol-1-yl)-1H-pyrrolo[2,3-c]pyridin-3-yl]-ethane-1,2-dione |
| US7183284B2 (en) * | 2004-12-29 | 2007-02-27 | Bristol-Myers Squibb Company | Aminium salts of 1,2,3-triazoles as prodrugs of drugs including antiviral agents |
| US7601715B2 (en) | 2005-06-22 | 2009-10-13 | Bristol-Myers Squibb Company | Process for preparing triazole substituted azaindoleoxoacetic piperazine derivatives and novel salt forms produced therein |
| US7396830B2 (en) * | 2005-10-04 | 2008-07-08 | Bristol-Myers Squibb Company | Piperazine amidines as antiviral agents |
| US7851476B2 (en) | 2005-12-14 | 2010-12-14 | Bristol-Myers Squibb Company | Crystalline forms of 1-benzoyl-4-[2-[4-methoxy-7-(3-methyl-1H-1,2,4-triazol-1-YL)-1-[(phosphonooxy)methyl]-1H-pyrrolo[2,3-C]pyridin-3-YL]-1,2-dioxoethyl]-piperazine |
| US7807671B2 (en) | 2006-04-25 | 2010-10-05 | Bristol-Myers Squibb Company | Diketo-piperazine and piperidine derivatives as antiviral agents |
| US7504399B2 (en) * | 2006-06-08 | 2009-03-17 | Bristol-Meyers Squibb Company | Piperazine enamines as antiviral agents |
| EP2046753A2 (en) * | 2006-07-06 | 2009-04-15 | Brystol-Myers Squibb Company | Pyridone/hydroxypyridine 11-beta hydroxysteroid dehydrogenase type i inhibitors |
| JP5351025B2 (ja) * | 2006-09-22 | 2013-11-27 | ノバルティス アーゲー | ヘテロ環式有機化合物 |
| CN102131810B (zh) | 2008-06-25 | 2014-02-26 | 百时美施贵宝公司 | 作为抗hiv剂的二酮稠合的吡咯并哌啶类和吡咯并哌嗪类 |
| JP5433691B2 (ja) | 2008-06-25 | 2014-03-05 | ブリストル−マイヤーズ スクイブ カンパニー | Ｈｉｖ結合阻害剤としてのジケトピペリジン誘導体 |
| EP2601174B1 (en) | 2010-08-06 | 2014-11-26 | Bristol-Myers Squibb Company | Substituted indole and azaindole oxoacetyl piperazinamide derivatives |
| ES2585396T3 (es) | 2010-12-02 | 2016-10-05 | VIIV Healthcare UK (No.5) Limited | Alquilamidas como inhibidores de la unión del VIH |
| EP2696937B1 (en) | 2011-04-12 | 2017-05-17 | VIIV Healthcare UK (No.5) Limited | Thioamide, amidoxime and amidrazone derivatives as hiv attachment inhibitors |
| US8835454B2 (en) | 2011-08-29 | 2014-09-16 | Bristol-Myers Squibb Company | Fused bicyclic diamine derivatives as HIV attachment inhibitors |
| ES2609579T3 (es) | 2011-08-29 | 2017-04-21 | VIIV Healthcare UK (No.5) Limited | Derivados espiro de diamina bicíclica como inhibidores de la unión del VIH |
| PT2812332T (pt) | 2012-02-08 | 2017-11-15 | Viiv Healthcare Uk (No 4) Ltd | Métodos para a preparação do composto profármaco piperazina inibidor da conjugação ao vih |
| WO2013138436A1 (en) | 2012-03-14 | 2013-09-19 | Bristol-Myers Squibb Company | Cyclolic hydrazine derivatives as hiv attachment inhibitors |
| WO2014060381A1 (de) | 2012-10-18 | 2014-04-24 | Bayer Cropscience Ag | Heterocyclische verbindungen als schädlingsbekämpfungsmittel |
| CN104884449A (zh) | 2012-10-31 | 2015-09-02 | 拜尔农作物科学股份公司 | 作为害虫防治剂的新的杂环化合物 |
| WO2016004272A1 (en) | 2014-07-02 | 2016-01-07 | Pharmacyclics Llc | Inhibitors of bruton's tyrosine kinase |
| PH12021553180A1 (en) | 2019-06-19 | 2022-11-07 | Viiv Healthcare Uk No 5 Ltd | Inhibitors of human immunodeficiency virus replication |
| US11862306B1 (en) | 2020-02-07 | 2024-01-02 | Cvs Pharmacy, Inc. | Customer health activity based system for secure communication and presentation of health information |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5563142A (en) * | 1989-12-28 | 1996-10-08 | The Upjohn Company | Diaromatic substituted compounds as anti-HIV-1 agents |
| FR2674856B1 (fr) * | 1991-04-05 | 1993-07-30 | Esteve Labor Dr | Nouveaux antihistaminiques non sedatifs, derives de benzimidazole, leur procede de preparation et leur utilisation en tant que medicaments. |
| GB9420521D0 (en) * | 1994-10-12 | 1994-11-30 | Smithkline Beecham Plc | Novel compounds |
| TW406075B (en) * | 1994-12-13 | 2000-09-21 | Upjohn Co | Alkyl substituted piperidinyl and piperazinyl anti-AIDS compounds |
| CN1310906C (zh) * | 1999-05-21 | 2007-04-18 | 肖斯公司 | 用作p38激酶抑制剂的吲哚类型的衍生物 |
| US6469006B1 (en) * | 1999-06-15 | 2002-10-22 | Bristol-Myers Squibb Company | Antiviral indoleoxoacetyl piperazine derivatives |
| WO2001007436A2 (en) * | 1999-07-28 | 2001-02-01 | Aventis Pharmaceuticals Inc. | Substituted oxoazaheterocyclyl compounds |
| WO2001047922A2 (en) * | 1999-12-24 | 2001-07-05 | Aventis Pharma Limited | Azaindoles |
| US20020061892A1 (en) * | 2000-02-22 | 2002-05-23 | Tao Wang | Antiviral azaindole derivatives |
| ES2250422T3 (es) * | 2000-07-10 | 2006-04-16 | Bristol-Myers Squibb Company | Composicion y actividad antiviral de derivados de piperazina indoloxoaceticos sustituidos. |
| US6825201B2 (en) * | 2001-04-25 | 2004-11-30 | Bristol-Myers Squibb Company | Indole, azaindole and related heterocyclic amidopiperazine derivatives |
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- 2002-01-02 CN CNB028078268A patent/CN100384423C/zh not_active Expired - Lifetime
- 2002-01-02 PT PT02707413T patent/PT1363705E/pt unknown
- 2002-01-02 WO PCT/US2002/000455 patent/WO2002062423A1/en not_active Ceased
- 2002-01-02 KR KR10-2003-7010208A patent/KR20030079979A/ko not_active Withdrawn
- 2002-01-02 DK DK02707413.7T patent/DK1363705T3/da active
- 2002-01-02 EE EEP200300359A patent/EE05424B1/xx unknown
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- 2002-01-02 CZ CZ20032316A patent/CZ303750B6/cs not_active IP Right Cessation
- 2002-01-02 ES ES02707413T patent/ES2387981T3/es not_active Expired - Lifetime
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- 2002-01-02 HU HU0304062A patent/HU229305B1/hu unknown
- 2002-01-02 RU RU2003127077/04A patent/RU2303038C2/ru active
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