ZA200409504B - Indole, azaindole and relate heterocyclic 4-alkenyl piperidine amides - Google Patents

Indole, azaindole and relate heterocyclic 4-alkenyl piperidine amides Download PDF

Info

Publication number: ZA200409504B
Authority: ZA; South Africa
Prior art keywords: alkyl; group; heteroaryl; compound; same
Prior art date: 2002-05-28

Application number

ZA200409504A

Other languages

English (en)

Inventor

Tao Wang

Nicholas A Meacnwell

Zhongxing Zhang

Zhilei Qiu

Clint A James

Carol Bachand

John F Kadow

Kap-Sun Yeung

Zhiwei Yin

Daniel H Deon

Edward H Ruediger

Original Assignee

Bristol Myers Squibb Co

Priority date (The priority date 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 date listed.)

2002-05-28

Filing date

2004-11-24

Publication date

2006-05-31

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=32312411&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=ZA200409504(B) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

2004-11-24 Application filed by Bristol Myers Squibb Co filed Critical Bristol Myers Squibb Co

2006-05-31 Publication of ZA200409504B publication Critical patent/ZA200409504B/en

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NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 title claims description 15
125000000623 heterocyclic group Chemical group 0.000 title description 16
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 title description 8
BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 title description 5
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 title description 4
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 title description 4
-1 osxadiazolyl Chemical group 0.000 claims description 151
125000000217 alkyl group Chemical group 0.000 claims description 150
125000001072 heteroaryl group Chemical group 0.000 claims description 135
150000001875 compounds Chemical class 0.000 claims description 107
229910052736 halogen Inorganic materials 0.000 claims description 65
150000002367 halogens Chemical class 0.000 claims description 65
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 62
229910052739 hydrogen Inorganic materials 0.000 claims description 38
239000001257 hydrogen Substances 0.000 claims description 35
125000003226 pyrazolyl group Chemical group 0.000 claims description 35
125000004076 pyridyl group Chemical group 0.000 claims description 34
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 29
125000001424 substituent group Chemical group 0.000 claims description 29
125000002541 furyl group Chemical group 0.000 claims description 28
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 28
125000003831 tetrazolyl group Chemical group 0.000 claims description 26
125000001544 thienyl group Chemical group 0.000 claims description 26
125000001425 triazolyl group Chemical group 0.000 claims description 26
125000002971 oxazolyl group Chemical group 0.000 claims description 24
125000002883 imidazolyl group Chemical group 0.000 claims description 23
125000001715 oxadiazolyl group Chemical group 0.000 claims description 23
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 22
230000000840 anti-viral effect Effects 0.000 claims description 22
125000001786 isothiazolyl group Chemical group 0.000 claims description 22
125000002098 pyridazinyl group Chemical group 0.000 claims description 22
125000001113 thiadiazolyl group Chemical group 0.000 claims description 22
125000003373 pyrazinyl group Chemical group 0.000 claims description 21
125000003545 alkoxy group Chemical group 0.000 claims description 20
125000000842 isoxazolyl group Chemical group 0.000 claims description 20
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 19
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
125000000335 thiazolyl group Chemical group 0.000 claims description 18
125000000714 pyrimidinyl group Chemical group 0.000 claims description 15
239000003814 drug Substances 0.000 claims description 14
150000002431 hydrogen Chemical class 0.000 claims description 13
239000000203 mixture Substances 0.000 claims description 13
125000004193 piperazinyl group Chemical group 0.000 claims description 13
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 12
125000000304 alkynyl group Chemical group 0.000 claims description 12
241000700605 Viruses Species 0.000 claims description 11
229910052799 carbon Inorganic materials 0.000 claims description 11
125000004306 triazinyl group Chemical group 0.000 claims description 11
125000004093 cyano group Chemical group *C#N 0.000 claims description 10
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 10
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 10
125000005309 thioalkoxy group Chemical group 0.000 claims description 10
125000000753 cycloalkyl group Chemical group 0.000 claims description 8
238000000034 method Methods 0.000 claims description 8
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
150000003839 salts Chemical class 0.000 claims description 8
241000124008 Mammalia Species 0.000 claims description 7
208000030507 AIDS Diseases 0.000 claims description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
239000003443 antiviral agent Substances 0.000 claims description 6
239000003795 chemical substances by application Substances 0.000 claims description 6
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 5
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 5
DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims description 4
XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 claims description 4
HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims description 4
229910052731 fluorine Inorganic materials 0.000 claims description 4
239000002835 hiv fusion inhibitor Substances 0.000 claims description 4
239000002955 immunomodulating agent Substances 0.000 claims description 4
229940121354 immunomodulator Drugs 0.000 claims description 4
230000002584 immunomodulator Effects 0.000 claims description 4
239000008194 pharmaceutical composition Substances 0.000 claims description 4
PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims description 3
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 3
229960005475 antiinfective agent Drugs 0.000 claims description 3
125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 3
239000003937 drug carrier Substances 0.000 claims description 3
239000011737 fluorine Substances 0.000 claims description 3
238000009472 formulation Methods 0.000 claims description 3
ICSAXRANXQSPQP-VUKDEKJYSA-M sodium;(5r,6s)-6-[(1r)-1-hydroxyethyl]-7-oxo-3-[(2r)-oxolan-2-yl]-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate Chemical compound [Na+].S([C@@H]1[C@H](C(N1C=1C([O-])=O)=O)[C@H](O)C)C=1[C@H]1CCCO1 ICSAXRANXQSPQP-VUKDEKJYSA-M 0.000 claims description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
MUQNGPZZQDCDFT-JNQJZLCISA-N Halcinonide Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H]3OC(C)(C)O[C@@]3(C(=O)CCl)[C@@]1(C)C[C@@H]2O MUQNGPZZQDCDFT-JNQJZLCISA-N 0.000 claims description 2
125000003943 azolyl group Chemical group 0.000 claims description 2
229940028332 halog Drugs 0.000 claims description 2
MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 claims description 2
125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 45
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 7
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 6
125000000168 pyrrolyl group Chemical group 0.000 claims 5
239000000126 substance Substances 0.000 claims 5
NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 claims 2
239000004599 antimicrobial Substances 0.000 claims 2
MHCVCKDNQYMGEX-UHFFFAOYSA-N 1,1'-biphenyl;phenoxybenzene Chemical group C1=CC=CC=C1C1=CC=CC=C1.C=1C=CC=CC=1OC1=CC=CC=C1 MHCVCKDNQYMGEX-UHFFFAOYSA-N 0.000 claims 1
BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 claims 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims 1
OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims 1
206010004966 Bite Diseases 0.000 claims 1
102100025027 E3 ubiquitin-protein ligase TRIM69 Human genes 0.000 claims 1
101000830203 Homo sapiens E3 ubiquitin-protein ligase TRIM69 Proteins 0.000 claims 1
241000820057 Ithone Species 0.000 claims 1
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical group C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 1
125000003282 alkyl amino group Chemical group 0.000 claims 1
150000002500 ions Chemical class 0.000 claims 1
125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims 1
229940055764 triaz Drugs 0.000 claims 1
238000003786 synthesis reaction Methods 0.000 description 23
230000015572 biosynthetic process Effects 0.000 description 21
229940079593 drug Drugs 0.000 description 12
239000003112 inhibitor Substances 0.000 description 12
238000002360 preparation method Methods 0.000 description 8
208000031886 HIV Infections Diseases 0.000 description 7
241000725303 Human immunodeficiency virus Species 0.000 description 7
241000713772 Human immunodeficiency virus 1 Species 0.000 description 7
239000003419 rna directed dna polymerase inhibitor Substances 0.000 description 7
HBOMLICNUCNMMY-XLPZGREQSA-N zidovudine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](N=[N+]=[N-])C1 HBOMLICNUCNMMY-XLPZGREQSA-N 0.000 description 7
238000006243 chemical reaction Methods 0.000 description 6
150000002475 indoles Chemical class 0.000 description 6
229960002555 zidovudine Drugs 0.000 description 6
WHBIGIKBNXZKFE-UHFFFAOYSA-N delavirdine Chemical compound CC(C)NC1=CC=CN=C1N1CCN(C(=O)C=2NC3=CC=C(NS(C)(=O)=O)C=C3C=2)CC1 WHBIGIKBNXZKFE-UHFFFAOYSA-N 0.000 description 5
125000004953 trihalomethyl group Chemical group 0.000 description 5
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
208000037357 HIV infectious disease Diseases 0.000 description 4
102100034343 Integrase Human genes 0.000 description 4
229940124821 NNRTIs Drugs 0.000 description 4
108010092799 RNA-directed DNA polymerase Proteins 0.000 description 4
125000003118 aryl group Chemical group 0.000 description 4
125000004429 atom Chemical group 0.000 description 4
208000033519 human immunodeficiency virus infectious disease Diseases 0.000 description 4
NQDJXKOVJZTUJA-UHFFFAOYSA-N nevirapine Chemical compound C12=NC=CC=C2C(=O)NC=2C(C)=CC=NC=2N1C1CC1 NQDJXKOVJZTUJA-UHFFFAOYSA-N 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
239000002726 nonnucleoside reverse transcriptase inhibitor Substances 0.000 description 4
238000002560 therapeutic procedure Methods 0.000 description 4
MVXVYAKCVDQRLW-UHFFFAOYSA-N 1h-pyrrolo[2,3-b]pyridine Chemical class C1=CN=C2NC=CC2=C1 MVXVYAKCVDQRLW-UHFFFAOYSA-N 0.000 description 3
KJHKTHWMRKYKJE-SUGCFTRWSA-N Kaletra Chemical compound N1([C@@H](C(C)C)C(=O)N[C@H](C[C@H](O)[C@H](CC=2C=CC=CC=2)NC(=O)COC=2C(=CC=CC=2C)C)CC=2C=CC=CC=2)CCCNC1=O KJHKTHWMRKYKJE-SUGCFTRWSA-N 0.000 description 3
150000001204 N-oxides Chemical class 0.000 description 3
WREGKURFCTUGRC-POYBYMJQSA-N Zalcitabine Chemical compound O=C1N=C(N)C=CN1[C@@H]1O[C@H](CO)CC1 WREGKURFCTUGRC-POYBYMJQSA-N 0.000 description 3
238000006480 benzoylation reaction Methods 0.000 description 3
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JTEGQNOMFQHVDC-NKWVEPMBSA-N lamivudine Chemical compound O=C1N=C(N)C=CN1[C@H]1O[C@@H](CO)SC1 JTEGQNOMFQHVDC-NKWVEPMBSA-N 0.000 description 3
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RCWISWVYKNLXHC-UHFFFAOYSA-N 1h-pyrrolo[2,3-b]pyridin-4-amine Chemical compound NC1=CC=NC2=C1C=CN2 RCWISWVYKNLXHC-UHFFFAOYSA-N 0.000 description 2
WFWKZHZTDPTPOV-UHFFFAOYSA-N 4-amino-n-[2-(ethylamino)ethyl]benzamide Chemical compound CCNCCNC(=O)C1=CC=C(N)C=C1 WFWKZHZTDPTPOV-UHFFFAOYSA-N 0.000 description 2
BXZVVICBKDXVGW-NKWVEPMBSA-N Didanosine Chemical compound O1[C@H](CO)CC[C@@H]1N1C(NC=NC2=O)=C2N=C1 BXZVVICBKDXVGW-NKWVEPMBSA-N 0.000 description 2
XPOQHMRABVBWPR-UHFFFAOYSA-N Efavirenz Natural products O1C(=O)NC2=CC=C(Cl)C=C2C1(C(F)(F)F)C#CC1CC1 XPOQHMRABVBWPR-UHFFFAOYSA-N 0.000 description 2
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XNKLLVCARDGLGL-JGVFFNPUSA-N Stavudine Chemical compound O=C1NC(=O)C(C)=CN1[C@H]1C=C[C@@H](CO)O1 XNKLLVCARDGLGL-JGVFFNPUSA-N 0.000 description 2
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QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
125000005334 azaindolyl group Chemical group N1N=C(C2=CC=CC=C12)* 0.000 description 2
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AJDPNPAGZMZOMN-UHFFFAOYSA-N diethyl (4-oxo-1,2,3-benzotriazin-3-yl) phosphate Chemical compound C1=CC=C2C(=O)N(OP(=O)(OCC)OCC)N=NC2=C1 AJDPNPAGZMZOMN-UHFFFAOYSA-N 0.000 description 2
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ASOMNDIOOKDVDC-UHFFFAOYSA-N 1h-indol-2-yl-[4-[3-(propan-2-ylamino)pyridin-2-yl]piperazin-1-yl]methanone Chemical compound CC(C)NC1=CC=CN=C1N1CCN(C(=O)C=2NC3=CC=CC=C3C=2)CC1 ASOMNDIOOKDVDC-UHFFFAOYSA-N 0.000 description 1
HNGJGZFTQRJUIF-UHFFFAOYSA-N 2,5-dihydroxy-3,6-bis(1h-indol-3-yl)cyclohexa-2,5-diene-1,4-dione Chemical compound C1=CC=C2C(C3=C(O)C(=O)C(C=4C5=CC=CC=C5NC=4)=C(C3=O)O)=CNC2=C1 HNGJGZFTQRJUIF-UHFFFAOYSA-N 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Virology (AREA)
Pharmacology & Pharmacy (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Oncology (AREA)
Communicable Diseases (AREA)
AIDS & HIV (AREA)
Tropical Medicine & Parasitology (AREA)
Molecular Biology (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

ZA200409504A 2002-05-28 2004-11-24 Indole, azaindole and relate heterocyclic 4-alkenyl piperidine amides ZA200409504B (en)

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US (1)	US20040063744A1 (fr)
EP (1)	EP1513832B1 (fr)
JP (1)	JP4446889B2 (fr)
KR (1)	KR101001811B1 (fr)
CN (1)	CN100528866C (fr)
AR (1)	AR040230A1 (fr)
AU (1)	AU2003301958B2 (fr)
BR (2)	BRPI0311541B1 (fr)
CA (1)	CA2487542C (fr)
CL (1)	CL2003001087A1 (fr)
CO (1)	CO5631440A2 (fr)
DK (1)	DK1513832T3 (fr)
ES (1)	ES2460728T3 (fr)
GE (1)	GEP20074152B (fr)
HR (1)	HRP20041137B1 (fr)
IL (1)	IL165200A (fr)
IS (1)	IS2945B (fr)
MX (1)	MXPA04011670A (fr)
MY (1)	MY139058A (fr)
NO (1)	NO329691B1 (fr)
NZ (1)	NZ536661A (fr)
PE (1)	PE20040526A1 (fr)
PL (1)	PL216388B1 (fr)
PT (1)	PT1513832E (fr)
RS (1)	RS53021B (fr)
RU (1)	RU2323934C2 (fr)
SI (1)	SI1513832T1 (fr)
TW (1)	TWI310381B (fr)
UA (1)	UA79470C2 (fr)
WO (1)	WO2004043337A2 (fr)
ZA (1)	ZA200409504B (fr)

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US6476034B2 (en) *	2000-02-22	2002-11-05	Bristol-Myers Squibb Company	Antiviral azaindole derivatives
US20040110785A1 (en) *	2001-02-02	2004-06-10	Tao Wang	Composition and antiviral activity of substituted azaindoleoxoacetic piperazine derivatives
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
US7087610B2 (en) *	2004-06-03	2006-08-08	Bristol-Myers Squibb Company	Benzothiazole antiviral agents
EP1753764B1 (fr)	2004-06-09	2008-10-29	Glaxo Group Limited	Derives de pyrrolopyridine
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
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
AR055601A1 (es) *	2005-08-09	2007-08-29	Glaxo Group Ltd	Compuestos derivados de imidazopiridina como ligandos de receptores canabinoides
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
US7572810B2 (en) *	2006-06-08	2009-08-11	Bristol-Myers Squibb Company	Alkene piperidine derivatives as antiviral agents
TWI443090B (zh) *	2007-05-25	2014-07-01	Abbvie Deutschland	作為代謝性麩胺酸受體２（ｍｇｌｕ２受體）之正向調節劑之雜環化合物
WO2009011912A1 (fr) *	2007-07-18	2009-01-22	Bristol-Myers Squibb Company	Composition de traitement du vih comprenant des particules apparentées au virus
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2003
- 2003-04-29 US US10/425,370 patent/US20040063744A1/en not_active Abandoned
- 2003-04-30 CN CNB038175657A patent/CN100528866C/zh not_active Expired - Fee Related
- 2003-04-30 ES ES03811179.5T patent/ES2460728T3/es not_active Expired - Lifetime
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- 2003-04-30 EP EP03811179.5A patent/EP1513832B1/fr not_active Expired - Lifetime
- 2003-04-30 GE GEAP8554A patent/GEP20074152B/en unknown
- 2003-04-30 WO PCT/US2003/013324 patent/WO2004043337A2/fr active Application Filing
- 2003-04-30 RU RU2004138565/04A patent/RU2323934C2/ru not_active IP Right Cessation
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Also Published As

Publication number	Publication date
GEP20074152B (en)	2007-07-10
RU2323934C2 (ru)	2008-05-10
AR040230A1 (es)	2005-03-23
CA2487542A1 (fr)	2004-05-27
WO2004043337A2 (fr)	2004-05-27
HRP20041137B1 (hr)	2014-11-21
ES2460728T3 (es)	2014-05-14
TW200406397A (en)	2004-05-01
NO329691B1 (no)	2010-11-29
TWI310381B (en)	2009-06-01
UA79470C2 (en)	2007-06-25
CO5631440A2 (es)	2006-04-28
EP1513832A4 (fr)	2010-03-10
CL2003001087A1 (es)	2005-02-11
SI1513832T1 (sl)	2014-04-30
IS7546A (is)	2004-11-22
IL165200A (en)	2011-01-31
RS101304A (sr)	2006-10-27
PT1513832E (pt)	2014-05-22
CA2487542C (fr)	2011-09-27
KR20050013558A (ko)	2005-02-04
KR101001811B1 (ko)	2010-12-15
MY139058A (en)	2009-08-28
PL373603A1 (en)	2005-09-05
JP2006507326A (ja)	2006-03-02
MXPA04011670A (es)	2005-03-07
WO2004043337A3 (fr)	2004-11-11
CN1671697A (zh)	2005-09-21
NO20045064L (no)	2005-02-23
IL165200A0 (en)	2005-12-18
JP4446889B2 (ja)	2010-04-07
HRP20041137A2 (en)	2005-06-30
NZ536661A (en)	2007-12-21
AU2003301958B2 (en)	2009-10-01
PL216388B1 (pl)	2014-03-31
US20040063744A1 (en)	2004-04-01
BR0311541A (pt)	2006-06-06
RS53021B (en)	2014-04-30
CN100528866C (zh)	2009-08-19
PE20040526A1 (es)	2004-08-28
IS2945B (is)	2016-05-15
EP1513832A2 (fr)	2005-03-16
AU2003301958A1 (en)	2004-06-03
BRPI0311541B1 (pt)	2018-04-24
DK1513832T3 (da)	2014-05-26
RU2004138565A (ru)	2005-07-20
EP1513832B1 (fr)	2014-03-05

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ZA200409504B (en)	2006-05-31	Indole, azaindole and relate heterocyclic 4-alkenyl piperidine amides
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EP1575493B1 (fr)	2013-12-11	Indole, azaindole et derives de piperazine sulfonylureido heterocyclique
WO2005004801A2 (fr)	2005-01-20	Indole, azaindole et derives de piperazine n-substitues heterocycliques apparentes