ZA200106592B - Functionalized heterocycles as chemokine receptor modulators. - Google Patents
Functionalized heterocycles as chemokine receptor modulators. Download PDFInfo
- Publication number
- ZA200106592B ZA200106592B ZA200106592A ZA200106592A ZA200106592B ZA 200106592 B ZA200106592 B ZA 200106592B ZA 200106592 A ZA200106592 A ZA 200106592A ZA 200106592 A ZA200106592 A ZA 200106592A ZA 200106592 B ZA200106592 B ZA 200106592B
- Authority
- ZA
- South Africa
- Prior art keywords
- methyl
- decahydro
- quinolizine
- pyrrolo
- carboxylic acid
- Prior art date
Links
- 102000009410 Chemokine receptor Human genes 0.000 title claims description 10
- 108050000299 Chemokine receptor Proteins 0.000 title claims description 10
- 125000000623 heterocyclic group Chemical group 0.000 title description 4
- -1 2-methylpropyl ester Chemical class 0.000 claims description 184
- 150000002148 esters Chemical class 0.000 claims description 73
- 125000000217 alkyl group Chemical group 0.000 claims description 55
- 125000004494 ethyl ester group Chemical group 0.000 claims description 53
- 229910052739 hydrogen Inorganic materials 0.000 claims description 47
- 239000001257 hydrogen Substances 0.000 claims description 47
- 150000001875 compounds Chemical class 0.000 claims description 35
- 125000003118 aryl group Chemical group 0.000 claims description 33
- 150000002431 hydrogen Chemical class 0.000 claims description 23
- 150000003839 salts Chemical class 0.000 claims description 23
- LDECUSDQMXVUMP-UHFFFAOYSA-N benzyl 3-[6-[[2-(butylamino)-1-[3-methoxycarbonyl-4-(2-methoxy-2-oxoethoxy)phenyl]-2-oxoethyl]-hexylamino]-6-oxohexyl]-4-methyl-2-oxo-6-(4-phenylphenyl)-1,6-dihydropyrimidine-5-carboxylate Chemical compound O=C1NC(C=2C=CC(=CC=2)C=2C=CC=CC=2)C(C(=O)OCC=2C=CC=CC=2)=C(C)N1CCCCCC(=O)N(CCCCCC)C(C(=O)NCCCC)C1=CC=C(OCC(=O)OC)C(C(=O)OC)=C1 LDECUSDQMXVUMP-UHFFFAOYSA-N 0.000 claims description 20
- 125000004429 atom Chemical group 0.000 claims description 19
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 17
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 101710149870 C-C chemokine receptor type 5 Proteins 0.000 claims description 10
- 102100035875 C-C chemokine receptor type 5 Human genes 0.000 claims description 10
- QUSNBJAOOMFDIB-UHFFFAOYSA-O ethylaminium Chemical compound CC[NH3+] QUSNBJAOOMFDIB-UHFFFAOYSA-O 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- 150000004702 methyl esters Chemical class 0.000 claims description 10
- 229950004354 phosphorylcholine Drugs 0.000 claims description 10
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 9
- 208000030507 AIDS Diseases 0.000 claims description 7
- 230000000694 effects Effects 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
- 125000004122 cyclic group Chemical group 0.000 claims description 6
- WQJFIWXYPKYBTO-UHFFFAOYSA-N indole-1-acetic acid Chemical compound C1=CC=C2N(CC(=O)O)C=CC2=C1 WQJFIWXYPKYBTO-UHFFFAOYSA-N 0.000 claims description 6
- 208000015181 infectious disease Diseases 0.000 claims description 6
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims description 6
- 239000004305 biphenyl Substances 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- DXASQZJWWGZNSF-UHFFFAOYSA-N n,n-dimethylmethanamine;sulfur trioxide Chemical group CN(C)C.O=S(=O)=O DXASQZJWWGZNSF-UHFFFAOYSA-N 0.000 claims description 5
- GUOHRXPYGSKUGT-UHFFFAOYSA-N quinolizinium Chemical compound C1=CC=CC2=CC=CC=[N+]21 GUOHRXPYGSKUGT-UHFFFAOYSA-N 0.000 claims description 5
- WBVHKJQWPYVDGG-UHFFFAOYSA-N 2-oxa-7,17-diazapentacyclo[11.8.0.01,17.03,11.06,10]henicosa-3,5,7,9,11,13,15,18,20-nonaene-9-carboxylic acid Chemical compound C1=CC=CN2C=CC=C(C=C34)C21OC4=CC=C1C3=C(C(=O)O)C=N1 WBVHKJQWPYVDGG-UHFFFAOYSA-N 0.000 claims description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 150000001204 N-oxides Chemical class 0.000 claims description 3
- 125000002252 acyl group Chemical group 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- NFGMWAKGHQALBE-KVGGNSOTSA-N (4-nitrophenyl)methyl (4r,5s,6s)-6-[(1r)-1-hydroxyethyl]-4-methyl-3-[(3s,5s)-1-[(4-nitrophenyl)methoxycarbonyl]-5-[(sulfamoylamino)methyl]pyrrolidin-3-yl]sulfanyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate Chemical compound N1([C@H](CNS(N)(=O)=O)C[C@@H](C1)SC=1[C@H](C)[C@@H]2[C@H](C(N2C=1C(=O)OCC=1C=CC(=CC=1)[N+]([O-])=O)=O)[C@H](O)C)C(=O)OCC1=CC=C([N+]([O-])=O)C=C1 NFGMWAKGHQALBE-KVGGNSOTSA-N 0.000 claims description 2
- WXAVSTZWKNIWCN-UHFFFAOYSA-N 1-(1-phenylethoxy)ethylbenzene Chemical compound C=1C=CC=CC=1C(C)OC(C)C1=CC=CC=C1 WXAVSTZWKNIWCN-UHFFFAOYSA-N 0.000 claims description 2
- WNWVKZTYMQWFHE-UHFFFAOYSA-N 4-ethylmorpholine Chemical group [CH2]CN1CCOCC1 WNWVKZTYMQWFHE-UHFFFAOYSA-N 0.000 claims description 2
- UQDJZUOBEZNCRM-UHFFFAOYSA-N C(C)OC(=O)C1=C(NC=2C1=C1CC3CCCN(C3(OC1=CC2)C)CC2=CC=CC=C2)C Chemical compound C(C)OC(=O)C1=C(NC=2C1=C1CC3CCCN(C3(OC1=CC2)C)CC2=CC=CC=C2)C UQDJZUOBEZNCRM-UHFFFAOYSA-N 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 2
- QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 2
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- QSSJZLPUHJDYKF-UHFFFAOYSA-N methyl 4-methylbenzoate Chemical group COC(=O)C1=CC=C(C)C=C1 QSSJZLPUHJDYKF-UHFFFAOYSA-N 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- MDHYEMXUFSJLGV-UHFFFAOYSA-N phenethyl acetate Chemical compound CC(=O)OCCC1=CC=CC=C1 MDHYEMXUFSJLGV-UHFFFAOYSA-N 0.000 claims description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims description 2
- 241000124008 Mammalia Species 0.000 claims 4
- 239000003814 drug Substances 0.000 claims 4
- 238000004519 manufacturing process Methods 0.000 claims 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 2
- 208000027866 inflammatory disease Diseases 0.000 claims 2
- SERVTOXIOYSDQO-UHFFFAOYSA-N 2h-chromen-2-ol Chemical compound C1=CC=C2C=CC(O)OC2=C1 SERVTOXIOYSDQO-UHFFFAOYSA-N 0.000 claims 1
- 125000002471 4H-quinolizinyl group Chemical class C=1(C=CCN2C=CC=CC12)* 0.000 claims 1
- 239000005711 Benzoic acid Substances 0.000 claims 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 1
- 150000008064 anhydrides Chemical class 0.000 claims 1
- 235000010233 benzoic acid Nutrition 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 101150047356 dec-1 gene Proteins 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- QXOKHIVHFRAHMT-UHFFFAOYSA-N ethyl 2-oxa-4,14-diazatetracyclo[8.7.0.03,8.011,15]heptadeca-1(17),3(8),4,6,9,11,13,15-octaene-12-carboxylate Chemical compound C(C)OC(=O)C=1C=NC=2C=1C1=CC3=CC=CN=C3OC1=CC=2 QXOKHIVHFRAHMT-UHFFFAOYSA-N 0.000 claims 1
- XBMIIVQPAWWEQI-UHFFFAOYSA-N ethyl 3,4,13-trimethyl-2-oxa-4,14-diazatetracyclo[8.7.0.03,8.011,15]heptadeca-1(10),11(15),12,16-tetraene-12-carboxylate Chemical compound C1C2=C3C(C(=O)OCC)=C(C)NC3=CC=C2OC2(C)C1CCCN2C XBMIIVQPAWWEQI-UHFFFAOYSA-N 0.000 claims 1
- HCPOCMMGKBZWSJ-UHFFFAOYSA-N ethyl 3-hydrazinyl-3-oxopropanoate Chemical compound CCOC(=O)CC(=O)NN HCPOCMMGKBZWSJ-UHFFFAOYSA-N 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 claims 1
- 210000004027 cell Anatomy 0.000 description 7
- 241000713772 Human immunodeficiency virus 1 Species 0.000 description 6
- 102100031650 C-X-C chemokine receptor type 4 Human genes 0.000 description 3
- 108700028369 Alleles Proteins 0.000 description 2
- 102100031172 C-C chemokine receptor type 1 Human genes 0.000 description 2
- 101710149814 C-C chemokine receptor type 1 Proteins 0.000 description 2
- 102100031151 C-C chemokine receptor type 2 Human genes 0.000 description 2
- 101710149815 C-C chemokine receptor type 2 Proteins 0.000 description 2
- 102100024167 C-C chemokine receptor type 3 Human genes 0.000 description 2
- 101710149862 C-C chemokine receptor type 3 Proteins 0.000 description 2
- 102100037853 C-C chemokine receptor type 4 Human genes 0.000 description 2
- 101710149863 C-C chemokine receptor type 4 Proteins 0.000 description 2
- 102100036166 C-X-C chemokine receptor type 1 Human genes 0.000 description 2
- 102100028989 C-X-C chemokine receptor type 2 Human genes 0.000 description 2
- 102100028990 C-X-C chemokine receptor type 3 Human genes 0.000 description 2
- 101710082514 C-X-C chemokine receptor type 3 Proteins 0.000 description 2
- 101710082513 C-X-C chemokine receptor type 4 Proteins 0.000 description 2
- 102000001327 Chemokine CCL5 Human genes 0.000 description 2
- 108010055166 Chemokine CCL5 Proteins 0.000 description 2
- 102000019034 Chemokines Human genes 0.000 description 2
- 108010012236 Chemokines Proteins 0.000 description 2
- 208000031886 HIV Infections Diseases 0.000 description 2
- 101000947174 Homo sapiens C-X-C chemokine receptor type 1 Proteins 0.000 description 2
- 241000725303 Human immunodeficiency virus Species 0.000 description 2
- 108010018951 Interleukin-8B Receptors Proteins 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 102000005962 receptors Human genes 0.000 description 2
- 108020003175 receptors Proteins 0.000 description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
- 108700011778 CCR5 Proteins 0.000 description 1
- 102000004274 CCR5 Receptors Human genes 0.000 description 1
- 108010017088 CCR5 Receptors Proteins 0.000 description 1
- 102000003688 G-Protein-Coupled Receptors Human genes 0.000 description 1
- 108090000045 G-Protein-Coupled Receptors Proteins 0.000 description 1
- 208000037357 HIV infectious disease Diseases 0.000 description 1
- 101000922348 Homo sapiens C-X-C chemokine receptor type 4 Proteins 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000007910 cell fusion Effects 0.000 description 1
- 230000035605 chemotaxis Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 238000012217 deletion Methods 0.000 description 1
- 230000037430 deletion Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- RINFBAICZVKAOL-UHFFFAOYSA-N ethyl 3,4-diethyl-13-methyl-2-oxa-4,14-diazatetracyclo[8.7.0.03,8.011,15]heptadeca-1(10),11(15),12,16-tetraene-12-carboxylate Chemical compound C1C2=C3C(C(=O)OCC)=C(C)NC3=CC=C2OC2(CC)C1CCCN2CC RINFBAICZVKAOL-UHFFFAOYSA-N 0.000 description 1
- OXXIGOWSWOSXFB-UHFFFAOYSA-N ethyl 3-ethyl-4,13-dimethyl-2-oxa-4,14-diazatetracyclo[8.7.0.03,8.011,15]heptadeca-1(10),11(15),12,16-tetraene-12-carboxylate Chemical compound C1C2=C3C(C(=O)OCC)=C(C)NC3=CC=C2OC2(CC)C1CCCN2C OXXIGOWSWOSXFB-UHFFFAOYSA-N 0.000 description 1
- KKOTWZVRVQPLDT-UHFFFAOYSA-N ethyl 6h-indolo[4,5-g]quinoline-1-carboxylate Chemical compound C1=CC=C2C=C3C4=C(C(=O)OCC)C=NC4=CC=C3CC2=N1 KKOTWZVRVQPLDT-UHFFFAOYSA-N 0.000 description 1
- 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 210000000265 leukocyte Anatomy 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 230000008506 pathogenesis Effects 0.000 description 1
- 230000000770 proinflammatory effect Effects 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
- C07D491/14—Ortho-condensed systems
-
- 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
- C07D455/00—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
- C07D455/02—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing not further condensed quinolizine ring systems
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Virology (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Molecular Biology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Tropical Medicine & Parasitology (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- AIDS & HIV (AREA)
- Communicable Diseases (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11565499P | 1999-01-13 | 1999-01-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200106592B true ZA200106592B (en) | 2002-08-12 |
Family
ID=22362668
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200106592A ZA200106592B (en) | 1999-01-13 | 2001-08-10 | Functionalized heterocycles as chemokine receptor modulators. |
Country Status (20)
| Country | Link |
|---|---|
| EP (1) | EP1144415A2 (pt) |
| JP (1) | JP2002534526A (pt) |
| KR (1) | KR20010086166A (pt) |
| CN (1) | CN1344270A (pt) |
| AP (1) | AP2001002228A0 (pt) |
| AU (1) | AU1940900A (pt) |
| BR (1) | BR9916905A (pt) |
| CA (1) | CA2372197A1 (pt) |
| CZ (1) | CZ20012502A3 (pt) |
| EA (1) | EA200100774A1 (pt) |
| HK (1) | HK1044539A1 (pt) |
| HU (1) | HUP0202932A3 (pt) |
| IL (1) | IL144289A0 (pt) |
| MX (1) | MXPA01007033A (pt) |
| NO (1) | NO20013456L (pt) |
| OA (1) | OA11820A (pt) |
| PL (1) | PL349348A1 (pt) |
| SK (1) | SK9972001A3 (pt) |
| WO (1) | WO2000042045A2 (pt) |
| ZA (1) | ZA200106592B (pt) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1377549A1 (en) | 2001-03-12 | 2004-01-07 | Millennium Pharmaceuticals, Inc. | Functionalized heterocycles as modulators of chemokine receptor function and methods of use therefor |
| ES2566056T3 (es) * | 2001-03-29 | 2016-04-08 | Eli Lilly And Company | N-(2-ariletil)bencilaminas como antagonistas del receptor 5-HT6 |
| WO2003035650A1 (fr) * | 2001-09-25 | 2003-05-01 | Takeda Chemical Industries, Ltd. | Inhibiteur d'entree |
| TWI344955B (en) | 2003-03-14 | 2011-07-11 | Ono Pharmaceutical Co | Heterocyclic rinf having nitrogen atom derivatives and medicament containing the derivatives as active ingredient |
| US7498323B2 (en) | 2003-04-18 | 2009-03-03 | Ono Pharmaceuticals Co., Ltd. | Spiro-piperidine compounds and medicinal use thereof |
| TWI400232B (zh) | 2004-09-13 | 2013-07-01 | Ono Pharmaceutical Co | 含氮雜環衍生物及以該含氮雜環衍生物為有效成分之藥劑 |
| JPWO2006129679A1 (ja) | 2005-05-31 | 2009-01-08 | 小野薬品工業株式会社 | スピロピペリジン化合物およびその医薬用途 |
| US7915286B2 (en) | 2005-09-16 | 2011-03-29 | Ranbaxy Laboratories Limited | Substituted pyrazolo [3,4-b] pyridines as phosphodiesterase inhibitors |
| US8318931B2 (en) | 2005-10-28 | 2012-11-27 | Ono Pharmaceutical Co., Ltd. | Chemokine receptor antagonists and use thereof |
| JP5217438B2 (ja) | 2005-11-18 | 2013-06-19 | 小野薬品工業株式会社 | 塩基性基を含有する化合物およびその用途 |
| JP2009526863A (ja) * | 2006-02-15 | 2009-07-23 | アラーガン、インコーポレイテッド | スフィンゴシン−１−リン酸（ｓ１ｐ）受容体アンタゴニスト生物学的活性を有するアリールまたはヘテロアリール基を持つインドール−３−カルボン酸アミド、エステル、チオアミドおよびチオールエステル化合物 |
| CN101460458A (zh) | 2006-02-15 | 2009-06-17 | 阿勒根公司 | 具有1－磷酸－鞘氨醇(s1p)受体拮抗剂生物活性的带芳基或者杂芳基基团的吲哚－3－羧酸的酰胺、酯、硫代酰胺和硫羟酸酯化合物 |
| AU2007225836A1 (en) | 2006-03-10 | 2007-09-20 | Ono Pharmaceutical Co., Ltd. | Nitrogenated heterocyclic derivative, and pharmaceutical agent comprising the derivative as active ingredient |
| JP5257068B2 (ja) | 2006-05-16 | 2013-08-07 | 小野薬品工業株式会社 | 保護されていてもよい酸性基を含有する化合物およびその用途 |
| EA016633B1 (ru) * | 2006-05-23 | 2012-06-29 | Общество С Ограниченной Ответственностью "Инновационная Фармацевтика" | Замещенные индолы, способ их получения и применения |
| EP2055705A4 (en) | 2006-07-31 | 2014-08-20 | Ono Pharmaceutical Co | COMPOUND WITH A CYCLIC GROUP BOUND BY A SPIRO BINDING THEREOF AND APPLY THEREOF |
| EP2125723A1 (en) | 2007-01-11 | 2009-12-02 | Allergan, Inc. | 6-substituted indole-3-carboxylic acid amide compounds having sphingosine-1-phosphate (s1p) receptor antagonist biological activity |
| US8524917B2 (en) | 2007-01-11 | 2013-09-03 | Allergan, Inc. | 6-substituted indole-3-carboxylic acid amide compounds having sphingosine-1-phosphate (S1P) receptor antagonist biological activity |
| WO2010129351A1 (en) | 2009-04-28 | 2010-11-11 | Schepens Eye Research Institute | Method to identify and treat age-related macular degeneration |
| WO2011143430A1 (en) | 2010-05-12 | 2011-11-17 | Abbott Laboratories | Indazole inhibitors of kinase |
| WO2013024022A1 (en) | 2011-08-12 | 2013-02-21 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods and pharmaceutical compositions for treatment of pulmonary hypertension |
| JO3459B1 (ar) | 2012-09-09 | 2020-07-05 | H Lundbeck As | تركيبات صيدلانية لعلاج مرض الزهايمر |
| CN104193669B (zh) * | 2014-08-01 | 2016-12-07 | 大连理工大学 | 一类阿比朵尔类似物或其盐、其制备方法及应用 |
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| CN110256324A (zh) * | 2019-06-13 | 2019-09-20 | 苏州莱安医药化学技术有限公司 | 一种2-甲基-5-羟基吲哚的制备方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3549641A (en) * | 1966-06-28 | 1970-12-22 | Warner Lambert Pharmaceutical | Pyrano pyridines and process for their production |
| US3518258A (en) * | 1967-05-09 | 1970-06-30 | Warner Lambert Pharmaceutical | Pyrano(3,2-i)quinolizine and process for the production |
| US3565903A (en) * | 1967-11-24 | 1971-02-23 | Warner Lambert Pharmaceutical | Pyrano(2,3-b)quinolines and process for their production |
| US5635510A (en) * | 1993-05-06 | 1997-06-03 | Merrell Pharmaceuticals Inc. | Substituted pyrrolidin-3-yl-alkyl-piperidines |
| HRP960352A2 (en) * | 1996-07-26 | 1998-08-31 | Pliva Pharm & Chem Works | Novel coumarin quinoline carboxylic acids |
| US6403587B1 (en) * | 1997-02-26 | 2002-06-11 | Pfizer Inc. | Heteroaryl-hexanoic acid amide derivatives, their preparation and their use as selective inhibitors of MIP-1-α binding to its CCR 1 receptor |
| AU2654399A (en) * | 1998-02-02 | 1999-08-16 | Merck & Co., Inc. | Cyclic amine modulators of chemokine receptor activity |
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1999
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- 1999-12-20 WO PCT/US1999/030434 patent/WO2000042045A2/en not_active Application Discontinuation
- 1999-12-20 OA OA1200100187A patent/OA11820A/en unknown
- 1999-12-20 EP EP99963110A patent/EP1144415A2/en not_active Withdrawn
- 1999-12-20 CN CN99816475A patent/CN1344270A/zh active Pending
- 1999-12-20 AU AU19409/00A patent/AU1940900A/en not_active Abandoned
- 1999-12-20 CZ CZ20012502A patent/CZ20012502A3/cs unknown
- 1999-12-20 PL PL99349348A patent/PL349348A1/xx not_active Application Discontinuation
- 1999-12-20 HU HU0202932A patent/HUP0202932A3/hu unknown
- 1999-12-20 CA CA002372197A patent/CA2372197A1/en not_active Abandoned
- 1999-12-20 JP JP2000593612A patent/JP2002534526A/ja active Pending
- 1999-12-20 SK SK997-2001A patent/SK9972001A3/sk unknown
- 1999-12-20 IL IL14428999A patent/IL144289A0/xx unknown
- 1999-12-20 EA EA200100774A patent/EA200100774A1/ru unknown
- 1999-12-20 MX MXPA01007033A patent/MXPA01007033A/es unknown
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- 1999-12-20 AP APAP/P/2001/002228A patent/AP2001002228A0/en unknown
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2001
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- 2001-08-10 ZA ZA200106592A patent/ZA200106592B/en unknown
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2002
- 2002-08-28 HK HK02106357.2A patent/HK1044539A1/zh unknown
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| Publication number | Publication date |
|---|---|
| NO20013456L (no) | 2001-09-12 |
| AP2001002228A0 (en) | 2001-09-30 |
| KR20010086166A (ko) | 2001-09-08 |
| CZ20012502A3 (cs) | 2002-03-13 |
| HK1044539A1 (zh) | 2002-10-25 |
| OA11820A (en) | 2005-08-17 |
| WO2000042045A2 (en) | 2000-07-20 |
| CA2372197A1 (en) | 2000-07-20 |
| WO2000042045A3 (en) | 2000-11-09 |
| EA200100774A1 (ru) | 2002-02-28 |
| BR9916905A (pt) | 2002-01-29 |
| MXPA01007033A (es) | 2003-07-21 |
| HUP0202932A3 (en) | 2003-07-28 |
| NO20013456D0 (no) | 2001-07-12 |
| HUP0202932A2 (hu) | 2002-12-28 |
| EP1144415A2 (en) | 2001-10-17 |
| JP2002534526A (ja) | 2002-10-15 |
| AU1940900A (en) | 2000-08-01 |
| IL144289A0 (en) | 2002-05-23 |
| SK9972001A3 (en) | 2002-03-05 |
| CN1344270A (zh) | 2002-04-10 |
| PL349348A1 (en) | 2002-07-15 |
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