TW200902518A - Substituted heterocyclic derivatives and their pharmaceutical use and compositions - Google Patents
Substituted heterocyclic derivatives and their pharmaceutical use and compositions Download PDFInfo
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- TW200902518A TW200902518A TW097117046A TW97117046A TW200902518A TW 200902518 A TW200902518 A TW 200902518A TW 097117046 A TW097117046 A TW 097117046A TW 97117046 A TW97117046 A TW 97117046A TW 200902518 A TW200902518 A TW 200902518A
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- group
- alkyl
- alkoxy
- propyl
- compound
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- 239000000203 mixture Substances 0.000 title claims description 148
- 125000000623 heterocyclic group Chemical group 0.000 title claims description 18
- 150000001875 compounds Chemical class 0.000 claims abstract description 181
- -1 (c3-c) Chemical group 0.000 claims description 146
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 124
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 104
- 125000000217 alkyl group Chemical group 0.000 claims description 101
- 125000003545 alkoxy group Chemical group 0.000 claims description 64
- 238000000034 method Methods 0.000 claims description 62
- 125000003118 aryl group Chemical group 0.000 claims description 44
- BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Substances OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 42
- 150000003839 salts Chemical class 0.000 claims description 38
- 239000002253 acid Substances 0.000 claims description 33
- 125000001072 heteroaryl group Chemical group 0.000 claims description 29
- 239000000651 prodrug Substances 0.000 claims description 28
- 229940002612 prodrug Drugs 0.000 claims description 28
- XJLSEXAGTJCILF-RXMQYKEDSA-N (R)-nipecotic acid zwitterion Chemical compound OC(=O)[C@@H]1CCCNC1 XJLSEXAGTJCILF-RXMQYKEDSA-N 0.000 claims description 27
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 26
- 229910052736 halogen Inorganic materials 0.000 claims description 24
- 150000002367 halogens Chemical class 0.000 claims description 24
- 239000001257 hydrogen Substances 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 24
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 23
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 21
- GYSCBCSGKXNZRH-UHFFFAOYSA-N 1-benzothiophene-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=CC2=C1 GYSCBCSGKXNZRH-UHFFFAOYSA-N 0.000 claims description 20
- 230000000670 limiting effect Effects 0.000 claims description 19
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 18
- 125000004122 cyclic group Chemical group 0.000 claims description 18
- 239000003814 drug Substances 0.000 claims description 18
- 235000019253 formic acid Nutrition 0.000 claims description 18
- 239000012453 solvate Substances 0.000 claims description 16
- 150000001412 amines Chemical class 0.000 claims description 15
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 15
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 15
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 14
- 125000004429 atom Chemical group 0.000 claims description 14
- 239000007789 gas Chemical group 0.000 claims description 14
- GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Natural products CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- 125000001424 substituent group Chemical group 0.000 claims description 13
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 12
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- 239000001301 oxygen Chemical group 0.000 claims description 12
- 239000008194 pharmaceutical composition Substances 0.000 claims description 12
- 238000011282 treatment Methods 0.000 claims description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 125000003277 amino group Chemical group 0.000 claims description 9
- 125000004104 aryloxy group Chemical group 0.000 claims description 9
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 8
- 125000004414 alkyl thio group Chemical group 0.000 claims description 8
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- 208000015181 infectious disease Diseases 0.000 claims description 8
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- 125000003282 alkyl amino group Chemical group 0.000 claims description 7
- 125000002619 bicyclic group Chemical group 0.000 claims description 7
- 125000005842 heteroatom Chemical group 0.000 claims description 7
- 125000002950 monocyclic group Chemical group 0.000 claims description 7
- 238000006467 substitution reaction Methods 0.000 claims description 7
- 125000003396 thiol group Chemical class [H]S* 0.000 claims description 7
- 241000124008 Mammalia Species 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 150000001735 carboxylic acids Chemical class 0.000 claims description 6
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 5
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 5
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
- 229910052717 sulfur Chemical group 0.000 claims description 5
- 239000011593 sulfur Chemical group 0.000 claims description 5
- 125000006693 (C2-C9) heterocyclyl group Chemical group 0.000 claims description 4
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 4
- 125000002837 carbocyclic group Chemical group 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 238000009833 condensation Methods 0.000 claims description 4
- 230000005494 condensation Effects 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
- 239000003981 vehicle Substances 0.000 claims description 4
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 3
- 125000006612 decyloxy group Chemical group 0.000 claims description 3
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 230000036961 partial effect Effects 0.000 claims description 3
- 230000002265 prevention Effects 0.000 claims description 3
- 125000003003 spiro group Chemical group 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 2
- 208000035143 Bacterial infection Diseases 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 241001529936 Murinae Species 0.000 claims description 2
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 2
- 208000022362 bacterial infectious disease Diseases 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 2
- 239000003995 emulsifying agent Substances 0.000 claims description 2
- 239000000839 emulsion Substances 0.000 claims description 2
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 2
- 125000001207 fluorophenyl group Chemical group 0.000 claims description 2
- 125000004470 heterocyclooxy group Chemical group 0.000 claims description 2
- RNIXSZHNJLUJGC-UHFFFAOYSA-N hydroxy(nitro)cyanamide Chemical compound N#CN(O)[N+]([O-])=O RNIXSZHNJLUJGC-UHFFFAOYSA-N 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 229940124597 therapeutic agent Drugs 0.000 claims 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- RMOZJBUKCIBNPM-UHFFFAOYSA-N 1-cyano-1-nitroguanidine Chemical compound NC(=N)N(C#N)[N+]([O-])=O RMOZJBUKCIBNPM-UHFFFAOYSA-N 0.000 claims 1
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims 1
- 239000005711 Benzoic acid Substances 0.000 claims 1
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims 1
- 102100035353 Cyclin-dependent kinase 2-associated protein 1 Human genes 0.000 claims 1
- 241000736199 Paeonia Species 0.000 claims 1
- 235000006484 Paeonia officinalis Nutrition 0.000 claims 1
- 102000005890 Spectrin Human genes 0.000 claims 1
- 108010019965 Spectrin Proteins 0.000 claims 1
- 150000003973 alkyl amines Chemical class 0.000 claims 1
- 125000005577 anthracene group Chemical group 0.000 claims 1
- 125000005427 anthranyl group Chemical group 0.000 claims 1
- 125000005366 cycloalkylthio group Chemical group 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000004404 heteroalkyl group Chemical group 0.000 claims 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims 1
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims 1
- 239000003016 pheromone Substances 0.000 claims 1
- 239000010948 rhodium Substances 0.000 claims 1
- 229910052703 rhodium Inorganic materials 0.000 claims 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical group [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims 1
- 125000006413 ring segment Chemical group 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 46
- 239000004599 antimicrobial Substances 0.000 abstract description 2
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- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 35
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- NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 description 1
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- JTJMJGYZQZDUJJ-UHFFFAOYSA-N phencyclidine Chemical compound C1CCCCN1C1(C=2C=CC=CC=2)CCCCC1 JTJMJGYZQZDUJJ-UHFFFAOYSA-N 0.000 description 1
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- UXCDUFKZSUBXGM-UHFFFAOYSA-N phosphoric tribromide Chemical compound BrP(Br)(Br)=O UXCDUFKZSUBXGM-UHFFFAOYSA-N 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
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- LZMJNVRJMFMYQS-UHFFFAOYSA-N poseltinib Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(OC=C2)C2=N1 LZMJNVRJMFMYQS-UHFFFAOYSA-N 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- CUQOHAYJWVTKDE-UHFFFAOYSA-N potassium;butan-1-olate Chemical compound [K+].CCCC[O-] CUQOHAYJWVTKDE-UHFFFAOYSA-N 0.000 description 1
- 238000000634 powder X-ray diffraction Methods 0.000 description 1
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- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000005180 public health Effects 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- GJAWHXHKYYXBSV-UHFFFAOYSA-N pyridinedicarboxylic acid Natural products OC(=O)C1=CC=CN=C1C(O)=O GJAWHXHKYYXBSV-UHFFFAOYSA-N 0.000 description 1
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- 238000012799 strong cation exchange Methods 0.000 description 1
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- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 125000004354 sulfur functional group Chemical group 0.000 description 1
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- 239000013589 supplement Substances 0.000 description 1
- 230000009747 swallowing Effects 0.000 description 1
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- LRBQNJMCXXYXIU-NRMVVENXSA-N tannic acid Chemical compound OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@@H]2[C@H]([C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-NRMVVENXSA-N 0.000 description 1
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- 229940095064 tartrate Drugs 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
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- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- NYERMPLPURRVGM-UHFFFAOYSA-N thiazepine Chemical compound S1C=CC=CC=N1 NYERMPLPURRVGM-UHFFFAOYSA-N 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- JOUDBUYBGJYFFP-FOCLMDBBSA-N thioindigo Chemical compound S\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2S1 JOUDBUYBGJYFFP-FOCLMDBBSA-N 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- AHDDRJBFJBDEPW-DTWKUNHWSA-N trans-2-Phenylcyclopropanecarboxylic acid Chemical compound OC(=O)[C@@H]1C[C@H]1C1=CC=CC=C1 AHDDRJBFJBDEPW-DTWKUNHWSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 229960000281 trometamol Drugs 0.000 description 1
- 238000002525 ultrasonication Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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Classifications
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- 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
-
- 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
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
- C07D401/14—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 three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- 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
-
- 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
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
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| US20120189546A1 (en) * | 2009-07-11 | 2012-07-26 | Bayer Pharma Aktiengesellschaft | Radiolabelling Method Using Cycloalkyl Groups |
| MA41169A (fr) | 2014-12-17 | 2017-10-24 | Acraf | Composés antibactériens à large spectre d'activité |
| AU2017276627A1 (en) | 2016-06-08 | 2018-12-20 | Aziende Chimiche Riunite Angelini Francesco A.C.R.A.F. S.P.A. | New antibacterial compounds |
| JP6755775B2 (ja) * | 2016-11-04 | 2020-09-16 | 富士アミドケミカル株式会社 | 4−フルオロイソキノリンの製法 |
| CN108627579B (zh) * | 2017-03-24 | 2020-12-01 | 上海安谱实验科技股份有限公司 | Pbt制品中多环芳烃的提取方法 |
| WO2019133605A1 (en) * | 2017-12-26 | 2019-07-04 | Astellas Pharma Inc. | Process for the preparation of an amino-pyrimidine and intermediates thereof |
| AU2019375983A1 (en) | 2018-11-09 | 2021-06-10 | Vivace Therapeutics, Inc. | Bicyclic compounds |
| HUE070525T2 (hu) | 2019-04-16 | 2025-06-28 | Vivace Therapeutics Inc | Biciklusos vegyületek |
| CN111848423B (zh) * | 2019-04-30 | 2022-10-14 | 尚科生物医药(上海)有限公司 | 3-氧代环丁基氨基甲酸叔丁酯的制备方法 |
| WO2021257863A1 (en) | 2020-06-19 | 2021-12-23 | Incyte Corporation | Pyrrolotriazine compounds as jak2 v617f inhibitors |
| US11691971B2 (en) | 2020-06-19 | 2023-07-04 | Incyte Corporation | Naphthyridinone compounds as JAK2 V617F inhibitors |
| US11767323B2 (en) | 2020-07-02 | 2023-09-26 | Incyte Corporation | Tricyclic pyridone compounds as JAK2 V617F inhibitors |
| IL299612A (en) | 2020-07-02 | 2023-03-01 | Incyte Corp | Tricyclic urea compounds as JAK2 V617F inhibitors |
| US11661422B2 (en) | 2020-08-27 | 2023-05-30 | Incyte Corporation | Tricyclic urea compounds as JAK2 V617F inhibitors |
| WO2022140231A1 (en) | 2020-12-21 | 2022-06-30 | Incyte Corporation | Deazaguaine compounds as jak2 v617f inhibitors |
| US11958861B2 (en) | 2021-02-25 | 2024-04-16 | Incyte Corporation | Spirocyclic lactams as JAK2 V617F inhibitors |
| AU2022380979A1 (en) | 2021-11-02 | 2024-06-06 | Flare Therapeutics Inc. | Pparg inverse agonists and uses thereof |
| EP4493558A1 (en) | 2022-03-17 | 2025-01-22 | Incyte Corporation | Tricyclic urea compounds as jak2 v617f inhibitors |
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| US3869461A (en) * | 1968-07-02 | 1975-03-04 | Hoffmann La Roche | Intermediates for quinine, quinidine and derivatives thereof |
| US4096146A (en) * | 1968-07-02 | 1978-06-20 | Hoffmann-La Roche Inc. | 4-[5(R)-Alkyl(or alkenyl)-4(S)-quinuclidin-2(S) or 2(R)-ylcarbonyl]-quinolines, antipodes or racemates thereof and processes for their preparation |
| US3828048A (en) * | 1970-10-14 | 1974-08-06 | Res Et D Applic Scient Sogeras | Alkylsulfonic derivatives of quinine alkaloids |
| US4002757A (en) * | 1974-12-26 | 1977-01-11 | A. H. Robins Company, Incorporated | N-(1-substituted-3-pyrrolidinyl)-4-quinolinecarboxamides |
| PT66682B (pt) * | 1976-06-18 | 1978-11-15 | Ind Biolog Francaise | /(quinolyl-4)-propyl-1/-4 piperidines leur preparation et leur utilisation comme medicaments /(quinolyl-4)-propyl/-4 piperidines leur preparation et leur utilisation comme medicaments |
| NL7908031A (nl) * | 1979-11-01 | 1981-06-01 | Acf Chemiefarma Nv | Nieuwe chinolinederivaten en farmaceutische preparaten die een dergelijke verbinding bevatten, alsmede werk- wijze voor het bereiden van deze verbindingen. |
| FR2471981A1 (fr) * | 1979-12-21 | 1981-06-26 | Pharmindustrie | Nouveaux derives de la (piperidyl-4)-2 (quinolyl-4)-1 ethanone, produits intermediaires et procedes pour leur preparation, et leur utilisation comme medicaments |
| FR2495470A1 (fr) * | 1980-12-05 | 1982-06-11 | Pharmindustrie | Nouveaux medicaments a base de derives de (quinolyl-4)-1 (piperidyl-4)-2 ethanol ou (quinolyl-4)-1 (piperidyl-4)-3 propanol |
| US4757079A (en) * | 1986-06-24 | 1988-07-12 | Dynamac Corporaton | Anti-hypertensive piperidine compounds |
| FI95572C (fi) * | 1987-06-22 | 1996-02-26 | Eisai Co Ltd | Menetelmä lääkeaineena käyttökelpoisen piperidiinijohdannaisten tai sen farmaseuttisen suolan valmistamiseksi |
| US5260331A (en) * | 1989-01-02 | 1993-11-09 | John Wyeth & Brother Limited | Composition for treating depression with (S- or O-heteroaryl)alkyl amines |
| FR2642069B1 (fr) * | 1989-01-20 | 1991-04-12 | Rhone Poulenc Sante | Nouveaux derives du benzopyranne, leur preparation et les compositions pharmaceutiques qui les contiennent |
| CA2056405A1 (en) * | 1990-04-06 | 1991-10-07 | Mitsumasa Shino | Solid oral preparation containing catechol compound |
| DE69231679T2 (de) * | 1991-04-03 | 2001-10-31 | Korea Research Institute Of Chemical Technology, Daejeon | 2-chinolinonderivate, verfahren zu deren herstellung und diese enthaltende fungizide und insektizide |
| CA2075154A1 (en) * | 1991-08-06 | 1993-02-07 | Neelakantan Balasubramanian | Peptide aldehydes as antithrombotic agents |
| GB9216297D0 (en) * | 1991-08-15 | 1992-09-16 | Ici Plc | Therapeutic agents |
| FR2695126B1 (fr) * | 1992-08-27 | 1994-11-10 | Sanofi Elf | Dérivés d'acide thiényl ou pyrrolyl carboxyliques, leur préparation et médicaments les contenant. |
| DE4321030A1 (de) * | 1993-06-24 | 1995-01-05 | Bayer Ag | 4-bicyclisch substituierte Dihydropyridine, Verfahren zu ihrer Herstellung und ihre Verwendung in Arzneimittel |
| GB9318691D0 (en) * | 1993-09-09 | 1993-10-27 | Merck Sharp & Dohme | Therapeutic agents |
| US5512581A (en) * | 1994-07-18 | 1996-04-30 | Abbott Laboratories | Iminoxycarboxylates and derivatives as inhibitors of leukotriene biosynthesis |
| US6083977A (en) * | 1994-12-30 | 2000-07-04 | Ligand Pharmaceuticals Incorporated | Trienoic retinoid compounds and methods |
| US5741789A (en) * | 1995-01-17 | 1998-04-21 | Eli Lilly And Company | Compounds having effects on serotonin-related systems |
| US6008230A (en) * | 1995-10-16 | 1999-12-28 | Fujisawa Pharmaceutical Co., Ltd. | Quinoline compounds as H+ -ATPases |
| DE19613329A1 (de) * | 1996-04-03 | 1997-10-09 | Hoechst Schering Agrevo Gmbh | Substituierte Pyridine/Pyrimidine, Verfahren zu ihrer Herstellung und ihre Verwendung als Schädlingsbekämpfungsmittel |
| EP0918522A4 (en) * | 1996-05-20 | 1999-08-18 | Merck & Co Inc | GONADOLIBERIN ANTAGONISTS |
| US6147088A (en) * | 1996-05-20 | 2000-11-14 | Merck & Co., Inc. | Antagonists of gonadotropin releasing hormone |
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-
2008
- 2008-04-29 KR KR1020097025640A patent/KR20090130347A/ko not_active Ceased
- 2008-04-29 KR KR1020127000612A patent/KR20120011093A/ko not_active Withdrawn
- 2008-04-29 MX MX2009012117A patent/MX2009012117A/es not_active Application Discontinuation
- 2008-04-29 AU AU2008249745A patent/AU2008249745B2/en not_active Ceased
- 2008-04-29 CA CA002685888A patent/CA2685888A1/en not_active Abandoned
- 2008-04-29 JP JP2010507014A patent/JP2010526130A/ja not_active Withdrawn
- 2008-04-29 CN CN200880020428A patent/CN101679357A/zh active Pending
- 2008-04-29 EP EP12165102A patent/EP2481735A1/en not_active Withdrawn
- 2008-04-29 WO PCT/IB2008/001076 patent/WO2008139288A2/en not_active Ceased
- 2008-04-29 EP EP08737576A patent/EP2155716A2/en not_active Withdrawn
- 2008-05-07 AR ARP080101937A patent/AR066478A1/es not_active Application Discontinuation
- 2008-05-07 PE PE2008000800A patent/PE20090240A1/es not_active Application Discontinuation
- 2008-05-08 TW TW097117046A patent/TW200902518A/zh unknown
- 2008-05-08 US US12/117,071 patent/US20080280879A1/en not_active Abandoned
- 2008-05-08 UY UY31071A patent/UY31071A1/es not_active Application Discontinuation
- 2008-05-09 CL CL2008001367A patent/CL2008001367A1/es unknown
- 2008-05-09 PA PA20088779801A patent/PA8779801A1/es unknown
-
2009
- 2009-10-29 IL IL201830A patent/IL201830A0/en unknown
- 2009-11-04 ZA ZA200907761A patent/ZA200907761B/xx unknown
-
2010
- 2010-12-20 US US12/972,620 patent/US20110092480A1/en not_active Abandoned
-
2011
- 2011-11-22 US US13/302,151 patent/US20120065188A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| WO2008139288A3 (en) | 2009-03-26 |
| US20110092480A1 (en) | 2011-04-21 |
| KR20090130347A (ko) | 2009-12-22 |
| EP2155716A2 (en) | 2010-02-24 |
| AR066478A1 (es) | 2009-08-19 |
| AU2008249745A1 (en) | 2008-11-20 |
| US20120065188A1 (en) | 2012-03-15 |
| JP2010526130A (ja) | 2010-07-29 |
| UY31071A1 (es) | 2009-01-05 |
| PE20090240A1 (es) | 2009-03-19 |
| AU2008249745B2 (en) | 2012-01-12 |
| US20080280879A1 (en) | 2008-11-13 |
| CN101679357A (zh) | 2010-03-24 |
| EP2481735A1 (en) | 2012-08-01 |
| PA8779801A1 (es) | 2009-01-23 |
| MX2009012117A (es) | 2009-11-23 |
| ZA200907761B (en) | 2010-08-25 |
| IL201830A0 (en) | 2010-06-16 |
| KR20120011093A (ko) | 2012-02-06 |
| WO2008139288A2 (en) | 2008-11-20 |
| CL2008001367A1 (es) | 2008-11-07 |
| CA2685888A1 (en) | 2008-11-20 |
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