CA2658913C - Substituted aniline derivatives - Google Patents
Substituted aniline derivatives Download PDFInfo
- Publication number
- CA2658913C CA2658913C CA2658913A CA2658913A CA2658913C CA 2658913 C CA2658913 C CA 2658913C CA 2658913 A CA2658913 A CA 2658913A CA 2658913 A CA2658913 A CA 2658913A CA 2658913 C CA2658913 C CA 2658913C
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- compound
- pharmaceutically acceptable
- solvate
- polymorph
- 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.)
- Expired - Fee Related
Links
- 125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 title 1
- 238000011282 treatment Methods 0.000 claims abstract description 42
- 208000031888 Mycoses Diseases 0.000 claims abstract description 31
- 206010017533 Fungal infection Diseases 0.000 claims abstract description 30
- 150000001875 compounds Chemical class 0.000 claims description 429
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 186
- 150000003839 salts Chemical class 0.000 claims description 107
- 229910052739 hydrogen Inorganic materials 0.000 claims description 90
- 239000001257 hydrogen Substances 0.000 claims description 89
- 229910052736 halogen Inorganic materials 0.000 claims description 76
- 150000002367 halogens Chemical class 0.000 claims description 74
- 239000012453 solvate Substances 0.000 claims description 65
- 239000008194 pharmaceutical composition Substances 0.000 claims description 55
- 239000003814 drug Substances 0.000 claims description 54
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 42
- 238000002360 preparation method Methods 0.000 claims description 31
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 30
- 230000015572 biosynthetic process Effects 0.000 claims description 29
- 125000005842 heteroatom Chemical group 0.000 claims description 28
- 229920001503 Glucan Polymers 0.000 claims description 27
- 230000001225 therapeutic effect Effects 0.000 claims description 22
- 229940121375 antifungal agent Drugs 0.000 claims description 19
- 241000222122 Candida albicans Species 0.000 claims description 17
- 230000000843 anti-fungal effect Effects 0.000 claims description 15
- 239000006071 cream Substances 0.000 claims description 14
- 230000012010 growth Effects 0.000 claims description 12
- 238000001990 intravenous administration Methods 0.000 claims description 12
- 241000222120 Candida <Saccharomycetales> Species 0.000 claims description 11
- 239000003085 diluting agent Substances 0.000 claims description 11
- 241001225321 Aspergillus fumigatus Species 0.000 claims description 10
- 239000000499 gel Substances 0.000 claims description 10
- 230000000699 topical effect Effects 0.000 claims description 10
- 206010028980 Neoplasm Diseases 0.000 claims description 9
- 239000002674 ointment Substances 0.000 claims description 9
- 206010007134 Candida infections Diseases 0.000 claims description 8
- 201000011510 cancer Diseases 0.000 claims description 8
- 201000003984 candidiasis Diseases 0.000 claims description 8
- 238000007918 intramuscular administration Methods 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 238000007920 subcutaneous administration Methods 0.000 claims description 8
- 206010061598 Immunodeficiency Diseases 0.000 claims description 7
- 208000002474 Tinea Diseases 0.000 claims description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 7
- 230000003115 biocidal effect Effects 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 239000006072 paste Substances 0.000 claims description 7
- 230000002035 prolonged effect Effects 0.000 claims description 7
- 239000007921 spray Substances 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 230000000153 supplemental effect Effects 0.000 claims description 7
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- 230000036436 anti-hiv Effects 0.000 claims description 5
- 229940125708 antidiabetic agent Drugs 0.000 claims description 5
- 239000003472 antidiabetic agent Substances 0.000 claims description 5
- 239000012829 chemotherapy agent Substances 0.000 claims description 5
- 206010012601 diabetes mellitus Diseases 0.000 claims description 5
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 108010064760 Anidulafungin Proteins 0.000 claims description 4
- 108010021062 Micafungin Proteins 0.000 claims description 4
- 229960003348 anidulafungin Drugs 0.000 claims description 4
- JHVAMHSQVVQIOT-MFAJLEFUSA-N anidulafungin Chemical compound C1=CC(OCCCCC)=CC=C1C1=CC=C(C=2C=CC(=CC=2)C(=O)N[C@@H]2C(N[C@H](C(=O)N3C[C@H](O)C[C@H]3C(=O)N[C@H](C(=O)N[C@H](C(=O)N3C[C@H](C)[C@H](O)[C@H]3C(=O)N[C@H](O)[C@H](O)C2)[C@@H](C)O)[C@H](O)[C@@H](O)C=2C=CC(O)=CC=2)[C@@H](C)O)=O)C=C1 JHVAMHSQVVQIOT-MFAJLEFUSA-N 0.000 claims description 4
- JYIKNQVWKBUSNH-WVDDFWQHSA-N caspofungin Chemical compound C1([C@H](O)[C@@H](O)[C@H]2C(=O)N[C@H](C(=O)N3CC[C@H](O)[C@H]3C(=O)N[C@H](NCCN)[C@H](O)C[C@@H](C(N[C@H](C(=O)N3C[C@H](O)C[C@H]3C(=O)N2)[C@@H](C)O)=O)NC(=O)CCCCCCCC[C@@H](C)C[C@@H](C)CC)[C@H](O)CCN)=CC=C(O)C=C1 JYIKNQVWKBUSNH-WVDDFWQHSA-N 0.000 claims description 4
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- XMAYWYJOQHXEEK-OZXSUGGESA-N (2R,4S)-ketoconazole Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1OC[C@@H]1O[C@@](CN2C=NC=C2)(C=2C(=CC(Cl)=CC=2)Cl)OC1 XMAYWYJOQHXEEK-OZXSUGGESA-N 0.000 claims description 3
- BLSQLHNBWJLIBQ-OZXSUGGESA-N (2R,4S)-terconazole Chemical compound C1CN(C(C)C)CCN1C(C=C1)=CC=C1OC[C@@H]1O[C@@](CN2N=CN=C2)(C=2C(=CC(Cl)=CC=2)Cl)OC1 BLSQLHNBWJLIBQ-OZXSUGGESA-N 0.000 claims description 3
- MQHLMHIZUIDKOO-OKZBNKHCSA-N (2R,6S)-2,6-dimethyl-4-[(2S)-2-methyl-3-[4-(2-methylbutan-2-yl)phenyl]propyl]morpholine Chemical compound C1=CC(C(C)(C)CC)=CC=C1C[C@H](C)CN1C[C@@H](C)O[C@@H](C)C1 MQHLMHIZUIDKOO-OKZBNKHCSA-N 0.000 claims description 3
- MPIPASJGOJYODL-SFHVURJKSA-N (R)-isoconazole Chemical compound ClC1=CC(Cl)=CC=C1[C@@H](OCC=1C(=CC=CC=1Cl)Cl)CN1C=NC=C1 MPIPASJGOJYODL-SFHVURJKSA-N 0.000 claims description 3
- AFNXATANNDIXLG-SFHVURJKSA-N 1-[(2r)-2-[(4-chlorophenyl)methylsulfanyl]-2-(2,4-dichlorophenyl)ethyl]imidazole Chemical compound C1=CC(Cl)=CC=C1CS[C@H](C=1C(=CC(Cl)=CC=1)Cl)CN1C=NC=C1 AFNXATANNDIXLG-SFHVURJKSA-N 0.000 claims description 3
- ZCJYUTQZBAIHBS-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenyl)-2-{[4-(phenylsulfanyl)benzyl]oxy}ethyl]imidazole Chemical compound ClC1=CC(Cl)=CC=C1C(OCC=1C=CC(SC=2C=CC=CC=2)=CC=1)CN1C=NC=C1 ZCJYUTQZBAIHBS-UHFFFAOYSA-N 0.000 claims description 3
- OCAPBUJLXMYKEJ-UHFFFAOYSA-N 1-[biphenyl-4-yl(phenyl)methyl]imidazole Chemical compound C1=NC=CN1C(C=1C=CC(=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 OCAPBUJLXMYKEJ-UHFFFAOYSA-N 0.000 claims description 3
- LEZWWPYKPKIXLL-UHFFFAOYSA-N 1-{2-(4-chlorobenzyloxy)-2-(2,4-dichlorophenyl)ethyl}imidazole Chemical compound C1=CC(Cl)=CC=C1COC(C=1C(=CC(Cl)=CC=1)Cl)CN1C=NC=C1 LEZWWPYKPKIXLL-UHFFFAOYSA-N 0.000 claims description 3
- QXHHHPZILQDDPS-UHFFFAOYSA-N 1-{2-[(2-chloro-3-thienyl)methoxy]-2-(2,4-dichlorophenyl)ethyl}imidazole Chemical compound S1C=CC(COC(CN2C=NC=C2)C=2C(=CC(Cl)=CC=2)Cl)=C1Cl QXHHHPZILQDDPS-UHFFFAOYSA-N 0.000 claims description 3
- JLGKQTAYUIMGRK-UHFFFAOYSA-N 1-{2-[(7-chloro-1-benzothiophen-3-yl)methoxy]-2-(2,4-dichlorophenyl)ethyl}imidazole Chemical compound ClC1=CC(Cl)=CC=C1C(OCC=1C2=CC=CC(Cl)=C2SC=1)CN1C=NC=C1 JLGKQTAYUIMGRK-UHFFFAOYSA-N 0.000 claims description 3
- FRPZMMHWLSIFAZ-UHFFFAOYSA-N 10-undecenoic acid Chemical compound OC(=O)CCCCCCCCC=C FRPZMMHWLSIFAZ-UHFFFAOYSA-N 0.000 claims description 3
- VHVPQPYKVGDNFY-DFMJLFEVSA-N 2-[(2r)-butan-2-yl]-4-[4-[4-[4-[[(2r,4s)-2-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]phenyl]-1,2,4-triazol-3-one Chemical compound O=C1N([C@H](C)CC)N=CN1C1=CC=C(N2CCN(CC2)C=2C=CC(OC[C@@H]3O[C@](CN4N=CN=C4)(OC3)C=3C(=CC(Cl)=CC=3)Cl)=CC=2)C=C1 VHVPQPYKVGDNFY-DFMJLFEVSA-N 0.000 claims description 3
- MBRHNTMUYWQHMR-UHFFFAOYSA-N 2-aminoethanol;6-cyclohexyl-1-hydroxy-4-methylpyridin-2-one Chemical compound NCCO.ON1C(=O)C=C(C)C=C1C1CCCCC1 MBRHNTMUYWQHMR-UHFFFAOYSA-N 0.000 claims description 3
- APKFDSVGJQXUKY-KKGHZKTASA-N Amphotericin-B Natural products O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1C=CC=CC=CC=CC=CC=CC=C[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 APKFDSVGJQXUKY-KKGHZKTASA-N 0.000 claims description 3
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- CTETYYAZBPJBHE-UHFFFAOYSA-N Haloprogin Chemical compound ClC1=CC(Cl)=C(OCC#CI)C=C1Cl CTETYYAZBPJBHE-UHFFFAOYSA-N 0.000 claims description 3
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- BYBLEWFAAKGYCD-UHFFFAOYSA-N Miconazole Chemical compound ClC1=CC(Cl)=CC=C1COC(C=1C(=CC(Cl)=CC=1)Cl)CN1C=NC=C1 BYBLEWFAAKGYCD-UHFFFAOYSA-N 0.000 claims description 3
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- AWGBZRVEGDNLDZ-UHFFFAOYSA-N Rimocidin Natural products C1C(C(C(O)C2)C(O)=O)OC2(O)CC(O)CCCC(=O)CC(O)C(CC)C(=O)OC(CCC)CC=CC=CC=CC=CC1OC1OC(C)C(O)C(N)C1O AWGBZRVEGDNLDZ-UHFFFAOYSA-N 0.000 claims description 3
- AWGBZRVEGDNLDZ-JCUCCFEFSA-N Rimocidine Chemical compound O([C@H]1/C=C/C=C/C=C/C=C/C[C@H](OC(=O)[C@@H](CC)[C@H](O)CC(=O)CCC[C@H](O)C[C@@]2(O)O[C@H]([C@@H]([C@@H](O)C2)C(O)=O)C1)CCC)[C@@H]1O[C@H](C)[C@@H](O)[C@H](N)[C@@H]1O AWGBZRVEGDNLDZ-JCUCCFEFSA-N 0.000 claims description 3
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- APKFDSVGJQXUKY-INPOYWNPSA-N amphotericin B Chemical compound O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 APKFDSVGJQXUKY-INPOYWNPSA-N 0.000 claims description 3
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- ABJKWBDEJIDSJZ-UHFFFAOYSA-N butenafine Chemical compound C=1C=CC2=CC=CC=C2C=1CN(C)CC1=CC=C(C(C)(C)C)C=C1 ABJKWBDEJIDSJZ-UHFFFAOYSA-N 0.000 claims description 3
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- SWLMUYACZKCSHZ-UHFFFAOYSA-N butoconazole Chemical compound C1=CC(Cl)=CC=C1CCC(SC=1C(=CC=CC=1Cl)Cl)CN1C=NC=C1 SWLMUYACZKCSHZ-UHFFFAOYSA-N 0.000 claims description 3
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- RFHAOTPXVQNOHP-UHFFFAOYSA-N fluconazole Chemical compound C1=NC=NN1CC(C=1C(=CC(F)=CC=1)F)(O)CN1C=NC=N1 RFHAOTPXVQNOHP-UHFFFAOYSA-N 0.000 claims description 3
- XRECTZIEBJDKEO-UHFFFAOYSA-N flucytosine Chemical compound NC1=NC(=O)NC=C1F XRECTZIEBJDKEO-UHFFFAOYSA-N 0.000 claims description 3
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- DDFOUSQFMYRUQK-RCDICMHDSA-N isavuconazole Chemical compound C=1SC([C@H](C)[C@](O)(CN2N=CN=C2)C=2C(=CC=C(F)C=2)F)=NC=1C1=CC=C(C#N)C=C1 DDFOUSQFMYRUQK-RCDICMHDSA-N 0.000 claims description 3
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- 229940087450 zerit Drugs 0.000 description 1
- 229940052255 ziagen Drugs 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 229950009268 zinostatin Drugs 0.000 description 1
- 239000002076 α-tocopherol Substances 0.000 description 1
- 235000004835 α-tocopherol Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/14—Nitrogen atoms not forming part of a nitro radical
-
- 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
- A61P31/10—Antimycotics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic 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
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/02—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D223/06—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D223/12—Nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D267/00—Heterocyclic compounds containing rings of more than six members having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D267/02—Seven-membered rings
- C07D267/08—Seven-membered rings having the hetero atoms in positions 1 and 4
- C07D267/10—Seven-membered rings having the hetero atoms in positions 1 and 4 not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D281/00—Heterocyclic compounds containing rings of more than six members having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D281/02—Seven-membered rings
- C07D281/04—Seven-membered rings having the hetero atoms in positions 1 and 4
- C07D281/06—Seven-membered rings having the hetero atoms in positions 1 and 4 not condensed with other rings
-
- 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
- C07D401/12—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 chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- C07D417/12—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 chain containing hetero atoms as chain links
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Tropical Medicine & Parasitology (AREA)
- Engineering & Computer Science (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Peptides Or Proteins (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Pyrrole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0614678.1 | 2006-07-24 | ||
| GB0614677A GB0614677D0 (en) | 2006-07-24 | 2006-07-24 | Substituted Aniline Derivatives |
| GB0614677.3 | 2006-07-24 | ||
| GB0614678A GB0614678D0 (en) | 2006-07-24 | 2006-07-24 | Substituted aniline derivatives |
| GB0704648.5 | 2007-03-09 | ||
| GB0704648A GB0704648D0 (en) | 2007-03-09 | 2007-03-09 | Substituted aniline derivatives |
| GB0704645.1 | 2007-03-09 | ||
| GB0704645A GB0704645D0 (en) | 2007-03-09 | 2007-03-09 | Substituted aniline derivatives |
| PCT/GB2007/002815 WO2008012524A1 (en) | 2006-07-24 | 2007-07-24 | Substituted aniline derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2658913A1 CA2658913A1 (en) | 2008-01-31 |
| CA2658913C true CA2658913C (en) | 2015-07-21 |
Family
ID=38484243
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2658913A Expired - Fee Related CA2658913C (en) | 2006-07-24 | 2007-07-24 | Substituted aniline derivatives |
Country Status (6)
| Country | Link |
|---|---|
| US (3) | US7678785B2 (enExample) |
| EP (1) | EP2046739B1 (enExample) |
| JP (1) | JP5468900B2 (enExample) |
| AU (1) | AU2007279092B2 (enExample) |
| CA (1) | CA2658913C (enExample) |
| WO (1) | WO2008012524A1 (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7678785B2 (en) * | 2006-07-24 | 2010-03-16 | Ucb Pharma S.A. | Substituted aniline derivatives |
| NZ576324A (en) * | 2006-10-31 | 2011-08-26 | Cadila Healthcare Ltd | Selective tr-beta 1 agonist |
| TWI386204B (zh) * | 2008-04-10 | 2013-02-21 | Mitsubishi Tanabe Pharma Corp | 高半胱胺酸合成酶抑制劑 |
| CA2726703A1 (en) * | 2008-06-16 | 2009-12-23 | F. Hoffmann-La Roche Ag | Heteroaromatic monoamides as orexinin receptor antagonists |
| WO2011043480A1 (ja) * | 2009-10-09 | 2011-04-14 | 田辺三菱製薬株式会社 | ホモシステイン合成酵素阻害薬 |
| CA2821807A1 (en) * | 2010-12-21 | 2012-06-28 | Nestec S.A. | Methods and compositions suitable for managing blood glucose in animals |
| RU2541532C2 (ru) * | 2012-10-16 | 2015-02-20 | Федеральное Государственное Бюджетное Учреждение Науки Институт Нефтехимии И Катализа Ран | Ди-[4-(диметиламинометилсульфанил)-фениловый] эфир щавелевокислый - водорастворимое средство для борьбы с почвенной и поверхностно-семенной инфекцией |
| CN106563929B (zh) | 2015-10-08 | 2019-09-17 | 利宝地工程有限公司 | 修复和制造涡轮发动机部件的方法及涡轮发动机部件 |
| WO2018048882A1 (en) | 2016-09-06 | 2018-03-15 | The Research Foundation For The State University Of New York | Positron imaging tomography imaging agent composition and method for bacterial infection |
| EP3824906A1 (en) | 2016-12-21 | 2021-05-26 | Amgen Inc. | Anti-tnf alpha antibody formulations |
| CN108172553A (zh) * | 2018-01-17 | 2018-06-15 | 杭州暖芯迦电子科技有限公司 | 一种视网膜假体植入芯片的封装结构及其封装方法 |
| CN116947678B (zh) * | 2023-07-24 | 2025-07-08 | 河南大学 | 一类氮原子双取代芳香环类小分子有机化合物及其衍生物及其在制备抗菌药物中的应用 |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2676188A (en) * | 1950-12-16 | 1954-04-20 | American Home Prod | Acylated glycinamides |
| US4205168A (en) * | 1973-09-24 | 1980-05-27 | Chevron Research Company | N-Carbamylalkyl-2,6-dialkyl-α-haloacetanilides |
| US3944607A (en) * | 1974-10-17 | 1976-03-16 | Chevron Research Company | Herbicidal N-(N'-alkynylcarbamylmethyl)-2,6-dialkyl-α-haloacetanilides |
| JPS51125741A (en) * | 1974-10-17 | 1976-11-02 | Chevron Res | Weed killer |
| LU78804A1 (de) * | 1977-12-30 | 1979-07-20 | Byk Gulden Lomberg Chem Fab | N-substituierte w-aminoalkanoyl-w-aminoalkansaeuren,ihre verwendung und verfahren zu ihrer herstellung sowie diese verbindungen enthaltende arzneimittel |
| DE3114351A1 (de) * | 1981-04-09 | 1982-11-04 | Hoechst Ag, 6000 Frankfurt | "oxindol-derivate, verfahren zu ihrer herstellung und sie enthaltende arzneimittel mit neuroanaboler wirkung" |
| JPS58154567A (ja) * | 1982-03-09 | 1983-09-14 | Teikoku Chem Ind Corp Ltd | チオフエノ−ル誘導体及びその製造方法 |
| US4736066A (en) * | 1982-07-19 | 1988-04-05 | E. R. Squibb & Sons, Inc. | Intermediate for substituted peptide compounds |
| JPH01211560A (ja) * | 1988-02-18 | 1989-08-24 | Sagami Chem Res Center | β−ラクタム誘導体の製造方法 |
| IT1224627B (it) * | 1988-04-12 | 1990-10-04 | Guidotti & C Spa Labor | Ammidi di acidi ciclometilen_1,2_dicarbossilici adattivita' terapeutica, procedimenti per la loro preparazione e composizioni farmaceutiche che le contengono. |
| ES2087038B1 (es) * | 1994-11-07 | 1997-03-16 | Uriach & Cia Sa J | Nuevas piperidinas con actividad antagonista del paf. |
| US6350761B1 (en) * | 1999-07-30 | 2002-02-26 | Berlex Laboratories, Inc. | Benzenamine derivatives as anti-coagulants |
| CN102050758A (zh) * | 2000-09-14 | 2011-05-11 | 田边三菱制药株式会社 | 酰胺衍生物及其制备药物的用途 |
| RU2247716C2 (ru) | 2003-03-27 | 2005-03-10 | Российский химико-технологический университет им. Д.И. Менделеева (РХТУ) | Замещенные метил-n-амидооксамоил-n-фенил-d, l-аланинаты и их способы получения |
| EP1669348A4 (en) * | 2003-09-30 | 2009-03-11 | Eisai R&D Man Co Ltd | NEW ANTIPILIC AGENT CONTAINING A HETEROCYCLIC COMPOUND |
| JP2005202314A (ja) * | 2004-01-19 | 2005-07-28 | Fuji Photo Film Co Ltd | 重合性組成物及びそれを用いた画像形成材料 |
| EP1717238A4 (en) * | 2004-02-16 | 2008-03-05 | Daiichi Seiyaku Co | FUNGICIDES HETEROCYCLIC COMPOUNDS |
| WO2006012441A1 (en) * | 2004-07-23 | 2006-02-02 | Susan Marie Royalty | Peptidase inhibitors |
| JP4874958B2 (ja) * | 2005-03-30 | 2012-02-15 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | ピリジン誘導体を含有する抗真菌剤 |
| US7737166B2 (en) * | 2005-08-17 | 2010-06-15 | Daiichi Sankyo Company, Limited | Antifungal bicyclic hetero ring compounds |
| US7678785B2 (en) | 2006-07-24 | 2010-03-16 | Ucb Pharma S.A. | Substituted aniline derivatives |
-
2007
- 2007-07-24 US US11/782,337 patent/US7678785B2/en not_active Expired - Fee Related
- 2007-07-24 EP EP07766352.4A patent/EP2046739B1/en not_active Not-in-force
- 2007-07-24 AU AU2007279092A patent/AU2007279092B2/en not_active Ceased
- 2007-07-24 JP JP2009521335A patent/JP5468900B2/ja not_active Expired - Fee Related
- 2007-07-24 WO PCT/GB2007/002815 patent/WO2008012524A1/en not_active Ceased
- 2007-07-24 CA CA2658913A patent/CA2658913C/en not_active Expired - Fee Related
-
2010
- 2010-01-13 US US12/687,008 patent/US8071582B2/en not_active Expired - Fee Related
-
2011
- 2011-10-07 US US13/269,321 patent/US8624022B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US8624022B2 (en) | 2014-01-07 |
| AU2007279092A1 (en) | 2008-01-31 |
| EP2046739A1 (en) | 2009-04-15 |
| US20080045497A1 (en) | 2008-02-21 |
| JP5468900B2 (ja) | 2014-04-09 |
| US8071582B2 (en) | 2011-12-06 |
| US20110014271A1 (en) | 2011-01-20 |
| CA2658913A1 (en) | 2008-01-31 |
| US20120029188A1 (en) | 2012-02-02 |
| EP2046739B1 (en) | 2015-08-26 |
| AU2007279092B2 (en) | 2012-12-13 |
| JP2009544676A (ja) | 2009-12-17 |
| WO2008012524A1 (en) | 2008-01-31 |
| US7678785B2 (en) | 2010-03-16 |
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Legal Events
| Date | Code | Title | Description |
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| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20170724 |