JPH10507174A - 抗微生物活性を有する環状ヘキサペプチド化合物 - Google Patents
抗微生物活性を有する環状ヘキサペプチド化合物Info
- Publication number
- JPH10507174A JPH10507174A JP8512472A JP51247296A JPH10507174A JP H10507174 A JPH10507174 A JP H10507174A JP 8512472 A JP8512472 A JP 8512472A JP 51247296 A JP51247296 A JP 51247296A JP H10507174 A JPH10507174 A JP H10507174A
- Authority
- JP
- Japan
- Prior art keywords
- alkoxy
- phenyl
- substituted
- alkyl
- aryl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 title claims description 156
- 230000000845 anti-microbial effect Effects 0.000 title abstract description 9
- 125000004122 cyclic group Chemical group 0.000 title description 2
- 150000003839 salts Chemical class 0.000 claims abstract description 34
- 238000000034 method Methods 0.000 claims abstract description 12
- 238000011282 treatment Methods 0.000 claims abstract description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 5
- 241001465754 Metazoa Species 0.000 claims abstract description 4
- 230000001225 therapeutic effect Effects 0.000 claims abstract description 3
- 230000000069 prophylactic effect Effects 0.000 claims abstract 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 509
- -1 indolylcarbonyl Chemical group 0.000 claims description 303
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 292
- 125000000217 alkyl group Chemical group 0.000 claims description 275
- 125000003118 aryl group Chemical group 0.000 claims description 236
- 125000001589 carboacyl group Chemical group 0.000 claims description 185
- 125000001424 substituent group Chemical group 0.000 claims description 164
- 125000003435 aroyl group Chemical group 0.000 claims description 103
- 239000000203 mixture Substances 0.000 claims description 102
- 125000000623 heterocyclic group Chemical group 0.000 claims description 95
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 65
- 125000001624 naphthyl group Chemical group 0.000 claims description 51
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 50
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 49
- 229910052757 nitrogen Inorganic materials 0.000 claims description 40
- 125000001038 naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 claims description 33
- 125000004043 oxo group Chemical group O=* 0.000 claims description 33
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 31
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 28
- 229920006395 saturated elastomer Polymers 0.000 claims description 27
- 125000004434 sulfur atom Chemical group 0.000 claims description 26
- 229920001184 polypeptide Polymers 0.000 claims description 19
- 102000004196 processed proteins & peptides Human genes 0.000 claims description 19
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 19
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 15
- 125000004104 aryloxy group Chemical group 0.000 claims description 13
- 125000002950 monocyclic group Chemical group 0.000 claims description 13
- 125000003342 alkenyl group Chemical group 0.000 claims description 12
- 125000005843 halogen group Chemical group 0.000 claims description 12
- 125000005936 piperidyl group Chemical group 0.000 claims description 12
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 11
- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical group C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 125000002541 furyl group Chemical group 0.000 claims description 10
- 125000004193 piperazinyl group Chemical group 0.000 claims description 10
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 10
- 125000001425 triazolyl group Chemical group 0.000 claims description 10
- 125000003277 amino group Chemical group 0.000 claims description 9
- 125000002971 oxazolyl group Chemical group 0.000 claims description 9
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Chemical group C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 9
- 125000001769 aryl amino group Chemical group 0.000 claims description 8
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 125000005036 alkoxyphenyl group Chemical group 0.000 claims description 5
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 5
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 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
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 5
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
- 208000035473 Communicable disease Diseases 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical group 0.000 claims description 3
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 3
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 2
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 1
- 101100490437 Mus musculus Acvrl1 gene Proteins 0.000 claims 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 1
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N benzo-alpha-pyrone Natural products C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 claims 1
- 125000005872 benzooxazolyl group Chemical group 0.000 claims 1
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- 229960000956 coumarin Drugs 0.000 claims 1
- 235000001671 coumarin Nutrition 0.000 claims 1
- 125000000332 coumarinyl group Chemical group O1C(=O)C(=CC2=CC=CC=C12)* 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 244000000010 microbial pathogen Species 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 425
- 206010035660 Pneumocystis Infections Diseases 0.000 abstract description 3
- 230000000843 anti-fungal effect Effects 0.000 abstract description 3
- 208000015181 infectious disease Diseases 0.000 abstract description 3
- 229920002498 Beta-glucan Polymers 0.000 abstract description 2
- 206010073756 Pneumocystis jirovecii infection Diseases 0.000 abstract description 2
- 230000002401 inhibitory effect Effects 0.000 abstract description 2
- 201000000317 pneumocystosis Diseases 0.000 abstract description 2
- 208000005384 Pneumocystis Pneumonia Diseases 0.000 abstract 1
- 206010073755 Pneumocystis jirovecii pneumonia Diseases 0.000 abstract 1
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 508
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 155
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 143
- 238000000921 elemental analysis Methods 0.000 description 120
- 239000011734 sodium Substances 0.000 description 92
- 230000002829 reductive effect Effects 0.000 description 90
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 85
- 239000000243 solution Substances 0.000 description 83
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 78
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 78
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 77
- 235000019341 magnesium sulphate Nutrition 0.000 description 77
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 56
- 229910052739 hydrogen Inorganic materials 0.000 description 56
- 239000012044 organic layer Substances 0.000 description 51
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
- 239000011541 reaction mixture Substances 0.000 description 47
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 42
- 239000000706 filtrate Substances 0.000 description 38
- 238000001914 filtration Methods 0.000 description 37
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 35
- 239000012267 brine Substances 0.000 description 33
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 33
- 238000003756 stirring Methods 0.000 description 32
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 31
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 30
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 29
- 239000002904 solvent Substances 0.000 description 29
- UCGKVWNBKILEDM-UHFFFAOYSA-N C1=CC=C2[N+]([O-])=NNC2=C1 Chemical compound C1=CC=C2[N+]([O-])=NNC2=C1 UCGKVWNBKILEDM-UHFFFAOYSA-N 0.000 description 27
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- 239000002253 acid Substances 0.000 description 27
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 25
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 25
- 239000002244 precipitate Substances 0.000 description 23
- 239000000725 suspension Substances 0.000 description 22
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 22
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 19
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 18
- 238000004440 column chromatography Methods 0.000 description 18
- 229940095102 methyl benzoate Drugs 0.000 description 18
- 238000010992 reflux Methods 0.000 description 18
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 17
- 125000005447 octyloxy 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])O* 0.000 description 17
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 17
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 16
- 239000008188 pellet Substances 0.000 description 16
- 239000000843 powder Substances 0.000 description 16
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 13
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 13
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 12
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 11
- 239000005711 Benzoic acid Substances 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 235000010233 benzoic acid Nutrition 0.000 description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- 238000001816 cooling Methods 0.000 description 9
- 125000005446 heptyloxy 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])O* 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 239000007858 starting material Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 8
- 125000005605 benzo group Chemical group 0.000 description 8
- 239000000499 gel Substances 0.000 description 8
- 125000004284 isoxazol-3-yl group Chemical group [H]C1=C([H])C(*)=NO1 0.000 description 8
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 8
- 239000000741 silica gel Substances 0.000 description 8
- 229910002027 silica gel Inorganic materials 0.000 description 8
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 7
- 238000004587 chromatography analysis Methods 0.000 description 7
- 238000010828 elution Methods 0.000 description 7
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 6
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 6
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 150000004702 methyl esters Chemical class 0.000 description 6
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 6
- 238000010898 silica gel chromatography Methods 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 5
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 5
- 239000000443 aerosol Substances 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 5
- 125000003104 hexanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- 125000001400 nonyl group Chemical group [H]C([*])([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])[H] 0.000 description 5
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- 239000011780 sodium chloride Substances 0.000 description 5
- 125000005425 toluyl group Chemical group 0.000 description 5
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
- 125000002877 alkyl aryl group Chemical group 0.000 description 4
- 239000012298 atmosphere Substances 0.000 description 4
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 4
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 4
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- MHYCRLGKOZWVEF-UHFFFAOYSA-N ethyl acetate;hydrate Chemical compound O.CCOC(C)=O MHYCRLGKOZWVEF-UHFFFAOYSA-N 0.000 description 4
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 4
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- 239000003456 ion exchange resin Substances 0.000 description 4
- 229920003303 ion-exchange polymer Polymers 0.000 description 4
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- 229910052749 magnesium Inorganic materials 0.000 description 4
- 125000002757 morpholinyl group Chemical group 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
- 150000002923 oximes Chemical class 0.000 description 4
- 239000002304 perfume Substances 0.000 description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 description 4
- 239000012312 sodium hydride Substances 0.000 description 4
- 229910000104 sodium hydride Inorganic materials 0.000 description 4
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 3
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- 238000002329 infrared spectrum Methods 0.000 description 1
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- 238000002347 injection Methods 0.000 description 1
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- 125000000400 lauroyl group Chemical group O=C([*])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])C([H])([H])[H] 0.000 description 1
- JILPJDVXYVTZDQ-UHFFFAOYSA-N lithium methoxide Chemical compound [Li+].[O-]C JILPJDVXYVTZDQ-UHFFFAOYSA-N 0.000 description 1
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- 125000002960 margaryl group Chemical group [H]C([*])([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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
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- KSQITGOTJMYVHT-UHFFFAOYSA-N methyl 3-[4-(4-heptylphenyl)phenyl]propanoate Chemical compound C1=CC(CCCCCCC)=CC=C1C1=CC=C(CCC(=O)OC)C=C1 KSQITGOTJMYVHT-UHFFFAOYSA-N 0.000 description 1
- SSKROZKPITVKMK-UHFFFAOYSA-N methyl 4-(1-heptylpyrazol-4-yl)benzoate Chemical compound C1=NN(CCCCCCC)C=C1C1=CC=C(C(=O)OC)C=C1 SSKROZKPITVKMK-UHFFFAOYSA-N 0.000 description 1
- OSEDFBIVKALVNN-UHFFFAOYSA-N methyl 4-(c-chloro-n-hydroxycarbonimidoyl)benzoate Chemical compound COC(=O)C1=CC=C(C(Cl)=NO)C=C1 OSEDFBIVKALVNN-UHFFFAOYSA-N 0.000 description 1
- HGVBEQHEDXPHBI-UHFFFAOYSA-N methyl 4-(hydrazinecarbonyl)benzoate Chemical compound COC(=O)C1=CC=C(C(=O)NN)C=C1 HGVBEQHEDXPHBI-UHFFFAOYSA-N 0.000 description 1
- VVHXCSFDEMZQFY-UHFFFAOYSA-N methyl 4-(hydroxyiminomethyl)benzoate Chemical compound COC(=O)C1=CC=C(C=NO)C=C1 VVHXCSFDEMZQFY-UHFFFAOYSA-N 0.000 description 1
- WNYDFMUZTKXZNM-UHFFFAOYSA-N methyl 4-[(decanoylamino)carbamoyl]benzoate Chemical compound CCCCCCCCCC(=O)NNC(=O)C1=CC=C(C(=O)OC)C=C1 WNYDFMUZTKXZNM-UHFFFAOYSA-N 0.000 description 1
- RUTXRPSNXSBXSF-UHFFFAOYSA-N methyl 4-[[(4-hexoxybenzoyl)amino]carbamoyl]benzoate Chemical compound C1=CC(OCCCCCC)=CC=C1C(=O)NNC(=O)C1=CC=C(C(=O)OC)C=C1 RUTXRPSNXSBXSF-UHFFFAOYSA-N 0.000 description 1
- CVXXHXPNTZBZEL-UHFFFAOYSA-N methyl 4-carbonochloridoylbenzoate Chemical compound COC(=O)C1=CC=C(C(Cl)=O)C=C1 CVXXHXPNTZBZEL-UHFFFAOYSA-N 0.000 description 1
- IVYQLXCACCEQHM-UHFFFAOYSA-N methyl 4-hexoxybenzoate Chemical compound CCCCCCOC1=CC=C(C(=O)OC)C=C1 IVYQLXCACCEQHM-UHFFFAOYSA-N 0.000 description 1
- MPUYLLIQJZUWBZ-UHFFFAOYSA-N methyl 6-(8-bromooctoxy)naphthalene-2-carboxylate Chemical compound C1=C(OCCCCCCCCBr)C=CC2=CC(C(=O)OC)=CC=C21 MPUYLLIQJZUWBZ-UHFFFAOYSA-N 0.000 description 1
- WPRSDVPSRCCIEQ-UHFFFAOYSA-N methyl 6-(8-methoxyoctoxy)naphthalene-2-carboxylate Chemical compound C1=C(C(=O)OC)C=CC2=CC(OCCCCCCCCOC)=CC=C21 WPRSDVPSRCCIEQ-UHFFFAOYSA-N 0.000 description 1
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- 244000005700 microbiome Species 0.000 description 1
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- XONPDZSGENTBNJ-UHFFFAOYSA-N molecular hydrogen;sodium Chemical compound [Na].[H][H] XONPDZSGENTBNJ-UHFFFAOYSA-N 0.000 description 1
- 125000001419 myristoyl group Chemical group O=C([*])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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- XPIHNCHVIZFNFJ-UHFFFAOYSA-N n'-hydroxy-4-octoxybenzenecarboximidamide Chemical compound CCCCCCCCOC1=CC=C(C(=N)NO)C=C1 XPIHNCHVIZFNFJ-UHFFFAOYSA-N 0.000 description 1
- UHAAFJWANJYDIS-UHFFFAOYSA-N n,n'-diethylmethanediimine Chemical compound CCN=C=NCC UHAAFJWANJYDIS-UHFFFAOYSA-N 0.000 description 1
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- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
- FMASTMURQSHELY-UHFFFAOYSA-N n-(4-fluoro-2-methylphenyl)-3-methyl-n-[(2-methyl-1h-indol-4-yl)methyl]pyridine-4-carboxamide Chemical compound C1=CC=C2NC(C)=CC2=C1CN(C=1C(=CC(F)=CC=1)C)C(=O)C1=CC=NC=C1C FMASTMURQSHELY-UHFFFAOYSA-N 0.000 description 1
- JVHPKYBRJQNPAT-UHFFFAOYSA-N n-cyclohexyl-2,2-diphenylethenimine Chemical compound C1CCCCC1N=C=C(C=1C=CC=CC=1)C1=CC=CC=C1 JVHPKYBRJQNPAT-UHFFFAOYSA-N 0.000 description 1
- NNKPHNTWNILINE-UHFFFAOYSA-N n-cyclopropyl-3-fluoro-4-methyl-5-[3-[[1-[2-[2-(methylamino)ethoxy]phenyl]cyclopropyl]amino]-2-oxopyrazin-1-yl]benzamide Chemical compound CNCCOC1=CC=CC=C1C1(NC=2C(N(C=3C(=C(F)C=C(C=3)C(=O)NC3CC3)C)C=CN=2)=O)CC1 NNKPHNTWNILINE-UHFFFAOYSA-N 0.000 description 1
- 125000004998 naphthylethyl group Chemical group C1(=CC=CC2=CC=CC=C12)CC* 0.000 description 1
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- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000001196 nonadecyl group Chemical group [H]C([*])([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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002801 octanoyl group Chemical group C(CCCCCCC)(=O)* 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 125000002958 pentadecyl group Chemical group [H]C([*])([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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- WEYVCQFUGFRXOM-UHFFFAOYSA-N perazine Chemical compound C1CN(C)CCN1CCCN1C2=CC=CC=C2SC2=CC=CC=C21 WEYVCQFUGFRXOM-UHFFFAOYSA-N 0.000 description 1
- 229960002195 perazine Drugs 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 1
- CEMSSDOOIJDOBQ-UHFFFAOYSA-N phenyl n-(4-octylphenyl)carbamate Chemical compound C1=CC(CCCCCCCC)=CC=C1NC(=O)OC1=CC=CC=C1 CEMSSDOOIJDOBQ-UHFFFAOYSA-N 0.000 description 1
- CMPQUABWPXYYSH-UHFFFAOYSA-N phenyl phosphate Chemical compound OP(O)(=O)OC1=CC=CC=C1 CMPQUABWPXYYSH-UHFFFAOYSA-N 0.000 description 1
- 125000001129 phenylbutoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000004346 phenylpentyl group Chemical group C1(=CC=CC=C1)CCCCC* 0.000 description 1
- 125000004344 phenylpropyl group Chemical group 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 229940081066 picolinic acid Drugs 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 239000003361 porogen Substances 0.000 description 1
- 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
- 159000000001 potassium salts Chemical class 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 238000002953 preparative HPLC Methods 0.000 description 1
- OGHBATFHNDZKSO-UHFFFAOYSA-N propan-2-olate Chemical compound CC(C)[O-] OGHBATFHNDZKSO-UHFFFAOYSA-N 0.000 description 1
- IVRIRQXJSNCSPQ-UHFFFAOYSA-N propan-2-yl carbonochloridate Chemical compound CC(C)OC(Cl)=O IVRIRQXJSNCSPQ-UHFFFAOYSA-N 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- DSNYFFJTZPIKFZ-UHFFFAOYSA-N propoxybenzene Chemical group CCCOC1=CC=CC=C1 DSNYFFJTZPIKFZ-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UORVCLMRJXCDCP-UHFFFAOYSA-N propynoic acid Chemical compound OC(=O)C#C UORVCLMRJXCDCP-UHFFFAOYSA-N 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000004289 pyrazol-3-yl group Chemical group [H]N1N=C(*)C([H])=C1[H] 0.000 description 1
- 125000003072 pyrazolidinyl group Chemical group 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000004366 reverse phase liquid chromatography Methods 0.000 description 1
- XIIOFHFUYBLOLW-UHFFFAOYSA-N selpercatinib Chemical compound OC(COC=1C=C(C=2N(C=1)N=CC=2C#N)C=1C=NC(=CC=1)N1CC2N(C(C1)C2)CC=1C=NC(=CC=1)OC)(C)C XIIOFHFUYBLOLW-UHFFFAOYSA-N 0.000 description 1
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- SUBJHSREKVAVAR-UHFFFAOYSA-N sodium;methanol;methanolate Chemical compound [Na+].OC.[O-]C SUBJHSREKVAVAR-UHFFFAOYSA-N 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 125000003696 stearoyl group Chemical group O=C([*])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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- DHCDFWKWKRSZHF-UHFFFAOYSA-N sulfurothioic S-acid Chemical compound OS(O)(=O)=S DHCDFWKWKRSZHF-UHFFFAOYSA-N 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- AKYPBZWRIQWWIO-SANMLTNESA-N tert-butyl (3s)-7-octoxy-3-(3-oxidobenzotriazol-3-ium-1-carbonyl)-3,4-dihydro-1h-isoquinoline-2-carboxylate Chemical compound N1=[N+]([O-])C2=CC=CC=C2N1C(=O)[C@@H]1CC2=CC=C(OCCCCCCCC)C=C2CN1C(=O)OC(C)(C)C AKYPBZWRIQWWIO-SANMLTNESA-N 0.000 description 1
- YEHWSWXESXPBOS-UHFFFAOYSA-N tert-butyl 4-(4-hydroxyphenyl)piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1C1=CC=C(O)C=C1 YEHWSWXESXPBOS-UHFFFAOYSA-N 0.000 description 1
- JSBPGDXOXSDAFB-UHFFFAOYSA-N tert-butyl 4-(4-octoxyphenyl)piperazine-1-carboxylate Chemical compound C1=CC(OCCCCCCCC)=CC=C1N1CCN(C(=O)OC(C)(C)C)CC1 JSBPGDXOXSDAFB-UHFFFAOYSA-N 0.000 description 1
- GYFFHWLYRIUEKJ-UHFFFAOYSA-N tert-butyl 4-[4-(5-oxo-1h-1,2,4-triazol-4-yl)phenyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1C1=CC=C(N2C(NN=C2)=O)C=C1 GYFFHWLYRIUEKJ-UHFFFAOYSA-N 0.000 description 1
- FIRYGSLIQPPZFE-UHFFFAOYSA-N tert-butyl 4-[4-(hydrazinecarbonylamino)phenyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1C1=CC=C(NC(=O)NN)C=C1 FIRYGSLIQPPZFE-UHFFFAOYSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 125000005247 tetrazinyl group Chemical group N1=NN=NC(=C1)* 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([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])C([H])([H])C([H])([H])[H] 0.000 description 1
- NHDIQVFFNDKAQU-UHFFFAOYSA-N tripropan-2-yl borate Chemical compound CC(C)OB(OC(C)C)OC(C)C NHDIQVFFNDKAQU-UHFFFAOYSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 229960003986 tuaminoheptane Drugs 0.000 description 1
- 238000010267 two-fold dilution method Methods 0.000 description 1
- 125000000297 undecanoyl group Chemical group O=C([*])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])[H] 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([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])[H] 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/50—Cyclic peptides containing at least one abnormal peptide link
- C07K7/54—Cyclic peptides containing at least one abnormal peptide link with at least one abnormal peptide link in the ring
- C07K7/56—Cyclic peptides containing at least one abnormal peptide link with at least one abnormal peptide link in the ring the cyclisation not occurring through 2,4-diamino-butanoic acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
- A61K38/12—Cyclic peptides, e.g. bacitracins; Polymyxins; Gramicidins S, C; Tyrocidins A, B or C
-
- 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
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Biophysics (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Biochemistry (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Gastroenterology & Hepatology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Epidemiology (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Peptides Or Proteins (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Abstract
Description
Claims (1)
- 【特許請求の範囲】 1.次の一般式のポリペプチド化合物およびその医薬として許容しうる塩: 式中、R1は、少なくとも1個の窒素原子を含有し、1個以上の適当な置換基を 有していてもよい不飽和6員複素単環基で置換された低級アルカノイル; 1個以上の適当な置換基を有していてもよい1,2,3,4−テトラヒドロイソ キノリンで置換された低級アルカノイル; 少なくとも1個の酸素原子を含有し、1個以上の適当な置換基を有していても よい不飽和縮合複素環基で置換された低級アルカノイル; 1〜3個の硫黄原子を含有し、1個以上の適当な置換基を有していてもよい不 飽和縮合複素環基で置換された低級アルカノイル; 2個以上の窒素原子を含有し、1個以上の適当な置換基を有していてもよい不 飽和縮合複素環基で置換された低級アルカノイル; 少なくとも1個の窒素原子を含有し、1個以上の適当な置換基を有していても よい飽和3〜8員複素単環基で置換された低級アルカノイル; 1個以上の適当な置換基を有していてもよいアリールで置換されたアル低級ア ルケノイル; 1個以上の高級アルコキシを有していてもよいナフチル低級アルケノイル; 1個以上の適当な置換基を有していてもよい低級アルキノイル; 高級アルコキシを有するナフチルで置換された(C2〜C6)アルカノイル; 1個以上の適当な置換基を有するアリールで置換され、1個以上の適当な置換 基を有していてもよいアル(C2〜C6)アルカノイル; 1個以上の適当な置換基を有していてもよい複素環基で置換され、1個以上の 適当な置換基を有していてもよいアロイル; 複素環部分が1個以上の適当な置換基を有していてもよい複素環高級アルコキ シを有するアリールで置換されたアロイル; 低級アルコキシ高級アルコキシを有するアリールで置換されたアロイル; 低級アルケニル低級アルコキシを有するアリールで置換されたアロイル; 2個の低級アルコキシで置換されたアロイル; 低級アルキルを有するアリールで置換されたアロイル; 高級アルキルを有するアリールで置換されたアロイル; 1個以上の適当な置換基を有していてもよいアリールオキシ低級アルカノイル ; 1個以上の適当な置換基を有していてもよいアル低級アルコキシ低級アルカノ イル; 1個以上の適当な置換基を有していてもよいアリールアミノ低級アルカノイル ; 低級アルキルと高級アルコキシを有するアリールとを有するピラゾリルで置換 された低級アルカノイル; 高級アルカノイル部分が1個以上の適当な置換基を有していてもよい低級アル コキシ高級アルカノイル; 1個以上の適当な置換基を有していてもよい複素環オキシを有するアリールで 置換されたアロイル; 低級アルキルを有するシクロ低級アルキルで置換されたアロイル; 高級アルキルを有するインドリルカルボニル; 低級アルキルを有するナフトイル; 高級アルキルを有するナフトイル; 低級アルコキシ高級アルコキシを有するナフトイル; 低級アルコキシ低級アルコキシ高級アルコキシを有するアリールで置換された アロイル; 低級アルコキシ低級アルコキシを有するアリールで置換されたアロイル; 低級アルコキシを有するアリールを有するアリールで置換されたアロイル; 低級アルコキシ低級アルコキシを有するアリールを有するアリールで置換され たアロイル; 複素環オキシ高級アルコキシを有するアリールで置換されたアロイル; アリールオキシ低級アルコキシを有するアリールで置換されたアロイル; 複素環カルボニル高級アルコキシを有するアリールで置換されたアロイル; 高級アルコキシを有するアリールを有するオキサゾリルで置換された低級アル カノイル; 低級アルコキシを有するアリールで置換されたアリールを有するフリルで置換 された低級アルカノイル; オキソと高級アルキルを有するアリールとを有するトリアゾリルで置換された 低級アルカノイル; ヒドロキシを有する高級アルカノイル; アル低級アルキルおよびヒドロキシを有する高級アルカノイル; 3−メチルトリデセノイル;または 高級アルコキシを有するアリールで置換され、アミノまたは保護されたアミノ を有していてもよい(C2〜C6)アルカノイルである。 2.請求の範囲第1項の化合物であって、 R1が、少なくとも1個の窒素原子を含有し、低級アルコキシ、高級アルコキ シ、低級アルキル、高級アルキル、高級アルコキシ低級アルキル、低級アルコキ シを有するフェニル、高級アルコキシを有するフェニル、低級アルコキシを有す るナフチル、高級アルコキシを有するナフチル、低級アルキルを有するフェニル 、高級アルキルを有するフェニル、高級アルコキシを有するナフトイル、低級ア ルキルを有するフェニルで置換されたフェニル、少なくとも1個の窒素原子を 含有し、高級アルコキシを有するフェニルを有していてもよい3〜8員飽和複素 単環基、低級アルコキシを有するフェニルで置換されたフェニル、少なくとも1 個の窒素原子を含有し、低級アルコキシ高級アルコキシを有するフェニルを有し ていてもよい3〜8員飽和複素単環基、少なくとも1個の窒素原子を含有し、低 級アルコキシを有するフェニルを有していてもよい3〜8員飽和複素単環基およ びオキソからなる群から選ばれた1〜3個の置換基を有していてもよい不飽和6 員複素単環基で置換された低級アルカノイル; 高級アルコキシおよび低級アルコキシカルボニルを有する1,2,3,4−テト ラヒドロイソキノリンで置換された低級アルカノイル; 少なくとも1個の酸素原子を含有し、低級アルコキシ、高級アルコキシ、低級 アルキル、高級アルキル、高級アルコキシ低級アルキル、低級アルコキシを有す るフェニル、高級アルコキシを有するフェニル、低級アルコキシを有するナフチ ル、高級アルコキシを有するナフチル、低級アルキルを有するフェニル、高級ア ルキルを有するフェニル、高級アルコキシを有するナフトイル、低級アルキルを 有するフェニルで置換されたフェニル、少なくとも1個の窒素原子を含有し、高 級アルコキシを有していてもよい不飽和6員複素単環基およびオキソからなる群 から選ばれた1〜3個の置換基を有していてもよい不飽和縮合複素環基で置換さ れた低級アルカノイル; 1〜3個の硫黄原子を含有し、低級アルコキシ、高級アルコキシ、低級アルキ ル、高級アルキル、高級アルコキシ低級アルキル、低級アルコキシを有するフェ ニル、高級アルコキシを有するフェニル、低級アルコキシを有するナフチル、高 級アルコキシを有するナフチル、低級アルキルを有するフェニル、高級アルキル を有するフェニル、高級アルコキシを有するナフトイル、低級アルキルを有する フェニルで置換されたフェニルおよびオキソからなる群から選ばれた1〜3個の 置換基を有していてもよい不飽和縮合複素環基で置換された低級アルカノイル; 2個以上の窒素原子を含有し、低級アルコキシ、高級アルコキシ、低級アルキ ル、高級アルキル、高級アルコキシ低級アルキル、低級アルコキシを有するフェ ニル、高級アルコキシを有するフェニル、低級アルコキシを有するナフチル、高 級アルコキシを有するフェニル、低級アルキルを有するフェニル、高級アルキル を有するフェニル、高級アルコキシを有するナフトイル、低級アルキルを有する フェニルで置換されたフェニルおよびオキソからなる群から選ばれた1〜3個の 置換基を有していてもよい不飽和縮合複素環基で置換された低級アルカノイル; または、 少なくとも1個の窒素原子を含有し、低級アルコキシ、高級アルコキシ、低級 アルキル、高級アルキル、高級アルコキシ低級アルキル、低級アルコキシを有す るフェニル、高級アルコキシを有するフェニル、低級アルコキシを有するナフチ ル、高級アルコキシを有するナフチル、低級アルキルを有するフェニル、高級ア ルキルを有するフェニル、高級アルコキシを有するナフトイル、低級アルキルを 有するフェニルで置換されたフェニルおよびオキソからなる群から選ばれた1〜 3個の置換基を有していてもよい飽和3〜8員複素単環基で置換された低級アル カノイルである化合物。 3.請求の範囲第1項の化合物であって、 R1が、低級アルコキシ、高級アルコキシ、低級アルキル、高級アルキル、高 級アルコキシ低級アルキル、低級アルコキシを有するフェニル、高級アルコキシ を有するフェニル、低級アルコキシを有するナフチル、高級アルコキシを有する ナフチル、低級アルキルを有するフェニル、高級アルキルを有するフェニル、高 級アルコキシを有するナフトイル、低級アルキルを有するフェニルで置換された フェニル、低級アルコキシ低級アルキル、ハロ低級アルコキシ、低級アルケニル オキシ、ハロ高級アルコキシ、低級アルコキシ高級アルコキシおよびオキソから なる群から選ばれた1〜3個の置換基を有していてもよいアリールで置換された アル低級アルケノイル; 1〜3個の高級アルコキシを有していてもよいナフチル低級アルケノイル; 低級アルコキシ、高級アルコキシ、低級アルキル、高級アルキル、高級アルコ キシ低級アルキル、低級アルコキシを有するフェニル、高級アルコキシを有する フェニル、低級アルコキシを有するナフチル、高級アルコキシを有するナフチル 、低級アルキルを有するフェニル、高級アルキルを有するフェニル、高級アルコ キシを有するナフトイル、低級アルキルを有するフェニルで置換されたフェニ ルおよびオキソからなる群から選ばれた1〜3個の置換基を有していてもよい低 級アルキノイル; 低級アルコキシ、高級アルコキシ、低級アルキル、高級アルキル、高級アルコ キシ低級アルキル、低級アルコキシを有するフェニル、高級アルコキシを有する フェニル、低級アルコキシを有するナフチル、高級アルコキシを有するナフチル 、低級アルキルを有するフェニル、高級アルキルを有するフェニル、高級アルコ キシを有するナフトイル、低級アルキルを有するフェニルで置換されたフェニル 、低級アルコキシ低級アルコキシを有するフェニルおよびオキソからなる群から 選ばれた1〜3個の置換基を有するアリールで置換され、ヒドロキシ、オキソ、 保護されたアミノまたはアミノを有していてもよいアル(C2〜C6)アルカノイ ル;または、 高級アルコキシを有するナフチルで置換された(C2〜C6)アルカノイルであ る化合物。 4.請求の範囲第1項の化合物であって、 R1が、低級アルコキシ、高級アルコキシ、低級アルキル、高級アルキル、高 級アルコキシ低級アルキル、低級アルコキシを有するフェニル、高級アルコキシ を有するフェニル、低級アルコキシを有するナフチル、高級アルコキシを有する ナフチル、低級アルキルを有するフェニル、高級アルキルを有するフェニル、高 級アルコキシを有するナフトイル、低級アルキルを有するフェニルで置換された フェニル、低級アルコキシ高級アルコキシを有するフェニル、高級アルケニルオ キシを有するフェニル、低級アルコキシを有するフェニルで置換された複素環基 、複素環基、フェニルを有するシクロ低級アルキル、シクロ低級アルキルを有す るフェニル、低級アルキルおよびオキソを有する複素環基で置換されたフェニル 、低級アルキルを有するシクロ低級アルキル、低級アルコキシを有するフェニル で置換されたフェニル、複素環基を有するフェニルおよびオキソからなる群から 選ばれた1〜3個の置換基を有していてもよい複素環基で置換され、ハロゲンを 有していてもよいアロイル; 複素環基が低級アルキルを有していてもよい複素環高級アルコキシを有するア リールで置換されたアロイル; 低級アルコキシ高級アルコキシを有するアリールで置換されたアロイル; 低級アルケニル低級アルコキシを有するアリールで置換されたアロイル; 2個の低級アルコキシで置換されたアロイル; 低級アルキルを有するアリールで置換されたアロイル;または、 高級アルキルを有するアリールで置換されたアロイルである化合物。 5.請求の範囲第1項の化合物であって、 R1が、低級アルコキシ、高級アルコキシ、低級アルキル、高級アルキル、高 級アルコキシ低級アルキル、低級アルコキシを有するフェニル、高級アルコキシ を有するフェニル、低級アルコキシを有するナフチル、高級アルコキシを有する ナフチル、低級アルキルを有するフェニル、高級アルキルを有するフェニル、高 級アルコキシを有するナフトイル、低級アルキルを有するフェニルで置換された フェニルおよびオキソからなる群から選ばれた1〜3個の置換基を有していても よいアリールオキシ低級アルカノイル; 低級アルコキシ、高級アルコキシ、低級アルキル、高級アルキル、高級アルコ キシ低級アルキル、低級アルコキシを有するフェニル、高級アルコキシを有する フェニル、低級アルコキシを有するナフチル、高級アルコキシを有するナフチル 、低級アルキルを有するフェニル、高級アルキルを有するフェニル、高級アルコ キシを有するナフトイル、低級アルキルを有するフェニルで置換されたフェニル およびオキソからなる群から選ばれた1〜3個の置換基を有していてもよいアル 低級アルコキシ低級アルカノイル;または、 低級アルコキシ、高級アルコキシ、低級アルキル、高級アルキル、高級アルコ キシ低級アルキル、低級アルコキシを有するフェニル、高級アルコキシを有する フェニル、低級アルコキシを有するナフチル、高級アルコキシを有するナフチル 、低級アルキルを有するフェニル、高級アルキルを有するフェニル、高級アルコ キシを有するナフトイル、低級アルキルを有するフェニルで置換されたフェニル およびオキソからなる群から選ばれた1〜3個の置換基を有していてもよいアリ ールアミノ低級アルカノイルである化合物。 6.請求の範囲第1項の化合物であって、 R1が、低級アルキルと高級アルコキシを有するアリールとを有するピラゾー ルで置換された低級アルカノイル; 高級アルカノイル部分がアミノまたは保護されたアミノを有していてもよい低 級アルコキシ高級アルカノイル; フェニルを有していてもよい複素環オキシを有するアリールで置換されたアロ イル; 低級アルキルを有するシクロ低級アルキルで置換されたアロイル; 高級アルキルを有するインドリルカルボニル; 低級アルキルを有するナフトイル; 高級アルキルを有するナフトイル; 低級アルコキシ高級アルコキシを有するナフトイル; 低級アルコキシ低級アルコキシ高級アルコキシを有するアリールで置換された アロイル; 低級アルコキシ低級アルコキシを有するアリールで置換されたアロイル; 低級アルコキシを有するフェニルを有するアリールで置換されたアロイル; 低級アルコキシ低級アルコキシを有するフェニルを有するアリールで置換され たアロイル; 複素環高級アルコキシを有するアリールで置換されたアロイル; フェノキシ低級アルコキシを有するアリールで置換されたアロイル; 複素環カルボニル高級アルコキシを有するアリールで置換されたアロイル; 高級アルコキシを有するアリールを有するオキサゾリルで置換された低級アル カノイル; 低級アルコキシを有するフェニルで置換されたアリールを有するフリルで置換 された低級アルカノイル; オキソと高級アルキルを有するフェニルとを有するトリアゾリルで置換された 低級アルカノイル; ヒドロキシを有する高級アルカノイル; ベンジルおよびヒドロキシを有する高級アルカノイル; 3−メチルトリデセノイル;または、 高級アルコキシを有するアリールで置換されており、アミノまたは保護された アミノを有していてもよい(C2〜C6)アルカノイルである化合物。 7.請求の範囲第2項の化合物であって、 R1が、各々に、高級アルコキシ、高級アルコキシ低級アルキル、高級アルコ キシを有するフェニル、低級アルコキシを有するフェニルで置換されたフェニル 、高級アルコキシを有するフェニルで置換されたピペラジニル、低級アルコキシ 高級アルコキシを有するフェニルで置換されたピペラジニルおよび低級アルコキ シを有するフェニルで置換されたピペラジニルからなる群から選ばれた1〜3個 の置換基を有していてもよいピリジルまたはピリダジニルで置換された低級アル カノイル; 高級アルコキシおよび低級アルコキシカルボニルを有する1,2,3,4−テト ラヒドロイソキノリンで置換された低級アルカノイル; 高級アルコキシおよびオキソからなる群から選ばれた1〜3個の置換基を有し ていてもよいクマリンで置換された低級アルカノイル; 1〜3個の高級アルコキシを有していてもよいベンゾチオフェニルで置換され た低級アルカノイル; 高級アルコキシおよび低級アルキルからなる群から選ばれた1〜3個の置換基 を有していてもよいベンゾ[b]フラニルで置換された低級アルカノイル; 高級アルキル、低級アルコキシを有するフェニル、低級アルキルを有するフェ ニルで置換されたフェニルおよび高級アルコキシを有するピリジルからなる群か ら選ばれた1〜3個の置換基を有していてもよいベンゾオキサゾリルで置換され た低級アルカノイル; 高級アルキル、および低級アルコキシを有するフェニルからなる群から選ばれ た1〜3個の置換基を有していてもよいベンゾイミダゾリルで置換された低級ア ルカノイル;または、 各々に、高級アルコキシを有するフェニルおよび高級アルコキシを有するナフ トイルからなる群から選ばれた1〜3個の置換基を有していてもよいピペリジル またはピペラジニルで置換された低級アルカノイルである化合物。 8.請求の範囲第3項の化合物であって、 R1が、低級アルコキシ、低級アルキル、高級アルキル、低級アルコキシ低級 アルキル、ハロ低級アルコキシ、低級アルケニルオキシ、ハロ高級アルコキシお よび低級アルコキシ高級アルコキシからなる群から選ばれた1〜3個の置換基を 有していてもよいフェニルで置換されたフェニル低級アルケノイル; 1〜3個の高級アルコキシを有していてもよいナフチル低級アルケノイル; 高級アルコキシを有するナフチル、および低級アルキルを有するフェニルで置 換されたフェニルからなる群から選ばれた1〜3個の置換基を有していてもよい 低級アルキノイル; 低級アルコキシ、高級アルコキシ、低級アルキル、高級アルキル、および低級 アルコキシ低級アルキルを有するフェニルからなる群から選ばれた1〜3個の置 換基を有するフェニルで置換されており、ヒドロキシ、オキソ、保護されたアミ ノまたはアミノを有していてもよいフェニル(C2〜C6)アルカノイル;または 、 高級アルコキシを有するナフチルで置換された(C2〜C6)アルカノイルであ る化合物。 9.請求の範囲第4項の化合物であって、 R1が、少なくとも1個の窒素原子を含有し、フェニル、低級アルコキシを有 するフェニル、高級アルコキシを有するフェニル、低級アルキルを有するフェニ ル、低級アルコキシ高級アルコキシを有するフェニル、高級アルケニルオキシを 有するフェニル、低級アルコキシを有するフェニルで置換されたピペリジル、ピ ペリジル、フェニルを有するシクロ低級アルキル、シクロ低級アルキルを有する フェニルならびにオキソおよび低級アルキルを有するトリアゾリルで置換された フェニルからなる群から選ばれた1〜3個の置換基を有していてもよい飽和6員 複素単環基で置換されており、ハロゲンを有していてもよいベンゾイル; 1〜2個の酸素原子と1〜3個の窒素原子とを含有し、高級アルキル、低級ア ルコキシを有するフェニル、高級アルコキシを有するフェニル、低級アルコキシ 高級アルコキシを有するフェニル、および低級アルコキシを有するフェニルで置 換されたフェニルからなる群から選ばれた1〜3個の置換基を有していてもよい 不飽和5員複素単環基で置換されたベンゾイル; 1または2個の窒素原子を含有し、高級アルキル、および低級アルコキシを有 するフェニルからなる群から選ばれた1〜3個の置換基を有していてもよい5ま た6員複素単環基で置換されたベンゾイル; 1〜2個の窒素原子と1〜2個の硫黄原子とを含有し、低級アルコキシを有す るフェニル、高級アルコキシを有するフェニル、低級アルキルを有するシクロ低 級アルキル、低級アルコキシを有するフェニルで置換されたフェニル、シクロ低 級アルキルを有するフェニル、ピペリジンを有するフェニルおよび低級アルコキ シ高級アルコキシを有するフェニルからなる群から選ばれた1〜3個の置換基を 有していてもよい5員複素単環基で置換されたベンゾイル; 少なくとも1個の窒素原子を含有する不飽和3〜8員複素単環基で置換された 高級アルコキシを有するフェニルで置換されたベンゾイル; 1〜2個の酸素原子と1〜3個の窒素原子とを含有し、低級アルキルを有して いてもよい飽和6員複素単環基で置換された高級アルコキシを有するフェニルで 置換されたベンゾイル; 低級アルコキシ高級アルコキシを有するフェニルで置換されたベンゾイル; 低級アルケニル低級アルコキシを有するフェニルで置換されたベンゾイル; 2個の低級アルコキシで置換されたベンゾイル; 低級アルキルを有するフェニルで置換されたベンゾイル;または、 高級アルキルを有するフェニルで置換されたベンゾイルである化合物。 10.請求の範囲第5項の化合物であって、 R1が、1〜3個の高級アルコキシを有していてもよいフェニルオキシ低級ア ルカノイル; 1〜3個の高級アルコキシを有していてもよいフェニル低級アルコキシ低級ア ルカノイル;または、 1〜3個の高級アルコキシを有していてもよいフェニルアミノ低級アルカノイ ルである化合物。 11.請求の範囲第1項の化合物であって、 R1が、低級アルコキシを有するフェニル、高級アルコキシを有するフェニル 、低級アルキルを有するフェニル、低級アルコキシ高級アルコキシを有するフェ ニル、高級アルケニルオキシを有するフェニル、低級アルコキシを有するフェニ ルで置換されたピペリジル、フェニルを有するシクロ低級アルキル、シクロ低級 アルキルを有するフェニルならびにオキソおよび低級アルキルを有するトリアゾ リルで置換されたフェニルからなる群から選ばれた1〜3個の置換基を有してい てもよいピペラジニルで置換され、ハロゲンを有していてもよいベンゾイル; 高級アルキル、低級アルコキシを有するフェニル、高級アルコキシを有するフ ェニル、低級アルコキシ高級アルコキシを有するフェニル、および低級アルコキ シを有するフェニルで置換されたフェニルからなる群から選ばれた1〜3個の置 換基を有していてもよいイソオキサゾリルで置換されたベンゾイル; 低級アルコキシ高級アルコキシを有するフェニルで置換されたベンゾイル; 低級アルキルを有するフェニルで置換されたベンゾイル; 高級アルキルを有するフェニルで置換されたベンゾイル; 低級アルコキシ、低級アルキル、高級アルキル、低級アルコキシ低級アルキル 、ハロ低級アルコキシ、低級アルケニルオキシ、ハロ高級アルコキシおよび低級 アルコキシ高級アルコキシからなる群から選ばれた1〜3個の置換基を有してい てもよいフェニルで置換されたフェニル低級アルケノイル; 低級アルコキシを有するフェニル、高級アルコキシを有するフェニル、低級ア ルキルを有するシクロ低級アルキル、低級アルコキシを有するフェニルで置換さ れたフェニル、シクロ低級アルキルを有するフェニル、ピペリジルを有するフェ ニル、および低級アルコキシ高級アルコキシを有するフェニルからなる群から選 ばれた1〜3個の置換基を有していてもよいチアジアゾリルで置換されたベ ンゾイル;または、 低級アルコキシを有するフェニル、高級アルコキシを有するフェニル、低級ア ルコキシ高級アルコキシを有するフェニル、高級アルキル、および低級アルコキ シを有するフェニルで置換されたフェニルからなる群から選ばれた1〜3個の置 換基を有していてもよいオキサジアゾリルで置換されたベンゾイルである化合物 。 12.請求の範囲第11項の化合物であって、 R1が、低級アルコキシ高級アルコキシを有するフェニルで置換されたベンゾ イル;または、 低級アルキルを有するフェニルで置換されたベンゾイルである化合物。 13.請求の範囲第11項の化合物であって、 R1が、低級アルコキシを有するフェニルを有していてもよいピペラジニルで 置換されたベンゾイル; 低級アルコキシを有するフェニルを有していてもよいイソオキサゾリルで置換 されたベンゾイル; 低級アルコキシ高級アルコキシを有するフェニルを有していてもよいチアジア ゾリルで置換されたベンゾイル;または、 低級アルコキシを有するフェニルを有していてもよいオキサジアゾリルで置換 されたベンゾイルである化合物。 14.請求の範囲第11項の化合物であって、 R1が、低級アルコキシを有していてもよいフェニルで置換されたフェニル低 級アルケノイルである化合物。 15.式[I] [式中、R1は、少なくとも1個の窒素原子を含有し、1個以上の適当な置換基 を有していてもよい不飽和6員複素単環基で置換された低級アルカノイル; 1個以上の適当な置換基を有していてもよい1,2,3,4−テトラヒドロイソ キノリンで置換された低級アルカノイル; 少なくとも1個の酸素原子を含有し、1個以上の適当な置換基を有していても よい不飽和縮合複素環基で置換された低級アルカノイル; 1〜3個の硫黄原子を含有し、1個以上の適当な置換基を有していてもよい不 飽和縮合複素環基で置換された低級アルカノイル; 2個以上の窒素原子を含有し、1個以上の適当な置換基を有していてもよい不 飽和縮合複素環基で置換された低級アルカノイル; 少なくとも1個の窒素原子を含有し、1個以上の適当な置換基を有していても よい飽和3〜8員複素単環基で置換された低級アルカノイル; 1個以上の適当な置換基を有していてもよいアリールで置換されたアル低級ア ルケノイル; 1個以上の高級アルコキシを有していてもよいナフチル低級アルケノイル; 1個以上の適当な置換基を有していてもよい低級アルキノイル; 高級アルコキシを有するナフチルで置換されたC2〜C6アルカノイル; 1個以上の適当な置換基を有するアリールで置換され、1個以上の適当な置換 基を有していてもよいアルC2〜C6アルカノイル; 1個以上の適当な置換基を有していてもよい複素環基で置換され、1個以上の 適当な置換基を有していてもよいアロイル; 複素環部分から1個以上の適当な置換基を有していてもよい複素環高級アルコ キシを有するアリールで置換されたアロイル; 低級アルコキシ高級アルコキシを有するアリールで置換されたアロイル; 低級アルケニル低級アルコキシを有するアリールで置換されたアロイル; 2個の低級アルコキシで置換されたアロイル; 低級アルキルを有するアリールで置換されたアロイル; 高級アルキルを有するアリールで置換されたアロイル; 1個以上の適当な置換基を有していてもよいアリールオキシ低級アルカノイル ; 1個以上の適当な置換基を有していてもよいアル低級アルコキシ低級アルカノ イル; 1個以上の適当な置換基を有していてもよいアリールアミノ低級アルカノイル ; 低級アルキルと高級アルコキシを有するアリールとを有するピラゾリルで置換 された低級アルカノイル; 高級アルカノイル部分が1個以上の適当な置換基を有していてもよい低級アル コキシ高級アルカノイル; 1個以上の適当な置換基を有していてもよい複素環オキシを有するアリールで 置換されたアロイル; 低級アルキルを有するシクロ低級アルキルで置換されたアロイル; 高級アルキルを有するインドリルカルボニル; 低級アルキルを有するナフトイル; 高級アルキルを有するナフトイル; 低級アルコキシ高級アルコキシを有するナフトイル; 低級アルコキシ低級アルコキシ高級アルコキシを有するアリールで置換された アロイル; 低級アルコキシ低級アルコキシを有するアリールで置換されたアロイル; 低級アルコキシを有するアリールを有するアリールで置換されたアロイル; 低級アルコキシ低級アルコキシを有するアリールを有するアリールで置換され たアロイル; 複素環オキシ高級アルコキシを有するアリールで置換されたアロイル; アリールオキシ低級アルコキシを有するアリールで置換されたアロイル; 複素環カルボニル高級アルコキシを有するアリールで置換されたアロイル; 高級アルコキシを有するアリールを有するオキサゾリルで置換された低級アル カノイル; 低級アルコキシを有するアリールで置換されたアリールを有するフリルで置換 された低級アルカノイル; オキソと高級アルキルを有するアリールとを有するトリアゾリルで置換された 低級アルカノイル; ヒドロキシを有する高級アルカノイル; アル低級アルキルおよびヒドロキシを有する高級アルカノイル; 3−メチルトリデセノイル;または 高級アルコキシを有するアリールで置換され、アミノまたは保護されたアミノ を有していてもよいC2〜C6アルカノイルである] のポリペプチド化合物およびその医薬として許容しうる塩の製造法であって、 1)式 の化合物またはそのアミノ基における反応性誘導体もしくはそれらの塩を、式 R1−OH [III] [ここに、R1は上に定義した通りである]の化合物またはそのカルボキシ基に おける反応性誘導体もしくはそれらの塩と反応させて、式 [ここに、R1は上に定義した通りである]の化合物[I]またはその塩を生成 させることを特徴とする該製造法。 16.請求の範囲第1項の化合物またはその医薬として許容しうる塩を有効成分と し、これを製薬上許容しうる担体または賦形剤との混合物の形で含有する医薬組 成物。 17.請求の範囲第1項の化合物またはその医薬として許容しうる塩の医薬として の使用。 18.医薬として使用するための請求の範囲第1項の化合物またはその医薬として 許容しうる塩。 19.請求の範囲第1項の化合物またはその医薬として許容しうる塩をヒトまたは 動物に投与することを特徴とする、病原微生物により惹起される感染症の予防的 および/または治療的処置方法。
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GB9420425A GB9420425D0 (en) | 1994-10-07 | 1994-10-07 | New compound |
GBGB9508745.8A GB9508745D0 (en) | 1995-04-28 | 1995-04-28 | New compound |
GB9508745.8 | 1995-04-28 | ||
PCT/JP1995/001983 WO1996011210A1 (en) | 1994-10-07 | 1995-09-29 | Cyclic hexapeptides having antibiotic activity |
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JP13675698A Expired - Lifetime JP3518665B2 (ja) | 1994-10-07 | 1998-05-19 | 抗微生物活性を有する新規環状ヘキサペプチド化合物 |
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EP (1) | EP0788511B1 (ja) |
JP (2) | JP2897427B2 (ja) |
KR (1) | KR100353303B1 (ja) |
CN (1) | CN1203089C (ja) |
AR (1) | AR041770A1 (ja) |
AT (1) | ATE229541T1 (ja) |
AU (1) | AU696949B2 (ja) |
BR (2) | BRPI9504791B8 (ja) |
CA (1) | CA2202058C (ja) |
DE (2) | DE69529172T2 (ja) |
DK (1) | DK0788511T3 (ja) |
ES (1) | ES2187575T3 (ja) |
FI (1) | FI119988B (ja) |
FR (1) | FR08C0028I2 (ja) |
HK (1) | HK1004136A1 (ja) |
HU (1) | HU228151B1 (ja) |
IL (1) | IL115484A (ja) |
LU (1) | LU91452I2 (ja) |
MX (1) | MX9702531A (ja) |
NL (1) | NL300352I2 (ja) |
NO (2) | NO328483B1 (ja) |
OA (1) | OA10475A (ja) |
PT (1) | PT788511E (ja) |
RU (1) | RU2165423C2 (ja) |
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WO (1) | WO1996011210A1 (ja) |
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1995
- 1995-09-29 US US08/809,723 patent/US6107458A/en not_active Expired - Lifetime
- 1995-09-29 RU RU97107338/04A patent/RU2165423C2/ru active Protection Beyond IP Right Term
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Cited By (10)
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JP2002363097A (ja) * | 1999-07-01 | 2002-12-18 | Fujisawa Pharmaceut Co Ltd | 安定化された凍結乾燥型医薬組成物 |
US6774104B1 (en) | 1999-07-01 | 2004-08-10 | Fujisawa Pharmaceutical Co., Ltd. | Stabilized pharmaceutical composition in lyophilized form |
US7112565B2 (en) | 1999-07-01 | 2006-09-26 | Astellas Pharma Inc. | Stabilized pharmaceutical composition in lyophilized form |
JP4691866B2 (ja) * | 1999-07-01 | 2011-06-01 | アステラス製薬株式会社 | 安定化された凍結乾燥型医薬組成物 |
WO2007043400A1 (ja) * | 2005-10-07 | 2007-04-19 | Kissei Pharmaceutical Co., Ltd. | 含窒素芳香族複素環化合物およびそれを含有する医薬組成物 |
JPWO2007043400A1 (ja) * | 2005-10-07 | 2009-04-16 | キッセイ薬品工業株式会社 | 含窒素芳香族複素環化合物およびそれを含有する医薬組成物 |
JP5222561B2 (ja) * | 2005-10-07 | 2013-06-26 | キッセイ薬品工業株式会社 | 含窒素芳香族複素環化合物およびそれを含有する医薬組成物 |
US8435999B2 (en) | 2007-08-13 | 2013-05-07 | Monsanto Technology Llc | Compositions and methods for controlling nematodes |
JP2017519043A (ja) * | 2014-05-29 | 2017-07-13 | シャンハイ テックウェル バイオファーマシューティカル カンパニー リミテッドShanghai Techwell Biopharmaceutical Co.,Ltd | シクロペプチド系化合物の溶媒和物およびその製造方法と使用 |
WO2020013116A1 (ja) * | 2018-07-10 | 2020-01-16 | 京都薬品工業株式会社 | Ptp-1b阻害剤およびその用途 |
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