TW200402419A - Novel compounds - Google Patents

Novel compounds Download PDF

Info

Publication number: TW200402419A
Authority: TW; Taiwan
Prior art keywords: methyl; formula; compound; substituted; group
Prior art date: 2002-03-28

Application number

TW092106767A

Other languages

English (en)

Chinese (zh)

Inventor

Rachael Ann Ancliff

Caroline Mary Cook

Colin David Eldred

Paul Martin Gore

Lee Andrew Harrison

Martin Gore Paul

Andrew Harrison Lee

Alistair Hayes Martin

Teanby Hodgson Simon

Bruce Judd Duncan

Elaine Keeling Suzanne

Michael Robertson Graeme

Swanson Stephen

John Walker Andrew

Wilkinson Mark

Original Assignee

Glaxo Group Ltd

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2002-03-28

Filing date

2003-03-26

Publication date

2004-02-16

2003-03-26 Application filed by Glaxo Group Ltd filed Critical Glaxo Group Ltd

2004-02-16 Publication of TW200402419A publication Critical patent/TW200402419A/zh

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 251
125000001072 heteroaryl group Chemical group 0.000 claims abstract description 43
150000003839 salts Chemical class 0.000 claims abstract description 32
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 21
239000012453 solvate Substances 0.000 claims abstract description 21
239000001257 hydrogen Substances 0.000 claims abstract description 19
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 14
125000003107 substituted aryl group Chemical group 0.000 claims abstract description 4
-1 pyrazol-4-yl Chemical group 0.000 claims description 165
239000000203 mixture Substances 0.000 claims description 115
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 65
238000000034 method Methods 0.000 claims description 57
125000000217 alkyl group Chemical group 0.000 claims description 40
125000004312 morpholin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC([H])(*)C1([H])[H] 0.000 claims description 39
125000006512 3,4-dichlorobenzyl group Chemical group [H]C1=C(Cl)C(Cl)=C([H])C(=C1[H])C([H])([H])* 0.000 claims description 23
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 21
239000002253 acid Substances 0.000 claims description 18
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 17
125000003277 amino group Chemical group 0.000 claims description 16
208000006673 asthma Diseases 0.000 claims description 14
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 11
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 10
OQLZINXFSUDMHM-UHFFFAOYSA-N Acetamidine Chemical compound CC(N)=N OQLZINXFSUDMHM-UHFFFAOYSA-N 0.000 claims description 10
235000019253 formic acid Nutrition 0.000 claims description 10
239000000126 substance Substances 0.000 claims description 10
239000000460 chlorine Substances 0.000 claims description 9
239000007822 coupling agent Substances 0.000 claims description 9
150000001412 amines Chemical class 0.000 claims description 8
125000006286 dichlorobenzyl group Chemical group 0.000 claims description 8
239000003814 drug Substances 0.000 claims description 8
230000004968 inflammatory condition Effects 0.000 claims description 8
238000005897 peptide coupling reaction Methods 0.000 claims description 8
125000006239 protecting group Chemical group 0.000 claims description 8
206010039083 rhinitis Diseases 0.000 claims description 8
229910052801 chlorine Inorganic materials 0.000 claims description 7
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
125000004076 pyridyl group Chemical group 0.000 claims description 7
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 6
125000000842 isoxazolyl group Chemical group 0.000 claims description 6
239000008194 pharmaceutical composition Substances 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
239000012190 activator Substances 0.000 claims description 5
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
125000001309 chloro group Chemical group Cl* 0.000 claims description 5
229940124597 therapeutic agent Drugs 0.000 claims description 5
125000003226 pyrazolyl group Chemical group 0.000 claims description 4
125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 3
125000006509 3,4-difluorobenzyl group Chemical group [H]C1=C(F)C(F)=C([H])C(=C1[H])C([H])([H])* 0.000 claims description 3
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 3
239000000969 carrier Substances 0.000 claims description 3
239000003085 diluting agent Substances 0.000 claims description 3
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 3
125000004284 isoxazol-3-yl group Chemical group [H]C1=C([H])C(*)=NO1 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
125000002971 oxazolyl group Chemical group 0.000 claims description 3
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 2
125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 2
125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims description 2
DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
KACZQOKEFKFNDB-UHFFFAOYSA-N ethyl 1h-pyrazole-4-carboxylate Chemical compound CCOC(=O)C=1C=NNC=1 KACZQOKEFKFNDB-UHFFFAOYSA-N 0.000 claims description 2
125000006260 ethylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])C([H])([H])[H] 0.000 claims description 2
125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 claims description 2
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims 3
125000004505 1,2,4-oxadiazol-5-yl group Chemical group O1N=CN=C1* 0.000 claims 1
DQMLFUMEBNHPPB-UHFFFAOYSA-N 2-Methylthiazolidine Chemical compound CC1NCCS1 DQMLFUMEBNHPPB-UHFFFAOYSA-N 0.000 claims 1
CUMCMYMKECWGHO-UHFFFAOYSA-N 3-methyl-1,2-oxazole Chemical compound CC=1C=CON=1 CUMCMYMKECWGHO-UHFFFAOYSA-N 0.000 claims 1
UJQZTMFRMLEYQN-UHFFFAOYSA-N 3-methyloxane Chemical compound CC1CCCOC1 UJQZTMFRMLEYQN-UHFFFAOYSA-N 0.000 claims 1
150000001409 amidines Chemical class 0.000 claims 1
208000027697 autoimmune lymphoproliferative syndrome due to CTLA4 haploinsuffiency Diseases 0.000 claims 1
125000006630 butoxycarbonylamino group Chemical group 0.000 claims 1
150000007857 hydrazones Chemical class 0.000 claims 1
125000004499 isoxazol-5-yl group Chemical group O1N=CC=C1* 0.000 claims 1
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 1
125000002757 morpholinyl group Chemical group 0.000 claims 1
GMXYRSGLFXGKBT-UHFFFAOYSA-N n-ethyl-9h-fluorene-3-carboxamide Chemical compound C1=CC=C2C3=CC(C(=O)NCC)=CC=C3CC2=C1 GMXYRSGLFXGKBT-UHFFFAOYSA-N 0.000 claims 1
VYCBCTICMMPTLJ-UHFFFAOYSA-N n-ethylfuran-2-carboxamide Chemical compound CCNC(=O)C1=CC=CO1 VYCBCTICMMPTLJ-UHFFFAOYSA-N 0.000 claims 1
230000035479 physiological effects, processes and functions Effects 0.000 claims 1
238000006467 substitution reaction Methods 0.000 claims 1
125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 claims 1
125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims 1
125000004495 thiazol-4-yl group Chemical group S1C=NC(=C1)* 0.000 claims 1
125000003396 thiol group Chemical group [H]S* 0.000 claims 1
102100024167 C-C chemokine receptor type 3 Human genes 0.000 abstract description 18
101710149862 C-C chemokine receptor type 3 Proteins 0.000 abstract description 18
239000005557 antagonist Substances 0.000 abstract description 8
125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract description 4
238000002560 therapeutic procedure Methods 0.000 abstract description 2
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 214
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 114
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 100
239000000243 solution Substances 0.000 description 89
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 63
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 60
239000002904 solvent Substances 0.000 description 60
238000004895 liquid chromatography mass spectrometry Methods 0.000 description 57
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 53
238000006243 chemical reaction Methods 0.000 description 52
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 39
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 39
229910052757 nitrogen Inorganic materials 0.000 description 38
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
235000002639 sodium chloride Nutrition 0.000 description 25
238000001308 synthesis method Methods 0.000 description 25
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 24
239000002585 base Substances 0.000 description 24
239000007787 solid Substances 0.000 description 22
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 20
125000001424 substituent group Chemical group 0.000 description 20
238000002360 preparation method Methods 0.000 description 19
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 18
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 17
210000004027 cell Anatomy 0.000 description 17
238000005342 ion exchange Methods 0.000 description 16
238000003756 stirring Methods 0.000 description 16
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
210000000265 leukocyte Anatomy 0.000 description 15
239000000047 product Substances 0.000 description 15
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 14
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 13
210000003979 eosinophil Anatomy 0.000 description 13
238000001819 mass spectrum Methods 0.000 description 13
238000002953 preparative HPLC Methods 0.000 description 13
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 12
229910021529 ammonia Inorganic materials 0.000 description 12
239000012074 organic phase Substances 0.000 description 12
229920006395 saturated elastomer Polymers 0.000 description 12
125000002887 hydroxy group Chemical group [H]O* 0.000 description 11
239000003921 oil Substances 0.000 description 11
235000019198 oils Nutrition 0.000 description 11
235000011121 sodium hydroxide Nutrition 0.000 description 11
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 10
239000007864 aqueous solution Substances 0.000 description 10
125000000623 heterocyclic group Chemical group 0.000 description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
238000001816 cooling Methods 0.000 description 9
238000004128 high performance liquid chromatography Methods 0.000 description 9
239000011347 resin Substances 0.000 description 9
229920005989 resin Polymers 0.000 description 9
235000017557 sodium bicarbonate Nutrition 0.000 description 9
229910000030 sodium bicarbonate Inorganic materials 0.000 description 9
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 9
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
125000003545 alkoxy group Chemical group 0.000 description 8
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 8
201000010099 disease Diseases 0.000 description 8
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 8
239000000741 silica gel Substances 0.000 description 8
229910002027 silica gel Inorganic materials 0.000 description 8
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
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 8
FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical group Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 7
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 7
238000005481 NMR spectroscopy Methods 0.000 description 7
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 7
238000010992 reflux Methods 0.000 description 7
239000000725 suspension Substances 0.000 description 7
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
230000004913 activation Effects 0.000 description 6
125000003118 aryl group Chemical group 0.000 description 6
239000003795 chemical substances by application Substances 0.000 description 6
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
230000002757 inflammatory effect Effects 0.000 description 6
239000007788 liquid Substances 0.000 description 6
238000002414 normal-phase solid-phase extraction Methods 0.000 description 6
239000003960 organic solvent Substances 0.000 description 6
239000001301 oxygen Substances 0.000 description 6
229910052760 oxygen Inorganic materials 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
239000002002 slurry Substances 0.000 description 6
210000001519 tissue Anatomy 0.000 description 6
108010059616 Activins Proteins 0.000 description 5
102000005606 Activins Human genes 0.000 description 5
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
101150041968 CDC13 gene Proteins 0.000 description 5
241000400611 Eucalyptus deanei Species 0.000 description 5
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 5
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 5
125000004453 alkoxycarbonyl group Chemical group 0.000 description 5
125000003806 alkyl carbonyl amino group Chemical group 0.000 description 5
125000004390 alkyl sulfonyl group Chemical group 0.000 description 5
238000004458 analytical method Methods 0.000 description 5
239000008346 aqueous phase Substances 0.000 description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
229910052794 bromium Inorganic materials 0.000 description 5
239000012230 colorless oil Substances 0.000 description 5
239000012043 crude product Substances 0.000 description 5
YQGOJNYOYNNSMM-UHFFFAOYSA-N eosin Chemical compound [Na+].OC(=O)C1=CC=CC=C1C1=C2C=C(Br)C(=O)C(Br)=C2OC2=C(Br)C(O)=C(Br)C=C21 YQGOJNYOYNNSMM-UHFFFAOYSA-N 0.000 description 5
238000003818 flash chromatography Methods 0.000 description 5
125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 5
239000007789 gas Substances 0.000 description 5
125000005843 halogen group Chemical group 0.000 description 5
230000002209 hydrophobic effect Effects 0.000 description 5
229910052943 magnesium sulfate Inorganic materials 0.000 description 5
239000002798 polar solvent Substances 0.000 description 5
229920001296 polysiloxane Polymers 0.000 description 5
150000003254 radicals Chemical class 0.000 description 5
238000010189 synthetic method Methods 0.000 description 5
238000012360 testing method Methods 0.000 description 5
239000003039 volatile agent Substances 0.000 description 5
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical group C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 4
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 4
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
206010061218 Inflammation Diseases 0.000 description 4
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
229920002472 Starch Polymers 0.000 description 4
230000002378 acidificating effect Effects 0.000 description 4
239000000488 activin Substances 0.000 description 4
125000003368 amide group Chemical group 0.000 description 4
235000011114 ammonium hydroxide Nutrition 0.000 description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
239000012267 brine Substances 0.000 description 4
OWIUPIRUAQMTTK-UHFFFAOYSA-N carbazic acid Chemical compound NNC(O)=O OWIUPIRUAQMTTK-UHFFFAOYSA-N 0.000 description 4
238000004587 chromatography analysis Methods 0.000 description 4
125000004093 cyano group Chemical group *C#N 0.000 description 4
150000002148 esters Chemical group 0.000 description 4
IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 4
238000001704 evaporation Methods 0.000 description 4
239000000284 extract Substances 0.000 description 4
238000001914 filtration Methods 0.000 description 4
239000000499 gel Substances 0.000 description 4
239000011261 inert gas Substances 0.000 description 4
208000027866 inflammatory disease Diseases 0.000 description 4
230000004054 inflammatory process Effects 0.000 description 4
235000019341 magnesium sulphate Nutrition 0.000 description 4
BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
235000019260 propionic acid Nutrition 0.000 description 4
238000000159 protein binding assay Methods 0.000 description 4
102000005962 receptors Human genes 0.000 description 4
108020003175 receptors Proteins 0.000 description 4
230000004044 response Effects 0.000 description 4
239000000523 sample Substances 0.000 description 4
238000000926 separation method Methods 0.000 description 4
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
239000007921 spray Substances 0.000 description 4
239000008107 starch Substances 0.000 description 4
229940032147 starch Drugs 0.000 description 4
230000009466 transformation Effects 0.000 description 4
125000001425 triazolyl group Chemical group 0.000 description 4
238000005406 washing Methods 0.000 description 4
UBWXUGDQUBIEIZ-UHFFFAOYSA-N (13-methyl-3-oxo-2,6,7,8,9,10,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-17-yl) 3-phenylpropanoate Chemical compound CC12CCC(C3CCC(=O)C=C3CC3)C3C1CCC2OC(=O)CCC1=CC=CC=C1 UBWXUGDQUBIEIZ-UHFFFAOYSA-N 0.000 description 3
AGQOIYCTCOEHGR-UHFFFAOYSA-N 5-methyl-1,2-oxazole Chemical compound CC1=CC=NO1 AGQOIYCTCOEHGR-UHFFFAOYSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
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229940116362 tragacanth Drugs 0.000 description 1
238000002054 transplantation Methods 0.000 description 1
229960005294 triamcinolone Drugs 0.000 description 1
GFNANZIMVAIWHM-OBYCQNJPSA-N triamcinolone Chemical compound O=C1C=C[C@]2(C)[C@@]3(F)[C@@H](O)C[C@](C)([C@@]([C@H](O)C4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 GFNANZIMVAIWHM-OBYCQNJPSA-N 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
PQDJYEQOELDLCP-UHFFFAOYSA-N trimethylsilane Chemical compound C[SiH](C)C PQDJYEQOELDLCP-UHFFFAOYSA-N 0.000 description 1
239000002753 trypsin inhibitor Substances 0.000 description 1
229960004799 tryptophan Drugs 0.000 description 1
241001529453 unidentified herpesvirus Species 0.000 description 1
229910052720 vanadium Inorganic materials 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
238000002424 x-ray crystallography Methods 0.000 description 1

Classifications

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- C07D265/30—1,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings
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- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- 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
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
- 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
- C07D417/14—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

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Medicinal Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Veterinary Medicine (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Immunology (AREA)
Pulmonology (AREA)
Diabetes (AREA)
Oncology (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Heart & Thoracic Surgery (AREA)
Dermatology (AREA)
Urology & Nephrology (AREA)
Cardiology (AREA)
Virology (AREA)
Rheumatology (AREA)
Communicable Diseases (AREA)
Orthopedic Medicine & Surgery (AREA)
AIDS & HIV (AREA)
Vascular Medicine (AREA)
Emergency Medicine (AREA)
Endocrinology (AREA)
Hematology (AREA)
Obesity (AREA)
Hospice & Palliative Care (AREA)
Tropical Medicine & Parasitology (AREA)
Molecular Biology (AREA)
Pain & Pain Management (AREA)

TW092106767A 2002-03-28 2003-03-26 Novel compounds TW200402419A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GBGB0208158.6A GB0208158D0 (en)	2002-03-28	2002-03-28	Novel compounds

Publications (1)

Publication Number	Publication Date
TW200402419A true TW200402419A (en)	2004-02-16

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ID=9934527

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
TW092106767A TW200402419A (en)	2002-03-28	2003-03-26	Novel compounds

Country Status (7)

Country	Link
EP (1)	EP1487827A1 (fr)
JP (1)	JP2005527564A (fr)
AR (1)	AR039173A1 (fr)
AU (1)	AU2003216907A1 (fr)
GB (1)	GB0208158D0 (fr)
TW (1)	TW200402419A (fr)
WO (1)	WO2003082862A1 (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2006028284A1 (fr)	2004-09-08	2006-03-16	Mitsubishi Pharma Corporation	Dérivé de morpholine
WO2007011292A1 (fr) *	2005-07-21	2007-01-25	Astrazeneca Ab	Dérivés de n-benzyl-morpholine en tant que modulateurs du récepteur de chimiokine

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4870074A (en) *	1986-04-30	1989-09-26	Dainippon Pharmaceutical Co., Ltd.	Substituted benzamide derivatives, for enhancing gastrointestinal motility
CA2372887A1 (fr) *	1999-05-25	2000-11-30	Sepracor Inc.	Composes heterocycliques analgesiques et procedes d'utilisation de ces derniers
IL155093A0 (en) *	2000-09-29	2003-10-31	Glaxo Group Ltd	Morpholin-acetamide derivatives for the treatment on inflammatory diseases

2002
- 2002-03-28 GB GBGB0208158.6A patent/GB0208158D0/en not_active Ceased
2003
- 2003-03-26 TW TW092106767A patent/TW200402419A/zh unknown
- 2003-03-27 WO PCT/EP2003/003347 patent/WO2003082862A1/fr not_active Ceased
- 2003-03-27 EP EP03712119A patent/EP1487827A1/fr not_active Withdrawn
- 2003-03-27 AU AU2003216907A patent/AU2003216907A1/en not_active Abandoned
- 2003-03-27 AR ARP030101086A patent/AR039173A1/es not_active Application Discontinuation
- 2003-03-27 JP JP2003580327A patent/JP2005527564A/ja active Pending

Also Published As

Publication number	Publication date
GB0208158D0 (en)	2002-05-22
AR039173A1 (es)	2005-02-09
WO2003082862A1 (fr)	2003-10-09
JP2005527564A (ja)	2005-09-15
EP1487827A1 (fr)	2004-12-22
AU2003216907A1 (en)	2003-10-13

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