JPH08501564A - 新規なエポキシド含有化合物 - Google Patents

新規なエポキシド含有化合物

Info

Publication number: JPH08501564A
Authority: JP; Japan
Prior art keywords: mmol; dimethylxanthine; solution; added; dichloromethane
Prior art date: 1992-09-22
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.): Pending

Application number

JP6508445A

Other languages

English (en)

Japanese (ja)

Inventor

アンダライナー，ゲイル

クレイン，ジェイ・ピーター

ミッチニック，ジョン

リー，アリステア

クマー，アニル

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

CTI Biopharma Corp

Original Assignee

Cell Therapeutics Inc

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.)

1992-09-22

Filing date

1993-09-22

Publication date

1996-02-20

1992-09-22 Priority claimed from US07/949,330 external-priority patent/US5288721A/en

1993-09-22 Application filed by Cell Therapeutics Inc filed Critical Cell Therapeutics Inc

1996-02-20 Publication of JPH08501564A publication Critical patent/JPH08501564A/ja

Status Pending legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 75
150000002118 epoxides Chemical class 0.000 title description 6
239000012453 solvate Substances 0.000 claims abstract description 7
125000000217 alkyl group Chemical group 0.000 claims abstract description 6
150000003839 salts Chemical class 0.000 claims abstract description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 4
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims abstract description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 200
229960004559 theobromine Drugs 0.000 claims description 80
-1 pyrrole amide Chemical class 0.000 claims description 77
238000006243 chemical reaction Methods 0.000 claims description 63
LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical compound O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 claims description 42
ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 claims description 25
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 21
XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical class C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 claims description 21
KNCYXPMJDCCGSJ-UHFFFAOYSA-N piperidine-2,6-dione Chemical compound O=C1CCCC(=O)N1 KNCYXPMJDCCGSJ-UHFFFAOYSA-N 0.000 claims description 21
229940075420 xanthine Drugs 0.000 claims description 17
PFWLFWPASULGAN-UHFFFAOYSA-N 7-methylxanthine Chemical compound N1C(=O)NC(=O)C2=C1N=CN2C PFWLFWPASULGAN-UHFFFAOYSA-N 0.000 claims description 14
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 12
RWQNBRDOKXIBIV-UHFFFAOYSA-N thymine Chemical compound CC1=CNC(=O)NC1=O RWQNBRDOKXIBIV-UHFFFAOYSA-N 0.000 claims description 12
229940035893 uracil Drugs 0.000 claims description 12
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
239000008194 pharmaceutical composition Substances 0.000 claims description 9
208000023275 Autoimmune disease Diseases 0.000 claims description 7
125000000623 heterocyclic group Chemical group 0.000 claims description 7
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 6
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 6
206010020751 Hypersensitivity Diseases 0.000 claims description 6
238000000034 method Methods 0.000 claims description 6
229940113082 thymine Drugs 0.000 claims description 6
QGNQEODJYRGEJX-UHFFFAOYSA-N 4h-isoquinoline-1,3-dione Chemical compound C1=CC=C2C(=O)NC(=O)CC2=C1 QGNQEODJYRGEJX-UHFFFAOYSA-N 0.000 claims description 5
208000035475 disorder Diseases 0.000 claims description 5
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 4
208000036142 Viral infection Diseases 0.000 claims description 4
125000002837 carbocyclic group Chemical group 0.000 claims description 4
208000037803 restenosis Diseases 0.000 claims description 4
KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 claims description 4
230000009385 viral infection Effects 0.000 claims description 4
206010061218 Inflammation Diseases 0.000 claims description 3
208000030961 allergic reaction Diseases 0.000 claims description 3
230000028993 immune response Effects 0.000 claims description 3
230000004054 inflammatory process Effects 0.000 claims description 3
239000000546 pharmaceutical excipient Substances 0.000 claims description 3
XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 claims description 3
KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 2
NMIZONYLXCOHEF-UHFFFAOYSA-N 1h-imidazole-2-carboxamide Chemical compound NC(=O)C1=NC=CN1 NMIZONYLXCOHEF-UHFFFAOYSA-N 0.000 claims description 2
RLOQBKJCOAXOLR-UHFFFAOYSA-N 1h-pyrrole-2-carboxamide Chemical compound NC(=O)C1=CC=CN1 RLOQBKJCOAXOLR-UHFFFAOYSA-N 0.000 claims description 2
NJOYYTJYAMKQAG-UHFFFAOYSA-N 8-amino-3-methyl-7h-purine-2,6-dione Chemical compound O=C1NC(=O)N(C)C2=C1NC(N)=N2 NJOYYTJYAMKQAG-UHFFFAOYSA-N 0.000 claims description 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 2
206010020772 Hypertension Diseases 0.000 claims description 2
206010028116 Mucosal inflammation Diseases 0.000 claims description 2
201000010927 Mucositis Diseases 0.000 claims description 2
JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 claims description 2
229940076134 benzene Drugs 0.000 claims description 2
210000003169 central nervous system Anatomy 0.000 claims description 2
LOGSONSNCYTHPS-UHFFFAOYSA-N cyclopentane-1,3-dione Chemical compound O=C1CCC(=O)C1 LOGSONSNCYTHPS-UHFFFAOYSA-N 0.000 claims description 2
YVIVRJLWYJGJTJ-UHFFFAOYSA-N gamma-Valerolactam Chemical compound CC1CCC(=O)N1 YVIVRJLWYJGJTJ-UHFFFAOYSA-N 0.000 claims description 2
229940088597 hormone Drugs 0.000 claims description 2
239000005556 hormone Substances 0.000 claims description 2
VDBNYAPERZTOOF-UHFFFAOYSA-N isoquinolin-1(2H)-one Chemical compound C1=CC=C2C(=O)NC=CC2=C1 VDBNYAPERZTOOF-UHFFFAOYSA-N 0.000 claims description 2
XOOMNEFVDUTJPP-UHFFFAOYSA-N naphthalene-1,3-diol Chemical compound C1=CC=CC2=CC(O)=CC(O)=C21 XOOMNEFVDUTJPP-UHFFFAOYSA-N 0.000 claims description 2
201000008383 nephritis Diseases 0.000 claims description 2
LDNSHTVNGGHGQJ-UHFFFAOYSA-N pyrrole-1-carboxamide Chemical compound NC(=O)N1C=CC=C1 LDNSHTVNGGHGQJ-UHFFFAOYSA-N 0.000 claims description 2
JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims description 2
229960002317 succinimide Drugs 0.000 claims description 2
HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 claims 2
RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 claims 1
AKWIAIDKXNKXDI-UHFFFAOYSA-N 1h-pyrrole-3-carboxamide Chemical compound NC(=O)C=1C=CNC=1 AKWIAIDKXNKXDI-UHFFFAOYSA-N 0.000 claims 1
CIFFBTOJCKSRJY-UHFFFAOYSA-N 3α,4,7,7α-tetrahydro-1h-isoindole-1,3(2h)-dione Chemical compound C1C=CCC2C(=O)NC(=O)C21 CIFFBTOJCKSRJY-UHFFFAOYSA-N 0.000 claims 1
LNDZXOWGUAIUBG-UHFFFAOYSA-N 6-aminouracil Chemical compound NC1=CC(=O)NC(=O)N1 LNDZXOWGUAIUBG-UHFFFAOYSA-N 0.000 claims 1
CBQMKYHLDADRLN-UHFFFAOYSA-N 7-methylhypoxanthine Chemical compound N1C=NC(=O)C2=C1N=CN2C CBQMKYHLDADRLN-UHFFFAOYSA-N 0.000 claims 1
208000012902 Nervous system disease Diseases 0.000 claims 1
206010045171 Tumour pain Diseases 0.000 claims 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
230000019522 cellular metabolic process Effects 0.000 claims 1
125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
239000003937 drug carrier Substances 0.000 claims 1
229910052736 halogen Inorganic materials 0.000 claims 1
150000002367 halogens Chemical class 0.000 claims 1
150000004702 methyl esters Chemical class 0.000 claims 1
229940075566 naphthalene Drugs 0.000 claims 1
229910052760 oxygen Inorganic materials 0.000 claims 1
239000001301 oxygen Substances 0.000 claims 1
239000000203 mixture Substances 0.000 abstract description 99
125000001475 halogen functional group Chemical group 0.000 abstract description 2
125000004430 oxygen atom Chemical group O* 0.000 abstract description 2
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 541
239000000243 solution Substances 0.000 description 225
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 174
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 159
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 123
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 100
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 92
239000002904 solvent Substances 0.000 description 92
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 85
239000011541 reaction mixture Substances 0.000 description 85
238000003756 stirring Methods 0.000 description 82
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 77
239000012044 organic layer Substances 0.000 description 75
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 73
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 68
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 62
239000007787 solid Substances 0.000 description 61
239000000284 extract Substances 0.000 description 60
230000002829 reductive effect Effects 0.000 description 53
238000000746 purification Methods 0.000 description 51
GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 51
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 45
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 45
229960001760 dimethyl sulfoxide Drugs 0.000 description 44
239000003480 eluent Substances 0.000 description 44
229910052943 magnesium sulfate Inorganic materials 0.000 description 44
235000019341 magnesium sulphate Nutrition 0.000 description 44
YAPQBXQYLJRXSA-UHFFFAOYSA-N theobromine Chemical compound CN1C(=O)NC(=O)C2=C1N=CN2C YAPQBXQYLJRXSA-UHFFFAOYSA-N 0.000 description 44
210000004027 cell Anatomy 0.000 description 43
239000012043 crude product Substances 0.000 description 41
239000000741 silica gel Substances 0.000 description 41
229910002027 silica gel Inorganic materials 0.000 description 41
239000010410 layer Substances 0.000 description 40
229910052938 sodium sulfate Inorganic materials 0.000 description 40
235000011152 sodium sulphate Nutrition 0.000 description 40
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 38
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 38
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 37
230000015572 biosynthetic process Effects 0.000 description 36
238000003786 synthesis reaction Methods 0.000 description 35
238000003818 flash chromatography Methods 0.000 description 34
239000003921 oil Substances 0.000 description 33
235000019198 oils Nutrition 0.000 description 33
239000011734 sodium Substances 0.000 description 31
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 30
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 30
239000012267 brine Substances 0.000 description 30
229910052708 sodium Inorganic materials 0.000 description 30
229910000104 sodium hydride Inorganic materials 0.000 description 30
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 29
239000012312 sodium hydride Substances 0.000 description 29
108060008682 Tumor Necrosis Factor Proteins 0.000 description 25
235000010265 sodium sulphite Nutrition 0.000 description 25
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 24
239000003814 drug Substances 0.000 description 24
235000017557 sodium bicarbonate Nutrition 0.000 description 24
229910000030 sodium bicarbonate Inorganic materials 0.000 description 24
102000003390 tumor necrosis factor Human genes 0.000 description 23
230000000694 effects Effects 0.000 description 22
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
229940079593 drug Drugs 0.000 description 21
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 20
238000004587 chromatography analysis Methods 0.000 description 20
229920006395 saturated elastomer Polymers 0.000 description 20
LFTLOKWAGJYHHR-UHFFFAOYSA-N N-methylmorpholine N-oxide Chemical compound CN1(=O)CCOCC1 LFTLOKWAGJYHHR-UHFFFAOYSA-N 0.000 description 18
102000000589 Interleukin-1 Human genes 0.000 description 17
108010002352 Interleukin-1 Proteins 0.000 description 17
230000035755 proliferation Effects 0.000 description 17
239000000725 suspension Substances 0.000 description 17
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 16
239000003208 petroleum Substances 0.000 description 16
230000000638 stimulation Effects 0.000 description 16
239000012230 colorless oil Substances 0.000 description 15
201000010099 disease Diseases 0.000 description 15
230000002265 prevention Effects 0.000 description 15
102000010780 Platelet-Derived Growth Factor Human genes 0.000 description 14
108010038512 Platelet-Derived Growth Factor Proteins 0.000 description 14
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 14
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 14
239000000377 silicon dioxide Substances 0.000 description 13
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 13
239000007788 liquid Substances 0.000 description 12
229910000042 hydrogen bromide Inorganic materials 0.000 description 11
108010062580 Concanavalin A Proteins 0.000 description 10
239000002253 acid Substances 0.000 description 10
ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 10
YPLVPFUSXYSHJD-UHFFFAOYSA-N 11-bromoundec-1-ene Chemical compound BrCCCCCCCCCC=C YPLVPFUSXYSHJD-UHFFFAOYSA-N 0.000 description 9
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 9
239000007864 aqueous solution Substances 0.000 description 9
239000012141 concentrate Substances 0.000 description 9
239000011777 magnesium Substances 0.000 description 9
229910052749 magnesium Inorganic materials 0.000 description 9
DWZAJFZEYZIHPO-UHFFFAOYSA-N santin Chemical compound C1=CC(OC)=CC=C1C1=C(OC)C(=O)C2=C(O)C(OC)=C(O)C=C2O1 DWZAJFZEYZIHPO-UHFFFAOYSA-N 0.000 description 9
GMSNIKWWOQHZGF-UHFFFAOYSA-N 3-methyl-9H-xanthine Chemical compound O=C1NC(=O)N(C)C2=C1N=CN2 GMSNIKWWOQHZGF-UHFFFAOYSA-N 0.000 description 8
AWUCVROLDVIAJX-UHFFFAOYSA-N alpha-glycerophosphate Natural products OCC(O)COP(O)(O)=O AWUCVROLDVIAJX-UHFFFAOYSA-N 0.000 description 8
DGODWNOPHMXOTR-UHFFFAOYSA-N dipotassium;dioxido(dioxo)osmium;dihydrate Chemical compound O.O.[K+].[K+].[O-][Os]([O-])(=O)=O DGODWNOPHMXOTR-UHFFFAOYSA-N 0.000 description 8
239000012266 salt solution Substances 0.000 description 8
NHAXKHSVJBVINX-UHFFFAOYSA-N 3,7-dimethylpurine-2,6-dione;sodium Chemical compound [Na].CN1C(=O)NC(=O)C2=C1N=CN2C NHAXKHSVJBVINX-UHFFFAOYSA-N 0.000 description 7
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 7
206010028980 Neoplasm Diseases 0.000 description 7
230000000735 allogeneic effect Effects 0.000 description 7
238000004440 column chromatography Methods 0.000 description 7
239000013078 crystal Substances 0.000 description 7
239000005457 ice water Substances 0.000 description 7
150000003949 imides Chemical class 0.000 description 7
239000012285 osmium tetroxide Substances 0.000 description 7
229910000489 osmium tetroxide Inorganic materials 0.000 description 7
230000037361 pathway Effects 0.000 description 7
239000012047 saturated solution Substances 0.000 description 7
239000011780 sodium chloride Substances 0.000 description 7
XGRLSUFHELJJAB-JGSYTFBMSA-M sodium;[(2r)-2-hydroxy-3-[(z)-octadec-9-enoyl]oxypropyl] hydrogen phosphate Chemical compound [Na+].CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](O)COP(O)([O-])=O XGRLSUFHELJJAB-JGSYTFBMSA-M 0.000 description 7
125000006043 5-hexenyl group Chemical group 0.000 description 6
RIMXEJYJXDBLIE-UHFFFAOYSA-N 6-bromohex-1-ene Chemical compound BrCCCCC=C RIMXEJYJXDBLIE-UHFFFAOYSA-N 0.000 description 6
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
239000012359 Methanesulfonyl chloride Substances 0.000 description 6
206010040070 Septic Shock Diseases 0.000 description 6
241000212342 Sium Species 0.000 description 6
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 6
210000001185 bone marrow Anatomy 0.000 description 6
238000010322 bone marrow transplantation Methods 0.000 description 6
NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 6
JMVOCSLPMGHXPG-UHFFFAOYSA-N dipotassium;dioxido(dioxo)osmium Chemical compound [K+].[K+].[O-][Os]([O-])(=O)=O JMVOCSLPMGHXPG-UHFFFAOYSA-N 0.000 description 6
210000003780 hair follicle Anatomy 0.000 description 6
230000005764 inhibitory process Effects 0.000 description 6
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 6
230000003287 optical effect Effects 0.000 description 6
239000012074 organic phase Substances 0.000 description 6
JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 6
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
IQFYYKKMVGJFEH-OFKYTIFKSA-N 1-[(2r,4s,5r)-4-hydroxy-5-(tritiooxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione Chemical compound C1[C@H](O)[C@@H](CO[3H])O[C@H]1N1C(=O)NC(=O)C(C)=C1 IQFYYKKMVGJFEH-OFKYTIFKSA-N 0.000 description 5
ZSLUVFAKFWKJRC-IGMARMGPSA-N 232Th Chemical compound [232Th] ZSLUVFAKFWKJRC-IGMARMGPSA-N 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
241000699666 Mus <mouse, genus> Species 0.000 description 5
229910052776 Thorium Inorganic materials 0.000 description 5
210000004271 bone marrow stromal cell Anatomy 0.000 description 5
239000006071 cream Substances 0.000 description 5
231100000673 dose–response relationship Toxicity 0.000 description 5
239000000463 material Substances 0.000 description 5
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RPGWZZNNEUHDAQ-UHFFFAOYSA-N phenylphosphine Chemical compound PC1=CC=CC=C1 RPGWZZNNEUHDAQ-UHFFFAOYSA-N 0.000 description 1
QGVLYPPODPLXMB-QXYKVGAMSA-N phorbol Natural products C[C@@H]1[C@@H](O)[C@]2(O)[C@H]([C@H]3C=C(CO)C[C@@]4(O)[C@H](C=C(C)C4=O)[C@@]13O)C2(C)C QGVLYPPODPLXMB-QXYKVGAMSA-N 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 description 1
150000008104 phosphatidylethanolamines Chemical class 0.000 description 1
125000005543 phthalimide group Chemical class 0.000 description 1
231100000572 poisoning Toxicity 0.000 description 1
230000000607 poisoning effect Effects 0.000 description 1
239000013641 positive control Substances 0.000 description 1
NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
229910000105 potassium hydride Inorganic materials 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
238000011533 pre-incubation Methods 0.000 description 1
230000008569 process Effects 0.000 description 1
230000000750 progressive effect Effects 0.000 description 1
230000000770 proinflammatory effect Effects 0.000 description 1
230000000069 prophylactic effect Effects 0.000 description 1
201000003651 pulmonary sarcoidosis Diseases 0.000 description 1
210000003492 pulmonary vein Anatomy 0.000 description 1
238000010791 quenching Methods 0.000 description 1
238000011084 recovery Methods 0.000 description 1
230000009467 reduction Effects 0.000 description 1
230000001172 regenerating effect Effects 0.000 description 1
238000007634 remodeling Methods 0.000 description 1
230000008439 repair process Effects 0.000 description 1
230000029058 respiratory gaseous exchange Effects 0.000 description 1
231100000241 scar Toxicity 0.000 description 1
230000035939 shock Effects 0.000 description 1
230000019491 signal transduction Effects 0.000 description 1
210000003491 skin Anatomy 0.000 description 1
208000019116 sleep disease Diseases 0.000 description 1
210000000329 smooth muscle myocyte Anatomy 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 1
229910001948 sodium oxide Inorganic materials 0.000 description 1
WZWGGYFEOBVNLA-UHFFFAOYSA-N sodium;dihydrate Chemical compound O.O.[Na] WZWGGYFEOBVNLA-UHFFFAOYSA-N 0.000 description 1
241000894007 species Species 0.000 description 1
239000000021 stimulant Substances 0.000 description 1
230000004936 stimulating effect Effects 0.000 description 1
108091007196 stromelysin Proteins 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
125000003375 sulfoxide group Chemical group 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
230000004083 survival effect Effects 0.000 description 1
210000000225 synapse Anatomy 0.000 description 1
230000002195 synergetic effect Effects 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
229940065721 systemic for obstructive airway disease xanthines Drugs 0.000 description 1
229940037128 systemic glucocorticoids Drugs 0.000 description 1
229910052714 tellurium Inorganic materials 0.000 description 1
BWMISRWJRUSYEX-SZKNIZGXSA-N terbinafine hydrochloride Chemical compound Cl.C1=CC=C2C(CN(C\C=C\C#CC(C)(C)C)C)=CC=CC2=C1 BWMISRWJRUSYEX-SZKNIZGXSA-N 0.000 description 1
238000010998 test method Methods 0.000 description 1
JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
201000004647 tinea pedis Diseases 0.000 description 1
230000000451 tissue damage Effects 0.000 description 1
231100000827 tissue damage Toxicity 0.000 description 1
230000009772 tissue formation Effects 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
231100000167 toxic agent Toxicity 0.000 description 1
239000003440 toxic substance Substances 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
238000002054 transplantation Methods 0.000 description 1
230000008733 trauma Effects 0.000 description 1
210000004881 tumor cell Anatomy 0.000 description 1
230000004614 tumor growth Effects 0.000 description 1
230000006433 tumor necrosis factor production Effects 0.000 description 1
OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
241000701161 unidentified adenovirus Species 0.000 description 1
210000002700 urine Anatomy 0.000 description 1
238000007738 vacuum evaporation Methods 0.000 description 1
239000004474 valine Substances 0.000 description 1
210000003462 vein Anatomy 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/36—Compounds containing oxirane rings with hydrocarbon radicals, substituted by nitrogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/04—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms
- C07D473/06—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3
- C07D473/10—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3 with methyl radicals in positions 3 and 7, e.g. theobromine

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Immunology (AREA)
Virology (AREA)
Pulmonology (AREA)
Communicable Diseases (AREA)
Oncology (AREA)
Pain & Pain Management (AREA)
Rheumatology (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Endocrinology (AREA)
Reproductive Health (AREA)
Urology & Nephrology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

JP6508445A 1992-09-22 1993-09-22 新規なエポキシド含有化合物 Pending JPH08501564A (ja)

Applications Claiming Priority (5)

Application Number	Priority Date	Filing Date	Title
US07/949,330 US5288721A (en)	1992-09-22	1992-09-22	Substituted epoxyalkyl xanthines
US99165592A	1992-12-16	1992-12-16
US07/991,655		1992-12-16
US07/949,330		1992-12-16
PCT/US1993/009073 WO1994006431A1 (fr)	1992-09-22	1993-09-22	Nouveaux composes epoxy

Publications (1)

Publication Number	Publication Date
JPH08501564A true JPH08501564A (ja)	1996-02-20

Family

ID=27130287

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP6508445A Pending JPH08501564A (ja)	1992-09-22	1993-09-22	新規なエポキシド含有化合物

Country Status (5)

Country	Link
EP (1)	EP0662834A4 (fr)
JP (1)	JPH08501564A (fr)
AU (1)	AU5138493A (fr)
CA (1)	CA2145192A1 (fr)
WO (1)	WO1994006431A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO1998052919A1 (fr) *	1997-05-21	1998-11-26	Japan Tobacco Inc.	Derives de phtalimide et produit pharmaceutique contenant ces derives

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AU670125B2 (en) *	1992-09-15	1996-07-04	Immunex Corporation	Method of treating tnf-dependent inflammation using tumor necrosis factor antagonists
US5446046A (en) *	1993-10-28	1995-08-29	University Of Florida Research Foundation	A1 adenosine receptor agonists and antagonists as diuretics
EP0739203A4 (fr) *	1994-01-14	2000-12-20	Cell Therapeutics Inc	Methode de traitement d'affections dues a la proliferation cellulaire en reponse aux pdgf, egf, fgf et vegf
JPH09511496A (ja) *	1994-02-18	1997-11-18	セル・セラピューティックス・インコーポレーテッド	細胞内メッセンジャー
US7276506B2 (en)	1998-12-28	2007-10-02	4 Aza Bioscience Nv	Immunosuppressive effects of pteridine derivatives
US6946465B2 (en) *	1999-02-02	2005-09-20	4 Aza Bioscience Nv	Immunosuppressive effects of pteridine derivatives
WO2008009078A2 (fr)	2006-07-20	2008-01-24	Gilead Sciences, Inc.	Dérivés de la quinazoline tri-substitués en 4,6-dl et en 2,4,6 utilisables pour traiter les infections virales
US10144736B2 (en)	2006-07-20	2018-12-04	Gilead Sciences, Inc.	Substituted pteridines useful for the treatment and prevention of viral infections
US9670205B2 (en)	2015-03-04	2017-06-06	Gilead Sciences, Inc.	Toll like receptor modulator compounds
WO2018045150A1 (fr)	2016-09-02	2018-03-08	Gilead Sciences, Inc.	Dérivés de 4,6-diamino-pyrido [3,2-d] pyrimidine en tant que modulateurs du récepteur de type toll
AU2017318601B2 (en)	2016-09-02	2020-09-03	Gilead Sciences, Inc.	Toll like receptor modulator compounds
TWI751516B (zh)	2019-04-17	2022-01-01	美商基利科學股份有限公司	類鐸受體調節劑之固體形式
TW202212339A (zh)	2019-04-17	2022-04-01	美商基利科學股份有限公司	類鐸受體調節劑之固體形式
TWI879779B (zh)	2019-06-28	2025-04-11	美商基利科學股份有限公司	類鐸受體調節劑化合物的製備方法

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH472424A (de) *	1965-03-23	1969-05-15	Ciba Geigy	Verfahren zur Herstellung von neuen Polyepoxydverbindungen und deren Anwendung
US5158967A (en) *	1991-06-12	1992-10-27	E. R. Squibb & Sons, Inc.	7-oxabicycloheptyl substituted heterocyclic amide prostaglandin analogs useful in the treatment of thrombotic and vasospastic disease

1993
- 1993-09-22 CA CA002145192A patent/CA2145192A1/fr not_active Abandoned
- 1993-09-22 WO PCT/US1993/009073 patent/WO1994006431A1/fr not_active Ceased
- 1993-09-22 AU AU51384/93A patent/AU5138493A/en not_active Abandoned
- 1993-09-22 EP EP93922366A patent/EP0662834A4/fr not_active Withdrawn
- 1993-09-22 JP JP6508445A patent/JPH08501564A/ja active Pending

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO1998052919A1 (fr) *	1997-05-21	1998-11-26	Japan Tobacco Inc.	Derives de phtalimide et produit pharmaceutique contenant ces derives

Also Published As

Publication number	Publication date
CA2145192A1 (fr)	1994-03-31
WO1994006431A1 (fr)	1994-03-31
EP0662834A1 (fr)	1995-07-19
EP0662834A4 (fr)	1996-04-17
AU5138493A (en)	1994-04-12

Publication	Publication Date	Title
US5780476A (en)	1998-07-14	Hydroxyl-containing xanthine compounds
CA2748864C (fr)	2015-03-03	Composes amino-heterocycliques employes en tant qu'inhibiteurs de pde9
JPH08501564A (ja)	1996-02-20	新規なエポキシド含有化合物
JP2002087961A (ja)	2002-03-27	鏡像異性体ヒドロキシル化キサンチン化合物
US5817662A (en)	1998-10-06	Substituted amino alkyl compounds
TWI295670B (en)	2008-04-11	Vanilloid receptor ligands and their use in treatments
JP3182213B2 (ja)	2001-07-03	ピリミジンの新誘導体、それらの製造法、得られる中間体、それらの薬剤としての使用及びそれらを含有する製薬組成物
CN1330652A (zh)	2002-01-09	用作5HT2C激动剂的2,3,4,4a－四氢－1H－吡嗪并(1,2－a)喹喔啉－5(6H)酮衍生物
CA2117377C (fr)	2006-05-30	Composes aminoalkyl substitues
CN1354749A (zh)	2002-06-19	改善性功能障碍的a1b－肾上腺素能受体的选择性拮抗剂的应用
CN1040326C (zh)	1998-10-21	咪唑并吡啶paf/h1拮抗剂的制备方法
WO1994011001A1 (fr)	1994-05-26	Composes a teneur hydroxyle
EP0719267B1 (fr)	2002-07-31	Inhibiteurs de la signalisation cellulaire vehiculee par des messagers secondaires
EP0484071A2 (fr)	1992-05-06	Synergie d'inhibiteurs de HIV reverse transcriptase
US5770595A (en)	1998-06-23	Oxime substituted therapeutic compounds
WO1994022863A9 (fr)	1994-12-22	Inhibiteurs de la signalisation cellulaire vehiculee par des messagers secondaires
JPH072831A (ja)	1995-01-06	ベータ−３選択性アドレナリン作動剤としてのアミノシクロアルカノベンゾジオキソール類
HUT72740A (en)	1996-05-28	Dimethylbenzofurans and dimethylbenzopyrans and they use for preparing pharmaceutical compositions having 5-ht3 antagonistic activity
HUT72677A (en)	1996-05-28	Xanthine derivatives as adenosine a1 receptor antagonists
US6121270A (en)	2000-09-19	Epoxide-containing compounds
JPH0427984B2 (fr)	1992-05-13
AU9051898A (en)	1999-01-14	Second messenger cell signalling inhibitors
HK1066795A (en)	2005-04-01	Substituted amino alkyl compounds

JPH08501564A - 新規なエポキシド含有化合物 - Google Patents

Info

Links

Classifications

Landscapes

Applications Claiming Priority (5)

Publications (1)

Family

ID=27130287

Family Applications (1)

Country Status (5)

Cited By (1)

Families Citing this family (14)

Family Cites Families (2)

Cited By (1)

Also Published As

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