SE467974B - 5-oxi-derivat av tetrahydrofuran, foerfarande foer framstaellning av detta och en terapeutisk komposition - Google Patents

5-oxi-derivat av tetrahydrofuran, foerfarande foer framstaellning av detta och en terapeutisk komposition

Info

Publication number: SE467974B
Authority: SE; Sweden
Prior art keywords: group; alkyl; carbon atoms; independently; straight
Prior art date: 1987-01-27

Application number

SE8800171A

Other languages

English (en)

Swedish (sv)

Other versions

SE8800171D0 (sv

SE8800171L (sv

Inventor

J-J Godfroid

Original Assignee

Scras

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.)

1987-01-27

Filing date

1988-01-20

Publication date

1992-10-12

1988-01-20 Application filed by Scras filed Critical Scras

1988-01-20 Publication of SE8800171D0 publication Critical patent/SE8800171D0/xx

1988-07-28 Publication of SE8800171L publication Critical patent/SE8800171L/xx

1992-10-12 Publication of SE467974B publication Critical patent/SE467974B/sv

Links

239000000203 mixture Substances 0.000 title claims description 14
238000000034 method Methods 0.000 title claims description 5
WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 title claims description 4
230000001225 therapeutic effect Effects 0.000 title claims description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 44
125000000217 alkyl group Chemical group 0.000 claims description 23
125000004432 carbon atom Chemical group C* 0.000 claims description 21
-1 bromofluoromethyl Chemical group 0.000 claims description 12
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 11
238000002360 preparation method Methods 0.000 claims description 11
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 10
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 10
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 8
125000003342 alkenyl group Chemical group 0.000 claims description 8
VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 claims description 7
JVZRCNQLWOELDU-UHFFFAOYSA-N gamma-Phenylpyridine Natural products C1=CC=CC=C1C1=CC=NC=C1 JVZRCNQLWOELDU-UHFFFAOYSA-N 0.000 claims description 7
229910052801 chlorine Inorganic materials 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 6
239000000460 chlorine Substances 0.000 claims description 5
125000003277 amino group Chemical group 0.000 claims description 4
150000003863 ammonium salts Chemical class 0.000 claims description 4
150000001450 anions Chemical class 0.000 claims description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 4
229910052740 iodine Inorganic materials 0.000 claims description 4
DWKPPFQULDPWHX-UHFFFAOYSA-N methyl 2-aminopropanoate Chemical compound COC(=O)C(C)N DWKPPFQULDPWHX-UHFFFAOYSA-N 0.000 claims description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
125000003884 phenylalkyl group Chemical group 0.000 claims description 4
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 3
239000004480 active ingredient Substances 0.000 claims description 2
150000001351 alkyl iodides Chemical class 0.000 claims description 2
239000000010 aprotic solvent Substances 0.000 claims description 2
239000002243 precursor Substances 0.000 claims description 2
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
125000005270 trialkylamine group Chemical group 0.000 claims description 2
125000000753 cycloalkyl group Chemical group 0.000 claims 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 4
229910052739 hydrogen Inorganic materials 0.000 claims 4
239000001257 hydrogen Substances 0.000 claims 4
125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims 4
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
125000000304 alkynyl group Chemical group 0.000 claims 3
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 3
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 2
229910052794 bromium Inorganic materials 0.000 claims 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
125000000392 cycloalkenyl group Chemical group 0.000 claims 1
125000005356 cycloalkylalkenyl group Chemical group 0.000 claims 1
150000002431 hydrogen Chemical class 0.000 claims 1
239000000546 pharmaceutical excipient Substances 0.000 claims 1
150000003222 pyridines Chemical class 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
108010003541 Platelet Activating Factor Proteins 0.000 description 15
HVAUUPRFYPCOCA-AREMUKBSSA-N 2-O-acetyl-1-O-hexadecyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCCOC[C@@H](OC(C)=O)COP([O-])(=O)OCC[N+](C)(C)C HVAUUPRFYPCOCA-AREMUKBSSA-N 0.000 description 13
FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 11
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
238000001704 evaporation Methods 0.000 description 9
230000008020 evaporation Effects 0.000 description 9
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 8
239000002904 solvent Substances 0.000 description 8
239000007787 solid Substances 0.000 description 7
DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 6
UQHSYJSAILMYCL-UHFFFAOYSA-N 2-tridecyl-2,3-dihydrofuran Chemical compound CCCCCCCCCCCCCC1CC=CO1 UQHSYJSAILMYCL-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
241000283973 Oryctolagus cuniculus Species 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
230000008602 contraction Effects 0.000 description 5
YEESKJGWJFYOOK-IJHYULJSSA-N leukotriene D4 Chemical compound CCCCC\C=C/C\C=C/C=C/C=C/[C@H]([C@@H](O)CCCC(O)=O)SC[C@H](N)C(=O)NCC(O)=O YEESKJGWJFYOOK-IJHYULJSSA-N 0.000 description 5
230000008018 melting Effects 0.000 description 5
238000002844 melting Methods 0.000 description 5
239000003921 oil Substances 0.000 description 5
239000000741 silica gel Substances 0.000 description 5
229910002027 silica gel Inorganic materials 0.000 description 5
238000004809 thin layer chromatography Methods 0.000 description 5
230000000694 effects Effects 0.000 description 4
239000003480 eluent Substances 0.000 description 4
229960001340 histamine Drugs 0.000 description 4
239000003208 petroleum Substances 0.000 description 4
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 4
LDLCZOVUSADOIV-UHFFFAOYSA-N 2-bromoethanol Chemical compound OCCBr LDLCZOVUSADOIV-UHFFFAOYSA-N 0.000 description 3
CEDTWAXBIMRBDS-UHFFFAOYSA-N 2-hexyl-2,3-dihydrofuran Chemical compound CCCCCCC1CC=CO1 CEDTWAXBIMRBDS-UHFFFAOYSA-N 0.000 description 3
JNTPTNNCGDAGEJ-UHFFFAOYSA-N 6-chlorohexan-1-ol Chemical compound OCCCCCCCl JNTPTNNCGDAGEJ-UHFFFAOYSA-N 0.000 description 3
241000114726 Acetes Species 0.000 description 3
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
125000001309 chloro group Chemical group Cl* 0.000 description 3
239000002158 endotoxin Substances 0.000 description 3
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 3
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 3
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
VNYSSYRCGWBHLG-AMOLWHMGSA-N leukotriene B4 Chemical compound CCCCC\C=C/C[C@@H](O)\C=C\C=C\C=C/[C@@H](O)CCCC(O)=O VNYSSYRCGWBHLG-AMOLWHMGSA-N 0.000 description 3
239000000243 solution Substances 0.000 description 3
238000006467 substitution reaction Methods 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
CDHUYLPDPJKKMD-UHFFFAOYSA-N 2-hexadecyl-2,3-dihydrofuran Chemical compound CCCCCCCCCCCCCCCCC1CC=CO1 CDHUYLPDPJKKMD-UHFFFAOYSA-N 0.000 description 2
MVQVNTPHUGQQHK-UHFFFAOYSA-N 3-pyridinemethanol Chemical compound OCC1=CC=CN=C1 MVQVNTPHUGQQHK-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 2
241000283977 Oryctolagus Species 0.000 description 2
206010040070 Septic Shock Diseases 0.000 description 2
150000001414 amino alcohols Chemical class 0.000 description 2
239000005557 antagonist Substances 0.000 description 2
GDCXBZMWKSBSJG-UHFFFAOYSA-N azane;4-methylbenzenesulfonic acid Chemical compound [NH4+].CC1=CC=C(S([O-])(=O)=O)C=C1 GDCXBZMWKSBSJG-UHFFFAOYSA-N 0.000 description 2
230000005540 biological transmission Effects 0.000 description 2
239000008280 blood Substances 0.000 description 2
210000004369 blood Anatomy 0.000 description 2
150000001805 chlorine compounds Chemical class 0.000 description 2
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
229960002887 deanol Drugs 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
230000005764 inhibitory process Effects 0.000 description 2
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
210000004072 lung Anatomy 0.000 description 2
230000035515 penetration Effects 0.000 description 2
239000000843 powder Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 2
206010043554 thrombocytopenia Diseases 0.000 description 2
CYCJXCQLIDUSAT-UHFFFAOYSA-M trimethyl-[2-(5-tridecyloxolan-2-yl)oxyethyl]azanium;bromide Chemical compound [Br-].CCCCCCCCCCCCCC1CCC(OCC[N+](C)(C)C)O1 CYCJXCQLIDUSAT-UHFFFAOYSA-M 0.000 description 2
WPJFPTSGSOSOKZ-UHFFFAOYSA-N 1-[3-[1-(5-hexyloxolan-2-yl)oxyethoxy]propyl]piperidine Chemical compound O1C(CCCCCC)CCC1OC(C)OCCCN1CCCCC1 WPJFPTSGSOSOKZ-UHFFFAOYSA-N 0.000 description 1
AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 1
AHOJTPZHHMJMCW-UHFFFAOYSA-N 1-ethylpiperidin-4-ol Chemical compound CCN1CCC(O)CC1 AHOJTPZHHMJMCW-UHFFFAOYSA-N 0.000 description 1
BDNFVFMYPFGAIP-UHFFFAOYSA-N 2-(2-bromoethoxy)-5-tridecyloxolane Chemical compound CCCCCCCCCCCCCC1CCC(OCCBr)O1 BDNFVFMYPFGAIP-UHFFFAOYSA-N 0.000 description 1
GVMTZIMCHHIXJZ-UHFFFAOYSA-N 2-(2-methylpropyl)-2,3-dihydrofuran Chemical compound CC(C)CC1CC=CO1 GVMTZIMCHHIXJZ-UHFFFAOYSA-N 0.000 description 1
JMGMVAUCLKONOL-UHFFFAOYSA-N 2-(3,4,5-trimethoxyphenyl)-2,3-dihydrofuran Chemical compound COC1=C(OC)C(OC)=CC(C2OC=CC2)=C1 JMGMVAUCLKONOL-UHFFFAOYSA-N 0.000 description 1
YFUQLZPIMNLPTE-UHFFFAOYSA-M 2-(5-heptyloxolan-2-yl)oxyethyl-trimethylazanium;iodide Chemical compound [I-].CCCCCCCC1CCC(OCC[N+](C)(C)C)O1 YFUQLZPIMNLPTE-UHFFFAOYSA-M 0.000 description 1
SANHQHFCOIHPDN-UHFFFAOYSA-N 2-ethoxy-3-piperidin-1-ylpropan-1-ol Chemical compound OCC(CN1CCCCC1)OCC SANHQHFCOIHPDN-UHFFFAOYSA-N 0.000 description 1
AHLLUGFHSVGVOX-UHFFFAOYSA-N 2-heptyl-2,3-dihydrofuran Chemical compound CCCCCCCC1CC=CO1 AHLLUGFHSVGVOX-UHFFFAOYSA-N 0.000 description 1
SLDNUFALUGNXBN-UHFFFAOYSA-N 2-icosyl-2,3-dihydrofuran Chemical compound CCCCCCCCCCCCCCCCCCCCC1CC=CO1 SLDNUFALUGNXBN-UHFFFAOYSA-N 0.000 description 1
RLTUNVAOHOIENQ-UHFFFAOYSA-M 3-(5-icosyloxolan-2-yl)oxy-1,2-dimethylpyridin-1-ium;iodide Chemical compound [I-].O1C(CCCCCCCCCCCCCCCCCCCC)CCC1OC1=CC=C[N+](C)=C1C RLTUNVAOHOIENQ-UHFFFAOYSA-M 0.000 description 1
PYSGFFTXMUWEOT-UHFFFAOYSA-N 3-(dimethylamino)propan-1-ol Chemical compound CN(C)CCCO PYSGFFTXMUWEOT-UHFFFAOYSA-N 0.000 description 1
RQFUZUMFPRMVDX-UHFFFAOYSA-N 3-Bromo-1-propanol Chemical compound OCCCBr RQFUZUMFPRMVDX-UHFFFAOYSA-N 0.000 description 1
XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
YZXBAPSDXZZRGB-DOFZRALJSA-M Arachidonate Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC([O-])=O YZXBAPSDXZZRGB-DOFZRALJSA-M 0.000 description 1
BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
238000012935 Averaging Methods 0.000 description 1
241000219198 Brassica Species 0.000 description 1
235000003351 Brassica cretica Nutrition 0.000 description 1
235000003343 Brassica rupestris Nutrition 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
241000700198 Cavia Species 0.000 description 1
241000588724 Escherichia coli Species 0.000 description 1
241000272168 Laridae Species 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 description 1
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
229960001138 acetylsalicylic acid Drugs 0.000 description 1
239000002253 acid Substances 0.000 description 1
230000001154 acute effect Effects 0.000 description 1
230000002776 aggregation Effects 0.000 description 1
238000004220 aggregation Methods 0.000 description 1
230000001387 anti-histamine Effects 0.000 description 1
239000000739 antihistaminic agent Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
229940114078 arachidonate Drugs 0.000 description 1
210000001367 artery Anatomy 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 1
WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
239000007979 citrate buffer Substances 0.000 description 1
230000009989 contractile response Effects 0.000 description 1
239000003814 drug Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000000499 gel Substances 0.000 description 1
UQEAIHBTYFGYIE-UHFFFAOYSA-N hexamethyldisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 description 1
229940073561 hexamethyldisiloxane Drugs 0.000 description 1
SMWDFEZZVXVKRB-UHFFFAOYSA-O hydron;quinoline Chemical compound [NH+]1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-O 0.000 description 1
PSXRWZBTVAZNSF-UHFFFAOYSA-N hydron;quinoline;chloride Chemical compound Cl.N1=CC=CC2=CC=CC=C21 PSXRWZBTVAZNSF-UHFFFAOYSA-N 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
239000011630 iodine Substances 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
201000002364 leukopenia Diseases 0.000 description 1
231100001022 leukopenia Toxicity 0.000 description 1
150000002617 leukotrienes Chemical class 0.000 description 1
239000000463 material Substances 0.000 description 1
YECBIJXISLIIDS-UHFFFAOYSA-N mepyramine Chemical compound C1=CC(OC)=CC=C1CN(CCN(C)C)C1=CC=CC=N1 YECBIJXISLIIDS-UHFFFAOYSA-N 0.000 description 1
229960000582 mepyramine Drugs 0.000 description 1
ANSUDRATXSJBLY-VKHMYHEASA-N methyl (2s)-2-amino-3-hydroxypropanoate Chemical compound COC(=O)[C@@H](N)CO ANSUDRATXSJBLY-VKHMYHEASA-N 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
235000010460 mustard Nutrition 0.000 description 1
230000000956 myotropic effect Effects 0.000 description 1
NWHBBSJXRTZFKL-UHFFFAOYSA-N n,n-dimethyl-2-(5-tridecyloxolan-2-yl)oxyethanamine Chemical compound CCCCCCCCCCCCCC1CCC(OCCN(C)C)O1 NWHBBSJXRTZFKL-UHFFFAOYSA-N 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
230000037361 pathway Effects 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000012071 phase Substances 0.000 description 1
125000003386 piperidinyl group Chemical group 0.000 description 1
JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
238000000197 pyrolysis Methods 0.000 description 1
238000011084 recovery Methods 0.000 description 1
230000004044 response Effects 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
230000003595 spectral effect Effects 0.000 description 1
208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
DSNBHJFQCNUKMA-SCKDECHMSA-N thromboxane A2 Chemical compound OC(=O)CCC\C=C/C[C@@H]1[C@@H](/C=C/[C@@H](O)CCCCC)O[C@@H]2O[C@H]1C2 DSNBHJFQCNUKMA-SCKDECHMSA-N 0.000 description 1
231100000027 toxicology Toxicity 0.000 description 1
AHLRIDQWYZNBON-UHFFFAOYSA-M trimethyl-[2-(5-tridecyloxolan-2-yl)oxyethyl]azanium;iodide Chemical compound [I-].CCCCCCCCCCCCCC1CCC(OCC[N+](C)(C)C)O1 AHLRIDQWYZNBON-UHFFFAOYSA-M 0.000 description 1
CYCJXCQLIDUSAT-UMIAIAFLSA-M trimethyl-[2-[(2r,5s)-5-tridecyloxolan-2-yl]oxyethyl]azanium;bromide Chemical compound [Br-].CCCCCCCCCCCCC[C@H]1CC[C@H](OCC[N+](C)(C)C)O1 CYCJXCQLIDUSAT-UMIAIAFLSA-M 0.000 description 1
XSSMGUJFXVNSKA-UHFFFAOYSA-M trimethyl-[2-[5-(3,4,5-trimethoxyphenyl)oxolan-2-yl]oxyethyl]azanium;iodide Chemical compound [I-].COC1=C(OC)C(OC)=CC(C2OC(OCC[N+](C)(C)C)CC2)=C1 XSSMGUJFXVNSKA-UHFFFAOYSA-M 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A41—WEARING APPAREL
- A41B—SHIRTS; UNDERWEAR; BABY LINEN; HANDKERCHIEFS
- A41B11/00—Hosiery; Panti-hose
- 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
- C07D405/12—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 chain containing hetero atoms as chain links
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/18—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/20—Oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/94—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom spiro-condensed with carbocyclic rings or ring systems, e.g. griseofulvins
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Bioinformatics & Cheminformatics (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Hematology (AREA)
Diabetes (AREA)
Pulmonology (AREA)
Textile Engineering (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Furan Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Steroid Compounds (AREA)

SE8800171A 1987-01-27 1988-01-20 5-oxi-derivat av tetrahydrofuran, foerfarande foer framstaellning av detta och en terapeutisk komposition SE467974B (sv)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB878701727A GB8701727D0 (en)	1987-01-27	1987-01-27	Tetrahydrofuran derivatives

Publications (3)

Publication Number	Publication Date
SE8800171D0 SE8800171D0 (sv)	1988-01-20
SE8800171L SE8800171L (sv)	1988-07-28
SE467974B true SE467974B (sv)	1992-10-12

Family

ID=10611264

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SE8800171A SE467974B (sv)	1987-01-27	1988-01-20	5-oxi-derivat av tetrahydrofuran, foerfarande foer framstaellning av detta och en terapeutisk komposition

Country Status (31)

Country	Link
US (1)	US4888337A (es)
JP (1)	JPS63192767A (es)
KR (1)	KR900004696B1 (es)
AR (1)	AR243888A1 (es)
AT (1)	AT397800B (es)
AU (1)	AU610787B2 (es)
BE (1)	BE1000694A3 (es)
CA (1)	CA1329205C (es)
CH (1)	CH678426A5 (es)
DE (1)	DE3802362A1 (es)
DK (1)	DK36588A (es)
ES (1)	ES2005504A6 (es)
FI (1)	FI93727C (es)
FR (2)	FR2611139B1 (es)
GB (2)	GB8701727D0 (es)
HK (1)	HK17993A (es)
IE (1)	IE61326B1 (es)
IN (1)	IN169175B (es)
IT (1)	IT1221779B (es)
LU (1)	LU87114A1 (es)
MA (1)	MA21167A1 (es)
MY (1)	MY102310A (es)
NL (1)	NL192520C (es)
NO (1)	NO173332C (es)
NZ (1)	NZ223156A (es)
OA (1)	OA08709A (es)
PT (1)	PT86641B (es)
SE (1)	SE467974B (es)
SG (1)	SG125992G (es)
TN (1)	TNSN88003A1 (es)
ZA (1)	ZA8878B (es)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB8712694D0 (en) *	1987-05-29	1987-07-01	Scras	Tetrahydrofurans etc
GB8712693D0 (en) *	1987-05-29	1987-07-01	Scras	Tetrahydrofurans etc
ES2013834A6 (es) *	1989-01-30	1990-06-01	Uriach & Cia Sa J	Procedimiento para la obtencion de derivados 4-sustituidos de 2-alcoxitetrahidrofurano.
GB9009469D0 (en) *	1990-04-27	1990-06-20	British Bio Technology	Compounds
GB9104746D0 (en) *	1991-03-06	1991-04-17	British Bio Technology	Compounds
GB9114337D0 (en) *	1991-07-03	1991-08-21	British Bio Technology	Compounds
GB9122308D0 (en) *	1991-10-21	1991-12-04	British Bio Technology	Compounds
ES2062943B1 (es) *	1993-03-23	1995-11-16	Uriach & Cia Sa J	Nuevos derivados de la (2-metil-3-piridil) cianometilpiperazinas.
KR100863572B1 (ko)	2007-05-04	2008-10-15	충남대학교산학협력단	신규 페로몬 성 냄새 물질 및 이를 함유하는 돼지의 발정유도용 조성물
US20120226002A1 (en)	2011-03-04	2012-09-06	Gelest Technologies, Inc.	Silicon compounds derived from furfuryl alcohols and methods of preparation

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2185220A (en) *	1938-08-17	1940-01-02	Smith Kline French Lab	Medicinal agent
CH625784A5 (en) *	1976-09-17	1981-10-15	Ciba Geigy Ag	Microbicides
US4289884A (en) *	1979-01-08	1981-09-15	Shell Oil Company	Herbicidal tetrahydrofuran derivatives
DE3413996A1 (de) *	1984-04-13	1985-10-24	Bayer Ag, 5090 Leverkusen	Tetrahydrofuran-2-ylmethylamine
GB8712694D0 (en) *	1987-05-29	1987-07-01	Scras	Tetrahydrofurans etc
GB8712693D0 (en) *	1987-05-29	1987-07-01	Scras	Tetrahydrofurans etc

1987
- 1987-01-27 GB GB878701727A patent/GB8701727D0/en active Pending
1988
- 1988-01-05 IN IN07/DEL/88A patent/IN169175B/en unknown
- 1988-01-06 ZA ZA8878A patent/ZA8878B/xx unknown
- 1988-01-11 NZ NZ223156A patent/NZ223156A/xx unknown
- 1988-01-11 MY MYPI88000021A patent/MY102310A/en unknown
- 1988-01-13 AR AR88309829A patent/AR243888A1/es active
- 1988-01-14 NL NL8800078A patent/NL192520C/nl not_active IP Right Cessation
- 1988-01-15 US US07/144,238 patent/US4888337A/en not_active Expired - Lifetime
- 1988-01-18 FI FI880190A patent/FI93727C/fi not_active IP Right Cessation
- 1988-01-20 SE SE8800171A patent/SE467974B/sv not_active IP Right Cessation
- 1988-01-21 CH CH202/88A patent/CH678426A5/fr not_active IP Right Cessation
- 1988-01-22 ES ES8800154A patent/ES2005504A6/es not_active Expired
- 1988-01-25 BE BE8800082A patent/BE1000694A3/fr active
- 1988-01-25 NO NO880294A patent/NO173332C/no not_active IP Right Cessation
- 1988-01-26 IE IE18888A patent/IE61326B1/en not_active IP Right Cessation
- 1988-01-26 TN TNTNSN88003A patent/TNSN88003A1/fr unknown
- 1988-01-26 CA CA000557392A patent/CA1329205C/en not_active Expired - Fee Related
- 1988-01-26 KR KR1019880000599A patent/KR900004696B1/ko not_active IP Right Cessation
- 1988-01-26 DK DK036588A patent/DK36588A/da not_active Application Discontinuation
- 1988-01-26 GB GB8801652A patent/GB2200634B/en not_active Expired - Fee Related
- 1988-01-26 LU LU87114A patent/LU87114A1/fr unknown
- 1988-01-26 MA MA21404A patent/MA21167A1/fr unknown
- 1988-01-27 DE DE3802362A patent/DE3802362A1/de active Granted
- 1988-01-27 OA OA59270A patent/OA08709A/xx unknown
- 1988-01-27 JP JP63014781A patent/JPS63192767A/ja active Pending
- 1988-01-27 IT IT19222/88A patent/IT1221779B/it active
- 1988-01-27 AU AU10760/88A patent/AU610787B2/en not_active Ceased
- 1988-01-27 PT PT86641A patent/PT86641B/pt not_active IP Right Cessation
- 1988-01-27 FR FR888800908A patent/FR2611139B1/fr not_active Expired
- 1988-01-27 AT AT0016688A patent/AT397800B/de not_active IP Right Cessation
- 1988-01-27 FR FR888800909A patent/FR2609988B1/fr not_active Expired
1992
- 1992-12-10 SG SG1259/92A patent/SG125992G/en unknown
1993
- 1993-03-04 HK HK179/93A patent/HK17993A/xx not_active IP Right Cessation

Also Published As

Publication number	Publication date
BE1000694A3 (fr)	1989-03-14
PT86641A (pt)	1988-02-01
LU87114A1 (fr)	1988-05-03
GB2200634B (en)	1990-09-12
IT1221779B (it)	1990-07-12
FR2611139A1 (fr)	1988-08-26
NO880294L (no)	1988-07-28
FI93727B (fi)	1995-02-15
FR2609988B1 (fr)	1989-12-22
DE3802362A1 (de)	1988-08-04
NO173332C (no)	1993-12-01
US4888337A (en)	1989-12-19
NL192520C (nl)	1997-09-02
ES2005504A6 (es)	1989-03-01
AU1076088A (en)	1988-07-28
SG125992G (en)	1993-02-19
CH678426A5 (es)	1991-09-13
FR2611139B1 (fr)	1989-12-22
PT86641B (pt)	1992-01-31
AR243888A1 (es)	1993-09-30
NZ223156A (en)	1989-08-29
NL8800078A (nl)	1988-08-16
AT397800B (de)	1994-06-27
TNSN88003A1 (fr)	1990-07-10
IE61326B1 (en)	1994-11-02
GB2200634A (en)	1988-08-10
SE8800171D0 (sv)	1988-01-20
GB8801652D0 (en)	1988-02-24
SE8800171L (sv)	1988-07-28
OA08709A (fr)	1989-03-31
DK36588A (da)	1988-07-28
IE880188L (en)	1988-07-27
KR900004696B1 (ko)	1990-07-02
NL192520B (nl)	1997-05-01
IT8819222A0 (it)	1988-01-27
MY102310A (en)	1992-05-28
MA21167A1 (fr)	1988-10-01
ATA16688A (de)	1993-11-15
AU610787B2 (en)	1991-05-23
FR2609988A1 (fr)	1988-07-29
HK17993A (en)	1993-03-12
NO880294D0 (no)	1988-01-25
CA1329205C (en)	1994-05-03
FI880190A (fi)	1988-07-28
DK36588D0 (da)	1988-01-26
ZA8878B (en)	1988-08-31
GB8701727D0 (en)	1987-03-04
FI93727C (fi)	1995-05-26
NO173332B (no)	1993-08-23
FI880190A0 (fi)	1988-01-18
JPS63192767A (ja)	1988-08-10
IN169175B (es)	1991-09-14
KR880009010A (ko)	1988-09-13

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JP2848811B2 (ja)	1999-01-20	トリアゾール系抗真菌薬製造に有用な中間体
EP0247320B1 (de)	1990-12-27	5-Arylalkyl-4-alkoxy-2(5H)-furanone, Zwischenprodukte und Verfahren zu ihrer Herstellung sowie ihre Anwendung als therapeutische Wirkstoffe
US4155909A (en)	1979-05-22	2-Alkyl nicotinoids and processes for their production
SE467974B (sv)	1992-10-12	5-oxi-derivat av tetrahydrofuran, foerfarande foer framstaellning av detta och en terapeutisk komposition
DE3522579C2 (de)	1995-10-12	Neue 1,4-Dihydropyridin-Derivate und Salze derselben, Verfahren zur Herstellung derselben und pharmazeutische Mittel mit einem Gehalt derselben
LU85245A1 (fr)	1984-11-14	Nouveaux composes azoliques,leur preparation et leur utilisation comme antifongiques et fongicides
SU621301A3 (ru)	1978-08-25	Фунгицидна композици
DE69008205T2 (de)	1994-10-06	Abkömmlinge von Benzocycloalkenyldihydroxyalkansäuren, Verfahren zu deren Herstellung und diese enthaltende Pharmazeutika.
Sundberg et al.	1976	Lithiation of methoxyindoles
EP0433233A1 (de)	1991-06-19	Heterocyclische Verbindungen
DE19835324A1 (de)	2000-02-10	Cyclopentabenzofuran-Derivate und ihre Verwendung
NL8920307A (nl)	1990-03-01	Stereospecifieke werkwijze voor de bereiding van enantiomeren van furo3,4-c-pyridine, aldus verkregen verbindingen en therapeutische preparaten die ze bevatten.
FI79536C (fi)	1990-01-10	Foerfarande foer framstaellning av piperidindionderivat med myokardisk skyddsverkan samt med rytmstoerningar bekaempande verkan.
EP0354508A2 (de)	1990-02-14	Benzopyranolderivate
SE434836B (sv)	1984-08-20	Tiazolidinforeningar
IL103229A (en)	1996-09-12	History of imidazolylmethyl-pyridine, their preparation and pharmaceutical preparations containing them
CA1209995A (fr)	1986-08-19	Procede pour la preparation de composes de nicotinamide 1-oxyde n-substitue et de ses sels, et les composes et sels ainsi obtenus
DD281385A5 (de)	1990-08-08	Verfahren zur herstellung von einem 1,3-dioxynalkansaeurederivat
DE3520104C2 (de)	1997-01-23	Naphthoxazine, ihre Herstellung und Verwendung
FR2615736A1 (fr)	1988-12-02	Compositions therapeutiques a base de nouveaux methoxy-5 alcoyl ammonium tetrahydrofuranes et tetrahydrothiophenes
DE3719326C2 (de)	1995-05-11	Fungizide Wirkstoffkombinationen
JPS6157301B2 (es)	1986-12-06
JPS61233667A (ja)	1986-10-17	ジヒドロピリジン、その製造法および該化合物を含有する高血圧治療剤
Atta et al.	1986	Functionally substituted vinyl carbanions, 25. Heteroatom influence on vinylic deprotonation
Chignell et al.	1965	Structures Related to Morphine. XXVIII. 1 Alternative Syntheses of α-and β-2, 9-Dimethyl-2'-hydroxy-5-propyl-6, 7-benzomorphan