DE2536675A1 - Neue 3-(4-thieno-bzw.-furo eckige klammer auf 3,2-c eckige klammer zu pyridinyloxy) -2- propanol-derivate, ihre verwendung und herstellung - Google Patents

Neue 3-(4-thieno-bzw.-furo eckige klammer auf 3,2-c eckige klammer zu pyridinyloxy) -2- propanol-derivate, ihre verwendung und herstellung

Info

Publication number: DE2536675A1
Authority: DE; Germany
Prior art keywords: tert; formula; compounds; butylamino; carbon atoms
Prior art date: 1974-08-27
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 Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Withdrawn

Application number

DE19752536675

Other languages

German (de)

English (en)

Inventor

Franz Troxler

Erik Wiskott

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.)

Sandoz AG

Original Assignee

Sandoz AG

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.)

1974-08-27

Filing date

1975-08-18

Publication date

1976-03-11

1974-08-27 Priority claimed from CH1169074A external-priority patent/CH597236A5/de

1975-04-08 Priority claimed from CH443375A external-priority patent/CH611899A5/de

1975-08-18 Application filed by Sandoz AG filed Critical Sandoz AG

1976-03-11 Publication of DE2536675A1 publication Critical patent/DE2536675A1/de

Status Withdrawn legal-status Critical Current

Links

-1 PYRIDINYLOXY Chemical class 0.000 title claims description 24
238000004519 manufacturing process Methods 0.000 title claims description 3
150000001875 compounds Chemical class 0.000 claims description 45
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 32
125000004432 carbon atom Chemical group C* 0.000 claims description 25
238000000034 method Methods 0.000 claims description 25
239000002253 acid Substances 0.000 claims description 19
239000001257 hydrogen Substances 0.000 claims description 18
229910052739 hydrogen Inorganic materials 0.000 claims description 18
150000003839 salts Chemical class 0.000 claims description 18
239000000460 chlorine Substances 0.000 claims description 17
229910052801 chlorine Inorganic materials 0.000 claims description 17
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 15
229910052794 bromium Inorganic materials 0.000 claims description 15
125000000217 alkyl group Chemical group 0.000 claims description 14
238000006243 chemical reaction Methods 0.000 claims description 14
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 13
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 12
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
125000004093 cyano group Chemical group *C#N 0.000 claims description 8
229910052717 sulfur Inorganic materials 0.000 claims description 8
239000011593 sulfur Substances 0.000 claims description 8
KFZMGEQAYNKOFK-UHFFFAOYSA-N 2-propanol Substances CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 6
125000000129 anionic group Chemical group 0.000 claims description 6
229910052731 fluorine Inorganic materials 0.000 claims description 6
150000002431 hydrogen Chemical class 0.000 claims description 6
229910052799 carbon Inorganic materials 0.000 claims description 5
229910052757 nitrogen Inorganic materials 0.000 claims description 5
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
125000000753 cycloalkyl group Chemical group 0.000 claims description 4
239000011737 fluorine Substances 0.000 claims description 4
125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
125000000160 oxazolidinyl group Chemical group 0.000 claims description 4
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 3
125000004430 oxygen atom Chemical group O* 0.000 claims description 3
125000005359 phenoxyalkyl group Chemical group 0.000 claims description 3
JWBMVCAZXJMSOX-LURJTMIESA-N (2s)-3-(tert-butylamino)propane-1,2-diol Chemical compound CC(C)(C)NC[C@H](O)CO JWBMVCAZXJMSOX-LURJTMIESA-N 0.000 claims description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
125000002252 acyl group Chemical group 0.000 claims description 2
125000001153 fluoro group Chemical group F* 0.000 claims description 2
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
239000007787 solid Substances 0.000 claims description 2
230000003301 hydrolyzing effect Effects 0.000 claims 3
JUKXEIULFQWJAK-NSHDSACASA-N (2S)-1-(tert-butylamino)-3-(2-methylthieno[3,2-c]pyridin-4-yl)oxypropan-2-ol Chemical compound N1=CC=C2SC(C)=CC2=C1OC[C@@H](O)CNC(C)(C)C JUKXEIULFQWJAK-NSHDSACASA-N 0.000 claims 1
125000004429 atom Chemical group 0.000 claims 1
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 1
125000006318 tert-butyl amino group Chemical group [H]N(*)C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 7
FWWOWPGPERBCNJ-UHFFFAOYSA-N 2-hydroxy-4-(2-hydroxyethoxy)-4-oxobutanoic acid Chemical compound OCCOC(=O)CC(O)C(O)=O FWWOWPGPERBCNJ-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 6
150000003254 radicals Chemical class 0.000 description 5
239000007858 starting material Substances 0.000 description 5
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
238000010992 reflux Methods 0.000 description 4
239000000126 substance Substances 0.000 description 4
VFTOHJFKIJLYKN-UHFFFAOYSA-N 7-nitro-9h-fluoren-2-ol Chemical group [O-][N+](=O)C1=CC=C2C3=CC=C(O)C=C3CC2=C1 VFTOHJFKIJLYKN-UHFFFAOYSA-N 0.000 description 3
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 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
150000001721 carbon Chemical group 0.000 description 3
230000000694 effects Effects 0.000 description 3
VZCYOOQTPOCHFL-OWOJBTEDSA-M fumarate(1-) Chemical compound OC(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-M 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 3
JWBMVCAZXJMSOX-ZCFIWIBFSA-N (2r)-3-(tert-butylamino)propane-1,2-diol Chemical compound CC(C)(C)NC[C@@H](O)CO JWBMVCAZXJMSOX-ZCFIWIBFSA-N 0.000 description 2
JMWVYCBWLOCZAB-UHFFFAOYSA-N 4-chloro-2-methylthieno[3,2-c]pyridine Chemical compound N1=CC=C2SC(C)=CC2=C1Cl JMWVYCBWLOCZAB-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
MNQZXJOMYWMBOU-GSVOUGTGSA-N L-(-)-glyceraldehyde Chemical compound OC[C@H](O)C=O MNQZXJOMYWMBOU-GSVOUGTGSA-N 0.000 description 2
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
125000005119 alkyl cycloalkyl group Chemical group 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
239000002585 base Substances 0.000 description 2
238000009835 boiling Methods 0.000 description 2
230000015556 catabolic process Effects 0.000 description 2
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
238000006731 degradation reaction Methods 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
230000002503 metabolic effect Effects 0.000 description 2
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 2
XTEGVFVZDVNBPF-UHFFFAOYSA-L naphthalene-1,5-disulfonate(2-) Chemical compound C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1S([O-])(=O)=O XTEGVFVZDVNBPF-UHFFFAOYSA-L 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
239000011591 potassium Substances 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
238000006467 substitution reaction Methods 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
SQYMXIHEANTFFY-FBLFFUNLSA-N (2R)-3-tert-butyl-5-[(2-methylthieno[3,2-c]pyridin-4-yl)oxymethyl]-2-phenyl-1,3-oxazolidine Chemical compound C1([C@@H]2N(CC(O2)COC2=C3C=C(SC3=CC=N2)C)C(C)(C)C)=CC=CC=C1 SQYMXIHEANTFFY-FBLFFUNLSA-N 0.000 description 1
JERBWURCWWHQBK-UHFFFAOYSA-N (3-tert-butyl-2-phenyl-1,3-oxazolidin-5-yl)methanol Chemical compound CC(C)(C)N1CC(CO)OC1C1=CC=CC=C1 JERBWURCWWHQBK-UHFFFAOYSA-N 0.000 description 1
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
ZPXMCDDVPLMEFT-UHFFFAOYSA-N 2-methyl-2-phenyl-1,3-oxazolidine Chemical compound C=1C=CC=CC=1C1(C)NCCO1 ZPXMCDDVPLMEFT-UHFFFAOYSA-N 0.000 description 1
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
UWDMKTDPDJCJOP-UHFFFAOYSA-N 4-hydroxy-2,2,6,6-tetramethylpiperidin-1-ium-4-carboxylate Chemical compound CC1(C)CC(O)(C(O)=O)CC(C)(C)N1 UWDMKTDPDJCJOP-UHFFFAOYSA-N 0.000 description 1
VAUMDUIUEPIGHM-UHFFFAOYSA-N 5-Methyl-2-thiophenecarboxaldehyde Chemical compound CC1=CC=C(C=O)S1 VAUMDUIUEPIGHM-UHFFFAOYSA-N 0.000 description 1
MNQZXJOMYWMBOU-VKHMYHEASA-N D-glyceraldehyde Chemical compound OC[C@@H](O)C=O MNQZXJOMYWMBOU-VKHMYHEASA-N 0.000 description 1
LELOWRISYMNNSU-UHFFFAOYSA-N Hydrocyanic acid Natural products N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 1
WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 description 1
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
230000001133 acceleration Effects 0.000 description 1
IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
239000000654 additive Substances 0.000 description 1
230000000996 additive effect Effects 0.000 description 1
238000006136 alcoholysis reaction Methods 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
125000004414 alkyl thio group Chemical group 0.000 description 1
230000003288 anthiarrhythmic effect Effects 0.000 description 1
206010003119 arrhythmia Diseases 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
102000012740 beta Adrenergic Receptors Human genes 0.000 description 1
108010079452 beta Adrenergic Receptors Proteins 0.000 description 1
230000000903 blocking effect Effects 0.000 description 1
244000309464 bull Species 0.000 description 1
ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
238000005660 chlorination reaction Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 1
208000029078 coronary artery disease Diseases 0.000 description 1
239000013078 crystal Substances 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
239000003814 drug Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
235000021588 free fatty acids Nutrition 0.000 description 1
239000007789 gas Substances 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
WARQUFORVQESFF-UHFFFAOYSA-N isocyanatoethene Chemical class C=CN=C=O WARQUFORVQESFF-UHFFFAOYSA-N 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
IIYILCZIHLINSB-BTVCFUMJSA-N lead;(2r,3s,4r,5r)-2,3,4,5,6-pentahydroxyhexanal Chemical compound [Pb].OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O IIYILCZIHLINSB-BTVCFUMJSA-N 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000000203 mixture Substances 0.000 description 1
238000006396 nitration reaction Methods 0.000 description 1
150000002917 oxazolidines Chemical class 0.000 description 1
125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
UXCDUFKZSUBXGM-UHFFFAOYSA-N phosphoric tribromide Chemical compound BrP(Br)(Br)=O UXCDUFKZSUBXGM-UHFFFAOYSA-N 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
WLMSZVULHUTVRG-UHFFFAOYSA-N prop-2-enoyl azide Chemical compound C=CC(=O)N=[N+]=[N-] WLMSZVULHUTVRG-UHFFFAOYSA-N 0.000 description 1
238000011321 prophylaxis Methods 0.000 description 1
125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
238000012552 review Methods 0.000 description 1
XMVJITFPVVRMHC-UHFFFAOYSA-N roxarsone Chemical group OC1=CC=C([As](O)(O)=O)C=C1[N+]([O-])=O XMVJITFPVVRMHC-UHFFFAOYSA-N 0.000 description 1
238000003756 stirring Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/04—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D263/06—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by oxygen atoms, attached to ring carbon atoms

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Pyridine Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

DE19752536675 1974-08-27 1975-08-18 Neue 3-(4-thieno-bzw.-furo eckige klammer auf 3,2-c eckige klammer zu pyridinyloxy) -2- propanol-derivate, ihre verwendung und herstellung Withdrawn DE2536675A1 (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CH1169074A CH597236A5 (en)	1974-08-27	1974-08-27	1-Amino-3-(thieno (3,2-c)pyridine-4-yl-oxy)-2-propanols
CH443375A CH611899A5 (en)	1975-04-08	1975-04-08	Process for the preparation of novel thieno[3,2-c]pyridine derivatives

Publications (1)

Publication Number	Publication Date
DE2536675A1 true DE2536675A1 (de)	1976-03-11

Family

ID=25695446

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DE19752536675 Withdrawn DE2536675A1 (de)	1974-08-27	1975-08-18	Neue 3-(4-thieno-bzw.-furo eckige klammer auf 3,2-c eckige klammer zu pyridinyloxy) -2- propanol-derivate, ihre verwendung und herstellung

Country Status (13)

Country	Link
JP (1)	JPS5148693A (da)
AU (1)	AU8427775A (da)
DD (1)	DD121945A5 (da)
DE (1)	DE2536675A1 (da)
DK (1)	DK372475A (da)
ES (1)	ES440430A1 (da)
FI (1)	FI752331A (da)
FR (1)	FR2282886A1 (da)
GB (1)	GB1509256A (da)
IL (1)	IL47991A0 (da)
NL (1)	NL7509943A (da)
NO (1)	NO752881L (da)
SE (1)	SE7509270L (da)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2007066127A2 (en)	2005-12-09	2007-06-14	Xention Limited	Thieno ( 3 , 2-c) pyridine compounds

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2452490A1 (fr) *	1979-03-30	1980-10-24	Sanofi Sa	Nouveaux derives des thieno(2,3-c) et 3,2-c) pyridines, leur procede de preparation et leur application therapeutique
US20100137388A1 (en) *	2007-04-19	2010-06-03	Barden Christopher J	Therapeutic Pro-Antibiotic Agents and Methods of Use Thereof

1975
- 1975-08-18 DK DK372475A patent/DK372475A/da unknown
- 1975-08-18 FI FI752331A patent/FI752331A/fi not_active Application Discontinuation
- 1975-08-18 DE DE19752536675 patent/DE2536675A1/de not_active Withdrawn
- 1975-08-19 NO NO752881A patent/NO752881L/no unknown
- 1975-08-19 SE SE7509270A patent/SE7509270L/xx unknown
- 1975-08-22 FR FR7525983A patent/FR2282886A1/fr active Granted
- 1975-08-22 NL NL7509943A patent/NL7509943A/xx not_active Application Discontinuation
- 1975-08-22 GB GB34917/75A patent/GB1509256A/en not_active Expired
- 1975-08-25 ES ES440430A patent/ES440430A1/es not_active Expired
- 1975-08-26 IL IL47991A patent/IL47991A0/xx unknown
- 1975-08-26 JP JP50102626A patent/JPS5148693A/ja active Pending
- 1975-08-26 DD DD188030A patent/DD121945A5/xx unknown
- 1975-08-26 AU AU84277/75A patent/AU8427775A/en not_active Expired

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2007066127A2 (en)	2005-12-09	2007-06-14	Xention Limited	Thieno ( 3 , 2-c) pyridine compounds

Also Published As

Publication number	Publication date
AU8427775A (en)	1977-03-03
GB1509256A (en)	1978-05-04
FI752331A (da)	1976-02-28
ES440430A1 (es)	1977-08-16
FR2282886A1 (fr)	1976-03-26
SE7509270L (sv)	1976-03-01
FR2282886B1 (da)	1980-04-18
NO752881L (da)	1976-03-01
DD121945A5 (da)	1976-09-05
DK372475A (da)	1976-02-28
JPS5148693A (da)	1976-04-26
NL7509943A (nl)	1976-03-02
IL47991A0 (en)	1975-11-25

Publication	Publication Date	Title
EP0006524A1 (de)	1980-01-09	Neue Tetrahydropyridin- und Piperidinderivate und deren Säureadditionssalze, Verfahren zu deren Herstellung und solche enthaltende pharmazeutische Zusammensetzungen
DE60121431T2 (de)	2007-01-18	Ein pyridin-n-oxid-derivat und ein prozess zu seiner umsetzung in pharmazeutische wirkstoffe
DE69224507T2 (de)	1998-08-20	Beta-Oxo-Beta-Benzenepropanthioamidderivate
DE4038335A1 (de)	1992-06-04	Neue pyridinderivate, verfahren zu ihrer herstellung und verwendung als arzneimittel
DE1809386A1 (de)	1970-06-11	Verfahren zur Herstellung von 1,5-disubstituierten 4-Cyanopyrazolen
EP0174910A2 (de)	1986-03-19	Verfahren zur Herstellung von 4-Phenyl-pyrrol-derivaten
DE102004041531A1 (de)	2006-03-02	Verfahren zum Herstellen von Biphenylaminen
EP0380712A1 (de)	1990-08-08	Verfahren zur Herstellung von 2,6-Dichlordiphenylaminessigsäurederivaten
DE2536675A1 (de)	1976-03-11	Neue 3-(4-thieno-bzw.-furo eckige klammer auf 3,2-c eckige klammer zu pyridinyloxy) -2- propanol-derivate, ihre verwendung und herstellung
DE2118315C3 (de)	1975-04-03	2-(1H)-Chinazolinonderivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
DE2406881A1 (de)	1974-08-29	Neue carbonsaeure-derivate und verfahren zu deren herstellung
DE2633992A1 (de)	1978-02-09	Neue pyrazol-derivate, ihre herstellung und verwendung
DE1668968A1 (de)	1971-10-14	Neue organische Verbindungen
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DE69018619T2 (de)	1995-09-21	Alpha, beta-ungesättigte ketone und ketoximderivat.
CH622796A5 (en)	1981-04-30	Process for the preparation of novel thieno[3,2-c]pyridine derivatives
AT366370B (de)	1982-04-13	Verfahren zur herstellung von neuen benz(g) isochinolinderivaten
AT360992B (de)	1981-02-10	Verfahren zur herstellung neuer phenylazacyclo- alkane und von deren salzen und optisch aktiven verbindungen
DE2656573C2 (de)	1979-01-11	Verfahren zur Herstellung von Nsubstituierten 3-(6-Halogen-3-carbalkoxy-4-pyridylamino)-propionsäureestern
AT376417B (de)	1984-11-26	Verfahren zur herstellung von phenylaethanolaminen und ihren salzen
DE2348951A1 (de)	1974-04-11	Octahydroisochinoline, ihre salze, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
AT282629B (de)	1970-07-10	Verfahren zur herstellung neuer zimtsaeureamide
AT360995B (de)	1981-02-10	Verfahren zur herstellung neuer phenylazacyclo- alkane und von deren salzen und optisch aktiven verbindungen
CH527200A (de)	1972-08-31	Verfahren zur Herstellung von neuen, Nitrogruppen enthaltenden Chinazolinonderivaten
DE2113254C3 (de)	1978-01-26	Verfahren zur Herstellung von γ-Piperidinoburyrophenonderivaten

Legal Events

Date	Code	Title	Description
1982-12-09	8139	Disposal/non-payment of the annual fee

DE2536675A1 - Neue 3-(4-thieno-bzw.-furo eckige klammer auf 3,2-c eckige klammer zu pyridinyloxy) -2- propanol-derivate, ihre verwendung und herstellung - Google Patents

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Applications Claiming Priority (2)

Publications (1)

Family

ID=25695446

Family Applications (1)

Country Status (13)

Cited By (1)

Families Citing this family (2)

Cited By (1)

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