DD287498A5 - Verfahren zur herstellung von sulfamiden - Google Patents

Verfahren zur herstellung von sulfamiden Download PDF

Info

Publication number: DD287498A5
Authority: DD; German Democratic Republic
Prior art keywords: acid; ethyl; mmol; general formula; group
Prior art date: 1988-08-31

Application number

DD89332133A

Other languages

German (de)

English (en)

Inventor

Hansjoerg Beck

Ernst-Christian Witte

Karlheinz Stegmeier

Liesel Doerge

Original Assignee

��@��@��k��

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.)

1988-08-31

Filing date

1989-08-28

Publication date

1991-02-28

1989-08-28 Application filed by ��@��@��k�� filed Critical ��@��@��k��

1991-02-28 Publication of DD287498A5 publication Critical patent/DD287498A5/de

Links

238000004519 manufacturing process Methods 0.000 title 1
238000000034 method Methods 0.000 claims abstract description 19
238000002360 preparation method Methods 0.000 claims abstract description 15
230000008569 process Effects 0.000 claims abstract description 9
229940124530 sulfonamide Drugs 0.000 claims abstract description 6
150000003456 sulfonamides Chemical class 0.000 claims abstract description 6
150000001875 compounds Chemical class 0.000 claims description 74
-1 cyanomethyl Chemical group 0.000 claims description 59
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 39
239000002253 acid Substances 0.000 claims description 29
ULRPISSMEBPJLN-UHFFFAOYSA-N 2h-tetrazol-5-amine Chemical compound NC1=NN=NN1 ULRPISSMEBPJLN-UHFFFAOYSA-N 0.000 claims description 16
150000003839 salts Chemical class 0.000 claims description 16
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical class OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 14
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
150000002148 esters Chemical class 0.000 claims description 8
JUINSXZKUKVTMD-UHFFFAOYSA-N hydrogen azide Chemical compound N=[N+]=[N-] JUINSXZKUKVTMD-UHFFFAOYSA-N 0.000 claims description 8
150000001408 amides Chemical class 0.000 claims description 7
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
125000004093 cyano group Chemical group *C#N 0.000 claims description 6
150000002825 nitriles Chemical class 0.000 claims description 6
150000008064 anhydrides Chemical class 0.000 claims description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
229910052760 oxygen Inorganic materials 0.000 claims description 5
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
150000004820 halides Chemical class 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
150000007530 organic bases Chemical class 0.000 claims description 4
239000001301 oxygen Substances 0.000 claims description 4
150000001735 carboxylic acids Chemical class 0.000 claims description 3
150000007529 inorganic bases Chemical class 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
150000007928 imidazolide derivatives Chemical class 0.000 claims description 2
230000003287 optical effect Effects 0.000 claims description 2
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
150000003842 bromide salts Chemical class 0.000 claims 1
150000003841 chloride salts Chemical class 0.000 claims 1
125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
238000011282 treatment Methods 0.000 abstract description 9
150000003180 prostaglandins Chemical class 0.000 abstract description 5
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 abstract description 5
208000030159 metabolic disease Diseases 0.000 abstract description 4
239000003814 drug Substances 0.000 abstract description 3
229940079593 drug Drugs 0.000 abstract 1
230000002401 inhibitory effect Effects 0.000 abstract 1
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 75
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 73
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 69
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 54
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 49
239000000243 solution Substances 0.000 description 47
239000013078 crystal Substances 0.000 description 41
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 37
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 35
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 28
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
238000006243 chemical reaction Methods 0.000 description 27
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 26
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 26
239000000203 mixture Substances 0.000 description 26
239000002904 solvent Substances 0.000 description 24
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
239000000047 product Substances 0.000 description 18
239000002244 precipitate Substances 0.000 description 16
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 13
229910000041 hydrogen chloride Inorganic materials 0.000 description 13
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 12
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
238000009833 condensation Methods 0.000 description 12
230000005494 condensation Effects 0.000 description 12
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 11
239000008346 aqueous phase Substances 0.000 description 11
239000012074 organic phase Substances 0.000 description 11
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
150000001412 amines Chemical class 0.000 description 10
239000012230 colorless oil Substances 0.000 description 10
239000011734 sodium Substances 0.000 description 10
229910052938 sodium sulfate Inorganic materials 0.000 description 10
235000011152 sodium sulphate Nutrition 0.000 description 10
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
150000001732 carboxylic acid derivatives Chemical class 0.000 description 9
239000012071 phase Substances 0.000 description 9
239000007858 starting material Substances 0.000 description 9
239000000725 suspension Substances 0.000 description 9
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
238000005984 hydrogenation reaction Methods 0.000 description 8
125000006239 protecting group Chemical group 0.000 description 8
238000003756 stirring Methods 0.000 description 8
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 7
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 7
239000003513 alkali Substances 0.000 description 7
235000019270 ammonium chloride Nutrition 0.000 description 7
230000009467 reduction Effects 0.000 description 7
238000012360 testing method Methods 0.000 description 7
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 6
229910052943 magnesium sulfate Inorganic materials 0.000 description 6
235000019341 magnesium sulphate Nutrition 0.000 description 6
KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
238000010992 reflux Methods 0.000 description 6
239000000126 substance Substances 0.000 description 6
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
KJUGUADJHNHALS-UHFFFAOYSA-N 1H-tetrazole Substances C=1N=NNN=1 KJUGUADJHNHALS-UHFFFAOYSA-N 0.000 description 5
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 5
PIAOLBVUVDXHHL-UHFFFAOYSA-N 2-nitroethenylbenzene Chemical compound [O-][N+](=O)C=CC1=CC=CC=C1 PIAOLBVUVDXHHL-UHFFFAOYSA-N 0.000 description 5
ZLYBFBAHAQEEQQ-UHFFFAOYSA-N 4-chlorobenzenesulfonyl chloride Chemical compound ClC1=CC=C(S(Cl)(=O)=O)C=C1 ZLYBFBAHAQEEQQ-UHFFFAOYSA-N 0.000 description 5
241001465754 Metazoa Species 0.000 description 5
MODKMHXGCGKTLE-UHFFFAOYSA-N N-acetylphenylethylamine Chemical compound CC(=O)NCCC1=CC=CC=C1 MODKMHXGCGKTLE-UHFFFAOYSA-N 0.000 description 5
150000008044 alkali metal hydroxides Chemical class 0.000 description 5
239000002585 base Substances 0.000 description 5
WVDDGKGOMKODPV-UHFFFAOYSA-N hydroxymethyl benzene Natural products OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 5
JBFYUZGYRGXSFL-UHFFFAOYSA-N imidazolide Chemical compound C1=C[N-]C=N1 JBFYUZGYRGXSFL-UHFFFAOYSA-N 0.000 description 5
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 5
LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical compound OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
238000005160 1H NMR spectroscopy Methods 0.000 description 4
AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
239000002841 Lewis acid Substances 0.000 description 4
BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
229960000583 acetic acid Drugs 0.000 description 4
230000002776 aggregation Effects 0.000 description 4
238000004220 aggregation Methods 0.000 description 4
229910052783 alkali metal Inorganic materials 0.000 description 4
125000005210 alkyl ammonium group Chemical group 0.000 description 4
230000003042 antagnostic effect Effects 0.000 description 4
GRSTVVGJSKHCCS-UHFFFAOYSA-N bis(1h-imidazol-2-yl)methanone Chemical compound N=1C=CNC=1C(=O)C1=NC=CN1 GRSTVVGJSKHCCS-UHFFFAOYSA-N 0.000 description 4
229910052799 carbon Inorganic materials 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
238000001816 cooling Methods 0.000 description 4
238000001035 drying Methods 0.000 description 4
230000000694 effects Effects 0.000 description 4
239000012362 glacial acetic acid Substances 0.000 description 4
150000007517 lewis acids Chemical class 0.000 description 4
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 4
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
238000001953 recrystallisation Methods 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
HRNSMAALDOVHSE-UHFFFAOYSA-N 1-nitro-2-phenylethenol Chemical compound [O-][N+](=O)C(O)=CC1=CC=CC=C1 HRNSMAALDOVHSE-UHFFFAOYSA-N 0.000 description 3
125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
208000024172 Cardiovascular disease Diseases 0.000 description 3
238000005481 NMR spectroscopy Methods 0.000 description 3
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
125000000217 alkyl group Chemical group 0.000 description 3
125000003277 amino group Chemical group 0.000 description 3
239000005557 antagonist Substances 0.000 description 3
239000011230 binding agent Substances 0.000 description 3
238000009835 boiling Methods 0.000 description 3
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
238000001914 filtration Methods 0.000 description 3
239000005457 ice water Substances 0.000 description 3
239000012442 inert solvent Substances 0.000 description 3
238000002347 injection Methods 0.000 description 3
239000007924 injection Substances 0.000 description 3
230000003907 kidney function Effects 0.000 description 3
UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 3
HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 description 3
230000007935 neutral effect Effects 0.000 description 3
239000003921 oil Substances 0.000 description 3
235000019198 oils Nutrition 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
231100000915 pathological change Toxicity 0.000 description 3
230000036285 pathological change Effects 0.000 description 3
SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 description 3
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
229910000104 sodium hydride Inorganic materials 0.000 description 3
239000007787 solid Substances 0.000 description 3
125000003831 tetrazolyl group Chemical group 0.000 description 3
RZWIIPASKMUIAC-VQTJNVASSA-N thromboxane Chemical compound CCCCCCCC[C@H]1OCCC[C@@H]1CCCCCCC RZWIIPASKMUIAC-VQTJNVASSA-N 0.000 description 3
ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 3
DZGWFCGJZKJUFP-UHFFFAOYSA-N tyramine Chemical compound NCCC1=CC=C(O)C=C1 DZGWFCGJZKJUFP-UHFFFAOYSA-N 0.000 description 3
229960003732 tyramine Drugs 0.000 description 3
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
AWBCIZDYUXMRKU-UHFFFAOYSA-N 2-[3-(2-aminoethyl)phenoxy]acetic acid Chemical compound NCCC1=CC=CC(OCC(O)=O)=C1 AWBCIZDYUXMRKU-UHFFFAOYSA-N 0.000 description 2
YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 description 2
VLLSCJFPVSQXDM-UHFFFAOYSA-N 2-phenoxyacetonitrile Chemical compound N#CCOC1=CC=CC=C1 VLLSCJFPVSQXDM-UHFFFAOYSA-N 0.000 description 2
NWBJKWCWQKPHNF-UHFFFAOYSA-N 2-phenyl-n-(2h-tetrazol-5-yl)acetamide Chemical compound N1=NNN=C1NC(=O)CC1=CC=CC=C1 NWBJKWCWQKPHNF-UHFFFAOYSA-N 0.000 description 2
HHHDJHHNEURCNV-UHFFFAOYSA-N 4-chlorobenzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=C(Cl)C=C1 HHHDJHHNEURCNV-UHFFFAOYSA-N 0.000 description 2
RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
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 2
229910010082 LiAlH Inorganic materials 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
239000007868 Raney catalyst Substances 0.000 description 2
229910000564 Raney nickel Inorganic materials 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
229910001854 alkali hydroxide Inorganic materials 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
YDPLDMLRERBXAV-UHFFFAOYSA-N aluminum;triazide Chemical compound [Al+3].[N-]=[N+]=[N-].[N-]=[N+]=[N-].[N-]=[N+]=[N-] YDPLDMLRERBXAV-UHFFFAOYSA-N 0.000 description 2
239000000908 ammonium hydroxide Substances 0.000 description 2
UAZDIGCOBKKMPU-UHFFFAOYSA-O azanium;azide Chemical compound [NH4+].[N-]=[N+]=[N-] UAZDIGCOBKKMPU-UHFFFAOYSA-O 0.000 description 2
150000001540 azides Chemical class 0.000 description 2
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
235000019445 benzyl alcohol Nutrition 0.000 description 2
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 2
229940073608 benzyl chloride Drugs 0.000 description 2
HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
WPNIYZLEKVXEAC-UHFFFAOYSA-N benzyl n-[2-(3-hydroxyphenyl)ethyl]carbamate Chemical compound OC1=CC=CC(CCNC(=O)OCC=2C=CC=CC=2)=C1 WPNIYZLEKVXEAC-UHFFFAOYSA-N 0.000 description 2
DFRGAHOZQCQHRX-UHFFFAOYSA-N benzyl n-[2-[3-(oxan-2-yloxy)phenyl]ethyl]carbamate Chemical compound C=1C=CC=CC=1COC(=O)NCCC(C=1)=CC=CC=1OC1CCCCO1 DFRGAHOZQCQHRX-UHFFFAOYSA-N 0.000 description 2
SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 2
210000004369 blood Anatomy 0.000 description 2
239000008280 blood Substances 0.000 description 2
230000037396 body weight Effects 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
239000000872 buffer Substances 0.000 description 2
229910002091 carbon monoxide Inorganic materials 0.000 description 2
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 description 2
238000006114 decarboxylation reaction Methods 0.000 description 2
239000012024 dehydrating agents‎ Substances 0.000 description 2
239000003480 eluent Substances 0.000 description 2
MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 2
125000004494 ethyl ester group Chemical group 0.000 description 2
239000007789 gas Substances 0.000 description 2
229920006158 high molecular weight polymer Polymers 0.000 description 2
229910052500 inorganic mineral Inorganic materials 0.000 description 2
239000007788 liquid Substances 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
229920000609 methyl cellulose Polymers 0.000 description 2
239000001923 methylcellulose Substances 0.000 description 2
235000010755 mineral Nutrition 0.000 description 2
239000011707 mineral Substances 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
229940117803 phenethylamine Drugs 0.000 description 2
229960003424 phenylacetic acid Drugs 0.000 description 2
239000003279 phenylacetic acid Substances 0.000 description 2
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 2
239000002798 polar solvent Substances 0.000 description 2
229920000137 polyphosphoric acid Polymers 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000012429 reaction media Substances 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
239000012312 sodium hydride Substances 0.000 description 2
208000010110 spontaneous platelet aggregation Diseases 0.000 description 2
230000004083 survival effect Effects 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
150000003536 tetrazoles Chemical class 0.000 description 2
PCTNAMGLSYHIPL-UHFFFAOYSA-N tin(4+) tetraazide Chemical compound [Sn+4].[N-]=[N+]=[N-].[N-]=[N+]=[N-].[N-]=[N+]=[N-].[N-]=[N+]=[N-] PCTNAMGLSYHIPL-UHFFFAOYSA-N 0.000 description 2
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
QFDUTPNKBRXHTC-UHFFFAOYSA-N zinc diazide Chemical compound [Zn++].[N-]=[N+]=[N-].[N-]=[N+]=[N-] QFDUTPNKBRXHTC-UHFFFAOYSA-N 0.000 description 2
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
125000004209 (C1-C8) alkyl group Chemical group 0.000 description 1
WXUAQHNMJWJLTG-VKHMYHEASA-N (S)-methylsuccinic acid Chemical compound OC(=O)[C@@H](C)CC(O)=O WXUAQHNMJWJLTG-VKHMYHEASA-N 0.000 description 1
125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 1
YZUPZGFPHUVJKC-UHFFFAOYSA-N 1-bromo-2-methoxyethane Chemical compound COCCBr YZUPZGFPHUVJKC-UHFFFAOYSA-N 0.000 description 1
RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
OMAFFHIGWTVZOH-UHFFFAOYSA-N 1-methyltetrazole Chemical compound CN1C=NN=N1 OMAFFHIGWTVZOH-UHFFFAOYSA-N 0.000 description 1
QWAVNXZAQASOML-UHFFFAOYSA-N 1-phenoxypropan-2-one Chemical compound CC(=O)COC1=CC=CC=C1 QWAVNXZAQASOML-UHFFFAOYSA-N 0.000 description 1
PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
IOXOZOPLBFXYLM-UHFFFAOYSA-N 2-(4-nitrophenyl)ethanamine Chemical compound NCCC1=CC=C([N+]([O-])=O)C=C1 IOXOZOPLBFXYLM-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
DCJVXUKMTXCPLB-UHFFFAOYSA-N 2-[3-(oxan-2-yloxy)phenyl]ethanamine Chemical compound NCCC1=CC=CC(OC2OCCCC2)=C1 DCJVXUKMTXCPLB-UHFFFAOYSA-N 0.000 description 1
KSDLMZGXBJMPGK-UHFFFAOYSA-N 2-[3-[2-(phenylmethoxycarbonylamino)ethyl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=CC(CCNC(=O)OCC=2C=CC=CC=2)=C1 KSDLMZGXBJMPGK-UHFFFAOYSA-N 0.000 description 1
HZIROSQHFKBTPF-UHFFFAOYSA-N 2-[3-[2-[(4-bromophenyl)sulfonylamino]ethyl]phenoxy]-n-(2h-tetrazol-5-yl)acetamide Chemical compound C1=CC(Br)=CC=C1S(=O)(=O)NCCC1=CC=CC(OCC(=O)NC=2NN=NN=2)=C1 HZIROSQHFKBTPF-UHFFFAOYSA-N 0.000 description 1
GROSXDULGYZWAV-UHFFFAOYSA-N 2-[3-[2-[(4-chlorophenyl)sulfonylamino]ethyl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=CC(CCNS(=O)(=O)C=2C=CC(Cl)=CC=2)=C1 GROSXDULGYZWAV-UHFFFAOYSA-N 0.000 description 1
PVQGFSYWDGVIKS-UHFFFAOYSA-N 2-[3-[2-[(4-chlorophenyl)sulfonylamino]ethyl]phenoxy]propanedioic acid Chemical compound OC(=O)C(C(O)=O)OC1=CC=CC(CCNS(=O)(=O)C=2C=CC(Cl)=CC=2)=C1 PVQGFSYWDGVIKS-UHFFFAOYSA-N 0.000 description 1
FISNNLDVYJHQMG-UHFFFAOYSA-N 2-[3-[2-[[4-(trifluoromethyl)phenyl]sulfonylamino]ethyl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=CC(CCNS(=O)(=O)C=2C=CC(=CC=2)C(F)(F)F)=C1 FISNNLDVYJHQMG-UHFFFAOYSA-N 0.000 description 1
LQDQPJQZRPZDON-UHFFFAOYSA-N 2-[3-[[(4-fluorophenyl)sulfonylamino]methyl]phenoxy]-n-(2h-tetrazol-5-yl)acetamide Chemical compound C1=CC(F)=CC=C1S(=O)(=O)NCC1=CC=CC(OCC(=O)NC=2NN=NN=2)=C1 LQDQPJQZRPZDON-UHFFFAOYSA-N 0.000 description 1
MMOWTZBBAJAEGV-UHFFFAOYSA-N 2-[4-(2h-tetrazol-5-ylmethoxy)phenyl]ethanamine Chemical compound C1=CC(CCN)=CC=C1OCC1=NN=NN1 MMOWTZBBAJAEGV-UHFFFAOYSA-N 0.000 description 1
BCCGHFWVISPPSY-UHFFFAOYSA-N 2-[4-[2-[(4-chlorophenyl)sulfonylamino]ethyl]phenoxy]-n-(2h-tetrazol-5-yl)acetamide Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)NCCC(C=C1)=CC=C1OCC(=O)NC1=NN=NN1 BCCGHFWVISPPSY-UHFFFAOYSA-N 0.000 description 1
RMWMQDPGZUPJBR-UHFFFAOYSA-N 2-[4-[2-[[4-(trifluoromethyl)phenyl]sulfonylamino]ethyl]phenyl]acetic acid Chemical compound C1=CC(CC(=O)O)=CC=C1CCNS(=O)(=O)C1=CC=C(C(F)(F)F)C=C1 RMWMQDPGZUPJBR-UHFFFAOYSA-N 0.000 description 1
WEJCCVBZFBULSI-UHFFFAOYSA-N 2-[4-[[(4-chlorophenyl)sulfonylamino]methyl]phenoxy]acetic acid Chemical compound C1=CC(OCC(=O)O)=CC=C1CNS(=O)(=O)C1=CC=C(Cl)C=C1 WEJCCVBZFBULSI-UHFFFAOYSA-N 0.000 description 1
SNDPXSYFESPGGJ-UHFFFAOYSA-N 2-aminopentanoic acid Chemical compound CCCC(N)C(O)=O SNDPXSYFESPGGJ-UHFFFAOYSA-N 0.000 description 1
IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical compound OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 description 1
SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 1
JVSMPWHQUPKRNV-UHFFFAOYSA-N 2h-tetrazol-5-amine;hydrate Chemical compound O.NC=1N=NNN=1 JVSMPWHQUPKRNV-UHFFFAOYSA-N 0.000 description 1
LHOXYFFMOPWNRY-UHFFFAOYSA-N 3-[2-(benzylamino)ethyl]phenol Chemical compound OC1=CC=CC(CCNCC=2C=CC=CC=2)=C1 LHOXYFFMOPWNRY-UHFFFAOYSA-N 0.000 description 1
NYXUZWMLYJOHGO-UHFFFAOYSA-N 4-[4-[2-[(4-bromophenyl)sulfonylamino]ethyl]phenyl]-4-oxo-n-(2h-tetrazol-5-yl)butanamide Chemical compound C1=CC(Br)=CC=C1S(=O)(=O)NCCC1=CC=C(C(=O)CCC(=O)NC=2NN=NN=2)C=C1 NYXUZWMLYJOHGO-UHFFFAOYSA-N 0.000 description 1
OWLSLOAXNVIFRC-UHFFFAOYSA-N 4-[4-[2-[(4-chlorophenyl)sulfonylamino]ethyl]phenyl]-4-hydroxybutanoic acid Chemical compound C1=CC(C(CCC(O)=O)O)=CC=C1CCNS(=O)(=O)C1=CC=C(Cl)C=C1 OWLSLOAXNVIFRC-UHFFFAOYSA-N 0.000 description 1
XRMIQIGVCIIOCV-UHFFFAOYSA-N 4-[4-[2-[(4-cyanophenyl)sulfonylamino]ethyl]phenyl]-4-oxobutanoic acid Chemical compound C1=CC(C(=O)CCC(=O)O)=CC=C1CCNS(=O)(=O)C1=CC=C(C#N)C=C1 XRMIQIGVCIIOCV-UHFFFAOYSA-N 0.000 description 1
QPJOFEGDXFNAEP-UHFFFAOYSA-N 4-chloro-n-[2-(4-nitrophenyl)ethyl]benzenesulfonamide Chemical compound C1=CC([N+](=O)[O-])=CC=C1CCNS(=O)(=O)C1=CC=C(Cl)C=C1 QPJOFEGDXFNAEP-UHFFFAOYSA-N 0.000 description 1
KBPVCFUNLQTECB-UHFFFAOYSA-N 4-chloro-n-[2-[4-(2h-tetrazole-5-carbonyl)phenyl]ethyl]benzenesulfonamide Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)NCCC1=CC=C(C(=O)C=2NN=NN=2)C=C1 KBPVCFUNLQTECB-UHFFFAOYSA-N 0.000 description 1
DBMFYTQPPBBKHI-UHFFFAOYSA-N 4-cyanobenzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=C(C#N)C=C1 DBMFYTQPPBBKHI-UHFFFAOYSA-N 0.000 description 1
BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 description 1
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 1
JKRRYTWEDNUVKT-UHFFFAOYSA-N 5-[4-(2-aminoethyl)phenyl]pentanoic acid Chemical compound NCCC1=CC=C(CCCCC(O)=O)C=C1 JKRRYTWEDNUVKT-UHFFFAOYSA-N 0.000 description 1
206010001052 Acute respiratory distress syndrome Diseases 0.000 description 1
229920001817 Agar Polymers 0.000 description 1
229910000838 Al alloy Inorganic materials 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical compound NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
206010006482 Bronchospasm Diseases 0.000 description 1
FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
RENMDAKOXSCIGH-UHFFFAOYSA-N Chloroacetonitrile Chemical compound ClCC#N RENMDAKOXSCIGH-UHFFFAOYSA-N 0.000 description 1
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
241000206672 Gelidium Species 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
229930194542 Keto Natural products 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
229930195725 Mannitol Natural products 0.000 description 1
241000699666 Mus <mouse, genus> Species 0.000 description 1
238000011785 NMRI mouse Methods 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
208000030831 Peripheral arterial occlusive disease Diseases 0.000 description 1
229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
239000004698 Polyethylene Substances 0.000 description 1
208000010378 Pulmonary Embolism Diseases 0.000 description 1
208000013616 Respiratory Distress Syndrome Diseases 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
208000007107 Stomach Ulcer Diseases 0.000 description 1
101150046432 Tril gene Proteins 0.000 description 1
JQSIHOWVTRFFNR-UHFFFAOYSA-N [NH4+].[NH4+].C=C.CC([O-])=O.CC([O-])=O Chemical compound [NH4+].[NH4+].C=C.CC([O-])=O.CC([O-])=O JQSIHOWVTRFFNR-UHFFFAOYSA-N 0.000 description 1
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
230000003213 activating effect Effects 0.000 description 1
125000004442 acylamino group Chemical group 0.000 description 1
239000000654 additive Substances 0.000 description 1
201000000028 adult respiratory distress syndrome Diseases 0.000 description 1
235000010419 agar Nutrition 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
238000010640 amide synthesis reaction Methods 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
238000013459 approach Methods 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
208000006673 asthma Diseases 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
JXHYCCGOZUGBFD-UHFFFAOYSA-N benzoic acid;hydrochloride Chemical compound Cl.OC(=O)C1=CC=CC=C1 JXHYCCGOZUGBFD-UHFFFAOYSA-N 0.000 description 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
RKEFXYGKUOTQKH-UHFFFAOYSA-N benzyl n-[2-[3-[2-oxo-2-(2h-tetrazol-5-ylamino)ethoxy]phenyl]ethyl]carbamate Chemical compound N=1N=NNC=1NC(=O)COC(C=1)=CC=CC=1CCNC(=O)OCC1=CC=CC=C1 RKEFXYGKUOTQKH-UHFFFAOYSA-N 0.000 description 1
125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
230000033228 biological regulation Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
150000001649 bromium compounds Chemical class 0.000 description 1
230000007885 bronchoconstriction Effects 0.000 description 1
UETLMBWMVIQIGU-UHFFFAOYSA-N calcium azide Chemical compound [Ca+2].[N-]=[N+]=[N-].[N-]=[N+]=[N-] UETLMBWMVIQIGU-UHFFFAOYSA-N 0.000 description 1
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
239000000920 calcium hydroxide Substances 0.000 description 1
229910001861 calcium hydroxide Inorganic materials 0.000 description 1
239000001506 calcium phosphate Substances 0.000 description 1
229910000389 calcium phosphate Inorganic materials 0.000 description 1
235000011010 calcium phosphates Nutrition 0.000 description 1
150000001718 carbodiimides Chemical class 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
239000000969 carrier Substances 0.000 description 1
238000005341 cation exchange Methods 0.000 description 1
230000002490 cerebral effect Effects 0.000 description 1
KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
230000015271 coagulation Effects 0.000 description 1
238000005345 coagulation Methods 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
239000008139 complexing agent Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
238000000502 dialysis Methods 0.000 description 1
150000005690 diesters Chemical class 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
BCWATXUNISVFLV-UHFFFAOYSA-N diethyl 2-[3-(2-aminoethyl)phenoxy]propanedioate;sulfuric acid Chemical compound OS(O)(=O)=O.CCOC(=O)C(C(=O)OCC)OC1=CC=CC(CCN)=C1 BCWATXUNISVFLV-UHFFFAOYSA-N 0.000 description 1
WLWCQKMQYZFTDR-UHFFFAOYSA-N diethyl 2-chloropropanedioate Chemical compound CCOC(=O)C(Cl)C(=O)OCC WLWCQKMQYZFTDR-UHFFFAOYSA-N 0.000 description 1
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
238000010494 dissociation reaction Methods 0.000 description 1
230000005593 dissociations Effects 0.000 description 1
239000000975 dye Substances 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
HWJHWSBFPPPIPD-UHFFFAOYSA-N ethoxyethane;propan-2-one Chemical compound CC(C)=O.CCOCC HWJHWSBFPPPIPD-UHFFFAOYSA-N 0.000 description 1
MGZFVSUXQXCEHM-UHFFFAOYSA-N ethyl 2-phenoxyacetate Chemical compound CCOC(=O)COC1=CC=CC=C1 MGZFVSUXQXCEHM-UHFFFAOYSA-N 0.000 description 1
HBKNZSDLEWJQOB-UHFFFAOYSA-N ethyl 5-[4-(2-aminoethyl)phenyl]pentanoate Chemical compound CCOC(=O)CCCCC1=CC=C(CCN)C=C1 HBKNZSDLEWJQOB-UHFFFAOYSA-N 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
239000012065 filter cake Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
238000005194 fractionation Methods 0.000 description 1
239000012458 free base Substances 0.000 description 1
229910021485 fumed silica Inorganic materials 0.000 description 1
238000003304 gavage Methods 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
150000003977 halocarboxylic acids Chemical class 0.000 description 1
230000002140 halogenating effect Effects 0.000 description 1
230000036541 health Effects 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
230000000302 ischemic effect Effects 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
210000003734 kidney Anatomy 0.000 description 1
239000008101 lactose Substances 0.000 description 1
231100000636 lethal dose Toxicity 0.000 description 1
GUWHRJQTTVADPB-UHFFFAOYSA-N lithium azide Chemical compound [Li+].[N-]=[N+]=[N-] GUWHRJQTTVADPB-UHFFFAOYSA-N 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
TWRAJPCQPHBABR-UHFFFAOYSA-N magnesium;diazide Chemical compound [Mg+2].[N-]=[N+]=[N-].[N-]=[N+]=[N-] TWRAJPCQPHBABR-UHFFFAOYSA-N 0.000 description 1
150000002691 malonic acids Chemical class 0.000 description 1
NNICRUQPODTGRU-UHFFFAOYSA-N mandelonitrile Chemical compound N#CC(O)C1=CC=CC=C1 NNICRUQPODTGRU-UHFFFAOYSA-N 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
229910052751 metal Chemical class 0.000 description 1
239000002184 metal Chemical class 0.000 description 1
JPXPYZMVOOFKQY-UHFFFAOYSA-N methyl 5-[4-(2-acetamidoethyl)phenyl]pentanoate Chemical compound COC(=O)CCCCC1=CC=C(CCNC(C)=O)C=C1 JPXPYZMVOOFKQY-UHFFFAOYSA-N 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
SGTPARNYBYMTDZ-UHFFFAOYSA-N n-(2h-tetrazol-5-yl)butanamide Chemical compound CCCC(=O)NC=1N=NNN=1 SGTPARNYBYMTDZ-UHFFFAOYSA-N 0.000 description 1
JPZJDJXBSCXECQ-UHFFFAOYSA-N n-[2-(4-aminophenyl)ethyl]-4-chlorobenzenesulfonamide Chemical compound C1=CC(N)=CC=C1CCNS(=O)(=O)C1=CC=C(Cl)C=C1 JPZJDJXBSCXECQ-UHFFFAOYSA-N 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
125000002560 nitrile group Chemical group 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
239000004006 olive oil Substances 0.000 description 1
235000008390 olive oil Nutrition 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
229940124531 pharmaceutical excipient Drugs 0.000 description 1
238000003408 phase transfer catalysis Methods 0.000 description 1
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
210000004623 platelet-rich plasma Anatomy 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
TZLVRPLSVNESQC-UHFFFAOYSA-N potassium azide Chemical compound [K+].[N-]=[N+]=[N-] TZLVRPLSVNESQC-UHFFFAOYSA-N 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002243 precursor Substances 0.000 description 1
230000002265 prevention Effects 0.000 description 1
VFTSNLXEOAUWMW-UHFFFAOYSA-N propanedioic acid sulfuric acid Chemical compound C(CC(=O)O)(=O)O.S(=O)(=O)(O)O VFTSNLXEOAUWMW-UHFFFAOYSA-N 0.000 description 1
238000011321 prophylaxis Methods 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
239000003586 protic polar solvent Substances 0.000 description 1
150000003242 quaternary ammonium salts Chemical class 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical class OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 1
230000007017 scission Effects 0.000 description 1
210000002460 smooth muscle Anatomy 0.000 description 1
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
239000008279 sol Substances 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
229940095064 tartrate Drugs 0.000 description 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 description 1
230000001732 thrombotic effect Effects 0.000 description 1
HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
239000010936 titanium Substances 0.000 description 1
XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
UBKFNPJMWUJHGB-UHFFFAOYSA-N titanium(4+);tetraazide Chemical compound [Ti+4].[N-]=[N+]=[N-].[N-]=[N+]=[N-].[N-]=[N+]=[N-].[N-]=[N+]=[N-] UBKFNPJMWUJHGB-UHFFFAOYSA-N 0.000 description 1
238000006276 transfer reaction Methods 0.000 description 1
238000002054 transplantation Methods 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
238000001291 vacuum drying Methods 0.000 description 1
229910052720 vanadium Inorganic materials 0.000 description 1
235000019871 vegetable fat Nutrition 0.000 description 1
210000003462 vein Anatomy 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1
235000005074 zinc chloride Nutrition 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- 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
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
- C07D257/06—Five-membered rings with nitrogen atoms directly attached to the ring carbon atom

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
General Chemical & Material Sciences (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Public Health (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Hematology (AREA)
Diabetes (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Medicinal Preparation (AREA)

DD89332133A 1988-08-31 1989-08-28 Verfahren zur herstellung von sulfamiden DD287498A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE3829431A DE3829431A1 (de)	1988-08-31	1988-08-31	Sulfonamide mit tetrazolylrest, verfahren zur ihrer herstellung sowie arzneimittel

Publications (1)

Publication Number	Publication Date
DD287498A5 true DD287498A5 (de)	1991-02-28

Family

ID=6361909

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD89332133A DD287498A5 (de)	1988-08-31	1989-08-28	Verfahren zur herstellung von sulfamiden

Country Status (19)

Country	Link
US (1)	US5037990A (pl)
EP (1)	EP0356989B1 (pl)
JP (1)	JPH02108677A (pl)
KR (1)	KR900003139A (pl)
CN (1)	CN1045780A (pl)
AT (1)	ATE103909T1 (pl)
AU (1)	AU622213B2 (pl)
DD (1)	DD287498A5 (pl)
DE (2)	DE3829431A1 (pl)
DK (1)	DK423289A (pl)
FI (1)	FI894068A7 (pl)
HU (1)	HU203085B (pl)
IL (1)	IL91409A0 (pl)
MX (1)	MX17326A (pl)
NO (1)	NO893482L (pl)
PH (1)	PH27520A (pl)
PL (2)	PL161322B1 (pl)
PT (1)	PT91576B (pl)
ZA (1)	ZA896617B (pl)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5296608A (en) *	1988-04-25	1994-03-22	Hoffman-La Roche Inc.	Intermediates for analogs of tyrosine sulfate or tyrosine phosphate containing peptides
DE4040619A1 (de) *	1990-12-19	1992-06-25	Boehringer Mannheim Gmbh	Neue aliphatische amide, verfahren zu ihrer herstellung sowie arzneimittel, die diese verbindungen enthalten
DE4041780A1 (de) *	1990-12-24	1992-06-25	Boehringer Mannheim Gmbh	Neue amine, verfahren zu ihrer herstellung, sowie diese verbindungen enthaltende arzneimittel
US5686478A (en) *	1993-07-20	1997-11-11	Merck & Co. Inc.	Endothelin antagonists
JP3671266B2 (ja) *	1996-03-21	2005-07-13	東洋化成工業株式会社	５−置換テトラゾール類の製造方法
CN107759477A (zh) *	2017-11-20	2018-03-06	阿里化学(常州)有限公司	一种对硝基苯乙胺盐酸盐的生产制备方法

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB8333665D0 (en) *	1983-12-16	1984-01-25	Lilly Industries Ltd	Organic compounds
GB8528398D0 (en) *	1985-11-19	1985-12-24	Glaxo Group Ltd	Chemical compounds
DE3610643A1 (de) *	1986-03-29	1987-10-01	Boehringer Mannheim Gmbh	Neue phenoxyalkylcarbonsaeure-derivate, verfahren zu ihrer herstellung sowie diese verbindungen enthaltende arzneimittel

1988
- 1988-08-31 DE DE3829431A patent/DE3829431A1/de not_active Withdrawn
1989
- 1989-08-24 PH PH39150A patent/PH27520A/en unknown
- 1989-08-24 AU AU40251/89A patent/AU622213B2/en not_active Ceased
- 1989-08-24 IL IL91409A patent/IL91409A0/xx unknown
- 1989-08-28 HU HU894428A patent/HU203085B/hu not_active IP Right Cessation
- 1989-08-28 PL PL1989281186A patent/PL161322B1/pl unknown
- 1989-08-28 PL PL1989285118A patent/PL161381B1/pl unknown
- 1989-08-28 DD DD89332133A patent/DD287498A5/de not_active IP Right Cessation
- 1989-08-28 DK DK423289A patent/DK423289A/da not_active Application Discontinuation
- 1989-08-28 MX MX1732689A patent/MX17326A/es unknown
- 1989-08-29 EP EP89115911A patent/EP0356989B1/de not_active Expired - Lifetime
- 1989-08-29 DE DE89115911T patent/DE58907390D1/de not_active Expired - Fee Related
- 1989-08-29 AT AT89115911T patent/ATE103909T1/de not_active IP Right Cessation
- 1989-08-30 NO NO89893482A patent/NO893482L/no unknown
- 1989-08-30 FI FI894068A patent/FI894068A7/fi not_active IP Right Cessation
- 1989-08-30 ZA ZA896617A patent/ZA896617B/xx unknown
- 1989-08-30 PT PT91576A patent/PT91576B/pt not_active IP Right Cessation
- 1989-08-31 JP JP1223364A patent/JPH02108677A/ja active Pending
- 1989-08-31 KR KR1019890012469A patent/KR900003139A/ko not_active Withdrawn
- 1989-08-31 US US07/401,317 patent/US5037990A/en not_active Expired - Fee Related
- 1989-08-31 CN CN89107180A patent/CN1045780A/zh active Pending

Also Published As

Publication number	Publication date
FI894068A0 (fi)	1989-08-30
DE3829431A1 (de)	1990-03-01
NO893482D0 (no)	1989-08-30
IL91409A0 (en)	1990-04-29
DK423289A (da)	1990-03-01
HU203085B (en)	1991-05-28
DK423289D0 (da)	1989-08-28
AU622213B2 (en)	1992-04-02
FI894068L (fi)	1990-03-01
PH27520A (en)	1993-08-18
EP0356989A3 (de)	1991-06-12
PT91576A (pt)	1990-03-08
EP0356989A2 (de)	1990-03-07
AU4025189A (en)	1990-03-08
US5037990A (en)	1991-08-06
JPH02108677A (ja)	1990-04-20
PT91576B (pt)	1995-05-04
ATE103909T1 (de)	1994-04-15
EP0356989B1 (de)	1994-04-06
CN1045780A (zh)	1990-10-03
FI894068A7 (fi)	1990-03-01
NO893482L (no)	1990-03-01
DE58907390D1 (de)	1994-05-11
HUT53091A (en)	1990-09-28
PL161381B1 (pl)	1993-06-30
ZA896617B (en)	1990-06-27
MX17326A (es)	1994-01-31
PL161322B1 (pl)	1993-06-30
PL285118A1 (en)	1991-04-22
KR900003139A (ko)	1990-03-23

Legal Events

Date	Code	Title	Description
1994-03-17	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
DE2543252C2 (de)	1986-09-18	Phenylsulfinylalkylamidine, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel
DE2419970C3 (de)	1980-06-12	3-<l-Pyrrolidinyl)-4-phenoxy-5sulfamoylbenzoesäure und Verfahren zu ihrer Herstellung
EP1368300A1 (de)	2003-12-10	Substituierte aminodicarbonsäurederivate
DD252187A5 (de)	1987-12-09	Verfahren zur herstellung von sulfonyl-phenylalkylaminen
EP1216225A2 (de)	2002-06-26	Neuartige aminodicarbonsäurederivate mit pharmazeutischen eigenschaften
WO1993004035A1 (de)	1993-03-04	Neue 3,5-di-tert.butyl-4-hydroxyphenyl-derivate, verfahren zu ihrer herstellung und arzneimittel
DE69408580T2 (de)	1998-06-18	2-amino-1,2,3,4-tetrahydronaphthalenderivate mit cardiovaskulärer wirkung
DE69911726T2 (de)	2004-07-29	Derivate von Arylcarbonsäuren und Tetrazolen mit einer Carbamoyloxy-Gruppe
DD287498A5 (de)	1991-02-28	Verfahren zur herstellung von sulfamiden
DE2903615A1 (de)	1980-06-26	Guajakacylester von mercaptopropionsaeurederivaten, verfahren zu ihrer herstellung und ihre therapeutische verwendung
EP0361113B1 (de)	1993-07-07	Sulfonamidoalkyl-cyclohexan-Verbindungen, Verfahren zu ihrer Herstellung sowie Arzneimittel
DE3875030T2 (de)	1993-03-04	Leukotrien-antagonisten.
DE3872576T2 (de)	1993-03-04	Leukotrienantagonisten.
CA1276644C (fr)	1990-11-20	Benzamides, leur procede de preparation et leur application dans le domaine therapeutique
US5173500A (en)	1992-12-22	Pharmaceutical compositions and methods of sulphonamides containing a tetrazolyl radical
DE69107274T2 (de)	1995-07-13	Phenoxyessigsäure-Derivate, Verfahren zu ihrer Herstellung, und pharmazeutische Zusammensetzungen die sie enthalten.
DE68913159T2 (de)	1994-05-26	Thiophencarboxamid-Derivate und ihre Verwendung als Heilmittel.
DE2516267C2 (de)	1982-07-01	Verfahren zur Herstellung von 2-(4- Isobutylphenyl)-propiohydroxamsäure
EP0222961A1 (de)	1987-05-27	Neue fluorierte Resorcinether
CH616406A5 (en)	1980-03-31	Process for the preparation of novel oxime derivatives
AT211297B (de)	1960-09-26	Verfahren zur Herstellung des neuen 5-Chlortoluol-2,4-disulfonsäureamids und dessen Alkalimetallsalze
AT364836B (de)	1981-11-25	Verfahren zur herstellung von neuen o-substituierten derivaten des (+)-cyanidan-3-ols und deren salzen
AT326681B (de)	1975-12-29	Verfahren zur herstellung von neuen carbamoylaminoalkyl-benzolsulfonylharnstoffen und deren salzen
DE1900948C (de)	1971-09-23	Cis- und trans-2-Methyl-5-(3, 4, S-trimethoxybenzamidoJ-decahydroisochinolin
DE2637596A1 (de)	1977-03-03	3-(5-aryl-2-furyl)-3-hydroxypropionsaeuren und deren aethylester