CS208656B2 - Method of preparation of the 1-acyl-kyanaziridines - Google Patents

Method of preparation of the 1-acyl-kyanaziridines Download PDF

Info

Publication number: CS208656B2
Authority: CS; Czechoslovakia
Prior art keywords: ether; residue; solution; acid; phenyl
Prior art date: 1977-07-11

Application number

CS784544A

Other languages

Czech (cs)

English (en)

Inventor

Herbert Berger

Rudi Gall

Wolfgang Kampe

Uwe Bicker

Rolf Kuhn

Original Assignee

Boehringer Mannheim Gmbh

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.)

1977-07-11

Filing date

1978-07-07

Publication date

1981-09-15

1978-07-07 Application filed by Boehringer Mannheim Gmbh filed Critical Boehringer Mannheim Gmbh

1981-09-15 Publication of CS208656B2 publication Critical patent/CS208656B2/cs

Links

238000002360 preparation method Methods 0.000 title claims description 12
238000000034 method Methods 0.000 title claims description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 442
150000001875 compounds Chemical class 0.000 claims description 81
-1 chloro, methyl Chemical group 0.000 claims description 72
239000002253 acid Substances 0.000 claims description 44
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 39
PGZUFTROELAOMP-UHFFFAOYSA-N aziridine-2-carbonitrile Chemical compound N#CC1CN1 PGZUFTROELAOMP-UHFFFAOYSA-N 0.000 claims description 19
125000004432 carbon atom Chemical group C* 0.000 claims description 18
229920006395 saturated elastomer Polymers 0.000 claims description 18
150000003839 salts Chemical class 0.000 claims description 17
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 16
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 15
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
229910052739 hydrogen Inorganic materials 0.000 claims description 10
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
229910052717 sulfur Inorganic materials 0.000 claims description 8
229910052799 carbon Inorganic materials 0.000 claims description 7
125000000217 alkyl group Chemical group 0.000 claims description 6
239000003960 organic solvent Substances 0.000 claims description 6
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 6
229910052736 halogen Inorganic materials 0.000 claims description 5
239000001257 hydrogen Substances 0.000 claims description 5
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
239000008346 aqueous phase Substances 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
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
150000002367 halogens Chemical class 0.000 claims description 4
239000011593 sulfur Substances 0.000 claims description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
229910052783 alkali metal Inorganic materials 0.000 claims description 3
RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 claims description 3
239000011230 binding agent Substances 0.000 claims description 3
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 3
150000007530 organic bases Chemical class 0.000 claims description 3
229910052760 oxygen Inorganic materials 0.000 claims description 3
229930195734 saturated hydrocarbon Natural products 0.000 claims description 3
125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims description 3
229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 3
125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 claims description 2
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
150000001340 alkali metals Chemical class 0.000 claims description 2
125000004414 alkyl thio group Chemical group 0.000 claims description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 claims description 2
125000004093 cyano group Chemical group *C#N 0.000 claims description 2
125000000753 cycloalkyl group Chemical group 0.000 claims description 2
125000004356 hydroxy functional group Chemical group O* 0.000 claims description 2
150000007529 inorganic bases Chemical class 0.000 claims description 2
125000001624 naphthyl group Chemical group 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
239000001301 oxygen Substances 0.000 claims description 2
KIWUVOGUEXMXSV-UHFFFAOYSA-N rhodanine Chemical compound O=C1CSC(=S)N1 KIWUVOGUEXMXSV-UHFFFAOYSA-N 0.000 claims description 2
125000004434 sulfur atom Chemical group 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
125000004417 unsaturated alkyl group Chemical group 0.000 claims description 2
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 4
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 2
229930192474 thiophene Natural products 0.000 claims 2
YQQSRZSUGBETRS-UHFFFAOYSA-N 1h-pyridazine-6-thione Chemical compound SC1=CC=CN=N1 YQQSRZSUGBETRS-UHFFFAOYSA-N 0.000 claims 1
HUTHUTALXJNNRS-UHFFFAOYSA-N 2-cyclohexylpyridine Chemical compound C1CCCCC1C1=CC=CC=N1 HUTHUTALXJNNRS-UHFFFAOYSA-N 0.000 claims 1
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 1
125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims 1
125000003545 alkoxy group Chemical group 0.000 claims 1
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
125000006627 ethoxycarbonylamino group Chemical group 0.000 claims 1
125000005843 halogen group Chemical group 0.000 claims 1
125000001183 hydrocarbyl group Chemical group 0.000 claims 1
QJRYYOWARFCJQZ-UHFFFAOYSA-N pyrrolidine-1-carbonitrile Chemical class N#CN1CCCC1 QJRYYOWARFCJQZ-UHFFFAOYSA-N 0.000 claims 1
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 abstract description 6
229910000147 aluminium phosphate Inorganic materials 0.000 abstract description 3
230000003327 cancerostatic effect Effects 0.000 abstract description 2
ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 abstract 1
230000004936 stimulating effect Effects 0.000 abstract 1
RVEZZJVBDQCTEF-UHFFFAOYSA-N sulfenic acid Chemical compound SO RVEZZJVBDQCTEF-UHFFFAOYSA-N 0.000 abstract 1
239000000243 solution Substances 0.000 description 115
239000003921 oil Substances 0.000 description 72
235000019198 oils Nutrition 0.000 description 72
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 68
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 65
239000000706 filtrate Substances 0.000 description 60
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 54
ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 45
239000000126 substance Substances 0.000 description 44
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 40
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 39
238000003756 stirring Methods 0.000 description 38
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 32
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 32
238000001816 cooling Methods 0.000 description 30
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 26
239000007787 solid Substances 0.000 description 23
238000001228 spectrum Methods 0.000 description 23
239000000741 silica gel Substances 0.000 description 22
229910002027 silica gel Inorganic materials 0.000 description 22
238000001819 mass spectrum Methods 0.000 description 21
239000000203 mixture Substances 0.000 description 21
239000000047 product Substances 0.000 description 21
239000013078 crystal Substances 0.000 description 19
239000012452 mother liquor Substances 0.000 description 18
239000012071 phase Substances 0.000 description 17
229940086542 triethylamine Drugs 0.000 description 17
238000004458 analytical method Methods 0.000 description 16
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
238000001704 evaporation Methods 0.000 description 15
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 14
239000003480 eluent Substances 0.000 description 14
239000000463 material Substances 0.000 description 14
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
229910052757 nitrogen Inorganic materials 0.000 description 13
229910000030 sodium bicarbonate Inorganic materials 0.000 description 13
235000017557 sodium bicarbonate Nutrition 0.000 description 13
239000000725 suspension Substances 0.000 description 13
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
239000007864 aqueous solution Substances 0.000 description 12
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical class CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 11
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 11
238000000746 purification Methods 0.000 description 11
239000007858 starting material Substances 0.000 description 11
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
230000008020 evaporation Effects 0.000 description 10
239000012074 organic phase Substances 0.000 description 10
239000002244 precipitate Substances 0.000 description 10
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
238000000921 elemental analysis Methods 0.000 description 9
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
229960002449 glycine Drugs 0.000 description 8
238000001665 trituration Methods 0.000 description 8
LNQCUTNLHUQZLR-VNPYQEQNSA-N Iridin Natural products O(C)c1c(O)c2C(=O)C(c3cc(OC)c(OC)c(O)c3)=COc2cc1O[C@H]1[C@@H](O)[C@@H](O)[C@H](O)[C@H](CO)O1 LNQCUTNLHUQZLR-VNPYQEQNSA-N 0.000 description 7
238000002844 melting Methods 0.000 description 7
230000008018 melting Effects 0.000 description 7
239000011734 sodium Substances 0.000 description 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
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 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
239000012230 colorless oil Substances 0.000 description 6
108010047623 iridine Proteins 0.000 description 6
210000000265 leukocyte Anatomy 0.000 description 6
238000000926 separation method Methods 0.000 description 6
229910052708 sodium Inorganic materials 0.000 description 6
239000004471 Glycine Substances 0.000 description 5
241000700159 Rattus Species 0.000 description 5
150000001412 amines Chemical class 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
239000012043 crude product Substances 0.000 description 5
150000003840 hydrochlorides Chemical class 0.000 description 5
239000003208 petroleum Substances 0.000 description 5
150000003254 radicals Chemical group 0.000 description 5
239000000377 silicon dioxide Substances 0.000 description 5
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 4
239000004480 active ingredient Substances 0.000 description 4
238000001035 drying Methods 0.000 description 4
239000000284 extract Substances 0.000 description 4
238000002329 infrared spectrum Methods 0.000 description 4
239000000314 lubricant Substances 0.000 description 4
229910000029 sodium carbonate Inorganic materials 0.000 description 4
235000017550 sodium carbonate Nutrition 0.000 description 4
239000002904 solvent Substances 0.000 description 4
VDNMXWRIILTOEY-UHFFFAOYSA-N 2-[(2-cyclohexylacetyl)amino]acetic acid Chemical compound OC(=O)CNC(=O)CC1CCCCC1 VDNMXWRIILTOEY-UHFFFAOYSA-N 0.000 description 3
MYTAKEVMLYCYIE-UHFFFAOYSA-N 2-[(2-phenoxyacetyl)amino]acetic acid Chemical compound OC(=O)CNC(=O)COC1=CC=CC=C1 MYTAKEVMLYCYIE-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
210000004027 cell Anatomy 0.000 description 3
239000003814 drug Substances 0.000 description 3
235000013905 glycine and its sodium salt Nutrition 0.000 description 3
230000003308 immunostimulating effect Effects 0.000 description 3
210000004698 lymphocyte Anatomy 0.000 description 3
239000000155 melt Substances 0.000 description 3
JKRHDMPWBFBQDZ-UHFFFAOYSA-N n'-hexylmethanediimine Chemical compound CCCCCCN=C=N JKRHDMPWBFBQDZ-UHFFFAOYSA-N 0.000 description 3
238000012360 testing method Methods 0.000 description 3
238000010626 work up procedure Methods 0.000 description 3
KPZGRMZPZLOPBS-UHFFFAOYSA-N 1,3-dichloro-2,2-bis(chloromethyl)propane Chemical compound ClCC(CCl)(CCl)CCl KPZGRMZPZLOPBS-UHFFFAOYSA-N 0.000 description 2
MOMFXATYAINJML-UHFFFAOYSA-N 2-Acetylthiazole Chemical group CC(=O)C1=NC=CS1 MOMFXATYAINJML-UHFFFAOYSA-N 0.000 description 2
VABYVFZVTIDNOA-UHFFFAOYSA-N 2-cyclohexylacetyl chloride Chemical compound ClC(=O)CC1CCCCC1 VABYVFZVTIDNOA-UHFFFAOYSA-N 0.000 description 2
QCXCIYPOMMIBHO-UHFFFAOYSA-N 2-methyl-1,3-thiazole-5-carboxylic acid Chemical compound CC1=NC=C(C(O)=O)S1 QCXCIYPOMMIBHO-UHFFFAOYSA-N 0.000 description 2
INUNLMUAPJVRME-UHFFFAOYSA-N 3-chloropropanoyl chloride Chemical compound ClCCC(Cl)=O INUNLMUAPJVRME-UHFFFAOYSA-N 0.000 description 2
KVCQTKNUUQOELD-UHFFFAOYSA-N 4-amino-n-[1-(3-chloro-2-fluoroanilino)-6-methylisoquinolin-5-yl]thieno[3,2-d]pyrimidine-7-carboxamide Chemical compound N=1C=CC2=C(NC(=O)C=3C4=NC=NC(N)=C4SC=3)C(C)=CC=C2C=1NC1=CC=CC(Cl)=C1F KVCQTKNUUQOELD-UHFFFAOYSA-N 0.000 description 2
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
108010010803 Gelatin Proteins 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
OKJIRPAQVSHGFK-UHFFFAOYSA-N N-acetylglycine Chemical compound CC(=O)NCC(O)=O OKJIRPAQVSHGFK-UHFFFAOYSA-N 0.000 description 2
QIAFMBKCNZACKA-UHFFFAOYSA-N N-benzoylglycine Chemical compound OC(=O)CNC(=O)C1=CC=CC=C1 QIAFMBKCNZACKA-UHFFFAOYSA-N 0.000 description 2
ROXXNENGCGLRSW-UHFFFAOYSA-N N-cyclohexylcarbonylglycine Natural products OC(=O)CNC(=O)C1CCCCC1 ROXXNENGCGLRSW-UHFFFAOYSA-N 0.000 description 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 2
125000002619 bicyclic group Chemical group 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
239000000872 buffer Substances 0.000 description 2
UCAGLBKTLXCODC-UHFFFAOYSA-N carzenide Chemical compound NS(=O)(=O)C1=CC=C(C(O)=O)C=C1 UCAGLBKTLXCODC-UHFFFAOYSA-N 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
239000004927 clay Substances 0.000 description 2
238000004140 cleaning Methods 0.000 description 2
238000004440 column chromatography Methods 0.000 description 2
125000004122 cyclic group Chemical group 0.000 description 2
KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 2
230000000694 effects Effects 0.000 description 2
210000003743 erythrocyte Anatomy 0.000 description 2
229910052731 fluorine Inorganic materials 0.000 description 2
239000011737 fluorine Substances 0.000 description 2
229920000159 gelatin Polymers 0.000 description 2
239000008273 gelatin Substances 0.000 description 2
235000019322 gelatine Nutrition 0.000 description 2
235000011852 gelatine desserts Nutrition 0.000 description 2
229920006158 high molecular weight polymer Polymers 0.000 description 2
150000002430 hydrocarbons Chemical group 0.000 description 2
208000015181 infectious disease Diseases 0.000 description 2
238000001990 intravenous administration Methods 0.000 description 2
239000007788 liquid Substances 0.000 description 2
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
230000003287 optical effect Effects 0.000 description 2
239000007800 oxidant agent Substances 0.000 description 2
LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical compound OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 description 2
SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 2
FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical compound C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 description 2
235000012239 silicon dioxide Nutrition 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
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PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
229910001919 chlorite Inorganic materials 0.000 description 1
229910052619 chlorite group Inorganic materials 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
QBWCMBCROVPCKQ-UHFFFAOYSA-N chlorous acid Chemical compound OCl=O QBWCMBCROVPCKQ-UHFFFAOYSA-N 0.000 description 1
230000004087 circulation Effects 0.000 description 1
229910052681 coesite Inorganic materials 0.000 description 1
229910052906 cristobalite Inorganic materials 0.000 description 1
QPJDMGCKMHUXFD-UHFFFAOYSA-N cyanogen chloride Chemical compound ClC#N QPJDMGCKMHUXFD-UHFFFAOYSA-N 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000003678 cyclohexadienyl group Chemical group C1(=CC=CCC1)* 0.000 description 1
125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 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
WUESWDIHTKHGQA-UHFFFAOYSA-N cyclohexylurea Chemical compound NC(=O)NC1CCCCC1 WUESWDIHTKHGQA-UHFFFAOYSA-N 0.000 description 1
125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 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
YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 description 1
229910000071 diazene Inorganic materials 0.000 description 1
NPOMSUOUAZCMBL-UHFFFAOYSA-N dichloromethane;ethoxyethane Chemical compound ClCCl.CCOCC NPOMSUOUAZCMBL-UHFFFAOYSA-N 0.000 description 1
QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
HDULBKVLSJEMGN-UHFFFAOYSA-N dicyclohexylphosphane Chemical compound C1CCCCC1PC1CCCCC1 HDULBKVLSJEMGN-UHFFFAOYSA-N 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
HVBMYHDTXIDFKE-UHFFFAOYSA-N diethyl hydrogen phosphate;ethyl dihydrogen phosphate Chemical compound CCOP(O)(O)=O.CCOP(O)(=O)OCC HVBMYHDTXIDFKE-UHFFFAOYSA-N 0.000 description 1
CEYULKASIQJZGP-UHFFFAOYSA-L disodium;2-(carboxymethyl)-2-hydroxybutanedioate Chemical compound [Na+].[Na+].[O-]C(=O)CC(O)(C(=O)O)CC([O-])=O CEYULKASIQJZGP-UHFFFAOYSA-L 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
239000008298 dragée Substances 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
125000001033 ether group Chemical group 0.000 description 1
DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 1
MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 1
JTTXRFNOFFGPFI-UHFFFAOYSA-N ethyl 4-(chloromethyl)benzoate Chemical compound CCOC(=O)C1=CC=C(CCl)C=C1 JTTXRFNOFFGPFI-UHFFFAOYSA-N 0.000 description 1
229920001249 ethyl cellulose Polymers 0.000 description 1
235000019325 ethyl cellulose Nutrition 0.000 description 1
NTQSYKUASYNENN-UHFFFAOYSA-N ethyl n-[2-(2-cyanoaziridin-1-yl)-2-oxoethyl]carbamate Chemical compound CCOC(=O)NCC(=O)N1CC1C#N NTQSYKUASYNENN-UHFFFAOYSA-N 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
210000001061 forehead Anatomy 0.000 description 1
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerol Substances OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 1
125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 description 1
239000004519 grease Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
239000005457 ice water Substances 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
230000002458 infectious effect Effects 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000002198 insoluble material Substances 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
LNQCUTNLHUQZLR-OZJWLQQPSA-N iridin Chemical compound OC1=C(OC)C(OC)=CC(C=2C(C3=C(O)C(OC)=C(O[C@H]4[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O4)O)C=C3OC=2)=O)=C1 LNQCUTNLHUQZLR-OZJWLQQPSA-N 0.000 description 1
229910052741 iridium Inorganic materials 0.000 description 1
GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
230000007794 irritation Effects 0.000 description 1
238000002955 isolation Methods 0.000 description 1
ULYZAYCEDJDHCC-UHFFFAOYSA-N isopropyl chloride Chemical compound CC(C)Cl ULYZAYCEDJDHCC-UHFFFAOYSA-N 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
239000008101 lactose Substances 0.000 description 1
238000002386 leaching Methods 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
229910052748 manganese Inorganic materials 0.000 description 1
239000011572 manganese Substances 0.000 description 1
238000004949 mass spectrometry Methods 0.000 description 1
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
TXOUDPQJASQYBZ-UHFFFAOYSA-N n,n'-dihexylmethanediimine Chemical compound CCCCCCN=C=NCCCCCC TXOUDPQJASQYBZ-UHFFFAOYSA-N 0.000 description 1
JYMBBLGHGHYXBQ-UHFFFAOYSA-N n-[2-(2-cyanoaziridin-1-yl)-2-oxoethyl]-2-methoxyacetamide Chemical compound COCC(=O)NCC(=O)N1CC1C#N JYMBBLGHGHYXBQ-UHFFFAOYSA-N 0.000 description 1
RDLKXGHIFGLLRH-UHFFFAOYSA-N n-[3-(2-cyanoaziridin-1-yl)-3-oxopropyl]acetamide Chemical compound CC(=O)NCCC(=O)N1CC1C#N RDLKXGHIFGLLRH-UHFFFAOYSA-N 0.000 description 1
MMIROGAREFWNKF-UHFFFAOYSA-N n-[4-(2-cyanoaziridin-1-yl)-4-oxobutyl]acetamide Chemical compound CC(=O)NCCCC(=O)N1CC1C#N MMIROGAREFWNKF-UHFFFAOYSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
239000004006 olive oil Substances 0.000 description 1
235000008390 olive oil Nutrition 0.000 description 1
150000004967 organic peroxy acids Chemical class 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
230000001717 pathogenic effect Effects 0.000 description 1
UWJJYHHHVWZFEP-UHFFFAOYSA-N pentane-1,1-diol Chemical compound CCCCC(O)O UWJJYHHHVWZFEP-UHFFFAOYSA-N 0.000 description 1
230000003836 peripheral circulation Effects 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
125000006678 phenoxycarbonyl group Chemical group 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
239000006187 pill Substances 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
239000000843 powder Substances 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
230000035755 proliferation Effects 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical compound [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 description 1
PSAYJRPASWETSH-UHFFFAOYSA-N pyridine-2-carbonyl chloride Chemical compound ClC(=O)C1=CC=CC=N1 PSAYJRPASWETSH-UHFFFAOYSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000011084 recovery Methods 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
230000033764 rhythmic process Effects 0.000 description 1
125000005624 silicic acid group Chemical class 0.000 description 1
XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
239000002002 slurry Substances 0.000 description 1
210000000813 small intestine Anatomy 0.000 description 1
239000004289 sodium hydrogen sulphite Substances 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
239000004334 sorbic acid Substances 0.000 description 1
235000010199 sorbic acid Nutrition 0.000 description 1
229940075582 sorbic acid Drugs 0.000 description 1
238000004611 spectroscopical analysis Methods 0.000 description 1
210000000952 spleen Anatomy 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
239000010959 steel Substances 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
229910052682 stishovite Inorganic materials 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
JDVPQXZIJDEHAN-UHFFFAOYSA-N succinamic acid Chemical compound NC(=O)CCC(O)=O JDVPQXZIJDEHAN-UHFFFAOYSA-N 0.000 description 1
150000003457 sulfones Chemical class 0.000 description 1
150000003462 sulfoxides Chemical class 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
GZHWPYMWTAUJPC-UHFFFAOYSA-N terephthalic acid;dihydrochloride Chemical compound Cl.Cl.OC(=O)C1=CC=C(C(O)=O)C=C1 GZHWPYMWTAUJPC-UHFFFAOYSA-N 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
UVZICZIVKIMRNE-UHFFFAOYSA-N thiodiacetic acid Chemical compound OC(=O)CSCC(O)=O UVZICZIVKIMRNE-UHFFFAOYSA-N 0.000 description 1
125000000101 thioether group Chemical group 0.000 description 1
125000003396 thiol group Chemical group [H]S* 0.000 description 1
QIQITDHWZYEEPA-UHFFFAOYSA-N thiophene-2-carbonyl chloride Chemical compound ClC(=O)C1=CC=CS1 QIQITDHWZYEEPA-UHFFFAOYSA-N 0.000 description 1
229940113082 thymine Drugs 0.000 description 1
VPYJNCGUESNPMV-UHFFFAOYSA-N triallylamine Chemical compound C=CCN(CC=C)CC=C VPYJNCGUESNPMV-UHFFFAOYSA-N 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
229910052905 tridymite Inorganic materials 0.000 description 1
HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 description 1
235000019871 vegetable fat Nutrition 0.000 description 1
210000003462 vein Anatomy 0.000 description 1
239000000052 vinegar Substances 0.000 description 1
235000021419 vinegar Nutrition 0.000 description 1
230000009385 viral infection Effects 0.000 description 1
238000005406 washing Methods 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
229910052726 zirconium Inorganic materials 0.000 description 1

Classifications

- 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
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three 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
- C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/04—Immunostimulants
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D203/00—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom
- C07D203/04—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D203/06—Heterocyclic compounds containing three-membered rings with one nitrogen 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
- C07D203/16—Heterocyclic compounds containing three-membered rings with one nitrogen 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 acylated ring nitrogen atoms
- C07D203/18—Heterocyclic compounds containing three-membered rings with one nitrogen 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 acylated ring nitrogen atoms by carboxylic acids, or by sulfur or nitrogen analogues thereof
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D203/00—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom
- C07D203/04—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D203/06—Heterocyclic compounds containing three-membered rings with one nitrogen 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
- C07D203/22—Heterocyclic compounds containing three-membered rings with one nitrogen 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 directly attached to the ring nitrogen atom
- C07D203/24—Sulfur atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three 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
- C07D231/16—Halogen atoms or nitro radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three 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
- C07D231/18—One oxygen or sulfur atom
- C07D231/20—One oxygen atom attached in position 3 or 5
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three 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
- C07D231/18—One oxygen or sulfur atom
- C07D231/20—One oxygen atom attached in position 3 or 5
- C07D231/22—One oxygen atom attached in position 3 or 5 with aryl radicals attached to ring nitrogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/564—Three-membered rings
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F42—AMMUNITION; BLASTING
- F42B—EXPLOSIVE CHARGES, e.g. FOR BLASTING, FIREWORKS, AMMUNITION
- F42B3/00—Blasting cartridges, i.e. case and explosive
- F42B3/087—Flexible or deformable blasting cartridges, e.g. bags or hoses for slurries

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Public Health (AREA)
Immunology (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Biochemistry (AREA)
Molecular Biology (AREA)
General Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Communicable Diseases (AREA)
Oncology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Plural Heterocyclic Compounds (AREA)
Pyridine Compounds (AREA)

CS784544A 1977-07-11 1978-07-07 Method of preparation of the 1-acyl-kyanaziridines CS208656B2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19772731264 DE2731264A1 (de)	1977-07-11	1977-07-11	Neue 1-acyl-2-cyanaziridine, verfahren zu deren herstellung und diese verbindungen enthaltende pharmazeutische zubereitungen

Publications (1)

Publication Number	Publication Date
CS208656B2 true CS208656B2 (en)	1981-09-15

Family

ID=6013651

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS784544A CS208656B2 (en)	1977-07-11	1978-07-07	Method of preparation of the 1-acyl-kyanaziridines

Country Status (26)

Country	Link
US (1)	US4267174A (de)
JP (1)	JPS5436254A (de)
AT (1)	AT356663B (de)
AU (2)	AU519219B2 (de)
BE (1)	BE868796A (de)
CA (1)	CA1086309A (de)
CS (1)	CS208656B2 (de)
DD (1)	DD137710A5 (de)
DE (1)	DE2731264A1 (de)
DK (1)	DK306978A (de)
ES (1)	ES471512A1 (de)
FI (1)	FI782157A7 (de)
FR (1)	FR2397403A1 (de)
GB (1)	GB1594079A (de)
HU (1)	HU179428B (de)
IL (1)	IL55109A (de)
IT (1)	IT1096910B (de)
LU (1)	LU79937A1 (de)
NL (1)	NL7807276A (de)
NO (1)	NO782399L (de)
NZ (1)	NZ187794A (de)
PL (1)	PL126639B1 (de)
PT (1)	PT68263A (de)
SE (1)	SE7807642L (de)
SU (1)	SU1077565A3 (de)
ZA (1)	ZA783829B (de)

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CA2515963A1 (en) *	2003-02-24	2004-09-10	Arena Pharmaceuticals, Inc.	Phenyl- and pyridylpiperidine-derivatives as modulators of glucose metabolism
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HRP20090093T3 (en) *	2004-06-04	2009-03-31	Arena Pharmaceuticals Inc.	Substituted aryl and heteroaryl derivatives as modulators of metabolism and the prophylaxis and treatment of disorders related thereto
DOP2006000010A (es)	2005-01-10	2006-07-31	Arena Pharm Inc	Procedimiento para preparar eteres aromáticos
MY148521A (en) *	2005-01-10	2013-04-30	Arena Pharm Inc	Substituted pyridinyl and pyrimidinyl derivatives as modulators of metabolism and the treatment of disorders related thereto
EP1931654B1 (de) *	2005-09-16	2009-04-22	Arena Pharmaceuticals, Inc.	Stoffwechselmodulatoren und behandlung damit verbundener erkrankungen
TW200811140A (en) *	2006-07-06	2008-03-01	Arena Pharm Inc	Modulators of metabolism and the treatment of disorders related thereto
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CN108558740B (zh)	2010-01-27	2021-10-19	艾尼纳制药公司	S1p1受体调节剂及其盐的制备方法
SG188548A1 (en)	2010-09-22	2013-04-30	Arena Pharm Inc	Modulators of the gpr119 receptor and the treatment of disorders related thereto
PL3242666T3 (pl)	2015-01-06	2025-02-17	Arena Pharmaceuticals, Inc.	Związek do zastosowania w leczeniu dolegliwości związanych z receptorem s1p1
HUE060476T2 (hu)	2015-06-22	2023-03-28	Arena Pharm Inc	(R)-2-(7-(4-ciklopentil-3-(trifluormetil)benziloxi)-1,2,3,4- tetrahidrociklopenta[B]indol-3-il)ecetsav kristályos L-arginin-sója S1P1 receptorral kapcsolatos rendellenességek esetén való alkalmazásra
WO2018151873A1 (en)	2017-02-16	2018-08-23	Arena Pharmaceuticals, Inc.	Compounds and methods for treatment of primary biliary cholangitis
US12156866B2 (en)	2018-06-06	2024-12-03	Arena Pharmaceuticals, Inc.	Methods of treating conditions related to the S1P1 receptor
LV15518A (lv) *	2019-02-18	2020-08-20	Latvijas Organiskās Sintēzes Institūts	Aziridīn-2-karboksamīda atvasinājumi kā tioredoksīnreduktāzes inhibitori ar pretvēža un pretmetastatisku iedarbību un to sintēze
US20230039836A1 (en) *	2020-01-10	2023-02-09	Uniwersytet Jagiellonski	Aromatic sulphonamides derivatives that inhibits pdi a3, their synthesis and use
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1977
- 1977-07-11 DE DE19772731264 patent/DE2731264A1/de not_active Withdrawn
1978
- 1978-05-17 GB GB20099/78A patent/GB1594079A/en not_active Expired
- 1978-06-16 US US05/916,389 patent/US4267174A/en not_active Expired - Lifetime
- 1978-07-04 ZA ZA783829A patent/ZA783829B/xx unknown
- 1978-07-04 SU SU782631500A patent/SU1077565A3/ru active
- 1978-07-04 CA CA306,740A patent/CA1086309A/en not_active Expired
- 1978-07-04 FI FI782157A patent/FI782157A7/fi not_active Application Discontinuation
- 1978-07-05 PL PL1978208195A patent/PL126639B1/pl unknown
- 1978-07-05 NL NL7807276A patent/NL7807276A/xx not_active Application Discontinuation
- 1978-07-06 AU AU37826/78A patent/AU519219B2/en not_active Expired
- 1978-07-06 AU AU37826/78A patent/AU3782678A/en active Granted
- 1978-07-06 DD DD78206567A patent/DD137710A5/de unknown
- 1978-07-06 ES ES471512A patent/ES471512A1/es not_active Expired
- 1978-07-06 BE BE189121A patent/BE868796A/xx unknown
- 1978-07-07 LU LU79937A patent/LU79937A1/de unknown
- 1978-07-07 CS CS784544A patent/CS208656B2/cs unknown
- 1978-07-07 NZ NZ187794A patent/NZ187794A/xx unknown
- 1978-07-07 DK DK783069A patent/DK306978A/da not_active Application Discontinuation
- 1978-07-07 SE SE7807642A patent/SE7807642L/xx unknown
- 1978-07-07 PT PT68263A patent/PT68263A/de unknown
- 1978-07-07 IT IT25474/78A patent/IT1096910B/it active
- 1978-07-09 IL IL55109A patent/IL55109A/xx unknown
- 1978-07-10 AT AT496478A patent/AT356663B/de not_active IP Right Cessation
- 1978-07-10 HU HU78BO1723A patent/HU179428B/hu unknown
- 1978-07-10 FR FR7820468A patent/FR2397403A1/fr not_active Withdrawn
- 1978-07-10 NO NO782399A patent/NO782399L/no unknown
- 1978-07-11 JP JP8364578A patent/JPS5436254A/ja active Pending

Also Published As

Publication number	Publication date
SU1077565A3 (ru)	1984-02-29
ATA496478A (de)	1979-10-15
NL7807276A (nl)	1979-01-15
US4267174A (en)	1981-05-12
PL208195A1 (de)	1980-03-24
FR2397403A1 (fr)	1979-02-09
PT68263A (de)	1978-08-01
CA1086309A (en)	1980-09-23
LU79937A1 (de)	1980-02-14
JPS5436254A (en)	1979-03-16
AU3782678A (en)	1980-01-10
PL126639B1 (en)	1983-08-31
DK306978A (da)	1979-01-12
IT7825474A0 (it)	1978-07-07
ES471512A1 (es)	1979-10-01
HU179428B (en)	1982-10-28
AU3782578A (en)	1980-01-10
NO782399L (no)	1979-01-12
GB1594079A (en)	1981-07-30
IL55109A0 (en)	1978-09-29
IL55109A (en)	1982-07-30
IT1096910B (it)	1985-08-26
AU519219B2 (en)	1981-11-19
BE868796A (fr)	1979-01-08
FI782157A7 (fi)	1979-01-12
NZ187794A (en)	1980-05-08
SE7807642L (sv)	1979-03-14
ZA783829B (en)	1980-03-26
AT356663B (de)	1980-05-12
DD137710A5 (de)	1979-09-19
DE2731264A1 (de)	1979-02-01

Publication	Publication Date	Title
CS208656B2 (en)	1981-09-15	Method of preparation of the 1-acyl-kyanaziridines
DE69310475T2 (de)	1997-09-04	Benzokondensierte Lactame
EP0303697B1 (de)	1997-10-01	Derivate des physiologisch aktiven mittels k-252
AU2013296627C9 (en)	2018-03-22	Deuterated ibrutinib
JPH0358357B2 (de)	1991-09-05
CY1205A (en)	1983-12-31	Penicillin derivatives
ZA200108774B (en)	2003-01-24	Carboxylic acid derivatives that inhibit the binding of integrins to their receptors.
RU2233278C9 (ru)	2009-11-27	Пиримидиноновые соединения, способ их получения и фармацевтическая композиция
JPS649985B2 (de)	1989-02-21
EP1561749A1 (de)	2005-08-10	Inhibitoren der TNF-Alpha Bildung zur Behandlung von Autoimmunerkrankungen
JPH0826036B2 (ja)	1996-03-13	生理活性物質ｋ−２５２の誘導体
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US5180724A (en)	1993-01-19	Carboxamide amino acid heterobicyclic paf antagonists
RU2297420C2 (ru)	2007-04-20	Средство против кислотоустойчивых бактерий, содержащее гетероциклические производные бензоксазина в качестве активного компонента
DK169031B1 (da)	1994-08-01	1,2,3,4-Tetrahydro-3-carbamoyl-2-thioxo/oxo-5-pyrimidencarboxylsyre-derivater og farmaceutiske præparater indeholdende sådanne
JP2025156455A (ja)	2025-10-14	チアゾロ［５，４－ｂ］ピリジンＭＡＬＴ－１阻害剤
JP3122161B2 (ja)	2001-01-09	γ−ラクトン免疫抑制剤
EP0950418A2 (de)	1999-10-20	Zusammensetzung zur Prävention und Behandlung von ischämischen Erkrankungen
EP0605434B1 (de)	1998-08-19	Imidazo (4,5-c)pyridinderivate als paf antagonisten
JP4149172B2 (ja)	2008-09-10	インテグリンと受容体との結合を阻害するカルボン酸誘導体
JPH01110626A (ja)	1989-04-27	ナフチリジン抗嫌気菌用化合物
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