NO782399L - Fremgangsmaate ved fremstilling av 1-acyl-2-cyanaziridiner - Google Patents

Fremgangsmaate ved fremstilling av 1-acyl-2-cyanaziridiner

Info

Publication number: NO782399L
Authority: NO; Norway
Prior art keywords: group; cyanaziridine; optionally; ether; substituted
Prior art date: 1977-07-11

Application number

NO782399A

Other languages

English (en)

Norwegian (no)

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

1978-07-10

Publication date

1979-01-12

1978-07-10 Application filed by Boehringer Mannheim Gmbh filed Critical Boehringer Mannheim Gmbh

1979-01-12 Publication of NO782399L publication Critical patent/NO782399L/no

Links

238000000034 method Methods 0.000 title claims description 9
238000002360 preparation method Methods 0.000 title claims description 8
150000001875 compounds Chemical class 0.000 claims description 136
PGZUFTROELAOMP-UHFFFAOYSA-N aziridine-2-carbonitrile Chemical compound N#CC1CN1 PGZUFTROELAOMP-UHFFFAOYSA-N 0.000 claims description 123
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 47
-1 ureido- Chemical class 0.000 claims description 45
125000003118 aryl group Chemical group 0.000 claims description 31
125000000217 alkyl group Chemical group 0.000 claims description 25
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
229920006395 saturated elastomer Polymers 0.000 claims description 24
239000002253 acid Substances 0.000 claims description 23
125000003545 alkoxy group Chemical group 0.000 claims description 23
229910052736 halogen Inorganic materials 0.000 claims description 23
150000002367 halogens Chemical class 0.000 claims description 23
125000002252 acyl group Chemical group 0.000 claims description 19
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 14
125000004432 carbon atom Chemical group C* 0.000 claims description 14
125000004423 acyloxy group Chemical group 0.000 claims description 13
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 13
150000003839 salts Chemical class 0.000 claims description 13
125000004414 alkyl thio group Chemical group 0.000 claims description 12
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 12
150000002825 nitriles Chemical class 0.000 claims description 12
125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 11
125000003277 amino group Chemical group 0.000 claims description 11
125000000753 cycloalkyl group Chemical group 0.000 claims description 11
125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 10
125000000623 heterocyclic group Chemical group 0.000 claims description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 8
125000004417 unsaturated alkyl group Chemical group 0.000 claims description 8
229910052760 oxygen Chemical group 0.000 claims description 7
239000001301 oxygen Chemical group 0.000 claims description 7
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 6
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 4
125000004104 aryloxy group Chemical group 0.000 claims description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
125000001072 heteroaryl group Chemical group 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
239000012442 inert solvent Substances 0.000 claims description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
XNMVAVGXJZFTEH-BUYFANAVSA-N (1r,2s,4r)-4,7,7-trimethyl-3-oxobicyclo[2.2.1]heptane-2-carboxylic acid Chemical group C1C[C@@]2(C)C(=O)[C@@H](C(O)=O)[C@@H]1C2(C)C XNMVAVGXJZFTEH-BUYFANAVSA-N 0.000 claims description 3
125000005110 aryl thio group Chemical group 0.000 claims description 3
239000011230 binding agent Substances 0.000 claims description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
229930195734 saturated hydrocarbon Natural products 0.000 claims description 3
229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 3
BTXXTMOWISPQSJ-UHFFFAOYSA-N 4,4,4-trifluorobutan-2-one Chemical group CC(=O)CC(F)(F)F BTXXTMOWISPQSJ-UHFFFAOYSA-N 0.000 claims description 2
BQACOLQNOUYJCE-FYZZASKESA-N Abietic acid Chemical group CC(C)C1=CC2=CC[C@]3(C)[C@](C)(CCC[C@@]3(C)C(=O)O)[C@H]2CC1 BQACOLQNOUYJCE-FYZZASKESA-N 0.000 claims description 2
RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Chemical group C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 claims description 2
239000004215 Carbon black (E152) Substances 0.000 claims description 2
239000005864 Sulphur Substances 0.000 claims description 2
125000004442 acylamino group Chemical group 0.000 claims description 2
125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims description 2
125000005530 alkylenedioxy group Chemical group 0.000 claims description 2
125000004391 aryl sulfonyl group Chemical group 0.000 claims description 2
150000001540 azides Chemical group 0.000 claims description 2
KXDHJXZQYSOELW-UHFFFAOYSA-N carbamic acid group Chemical group C(N)(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 2
238000009833 condensation Methods 0.000 claims description 2
230000005494 condensation Effects 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
229930195733 hydrocarbon Natural products 0.000 claims description 2
125000001624 naphthyl group Chemical group 0.000 claims description 2
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims 2
125000004356 hydroxy functional group Chemical group O* 0.000 claims 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims 1
125000005138 alkoxysulfonyl group Chemical group 0.000 claims 1
150000005840 aryl radicals Chemical class 0.000 claims 1
125000001183 hydrocarbyl group Chemical group 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 497
239000000243 solution Substances 0.000 description 128
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 125
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 106
239000003921 oil Substances 0.000 description 82
235000019198 oils Nutrition 0.000 description 82
ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 72
239000000706 filtrate Substances 0.000 description 69
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 62
150000002168 ethanoic acid esters Chemical class 0.000 description 58
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 54
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 49
238000001704 evaporation Methods 0.000 description 49
230000008020 evaporation Effects 0.000 description 44
238000003756 stirring Methods 0.000 description 41
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 35
239000000741 silica gel Substances 0.000 description 35
229910002027 silica gel Inorganic materials 0.000 description 35
238000001816 cooling Methods 0.000 description 33
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 32
239000000047 product Substances 0.000 description 30
238000001819 mass spectrum Methods 0.000 description 28
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 26
235000017557 sodium bicarbonate Nutrition 0.000 description 24
229910000030 sodium bicarbonate Inorganic materials 0.000 description 24
238000000921 elemental analysis Methods 0.000 description 23
239000012071 phase Substances 0.000 description 22
239000000126 substance Substances 0.000 description 22
239000000203 mixture Substances 0.000 description 21
239000012452 mother liquor Substances 0.000 description 19
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 16
239000013078 crystal Substances 0.000 description 16
239000003480 eluent Substances 0.000 description 16
239000007787 solid Substances 0.000 description 16
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 14
238000000746 purification Methods 0.000 description 14
239000000725 suspension Substances 0.000 description 14
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 14
150000003840 hydrochlorides Chemical class 0.000 description 13
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
239000007858 starting material Substances 0.000 description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
238000001665 trituration Methods 0.000 description 11
229910052757 nitrogen Inorganic materials 0.000 description 10
239000012074 organic phase Substances 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
229960002449 glycine Drugs 0.000 description 9
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
238000000926 separation method Methods 0.000 description 8
ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 8
238000002329 infrared spectrum Methods 0.000 description 7
239000000463 material Substances 0.000 description 7
239000003208 petroleum Substances 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 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
239000012043 crude product Substances 0.000 description 6
239000000284 extract Substances 0.000 description 6
230000003308 immunostimulating effect Effects 0.000 description 6
238000004519 manufacturing process Methods 0.000 description 6
239000000155 melt Substances 0.000 description 6
125000001424 substituent group Chemical group 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
239000004471 Glycine Substances 0.000 description 5
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical compound C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 4
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 4
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
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 4
150000007513 acids Chemical class 0.000 description 4
238000007792 addition Methods 0.000 description 4
229910052799 carbon Inorganic materials 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
125000004122 cyclic group Chemical group 0.000 description 4
238000001035 drying Methods 0.000 description 4
108010047623 iridine Proteins 0.000 description 4
KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
BYYFJADNNPSTCO-UHFFFAOYSA-N 2-[(2-butylsulfanylacetyl)amino]acetic acid Chemical compound CCCCSCC(=O)NCC(O)=O BYYFJADNNPSTCO-UHFFFAOYSA-N 0.000 description 3
NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
VTYYLEPIZMXCLO-UHFFFAOYSA-L calcium carbonate Substances [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 3
230000003327 cancerostatic effect Effects 0.000 description 3
239000003814 drug Substances 0.000 description 3
235000019439 ethyl acetate Nutrition 0.000 description 3
235000013905 glycine and its sodium salt Nutrition 0.000 description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
239000012265 solid product Substances 0.000 description 3
229910052717 sulfur Inorganic materials 0.000 description 3
238000005406 washing Methods 0.000 description 3
238000010626 work up procedure Methods 0.000 description 3
CYTLOMOEKMHGPM-UHFFFAOYSA-N 1-methyl-3-nitropyrazole-4-carbonyl chloride Chemical compound CN1C=C(C(Cl)=O)C([N+]([O-])=O)=N1 CYTLOMOEKMHGPM-UHFFFAOYSA-N 0.000 description 2
YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
RVHGZLBJHUREQW-UHFFFAOYSA-N 2-(1-benzofuran-2-carbonylamino)acetic acid Chemical compound C1=CC=C2OC(C(=O)NCC(=O)O)=CC2=C1 RVHGZLBJHUREQW-UHFFFAOYSA-N 0.000 description 2
NDLLIOPAEOBFKZ-UHFFFAOYSA-N 2-(cyclopropanecarbonylamino)acetic acid Chemical compound OC(=O)CNC(=O)C1CC1 NDLLIOPAEOBFKZ-UHFFFAOYSA-N 0.000 description 2
SYPPNKVSWGEQBC-UHFFFAOYSA-N 2-[(1-methyl-3-nitropyrazole-4-carbonyl)amino]acetic acid Chemical compound CN1C=C(C(=O)NCC(O)=O)C([N+]([O-])=O)=N1 SYPPNKVSWGEQBC-UHFFFAOYSA-N 0.000 description 2
OVJKNWZFRRCVGV-UHFFFAOYSA-N 2-[(2-phenylsulfanylacetyl)amino]acetic acid Chemical compound OC(=O)CNC(=O)CSC1=CC=CC=C1 OVJKNWZFRRCVGV-UHFFFAOYSA-N 0.000 description 2
VABYVFZVTIDNOA-UHFFFAOYSA-N 2-cyclohexylacetyl chloride Chemical compound ClC(=O)CC1CCCCC1 VABYVFZVTIDNOA-UHFFFAOYSA-N 0.000 description 2
OFTKFKYVSBNYEC-UHFFFAOYSA-N 2-furoyl chloride Chemical compound ClC(=O)C1=CC=CO1 OFTKFKYVSBNYEC-UHFFFAOYSA-N 0.000 description 2
SJSOFNCYXJUNBT-UHFFFAOYSA-N 3,4,5-trimethoxybenzoic acid Chemical compound COC1=CC(C(O)=O)=CC(OC)=C1OC SJSOFNCYXJUNBT-UHFFFAOYSA-N 0.000 description 2
JOOXCMJARBKPKM-UHFFFAOYSA-N 4-oxopentanoic acid Chemical compound CC(=O)CCC(O)=O JOOXCMJARBKPKM-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
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 2
GUUVPOWQJOLRAS-UHFFFAOYSA-N Diphenyl disulfide Chemical compound C=1C=CC=CC=1SSC1=CC=CC=C1 GUUVPOWQJOLRAS-UHFFFAOYSA-N 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
229930195725 Mannitol Natural products 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
KSPQDMRTZZYQLM-UHFFFAOYSA-N N-(2-furoyl)glycine Chemical compound OC(=O)CNC(=O)C1=CC=CO1 KSPQDMRTZZYQLM-UHFFFAOYSA-N 0.000 description 2
KTHDTJVBEPMMGL-VKHMYHEASA-N N-acetyl-L-alanine Chemical compound OC(=O)[C@H](C)NC(C)=O KTHDTJVBEPMMGL-VKHMYHEASA-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
238000005481 NMR spectroscopy Methods 0.000 description 2
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
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239000013543 active substance Substances 0.000 description 2
239000003513 alkali Substances 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
239000000872 buffer Substances 0.000 description 2
JXIDRUSBYYMCON-UHFFFAOYSA-N butan-2-one;heptane Chemical compound CCC(C)=O.CCCCCCC JXIDRUSBYYMCON-UHFFFAOYSA-N 0.000 description 2
235000010216 calcium carbonate Nutrition 0.000 description 2
125000002837 carbocyclic group Chemical group 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
210000004027 cell Anatomy 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
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238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
235000014113 dietary fatty acids Nutrition 0.000 description 2
238000004090 dissolution Methods 0.000 description 2
210000003743 erythrocyte Anatomy 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
239000000194 fatty acid Substances 0.000 description 2
229930195729 fatty acid Natural products 0.000 description 2
150000004665 fatty acids Chemical class 0.000 description 2
229910052731 fluorine Inorganic materials 0.000 description 2
239000011737 fluorine Substances 0.000 description 2
239000004519 grease Substances 0.000 description 2
125000005842 heteroatom Chemical group 0.000 description 2
150000002430 hydrocarbons Chemical group 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
238000001990 intravenous administration Methods 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
210000000265 leukocyte Anatomy 0.000 description 2
239000007788 liquid Substances 0.000 description 2
210000004698 lymphocyte Anatomy 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
239000000594 mannitol Substances 0.000 description 2
235000010355 mannitol Nutrition 0.000 description 2
JDRMYOQETPMYQX-UHFFFAOYSA-N monomethyl succinate Chemical compound COC(=O)CCC(O)=O JDRMYOQETPMYQX-UHFFFAOYSA-N 0.000 description 2
150000002829 nitrogen Chemical class 0.000 description 2
230000003204 osmotic effect Effects 0.000 description 2
YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
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229920000609 methyl cellulose Polymers 0.000 description 1
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NRSCPTLHWVWLLH-UHFFFAOYSA-N p-methylhippuric acid Chemical compound CC1=CC=C(C(=O)NCC(O)=O)C=C1 NRSCPTLHWVWLLH-UHFFFAOYSA-N 0.000 description 1
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CMPQUABWPXYYSH-UHFFFAOYSA-N phenyl phosphate Chemical compound OP(O)(=O)OC1=CC=CC=C1 CMPQUABWPXYYSH-UHFFFAOYSA-N 0.000 description 1
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WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
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PSAYJRPASWETSH-UHFFFAOYSA-N pyridine-2-carbonyl chloride Chemical compound ClC(=O)C1=CC=CC=N1 PSAYJRPASWETSH-UHFFFAOYSA-N 0.000 description 1
150000003222 pyridines Chemical class 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
KIWUVOGUEXMXSV-UHFFFAOYSA-N rhodanine Chemical compound O=C1CSC(=S)N1 KIWUVOGUEXMXSV-UHFFFAOYSA-N 0.000 description 1
238000006798 ring closing metathesis reaction Methods 0.000 description 1
125000005624 silicic acid group Chemical class 0.000 description 1
235000012239 silicon dioxide Nutrition 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
210000000813 small intestine Anatomy 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
239000004334 sorbic acid Substances 0.000 description 1
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238000001228 spectrum Methods 0.000 description 1
210000004989 spleen cell Anatomy 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
230000000638 stimulation Effects 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
125000003107 substituted aryl group Chemical group 0.000 description 1
150000003450 sulfenic acids Chemical class 0.000 description 1
150000003455 sulfinic acids Chemical class 0.000 description 1
150000003457 sulfones 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
LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
125000004149 thio group Chemical group *S* 0.000 description 1
UVZICZIVKIMRNE-UHFFFAOYSA-N thiodiacetic acid Chemical compound OC(=O)CSCC(O)=O UVZICZIVKIMRNE-UHFFFAOYSA-N 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
125000000464 thioxo group Chemical group S=* 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 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
235000019871 vegetable fat Nutrition 0.000 description 1
230000009385 viral infection Effects 0.000 description 1
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239000008096 xylene Substances 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)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
General Chemical & Material Sciences (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
Immunology (AREA)
Engineering & Computer Science (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Biochemistry (AREA)
General Engineering & Computer Science (AREA)
Molecular Biology (AREA)
Communicable Diseases (AREA)
Oncology (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Pyridine Compounds (AREA)

NO782399A 1977-07-11 1978-07-10 Fremgangsmaate ved fremstilling av 1-acyl-2-cyanaziridiner NO782399L (no)

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
NO782399L true NO782399L (no)	1979-01-12

Family

ID=6013651

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO782399A NO782399L (no)	1977-07-11	1978-07-10	Fremgangsmaate ved fremstilling av 1-acyl-2-cyanaziridiner

Country Status (26)

Country	Link
US (1)	US4267174A (de)
JP (1)	JPS5436254A (de)
AT (1)	AT356663B (de)
AU (2)	AU3782678A (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)

Families Citing this family (22)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2906603A1 (de) *	1979-02-21	1980-09-04	Boehringer Mannheim Gmbh	N-substituierte aziridin-2-carbonsaeurederivate, verfahren zu deren herstellung sowie diese substanzen enthaltende arzneimittel
US4393000A (en) *	1979-12-12	1983-07-12	Mitsui Toatsu Chemicals, Inc.	Cyclization process for producing aziridine-2-carboxylic acid or its salts
US4925835A (en) *	1986-05-01	1990-05-15	Sloan-Kettering Institute For Cancer Research	Aziridinyl putrescine containing compositions and their uses in treating prostate cancer
US6982263B2 (en) *	2001-06-08	2006-01-03	Boehringer Ingelheim Pharmaceuticals, Inc.	Nitriles useful as reversible inhibitors of cysteine proteases
MXPA05007485A (es)	2003-01-14	2006-01-30	Arena Pharm Inc	Derivados de arilo y heteroarilo 1,2,3-trisubstituidos como moduladores del metabolismo y la profilaxis y tratamiento de trastornos relacionados con ello tales como diabetes e hiperglicemia.
WO2004076413A2 (en) *	2003-02-24	2004-09-10	Arena Pharmaceuticals, Inc.	Phenyl- and pyridylpiperidine-derivatives as modulators of glucose metabolism
AR045047A1 (es) *	2003-07-11	2005-10-12	Arena Pharm Inc	Derivados arilo y heteroarilo trisustituidos como moduladores del metabolismo y de la profilaxis y tratamiento de desordenes relacionados con los mismos
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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 SU SU782631500A patent/SU1077565A3/ru active
- 1978-07-04 FI FI782157A patent/FI782157A7/fi not_active Application Discontinuation
- 1978-07-04 ZA ZA783829A patent/ZA783829B/xx unknown
- 1978-07-04 CA CA306,740A patent/CA1086309A/en not_active Expired
- 1978-07-05 PL PL1978208195A patent/PL126639B1/pl unknown
- 1978-07-05 NL NL7807276A patent/NL7807276A/xx not_active Application Discontinuation
- 1978-07-06 ES ES471512A patent/ES471512A1/es not_active Expired
- 1978-07-06 DD DD78206567A patent/DD137710A5/de unknown
- 1978-07-06 BE BE189121A patent/BE868796A/xx unknown
- 1978-07-06 AU AU37826/78A patent/AU3782678A/en active Granted
- 1978-07-06 AU AU37826/78A patent/AU519219B2/en not_active Expired
- 1978-07-07 DK DK783069A patent/DK306978A/da not_active Application Discontinuation
- 1978-07-07 CS CS784544A patent/CS208656B2/cs unknown
- 1978-07-07 SE SE7807642A patent/SE7807642L/xx unknown
- 1978-07-07 IT IT25474/78A patent/IT1096910B/it active
- 1978-07-07 LU LU79937A patent/LU79937A1/de unknown
- 1978-07-07 NZ NZ187794A patent/NZ187794A/xx unknown
- 1978-07-07 PT PT68263A patent/PT68263A/de unknown
- 1978-07-09 IL IL55109A patent/IL55109A/xx unknown
- 1978-07-10 HU HU78BO1723A patent/HU179428B/hu unknown
- 1978-07-10 FR FR7820468A patent/FR2397403A1/fr not_active Withdrawn
- 1978-07-10 AT AT496478A patent/AT356663B/de not_active IP Right Cessation
- 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
AU519219B2 (en)	1981-11-19
BE868796A (fr)	1979-01-08
AT356663B (de)	1980-05-12
LU79937A1 (de)	1980-02-14
IT7825474A0 (it)	1978-07-07
DD137710A5 (de)	1979-09-19
NL7807276A (nl)	1979-01-15
IL55109A0 (en)	1978-09-29
JPS5436254A (en)	1979-03-16
CA1086309A (en)	1980-09-23
FR2397403A1 (fr)	1979-02-09
ZA783829B (en)	1980-03-26
IT1096910B (it)	1985-08-26
GB1594079A (en)	1981-07-30
IL55109A (en)	1982-07-30
PL126639B1 (en)	1983-08-31
NZ187794A (en)	1980-05-08
FI782157A7 (fi)	1979-01-12
DK306978A (da)	1979-01-12
ES471512A1 (es)	1979-10-01
AU3782578A (en)	1980-01-10
AU3782678A (en)	1980-01-10
CS208656B2 (en)	1981-09-15
HU179428B (en)	1982-10-28
SE7807642L (sv)	1979-03-14
US4267174A (en)	1981-05-12
PL208195A1 (de)	1980-03-24
PT68263A (de)	1978-08-01
DE2731264A1 (de)	1979-02-01
ATA496478A (de)	1979-10-15
SU1077565A3 (ru)	1984-02-29

Publication	Publication Date	Title
NO782399L (no)	1979-01-12	Fremgangsmaate ved fremstilling av 1-acyl-2-cyanaziridiner
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NO892982L (no)	1990-02-05	Tetrahydro-1-benz-(c,d)-indolpropionsyre-sulfonamider.
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AU2021394226B2 (en)	2024-10-03	Benzylamine or benzyl alcohol derivative and use thereof
EP0295049B1 (de)	1991-10-09	Thiophensulfonamide zur Behandlung von Glaukom
CA2081330C (en)	2002-02-05	3-indolyl thioacetate derivatives
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DK155996B (da)	1989-06-12	Analogifremgangsmaade til fremstilling af substituerede beta-oxo-alfa-phenylcarbamoyl-pyrrolpropionitriler eller deres enolform eller enol-c(1-4)-alkylethere eller enol-c(1-4)-alkanoylestere deraf eller salte deraf med baser
NO773377L (no)	1978-04-06	Fremgangsmaate ved fremstilling av 1-(n-acyl-carbamoyl)-2-cyanaziridiner
KR930006776B1 (ko)	1993-07-23	치환된 이속사졸 유도체의 제조방법
NO180085B (no)	1996-11-04	Acylsulfonamido- og sulfonamidopyridin-2-karboksylsyreestere og deres anvendelse som legemidler
EP0371342B1 (de)	1994-12-14	2-Halogensubstituierte N-Indolylethyl-sulfonsäureamide, Verfahren zu ihrer Herstellung und ihre Verwendung in Arzneimitteln
CN119119019B (zh)	2025-11-11	一种杂环磺酰胺/磺酸酯衍生物及其制备方法、应用
NO155097B (no)	1986-11-03	Analogifremgangsmaate ved fremstilling av terapeutisk aktivt n-(1'-allyl-2'-pyrrolidinylmethyl)-2-methoxy-4-amino-5-methylsulfamoylbenzamid.
CN111793011B (zh)	2021-08-20	一种苯乙烯砜类nlrp3炎性小体抑制剂及其制备方法与应用
EP0518904B1 (de)	1994-11-30	S-(2-thenoyl)-thiolactonsäure mit pharmazeutischer wirkung
NO792510L (no)	1980-02-01	Fremgangsmaate ved fremstilling av oxadiazolotriazin-derivater
EP0145304B1 (de)	1988-04-20	Tetrahydro-beta-carbolinderivate und Verfahren zu ihrer Herstellung
CS252828B2 (en)	1987-10-15	Method of n,3-disubstituted 2-oxindole-1-carboxamides production
JPS5833222B2 (ja)	1983-07-18	新規ジペプチド類
NO841217L (no)	1985-09-30	Fremgangsmaate til fremstilling av beta-oxo-alfa-carbamoyl-pyrrolpropionitriler
NO151323B (no)	1984-12-10	Analogifremgangsmaate til fremstilling av et terapeutisk aktivt n-(2-tienyl)-2-okso-2,3-dihydro-benzo(b)tiofen-3-karboksamid
CH636607A5 (en)	1983-06-15	1-(N-Acylcarbamoyl)-2-cyanoaziridines having cancerostatic and immunostimulatory effects, and processes for the preparation thereof