LV10619B - Therapeutic agents - Google Patents
Therapeutic agents Download PDFInfo
- Publication number
- LV10619B LV10619B LVP-93-815A LV930815A LV10619B LV 10619 B LV10619 B LV 10619B LV 930815 A LV930815 A LV 930815A LV 10619 B LV10619 B LV 10619B
- Authority
- LV
- Latvia
- Prior art keywords
- methyl
- mixture
- morpholinophenyl
- carbon atoms
- formula
- Prior art date
Links
- 239000003814 drug Substances 0.000 title 1
- 229940124597 therapeutic agent Drugs 0.000 title 1
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 102
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 47
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 22
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 21
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 20
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 16
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 7
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 7
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims abstract description 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 94
- 125000002947 alkylene group Chemical group 0.000 claims description 20
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 18
- 229910052799 carbon Inorganic materials 0.000 claims description 15
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 14
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 125000003277 amino group Chemical group 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000002837 carbocyclic group Chemical group 0.000 claims description 3
- 125000006353 oxyethylene group Chemical group 0.000 claims description 3
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims 1
- 241000320892 Clerodendrum phlomidis Species 0.000 claims 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 claims 1
- 244000046052 Phaseolus vulgaris Species 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 1
- 229910002091 carbon monoxide Inorganic materials 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
- 210000002966 serum Anatomy 0.000 claims 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- 125000004001 thioalkyl group Chemical group 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 146
- 150000003839 salts Chemical class 0.000 abstract description 52
- 125000000753 cycloalkyl group Chemical group 0.000 abstract description 13
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract description 9
- 125000004093 cyano group Chemical group *C#N 0.000 abstract description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract description 3
- 229940126904 hypoglycaemic agent Drugs 0.000 abstract 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 360
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 259
- 239000000203 mixture Substances 0.000 description 253
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 209
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 183
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 178
- -1 sulphinyl Chemical group 0.000 description 166
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 159
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 109
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 99
- 238000006243 chemical reaction Methods 0.000 description 91
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 71
- 239000000243 solution Substances 0.000 description 66
- 239000000047 product Substances 0.000 description 60
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl chloride Substances ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 59
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 57
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 56
- 239000003921 oil Substances 0.000 description 53
- 235000019198 oils Nutrition 0.000 description 53
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 48
- 239000007787 solid Substances 0.000 description 46
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 45
- 238000010992 reflux Methods 0.000 description 43
- 239000002904 solvent Substances 0.000 description 43
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 43
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 42
- 229940093499 ethyl acetate Drugs 0.000 description 33
- 235000019439 ethyl acetate Nutrition 0.000 description 33
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 30
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 30
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 30
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 29
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 28
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 26
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 24
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 23
- 238000000034 method Methods 0.000 description 23
- 239000001530 fumaric acid Substances 0.000 description 22
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 20
- 238000004587 chromatography analysis Methods 0.000 description 20
- QKWLVAYDAHQMLG-UHFFFAOYSA-N 2-morpholin-4-ylaniline Chemical compound NC1=CC=CC=C1N1CCOCC1 QKWLVAYDAHQMLG-UHFFFAOYSA-N 0.000 description 19
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 19
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 18
- 239000012267 brine Substances 0.000 description 16
- 229940046892 lead acetate Drugs 0.000 description 16
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 16
- 238000001704 evaporation Methods 0.000 description 15
- 230000008020 evaporation Effects 0.000 description 15
- 239000000284 extract Substances 0.000 description 15
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 14
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 14
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 14
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 13
- 238000005859 coupling reaction Methods 0.000 description 13
- LGDSHSYDSCRFAB-UHFFFAOYSA-N Methyl isothiocyanate Chemical compound CN=C=S LGDSHSYDSCRFAB-UHFFFAOYSA-N 0.000 description 12
- KQNKJJBFUFKYFX-UHFFFAOYSA-N acetic acid;trihydrate Chemical compound O.O.O.CC(O)=O KQNKJJBFUFKYFX-UHFFFAOYSA-N 0.000 description 12
- 238000002360 preparation method Methods 0.000 description 12
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 12
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 11
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 11
- 238000001914 filtration Methods 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 229910021529 ammonia Inorganic materials 0.000 description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 10
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
- YIMGGHGOVMBIJO-UHFFFAOYSA-N 1,1-dimethyl-2-(2-morpholin-4-ylphenyl)guanidine Chemical compound CN(C)C(N)=NC1=CC=CC=C1N1CCOCC1 YIMGGHGOVMBIJO-UHFFFAOYSA-N 0.000 description 9
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 9
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 9
- 150000001412 amines Chemical class 0.000 description 9
- 235000011114 ammonium hydroxide Nutrition 0.000 description 9
- 238000004440 column chromatography Methods 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 description 9
- WOCANZVRSXYFPS-UHFFFAOYSA-N methyl n'-(2-morpholin-4-ylphenyl)carbamimidothioate;hydroiodide Chemical compound I.CSC(=N)NC1=CC=CC=C1N1CCOCC1 WOCANZVRSXYFPS-UHFFFAOYSA-N 0.000 description 9
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 9
- 230000007935 neutral effect Effects 0.000 description 9
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 8
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 description 8
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 8
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 8
- 239000003826 tablet Substances 0.000 description 8
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 7
- SRVXSISGYBMIHR-UHFFFAOYSA-N 3-[3-[3-(2-amino-2-oxoethyl)phenyl]-5-chlorophenyl]-3-(5-methyl-1,3-thiazol-2-yl)propanoic acid Chemical compound S1C(C)=CN=C1C(CC(O)=O)C1=CC(Cl)=CC(C=2C=C(CC(N)=O)C=CC=2)=C1 SRVXSISGYBMIHR-UHFFFAOYSA-N 0.000 description 7
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 7
- 239000002585 base Substances 0.000 description 7
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 7
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 101000986989 Naja kaouthia Acidic phospholipase A2 CM-II Proteins 0.000 description 6
- 239000010949 copper Substances 0.000 description 6
- 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 6
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 6
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 5
- BNBJMXCRCHPDIG-UHFFFAOYSA-N 2-(morpholin-4-ylmethyl)aniline Chemical compound NC1=CC=CC=C1CN1CCOCC1 BNBJMXCRCHPDIG-UHFFFAOYSA-N 0.000 description 5
- HNAAKIPAJBGKCC-UHFFFAOYSA-N 2-morpholin-4-ylaniline;hydrochloride Chemical compound Cl.NC1=CC=CC=C1N1CCOCC1 HNAAKIPAJBGKCC-UHFFFAOYSA-N 0.000 description 5
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
- 230000001476 alcoholic effect Effects 0.000 description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
- 239000002775 capsule Substances 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 239000008103 glucose Substances 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 239000010410 layer Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 description 5
- UKLNMMHNWFDKNT-UHFFFAOYSA-M sodium chlorite Chemical compound [Na+].[O-]Cl=O UKLNMMHNWFDKNT-UHFFFAOYSA-M 0.000 description 5
- 229960002218 sodium chlorite Drugs 0.000 description 5
- 229910001220 stainless steel Inorganic materials 0.000 description 5
- 239000010935 stainless steel Substances 0.000 description 5
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 5
- COSWCAGTKRUTQV-UHFFFAOYSA-N 1,1,3-trimethylurea Chemical compound CNC(=O)N(C)C COSWCAGTKRUTQV-UHFFFAOYSA-N 0.000 description 4
- OQLZINXFSUDMHM-UHFFFAOYSA-N Acetamidine Chemical compound CC(N)=N OQLZINXFSUDMHM-UHFFFAOYSA-N 0.000 description 4
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 4
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 4
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 239000004202 carbamide Substances 0.000 description 4
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 4
- OAGOUCJGXNLJNL-UHFFFAOYSA-N dimethylcyanamide Chemical compound CN(C)C#N OAGOUCJGXNLJNL-UHFFFAOYSA-N 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 4
- 125000001153 fluoro group Chemical group F* 0.000 description 4
- 239000012458 free base Substances 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- KRZGKJJPEOUIBI-UHFFFAOYSA-N hydron;thiourea;iodide Chemical compound I.NC(S)=N KRZGKJJPEOUIBI-UHFFFAOYSA-N 0.000 description 4
- 230000002218 hypoglycaemic effect Effects 0.000 description 4
- LRDFRRGEGBBSRN-UHFFFAOYSA-N isobutyronitrile Chemical compound CC(C)C#N LRDFRRGEGBBSRN-UHFFFAOYSA-N 0.000 description 4
- 150000002540 isothiocyanates Chemical class 0.000 description 4
- 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 239000008194 pharmaceutical composition Substances 0.000 description 4
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- 230000001225 therapeutic effect Effects 0.000 description 4
- AQYPBQKDGHHKBD-UHFFFAOYSA-N (2-morpholin-4-ylphenyl)cyanamide Chemical compound N#CNC1=CC=CC=C1N1CCOCC1 AQYPBQKDGHHKBD-UHFFFAOYSA-N 0.000 description 3
- CMMLLKHOSNEVFO-UHFFFAOYSA-N (2-morpholin-4-ylphenyl)thiourea Chemical compound NC(=S)NC1=CC=CC=C1N1CCOCC1 CMMLLKHOSNEVFO-UHFFFAOYSA-N 0.000 description 3
- OWOQFKKPHWXCKM-UHFFFAOYSA-N 1,1-dimethyl-3-(2-morpholin-4-ylphenyl)thiourea Chemical compound CN(C)C(=S)NC1=CC=CC=C1N1CCOCC1 OWOQFKKPHWXCKM-UHFFFAOYSA-N 0.000 description 3
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 3
- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 3
- ASUDFOJKTJLAIK-UHFFFAOYSA-N 2-methoxyethanamine Chemical compound COCCN ASUDFOJKTJLAIK-UHFFFAOYSA-N 0.000 description 3
- NSVHSRBHIFWVGP-UHFFFAOYSA-N 5-fluoro-2-morpholin-4-ylaniline Chemical compound NC1=CC(F)=CC=C1N1CCOCC1 NSVHSRBHIFWVGP-UHFFFAOYSA-N 0.000 description 3
- ZRPZPNYZFSJUPA-UHFFFAOYSA-N ARS-1620 Chemical compound Oc1cccc(F)c1-c1c(Cl)cc2c(ncnc2c1F)N1CCN(CC1)C(=O)C=C ZRPZPNYZFSJUPA-UHFFFAOYSA-N 0.000 description 3
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- 239000005864 Sulphur Substances 0.000 description 3
- LXRZVMYMQHNYJB-UNXOBOICSA-N [(1R,2S,4R)-4-[[5-[4-[(1R)-7-chloro-1,2,3,4-tetrahydroisoquinolin-1-yl]-5-methylthiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound CC1=C(C=C(S1)C(=O)C1=C(N[C@H]2C[C@H](O)[C@@H](COS(N)(=O)=O)C2)N=CN=C1)[C@@H]1NCCC2=C1C=C(Cl)C=C2 LXRZVMYMQHNYJB-UNXOBOICSA-N 0.000 description 3
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- RCJVRSBWZCNNQT-UHFFFAOYSA-N dichloridooxygen Chemical compound ClOCl RCJVRSBWZCNNQT-UHFFFAOYSA-N 0.000 description 3
- 229940071870 hydroiodic acid Drugs 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 239000008101 lactose Substances 0.000 description 3
- 235000019359 magnesium stearate Nutrition 0.000 description 3
- 239000002609 medium Substances 0.000 description 3
- KMYMSTJFWMBXPQ-UHFFFAOYSA-N methyl n'-ethyl-n-(2-morpholin-4-ylphenyl)carbamimidothioate;hydroiodide Chemical compound I.CCN=C(SC)NC1=CC=CC=C1N1CCOCC1 KMYMSTJFWMBXPQ-UHFFFAOYSA-N 0.000 description 3
- AYBOKXXQIIWKAJ-UHFFFAOYSA-N methyl n'-methyl-n-(2-morpholin-4-ylphenyl)carbamimidothioate;hydroiodide Chemical compound I.CSC(=NC)NC1=CC=CC=C1N1CCOCC1 AYBOKXXQIIWKAJ-UHFFFAOYSA-N 0.000 description 3
- NPTMHWWBARRCMP-UHFFFAOYSA-N methyl n'-methyl-n-(5-methyl-2-morpholin-4-ylphenyl)carbamimidothioate;hydroiodide Chemical compound I.CSC(=NC)NC1=CC(C)=CC=C1N1CCOCC1 NPTMHWWBARRCMP-UHFFFAOYSA-N 0.000 description 3
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 239000011574 phosphorus Substances 0.000 description 3
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 3
- 239000012429 reaction media Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000012047 saturated solution Substances 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 3
- 239000000829 suppository Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 150000003585 thioureas Chemical class 0.000 description 3
- FMZUSBBVCUQQBC-UHFFFAOYSA-N (2-methyl-6-piperidin-1-ylphenyl)thiourea Chemical compound CC1=CC=CC(N2CCCCC2)=C1NC(N)=S FMZUSBBVCUQQBC-UHFFFAOYSA-N 0.000 description 2
- VGICPVCQAZPROO-UHFFFAOYSA-N (3-methyl-2-morpholin-4-ylphenyl)thiourea Chemical compound CC1=CC=CC(NC(N)=S)=C1N1CCOCC1 VGICPVCQAZPROO-UHFFFAOYSA-N 0.000 description 2
- KUYYWVDLLLFAAA-UHFFFAOYSA-N (5-chloro-2-morpholin-4-ylphenyl)cyanamide Chemical compound N#CNC1=CC(Cl)=CC=C1N1CCOCC1 KUYYWVDLLLFAAA-UHFFFAOYSA-N 0.000 description 2
- FDOGAHCLAIGGEZ-UHFFFAOYSA-N (5-chloro-2-morpholin-4-ylphenyl)thiourea Chemical compound NC(=S)NC1=CC(Cl)=CC=C1N1CCOCC1 FDOGAHCLAIGGEZ-UHFFFAOYSA-N 0.000 description 2
- SOWKCCAHSVVGPU-UHFFFAOYSA-N (5-fluoro-2-morpholin-4-ylphenyl)thiourea Chemical compound NC(=S)NC1=CC(F)=CC=C1N1CCOCC1 SOWKCCAHSVVGPU-UHFFFAOYSA-N 0.000 description 2
- HBAIZGPCSAAFSU-UHFFFAOYSA-N 1-(2-hydroxyethyl)imidazolidin-2-one Chemical compound OCCN1CCNC1=O HBAIZGPCSAAFSU-UHFFFAOYSA-N 0.000 description 2
- ATDLANNMDBYQDO-UHFFFAOYSA-N 1-(2-isothiocyanato-3-methylphenyl)piperidine Chemical compound CC1=CC=CC(N2CCCCC2)=C1N=C=S ATDLANNMDBYQDO-UHFFFAOYSA-N 0.000 description 2
- CJMUPCHCOYBPLD-UHFFFAOYSA-N 1-(2-isothiocyanatophenyl)piperidine Chemical compound S=C=NC1=CC=CC=C1N1CCCCC1 CJMUPCHCOYBPLD-UHFFFAOYSA-N 0.000 description 2
- OAXRDUZQOFLVPR-UHFFFAOYSA-N 1-butyl-3-(2-morpholin-4-ylphenyl)thiourea Chemical compound CCCCNC(=S)NC1=CC=CC=C1N1CCOCC1 OAXRDUZQOFLVPR-UHFFFAOYSA-N 0.000 description 2
- JZDBCWJVHNVLLS-UHFFFAOYSA-N 1-ethyl-1,3,3-trimethyl-2-(2-morpholin-4-ylphenyl)guanidine Chemical compound CCN(C)C(N(C)C)=NC1=CC=CC=C1N1CCOCC1 JZDBCWJVHNVLLS-UHFFFAOYSA-N 0.000 description 2
- XRNUJRCHADWHOJ-UHFFFAOYSA-N 1-ethyl-3-(2-morpholin-4-ylphenyl)thiourea Chemical compound CCNC(=S)NC1=CC=CC=C1N1CCOCC1 XRNUJRCHADWHOJ-UHFFFAOYSA-N 0.000 description 2
- PWKNBLFSJAVFAB-UHFFFAOYSA-N 1-fluoro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1F PWKNBLFSJAVFAB-UHFFFAOYSA-N 0.000 description 2
- NOGFHTGYPKWWRX-UHFFFAOYSA-N 2,2,6,6-tetramethyloxan-4-one Chemical compound CC1(C)CC(=O)CC(C)(C)O1 NOGFHTGYPKWWRX-UHFFFAOYSA-N 0.000 description 2
- FNHMJTUQUPQWJN-UHFFFAOYSA-N 2,2-dimethylpropanimidamide Chemical compound CC(C)(C)C(N)=N FNHMJTUQUPQWJN-UHFFFAOYSA-N 0.000 description 2
- MKJDUTHNQPJPAI-UHFFFAOYSA-N 2-(2-oxoimidazolidin-1-yl)ethyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCCN1CCNC1=O MKJDUTHNQPJPAI-UHFFFAOYSA-N 0.000 description 2
- GNFAFICJRPMXKZ-UHFFFAOYSA-N 2-(3-aminobutan-2-ylamino)ethanol Chemical compound CC(N)C(C)NCCO GNFAFICJRPMXKZ-UHFFFAOYSA-N 0.000 description 2
- ICSHCPATZANHRG-UHFFFAOYSA-N 2-(3-methyl-2-oxoimidazolidin-1-yl)ethyl acetate Chemical compound CN1CCN(CCOC(C)=O)C1=O ICSHCPATZANHRG-UHFFFAOYSA-N 0.000 description 2
- DYPMOFPPFNCXLJ-UHFFFAOYSA-N 2-(3-methyl-2-oxoimidazolidin-1-yl)ethyl benzoate Chemical compound O=C1N(C)CCN1CCOC(=O)C1=CC=CC=C1 DYPMOFPPFNCXLJ-UHFFFAOYSA-N 0.000 description 2
- ASEWKVACNDUPPV-UHFFFAOYSA-N 2-(morpholin-4-ylmethyl)aniline;dihydrochloride Chemical compound Cl.Cl.NC1=CC=CC=C1CN1CCOCC1 ASEWKVACNDUPPV-UHFFFAOYSA-N 0.000 description 2
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- DAAVYQQFXKNSLP-UHFFFAOYSA-N 2-methyl-1-(2-morpholin-4-ylphenyl)-3-pentylguanidine Chemical compound CCCCCNC(NC)=NC1=CC=CC=C1N1CCOCC1 DAAVYQQFXKNSLP-UHFFFAOYSA-N 0.000 description 2
- GBSFGJLUSXBIHM-UHFFFAOYSA-N 2-methyl-6-morpholin-4-ylaniline Chemical compound CC1=CC=CC(N2CCOCC2)=C1N GBSFGJLUSXBIHM-UHFFFAOYSA-N 0.000 description 2
- WECUSHSUUIHVCH-UHFFFAOYSA-N 2-methyl-n'-(2-morpholin-4-ylphenyl)propanimidamide Chemical compound CC(C)C(=N)NC1=CC=CC=C1N1CCOCC1 WECUSHSUUIHVCH-UHFFFAOYSA-N 0.000 description 2
- DPJCXCZTLWNFOH-UHFFFAOYSA-N 2-nitroaniline Chemical compound NC1=CC=CC=C1[N+]([O-])=O DPJCXCZTLWNFOH-UHFFFAOYSA-N 0.000 description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
- OYECAJPUPWFCSL-UHFFFAOYSA-N 2-piperidin-1-ylaniline Chemical compound NC1=CC=CC=C1N1CCCCC1 OYECAJPUPWFCSL-UHFFFAOYSA-N 0.000 description 2
- BFPUBGCFJMIZDF-UHFFFAOYSA-N 2-pyrrolidin-1-ylaniline Chemical compound NC1=CC=CC=C1N1CCCC1 BFPUBGCFJMIZDF-UHFFFAOYSA-N 0.000 description 2
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 2
- UXQVCAUVMIYSDD-UHFFFAOYSA-N 3-isothiocyanato-4-morpholin-4-ylbenzonitrile Chemical compound S=C=NC1=CC(C#N)=CC=C1N1CCOCC1 UXQVCAUVMIYSDD-UHFFFAOYSA-N 0.000 description 2
- LZNKUJZSQSIVJR-UHFFFAOYSA-N 4-(2-isothiocyanato-3-methylphenyl)morpholine Chemical compound CC1=CC=CC(N2CCOCC2)=C1N=C=S LZNKUJZSQSIVJR-UHFFFAOYSA-N 0.000 description 2
- OKTXVZOPNMPSAU-UHFFFAOYSA-N 4-(2-isothiocyanato-5-methoxyphenyl)morpholine Chemical compound COC1=CC=C(N=C=S)C(N2CCOCC2)=C1 OKTXVZOPNMPSAU-UHFFFAOYSA-N 0.000 description 2
- IBDNPMVERHVYDJ-UHFFFAOYSA-N 4-(2-isothiocyanatophenyl)-1,2,4-oxathiazinane Chemical compound S=C=NC1=CC=CC=C1N1CSOCC1 IBDNPMVERHVYDJ-UHFFFAOYSA-N 0.000 description 2
- PKZODHURUCXOAG-UHFFFAOYSA-N 4-(2-isothiocyanatophenyl)morpholine Chemical compound S=C=NC1=CC=CC=C1N1CCOCC1 PKZODHURUCXOAG-UHFFFAOYSA-N 0.000 description 2
- OFWPPBDBRPIZRT-UHFFFAOYSA-N 4-(4-chloro-2-isothiocyanatophenyl)morpholine Chemical compound S=C=NC1=CC(Cl)=CC=C1N1CCOCC1 OFWPPBDBRPIZRT-UHFFFAOYSA-N 0.000 description 2
- KHVJNKFFYBDEAF-UHFFFAOYSA-N 4-(4-fluoro-2-isothiocyanatophenyl)morpholine Chemical compound S=C=NC1=CC(F)=CC=C1N1CCOCC1 KHVJNKFFYBDEAF-UHFFFAOYSA-N 0.000 description 2
- UPERWIGIMKKWRJ-UHFFFAOYSA-N 4-[2-isothiocyanato-4-(trifluoromethyl)phenyl]morpholine Chemical compound S=C=NC1=CC(C(F)(F)F)=CC=C1N1CCOCC1 UPERWIGIMKKWRJ-UHFFFAOYSA-N 0.000 description 2
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 2
- XBDOGBDXBXBNLH-UHFFFAOYSA-N 5-chloro-2-(morpholin-4-ylmethyl)aniline Chemical compound NC1=CC(Cl)=CC=C1CN1CCOCC1 XBDOGBDXBXBNLH-UHFFFAOYSA-N 0.000 description 2
- UNDBLGNMBLCRNJ-UHFFFAOYSA-N 5-chloro-2-morpholin-4-ylaniline Chemical compound NC1=CC(Cl)=CC=C1N1CCOCC1 UNDBLGNMBLCRNJ-UHFFFAOYSA-N 0.000 description 2
- FABHEYAZAOCBCH-UHFFFAOYSA-N 5-methyl-2-morpholin-4-ylaniline Chemical compound NC1=CC(C)=CC=C1N1CCOCC1 FABHEYAZAOCBCH-UHFFFAOYSA-N 0.000 description 2
- IOZYVTAARYKVDH-UHFFFAOYSA-N 5-methylsulfanyl-2-morpholin-4-ylaniline Chemical compound NC1=CC(SC)=CC=C1N1CCOCC1 IOZYVTAARYKVDH-UHFFFAOYSA-N 0.000 description 2
- 229920001817 Agar Polymers 0.000 description 2
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
- 229920000623 Cellulose acetate phthalate Polymers 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- RFFFKMOABOFIDF-UHFFFAOYSA-N Pentanenitrile Chemical compound CCCCC#N RFFFKMOABOFIDF-UHFFFAOYSA-N 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- BCPHWOMNTSHTTN-UHFFFAOYSA-N [2-(2-methylpyrrolidin-1-yl)phenyl]thiourea Chemical compound CC1CCCN1C1=CC=CC=C1NC(N)=S BCPHWOMNTSHTTN-UHFFFAOYSA-N 0.000 description 2
- LNDXVNYTVMIKED-UHFFFAOYSA-N [2-morpholin-4-yl-5-(trifluoromethyl)phenyl]thiourea Chemical compound NC(=S)NC1=CC(C(F)(F)F)=CC=C1N1CCOCC1 LNDXVNYTVMIKED-UHFFFAOYSA-N 0.000 description 2
- 239000008272 agar Substances 0.000 description 2
- LHIJANUOQQMGNT-UHFFFAOYSA-N aminoethylethanolamine Chemical compound NCCNCCO LHIJANUOQQMGNT-UHFFFAOYSA-N 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- CPEKAXYCDKETEN-UHFFFAOYSA-N benzoyl isothiocyanate Chemical compound S=C=NC(=O)C1=CC=CC=C1 CPEKAXYCDKETEN-UHFFFAOYSA-N 0.000 description 2
- KXHPPCXNWTUNSB-UHFFFAOYSA-M benzyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1=CC=CC=C1 KXHPPCXNWTUNSB-UHFFFAOYSA-M 0.000 description 2
- 125000006309 butyl amino group Chemical group 0.000 description 2
- LIMQQADUEULBSO-UHFFFAOYSA-N butyl isothiocyanate Chemical compound CCCCN=C=S LIMQQADUEULBSO-UHFFFAOYSA-N 0.000 description 2
- KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 description 2
- 150000001718 carbodiimides Chemical class 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 229940081734 cellulose acetate phthalate Drugs 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000013256 coordination polymer Substances 0.000 description 2
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 2
- 229960003280 cupric chloride Drugs 0.000 description 2
- 229940045803 cuprous chloride Drugs 0.000 description 2
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- 239000002702 enteric coating Substances 0.000 description 2
- 238000009505 enteric coating Methods 0.000 description 2
- XWBDWHCCBGMXKG-UHFFFAOYSA-N ethanamine;hydron;chloride Chemical compound Cl.CCN XWBDWHCCBGMXKG-UHFFFAOYSA-N 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 239000007903 gelatin capsule Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 125000005394 methallyl group Chemical group 0.000 description 2
- GCGDHCBOYJRUML-UHFFFAOYSA-N methyl n'-(2-morpholin-4-ylphenyl)carbamimidothioate Chemical compound CSC(=N)NC1=CC=CC=C1N1CCOCC1 GCGDHCBOYJRUML-UHFFFAOYSA-N 0.000 description 2
- 150000004682 monohydrates Chemical class 0.000 description 2
- YTHNKOKVVLANER-UHFFFAOYSA-N n'-[2-(morpholin-4-ylmethyl)phenyl]morpholine-4-carboximidamide Chemical compound C1COCCN1C(=N)NC1=CC=CC=C1CN1CCOCC1 YTHNKOKVVLANER-UHFFFAOYSA-N 0.000 description 2
- QMKKJBRRKIKWFK-UHFFFAOYSA-N n,2,2-trimethylpropanamide Chemical compound CNC(=O)C(C)(C)C QMKKJBRRKIKWFK-UHFFFAOYSA-N 0.000 description 2
- XUYVJGGBHWQISS-UHFFFAOYSA-N n-(2-morpholin-4-ylphenyl)-2,3,4,5-tetrahydropyridin-6-amine Chemical compound N1CCCCC1=NC1=CC=CC=C1N1CCOCC1 XUYVJGGBHWQISS-UHFFFAOYSA-N 0.000 description 2
- DRXOHRSIPOXMOU-UHFFFAOYSA-N n-[(2-pyrrolidin-1-ylphenyl)carbamothioyl]benzamide Chemical compound C=1C=CC=CC=1C(=O)NC(=S)NC1=CC=CC=C1N1CCCC1 DRXOHRSIPOXMOU-UHFFFAOYSA-N 0.000 description 2
- VCDBLXGXXUBKIS-UHFFFAOYSA-N n-methyl-n'-(2-morpholin-4-ylphenyl)methanediimine Chemical compound CN=C=NC1=CC=CC=C1N1CCOCC1 VCDBLXGXXUBKIS-UHFFFAOYSA-N 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- QKFJKGMPGYROCL-UHFFFAOYSA-N phenyl isothiocyanate Chemical compound S=C=NC1=CC=CC=C1 QKFJKGMPGYROCL-UHFFFAOYSA-N 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- FWPIDFUJEMBDLS-UHFFFAOYSA-L tin(II) chloride dihydrate Chemical compound O.O.Cl[Sn]Cl FWPIDFUJEMBDLS-UHFFFAOYSA-L 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- 238000001665 trituration Methods 0.000 description 2
- VCGRFBXVSFAGGA-UHFFFAOYSA-N (1,1-dioxo-1,4-thiazinan-4-yl)-[6-[[3-(4-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]methoxy]pyridin-3-yl]methanone Chemical compound CC=1ON=C(C=2C=CC(F)=CC=2)C=1COC(N=C1)=CC=C1C(=O)N1CCS(=O)(=O)CC1 VCGRFBXVSFAGGA-UHFFFAOYSA-N 0.000 description 1
- JEHAYQACLBXPFA-UHFFFAOYSA-N (2-methyl-6-morpholin-4-ylphenyl)thiourea Chemical compound CC1=CC=CC(N2CCOCC2)=C1NC(N)=S JEHAYQACLBXPFA-UHFFFAOYSA-N 0.000 description 1
- JFXFQLTTXMZHBM-UHFFFAOYSA-N (2-piperidin-1-ylphenyl)thiourea Chemical compound NC(=S)NC1=CC=CC=C1N1CCCCC1 JFXFQLTTXMZHBM-UHFFFAOYSA-N 0.000 description 1
- SMVFRCLPUWCZIF-UHFFFAOYSA-N (2-pyrrolidin-1-ylphenyl)thiourea Chemical compound NC(=S)NC1=CC=CC=C1N1CCCC1 SMVFRCLPUWCZIF-UHFFFAOYSA-N 0.000 description 1
- LOPWBKHHJFJKPO-UHFFFAOYSA-N (3-methyl-2-morpholin-4-ylphenyl)cyanamide Chemical compound CC1=CC=CC(NC#N)=C1N1CCOCC1 LOPWBKHHJFJKPO-UHFFFAOYSA-N 0.000 description 1
- AHVKUQNZOIILGF-UHFFFAOYSA-N (4-methoxy-2-morpholin-4-ylphenyl)cyanamide Chemical compound COC1=CC=C(NC#N)C(N2CCOCC2)=C1 AHVKUQNZOIILGF-UHFFFAOYSA-N 0.000 description 1
- LGVPAWVLLZMLPB-UHFFFAOYSA-N (4-methoxy-2-morpholin-4-ylphenyl)thiourea Chemical compound COC1=CC=C(NC(N)=S)C(N2CCOCC2)=C1 LGVPAWVLLZMLPB-UHFFFAOYSA-N 0.000 description 1
- VJRKYCLWDMCDTO-UHFFFAOYSA-N (5-cyano-2-morpholin-4-ylphenyl)thiourea Chemical compound NC(=S)NC1=CC(C#N)=CC=C1N1CCOCC1 VJRKYCLWDMCDTO-UHFFFAOYSA-N 0.000 description 1
- DYMVJWOTOQCATD-UHFFFAOYSA-N (5-fluoro-2-morpholin-4-ylphenyl)cyanamide Chemical compound N#CNC1=CC(F)=CC=C1N1CCOCC1 DYMVJWOTOQCATD-UHFFFAOYSA-N 0.000 description 1
- DYVNRINBPSJWRZ-UHFFFAOYSA-N (5-methyl-2-morpholin-4-ylphenyl)thiourea Chemical compound NC(=S)NC1=CC(C)=CC=C1N1CCOCC1 DYVNRINBPSJWRZ-UHFFFAOYSA-N 0.000 description 1
- YYFVQJWLZUNRAO-VQYXCCSOSA-N (E)-but-2-enedioic acid 2-[2-(5-methyl-2-morpholin-4-ylanilino)-4,5-dihydroimidazol-1-yl]ethanol Chemical compound OC(=O)\C=C\C(O)=O.OC(=O)\C=C\C(O)=O.OC(=O)\C=C\C(O)=O.Cc1ccc(N2CCOCC2)c(NC2=NCCN2CCO)c1.Cc1ccc(N2CCOCC2)c(NC2=NCCN2CCO)c1 YYFVQJWLZUNRAO-VQYXCCSOSA-N 0.000 description 1
- WHHDLFMIKFEKHM-WLHGVMLRSA-N (e)-but-2-enedioic acid;1,2-dimethyl-3-(5-methyl-2-morpholin-4-ylphenyl)guanidine Chemical compound OC(=O)\C=C\C(O)=O.CNC(=NC)NC1=CC(C)=CC=C1N1CCOCC1 WHHDLFMIKFEKHM-WLHGVMLRSA-N 0.000 description 1
- VFCPSDWWULELNJ-WLHGVMLRSA-N (e)-but-2-enedioic acid;1-(2-methoxyethyl)-2-methyl-3-(2-morpholin-4-ylphenyl)guanidine Chemical compound OC(=O)\C=C\C(O)=O.COCCNC(=NC)NC1=CC=CC=C1N1CCOCC1 VFCPSDWWULELNJ-WLHGVMLRSA-N 0.000 description 1
- FOOHLVMVJNXERH-WLHGVMLRSA-N (e)-but-2-enedioic acid;1-(2-methoxyethyl)-3-methyl-n-(2-morpholin-4-ylphenyl)imidazolidin-2-imine Chemical compound OC(=O)\C=C\C(O)=O.COCCN1CCN(C)C1=NC1=CC=CC=C1N1CCOCC1 FOOHLVMVJNXERH-WLHGVMLRSA-N 0.000 description 1
- IIVUJZFZKBHIGU-WLHGVMLRSA-N (e)-but-2-enedioic acid;1-cyclopentyl-2-methyl-3-(2-morpholin-4-ylphenyl)guanidine Chemical compound OC(=O)\C=C\C(O)=O.C=1C=CC=C(N2CCOCC2)C=1NC(=NC)NC1CCCC1 IIVUJZFZKBHIGU-WLHGVMLRSA-N 0.000 description 1
- KJJQAGBCYUBELI-WLHGVMLRSA-N (e)-but-2-enedioic acid;4-methyl-n-(2-morpholin-4-ylphenyl)-3,4-dihydro-2h-pyrrol-5-amine Chemical compound OC(=O)\C=C\C(O)=O.CC1CCNC1=NC1=CC=CC=C1N1CCOCC1 KJJQAGBCYUBELI-WLHGVMLRSA-N 0.000 description 1
- LHXCUWOJEALYLZ-WLHGVMLRSA-N (e)-but-2-enedioic acid;morpholine Chemical compound C1COCCN1.OC(=O)\C=C\C(O)=O LHXCUWOJEALYLZ-WLHGVMLRSA-N 0.000 description 1
- UKGJZDSUJSPAJL-YPUOHESYSA-N (e)-n-[(1r)-1-[3,5-difluoro-4-(methanesulfonamido)phenyl]ethyl]-3-[2-propyl-6-(trifluoromethyl)pyridin-3-yl]prop-2-enamide Chemical compound CCCC1=NC(C(F)(F)F)=CC=C1\C=C\C(=O)N[C@H](C)C1=CC(F)=C(NS(C)(=O)=O)C(F)=C1 UKGJZDSUJSPAJL-YPUOHESYSA-N 0.000 description 1
- ZGYIXVSQHOKQRZ-COIATFDQSA-N (e)-n-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]-3-cyano-7-[(3s)-oxolan-3-yl]oxyquinolin-6-yl]-4-(dimethylamino)but-2-enamide Chemical compound N#CC1=CN=C2C=C(O[C@@H]3COCC3)C(NC(=O)/C=C/CN(C)C)=CC2=C1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 ZGYIXVSQHOKQRZ-COIATFDQSA-N 0.000 description 1
- QKUOKKCUFHBMIO-UHFFFAOYSA-N 1,1,3,3-tetramethyl-2-(2-morpholin-4-ylphenyl)guanidine;hydroiodide Chemical compound I.CN(C)C(N(C)C)=NC1=CC=CC=C1N1CCOCC1 QKUOKKCUFHBMIO-UHFFFAOYSA-N 0.000 description 1
- AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 1
- HTMHPDAIJNNZKF-UHFFFAOYSA-N 1,1,3-trimethyl-2-(2-morpholin-4-ylphenyl)-3-pentylguanidine Chemical compound CCCCCN(C)C(N(C)C)=NC1=CC=CC=C1N1CCOCC1 HTMHPDAIJNNZKF-UHFFFAOYSA-N 0.000 description 1
- DLRNNHKSTRYTSW-UHFFFAOYSA-N 1,1-dimethyl-2-(5-methyl-2-morpholin-4-ylphenyl)guanidine;hydrochloride Chemical compound Cl.CN(C)C(N)=NC1=CC(C)=CC=C1N1CCOCC1 DLRNNHKSTRYTSW-UHFFFAOYSA-N 0.000 description 1
- ZFMPDYCKJRMUTD-UHFFFAOYSA-N 1,1-dimethyl-2-(5-methylsulfanyl-2-morpholin-4-ylphenyl)guanidine Chemical compound CN(C)C(N)=NC1=CC(SC)=CC=C1N1CCOCC1 ZFMPDYCKJRMUTD-UHFFFAOYSA-N 0.000 description 1
- UTHYUHJAUOKQOI-UHFFFAOYSA-N 1,1-dimethyl-2-(5-methylsulfinyl-2-morpholin-4-ylphenyl)guanidine Chemical compound CN(C)C(N)=NC1=CC(S(C)=O)=CC=C1N1CCOCC1 UTHYUHJAUOKQOI-UHFFFAOYSA-N 0.000 description 1
- OZTPZKOTNKOWFT-UHFFFAOYSA-N 1,1-dimethyl-2-[5-(2-methylpropyl)-2-morpholin-4-ylphenyl]guanidine Chemical compound CN(C)C(N)=NC1=CC(CC(C)C)=CC=C1N1CCOCC1 OZTPZKOTNKOWFT-UHFFFAOYSA-N 0.000 description 1
- HMMICDMDSIUFIP-UHFFFAOYSA-N 1,2-dimethyl-3-(2-morpholin-4-ylphenyl)guanidine Chemical compound CNC(NC)=NC1=CC=CC=C1N1CCOCC1 HMMICDMDSIUFIP-UHFFFAOYSA-N 0.000 description 1
- JZWXIHLNCRFQDL-UHFFFAOYSA-N 1,2-dimethyl-3-(5-methyl-2-morpholin-4-ylphenyl)guanidine Chemical compound CNC(NC)=NC1=CC(C)=CC=C1N1CCOCC1 JZWXIHLNCRFQDL-UHFFFAOYSA-N 0.000 description 1
- XOIJIQNLLZTAOI-UHFFFAOYSA-N 1,2-dimethyl-3-[2-(1,2,4-oxathiazinan-4-yl)phenyl]guanidine Chemical compound CNC(=NC)NC1=CC=CC=C1N1CSOCC1 XOIJIQNLLZTAOI-UHFFFAOYSA-N 0.000 description 1
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 description 1
- QLAJNZSPVITUCQ-UHFFFAOYSA-N 1,3,2-dioxathietane 2,2-dioxide Chemical compound O=S1(=O)OCO1 QLAJNZSPVITUCQ-UHFFFAOYSA-N 0.000 description 1
- TWFJBTCKIUQPKB-UHFFFAOYSA-N 1,3,3-trimethyl-n-(5-methyl-2-morpholin-4-ylphenyl)pyrrolidin-2-imine Chemical compound CN1CCC(C)(C)C1=NC1=CC(C)=CC=C1N1CCOCC1 TWFJBTCKIUQPKB-UHFFFAOYSA-N 0.000 description 1
- GCQFBOLMWGSTSM-UHFFFAOYSA-N 1,3,3-trimethyl-n-[2-(morpholin-4-ylmethyl)phenyl]pyrrolidin-2-imine;dihydroiodide Chemical compound I.I.CN1CCC(C)(C)C1=NC1=CC=CC=C1CN1CCOCC1 GCQFBOLMWGSTSM-UHFFFAOYSA-N 0.000 description 1
- KWPVLUWTOJHTFX-UHFFFAOYSA-N 1,3,3-trimethylpyrrolidin-2-one Chemical compound CN1CCC(C)(C)C1=O KWPVLUWTOJHTFX-UHFFFAOYSA-N 0.000 description 1
- ZBOWKDHBOFMERX-UHFFFAOYSA-N 1,3-diazepane Chemical compound C1CCNCNC1 ZBOWKDHBOFMERX-UHFFFAOYSA-N 0.000 description 1
- GCEHJHRQAICUDM-UHFFFAOYSA-N 1,3-dimethyl-n-[2-(morpholin-4-ylmethyl)phenyl]imidazolidin-2-imine Chemical compound CN1CCN(C)C1=NC1=CC=CC=C1CN1CCOCC1 GCEHJHRQAICUDM-UHFFFAOYSA-N 0.000 description 1
- APWRZPQBPCAXFP-UHFFFAOYSA-N 1-(1-oxo-2H-isoquinolin-5-yl)-5-(trifluoromethyl)-N-[2-(trifluoromethyl)pyridin-4-yl]pyrazole-4-carboxamide Chemical compound O=C1NC=CC2=C(C=CC=C12)N1N=CC(=C1C(F)(F)F)C(=O)NC1=CC(=NC=C1)C(F)(F)F APWRZPQBPCAXFP-UHFFFAOYSA-N 0.000 description 1
- HZEGLKPMKSWGIZ-UHFFFAOYSA-N 1-(2-hydroxyethyl)-3-methylimidazolidin-2-one Chemical compound CN1CCN(CCO)C1=O HZEGLKPMKSWGIZ-UHFFFAOYSA-N 0.000 description 1
- GJWWEGYULZSQLT-UHFFFAOYSA-N 1-(2-methoxyethyl)-1-methyl-2-(2-morpholin-4-ylphenyl)guanidine Chemical compound COCCN(C)C(N)=NC1=CC=CC=C1N1CCOCC1 GJWWEGYULZSQLT-UHFFFAOYSA-N 0.000 description 1
- SOOKQBIOWOIWBS-UHFFFAOYSA-N 1-(2-methoxyethyl)-2-methyl-3-(2-morpholin-4-ylphenyl)guanidine Chemical compound COCCNC(NC)=NC1=CC=CC=C1N1CCOCC1 SOOKQBIOWOIWBS-UHFFFAOYSA-N 0.000 description 1
- QHHCHYAXPBQVJX-UHFFFAOYSA-N 1-(2-methoxyethyl)-3-methylimidazolidin-2-one Chemical compound COCCN1CCN(C)C1=O QHHCHYAXPBQVJX-UHFFFAOYSA-N 0.000 description 1
- WTYRIHBHPIZRRM-UHFFFAOYSA-N 1-(5-chloro-2-morpholin-4-ylphenyl)-2,3-dimethylguanidine Chemical compound CNC(NC)=NC1=CC(Cl)=CC=C1N1CCOCC1 WTYRIHBHPIZRRM-UHFFFAOYSA-N 0.000 description 1
- XJSKGPGQKIJQSE-UHFFFAOYSA-N 1-(5-fluoro-2-morpholin-4-ylphenyl)-3-methylthiourea Chemical compound CNC(=S)NC1=CC(F)=CC=C1N1CCOCC1 XJSKGPGQKIJQSE-UHFFFAOYSA-N 0.000 description 1
- ABDDQTDRAHXHOC-QMMMGPOBSA-N 1-[(7s)-5,7-dihydro-4h-thieno[2,3-c]pyran-7-yl]-n-methylmethanamine Chemical compound CNC[C@@H]1OCCC2=C1SC=C2 ABDDQTDRAHXHOC-QMMMGPOBSA-N 0.000 description 1
- FSIJZZCFYKCPKD-UHFFFAOYSA-N 1-benzyl-3-methyl-n-(2-morpholin-4-ylphenyl)pyrrolidin-2-imine Chemical compound C=1C=CC=C(N2CCOCC2)C=1N=C1C(C)CCN1CC1=CC=CC=C1 FSIJZZCFYKCPKD-UHFFFAOYSA-N 0.000 description 1
- KHABMOXCEDCYAU-UHFFFAOYSA-N 1-benzyl-3-methylpyrrolidin-2-one Chemical compound O=C1C(C)CCN1CC1=CC=CC=C1 KHABMOXCEDCYAU-UHFFFAOYSA-N 0.000 description 1
- QFMDSZDYQRMENV-UHFFFAOYSA-N 1-butyl-1,3,3-trimethyl-2-(2-morpholin-4-ylphenyl)guanidine Chemical compound CCCCN(C)C(N(C)C)=NC1=CC=CC=C1N1CCOCC1 QFMDSZDYQRMENV-UHFFFAOYSA-N 0.000 description 1
- ODWQLZXUHXWHON-UHFFFAOYSA-N 1-butyl-2-methyl-3-(2-methyl-6-morpholin-4-ylphenyl)guanidine Chemical compound CCCCNC(NC)=NC1=C(C)C=CC=C1N1CCOCC1 ODWQLZXUHXWHON-UHFFFAOYSA-N 0.000 description 1
- YMJLUEVJOLZYNU-UHFFFAOYSA-N 1-butyl-2-methyl-3-(2-morpholin-4-ylphenyl)guanidine Chemical compound CCCCNC(NC)=NC1=CC=CC=C1N1CCOCC1 YMJLUEVJOLZYNU-UHFFFAOYSA-N 0.000 description 1
- BHLVVJWAZJHDHN-UHFFFAOYSA-N 1-butyl-2-methyl-3-[2-(1,2,4-oxathiazinan-4-yl)phenyl]guanidine Chemical compound CCCCNC(=NC)NC1=CC=CC=C1N1CSOCC1 BHLVVJWAZJHDHN-UHFFFAOYSA-N 0.000 description 1
- OPIOJBPNNOORPK-UHFFFAOYSA-N 1-butyl-3-(5-chloro-2-morpholin-4-ylphenyl)thiourea Chemical compound CCCCNC(=S)NC1=CC(Cl)=CC=C1N1CCOCC1 OPIOJBPNNOORPK-UHFFFAOYSA-N 0.000 description 1
- BFCFYVKQTRLZHA-UHFFFAOYSA-N 1-chloro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Cl BFCFYVKQTRLZHA-UHFFFAOYSA-N 0.000 description 1
- COHGYJIGGRNMAU-UHFFFAOYSA-N 1-cyclohexyl-n-(2-morpholin-4-ylphenyl)pyrrolidin-2-imine Chemical compound C=1C=CC=C(N2CCOCC2)C=1N=C1CCCN1C1CCCCC1 COHGYJIGGRNMAU-UHFFFAOYSA-N 0.000 description 1
- WJPCLVRIKPPQNQ-UHFFFAOYSA-N 1-ethyl-1-(2-methoxyethyl)-2-(2-morpholin-4-ylphenyl)guanidine Chemical compound COCCN(CC)C(N)=NC1=CC=CC=C1N1CCOCC1 WJPCLVRIKPPQNQ-UHFFFAOYSA-N 0.000 description 1
- DYAJNGLMRPAFOA-UHFFFAOYSA-N 1-ethyl-2-methyl-3-(2-morpholin-4-ylphenyl)guanidine Chemical compound CCNC(NC)=NC1=CC=CC=C1N1CCOCC1 DYAJNGLMRPAFOA-UHFFFAOYSA-N 0.000 description 1
- ZWXTUKIOAVCZIO-UHFFFAOYSA-N 1-methyl-1-(2-methylsulfanylethyl)-2-(2-morpholin-4-ylphenyl)guanidine Chemical compound CSCCN(C)C(N)=NC1=CC=CC=C1N1CCOCC1 ZWXTUKIOAVCZIO-UHFFFAOYSA-N 0.000 description 1
- HPVGVXDYXJMSKS-UHFFFAOYSA-N 1-methyl-3-(2-morpholin-4-ylphenyl)thiourea Chemical compound CNC(=S)NC1=CC=CC=C1N1CCOCC1 HPVGVXDYXJMSKS-UHFFFAOYSA-N 0.000 description 1
- MOOWCIKASIHXIX-UHFFFAOYSA-N 1-methyl-3-(2-pyrrolidin-1-ylphenyl)thiourea Chemical compound CNC(=S)NC1=CC=CC=C1N1CCCC1 MOOWCIKASIHXIX-UHFFFAOYSA-N 0.000 description 1
- DFVVGPBWZWKHKC-UHFFFAOYSA-N 1-methyl-3-(5-methyl-2-morpholin-4-ylphenyl)thiourea Chemical compound CNC(=S)NC1=CC(C)=CC=C1N1CCOCC1 DFVVGPBWZWKHKC-UHFFFAOYSA-N 0.000 description 1
- MJZXRUUSBOCTAD-UHFFFAOYSA-N 1-methyl-3-(5-methylsulfanyl-2-morpholin-4-ylphenyl)thiourea Chemical compound CNC(=S)NC1=CC(SC)=CC=C1N1CCOCC1 MJZXRUUSBOCTAD-UHFFFAOYSA-N 0.000 description 1
- MJCLSUBNHFVDQJ-UHFFFAOYSA-N 1-methyl-n-(2-methyl-6-piperidin-1-ylphenyl)-4,5-dihydroimidazol-2-amine Chemical compound CN1CCNC1=NC1=C(C)C=CC=C1N1CCCCC1 MJCLSUBNHFVDQJ-UHFFFAOYSA-N 0.000 description 1
- PLHASRCTCBQIIR-UHFFFAOYSA-N 1-methyl-n-(2-morpholin-4-ylphenyl)-4,5-dihydroimidazol-2-amine Chemical compound CN1CCNC1=NC1=CC=CC=C1N1CCOCC1 PLHASRCTCBQIIR-UHFFFAOYSA-N 0.000 description 1
- XLJRZZRNMMXNPR-UHFFFAOYSA-N 1-methyl-n-(2-morpholin-4-ylphenyl)piperidin-2-imine Chemical compound CN1CCCCC1=NC1=CC=CC=C1N1CCOCC1 XLJRZZRNMMXNPR-UHFFFAOYSA-N 0.000 description 1
- IYHHDNZKIXBUNT-UHFFFAOYSA-N 1-methyl-n-(2-pyrrolidin-1-ylphenyl)-4,5-dihydroimidazol-2-amine Chemical compound CN1CCNC1=NC1=CC=CC=C1N1CCCC1 IYHHDNZKIXBUNT-UHFFFAOYSA-N 0.000 description 1
- YIPUPBDKFULKBJ-UHFFFAOYSA-N 1-methyl-n-(2-pyrrolidin-1-ylphenyl)pyrrolidin-2-imine Chemical compound CN1CCCC1=NC1=CC=CC=C1N1CCCC1 YIPUPBDKFULKBJ-UHFFFAOYSA-N 0.000 description 1
- YDVUQEDSAJAWFE-UHFFFAOYSA-N 1-tert-butyl-2-methyl-3-(2-morpholin-4-ylphenyl)guanidine Chemical compound CC(C)(C)NC(NC)=NC1=CC=CC=C1N1CCOCC1 YDVUQEDSAJAWFE-UHFFFAOYSA-N 0.000 description 1
- UZHCKBIVXRUPHH-UHFFFAOYSA-N 2,2-dimethyl-N'-(2-morpholin-4-ylphenyl)propanimidamide N'-(2-morpholin-4-ylphenyl)pentanimidamide Chemical compound O1CCN(CC1)C1=C(C=CC=C1)NC(C(C)(C)C)=N.O1CCN(CC1)C1=C(C=CC=C1)NC(CCCC)=N UZHCKBIVXRUPHH-UHFFFAOYSA-N 0.000 description 1
- KLENHQWVLWXXIT-UHFFFAOYSA-N 2,2-dimethyl-N'-[2-(morpholin-4-ylmethyl)phenyl]propanimidamide 2,2-dimethyl-N'-(2-morpholin-4-ylphenyl)propanimidamide Chemical compound O1CCN(CC1)CC1=C(C=CC=C1)NC(C(C)(C)C)=N.O1CCN(CC1)C1=C(C=CC=C1)NC(C(C)(C)C)=N KLENHQWVLWXXIT-UHFFFAOYSA-N 0.000 description 1
- SLSVHNSMVHATQA-UHFFFAOYSA-N 2,2-dimethyl-n'-(2-morpholin-4-ylphenyl)propanimidamide Chemical compound CC(C)(C)C(=N)NC1=CC=CC=C1N1CCOCC1 SLSVHNSMVHATQA-UHFFFAOYSA-N 0.000 description 1
- TVXXNUVILCBXRU-UHFFFAOYSA-N 2-(2-methoxyethyl)-1-(2-piperidin-1-ylphenyl)guanidine Chemical compound COCCNC(N)=NC1=CC=CC=C1N1CCCCC1 TVXXNUVILCBXRU-UHFFFAOYSA-N 0.000 description 1
- NZUZWGVKWAAUMH-UHFFFAOYSA-N 2-(5-cyano-2-morpholin-4-ylphenyl)-1,1-dimethylguanidine Chemical compound CN(C)C(N)=NC1=CC(C#N)=CC=C1N1CCOCC1 NZUZWGVKWAAUMH-UHFFFAOYSA-N 0.000 description 1
- ZTNWZRBNTYKWHF-UHFFFAOYSA-N 2-(5-fluoro-2-morpholin-4-ylphenyl)-1,1-dimethylguanidine Chemical compound CN(C)C(N)=NC1=CC(F)=CC=C1N1CCOCC1 ZTNWZRBNTYKWHF-UHFFFAOYSA-N 0.000 description 1
- OYWABPAKFLVUFX-UHFFFAOYSA-N 2-[3-methyl-2-(2-morpholin-4-ylphenyl)iminoimidazolidin-1-yl]ethanol Chemical compound CN1CCN(CCO)C1=NC1=CC=CC=C1N1CCOCC1 OYWABPAKFLVUFX-UHFFFAOYSA-N 0.000 description 1
- BLOJHKBEZQXFEB-UHFFFAOYSA-N 2-butyl-1-ethyl-3-(2-morpholin-4-ylphenyl)guanidine Chemical compound CCCCNC(NCC)=NC1=CC=CC=C1N1CCOCC1 BLOJHKBEZQXFEB-UHFFFAOYSA-N 0.000 description 1
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 1
- ZYIDUOWXYLAIOF-UHFFFAOYSA-N 2-isothiocyanato-n,n-bis(2-methoxyethyl)aniline Chemical compound COCCN(CCOC)C1=CC=CC=C1N=C=S ZYIDUOWXYLAIOF-UHFFFAOYSA-N 0.000 description 1
- IWXICDBISVWHGV-UHFFFAOYSA-N 2-methyl-6-piperidin-1-ylaniline Chemical compound CC1=CC=CC(N2CCCCC2)=C1N IWXICDBISVWHGV-UHFFFAOYSA-N 0.000 description 1
- YQWKOWYZWMCMJV-UHFFFAOYSA-N 2-methyl-n'-(5-methylsulfanyl-2-morpholin-4-ylphenyl)propanimidamide Chemical compound CC(C)C(=N)NC1=CC(SC)=CC=C1N1CCOCC1 YQWKOWYZWMCMJV-UHFFFAOYSA-N 0.000 description 1
- CYWGSFFHHMQKET-UHFFFAOYSA-N 2-methylsulfanylethanamine Chemical compound CSCCN CYWGSFFHHMQKET-UHFFFAOYSA-N 0.000 description 1
- CNVOJNRNRNAOOP-UHFFFAOYSA-N 2-morpholin-4-yl-5-(trifluoromethyl)aniline Chemical compound NC1=CC(C(F)(F)F)=CC=C1N1CCOCC1 CNVOJNRNRNAOOP-UHFFFAOYSA-N 0.000 description 1
- POYIPJPJYWWRGJ-UHFFFAOYSA-N 2-n-cyclohexyl-2-n-methyl-1-n-(2,3,4,5-tetrahydropyridin-6-yl)benzene-1,2-diamine Chemical compound C=1C=CC=C(NC=2CCCCN=2)C=1N(C)C1CCCCC1 POYIPJPJYWWRGJ-UHFFFAOYSA-N 0.000 description 1
- HCDMJFOHIXMBOV-UHFFFAOYSA-N 3-(2,6-difluoro-3,5-dimethoxyphenyl)-1-ethyl-8-(morpholin-4-ylmethyl)-4,7-dihydropyrrolo[4,5]pyrido[1,2-d]pyrimidin-2-one Chemical compound C=1C2=C3N(CC)C(=O)N(C=4C(=C(OC)C=C(OC)C=4F)F)CC3=CN=C2NC=1CN1CCOCC1 HCDMJFOHIXMBOV-UHFFFAOYSA-N 0.000 description 1
- QYIXXHWXUTYAHZ-UHFFFAOYSA-N 3-(2-methoxyethyl)-1-methylpiperidin-2-one Chemical compound COCCC1CCCN(C)C1=O QYIXXHWXUTYAHZ-UHFFFAOYSA-N 0.000 description 1
- YGYGASJNJTYNOL-CQSZACIVSA-N 3-[(4r)-2,2-dimethyl-1,1-dioxothian-4-yl]-5-(4-fluorophenyl)-1h-indole-7-carboxamide Chemical compound C1CS(=O)(=O)C(C)(C)C[C@@H]1C1=CNC2=C(C(N)=O)C=C(C=3C=CC(F)=CC=3)C=C12 YGYGASJNJTYNOL-CQSZACIVSA-N 0.000 description 1
- WNEODWDFDXWOLU-QHCPKHFHSA-N 3-[3-(hydroxymethyl)-4-[1-methyl-5-[[5-[(2s)-2-methyl-4-(oxetan-3-yl)piperazin-1-yl]pyridin-2-yl]amino]-6-oxopyridin-3-yl]pyridin-2-yl]-7,7-dimethyl-1,2,6,8-tetrahydrocyclopenta[3,4]pyrrolo[3,5-b]pyrazin-4-one Chemical compound C([C@@H](N(CC1)C=2C=NC(NC=3C(N(C)C=C(C=3)C=3C(=C(N4C(C5=CC=6CC(C)(C)CC=6N5CC4)=O)N=CC=3)CO)=O)=CC=2)C)N1C1COC1 WNEODWDFDXWOLU-QHCPKHFHSA-N 0.000 description 1
- ZFRALOPNZCFSBA-UHFFFAOYSA-N 3-amino-4-morpholin-4-ylbenzonitrile Chemical compound NC1=CC(C#N)=CC=C1N1CCOCC1 ZFRALOPNZCFSBA-UHFFFAOYSA-N 0.000 description 1
- CIRFKYGQEXNBBW-UHFFFAOYSA-N 3-methyl-2-morpholin-4-ylaniline Chemical compound CC1=CC=CC(N)=C1N1CCOCC1 CIRFKYGQEXNBBW-UHFFFAOYSA-N 0.000 description 1
- KWXVDTBFJCZOTP-UHFFFAOYSA-N 4,5-dimethyl-n-(2-morpholin-4-ylphenyl)-4,5-dihydro-1h-imidazol-2-amine Chemical compound N1C(C)C(C)NC1=NC1=CC=CC=C1N1CCOCC1 KWXVDTBFJCZOTP-UHFFFAOYSA-N 0.000 description 1
- RDRZXBQWXVHWLR-UHFFFAOYSA-N 4-(2-isothiocyanato-4-methylphenyl)morpholine Chemical compound S=C=NC1=CC(C)=CC=C1N1CCOCC1 RDRZXBQWXVHWLR-UHFFFAOYSA-N 0.000 description 1
- GYILGUCNWIUUOX-UHFFFAOYSA-N 4-(2-isothiocyanato-6-methylphenyl)morpholine Chemical compound CC1=CC=CC(N=C=S)=C1N1CCOCC1 GYILGUCNWIUUOX-UHFFFAOYSA-N 0.000 description 1
- ZNIVBGRYSLARJS-UHFFFAOYSA-N 4-(2-morpholin-4-ylphenyl)morpholine Chemical compound C1COCCN1C1=CC=CC=C1N1CCOCC1 ZNIVBGRYSLARJS-UHFFFAOYSA-N 0.000 description 1
- JLAKCHGEEBPDQI-UHFFFAOYSA-N 4-(4-fluorobenzyl)piperidine Chemical compound C1=CC(F)=CC=C1CC1CCNCC1 JLAKCHGEEBPDQI-UHFFFAOYSA-N 0.000 description 1
- VJPPLCNBDLZIFG-ZDUSSCGKSA-N 4-[(3S)-3-(but-2-ynoylamino)piperidin-1-yl]-5-fluoro-2,3-dimethyl-1H-indole-7-carboxamide Chemical compound C(C#CC)(=O)N[C@@H]1CN(CCC1)C1=C2C(=C(NC2=C(C=C1F)C(=O)N)C)C VJPPLCNBDLZIFG-ZDUSSCGKSA-N 0.000 description 1
- JDXRMEMHYIYRAN-UHFFFAOYSA-N 4-methoxy-2-morpholin-4-ylaniline Chemical compound COC1=CC=C(N)C(N2CCOCC2)=C1 JDXRMEMHYIYRAN-UHFFFAOYSA-N 0.000 description 1
- XLTKBLYQTBYDDN-UHFFFAOYSA-N 4-methyl-n'-(2-morpholin-4-ylphenyl)piperidine-1-carboximidamide Chemical compound C1CC(C)CCN1C(=N)NC1=CC=CC=C1N1CCOCC1 XLTKBLYQTBYDDN-UHFFFAOYSA-N 0.000 description 1
- USFKFIGZQHXLEV-UHFFFAOYSA-N 5-methyl-n-(2-morpholin-4-ylphenyl)-4,5-dihydro-1h-imidazol-2-amine Chemical compound N1C(C)CNC1=NC1=CC=CC=C1N1CCOCC1 USFKFIGZQHXLEV-UHFFFAOYSA-N 0.000 description 1
- DEXFNLNNUZKHNO-UHFFFAOYSA-N 6-[3-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-3-oxopropyl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)C(CCC1=CC2=C(NC(O2)=O)C=C1)=O DEXFNLNNUZKHNO-UHFFFAOYSA-N 0.000 description 1
- CYJRNFFLTBEQSQ-UHFFFAOYSA-N 8-(3-methyl-1-benzothiophen-5-yl)-N-(4-methylsulfonylpyridin-3-yl)quinoxalin-6-amine Chemical compound CS(=O)(=O)C1=C(C=NC=C1)NC=1C=C2N=CC=NC2=C(C=1)C=1C=CC2=C(C(=CS2)C)C=1 CYJRNFFLTBEQSQ-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 101100439664 Arabidopsis thaliana CHR8 gene Proteins 0.000 description 1
- 235000003911 Arachis Nutrition 0.000 description 1
- 244000105624 Arachis hypogaea Species 0.000 description 1
- MPHOWMDBCDBDTM-UHFFFAOYSA-N C(C=CC(=O)O)(=O)O.C(CCC)(=N)N Chemical compound C(C=CC(=O)O)(=O)O.C(CCC)(=N)N MPHOWMDBCDBDTM-UHFFFAOYSA-N 0.000 description 1
- MHUCIXCIYCLEDU-UHFFFAOYSA-N C(C=CC(=O)O)(=O)O.C(CCC)NC(=NC1=C(C=CC=C1)N1CCOCC1)NC Chemical compound C(C=CC(=O)O)(=O)O.C(CCC)NC(=NC1=C(C=CC=C1)N1CCOCC1)NC MHUCIXCIYCLEDU-UHFFFAOYSA-N 0.000 description 1
- HFXWYQIHUJVIAO-UHFFFAOYSA-N C(C=CC(=O)O)(=O)O.CNC(=NC1=C(C=CC=C1)N1CCOCC1)N(C)C Chemical compound C(C=CC(=O)O)(=O)O.CNC(=NC1=C(C=CC=C1)N1CCOCC1)N(C)C HFXWYQIHUJVIAO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 101100260565 Dictyostelium discoideum thyA gene Proteins 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical class NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 239000004366 Glucose oxidase Substances 0.000 description 1
- 108010015776 Glucose oxidase Proteins 0.000 description 1
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
- 241000282414 Homo sapiens Species 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 239000001358 L(+)-tartaric acid Substances 0.000 description 1
- 235000011002 L(+)-tartaric acid Nutrition 0.000 description 1
- FEWJPZIEWOKRBE-LWMBPPNESA-N L-(+)-Tartaric acid Natural products OC(=O)[C@@H](O)[C@H](O)C(O)=O FEWJPZIEWOKRBE-LWMBPPNESA-N 0.000 description 1
- 235000019759 Maize starch Nutrition 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- KQJQICVXLJTWQD-UHFFFAOYSA-N N-Methylthiourea Chemical compound CNC(N)=S KQJQICVXLJTWQD-UHFFFAOYSA-N 0.000 description 1
- VCUFZILGIRCDQQ-KRWDZBQOSA-N N-[[(5S)-2-oxo-3-(2-oxo-3H-1,3-benzoxazol-6-yl)-1,3-oxazolidin-5-yl]methyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C1O[C@H](CN1C1=CC2=C(NC(O2)=O)C=C1)CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F VCUFZILGIRCDQQ-KRWDZBQOSA-N 0.000 description 1
- NBFUFGIKFRIZDP-UHFFFAOYSA-N N1C(CCCC1)=NC1=C(C=CC=C1)N1CCCCCC1.CN1C(CCCC1)=NC1=C(C=CC=C1)N1CCCCC1 Chemical compound N1C(CCCC1)=NC1=C(C=CC=C1)N1CCCCCC1.CN1C(CCCC1)=NC1=C(C=CC=C1)N1CCCCC1 NBFUFGIKFRIZDP-UHFFFAOYSA-N 0.000 description 1
- BJJXEIIEASWRLT-UHFFFAOYSA-N OC(=O)C(O)C(O)C(O)=O.CN(C)C(N)=NC1=CC(C)=CC=C1N1CCOCC1 Chemical compound OC(=O)C(O)C(O)C(O)=O.CN(C)C(N)=NC1=CC(C)=CC=C1N1CCOCC1 BJJXEIIEASWRLT-UHFFFAOYSA-N 0.000 description 1
- MTOBMCZGNBSOKJ-UHFFFAOYSA-N OC(=O)C(O)C(O)C(O)=O.CN(C)C(N)=NC1=CC=CC=C1N1CCOCC1 Chemical compound OC(=O)C(O)C(O)C(O)=O.CN(C)C(N)=NC1=CC=CC=C1N1CCOCC1 MTOBMCZGNBSOKJ-UHFFFAOYSA-N 0.000 description 1
- 239000004218 Orcein Substances 0.000 description 1
- 241000320734 Oxychloris Species 0.000 description 1
- 239000005662 Paraffin oil Substances 0.000 description 1
- 239000005700 Putrescine Substances 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 239000004231 Riboflavin-5-Sodium Phosphate Substances 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 239000004288 Sodium dehydroacetate Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 239000004234 Yellow 2G Substances 0.000 description 1
- ZYTBQICKIJOOAB-UHFFFAOYSA-N [2-(1,2,4-oxathiazinan-4-yl)phenyl]thiourea Chemical compound NC(=S)NC1=CC=CC=C1N1CSOCC1 ZYTBQICKIJOOAB-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 125000004450 alkenylene group Chemical group 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 150000001409 amidines Chemical class 0.000 description 1
- 235000001014 amino acid Nutrition 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 230000003178 anti-diabetic effect Effects 0.000 description 1
- 239000003472 antidiabetic agent Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 239000004176 azorubin Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 238000006480 benzoylation reaction Methods 0.000 description 1
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 description 1
- 230000000740 bleeding effect Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- GHWVXCQZPNWFRO-UHFFFAOYSA-N butane-2,3-diamine Chemical compound CC(N)C(C)N GHWVXCQZPNWFRO-UHFFFAOYSA-N 0.000 description 1
- RXKUYBRRTKRGME-UHFFFAOYSA-N butanimidamide Chemical compound CCCC(N)=N RXKUYBRRTKRGME-UHFFFAOYSA-N 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 1
- NISGSNTVMOOSJQ-UHFFFAOYSA-N cyclopentanamine Chemical compound NC1CCCC1 NISGSNTVMOOSJQ-UHFFFAOYSA-N 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
- 150000004985 diamines Chemical class 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 125000001891 dimethoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000000555 dodecyl gallate Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000002662 enteric coated tablet Substances 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
- 229940012017 ethylenediamine Drugs 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
- 235000019420 glucose oxidase Nutrition 0.000 description 1
- 229940116332 glucose oxidase Drugs 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000004120 green S Substances 0.000 description 1
- PJJJBBJSCAKJQF-UHFFFAOYSA-N guanidinium chloride Chemical compound [Cl-].NC(N)=[NH2+] PJJJBBJSCAKJQF-UHFFFAOYSA-N 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 201000001421 hyperglycemia Diseases 0.000 description 1
- GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical compound C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 230000001050 lubricating effect Effects 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- QMPBGXKGFCGWPA-UHFFFAOYSA-N methyl 3-amino-4-morpholin-4-ylbenzoate Chemical compound NC1=CC(C(=O)OC)=CC=C1N1CCOCC1 QMPBGXKGFCGWPA-UHFFFAOYSA-N 0.000 description 1
- VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 description 1
- LRIKLWSXYJULHZ-UHFFFAOYSA-N methyl n'-(2-methyl-6-morpholin-4-ylphenyl)carbamimidothioate;hydroiodide Chemical compound I.CSC(=N)NC1=C(C)C=CC=C1N1CCOCC1 LRIKLWSXYJULHZ-UHFFFAOYSA-N 0.000 description 1
- XLOFXCBOAGRHBN-UHFFFAOYSA-N methyl n'-(2-methyl-6-piperidin-1-ylphenyl)carbamimidothioate;hydroiodide Chemical compound I.CSC(=N)NC1=C(C)C=CC=C1N1CCCCC1 XLOFXCBOAGRHBN-UHFFFAOYSA-N 0.000 description 1
- KPUVGABEMJNVLO-UHFFFAOYSA-N methyl n'-(2-piperidin-1-ylphenyl)carbamimidothioate;hydroiodide Chemical compound I.CSC(=N)NC1=CC=CC=C1N1CCCCC1 KPUVGABEMJNVLO-UHFFFAOYSA-N 0.000 description 1
- KRQBZRGVESUBIQ-UHFFFAOYSA-N methyl n'-(2-pyrrolidin-1-ylphenyl)carbamimidothioate;hydroiodide Chemical compound I.CSC(=N)NC1=CC=CC=C1N1CCCC1 KRQBZRGVESUBIQ-UHFFFAOYSA-N 0.000 description 1
- RIZLGMNLTRFXHX-UHFFFAOYSA-N methyl n'-(5-methyl-2-morpholin-4-ylphenyl)carbamimidothioate;hydroiodide Chemical compound I.CSC(=N)NC1=CC(C)=CC=C1N1CCOCC1 RIZLGMNLTRFXHX-UHFFFAOYSA-N 0.000 description 1
- ZBUADBRYAPNCGZ-UHFFFAOYSA-N methyl n'-butyl-n-(2-morpholin-4-ylphenyl)carbamimidothioate;hydroiodide Chemical compound I.CCCCN=C(SC)NC1=CC=CC=C1N1CCOCC1 ZBUADBRYAPNCGZ-UHFFFAOYSA-N 0.000 description 1
- ONLUETIGUPBGLU-UHFFFAOYSA-N methyl n'-butyl-n-(5-chloro-2-morpholin-4-ylphenyl)carbamimidothioate;hydroiodide Chemical compound I.CCCCN=C(SC)NC1=CC(Cl)=CC=C1N1CCOCC1 ONLUETIGUPBGLU-UHFFFAOYSA-N 0.000 description 1
- NHEVAEXMMBQRRK-UHFFFAOYSA-N methyl n'-methyl-n-(2-methyl-6-morpholin-4-ylphenyl)carbamimidothioate;hydroiodide Chemical compound I.CSC(=NC)NC1=C(C)C=CC=C1N1CCOCC1 NHEVAEXMMBQRRK-UHFFFAOYSA-N 0.000 description 1
- WDAZZMDUAXHHCO-UHFFFAOYSA-N methyl n'-methyl-n-(2-morpholin-4-ylphenyl)carbamimidothioate Chemical compound CSC(=NC)NC1=CC=CC=C1N1CCOCC1 WDAZZMDUAXHHCO-UHFFFAOYSA-N 0.000 description 1
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 125000004372 methylthioethyl group Chemical group [H]C([H])([H])SC([H])([H])C([H])([H])* 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- VSEAAEQOQBMPQF-UHFFFAOYSA-N morpholin-3-one Chemical compound O=C1COCCN1 VSEAAEQOQBMPQF-UHFFFAOYSA-N 0.000 description 1
- BOQOXLAQTDFJKU-UHFFFAOYSA-N morpholine-4-carbonitrile Chemical compound N#CN1CCOCC1 BOQOXLAQTDFJKU-UHFFFAOYSA-N 0.000 description 1
- FFLYAXRFHNBAPK-UHFFFAOYSA-N n',2,2-trimethyl-n-(2-morpholin-4-ylphenyl)propanimidamide Chemical compound CNC(C(C)(C)C)=NC1=CC=CC=C1N1CCOCC1 FFLYAXRFHNBAPK-UHFFFAOYSA-N 0.000 description 1
- ZHOLTTIAXKORSU-UHFFFAOYSA-N n',2-dimethyl-n-(2-morpholin-4-ylphenyl)propanimidamide Chemical compound CNC(C(C)C)=NC1=CC=CC=C1N1CCOCC1 ZHOLTTIAXKORSU-UHFFFAOYSA-N 0.000 description 1
- GAGYTSOEDMAYIA-UHFFFAOYSA-N n'-(2-morpholin-4-ylphenyl)butanimidamide Chemical compound CCCC(=N)NC1=CC=CC=C1N1CCOCC1 GAGYTSOEDMAYIA-UHFFFAOYSA-N 0.000 description 1
- PTGWNQXYFRYROU-UHFFFAOYSA-N n'-(2-morpholin-4-ylphenyl)ethanimidamide Chemical compound CC(=N)NC1=CC=CC=C1N1CCOCC1 PTGWNQXYFRYROU-UHFFFAOYSA-N 0.000 description 1
- SPVWQWQRTCPMHZ-UHFFFAOYSA-N n'-(2-morpholin-4-ylphenyl)pentanimidamide Chemical compound CCCCC(=N)NC1=CC=CC=C1N1CCOCC1 SPVWQWQRTCPMHZ-UHFFFAOYSA-N 0.000 description 1
- BLUUWKVYAFKWFO-UHFFFAOYSA-N n'-(2-morpholin-4-ylphenyl)propanimidamide Chemical compound CCC(=N)NC1=CC=CC=C1N1CCOCC1 BLUUWKVYAFKWFO-UHFFFAOYSA-N 0.000 description 1
- DDGHEXMCECQCSC-UHFFFAOYSA-N n'-(4-methyl-2-morpholin-4-ylphenyl)ethanimidamide Chemical compound CC(=N)NC1=CC=C(C)C=C1N1CCOCC1 DDGHEXMCECQCSC-UHFFFAOYSA-N 0.000 description 1
- BENIFPFKIDBRNI-UHFFFAOYSA-N n'-(5-fluoro-2-morpholin-4-ylphenyl)-2-methylpropanimidamide Chemical compound CC(C)C(=N)NC1=CC(F)=CC=C1N1CCOCC1 BENIFPFKIDBRNI-UHFFFAOYSA-N 0.000 description 1
- KIEGXUWMAQWRKA-UHFFFAOYSA-N n'-(5-methyl-2-morpholin-4-ylphenyl)ethanimidamide Chemical compound CC(=N)NC1=CC(C)=CC=C1N1CCOCC1 KIEGXUWMAQWRKA-UHFFFAOYSA-N 0.000 description 1
- BCNGNVMRFRJLIL-UHFFFAOYSA-N n'-methyl-n-(2-morpholin-4-ylphenyl)cyclohexanecarboximidamide Chemical compound C1CCCCC1C(NC)=NC1=CC=CC=C1N1CCOCC1 BCNGNVMRFRJLIL-UHFFFAOYSA-N 0.000 description 1
- ANFVEMGNELYSAN-UHFFFAOYSA-N n'-methyl-n-(2-morpholin-4-ylphenyl)ethanimidamide Chemical compound CNC(C)=NC1=CC=CC=C1N1CCOCC1 ANFVEMGNELYSAN-UHFFFAOYSA-N 0.000 description 1
- MOYZWYDTBGRGIZ-UHFFFAOYSA-N n'-methyl-n-(2-morpholin-4-ylphenyl)pyrrolidine-1-carboximidamide Chemical compound C1CCCN1C(NC)=NC1=CC=CC=C1N1CCOCC1 MOYZWYDTBGRGIZ-UHFFFAOYSA-N 0.000 description 1
- KFIGICHILYTCJF-UHFFFAOYSA-N n'-methylethane-1,2-diamine Chemical compound CNCCN KFIGICHILYTCJF-UHFFFAOYSA-N 0.000 description 1
- QHJABUZHRJTCAR-UHFFFAOYSA-N n'-methylpropane-1,3-diamine Chemical compound CNCCCN QHJABUZHRJTCAR-UHFFFAOYSA-N 0.000 description 1
- JLVSRHVJVVXWST-UHFFFAOYSA-N n,n-diethyl-n'-(2-morpholin-4-ylphenyl)ethanimidamide Chemical compound CCN(CC)C(C)=NC1=CC=CC=C1N1CCOCC1 JLVSRHVJVVXWST-UHFFFAOYSA-N 0.000 description 1
- WJFNJZOOKPGLSV-UHFFFAOYSA-N n,n-dimethyl-n'-(2-morpholin-4-ylphenyl)morpholine-4-carboximidamide Chemical compound C1COCCN1C(N(C)C)=NC1=CC=CC=C1N1CCOCC1 WJFNJZOOKPGLSV-UHFFFAOYSA-N 0.000 description 1
- HEMGZLKNTCPOPL-UHFFFAOYSA-N n,n-dimethyl-n'-(2-morpholin-4-ylphenyl)piperidine-1-carboximidamide Chemical compound C1CCCCN1C(N(C)C)=NC1=CC=CC=C1N1CCOCC1 HEMGZLKNTCPOPL-UHFFFAOYSA-N 0.000 description 1
- KFCXHZRPFJLAND-UHFFFAOYSA-N n,n-dimethylmorpholine-4-carboxamide Chemical compound CN(C)C(=O)N1CCOCC1 KFCXHZRPFJLAND-UHFFFAOYSA-N 0.000 description 1
- FYYRPPUFMRGGNG-UHFFFAOYSA-N n,n-dimethylpiperidine-1-carboxamide Chemical compound CN(C)C(=O)N1CCCCC1 FYYRPPUFMRGGNG-UHFFFAOYSA-N 0.000 description 1
- QLGKMTXCOUHUOL-UHFFFAOYSA-N n-(2-morpholin-4-ylphenyl)-3,6-dihydro-2h-1,4-oxazin-5-amine Chemical compound N1CCOCC1=NC1=CC=CC=C1N1CCOCC1 QLGKMTXCOUHUOL-UHFFFAOYSA-N 0.000 description 1
- AUKVFTUAYBEYBA-UHFFFAOYSA-N n-(2-morpholin-4-ylphenyl)-4,5-dihydro-1h-imidazol-2-amine Chemical compound N1CCNC1=NC1=CC=CC=C1N1CCOCC1 AUKVFTUAYBEYBA-UHFFFAOYSA-N 0.000 description 1
- FMZCPZIVWDIHBF-UHFFFAOYSA-N n-(2-thiomorpholin-4-ylphenyl)-2,3,4,5-tetrahydropyridin-6-amine Chemical compound N1CCCCC1=NC1=CC=CC=C1N1CCSCC1 FMZCPZIVWDIHBF-UHFFFAOYSA-N 0.000 description 1
- KWLRNZLUUOENAZ-UHFFFAOYSA-N n-[2-(morpholin-4-ylmethyl)phenyl]-2,3,4,5-tetrahydropyridin-6-amine Chemical compound C=1C=CC=C(N=C2NCCCC2)C=1CN1CCOCC1 KWLRNZLUUOENAZ-UHFFFAOYSA-N 0.000 description 1
- ICUDHATVRDMKPB-UHFFFAOYSA-N n-[5-chloro-2-(morpholin-4-ylmethyl)phenyl]-1,3-dimethylimidazolidin-2-imine Chemical compound CN1CCN(C)C1=NC1=CC(Cl)=CC=C1CN1CCOCC1 ICUDHATVRDMKPB-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
- WIIWCWCZHZBQFZ-UHFFFAOYSA-N n-phenyl-1,2,4-oxathiazinan-4-amine Chemical compound C1SOCCN1NC1=CC=CC=C1 WIIWCWCZHZBQFZ-UHFFFAOYSA-N 0.000 description 1
- DYUWTXWIYMHBQS-UHFFFAOYSA-N n-prop-2-enylprop-2-en-1-amine Chemical compound C=CCNCC=C DYUWTXWIYMHBQS-UHFFFAOYSA-N 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000005022 packaging material Substances 0.000 description 1
- WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
- LPXCHPSTROLSJX-UHFFFAOYSA-N pentanimidamide Chemical compound CCCCC(N)=N LPXCHPSTROLSJX-UHFFFAOYSA-N 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000002831 pharmacologic agent Substances 0.000 description 1
- 229940117953 phenylisothiocyanate Drugs 0.000 description 1
- JAMNHZBIQDNHMM-UHFFFAOYSA-N pivalonitrile Chemical compound CC(C)(C)C#N JAMNHZBIQDNHMM-UHFFFAOYSA-N 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- LZMJNVRJMFMYQS-UHFFFAOYSA-N poseltinib Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(OC=C2)C2=N1 LZMJNVRJMFMYQS-UHFFFAOYSA-N 0.000 description 1
- 239000004323 potassium nitrate Substances 0.000 description 1
- 239000004302 potassium sorbate Substances 0.000 description 1
- GNFWGDKKNWGGJY-UHFFFAOYSA-N propanimidamide Chemical compound CCC(N)=N GNFWGDKKNWGGJY-UHFFFAOYSA-N 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- PIGIRWPZTWLVLB-UHFFFAOYSA-N pyrrolidine-1-carboximidamide Chemical compound NC(=N)N1CCCC1 PIGIRWPZTWLVLB-UHFFFAOYSA-N 0.000 description 1
- 239000004180 red 2G Substances 0.000 description 1
- 239000011369 resultant mixture Substances 0.000 description 1
- 238000006748 scratching Methods 0.000 description 1
- 230000002393 scratching effect Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- XIIOFHFUYBLOLW-UHFFFAOYSA-N selpercatinib Chemical compound OC(COC=1C=C(C=2N(C=1)N=CC=2C#N)C=1C=NC(=CC=1)N1CC2N(C(C1)C2)CC=1C=NC(=CC=1)OC)(C)C XIIOFHFUYBLOLW-UHFFFAOYSA-N 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
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000004402 sodium ethyl p-hydroxybenzoate Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000004317 sodium nitrate Substances 0.000 description 1
- 239000004328 sodium tetraborate Substances 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000002511 suppository base Substances 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 101150068774 thyX gene Proteins 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 150000004684 trihydrates Chemical class 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- MECHNRXZTMCUDQ-RKHKHRCZSA-N vitamin D2 Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)/C=C/[C@H](C)C(C)C)=C\C=C1\C[C@@H](O)CCC1=C MECHNRXZTMCUDQ-RKHKHRCZSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/135—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C257/00—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines
- C07C257/10—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/18—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/02—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D223/06—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings 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
- C07D223/12—Nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D225/00—Heterocyclic compounds containing rings of more than seven members having one nitrogen atom as the only ring hetero atom
- C07D225/04—Heterocyclic compounds containing rings of more than seven members having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D233/44—Nitrogen atoms not forming part of a nitro radical
- C07D233/50—Nitrogen atoms not forming part of a nitro radical with carbocyclic radicals directly attached to said nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Diabetes (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Endocrinology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Emergency Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Indole Compounds (AREA)
- Steroid Compounds (AREA)
- Saccharide Compounds (AREA)
- Thermotherapy And Cooling Therapy Devices (AREA)
- Soy Sauces And Products Related Thereto (AREA)
- Investigating Or Analysing Materials By Optical Means (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB898903592A GB8903592D0 (en) | 1989-02-16 | 1989-02-16 | Therapeutic agents |
Publications (2)
Publication Number | Publication Date |
---|---|
LV10619A LV10619A (lv) | 1995-04-20 |
LV10619B true LV10619B (en) | 1995-08-20 |
Family
ID=10651840
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
LVP-93-815A LV10619B (en) | 1989-02-16 | 1993-06-30 | Therapeutic agents |
Country Status (26)
Country | Link |
---|---|
US (2) | US5223498A (da) |
EP (1) | EP0385038B1 (da) |
JP (1) | JP2545475B2 (da) |
AT (1) | ATE90074T1 (da) |
BG (1) | BG60557B1 (da) |
CS (1) | CS277609B6 (da) |
DD (1) | DD294023A5 (da) |
DE (1) | DE68906880T2 (da) |
DK (1) | DK640889A (da) |
ES (1) | ES2055115T3 (da) |
FI (1) | FI95565C (da) |
GB (1) | GB8903592D0 (da) |
GE (1) | GEP19981040B (da) |
HU (1) | HU211571A9 (da) |
IL (1) | IL92963A (da) |
LT (3) | LT3960B (da) |
LV (1) | LV10619B (da) |
MY (1) | MY105052A (da) |
NO (1) | NO177993C (da) |
PL (2) | PL161961B1 (da) |
PT (1) | PT92770B (da) |
RO (2) | RO105807B1 (da) |
RU (3) | RU1826969C (da) |
UA (2) | UA27713C2 (da) |
YU (1) | YU48164B (da) |
ZA (1) | ZA899941B (da) |
Families Citing this family (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3766696D1 (de) * | 1986-12-27 | 1991-01-24 | Konishiroku Photo Ind | Lichtempfindliches photographisches silberhalogenidmaterial. |
IN172842B (da) * | 1990-05-17 | 1993-12-11 | Boots Pharmaceuticals Limited | |
GB9418912D0 (en) * | 1994-09-20 | 1994-11-09 | Fisons Corp | Pharmaceutically active compounds |
AU4176396A (en) * | 1994-12-08 | 1996-06-26 | Knoll Aktiengesellschaft | Use of substituted phenylamidine and phenylguanidine compounds for the treatment of cerebral and cardiac ischaemia, convulsion and sickle cell anaemia |
TW397812B (en) * | 1995-02-11 | 2000-07-11 | Astra Ab | Bicyclic isothiourea derivatives useful in therapy |
WO1997046515A1 (fr) * | 1996-06-04 | 1997-12-11 | Chugai Seiyaku Kabushiki Kaisha | Benzenes substitues ne presentant pas d'effets inhibiteurs |
US6756389B2 (en) * | 1996-08-09 | 2004-06-29 | Cambridge Neuroscience, Inc. | Pharmaceutically active compounds and methods of use |
US6187203B1 (en) * | 1998-12-01 | 2001-02-13 | Academia Sinica | Sample purification apparatus and method |
US20030212116A1 (en) * | 1999-12-28 | 2003-11-13 | Toshio Niki | Heterocyclic imino compounds and fungicides and insecticides for agricultural and horitcultural use |
BR0107179A (pt) * | 2000-09-07 | 2002-07-02 | Bayer Ag | Amidinas cìclicas e acìclicas e composições farmacêuticas contendo as mesmas para uso como agentes de ligação de receptor de progesterona |
PE20070182A1 (es) * | 2005-07-29 | 2007-03-06 | Wyeth Corp | Derivados cianopirrol-fenil amida como moduladores del receptor de progesterona |
PE20070341A1 (es) * | 2005-07-29 | 2007-04-13 | Wyeth Corp | Derivados de pirrol como moduladores del receptor de progesterona |
PE20070404A1 (es) * | 2005-07-29 | 2007-05-10 | Wyeth Corp | Compuestos derivados de cianopirrol-sulfonamida como moduladores del receptor de progesterona |
Family Cites Families (86)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DD81857A (da) * | ||||
US77978A (en) | 1868-05-19 | Improvement in low-water indicators | ||
CA372219A (en) | 1938-03-01 | Kienzle Fritz | Perforating device | |
US672015A (en) | 1900-10-05 | 1901-04-16 | Alfred Schlatter | Automatic switch for groups of transformers. |
GB861527A (en) * | 1958-05-16 | 1961-02-22 | Ici Ltd | New salts of penicillins |
US3622596A (en) * | 1960-10-14 | 1971-11-23 | A Wander Sa Dr | Carbanilide compounds |
CH459172A (de) * | 1961-09-11 | 1968-07-15 | Wander Ag Dr A | Verfahren zur Herstellung mehrbasischer Verbindungen |
US3867448A (en) * | 1962-03-08 | 1975-02-18 | Ciba Geigy Ag | Trifluoromethylphenyl-formamadines and acetamidines |
BE639393A (da) * | 1962-10-30 | |||
US3320229A (en) * | 1963-08-26 | 1967-05-16 | Stauffer Chemical Co | Complexes of guanidines with completely halogenated acetones |
US3479437A (en) * | 1963-08-26 | 1969-11-18 | Stauffer Chemical Co | Guanidine complexes as fungicides |
US3636219A (en) * | 1964-03-02 | 1972-01-18 | Du Pont | Anticholinergic compositions containing certain thiazolines or imidazolines |
US3399211A (en) * | 1964-03-10 | 1968-08-27 | Merck & Co Inc | Production of 2-aryl-4(5)-nitroimidazoles |
US3479401A (en) * | 1966-06-28 | 1969-11-18 | Merck & Co Inc | Guanidinoaryl and guanidinomethylaryl compounds |
DE1670274A1 (de) * | 1966-10-31 | 1970-07-16 | Boehringer Sohn Ingelheim | Neues Verfahren zur Herstellung von 2-Arylamino-1,3-diazacycloalkenen-(2) |
IL30281A (en) * | 1967-07-11 | 1971-12-29 | Chinoin Gyogyszer Es Vegyeszet | Amidine history and process for their preparation |
DE2029297A1 (de) * | 1970-06-13 | 1971-12-30 | Farbenfabriken Bayer Ag, 5090 Leverkusen | Neue Aminophenyl-cycloamidine, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
US3911014A (en) * | 1970-06-13 | 1975-10-07 | Bayer Ag | Aminophenylamidines, their production and their medicinal use |
US3903302A (en) * | 1970-06-13 | 1975-09-02 | Bayer Ag | Aminophenylamidines as anthelmintic agents |
US3919315A (en) * | 1970-06-13 | 1975-11-11 | Bayer Ag | New aminophenylamidines, their production and their medicinal use |
US3925471A (en) * | 1970-06-13 | 1975-12-09 | Bayer Ag | Aminophenylamidines their production and their medicinal use |
US3925470A (en) * | 1970-06-13 | 1975-12-09 | Bayer Ag | Aminophenylamidines, their production and their medicinal use |
US3911013A (en) * | 1970-06-13 | 1975-10-07 | Bayer Ag | New aminophenylamidines, their production and their medicinal use |
US4018814A (en) * | 1970-06-13 | 1977-04-19 | Bayer Aktiengesellschaft | Aromatic amides and carbomates of phenylamidines |
US3923888A (en) * | 1970-06-13 | 1975-12-02 | Bayer Ag | Aminophenylamidines, their production and their medicinal use |
DE2029298C3 (de) * | 1970-06-13 | 1980-04-17 | Bayer Ag, 5090 Leverkusen | Aminophenylamidine, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel |
DE2029299C3 (de) * | 1970-06-13 | 1980-08-21 | Bayer Ag, 5090 Leverkusen | Neue Aminophenylamidine, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel |
US4013676A (en) * | 1970-06-13 | 1977-03-22 | Bayer Aktiengesellschaft | Aminophenylamidines, their production and their pharmaceutical use |
US3911010A (en) * | 1970-06-13 | 1975-10-07 | Bayer Ag | Aminophenylamidines, their production and their pharmaceutical use |
US3996247A (en) * | 1970-06-13 | 1976-12-07 | Bayer Aktiengesellschaft | Substituted 4-aminophenylamidines |
FR2098352A7 (en) * | 1970-07-13 | 1972-03-10 | Fahlberg List Veb | Hydroxyguanidines - with selective herbicidal activity |
GB1311913A (en) * | 1970-09-05 | 1973-03-28 | Fahlberg List Veb | Herbicidal hydroxyguanidines |
DE2350696A1 (de) * | 1972-10-12 | 1974-04-18 | Ciba Geigy Ag | Neue ester |
US3965176A (en) * | 1973-06-20 | 1976-06-22 | Schering Corporation | Novel substituted amidines |
IL44905A (en) * | 1973-06-25 | 1977-03-31 | Ciba Geigy Ag | N-alkyl-n-(n-alkylformimidoyl)-n'-phenylformamidine derivatives their preparation and use in pest control |
SE7411169L (sv) * | 1974-09-04 | 1976-03-05 | Wander Ag Dr A | Forfarande for framstellning av nya organiska foreningar |
JPS51118832A (en) * | 1975-04-09 | 1976-10-19 | Sumitomo Chem Co Ltd | A non-medical antibacterial, 3-pyridyl substituted guanidine |
US4211867A (en) * | 1976-03-19 | 1980-07-08 | Mcneil Laboratories, Incorporated | Nitrogen heterocyclic carboximidamide compounds |
DE2626128A1 (de) * | 1976-06-11 | 1977-12-22 | Beiersdorf Ag | N-substituierte benzimidazolin-2-one und verfahren zu deren herstellung |
US4182865A (en) * | 1978-09-18 | 1980-01-08 | Mcneil Laboratories, Inc. | Diaza-cyclic derivatives of guanidine |
US4414211A (en) * | 1978-09-18 | 1983-11-08 | Mcneilab, Inc. | Heterocyclic derivatives of guanidine |
DE2848786C3 (de) * | 1978-11-10 | 1981-05-21 | Ibm Deutschland Gmbh, 7000 Stuttgart | Schaltungsanordnung für die Synchronisierung der Auftrittszeitpunkte von Druckhammeraufschlag mit dem Eintreffen der Drucktype an der Druckstelle |
AU5263779A (en) * | 1978-11-29 | 1980-05-29 | Beecham Group Limited | Derivatives of thiazolidin-2-ylidene and oxazolidin-2-ylidene with hypoglycaemic acitivity |
US4247705A (en) * | 1979-02-06 | 1981-01-27 | A. H. Robins Company, Inc. | 4-Substituted 2-iminoimidazolidine compounds |
ZA801680B (en) * | 1979-04-03 | 1981-03-25 | Fujisawa Pharmaceutical Co | 2-imidazoline derivatives,process for the preparation thereof and the pharmaceutical composition of the same |
ZA802161B (en) * | 1979-04-11 | 1981-04-29 | Ciba Geigy Ag | Guanidines,processes for producing them,and pharmaceutical preparations containing sucn compounds |
IN150250B (da) * | 1979-04-16 | 1982-08-28 | Ciba Geigy India Ltd | |
EP0018134B1 (en) * | 1979-04-21 | 1984-03-14 | Beecham Group Plc | Dihydropyridine derivatives, processes for their preparation and pharmaceutical compositions containing them |
US4342764A (en) * | 1979-05-29 | 1982-08-03 | Ciba-Geigy Corporation | Guanidine compounds, pharmaceutical compositions and use |
JPS55160764A (en) * | 1979-05-29 | 1980-12-13 | Ciba Geigy Ag | Guanidine* its manufacture and pharmaceutic medicine containing same |
DD144919A1 (de) * | 1979-07-20 | 1980-11-12 | Rainer Beckert | Verfahren zur herstellung von 2,5-diaryl-3,4-diarylimino-1,2,5-thiadiazolidin-s-oxiden |
JPS5618969A (en) * | 1979-07-24 | 1981-02-23 | Toyama Chem Co Ltd | Novel 1-(4-aminobenzyl)-2,3-dioxopiperazine derivative, its acid addition salt, and their preparation |
US4340609A (en) * | 1980-01-02 | 1982-07-20 | William H. Rorer, Inc. | Amidinourea derivative veterinary compositions for suppression of parasitemia |
US4287201A (en) * | 1980-03-03 | 1981-09-01 | Merck & Co., Inc. | Anovulatory method and chicken feed compositions |
US4281004A (en) * | 1980-03-31 | 1981-07-28 | Pfizer Inc. | Phenylguanidine therapeutic agents |
DE3168754D1 (en) * | 1980-07-09 | 1985-03-21 | Beecham Group Plc | Clonidine derivatives useful in the treatment of diarrhoea |
US4348406A (en) * | 1980-10-20 | 1982-09-07 | Schering Corporation | Novel guanidine derivatives |
DE3100575A1 (de) * | 1981-01-10 | 1982-09-02 | Dr. Karl Thomae Gmbh, 7950 Biberach | "neue benzoesaeuren, ihre herstellung und ihre verwendung als arzneimittel" |
US4735959A (en) * | 1981-01-10 | 1988-04-05 | Dr. Karl Thomae Gmbh | Carboxylic acid amides and pharmaceutical compositions containing them |
DE3225188A1 (de) * | 1982-07-06 | 1984-01-12 | Dr. Karl Thomae Gmbh, 7950 Biberach | Neue phenylessigsaeurederivate, ihre herstellung und diese verbindungen enthaltende arzneimittel |
EP0070084A3 (en) * | 1981-04-24 | 1983-02-16 | Beecham Group Plc | Imidazoline derivatives |
US4461904A (en) * | 1981-11-20 | 1984-07-24 | Alcon Laboratories, Inc. | 2-(Trisubstituted phenylimino)-imidazolines |
DE3375783D1 (en) * | 1982-07-06 | 1988-04-07 | Thomae Gmbh Dr K | Phenyl-acetic-acid derivatives, their preparation and pharmaceutical compostions containing them |
US4533739A (en) * | 1982-10-12 | 1985-08-06 | G. D. Searle & Co. | 2-[(Aminophenyl and amidophenyl)amino]-1-azacycloalkanes having antidiarrheal activity |
IL70665A (en) * | 1983-01-13 | 1987-08-31 | Rhone Poulenc Sante | Condensed pyrrole carboxylic acid derivative intermediates for pharmaceuticals and their preparation |
FR2539417A1 (fr) * | 1983-01-13 | 1984-07-20 | Rhone Poulenc Sante | Nouveaux pyrrolo-1, 2 heterocycles, leur preparation et les medicaments qui les contiennent |
SU1114674A1 (ru) * | 1983-02-08 | 1984-09-23 | Предприятие П/Я Р-6913 | Способ получени гидрохлоридов производных @ , @ -дифенил бензамидина |
GB8304593D0 (en) * | 1983-02-18 | 1983-03-23 | Beecham Group Plc | Amidines |
US4619931A (en) * | 1983-02-28 | 1986-10-28 | Janssen Pharmaceutica, N.V. | [[4-[4-(4-phenyl-1-piperazinyl)phenoxymethyl]-1,3-dioxolan-2-yl]methyl]-1H-imidazoles and 1H-1,2,4-triazoles |
US4735942A (en) * | 1984-01-09 | 1988-04-05 | Janssen Pharmaceutica, N.V. | [[4-[4-(4-phenyl-1-piperazinyl)phenoxymethyl]-1,3-dioxolan-2-yl]-methyl]-1H-imidazoles and 1H-1,2,4-triazoles having antimicrobial properties |
US4861879A (en) * | 1983-02-28 | 1989-08-29 | Janssen Pharmaceutica N.V. | [[4-[4-Phenyl-1-piperazinyl)phenoxymethyl]-1-3-dioxolan-2-yl]-methyl]-1H-imidazoles and 1H-1,2,4-triazoles |
FR2549049B1 (fr) * | 1983-07-13 | 1986-06-20 | Chauvin Blache Lab | Nouvelles amidines, leur procede de preparation et leur application therapeutique |
US4723029A (en) * | 1983-09-23 | 1988-02-02 | Schering Corporation | Organic acid-substituted guanidine anthelmintics |
US4701447A (en) * | 1983-09-23 | 1987-10-20 | Schering Corporation | N-((2-nitro)phenyl)-N' (organic acid) guanidine anthelmintics |
JPS60100559A (ja) * | 1983-11-05 | 1985-06-04 | Morishita Seiyaku Kk | 2−アニリノ−1,6−ジヒドロ−6−オキソ−5−ピリミジンカルボン酸誘導体,その製法及び該化合物を含有する抗アレルギ−剤 |
US4579951A (en) * | 1984-03-19 | 1986-04-01 | G. D. Searle & Co. | Substituted (azacycloalk-2-yl)iminophenols and esters thereof |
US4560690A (en) * | 1984-04-30 | 1985-12-24 | Pfizer Inc. | 2-(N-substituted guanidino)-4-hetero-arylthiazole antiulcer agents |
EP0164204A1 (en) * | 1984-05-12 | 1985-12-11 | FISONS plc | Novel pharmaceutically useful pyrimidines |
HU192986B (en) * | 1984-05-23 | 1987-08-28 | Egyt Gyogyszervegyeszeti Gyar | Process for production of imidasodiline derivatives |
US4693850A (en) * | 1985-03-15 | 1987-09-15 | Mcneilab, Inc. | Methane sulfonic acid derivatives |
US4656270A (en) * | 1985-03-15 | 1987-04-07 | Mcneilab, Inc. | Process for producing guanidines such as linogliride |
DE3518917A1 (de) * | 1985-05-25 | 1986-11-27 | Bayer Ag, 5090 Leverkusen | Substituierte benzochinolizine, verfahren zur herstellung und ihre verwendung in arzneimitteln |
DE3529692A1 (de) * | 1985-08-20 | 1987-02-26 | Bayer Ag | Verwendung von lactamamiden als leistungsfoerderer bei tieren |
CA1292472C (en) * | 1985-12-03 | 1991-11-26 | Alfonsus Guilielmus Knaeps | Derivatives of ¬¬4-¬4-(4-phenyl-1-piperazinyl)- phenoxymethyl|-1,3-dioxolan-2-yl|methyl|-1h-imidazoles and 1h-1,2,4-triazoles |
ATE135699T1 (de) * | 1986-01-13 | 1996-04-15 | American Cyanamid Co | 4,5,6-substituierte 2-pyrimidinamine |
GB8602025D0 (en) | 1986-01-28 | 1986-03-05 | Reid M | Orthopaedic trolley |
-
1989
- 1989-02-16 GB GB898903592A patent/GB8903592D0/en active Pending
- 1989-12-13 FI FI895956A patent/FI95565C/fi not_active IP Right Cessation
- 1989-12-14 NO NO895023A patent/NO177993C/no not_active IP Right Cessation
- 1989-12-18 DK DK640889A patent/DK640889A/da not_active Application Discontinuation
- 1989-12-19 MY MYPI89001812A patent/MY105052A/en unknown
- 1989-12-27 CS CS897433A patent/CS277609B6/cs not_active IP Right Cessation
- 1989-12-28 BG BG90783A patent/BG60557B1/bg unknown
- 1989-12-28 ES ES89313636T patent/ES2055115T3/es not_active Expired - Lifetime
- 1989-12-28 US US07/458,237 patent/US5223498A/en not_active Expired - Lifetime
- 1989-12-28 YU YU248589A patent/YU48164B/sh unknown
- 1989-12-28 EP EP89313636A patent/EP0385038B1/en not_active Expired - Lifetime
- 1989-12-28 DE DE8989313636T patent/DE68906880T2/de not_active Expired - Fee Related
- 1989-12-28 AT AT89313636T patent/ATE90074T1/de not_active IP Right Cessation
- 1989-12-28 ZA ZA899941A patent/ZA899941B/xx unknown
- 1989-12-29 PL PL89295913A patent/PL161961B1/pl unknown
- 1989-12-29 RU SU894742813A patent/RU1826969C/ru active
- 1989-12-29 PT PT92770A patent/PT92770B/pt not_active IP Right Cessation
- 1989-12-29 DD DD89336816A patent/DD294023A5/de unknown
- 1989-12-29 PL PL28307489A patent/PL162960B1/pl unknown
- 1989-12-29 UA UA5011043A patent/UA27713C2/uk unknown
- 1989-12-29 JP JP1345135A patent/JP2545475B2/ja not_active Expired - Fee Related
- 1989-12-29 UA UA4742813A patent/UA19156A/uk unknown
- 1989-12-30 RO RO143555A patent/RO105807B1/ro unknown
- 1989-12-30 RO RO147103A patent/RO107945B1/ro unknown
-
1990
- 1990-01-03 IL IL9296390A patent/IL92963A/en not_active IP Right Cessation
- 1990-12-03 RU SU904831862A patent/RU1797610C/ru active
-
1992
- 1992-02-27 RU SU925011043A patent/RU2052452C1/ru active
-
1993
- 1993-01-27 US US08/009,807 patent/US5373008A/en not_active Expired - Fee Related
- 1993-06-30 LV LVP-93-815A patent/LV10619B/en unknown
- 1993-12-21 LT LTIP1647A patent/LT3960B/lt not_active IP Right Cessation
- 1993-12-21 LT LTIP1648A patent/LT3961B/lt not_active IP Right Cessation
- 1993-12-21 LT LTIP1646A patent/LT3958B/lt not_active IP Right Cessation
-
1994
- 1994-10-06 GE GEAP19942233A patent/GEP19981040B/en unknown
-
1995
- 1995-06-30 HU HU95P/P00688P patent/HU211571A9/hu unknown
Also Published As
Similar Documents
Publication | Publication Date | Title |
---|---|---|
LV10619B (en) | Therapeutic agents | |
FI66861B (fi) | Foerfarande foer framstaellning av n,n2-disubstituerade propylendiaminer med antihypertensiv verkan | |
FI109534B (fi) | Menetelmä farmakologisesti vaikuttavien pyrimidiinijohdannaisten valmistamiseksi | |
Iwanami et al. | Synthesis and neuroleptic activity of benzamides. Cis-N-(1-benzyl-2-methylpyrrolidin-3-yl)-5-chloro-2-methoxy-4-(methylamino) benzamide and related compounds | |
PL179255B1 (pl) | N owe pochodne 4-aminopiperydylo-(1 )-benzoiloguanidyny, sposób ich wytwarzania oraz preparat farmaceutyczny PL PL PL PL PL PL PL | |
NZ250878A (en) | Substituted sulphamoyl derivatives and medicaments | |
CZ29996A3 (en) | Amidine derivatives with activities of nitrogen oxide sythetase | |
SK283463B6 (sk) | Indolínové deriváty, spôsob ich prípravy, medziprodukty tohto spôsobu a farmaceutický prostriedok obsahujúci tieto deriváty | |
US5302720A (en) | Biphenyl-substituted guanidine derivatives useful as hypoglycaemic agents | |
FI80019C (fi) | Foerfarande foer framstaellning av terapeutiskt anvaendbara n-(piperidinyl-alkyl)karboxamider. | |
WO2011138265A2 (en) | Indole and indazole derivatives as orexin receptor antagonists | |
CZ20032342A3 (cs) | Inhibitory peptid-deformylázy | |
US6569880B2 (en) | Bis(benzimidazole) derivatives serving as potassium blocking agents | |
AU632778B2 (en) | Hypoglycaemic amidines and guanidines | |
EA001399B1 (ru) | Ингибиторы пролилэндопептидазы | |
Dahlgren et al. | New inhibitors of the malaria aspartyl proteases plasmepsin I and II | |
CS225804B2 (cs) | Způsob výroby heterocyklických derivátů guanidinu | |
NO312896B1 (no) | Nye 4-(1-piperazinyl)benzosyrederivater, fremgangsmåte for fremstilling derav, samt farmasöytiske preparater som omfatter dem | |
SI8912485A (sl) | Nova hipoglikemična sredstva in postopek za njihovo pripravo | |
US20020165236A1 (en) | Compounds for the treatment of protozoal diseases | |
ZA200406548B (en) | Process for the preparation of morpholine derivatives and intermediates therefor. | |
JP3930081B2 (ja) | 2−ウレイド−ベンズアミド誘導体 | |
JPS62252762A (ja) | ピログルタミド誘導体 | |
WO2006018815A1 (en) | Piperazine derivatives as adrenergic receptor antagonists |