CS277609B6 - Amino(methyl)phenyl derivatives, process for their preparation and use - Google Patents
Amino(methyl)phenyl derivatives, process for their preparation and use Download PDFInfo
- Publication number
- CS277609B6 CS277609B6 CS897433A CS743389A CS277609B6 CS 277609 B6 CS277609 B6 CS 277609B6 CS 897433 A CS897433 A CS 897433A CS 743389 A CS743389 A CS 743389A CS 277609 B6 CS277609 B6 CS 277609B6
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- group
- methyl
- formula
- phenyl
- carbon atoms
- Prior art date
Links
- -1 Amino(methyl)phenyl Chemical class 0.000 title claims description 227
- 238000000034 method Methods 0.000 title description 23
- 238000002360 preparation method Methods 0.000 title description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 149
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 42
- 150000003839 salts Chemical class 0.000 claims abstract description 29
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 27
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 26
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 20
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 15
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 12
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 7
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 4
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 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 36
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 33
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 30
- 239000001257 hydrogen Substances 0.000 claims description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims description 25
- 150000003254 radicals Chemical class 0.000 claims description 20
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 15
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 15
- 229910052799 carbon Inorganic materials 0.000 claims description 14
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 13
- 125000002947 alkylene group Chemical group 0.000 claims description 13
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 12
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 10
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 10
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 9
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 8
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 8
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 8
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- 101150065749 Churc1 gene Proteins 0.000 claims description 5
- 125000003277 amino group Chemical group 0.000 claims description 5
- 125000005394 methallyl group Chemical group 0.000 claims description 5
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 5
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 5
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims description 4
- 102100038239 Protein Churchill Human genes 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 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 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 2
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims description 2
- 125000002837 carbocyclic group Chemical group 0.000 claims description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 2
- 125000004450 alkenylene group Chemical group 0.000 claims 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims 1
- 125000006353 oxyethylene group Chemical group 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract description 5
- 125000004644 alkyl sulfinyl group Chemical group 0.000 abstract description 3
- 229940126904 hypoglycaemic agent Drugs 0.000 abstract description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
- 125000004390 alkyl sulfonyl group Chemical group 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 366
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 249
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 228
- 239000000203 mixture Substances 0.000 description 216
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 210
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 174
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 160
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 93
- 239000000243 solution Substances 0.000 description 80
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 74
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 66
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 65
- 239000000047 product Substances 0.000 description 64
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 59
- 238000006243 chemical reaction Methods 0.000 description 55
- 239000003921 oil Substances 0.000 description 47
- 235000019198 oils Nutrition 0.000 description 47
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 46
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 45
- 239000007787 solid Substances 0.000 description 43
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 42
- 239000002904 solvent Substances 0.000 description 41
- 238000010992 reflux Methods 0.000 description 38
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 35
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 33
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 28
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 24
- 239000001530 fumaric acid Substances 0.000 description 24
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-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
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 22
- QKWLVAYDAHQMLG-UHFFFAOYSA-N 2-morpholin-4-ylaniline Chemical compound NC1=CC=CC=C1N1CCOCC1 QKWLVAYDAHQMLG-UHFFFAOYSA-N 0.000 description 21
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
- 239000003480 eluent Substances 0.000 description 20
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 19
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 18
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 18
- 239000004480 active ingredient Substances 0.000 description 16
- 238000001704 evaporation Methods 0.000 description 16
- 229940046892 lead acetate Drugs 0.000 description 16
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 229910021529 ammonia Inorganic materials 0.000 description 15
- 230000008020 evaporation Effects 0.000 description 15
- 239000011541 reaction mixture Substances 0.000 description 15
- 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
- KQNKJJBFUFKYFX-UHFFFAOYSA-N acetic acid;trihydrate Chemical compound O.O.O.CC(O)=O KQNKJJBFUFKYFX-UHFFFAOYSA-N 0.000 description 13
- 239000012267 brine Substances 0.000 description 13
- 238000004587 chromatography analysis Methods 0.000 description 13
- 238000004440 column chromatography Methods 0.000 description 13
- 238000006482 condensation reaction Methods 0.000 description 13
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 13
- 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 12
- LGDSHSYDSCRFAB-UHFFFAOYSA-N Methyl isothiocyanate Chemical compound CN=C=S LGDSHSYDSCRFAB-UHFFFAOYSA-N 0.000 description 12
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- 239000008103 glucose Substances 0.000 description 12
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 12
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 11
- 238000009835 boiling Methods 0.000 description 11
- 239000000284 extract Substances 0.000 description 11
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 11
- 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 11
- 239000003826 tablet Substances 0.000 description 11
- 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 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 238000002844 melting Methods 0.000 description 10
- 230000008018 melting Effects 0.000 description 10
- 230000007935 neutral effect Effects 0.000 description 10
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 9
- 150000001412 amines Chemical class 0.000 description 9
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 9
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 description 8
- 150000002431 hydrogen Chemical class 0.000 description 8
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 8
- 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
- 239000002585 base Substances 0.000 description 7
- 239000012047 saturated solution Substances 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
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 239000002775 capsule Substances 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 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 6
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 description 6
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- AQYPBQKDGHHKBD-UHFFFAOYSA-N (2-morpholin-4-ylphenyl)cyanamide Chemical compound N#CNC1=CC=CC=C1N1CCOCC1 AQYPBQKDGHHKBD-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
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 5
- 239000004202 carbamide Substances 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- OAGOUCJGXNLJNL-UHFFFAOYSA-N dimethylcyanamide Chemical compound CN(C)C#N OAGOUCJGXNLJNL-UHFFFAOYSA-N 0.000 description 5
- 239000010410 layer Substances 0.000 description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 description 5
- 229910001220 stainless steel Inorganic materials 0.000 description 5
- 239000010935 stainless steel Substances 0.000 description 5
- 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 4
- 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 4
- BNBJMXCRCHPDIG-UHFFFAOYSA-N 2-(morpholin-4-ylmethyl)aniline Chemical compound NC1=CC=CC=C1CN1CCOCC1 BNBJMXCRCHPDIG-UHFFFAOYSA-N 0.000 description 4
- WDYVUKGVKRZQNM-UHFFFAOYSA-N 6-phosphonohexylphosphonic acid Chemical compound OP(O)(=O)CCCCCCP(O)(O)=O WDYVUKGVKRZQNM-UHFFFAOYSA-N 0.000 description 4
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 4
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 239000002552 dosage form Substances 0.000 description 4
- 239000012259 ether extract Substances 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 239000012458 free base Substances 0.000 description 4
- LRDFRRGEGBBSRN-UHFFFAOYSA-N isobutyronitrile Chemical compound CC(C)C#N LRDFRRGEGBBSRN-UHFFFAOYSA-N 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 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 4
- 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 4
- 239000008194 pharmaceutical composition Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000010898 silica gel chromatography Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000000829 suppository Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- CMMLLKHOSNEVFO-UHFFFAOYSA-N (2-morpholin-4-ylphenyl)thiourea Chemical compound NC(=S)NC1=CC=CC=C1N1CCOCC1 CMMLLKHOSNEVFO-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
- HBAIZGPCSAAFSU-UHFFFAOYSA-N 1-(2-hydroxyethyl)imidazolidin-2-one Chemical compound OCCN1CCNC1=O HBAIZGPCSAAFSU-UHFFFAOYSA-N 0.000 description 3
- 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 3
- BCQIXIZMDBMYDB-UHFFFAOYSA-N 2-(2-morpholin-4-ylphenyl)guanidine Chemical compound NC(N)=NC1=CC=CC=C1N1CCOCC1 BCQIXIZMDBMYDB-UHFFFAOYSA-N 0.000 description 3
- FQSYRJIMZVMLBM-UHFFFAOYSA-N 2-(5-chloro-2-morpholin-4-ylphenyl)-1,1-dimethylguanidine Chemical compound CN(C)C(N)=NC1=CC(Cl)=CC=C1N1CCOCC1 FQSYRJIMZVMLBM-UHFFFAOYSA-N 0.000 description 3
- ASUDFOJKTJLAIK-UHFFFAOYSA-N 2-methoxyethanamine Chemical compound COCCN ASUDFOJKTJLAIK-UHFFFAOYSA-N 0.000 description 3
- 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 3
- FABHEYAZAOCBCH-UHFFFAOYSA-N 5-methyl-2-morpholin-4-ylaniline Chemical compound NC1=CC(C)=CC=C1N1CCOCC1 FABHEYAZAOCBCH-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
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-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
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 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
- 239000002253 acid Substances 0.000 description 3
- 230000001476 alcoholic effect Effects 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 235000011114 ammonium hydroxide Nutrition 0.000 description 3
- 150000001450 anions Chemical class 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 3
- 229940045803 cuprous chloride Drugs 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 229940071870 hydroiodic acid Drugs 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 239000008101 lactose Substances 0.000 description 3
- 239000002609 medium Substances 0.000 description 3
- PTGWNQXYFRYROU-UHFFFAOYSA-N n'-(2-morpholin-4-ylphenyl)ethanimidamide Chemical compound CC(=N)NC1=CC=CC=C1N1CCOCC1 PTGWNQXYFRYROU-UHFFFAOYSA-N 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 239000012429 reaction media Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- UKLNMMHNWFDKNT-UHFFFAOYSA-M sodium chlorite Chemical compound [Na+].[O-]Cl=O UKLNMMHNWFDKNT-UHFFFAOYSA-M 0.000 description 3
- 229960002218 sodium chlorite Drugs 0.000 description 3
- 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 2
- JFXFQLTTXMZHBM-UHFFFAOYSA-N (2-piperidin-1-ylphenyl)thiourea Chemical compound NC(=S)NC1=CC=CC=C1N1CCCCC1 JFXFQLTTXMZHBM-UHFFFAOYSA-N 0.000 description 2
- SMVFRCLPUWCZIF-UHFFFAOYSA-N (2-pyrrolidin-1-ylphenyl)thiourea Chemical compound NC(=S)NC1=CC=CC=C1N1CCCC1 SMVFRCLPUWCZIF-UHFFFAOYSA-N 0.000 description 2
- LOPWBKHHJFJKPO-UHFFFAOYSA-N (3-methyl-2-morpholin-4-ylphenyl)cyanamide Chemical compound CC1=CC=CC(NC#N)=C1N1CCOCC1 LOPWBKHHJFJKPO-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
- 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 2
- 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 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
- 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 2
- DYMVJWOTOQCATD-UHFFFAOYSA-N (5-fluoro-2-morpholin-4-ylphenyl)cyanamide Chemical compound N#CNC1=CC(F)=CC=C1N1CCOCC1 DYMVJWOTOQCATD-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
- 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 2
- 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 2
- DCEQKRORMZMZHV-UHFFFAOYSA-N 1,1-diethyl-2-(2-morpholin-4-ylphenyl)guanidine Chemical compound CCN(CC)C(N)=NC1=CC=CC=C1N1CCOCC1 DCEQKRORMZMZHV-UHFFFAOYSA-N 0.000 description 2
- WVLQNRALFCAULM-UHFFFAOYSA-N 1,1-dimethyl-2-(2-methyl-6-morpholin-4-ylphenyl)guanidine Chemical compound CN(C)C(N)=NC1=C(C)C=CC=C1N1CCOCC1 WVLQNRALFCAULM-UHFFFAOYSA-N 0.000 description 2
- OHFMKFHVEXXQGP-UHFFFAOYSA-N 1,1-dimethyl-2-(2-piperidin-1-ylphenyl)guanidine Chemical compound CN(C)C(N)=NC1=CC=CC=C1N1CCCCC1 OHFMKFHVEXXQGP-UHFFFAOYSA-N 0.000 description 2
- RSCWEEQQDARHSS-UHFFFAOYSA-N 1,1-dimethyl-2-(2-pyrrolidin-1-ylphenyl)guanidine Chemical compound CN(C)C(N)=NC1=CC=CC=C1N1CCCC1 RSCWEEQQDARHSS-UHFFFAOYSA-N 0.000 description 2
- BRKNKZKJTGFCIB-UHFFFAOYSA-N 1,1-dimethyl-2-(3-methyl-2-morpholin-4-ylphenyl)guanidine Chemical compound CN(C)C(N)=NC1=CC=CC(C)=C1N1CCOCC1 BRKNKZKJTGFCIB-UHFFFAOYSA-N 0.000 description 2
- CMFUNUPPYXTXKB-UHFFFAOYSA-N 1,1-dimethyl-2-(5-methyl-2-morpholin-4-ylphenyl)guanidine Chemical compound CN(C)C(N)=NC1=CC(C)=CC=C1N1CCOCC1 CMFUNUPPYXTXKB-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 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 2
- DLFWLHAFKJXQFP-UHFFFAOYSA-N 1,1-dimethyl-2-[2-(1,2,4-oxathiazinan-4-yl)phenyl]guanidine Chemical compound CN(C)C(N)=NC1=CC=CC=C1N1CSOCC1 DLFWLHAFKJXQFP-UHFFFAOYSA-N 0.000 description 2
- UWDMXYWIYRWPCF-UHFFFAOYSA-N 1,1-dimethyl-2-[2-morpholin-4-yl-5-(trifluoromethyl)phenyl]guanidine Chemical compound CN(C)C(N)=NC1=CC(C(F)(F)F)=CC=C1N1CCOCC1 UWDMXYWIYRWPCF-UHFFFAOYSA-N 0.000 description 2
- 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 2
- UUIQBSIKJZRPKD-UHFFFAOYSA-N 1,1-dimethyl-2-[5-(methylsulfanylmethyl)-2-morpholin-4-ylphenyl]guanidine Chemical compound CN(C)C(N)=NC1=CC(CSC)=CC=C1N1CCOCC1 UUIQBSIKJZRPKD-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 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 2
- FBCAJWQEFIFURV-UHFFFAOYSA-N 1,3-dimethyl-n-(2-morpholin-4-ylphenyl)imidazolidin-2-imine Chemical compound CN1CCN(C)C1=NC1=CC=CC=C1N1CCOCC1 FBCAJWQEFIFURV-UHFFFAOYSA-N 0.000 description 2
- RKNLYMYCMBQNSG-UHFFFAOYSA-N 1,3-dimethyl-n-(2-thiomorpholin-4-ylphenyl)imidazolidin-2-imine Chemical compound CN1CCN(C)C1=NC1=CC=CC=C1N1CCSCC1 RKNLYMYCMBQNSG-UHFFFAOYSA-N 0.000 description 2
- 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 2
- CJMUPCHCOYBPLD-UHFFFAOYSA-N 1-(2-isothiocyanatophenyl)piperidine Chemical compound S=C=NC1=CC=CC=C1N1CCCCC1 CJMUPCHCOYBPLD-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 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 2
- DUYFRKLRCIVNBM-UHFFFAOYSA-N 1-(2-morpholin-4-ylphenyl)-2,3-dipropylguanidine Chemical compound CCCNC(NCCC)=NC1=CC=CC=C1N1CCOCC1 DUYFRKLRCIVNBM-UHFFFAOYSA-N 0.000 description 2
- LHSJVYODFKJLOR-UHFFFAOYSA-N 1-butyl-2-methyl-3-(5-methyl-2-morpholin-4-ylphenyl)guanidine Chemical compound CCCCNC(NC)=NC1=CC(C)=CC=C1N1CCOCC1 LHSJVYODFKJLOR-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
- 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 2
- BFCFYVKQTRLZHA-UHFFFAOYSA-N 1-chloro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Cl BFCFYVKQTRLZHA-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
- 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 2
- PWKNBLFSJAVFAB-UHFFFAOYSA-N 1-fluoro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1F PWKNBLFSJAVFAB-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 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 2
- 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 2
- 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 2
- YDSSRNGAJGVEOD-UHFFFAOYSA-N 1-methyl-n-(2-morpholin-4-ylphenyl)-5,6-dihydro-4h-pyrimidin-2-amine Chemical compound CN1CCCNC1=NC1=CC=CC=C1N1CCOCC1 YDSSRNGAJGVEOD-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
- UXQSLUMLBUONSI-UHFFFAOYSA-N 2-(2-methoxyethyl)-1-(2-morpholin-4-ylphenyl)guanidine Chemical compound COCCNC(N)=NC1=CC=CC=C1N1CCOCC1 UXQSLUMLBUONSI-UHFFFAOYSA-N 0.000 description 2
- 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 2
- VTVRFGMLMKNNAQ-UHFFFAOYSA-N 2-(2-methylsulfanylethyl)-1-(2-morpholin-4-ylphenyl)guanidine Chemical compound CSCCNC(N)=NC1=CC=CC=C1N1CCOCC1 VTVRFGMLMKNNAQ-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
- VFQRQOCAKNYDLF-UHFFFAOYSA-N 2-(4-methoxy-2-morpholin-4-ylphenyl)-1,1-dimethylguanidine Chemical compound COC1=CC=C(N=C(N)N(C)C)C(N2CCOCC2)=C1 VFQRQOCAKNYDLF-UHFFFAOYSA-N 0.000 description 2
- 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 2
- LGTLXSYUSFFCRQ-UHFFFAOYSA-N 2-(5-ethyl-2-morpholin-4-ylphenyl)-1,1-dimethylguanidine Chemical compound CN(C)C(N)=NC1=CC(CC)=CC=C1N1CCOCC1 LGTLXSYUSFFCRQ-UHFFFAOYSA-N 0.000 description 2
- 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 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
- FVZSEOMQJAGBTM-UHFFFAOYSA-N 2-[2-(2-morpholin-4-ylanilino)-4,5-dihydroimidazol-1-yl]ethanol Chemical compound OCCN1CCNC1=NC1=CC=CC=C1N1CCOCC1 FVZSEOMQJAGBTM-UHFFFAOYSA-N 0.000 description 2
- MWISMCWBKSGBSE-UHFFFAOYSA-N 2-[3-methyl-2-(2-morpholin-4-ylphenyl)iminoimidazolidin-1-yl]ethyl acetate Chemical compound CN1CCN(CCOC(C)=O)C1=NC1=CC=CC=C1N1CCOCC1 MWISMCWBKSGBSE-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 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 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
- 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 2
- DPJCXCZTLWNFOH-UHFFFAOYSA-N 2-nitroaniline Chemical compound NC1=CC=CC=C1[N+]([O-])=O DPJCXCZTLWNFOH-UHFFFAOYSA-N 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
- 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
- RDRZXBQWXVHWLR-UHFFFAOYSA-N 4-(2-isothiocyanato-4-methylphenyl)morpholine Chemical compound S=C=NC1=CC(C)=CC=C1N1CCOCC1 RDRZXBQWXVHWLR-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
- GYILGUCNWIUUOX-UHFFFAOYSA-N 4-(2-isothiocyanato-6-methylphenyl)morpholine Chemical compound CC1=CC=CC(N=C=S)=C1N1CCOCC1 GYILGUCNWIUUOX-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
- 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
- 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
- NSVHSRBHIFWVGP-UHFFFAOYSA-N 5-fluoro-2-morpholin-4-ylaniline Chemical compound NC1=CC(F)=CC=C1N1CCOCC1 NSVHSRBHIFWVGP-UHFFFAOYSA-N 0.000 description 2
- 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 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
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- 229920002261 Corn starch Polymers 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 2
- 101000986989 Naja kaouthia Acidic phospholipase A2 CM-II Proteins 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
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- 239000005708 Sodium hypochlorite Substances 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
- 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 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
- 239000013543 active substance Substances 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
- 239000003472 antidiabetic agent Substances 0.000 description 2
- 238000003556 assay Methods 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
- GHWVXCQZPNWFRO-UHFFFAOYSA-N butane-2,3-diamine Chemical compound CC(N)C(C)N GHWVXCQZPNWFRO-UHFFFAOYSA-N 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
- 150000001718 carbodiimides Chemical class 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 229940081734 cellulose acetate phthalate Drugs 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- MPTQRFCYZCXJFQ-UHFFFAOYSA-L copper(II) chloride dihydrate Chemical compound O.O.[Cl-].[Cl-].[Cu+2] MPTQRFCYZCXJFQ-UHFFFAOYSA-L 0.000 description 2
- 239000008120 corn starch Substances 0.000 description 2
- 229940099112 cornstarch Drugs 0.000 description 2
- RCJVRSBWZCNNQT-UHFFFAOYSA-N dichloridooxygen Chemical compound ClOCl RCJVRSBWZCNNQT-UHFFFAOYSA-N 0.000 description 2
- 239000002027 dichloromethane extract Substances 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
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 2
- XWBDWHCCBGMXKG-UHFFFAOYSA-N ethanamine;hydron;chloride Chemical compound Cl.CCN XWBDWHCCBGMXKG-UHFFFAOYSA-N 0.000 description 2
- 210000004051 gastric juice Anatomy 0.000 description 2
- 239000007903 gelatin capsule Substances 0.000 description 2
- UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical compound O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 description 2
- 150000003840 hydrochlorides Chemical class 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
- 150000002540 isothiocyanates Chemical class 0.000 description 2
- 230000002045 lasting effect Effects 0.000 description 2
- FTIAGMOESLWRPG-UHFFFAOYSA-N methyl 3-[[amino(dimethylamino)methylidene]amino]-4-morpholin-4-ylbenzoate Chemical compound CN(C)C(N)=NC1=CC(C(=O)OC)=CC=C1N1CCOCC1 FTIAGMOESLWRPG-UHFFFAOYSA-N 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
- 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 2
- 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 2
- BFYVOZVZQKMNEB-UHFFFAOYSA-N methyl n'-ethyl-n-(2-morpholin-4-ylphenyl)carbamimidothioate Chemical compound CCN=C(SC)NC1=CC=CC=C1N1CCOCC1 BFYVOZVZQKMNEB-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 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 2
- GAGYTSOEDMAYIA-UHFFFAOYSA-N n'-(2-morpholin-4-ylphenyl)butanimidamide Chemical compound CCCC(=N)NC1=CC=CC=C1N1CCOCC1 GAGYTSOEDMAYIA-UHFFFAOYSA-N 0.000 description 2
- HFJHZSQLRZVYMR-UHFFFAOYSA-N n'-(2-morpholin-4-ylphenyl)morpholine-4-carboximidamide Chemical compound C1COCCN1C(=N)NC1=CC=CC=C1N1CCOCC1 HFJHZSQLRZVYMR-UHFFFAOYSA-N 0.000 description 2
- SPVWQWQRTCPMHZ-UHFFFAOYSA-N n'-(2-morpholin-4-ylphenyl)pentanimidamide Chemical compound CCCCC(=N)NC1=CC=CC=C1N1CCOCC1 SPVWQWQRTCPMHZ-UHFFFAOYSA-N 0.000 description 2
- BLUUWKVYAFKWFO-UHFFFAOYSA-N n'-(2-morpholin-4-ylphenyl)propanimidamide Chemical compound CCC(=N)NC1=CC=CC=C1N1CCOCC1 BLUUWKVYAFKWFO-UHFFFAOYSA-N 0.000 description 2
- 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 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
- 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 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
- 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 2
- MUYXRSPUPCCOHU-UHFFFAOYSA-N n-[5-chloro-2-(morpholin-4-ylmethyl)phenyl]-2,3,4,5-tetrahydropyridin-6-amine Chemical compound C1CCCNC1=NC1=CC(Cl)=CC=C1CN1CCOCC1 MUYXRSPUPCCOHU-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
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 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
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 2
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
- 235000013855 polyvinylpyrrolidone Nutrition 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
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 2
- 239000012265 solid product Substances 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 150000003585 thioureas Chemical class 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
- 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 1
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 description 1
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 description 1
- ZYPZFGGOCOBOJP-WLHGVMLRSA-N (E)-but-2-enedioic acid N'-(2-morpholin-4-ylphenyl)butanimidamide Chemical compound OC(=O)\C=C\C(O)=O.CCCC(=N)NC1=CC=CC=C1N1CCOCC1 ZYPZFGGOCOBOJP-WLHGVMLRSA-N 0.000 description 1
- UDXDIKPMGDAKBJ-WLHGVMLRSA-N (E)-but-2-enedioic acid N-[5-chloro-2-(morpholin-4-ylmethyl)phenyl]-1,3-dimethylimidazolidin-2-imine Chemical compound OC(=O)\C=C\C(O)=O.CN1CCN(C)C1=NC1=CC(Cl)=CC=C1CN1CCOCC1 UDXDIKPMGDAKBJ-WLHGVMLRSA-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
- OULNZNAOEADVJM-WLHGVMLRSA-N (e)-but-2-enedioic acid;2-[3-methyl-2-(2-morpholin-4-ylphenyl)iminoimidazolidin-1-yl]ethyl benzoate Chemical compound OC(=O)\C=C\C(O)=O.C=1C=CC=C(N2CCOCC2)C=1N=C1N(C)CCN1CCOC(=O)C1=CC=CC=C1 OULNZNAOEADVJM-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
- BBDLIWIEMWDHTB-WLHGVMLRSA-N (e)-but-2-enedioic acid;n-(2-morpholin-4-ylphenyl)-2,3,4,5-tetrahydropyridin-6-amine Chemical compound OC(=O)\C=C\C(O)=O.N1CCCCC1=NC1=CC=CC=C1N1CCOCC1 BBDLIWIEMWDHTB-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
- MHCVCKDNQYMGEX-UHFFFAOYSA-N 1,1'-biphenyl;phenoxybenzene Chemical group C1=CC=CC=C1C1=CC=CC=C1.C=1C=CC=CC=1OC1=CC=CC=C1 MHCVCKDNQYMGEX-UHFFFAOYSA-N 0.000 description 1
- GPCBEYBKBZUWEP-UHFFFAOYSA-N 1,1,2-trimethyl-3-(2-morpholin-4-ylphenyl)guanidine Chemical compound CNC(N(C)C)=NC1=CC=CC=C1N1CCOCC1 GPCBEYBKBZUWEP-UHFFFAOYSA-N 0.000 description 1
- QAXPTEZFLCHEJH-UHFFFAOYSA-N 1,1,3,3-tetramethyl-2-(2-morpholin-4-ylphenyl)guanidine Chemical compound CN(C)C(N(C)C)=NC1=CC=CC=C1N1CCOCC1 QAXPTEZFLCHEJH-UHFFFAOYSA-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
- FHCKDCVPDZBKEA-UHFFFAOYSA-N 1,1,3-trimethyl-3-pentylurea Chemical compound CCCCCN(C)C(=O)N(C)C FHCKDCVPDZBKEA-UHFFFAOYSA-N 0.000 description 1
- BLUKMJWFJBXGQX-UHFFFAOYSA-N 1,1-bis(2-methoxyethyl)-2-(2-morpholin-4-ylphenyl)guanidine Chemical compound COCCN(CCOC)C(N)=NC1=CC=CC=C1N1CCOCC1 BLUKMJWFJBXGQX-UHFFFAOYSA-N 0.000 description 1
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 1
- SIVXCXCJKJYJST-UHFFFAOYSA-N 1,1-dimethyl-2-(2-morpholin-4-ylphenyl)guanidine;hydrochloride Chemical compound Cl.CN(C)C(N)=NC1=CC=CC=C1N1CCOCC1 SIVXCXCJKJYJST-UHFFFAOYSA-N 0.000 description 1
- OSKSHTLFBRFGHZ-UHFFFAOYSA-N 1,1-dimethyl-2-(4-methyl-2-morpholin-4-ylphenyl)guanidine Chemical compound CN(C)C(N)=NC1=CC=C(C)C=C1N1CCOCC1 OSKSHTLFBRFGHZ-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
- CRRSHNAWOFPFCT-UHFFFAOYSA-N 1,1-dimethyl-2-[2-(4-methylpiperazin-1-yl)phenyl]guanidine Chemical compound CN(C)C(N)=NC1=CC=CC=C1N1CCN(C)CC1 CRRSHNAWOFPFCT-UHFFFAOYSA-N 0.000 description 1
- UQIUWSUPVVOCBM-UHFFFAOYSA-N 1,1-dimethyl-2-[2-(morpholin-4-ylmethyl)phenyl]guanidine Chemical compound CN(C)C(=N)NC1=CC=CC=C1CN1CCOCC1 UQIUWSUPVVOCBM-UHFFFAOYSA-N 0.000 description 1
- VYSBQCYINNMTQS-UHFFFAOYSA-N 1,2-diethyl-3-(2-morpholin-4-ylphenyl)guanidine Chemical compound CCNC(NCC)=NC1=CC=CC=C1N1CCOCC1 VYSBQCYINNMTQS-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
- LMRJJUFCFVLEEW-UHFFFAOYSA-N 1,3,3-trimethyl-n-(2-morpholin-4-ylphenyl)pyrrolidin-2-imine Chemical compound CN1CCC(C)(C)C1=NC1=CC=CC=C1N1CCOCC1 LMRJJUFCFVLEEW-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
- ZBOWKDHBOFMERX-UHFFFAOYSA-N 1,3-diazepane Chemical group C1CCNCNC1 ZBOWKDHBOFMERX-UHFFFAOYSA-N 0.000 description 1
- MSVZOIZEBAPKPL-UHFFFAOYSA-N 1,3-diethyl-n-(2-morpholin-4-ylphenyl)imidazolidin-2-imine Chemical compound CCN1CCN(CC)C1=NC1=CC=CC=C1N1CCOCC1 MSVZOIZEBAPKPL-UHFFFAOYSA-N 0.000 description 1
- GVVZVAGNYVMATE-UHFFFAOYSA-N 1,3-dimethyl-n-(2-morpholin-4-ylphenyl)piperidin-2-imine Chemical compound CC1CCCN(C)C1=NC1=CC=CC=C1N1CCOCC1 GVVZVAGNYVMATE-UHFFFAOYSA-N 0.000 description 1
- ZTFWZAJHLUMJAL-UHFFFAOYSA-N 1,3-dimethyl-n-(2-morpholin-4-ylphenyl)pyrrolidin-2-imine Chemical compound CC1CCN(C)C1=NC1=CC=CC=C1N1CCOCC1 ZTFWZAJHLUMJAL-UHFFFAOYSA-N 0.000 description 1
- SXBICAFABXAEEI-UHFFFAOYSA-N 1,3-dimethyl-n-(2-piperidin-1-ylphenyl)imidazolidin-2-imine Chemical compound CN1CCN(C)C1=NC1=CC=CC=C1N1CCCCC1 SXBICAFABXAEEI-UHFFFAOYSA-N 0.000 description 1
- NLDXUHLLRZRPPI-UHFFFAOYSA-N 1,3-dimethyl-n-(2-piperidin-1-ylphenyl)pyrrolidin-2-imine Chemical compound CC1CCN(C)C1=NC1=CC=CC=C1N1CCCCC1 NLDXUHLLRZRPPI-UHFFFAOYSA-N 0.000 description 1
- YQROWQYOQIEYLM-UHFFFAOYSA-N 1,3-dimethyl-n-(2-pyrrolidin-1-ylphenyl)imidazolidin-2-imine Chemical compound CN1CCN(C)C1=NC1=CC=CC=C1N1CCCC1 YQROWQYOQIEYLM-UHFFFAOYSA-N 0.000 description 1
- HXQGIEVGRXTPBO-UHFFFAOYSA-N 1,3-dimethyl-n-(2-pyrrolidin-1-ylphenyl)pyrrolidin-2-imine Chemical compound CC1CCN(C)C1=NC1=CC=CC=C1N1CCCC1 HXQGIEVGRXTPBO-UHFFFAOYSA-N 0.000 description 1
- FRJXJALHMLVPTD-UHFFFAOYSA-N 1,3-dimethyl-n-(5-methyl-2-morpholin-4-ylphenyl)imidazolidin-2-imine Chemical compound CN1CCN(C)C1=NC1=CC(C)=CC=C1N1CCOCC1 FRJXJALHMLVPTD-UHFFFAOYSA-N 0.000 description 1
- QXVBIBNQLKQRBU-UHFFFAOYSA-N 1,3-dimethyl-n-[2-(1-oxo-1,4-thiazinan-4-yl)phenyl]imidazolidin-2-imine;hydrate Chemical compound O.CN1CCN(C)C1=NC1=CC=CC=C1N1CCS(=O)CC1 QXVBIBNQLKQRBU-UHFFFAOYSA-N 0.000 description 1
- XMMINWBWZFWZKG-UHFFFAOYSA-N 1,3-dimethyl-n-[2-(2-methylpyrrolidin-1-yl)phenyl]imidazolidin-2-imine Chemical compound CC1CCCN1C1=CC=CC=C1N=C1N(C)CCN1C XMMINWBWZFWZKG-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
- ATDLANNMDBYQDO-UHFFFAOYSA-N 1-(2-isothiocyanato-3-methylphenyl)piperidine Chemical compound CC1=CC=CC(N2CCCCC2)=C1N=C=S ATDLANNMDBYQDO-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
- WWYWCNBRRSJGKX-UHFFFAOYSA-N 1-(2-methylpropyl)-n-(2-morpholin-4-ylphenyl)imidazolidin-2-amine Chemical compound CC(C)CN1CCNC1NC1=CC=CC=C1N1CCOCC1 WWYWCNBRRSJGKX-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
- WZSMSVBKFDAORG-UHFFFAOYSA-N 1-benzyl-n-(2-morpholin-4-ylphenyl)-4,5-dihydroimidazol-2-amine Chemical compound C=1C=CC=CC=1CN1CCNC1=NC1=CC=CC=C1N1CCOCC1 WZSMSVBKFDAORG-UHFFFAOYSA-N 0.000 description 1
- UEUXPZLKJYJELL-UHFFFAOYSA-N 1-butan-2-yl-2-methyl-3-(2-morpholin-4-ylphenyl)guanidine Chemical compound CCC(C)NC(NC)=NC1=CC=CC=C1N1CCOCC1 UEUXPZLKJYJELL-UHFFFAOYSA-N 0.000 description 1
- XSMQZBJOJPZQCX-UHFFFAOYSA-N 1-butyl-1,3,3-trimethylurea Chemical compound CCCCN(C)C(=O)N(C)C XSMQZBJOJPZQCX-UHFFFAOYSA-N 0.000 description 1
- DMZQVBMPUFJGFR-UHFFFAOYSA-N 1-butyl-1-methyl-2-(2-morpholin-4-ylphenyl)guanidine Chemical compound CCCCN(C)C(N)=NC1=CC=CC=C1N1CCOCC1 DMZQVBMPUFJGFR-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
- RNLYKKWFTSHADR-UHFFFAOYSA-N 1-butyl-2-methyl-3-(5-methylsulfanyl-2-morpholin-4-ylphenyl)guanidine Chemical compound CCCCNC(NC)=NC1=CC(SC)=CC=C1N1CCOCC1 RNLYKKWFTSHADR-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
- LFTAGZLDVBSLSD-UHFFFAOYSA-N 1-butyl-3-(5-fluoro-2-morpholin-4-ylphenyl)-2-methylguanidine Chemical compound CCCCNC(NC)=NC1=CC(F)=CC=C1N1CCOCC1 LFTAGZLDVBSLSD-UHFFFAOYSA-N 0.000 description 1
- TVYZTYVVHJYLAY-UHFFFAOYSA-N 1-butyl-3-methyl-n-(2-morpholin-4-ylphenyl)imidazolidin-2-imine Chemical compound CCCCN1CCN(C)C1=NC1=CC=CC=C1N1CCOCC1 TVYZTYVVHJYLAY-UHFFFAOYSA-N 0.000 description 1
- RPPHJNJPSQKJRX-UHFFFAOYSA-N 1-butyl-n-(2-morpholin-4-ylphenyl)-4,5-dihydroimidazol-2-amine Chemical compound CCCCN1CCNC1=NC1=CC=CC=C1N1CCOCC1 RPPHJNJPSQKJRX-UHFFFAOYSA-N 0.000 description 1
- FDWSOUQUHMMBJU-UHFFFAOYSA-N 1-cyclohexyl-n-(2-morpholin-4-ylphenyl)-4,5-dihydroimidazol-2-amine Chemical compound C=1C=CC=C(N2CCOCC2)C=1N=C1NCCN1C1CCCCC1 FDWSOUQUHMMBJU-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
- RSXWUQJXTHYTPD-UHFFFAOYSA-N 1-cyclopentyl-2-methyl-3-(2-morpholin-4-ylphenyl)guanidine Chemical compound C=1C=CC=C(N2CCOCC2)C=1N=C(NC)NC1CCCC1 RSXWUQJXTHYTPD-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
- FGFWHCOPGCHCKF-UHFFFAOYSA-N 1-ethyl-1-methyl-2-(2-morpholin-4-ylphenyl)guanidine Chemical compound CCN(C)C(N)=NC1=CC=CC=C1N1CCOCC1 FGFWHCOPGCHCKF-UHFFFAOYSA-N 0.000 description 1
- CUWPAUHFMFDKNB-UHFFFAOYSA-N 1-ethyl-3,3-dimethyl-n-(2-morpholin-4-ylphenyl)pyrrolidin-2-imine Chemical compound CCN1CCC(C)(C)C1=NC1=CC=CC=C1N1CCOCC1 CUWPAUHFMFDKNB-UHFFFAOYSA-N 0.000 description 1
- 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 1
- SSGRPLGNJVZTAE-UHFFFAOYSA-N 1-ethyl-3-methyl-n-(2-morpholin-4-ylphenyl)imidazolidin-2-imine Chemical compound CCN1CCN(C)C1=NC1=CC=CC=C1N1CCOCC1 SSGRPLGNJVZTAE-UHFFFAOYSA-N 0.000 description 1
- UZOJONCEBOQBSR-UHFFFAOYSA-N 1-ethyl-n-(2-morpholin-4-ylphenyl)-4,5-dihydroimidazol-2-amine Chemical compound CCN1CCNC1=NC1=CC=CC=C1N1CCOCC1 UZOJONCEBOQBSR-UHFFFAOYSA-N 0.000 description 1
- URMBNSKAFXNOFU-UHFFFAOYSA-N 1-ethyl-n-(2-morpholin-4-ylphenyl)piperidin-2-imine Chemical compound CCN1CCCCC1=NC1=CC=CC=C1N1CCOCC1 URMBNSKAFXNOFU-UHFFFAOYSA-N 0.000 description 1
- BHCMHZPLLGANTK-UHFFFAOYSA-N 1-ethyl-n-(2-morpholin-4-ylphenyl)pyrrolidin-2-imine Chemical compound CCN1CCCC1=NC1=CC=CC=C1N1CCOCC1 BHCMHZPLLGANTK-UHFFFAOYSA-N 0.000 description 1
- OBKHQQTXDGZGOM-UHFFFAOYSA-N 1-ethyl-n-(2-pyrrolidin-1-ylphenyl)piperidin-2-imine Chemical compound CCN1CCCCC1=NC1=CC=CC=C1N1CCCC1 OBKHQQTXDGZGOM-UHFFFAOYSA-N 0.000 description 1
- RRLCNWRKOSQAIK-UHFFFAOYSA-N 1-methyl-3-(2-methyl-6-morpholin-4-ylphenyl)thiourea Chemical compound CNC(=S)NC1=C(C)C=CC=C1N1CCOCC1 RRLCNWRKOSQAIK-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
- NWEHVXSRPOXOKH-UHFFFAOYSA-N 1-methyl-n-(2-methyl-6-morpholin-4-ylphenyl)-4,5-dihydroimidazol-2-amine Chemical compound CN1CCNC1=NC1=C(C)C=CC=C1N1CCOCC1 NWEHVXSRPOXOKH-UHFFFAOYSA-N 0.000 description 1
- ZMEKGPLRQCYJOP-UHFFFAOYSA-N 1-methyl-n-(2-methyl-6-morpholin-4-ylphenyl)piperidin-2-imine Chemical compound CN1CCCCC1=NC1=C(C)C=CC=C1N1CCOCC1 ZMEKGPLRQCYJOP-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
- XADJKLIFFLCMST-UHFFFAOYSA-N 1-methyl-n-(2-methyl-6-pyrrolidin-1-ylphenyl)piperidin-2-imine Chemical compound CN1CCCCC1=NC1=C(C)C=CC=C1N1CCCC1 XADJKLIFFLCMST-UHFFFAOYSA-N 0.000 description 1
- FYPUQKVUHGCKRS-UHFFFAOYSA-N 1-methyl-n-(2-morpholin-4-ylphenyl)-3-propan-2-ylpyrrolidin-2-imine Chemical compound CC(C)C1CCN(C)C1=NC1=CC=CC=C1N1CCOCC1 FYPUQKVUHGCKRS-UHFFFAOYSA-N 0.000 description 1
- NTHRGARCNRHDKS-UHFFFAOYSA-N 1-methyl-n-(2-morpholin-4-ylphenyl)azepan-2-imine Chemical compound CN1CCCCCC1=NC1=CC=CC=C1N1CCOCC1 NTHRGARCNRHDKS-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
- ROKMPTLBWWIORC-UHFFFAOYSA-N 1-methyl-n-(2-morpholin-4-ylphenyl)pyrrolidin-2-imine Chemical compound CN1CCCC1=NC1=CC=CC=C1N1CCOCC1 ROKMPTLBWWIORC-UHFFFAOYSA-N 0.000 description 1
- PPLYCNNTUKCKML-UHFFFAOYSA-N 1-methyl-n-(2-piperidin-1-ylphenyl)-4,5-dihydroimidazol-2-amine Chemical compound CN1CCNC1=NC1=CC=CC=C1N1CCCCC1 PPLYCNNTUKCKML-UHFFFAOYSA-N 0.000 description 1
- KEROIBQQZFRYAV-UHFFFAOYSA-N 1-methyl-n-(2-piperidin-1-ylphenyl)piperidin-2-imine Chemical compound CN1CCCCC1=NC1=CC=CC=C1N1CCCCC1 KEROIBQQZFRYAV-UHFFFAOYSA-N 0.000 description 1
- FOIJJOOWHDTOEV-UHFFFAOYSA-N 1-methyl-n-(2-piperidin-1-ylphenyl)pyrrolidin-2-imine Chemical compound CN1CCCC1=NC1=CC=CC=C1N1CCCCC1 FOIJJOOWHDTOEV-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
- SQEBXHRIOBJOTB-UHFFFAOYSA-N 1-methyl-n-(2-pyrrolidin-1-ylphenyl)azepan-2-imine Chemical compound CN1CCCCCC1=NC1=CC=CC=C1N1CCCC1 SQEBXHRIOBJOTB-UHFFFAOYSA-N 0.000 description 1
- FOOOEWAGOWJAPJ-UHFFFAOYSA-N 1-methyl-n-(2-pyrrolidin-1-ylphenyl)piperidin-2-imine Chemical compound CN1CCCCC1=NC1=CC=CC=C1N1CCCC1 FOOOEWAGOWJAPJ-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
- PXZTVCGSBSXRPN-UHFFFAOYSA-N 1-methyl-n-(5-methyl-2-morpholin-4-ylphenyl)-4,5-dihydroimidazol-2-amine Chemical compound CN1CCNC1=NC1=CC(C)=CC=C1N1CCOCC1 PXZTVCGSBSXRPN-UHFFFAOYSA-N 0.000 description 1
- ZFDLXOQPUADSDX-UHFFFAOYSA-N 1-methyl-n-(5-methyl-2-morpholin-4-ylphenyl)piperidin-2-imine Chemical compound CN1CCCCC1=NC1=CC(C)=CC=C1N1CCOCC1 ZFDLXOQPUADSDX-UHFFFAOYSA-N 0.000 description 1
- YFDFVPCGHCPYCB-UHFFFAOYSA-N 1-methyl-n-[2-(morpholin-4-ylmethyl)phenyl]pyrrolidin-2-imine Chemical compound CN1CCCC1=NC1=CC=CC=C1CN1CCOCC1 YFDFVPCGHCPYCB-UHFFFAOYSA-N 0.000 description 1
- FQARWNLGFGLXLH-UHFFFAOYSA-N 1-methyl-n-[2-(morpholin-4-ylmethyl)phenyl]pyrrolidin-2-imine;dihydroiodide Chemical compound I.I.CN1CCCC1=NC1=CC=CC=C1CN1CCOCC1 FQARWNLGFGLXLH-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
- KVDQSIAWZJZZQV-UHFFFAOYSA-N 1-tert-butyl-2-methyl-3-(4-methyl-2-morpholin-4-ylphenyl)guanidine Chemical compound CC(C)(C)NC(NC)=NC1=CC=C(C)C=C1N1CCOCC1 KVDQSIAWZJZZQV-UHFFFAOYSA-N 0.000 description 1
- XJGCEDDGGJFSKH-UHFFFAOYSA-N 1-tert-butyl-2-methyl-3-(4-methylsulfanyl-2-morpholin-4-ylphenyl)guanidine Chemical compound CC(C)(C)NC(NC)=NC1=CC=C(SC)C=C1N1CCOCC1 XJGCEDDGGJFSKH-UHFFFAOYSA-N 0.000 description 1
- ZFFAFLAJTAZNCA-UHFFFAOYSA-N 1-tert-butyl-2-methyl-3-[4-(methylsulfanylmethyl)-2-morpholin-4-ylphenyl]guanidine Chemical compound CC(C)(C)NC(NC)=NC1=CC=C(CSC)C=C1N1CCOCC1 ZFFAFLAJTAZNCA-UHFFFAOYSA-N 0.000 description 1
- FFDFAJXOJISEAE-UHFFFAOYSA-N 1-tert-butyl-3-(4-fluoro-2-morpholin-4-ylphenyl)-2-methylguanidine;1-tert-butyl-2-methyl-3-(2-morpholin-4-ylphenyl)guanidine Chemical compound CC(C)(C)NC(=NC)NC1=CC=CC=C1N1CCOCC1.CC(C)(C)NC(=NC)NC1=CC=C(F)C=C1N1CCOCC1 FFDFAJXOJISEAE-UHFFFAOYSA-N 0.000 description 1
- AMMWRKZFZVSSRG-UHFFFAOYSA-N 2,3-dihydroxybutanedioic acid;morpholine Chemical compound C1COCC[NH2+]1.OC(=O)C(O)C(O)C([O-])=O AMMWRKZFZVSSRG-UHFFFAOYSA-N 0.000 description 1
- WFDMHFWYPBYQMA-UHFFFAOYSA-N 2,6-dimethyl-n'-(2-morpholin-4-ylphenyl)morpholine-4-carboximidamide Chemical compound C1C(C)OC(C)CN1C(=N)NC1=CC=CC=C1N1CCOCC1 WFDMHFWYPBYQMA-UHFFFAOYSA-N 0.000 description 1
- DGNVJSAZKRFGMJ-UHFFFAOYSA-N 2-(2-methylpyrrolidin-1-yl)aniline Chemical compound CC1CCCN1C1=CC=CC=C1N DGNVJSAZKRFGMJ-UHFFFAOYSA-N 0.000 description 1
- DSHPEUMNBHBDRW-UHFFFAOYSA-N 2-(3-chloro-2-morpholin-4-ylphenyl)-1,1-dimethylguanidine Chemical compound CN(C)C(N)=NC1=CC=CC(Cl)=C1N1CCOCC1 DSHPEUMNBHBDRW-UHFFFAOYSA-N 0.000 description 1
- AKNMIDRCCYRVMN-UHFFFAOYSA-N 2-(4-chloro-2-morpholin-4-ylphenyl)-1,1-dimethylguanidine Chemical compound CN(C)C(N)=NC1=CC=C(Cl)C=C1N1CCOCC1 AKNMIDRCCYRVMN-UHFFFAOYSA-N 0.000 description 1
- BDBQEPCNYHQKHK-UHFFFAOYSA-N 2-(5-methoxy-2-morpholin-4-ylphenyl)-1,1-dimethylguanidine Chemical compound CN(C)C(N)=NC1=CC(OC)=CC=C1N1CCOCC1 BDBQEPCNYHQKHK-UHFFFAOYSA-N 0.000 description 1
- TZNXOZVBUNLKPB-UHFFFAOYSA-N 2-N-(2-methoxyethyl)-2-N-methyl-1-N-(2,3,4,5-tetrahydropyridin-6-yl)benzene-1,2-diamine Chemical compound COCCN(C)C1=CC=CC=C1NC1=NCCCC1 TZNXOZVBUNLKPB-UHFFFAOYSA-N 0.000 description 1
- SMTSEALACYXRCH-UHFFFAOYSA-N 2-[(1,3-dimethylimidazolidin-2-ylidene)amino]-n,n-diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1N=C1N(C)CCN1C SMTSEALACYXRCH-UHFFFAOYSA-N 0.000 description 1
- GDRFPNKEGVXWST-UHFFFAOYSA-N 2-[1-(2-morpholin-4-ylanilino)ethylideneamino]ethyl acetate Chemical compound CC(=O)OCCNC(C)=NC1=CC=CC=C1N1CCOCC1 GDRFPNKEGVXWST-UHFFFAOYSA-N 0.000 description 1
- NOIYYCBPMLECGZ-UHFFFAOYSA-N 2-[2-[2-methoxyethyl(methyl)amino]phenyl]-1,1-dimethylguanidine Chemical compound COCCN(C)C1=CC=CC=C1N=C(N)N(C)C NOIYYCBPMLECGZ-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
- QKDYIUDGNZAYPO-UHFFFAOYSA-N 2-[4,5-dimethyl-2-(2-morpholin-4-ylanilino)-4,5-dihydroimidazol-1-yl]ethanol Chemical compound OCCN1C(C)C(C)N=C1NC1=CC=CC=C1N1CCOCC1 QKDYIUDGNZAYPO-UHFFFAOYSA-N 0.000 description 1
- BMKNHYSUYQXQBX-UHFFFAOYSA-N 2-butyl-1-(2-morpholin-4-ylphenyl)guanidine Chemical compound CCCCNC(N)=NC1=CC=CC=C1N1CCOCC1 BMKNHYSUYQXQBX-UHFFFAOYSA-N 0.000 description 1
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 1
- KXOGDEVRJMWOSP-UHFFFAOYSA-N 2-ethyl-1-(2-morpholin-4-ylphenyl)guanidine Chemical compound CCNC(N)=NC1=CC=CC=C1N1CCOCC1 KXOGDEVRJMWOSP-UHFFFAOYSA-N 0.000 description 1
- IBZKBSXREAQDTO-UHFFFAOYSA-N 2-methoxy-n-(2-methoxyethyl)ethanamine Chemical compound COCCNCCOC IBZKBSXREAQDTO-UHFFFAOYSA-N 0.000 description 1
- QLLZYTCKRHEBAI-UHFFFAOYSA-N 2-methyl-1-(2-methylpropyl)-3-(2-morpholin-4-ylphenyl)guanidine Chemical compound CC(C)CNC(NC)=NC1=CC=CC=C1N1CCOCC1 QLLZYTCKRHEBAI-UHFFFAOYSA-N 0.000 description 1
- BSZMEBLZPOKRNW-UHFFFAOYSA-N 2-methyl-1-(2-morpholin-4-ylphenyl)-3-propylguanidine Chemical compound CCCNC(NC)=NC1=CC=CC=C1N1CCOCC1 BSZMEBLZPOKRNW-UHFFFAOYSA-N 0.000 description 1
- HSFSECZWADULIV-UHFFFAOYSA-N 2-methyl-1-(2-morpholin-4-ylphenyl)guanidine Chemical compound CNC(N)=NC1=CC=CC=C1N1CCOCC1 HSFSECZWADULIV-UHFFFAOYSA-N 0.000 description 1
- ULZVZRVDMKHKAL-UHFFFAOYSA-N 2-methyl-2-n-propan-2-ylpropane-1,2-diamine Chemical compound CC(C)NC(C)(C)CN ULZVZRVDMKHKAL-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
- 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
- VWMWWYQIPLGBPM-UHFFFAOYSA-N 2-n,2-n-bis(2-methoxyethyl)benzene-1,2-diamine Chemical compound COCCN(CCOC)C1=CC=CC=C1N VWMWWYQIPLGBPM-UHFFFAOYSA-N 0.000 description 1
- GKKXQISZWPOTCT-UHFFFAOYSA-N 2-n,2-n-dimethyl-1-n-(2,3,4,5-tetrahydropyridin-6-yl)benzene-1,2-diamine Chemical compound CN(C)C1=CC=CC=C1N=C1NCCCC1 GKKXQISZWPOTCT-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
- JRVCXHWYBZCOPY-UHFFFAOYSA-N 3,3-diethyl-1-methyl-n-(2-morpholin-4-ylphenyl)pyrrolidin-2-imine Chemical compound CCC1(CC)CCN(C)C1=NC1=CC=CC=C1N1CCOCC1 JRVCXHWYBZCOPY-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
- 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
- OZSNMDQOXOXTNX-UHFFFAOYSA-N 3-[2-(2-morpholin-4-ylphenyl)iminopiperidin-1-yl]propanenitrile Chemical compound N#CCCN1CCCCC1=NC1=CC=CC=C1N1CCOCC1 OZSNMDQOXOXTNX-UHFFFAOYSA-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
- PKZODHURUCXOAG-UHFFFAOYSA-N 4-(2-isothiocyanatophenyl)morpholine Chemical compound S=C=NC1=CC=CC=C1N1CCOCC1 PKZODHURUCXOAG-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
- 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
- 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 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
- DZXPRKXHRYJXIX-UHFFFAOYSA-N 4-methyl-n'-(2-morpholin-4-ylphenyl)piperazine-1-carboximidamide Chemical compound C1CN(C)CCN1C(=N)NC1=CC=CC=C1N1CCOCC1 DZXPRKXHRYJXIX-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
- WXUOQYOAFQPCOR-UHFFFAOYSA-N 4-methyl-n-(2-morpholin-4-ylphenyl)-3,4-dihydro-2h-pyrrol-5-amine Chemical compound CC1CCNC1=NC1=CC=CC=C1N1CCOCC1 WXUOQYOAFQPCOR-UHFFFAOYSA-N 0.000 description 1
- UVCRCPDVBFUATI-UHFFFAOYSA-N 5,5-dimethyl-n-(2-morpholin-4-ylphenyl)-3,4-dihydropyrrol-2-amine Chemical compound N1C(C)(C)CCC1=NC1=CC=CC=C1N1CCOCC1 UVCRCPDVBFUATI-UHFFFAOYSA-N 0.000 description 1
- OHVZGXJTAXZUBJ-UHFFFAOYSA-N 5,5-dimethyl-n-(2-morpholin-4-ylphenyl)-3-propan-2-yl-4h-imidazol-2-amine Chemical compound CC(C)N1CC(C)(C)NC1=NC1=CC=CC=C1N1CCOCC1 OHVZGXJTAXZUBJ-UHFFFAOYSA-N 0.000 description 1
- IIDYOEJOFYEQMP-UHFFFAOYSA-N 5-(2-methylpropyl)-2-morpholin-4-ylaniline;hydrochloride Chemical compound Cl.NC1=CC(CC(C)C)=CC=C1N1CCOCC1 IIDYOEJOFYEQMP-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
- OQLZINXFSUDMHM-UHFFFAOYSA-N Acetamidine Chemical compound CC(N)=N OQLZINXFSUDMHM-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- BEAAHOZFSQXRJJ-UHFFFAOYSA-N C(C=CC(=O)O)(=O)O.C(C)(C)N1C(NC(C1)(C)C)=NC1=C(C=CC=C1)N1CCOCC1 Chemical compound C(C=CC(=O)O)(=O)O.C(C)(C)N1C(NC(C1)(C)C)=NC1=C(C=CC=C1)N1CCOCC1 BEAAHOZFSQXRJJ-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
- DINDIWUZFLRNQW-UHFFFAOYSA-N C(CCC)CN(C(NC)=NC1=C(C=CC=C1)N1CCOCC1)C Chemical compound C(CCC)CN(C(NC)=NC1=C(C=CC=C1)N1CCOCC1)C DINDIWUZFLRNQW-UHFFFAOYSA-N 0.000 description 1
- HPMVDWKYEKLYML-WLHGVMLRSA-N C(\C=C\C(=O)O)(=O)O.CN(C(=N)NC1=C(C=CC=C1)CN1CCOCC1)C Chemical compound C(\C=C\C(=O)O)(=O)O.CN(C(=N)NC1=C(C=CC=C1)CN1CCOCC1)C HPMVDWKYEKLYML-WLHGVMLRSA-N 0.000 description 1
- WKUKVVBDDOMAFN-VQYXCCSOSA-N C(\C=C\C(=O)O)(=O)O.CN1C(C(CCC1)CCOC)=NC1=C(C=CC=C1)N1CCOCC1.C(\C=C\C(=O)O)(=O)O.C(\C=C\C(=O)O)(=O)O.CN1C(C(CCC1)CCOC)=NC1=C(C=CC=C1)N1CCOCC1 Chemical compound C(\C=C\C(=O)O)(=O)O.CN1C(C(CCC1)CCOC)=NC1=C(C=CC=C1)N1CCOCC1.C(\C=C\C(=O)O)(=O)O.C(\C=C\C(=O)O)(=O)O.CN1C(C(CCC1)CCOC)=NC1=C(C=CC=C1)N1CCOCC1 WKUKVVBDDOMAFN-VQYXCCSOSA-N 0.000 description 1
- HWRHTFJPYDLSDA-VQYXCCSOSA-N C(\C=C\C(=O)O)(=O)O.N1CCOCC1.C(\C=C\C(=O)O)(=O)O.C(\C=C\C(=O)O)(=O)O.N1CCOCC1 Chemical compound C(\C=C\C(=O)O)(=O)O.N1CCOCC1.C(\C=C\C(=O)O)(=O)O.C(\C=C\C(=O)O)(=O)O.N1CCOCC1 HWRHTFJPYDLSDA-VQYXCCSOSA-N 0.000 description 1
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 239000004366 Glucose oxidase Substances 0.000 description 1
- 108010015776 Glucose oxidase Proteins 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
- 241001465754 Metazoa Species 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-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
- 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
- 239000005662 Paraffin oil Substances 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 239000005700 Putrescine Substances 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
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 239000004288 Sodium dehydroacetate Substances 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
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 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 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
- 150000008043 acidic salts Chemical class 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
- 239000002671 adjuvant Substances 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 150000001409 amidines Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 229940125708 antidiabetic agent Drugs 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 239000004176 azorubin Substances 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
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 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
- 150000008050 dialkyl sulfates Chemical class 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- SPWVRYZQLGQKGK-UHFFFAOYSA-N dichloromethane;hexane Chemical compound ClCCl.CCCCCC SPWVRYZQLGQKGK-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 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
- 238000010828 elution Methods 0.000 description 1
- 239000002662 enteric coated tablet Substances 0.000 description 1
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 235000019420 glucose oxidase Nutrition 0.000 description 1
- 229940116332 glucose oxidase Drugs 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 201000001421 hyperglycemia Diseases 0.000 description 1
- 230000002218 hypoglycaemic effect Effects 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- ACKFDYCQCBEDNU-UHFFFAOYSA-J lead(2+);tetraacetate Chemical compound [Pb+2].CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O ACKFDYCQCBEDNU-UHFFFAOYSA-J 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 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
- KQRCDTWONYPWLI-UHFFFAOYSA-N methyl 4-morpholin-4-yl-3-(2,3,4,5-tetrahydropyridin-6-ylamino)benzoate Chemical compound C1CCCNC1=NC1=CC(C(=O)OC)=CC=C1N1CCOCC1 KQRCDTWONYPWLI-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
- 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
- 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
- FKUVAHAHEKIBCO-UHFFFAOYSA-N methyl n'-[2-(1,2,4-oxathiazinan-4-yl)phenyl]carbamimidothioate Chemical compound CSC(=N)NC1=CC=CC=C1N1CSOCC1 FKUVAHAHEKIBCO-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
- RBPCZFFBMVBTBD-UHFFFAOYSA-N methyl n'-methyl-n-(2-pyrrolidin-1-ylphenyl)carbamimidothioate;hydroiodide Chemical compound I.CSC(=NC)NC1=CC=CC=C1N1CCCC1 RBPCZFFBMVBTBD-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
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- VSEAAEQOQBMPQF-UHFFFAOYSA-N morpholin-3-one Chemical compound O=C1COCCN1 VSEAAEQOQBMPQF-UHFFFAOYSA-N 0.000 description 1
- YYLDXZJRWZUZAH-UHFFFAOYSA-N morpholin-4-yl(phenyl)methanamine Chemical compound C=1C=CC=CC=1C(N)N1CCOCC1 YYLDXZJRWZUZAH-UHFFFAOYSA-N 0.000 description 1
- BOQOXLAQTDFJKU-UHFFFAOYSA-N morpholine-4-carbonitrile Chemical compound N#CN1CCOCC1 BOQOXLAQTDFJKU-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
- ZKGWYQRILKGVKS-UHFFFAOYSA-N n'-(2-morpholin-4-ylphenyl)pyrrolidine-1-carboximidamide Chemical compound C1CCCN1C(=N)NC1=CC=CC=C1N1CCOCC1 ZKGWYQRILKGVKS-UHFFFAOYSA-N 0.000 description 1
- SXUKWCFCQIRVIL-UHFFFAOYSA-N n'-(2-piperidin-1-ylphenyl)morpholine-4-carboximidamide Chemical compound C1COCCN1C(=N)NC1=CC=CC=C1N1CCCCC1 SXUKWCFCQIRVIL-UHFFFAOYSA-N 0.000 description 1
- JYIZFVNGKKMMCD-UHFFFAOYSA-N n'-(2-piperidin-1-ylphenyl)piperidine-1-carboximidamide Chemical compound C1CCCCN1C(=N)NC1=CC=CC=C1N1CCCCC1 JYIZFVNGKKMMCD-UHFFFAOYSA-N 0.000 description 1
- POFNECNFUBKBGM-UHFFFAOYSA-N n'-(4-fluoro-2-morpholin-4-ylphenyl)ethanimidamide Chemical compound CC(=N)NC1=CC=C(F)C=C1N1CCOCC1 POFNECNFUBKBGM-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
- DLUZRIVYSNQWOA-UHFFFAOYSA-N n'-(4-methylsulfanyl-2-morpholin-4-ylphenyl)ethanimidamide Chemical compound CSC1=CC=C(NC(C)=N)C(N2CCOCC2)=C1 DLUZRIVYSNQWOA-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
- ABCDSFYPODLHHZ-UHFFFAOYSA-N n'-[2-(1,2,4-oxathiazinan-4-yl)phenyl]ethanimidamide Chemical compound CC(=N)NC1=CC=CC=C1N1CSOCC1 ABCDSFYPODLHHZ-UHFFFAOYSA-N 0.000 description 1
- HQCQZAJGOWDOOB-UHFFFAOYSA-N n'-[2-(morpholin-4-ylmethyl)phenyl]ethanimidamide Chemical compound CC(=N)NC1=CC=CC=C1CN1CCOCC1 HQCQZAJGOWDOOB-UHFFFAOYSA-N 0.000 description 1
- KALSSKJXBSHPBY-UHFFFAOYSA-N n'-[4-(methylsulfanylmethyl)-2-morpholin-4-ylphenyl]ethanimidamide Chemical compound CSCC1=CC=C(NC(C)=N)C(N2CCOCC2)=C1 KALSSKJXBSHPBY-UHFFFAOYSA-N 0.000 description 1
- RFOYTEPIYSHZOL-UHFFFAOYSA-N n'-butyl-n-(2-morpholin-4-ylphenyl)ethanimidamide Chemical compound CCCCNC(C)=NC1=CC=CC=C1N1CCOCC1 RFOYTEPIYSHZOL-UHFFFAOYSA-N 0.000 description 1
- KJEHJFZPGYRZSQ-UHFFFAOYSA-N n'-ethyl-n-(2-morpholin-4-ylphenyl)butanimidamide Chemical compound CCCC(NCC)=NC1=CC=CC=C1N1CCOCC1 KJEHJFZPGYRZSQ-UHFFFAOYSA-N 0.000 description 1
- XKWMGQMSEIGCLI-UHFFFAOYSA-N n'-ethyl-n-(2-morpholin-4-ylphenyl)propanimidamide Chemical compound CCNC(CC)=NC1=CC=CC=C1N1CCOCC1 XKWMGQMSEIGCLI-UHFFFAOYSA-N 0.000 description 1
- QJJHFYANTFCVCU-UHFFFAOYSA-N n'-methyl-n-(2-morpholin-4-ylphenyl)butanimidamide Chemical compound CCCC(NC)=NC1=CC=CC=C1N1CCOCC1 QJJHFYANTFCVCU-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
- GNJFKDGGDZJFNE-UHFFFAOYSA-N n'-methyl-n-(2-morpholin-4-ylphenyl)hexanimidamide Chemical compound CCCCCC(NC)=NC1=CC=CC=C1N1CCOCC1 GNJFKDGGDZJFNE-UHFFFAOYSA-N 0.000 description 1
- YBLQLBPYIJUTQF-UHFFFAOYSA-N n'-methyl-n-(2-morpholin-4-ylphenyl)pentanimidamide Chemical compound CCCCC(NC)=NC1=CC=CC=C1N1CCOCC1 YBLQLBPYIJUTQF-UHFFFAOYSA-N 0.000 description 1
- VEEWPXSQDLINGZ-UHFFFAOYSA-N n'-methyl-n-(2-morpholin-4-ylphenyl)propanimidamide Chemical compound CCC(NC)=NC1=CC=CC=C1N1CCOCC1 VEEWPXSQDLINGZ-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
- YRHCBULSLFMFHF-UHFFFAOYSA-N n,n-dimethyl-n'-(2-morpholin-4-ylphenyl)butanimidamide Chemical compound CCCC(N(C)C)=NC1=CC=CC=C1N1CCOCC1 YRHCBULSLFMFHF-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
- 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
- OJNBSUANJZAIPO-UHFFFAOYSA-N n-(2-chloro-6-morpholin-4-ylphenyl)-2,3,4,5-tetrahydropyridin-6-amine Chemical compound C1CCCNC1=NC=1C(Cl)=CC=CC=1N1CCOCC1 OJNBSUANJZAIPO-UHFFFAOYSA-N 0.000 description 1
- WEEMVACVDVUOCW-UHFFFAOYSA-N n-(2-methyl-6-morpholin-4-ylphenyl)-2,3,4,5-tetrahydropyridin-6-amine Chemical compound C1CCCNC1=NC=1C(C)=CC=CC=1N1CCOCC1 WEEMVACVDVUOCW-UHFFFAOYSA-N 0.000 description 1
- LHXHLHFNNQONBP-UHFFFAOYSA-N n-(2-methyl-6-pyrrolidin-1-ylphenyl)-2,3,4,5-tetrahydropyridin-6-amine Chemical compound C1CCCNC1=NC=1C(C)=CC=CC=1N1CCCC1 LHXHLHFNNQONBP-UHFFFAOYSA-N 0.000 description 1
- DRYWHEFETHTUHL-UHFFFAOYSA-N n-(2-morpholin-4-ylphenyl)-1-pentylimidazolidin-2-amine Chemical compound CCCCCN1CCNC1NC1=CC=CC=C1N1CCOCC1 DRYWHEFETHTUHL-UHFFFAOYSA-N 0.000 description 1
- DOVLTZNYRFWUEE-UHFFFAOYSA-N n-(2-morpholin-4-ylphenyl)-1-propan-2-yl-4,5-dihydroimidazol-2-amine Chemical compound CC(C)N1CCNC1=NC1=CC=CC=C1N1CCOCC1 DOVLTZNYRFWUEE-UHFFFAOYSA-N 0.000 description 1
- VZAAQLWZUGMRDQ-UHFFFAOYSA-N n-(2-morpholin-4-ylphenyl)-1-propan-2-ylpiperidin-2-imine Chemical compound CC(C)N1CCCCC1=NC1=CC=CC=C1N1CCOCC1 VZAAQLWZUGMRDQ-UHFFFAOYSA-N 0.000 description 1
- VHTDNBJJRJSKMK-UHFFFAOYSA-N n-(2-morpholin-4-ylphenyl)-1-propyl-4,5-dihydroimidazol-2-amine Chemical compound CCCN1CCNC1=NC1=CC=CC=C1N1CCOCC1 VHTDNBJJRJSKMK-UHFFFAOYSA-N 0.000 description 1
- LVBUTRFTWZSHLH-UHFFFAOYSA-N n-(2-morpholin-4-ylphenyl)-2,3,4,5,6,7-hexahydroazocin-8-amine Chemical compound C1COCCN1C1=CC=CC=C1N=C1NCCCCCC1 LVBUTRFTWZSHLH-UHFFFAOYSA-N 0.000 description 1
- ZGXUOMBFQIDJEH-UHFFFAOYSA-N n-(2-morpholin-4-ylphenyl)-3,4,5,6-tetrahydro-2h-azepin-7-amine Chemical compound C1COCCN1C1=CC=CC=C1N=C1NCCCCC1 ZGXUOMBFQIDJEH-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
- CVPDWCGLTZFFOL-UHFFFAOYSA-N n-(2-morpholin-4-ylphenyl)-3,6-dihydro-2h-1,4-oxazin-5-amine;hydrochloride Chemical compound Cl.N1CCOCC1=NC1=CC=CC=C1N1CCOCC1 CVPDWCGLTZFFOL-UHFFFAOYSA-N 0.000 description 1
- AKQLUDQDDATCNB-UHFFFAOYSA-N n-(2-morpholin-4-ylphenyl)-4,5,6,7-tetrahydro-1h-1,3-diazepin-2-amine Chemical compound C1COCCN1C1=CC=CC=C1N=C1NCCCCN1 AKQLUDQDDATCNB-UHFFFAOYSA-N 0.000 description 1
- SQTRTTPLGQWQCH-UHFFFAOYSA-N n-(2-morpholin-4-ylphenyl)-n'-propylethanimidamide Chemical compound CCCN=C(C)NC1=CC=CC=C1N1CCOCC1 SQTRTTPLGQWQCH-UHFFFAOYSA-N 0.000 description 1
- OZTPOKLNXVGNKD-UHFFFAOYSA-N n-(2-piperidin-1-ylphenyl)-2,3,4,5-tetrahydropyridin-6-amine Chemical compound C1CCCCN1C1=CC=CC=C1N=C1NCCCC1 OZTPOKLNXVGNKD-UHFFFAOYSA-N 0.000 description 1
- QBCIXOALVNCLMU-UHFFFAOYSA-N n-(2-piperidin-1-ylphenyl)-4,5-dihydro-1h-imidazol-2-amine Chemical compound N1CCNC1=NC1=CC=CC=C1N1CCCCC1 QBCIXOALVNCLMU-UHFFFAOYSA-N 0.000 description 1
- NYGIIVOCRUXDJY-UHFFFAOYSA-N n-(2-pyrrolidin-1-ylphenyl)-2,3,4,5-tetrahydropyridin-6-amine Chemical compound C1CCCN1C1=CC=CC=C1N=C1NCCCC1 NYGIIVOCRUXDJY-UHFFFAOYSA-N 0.000 description 1
- AJXDWORUPGNCOS-UHFFFAOYSA-N n-(3-chloro-2-morpholin-4-ylphenyl)-2,3,4,5-tetrahydropyridin-6-amine Chemical compound C1COCCN1C=1C(Cl)=CC=CC=1N=C1CCCCN1 AJXDWORUPGNCOS-UHFFFAOYSA-N 0.000 description 1
- JDGKOWBWHFMWNU-UHFFFAOYSA-N n-(3-methyl-2-morpholin-4-ylphenyl)-2,3,4,5-tetrahydropyridin-6-amine Chemical compound C1COCCN1C=1C(C)=CC=CC=1N=C1CCCCN1 JDGKOWBWHFMWNU-UHFFFAOYSA-N 0.000 description 1
- ASQSYGFOYJSIOH-UHFFFAOYSA-N n-(3-methyl-2-pyrrolidin-1-ylphenyl)-2,3,4,5-tetrahydropyridin-6-amine Chemical compound C1CCCN1C=1C(C)=CC=CC=1N=C1CCCCN1 ASQSYGFOYJSIOH-UHFFFAOYSA-N 0.000 description 1
- YALZTUFPTJYCDN-UHFFFAOYSA-N n-(4,5-dimethoxy-2-morpholin-4-ylphenyl)-1,3-dimethylimidazolidin-2-imine Chemical compound C1COCCN1C=1C=C(OC)C(OC)=CC=1N=C1N(C)CCN1C YALZTUFPTJYCDN-UHFFFAOYSA-N 0.000 description 1
- FHSXJYGLINMHHB-UHFFFAOYSA-N n-(4-chloro-2-morpholin-4-ylphenyl)-2,3,4,5-tetrahydropyridin-6-amine Chemical compound C1COCCN1C1=CC(Cl)=CC=C1N=C1CCCCN1 FHSXJYGLINMHHB-UHFFFAOYSA-N 0.000 description 1
- YUIRJDTYJSZAAO-UHFFFAOYSA-N n-(4-methyl-2-morpholin-4-ylphenyl)-2,3,4,5-tetrahydropyridin-6-amine Chemical compound C1COCCN1C1=CC(C)=CC=C1N=C1CCCCN1 YUIRJDTYJSZAAO-UHFFFAOYSA-N 0.000 description 1
- SWRXESBFNZUCHZ-UHFFFAOYSA-N n-(5-chloro-2-morpholin-4-ylphenyl)-1,3-dimethylimidazolidin-2-imine Chemical compound CN1CCN(C)C1=NC1=CC(Cl)=CC=C1N1CCOCC1 SWRXESBFNZUCHZ-UHFFFAOYSA-N 0.000 description 1
- CPCFZXIEHYIZHU-UHFFFAOYSA-N n-(5-chloro-2-morpholin-4-ylphenyl)-1-methylpiperidin-2-imine Chemical compound CN1CCCCC1=NC1=CC(Cl)=CC=C1N1CCOCC1 CPCFZXIEHYIZHU-UHFFFAOYSA-N 0.000 description 1
- XIIBDRQMROPSGV-UHFFFAOYSA-N n-(5-chloro-2-morpholin-4-ylphenyl)-2,3,4,5-tetrahydropyridin-6-amine Chemical compound C1CCCNC1=NC1=CC(Cl)=CC=C1N1CCOCC1 XIIBDRQMROPSGV-UHFFFAOYSA-N 0.000 description 1
- ABVBMUXSDARHOG-UHFFFAOYSA-N n-(5-chloro-2-pyrrolidin-1-ylphenyl)-1-methylpiperidin-2-imine Chemical compound CN1CCCCC1=NC1=CC(Cl)=CC=C1N1CCCC1 ABVBMUXSDARHOG-UHFFFAOYSA-N 0.000 description 1
- XJODFGYWLXTNQT-UHFFFAOYSA-N n-(5-chloro-2-pyrrolidin-1-ylphenyl)-2,3,4,5-tetrahydropyridin-6-amine Chemical compound C1CCCNC1=NC1=CC(Cl)=CC=C1N1CCCC1 XJODFGYWLXTNQT-UHFFFAOYSA-N 0.000 description 1
- VXLNVHVAAXUZDI-UHFFFAOYSA-N n-(5-ethyl-2-morpholin-4-ylphenyl)-2,3,4,5-tetrahydropyridin-6-amine Chemical compound C1CCCNC1=NC1=CC(CC)=CC=C1N1CCOCC1 VXLNVHVAAXUZDI-UHFFFAOYSA-N 0.000 description 1
- TZTMUGVZEDSSJI-UHFFFAOYSA-N n-(5-fluoro-2-morpholin-4-ylphenyl)-1,3-dimethylimidazolidin-2-imine Chemical compound CN1CCN(C)C1=NC1=CC(F)=CC=C1N1CCOCC1 TZTMUGVZEDSSJI-UHFFFAOYSA-N 0.000 description 1
- IVBZPJFGCXHOEB-UHFFFAOYSA-N n-(5-fluoro-2-morpholin-4-ylphenyl)-1-methylpiperidin-2-imine Chemical compound CN1CCCCC1=NC1=CC(F)=CC=C1N1CCOCC1 IVBZPJFGCXHOEB-UHFFFAOYSA-N 0.000 description 1
- BYWVBEWPBFXWGM-UHFFFAOYSA-N n-(5-fluoro-2-morpholin-4-ylphenyl)-2,3,4,5-tetrahydropyridin-6-amine Chemical compound C1CCCNC1=NC1=CC(F)=CC=C1N1CCOCC1 BYWVBEWPBFXWGM-UHFFFAOYSA-N 0.000 description 1
- GIXAGODLDAEVQU-UHFFFAOYSA-N n-(5-methoxy-2-morpholin-4-ylphenyl)-1,3-dimethylimidazolidin-2-imine Chemical compound CN1CCN(C)C1=NC1=CC(OC)=CC=C1N1CCOCC1 GIXAGODLDAEVQU-UHFFFAOYSA-N 0.000 description 1
- CKZJYFMGBJDEPG-UHFFFAOYSA-N n-(5-methoxy-2-morpholin-4-ylphenyl)-2,3,4,5-tetrahydropyridin-6-amine Chemical compound C1CCCNC1=NC1=CC(OC)=CC=C1N1CCOCC1 CKZJYFMGBJDEPG-UHFFFAOYSA-N 0.000 description 1
- BXHFANRNGOPUKL-UHFFFAOYSA-N n-(5-methyl-2-morpholin-4-ylphenyl)-2,3,4,5-tetrahydropyridin-6-amine Chemical compound C1CCCNC1=NC1=CC(C)=CC=C1N1CCOCC1 BXHFANRNGOPUKL-UHFFFAOYSA-N 0.000 description 1
- YNUWVCBAWIDKGI-UHFFFAOYSA-N n-(5-methyl-2-pyrrolidin-1-ylphenyl)-2,3,4,5-tetrahydropyridin-6-amine Chemical compound C1CCCNC1=NC1=CC(C)=CC=C1N1CCCC1 YNUWVCBAWIDKGI-UHFFFAOYSA-N 0.000 description 1
- WYAFYQBIBCAMTD-UHFFFAOYSA-N n-(5-methylsulfonyl-2-morpholin-4-ylphenyl)-2,3,4,5-tetrahydropyridin-6-amine Chemical compound C1CCCNC1=NC1=CC(S(=O)(=O)C)=CC=C1N1CCOCC1 WYAFYQBIBCAMTD-UHFFFAOYSA-N 0.000 description 1
- PHZKNSSXUWCHPU-UHFFFAOYSA-N n-[2-(1,3-dihydroisoindol-2-yl)phenyl]-2,3,4,5-tetrahydropyridin-6-amine Chemical compound C1C2=CC=CC=C2CN1C1=CC=CC=C1N=C1CCCCN1 PHZKNSSXUWCHPU-UHFFFAOYSA-N 0.000 description 1
- DBGFSXNYTKUPOV-UHFFFAOYSA-N n-[2-(2,6-dimethylmorpholin-4-yl)phenyl]-1,3-dimethylimidazolidin-2-imine Chemical compound C1C(C)OC(C)CN1C1=CC=CC=C1N=C1N(C)CCN1C DBGFSXNYTKUPOV-UHFFFAOYSA-N 0.000 description 1
- PGPUZHHQYCUQOW-UHFFFAOYSA-N n-[2-(2,6-dimethylmorpholin-4-yl)phenyl]-2,3,4,5-tetrahydropyridin-6-amine Chemical compound C1C(C)OC(C)CN1C1=CC=CC=C1N=C1NCCCC1 PGPUZHHQYCUQOW-UHFFFAOYSA-N 0.000 description 1
- SLVKOGNBDXFZEB-UHFFFAOYSA-N n-[2-(2-methylpyrrolidin-1-yl)phenyl]-2,3,4,5-tetrahydropyridin-6-amine Chemical compound CC1CCCN1C1=CC=CC=C1N=C1NCCCC1 SLVKOGNBDXFZEB-UHFFFAOYSA-N 0.000 description 1
- UVZGMFMVSXSRQB-UHFFFAOYSA-N n-[2-(3,6-dihydro-2h-pyridin-1-yl)phenyl]-2,3,4,5-tetrahydropyridin-6-amine Chemical compound N1CCCCC1=NC1=CC=CC=C1N1CC=CCC1 UVZGMFMVSXSRQB-UHFFFAOYSA-N 0.000 description 1
- NFCIRZCTVCMBCQ-UHFFFAOYSA-N n-[2-(4-methylpiperidin-1-yl)phenyl]-2,3,4,5-tetrahydropyridin-6-amine Chemical compound C1CC(C)CCN1C1=CC=CC=C1N=C1NCCCC1 NFCIRZCTVCMBCQ-UHFFFAOYSA-N 0.000 description 1
- FAKVHTGDHWPUGT-UHFFFAOYSA-N n-[2-(azepan-1-yl)phenyl]-2,3,4,5-tetrahydropyridin-6-amine Chemical compound N1CCCCC1=NC1=CC=CC=C1N1CCCCCC1 FAKVHTGDHWPUGT-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
- LYZQOWXMYRIRRO-UHFFFAOYSA-N n-[[2-(2-methylpyrrolidin-1-yl)phenyl]carbamothioyl]benzamide Chemical compound CC1CCCN1C1=CC=CC=C1NC(=S)NC(=O)C1=CC=CC=C1 LYZQOWXMYRIRRO-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
- QSGLLJPRFQMSJN-UHFFFAOYSA-N n-ethyl-2-morpholin-4-ylaniline Chemical compound CCNC1=CC=CC=C1N1CCOCC1 QSGLLJPRFQMSJN-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([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
- 239000012074 organic phase Substances 0.000 description 1
- KDLHZDBZIXYQEI-VENIDDJXSA-N palladium-100 Chemical compound [100Pd] KDLHZDBZIXYQEI-VENIDDJXSA-N 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
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000002831 pharmacologic agent Substances 0.000 description 1
- 125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 description 1
- JAMNHZBIQDNHMM-UHFFFAOYSA-N pivalonitrile Chemical compound CC(C)(C)C#N JAMNHZBIQDNHMM-UHFFFAOYSA-N 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
- 239000000843 powder Substances 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
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical class O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000004180 red 2G Substances 0.000 description 1
- 238000006748 scratching Methods 0.000 description 1
- 230000002393 scratching effect Effects 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
- 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
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000004328 sodium tetraborate Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000002511 suppository base Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 125000000464 thioxo group Chemical group S=* 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000010626 work up procedure 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)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Emergency Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Endocrinology (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)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Indole Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Saccharide Compounds (AREA)
- Steroid Compounds (AREA)
- Investigating Or Analysing Materials By Optical Means (AREA)
- Soy Sauces And Products Related Thereto (AREA)
- Thermotherapy And Cooling Therapy Devices (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 |
---|---|
CS743389A3 CS743389A3 (en) | 1992-03-18 |
CS277609B6 true CS277609B6 (en) | 1993-03-17 |
Family
ID=10651840
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CS897433A CS277609B6 (en) | 1989-02-16 | 1989-12-27 | Amino(methyl)phenyl derivatives, process for their preparation and use |
Country Status (26)
Country | Link |
---|---|
US (2) | US5223498A (uk) |
EP (1) | EP0385038B1 (uk) |
JP (1) | JP2545475B2 (uk) |
AT (1) | ATE90074T1 (uk) |
BG (1) | BG60557B1 (uk) |
CS (1) | CS277609B6 (uk) |
DD (1) | DD294023A5 (uk) |
DE (1) | DE68906880T2 (uk) |
DK (1) | DK640889A (uk) |
ES (1) | ES2055115T3 (uk) |
FI (1) | FI95565C (uk) |
GB (1) | GB8903592D0 (uk) |
GE (1) | GEP19981040B (uk) |
HU (1) | HU211571A9 (uk) |
IL (1) | IL92963A (uk) |
LT (3) | LT3960B (uk) |
LV (1) | LV10619B (uk) |
MY (1) | MY105052A (uk) |
NO (1) | NO177993C (uk) |
PL (2) | PL162960B1 (uk) |
PT (1) | PT92770B (uk) |
RO (2) | RO107945B1 (uk) |
RU (3) | RU1826969C (uk) |
UA (2) | UA19156A (uk) |
YU (1) | YU48164B (uk) |
ZA (1) | ZA899941B (uk) |
Families Citing this family (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0273712B1 (en) * | 1986-12-27 | 1990-12-12 | Konica Corporation | Light-sensitive silver halide photographic material |
IN172842B (uk) * | 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 |
AU2978197A (en) * | 1996-06-04 | 1998-01-05 | Chugai Seiyaku Kabushiki Kaisha | Substituted benzenes having nos inhibitory effects |
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 |
EP1243580A4 (en) * | 1999-12-28 | 2003-04-23 | Nissan Chemical Ind Ltd | HETEROCYCLIC IMINO COMPOUNDS, FUNGICIDES AND INSECTICIDES FOR USE IN AGRICULTURE AND GARDENING |
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 |
PE20070404A1 (es) * | 2005-07-29 | 2007-05-10 | Wyeth Corp | Compuestos derivados de cianopirrol-sulfonamida como moduladores del 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 |
Family Cites Families (86)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DD81857A (uk) * | ||||
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 |
NL299929A (uk) * | 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 |
US4013676A (en) * | 1970-06-13 | 1977-03-22 | Bayer Aktiengesellschaft | Aminophenylamidines, their production and their pharmaceutical use |
US3925470A (en) * | 1970-06-13 | 1975-12-09 | Bayer Ag | Aminophenylamidines, their production and their medicinal use |
US3903302A (en) * | 1970-06-13 | 1975-09-02 | Bayer Ag | Aminophenylamidines as anthelmintic agents |
US3925471A (en) * | 1970-06-13 | 1975-12-09 | 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 |
US3919315A (en) * | 1970-06-13 | 1975-11-11 | Bayer Ag | New aminophenylamidines, their production and their medicinal use |
DE2029299C3 (de) * | 1970-06-13 | 1980-08-21 | Bayer Ag, 5090 Leverkusen | Neue Aminophenylamidine, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel |
US3911010A (en) * | 1970-06-13 | 1975-10-07 | Bayer Ag | Aminophenylamidines, their production and their pharmaceutical use |
US3923888A (en) * | 1970-06-13 | 1975-12-02 | Bayer Ag | Aminophenylamidines, their production and their medicinal use |
US3996247A (en) * | 1970-06-13 | 1976-12-07 | Bayer Aktiengesellschaft | Substituted 4-aminophenylamidines |
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 |
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 |
CA1138451A (en) * | 1979-04-03 | 1982-12-28 | Ikuo Ueda | 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 (uk) * | 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 |
EP0099017B1 (de) * | 1982-07-06 | 1988-03-02 | Dr. Karl Thomae GmbH | Neue Phenylessigsäure-Derivate, ihre Herstellung und diese Verbindungen enthaltende Arzneimittel |
US4533739A (en) * | 1982-10-12 | 1985-08-06 | G. D. Searle & Co. | 2-[(Aminophenyl and amidophenyl)amino]-1-azacycloalkanes having antidiarrheal activity |
FR2539417A1 (fr) * | 1983-01-13 | 1984-07-20 | Rhone Poulenc Sante | Nouveaux pyrrolo-1, 2 heterocycles, leur preparation et les medicaments qui les contiennent |
NZ206808A (en) * | 1983-01-13 | 1986-04-11 | Rhone Poulenc Sante | Pyrrole derivatives |
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 |
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 |
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 |
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 |
FR2549049B1 (fr) * | 1983-07-13 | 1986-06-20 | Chauvin Blache Lab | Nouvelles amidines, leur procede de preparation et leur application therapeutique |
US4701447A (en) * | 1983-09-23 | 1987-10-20 | Schering Corporation | N-((2-nitro)phenyl)-N' (organic acid) guanidine anthelmintics |
US4723029A (en) * | 1983-09-23 | 1988-02-02 | Schering Corporation | Organic acid-substituted 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 |
US4656270A (en) * | 1985-03-15 | 1987-04-07 | Mcneilab, Inc. | Process for producing guanidines such as linogliride |
US4693850A (en) * | 1985-03-15 | 1987-09-15 | Mcneilab, Inc. | Methane sulfonic acid derivatives |
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 |
DE3751742T3 (de) * | 1986-01-13 | 2002-11-21 | American Cyanamid Co., Wayne | 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 ES ES89313636T patent/ES2055115T3/es not_active Expired - Lifetime
- 1989-12-28 EP EP89313636A patent/EP0385038B1/en not_active Expired - Lifetime
- 1989-12-28 ZA ZA899941A patent/ZA899941B/xx unknown
- 1989-12-28 YU YU248589A patent/YU48164B/sh unknown
- 1989-12-28 AT AT89313636T patent/ATE90074T1/de not_active IP Right Cessation
- 1989-12-28 BG BG90783A patent/BG60557B1/bg unknown
- 1989-12-28 US US07/458,237 patent/US5223498A/en not_active Expired - Lifetime
- 1989-12-28 DE DE8989313636T patent/DE68906880T2/de not_active Expired - Fee Related
- 1989-12-29 DD DD89336816A patent/DD294023A5/de unknown
- 1989-12-29 PL PL28307489A patent/PL162960B1/pl unknown
- 1989-12-29 UA UA4742813A patent/UA19156A/uk unknown
- 1989-12-29 PT PT92770A patent/PT92770B/pt not_active IP Right Cessation
- 1989-12-29 RU SU894742813A patent/RU1826969C/ru active
- 1989-12-29 JP JP1345135A patent/JP2545475B2/ja not_active Expired - Fee Related
- 1989-12-29 UA UA5011043A patent/UA27713C2/uk unknown
- 1989-12-29 PL PL89295913A patent/PL161961B1/pl unknown
- 1989-12-30 RO RO147103A patent/RO107945B1/ro unknown
- 1989-12-30 RO RO143555A patent/RO105807B1/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 LTIP1646A patent/LT3958B/lt not_active IP Right Cessation
- 1993-12-21 LT LTIP1648A patent/LT3961B/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 |
---|---|---|
FI114023B (fi) | Menetelmä uusien terapeuttisesti käyttökelpoisten kinatsolinonien valmistamiseksi | |
US5998399A (en) | Guanidine derivatives useful in therapy as inhibitors of nitric oxide synthetase | |
CZ282919B6 (cs) | Nové N-alkylenpiperidinové sloučeniny a jejich enantiomery, způsob jejich přípravy a farmaceutické prostředky, které je obsahují | |
US5302720A (en) | Biphenyl-substituted guanidine derivatives useful as hypoglycaemic agents | |
CS277609B6 (en) | Amino(methyl)phenyl derivatives, process for their preparation and use | |
NO338104B1 (no) | Tetrahydroisoquinolin-sulfonamid-derivater, farmasøytiske preparater inneholdende slike og anvendelse derav som terapeutisk middel | |
KR0168398B1 (ko) | 당뇨병 및 과혈당증 치료제로 유용한 화합물 및 이의 제조방법 | |
FI58638B (fi) | Foerfarande foer framstaellning av antibakteriellt verksamma 2,4-diamino-5-bensylpyrimidiner och salter daerav | |
CS255884B2 (en) | Process for preparing derivatives of substituted 3-phenyliminothiazolidine | |
PT86251B (pt) | Processo de preparacao de derivados piridinilo de 2-aminoacetamida | |
SI8912485A (sl) | Nova hipoglikemična sredstva in postopek za njihovo pripravo | |
JPS62252762A (ja) | ピログルタミド誘導体 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
IF00 | In force as of 2000-06-30 in czech republic | ||
MM4A | Patent lapsed due to non-payment of fee |
Effective date: 20021227 |