HRP20090121T5 - Kondenzirani derivati kinolina i njihova upotreba - Google Patents

Info

Publication number

HRP20090121T5

HRP20090121T5 HR20090121T HRP20090121T HRP20090121T5 HR P20090121 T5 HRP20090121 T5 HR P20090121T5 HR 20090121 T HR20090121 T HR 20090121T HR P20090121 T HRP20090121 T HR P20090121T HR P20090121 T5 HRP20090121 T5 HR P20090121T5

Authority

HR

Croatia

Prior art keywords

optionally

substituent

group

carbonyl

6alkyl

Prior art date

2004-04-28

Links

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• Global Dossier
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• 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 title description 3
• 125000001424 substituent group Chemical group 0.000 claims abstract description 519
• 150000001875 compounds Chemical class 0.000 claims abstract description 394
• 150000002367 halogens Chemical class 0.000 claims abstract description 141
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 138
• 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 113
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 99
• 150000003839 salts Chemical class 0.000 claims abstract description 86
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 72
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 67
• 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 50
• 239000003795 chemical substances by application Substances 0.000 claims abstract description 37
• 238000011282 treatment Methods 0.000 claims abstract description 21
• 238000011321 prophylaxis Methods 0.000 claims abstract description 19
• 125000002252 acyl group Chemical group 0.000 claims abstract description 15
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims abstract description 15
• 125000004122 cyclic group Chemical group 0.000 claims abstract description 14
• 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 12
• 125000005090 alkenylcarbonyl group Chemical group 0.000 claims abstract description 11
• 238000004519 manufacturing process Methods 0.000 claims abstract description 9
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 6
• -1 hydroxy, amino Chemical group 0.000 claims description 326
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 147
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 110
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 93
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 71
• 150000002430 hydrocarbons Chemical group 0.000 claims description 64
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 58
• 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 50
• 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 38
• 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 35
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 28
• 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 23
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 22
• 125000006624 (C1-C6) alkoxycarbonylamino group Chemical group 0.000 claims description 21
• 108010040722 Neurokinin-2 Receptors Proteins 0.000 claims description 20
• 102100037342 Substance-K receptor Human genes 0.000 claims description 20
• 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 19
• 125000006239 protecting group Chemical group 0.000 claims description 18
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 17
• 201000010099 disease Diseases 0.000 claims description 15
• 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 14
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 14
• 125000003118 aryl group Chemical group 0.000 claims description 13
• 239000008177 pharmaceutical agent Substances 0.000 claims description 13
• RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 12
• 125000000217 alkyl group Chemical group 0.000 claims description 12
• 239000002464 receptor antagonist Substances 0.000 claims description 12
• 229940044551 receptor antagonist Drugs 0.000 claims description 12
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 10
• XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 9
• GPRLTFBKWDERLU-UHFFFAOYSA-N bicyclo[2.2.2]octane Chemical compound C1CC2CCC1CC2 GPRLTFBKWDERLU-UHFFFAOYSA-N 0.000 claims description 9
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 9
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 9
• 208000014540 Functional gastrointestinal disease Diseases 0.000 claims description 7
• 230000001419 dependent effect Effects 0.000 claims description 7
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 6
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
• DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims description 6
• 125000005544 phthalimido group Chemical group 0.000 claims description 6
• 125000003386 piperidinyl group Chemical group 0.000 claims description 6
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 5
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 5
• 125000005129 aryl carbonyl group Chemical group 0.000 claims description 5
• GZGZZIWUTHPTJN-BHHQIGSJSA-N 1-[(1r,2s)-2-[(3ar,4r,9br)-4-(methoxymethyl)-2,3,3a,4,5,9b-hexahydropyrrolo[3,2-c]quinoline-1-carbonyl]cyclohexyl]-3-(4-pyrazol-1-ylphenyl)urea Chemical group N([C@@H]1CCCC[C@@H]1C(=O)N1CC[C@H]2[C@@H]1C1=CC=CC=C1N[C@H]2COC)C(=O)NC(C=C1)=CC=C1N1C=CC=N1 GZGZZIWUTHPTJN-BHHQIGSJSA-N 0.000 claims description 4
• 101800000399 Neurokinin A Proteins 0.000 claims description 4
• 238000006482 condensation reaction Methods 0.000 claims description 4
• 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 3
• 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims description 3
• 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 3
• FHDFHPQXVJGIGY-IWEOIBJYSA-N n-[(1r,2s)-2-[(3ar,4r,9br)-4-(1h-imidazol-2-yl)-2,3,3a,4,5,9b-hexahydropyrrolo[3,2-c]quinoline-1-carbonyl]cyclohexyl]-4-cyanobenzamide Chemical group C1([C@@H]2NC3=CC=CC=C3[C@H]3[C@@H]2CCN3C(=O)[C@H]2CCCC[C@H]2NC(=O)C=2C=CC(=CC=2)C#N)=NC=CN1 FHDFHPQXVJGIGY-IWEOIBJYSA-N 0.000 claims description 3
• HZZPIUMZUICXOU-OZHIHCJWSA-N n-[(1r,2s)-2-[(3ar,4r,9br)-4-(1h-imidazol-2-yl)-2,3,3a,4,5,9b-hexahydropyrrolo[3,2-c]quinoline-1-carbonyl]cyclohexyl]benzamide Chemical group C1([C@@H]2NC3=CC=CC=C3[C@H]3[C@@H]2CCN3C(=O)[C@H]2CCCC[C@H]2NC(=O)C=2C=CC=CC=2)=NC=CN1 HZZPIUMZUICXOU-OZHIHCJWSA-N 0.000 claims description 3
• JMAWVPBEIPDAKE-MZJRLMRESA-N 1-[(1r,2s)-2-[(3ar,4r,9br)-4-phenyl-2,3,3a,4,5,9b-hexahydropyrrolo[3,2-c]quinoline-1-carbonyl]cyclohexyl]-3-phenylurea Chemical group C1([C@@H]2NC3=CC=CC=C3[C@H]3[C@@H]2CCN3C(=O)[C@H]2CCCC[C@H]2NC(=O)NC=2C=CC=CC=2)=CC=CC=C1 JMAWVPBEIPDAKE-MZJRLMRESA-N 0.000 claims description 2
• 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 2
• UKIXMERQKUXWJA-RMNHWBOMSA-N n-[(1r,2s)-2-[(3ar,4r,9br)-4-(methoxymethyl)-2,3,3a,4,5,9b-hexahydropyrrolo[3,2-c]quinoline-1-carbonyl]cyclohexyl]-4-(difluoromethoxy)benzamide Chemical group N([C@@H]1CCCC[C@@H]1C(=O)N1CC[C@H]2[C@@H]1C1=CC=CC=C1N[C@H]2COC)C(=O)C1=CC=C(OC(F)F)C=C1 UKIXMERQKUXWJA-RMNHWBOMSA-N 0.000 claims description 2
• BHYDIFHAROFHIZ-NEFLSZPGSA-N n-[(1r,2s)-2-[(3ar,4s,9br)-4-propyl-2,3,3a,4,5,9b-hexahydropyrrolo[3,2-c]quinoline-1-carbonyl]cyclohexyl]-2-methyl-3h-benzimidazole-5-carboxamide Chemical group C1=C2NC(C)=NC2=CC(C(=O)N[C@@H]2CCCC[C@@H]2C(=O)N2CC[C@H]3[C@@H]2C2=CC=CC=C2N[C@H]3CCC)=C1 BHYDIFHAROFHIZ-NEFLSZPGSA-N 0.000 claims description 2
• 125000003545 alkoxy group Chemical group 0.000 claims 11
• HEAUFJZALFKPBA-YRVBCFNBSA-N Neurokinin A Chemical compound C([C@@H](C(=O)N[C@H](C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(N)=O)C(C)C)NC(=O)[C@H](CO)NC(=O)[C@H](CC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CCCCN)NC(=O)[C@@H](N)CC=1NC=NC=1)C(C)O)C1=CC=CC=C1 HEAUFJZALFKPBA-YRVBCFNBSA-N 0.000 claims 3
• 102400000097 Neurokinin A Human genes 0.000 claims 3
• 125000003710 aryl alkyl group Chemical group 0.000 claims 2
• 125000002102 aryl alkyloxo group Chemical group 0.000 claims 2
• 125000005100 aryl amino carbonyl group Chemical group 0.000 claims 2
• 125000004104 aryloxy group Chemical group 0.000 claims 2
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 2
• 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims 1
• 208000025865 Ulcer Diseases 0.000 claims 1
• 125000005115 alkyl carbamoyl group Chemical group 0.000 claims 1
• 125000005281 alkyl ureido group Chemical group 0.000 claims 1
• 125000005530 alkylenedioxy group Chemical group 0.000 claims 1
• 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 claims 1
• 125000001769 aryl amino group Chemical group 0.000 claims 1
• ILIGRHYVKLHSCF-WXGGYGAESA-N n-[(1r,2s)-2-[(3ar,4r,9br)-4-(methoxymethyl)-2,3,3a,4,5,9b-hexahydropyrrolo[3,2-c]quinoline-1-carbonyl]cyclohexyl]-4-(dimethylamino)benzamide Chemical group N([C@@H]1CCCC[C@@H]1C(=O)N1CC[C@H]2[C@@H]1C1=CC=CC=C1N[C@H]2COC)C(=O)C1=CC=C(N(C)C)C=C1 ILIGRHYVKLHSCF-WXGGYGAESA-N 0.000 claims 1
• ZBHOKIIPGTWXTA-YZNGJPBSSA-N n-[(1r,2s)-2-[(3ar,4r,9br)-4-(methoxymethyl)-2,3,3a,4,5,9b-hexahydropyrrolo[3,2-c]quinoline-1-carbonyl]cyclohexyl]-4-(methylamino)benzamide Chemical group C1=CC(NC)=CC=C1C(=O)N[C@H]1[C@@H](C(=O)N2[C@@H]3[C@@H]([C@@H](NC4=CC=CC=C43)COC)CC2)CCCC1 ZBHOKIIPGTWXTA-YZNGJPBSSA-N 0.000 claims 1
• KCTUVUALNVBCGT-RMNHWBOMSA-N n-[(1r,2s)-2-[(3ar,4r,9br)-4-(methoxymethyl)-2,3,3a,4,5,9b-hexahydropyrrolo[3,2-c]quinoline-1-carbonyl]cyclohexyl]-4-(trifluoromethoxy)benzamide Chemical group N([C@@H]1CCCC[C@@H]1C(=O)N1CC[C@H]2[C@@H]1C1=CC=CC=C1N[C@H]2COC)C(=O)C1=CC=C(OC(F)(F)F)C=C1 KCTUVUALNVBCGT-RMNHWBOMSA-N 0.000 claims 1
• KOFHYLXEWKAQSR-RMNHWBOMSA-N n-[(1r,2s)-2-[(3ar,4r,9br)-4-(methoxymethyl)-2,3,3a,4,5,9b-hexahydropyrrolo[3,2-c]quinoline-1-carbonyl]cyclohexyl]-4-(trifluoromethyl)benzamide Chemical group N([C@@H]1CCCC[C@@H]1C(=O)N1CC[C@H]2[C@@H]1C1=CC=CC=C1N[C@H]2COC)C(=O)C1=CC=C(C(F)(F)F)C=C1 KOFHYLXEWKAQSR-RMNHWBOMSA-N 0.000 claims 1
• 208000011580 syndromic disease Diseases 0.000 claims 1
• 231100000397 ulcer Toxicity 0.000 claims 1
• 150000003573 thiols Chemical class 0.000 abstract description 5
• 208000020401 Depressive disease Diseases 0.000 abstract description 3
• 125000004432 carbon atom Chemical group C* 0.000 abstract description 3
• 208000024714 major depressive disease Diseases 0.000 abstract description 3
• 201000003995 melancholia Diseases 0.000 abstract description 3
• 125000001183 hydrocarbyl group Chemical group 0.000 abstract 5
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 285
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 234
• 239000000203 mixture Substances 0.000 description 209
• 230000000052 comparative effect Effects 0.000 description 130
• 230000002829 reductive effect Effects 0.000 description 123
• 239000000243 solution Substances 0.000 description 123
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 120
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 110
• 239000002904 solvent Substances 0.000 description 108
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 93
• 239000011541 reaction mixture Substances 0.000 description 89
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 84
• 239000000284 extract Substances 0.000 description 67
• 238000005160 1H NMR spectroscopy Methods 0.000 description 66
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 60
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 60
• 235000019341 magnesium sulphate Nutrition 0.000 description 60
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 58
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 58
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 57
• OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 57
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 56
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 54
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 51
• 239000000741 silica gel Substances 0.000 description 49
• 229910002027 silica gel Inorganic materials 0.000 description 49
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 45
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 44
• 238000004440 column chromatography Methods 0.000 description 44
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 42
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 42
• 239000003814 drug Substances 0.000 description 38
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 32
• 229940079593 drug Drugs 0.000 description 32
• 238000001816 cooling Methods 0.000 description 30
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 30
• 238000002360 preparation method Methods 0.000 description 29
• 235000017557 sodium bicarbonate Nutrition 0.000 description 29
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 29
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 29
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 28
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
• 238000000034 method Methods 0.000 description 27
• 239000007864 aqueous solution Substances 0.000 description 25
• 229920006395 saturated elastomer Polymers 0.000 description 25
• 125000000041 C6-C10 aryl group Chemical group 0.000 description 22
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 22
• 238000010898 silica gel chromatography Methods 0.000 description 22
• 238000006243 chemical reaction Methods 0.000 description 21
• 239000007787 solid Substances 0.000 description 20
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 19
• 239000013078 crystal Substances 0.000 description 19
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 18
• 239000003921 oil Substances 0.000 description 18
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 17
• 229910052938 sodium sulfate Inorganic materials 0.000 description 17
• 235000011152 sodium sulphate Nutrition 0.000 description 17
• 239000007832 Na2SO4 Substances 0.000 description 16
• 239000012230 colorless oil Substances 0.000 description 16
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 16
• 238000001914 filtration Methods 0.000 description 15
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 15
• 238000010992 reflux Methods 0.000 description 15
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 14
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 14
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 14
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 14
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 14
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 14
• 229910052794 bromium Inorganic materials 0.000 description 14
• 239000004202 carbamide Substances 0.000 description 14
• 239000000460 chlorine Substances 0.000 description 14
• 229910052801 chlorine Inorganic materials 0.000 description 14
• 239000011737 fluorine Substances 0.000 description 14
• 229910052731 fluorine Inorganic materials 0.000 description 14
• 239000011630 iodine Substances 0.000 description 14
• 229910052740 iodine Inorganic materials 0.000 description 14
• 239000000843 powder Substances 0.000 description 14
• 239000000725 suspension Substances 0.000 description 14
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical class OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 13
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 13
• UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 13
• 239000000706 filtrate Substances 0.000 description 13
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 13
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 13
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 13
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 13
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 13
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 12
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 11
• 230000037396 body weight Effects 0.000 description 11
• 239000003112 inhibitor Substances 0.000 description 11
• 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 11
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 10
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 10
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
• 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 10
• 238000005886 esterification reaction Methods 0.000 description 10
• 239000012044 organic layer Substances 0.000 description 10
• 239000012312 sodium hydride Substances 0.000 description 10
• 229910000104 sodium hydride Inorganic materials 0.000 description 10
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 9
• 239000002253 acid Substances 0.000 description 9
• 239000003054 catalyst Substances 0.000 description 9
• 239000010410 layer Substances 0.000 description 9
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