JP2004525876A - 抗細菌活性を有する新規複素環式化合物、それらの調製方法、およびそれらを含有する薬学的組成物 - Google Patents

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Publication number

JP2004525876A

JP2004525876A JP2002552914A JP2002552914A JP2004525876A JP 2004525876 A JP2004525876 A JP 2004525876A JP 2002552914 A JP2002552914 A JP 2002552914A JP 2002552914 A JP2002552914 A JP 2002552914A JP 2004525876 A JP2004525876 A JP 2004525876A

Authority

JP

Japan

Prior art keywords

alkyl

oxazolan

oxo

salt

phenyl

Prior art date

2000-12-26

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Withdrawn

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• 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 20
• 238000000034 method Methods 0.000 title claims description 55
• 238000002360 preparation method Methods 0.000 title description 22
• 230000000844 anti-bacterial effect Effects 0.000 title description 4
• 150000002391 heterocyclic compounds Chemical class 0.000 title 1
• 150000003839 salts Chemical class 0.000 claims abstract description 354
• -1 oxazolidinone compound Chemical class 0.000 claims abstract description 277
• 239000012453 solvate Substances 0.000 claims abstract description 28
• 150000001875 compounds Chemical class 0.000 claims description 350
• 125000000217 alkyl group Chemical group 0.000 claims description 288
• 229910052739 hydrogen Inorganic materials 0.000 claims description 133
• 239000001257 hydrogen Substances 0.000 claims description 131
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 118
• 125000003545 alkoxy group Chemical group 0.000 claims description 105
• 125000003118 aryl group Chemical group 0.000 claims description 98
• 125000005843 halogen group Chemical group 0.000 claims description 85
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 74
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 69
• 125000003282 alkyl amino group Chemical group 0.000 claims description 68
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 67
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 64
• 239000000203 mixture Substances 0.000 claims description 64
• 125000004104 aryloxy group Chemical group 0.000 claims description 63
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 62
• 150000002431 hydrogen Chemical class 0.000 claims description 61
• YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 53
• 229910052717 sulfur Inorganic materials 0.000 claims description 50
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 49
• 229910052760 oxygen Inorganic materials 0.000 claims description 49
• 125000005842 heteroatom Chemical group 0.000 claims description 45
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 44
• 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 43
• 125000000623 heterocyclic group Chemical group 0.000 claims description 42
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 41
• 229910052736 halogen Inorganic materials 0.000 claims description 39
• 150000002367 halogens Chemical class 0.000 claims description 39
• 239000000243 solution Substances 0.000 claims description 39
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 38
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 38
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 35
• 239000002585 base Substances 0.000 claims description 32
• 125000004475 heteroaralkyl group Chemical group 0.000 claims description 32
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 30
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 30
• 125000005129 aryl carbonyl group Chemical group 0.000 claims description 30
• GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims description 29
• 101150065749 Churc1 gene Proteins 0.000 claims description 29
• 102100038239 Protein Churchill Human genes 0.000 claims description 29
• 125000004432 carbon atom Chemical group C* 0.000 claims description 29
• 125000001072 heteroaryl group Chemical group 0.000 claims description 29
• 125000001769 aryl amino group Chemical group 0.000 claims description 28
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 28
• 125000006574 non-aromatic ring group Chemical group 0.000 claims description 27
• 125000003342 alkenyl group Chemical group 0.000 claims description 26
• 229910052731 fluorine Inorganic materials 0.000 claims description 26
• UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 25
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 23
• 150000001540 azides Chemical class 0.000 claims description 20
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 18
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 18
• 239000002253 acid Substances 0.000 claims description 17
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 17
• 125000002252 acyl group Chemical group 0.000 claims description 16
• IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical group [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 claims description 16
• HXIRTSKHPFRRKO-UHFFFAOYSA-N o-methyl carbamothioate Chemical compound COC(N)=S HXIRTSKHPFRRKO-UHFFFAOYSA-N 0.000 claims description 13
• LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 13
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 13
• 239000011737 fluorine Substances 0.000 claims description 12
• 125000004685 alkoxythiocarbonyl group Chemical group 0.000 claims description 11
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 11
• 229940024606 amino acid Drugs 0.000 claims description 11
• 235000001014 amino acid Nutrition 0.000 claims description 11
• 208000035143 Bacterial infection Diseases 0.000 claims description 10
• ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical class NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 10
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 10
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 10
• 150000001413 amino acids Chemical class 0.000 claims description 10
• 208000022362 bacterial infectious disease Diseases 0.000 claims description 10
• GTCAXTIRRLKXRU-UHFFFAOYSA-N carbamic acid methyl ester Natural products COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 claims description 10
• ZBKFYXZXZJPWNQ-UHFFFAOYSA-N isothiocyanate group Chemical group [N-]=C=S ZBKFYXZXZJPWNQ-UHFFFAOYSA-N 0.000 claims description 10
• 125000004423 acyloxy group Chemical group 0.000 claims description 9
• 125000005090 alkenylcarbonyl group Chemical group 0.000 claims description 9
• 125000005092 alkenyloxycarbonyl group Chemical group 0.000 claims description 9
• 125000001424 substituent group Chemical group 0.000 claims description 9
• KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 claims description 8
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 8
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 8
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 8
• 239000003085 diluting agent Substances 0.000 claims description 8
• ZWWAJMUJXCLKDI-UHFFFAOYSA-N ethylsulfanyl carbamate Chemical compound C(N)(=O)OSCC ZWWAJMUJXCLKDI-UHFFFAOYSA-N 0.000 claims description 8
• 150000002540 isothiocyanates Chemical class 0.000 claims description 8
• 125000003441 thioacyl group Chemical group 0.000 claims description 8
• 238000007796 conventional method Methods 0.000 claims description 7
• 125000001153 fluoro group Chemical group F* 0.000 claims description 7
• KOUKXHPPRFNWPP-UHFFFAOYSA-N pyrazine-2,5-dicarboxylic acid;hydrate Chemical compound O.OC(=O)C1=CN=C(C(O)=O)C=N1 KOUKXHPPRFNWPP-UHFFFAOYSA-N 0.000 claims description 7
• 239000000725 suspension Substances 0.000 claims description 7
• CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Chemical class CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 6
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
• WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 claims description 6
• HRKQOINLCJTGBK-UHFFFAOYSA-N dihydroxidosulfur Chemical compound OSO HRKQOINLCJTGBK-UHFFFAOYSA-N 0.000 claims description 6
• SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Chemical class CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 6
• 125000006533 methyl amino methyl group Chemical group [H]N(C([H])([H])[H])C([H])([H])* 0.000 claims description 6
• 125000000464 thioxo group Chemical group S=* 0.000 claims description 6
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 5
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 5
• 230000003301 hydrolyzing effect Effects 0.000 claims description 5
• VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 5
• 239000000843 powder Substances 0.000 claims description 5
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
• 125000004076 pyridyl group Chemical group 0.000 claims description 5
• XYVMOLOUBJBNBF-UHFFFAOYSA-N 3h-1,3-oxazol-2-one Chemical compound OC1=NC=CO1 XYVMOLOUBJBNBF-UHFFFAOYSA-N 0.000 claims description 4
• QWOJMRHUQHTCJG-UHFFFAOYSA-N CC([CH2-])=O Chemical group CC([CH2-])=O QWOJMRHUQHTCJG-UHFFFAOYSA-N 0.000 claims description 4
• DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 4
• MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 claims description 4
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 4
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 4
• 125000003302 alkenyloxy group Chemical group 0.000 claims description 4
• 150000001350 alkyl halides Chemical class 0.000 claims description 4
• 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 4
• RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 claims description 4
• 239000002775 capsule Substances 0.000 claims description 4
• 239000003795 chemical substances by application Substances 0.000 claims description 4
• 239000003937 drug carrier Substances 0.000 claims description 4
• KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 claims description 4
• 150000004820 halides Chemical class 0.000 claims description 4
• XWJIZTGLGRHGPN-LBPRGKRZSA-N n-[[(5s)-3-[3-fluoro-4-(2-oxo-1,3-oxazolidin-3-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]butanamide Chemical compound O=C1O[C@@H](CNC(=O)CCC)CN1C(C=C1F)=CC=C1N1C(=O)OCC1 XWJIZTGLGRHGPN-LBPRGKRZSA-N 0.000 claims description 4
• 150000007530 organic bases Chemical class 0.000 claims description 4
• 239000006188 syrup Substances 0.000 claims description 4
• 235000020357 syrup Nutrition 0.000 claims description 4
• 239000003826 tablet Substances 0.000 claims description 4
• YAPQBXQYLJRXSA-UHFFFAOYSA-N theobromine Chemical compound CN1C(=O)NC(=O)C2=C1N=CN2C YAPQBXQYLJRXSA-UHFFFAOYSA-N 0.000 claims description 4
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 3
• 239000004475 Arginine Substances 0.000 claims description 3
• FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 3
• ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 claims description 3
• ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 claims description 3
• KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims description 3
• KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 3
• 239000004472 Lysine Substances 0.000 claims description 3
• ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 claims description 3
• 125000000304 alkynyl group Chemical group 0.000 claims description 3
• ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims description 3
• 235000010323 ascorbic acid Nutrition 0.000 claims description 3
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 3
• 125000004369 butenyl group Chemical group C(=CCC)* 0.000 claims description 3
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
• OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 claims description 3
• 229960001231 choline Drugs 0.000 claims description 3
• ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 3
• 150000002357 guanidines Chemical class 0.000 claims description 3
• 125000004970 halomethyl group Chemical group 0.000 claims description 3
• CFHGBZLNZZVTAY-UHFFFAOYSA-N lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 claims description 3
• 229910052744 lithium Inorganic materials 0.000 claims description 3
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
• 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 3
• ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 claims description 3
• LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 claims description 3
• 229960000281 trometamol Drugs 0.000 claims description 3
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
• MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 claims description 2
• BLBQHONHPVUNNA-SECBINFHSA-N (5r)-3-[2-fluoro-4-(2-oxo-1,3-oxazolidin-3-yl)phenyl]-5-(hydroxymethyl)-1,3-oxazolidin-2-one Chemical compound O=C1O[C@@H](CO)CN1C1=CC=C(N2C(OCC2)=O)C=C1F BLBQHONHPVUNNA-SECBINFHSA-N 0.000 claims description 2
• UVKKXZAOOHKQGK-SECBINFHSA-N (5r)-3-[3-fluoro-4-(2-oxo-1,3-oxazolidin-3-yl)phenyl]-5-(hydroxymethyl)-1,3-oxazolidin-2-one Chemical compound O=C1O[C@@H](CO)CN1C(C=C1F)=CC=C1N1C(=O)OCC1 UVKKXZAOOHKQGK-SECBINFHSA-N 0.000 claims description 2
• BAWYOZIGOLWAPE-OAHLLOKOSA-N (5r)-3-[3-fluoro-4-(2-oxo-3-phenylimidazolidin-1-yl)phenyl]-5-(hydroxymethyl)-1,3-oxazolidin-2-one Chemical compound O=C1O[C@@H](CO)CN1C(C=C1F)=CC=C1N1C(=O)N(C=2C=CC=CC=2)CC1 BAWYOZIGOLWAPE-OAHLLOKOSA-N 0.000 claims description 2
• PHBJXIQJUQZHSI-SECBINFHSA-N (5r)-3-[3-fluoro-4-(2-sulfanylidene-1,3-oxazolidin-3-yl)phenyl]-5-(hydroxymethyl)-1,3-oxazolidin-2-one Chemical compound O=C1O[C@@H](CO)CN1C(C=C1F)=CC=C1N1C(=S)OCC1 PHBJXIQJUQZHSI-SECBINFHSA-N 0.000 claims description 2
• GSTGCXIFAFUZHT-SECBINFHSA-N (5r)-3-[3-fluoro-4-(2-sulfanylidene-1,3-thiazolidin-3-yl)phenyl]-5-(hydroxymethyl)-1,3-oxazolidin-2-one Chemical compound O=C1O[C@@H](CO)CN1C(C=C1F)=CC=C1N1C(=S)SCC1 GSTGCXIFAFUZHT-SECBINFHSA-N 0.000 claims description 2
• KGCOHZKSIRCQDH-SNVBAGLBSA-N (5r)-3-[3-fluoro-4-(3-methyl-2-oxoimidazolidin-1-yl)phenyl]-5-(hydroxymethyl)-1,3-oxazolidin-2-one Chemical compound O=C1N(C)CCN1C1=CC=C(N2C(O[C@@H](CO)C2)=O)C=C1F KGCOHZKSIRCQDH-SNVBAGLBSA-N 0.000 claims description 2
• DZHVONJUCHHDJE-SNVBAGLBSA-N (5r)-3-[3-fluoro-4-(3-methyl-2-sulfanylideneimidazolidin-1-yl)phenyl]-5-(hydroxymethyl)-1,3-oxazolidin-2-one Chemical compound S=C1N(C)CCN1C1=CC=C(N2C(O[C@@H](CO)C2)=O)C=C1F DZHVONJUCHHDJE-SNVBAGLBSA-N 0.000 claims description 2
• KIIOFADAAYVPRJ-SNVBAGLBSA-N (5r)-3-[3-fluoro-4-(3-methyl-4-oxoimidazolidin-1-yl)phenyl]-5-(hydroxymethyl)-1,3-oxazolidin-2-one Chemical compound C1C(=O)N(C)CN1C1=CC=C(N2C(O[C@@H](CO)C2)=O)C=C1F KIIOFADAAYVPRJ-SNVBAGLBSA-N 0.000 claims description 2
• ZVXJDSDSXAJDMX-CYBMUJFWSA-N (5r)-3-[3-fluoro-4-[3-(2-fluorophenyl)-2-oxoimidazolidin-1-yl]phenyl]-5-(hydroxymethyl)-1,3-oxazolidin-2-one Chemical compound O=C1O[C@@H](CO)CN1C(C=C1F)=CC=C1N1C(=O)N(C=2C(=CC=CC=2)F)CC1 ZVXJDSDSXAJDMX-CYBMUJFWSA-N 0.000 claims description 2
• LRLPGFQPBBUZCS-QGZVFWFLSA-N (5r)-3-[3-fluoro-4-[3-[(4-methoxyphenyl)methyl]-4-oxoimidazolidin-1-yl]phenyl]-5-(hydroxymethyl)-1,3-oxazolidin-2-one Chemical compound C1=CC(OC)=CC=C1CN1C(=O)CN(C=2C(=CC(=CC=2)N2C(O[C@@H](CO)C2)=O)F)C1 LRLPGFQPBBUZCS-QGZVFWFLSA-N 0.000 claims description 2
• DWATUUKBXZBUNF-GOSISDBHSA-N (5r)-3-[4-(3-benzyl-2-oxoimidazolidin-1-yl)phenyl]-5-(hydroxymethyl)-1,3-oxazolidin-2-one Chemical compound O=C1O[C@@H](CO)CN1C1=CC=C(N2C(N(CC=3C=CC=CC=3)CC2)=O)C=C1 DWATUUKBXZBUNF-GOSISDBHSA-N 0.000 claims description 2
• NHHFXULAHBKCJV-SNVBAGLBSA-N (5r)-5-(aminomethyl)-3-[3-fluoro-4-(3-methyl-4-oxoimidazolidin-1-yl)phenyl]-1,3-oxazolidin-2-one Chemical compound C1C(=O)N(C)CN1C1=CC=C(N2C(O[C@H](CN)C2)=O)C=C1F NHHFXULAHBKCJV-SNVBAGLBSA-N 0.000 claims description 2
• CKONPXQNHZXJQM-LLVKDONJSA-N (5r)-5-(aminomethyl)-3-[4-(2-oxo-1,3-oxazolidin-3-yl)phenyl]-1,3-oxazolidin-2-one Chemical compound O=C1O[C@H](CN)CN1C1=CC=C(N2C(OCC2)=O)C=C1 CKONPXQNHZXJQM-LLVKDONJSA-N 0.000 claims description 2
• XFFMZCPPUQOLRW-MRXNPFEDSA-N (5r)-5-(aminomethyl)-3-[4-(3-benzyl-4-oxoimidazolidin-1-yl)-3-fluorophenyl]-1,3-oxazolidin-2-one Chemical compound O=C1O[C@H](CN)CN1C(C=C1F)=CC=C1N1CC(=O)N(CC=2C=CC=CC=2)C1 XFFMZCPPUQOLRW-MRXNPFEDSA-N 0.000 claims description 2
• BAUYXWOSBYZLIU-VIFPVBQESA-N (5r)-5-(azidomethyl)-3-[2-fluoro-4-(2-oxo-1,3-oxazolidin-3-yl)phenyl]-1,3-oxazolidin-2-one Chemical compound FC1=CC(N2C(OCC2)=O)=CC=C1N1C[C@H](CN=[N+]=[N-])OC1=O BAUYXWOSBYZLIU-VIFPVBQESA-N 0.000 claims description 2
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• HHKOTYAQIYFYBG-ZDUSSCGKSA-N n-[[(5s)-2-oxo-3-[4-(2-oxo-1,3-oxazolidin-3-yl)phenyl]-1,3-oxazolidin-5-yl]methyl]ethanethioamide Chemical compound O=C1O[C@@H](CNC(=S)C)CN1C1=CC=C(N2C(OCC2)=O)C=C1 HHKOTYAQIYFYBG-ZDUSSCGKSA-N 0.000 claims description 2
• OJHAZXKLQOVZKF-NSHDSACASA-N n-[[(5s)-3-[2-fluoro-4-(2-oxo-1,3-oxazolidin-3-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C1=CC=C(N2C(OCC2)=O)C=C1F OJHAZXKLQOVZKF-NSHDSACASA-N 0.000 claims description 2
• VBMXGKCKHFZJAN-JTQLQIEISA-N n-[[(5s)-3-[3,5-difluoro-4-(2-oxo-1,3-oxazolidin-3-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC(F)=C1N1C(=O)OCC1 VBMXGKCKHFZJAN-JTQLQIEISA-N 0.000 claims description 2
• GPVNIESOLQKJJF-JTQLQIEISA-N n-[[(5s)-3-[3,5-difluoro-4-(2-oxo-1,3-oxazolidin-3-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]ethanethioamide Chemical compound O=C1O[C@@H](CNC(=S)C)CN1C(C=C1F)=CC(F)=C1N1C(=O)OCC1 GPVNIESOLQKJJF-JTQLQIEISA-N 0.000 claims description 2
• ZFUOXOUFJFNDAU-JTQLQIEISA-N n-[[(5s)-3-[3,5-difluoro-4-(2-oxo-1,3-oxazolidin-3-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]propanamide Chemical compound O=C1O[C@@H](CNC(=O)CC)CN1C(C=C1F)=CC(F)=C1N1C(=O)OCC1 ZFUOXOUFJFNDAU-JTQLQIEISA-N 0.000 claims description 2
• FWBGGMRUKIISSM-JTQLQIEISA-N n-[[(5s)-3-[3,5-difluoro-4-(2-oxo-1,3-oxazolidin-3-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]propanethioamide Chemical compound O=C1O[C@@H](CNC(=S)CC)CN1C(C=C1F)=CC(F)=C1N1C(=O)OCC1 FWBGGMRUKIISSM-JTQLQIEISA-N 0.000 claims description 2
• BSGRZZDQXJMOJA-NSHDSACASA-N n-[[(5s)-3-[3-fluoro-4-(2-oxo-1,3-oxazolidin-3-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1C(=O)OCC1 BSGRZZDQXJMOJA-NSHDSACASA-N 0.000 claims description 2
• PDXRYOZTTDVMOC-NSHDSACASA-N n-[[(5s)-3-[3-fluoro-4-(2-oxo-1,3-oxazolidin-3-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]ethanethioamide Chemical compound O=C1O[C@@H](CNC(=S)C)CN1C(C=C1F)=CC=C1N1C(=O)OCC1 PDXRYOZTTDVMOC-NSHDSACASA-N 0.000 claims description 2
• PPFRJJNAUIDSFO-JTQLQIEISA-N n-[[(5s)-3-[3-fluoro-4-(2-oxo-1,3-oxazolidin-3-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]formamide Chemical compound FC1=CC(N2C(O[C@@H](CNC=O)C2)=O)=CC=C1N1CCOC1=O PPFRJJNAUIDSFO-JTQLQIEISA-N 0.000 claims description 2
• KLERNSIVAUASCY-HNNXBMFYSA-N n-[[(5s)-3-[3-fluoro-4-(2-oxo-1,3-oxazolidin-3-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]heptanamide Chemical compound O=C1O[C@@H](CNC(=O)CCCCCC)CN1C(C=C1F)=CC=C1N1C(=O)OCC1 KLERNSIVAUASCY-HNNXBMFYSA-N 0.000 claims description 2
• UJECIDDUVQIHED-ZDUSSCGKSA-N n-[[(5s)-3-[3-fluoro-4-(2-oxo-1,3-oxazolidin-3-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]pentanamide Chemical compound O=C1O[C@@H](CNC(=O)CCCC)CN1C(C=C1F)=CC=C1N1C(=O)OCC1 UJECIDDUVQIHED-ZDUSSCGKSA-N 0.000 claims description 2
• JZUFKJITPSOJLH-NSHDSACASA-N n-[[(5s)-3-[3-fluoro-4-(2-oxo-1,3-oxazolidin-3-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]prop-2-enamide Chemical compound FC1=CC(N2C(O[C@@H](CNC(=O)C=C)C2)=O)=CC=C1N1CCOC1=O JZUFKJITPSOJLH-NSHDSACASA-N 0.000 claims description 2
• HVTTVYRIJMSUPF-NSHDSACASA-N n-[[(5s)-3-[3-fluoro-4-(2-oxo-1,3-oxazolidin-3-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]propanamide Chemical compound O=C1O[C@@H](CNC(=O)CC)CN1C(C=C1F)=CC=C1N1C(=O)OCC1 HVTTVYRIJMSUPF-NSHDSACASA-N 0.000 claims description 2
• UVOAHHKBBZCZKF-KRWDZBQOSA-N n-[[(5s)-3-[3-fluoro-4-(2-oxo-3-phenylimidazolidin-1-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1C(=O)N(C=2C=CC=CC=2)CC1 UVOAHHKBBZCZKF-KRWDZBQOSA-N 0.000 claims description 2
• NGZTXIMPNRSEKY-NSHDSACASA-N n-[[(5s)-3-[3-fluoro-4-(2-sulfanylidene-1,3-oxazolidin-3-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1C(=S)OCC1 NGZTXIMPNRSEKY-NSHDSACASA-N 0.000 claims description 2
• GDNXYPAJKULNKA-NSHDSACASA-N n-[[(5s)-3-[3-fluoro-4-(2-sulfanylidene-1,3-thiazolidin-3-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1C(=S)SCC1 GDNXYPAJKULNKA-NSHDSACASA-N 0.000 claims description 2
• QJTQLQQCMPPXIX-LBPRGKRZSA-N n-[[(5s)-3-[3-fluoro-4-(3-methyl-2-oxoimidazolidin-1-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1N(C)CCN1C1=CC=C(N2C(O[C@@H](CNC(C)=O)C2)=O)C=C1F QJTQLQQCMPPXIX-LBPRGKRZSA-N 0.000 claims description 2
• ZTYUCAGUOAVOCG-LBPRGKRZSA-N n-[[(5s)-3-[3-fluoro-4-(3-methyl-2-sulfanylideneimidazolidin-1-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound S=C1N(C)CCN1C1=CC=C(N2C(O[C@@H](CNC(C)=O)C2)=O)C=C1F ZTYUCAGUOAVOCG-LBPRGKRZSA-N 0.000 claims description 2
• QHJZGZQOGRGISM-LBPRGKRZSA-N n-[[(5s)-3-[3-fluoro-4-(3-methyl-2-sulfanylideneimidazolidin-1-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]ethanethioamide Chemical compound S=C1N(C)CCN1C1=CC=C(N2C(O[C@@H](CNC(C)=S)C2)=O)C=C1F QHJZGZQOGRGISM-LBPRGKRZSA-N 0.000 claims description 2
• SRVLYUMAWSUPOZ-LBPRGKRZSA-N n-[[(5s)-3-[3-fluoro-4-(3-methyl-4-oxoimidazolidin-1-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound C1C(=O)N(C)CN1C1=CC=C(N2C(O[C@@H](CNC(C)=O)C2)=O)C=C1F SRVLYUMAWSUPOZ-LBPRGKRZSA-N 0.000 claims description 2
• JMWLIUDYAWSYNE-LBPRGKRZSA-N n-[[(5s)-3-[3-fluoro-4-(3-methyl-4-oxoimidazolidin-1-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]ethanethioamide Chemical compound C1C(=O)N(C)CN1C1=CC=C(N2C(O[C@@H](CNC(C)=S)C2)=O)C=C1F JMWLIUDYAWSYNE-LBPRGKRZSA-N 0.000 claims description 2
• GSNJCUXZBQBDKD-KRWDZBQOSA-N n-[[(5s)-3-[3-fluoro-4-[3-(4-fluorophenyl)-2-oxoimidazolidin-1-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1C(=O)N(C=2C=CC(F)=CC=2)CC1 GSNJCUXZBQBDKD-KRWDZBQOSA-N 0.000 claims description 2
• IAOBXRUJPCCRQZ-FQEVSTJZSA-N n-[[(5s)-3-[4-(3-benzyl-2-oxoimidazolidin-1-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C1=CC=C(N2C(N(CC=3C=CC=CC=3)CC2)=O)C=C1 IAOBXRUJPCCRQZ-FQEVSTJZSA-N 0.000 claims description 2
• TWAFVIDWSSCIDY-SFHVURJKSA-N n-[[(5s)-3-[4-(3-benzyl-4-oxoimidazolidin-1-yl)-3-fluorophenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1CC(=O)N(CC=2C=CC=CC=2)C1 TWAFVIDWSSCIDY-SFHVURJKSA-N 0.000 claims description 2
• DJXDARFOMVOEQB-AWEZNQCLSA-N n-[[(5s)-3-[4-(3-methyl-2-oxoimidazolidin-1-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1N(C)CCN1C1=CC=C(N2C(O[C@@H](CNC(C)=O)C2)=O)C=C1 DJXDARFOMVOEQB-AWEZNQCLSA-N 0.000 claims description 2
• VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims description 2
• COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 claims description 2
• 229910052700 potassium Inorganic materials 0.000 claims description 2
• MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 claims description 2
• 229960004919 procaine Drugs 0.000 claims description 2
• JKWONDKDFCXETQ-UHFFFAOYSA-N propan-2-ylcarbamothioic s-acid Chemical compound CC(C)NC(S)=O JKWONDKDFCXETQ-UHFFFAOYSA-N 0.000 claims description 2
• 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims description 2
• 230000002829 reductive effect Effects 0.000 claims description 2
• 229910052708 sodium Inorganic materials 0.000 claims description 2
• KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 claims description 2
• 229960004559 theobromine Drugs 0.000 claims description 2
• KYMBYSLLVAOCFI-UHFFFAOYSA-N thiamine Chemical compound CC1=C(CCO)SCN1CC1=CN=C(C)N=C1N KYMBYSLLVAOCFI-UHFFFAOYSA-N 0.000 claims description 2
• 235000019157 thiamine Nutrition 0.000 claims description 2
• 229960003495 thiamine Drugs 0.000 claims description 2
• 239000011721 thiamine Substances 0.000 claims description 2
• 229930192474 thiophene Natural products 0.000 claims description 2
• FGMPLJWBKKVCDB-UHFFFAOYSA-N trans-L-hydroxy-proline Natural products ON1CCCC1C(O)=O FGMPLJWBKKVCDB-UHFFFAOYSA-N 0.000 claims description 2
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 2
• 125000005270 trialkylamine group Chemical group 0.000 claims description 2
• YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 claims description 2
• OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 claims description 2
• 239000004474 valine Substances 0.000 claims description 2
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 101
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 26
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 25
• 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 21
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 10
• 238000004519 manufacturing process Methods 0.000 claims 4
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 3
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 2
• 125000006529 (C3-C6) alkyl group Chemical group 0.000 claims 2
• BNCMOAYLLRWVTM-JTQLQIEISA-N (5r)-5-(azidomethyl)-3-[3-fluoro-4-(3-methyl-4-oxoimidazolidin-1-yl)phenyl]-1,3-oxazolidin-2-one Chemical compound C1C(=O)N(C)CN1C1=CC=C(N2C(O[C@@H](CN=[N+]=[N-])C2)=O)C=C1F BNCMOAYLLRWVTM-JTQLQIEISA-N 0.000 claims 1
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
• KPGXRSRHYNQIFN-UHFFFAOYSA-N 2-oxoglutaric acid Chemical class OC(=O)CCC(=O)C(O)=O KPGXRSRHYNQIFN-UHFFFAOYSA-N 0.000 claims 1
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
• BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims 1
• POSCEOZJLWACHU-OYKVQYDMSA-N C1COC(=O)N1C2=CC=C(C=C2)N3C[C@H](OC3=O)C(NCCC4=CC=CC=N4)NC=S Chemical compound C1COC(=O)N1C2=CC=C(C=C2)N3C[C@H](OC3=O)C(NCCC4=CC=CC=N4)NC=S POSCEOZJLWACHU-OYKVQYDMSA-N 0.000 claims 1
• KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims 1
• 150000000994 L-ascorbates Chemical class 0.000 claims 1
• 229910002651 NO3 Inorganic materials 0.000 claims 1
• NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims 1
• QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 1
• GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims 1
• UPABQMWFWCMOFV-UHFFFAOYSA-N benethamine Chemical compound C=1C=CC=CC=1CNCCC1=CC=CC=C1 UPABQMWFWCMOFV-UHFFFAOYSA-N 0.000 claims 1
• 150000001558 benzoic acid derivatives Chemical class 0.000 claims 1
• QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 claims 1
• 150000002315 glycerophosphates Chemical class 0.000 claims 1
• BXWXOMYIEPEBDZ-MYJWUSKBSA-N n-[[(5s)-2-oxo-3-[4-(2-oxo-1,3-oxazolidin-3-yl)phenyl]-1,3-oxazolidin-5-yl]-(pyridin-2-ylamino)methyl]methanethioamide Chemical compound O=C1OCCN1C1=CC=C(N2C(O[C@@H](C2)C(NC=S)NC=2N=CC=CC=2)=O)C=C1 BXWXOMYIEPEBDZ-MYJWUSKBSA-N 0.000 claims 1
• NXVJUNKFDJVOAX-LBPRGKRZSA-N n-[[(5s)-3-[3-fluoro-4-(3-methyl-2-oxoimidazolidin-1-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]ethanethioamide Chemical compound O=C1N(C)CCN1C1=CC=C(N2C(O[C@@H](CNC(C)=S)C2)=O)C=C1F NXVJUNKFDJVOAX-LBPRGKRZSA-N 0.000 claims 1
• VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 claims 1
• NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 1
• 239000010452 phosphate Substances 0.000 claims 1
• 150000003873 salicylate salts Chemical class 0.000 claims 1
• 229940095064 tartrate Drugs 0.000 claims 1
• 238000006243 chemical reaction Methods 0.000 description 117
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 99
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 98
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 69
• 239000002904 solvent Substances 0.000 description 61
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 52
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 51
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 44
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 40
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 37
• 239000011541 reaction mixture Substances 0.000 description 34
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 34
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 32
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 30
• 230000035484 reaction time Effects 0.000 description 30
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 27
• ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 26
• 229910000104 sodium hydride Inorganic materials 0.000 description 26
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 25
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• 0 CN1CCC(*)CC1 Chemical compound CN1CCC(*)CC1 0.000 description 24
• 239000007787 solid Substances 0.000 description 23
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 21
• 229910000027 potassium carbonate Inorganic materials 0.000 description 21
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• 239000000460 chlorine Substances 0.000 description 20
• 229910052757 nitrogen Inorganic materials 0.000 description 19
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• 229910052801 chlorine Inorganic materials 0.000 description 17
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 17
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
• 229910052786 argon Inorganic materials 0.000 description 16
• 239000012267 brine Substances 0.000 description 16
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 15
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
• 239000000047 product Substances 0.000 description 15
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