HUT76289A

HUT76289A - Carbamate derivative and medicinal composition containing the same

Carbamate derivative and medicinal composition containing the same Download PDF

Info

Publication number: HUT76289A
Authority: HU; Hungary
Prior art keywords: carbamate; group; formula; ring; compound
Prior art date: 1994-02-10

Application number

HU9602188A

Other languages

English (en)

Hungarian (hu)

Other versions

HU9602188D0 (en

Inventor

Masahiko Hayakawa

Ken Ikeda

Yasuo Isomura

Koichiro Morihira

Ryo Naito

Makoto Takeuchi

Original Assignee

Yamanouchi Pharma Co Ltd

Priority date

1994-02-10

Filing date

1995-02-08

Publication date

1997-07-28

1995-02-08 Application filed by Yamanouchi Pharma Co Ltd filed Critical Yamanouchi Pharma Co Ltd

1996-10-28 Publication of HU9602188D0 publication Critical patent/HU9602188D0/hu

1997-07-28 Publication of HUT76289A publication Critical patent/HUT76289A/hu

Links

AKZWRTCWNXHHFR-PDIZUQLASA-N [(3S)-oxolan-3-yl] N-[(2S,3S)-4-[(5S)-5-benzyl-3-[(2R)-2-carbamoyloxy-2,3-dihydro-1H-inden-1-yl]-4-oxo-3H-pyrrol-5-yl]-3-hydroxy-1-phenylbutan-2-yl]carbamate Chemical compound NC(=O)O[C@@H]1Cc2ccccc2C1C1C=N[C@](C[C@H](O)[C@H](Cc2ccccc2)NC(=O)O[C@H]2CCOC2)(Cc2ccccc2)C1=O AKZWRTCWNXHHFR-PDIZUQLASA-N 0.000 title claims description 10
239000000203 mixture Substances 0.000 title description 64
150000003839 salts Chemical class 0.000 claims abstract description 31
125000001424 substituent group Chemical group 0.000 claims abstract description 18
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 16
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 10
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 9
239000012453 solvate Substances 0.000 claims abstract description 7
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 6
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 6
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 5
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 5
208000023504 respiratory system disease Diseases 0.000 claims abstract description 5
238000011282 treatment Methods 0.000 claims abstract description 5
208000018522 Gastrointestinal disease Diseases 0.000 claims abstract description 4
125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 3
230000002265 prevention Effects 0.000 claims abstract description 3
125000000217 alkyl group Chemical group 0.000 claims description 41
125000003710 aryl alkyl group Chemical group 0.000 claims description 15
125000003342 alkenyl group Chemical group 0.000 claims description 13
125000000304 alkynyl group Chemical group 0.000 claims description 13
230000003551 muscarinic effect Effects 0.000 claims description 13
125000005842 heteroatom Chemical group 0.000 claims description 10
229910052739 hydrogen Inorganic materials 0.000 claims description 10
239000003681 muscarinic M3 receptor antagonist Substances 0.000 claims description 8
206010046543 Urinary incontinence Diseases 0.000 claims description 7
125000003545 alkoxy group Chemical group 0.000 claims description 7
150000001450 anions Chemical class 0.000 claims description 7
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 7
229910052736 halogen Inorganic materials 0.000 claims description 7
150000002367 halogens Chemical class 0.000 claims description 7
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 7
239000001257 hydrogen Substances 0.000 claims description 6
206010006458 Bronchitis chronic Diseases 0.000 claims description 5
239000004480 active ingredient Substances 0.000 claims description 5
206010006451 bronchitis Diseases 0.000 claims description 5
208000007451 chronic bronchitis Diseases 0.000 claims description 5
201000010099 disease Diseases 0.000 claims description 5
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 4
208000006673 asthma Diseases 0.000 claims description 4
208000002551 irritable bowel syndrome Diseases 0.000 claims description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
239000008194 pharmaceutical composition Substances 0.000 claims description 4
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 3
206010063057 Cystitis noninfective Diseases 0.000 claims description 3
206010020853 Hypertonic bladder Diseases 0.000 claims description 3
201000003139 chronic cystitis Diseases 0.000 claims description 3
125000003396 thiol group Chemical group [H]S* 0.000 claims description 3
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 2
206010048994 Bladder spasm Diseases 0.000 claims description 2
208000000693 Neurogenic Urinary Bladder Diseases 0.000 claims description 2
206010029279 Neurogenic bladder Diseases 0.000 claims description 2
230000000422 nocturnal effect Effects 0.000 claims description 2
210000002700 urine Anatomy 0.000 claims description 2
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 2
210000001635 urinary tract Anatomy 0.000 claims 2
241000162682 Heterogen Species 0.000 claims 1
208000019693 Lung disease Diseases 0.000 claims 1
208000023819 chronic asthma Diseases 0.000 claims 1
230000001684 chronic effect Effects 0.000 claims 1
201000003146 cystitis Diseases 0.000 claims 1
230000001272 neurogenic effect Effects 0.000 claims 1
230000000414 obstructive effect Effects 0.000 claims 1
150000004657 carbamic acid derivatives Chemical class 0.000 abstract description 12
229920006395 saturated elastomer Polymers 0.000 abstract description 11
125000004432 carbon atom Chemical group C* 0.000 abstract description 10
230000008485 antagonism Effects 0.000 abstract description 5
150000004677 hydrates Chemical class 0.000 abstract description 5
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 abstract description 4
208000014001 urinary system disease Diseases 0.000 abstract description 3
239000003795 chemical substances by application Substances 0.000 abstract description 2
102000007202 Muscarinic M3 Receptor Human genes 0.000 abstract 1
108010008405 Muscarinic M3 Receptor Proteins 0.000 abstract 1
238000004132 cross linking Methods 0.000 abstract 1
-1 piperidin-4-ol ester compounds Chemical class 0.000 description 160
150000001875 compounds Chemical class 0.000 description 149
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 148
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 96
239000002904 solvent Substances 0.000 description 58
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 52
239000000460 chlorine Substances 0.000 description 50
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 48
238000004458 analytical method Methods 0.000 description 47
238000002844 melting Methods 0.000 description 47
230000008018 melting Effects 0.000 description 47
239000007858 starting material Substances 0.000 description 45
239000000243 solution Substances 0.000 description 40
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 39
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 33
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 33
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 30
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
238000006243 chemical reaction Methods 0.000 description 25
239000013078 crystal Substances 0.000 description 25
238000000034 method Methods 0.000 description 25
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
102000005962 receptors Human genes 0.000 description 19
108020003175 receptors Proteins 0.000 description 19
238000012360 testing method Methods 0.000 description 19
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
239000007787 solid Substances 0.000 description 18
239000012044 organic layer Substances 0.000 description 17
238000010898 silica gel chromatography Methods 0.000 description 15
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 14
238000001816 cooling Methods 0.000 description 14
230000008569 process Effects 0.000 description 14
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 13
239000012267 brine Substances 0.000 description 13
238000002360 preparation method Methods 0.000 description 13
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 13
230000000694 effects Effects 0.000 description 12
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 12
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 11
125000003118 aryl group Chemical group 0.000 description 11
238000004519 manufacturing process Methods 0.000 description 11
239000000463 material Substances 0.000 description 11
210000003932 urinary bladder Anatomy 0.000 description 11
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
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 10
102000014415 Muscarinic acetylcholine receptor Human genes 0.000 description 10
108050003473 Muscarinic acetylcholine receptor Proteins 0.000 description 10
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
230000008602 contraction Effects 0.000 description 10
239000003480 eluent Substances 0.000 description 10
239000008101 lactose Substances 0.000 description 10
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 9
229910052799 carbon Inorganic materials 0.000 description 9
238000003756 stirring Methods 0.000 description 9
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 8
206010006482 Bronchospasm Diseases 0.000 description 8
RKUNBYITZUJHSG-UHFFFAOYSA-N Hyosciamin-hydrochlorid Natural products CN1C(C2)CCC1CC2OC(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-UHFFFAOYSA-N 0.000 description 8
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
RKUNBYITZUJHSG-SPUOUPEWSA-N atropine Chemical compound O([C@H]1C[C@H]2CC[C@@H](C1)N2C)C(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-SPUOUPEWSA-N 0.000 description 8
229960000396 atropine Drugs 0.000 description 8
239000003054 catalyst Substances 0.000 description 8
238000010438 heat treatment Methods 0.000 description 8
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 8
229910000041 hydrogen chloride Inorganic materials 0.000 description 8
239000012442 inert solvent Substances 0.000 description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 8
JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 7
229930003347 Atropine Natural products 0.000 description 7
239000007995 HEPES buffer Substances 0.000 description 7
150000001412 amines Chemical class 0.000 description 7
238000003556 assay Methods 0.000 description 7
239000003921 oil Substances 0.000 description 7
235000019198 oils Nutrition 0.000 description 7
AGZCCVMWUZINGV-UHFFFAOYSA-N piperidin-4-yl n-(2-phenylphenyl)carbamate Chemical compound C1CNCCC1OC(=O)NC1=CC=CC=C1C1=CC=CC=C1 AGZCCVMWUZINGV-UHFFFAOYSA-N 0.000 description 7
239000003826 tablet Substances 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
238000009472 formulation Methods 0.000 description 6
235000019359 magnesium stearate Nutrition 0.000 description 6
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 5
229940121948 Muscarinic receptor antagonist Drugs 0.000 description 5
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
239000002253 acid Substances 0.000 description 5
230000007885 bronchoconstriction Effects 0.000 description 5
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 5
230000005764 inhibitory process Effects 0.000 description 5
150000002825 nitriles Chemical class 0.000 description 5
229910052760 oxygen Inorganic materials 0.000 description 5
229910000027 potassium carbonate Inorganic materials 0.000 description 5
239000000843 powder Substances 0.000 description 5
SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
230000001020 rhythmical effect Effects 0.000 description 5
239000012312 sodium hydride Substances 0.000 description 5
229910000104 sodium hydride Inorganic materials 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
238000005303 weighing Methods 0.000 description 5
XHIQZUNDUKHSQA-UHFFFAOYSA-N 1-azabicyclo[2.2.2]octan-4-yl n-(2-phenylphenyl)carbamate Chemical compound C1CN(CC2)CCC12OC(=O)NC1=CC=CC=C1C1=CC=CC=C1 XHIQZUNDUKHSQA-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
238000007126 N-alkylation reaction Methods 0.000 description 4
241000700159 Rattus Species 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 4
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
150000001350 alkyl halides Chemical class 0.000 description 4
125000003277 amino group Chemical group 0.000 description 4
229910021529 ammonia Inorganic materials 0.000 description 4
235000019270 ammonium chloride Nutrition 0.000 description 4
239000002585 base Substances 0.000 description 4
230000027455 binding Effects 0.000 description 4
150000001721 carbon Chemical group 0.000 description 4
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
238000010828 elution Methods 0.000 description 4
239000008187 granular material Substances 0.000 description 4
239000007924 injection Substances 0.000 description 4
238000002347 injection Methods 0.000 description 4
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 4
239000007788 liquid Substances 0.000 description 4
238000002156 mixing Methods 0.000 description 4
239000003149 muscarinic antagonist Substances 0.000 description 4
235000006408 oxalic acid Nutrition 0.000 description 4
239000002504 physiological saline solution Substances 0.000 description 4
239000000047 product Substances 0.000 description 4
125000004368 propenyl group Chemical group C(=CC)* 0.000 description 4
238000001525 receptor binding assay Methods 0.000 description 4
210000003296 saliva Anatomy 0.000 description 4
229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
235000017557 sodium bicarbonate Nutrition 0.000 description 4
210000001519 tissue Anatomy 0.000 description 4
KYDOSBOZOAMBJZ-UHFFFAOYSA-N 1,3-bis(2-cyclohex-2-en-1-ylphenyl)urea Chemical compound C=1C=CC=C(C2C=CCCC2)C=1NC(=O)NC1=CC=CC=C1C1CCCC=C1 KYDOSBOZOAMBJZ-UHFFFAOYSA-N 0.000 description 3
ILYSAKHOYBPSPC-UHFFFAOYSA-N 2-phenylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C1=CC=CC=C1 ILYSAKHOYBPSPC-UHFFFAOYSA-N 0.000 description 3
IVLICPVPXWEGCA-UHFFFAOYSA-N 3-quinuclidinol Chemical compound C1C[C@@H]2C(O)C[N@]1CC2 IVLICPVPXWEGCA-UHFFFAOYSA-N 0.000 description 3
208000009079 Bronchial Spasm Diseases 0.000 description 3
208000014181 Bronchial disease Diseases 0.000 description 3
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
229920000168 Microcrystalline cellulose Polymers 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
229910000564 Raney nickel Inorganic materials 0.000 description 3
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
125000002252 acyl group Chemical group 0.000 description 3
239000002168 alkylating agent Substances 0.000 description 3
229940100198 alkylating agent Drugs 0.000 description 3
150000003863 ammonium salts Chemical class 0.000 description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
239000003638 chemical reducing agent Substances 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
MKRTXPORKIRPDG-UHFFFAOYSA-N diphenylphosphoryl azide Chemical compound C=1C=CC=CC=1P(=O)(N=[N+]=[N-])C1=CC=CC=C1 MKRTXPORKIRPDG-UHFFFAOYSA-N 0.000 description 3
239000003814 drug Substances 0.000 description 3
206010013781 dry mouth Diseases 0.000 description 3
PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 3
LJQKCYFTNDAAPC-UHFFFAOYSA-N ethanol;ethyl acetate Chemical compound CCO.CCOC(C)=O LJQKCYFTNDAAPC-UHFFFAOYSA-N 0.000 description 3
125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 3
239000006260 foam Substances 0.000 description 3
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 3
239000004220 glutamic acid Substances 0.000 description 3
235000013922 glutamic acid Nutrition 0.000 description 3
238000005984 hydrogenation reaction Methods 0.000 description 3
125000002883 imidazolyl group Chemical group 0.000 description 3
238000001727 in vivo Methods 0.000 description 3
239000003701 inert diluent Substances 0.000 description 3
239000012528 membrane Substances 0.000 description 3
XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 3
239000008108 microcrystalline cellulose Substances 0.000 description 3
235000019813 microcrystalline cellulose Nutrition 0.000 description 3
229940016286 microcrystalline cellulose Drugs 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
125000006501 nitrophenyl group Chemical group 0.000 description 3
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 3
239000001301 oxygen Substances 0.000 description 3
239000000546 pharmaceutical excipient Substances 0.000 description 3
125000003386 piperidinyl group Chemical group 0.000 description 3
229910003446 platinum oxide Inorganic materials 0.000 description 3
125000004076 pyridyl group Chemical group 0.000 description 3
125000000168 pyrrolyl group Chemical group 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
238000010992 reflux Methods 0.000 description 3
230000028327 secretion Effects 0.000 description 3
239000012279 sodium borohydride Substances 0.000 description 3
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